#------------------------------------------------------------------------------
#$Date: 2025-04-05 04:43:15 +0200 (Sat 05 de Apr de 2025) $
#$Revision: 298869 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/97/7249759.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_7249759
loop_
_publ_author_name
'Nagdeve, Rahul D.'
'Thakur, Jyoti Swarup'
'Chandrashekharappa, Sandeep'
'Mondal, Pradip Kumar'
'Deb, Pran Kishore'
'Polentarutti, Maurizio'
'Bairagi, Keshab M.'
'Rakshit, Gourav'
'Alwassil, Osama I.'
'Pillay, Melendhran'
'Venugopala, Katharigatta N.'
'Nayak, Susanta K.'
_publ_section_title
;
 Structural analysis, in vitro anti-tubercular activities, and in silico
 ADMET evaluation of ethyl 7-methoxy-3-(4-substituted
 benzoyl)indolizine-1-carboxylates
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1707
_journal_page_last               1721
_journal_paper_doi               10.1039/D4CE01018C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C22 H20 N2 O8'
_chemical_formula_sum            'C22 H20 N2 O8'
_chemical_formula_weight         440.40
_chemical_melting_point          184
_chemical_name_common            Indolizine
_chemical_name_systematic
;
diethyl 7-methoxy-3-(4-nitrobenzoyl)indolizine-1,2-dicarboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-12-01 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.91(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.833(2)
_cell_length_b                   17.576(4)
_cell_length_c                   19.870(4)
_cell_measurement_reflns_used    69300
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      1.5
_cell_volume                     4057.8(15)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Elettra Synchrotron - XRD1 BL'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            69300
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.756
_diffrn_reflns_theta_min         1.536
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      1.44
_exptl_crystal_description       Cubed
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.948
_exptl_transmission_factor_min   0.989
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         12079
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0586P)²+1.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9381
_reflns_number_total             12079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01018c2.cif
_cod_data_source_block           5h
_cod_depositor_comments
'Adding full bibliography for 7249753--7249759.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249759
_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.
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O6B O -0.54629(8) 0.23092(6) 0.05353(5) 0.0303(2) Uani 1 1 d . . . . .
O4B O 0.08087(8) 0.38860(6) 0.17205(5) 0.02801(19) Uani 1 1 d . . . . .
O3B O 0.12802(8) 0.34028(6) 0.07602(5) 0.0286(2) Uani 1 1 d . . . . .
O6A O 1.55966(8) 0.37058(6) 0.46036(5) 0.0301(2) Uani 1 1 d . . . . .
O2B O -0.08305(9) 0.46559(5) 0.06820(5) 0.0311(2) Uani 1 1 d . . . . .
O5B O -0.02925(9) 0.09915(5) 0.10513(6) 0.0314(2) Uani 1 1 d . . . . .
O4A O 0.92478(9) 0.24616(6) 0.29417(5) 0.0325(2) Uani 1 1 d . . . . .
O5A O 1.04533(9) 0.50193(6) 0.42278(6) 0.0350(2) Uani 1 1 d . . . . .
O3A O 0.88076(9) 0.25784(6) 0.39922(5) 0.0333(2) Uani 1 1 d . . . . .
O7B1 O 0.50210(10) 0.25439(7) 0.28533(6) 0.0420(3) Uani 1 1 d . . . . .
O1B O -0.26899(10) 0.45884(6) 0.07892(8) 0.0456(3) Uani 1 1 d . . . . .
O1A O 1.28055(10) 0.14719(6) 0.40075(8) 0.0473(3) Uani 1 1 d . . . . .
N1A N 1.20750(9) 0.38288(6) 0.41421(6) 0.0245(2) Uani 1 1 d . . . . .
N1B N -0.19418(9) 0.22142(6) 0.08972(6) 0.0233(2) Uani 1 1 d . . . . .
O7A1 O 0.52349(11) 0.39528(8) 0.19737(6) 0.0467(3) Uani 1 1 d . . . . .
O2A O 1.08839(10) 0.13887(6) 0.37751(9) 0.0549(4) Uani 1 1 d . . . . .
O7B2 O 0.54701(10) 0.17016(9) 0.21564(7) 0.0515(3) Uani 1 1 d . . . . .
O7A2 O 0.46983(10) 0.43577(9) 0.28886(7) 0.0533(3) Uani 1 1 d . . . . .
N2B N 0.47663(11) 0.20792(8) 0.23903(6) 0.0338(3) Uani 1 1 d . . . . .
N2A N 0.54428(11) 0.41885(8) 0.25636(7) 0.0362(3) Uani 1 1 d . . . . .
C5B C -0.24556(11) 0.29241(7) 0.08130(6) 0.0240(2) Uani 1 1 d . . . . .
