#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:41:06 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270498 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158323.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_7158323
loop_
_publ_author_name
'Shen, Jinhui'
'Yu, Aimin'
'Meng, Xiangtai'
_publ_section_title
;
 Stereoselective [4 + 3] annulation of azadienes and ethyl
 4-bromo-3-oxobutanoate: construction of benzindeno-fused azepine
 derivatives.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9026
_journal_page_last               9030
_journal_paper_doi               10.1039/d1ob01749g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C28 H25 N O5 S2'
_chemical_formula_sum            'C28 H25 N O5 S2'
_chemical_formula_weight         519.61
_chemical_name_systematic        ss
_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_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-07 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                84.830(2)
_cell_angle_beta                 78.631(2)
_cell_angle_gamma                85.649(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3217(11)
_cell_length_b                   10.3997(14)
_cell_length_c                   15.418(2)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.434
_cell_measurement_theta_min      2.473
_cell_volume                     1300.5(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14167
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.473
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0399 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.9413. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.371
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4576
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0615
_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)+(0.0637P)²+2.0487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3736
_reflns_number_total             4576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01749g2.cif
_cod_data_source_block           12
_cod_depositor_comments
'Adding full bibliography for 7158322--7158326.cif.'
_cod_database_code               7158323
_shelx_shelxl_version_number     2016/4
_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_max   0.998
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C16, C17, C18
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C8 \\sim C9 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within
1.7A with sigma of 0.001 and sigma for terminal atoms of 0.005
C8 \\sim C9 \\sim C10: within 1.7A with sigma of 0.001 and sigma for terminal
atoms of 0.005
4.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S001 S 0.27894(9) 0.37427(8) 0.30683(5) 0.0387(2) Uani 1 1 d . . . . .
S1 S 0.81828(10) 0.41589(9) 0.08723(5) 0.0448(2) Uani 1 1 d . . . . .
O1 O 0.2814(3) 0.3132(2) 0.22719(15) 0.0494(6) Uani 1 1 d . . . . .
O2 O 0.2627(3) 0.3005(2) 0.39037(16) 0.0538(6) Uani 1 1 d . . . . .
O3 O 0.7298(4) 0.3975(3) 0.44579(19) 0.0715(8) Uani 1 1 d . . . . .
O4 O 0.6750(4) 0.1064(3) 0.4717(2) 0.0818(10) Uani 1 1 d . . . . .
O5 O 0.9188(4) 0.1284(4) 0.3833(2) 0.0842(10) Uani 1 1 d . . . . .
N1 N 0.4537(3) 0.4459(3) 0.29325(16) 0.0390(6) Uani 1 1 d . . . . .
C1 C -0.2576(6) 0.8025(4) 0.3438(4) 0.0814(14) Uani 1 1 d . . . . .
H1A H -0.211171 0.885326 0.330522 0.122 Uiso 1 1 calc GR . . . .
H1B H -0.318059 0.796583 0.403716 0.122 Uiso 1 1 calc GR . . . .
H1C H -0.330071 0.792509 0.303810 0.122 Uiso 1 1 calc GR . . . .
C2 C -0.1220(4) 0.6972(3) 0.3333(3) 0.0515(9) Uani 1 1 d . . . . .
C3 C -0.0807(4) 0.6329(4) 0.2565(2) 0.0526(9) Uani 1 1 d . . . . .
H3 H -0.136302 0.656283 0.210187 0.063 Uiso 1 1 calc R . . . .
C4 C 0.0414(4) 0.5349(3) 0.2472(2) 0.0447(8) Uani 1 1 d . . . . .
H4 H 0.068265 0.493027 0.194957 0.054 Uiso 1 1 calc R . . . .
C5 C 0.1237(4) 0.4993(3) 0.3165(2) 0.0378(7) Uani 1 1 d . . . . .
C6 C 0.0836(4) 0.5625(4) 0.3937(2) 0.0479(8) Uani 1 1 d . . . . .
H6 H 0.138335 0.538592 0.440346 0.057 Uiso 1 1 calc R . . . .
C7 C -0.0375(5) 0.6608(4) 0.4014(2) 0.0543(9) Uani 1 1 d . . . . .
H7 H -0.063190 0.703543 0.453250 0.065 Uiso 1 1 calc R . . . .
C8 C 0.7076(9) 0.0613(7) 0.6208(4) 0.130(2) Uani 1 1 d . U . . .
