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#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/27/4032730.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_4032730
loop_
_publ_author_name
'Anguera, Gonzalo'
'Kauffmann, Brice'
'Borrell, José I'
'Borrós, Salvador'
'Sánchez-García, David'
_publ_section_title
;
 Stable 5,5'-Substituted 2,2'-Bipyrroles: Building Blocks for Macrocyclic
 and Materials Chemistry.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6904
_journal_page_last               6912
_journal_paper_doi               10.1021/acs.joc.7b00961
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C34 H28 N2 O4 S2'
_chemical_formula_weight         592.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                113.515(11)
_cell_angle_beta                 93.0640(10)
_cell_angle_gamma                114.23(3)
_cell_formula_units_Z            1
_cell_length_a                   8.282(6)
_cell_length_b                   9.706(9)
_cell_length_c                   10.928(7)
_cell_measurement_reflns_used    616
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4
_cell_measurement_theta_min      30.3
_cell_volume                     709.3(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b43 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b43 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b43 (Rigaku, 2015)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9217
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.738
_diffrn_reflns_theta_min         5.637
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    2.010
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       prism
_exptl_crystal_F_000             310
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0451
_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)+(0.0719P)²+0.2270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2282
_reflns_number_total             2539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00961_si_003.cif
_cod_data_source_block           pb2_a
_cod_original_cell_volume        709.4(9)
_cod_database_code               4032730
_shelx_shelxl_version_number     2014/7
_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   0.824
_shelx_estimated_absorpt_t_max   0.824
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
S001 S 0.93707(6) 0.66621(6) 0.49721(5) 0.0310(2) Uani 1 1 d . .
O002 O 0.22116(16) 0.50032(16) 0.20740(13) 0.0271(3) Uani 1 1 d . .
O003 O 0.17746(17) 0.72371(17) 0.23614(13) 0.0282(3) Uani 1 1 d . .
N004 N 0.68707(18) 0.96319(19) 0.55277(14) 0.0204(4) Uani 1 1 d . .
H004 H 0.7583 1.0564 0.6259 0.024 Uiso 1 1 calc R U
C005 C 1.0276(2) 0.9756(2) 0.67013(18) 0.0232(4) Uani 1 1 d . .
H005 H 1.0268 1.0789 0.7177 0.028 Uiso 1 1 calc R U
C006 C 0.4503(2) 0.7655(2) 0.37086(17) 0.0200(4) Uani 1 1 d . .
C007 C 0.7200(2) 0.8257(2) 0.49625(17) 0.0195(4) Uani 1 1 d . .
C008 C 0.2720(2) 0.6667(2) 0.26739(17) 0.0214(4) Uani 1 1 d . .
C009 C 0.5745(2) 0.6986(2) 0.38160(17) 0.0200(4) Uani 1 1 d . .
C00A C 0.5284(2) 0.9342(2) 0.47937(16) 0.0196(4) Uani 1 1 d . .
C00B C 0.8880(2) 0.8352(2) 0.55760(17) 0.0217(4) Uani 1 1 d . .
C00C C 0.5622(2) 0.5341(2) 0.28079(17) 0.0208(4) Uani 1 1 d . .
C00D C 0.6179(2) 0.5227(3) 0.16052(19) 0.0273(4) Uani 1 1 d . .
H00D H 0.6667 0.6186 0.1466 0.033 Uiso 1 1 calc R U
C00E C 0.4916(3) 0.3884(2) 0.29999(19) 0.0286(4) Uani 1 1 d . .
H00E H 0.4545 0.3936 0.3798 0.034 Uiso 1 1 calc R U
C00F C 1.1727(2) 0.9436(3) 0.70457(19) 0.0279(4) Uani 1 1 d . .
H00F H 1.2774 1.0244 0.7769 0.034 Uiso 1 1 calc R U
C00G C 0.6014(3) 0.3697(3) 0.0612(2) 0.0346(5) Uani 1 1 d . .