C11B C 0.06271(11) 0.34595(7) 0.11538(7) 0.0247(2) Uani 1 1 d . . . . .
C4B C -0.36618(11) 0.29891(8) 0.06783(7) 0.0263(2) Uani 1 1 d . . . . .
C1OB C -0.05182(11) 0.30768(7) 0.10601(6) 0.0236(2) Uani 1 1 d . . . . .
C5A C 1.25768(11) 0.31188(7) 0.41406(6) 0.0249(2) Uani 1 1 d . . . . .
C14B C -0.07383(11) 0.22954(7) 0.10662(6) 0.0235(2) Uani 1 1 d . . . . .
C21B C 0.20996(11) 0.14210(7) 0.12359(7) 0.0260(2) Uani 1 1 d . . . . .
C6B C -0.15647(11) 0.34683(7) 0.09012(7) 0.0252(2) Uani 1 1 d . . . . .
C16B C 0.12578(11) 0.17860(7) 0.15237(7) 0.0251(2) Uani 1 1 d . . . . .
C14A C 1.08741(11) 0.37696(7) 0.39317(7) 0.0251(2) Uani 1 1 d . . . . .
C11A C 0.94619(11) 0.26554(7) 0.36051(7) 0.0267(2) Uani 1 1 d . . . . .
C10A C 1.06380(11) 0.29972(7) 0.38060(7) 0.0254(2) Uani 1 1 d . . . . .
C1B C -0.25989(11) 0.15609(7) 0.08331(7) 0.0259(2) Uani 1 1 d . . . . .
C3B C -0.43070(11) 0.23337(8) 0.06339(7) 0.0260(2) Uani 1 1 d . . . . .
C15B C 0.00258(11) 0.16513(7) 0.11983(7) 0.0250(2) Uani 1 1 d . . . . .
C3A C 1.44350(11) 0.36890(8) 0.44442(7) 0.0266(2) Uani 1 1 d . . . . .
C20B C 0.32545(12) 0.15068(8) 0.15197(7) 0.0277(3) Uani 1 1 d . . . . .
C4A C 1.37805(11) 0.30413(8) 0.43021(7) 0.0263(2) Uani 1 1 d . . . . .
C16A C 0.89070(11) 0.43563(7) 0.35570(7) 0.0265(2) Uani 1 1 d . . . . .
C17A C 0.80302(12) 0.45611(8) 0.39039(7) 0.0277(3) Uani 1 1 d . . . . .
C15A C 1.01265(12) 0.44188(7) 0.39302(7) 0.0269(2) Uani 1 1 d . . . . .
C2B C -0.37615(11) 0.16120(8) 0.07022(7) 0.0268(2) Uani 1 1 d . . . . .
C19B C 0.35398(11) 0.19654(8) 0.20943(7) 0.0279(3) Uani 1 1 d . . . . .
C19A C 0.66550(12) 0.42685(8) 0.29035(7) 0.0290(3) Uani 1 1 d . . . . .
C6A C 1.16759(11) 0.25896(7) 0.39390(7) 0.0258(2) Uani 1 1 d . . . . .
C1A C 1.27404(12) 0.44719(8) 0.42840(7) 0.0277(3) Uani 1 1 d . . . . .
C18A C 0.68886(12) 0.45168(8) 0.35775(7) 0.0290(3) Uani 1 1 d . . . . .
C17B C 0.15700(12) 0.22238(8) 0.21138(7) 0.0289(3) Uani 1 1 d . . . . .
C2A C 1.39002(12) 0.44113(8) 0.44289(7) 0.0289(3) Uani 1 1 d . . . . .
C7B C -0.17726(12) 0.42859(8) 0.07898(7) 0.0290(3) Uani 1 1 d . . . . .
C18B C 0.27266(12) 0.23231(8) 0.24023(7) 0.0300(3) Uani 1 1 d . . . . .
C7A C 1.18711(12) 0.17689(8) 0.39129(8) 0.0303(3) Uani 1 1 d . . . . .
C20A C 0.75006(13) 0.40920(8) 0.25365(7) 0.0311(3) Uani 1 1 d . . . . .
C21A C 0.86415(12) 0.41351(8) 0.28701(7) 0.0301(3) Uani 1 1 d . . . . .
C12B C 0.18262(13) 0.43715(9) 0.18072(8) 0.0332(3) Uani 1 1 d . . . . .
C22A C 1.62007(13) 0.30099(8) 0.45268(8) 0.0318(3) Uani 1 1 d . . . . .
C22B C -0.60644(13) 0.30232(9) 0.04764(9) 0.0332(3) Uani 1 1 d . . . . .
C12A C 0.81263(13) 0.21164(9) 0.26782(8) 0.0342(3) Uani 1 1 d . . . . .
C13A C 0.82466(15) 0.12670(10) 0.26396(9) 0.0393(3) Uani 1 1 d . . . . .