H8A H 0.735456 0.149198 0.620659 0.195 Uiso 1 1 calc GR . . . .
H8B H 0.766692 0.006647 0.658911 0.195 Uiso 1 1 calc GR . . . .
H8C H 0.591758 0.055223 0.641944 0.195 Uiso 1 1 calc GR . . . .
C9 C 0.7487(9) 0.0225(7) 0.5367(4) 0.126(2) Uani 1 1 d . U . . .
H9A H 0.714546 -0.064620 0.536934 0.151 Uiso 1 1 calc R . . . .
H9B H 0.867259 0.020065 0.518308 0.151 Uiso 1 1 calc R . . . .
C10 C 0.7752(5) 0.1534(4) 0.4009(2) 0.0538(9) Uani 1 1 d . U . . .
C11 C 0.6806(4) 0.2493(3) 0.3458(2) 0.0419(7) Uani 1 1 d . . . . .
H11 H 0.574171 0.215151 0.345518 0.050 Uiso 1 1 calc R . . . .
C12 C 0.6511(4) 0.3741(3) 0.3920(2) 0.0426(8) Uani 1 1 d . . . . .
C13 C 0.5183(4) 0.4716(3) 0.3709(2) 0.0447(8) Uani 1 1 d . . . . .
H13A H 0.428844 0.472786 0.421823 0.054 Uiso 1 1 calc R . . . .
H13B H 0.561857 0.556692 0.361152 0.054 Uiso 1 1 calc R . . . .
C14 C 0.7757(4) 0.2670(3) 0.2487(2) 0.0429(7) Uani 1 1 d . . . . .
H14 H 0.887013 0.288828 0.251489 0.052 Uiso 1 1 calc R . . . .
C15 C 0.7927(7) 0.1438(4) 0.2015(3) 0.0799(8) Uani 1 1 d . U . . .
C16 C 0.9455(7) 0.0835(5) 0.1731(3) 0.0859(8) Uani 1 1 d . U . . .
H16 H 1.039653 0.114154 0.185871 0.103 Uiso 1 1 calc R . . . .
C17 C 0.9544(8) -0.0280(5) 0.1234(3) 0.0903(8) Uani 1 1 d . U . . .
H17 H 1.055427 -0.070472 0.103032 0.108 Uiso 1 1 calc R . . . .
C18 C 0.8177(8) -0.0703(5) 0.1065(3) 0.0898(8) Uani 1 1 d . U . . .
H18 H 0.826445 -0.142048 0.073652 0.108 Uiso 1 1 calc R . . . .
C19 C 0.6688(8) -0.0150(5) 0.1343(3) 0.0866(8) Uani 1 1 d . U . . .
H19 H 0.576044 -0.048180 0.121702 0.104 Uiso 1 1 calc R . . . .
C20 C 0.6550(7) 0.0931(4) 0.1825(3) 0.0816(8) Uani 1 1 d . U . . .
H20 H 0.551674 0.132300 0.202527 0.098 Uiso 1 1 calc R . . . .
C21 C 0.7050(4) 0.3762(3) 0.1928(2) 0.0375(7) Uani 1 1 d . . . . .
C22 C 0.5658(4) 0.4538(3) 0.21015(19) 0.0358(7) Uani 1 1 d . . . . .
C23 C 0.5464(4) 0.5516(3) 0.1399(2) 0.0381(7) Uani 1 1 d . . . . .
C24 C 0.6762(4) 0.5409(3) 0.0672(2) 0.0410(7) Uani 1 1 d . . . . .
C25 C 0.6829(5) 0.6238(4) -0.0096(2) 0.0520(9) Uani 1 1 d . . . . .
H25 H 0.769461 0.615726 -0.057509 0.062 Uiso 1 1 calc R . . . .
C26 C 0.5590(5) 0.7173(4) -0.0126(2) 0.0589(10) Uani 1 1 d . . . . .
H26 H 0.560583 0.772507 -0.063614 0.071 Uiso 1 1 calc R . . . .
C27 C 0.4309(5) 0.7312(4) 0.0595(3) 0.0579(10) Uani 1 1 d . . . . .
H27 H 0.348821 0.796329 0.056122 0.069 Uiso 1 1 calc R . . . .
C28 C 0.4233(4) 0.6498(3) 0.1362(2) 0.0473(8) Uani 1 1 d . . . . .
