# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2005
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_Cambridge 0177
_publ_contact_author_name 'Prof M Bryce'
_publ_contact_author_address
;
Department of Chemistry
University of Durham
South Road
DURHAM
DH1 3LE
;
_publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK
_publ_section_title
;
A versatile synthesis of pyrazolo[3,4-c]isoquinoline
derivatives by reaction of 4-aryl-5-aminopyrazoles with aryl/heteroaryl
aldehydes: the effect of the heterocycle on the reaction pathways
;
loop_
_publ_author_name
'M. Bryce'
'Andrei S. Batsanov'
'Natalya M. Bogdan'
'Sergei L. Bogza'
'Konstantin I. Kobrakov'
;
S.B.Lyubchik
;
'Anna A. Malienko'
'Igor F. Perepichka'
'Sergei Yu. Sujkov'
data_(10Dj)
_database_code_depnum_ccdc_archive 'CCDC 232595'
_audit_creation_method SHELXL-97
_chemical_name_systematic
; 1-Methyl-3-phenyl-5-(thienyl-2)-7,8-dimethoxypyrazolo[3,4]isoquinoline
;
_chemical_name_common
;1-Methyl-3-phenyl-5-(thienyl-2)-7,8-
dimethoxypyrazolo(3,4)isoquinoline
;
_chemical_melting_point '209.5--210 \% C'
_chemical_formula_moiety 'C23 H19 N3 O2 S'
_chemical_formula_sum 'C23 H19 N3 O2 S'
_chemical_formula_weight 401.47
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M Pca2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
_cell_length_a 22.845(4)
_cell_length_b 11.858(2)
_cell_length_c 7.188(1)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1947.2(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 123(2)
_cell_measurement_reflns_used 686
_cell_measurement_theta_min 12
_cell_measurement_theta_max 25
_exptl_crystal_description prism
_exptl_crystal_colour 'light brown'
_exptl_crystal_size_max 0.33
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.361
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 840
_exptl_absorpt_coefficient_mu 0.190
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0400
1.00 0.00 0.00 0.0400
0.00 1.00 0.00 0.0750
0.00 -1.00 0.00 0.0750
1.00 0.00 1.00 0.1400
-1.00 0.00 -1.00 0.1400
_exptl_special_details
; The data collection nominally covered over a hemisphere
of reciprocal space, by a combination of 4 sets of exposures;
each set had a different \f and/or 2\q angles and each
exposure (20 s) covered 0.3\% in \w. Crystal decay was
monitored by repeating 50 initial frames at the end of data
collection and comparing 156 duplicate reflections.
Crystal to detector distance 4.53 cm.
;
_diffrn_ambient_temperature 123(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SMART 1K CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number 13783
_diffrn_reflns_av_R_equivalents 0.0480
_diffrn_reflns_av_sigmaI/netI 0.0501
_diffrn_reflns_limit_h_min -29
_diffrn_reflns_limit_h_max 29
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 1.93
_diffrn_reflns_theta_max 27.56
_reflns_number_total 4490
_reflns_number_gt 3735
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART version 5.054 (Bruker, 1998)'
_computing_cell_refinement 'SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.02(7)
_refine_ls_number_reflns 4490
_refine_ls_number_parameters 271
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0528
_refine_ls_R_factor_gt 0.0392
_refine_ls_wR_factor_ref 0.0847
_refine_ls_wR_factor_gt 0.0797
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_restrained_S_all 1.015
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.46793(2) 0.50811(4) 0.44862(9) 0.02268(12) Uani 1 1 d . . .
O1 O 0.14273(6) 0.74403(11) 0.3812(2) 0.0229(3) Uani 1 1 d . . .
O2 O 0.23732(5) 0.85657(10) 0.4524(2) 0.0227(3) Uani 1 1 d . . .
N1 N 0.36562(7) 0.42059(13) 0.2429(2) 0.0186(4) Uani 1 1 d . . .
N2 N 0.31067(7) 0.25164(13) 0.1756(3) 0.0200(4) Uani 1 1 d . . .
N3 N 0.25285(8) 0.22000(13) 0.1601(2) 0.0203(4) Uani 1 1 d . . .
C1 C 0.19373(9) 0.68581(17) 0.3586(3) 0.0189(4) Uani 1 1 d . . .
C2 C 0.24553(9) 0.74783(15) 0.3959(3) 0.0182(4) Uani 1 1 d . . .
C3 C 0.29884(9) 0.69741(17) 0.3733(3) 0.0188(4) Uani 1 1 d . . .
H3 H 0.3333 0.7393 0.3984 0.023 Uiso 1 1 d R . .
C4 C 0.30380(8) 0.58371(16) 0.3133(3) 0.0167(4) Uani 1 1 d . . .
C5 C 0.25153(9) 0.52150(15) 0.2820(3) 0.0169(4) Uani 1 1 d . . .
C6 C 0.19673(9) 0.57504(16) 0.3041(3) 0.0184(4) Uani 1 1 d . . .
H6 H 0.1618 0.5342 0.2810 0.022 Uiso 1 1 d R . .
C7 C 0.25833(8) 0.40574(15) 0.2332(3) 0.0179(4) Uani 1 1 d . . .
C8 C 0.31509(9) 0.36426(15) 0.2199(3) 0.0182(4) Uani 1 1 d . . .
C9 C 0.35970(8) 0.52892(16) 0.2895(3) 0.0172(4) Uani 1 1 d . . .
C10 C 0.22142(9) 0.31156(16) 0.1943(3) 0.0188(4) Uani 1 1 d . . .
C11 C 0.35567(9) 0.16955(16) 0.1525(3) 0.0204(4) Uani 1 1 d . . .
C12 C 0.34694(9) 0.08292(16) 0.0257(3) 0.0254(5) Uani 1 1 d . . .
H12 H 0.3126 0.0807 -0.0482 0.030 Uiso 1 1 d R . .
C13 C 0.38941(10) -0.00057(18) 0.0087(3) 0.0318(6) Uani 1 1 d . . .
H13 H 0.3837 -0.0607 -0.0763 0.038 Uiso 1 1 d R . .
C14 C 0.43978(10) 0.00336(19) 0.1145(4) 0.0318(5) Uani 1 1 d . . .
H14 H 0.4684 -0.0541 0.1031 0.038 Uiso 1 1 d R . .
C15 C 0.44825(10) 0.09188(18) 0.2375(3) 0.0305(5) Uani 1 1 d . . .
H15 H 0.4832 0.0955 0.3084 0.037 Uiso 1 1 d R . .
C16 C 0.40631(9) 0.17499(17) 0.2579(3) 0.0259(5) Uani 1 1 d . . .
H16 H 0.4121 0.2350 0.3431 0.031 Uiso 1 1 d R . .
C17 C 0.15600(9) 0.30476(16) 0.1954(3) 0.0216(4) Uani 1 1 d . . .
H171 H 0.14391(17) 0.2290(9) 0.1623(17) 0.027(3) Uiso 1 1 d R . .