C8B C -0.09459(16) 0.54758(8) 0.05791(9) 0.0386(3) Uani 1 1 d . . . . .
C13B C 0.18918(16) 0.47833(11) 0.24739(9) 0.0416(4) Uani 1 1 d . . . . .
C9B C -0.0767(2) 0.58840(10) 0.12472(12) 0.0541(5) Uani 1 1 d . . . . .
C8A C 1.09513(18) 0.05645(10) 0.37336(17) 0.0730(8) Uani 1 1 d . . . . .
H8A1 H 1.176514 0.039775 0.382672 0.088 Uiso 1 1 calc R U . . .
H8A2 H 1.058722 0.038790 0.327004 0.088 Uiso 1 1 calc R U . . .
C9A C 1.0334(3) 0.02445(13) 0.42561(14) 0.0816(9) Uani 1 1 d . . . . .
H9A3 H 1.070883 0.041755 0.471290 0.122 Uiso 1 1 calc R U . . .
H9A1 H 1.035508 -0.031242 0.423832 0.122 Uiso 1 1 calc R U . . .
H9A2 H 0.953261 0.041773 0.416125 0.122 Uiso 1 1 calc R U . . .
H4B H -0.4000(16) 0.3498(11) 0.0632(9) 0.035(5) Uiso 1 1 d . . . . .
H21B H 0.1884(15) 0.1118(10) 0.0833(9) 0.029(4) Uiso 1 1 d . . . . .
H1B H -0.2189(15) 0.1073(10) 0.0883(9) 0.031(4) Uiso 1 1 d . . . . .
H20B H 0.3879(16) 0.1267(10) 0.1321(9) 0.033(4) Uiso 1 1 d . . . . .
H4A H 1.4131(16) 0.2540(11) 0.4312(9) 0.035(5) Uiso 1 1 d . . . . .
H17A H 0.8225(16) 0.4720(11) 0.4382(10) 0.038(5) Uiso 1 1 d . . . . .
H2B H -0.4251(17) 0.1161(11) 0.0653(10) 0.037(5) Uiso 1 1 d . . . . .
H1A H 1.2321(16) 0.4934(11) 0.4261(10) 0.039(5) Uiso 1 1 d . . . . .
H18A H 0.6245(16) 0.4666(11) 0.3816(10) 0.037(5) Uiso 1 1 d . . . . .
H17B H 0.0988(16) 0.2432(11) 0.2334(10) 0.036(5) Uiso 1 1 d . . . . .
H2A H 1.4355(16) 0.4870(11) 0.4518(9) 0.036(5) Uiso 1 1 d . . . . .
H18B H 0.2952(16) 0.2635(11) 0.2815(10) 0.035(5) Uiso 1 1 d . . . . .
H20A H 0.7311(18) 0.3938(12) 0.2068(11) 0.045(5) Uiso 1 1 d . . . . .
H21A H 0.9246(18) 0.3999(11) 0.2612(10) 0.043(5) Uiso 1 1 d . . . . .
H12C H 0.1715(16) 0.4718(11) 0.1401(10) 0.038(5) Uiso 1 1 d . . . . .
H12D H 0.2490(18) 0.4037(12) 0.1818(10) 0.043(5) Uiso 1 1 d . . . . .
H22A H 1.5990(17) 0.2804(11) 0.4046(10) 0.041(5) Uiso 1 1 d . . . . .
H22B H 1.6000(17) 0.2623(11) 0.4848(10) 0.041(5) Uiso 1 1 d . . . . .
H22C H 1.7050(17) 0.3150(11) 0.4611(10) 0.040(5) Uiso 1 1 d . . . . .
H22D H -0.5918(17) 0.3272(11) 0.0073(11) 0.042(5) Uiso 1 1 d . . . . .
H22E H -0.5864(16) 0.3320(11) 0.0902(10) 0.035(5) Uiso 1 1 d . . . . .
H22F H -0.6908(18) 0.2887(12) 0.0438(10) 0.045(5) Uiso 1 1 d . . . . .
H12A H 0.7882(16) 0.2358(11) 0.2209(10) 0.038(5) Uiso 1 1 d . . . . .
H12B H 0.7602(16) 0.2256(10) 0.2987(9) 0.033(4) Uiso 1 1 d . . . . .
H13A H 0.7478(19) 0.1055(12) 0.2402(11) 0.051(6) Uiso 1 1 d . . . . .
H13B H 0.8427(19) 0.1072(13) 0.3083(12) 0.054(6) Uiso 1 1 d . . . . .
H13C H 0.8852(18) 0.1119(12) 0.2350(11) 0.046(5) Uiso 1 1 d . . . . .
H8B1 H -0.172(2) 0.5573(12) 0.0285(11) 0.050(6) Uiso 1 1 d . . . . .