H00G H 0.6381 0.3639 -0.0189 0.042 Uiso 1 1 calc R U
C00H C 0.0272(3) 0.2097(3) 0.0479(2) 0.0326(5) Uani 1 1 d . .
H00A H -0.0875 0.1295 -0.0206 0.049 Uiso 1 1 calc R U
H00B H 0.0306 0.1814 0.1224 0.049 Uiso 1 1 calc R U
H00C H 0.1260 0.2056 0.0071 0.049 Uiso 1 1 calc R U
C00I C 0.0469(3) 0.3857(3) 0.1023(2) 0.0330(5) Uani 1 1 d . .
H00H H 0.0463 0.4170 0.0284 0.040 Uiso 1 1 calc R U
H00I H -0.0535 0.3912 0.1423 0.040 Uiso 1 1 calc R U
C00J C 0.5308(3) 0.2265(3) 0.0809(2) 0.0352(5) Uani 1 1 d . .
H00J H 0.5196 0.1243 0.0142 0.042 Uiso 1 1 calc R U
C00K C 1.1424(3) 0.7823(3) 0.6206(2) 0.0309(5) Uani 1 1 d . .
H00K H 1.2229 0.7405 0.6292 0.037 Uiso 1 1 calc R U
C00L C 0.4764(3) 0.2357(3) 0.2009(2) 0.0334(5) Uani 1 1 d . .
H00L H 0.4299 0.1398 0.2150 0.040 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0192 0.0096 '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 0.0330 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0517 0.0336 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3360 0.5650 '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_3
C00K S001 C00B 92.30(10) .
C008 O002 C00I 117.55(15) .
C00A N004 C007 112.04(14) .
C00A N004 H004 124.0 .
C007 N004 H004 124.0 .
C00B C005 C00F 112.27(18) .
C00B C005 H005 123.9 .
C00F C005 H005 123.9 .
C00A C006 C009 107.53(16) .
C00A C006 C008 128.28(16) .
C009 C006 C008 124.13(17) .
N004 C007 C009 107.57(16) .
N004 C007 C00B 120.09(15) .
C009 C007 C00B 132.32(18) .
O003 C008 O002 122.15(16) .
O003 C008 C006 126.72(17) .
O002 C008 C006 111.13(15) .
C007 C009 C006 106.67(17) .
C007 C009 C00C 125.88(16) .
C006 C009 C00C 127.07(15) .
N004 C00A C006 106.15(16) .
N004 C00A C00A 120.44(19) 2_676
C006 C00A C00A 133.4(2) 2_676
C005 C00B C007 126.07(18) .
C005 C00B S001 110.65(15) .
C007 C00B S001 123.28(14) .
C00D C00C C00E 118.33(17) .
C00D C00C C009 119.08(16) .
C00E C00C C009 122.56(17) .
C00G C00D C00C 120.87(18) .
C00G C00D H00D 119.6 .
C00C C00D H00D 119.6 .
C00L C00E C00C 120.74(18) .
C00L C00E H00E 119.6 .
C00C C00E H00E 119.6 .
C00K C00F C005 113.14(17) .
C00K C00F H00F 123.4 .
C005 C00F H00F 123.4 .
C00J C00G C00D 120.30(19) .
C00J C00G H00G 119.9 .
C00D C00G H00G 119.9 .
C00I C00H H00A 109.5 .
C00I C00H H00B 109.5 .
H00A C00H H00B 109.5 .
C00I C00H H00C 109.5 .
H00A C00H H00C 109.5 .
H00B C00H H00C 109.5 .
O002 C00I C00H 106.73(16) .
O002 C00I H00H 110.4 .
C00H C00I H00H 110.4 .
O002 C00I H00I 110.4 .
C00H C00I H00I 110.4 .
H00H C00I H00I 108.6 .
C00G C00J C00L 119.76(19) .
C00G C00J H00J 120.1 .
C00L C00J H00J 120.1 .
C00F C00K S001 111.64(15) .
C00F C00K H00K 124.2 .
