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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/72/7117234.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_7117234
loop_
_publ_author_name
'Tianyou Qin'
'Lu Cheng'
'Sean Xiao-An Zhang'
'Weiwei Liao'
_publ_section_title
;
 Stereoselective synthesis of organosulfur compounds incorporating
 N-aromatic heterocyclic motifs and quaternary carbon centers via a
 sulfa-Michael triggered tandem reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              9714
_journal_paper_doi               10.1039/C5cc01875G
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H18 Br N3 O'
_chemical_formula_sum            'C27 H18 Br N3 O'
_chemical_formula_weight         480.35
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-12 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1413(16)
_cell_length_b                   13.747(3)
_cell_length_c                   10.606(2)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      3.02
_cell_volume                     1128.6(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_sigmaI/netI    0.1627
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10791
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_T_max  0.7783
_exptl_absorpt_correction_T_min  0.7420
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.046(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                2111
_reflns_number_total             4949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01875g3.cif
_cod_data_source_block           7q76
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7117234
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.11230(14) -0.32153(8) 0.86289(10) 0.1044(4) Uani 1 1 d . . .
C1 C 0.1280(10) -0.0583(5) 0.8997(6) 0.0569(19) Uani 1 1 d . . .
H1 H 0.1497 -0.0067 0.9594 0.068 Uiso 1 1 calc R . .
C2 C 0.0429(11) -0.1366(5) 0.9241(7) 0.063(2) Uani 1 1 d . . .
H2 H 0.0080 -0.1393 0.9997 0.075 Uiso 1 1 calc R . .
C3 C 0.0083(10) -0.2127(4) 0.8347(7) 0.0547(18) Uani 1 1 d . . .
C4 C 0.0599(10) -0.2079(5) 0.7232(6) 0.0588(19) Uani 1 1 d . . .
H4 H 0.0353 -0.2591 0.6628 0.071 Uiso 1 1 calc R . .
C5 C 0.1480(9) -0.1273(5) 0.7003(6) 0.0529(18) Uani 1 1 d . . .
H5 H 0.1827 -0.1246 0.6247 0.063 Uiso 1 1 calc R . .
C6 C 0.1848(9) -0.0513(4) 0.7887(5) 0.0463(16) Uani 1 1 d . . .
C7 C 0.2661(9) 0.0420(4) 0.7650(5) 0.0468(17) Uani 1 1 d . . .
C8 C 0.5104(10) -0.0476(4) 0.7314(6) 0.0518(18) Uani 1 1 d . . .
H8 H 0.4978 -0.0978 0.7865 0.062 Uiso 1 1 calc R . .
C9 C 0.6268(10) -0.0547(4) 0.6684(6) 0.0507(19) Uani 1 1 d . . .
H9 H 0.7020 -0.1075 0.6860 0.061 Uiso 1 1 calc R . .
C10 C 0.6402(9) 0.0172(4) 0.5733(5) 0.0437(16) Uani 1 1 d . . .
C11 C 0.7338(10) 0.0013(5) 0.4832(7) 0.0569(18) Uani 1 1 d . . .
H11 H 0.7969 -0.0558 0.4885 0.068 Uiso 1 1 calc R . .
C12 C 0.7330(10) 0.0687(5) 0.3885(6) 0.061(2) Uani 1 1 d . . .
H12 H 0.7962 0.0576 0.3303 0.073 Uiso 1 1 calc R . .
C13 C 0.6399(10) 0.1519(5) 0.3792(6) 0.066(2) Uani 1 1 d . . .
H13 H 0.6373 0.1961 0.3123 0.079 Uiso 1 1 calc R . .
C14 C 0.5485(8) 0.1726(6) 0.4666(5) 0.0527(16) Uani 1 1 d . . .
H14 H 0.4867 0.2303 0.4604 0.063 Uiso 1 1 calc R . .
C15 C 0.5524(8) 0.1035(4) 0.5649(5) 0.0393(15) Uani 1 1 d . . .
