#------------------------------------------------------------------------------
#$Date: 2026-04-05 13:34:35 +0200 (Sun 05 de Apr de 2026) $
#$Revision: 305281 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/55/7135572.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7135572
loop_
_publ_author_name
'Jiang, Yihua'
'Souare, Sokhna'
'Robeyns, Koen'
'Leng, Fucheng'
'Collard, Laurent'
'Leyssens, Tom'
_publ_section_title
;
 Solvent-triggered breakdown of solid solution behaviour enables direct
 enantioselective crystallization of RS-phenprocoumon.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6613
_journal_page_last               6616
_journal_paper_doi               10.1039/d6cc00933f
_journal_volume                  62
_journal_year                    2026
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H15 O3, C20 H25 N2 O2, C2 H3 N'
_chemical_formula_sum            'C40 H43 N3 O5'
_chemical_formula_weight         645.77
_chemical_name_common            'Quinidine Phenprocoumon acetonitrile solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-02-10 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.466(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5022(4)
_cell_length_b                   9.4634(3)
_cell_length_c                   15.5437(4)
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.9710
_cell_measurement_theta_min      3.3550
_cell_volume                     1711.46(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'180 images, ΔΦ 1.0° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13195
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.003
_diffrn_reflns_theta_min         3.390
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       rod
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 2010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         6174
_refine_ls_number_restraints     320
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0332P)²+0.4119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.590
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.655
_reflns_number_gt                5862
_reflns_number_total             6174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cc00933f2.cif
_cod_data_source_block           yj_rsphCouQDN_acn
_cod_depositor_comments
'Adding full bibliography for 7135572--7135577.cif.'
_cod_original_cell_volume        1711.48(9)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7135572
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07762(12) 0.69058(17) 0.70719(9) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.034048 0.649075 0.659461 0.028 Uiso 1 1 calc R U . . .
C2 C 0.16859(16) 0.7556(2) 0.68859(12) 0.0163(4) Uani 1 1 d . . . . .
H2 H 0.213141 0.680541 0.671020 0.020 Uiso 1 1 calc R U . . .
C3 C 0.12348(16) 0.8597(2) 0.60919(12) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.02510(17) 0.9351(3) 0.59604(13) 0.0207(4) Uani 1 1 d . . . . .
H4 H -0.013016 0.926471 0.638614 0.025 Uiso 1 1 calc R U . . .
C5 C -0.01898(18) 1.0251(3) 0.51934(14) 0.0227(5) Uani 1 1 d . . . . .
H5 H -0.086181 1.078010 0.512535 0.027 Uiso 1 1 calc R U . . .
N6 N 0.02740(15) 1.0406(2) 0.45621(11) 0.0211(4) Uani 1 1 d . . . . .
C7 C 0.12591(17) 0.9682(2) 0.46819(13) 0.0182(4) Uani 1 1 d . . . . .
C8 C 0.17619(18) 0.9843(3) 0.40026(13) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.139585 1.042493 0.347909 0.026 Uiso 1 1 calc R U . . .
C9 C 0.27548(18) 0.9178(3) 0.40910(14) 0.0231(5) Uani 1 1 d . . . . .
H9 H 0.308292 0.929885 0.363276 0.028 Uiso 1 1 calc R U . . .
C10 C 0.33056(18) 0.8302(3) 0.48675(14) 0.0226(5) Uani 1 1 d . . . . .
C11 C 0.28389(17) 0.8096(3) 0.55323(13) 0.0212(4) Uani 1 1 d . . . . .
H11 H 0.321224 0.749719 0.604520 0.025 Uiso 1 1 calc R U . . .
C12 C 0.17994(16) 0.8780(2) 0.54492(12) 0.0173(4) Uani 1 1 d . . . . .
O13 O 0.43061(13) 0.7702(2) 0.48754(11) 0.0312(4) Uani 1 1 d . . . . .
C14 C 0.4845(2) 0.6705(4) 0.5594(2) 0.0452(8) Uani 1 1 d . . . . .
H14A H 0.507841 0.717952 0.619503 0.068 Uiso 1 1 calc R U . . .
H14B H 0.552345 0.630618 0.550974 0.068 Uiso 1 1 calc R U . . .
H14C H 0.430236 0.594464 0.556997 0.068 Uiso 1 1 calc R U . . .
C15 C 0.24955(17) 0.8309(2) 0.77587(13) 0.0183(4) Uani 1 1 d . . . . .
H15 H 0.294515 0.902845 0.756090 0.022 Uiso 1 1 calc R U . . .
