#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:17:05 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256161 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157594.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_7157594
loop_
_publ_author_name
'Shally, ?'
'Althagafi, Ismail'
'Shaw, Ranjay'
'Elagamy, Amr'
'Kumar, Abhinav'
'Pratap, Ramendra'
_publ_section_title
;
 A [5 + 1] annulation strategy for the synthesis of multifunctional
 biaryls and p-teraryls from 1,6-Michael acceptor ketene dithioacetals.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6407
_journal_page_last               6417
_journal_paper_doi               10.1039/d0ob00998a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 Br N3 O2 S'
_chemical_formula_sum            'C20 H14 Br N3 O2 S'
_chemical_formula_weight         440.30
_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
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                108.414(7)
_cell_angle_beta                 104.992(7)
_cell_angle_gamma                100.036(7)
_cell_formula_units_Z            2
_cell_length_a                   8.4509(8)
_cell_length_b                   10.7362(9)
_cell_length_c                   11.5735(9)
_cell_measurement_reflns_used    2361
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.3840
_cell_measurement_theta_min      3.7460
_cell_volume                     924.09(16)
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.,'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'xcalibur sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.366
_exptl_absorpt_coefficient_mu    2.358
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2179
_reflns_number_total             3255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00998a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7157593--7157594.cif.'
_cod_original_cell_volume        924.09(15)
_cod_database_code               7157594
_shelx_shelxl_version_number     2016/6
_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   0.650
_shelx_estimated_absorpt_t_max   0.704
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
Br Br 1.08518(13) 0.08775(9) 0.75330(7) 0.1163(5) Uani 1 1 d . . . . .
S S 0.16794(18) 0.44381(15) 0.47952(14) 0.0543(5) Uani 1 1 d . . . . .
O2 O -0.4244(7) 0.3370(6) -0.1177(6) 0.0998(17) Uani 1 1 d . . . . .
C19 C 0.5328(6) 0.0856(5) 0.2093(5) 0.0431(12) Uani 1 1 d . . . . .
O1 O -0.3067(7) 0.5506(6) -0.0035(6) 0.0904(16) Uani 1 1 d . . . . .
N1 N -0.3140(7) 0.4302(6) -0.0275(6) 0.0632(14) Uani 1 1 d . . . . .
N2 N 0.5862(6) 0.0136(5) 0.1442(4) 0.0574(12) Uani 1 1 d . . . . .
C6 C -0.1919(7) 0.2647(6) 0.0419(5) 0.0516(13) Uani 1 1 d . . . . .
H6 H -0.292139 0.197207 -0.013236 0.062 Uiso 1 1 calc R U . . .
C5 C -0.0600(7) 0.2319(5) 0.1127(5) 0.0504(13) Uani 1 1 d . . . . .
H5 H -0.071879 0.141598 0.105024 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2827(6) 0.3408(4) 0.4061(5) 0.0388(12) Uani 1 1 d . . . . .
C9 C 0.4521(6) 0.1762(4) 0.2802(4) 0.0365(11) Uani 1 1 d . . . . .
C11 C 0.4136(6) 0.3038(5) 0.4762(5) 0.0408(12) Uani 1 1 d . . . . .
H11 H 0.442553 0.334677 0.565597 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2361(6) 0.2940(5) 0.2705(4) 0.0366(11) Uani 1 1 d . . . . .
C14 C 0.7958(6) 0.1902(5) 0.4733(5) 0.0435(12) Uani 1 1 d . . . . .
H14 H 0.812447 0.213417 0.405502 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0916(6) 0.3317(5) 0.1960(5) 0.0377(11) Uani 1 1 d . . . . .
C13 C 0.6405(7) 0.1881(5) 0.4955(5) 0.0412(12) Uani 1 1 d . . . . .
C3 C 0.1037(7) 0.4670(5) 0.2064(5) 0.0471(13) Uani 1 1 d . . . . .
H3 H 0.203396 0.535398 0.261144 0.056 Uiso 1 1 calc R U . . .
C2 C -0.0292(7) 0.4998(6) 0.1372(5) 0.0519(14) Uani 1 1 d . . . . .
H2 H -0.021182 0.590321 0.146899 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5020(6) 0.2224(5) 0.4165(4) 0.0379(11) Uani 1 1 d . . . . .
