#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:27:06 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/30/7133066.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_7133066
loop_
_publ_author_name
'Maeda, Bumpei'
'Akiyoshi, Ryohei'
'Tanaka, Daisuke'
'Sato, Kohei'
'Murakami, Kei'
_publ_section_title
;
 Synthesis of N-β-brominated alkenyl isothiocyanates
 via dehydrogenation of alkyl isothiocyanates.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6015
_journal_page_last               6018
_journal_paper_doi               10.1039/d4cc01666a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C13 H8 Br N S'
_chemical_formula_sum            'C13 H8 Br N S'
_chemical_formula_weight         290.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.820(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7154(2)
_cell_length_b                   14.3463(3)
_cell_length_c                   7.00360(10)
_cell_measurement_reflns_used    5302
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.6190
_cell_measurement_theta_min      3.8620
_cell_volume                     1147.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -36.00   0.50    0.91    -- -106.00 135.00   4.00   52
  2  ω   -118.00 -72.00   0.50    0.91    -- -106.00 135.00   4.00   92
  3  ω   -112.00 -81.00   0.50    0.91    -- -106.00 125.00 -90.00   62
  4  ω   -116.00 -79.00   0.50    0.91    -- -106.00 134.00-174.00   74
  5  ω    -67.00 -35.00   0.50    0.45    --  -42.33 134.00-174.00   64
  6  ω    -65.00 -40.00   0.50    0.91    -- -106.00   0.00 -60.00   50
  7  ω    -71.00 -37.00   0.50    0.91    -- -106.00  61.00-120.00   68
  8  ω    -67.00 -38.00   0.50    0.91    -- -106.00  61.00-150.00   58
  9  ω    -67.00 -37.00   0.50    0.91    -- -106.00   0.00 -90.00   60
 10  ω    -39.00  34.00   0.50    0.45    --  -42.33  37.00 -30.00  146
 11  ω    -17.00  36.00   0.50    0.45    --  -42.33  19.00  90.00  106
 12  ω    -69.00 -32.00   0.50    0.91    -- -106.00  61.00 150.00   74
 13  ω    -67.00 -33.00   0.50    0.91    -- -106.00  61.00  60.00   68
 14  ω    -65.00 -36.00   0.50    0.91    -- -106.00   0.00-120.00   58
 15  ω    -67.00 -35.00   0.50    0.91    -- -106.00   0.00-180.00   64
 16  ω    -67.00 -42.00   0.50    0.91    -- -106.00   0.00-150.00   50
 17  ω   -147.00-122.00   0.50    0.91    -- -106.00-134.00 117.00   50
 18  ω     37.00  97.00   0.50    0.45    --   42.33-134.00 117.00  120
 19  ω     52.00  77.00   0.50    0.91    --  106.05-134.00 117.00   50
 20  ω     33.00  61.00   0.50    0.91    --  106.05 -94.00 120.00   56
 21  ω     52.00  78.00   0.50    0.91    --  106.05 -94.00 150.00   52
 22  ω     76.00 103.00   0.50    0.91    --  106.05 -94.00 120.00   54
 23  ω     33.00  70.00   0.50    0.91    --  106.05 -61.00 -60.00   74
 24  ω    -37.00  19.00   0.50    0.45    --   42.33 -19.00 -90.00  112
 25  ω     76.00 102.00   0.50    0.45    --   42.33 135.00   4.00   52
 26  ω     68.00 126.00   0.50    0.91    --  106.05 135.00   4.00  116
 27  ω     67.00  92.00   0.50    0.45    --   42.33 134.00-174.00   50
 28  ω     74.00  99.00   0.50    0.91    --  106.05 134.00-174.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636967000
_diffrn_orient_matrix_UB_12      0.0943801000
_diffrn_orient_matrix_UB_13      0.0383484000
_diffrn_orient_matrix_UB_21      0.1176250000
_diffrn_orient_matrix_UB_22      -0.0512296000
_diffrn_orient_matrix_UB_23      0.0675039000
_diffrn_orient_matrix_UB_31      0.0171884000
_diffrn_orient_matrix_UB_32      0.0007314000
_diffrn_orient_matrix_UB_33      -0.2117806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6034
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.025
_diffrn_reflns_theta_max         67.025
_diffrn_reflns_theta_min         3.870
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.314
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0363
_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)+(0.0737P)²+0.0412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1903
_reflns_number_total             2037
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc01666a2.cif
_cod_data_source_block           murakamilab_hex_autored
_cod_depositor_comments
'Adding full bibliography for 7133066--7133067.cif.'