N16 N 0.33382(15) 0.7267(2) 0.83901(11) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.365045 0.666181 0.800918 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2781(2) 0.6335(3) 0.88796(14) 0.0244(5) Uani 1 1 d . . . . .
H17A H 0.331980 0.557511 0.920926 0.029 Uiso 1 1 calc R U . . .
H17B H 0.208803 0.588966 0.842491 0.029 Uiso 1 1 calc R U . . .
C18 C 0.24429(19) 0.7215(3) 0.95773(13) 0.0249(5) Uani 1 1 d . . . . .
H18 H 0.301484 0.701799 1.021058 0.030 Uiso 1 1 calc R U . . .
C19 C 0.25455(18) 0.8782(3) 0.93599(13) 0.0229(5) Uani 1 1 d . . . . .
H19 H 0.223402 0.938765 0.974089 0.027 Uiso 1 1 calc R U . . .
C20 C 0.18876(18) 0.9074(3) 0.83244(13) 0.0209(4) Uani 1 1 d . . . . .
H20A H 0.108664 0.873125 0.814032 0.025 Uiso 1 1 calc R U . . .
H20B H 0.186690 1.010306 0.820478 0.025 Uiso 1 1 calc R U . . .
C21 C 0.43125(18) 0.8064(3) 0.90780(14) 0.0271(5) Uani 1 1 d . . . . .
H21A H 0.474840 0.857670 0.875731 0.033 Uiso 1 1 calc R U . . .
H21B H 0.484217 0.739855 0.952463 0.033 Uiso 1 1 calc R U . . .
C22 C 0.38194(19) 0.9116(3) 0.95891(14) 0.0268(5) Uani 1 1 d . . . . .
H22A H 0.424405 0.904015 1.026407 0.032 Uiso 1 1 calc R U . . .
H22B H 0.390454 1.009280 0.939556 0.032 Uiso 1 1 calc R U . . .
C23 C 0.1280(2) 0.6756(3) 0.95503(16) 0.0359(6) Uani 1 1 d . . . . .
H23 H 0.061712 0.711149 0.907177 0.043 Uiso 1 1 calc R U . . .
C24 C 0.1139(2) 0.5877(3) 1.01637(17) 0.0384(6) Uani 1 1 d . . . . .
H24A H 0.178949 0.550858 1.064824 0.046 Uiso 1 1 calc R U . . .
H24B H 0.038656 0.561646 1.011910 0.046 Uiso 1 1 calc R U . . .
O31 O 0.4579(5) 0.1041(6) 0.7780(4) 0.0289(11) Uani 0.522(8) 1 d D U P A 1
C32 C 0.4912(7) 0.2245(8) 0.7735(9) 0.022(2) Uani 0.522(8) 1 d D U P A 1
O33 O 0.6115(7) 0.2337(9) 0.8003(19) 0.0210(17) Uani 0.522(8) 1 d D U P A 1
C34 C 0.6655(7) 0.3630(10) 0.8080(15) 0.023(4) Uani 0.522(8) 1 d D U P A 1
C35 C 0.7845(7) 0.3591(11) 0.8316(12) 0.017(2) Uani 0.522(8) 1 d D U P A 1
H35 H 0.825176 0.272050 0.842706 0.021 Uiso 0.522(8) 1 calc R U P A 1
C36 C 0.8408(9) 0.4865(11) 0.8381(14) 0.021(2) Uani 0.522(8) 1 d D U P A 1
H36 H 0.921202 0.487020 0.851109 0.025 Uiso 0.522(8) 1 calc R U P A 1
C37 C 0.7818(8) 0.6141(11) 0.8259(10) 0.0216(18) Uani 0.522(8) 1 d D U P A 1
H37 H 0.822767 0.700752 0.834773 0.026 Uiso 0.522(8) 1 calc R U P A 1
C38 C 0.6629(8) 0.6151(8) 0.8009(9) 0.0164(17) Uani 0.522(8) 1 d D U P A 1
H38 H 0.622547 0.702291 0.790847 0.020 Uiso 0.522(8) 1 calc R U P A 1
C39 C 0.6032(6) 0.4885(9) 0.7905(17) 0.0153(19) Uani 0.522(8) 1 d D U P A 1
C40 C 0.4768(5) 0.4809(8) 0.7572(7) 0.0119(14) Uani 0.522(8) 1 d D U P A 1
C41 C 0.4261(5) 0.3507(9) 0.7486(5) 0.0158(15) Uani 0.522(8) 1 d D U P A 1