H8B2 H -0.032(2) 0.5627(14) 0.0335(13) 0.065(7) Uiso 1 1 d . . . . .
H13E H 0.251(2) 0.5148(15) 0.2537(13) 0.071(7) Uiso 1 1 d . . . . .
H13F H 0.202(2) 0.4414(15) 0.2857(14) 0.069(7) Uiso 1 1 d . . . . .
H13D H 0.117(2) 0.5084(13) 0.2507(12) 0.059(6) Uiso 1 1 d . . . . .
H9B1 H -0.087(2) 0.6475(16) 0.1141(14) 0.074(8) Uiso 1 1 d . . . . .
H9B2 H 0.016(3) 0.5800(17) 0.1495(16) 0.098(10) Uiso 1 1 d . . . . .
H9B3 H -0.144(3) 0.5701(19) 0.1493(17) 0.102(10) Uiso 1 1 d . . . . .
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 0.0064 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C3B O6B C22B 117.28(11) . . ?
C11B O4B C12B 115.16(11) . . ?
C3A O6A C22A 117.40(11) . . ?
C7B O2B C8B 116.26(12) . . ?
C11A O4A C12A 116.60(11) . . ?
C1A N1A C5A 120.85(11) . . ?
C1A N1A C14A 128.91(11) . . ?
C5A N1A C14A 110.04(10) . . ?
C1B N1B C5B 120.82(11) . . ?
C1B N1B C14B 129.34(11) . . ?
C5B N1B C14B 109.81(10) . . ?
C7A O2A C8A 117.21(13) . . ?
O7B2 N2B O7B1 123.98(13) . . ?
O7B2 N2B C19B 117.70(13) . . ?
O7B1 N2B C19B 118.32(13) . . ?
O7A1 N2A O7A2 123.63(14) . . ?
O7A1 N2A C19A 118.28(13) . . ?
O7A2 N2A C19A 118.10(13) . . ?
N1B C5B C4B 120.20(11) . . ?
N1B C5B C6B 107.19(11) . . ?
C4B C5B C6B 132.60(12) . . ?
O3B C11B O4B 125.01(12) . . ?
O3B C11B C1OB 124.15(12) . . ?
O4B C11B C1OB 110.81(11) . . ?
C3B C4B C5B 118.38(12) . . ?
C3B C4B H4B 123.2(11) . . ?
C5B C4B H4B 118.4(11) . . ?
C14B C1OB C6B 109.07(11) . . ?
C14B C1OB C11B 127.42(11) . . ?
C6B C1OB C11B 123.38(11) . . ?
N1A C5A C4A 120.27(11) . . ?
N1A C5A C6A 107.06(11) . . ?
C4A C5A C6A 132.65(12) . . ?
C1OB C14B N1B 106.22(11) . . ?
C1OB C14B C15B 131.42(12) . . ?
N1B C14B C15B 122.36(11) . . ?
C20B C21B C16B 120.62(12) . . ?
C20B C21B H21B 119.3(10) . . ?
C16B C21B H21B 120.1(10) . . ?
C1OB C6B C5B 107.66(11) . . ?
C1OB C6B C7B 129.16(12) . . ?
C5B C6B C7B 123.06(12) . . ?
C17B C16B C21B 120.20(12) . . ?
C17B C16B C15B 122.17(12) . . ?
C21B C16B C15B 117.55(12) . . ?
C10A C14A N1A 106.33(11) . . ?
C10A C14A C15A 131.69(12) . . ?
N1A C14A C15A 121.76(11) . . ?
O3A C11A O4A 125.37(13) . . ?
O3A C11A C10A 123.69(12) . . ?
O4A C11A C10A 110.94(11) . . ?
C14A C10A C6A 108.89(11) . . ?
C14A C10A C11A 125.48(12) . . ?
C6A C10A C11A 125.53(12) . . ?
C2B C1B N1B 119.81(12) . . ?
C2B C1B H1B 122.8(10) . . ?
N1B C1B H1B 117.3(10) . . ?
O6B C3B C4B 124.95(12) . . ?
O6B C3B C2B 114.65(11) . . ?
C4B C3B C2B 120.39(12) . . ?
O5B C15B C14B 122.74(12) . . ?
O5B C15B C16B 118.56(11) . . ?
C14B C15B C16B 118.70(11) . . ?
O6A C3A C4A 125.06(12) . . ?
O6A C3A C2A 114.59(12) . . ?
C4A C3A C2A 120.36(12) . . ?
C21B C20B C19B 117.80(12) . . ?
C21B C20B H20B 122.8(11) . . ?
C19B C20B H20B 119.4(11) . . ?
C3A C4A C5A 118.25(12) . . ?
C3A C4A H4A 121.6(11) . . ?
