data_global

_publ_contact_author_email       STEVE.DAVIES@CHEM.OX.AC.UK

_publ_contact_author_name        'Prof Stephen G Davies'
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_address     
;
Dyson Perrins Laboratory
University of Oxford
South Parks Road
Oxford
Oxon
OX1 3QY
UNITED KINGDOM
;

_publ_section_title              
;
Asymmetric synthesis of the stereoisomers of
2-amino-5-carboxymethyl-cyclopentane-1-carboxylate
;

loop_
_publ_author_name
'Stephen G. Davies'
'J.Antonio Casaseca'
'David Diez'
'Sara H. Dominguez'
'Mohamed M. El Hammouni'
;
N.M.Garrido
;
'Julio G. Urones'

data_testr
_database_code_depnum_ccdc_archive 'CCDC 220744'

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C25 H31 N O4'
_chemical_formula_weight         409.51
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   18.0640(10)
_cell_length_b                   13.9610(10)
_cell_length_c                   9.1430(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2305.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.7
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Seifert XRD 3003 SC'
_diffrn_measurement_method       2theta-omega
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2087
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         65.35
_reflns_number_total             2087
_reflns_number_observed          1934
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       CRYSOM
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        XRAY80
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with
very negative F^2^
or flagged by the user for potential systematic errors.
Weighted R-factors
wR and all goodnesses 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
observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating
#_R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.
R-factors based
on F^2^ are statistically about twice as large as those
based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      
;
calc w=1/[\s^2^(Fo^2^)+(0.0937P)^2^+0.2319P] 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    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0467(25)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(42)
_refine_ls_number_reflns         2087
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_obs          0.0457
_refine_ls_wR_factor_all         0.1272
_refine_ls_wR_factor_obs         0.1210
_refine_ls_goodness_of_fit_all   1.047
_refine_ls_goodness_of_fit_obs   1.041
_refine_ls_restrained_S_all      1.047
_refine_ls_restrained_S_obs      1.041
_refine_ls_shift/esd_max         -0.002
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.08740(11) 0.40194(15) 0.4502(3) 0.0475(5) Uani 1 d . .
O1 O 0.19002(14) 0.5239(2) 0.7849(3) 0.0921(9) Uani 1 d . .
O2 O 0.0837(2) 0.5975(2) 0.7393(2) 0.0786(7) Uani 1 d . .
O3 O 0.22667(13) 0.8338(2) 0.4010(4) 0.0877(9) Uani 1 d . .
O4 O 0.34217(11) 0.7802(2) 0.4213(3) 0.0751(7) Uani 1 d . .
C1 C 0.08420(14) 0.5065(2) 0.4560(3) 0.0489(6) Uani 1 d . .
H1 H 0.04073(14) 0.5238(2) 0.5145(3) 0.059 Uiso 1 calc R .
C2 C 0.15274(14) 0.5466(2) 0.5354(3) 0.0482(6) Uani 1 d . .
H2 H 0.19447(14) 0.5040(2) 0.5141(3) 0.058 Uiso 1 calc R .
C3 C 0.16914(14) 0.6440(2) 0.4634(4) 0.0532(7) Uani 1 d . .
H3 H 0.13580(14) 0.6929(2) 0.5030(4) 0.064 Uiso 1 calc R .
C4 C 0.1495(2) 0.6240(2) 0.3034(4) 0.0685(9) Uani 1 d . .
H4A H 0.1407(2) 0.6832(2) 0.2508(4) 0.082 Uiso 1 calc R .
H4B H 0.1890(2) 0.5891(2) 0.2552(4) 0.082 Uiso 1 calc R .
C5 C 0.0798(2) 0.5642(2) 0.3107(4) 0.0707(9) Uani 1 d . .
H5A H 0.0771(2) 0.5211(2) 0.2277(4) 0.085 Uiso 1 calc R .
H5B H 0.0364(2) 0.6050(2) 0.3102(4) 0.085 Uiso 1 calc R .
C6 C 0.1454(2) 0.5534(2) 0.6987(4) 0.0565(7) Uani 1 d . .
C7 C 0.0711(3) 0.6102(3) 0.8942(4) 0.108(2) Uani 1 d . .
H7A H 0.0228(8) 0.6370(24) 0.9095(5) 0.161 Uiso 1 calc R .
H7B H 0.1078(12) 0.6526(21) 0.9336(9) 0.161 Uiso 1 calc R .
H7C H 0.0743(21) 0.5492(5) 0.9425(7) 0.161 Uiso 1 calc R .
C8 C 0.2491(2) 0.6741(2) 0.4871(4) 0.0624(8) Uani 1 d . .
H8A H 0.2595(2) 0.6722(2) 0.5911(4) 0.075 Uiso 1 calc R .
H8B H 0.2811(2) 0.6275(2) 0.4401(4) 0.075 Uiso 1 calc R .