O42 O 0.4212(4) 0.5994(6) 0.7371(3) 0.0187(9) Uani 0.522(8) 1 d D U P A 1
C43 C 0.2961(3) 0.3386(6) 0.7069(3) 0.0191(12) Uani 0.522(8) 1 d D U P A 1
H43 H 0.265495 0.435353 0.685979 0.023 Uiso 0.522(8) 1 calc R U P A 1
C44 C 0.2559(5) 0.2429(8) 0.6210(4) 0.0247(13) Uani 0.522(8) 1 d D U P A 1
H44A H 0.286102 0.146205 0.638881 0.030 Uiso 0.522(8) 1 calc R U P A 1
H44B H 0.170947 0.237749 0.596136 0.030 Uiso 0.522(8) 1 calc R U P A 1
C45 C 0.2966(16) 0.298(3) 0.5465(9) 0.032(4) Uani 0.522(8) 1 d D U P A 1
H45A H 0.380680 0.292991 0.568582 0.048 Uiso 0.522(8) 1 calc R U P A 1
H45B H 0.271714 0.395915 0.531963 0.048 Uiso 0.522(8) 1 calc R U P A 1
H45C H 0.263735 0.239596 0.490796 0.048 Uiso 0.522(8) 1 calc R U P A 1
O31B O 0.4901(6) 0.0571(7) 0.7773(4) 0.0347(13) Uani 0.478(8) 1 d D U P A 2
C32B C 0.5101(7) 0.1824(9) 0.7748(10) 0.024(2) Uani 0.478(8) 1 d D U P A 2
O33B O 0.6277(7) 0.2144(11) 0.801(2) 0.025(2) Uani 0.478(8) 1 d D U P A 2
C34B C 0.6639(7) 0.3525(10) 0.8055(14) 0.017(3) Uani 0.478(8) 1 d D U P A 2
C35B C 0.7810(9) 0.3770(15) 0.8288(17) 0.036(4) Uani 0.478(8) 1 d D U P A 2
H35B H 0.832291 0.299532 0.837783 0.043 Uiso 0.478(8) 1 calc R U P A 2
C36B C 0.8227(10) 0.5137(15) 0.8388(17) 0.035(3) Uani 0.478(8) 1 d D U P A 2
H36B H 0.902846 0.529981 0.856518 0.042 Uiso 0.478(8) 1 calc R U P A 2
C37B C 0.7475(9) 0.6273(13) 0.8231(11) 0.030(3) Uani 0.478(8) 1 d D U P A 2
H37B H 0.775520 0.721501 0.829294 0.036 Uiso 0.478(8) 1 calc R U P A 2
C38B C 0.6310(10) 0.6009(13) 0.7983(12) 0.031(3) Uani 0.478(8) 1 d D U P A 2
H38B H 0.579798 0.678589 0.788756 0.037 Uiso 0.478(8) 1 calc R U P A 2
C39B C 0.5867(7) 0.4648(11) 0.7869(18) 0.020(2) Uani 0.478(8) 1 d D U P A 2
C40B C 0.4625(6) 0.4339(10) 0.7548(8) 0.0166(19) Uani 0.478(8) 1 d D U P A 2
C41B C 0.4292(5) 0.2957(10) 0.7463(5) 0.0131(15) Uani 0.478(8) 1 d D U P A 2
O42B O 0.3939(4) 0.5413(7) 0.7342(3) 0.0206(10) Uani 0.478(8) 1 d D U P A 2
C43B C 0.3035(4) 0.2530(7) 0.7043(3) 0.0198(13) Uani 0.478(8) 1 d D U P A 2
H43B H 0.301932 0.147977 0.696848 0.024 Uiso 0.478(8) 1 calc R U P A 2
C44B C 0.2412(5) 0.3155(9) 0.6078(3) 0.0255(14) Uani 0.478(8) 1 d D U P A 2
H44C H 0.162977 0.274705 0.581407 0.031 Uiso 0.478(8) 1 calc R U P A 2
H44D H 0.233272 0.418804 0.613380 0.031 Uiso 0.478(8) 1 calc R U P A 2
C45B C 0.3035(18) 0.287(3) 0.5422(10) 0.034(5) Uani 0.478(8) 1 d D U P A 2
H45D H 0.318859 0.185859 0.541299 0.050 Uiso 0.478(8) 1 calc R U P A 2
H45E H 0.376294 0.339317 0.562976 0.050 Uiso 0.478(8) 1 calc R U P A 2
H45F H 0.255522 0.318461 0.479822 0.050 Uiso 0.478(8) 1 calc R U P A 2
C46 C 0.23895(18) 0.2875(3) 0.77341(15) 0.0251(5) Uani 1 1 d D . . . .