H172 H 0.1402(2) 0.3579(10) 0.1062(16) 0.027(3) Uiso 1 1 d R . .
H173 H 0.14153(19) 0.3229(10) 0.3186(15) 0.027(3) Uiso 1 1 d R . .
C18 C 0.08960(9) 0.68803(18) 0.3289(3) 0.0263(5) Uani 1 1 d . . .
H181 H 0.0910(2) 0.6692(10) 0.1985(18) 0.031(4) Uiso 1 1 d R . .
H182 H 0.0568(4) 0.7372(8) 0.3520(17) 0.031(4) Uiso 1 1 d R . .
H183 H 0.0852(3) 0.6200(11) 0.4012(16) 0.031(4) Uiso 1 1 d R . .
C19 C 0.28899(9) 0.92227(17) 0.4844(3) 0.0283(6) Uani 1 1 d . . .
H191 H 0.3130(5) 0.8858(8) 0.581(2) 0.042(4) Uiso 1 1 d R . .
H192 H 0.27779(17) 0.9985(11) 0.526(2) 0.042(4) Uiso 1 1 d R . .
H193 H 0.3117(4) 0.9276(10) 0.3682(16) 0.042(4) Uiso 1 1 d R . .
C20 C 0.41574(9) 0.58619(17) 0.3300(3) 0.0196(4) Uani 1 1 d . . .
C21 C 0.43574(9) 0.69356(16) 0.2986(3) 0.0219(4) Uani 1 1 d . . .
H21 H 0.4138 0.7495 0.2352 0.026 Uiso 1 1 d R . .
C22 C 0.49275(9) 0.71233(18) 0.3711(3) 0.0246(5) Uani 1 1 d . . .
H22 H 0.5131 0.7817 0.3601 0.030 Uiso 1 1 d R . .
C23 C 0.51506(8) 0.61968(17) 0.4581(3) 0.0250(4) Uani 1 1 d . . .
H23 H 0.5522 0.6175 0.5168 0.030 Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0180(2) 0.0234(2) 0.0266(2) 0.0006(2) -0.0020(3) 0.0020(2)
O1 0.0163(7) 0.0201(7) 0.0323(8) -0.0060(6) -0.0006(6) 0.0022(6)
O2 0.0197(7) 0.0161(6) 0.0325(8) -0.0067(7) -0.0017(8) 0.0002(5)
N1 0.0188(8) 0.0189(9) 0.0181(8) 0.0004(7) 0.0024(7) -0.0004(7)
N2 0.0185(8) 0.0162(8) 0.0252(9) -0.0013(7) 0.0006(7) 0.0002(7)
N3 0.0207(8) 0.0198(8) 0.0205(10) -0.0007(7) 0.0020(8) -0.0022(8)
C1 0.0190(10) 0.0204(10) 0.0172(10) 0.0009(8) 0.0003(8) 0.0037(8)
C2 0.0223(10) 0.0165(10) 0.0157(10) 0.0008(7) -0.0017(8) 0.0007(8)
C3 0.0179(9) 0.0193(10) 0.0192(10) -0.0016(8) -0.0024(8) -0.0030(8)
C4 0.0175(9) 0.0193(10) 0.0134(9) 0.0009(8) -0.0007(8) 0.0019(8)
C5 0.0179(9) 0.0195(9) 0.0134(9) 0.0011(8) -0.0006(8) -0.0005(8)
C6 0.0185(9) 0.0207(10) 0.0161(10) 0.0007(8) -0.0015(8) -0.0018(8)
C7 0.0199(11) 0.0174(9) 0.0163(10) 0.0015(8) 0.0015(8) -0.0009(8)
C8 0.0216(10) 0.0162(9) 0.0169(10) -0.0006(8) 0.0005(8) 0.0012(8)
C9 0.0199(10) 0.0161(9) 0.0156(10) 0.0024(7) 0.0010(8) -0.0007(8)
C10 0.0213(11) 0.0182(10) 0.0168(10) 0.0013(8) -0.0007(9) -0.0020(8)
C11 0.0223(10) 0.0159(10) 0.0231(11) 0.0042(8) 0.0075(9) 0.0009(8)
C12 0.0239(11) 0.0201(11) 0.0322(12) -0.0032(9) 0.0006(10) -0.0039(9)
C13 0.0347(12) 0.0176(10) 0.0430(15) -0.0083(10) 0.0093(11) -0.0008(10)
C14 0.0318(13) 0.0205(11) 0.0431(14) 0.0038(10) 0.0105(11) 0.0075(10)
C15 0.0273(12) 0.0301(12) 0.0341(12) 0.0025(11) -0.0014(10) 0.0070(10)
C16 0.0260(11) 0.0245(11) 0.0272(12) -0.0029(9) -0.0003(9) 0.0016(9)
C17 0.0217(11) 0.0193(10) 0.0237(11) -0.0002(8) -0.0009(9) -0.0025(9)
C18 0.0186(10) 0.0281(12) 0.0322(13) -0.0089(9) -0.0040(9) 0.0027(9)
C19 0.0248(11) 0.0179(10) 0.0420(16) -0.0071(9) -0.0033(10) 0.0003(9)
C20 0.0193(10) 0.0227(10) 0.0168(10) -0.0024(8) -0.0010(8) 0.0043(9)
C21 0.0218(10) 0.0219(11) 0.0219(10) -0.0004(9) 0.0010(9) 0.0000(9)
C22 0.0230(10) 0.0248(11) 0.0260(11) -0.0021(9) 0.0005(9) -0.0040(9)
C23 0.0171(9) 0.0335(11) 0.0243(10) -0.0052(10) -0.0018(10) -0.0030(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C23 1.707(2) . ?
S C20 1.734(2) . ?
O1 C1 1.364(2) . ?
O1 C18 1.434(2) . ?
O2 C2 1.365(2) . ?
O2 C19 1.433(2) . ?
N1 C9 1.334(2) . ?
N1 C8 1.344(2) . ?
N2 C8 1.377(2) . ?
N2 N3 1.378(2) . ?
N2 C11 1.426(3) . ?
N3 C10 1.325(2) . ?
C1 C6 1.373(3) . ?
C1 C2 1.419(3) . ?
C2 C3 1.366(3) . ?
C3 C4 1.420(3) . ?
C4 C5 1.422(3) . ?
C4 C9 1.443(3) . ?
C5 C6 1.413(3) . ?
C5 C7 1.425(3) . ?
C7 C8 1.390(3) . ?
C7 C10 1.427(3) . ?
C9 C20 1.478(3) . ?
C10 C17 1.497(3) . ?
C11 C16 1.385(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.382(3) . ?
C20 C21 1.371(3) . ?
C21 C22 1.420(3) . ?
C22 C23 1.363(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 S C20 92.27(10) . . ?
C1 O1 C18 117.24(15) . . ?
C2 O2 C19 116.63(15) . . ?
C9 N1 C8 114.98(17) . . ?
C8 N2 N3 110.68(16) . . ?