S001 C00K H00K 124.2 .
C00J C00L C00E 119.99(19) .
C00J C00L H00L 120.0 .
C00E C00L H00L 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S001 C00K 1.718(2) .
S001 C00B 1.733(2) .
O002 C008 1.335(3) .
O002 C00I 1.458(2) .
O003 C008 1.230(2) .
N004 C00A 1.361(2) .
N004 C007 1.377(3) .
N004 H004 0.8600 .
C005 C00B 1.387(3) .
C005 C00F 1.427(3) .
C005 H005 0.9300 .
C006 C00A 1.416(3) .
C006 C009 1.445(3) .
C006 C008 1.475(2) .
C007 C009 1.389(2) .
C007 C00B 1.463(3) .
C009 C00C 1.491(3) .
C00A C00A 1.454(4) 2_676
C00C C00D 1.394(3) .
C00C C00E 1.399(3) .
C00D C00G 1.390(3) .
C00D H00D 0.9300 .
C00E C00L 1.391(3) .
C00E H00E 0.9300 .
C00F C00K 1.364(3) .
C00F H00F 0.9300 .
C00G C00J 1.380(3) .
C00G H00G 0.9300 .
C00H C00I 1.500(3) .
C00H H00A 0.9600 .
C00H H00B 0.9600 .
C00H H00C 0.9600 .
C00I H00H 0.9700 .
C00I H00I 0.9700 .
C00J C00L 1.391(3) .
C00J H00J 0.9300 .
C00K H00K 0.9300 .
C00L H00L 0.9300 .
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_4
C00A N004 C007 C009 -1.18(18) .
C00A N004 C007 C00B 177.58(15) .
C00I O002 C008 O003 -0.3(2) .
C00I O002 C008 C006 180.00(15) .
C00A C006 C008 O003 18.0(3) .
C009 C006 C008 O003 -165.23(17) .
C00A C006 C008 O002 -162.28(16) .
C009 C006 C008 O002 14.4(2) .
N004 C007 C009 C006 -0.03(18) .
C00B C007 C009 C006 -178.59(17) .
N004 C007 C009 C00C 173.34(15) .
C00B C007 C009 C00C -5.2(3) .
C00A C006 C009 C007 1.16(18) .
C008 C006 C009 C007 -176.14(15) .
C00A C006 C009 C00C -172.11(15) .
C008 C006 C009 C00C 10.6(3) .
C007 N004 C00A C006 1.89(18) .
C007 N004 C00A C00A -178.52(18) 2_676
C009 C006 C00A N004 -1.83(18) .
C008 C006 C00A N004 175.32(16) .
C009 C006 C00A C00A 178.7(2) 2_676
C008 C006 C00A C00A -4.2(4) 2_676
C00F C005 C00B C007 179.95(16) .
C00F C005 C00B S001 0.42(19) .
N004 C007 C00B C005 -1.8(3) .
C009 C007 C00B C005 176.61(17) .
N004 C007 C00B S001 177.67(12) .
C009 C007 C00B S001 -3.9(3) .
C00K S001 C00B C005 -0.21(14) .
C00K S001 C00B C007 -179.75(15) .
C007 C009 C00C C00D -94.1(2) .
C006 C009 C00C C00D 77.9(2) .
C007 C009 C00C C00E 87.8(2) .
C006 C009 C00C C00E -100.2(2) .
C00E C00C C00D C00G 0.9(3) .
C009 C00C C00D C00G -177.26(16) .
C00D C00C C00E C00L -0.4(3) .
C009 C00C C00E C00L 177.67(16) .
C00B C005 C00F C00K -0.5(2) .
C00C C00D C00G C00J -0.6(3) .
C008 O002 C00I C00H 177.51(15) .
C00D C00G C00J C00L -0.2(3) .
C005 C00F C00K S001 0.3(2) .
C00B S001 C00K C00F -0.06(15) .
C00G C00J C00L C00E 0.6(3) .
C00C C00E C00L C00J -0.3(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095312