C16 C 0.4708(8) 0.1266(4) 0.6749(5) 0.0399(15) Uani 1 1 d . . .
C17 C 0.3287(10) 0.1969(4) 0.6199(5) 0.0446(16) Uani 1 1 d . . .
C18 C 0.6191(8) 0.1722(6) 0.7964(5) 0.0467(15) Uani 1 1 d . . .
H18 H 0.7115 0.1235 0.8161 0.056 Uiso 1 1 calc R . .
C19 C 0.7001(10) 0.2610(4) 0.7623(6) 0.0452(16) Uani 1 1 d . . .
C20 C 0.8612(11) 0.2535(5) 0.7476(6) 0.061(2) Uani 1 1 d . . .
H20 H 0.9180 0.1939 0.7608 0.073 Uiso 1 1 calc R . .
C21 C 0.9396(12) 0.3340(8) 0.7134(8) 0.088(3) Uani 1 1 d . . .
H21 H 1.0494 0.3288 0.7046 0.105 Uiso 1 1 calc R . .
C22 C 0.8561(13) 0.4206(7) 0.6926(7) 0.079(2) Uani 1 1 d . . .
H22 H 0.9091 0.4742 0.6682 0.094 Uiso 1 1 calc R . .
C23 C 0.6986(13) 0.4307(6) 0.7064(7) 0.070(2) Uani 1 1 d . . .
H23 H 0.6441 0.4910 0.6923 0.084 Uiso 1 1 calc R . .
C24 C 0.6179(10) 0.3522(4) 0.7413(6) 0.0521(18) Uani 1 1 d . . .
H24 H 0.5089 0.3593 0.7510 0.063 Uiso 1 1 calc R . .
C25 C 0.5698(10) 0.1781(7) 0.9234(6) 0.0653(19) Uani 1 1 d . . .
C26 C 0.6129(14) 0.1042(7) 1.0126(7) 0.104(4) Uani 1 1 d . . .
H26A H 0.5826 0.1073 1.0902 0.125 Uiso 1 1 calc R . .
H26B H 0.6728 0.0505 0.9962 0.125 Uiso 1 1 calc R . .
C27 C 0.4802(14) 0.2579(7) 0.9495(7) 0.080(3) Uani 1 1 d . . .
N1 N 0.4038(7) 0.0369(3) 0.7151(4) 0.0426(13) Uani 1 1 d . . .
N2 N 0.2313(9) 0.2539(4) 0.5651(5) 0.0599(17) Uani 1 1 d . . .
N3 N 0.4089(13) 0.3258(6) 0.9735(8) 0.130(4) Uani 1 1 d . . .
O1 O 0.2113(7) 0.1180(3) 0.7894(4) 0.0627(13) Uani 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 0.0061 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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 122.8(6) . .
C2 C1 H1 118.6 . .
C6 C1 H1 118.6 . .
C1 C2 C3 118.8(6) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.6 . .
C4 C3 C2 120.2(6) . .
C4 C3 Br1 119.6(5) . .
C2 C3 Br1 120.2(5) . .
C3 C4 C5 120.2(6) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.4(6) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C5 C6 C1 117.7(6) . .
C5 C6 C7 123.4(5) . .
C1 C6 C7 118.6(5) . .
O1 C7 N1 122.0(6) . .
O1 C7 C6 119.8(6) . .
N1 C7 C6 118.2(5) . .
C9 C8 N1 120.2(6) . .
C9 C8 H8 119.9 . .
N1 C8 H8 119.9 . .
C8 C9 C10 121.7(6) . .
C8 C9 H9 119.2 . .
C10 C9 H9 119.2 . .
C15 C10 C11 117.9(5) . .
C15 C10 C9 119.2(6) . .
C11 C10 C9 122.8(6) . .
C12 C11 C10 120.9(6) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C13 C12 C11 120.0(6) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C14 121.8(6) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C13 C14 C15 117.7(7) . .
C13 C14 H14 121.2 . .
C15 C14 H14 121.2 . .
C10 C15 C14 121.7(5) . .