C8 N2 C11 129.53(17) . . ?
N3 N2 C11 119.75(16) . . ?
C10 N3 N2 106.35(15) . . ?
O1 C1 C6 124.12(18) . . ?
O1 C1 C2 115.33(17) . . ?
C6 C1 C2 120.56(18) . . ?
O2 C2 C3 124.84(18) . . ?
O2 C2 C1 115.54(17) . . ?
C3 C2 C1 119.62(17) . . ?
C2 C3 C4 121.51(18) . . ?
C3 C4 C5 118.28(17) . . ?
C3 C4 C9 122.29(17) . . ?
C5 C4 C9 119.40(17) . . ?
C6 C5 C4 119.56(17) . . ?
C6 C5 C7 123.85(18) . . ?
C4 C5 C7 116.57(17) . . ?
C1 C6 C5 120.42(18) . . ?
C8 C7 C5 117.35(17) . . ?
C8 C7 C10 105.11(16) . . ?
C5 C7 C10 137.53(19) . . ?
N1 C8 N2 125.01(18) . . ?
N1 C8 C7 128.08(17) . . ?
N2 C8 C7 106.91(17) . . ?
N1 C9 C4 123.58(18) . . ?
N1 C9 C20 113.82(17) . . ?
C4 C9 C20 122.42(17) . . ?
N3 C10 C7 110.95(17) . . ?
N3 C10 C17 119.87(17) . . ?
C7 C10 C17 129.13(18) . . ?
C16 C11 C12 120.94(19) . . ?
C16 C11 N2 120.48(19) . . ?
C12 C11 N2 118.56(19) . . ?
C11 C12 C13 118.9(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 119.6(2) . . ?
C16 C15 C14 120.7(2) . . ?
C15 C16 C11 119.2(2) . . ?
C21 C20 C9 133.05(18) . . ?
C21 C20 S 110.33(15) . . ?
C9 C20 S 116.57(14) . . ?
C20 C21 C22 113.00(19) . . ?
C23 C22 C21 112.64(19) . . ?
C22 C23 S 111.74(16) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 174.48(17) . . . . ?
O1 C1 C2 O2 1.1(2) . . . . ?
C1 C2 O2 C19 -177.80(18) . . . . ?
N1 C9 C20 S -38.4(2) . . . . ?
N3 N2 C11 C12 34.3(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 27.56
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.207
_refine_diff_density_min -0.278
_refine_diff_density_rms 0.046
#===========================================END
data_(11D)
_database_code_depnum_ccdc_archive 'CCDC 232596'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
1-methyl-3-phenyl-7,8-dimethoxypyrazolo[3,4-c]isoquinoline,
acetonitile solvate
;
_chemical_name_common
;1-methyl-3-phenyl-7,8-dimethoxypyrazolo(3,4-c)isoquinoline,
acetonitile solvate
;
_chemical_melting_point '166--166.5 \% C'
_chemical_formula_moiety 'C19 H17 N3 O2,C2 H3 N'
_chemical_formula_sum 'C21 H20 N4 O2'
_chemical_formula_weight 360.41
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.086(1)
_cell_length_b 10.791(3)
_cell_length_c 12.850(2)
_cell_angle_alpha 104.16(2)
_cell_angle_beta 105.87(2)
_cell_angle_gamma 95.86(1)
_cell_volume 901.2(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 917
_cell_measurement_theta_min 12.0
_cell_measurement_theta_max 26.0
_exptl_crystal_description trapetzoid
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.328
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 380
_exptl_absorpt_coefficient_mu 0.088
_exptl_absorpt_correction_type integration
_exptl_absorpt_correction_T_min 0.9490
_exptl_absorpt_correction_T_max 0.9895
_exptl_absorpt_process_details
'XPREP (SHELXTL), R(int)=0.039 before correction'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 1.00 0.0700
0.00 1.00 -1.00 0.0700
0.00 0.00 1.00 0.0600
0.00 0.00 -1.00 0.0600
-1.00 0.00 1.00 0.2800
1.00 0.00 1.00 0.2800
_exptl_special_details
; The data collection nominally covered full sphere
of reciprocal space, by a combination of 5 sets of \w scans;
each set at different \f and/or 2\q angles and each
scan (10 sec exposure) covering 0.3\% in \w. Crystal to
detector distance 4.4 cm. Crystal decay was
monitored by repeating 50 initial frames at the end of data
collection and comparing 64 duplicate reflections.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'SMART 1K CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number 10258
_diffrn_reflns_av_R_equivalents 0.0326
_diffrn_reflns_av_sigmaI/netI 0.0385
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 1.72
_diffrn_reflns_theta_max 27.54
_reflns_number_total 4128
_reflns_number_gt 2988
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART version 5.049 (Bruker, 1997)'
_computing_cell_refinement 'SMART version 5.049 (Bruker, 1997)'
_computing_data_reduction 'SAINT version 5.00 (Bruker, 1998)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.1401P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4128
_refine_ls_number_parameters 324
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0653
_refine_ls_R_factor_gt 0.0404
_refine_ls_wR_factor_ref 0.1050
_refine_ls_wR_factor_gt 0.0951
_refine_ls_goodness_of_fit_ref 1.024
_refine_ls_restrained_S_all 1.024
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26383(15) 0.80985(9) 0.41678(8) 0.0246(2) Uani 1 1 d . . .
O2 O 0.25986(15) 0.62183(9) 0.25037(8) 0.0251(2) Uani 1 1 d . . .
N1 N 0.24487(17) 0.28036(11) 0.56571(10) 0.0202(3) Uani 1 1 d . . .
N2 N 0.23851(17) 0.37579(10) 0.75689(9) 0.0193(3) Uani 1 1 d . . .
N3 N 0.23686(17) 0.49667(10) 0.82351(10) 0.0204(3) Uani 1 1 d . . .
N4 N 0.3137(2) 1.12121(14) 0.22088(13) 0.0411(4) Uani 1 1 d . . .
C1 C 0.2588(2) 0.69227(13) 0.43823(12) 0.0200(3) Uani 1 1 d . . .
C2 C 0.25868(19) 0.58726(13) 0.34553(11) 0.0202(3) Uani 1 1 d . . .
C3 C 0.25811(19) 0.46446(13) 0.35749(12) 0.0195(3) Uani 1 1 d . . .
H3 H 0.265(2) 0.3938(15) 0.2973(13) 0.022(4) Uiso 1 1 d . . .
C4 C 0.25252(19) 0.44106(13) 0.46066(11) 0.0184(3) Uani 1 1 d . . .
C5 C 0.24965(18) 0.54479(12) 0.55177(11) 0.0182(3) Uani 1 1 d . . .
C6 C 0.25491(19) 0.67144(13) 0.53888(12) 0.0192(3) Uani 1 1 d . . .
H6 H 0.261(2) 0.7444(14) 0.6013(13) 0.020(4) Uiso 1 1 d . . .
C7 C 0.24434(19) 0.51134(12) 0.65145(11) 0.0177(3) Uani 1 1 d . . .
