# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
'Joelle Mayrargue'
'Jean-Francois Berrien'
'Liliane Ciceron'
'Michel Coquillay'
'Frederick Gay'
;
B.Meunier
;
'Olivier Provot'
'Anne Robert'

_publ_contact_author_name        'Prof Joelle Mayrargue'
_publ_contact_author_address     
;
Chimie Organique
Faculte de Pharmacie
5 rue J.-B. Clement
Chatenay-Malabry
92296 cx
FRANCE
;

_publ_contact_author_email       JOELLE.MAYRARGUE@CHIMORG.U-PSUD.FR

_publ_section_title              
;
Alkylation of manganese(II) tetraphenylporphyrin by a
trioxane-based antimalarial agent
;

data_jf15
_database_code_CSD               206129

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 O4'
_chemical_formula_weight         254.32

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'
O O 0.0106 0.0060 '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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.864(9)
_cell_length_b                   6.091(3)
_cell_length_c                   20.852(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.83(3)
_cell_angle_gamma                90.00
_cell_volume                     2612(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      7.1
_cell_measurement_theta_max      8.8

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'CAD4 Enraf-Nonius'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3849
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         27.97
_reflns_number_total             2486
_reflns_number_gt                1551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.  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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2486
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
O4 O 0.37639(6) 0.1276(2) 0.67148(7) 0.0291(4) Uani 1 1 d . . .
O1 O 0.39032(7) -0.2869(2) 0.62426(8) 0.0370(4) Uani 1 1 d . . .
O2 O 0.43953(7) -0.1156(2) 0.63464(8) 0.0346(4) Uani 1 1 d . . .
O17 O 0.31234(8) -0.4247(2) 0.65822(9) 0.0455(5) Uani 1 1 d . . .
H17 H 0.3298 -0.5446 0.6598 0.068 Uiso 1 1 calc R . .
C3 C 0.40859(10) 0.0953(3) 0.62293(11) 0.0282(5) Uani 1 1 d . . .
C5 C 0.32541(10) -0.0360(3) 0.66427(11) 0.0296(5) Uani 1 1 d . . .
C6 C 0.35970(10) -0.2603(3) 0.67548(11) 0.0319(5) Uani 1 1 d . . .
C7 C 0.46630(10) 0.2486(3) 0.63880(11) 0.0335(5) Uani 1 1 d . . .
H7A H 0.4976 0.2107 0.6829 0.040 Uiso 1 1 calc R . .
H7B H 0.4519 0.3979 0.6415 0.040 Uiso 1 1 calc R . .
C8 C 0.49919(12) 0.2370(4) 0.58516(12) 0.0441(6) Uani 1 1 d . . .
H8A H 0.5199 0.0948 0.5876 0.053 Uiso 1 1 calc R . .
H8B H 0.5328 0.3486 0.5947 0.053 Uiso 1 1 calc R . .
C9 C 0.45078(13) 0.2713(5) 0.51355(12) 0.0505(7) Uani 1 1 d . . .
H9B H 0.4341 0.4202 0.5093 0.061 Uiso 1 1 calc R . .
H9A H 0.4727 0.2521 0.4806 0.061 Uiso 1 1 calc R . .
C10 C 0.39457(13) 0.1103(4) 0.49820(12) 0.0464(6) Uani 1 1 d . . .
H10A H 0.4108 -0.0381 0.4986 0.056 Uiso 1 1 calc R . .
H10B H 0.3637 0.1394 0.4531 0.056 Uiso 1 1 calc R . .
C10A C 0.36030(10) 0.1300(4) 0.55083(10) 0.0337(5) Uani 1 1 d . . .
H10C H 0.3455 0.2825 0.5489 0.040 Uiso 1 1 calc R . .
C11 C 0.29968(11) -0.0120(4) 0.53518(12) 0.0397(6) Uani 1 1 d . . .
H11A H 0.3101 -0.1615 0.5265 0.048 Uiso 1 1 calc R . .
H11B H 0.2665 0.0423 0.4944 0.048 Uiso 1 1 calc R . .
C12 C 0.27335(10) -0.0108(4) 0.59413(12) 0.0375(5) Uani 1 1 d . . .
H12B H 0.2422 -0.1294 0.5875 0.045 Uiso 1 1 calc R . .
H12A H 0.2503 0.1260 0.5931 0.045 Uiso 1 1 calc R . .
C13 C 0.29823(11) 0.0115(4) 0.72099(12) 0.0393(6) Uani 1 1 d . . .
H13A H 0.2824 0.1615 0.7162 0.047 Uiso 1 1 calc R . .
H13B H 0.2614 -0.0846 0.7155 0.047 Uiso 1 1 calc R . .
C14 C 0.34676(12) -0.0183(5) 0.79216(13) 0.0496(7) Uani 1 1 d . . .
H14A H 0.3250 0.0020 0.8253 0.060 Uiso 1 1 calc R . .
H14B H 0.3805 0.0921 0.8006 0.060 Uiso 1 1 calc R . .
C15 C 0.37739(13) -0.2455(4) 0.80102(13) 0.0501(7) Uani 1 1 d . . .
H15A H 0.3444 -0.3555 0.7977 0.060 Uiso 1 1 calc R . .
H15B H 0.4102 -0.2568 0.8459 0.060 Uiso 1 1 calc R . .
C16 C 0.40839(11) -0.2897(4) 0.74688(11) 0.0404(6) Uani 1 1 d . . .
H16A H 0.4446 -0.1898 0.7534 0.049 Uiso 1 1 calc R . .
H16B H 0.4252 -0.4384 0.7520 0.049 Uiso 1 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
O4 0.0333(8) 0.0186(7) 0.0379(8) -0.0030(6) 0.0152(6) -0.0014(6)
O1 0.0480(9) 0.0155(7) 0.0509(10) -0.0029(6) 0.0212(7) 0.0000(6)
O2 0.0366(8) 0.0195(8) 0.0498(9) 0.0051(6) 0.0173(7) 0.0057(6)
O17 0.0485(10) 0.0204(8) 0.0655(12) -0.0016(7) 0.0165(8) -0.0076(7)
C3 0.0342(10) 0.0166(9) 0.0356(11) 0.0018(8) 0.0143(9) 0.0036(8)
C5 0.0296(10) 0.0209(10) 0.0389(12) -0.0006(8) 0.0125(9) -0.0018(8)
C6 0.0354(11) 0.0194(10) 0.0414(13) 0.0003(9) 0.0136(10) -0.0020(8)
C7 0.0348(11) 0.0219(11) 0.0431(13) -0.0007(9) 0.0125(10) -0.0021(9)
C8 0.0413(13) 0.0386(13) 0.0572(16) 0.0032(11) 0.0230(12) -0.0005(10)
C9 0.0589(16) 0.0511(16) 0.0495(16) 0.0094(12) 0.0291(13) 0.0025(12)
C10 0.0552(15) 0.0488(15) 0.0360(13) 0.0024(11) 0.0165(11) 0.0008(12)
C10A 0.0373(11) 0.0267(11) 0.0340(12) 0.0043(9) 0.0080(9) 0.0035(9)
C11 0.0375(12) 0.0354(12) 0.0373(13) -0.0003(10) 0.0011(10) 0.0000(10)
C12 0.0307(11) 0.0300(11) 0.0460(14) 0.0012(10) 0.0053(10) -0.0014(9)
C13 0.0402(12) 0.0313(12) 0.0528(15) -0.0008(11) 0.0243(12) -0.0013(10)
C14 0.0557(15) 0.0568(17) 0.0430(15) -0.0031(12) 0.0254(12) 0.0004(13)
C15 0.0514(14) 0.0565(17) 0.0411(14) 0.0120(12) 0.0139(11) -0.0032(13)
C16 0.0413(12) 0.0309(12) 0.0473(14) 0.0103(10) 0.0128(11) 0.0048(10)

