#------------------------------------------------------------------------------
#$Date: 2022-02-16 01:59:30 +0200 (Wed, 16 Feb 2022) $
#$Revision: 272982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/95/7709502.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_7709502
loop_
_publ_author_name
'Saab, Marina'
'Nelson, David J.'
'Leech, Matthew C.'
'Lam, Kevin'
'Nolan, Steven P.'
'Nahra, Fady'
'Van Hecke, Kristof'
_publ_section_title
;
 Reactions of N-heterocyclic carbene-based chalcogenoureas with halogens:
 a diverse range of outcomes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT00010E
_journal_year                    2022
_chemical_formula_moiety         'C29 H40 Br N2 S, Br3'
_chemical_formula_sum            'C29 H40 Br4 N2 S'
_chemical_formula_weight         768.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.132(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7651(2)
_cell_length_b                   16.9691(3)
_cell_length_c                   10.1288(2)
_cell_measurement_reflns_used    6503
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5340
_cell_measurement_theta_min      4.6330
_cell_volume                     1575.85(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00  46.00   1.00    1.00    --  -41.68   0.00  60.00  176
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-120.00   71
  3  ω     34.00 135.00   1.00    6.00    --  106.01 -61.00  90.00  101
  4  ω    103.00 178.00   1.00    6.00    --  106.01  77.00-150.00   75
  5  ω    103.00 178.00   1.00    6.00    --  106.01  77.00   0.00   75
  6  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 120.00   75
  7  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 -90.00   75
  8  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 150.00   75
  9  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 -60.00   75
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 11  ω     14.00 115.00   1.00    1.00    --   41.68  57.00 -90.00  101
 12  ω     33.00 112.00   1.00    6.00    --  106.01-125.00 -30.00   79
 13  ω     78.00 178.00   1.00    6.00    --  106.01  30.00-120.00  100
 14  ω     33.00 112.00   1.00    6.00    --  106.01-125.00  90.00   79
 15  ω     78.00 178.00   1.00    6.00    --  106.01  30.00  90.00  100
 16  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  30.00   81
 17  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 18  ω     77.00 112.00   1.00    6.00    --  106.01  61.00   0.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064072000
_diffrn_orient_matrix_UB_12      0.0764734000
_diffrn_orient_matrix_UB_13      0.0796819000
_diffrn_orient_matrix_UB_21      0.1513968000
_diffrn_orient_matrix_UB_22      -0.0184981000
_diffrn_orient_matrix_UB_23      0.1084683000
_diffrn_orient_matrix_UB_31      0.0725173000
_diffrn_orient_matrix_UB_32      0.0453291000
_diffrn_orient_matrix_UB_33      -0.0901839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15068
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.786
_diffrn_reflns_theta_min         4.650
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.999
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       irregular
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.062
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_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)+(0.0415P)²+2.9707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2866
_reflns_number_total             3254
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms--349
_cod_database_code               7709502
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C29 H40 N2 Se Br2'
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2021-10-05
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.791
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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_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 0.35143(5) 0.250000 0.34652(5) 0.01867(12) Uani 1 2 d S T P . .
S1 S 0.55103(10) 0.250000 0.54171(11) 0.0159(2) Uani 1 2 d S T P . .
N1 N 0.7746(3) 0.31395(14) 0.4710(3) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.6984(4) 0.250000 0.4850(4) 0.0140(7) Uani 1 2 d S T P . .
C2 C 0.9015(3) 0.29039(18) 0.4518(3) 0.0186(6) Uani 1 1 d . . . . .
C3 C 1.0151(4) 0.34648(18) 0.4430(4) 0.0240(7) Uani 1 1 d . . . . .
H3A H 1.088628 0.353514 0.536607 0.036 Uiso 1 1 calc GR . . . .
H3B H 0.969734 0.397383 0.407827 0.036 Uiso 1 1 calc GR . . . .
H3C H 1.061630 0.325513 0.378766 0.036 Uiso 1 1 calc GR . . . .
C4 C 0.7285(3) 0.39561(16) 0.4698(3) 0.0155(5) Uani 1 1 d . . . . .
C5 C 0.7835(3) 0.43900(17) 0.5947(3) 0.0171(6) Uani 1 1 d . . . . .
C6 C 0.7407(3) 0.51781(18) 0.5884(3) 0.0197(6) Uani 1 1 d . . . . .
H6 H 0.773490 0.549183 0.671039 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6514(3) 0.55096(17) 0.4637(4) 0.0218(6) Uani 1 1 d . . . . .
H7 H 0.624198 0.604817 0.461673 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6013(3) 0.50647(18) 0.3420(3) 0.0205(6) Uani 1 1 d . . . . .
H8 H 0.541253 0.530472 0.257129 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6376(3) 0.42696(17) 0.3419(3) 0.0174(6) Uani 1 1 d . . . . .
C10 C 0.5825(4) 0.37844(19) 0.2067(3) 0.0217(6) Uani 1 1 d . . . . .