C5A C4A H4A 120.1(11) . . ?
C21A C16A C17A 120.21(13) . . ?
C21A C16A C15A 121.47(12) . . ?
C17A C16A C15A 118.25(12) . . ?
C18A C17A C16A 120.26(13) . . ?
C18A C17A H17A 120.2(11) . . ?
C16A C17A H17A 119.6(11) . . ?
O5A C15A C14A 122.55(13) . . ?
O5A C15A C16A 119.01(12) . . ?
C14A C15A C16A 118.44(11) . . ?
C1B C2B C3B 120.35(12) . . ?
C1B C2B H2B 121.8(11) . . ?
C3B C2B H2B 117.8(11) . . ?
C18B C19B C20B 123.14(13) . . ?
C18B C19B N2B 118.45(13) . . ?
C20B C19B N2B 118.41(12) . . ?
C20A C19A C18A 123.33(13) . . ?
C20A C19A N2A 118.49(13) . . ?
C18A C19A N2A 118.19(13) . . ?
C10A C6A C5A 107.67(11) . . ?
C10A C6A C7A 129.42(12) . . ?
C5A C6A C7A 122.88(12) . . ?
C2A C1A N1A 119.82(12) . . ?
C2A C1A H1A 125.3(12) . . ?
N1A C1A H1A 114.9(12) . . ?
C17A C18A C19A 117.93(13) . . ?
C17A C18A H18A 121.5(11) . . ?
C19A C18A H18A 120.5(11) . . ?
C18B C17B C16B 119.99(13) . . ?
C18B C17B H17B 120.1(11) . . ?
C16B C17B H17B 119.8(11) . . ?
C1A C2A C3A 120.44(12) . . ?
C1A C2A H2A 118.8(11) . . ?
C3A C2A H2A 120.8(11) . . ?
O1B C7B O2B 124.03(13) . . ?
O1B C7B C6B 123.77(13) . . ?
O2B C7B C6B 112.20(12) . . ?
C19B C18B C17B 118.19(13) . . ?
C19B C18B H18B 121.5(11) . . ?
C17B C18B H18B 120.3(11) . . ?
O1A C7A O2A 124.01(13) . . ?
O1A C7A C6A 124.60(13) . . ?
O2A C7A C6A 111.39(12) . . ?
C19A C20A C21A 118.16(13) . . ?
C19A C20A H20A 121.3(12) . . ?
C21A C20A H20A 120.6(12) . . ?
C20A C21A C16A 120.01(13) . . ?
C20A C21A H21A 118.3(12) . . ?
C16A C21A H21A 121.7(12) . . ?
O4B C12B C13B 106.88(12) . . ?
O4B C12B H12C 106.3(11) . . ?
C13B C12B H12C 113.4(11) . . ?
O4B C12B H12D 107.0(12) . . ?
C13B C12B H12D 111.3(12) . . ?
H12C C12B H12D 111.5(16) . . ?
O6A C22A H22A 111.5(11) . . ?
O6A C22A H22B 109.2(12) . . ?
H22A C22A H22B 108.6(16) . . ?
O6A C22A H22C 105.8(11) . . ?
H22A C22A H22C 107.6(16) . . ?
H22B C22A H22C 114.1(16) . . ?
O6B C22B H22D 107.6(12) . . ?
O6B C22B H22E 111.0(11) . . ?
H22D C22B H22E 115.2(16) . . ?
O6B C22B H22F 105.4(12) . . ?
H22D C22B H22F 112.0(17) . . ?
H22E C22B H22F 105.3(16) . . ?
O4A C12A C13A 109.99(13) . . ?
O4A C12A H12A 103.7(11) . . ?
C13A C12A H12A 112.5(11) . . ?
O4A C12A H12B 108.0(11) . . ?
C13A C12A H12B 111.0(11) . . ?
H12A C12A H12B 111.4(15) . . ?
C12A C13A H13A 107.7(13) . . ?
C12A C13A H13B 109.0(14) . . ?
H13A C13A H13B 109.2(18) . . ?
C12A C13A H13C 111.1(12) . . ?
H13A C13A H13C 107.7(17) . . ?
H13B C13A H13C 112.1(18) . . ?
O2B C8B C9B 110.95(14) . . ?
O2B C8B H8B1 107.5(12) . . ?
C9B C8B H8B1 113.4(12) . . ?
O2B C8B H8B2 105.8(14) . . ?
C9B C8B H8B2 108.1(14) . . ?
H8B1 C8B H8B2 110.8(19) . . ?
C12B C13B H13E 110.2(15) . . ?
C12B C13B H13F 109.7(15) . . ?
H13E C13B H13F 110(2) . . ?
C12B C13B H13D 113.8(13) . . ?
H13E C13B H13D 106(2) . . ?
H13F C13B H13D 107.1(19) . . ?