C8 C 0.24208(19) 0.38179(13) 0.65144(11) 0.0185(3) Uani 1 1 d . . .
C9 C 0.25027(19) 0.31329(13) 0.47384(12) 0.0199(3) Uani 1 1 d . . .
H9 H 0.253(2) 0.2440(13) 0.4089(12) 0.014(3) Uiso 1 1 d . . .
C10 C 0.23892(19) 0.57750(13) 0.76064(11) 0.0191(3) Uani 1 1 d . . .
C11 C 0.2412(2) 0.26979(13) 0.80391(12) 0.0197(3) Uani 1 1 d . . .
C12 C 0.3011(2) 0.29575(14) 0.92108(12) 0.0242(3) Uani 1 1 d . . .
H12 H 0.348(2) 0.3868(16) 0.9691(14) 0.031(4) Uiso 1 1 d . . .
C13 C 0.2971(2) 0.19338(14) 0.96854(13) 0.0277(3) Uani 1 1 d . . .
H13 H 0.338(2) 0.2134(16) 1.0490(15) 0.035(5) Uiso 1 1 d . . .
C14 C 0.2382(2) 0.06618(15) 0.90100(14) 0.0283(3) Uani 1 1 d . . .
H14 H 0.239(2) -0.0046(16) 0.9350(14) 0.033(4) Uiso 1 1 d . . .
C15 C 0.1823(2) 0.04155(14) 0.78454(13) 0.0274(3) Uani 1 1 d . . .
H15 H 0.142(2) -0.0478(16) 0.7338(14) 0.035(4) Uiso 1 1 d . . .
C16 C 0.1820(2) 0.14217(13) 0.73534(13) 0.0234(3) Uani 1 1 d . . .
H16 H 0.140(2) 0.1247(14) 0.6541(14) 0.027(4) Uiso 1 1 d . . .
C17 C 0.2282(2) 0.71667(13) 0.80839(13) 0.0230(3) Uani 1 1 d . . .
H171 H 0.344(2) 0.7779(15) 0.8058(13) 0.031(4) Uiso 1 1 d . . .
H172 H 0.234(2) 0.7359(15) 0.8905(15) 0.032(4) Uiso 1 1 d . . .
H173 H 0.104(3) 0.7377(15) 0.7662(14) 0.036(5) Uiso 1 1 d . . .
C18 C 0.2627(3) 0.91857(15) 0.50626(14) 0.0275(3) Uani 1 1 d . . .
H181 H 0.384(2) 0.9360(15) 0.5744(14) 0.029(4) Uiso 1 1 d . . .
H182 H 0.137(2) 0.9046(15) 0.5276(14) 0.028(4) Uiso 1 1 d . . .
H183 H 0.269(2) 0.9938(15) 0.4765(13) 0.027(4) Uiso 1 1 d . . .
C19 C 0.2463(2) 0.51938(16) 0.15274(13) 0.0262(3) Uani 1 1 d . . .
H191 H 0.370(2) 0.4750(15) 0.1663(13) 0.032(4) Uiso 1 1 d . . .
H192 H 0.123(3) 0.4571(16) 0.1282(14) 0.033(4) Uiso 1 1 d . . .
H193 H 0.249(2) 0.5605(15) 0.0943(14) 0.031(4) Uiso 1 1 d . . .
C20 C 0.2950(2) 1.01055(16) 0.19631(13) 0.0286(3) Uani 1 1 d . . .
C21 C 0.2716(3) 0.86967(17) 0.16571(18) 0.0373(4) Uani 1 1 d . . .
H211 H 0.372(3) 0.843(2) 0.1306(18) 0.065(6) Uiso 1 1 d . . .
H212 H 0.141(3) 0.832(2) 0.1105(18) 0.064(6) Uiso 1 1 d . . .
H213 H 0.292(4) 0.839(2) 0.231(2) 0.090(8) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0349(6) 0.0205(5) 0.0229(5) 0.0091(4) 0.0122(4) 0.0085(4)
O2 0.0349(6) 0.0259(5) 0.0191(5) 0.0091(4) 0.0121(4) 0.0085(4)
N1 0.0211(6) 0.0198(6) 0.0205(6) 0.0053(5) 0.0077(5) 0.0053(4)
N2 0.0240(6) 0.0161(6) 0.0180(6) 0.0035(5) 0.0078(5) 0.0043(4)
N3 0.0234(6) 0.0174(6) 0.0210(6) 0.0046(5) 0.0080(5) 0.0052(4)
N4 0.0521(10) 0.0349(8) 0.0370(8) 0.0085(6) 0.0192(7) 0.0001(7)
C1 0.0180(7) 0.0215(7) 0.0227(7) 0.0095(6) 0.0064(5) 0.0052(5)
C2 0.0183(7) 0.0268(7) 0.0181(7) 0.0092(6) 0.0071(5) 0.0051(5)
C3 0.0176(7) 0.0232(7) 0.0180(7) 0.0046(6) 0.0066(5) 0.0053(5)
C4 0.0144(6) 0.0219(7) 0.0193(7) 0.0057(6) 0.0058(5) 0.0036(5)
C5 0.0143(6) 0.0207(7) 0.0193(7) 0.0055(6) 0.0049(5) 0.0033(5)
C6 0.0182(7) 0.0196(7) 0.0194(7) 0.0044(6) 0.0061(5) 0.0041(5)
C7 0.0153(6) 0.0176(6) 0.0204(7) 0.0056(5) 0.0056(5) 0.0036(5)
C8 0.0163(7) 0.0207(7) 0.0192(7) 0.0061(5) 0.0059(5) 0.0040(5)
C9 0.0181(7) 0.0216(7) 0.0194(7) 0.0036(6) 0.0068(5) 0.0043(5)
C10 0.0165(7) 0.0205(7) 0.0201(7) 0.0066(6) 0.0046(5) 0.0029(5)
C11 0.0192(7) 0.0199(7) 0.0238(7) 0.0102(6) 0.0083(6) 0.0063(5)
C12 0.0296(8) 0.0221(7) 0.0219(7) 0.0069(6) 0.0086(6) 0.0053(6)
C13 0.0335(9) 0.0303(8) 0.0226(8) 0.0118(7) 0.0092(7) 0.0083(6)
C14 0.0348(9) 0.0259(8) 0.0317(9) 0.0160(7) 0.0132(7) 0.0109(6)
C15 0.0357(9) 0.0188(7) 0.0295(8) 0.0074(6) 0.0120(7) 0.0065(6)
C16 0.0280(8) 0.0221(7) 0.0206(7) 0.0060(6) 0.0080(6) 0.0056(6)
C17 0.0284(8) 0.0182(7) 0.0224(8) 0.0046(6) 0.0087(6) 0.0046(6)
C18 0.0374(9) 0.0197(7) 0.0261(8) 0.0067(6) 0.0107(7) 0.0056(6)
C19 0.0313(9) 0.0301(8) 0.0184(7) 0.0061(6) 0.0102(6) 0.0067(7)
C20 0.0301(8) 0.0354(9) 0.0232(8) 0.0113(7) 0.0112(6) 0.0036(6)
C21 0.0390(10) 0.0319(9) 0.0478(11) 0.0162(8) 0.0190(9) 0.0095(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3618(16) . ?
