#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:23:13 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/30/7133091.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_7133091
loop_
_publ_author_name
'Songsermsawad, Sarita'
'Shemchuk, Oleksii'
'Robeyns, Koen'
'Collard, Laurent'
'E Flood, Adrian'
'Leyssens, Tom'
_publ_section_title
;
 Simultaneously resolving BINOL and proline using a stoichiometric
 cocrystal switch.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6607
_journal_page_last               6610
_journal_paper_doi               10.1039/d4cc02180k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H14 O2, 2(C5 H9 N O2)'
_chemical_formula_sum            'C30 H32 N2 O6'
_chemical_formula_weight         516.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                109.33(2)
_cell_angle_beta                 91.872(12)
_cell_angle_gamma                104.146(13)
_cell_formula_units_Z            2
_cell_length_a                   10.4050(9)
_cell_length_b                   10.991(2)
_cell_length_c                   12.216(3)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.9760
_cell_measurement_theta_min      3.1020
_cell_volume                     1268.4(4)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'60 images, ΔΦ 3.0° '
'53 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87597
_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    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cooling from ethanol solution'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0781
_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)+(0.0450P)²+0.6186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             4586
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02180k2.cif
_cod_data_source_block           alex_2BINOL-PRO
_cod_depositor_comments
'Adding full bibliography for 7133091--7133092.cif.'
_cod_original_cell_volume        1268.4(5)
_cod_database_code               7133091
_shelx_shelxl_version_number     2018/3
_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, -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 0.1604(2) 0.5785(2) 0.3888(2) 0.0427(6) Uani 1 1 d . . . . .
H1 H 0.181959 0.508878 0.378090 0.064 Uiso 1 1 calc R U . . .
C2 C 0.2239(3) 0.6429(3) 0.3194(3) 0.0336(8) Uani 1 1 d . . . . .
C3 C 0.2401(3) 0.7817(4) 0.3607(3) 0.0422(9) Uani 1 1 d . . . . .
H3 H 0.205450 0.821256 0.428628 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3054(4) 0.8585(4) 0.3025(3) 0.0459(9) Uani 1 1 d . . . . .
H4 H 0.317144 0.950594 0.331559 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3560(3) 0.7997(3) 0.1979(3) 0.0371(8) Uani 1 1 d . . . . .
C6 C 0.4283(3) 0.8793(4) 0.1385(3) 0.0491(10) Uani 1 1 d . . . . .
H6 H 0.440948 0.971578 0.167810 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4795(4) 0.8237(4) 0.0397(4) 0.0559(11) Uani 1 1 d . . . . .
H7 H 0.527423 0.877611 0.001838 0.067 Uiso 1 1 calc R U . . .
C8 C 0.4601(4) 0.6846(4) -0.0057(3) 0.0515(10) Uani 1 1 d . . . . .
H8 H 0.494661 0.646615 -0.074210 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3911(3) 0.6041(4) 0.0495(3) 0.0404(9) Uani 1 1 d . . . . .
H9 H 0.379921 0.512091 0.018451 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3363(3) 0.6592(3) 0.1537(3) 0.0307(8) Uani 1 1 d . . . . .
C11 C 0.2674(3) 0.5784(3) 0.2157(3) 0.0296(7) Uani 1 1 d . . . . .
O12 O 0.3856(2) 0.4600(2) 0.34311(19) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.450113 0.433564 0.354978 0.065 Uiso 1 1 calc R U . . .
C13 C 0.3128(3) 0.3759(3) 0.2392(3) 0.0314(8) Uani 1 1 d . . . . .
C14 C 0.3014(3) 0.2374(3) 0.2027(3) 0.0344(8) Uani 1 1 d . . . . .
H14 H 0.345743 0.204106 0.248738 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2260(3) 0.1523(3) 0.1009(3) 0.0397(9) Uani 1 1 d . . . . .
H15 H 0.219448 0.061217 0.077906 0.048 Uiso 1 1 calc R U . . .