C47 C 0.29889(18) 0.2733(3) 0.86768(14) 0.0228(4) Uani 1 1 d . . . . .
H47 H 0.380509 0.271414 0.890589 0.027 Uiso 1 1 calc R U . . .
C48 C 0.2424(2) 0.2620(3) 0.92917(15) 0.0270(5) Uani 1 1 d . . . . .
H48 H 0.284986 0.253280 0.993579 0.032 Uiso 1 1 calc R U . . .
C49 C 0.1239(2) 0.2635(4) 0.89635(18) 0.0391(7) Uani 1 1 d . . . . .
H49 H 0.084456 0.255189 0.938029 0.047 Uiso 1 1 calc R U . . .
C50 C 0.0630(2) 0.2770(4) 0.80300(19) 0.0386(6) Uani 1 1 d . . . . .
H50 H -0.018598 0.277147 0.780323 0.046 Uiso 1 1 calc R U . . .
C51 C 0.11964(19) 0.2902(3) 0.74199(15) 0.0281(5) Uani 1 1 d . . . . .
H51 H 0.076551 0.301355 0.677836 0.034 Uiso 1 1 calc R U . . .
N61 N 0.8585(5) -0.0354(7) 0.7529(4) 0.1020(19) Uani 0.934(7) 1 d D U P B 3
C62 C 0.7637(6) -0.0205(5) 0.7108(4) 0.0687(14) Uani 0.934(7) 1 d D U P B 3
C63 C 0.6414(5) -0.0059(5) 0.6586(3) 0.0771(15) Uani 0.934(7) 1 d D U P B 3
H63A H 0.625694 0.088651 0.631123 0.116 Uiso 0.934(7) 1 calc R U P B 3
H63B H 0.598974 -0.019381 0.699899 0.116 Uiso 0.934(7) 1 calc R U P B 3
H63C H 0.617118 -0.077167 0.609439 0.116 Uiso 0.934(7) 1 calc R U P B 3
N61B N 0.828(5) 0.055(9) 0.685(5) 0.1020(19) Uani 0.066(7) 1 d D . P B 4
C62B C 0.732(5) 0.042(7) 0.666(4) 0.0687(14) Uani 0.066(7) 1 d D . P B 4
C63B C 0.608(5) 0.041(9) 0.644(6) 0.0771(15) Uani 0.066(7) 1 d D . P B 4
H63D H 0.592861 0.039424 0.701284 0.116 Uiso 0.066(7) 1 calc R U P B 4
H63E H 0.574767 -0.042534 0.606925 0.116 Uiso 0.066(7) 1 calc R U P B 4
H63F H 0.574368 0.126544 0.608691 0.116 Uiso 0.066(7) 1 calc R U P B 4
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'
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
C2 O1 H1 109.5 . . ?
O1 C2 C3 111.20(15) . . ?
O1 C2 C15 109.90(14) . . ?
C3 C2 C15 110.16(17) . . ?
O1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C15 C2 H2 108.5 . . ?
C4 C3 C12 118.57(18) . . ?
C4 C3 C2 120.35(17) . . ?
C12 C3 C2 121.04(18) . . ?
C3 C4 C5 119.63(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N6 C5 C4 123.84(19) . . ?
N6 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C5 N6 C7 117.69(18) . . ?
N6 C7 C12 123.08(17) . . ?
N6 C7 C8 117.94(18) . . ?
C12 C7 C8 118.99(18) . . ?
C9 C8 C7 120.91(19) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.00(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
O13 C10 C11 124.89(19) . . ?
O13 C10 C9 114.06(17) . . ?
C11 C10 C9 121.05(19) . . ?
C10 C11 C12 119.67(19) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 119.36(17) . . ?
C11 C12 C3 123.56(18) . . ?
C7 C12 C3 117.07(18) . . ?
C10 O13 C14 116.67(17) . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N16 C15 C20 107.97(15) . . ?
N16 C15 C2 110.29(17) . . ?
C20 C15 C2 114.77(16) . . ?
N16 C15 H15 107.9 . . ?
C20 C15 H15 107.9 . . ?
C2 C15 H15 107.9 . . ?
C17 N16 C21 110.04(16) . . ?
C17 N16 C15 111.83(16) . . ?
C21 N16 C15 109.04(17) . . ?
C17 N16 H16 108.6 . . ?
C21 N16 H16 108.6 . . ?
C15 N16 H16 108.6 . . ?
N16 C17 C18 109.75(19) . . ?