C9 C 0.2685(2) 0.7713(2) 0.4310(4) 0.0593(8) Uani 1 d . .
C10 C 0.3697(2) 0.8728(3) 0.3774(6) 0.0955(13) Uani 1 d . .
H10A H 0.4225(3) 0.8698(7) 0.3665(39) 0.143 Uiso 1 calc R .
H10B H 0.3573(18) 0.9194(6) 0.4506(21) 0.143 Uiso 1 calc R .
H10C H 0.3477(16) 0.8907(12) 0.2859(22) 0.143 Uiso 1 calc R .
C11 C 0.01535(15) 0.3533(2) 0.4626(3) 0.0540(7) Uani 1 d . .
H11 H 0.02549(15) 0.2848(2) 0.4496(3) 0.065 Uiso 1 calc R .
C12 C -0.0394(2) 0.3804(4) 0.3421(4) 0.0870(13) Uani 1 d . .
H12A H -0.0538(14) 0.4462(8) 0.3536(21) 0.131 Uiso 1 calc R .
H12B H -0.0824(8) 0.3402(16) 0.3487(23) 0.131 Uiso 1 calc R .
H12C H -0.0164(6) 0.3718(22) 0.2483(4) 0.131 Uiso 1 calc R .
C13 C -0.01477(14) 0.3640(2) 0.6168(3) 0.0467(6) Uani 1 d . .
C14 C 0.03122(15) 0.3507(2) 0.7344(3) 0.0585(8) Uani 1 d . .
H14 H 0.08106(15) 0.3379(2) 0.7181(3) 0.070 Uiso 1 calc R .
C15 C 0.0056(2) 0.3559(3) 0.8756(4) 0.0695(9) Uani 1 d . .
H15 H 0.0382(2) 0.3469(3) 0.9531(4) 0.083 Uiso 1 calc R .
C16 C -0.0683(2) 0.3744(3) 0.9032(4) 0.0715(9) Uani 1 d . .
H16 H -0.0859(2) 0.3782(3) 0.9987(4) 0.086 Uiso 1 calc R .
C17 C -0.1148(2) 0.3869(3) 0.7874(4) 0.0738(10) Uani 1 d . .
H17 H -0.1646(2) 0.3995(3) 0.8042(4) 0.089 Uiso 1 calc R .
C18 C -0.0889(2) 0.3813(2) 0.6455(4) 0.0633(8) Uani 1 d . .
H18 H -0.1218(2) 0.3893(2) 0.5681(4) 0.076 Uiso 1 calc R .
C19 C 0.1351(2) 0.3625(2) 0.3364(3) 0.0600(8) Uani 1 d . .
H19A H 0.1776(2) 0.4040(2) 0.3232(3) 0.072 Uiso 1 calc R .
H19B H 0.1081(2) 0.3603(2) 0.2447(3) 0.072 Uiso 1 calc R .
C20 C 0.1610(2) 0.2635(2) 0.3751(4) 0.0573(7) Uani 1 d . .
C21 C 0.2066(2) 0.2489(3) 0.4957(4) 0.0719(9) Uani 1 d . .
H21 H 0.2210(2) 0.3012(3) 0.5518(4) 0.086 Uiso 1 calc R .
C22 C 0.2306(2) 0.1596(3) 0.5334(6) 0.0891(11) Uani 1 d . .
H22 H 0.2612(2) 0.1519(3) 0.6144(6) 0.107 Uiso 1 calc R .
C23 C 0.2103(3) 0.0823(3) 0.4540(8) 0.104(2) Uani 1 d . .
H23 H 0.2265(3) 0.0217(3) 0.4811(8) 0.125 Uiso 1 calc R .
C24 C 0.1666(3) 0.0927(3) 0.3359(7) 0.105(2) Uani 1 d . .
H24 H 0.1529(3) 0.0395(3) 0.2811(7) 0.126 Uiso 1 calc R .
C25 C 0.1417(2) 0.1839(3) 0.2958(5) 0.0845(11) Uani 1 d . .
H25 H 0.1116(2) 0.1907(3) 0.2140(5) 0.101 Uiso 1 calc 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
N1 0.0378(10) 0.0543(11) 0.0503(12) -0.0034(11) 0.0074(10) -0.0063(9)
O1 0.0754(15) 0.123(2) 0.078(2) 0.026(2) -0.0281(14) 0.0022(15)
O2 0.097(2) 0.0833(14) 0.0558(13) -0.0005(12) 0.0062(13) 0.0243(14)
O3 0.0660(13) 0.0597(12) 0.137(2) 0.0204(14) 0.030(2) 0.0069(11)
O4 0.0487(11) 0.0685(12) 0.108(2) 0.0005(13) 0.0107(13) -0.0120(10)
C1 0.0412(12) 0.0553(14) 0.0503(15) 0.0033(13) -0.0059(12) 0.0005(11)
C2 0.0377(12) 0.0472(12) 0.059(2) 0.0042(13) -0.0042(13) 0.0035(10)
C3 0.0416(13) 0.0482(13) 0.070(2) 0.0099(14) 0.0011(14) 0.0025(10)
C4 0.064(2) 0.072(2) 0.070(2) 0.020(2) -0.006(2) -0.006(2)
C5 0.068(2) 0.074(2) 0.070(2) 0.020(2) -0.012(2) -0.007(2)
C6 0.056(2) 0.0507(14) 0.063(2) 0.0093(14) -0.0121(15) -0.0057(13)
C7 0.165(5) 0.100(3) 0.058(2) -0.009(2) 0.022(3) 0.014(3)
C8 0.0477(14) 0.0554(14) 0.084(2) 0.008(2) 0.002(2) -0.0041(12)
C9 0.0494(14) 0.0531(14) 0.075(2) -0.0046(15) 0.0165(15) -0.0029(13)
C10 0.071(2) 0.086(2) 0.129(4) 0.008(3) 0.019(2) -0.031(2)
C11 0.0418(13) 0.065(2) 0.055(2) -0.0048(15) 0.0008(13) -0.0109(12)
C12 0.057(2) 0.140(4) 0.064(2) 0.000(2) -0.016(2) -0.026(2)
C13 0.0350(11) 0.0478(12) 0.057(2) 0.0008(13) 0.0049(12) -0.0035(10)
C14 0.0381(13) 0.082(2) 0.055(2) 0.007(2) 0.0037(13) 0.0062(13)
C15 0.055(2) 0.095(2) 0.059(2) 0.014(2) 0.002(2) 0.001(2)
C16 0.062(2) 0.085(2) 0.068(2) 0.005(2) 0.022(2) 0.000(2)
C17 0.044(2) 0.096(2) 0.081(2) 0.005(2) 0.019(2) 0.012(2)
C18 0.0385(13) 0.076(2) 0.076(2) 0.003(2) -0.0007(14) 0.0064(14)
C19 0.057(2) 0.069(2) 0.054(2) -0.0045(15) 0.0121(14) -0.0046(13)
C20 0.0446(13) 0.065(2) 0.062(2) -0.0140(15) 0.0170(15) -0.0070(12)
C21 0.057(2) 0.078(2) 0.082(2) -0.016(2) 0.005(2) 0.007(2)
C22 0.065(2) 0.098(3) 0.104(3) 0.008(3) 0.017(2) 0.022(2)
C23 0.079(3) 0.076(2) 0.157(5) 0.004(3) 0.043(3) 0.012(2)
C24 0.093(3) 0.069(2) 0.152(5) -0.041(3) 0.028(3) -0.018(2)
C25 0.077(2) 0.081(2) 0.096(3) -0.030(2) 0.005(2) -0.015(2)