H10 H 0.573027 0.322556 0.233724 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6908(4) 0.3799(2) 0.1278(4) 0.0315(8) Uani 1 1 d . . . . .
H11A H 0.705542 0.434351 0.103515 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.652169 0.348524 0.041600 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.784144 0.357611 0.187669 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.4333(4) 0.4053(2) 0.1093(4) 0.0291(7) Uani 1 1 d . . . . .
H12A H 0.363247 0.402242 0.158893 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.401008 0.371041 0.026292 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.439638 0.459742 0.079827 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.8821(3) 0.40370(19) 0.7322(3) 0.0221(6) Uani 1 1 d . . . . .
H13 H 0.911130 0.349721 0.712246 0.027 Uiso 1 1 calc R . . . .
C14 C 1.0211(4) 0.4523(2) 0.7977(4) 0.0330(8) Uani 1 1 d . . . . .
H14A H 1.070524 0.458810 0.728977 0.049 Uiso 1 1 calc GR . . . .
H14B H 1.086097 0.425035 0.880989 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.995695 0.504198 0.824950 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.7985(4) 0.3956(2) 0.8348(4) 0.0344(8) Uani 1 1 d . . . . .
H15A H 0.768807 0.447964 0.855930 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.861414 0.370851 0.921965 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.711668 0.362956 0.792180 0.052 Uiso 1 1 calc GR . . . .
Br2 Br 0.05976(6) 0.250000 0.10545(7) 0.04355(17) Uani 1 2 d S T P . .
Br3 Br 0.18151(6) 0.250000 -0.08645(5) 0.03082(14) Uani 1 2 d S T P . .
Br4 Br 0.32162(9) 0.250000 -0.25061(7) 0.05031(19) Uani 1 2 d S T P . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 2 1 0.0323
0 -4 6 0.0452
-6 -4 1 0.0731
0 4 -6 0.0162
5 4 -5 0.0167
-3 9 3 0.0478
-4 -6 5 0.0443
3 -9 -3 0.0328
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
C1 S1 Br1 106.12(15) . . ?
C1 N1 C2 109.7(2) . . ?
C1 N1 C4 125.9(2) . . ?
C2 N1 C4 124.4(2) . . ?
N1 C1 S1 126.05(17) 4_565 . ?
N1 C1 S1 126.05(17) . . ?
N1 C1 N1 106.9(3) 4_565 . ?
N1 C2 C3 123.2(3) . . ?
C2 C2 N1 106.86(16) 4_565 . ?
C2 C2 C3 129.80(17) 4_565 . ?
C5 C4 N1 118.1(3) . . ?
C9 C4 N1 117.7(3) . . ?
C9 C4 C5 124.1(3) . . ?
C4 C5 C13 123.1(3) . . ?
C6 C5 C4 116.5(3) . . ?
C6 C5 C13 120.4(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 C8 120.7(3) . . ?
C7 C8 C9 121.1(3) . . ?
C4 C9 C10 122.7(3) . . ?
C8 C9 C4 116.6(3) . . ?
C8 C9 C10 120.7(3) . . ?
C9 C10 C11 111.5(3) . . ?
C12 C10 C9 112.6(3) . . ?
C12 C10 C11 109.6(3) . . ?
C5 C13 C14 111.9(3) . . ?
C5 C13 C15 109.9(3) . . ?
C14 C13 C15 110.8(3) . . ?
Br4 Br3 Br2 174.33(3) . . ?
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 S1 2.2484(11) . ?
S1 C1 1.723(4) . ?
N1 C1 1.351(3) . ?
N1 C2 1.379(4) . ?
N1 C4 1.456(4) . ?
C2 C2 1.371(6) 4_565 ?
C2 C3 1.487(4) . ?
C4 C5 1.401(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.396(4) . ?
C5 C13 1.518(4) . ?
C6 C7 1.383(5) . ?
C7 C8 1.383(5) . ?
C8 C9 1.395(4) . ?
C9 C10 1.528(4) . ?
C10 C11 1.530(5) . ?
C10 C12 1.521(5) . ?
C13 C14 1.531(5) . ?
C13 C15 1.533(5) . ?
Br2 Br3 2.6042(9) . ?
Br3 Br4 2.4906(9) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.4177 2.1660 1.0342 0.2133 0.8923 0.3978
0.0022 -3.8324 5.7857 0.1679 0.6988 -0.6953
-5.8619 -4.0157 1.4044 -0.1576 -0.6609 -0.7338
0.1481 3.9319 -5.8165 -0.1637 -0.6812 0.7135
4.5921 3.6169 -5.3822 -0.1817 0.0445 0.9823
-2.8735 8.8654 3.3882 0.9664 -0.2315 -0.1121
-4.0982 -5.9341 4.7985 -0.0452 0.0098 -0.9989
2.6614 -9.1998 -3.1399 -0.9708 0.2325 0.0592