N16 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N16 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C23 C18 C19 115.5(2) . . ?
C23 C18 C17 109.58(19) . . ?
C19 C18 C17 107.43(17) . . ?
C23 C18 H18 108.0 . . ?
C19 C18 H18 108.0 . . ?
C17 C18 H18 108.0 . . ?
C22 C19 C18 108.14(19) . . ?
C22 C19 C20 108.54(17) . . ?
C18 C19 C20 110.32(18) . . ?
C22 C19 H19 109.9 . . ?
C18 C19 H19 109.9 . . ?
C20 C19 H19 109.9 . . ?
C15 C20 C19 109.04(17) . . ?
C15 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
C15 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
N16 C21 C22 108.67(17) . . ?
N16 C21 H21A 110.0 . . ?
C22 C21 H21A 110.0 . . ?
N16 C21 H21B 110.0 . . ?
C22 C21 H21B 110.0 . . ?
H21A C21 H21B 108.3 . . ?
C19 C22 C21 109.00(18) . . ?
C19 C22 H22A 109.9 . . ?
C21 C22 H22A 109.9 . . ?
C19 C22 H22B 109.9 . . ?
C21 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C18 122.9(2) . . ?
C24 C23 H23 118.5 . . ?
C18 C23 H23 118.5 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
O31 C32 O33 113.0(7) . . ?
O31 C32 C41 128.8(6) . . ?
O33 C32 C41 118.2(6) . . ?
C34 O33 C32 121.0(7) . . ?
O33 C34 C39 121.2(7) . . ?
O33 C34 C35 116.1(7) . . ?
C39 C34 C35 122.7(7) . . ?
C36 C35 C34 117.5(8) . . ?
C36 C35 H35 121.3 . . ?
C34 C35 H35 121.3 . . ?
C35 C36 C37 121.1(8) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C36 C37 C38 120.2(7) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C39 C38 C37 120.0(6) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 118.3(6) . . ?
C38 C39 C40 123.0(7) . . ?
C34 C39 C40 118.6(7) . . ?
O42 C40 C41 124.5(6) . . ?
O42 C40 C39 117.0(6) . . ?
C41 C40 C39 118.5(6) . . ?
C40 C41 C32 122.2(5) . . ?
C40 C41 C43 119.7(6) . . ?
C32 C41 C43 118.1(6) . . ?
C41 C43 C46 115.3(4) . . ?
C41 C43 C44 111.9(4) . . ?
C46 C43 C44 108.4(4) . . ?
C41 C43 H43 107.0 . . ?
C46 C43 H43 107.0 . . ?
C44 C43 H43 107.0 . . ?
C45 C44 C43 111.6(9) . . ?
C45 C44 H44A 109.3 . . ?
C43 C44 H44A 109.3 . . ?
C45 C44 H44B 109.3 . . ?
C43 C44 H44B 109.3 . . ?
H44A C44 H44B 108.0 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O31B C32B O33B 113.9(8) . . ?
O31B C32B C41B 127.7(7) . . ?
O33B C32B C41B 118.3(7) . . ?
C34B O33B C32B 120.6(8) . . ?
O33B C34B C35B 117.8(8) . . ?
O33B C34B C39B 121.6(7) . . ?
C35B C34B C39B 120.6(8) . . ?
C36B C35B C34B 120.1(9) . . ?
C36B C35B H35B 119.9 . . ?
C34B C35B H35B 119.9 . . ?
C35B C36B C37B 120.1(9) . . ?
C35B C36B H36B 119.9 . . ?
C37B C36B H36B 119.9 . . ?
C38B C37B C36B 118.9(9) . . ?
C38B C37B H37B 120.5 . . ?
C36B C37B H37B 120.5 . . ?
C37B C38B C39B 122.1(9) . . ?
C37B C38B H38B 118.9 . . ?
C39B C38B H38B 118.9 . . ?
C38B C39B C34B 117.9(7) . . ?
C38B C39B C40B 123.3(8) . . ?
C34B C39B C40B 118.8(7) . . ?
O42B C40B C41B 125.3(6) . . ?
O42B C40B C39B 116.6(7) . . ?
C41B C40B C39B 118.0(6) . . ?
C40B C41B C32B 122.2(5) . . ?
C40B C41B C43B 121.9(6) . . ?
C32B C41B C43B 115.9(7) . . ?
C41B C43B C44B 113.1(5) . . ?
C41B C43B C46 110.8(4) . . ?
C44B C43B C46 112.3(4) . . ?
C41B C43B H43B 106.7 . . ?
C44B C43B H43B 106.7 . . ?