C1 C -0.1747(7) 0.3977(6) 0.0530(5) 0.0491(14) Uani 1 1 d . . . . .
C8 C 0.3224(6) 0.2133(5) 0.2080(4) 0.0378(11) Uani 1 1 d . . . . .
C15 C 0.9224(7) 0.1594(5) 0.5482(5) 0.0545(14) Uani 1 1 d . . . . .
H15 H 1.023123 0.159063 0.529739 0.065 Uiso 1 1 calc R U . . .
C18 C 0.6236(8) 0.1556(5) 0.6002(5) 0.0533(14) Uani 1 1 d . . . . .
H18 H 0.522336 0.153812 0.618192 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7545(9) 0.1261(6) 0.6780(5) 0.0631(17) Uani 1 1 d . . . . .
H17 H 0.741565 0.104842 0.747553 0.076 Uiso 1 1 calc R U . . .
C20 C 0.2682(8) 0.4879(6) 0.6474(6) 0.0624(17) Uani 1 1 d . . . . .
H20A H 0.212442 0.544890 0.695010 0.094 Uiso 1 1 calc R U . . .
H20B H 0.260490 0.406275 0.665659 0.094 Uiso 1 1 calc R U . . .
H20C H 0.386046 0.536530 0.672472 0.094 Uiso 1 1 calc R U . . .
C16 C 0.9039(9) 0.1287(5) 0.6505(5) 0.0607(16) Uani 1 1 d . . . . .
N3 N 0.2777(6) 0.1658(4) 0.0763(4) 0.0532(12) Uani 1 1 d . . . . .
H3A H 0.195100 0.186219 0.031713 0.064 Uiso 1 1 calc R U . . .
H3B H 0.332157 0.115611 0.038077 0.064 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 0.0033 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'
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
_geom_angle_publ_flag
C20 S C12 104.2(3) . . ?
N2 C19 C9 174.1(6) . . ?
O2 N1 O1 123.7(6) . . ?
O2 N1 C1 118.5(5) . . ?
O1 N1 C1 117.6(6) . . ?
C1 C6 C5 119.6(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C11 C12 C7 119.9(4) . . ?
C11 C12 S 122.7(4) . . ?
C7 C12 S 117.4(4) . . ?
C10 C9 C8 122.0(4) . . ?
C10 C9 C19 120.9(5) . . ?
C8 C9 C19 117.1(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C8 C7 C12 119.8(5) . . ?
C8 C7 C4 121.0(4) . . ?
C12 C7 C4 119.3(4) . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C5 C4 C7 120.6(4) . . ?
C5 C4 C3 117.8(5) . . ?
C7 C4 C3 121.6(4) . . ?
C14 C13 C10 122.5(4) . . ?
C14 C13 C18 117.0(5) . . ?
C10 C13 C18 120.5(5) . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C13 C10 C9 123.4(4) . . ?
C13 C10 C11 119.4(4) . . ?
C9 C10 C11 117.2(5) . . ?
C2 C1 C6 121.0(5) . . ?
C2 C1 N1 120.1(5) . . ?
C6 C1 N1 118.9(5) . . ?
N3 C8 C7 120.6(5) . . ?
N3 C8 C9 120.1(4) . . ?
C7 C8 C9 119.3(4) . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C18 C13 121.5(6) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C18 C17 C16 118.9(5) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
S C20 H20A 109.5 . . ?
S C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C16 C17 120.5(6) . . ?
C15 C16 Br 119.2(5) . . ?
C17 C16 Br 120.3(5) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
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
Br C16 1.891(6) . ?
S C20 1.773(6) . ?
S C12 1.759(4) . ?
O2 N1 1.214(7) . ?
C19 N2 1.140(6) . ?
C19 C9 1.450(7) . ?
O1 N1 1.220(7) . ?
N1 C1 1.468(8) . ?
C6 C1 1.370(8) . ?
C6 C5 1.373(8) . ?
C6 H6 0.9300 . ?
C5 C4 1.396(7) . ?
C5 H5 0.9300 . ?
C12 C11 1.390(7) . ?
C12 C7 1.408(7) . ?
C9 C10 1.415(7) . ?
C9 C8 1.395(7) . ?