C8B C9B H9B1 107.6(15) . . ?
C8B C9B H9B2 107.0(16) . . ?
H9B1 C9B H9B2 107(2) . . ?
C8B C9B H9B3 105.8(18) . . ?
H9B1 C9B H9B3 108(2) . . ?
H9B2 C9B H9B3 121(2) . . ?
O2A C8A C9A 107.31(19) . . ?
O2A C8A H8A1 110.3 . . ?
C9A C8A H8A1 110.3 . . ?
O2A C8A H8A2 110.3 . . ?
C9A C8A H8A2 110.3 . . ?
H8A1 C8A H8A2 108.5 . . ?
C8A C9A H9A3 109.5 . . ?
C8A C9A H9A1 109.5 . . ?
H9A3 C9A H9A1 109.5 . . ?
C8A C9A H9A2 109.5 . . ?
H9A3 C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 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
O6B C3B 1.3451(16) . ?
O6B C22B 1.4365(17) . ?
O4B C11B 1.3359(16) . ?
O4B C12B 1.4590(17) . ?
O3B C11B 1.2031(16) . ?
O6A C3A 1.3512(16) . ?
O6A C22A 1.4394(17) . ?
O2B C7B 1.3424(17) . ?
O2B C8B 1.4584(17) . ?
O5B C15B 1.2371(16) . ?
O4A C11A 1.3383(17) . ?
O4A C12A 1.4630(17) . ?
O5A C15A 1.2357(17) . ?
O3A C11A 1.1979(17) . ?
O7B1 N2B 1.2244(17) . ?
O1B C7B 1.2084(18) . ?
O1A C7A 1.2049(18) . ?
N1A C1A 1.3758(16) . ?
N1A C5A 1.3821(16) . ?
N1A C14A 1.4071(17) . ?
N1B C1B 1.3791(16) . ?
N1B C5B 1.3841(16) . ?
N1B C14B 1.4073(16) . ?
O7A1 N2A 1.2234(18) . ?
O2A C7A 1.3285(18) . ?
O2A C8A 1.454(2) . ?
O7B2 N2B 1.2234(18) . ?
O7A2 N2A 1.2235(18) . ?
N2B C19B 1.4728(18) . ?
N2A C19A 1.4720(19) . ?
C5B C4B 1.4061(18) . ?
C5B C6B 1.4097(18) . ?
C11B C1OB 1.4928(18) . ?
C4B C3B 1.3754(18) . ?
C4B H4B 0.976(19) . ?
C1OB C14B 1.3982(17) . ?
C1OB C6B 1.3995(18) . ?
C5A C4A 1.4061(19) . ?
C5A C6A 1.4144(18) . ?
C14B C15B 1.4416(18) . ?
C21B C20B 1.3844(19) . ?
C21B C16B 1.3951(18) . ?
C21B H21B 0.954(18) . ?
C6B C7B 1.4675(18) . ?
C16B C17B 1.3925(19) . ?
C16B C15B 1.4976(18) . ?
C14A C10A 1.3991(18) . ?
C14A C15A 1.4434(18) . ?
C11A C10A 1.4988(18) . ?
C10A C6A 1.4031(19) . ?
C1B C2B 1.3539(19) . ?
C1B H1B 0.980(18) . ?
C3B C2B 1.4181(18) . ?
C3A C4A 1.3757(18) . ?
C3A C2A 1.4162(19) . ?
C20B C19B 1.386(2) . ?
C20B H20B 0.995(18) . ?
C4A H4A 0.972(19) . ?
C16A C21A 1.3966(19) . ?
C16A C17A 1.3971(19) . ?
C16A C15A 1.4963(19) . ?
C17A C18A 1.385(2) . ?
C17A H17A 0.974(19) . ?
C2B H2B 0.976(19) . ?
C19B C18B 1.385(2) . ?
C19A C20A 1.380(2) . ?
C19A C18A 1.386(2) . ?
C6A C7A 1.4632(19) . ?
C1A C2A 1.3521(19) . ?
C1A H1A 0.95(2) . ?
C18A H18A 1.006(19) . ?
C17B C18B 1.391(2) . ?
C17B H17B 0.956(19) . ?
C2A H2A 0.966(19) . ?
C18B H18B 0.981(19) . ?
C20A C21A 1.389(2) . ?
C20A H20A 0.95(2) . ?
C21A H21A 0.99(2) . ?
C12B C13B 1.499(2) . ?
C12B H12C 0.999(19) . ?
C12B H12D 0.98(2) . ?
C22A H22A 1.01(2) . ?
C22A H22B 0.99(2) . ?
C22A H22C 1.02(2) . ?
C22B H22D 0.96(2) . ?
C22B H22E 0.983(19) . ?
C22B H22F 1.02(2) . ?