O1 C18 1.4302(18) . ?
O2 C2 1.3647(16) . ?
O2 C19 1.4280(18) . ?
N1 C9 1.3223(18) . ?
N1 C8 1.3559(18) . ?
N2 N3 1.3772(16) . ?
N2 C8 1.3793(17) . ?
N2 C11 1.4178(17) . ?
N3 C10 1.3275(18) . ?
N4 C20 1.142(2) . ?
C1 C6 1.373(2) . ?
C1 C2 1.429(2) . ?
C2 C3 1.3706(19) . ?
C3 C4 1.4189(19) . ?
C3 H3 0.961(16) . ?
C4 C5 1.4144(19) . ?
C4 C9 1.4287(19) . ?
C5 C6 1.4144(19) . ?
C5 C7 1.4221(19) . ?
C6 H6 0.965(15) . ?
C7 C8 1.3964(19) . ?
C7 C10 1.4229(19) . ?
C9 H9 0.981(14) . ?
C10 C17 1.495(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.991(17) . ?
C13 C14 1.383(2) . ?
C13 H13 0.956(18) . ?
C14 C15 1.388(2) . ?
C14 H14 0.968(17) . ?
C15 C16 1.384(2) . ?
C15 H15 0.985(17) . ?
C16 H16 0.968(16) . ?
C17 H171 1.011(17) . ?
C17 H172 1.013(17) . ?
C17 H173 0.981(17) . ?
C18 H181 1.009(17) . ?
C18 H182 1.011(17) . ?
C18 H183 0.980(16) . ?
C19 H191 1.034(16) . ?
C19 H192 0.971(17) . ?
C19 H193 0.965(17) . ?
C20 C21 1.454(2) . ?
C21 H211 0.98(2) . ?
C21 H212 0.98(2) . ?
C21 H213 0.95(3) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C18 116.81(11) . . ?
C2 O2 C19 116.84(11) . . ?
C9 N1 C8 113.45(12) . . ?
N3 N2 C8 110.67(11) . . ?
N3 N2 C11 118.61(11) . . ?
C8 N2 C11 130.70(12) . . ?
C10 N3 N2 106.34(11) . . ?
O1 C1 C6 124.90(13) . . ?
O1 C1 C2 114.28(12) . . ?
C6 C1 C2 120.82(13) . . ?
O2 C2 C3 125.76(12) . . ?
O2 C2 C1 114.45(12) . . ?
C3 C2 C1 119.78(13) . . ?
C2 C3 C4 120.11(13) . . ?
C2 C3 H3 120.7(9) . . ?
C4 C3 H3 119.2(9) . . ?
C5 C4 C3 120.01(12) . . ?
C5 C4 C9 119.37(12) . . ?
C3 C4 C9 120.62(12) . . ?
C4 C5 C6 119.16(13) . . ?
C4 C5 C7 115.68(12) . . ?
C6 C5 C7 125.15(12) . . ?
C1 C6 C5 120.10(13) . . ?
C1 C6 H6 119.4(9) . . ?
C5 C6 H6 120.5(9) . . ?
C8 C7 C5 118.34(12) . . ?
C8 C7 C10 105.06(12) . . ?
C5 C7 C10 136.60(12) . . ?
N1 C8 N2 125.83(12) . . ?
N1 C8 C7 127.38(13) . . ?
N2 C8 C7 106.78(12) . . ?
N1 C9 C4 125.78(13) . . ?
N1 C9 H9 117.2(8) . . ?
C4 C9 H9 117.0(8) . . ?
N3 C10 C7 111.14(12) . . ?
N3 C10 C17 119.06(13) . . ?
C7 C10 C17 129.76(12) . . ?
C16 C11 C12 120.21(13) . . ?
C16 C11 N2 121.13(13) . . ?
C12 C11 N2 118.65(12) . . ?
C13 C12 C11 119.44(14) . . ?
C13 C12 H12 121.0(9) . . ?
C11 C12 H12 119.5(10) . . ?
C14 C13 C12 120.73(15) . . ?
C14 C13 H13 121.2(10) . . ?
C12 C13 H13 118.0(10) . . ?
C13 C14 C15 119.26(14) . . ?
C13 C14 H14 120.1(10) . . ?
C15 C14 H14 120.7(10) . . ?
C16 C15 C14 121.00(14) . . ?
C16 C15 H15 117.5(10) . . ?
C14 C15 H15 121.5(10) . . ?
C15 C16 C11 119.35(14) . . ?
C15 C16 H16 120.8(9) . . ?
C11 C16 H16 119.9(9) . . ?
C10 C17 H171 111.9(9) . . ?
C10 C17 H172 111.2(9) . . ?
H171 C17 H172 106.5(13) . . ?
C10 C17 H173 110.5(10) . . ?
H171 C17 H173 108.2(13) . . ?
H172 C17 H173 108.3(13) . . ?
O1 C18 H181 112.2(9) . . ?
O1 C18 H182 110.2(9) . . ?
H181 C18 H182 110.5(13) . . ?
O1 C18 H183 105.5(9) . . ?
H181 C18 H183 107.2(13) . . ?
H182 C18 H183 111.2(12) . . ?
O2 C19 H191 110.9(9) . . ?
O2 C19 H192 111.9(10) . . ?
H191 C19 H192 111.8(13) . . ?
O2 C19 H193 105.9(10) . . ?
H191 C19 H193 107.0(13) . . ?
H192 C19 H193 109.1(13) . . ?
N4 C20 C21 179.67(18) . . ?
C20 C21 H211 109.3(12) . . ?
C20 C21 H212 109.4(12) . . ?
H211 C21 H212 107.8(18) . . ?
C20 C21 H213 111.1(15) . . ?
H211 C21 H213 106.8(19) . . ?
H212 C21 H213 112(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 179.55(12) . . . . ?
O1 C1 C2 O2 -1.17(17) . . . . ?
C1 C2 O2 C19 -175.93(12) . . . . ?
N3 N2 C11 C12 -18.87(18) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H213 O1 0.95(3) 2.54(3) 3.455(2) 160(2) .
C21 H213 O2 0.95(3) 2.41(3) 3.126(2) 131(2) .