C46 C43B H43B 106.7 . . ?
C45B C44B C43B 112.9(10) . . ?
C45B C44B H44C 109.0 . . ?
C43B C44B H44C 109.0 . . ?
C45B C44B H44D 109.0 . . ?
C43B C44B H44D 109.0 . . ?
H44C C44B H44D 107.8 . . ?
C44B C45B H45D 109.5 . . ?
C44B C45B H45E 109.5 . . ?
H45D C45B H45E 109.5 . . ?
C44B C45B H45F 109.5 . . ?
H45D C45B H45F 109.5 . . ?
H45E C45B H45F 109.5 . . ?
C47 C46 C51 117.96(18) . . ?
C47 C46 C43 122.5(2) . . ?
C51 C46 C43 117.5(2) . . ?
C47 C46 C43B 118.7(2) . . ?
C51 C46 C43B 120.6(2) . . ?
C48 C47 C46 121.4(2) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C49 C48 C47 119.6(2) . . ?
C49 C48 H48 120.2 . . ?
C47 C48 H48 120.2 . . ?
C50 C49 C48 119.7(2) . . ?
C50 C49 H49 120.1 . . ?
C48 C49 H49 120.1 . . ?
C49 C50 C51 120.5(2) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 H50 119.7 . . ?
C50 C51 C46 120.7(2) . . ?
C50 C51 H51 119.6 . . ?
C46 C51 H51 119.6 . . ?
N61 C62 C63 177.9(6) . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
N61B C62B C63B 174(7) . . ?
C62B C63B H63D 109.5 . . ?
C62B C63B H63E 109.5 . . ?
H63D C63B H63E 109.5 . . ?
C62B C63B H63F 109.5 . . ?
H63D C63B H63F 109.5 . . ?
H63E C63B H63F 109.5 . . ?
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 C2 1.413(2) . ?
O1 H1 0.8400 . ?
C2 C3 1.518(3) . ?
C2 C15 1.539(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.371(3) . ?
C3 C12 1.429(3) . ?
C4 C5 1.404(3) . ?
C4 H4 0.9500 . ?
C5 N6 1.318(3) . ?
C5 H5 0.9500 . ?
N6 C7 1.361(3) . ?
C7 C12 1.420(3) . ?
C7 C8 1.421(3) . ?
C8 C9 1.353(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(3) . ?
C9 H9 0.9500 . ?
C10 O13 1.370(3) . ?
C10 C11 1.374(3) . ?
C11 C12 1.415(3) . ?
C11 H11 0.9500 . ?
O13 C14 1.429(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N16 1.513(3) . ?
C15 C20 1.537(3) . ?
C15 H15 1.0000 . ?
N16 C17 1.493(3) . ?
N16 C21 1.497(3) . ?
N16 H16 1.0000 . ?
C17 C18 1.545(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C23 1.503(3) . ?
C18 C19 1.536(3) . ?
C18 H18 1.0000 . ?
C19 C22 1.532(3) . ?
C19 C20 1.541(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.537(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.325(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
O31 C32 1.224(8) . ?
C32 O33 1.409(7) . ?
C32 C41 1.418(8) . ?
O33 C34 1.381(7) . ?
C34 C39 1.392(7) . ?
C34 C35 1.396(7) . ?
C35 C36 1.381(8) . ?
C35 H35 0.9500 . ?
C36 C37 1.391(8) . ?
C36 H36 0.9500 . ?
C37 C38 1.392(8) . ?
C37 H37 0.9500 . ?
C38 C39 1.389(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.474(7) . ?
C40 O42 1.295(7) . ?
C40 C41 1.369(8) . ?
C41 C43 1.518(6) . ?
C43 C46 1.534(4) . ?
C43 C44 1.538(6) . ?
C43 H43 1.0000 . ?
C44 C45 1.517(10) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
O31B C32B 1.216(8) . ?
C32B O33B 1.407(7) . ?
C32B C41B 1.429(8) . ?
O33B C34B 1.377(8) . ?
C34B C35B 1.393(8) . ?
C34B C39B 1.393(7) . ?
C35B C36B 1.382(9) . ?
C35B H35B 0.9500 . ?
C36B C37B 1.389(9) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.386(8) . ?
C37B H37B 0.9500 . ?
C38B C39B 1.387(9) . ?
C38B H38B 0.9500 . ?
C39B C40B 1.477(8) . ?
C40B O42B 1.292(8) . ?
C40B C41B 1.364(9) . ?
C41B C43B 1.519(6) . ?
C43B C44B 1.534(7) . ?