C12A C13A 1.503(2) . ?
C12A H12A 1.02(2) . ?
C12A H12B 0.982(18) . ?
C13A H13A 1.01(2) . ?
C13A H13B 0.93(2) . ?
C13A H13C 1.03(2) . ?
C8B C9B 1.488(3) . ?
C8B H8B1 1.00(2) . ?
C8B H8B2 1.00(2) . ?
C13B H13E 0.97(3) . ?
C13B H13F 0.99(3) . ?
C13B H13D 1.02(2) . ?
C9B H9B1 1.06(3) . ?
C9B H9B2 1.12(3) . ?
C9B H9B3 1.06(3) . ?
C8A C9A 1.488(4) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
C9A H9A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 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
C1B N1B C5B C4B 1.72(18) . . . . ?
C14B N1B C5B C4B -176.53(11) . . . . ?
C1B N1B C5B C6B -179.31(11) . . . . ?
C14B N1B C5B C6B 2.44(14) . . . . ?
C12B O4B C11B O3B 6.86(19) . . . . ?
C12B O4B C11B C1OB -171.42(11) . . . . ?
N1B C5B C4B C3B 0.04(19) . . . . ?
C6B C5B C4B C3B -178.63(14) . . . . ?
O3B C11B C1OB C14B 65.44(19) . . . . ?
O4B C11B C1OB C14B -116.27(14) . . . . ?
O3B C11B C1OB C6B -109.88(16) . . . . ?
O4B C11B C1OB C6B 68.42(16) . . . . ?
C1A N1A C5A C4A 1.61(19) . . . . ?
C14A N1A C5A C4A 176.97(11) . . . . ?
C1A N1A C5A C6A -176.61(12) . . . . ?
C14A N1A C5A C6A -1.25(14) . . . . ?
C6B C1OB C14B N1B 0.88(14) . . . . ?
C11B C1OB C14B N1B -174.98(12) . . . . ?
C6B C1OB C14B C15B 179.97(13) . . . . ?
C11B C1OB C14B C15B 4.1(2) . . . . ?
C1B N1B C14B C1OB 179.87(12) . . . . ?
C5B N1B C14B C1OB -2.07(14) . . . . ?
C1B N1B C14B C15B 0.7(2) . . . . ?
C5B N1B C14B C15B 178.74(11) . . . . ?
C14B C1OB C6B C5B 0.59(15) . . . . ?
C11B C1OB C6B C5B 176.65(11) . . . . ?
C14B C1OB C6B C7B -175.40(13) . . . . ?
C11B C1OB C6B C7B 0.7(2) . . . . ?
N1B C5B C6B C1OB -1.85(14) . . . . ?
C4B C5B C6B C1OB 176.95(14) . . . . ?
N1B C5B C6B C7B 174.43(12) . . . . ?
C4B C5B C6B C7B -6.8(2) . . . . ?
C20B C21B C16B C17B -1.9(2) . . . . ?
C20B C21B C16B C15B -178.58(12) . . . . ?
C1A N1A C14A C10A 175.56(13) . . . . ?
C5A N1A C14A C10A 0.68(14) . . . . ?
C1A N1A C14A C15A -9.3(2) . . . . ?
C5A N1A C14A C15A 175.79(12) . . . . ?
C12A O4A C11A O3A -1.1(2) . . . . ?
C12A O4A C11A C10A 179.71(12) . . . . ?
N1A C14A C10A C6A 0.17(14) . . . . ?
C15A C14A C10A C6A -174.25(14) . . . . ?
N1A C14A C10A C11A 176.62(12) . . . . ?
C15A C14A C10A C11A 2.2(2) . . . . ?
O3A C11A C10A C14A -73.23(19) . . . . ?
O4A C11A C10A C14A 106.00(15) . . . . ?
O3A C11A C10A C6A 102.65(17) . . . . ?
O4A C11A C10A C6A -78.12(17) . . . . ?
C5B N1B C1B C2B -1.57(19) . . . . ?
C14B N1B C1B C2B 176.30(12) . . . . ?
C22B O6B C3B C4B -0.4(2) . . . . ?
C22B O6B C3B C2B 178.75(12) . . . . ?
C5B C4B C3B O6B 177.23(12) . . . . ?
C5B C4B C3B C2B -1.89(19) . . . . ?
C1OB C14B C15B O5B -165.18(13) . . . . ?
N1B C14B C15B O5B 13.8(2) . . . . ?
C1OB C14B C15B C16B 14.5(2) . . . . ?
N1B C14B C15B C16B -166.52(11) . . . . ?
C17B C16B C15B O5B -130.47(14) . . . . ?
C21B C16B C15B O5B 46.12(17) . . . . ?
C17B C16B C15B C14B 49.83(17) . . . . ?
C21B C16B C15B C14B -133.59(13) . . . . ?