C10 C15 C16 117.7(5) . .
C14 C15 C16 120.4(5) . .
N1 C16 C17 110.4(5) . .
N1 C16 C15 109.5(4) . .
C17 C16 C15 107.6(4) . .
N1 C16 C18 110.6(5) . .
C17 C16 C18 111.4(5) . .
C15 C16 C18 107.2(5) . .
N2 C17 C16 170.4(6) . .
C19 C18 C25 115.5(6) . .
C19 C18 C16 114.1(5) . .
C25 C18 C16 113.3(5) . .
C19 C18 H18 104.1 . .
C25 C18 H18 104.1 . .
C16 C18 H18 104.1 . .
C20 C19 C24 118.3(6) . .
C20 C19 C18 118.6(6) . .
C24 C19 C18 123.1(6) . .
C19 C20 C21 120.4(7) . .
C19 C20 H20 119.8 . .
C21 C20 H20 119.8 . .
C22 C21 C20 119.8(8) . .
C22 C21 H21 120.1 . .
C20 C21 H21 120.1 . .
C23 C22 C21 121.5(8) . .
C23 C22 H22 119.3 . .
C21 C22 H22 119.3 . .
C22 C23 C24 120.0(8) . .
C22 C23 H23 120.0 . .
C24 C23 H23 120.0 . .
C23 C24 C19 120.0(7) . .
C23 C24 H24 120.0 . .
C19 C24 H24 120.0 . .
C26 C25 C27 119.3(6) . .
C26 C25 C18 119.6(8) . .
C27 C25 C18 121.1(7) . .
C25 C26 H26A 120.0 . .
C25 C26 H26B 120.0 . .
H26A C26 H26B 120.0 . .
N3 C27 C25 178.3(11) . .
C7 N1 C8 122.0(5) . .
C7 N1 C16 119.2(5) . .
C8 N1 C16 116.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.863(7) .
C1 C2 1.348(9) .
C1 C6 1.395(8) .
C1 H1 0.9300 .
C2 C3 1.381(9) .
C2 H2 0.9300 .
C3 C4 1.374(8) .
C4 C5 1.382(9) .
C4 H4 0.9300 .
C5 C6 1.374(8) .
C5 H5 0.9300 .
C6 C7 1.500(8) .
C7 O1 1.195(6) .
C7 N1 1.382(8) .
C8 C9 1.321(9) .
C8 N1 1.428(8) .
C8 H8 0.9300 .
C9 C10 1.440(8) .
C9 H9 0.9300 .
C10 C15 1.374(8) .
C10 C11 1.412(8) .
C11 C12 1.365(9) .
C11 H11 0.9300 .
C12 C13 1.359(9) .
C12 H12 0.9300 .
C13 C14 1.386(8) .
C13 H13 0.9300 .
C14 C15 1.403(8) .
C14 H14 0.9300 .
C15 C16 1.543(8) .
C16 N1 1.464(7) .
C16 C17 1.482(9) .
C16 C18 1.596(8) .
C17 N2 1.138(8) .
C18 C19 1.485(9) .
C18 C25 1.522(8) .
C18 H18 0.9800 .
C19 C20 1.371(10) .
C19 C24 1.407(9) .
C20 C21 1.382(11) .
C20 H20 0.9300 .
C21 C22 1.354(11) .
C21 H21 0.9300 .
C22 C23 1.342(11) .
C22 H22 0.9300 .
C23 C24 1.372(9) .
C23 H23 0.9300 .
C24 H24 0.9300 .
C25 C26 1.358(11) .
C25 C27 1.392(13) .
C26 H26A 0.9300 .
C26 H26B 0.9300 .
C27 N3 1.169(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
C6 C1 C2 C3 -0.8(11) . . . .
C1 C2 C3 C4 -0.2(11) . . . .
C1 C2 C3 Br1 -178.9(6) . . . .
C2 C3 C4 C5 0.6(10) . . . .
Br1 C3 C4 C5 179.4(5) . . . .