C16 C 0.1573(3) 0.2004(3) 0.0295(3) 0.0346(8) Uani 1 1 d . . . . .
C17 C 0.0780(3) 0.1142(3) -0.0766(3) 0.0436(9) Uani 1 1 d . . . . .
H17 H 0.071834 0.023127 -0.101356 0.052 Uiso 1 1 calc R U . . .
C18 C 0.0110(4) 0.1610(4) -0.1431(3) 0.0486(10) Uani 1 1 d . . . . .
H18 H -0.041050 0.102355 -0.212466 0.058 Uiso 1 1 calc R U . . .
C19 C 0.0204(3) 0.2986(4) -0.1070(3) 0.0455(9) Uani 1 1 d . . . . .
H19 H -0.026075 0.330739 -0.152629 0.055 Uiso 1 1 calc R U . . .
C20 C 0.0971(3) 0.3856(3) -0.0054(3) 0.0371(8) Uani 1 1 d . . . . .
H20 H 0.102603 0.476401 0.016793 0.044 Uiso 1 1 calc R U . . .
C21 C 0.1683(3) 0.3405(3) 0.0666(3) 0.0292(7) Uani 1 1 d . . . . .
C22 C 0.2496(3) 0.4299(3) 0.1740(3) 0.0280(7) Uani 1 1 d . . . . .
N31 N 0.8574(2) 0.3751(3) 0.3575(2) 0.0380(7) Uani 1 1 d . . . . .
H31A H 0.839962 0.448934 0.404638 0.046 Uiso 1 1 calc R U . . .
H31B H 0.932282 0.367051 0.388214 0.046 Uiso 1 1 calc R U . . .
C32 C 0.8724(4) 0.3828(4) 0.2391(3) 0.0518(10) Uani 1 1 d . . . . .
H32A H 0.810459 0.426750 0.217820 0.062 Uiso 1 1 calc R U . . .
H32B H 0.962755 0.430573 0.235045 0.062 Uiso 1 1 calc R U . . .
C33 C 0.8409(4) 0.2404(4) 0.1626(4) 0.0666(13) Uani 1 1 d . . . . .
H33A H 0.918228 0.206019 0.163360 0.080 Uiso 1 1 calc R U . . .
H33B H 0.812342 0.229684 0.082771 0.080 Uiso 1 1 calc R U . . .
C34 C 0.7296(4) 0.1689(4) 0.2132(3) 0.0567(11) Uani 1 1 d . . . . .
H34A H 0.737337 0.079973 0.204214 0.068 Uiso 1 1 calc R U . . .
H34B H 0.643505 0.160430 0.174129 0.068 Uiso 1 1 calc R U . . .
C35 C 0.7435(3) 0.2543(3) 0.3432(3) 0.0376(8) Uani 1 1 d . . . . .
H35 H 0.766487 0.205242 0.391494 0.045 Uiso 1 1 calc R U . . .
C36 C 0.6156(3) 0.2955(4) 0.3770(3) 0.0372(8) Uani 1 1 d . . . . .
O37 O 0.6108(2) 0.4092(3) 0.3778(2) 0.0474(7) Uani 1 1 d . . . . .
O38 O 0.5257(2) 0.2112(3) 0.3966(2) 0.0540(7) Uani 1 1 d . . . . .