C22A O6A C3A C4A 9.08(19) . . . . ?
C22A O6A C3A C2A -170.77(12) . . . . ?
C16B C21B C20B C19B -0.10(19) . . . . ?
O6A C3A C4A C5A -179.63(12) . . . . ?
C2A C3A C4A C5A 0.21(19) . . . . ?
N1A C5A C4A C3A -1.45(19) . . . . ?
C6A C5A C4A C3A 176.23(14) . . . . ?
C21A C16A C17A C18A 2.6(2) . . . . ?
C15A C16A C17A C18A 179.61(12) . . . . ?
C10A C14A C15A O5A 159.71(14) . . . . ?
N1A C14A C15A O5A -14.0(2) . . . . ?
C10A C14A C15A C16A -19.8(2) . . . . ?
N1A C14A C15A C16A 166.47(11) . . . . ?
C21A C16A C15A O5A 126.57(15) . . . . ?
C17A C16A C15A O5A -50.38(18) . . . . ?
C21A C16A C15A C14A -53.87(18) . . . . ?
C17A C16A C15A C14A 129.18(13) . . . . ?
N1B C1B C2B C3B -0.3(2) . . . . ?
O6B C3B C2B C1B -177.14(12) . . . . ?
C4B C3B C2B C1B 2.1(2) . . . . ?
C21B C20B C19B C18B 1.5(2) . . . . ?
C21B C20B C19B N2B -178.32(12) . . . . ?
O7B2 N2B C19B C18B 172.87(14) . . . . ?
O7B1 N2B C19B C18B -7.2(2) . . . . ?
O7B2 N2B C19B C20B -7.3(2) . . . . ?
O7B1 N2B C19B C20B 172.68(13) . . . . ?
O7A1 N2A C19A C20A 1.5(2) . . . . ?
O7A2 N2A C19A C20A -178.84(15) . . . . ?
O7A1 N2A C19A C18A -178.36(14) . . . . ?
O7A2 N2A C19A C18A 1.3(2) . . . . ?
C14A C10A C6A C5A -0.93(15) . . . . ?
C11A C10A C6A C5A -177.38(12) . . . . ?
C14A C10A C6A C7A 176.91(13) . . . . ?
C11A C10A C6A C7A 0.5(2) . . . . ?
N1A C5A C6A C10A 1.33(14) . . . . ?
C4A C5A C6A C10A -176.58(14) . . . . ?
N1A C5A C6A C7A -176.68(12) . . . . ?
C4A C5A C6A C7A 5.4(2) . . . . ?
C5A N1A C1A C2A -0.45(19) . . . . ?
C14A N1A C1A C2A -174.84(13) . . . . ?
C16A C17A C18A C19A -0.3(2) . . . . ?
C20A C19A C18A C17A -2.5(2) . . . . ?
N2A C19A C18A C17A 177.38(12) . . . . ?
C21B C16B C17B C18B 2.6(2) . . . . ?
C15B C16B C17B C18B 179.07(12) . . . . ?
N1A C1A C2A C3A -0.8(2) . . . . ?
O6A C3A C2A C1A -179.21(12) . . . . ?
C4A C3A C2A C1A 0.9(2) . . . . ?
C8B O2B C7B O1B 1.8(2) . . . . ?
C8B O2B C7B C6B -178.84(12) . . . . ?
C1OB C6B C7B O1B -164.72(15) . . . . ?
C5B C6B C7B O1B 19.9(2) . . . . ?
C1OB C6B C7B O2B 15.9(2) . . . . ?
C5B C6B C7B O2B -159.51(12) . . . . ?
C20B C19B C18B C17B -0.9(2) . . . . ?
N2B C19B C18B C17B 178.96(13) . . . . ?
C16B C17B C18B C19B -1.2(2) . . . . ?
C8A O2A C7A O1A -0.4(3) . . . . ?
C8A O2A C7A C6A 179.98(19) . . . . ?
C10A C6A C7A O1A 176.58(16) . . . . ?
C5A C6A C7A O1A -5.9(2) . . . . ?
C10A C6A C7A O2A -3.8(2) . . . . ?
C5A C6A C7A O2A 173.77(14) . . . . ?
C18A C19A C20A C21A 2.8(2) . . . . ?
N2A C19A C20A C21A -177.08(13) . . . . ?
C19A C20A C21A C16A -0.3(2) . . . . ?
C17A C16A C21A C20A -2.3(2) . . . . ?
C15A C16A C21A C20A -179.20(13) . . . . ?
C11B O4B C12B C13B -178.60(13) . . . . ?
C11A O4A C12A C13A -100.14(15) . . . . ?
C7B O2B C8B C9B 84.19(19) . . . . ?
C7A O2A C8A C9A 121.1(2) . . . . ?