_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
N1 C19 1.458(4) . ?
N1 C1 1.462(3) . ?
N1 C11 1.473(3) . ?
O1 C6 1.201(4) . ?
O2 C6 1.325(4) . ?
O2 C7 1.446(5) . ?
O3 C9 1.187(4) . ?
O4 C9 1.339(4) . ?
O4 C10 1.441(4) . ?
C1 C2 1.541(4) . ?
C1 C5 1.556(4) . ?
C1 H1 0.98 . ?
C2 C6 1.502(5) . ?
C2 C3 1.539(4) . ?
C2 H2 0.98 . ?
C3 C8 1.520(4) . ?
C3 C4 1.531(5) . ?
C3 H3 0.98 . ?
C4 C5 1.512(5) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C8 C9 1.492(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C11 C13 1.519(4) . ?
C11 C12 1.528(4) . ?
C11 H11 0.98 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C14 1.371(4) . ?
C13 C18 1.387(4) . ?
C14 C15 1.373(5) . ?
C14 H14 0.93 . ?
C15 C16 1.384(5) . ?
C15 H15 0.93 . ?
C16 C17 1.362(5) . ?
C16 H16 0.93 . ?
C17 C18 1.381(5) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C20 1.502(4) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 C25 1.372(4) . ?
C20 C21 1.391(5) . ?
C21 C22 1.365(5) . ?
C21 H21 0.93 . ?
C22 C23 1.352(7) . ?
C22 H22 0.93 . ?
C23 C24 1.345(8) . ?
C23 H23 0.93 . ?
C24 C25 1.399(6) . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?