N41 N 0.3303(3) 0.2957(3) 0.5322(3) 0.0379(9) Uani 0.907(4) 1 d D . P A 1
H41A H 0.391987 0.278106 0.485121 0.045 Uiso 0.907(4) 1 calc R U P A 1
H41B H 0.320096 0.375467 0.537435 0.045 Uiso 0.907(4) 1 calc R U P A 1
C42 C 0.3733(4) 0.2971(5) 0.6503(4) 0.0606(13) Uani 0.907(4) 1 d D . P A 1
H42A H 0.468078 0.304009 0.659635 0.073 Uiso 0.907(4) 1 calc R U P A 1
H42B H 0.355577 0.372013 0.710987 0.073 Uiso 0.907(4) 1 calc R U P A 1
C43 C 0.2947(6) 0.1699(8) 0.6563(6) 0.087(2) Uani 0.907(4) 1 d D . P A 1
H43A H 0.282895 0.177410 0.736494 0.105 Uiso 0.907(4) 1 calc R U P A 1
H43B H 0.337148 0.098948 0.622512 0.105 Uiso 0.907(4) 1 calc R U P A 1
C44 C 0.1621(4) 0.1440(6) 0.5851(5) 0.0837(19) Uani 0.907(4) 1 d D . P A 1
H44A H 0.114696 0.049584 0.557370 0.100 Uiso 0.907(4) 1 calc R U P A 1
H44B H 0.106066 0.194863 0.631152 0.100 Uiso 0.907(4) 1 calc R U P A 1
C45 C 0.2004(3) 0.1901(4) 0.4837(3) 0.0401(10) Uani 0.907(4) 1 d D . P A 1
H45 H 0.216250 0.115203 0.420025 0.048 Uiso 0.907(4) 1 calc R U P A 1
C46 C 0.0948(4) 0.2418(4) 0.4373(4) 0.0376(11) Uani 0.907(4) 1 d D . P A 1
O47 O 0.1166(6) 0.3649(4) 0.4611(8) 0.0469(13) Uani 0.907(4) 1 d D . P A 1
O48 O -0.0087(3) 0.1546(3) 0.3845(3) 0.0712(11) Uani 0.907(4) 1 d D . P A 1
N41B N 0.308(3) 0.164(3) 0.497(2) 0.054(7) Uani 0.093(4) 1 d D U P A 2
H41C H 0.246144 0.093745 0.448357 0.065 Uiso 0.093(4) 1 calc R U P A 2
H41D H 0.377511 0.182368 0.459415 0.065 Uiso 0.093(4) 1 calc R U P A 2
C42B C 0.350(5) 0.134(4) 0.601(3) 0.067(10) Uani 0.093(4) 1 d D U P A 2
H42C H 0.340123 0.038651 0.580880 0.081 Uiso 0.093(4) 1 calc R U P A 2
H42D H 0.442012 0.182339 0.631951 0.081 Uiso 0.093(4) 1 calc R U P A 2
C43B C 0.259(6) 0.179(5) 0.685(4) 0.075(11) Uani 0.093(4) 1 d D U P A 2
H43C H 0.297703 0.197459 0.764302 0.090 Uiso 0.093(4) 1 calc R U P A 2
H43D H 0.174056 0.111396 0.668488 0.090 Uiso 0.093(4) 1 calc R U P A 2
C44B C 0.243(4) 0.305(4) 0.668(2) 0.063(8) Uani 0.093(4) 1 d D U P A 2
H44C H 0.313070 0.382290 0.716763 0.076 Uiso 0.093(4) 1 calc R U P A 2
H44D H 0.157138 0.319175 0.688991 0.076 Uiso 0.093(4) 1 calc R U P A 2
C45B C 0.252(3) 0.283(3) 0.540(2) 0.051(8) Uani 0.093(4) 1 d D U P A 2
H45B H 0.316429 0.360574 0.533327 0.061 Uiso 0.093(4) 1 calc R U P A 2
C46B C 0.119(4) 0.261(3) 0.469(3) 0.044(8) Uani 0.093(4) 1 d D U P A 2
O47B O 0.093(7) 0.364(4) 0.463(8) 0.0469(13) Uani 0.093(4) 1 d D U P A 2
O48B O 0.072(3) 0.146(3) 0.397(3) 0.063(8) Uani 0.093(4) 1 d D U P A 2
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 C11 123.6(3) . . ?
O1 C2 C3 114.4(3) . . ?
C11 C2 C3 122.0(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 C10 119.3(3) . . ?
C6 C5 C10 119.7(3) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 117.7(3) . . ?
C5 C10 C11 120.1(3) . . ?
