#------------------------------------------------------------------------------
#$Date: 2022-02-16 01:59:30 +0200 (Wed, 16 Feb 2022) $
#$Revision: 272982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/95/7709515.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_7709515
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 I4 N2 Se'
_chemical_formula_sum            'C29 H40 I4 N2 Se'
_chemical_formula_weight         1003.19
_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             2021-09-07
_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                 110.816(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2704(2)
_cell_length_b                   16.8187(3)
_cell_length_c                   10.5634(2)
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5200
_cell_measurement_theta_min      4.4620
_cell_volume                     1705.56(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 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-120.00   99
  2  ω    -83.00  38.00   1.00    1.00    --  -41.68  19.00  60.00  121
  3  ω     27.00  98.00   1.00    1.00    --   41.68-125.00  60.00   71
  4  ω     23.00 107.00   1.00    6.50    --  106.01 -94.00 -60.00   84
  5  ω     97.00 178.00   1.00    6.50    --  106.01 125.00 -90.00   81
  6  ω    103.00 178.00   1.00    6.50    --  106.01  77.00  60.00   75
  7  ω     23.00 107.00   1.00    6.50    --  106.01 -94.00   0.00   84
  8  ω    103.00 178.00   1.00    6.50    --  106.01  77.00-150.00   75
  9  ω     33.00 112.00   1.00    6.50    --  106.01-125.00  90.00   79
 10  ω     33.00 132.00   1.00    6.50    --  106.01 -45.00 120.00   99
 11  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00-150.00   99
 12  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  30.00  101
 13  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
 14  ω     78.00 178.00   1.00    6.50    --  106.01  30.00-120.00  100
 15  ω     53.00 178.00   1.00    6.50    --  106.01  15.00   0.00  125
 16  ω     80.00 101.00   1.00    6.50    --  106.01  45.00  60.00   21
;
_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      -0.0175499000
_diffrn_orient_matrix_UB_12      0.0894288000
_diffrn_orient_matrix_UB_13      0.0211181000
_diffrn_orient_matrix_UB_21      -0.1594875000
_diffrn_orient_matrix_UB_22      -0.0103719000
_diffrn_orient_matrix_UB_23      -0.0539628000
_diffrn_orient_matrix_UB_31      0.0046423000
_diffrn_orient_matrix_UB_32      -0.0168421000
_diffrn_orient_matrix_UB_33      0.1448570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14762
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         4.478
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    30.052
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.633
_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            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_description       irregular
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.039
_refine_diff_density_max         6.202
_refine_diff_density_min         -2.223
_refine_diff_density_rms         0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0451
_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)+(0.0695P)²+4.7069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3028
_reflns_number_total             3515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt00010e2.cif
_cod_data_source_block           ms281--1
_cod_database_code               7709515
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C27 H36 I2 N2 Se'
_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   0.387
_shelx_estimated_absorpt_t_min   0.173
_reflns_odcompleteness_completeness 100.00
_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 2021-09-06
_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.762
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
I1 I 0.33228(5) 0.250000 0.32955(5) 0.01759(15) Uani 1 2 d S T P . .
I2 I 0.03510(7) 0.250000 0.09942(7) 0.0411(2) Uani 1 2 d S T P . .
I3 I 0.19122(6) 0.250000 -0.09444(6) 0.02741(17) Uani 1 2 d S T P . .
I4 I 0.37788(8) 0.250000 -0.23509(7) 0.0374(2) Uani 1 2 d S T P . .
Se1 Se 0.55771(9) 0.250000 0.54755(9) 0.0171(2) Uani 1 2 d S T P . .
N1 N 0.7860(5) 0.3147(3) 0.4825(5) 0.0164(10) Uani 1 1 d . . . . .
C1 C 0.7121(9) 0.250000 0.4928(9) 0.0159(16) Uani 1 2 d S T P . .
C2 C 0.9107(7) 0.2907(3) 0.4706(7) 0.0212(13) Uani 1 1 d . . . . .
C3 C 1.0226(7) 0.3472(4) 0.4706(8) 0.0275(15) Uani 1 1 d . . . . .
H3A H 1.083501 0.357949 0.564110 0.041 Uiso 1 1 calc GR . . . .
H3B H 0.980461 0.397022 0.426958 0.041 Uiso 1 1 calc GR . . . .
H3C H 1.077369 0.323725 0.420741 0.041 Uiso 1 1 calc GR . . . .
C4 C 0.7391(6) 0.3962(3) 0.4785(7) 0.0158(11) Uani 1 1 d . . . . .
C5 C 0.6560(7) 0.4278(4) 0.3524(7) 0.0191(12) Uani 1 1 d . . . . .
C6 C 0.6169(7) 0.5065(4) 0.3481(7) 0.0220(13) Uani 1 1 d . . . . .
H6 H 0.562686 0.530014 0.264116 0.026 Uiso 1 1 calc R . . . .
C7 C 0.6563(7) 0.5519(4) 0.4662(7) 0.0231(13) Uani 1 1 d . . . . .
H7 H 0.627606 0.605801 0.461868 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7358(7) 0.5196(4) 0.5884(7) 0.0210(12) Uani 1 1 d . . . . .
H8 H 0.760816 0.551406 0.667856 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7811(6) 0.4399(4) 0.5980(7) 0.0185(12) Uani 1 1 d . . . . .