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.231
_refine_diff_density_min -0.247
_refine_diff_density_rms 0.044
#=============================================END
data_(10Cd)
_database_code_depnum_ccdc_archive 'CCDC 232597'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
5-{4-(dimethylamino)phenyl}-
7,8-dimethoxypyrazolo[3,4-c]isoquinoline
;
_chemical_name_common
;5-(4-(dimethylamino)phenyl)-7,8-dimethoxypyrazolo(3,4-
c)isoquinoline
;
_chemical_melting_point '200--200.5 \% C'
_chemical_formula_moiety 'C35 H34 N4 O2'
_chemical_formula_sum 'C35 H34 N4 O2'
_chemical_formula_weight 542.66
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.944(4)
_cell_length_b 12.945(5)
_cell_length_c 13.918(7)
_cell_angle_alpha 64.13(2)
_cell_angle_beta 73.04(2)
_cell_angle_gamma 81.00(2)
_cell_volume 1386.1(12)
_cell_formula_units_Z 2
_cell_measurement_temperature 120(2)
_cell_measurement_reflns_used 421
_cell_measurement_theta_min 10.13
_cell_measurement_theta_max 20.79
_exptl_crystal_description plate
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_diffrn 1.300
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 576
_exptl_absorpt_coefficient_mu 0.082
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;The data collection nominally covered full sphere
of reciprocal space, by a combination of 4 sets of \w scans;
each set at different \f and/or 2\q angles and each
scan (40 sec exposure) covering 0.3\% in \w. Crystal to
detector distance 4.95 cm. The absense of crystal decay was
monitored by repeating 57 initial frames at the end of data
collection and comparing duplicate reflections.
;
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source
'60W microfocus Bede Microsource with glass polycapillary optics'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'APEX CCD area detector'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number 10374
_diffrn_reflns_av_R_equivalents 0.0923
_diffrn_reflns_av_sigmaI/netI 0.1520
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.38
_diffrn_reflns_theta_max 25.35
_reflns_number_total 5074
_reflns_number_gt 2568
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction 'SAINT version 6.28A (Bruker, 2002)'
_computing_structure_solution 'SHELXTL version 6.12 (Bruker, 2001)'
_computing_structure_refinement 'SHELXTL version 6.12 (Bruker, 2001)'
_computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)'
_computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.
Methyl groups were refined as rigid (rotating) bodies with a common
refined U(H) for each group. Other H atoms - riding.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0099P)^2^P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5074
_refine_ls_number_parameters 378
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1166
_refine_ls_R_factor_gt 0.0505
_refine_ls_wR_factor_ref 0.0932
_refine_ls_wR_factor_gt 0.0787
_refine_ls_goodness_of_fit_ref 0.835
_refine_ls_restrained_S_all 0.835
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8299(2) 0.44709(15) 0.56955(13) 0.0237(5) Uani 1 1 d . . .
O2 O 0.7850(2) 0.42841(15) 0.40565(13) 0.0238(5) Uani 1 1 d . . .
N1 N 0.1638(3) 0.22023(18) 0.71685(16) 0.0198(5) Uani 1 1 d . . .
N2 N 0.0853(3) 0.21062(18) 0.90192(16) 0.0198(5) Uani 1 1 d . . .
N3 N 0.1495(3) 0.23273(18) 0.96949(16) 0.0210(5) Uani 1 1 d . . .
N4 N 0.1847(3) 0.13706(18) 0.29479(16) 0.0208(5) Uani 1 1 d . . .
C1 C 0.6929(3) 0.4000(2) 0.5907(2) 0.0186(6) Uani 1 1 d . . .
C2 C 0.6680(3) 0.3879(2) 0.4999(2) 0.0186(6) Uani 1 1 d . . .
C3 C 0.5350(3) 0.3403(2) 0.5115(2) 0.0181(6) Uani 1 1 d . . .
H3 H 0.5193 0.3331 0.4501 0.022 Uiso 1 1 d R . .
C4 C 0.4191(3) 0.3004(2) 0.6135(2) 0.0174(6) Uani 1 1 d . . .
C5 C 0.4438(3) 0.3161(2) 0.70259(19) 0.0180(6) Uani 1 1 d . . .
C6 C 0.5817(3) 0.3652(2) 0.6891(2) 0.0181(6) Uani 1 1 d . . .
H6 H 0.5981 0.3748 0.7492 0.022 Uiso 1 1 d R . .
C7 C 0.3197(3) 0.2810(2) 0.80076(19) 0.0179(6) Uani 1 1 d . . .
C8 C 0.1889(3) 0.2392(2) 0.7992(2) 0.0180(6) Uani 1 1 d . . .
C9 C 0.2815(3) 0.2473(2) 0.6267(2) 0.0186(6) Uani 1 1 d . . .
C10 C 0.2876(3) 0.2754(2) 0.9100(2) 0.0189(6) Uani 1 1 d . . .
C11 C -0.0586(3) 0.1548(2) 0.9464(2) 0.0189(6) Uani 1 1 d . . .
C12 C -0.1114(3) 0.0969(2) 1.0602(2) 0.0215(7) Uani 1 1 d . . .
H12 H -0.0506 0.0938 1.1071 0.026 Uiso 1 1 d R . .
C13 C -0.2523(3) 0.0437(2) 1.1043(2) 0.0257(7) Uani 1 1 d . . .
H13 H -0.2885 0.0043 1.1820 0.031 Uiso 1 1 d R . .
C14 C -0.3420(3) 0.0468(2) 1.0376(2) 0.0254(7) Uani 1 1 d . . .
H14 H -0.4395 0.0103 1.0690 0.030 Uiso 1 1 d R . .
C15 C -0.2880(3) 0.1032(2) 0.9244(2) 0.0245(7) Uani 1 1 d . . .
H15 H -0.3487 0.1051 0.8779 0.029 Uiso 1 1 d R . .
C16 C -0.1474(3) 0.1569(2) 0.8787(2) 0.0225(7) Uani 1 1 d . . .
H16 H -0.1110 0.1951 0.8008 0.027 Uiso 1 1 d R . .
C17 C 0.3838(3) 0.3113(2) 0.96244(19) 0.0204(7) Uani 1 1 d . . .
H171 H 0.4940 0.2860 0.9414 0.027 Uiso 1 1 d R . .
H172 H 0.3464 0.2716 1.0436 0.027 Uiso 1 1 d R . .
C18 C 0.8598(3) 0.4678(2) 0.6552(2) 0.0262(7) Uani 1 1 d . . .
H181 H 0.7853 0.5267 0.6694 0.035(5) Uiso 1 1 d R . .
H182 H 0.9664 0.4944 0.6320 0.035(5) Uiso 1 1 d R . .
H183 H 0.8484 0.3965 0.7227 0.035(5) Uiso 1 1 d R . .
C19 C 0.7650(3) 0.4192(2) 0.3117(2) 0.0258(7) Uani 1 1 d . . .
H191 H 0.7562 0.3382 0.3288 0.024(4) Uiso 1 1 d R . .
H192 H 0.8554 0.4507 0.2492 0.024(4) Uiso 1 1 d R . .
H193 H 0.6698 0.4623 0.2925 0.024(4) Uiso 1 1 d R . .
C20 C 0.2588(3) 0.2189(2) 0.53944(19) 0.0181(6) Uani 1 1 d . . .
C21 C 0.3720(3) 0.1574(2) 0.4900(2) 0.0210(6) Uani 1 1 d . . .
H21 H 0.4686 0.1356 0.5102 0.025 Uiso 1 1 d R . .