C9 C10 C11 122.2(3) . . ?
C2 C11 C10 117.6(3) . . ?
C2 C11 C22 120.8(3) . . ?
C10 C11 C22 121.5(3) . . ?
C13 O12 H12 109.5 . . ?
O12 C13 C22 118.1(3) . . ?
O12 C13 C14 120.0(3) . . ?
C22 C13 C14 121.9(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 C21 119.2(3) . . ?
C15 C16 C21 118.7(3) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 119.7(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C16 117.6(3) . . ?
C20 C21 C22 122.5(3) . . ?
C16 C21 C22 119.9(3) . . ?
C13 C22 C21 118.1(3) . . ?
C13 C22 C11 119.7(3) . . ?
C21 C22 C11 122.1(3) . . ?
C32 N31 C35 107.0(2) . . ?
C32 N31 H31A 110.3 . . ?
C35 N31 H31A 110.3 . . ?
C32 N31 H31B 110.3 . . ?
C35 N31 H31B 110.3 . . ?
H31A N31 H31B 108.6 . . ?
C33 C32 N31 103.2(3) . . ?
C33 C32 H32A 111.1 . . ?
N31 C32 H32A 111.1 . . ?
C33 C32 H32B 111.1 . . ?
N31 C32 H32B 111.1 . . ?
H32A C32 H32B 109.1 . . ?
C32 C33 C34 104.9(3) . . ?
C32 C33 H33A 110.8 . . ?
C34 C33 H33A 110.8 . . ?
C32 C33 H33B 110.8 . . ?
C34 C33 H33B 110.8 . . ?
H33A C33 H33B 108.8 . . ?
C33 C34 C35 106.3(3) . . ?
C33 C34 H34A 110.5 . . ?
C35 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
C35 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 110.8(3) . . ?
N31 C35 C34 104.1(3) . . ?
C36 C35 C34 111.9(3) . . ?
N31 C35 H35 110.0 . . ?
C36 C35 H35 110.0 . . ?
C34 C35 H35 110.0 . . ?
O38 C36 O37 126.7(3) . . ?
O38 C36 C35 116.2(3) . . ?
O37 C36 C35 117.0(3) . . ?
C42 N41 C45 108.7(3) . . ?
C42 N41 H41A 110.0 . . ?
C45 N41 H41A 110.0 . . ?
C42 N41 H41B 110.0 . . ?
C45 N41 H41B 110.0 . . ?
H41A N41 H41B 108.3 . . ?
C43 C42 N41 105.4(4) . . ?
C43 C42 H42A 110.7 . . ?
N41 C42 H42A 110.7 . . ?
C43 C42 H42B 110.7 . . ?
N41 C42 H42B 110.7 . . ?
H42A C42 H42B 108.8 . . ?
C42 C43 C44 103.5(4) . . ?
C42 C43 H43A 111.1 . . ?
C44 C43 H43A 111.1 . . ?
C42 C43 H43B 111.1 . . ?
C44 C43 H43B 111.1 . . ?
H43A C43 H43B 109.0 . . ?
C45 C44 C43 104.2(4) . . ?
C45 C44 H44A 110.9 . . ?
C43 C44 H44A 110.9 . . ?
C45 C44 H44B 110.9 . . ?
C43 C44 H44B 110.9 . . ?
H44A C44 H44B 108.9 . . ?
N41 C45 C44 103.6(3) . . ?
N41 C45 C46 112.7(3) . . ?
C44 C45 C46 113.5(3) . . ?
N41 C45 H45 108.9 . . ?
C44 C45 H45 108.9 . . ?
C46 C45 H45 108.9 . . ?
O48 C46 O47 126.8(4) . . ?
O48 C46 C45 114.8(4) . . ?
O47 C46 C45 118.3(4) . . ?
C42B N41B C45B 107.9(10) . . ?
C42B N41B H41C 110.1 . . ?
C45B N41B H41C 110.1 . . ?
C42B N41B H41D 110.1 . . ?
