#------------------------------------------------------------------------------
#$Date: 2021-10-06 18:02:58 +0200 (Wed 06 de Oct de 2021) $
#$Revision: 269752 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/08/7060870.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_7060870
loop_
_publ_author_name
'Farran, Daniel'
'Vanthuyne, Nicolas'
'Bossa, Giulia'
'Belot, Vincent'
'Albalat, Muriel'
'Jean, Marion'
'Roussel, Christian'
_publ_section_title
;
 Slight structural modulation around a pivotal bond: high impact on
 enantiomeric stability
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16039
_journal_page_last               16047
_journal_paper_doi               10.1039/D1NJ03178C
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H10 Br N S Se'
_chemical_formula_sum            'C12 H10 Br N S Se'
_chemical_formula_weight         359.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2021-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.49830(10)
_cell_length_b                   7.8011(2)
_cell_length_c                   21.5964(3)
_cell_measurement_reflns_used    7632
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.7660
_cell_measurement_theta_min      4.0650
_cell_volume                     1263.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  92.00   1.00    1.00    --    0.00  57.00-150.00  134
  2  ω   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00-150.00   68
  3  ω   -147.00 -79.00   1.00   10.00    --  -52.94 -99.00 150.00   68
  4  ω     94.00 145.00   1.00   10.00    --   52.94 125.00 -60.00   51
  5  ω    -47.00  96.00   1.00   10.00    --   52.94 -77.00  60.00  143
  6  ω     15.00 152.00   1.00   20.00    --  105.88 -38.00 -60.00  137
  7  ω     64.00 178.00   1.00   20.00    --  105.88  50.00-150.00  114
  8  ω     12.00 150.00   1.00   20.00    --  105.88 -63.00  90.00  138
  9  ω     59.00 178.00   1.00   20.00    --  105.88  38.00-180.00  119
 10  ω     18.00 118.00   1.00   20.00    --  105.88-118.00 111.00  100
 11  ω   -101.00 -35.00   1.00    1.00    --    0.00-178.00 -60.00   66
 12  ω   -145.00 -11.00   1.00   10.00    --  -52.94 -57.00  90.00  134
 13  ω   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00-150.00  138
 14  ω   -144.00  -6.00   1.00   10.00    --  -52.94 -38.00 -30.00  138
 15  ω     59.00 178.00   1.00   20.00    --  105.88  38.00 -30.00  119
 16  ω     62.00 178.00   1.00   20.00    --  105.88  63.00  30.00  116
 17  ω    100.00 178.00   1.00   20.00    --  105.88 111.00  60.00   78
 18  ω     64.00 178.00   1.00   20.00    --  105.88  50.00 -90.00  114
 19  ω     62.00 178.00   1.00   20.00    --  105.88  63.00  90.00  116
 20  ω    -92.00  42.00   1.00    1.00    --    0.00 -57.00-150.00  134
 21  ω   -153.00-116.00   1.00   10.00    --  -52.94 -77.00-180.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1842338000
_diffrn_orient_matrix_UB_12      0.0234486000
_diffrn_orient_matrix_UB_13      0.0304082000
_diffrn_orient_matrix_UB_21      -0.0863863000
_diffrn_orient_matrix_UB_22      -0.0138642000
_diffrn_orient_matrix_UB_23      0.0645172000
_diffrn_orient_matrix_UB_31      0.0282937000
_diffrn_orient_matrix_UB_32      -0.1956185000
_diffrn_orient_matrix_UB_33      -0.0009570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11206
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.845
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.033
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
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    1.888
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0243
_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)+(0.0271P)²+0.7769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2243
_reflns_number_total             2313
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03178c2.cif
_cod_data_source_block           se5br1
_cod_depositor_comments
'Adding full bibliography for 7060869--7060872.cif.'
_cod_database_code               7060870
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c12 h10 Br1 n1 S1 Se1 '
_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.
;
_diffrn_oxdiff_ac3_digest_frames
;
01566d660f1d9561259bcb6f16fbc634e400031dc5e
;
_diffrn_oxdiff_ac3_digest_hkl
;
01537d13261c39bdd5ce080d65c47b74569f0e
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.586
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_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 0.64865(9) 0.20770(7) 0.65080(3) 0.06766(17) Uani 1 1 d . . . . .
Se1 Se 0.15204(6) 0.55366(8) 0.64624(2) 0.05597(16) Uani 1 1 d . . . . .
S1 S 0.25666(15) 0.48708(19) 0.50839(5) 0.0523(3) Uani 1 1 d . . . . .
N1 N 0.4965(4) 0.5353(5) 0.58908(15) 0.0408(8) Uani 1 1 d . . . . .
C1 C 0.3147(5) 0.5279(6) 0.58516(18) 0.0436(9) Uani 1 1 d . . . . .
C2 C 0.4778(6) 0.4846(7) 0.48492(19) 0.0477(10) Uani 1 1 d . . . . .
C3 C 0.5765(6) 0.4592(9) 0.4258(2) 0.0607(13) Uani 1 1 d . . . . .
H3A H 0.538600 0.540344 0.394407 0.073 Uiso 1 1 calc R . . . .
H3B H 0.562096 0.343491 0.410174 0.073 Uiso 1 1 calc R . . . .
C4 C 0.7706(7) 0.4935(9) 0.4467(2) 0.0658(14) Uani 1 1 d . . . . .
H4A H 0.846413 0.399194 0.433890 0.079 Uiso 1 1 calc R . . . .
H4B H 0.814427 0.597423 0.427327 0.079 Uiso 1 1 calc R . . . .
C5 C 0.7778(6) 0.5125(7) 0.5176(2) 0.0550(12) Uani 1 1 d . . . . .