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
C19 N1 C1 115.2(2) . . ?
C19 N1 C11 113.7(2) . . ?
C1 N1 C11 115.0(2) . . ?
C6 O2 C7 117.6(3) . . ?
C9 O4 C10 116.4(3) . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 C5 119.2(3) . . ?
C2 C1 C5 104.7(2) . . ?
N1 C1 H1 107.30(14) . . ?
C2 C1 H1 107.3(2) . . ?
C5 C1 H1 107.3(2) . . ?
C6 C2 C3 112.7(2) . . ?
C6 C2 C1 114.8(2) . . ?
C3 C2 C1 105.9(2) . . ?
C6 C2 H2 107.7(2) . . ?
C3 C2 H2 107.68(14) . . ?
C1 C2 H2 107.68(14) . . ?
C8 C3 C4 114.0(3) . . ?
C8 C3 C2 111.5(2) . . ?
C4 C3 C2 101.7(2) . . ?
C8 C3 H3 109.8(2) . . ?
C4 C3 H3 109.8(2) . . ?
C2 C3 H3 109.79(14) . . ?
C5 C4 C3 104.6(3) . . ?
C5 C4 H4A 110.8(2) . . ?
C3 C4 H4A 110.8(2) . . ?
C5 C4 H4B 110.8(2) . . ?
C3 C4 H4B 110.8(2) . . ?
H4A C4 H4B 108.9 . . ?
C4 C5 C1 106.3(3) . . ?
C4 C5 H5A 110.5(2) . . ?
C1 C5 H5A 110.5(2) . . ?
C4 C5 H5B 110.5(2) . . ?
C1 C5 H5B 110.5(2) . . ?
H5A C5 H5B 108.7 . . ?
O1 C6 O2 122.7(3) . . ?
O1 C6 C2 124.9(3) . . ?
O2 C6 C2 112.5(2) . . ?
O2 C7 H7A 109.5(3) . . ?
O2 C7 H7B 109.5(3) . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5(2) . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C3 115.2(3) . . ?
C9 C8 H8A 108.5(2) . . ?
C3 C8 H8A 108.5(2) . . ?
C9 C8 H8B 108.5(2) . . ?
C3 C8 H8B 108.5(2) . . ?
H8A C8 H8B 107.5 . . ?
O3 C9 O4 123.3(3) . . ?
O3 C9 C8 126.8(3) . . ?
O4 C9 C8 110.0(3) . . ?
O4 C10 H10A 109.5(2) . . ?
O4 C10 H10B 109.5(2) . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5(2) . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C13 110.0(2) . . ?
N1 C11 C12 113.7(3) . . ?
C13 C11 C12 114.4(3) . . ?
N1 C11 H11 106.0(2) . . ?
C13 C11 H11 106.0(2) . . ?
C12 C11 H11 106.0(2) . . ?
C11 C12 H12A 109.5(2) . . ?
C11 C12 H12B 109.5(2) . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5(2) . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.4(3) . . ?
C14 C13 C11 119.8(2) . . ?
C18 C13 C11 122.6(3) . . ?
C13 C14 C15 121.7(3) . . ?
C13 C14 H14 119.1(2) . . ?
C15 C14 H14 119.1(2) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8(2) . . ?
C16 C15 H15 119.8(2) . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.8(2) . . ?
C15 C16 H16 120.8(2) . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5(2) . . ?
C18 C17 H17 119.5(2) . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5(2) . . ?
C13 C18 H18 119.5(2) . . ?
N1 C19 C20 111.3(2) . . ?
N1 C19 H19A 109.37(15) . . ?
C20 C19 H19A 109.4(2) . . ?
N1 C19 H19B 109.4(2) . . ?
C20 C19 H19B 109.4(2) . . ?
H19A C19 H19B 108.0 . . ?
C25 C20 C21 116.8(3) . . ?
C25 C20 C19 122.8(3) . . ?
C21 C20 C19 120.4(3) . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 H21 119.2(3) . . ?
C20 C21 H21 119.2(2) . . ?
C23 C22 C21 120.4(5) . . ?
C23 C22 H22 119.8(3) . . ?
C21 C22 H22 119.8(3) . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.8(3) . . ?
C22 C23 H23 119.8(3) . . ?
C23 C24 C25 119.8(4) . . ?
C23 C24 H24 120.1(3) . . ?
C25 C24 H24 120.1(3) . . ?
C20 C25 C24 121.1(4) . . ?
C20 C25 H25 119.4(2) . . ?
C24 C25 H25 119.4(3) . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051