C22 C 0.3460(3) 0.1274(2) 0.41262(19) 0.0210(7) Uani 1 1 d . . .
H22 H 0.4245 0.0842 0.3817 0.025 Uiso 1 1 d R . .
C23 C 0.2077(3) 0.1594(2) 0.37818(19) 0.0204(7) Uani 1 1 d . . .
C24 C 0.0933(3) 0.2183(2) 0.4305(2) 0.0206(6) Uani 1 1 d . . .
H24 H -0.0042 0.2394 0.4115 0.025 Uiso 1 1 d R . .
C25 C 0.1196(3) 0.2462(2) 0.50937(19) 0.0196(6) Uani 1 1 d . . .
H25 H 0.0391 0.2855 0.5437 0.024 Uiso 1 1 d R . .
C26 C 0.3767(3) 0.4397(2) 0.93011(19) 0.0191(6) Uani 1 1 d . . .
C27 C 0.5098(3) 0.5038(2) 0.87536(19) 0.0227(7) Uani 1 1 d . . .
H27 H 0.6077 0.4667 0.8581 0.027 Uiso 1 1 d R . .
C28 C 0.5029(4) 0.6218(2) 0.8452(2) 0.0280(7) Uani 1 1 d . . .
H28 H 0.5951 0.6647 0.8070 0.034 Uiso 1 1 d R . .
C29 C 0.3611(4) 0.6764(2) 0.8709(2) 0.0315(8) Uani 1 1 d . . .
H29 H 0.3556 0.7570 0.8498 0.038 Uiso 1 1 d R . .
C30 C 0.2283(4) 0.6134(2) 0.9275(2) 0.0319(8) Uani 1 1 d . . .
H30 H 0.1314 0.6505 0.9470 0.038 Uiso 1 1 d R . .
C31 C 0.2353(3) 0.4954(2) 0.9561(2) 0.0250(7) Uani 1 1 d . . .
H31 H 0.1428 0.4528 0.9937 0.030 Uiso 1 1 d R . .
C32 C 0.2908(3) 0.0591(2) 0.2547(2) 0.0256(7) Uani 1 1 d . . .
H321 H 0.3995 0.0806 0.2391 0.033 Uiso 1 1 d R . .
H322 H 0.2726 0.0690 0.1843 0.033 Uiso 1 1 d R . .
C33 C 0.2741(4) -0.0672(2) 0.3345(2) 0.0331(8) Uani 1 1 d . . .
H331 H 0.2861 -0.0775 0.4059 0.041(5) Uiso 1 1 d R . .
H332 H 0.3549 -0.1135 0.3046 0.041(5) Uiso 1 1 d R . .
H333 H 0.1706 -0.0919 0.3442 0.041(5) Uiso 1 1 d R . .
C34 C 0.0408(3) 0.1729(2) 0.2592(2) 0.0242(7) Uani 1 1 d . . .
H341 H 0.0617 0.1791 0.1831 0.032 Uiso 1 1 d R . .
H342 H 0.0090 0.2506 0.2570 0.032 Uiso 1 1 d R . .
C35 C -0.0951(4) 0.0940(2) 0.3311(2) 0.0335(8) Uani 1 1 d . . .
H351 H -0.0712 0.0198 0.3259 0.040(5) Uiso 1 1 d R . .
H352 H -0.1897 0.1292 0.3058 0.040(5) Uiso 1 1 d R . .
H353 H -0.1122 0.0822 0.4080 0.040(5) Uiso 1 1 d R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0197(12) 0.0348(12) 0.0247(10) -0.0181(9) -0.0055(9) -0.0054(10)
O2 0.0228(12) 0.0322(12) 0.0186(10) -0.0135(9) -0.0021(9) -0.0041(9)
N1 0.0193(14) 0.0247(14) 0.0188(12) -0.0110(11) -0.0067(11) -0.0002(11)
N2 0.0219(14) 0.0248(14) 0.0177(12) -0.0113(10) -0.0054(11) -0.0059(11)
N3 0.0212(14) 0.0245(14) 0.0210(12) -0.0118(11) -0.0053(11) -0.0041(11)
N4 0.0242(14) 0.0246(14) 0.0195(12) -0.0136(10) -0.0089(11) 0.0035(11)
C1 0.0156(16) 0.0197(16) 0.0245(15) -0.0116(13) -0.0073(13) 0.0002(13)
C2 0.0190(17) 0.0183(16) 0.0169(14) -0.0076(12) -0.0019(13) -0.0002(13)
C3 0.0187(16) 0.0196(16) 0.0196(14) -0.0110(12) -0.0068(13) 0.0020(13)
C4 0.0202(16) 0.0148(16) 0.0191(14) -0.0078(12) -0.0078(13) 0.0023(13)
C5 0.0215(17) 0.0141(16) 0.0215(14) -0.0084(12) -0.0111(13) 0.0048(13)
C6 0.0187(16) 0.0220(16) 0.0172(14) -0.0109(12) -0.0058(12) 0.0004(13)
C7 0.0226(17) 0.0136(16) 0.0186(14) -0.0066(12) -0.0076(13) 0.0006(13)
C8 0.0198(17) 0.0136(16) 0.0167(14) -0.0044(12) -0.0022(13) -0.0005(13)
C9 0.0230(17) 0.0146(16) 0.0203(14) -0.0065(12) -0.0112(13) 0.0029(13)
C10 0.0209(17) 0.0185(16) 0.0189(14) -0.0084(12) -0.0064(13) -0.0002(13)
C11 0.0146(16) 0.0183(16) 0.0248(15) -0.0118(13) -0.0014(13) -0.0013(13)
C12 0.0235(17) 0.0229(17) 0.0216(15) -0.0125(13) -0.0053(13) -0.0011(14)
C13 0.0295(19) 0.0240(17) 0.0200(14) -0.0086(13) -0.0001(14) -0.0047(15)
C14 0.0192(17) 0.0258(18) 0.0315(16) -0.0134(14) -0.0009(14) -0.0070(14)
C15 0.0236(18) 0.0255(18) 0.0267(15) -0.0120(14) -0.0073(14) -0.0016(14)
C16 0.0211(17) 0.0253(17) 0.0200(14) -0.0088(13) -0.0046(13) -0.0010(14)
C17 0.0244(17) 0.0221(17) 0.0183(14) -0.0098(12) -0.0077(13) -0.0018(13)
C18 0.0248(18) 0.0334(19) 0.0250(15) -0.0130(14) -0.0090(14) -0.0058(15)
C19 0.0243(18) 0.0357(19) 0.0207(14) -0.0140(14) -0.0081(13) 0.0021(15)
C20 0.0212(17) 0.0180(16) 0.0144(13) -0.0049(12) -0.0050(13) -0.0028(13)
C21 0.0181(16) 0.0230(17) 0.0230(14) -0.0091(13) -0.0085(13) 0.0014(13)
C22 0.0206(17) 0.0219(17) 0.0226(14) -0.0123(13) -0.0053(13) 0.0023(13)
C23 0.0237(17) 0.0179(17) 0.0188(14) -0.0056(12) -0.0058(13) -0.0037(13)
C24 0.0194(17) 0.0223(16) 0.0216(14) -0.0090(13) -0.0088(13) 0.0021(13)
C25 0.0209(17) 0.0196(16) 0.0187(14) -0.0097(12) -0.0035(13) 0.0007(13)
C26 0.0263(18) 0.0224(17) 0.0149(13) -0.0100(12) -0.0105(13) -0.0008(14)
C27 0.0261(18) 0.0296(19) 0.0166(14) -0.0127(13) -0.0051(13) -0.0030(14)
C28 0.040(2) 0.0254(19) 0.0217(15) -0.0073(14) -0.0125(15) -0.0078(16)
C29 0.048(2) 0.0198(18) 0.0345(17) -0.0110(14) -0.0223(17) 0.0004(16)
C30 0.031(2) 0.034(2) 0.0400(18) -0.0232(16) -0.0150(16) 0.0084(16)
C31 0.0260(18) 0.0272(18) 0.0288(16) -0.0152(14) -0.0090(14) -0.0045(14)
C32 0.0284(18) 0.0293(19) 0.0230(14) -0.0154(14) -0.0080(13) 0.0052(14)
C33 0.040(2) 0.0301(19) 0.0348(17) -0.0191(15) -0.0113(15) 0.0045(16)
C34 0.0277(18) 0.0267(18) 0.0223(14) -0.0124(13) -0.0095(13) 0.0010(14)
C35 0.0314(19) 0.040(2) 0.0298(16) -0.0138(15) -0.0086(15) -0.0031(16)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.351(3) . ?