C43B C46 1.596(5) . ?
C43B H43B 1.0000 . ?
C44B C45B 1.516(11) . ?
C44B H44C 0.9900 . ?
C44B H44D 0.9900 . ?
C45B H45D 0.9800 . ?
C45B H45E 0.9800 . ?
C45B H45F 0.9800 . ?
C46 C47 1.387(3) . ?
C46 C51 1.390(3) . ?
C47 C48 1.385(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.379(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.376(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.381(3) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
N61 C62 1.133(7) . ?
C62 C63 1.451(7) . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
N61B C62B 1.135(14) . ?
C62B C63B 1.451(14) . ?
C63B H63D 0.9800 . ?
C63B H63E 0.9800 . ?
C63B H63F 0.9800 . ?
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
O1 C2 C3 C4 33.5(3) . . . . ?
C15 C2 C3 C4 -88.6(2) . . . . ?
O1 C2 C3 C12 -144.46(18) . . . . ?
C15 C2 C3 C12 93.5(2) . . . . ?
C12 C3 C4 C5 1.5(3) . . . . ?
C2 C3 C4 C5 -176.5(2) . . . . ?
C3 C4 C5 N6 1.5(4) . . . . ?
C4 C5 N6 C7 -2.2(3) . . . . ?
C5 N6 C7 C12 0.0(3) . . . . ?
C5 N6 C7 C8 179.9(2) . . . . ?
N6 C7 C8 C9 178.5(2) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 O13 -179.6(2) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
O13 C10 C11 C12 179.8(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C10 C11 C12 C3 178.2(2) . . . . ?
N6 C7 C12 C11 -178.3(2) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
N6 C7 C12 C3 2.9(3) . . . . ?
C8 C7 C12 C3 -177.08(19) . . . . ?
C4 C3 C12 C11 177.8(2) . . . . ?
C2 C3 C12 C11 -4.3(3) . . . . ?
C4 C3 C12 C7 -3.5(3) . . . . ?
C2 C3 C12 C7 174.47(19) . . . . ?
C11 C10 O13 C14 5.1(4) . . . . ?
C9 C10 O13 C14 -174.3(2) . . . . ?
O1 C2 C15 N16 82.6(2) . . . . ?
C3 C2 C15 N16 -154.50(16) . . . . ?
O1 C2 C15 C20 -39.5(2) . . . . ?
C3 C2 C15 C20 83.3(2) . . . . ?
C20 C15 N16 C17 51.6(2) . . . . ?
C2 C15 N16 C17 -74.5(2) . . . . ?
C20 C15 N16 C21 -70.3(2) . . . . ?
C2 C15 N16 C21 163.56(16) . . . . ?
C21 N16 C17 C18 53.3(2) . . . . ?
C15 N16 C17 C18 -68.0(2) . . . . ?
N16 C17 C18 C23 139.06(19) . . . . ?
N16 C17 C18 C19 12.8(2) . . . . ?
C23 C18 C19 C22 169.90(17) . . . . ?
C17 C18 C19 C22 -67.5(2) . . . . ?
C23 C18 C19 C20 -71.5(2) . . . . ?
C17 C18 C19 C20 51.1(2) . . . . ?
N16 C15 C20 C19 13.6(2) . . . . ?
C2 C15 C20 C19 137.05(19) . . . . ?
C22 C19 C20 C15 51.1(2) . . . . ?
C18 C19 C20 C15 -67.2(2) . . . . ?
C17 N16 C21 C22 -67.5(2) . . . . ?
C15 N16 C21 C22 55.5(2) . . . . ?
C18 C19 C22 C21 53.7(2) . . . . ?
C20 C19 C22 C21 -65.9(2) . . . . ?
N16 C21 C22 C19 11.2(2) . . . . ?
C19 C18 C23 C24 -139.2(3) . . . . ?
C17 C18 C23 C24 99.3(3) . . . . ?
O31 C32 O33 C34 -174(2) . . . . ?
C41 C32 O33 C34 4(3) . . . . ?
C32 O33 C34 C39 1(4) . . . . ?
C32 O33 C34 C35 -178(2) . . . . ?
O33 C34 C35 C36 179(2) . . . . ?
C39 C34 C35 C36 1(3) . . . . ?
C34 C35 C36 C37 3(3) . . . . ?
C35 C36 C37 C38 -4(3) . . . . ?
C36 C37 C38 C39 2(2) . . . . ?
C37 C38 C39 C34 2(3) . . . . ?
C37 C38 C39 C40 -175.1(16) . . . . ?
O33 C34 C39 C38 179(2) . . . . ?