H5A H 0.839390 0.416996 0.536774 0.066 Uiso 1 1 calc R . . . .
H5B H 0.834745 0.618954 0.529745 0.066 Uiso 1 1 calc R . . . .
C6 C 0.5850(5) 0.5125(6) 0.53300(18) 0.0424(9) Uani 1 1 d . . . . .
C7 C 0.5898(5) 0.5675(6) 0.6463(2) 0.0420(9) Uani 1 1 d . . . . .
C8 C 0.6061(7) 0.7345(7) 0.6673(2) 0.0548(12) Uani 1 1 d . . . . .
H8 H 0.554517 0.824355 0.645355 0.066 Uiso 1 1 calc R . . . .
C9 C 0.6998(7) 0.7663(7) 0.7210(2) 0.0618(14) Uani 1 1 d . . . . .
H9 H 0.711322 0.878330 0.735204 0.074 Uiso 1 1 calc R . . . .
C10 C 0.7756(7) 0.6359(8) 0.7536(2) 0.0595(13) Uani 1 1 d . . . . .
H10 H 0.838596 0.659834 0.789705 0.071 Uiso 1 1 calc R . . . .
C11 C 0.7599(6) 0.4686(7) 0.7337(2) 0.0546(12) Uani 1 1 d . . . . .
H11 H 0.810713 0.379607 0.756304 0.066 Uiso 1 1 calc R . . . .
C12 C 0.6670(6) 0.4353(6) 0.67936(18) 0.0425(9) 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 0.0181 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'
Se Se -0.7943 1.1372 '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
C2 S1 C1 92.36(19) . . ?
C1 N1 C6 114.6(3) . . ?
C1 N1 C7 123.0(3) . . ?
C6 N1 C7 122.4(3) . . ?
S1 C1 Se1 123.1(2) . . ?
N1 C1 Se1 128.5(3) . . ?
N1 C1 S1 108.4(3) . . ?
C3 C2 S1 136.7(3) . . ?
C6 C2 S1 110.3(3) . . ?
C6 C2 C3 113.0(4) . . ?
C2 C3 H3A 111.5 . . ?
C2 C3 H3B 111.5 . . ?
C2 C3 C4 101.2(4) . . ?
H3A C3 H3B 109.3 . . ?
C4 C3 H3A 111.5 . . ?
C4 C3 H3B 111.5 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.9(4) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 111.6 . . ?
C4 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
C6 C5 C4 100.9(4) . . ?
C6 C5 H5A 111.6 . . ?
C6 C5 H5B 111.6 . . ?
N1 C6 C5 131.3(4) . . ?
C2 C6 N1 114.3(4) . . ?
C2 C6 C5 114.4(4) . . ?
C8 C7 N1 119.2(4) . . ?
C12 C7 N1 121.1(4) . . ?
C12 C7 C8 119.7(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(5) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 Br1 120.2(3) . . ?
C7 C12 C11 120.5(4) . . ?
C11 C12 Br1 119.3(4) . . ?
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 1.884(4) . ?
Se1 C1 1.808(4) . ?
S1 C1 1.743(4) . ?
S1 C2 1.734(4) . ?
N1 C1 1.367(5) . ?
N1 C6 1.392(5) . ?
N1 C7 1.441(5) . ?
C2 C3 1.489(6) . ?
C2 C6 1.331(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.547(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.538(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.483(6) . ?
C7 C8 1.385(7) . ?
C7 C12 1.382(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(6) . ?
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
S1 C2 C3 C4 175.5(5) . . . . ?
S1 C2 C6 N1 0.4(6) . . . . ?
S1 C2 C6 C5 179.9(4) . . . . ?
N1 C7 C8 C9 -178.1(4) . . . . ?
N1 C7 C12 Br1 -1.0(5) . . . . ?
N1 C7 C12 C11 178.6(4) . . . . ?
C1 S1 C2 C3 180.0(6) . . . . ?
C1 S1 C2 C6 0.2(4) . . . . ?
C1 N1 C6 C2 -1.0(6) . . . . ?
C1 N1 C6 C5 179.6(5) . . . . ?
C1 N1 C7 C8 -80.8(6) . . . . ?
C1 N1 C7 C12 101.0(5) . . . . ?
C2 S1 C1 Se1 179.4(3) . . . . ?
C2 S1 C1 N1 -0.8(4) . . . . ?
C2 C3 C4 C5 7.6(7) . . . . ?
C3 C2 C6 N1 -179.5(5) . . . . ?
C3 C2 C6 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -7.5(6) . . . . ?
C4 C5 C6 N1 -175.9(5) . . . . ?
C4 C5 C6 C2 4.7(6) . . . . ?
C6 N1 C1 Se1 -179.1(4) . . . . ?
C6 N1 C1 S1 1.1(5) . . . . ?
C6 N1 C7 C8 97.9(5) . . . . ?
C6 N1 C7 C12 -80.3(6) . . . . ?
C6 C2 C3 C4 -4.8(7) . . . . ?
C7 N1 C1 Se1 -0.3(7) . . . . ?
C7 N1 C1 S1 179.9(3) . . . . ?
C7 N1 C6 C2 -179.8(4) . . . . ?
C7 N1 C6 C5 0.8(8) . . . . ?
C7 C8 C9 C10 -0.2(8) . . . . ?
C8 C7 C12 Br1 -179.1(3) . . . . ?
C8 C7 C12 C11 0.4(6) . . . . ?
C8 C9 C10 C11 -0.2(9) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C11 C12 Br1 178.8(4) . . . . ?
C10 C11 C12 C7 -0.8(7) . . . . ?
C12 C7 C8 C9 0.1(7) . . . . ?