C11 C10 1.382(7) . ?
C11 H11 0.9300 . ?
C7 C8 1.379(6) . ?
C7 C4 1.499(7) . ?
C14 C15 1.354(7) . ?
C14 C13 1.400(7) . ?
C14 H14 0.9300 . ?
C4 C3 1.401(7) . ?
C13 C10 1.467(7) . ?
C13 C18 1.396(7) . ?
C3 C2 1.371(8) . ?
C3 H3 0.9300 . ?
C2 C1 1.378(8) . ?
C2 H2 0.9300 . ?
C8 N3 1.368(6) . ?
C15 C16 1.363(8) . ?
C15 H15 0.9300 . ?
C18 C17 1.386(9) . ?
C18 H18 0.9300 . ?
C17 C16 1.378(9) . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
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
C1 C6 C5 C4 0.0(8) . . . . ?
C20 S C12 C11 3.4(5) . . . . ?
C20 S C12 C7 -177.4(4) . . . . ?
C7 C12 C11 C10 0.6(7) . . . . ?
S C12 C11 C10 179.8(3) . . . . ?
C11 C12 C7 C8 -1.0(7) . . . . ?
S C12 C7 C8 179.7(3) . . . . ?
C11 C12 C7 C4 178.4(4) . . . . ?
S C12 C7 C4 -0.8(6) . . . . ?
C6 C5 C4 C7 -178.6(5) . . . . ?
C6 C5 C4 C3 0.9(7) . . . . ?
C8 C7 C4 C5 66.3(6) . . . . ?
C12 C7 C4 C5 -113.1(5) . . . . ?
C8 C7 C4 C3 -113.2(5) . . . . ?
C12 C7 C4 C3 67.4(6) . . . . ?
C15 C14 C13 C10 179.4(4) . . . . ?
C15 C14 C13 C18 1.4(7) . . . . ?
C5 C4 C3 C2 0.1(7) . . . . ?
C7 C4 C3 C2 179.6(4) . . . . ?
C4 C3 C2 C1 -2.1(7) . . . . ?
C14 C13 C10 C9 42.9(7) . . . . ?
C18 C13 C10 C9 -139.1(5) . . . . ?
C14 C13 C10 C11 -137.2(5) . . . . ?
C18 C13 C10 C11 40.8(6) . . . . ?
C8 C9 C10 C13 -178.5(4) . . . . ?
C19 C9 C10 C13 2.6(7) . . . . ?
C8 C9 C10 C11 1.6(6) . . . . ?
C19 C9 C10 C11 -177.3(4) . . . . ?
C12 C11 C10 C13 179.2(4) . . . . ?
C12 C11 C10 C9 -0.9(7) . . . . ?
C3 C2 C1 C6 3.1(8) . . . . ?
C3 C2 C1 N1 -176.4(4) . . . . ?
C5 C6 C1 C2 -2.0(8) . . . . ?
C5 C6 C1 N1 177.4(5) . . . . ?
O2 N1 C1 C2 165.7(5) . . . . ?
O1 N1 C1 C2 -10.5(7) . . . . ?
O2 N1 C1 C6 -13.8(7) . . . . ?
O1 N1 C1 C6 170.1(5) . . . . ?
C12 C7 C8 N3 179.4(4) . . . . ?
C4 C7 C8 N3 -0.1(7) . . . . ?
C12 C7 C8 C9 1.8(7) . . . . ?
C4 C7 C8 C9 -177.7(4) . . . . ?
C10 C9 C8 N3 -179.7(4) . . . . ?
C19 C9 C8 N3 -0.7(7) . . . . ?
C10 C9 C8 C7 -2.1(7) . . . . ?
C19 C9 C8 C7 176.9(4) . . . . ?
C13 C14 C15 C16 -1.8(8) . . . . ?
C14 C13 C18 C17 -0.4(7) . . . . ?
C10 C13 C18 C17 -178.4(4) . . . . ?
C13 C18 C17 C16 -0.2(8) . . . . ?
C14 C15 C16 C17 1.2(8) . . . . ?
C14 C15 C16 Br -179.5(4) . . . . ?
C18 C17 C16 C15 -0.2(8) . . . . ?
C18 C17 C16 Br -179.5(4) . . . . ?