C35 C34 C39 C38 -3(3) . . . . ?
O33 C34 C39 C40 -4(4) . . . . ?
C35 C34 C39 C40 174.0(19) . . . . ?
C38 C39 C40 O42 0(3) . . . . ?
C34 C39 C40 O42 -176.5(17) . . . . ?
C38 C39 C40 C41 179.3(16) . . . . ?
C34 C39 C40 C41 3(3) . . . . ?
O42 C40 C41 C32 -178.7(10) . . . . ?
C39 C40 C41 C32 2.2(18) . . . . ?
O42 C40 C41 C43 4.2(13) . . . . ?
C39 C40 C41 C43 -174.9(13) . . . . ?
O31 C32 C41 C40 172.0(11) . . . . ?
O33 C32 C41 C40 -6(2) . . . . ?
O31 C32 C41 C43 -10.8(17) . . . . ?
O33 C32 C41 C43 171.6(15) . . . . ?
C40 C41 C43 C46 -114.0(7) . . . . ?
C32 C41 C43 C46 68.8(9) . . . . ?
C40 C41 C43 C44 121.6(8) . . . . ?
C32 C41 C43 C44 -55.6(9) . . . . ?
C41 C43 C44 C45 -59.1(11) . . . . ?
C46 C43 C44 C45 172.8(10) . . . . ?
O31B C32B O33B C34B -177(2) . . . . ?
C41B C32B O33B C34B 4(3) . . . . ?
C32B O33B C34B C35B -178(2) . . . . ?
C32B O33B C34B C39B 2(4) . . . . ?
O33B C34B C35B C36B -176(3) . . . . ?
C39B C34B C35B C36B 4(4) . . . . ?
C34B C35B C36B C37B -2(4) . . . . ?
C35B C36B C37B C38B 1(3) . . . . ?
C36B C37B C38B C39B -1(3) . . . . ?
C37B C38B C39B C34B 3(3) . . . . ?
C37B C38B C39B C40B -176.0(17) . . . . ?
O33B C34B C39B C38B 176(2) . . . . ?
C35B C34B C39B C38B -4(4) . . . . ?
O33B C34B C39B C40B -5(4) . . . . ?
C35B C34B C39B C40B 175(2) . . . . ?
C38B C39B C40B O42B 2(3) . . . . ?
C34B C39B C40B O42B -176.7(17) . . . . ?
C38B C39B C40B C41B -180.0(18) . . . . ?
C34B C39B C40B C41B 1(3) . . . . ?
O42B C40B C41B C32B -176.9(11) . . . . ?
C39B C40B C41B C32B 5.5(18) . . . . ?
O42B C40B C41B C43B 4.3(14) . . . . ?
C39B C40B C41B C43B -173.4(14) . . . . ?
O31B C32B C41B C40B 173.6(12) . . . . ?
O33B C32B C41B C40B -8(2) . . . . ?
O31B C32B C41B C43B -7.4(18) . . . . ?
O33B C32B C41B C43B 170.7(17) . . . . ?
C40B C41B C43B C44B 54.4(9) . . . . ?
C32B C41B C43B C44B -124.5(9) . . . . ?
C40B C41B C43B C46 -72.7(9) . . . . ?
C32B C41B C43B C46 108.4(9) . . . . ?
C41B C43B C44B C45B 52.0(13) . . . . ?
C46 C43B C44B C45B 178.3(11) . . . . ?
C41 C43 C46 C47 9.2(6) . . . . ?
C44 C43 C46 C47 135.4(4) . . . . ?
C41 C43 C46 C51 172.7(4) . . . . ?
C44 C43 C46 C51 -61.1(5) . . . . ?
C41B C43B C46 C47 -34.8(6) . . . . ?
C44B C43B C46 C47 -162.4(4) . . . . ?
C41B C43B C46 C51 164.1(4) . . . . ?
C44B C43B C46 C51 36.5(7) . . . . ?
C51 C46 C47 C48 0.1(4) . . . . ?
C43 C46 C47 C48 163.5(3) . . . . ?
C43B C46 C47 C48 -161.5(3) . . . . ?
C46 C47 C48 C49 0.6(4) . . . . ?
C47 C48 C49 C50 -0.4(4) . . . . ?
C48 C49 C50 C51 -0.5(5) . . . . ?
C49 C50 C51 C46 1.3(5) . . . . ?
C47 C46 C51 C50 -1.0(4) . . . . ?
C43 C46 C51 C50 -165.3(3) . . . . ?
C43B C46 C51 C50 160.2(4) . . . . ?