_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
O4 C3 1.429(2) . ?
O4 C5 1.464(2) . ?
O1 C6 1.449(3) . ?
O1 O2 1.461(2) . ?
O2 C3 1.434(2) . ?
O17 C6 1.397(3) . ?
C3 C7 1.513(3) . ?
C3 C10A 1.531(3) . ?
C5 C13 1.520(3) . ?
C5 C12 1.526(3) . ?
C5 C6 1.538(3) . ?
C6 C16 1.519(3) . ?
C7 C8 1.523(3) . ?
C8 C9 1.524(3) . ?
C9 C10 1.519(4) . ?
C10 C10A 1.529(3) . ?
C10A C11 1.522(3) . ?
C11 C12 1.524(3) . ?
C13 C14 1.514(4) . ?
C14 C15 1.521(4) . ?
C15 C16 1.525(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
C3 O4 C5 111.98(15) . . ?
C6 O1 O2 108.18(14) . . ?
C3 O2 O1 109.48(14) . . ?
O4 C3 O2 108.68(15) . . ?
O4 C3 C7 109.55(16) . . ?
O2 C3 C7 101.84(16) . . ?
O4 C3 C10A 109.60(16) . . ?
O2 C3 C10A 114.80(17) . . ?
C7 C3 C10A 112.07(17) . . ?
O4 C5 C13 105.99(16) . . ?
O4 C5 C12 108.92(17) . . ?
C13 C5 C12 111.41(18) . . ?
O4 C5 C6 105.91(15) . . ?
C13 C5 C6 110.48(18) . . ?
C12 C5 C6 113.67(18) . . ?
O17 C6 O1 102.56(16) . . ?
O17 C6 C16 112.34(17) . . ?
O1 C6 C16 111.33(17) . . ?
O17 C6 C5 108.49(17) . . ?
O1 C6 C5 108.10(16) . . ?
C16 C6 C5 113.39(18) . . ?
C3 C7 C8 112.17(18) . . ?
C7 C8 C9 111.7(2) . . ?
C10 C9 C8 111.2(2) . . ?
C9 C10 C10A 110.9(2) . . ?
C11 C10A C10 113.87(19) . . ?
C11 C10A C3 113.10(17) . . ?
C10 C10A C3 110.58(18) . . ?
C10A C11 C12 111.34(18) . . ?
C11 C12 C5 114.17(18) . . ?
C14 C13 C5 114.25(19) . . ?
C13 C14 C15 111.2(2) . . ?
C14 C15 C16 111.0(2) . . ?
C6 C16 C15 111.42(19) . . ?

_diffrn_measured_fraction_theta_max 0.793
_diffrn_reflns_theta_full        27.97
_diffrn_measured_fraction_theta_full 0.793
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.055