C10 C 0.8671(7) 0.4066(4) 0.7352(7) 0.0256(14) Uani 1 1 d . . . . .
H10 H 0.893662 0.350759 0.722453 0.031 Uiso 1 1 calc R . . . .
C11 C 1.0008(8) 0.4547(5) 0.8008(8) 0.0367(18) Uani 1 1 d . . . . .
H11A H 1.057370 0.452478 0.743203 0.055 Uiso 1 1 calc GR . . . .
H11B H 1.053659 0.432252 0.889918 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.976870 0.510094 0.811224 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.7827(8) 0.4049(6) 0.8276(7) 0.0361(17) Uani 1 1 d . . . . .
H12A H 0.759705 0.459382 0.845016 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.837298 0.379334 0.913482 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.696558 0.374837 0.783980 0.054 Uiso 1 1 calc GR . . . .
C13 C 0.6086(7) 0.3784(4) 0.2219(7) 0.0228(13) Uani 1 1 d . . . . .
H13 H 0.600371 0.321771 0.247152 0.027 Uiso 1 1 calc R . . . .
C14 C 0.7168(9) 0.3817(6) 0.1529(8) 0.043(2) Uani 1 1 d . . . . .
H14A H 0.742216 0.437153 0.145250 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.677498 0.358155 0.062292 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.799923 0.351819 0.206920 0.064 Uiso 1 1 calc GR . . . .
C15 C 0.4672(8) 0.4043(5) 0.1228(8) 0.0319(16) Uani 1 1 d . . . . .
H15A H 0.397424 0.399544 0.166045 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.440614 0.370350 0.042222 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.472382 0.459730 0.096403 0.048 Uiso 1 1 calc GR . . . .
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'
I I -0.3257 6.8362 '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'
Se Se -0.7943 1.1372 '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
-7 0 3 0.0338
1 2 -7 0.0402
6 0 -5 0.0361
1 -2 6 0.0132
-2 4 6 0.0132
1 10 -2 0.0301
1 -5 -6 0.0210
-1 -11 1 0.0290
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
Se1 I1 I2 170.90(3) . . ?
I3 I2 I1 85.47(2) . . ?
I4 I3 I2 170.20(3) . . ?
C1 Se1 I1 108.0(3) . . ?
C1 N1 C2 109.5(5) . . ?
C1 N1 C4 125.0(5) . . ?
C2 N1 C4 125.4(5) . . ?
N1 C1 Se1 125.9(4) . . ?
N1 C1 Se1 125.9(4) 4_565 . ?
N1 C1 N1 107.1(7) 4_565 . ?
N1 C2 C3 123.4(5) . . ?
C2 C2 N1 106.9(3) 4_565 . ?
C2 C2 C3 129.6(3) 4_565 . ?
C5 C4 N1 117.9(6) . . ?
C9 C4 N1 118.7(6) . . ?
C9 C4 C5 123.3(5) . . ?
C4 C5 C13 122.6(6) . . ?
C6 C5 C4 117.7(6) . . ?
C6 C5 C13 119.7(6) . . ?
C5 C6 C7 120.5(6) . . ?
C8 C7 C6 120.9(6) . . ?
C7 C8 C9 120.9(6) . . ?
C4 C9 C8 116.7(6) . . ?
C4 C9 C10 124.2(5) . . ?
C8 C9 C10 119.1(6) . . ?
C9 C10 C11 111.3(6) . . ?
C9 C10 C12 110.5(6) . . ?
C12 C10 C11 110.1(6) . . ?
C14 C13 C5 110.8(6) . . ?
C15 C13 C5 112.5(6) . . ?
C15 C13 C14 109.8(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
I1 I2 3.1546(9) . ?
I1 Se1 2.6218(11) . ?
I2 I3 3.0163(10) . ?
I3 I4 2.8119(10) . ?
Se1 C1 1.872(8) . ?
N1 C1 1.353(7) . ?
N1 C2 1.390(8) . ?
N1 C4 1.449(7) . ?
C2 C2 1.370(12) 4_565 ?
C2 C3 1.491(8) . ?
C4 C5 1.406(9) . ?
C4 C9 1.390(9) . ?
C5 C6 1.380(9) . ?
C5 C13 1.533(9) . ?
C6 C7 1.393(10) . ?
C7 C8 1.371(10) . ?
C8 C9 1.411(8) . ?
C9 C10 1.511(9) . ?
C10 C11 1.530(9) . ?
C10 C12 1.519(10) . ?
C13 C14 1.531(10) . ?
C13 C15 1.521(10) . ?
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
-6.6444 0.4210 2.8826 0.2151 0.8998 0.3796
0.8794 2.2334 -6.5393 0.0462 0.1895 -0.9808
6.2507 0.2718 -4.5084 -0.1806 -0.7564 -0.6286
1.2000 -2.3916 5.7083 -0.1144 -0.4746 0.8727
-1.6839 3.6336 6.4384 0.4905 -0.1166 0.8636
1.3791 10.2394 -2.2935 0.8431 -0.2024 -0.4983
1.4481 -5.1727 -5.9984 -0.6147 0.1464 -0.7751
-0.9640 -10.7782 0.7867 -0.9304 0.2231 0.2910