C45B N41B H41D 110.1 . . ?
H41C N41B H41D 108.4 . . ?
C43B C42B N41B 104.0(13) . . ?
C43B C42B H42C 110.9 . . ?
N41B C42B H42C 110.9 . . ?
C43B C42B H42D 110.9 . . ?
N41B C42B H42D 110.9 . . ?
H42C C42B H42D 109.0 . . ?
C42B C43B C44B 103.9(13) . . ?
C42B C43B H43C 111.0 . . ?
C44B C43B H43C 111.0 . . ?
C42B C43B H43D 111.0 . . ?
C44B C43B H43D 111.0 . . ?
H43C C43B H43D 109.0 . . ?
C43B C44B C45B 105.6(11) . . ?
C43B C44B H44C 110.6 . . ?
C45B C44B H44C 110.6 . . ?
C43B C44B H44D 110.6 . . ?
C45B C44B H44D 110.6 . . ?
H44C C44B H44D 108.8 . . ?
N41B C45B C44B 104.5(9) . . ?
N41B C45B C46B 112.5(13) . . ?
C44B C45B C46B 114.2(15) . . ?
N41B C45B H45B 108.5 . . ?
C44B C45B H45B 108.5 . . ?
C46B C45B H45B 108.5 . . ?
O48B C46B O47B 125(2) . . ?
O48B C46B C45B 114.4(15) . . ?
O47B C46B C45B 116.4(17) . . ?
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 1.365(4) . ?
O1 H1 0.8200 . ?
C2 C11 1.382(4) . ?
C2 C3 1.404(5) . ?
C3 C4 1.352(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.410(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(5) . ?
C5 C10 1.416(4) . ?
C6 C7 1.351(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.431(4) . ?
C11 C22 1.501(4) . ?
O12 C13 1.363(4) . ?
O12 H12 0.8200 . ?
C13 C22 1.374(4) . ?
C13 C14 1.410(4) . ?
C14 C15 1.358(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.414(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(4) . ?
C16 C21 1.428(4) . ?
C17 C18 1.350(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.405(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.411(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.439(4) . ?
N31 C32 1.488(4) . ?
N31 C35 1.504(4) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
C32 C33 1.480(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.505(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.535(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.534(4) . ?
C35 H35 0.9800 . ?
C36 O38 1.237(4) . ?
C36 O37 1.259(4) . ?
N41 C42 1.491(5) . ?
N41 C45 1.500(4) . ?
N41 H41A 0.8900 . ?
N41 H41B 0.8900 . ?
C42 C43 1.463(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.520(7) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.516(6) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.526(5) . ?
C45 H45 0.9800 . ?
C46 O48 1.239(5) . ?
C46 O47 1.246(5) . ?
N41B C42B 1.489(11) . ?
N41B C45B 1.499(10) . ?
N41B H41C 0.8900 . ?
N41B H41D 0.8900 . ?
C42B C43B 1.464(12) . ?
C42B H42C 0.9700 . ?
C42B H42D 0.9700 . ?
C43B C44B 1.516(13) . ?
C43B H43C 0.9700 . ?
C43B H43D 0.9700 . ?
C44B C45B 1.517(11) . ?
C44B H44C 0.9700 . ?
C44B H44D 0.9700 . ?
C45B C46B 1.529(11) . ?
C45B H45B 0.9800 . ?
C46B O48B 1.244(11) . ?
C46B O47B 1.251(11) . ?
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 177.7(3) . . . . ?
C11 C2 C3 C4 -3.4(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C3 C4 C5 C10 0.7(5) . . . . ?
C4 C5 C6 C7 178.5(4) . . . . ?
C10 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C4 C5 C10 C9 -178.7(3) . . . . ?
C6 C5 C10 C9 -0.1(5) . . . . ?
C4 C5 C10 C11 -0.9(5) . . . . ?
C6 C5 C10 C11 177.7(3) . . . . ?
C8 C9 C10 C5 -0.1(5) . . . . ?