O1 C18 1.432(3) . ?
O2 C2 1.364(3) . ?
O2 C19 1.427(3) . ?
N1 C9 1.329(3) . ?
N1 C8 1.356(3) . ?
N2 N3 1.377(3) . ?
N2 C8 1.383(3) . ?
N2 C11 1.413(3) . ?
N3 C10 1.317(3) . ?
N4 C23 1.387(3) . ?
N4 C34 1.449(3) . ?
N4 C32 1.454(3) . ?
C1 C6 1.369(3) . ?
C1 C2 1.422(3) . ?
C2 C3 1.360(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.421(3) . ?
C4 C9 1.429(4) . ?
C5 C6 1.403(4) . ?
C5 C7 1.427(3) . ?
C7 C8 1.372(4) . ?
C7 C10 1.434(3) . ?
C9 C20 1.487(3) . ?
C10 C17 1.508(3) . ?
C11 C16 1.388(4) . ?
C11 C12 1.390(3) . ?
C12 C13 1.375(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.382(3) . ?
C15 C16 1.375(4) . ?
C17 C26 1.516(3) . ?
C20 C25 1.374(4) . ?
C20 C21 1.397(3) . ?
C21 C22 1.380(3) . ?
C22 C23 1.394(4) . ?
C23 C24 1.402(3) . ?
C24 C25 1.383(3) . ?
C26 C27 1.383(4) . ?
C26 C31 1.387(4) . ?
C27 C28 1.393(3) . ?
C28 C29 1.382(4) . ?
C29 C30 1.376(4) . ?
C30 C31 1.396(4) . ?
C32 C33 1.524(4) . ?
C34 C35 1.520(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C18 117.8(2) . . ?
C2 O2 C19 116.5(2) . . ?
C9 N1 C8 114.6(2) . . ?
N3 N2 C8 109.8(2) . . ?
N3 N2 C11 119.4(2) . . ?
C8 N2 C11 130.5(2) . . ?
C10 N3 N2 106.6(2) . . ?
C23 N4 C34 121.2(2) . . ?
C23 N4 C32 120.6(2) . . ?
C34 N4 C32 117.2(2) . . ?
O1 C1 C6 125.7(2) . . ?
O1 C1 C2 114.5(2) . . ?
C6 C1 C2 119.8(3) . . ?
C3 C2 O2 125.8(2) . . ?
C3 C2 C1 119.9(2) . . ?
O2 C2 C1 114.3(2) . . ?
C2 C3 C4 121.7(2) . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C9 120.6(2) . . ?
C3 C4 C9 121.7(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 C7 124.8(2) . . ?
C4 C5 C7 115.3(2) . . ?
C1 C6 C5 121.1(2) . . ?
C8 C7 C5 117.8(2) . . ?
C8 C7 C10 104.6(2) . . ?
C5 C7 C10 137.6(2) . . ?
N1 C8 C7 128.1(2) . . ?
N1 C8 N2 123.8(2) . . ?
C7 C8 N2 107.9(2) . . ?
N1 C9 C4 123.1(2) . . ?
N1 C9 C20 114.7(2) . . ?
C4 C9 C20 122.2(2) . . ?
N3 C10 C7 111.2(2) . . ?
N3 C10 C17 118.3(2) . . ?
C7 C10 C17 130.5(2) . . ?
C16 C11 C12 119.7(3) . . ?
C16 C11 N2 121.3(2) . . ?
C12 C11 N2 119.0(2) . . ?
C13 C12 C11 119.5(3) . . ?
C12 C13 C14 121.1(3) . . ?
C13 C14 C15 119.2(3) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C11 119.9(2) . . ?
C10 C17 C26 113.7(2) . . ?
C25 C20 C21 117.2(2) . . ?
C25 C20 C9 120.5(2) . . ?
C21 C20 C9 122.1(3) . . ?
C22 C21 C20 121.3(3) . . ?
C21 C22 C23 121.7(2) . . ?
N4 C23 C22 122.3(2) . . ?
N4 C23 C24 121.3(3) . . ?
C22 C23 C24 116.4(2) . . ?
C25 C24 C23 121.3(3) . . ?
C20 C25 C24 122.0(2) . . ?
C27 C26 C31 118.5(3) . . ?
C27 C26 C17 121.3(2) . . ?
C31 C26 C17 120.2(2) . . ?
C26 C27 C28 121.2(3) . . ?
C29 C28 C27 119.7(3) . . ?
C30 C29 C28 119.7(3) . . ?
C29 C30 C31 120.3(3) . . ?
C26 C31 C30 120.5(3) . . ?
N4 C32 C33 114.2(2) . . ?
N4 C34 C35 115.1(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O1 C1 C2 176.7(2) . . . . ?
O1 C1 C2 C19 -2.0(5) . . . . ?
N3 C10 C17 C26 -100.4(3) . . . . ?
C10 C17 C26 C31 61.8(3) . . . . ?
N1 C9 C20 C25 46.1(3) . . . . ?
C28 C29 N4 C32 12.5(4) . . . . ?
C23 N4 C32 C33 72.6(3) . . . . ?
C33 C32 N4 C34 -96.4(3) . . . . ?
C32 N4 C34 C35 87.7(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.221
_refine_diff_density_min -0.268
_refine_diff_density_rms 0.055
#==========================================END