H28 H 0.337763 0.660280 0.184347 0.057 Uiso 1 1 calc R . . . .
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'
S S 0.1246 0.1234 '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
O1 S001 N1 106.70(13) . . ?
O1 S001 C5 108.84(15) . . ?
O2 S001 O1 120.78(16) . . ?
O2 S001 N1 106.13(14) . . ?
O2 S001 C5 107.67(15) . . ?
N1 S001 C5 105.77(14) . . ?
C24 S1 C21 91.88(15) . . ?
C10 O4 C9 117.1(4) . . ?
C13 N1 S001 119.5(2) . . ?
C22 N1 S001 122.1(2) . . ?
C22 N1 C13 116.4(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 C7 118.3(3) . . ?
C7 C2 C1 120.6(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S001 120.4(2) . . ?
C6 C5 S001 119.6(2) . . ?
C6 C5 C4 120.0(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
O4 C9 H9A 108.8 . . ?
O4 C9 H9B 108.8 . . ?
C8 C9 O4 113.7(5) . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O4 C10 C11 110.0(3) . . ?
O5 C10 O4 125.5(4) . . ?
O5 C10 C11 124.5(4) . . ?
C10 C11 H11 108.6 . . ?
C10 C11 C14 110.6(3) . . ?
C12 C11 C10 107.1(3) . . ?
C12 C11 H11 108.6 . . ?
C12 C11 C14 113.2(3) . . ?
C14 C11 H11 108.6 . . ?
O3 C12 C11 122.1(3) . . ?
O3 C12 C13 118.7(3) . . ?
C13 C12 C11 119.3(3) . . ?
N1 C13 C12 113.9(3) . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C11 C14 H14 106.8 . . ?
C15 C14 C11 112.4(3) . . ?
C15 C14 H14 106.8 . . ?
C15 C14 C21 109.2(3) . . ?
C21 C14 C11 114.2(3) . . ?
C21 C14 H14 106.8 . . ?
C16 C15 C14 120.7(5) . . ?
C16 C15 C20 119.1(5) . . ?
C20 C15 C14 120.2(4) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 118.0(6) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 118.3 . . ?
C17 C18 C19 123.3(5) . . ?
C19 C18 H18 118.3 . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(6) . . ?
C20 C19 H19 120.7 . . ?
C15 C20 C19 121.2(5) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C14 C21 S1 117.2(2) . . ?
C22 C21 S1 111.3(2) . . ?
C22 C21 C14 131.5(3) . . ?
N1 C22 C23 122.5(3) . . ?
C21 C22 N1 123.1(3) . . ?
C21 C22 C23 114.3(3) . . ?
C24 C23 C22 111.0(3) . . ?
C28 C23 C22 129.9(3) . . ?
C28 C23 C24 119.1(3) . . ?
C23 C24 S1 111.5(2) . . ?
C25 C24 S1 127.0(3) . . ?
C25 C24 C23 121.5(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 C24 118.3(3) . . ?
C26 C25 H25 120.8 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.0(3) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.1(3) . . ?
C28 C27 H27 119.4 . . ?
C23 C28 H28 120.6 . . ?
C27 C28 C23 118.8(3) . . ?
C27 C28 H28 120.6 . . ?
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
S001 O1 1.428(2) . ?
S001 O2 1.427(2) . ?
S001 N1 1.652(3) . ?
S001 C5 1.756(3) . ?
S1 C21 1.744(3) . ?
S1 C24 1.738(3) . ?
O3 C12 1.205(4) . ?
O4 C9 1.464(5) . ?
O4 C10 1.317(5) . ?
O5 C10 1.186(5) . ?
N1 C13 1.459(4) . ?
N1 C22 1.428(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(5) . ?
C2 C3 1.384(5) . ?
C2 C7 1.385(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C9 1.363(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.526(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.516(5) . ?
C11 C14 1.551(4) . ?
C12 C13 1.505(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9800 . ?
C14 C15 1.514(6) . ?
C14 C21 1.517(4) . ?
C15 C16 1.382(7) . ?
C15 C20 1.388(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.436(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.329(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.333(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.356(4) . ?
C22 C23 1.442(4) . ?
C23 C24 1.401(4) . ?
C23 C28 1.396(5) . ?
C24 C25 1.395(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.367(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.389(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.385(5) . ?
C28 H28 0.9300 . ?