C8 C9 C10 C11 -177.9(3) . . . . ?
O1 C2 C11 C10 -178.1(3) . . . . ?
C3 C2 C11 C10 3.1(4) . . . . ?
O1 C2 C11 C22 -1.6(4) . . . . ?
C3 C2 C11 C22 179.6(3) . . . . ?
C5 C10 C11 C2 -1.0(4) . . . . ?
C9 C10 C11 C2 176.7(3) . . . . ?
C5 C10 C11 C22 -177.5(3) . . . . ?
C9 C10 C11 C22 0.2(4) . . . . ?
O12 C13 C14 C15 178.1(3) . . . . ?
C22 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 -179.9(3) . . . . ?
C14 C15 C16 C21 -0.2(5) . . . . ?
C15 C16 C17 C18 178.8(3) . . . . ?
C21 C16 C17 C18 -0.9(5) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 -0.5(5) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
C15 C16 C21 C20 -179.1(3) . . . . ?
C17 C16 C21 C22 -179.4(3) . . . . ?
C15 C16 C21 C22 0.9(4) . . . . ?
O12 C13 C22 C21 -177.5(2) . . . . ?
C14 C13 C22 C21 0.9(4) . . . . ?
O12 C13 C22 C11 2.8(4) . . . . ?
C14 C13 C22 C11 -178.8(3) . . . . ?
C20 C21 C22 C13 178.7(3) . . . . ?
C16 C21 C22 C13 -1.2(4) . . . . ?
C20 C21 C22 C11 -1.6(4) . . . . ?
C16 C21 C22 C11 178.5(3) . . . . ?
C2 C11 C22 C13 -63.2(4) . . . . ?
C10 C11 C22 C13 113.2(3) . . . . ?
C2 C11 C22 C21 117.2(3) . . . . ?
C10 C11 C22 C21 -66.5(4) . . . . ?
C35 N31 C32 C33 -35.9(4) . . . . ?
N31 C32 C33 C34 37.5(4) . . . . ?
C32 C33 C34 C35 -25.6(4) . . . . ?
C32 N31 C35 C36 -100.7(3) . . . . ?
C32 N31 C35 C34 19.7(4) . . . . ?
C33 C34 C35 N31 3.6(4) . . . . ?
C33 C34 C35 C36 123.3(4) . . . . ?
N31 C35 C36 O38 -162.7(3) . . . . ?
C34 C35 C36 O38 81.6(4) . . . . ?
N31 C35 C36 O37 19.8(4) . . . . ?
C34 C35 C36 O37 -95.9(4) . . . . ?
C45 N41 C42 C43 16.8(5) . . . . ?
N41 C42 C43 C44 -33.8(6) . . . . ?
C42 C43 C44 C45 38.6(6) . . . . ?
C42 N41 C45 C44 7.2(4) . . . . ?
C42 N41 C45 C46 130.3(4) . . . . ?
C43 C44 C45 N41 -27.6(5) . . . . ?
C43 C44 C45 C46 -150.2(5) . . . . ?
N41 C45 C46 O48 172.1(4) . . . . ?
C44 C45 C46 O48 -70.4(5) . . . . ?
N41 C45 C46 O47 -11.8(7) . . . . ?
C44 C45 C46 O47 105.6(7) . . . . ?
C45B N41B C42B C43B 29(4) . . . . ?
N41B C42B C43B C44B -38(4) . . . . ?
C42B C43B C44B C45B 33(4) . . . . ?
C42B N41B C45B C44B -9(3) . . . . ?
C42B N41B C45B C46B -133(3) . . . . ?
C43B C44B C45B N41B -14(3) . . . . ?
C43B C44B C45B C46B 109(3) . . . . ?
N41B C45B C46B O48B 7(4) . . . . ?
C44B C45B C46B O48B -111(4) . . . . ?
N41B C45B C46B O47B -151(6) . . . . ?
C44B C45B C46B O47B 90(6) . . . . ?