_cod_database_code               7133066
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H S N Br'
_chemical_oxdiff_usercomment     '150 K'
_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   0.743
_shelx_estimated_absorpt_t_min   0.144
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C2(H2), C8(H8), C6(H6), C12(H12), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.519
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 1.00731(2) 0.40332(2) 0.23339(4) 0.03606(16) Uani 1 1 d . . . . .
S1 S 0.84955(6) 0.67484(5) 0.15899(10) 0.0401(2) Uani 1 1 d . . . . .
N1 N 0.79552(18) 0.51098(14) 0.3242(3) 0.0318(5) Uani 1 1 d . . . . .
C10 C 0.6113(2) 0.39129(15) 0.4656(4) 0.0250(5) Uani 1 1 d . . . . .
C13 C 0.8234(2) 0.57978(18) 0.2527(4) 0.0279(5) Uani 1 1 d . . . . .
C11 C 0.8155(2) 0.42521(17) 0.4151(3) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.5401(2) 0.35969(15) 0.5927(3) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.7352(2) 0.39701(14) 0.5417(4) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.5925(2) 0.33584(16) 0.7887(4) 0.0316(5) Uani 1 1 d . . . . .
H4 H 0.544892 0.314574 0.873270 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3681(2) 0.37207(19) 0.3283(4) 0.0345(6) Uani 1 1 d . . . . .
H7 H 0.285850 0.366445 0.280985 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5574(2) 0.41208(16) 0.2682(4) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.603933 0.432511 0.181055 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7824(2) 0.37338(18) 0.7330(3) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.864586 0.377609 0.782007 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4388(3) 0.40288(16) 0.2023(4) 0.0324(6) Uani 1 1 d . . . . .
H8 H 0.403795 0.417473 0.069987 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4178(2) 0.35025(17) 0.5189(4) 0.0318(5) Uani 1 1 d . . . . .
H6 H 0.369840 0.328543 0.602555 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9032(2) 0.37019(18) 0.3903(3) 0.0289(5) Uani 1 1 d . . . . .
H12 H 0.913168 0.311611 0.455108 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7106(2) 0.34298(18) 0.8575(3) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.744433 0.327414 0.989821 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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C13 N1 C11 154.5(2) . . ?
C5 C10 C1 118.2(2) . . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C1 123.0(2) . . ?
N1 C13 S1 174.9(2) . . ?
N1 C11 C1 116.9(2) . . ?
C12 C11 N1 121.5(2) . . ?
C12 C11 C1 121.6(2) . . ?
C4 C5 C10 119.7(2) . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 C10 119.2(2) . . ?
C10 C1 C11 121.1(2) . . ?
C2 C1 C10 120.2(2) . . ?
C2 C1 C11 118.6(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
Br1 C12 H12 118.5 . . ?
C11 C12 Br1 123.0(2) . . ?
C11 C12 H12 118.5 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
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
Br1 C12 1.875(2) . ?
S1 C13 1.573(3) . ?
N1 C13 1.185(3) . ?
N1 C11 1.381(3) . ?
C10 C5 1.423(3) . ?
C10 C1 1.433(3) . ?
C10 C9 1.418(4) . ?
C11 C1 1.486(3) . ?
C11 C12 1.337(3) . ?
C5 C4 1.416(4) . ?
C5 C6 1.418(3) . ?
C1 C2 1.374(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.363(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.409(4) . ?
C7 C6 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C8 1.370(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(3) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
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
N1 C11 C1 C10 57.6(3) . . . . ?
N1 C11 C1 C2 -124.5(2) . . . . ?
N1 C11 C12 Br1 0.4(3) . . . . ?
C10 C5 C4 C3 0.2(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C10 C1 C2 C3 0.2(4) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C13 N1 C11 C1 152.6(5) . . . . ?
C13 N1 C11 C12 -27.3(7) . . . . ?
C11 C1 C2 C3 -177.7(2) . . . . ?
C5 C10 C1 C11 177.2(2) . . . . ?
C5 C10 C1 C2 -0.7(3) . . . . ?
C5 C10 C9 C8 0.8(3) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?
C1 C10 C5 C4 0.5(3) . . . . ?
C1 C10 C5 C6 -177.8(2) . . . . ?
C1 C10 C9 C8 178.2(2) . . . . ?
C1 C11 C12 Br1 -179.54(17) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C9 C10 C5 C4 178.1(2) . . . . ?
C9 C10 C5 C6 -0.2(3) . . . . ?
C9 C10 C1 C11 -0.3(3) . . . . ?
C9 C10 C1 C2 -178.1(2) . . . . ?
C8 C7 C6 C5 1.0(4) . . . . ?
C6 C5 C4 C3 178.4(2) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C12 C11 C1 C10 -122.4(2) . . . . ?
C12 C11 C1 C2 55.5(3) . . . . ?