C3 C4 C5 C6 -0.1(10) . . . .
C4 C5 C6 C1 -0.9(9) . . . .
C4 C5 C6 C7 -174.5(6) . . . .
C2 C1 C6 C5 1.4(10) . . . .
C2 C1 C6 C7 175.3(7) . . . .
C5 C6 C7 O1 136.1(7) . . . .
C1 C6 C7 O1 -37.5(9) . . . .
C5 C6 C7 N1 -43.9(9) . . . .
C1 C6 C7 N1 142.5(6) . . . .
N1 C8 C9 C10 -5.6(10) . . . .
C8 C9 C10 C15 11.9(10) . . . .
C8 C9 C10 C11 -165.1(6) . . . .
C15 C10 C11 C12 -1.8(9) . . . .
C9 C10 C11 C12 175.3(7) . . . .
C10 C11 C12 C13 -0.6(11) . . . .
C11 C12 C13 C14 2.1(12) . . . .
C12 C13 C14 C15 -1.1(11) . . . .
C11 C10 C15 C14 2.8(9) . . . .
C9 C10 C15 C14 -174.4(6) . . . .
C11 C10 C15 C16 -172.0(5) . . . .
C9 C10 C15 C16 10.9(9) . . . .
C13 C14 C15 C10 -1.4(10) . . . .
C13 C14 C15 C16 173.2(6) . . . .
C10 C15 C16 N1 -36.8(8) . . . .
C14 C15 C16 N1 148.4(6) . . . .
C10 C15 C16 C17 -156.8(6) . . . .
C14 C15 C16 C17 28.4(8) . . . .
C10 C15 C16 C18 83.3(6) . . . .
C14 C15 C16 C18 -91.5(7) . . . .
N1 C16 C17 N2 -141(4) . . . .
C15 C16 C17 N2 -22(4) . . . .
C18 C16 C17 N2 96(4) . . . .
N1 C16 C18 C19 177.2(5) . . . .
C17 C16 C18 C19 -59.7(6) . . . .
C15 C16 C18 C19 57.8(6) . . . .
N1 C16 C18 C25 -47.9(8) . . . .
C17 C16 C18 C25 75.2(7) . . . .
C15 C16 C18 C25 -167.3(6) . . . .
C25 C18 C19 C20 122.1(7) . . . .
C16 C18 C19 C20 -104.0(7) . . . .
C25 C18 C19 C24 -59.3(8) . . . .
C16 C18 C19 C24 74.5(7) . . . .
C24 C19 C20 C21 0.1(10) . . . .
C18 C19 C20 C21 178.7(6) . . . .
C19 C20 C21 C22 -0.8(11) . . . .
C20 C21 C22 C23 1.0(13) . . . .
C21 C22 C23 C24 -0.5(12) . . . .
C22 C23 C24 C19 -0.2(11) . . . .
C20 C19 C24 C23 0.3(10) . . . .
C18 C19 C24 C23 -178.2(6) . . . .
C19 C18 C25 C26 -132.8(8) . . . .
C16 C18 C25 C26 92.9(8) . . . .
C19 C18 C25 C27 47.5(9) . . . .
C16 C18 C25 C27 -86.7(8) . . . .
C26 C25 C27 N3 81(29) . . . .
C18 C25 C27 N3 -99(29) . . . .
O1 C7 N1 C8 156.1(6) . . . .
C6 C7 N1 C8 -23.9(8) . . . .
O1 C7 N1 C16 -7.9(9) . . . .
C6 C7 N1 C16 172.1(5) . . . .
C9 C8 N1 C7 171.5(6) . . . .
C9 C8 N1 C16 -24.1(8) . . . .
C17 C16 N1 C7 -33.8(7) . . . .
C15 C16 N1 C7 -152.1(5) . . . .
C18 C16 N1 C7 89.9(7) . . . .
C17 C16 N1 C8 161.3(5) . . . .
C15 C16 N1 C8 43.0(7) . . . .
C18 C16 N1 C8 -74.9(6) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350598
