#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:44:03 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256109 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705110.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_7705110
loop_
_publ_author_name
'Saab, Marina'
'Nelson, David J.'
'Tzouras, Nikolaos V.'
'A C A Bayrakdar, Tahani'
'Nolan, Steven P.'
'Nahra, Fady'
'Van Hecke, Kristof'
_publ_section_title
;
 Straightforward access to chalcogenoureas derived from N-heterocyclic
 carbenes and their coordination chemistry.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12068
_journal_page_last               12081
_journal_paper_doi               10.1039/d0dt02558e
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C15 H24 N2 S'
_chemical_formula_sum            'C15 H24 N2 S'
_chemical_formula_weight         264.42
_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             2019-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-17 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.545(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9143(8)
_cell_length_b                   9.1573(4)
_cell_length_c                   12.6229(7)
_cell_measurement_reflns_used    3305
_cell_measurement_temperature    100.16(10)
_cell_measurement_theta_max      73.4680
_cell_measurement_theta_min      5.9450
_cell_volume                     1463.04(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.16(10)
_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 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 120.00   99
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00 -60.00   71
  3  ω      6.00  83.00   1.00    1.00    --   41.68 -99.00 150.00   77
  4  ω     78.00 178.00   1.00    1.00    --  106.01  30.00 -30.00  100
  5  ω     97.00 178.00   1.00    1.00    --  106.01 125.00-150.00   81
  6  ω     23.00 107.00   1.00    1.00    --  106.01 -94.00 -30.00   84
  7  ω     23.00 107.00   1.00    1.00    --  106.01 -94.00-150.00   84
  8  ω     97.00 178.00   1.00    1.00    --  106.01 125.00 -90.00   81
  9  ω    103.00 178.00   1.00    1.00    --  106.01  77.00-120.00   75
 10  ω     33.00 112.00   1.00    1.00    --  106.01-125.00  60.00   79
 11  ω     33.00 132.00   1.00    1.00    --  106.01 -45.00-150.00   99
 12  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -60.00  101
 13  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
 14  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  30.00  101
 15  ω     77.00 178.00   1.00    1.00    --  106.01  61.00-150.00  101
 16  ω     78.00 178.00   1.00    1.00    --  106.01  30.00  60.00  100
 17  ω     80.00 144.00   1.00    1.00    --  106.01  45.00 120.00   64
 18  ω     78.00 178.00   1.00    1.00    --  106.01  30.00-180.00  100
;
_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      -0.0372013000
_diffrn_orient_matrix_UB_12      0.1578445000
_diffrn_orient_matrix_UB_13      0.0026572000
_diffrn_orient_matrix_UB_21      0.0424883000
_diffrn_orient_matrix_UB_22      0.0451130000
_diffrn_orient_matrix_UB_23      -0.0901491000
_diffrn_orient_matrix_UB_31      -0.1078445000
_diffrn_orient_matrix_UB_32      -0.0367149000
_diffrn_orient_matrix_UB_33      -0.0992996000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.922
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0438
_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)+(0.0376P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2166
_reflns_number_total             2919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02558e2.cif
_cod_data_source_block           ms19
_cod_depositor_comments
'Adding full bibliography for 7705109--7705119.cif.'
_cod_original_cell_volume        1463.04(15)
_cod_database_code               7705110
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H24 N2 S'
_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 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, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_olex2_date_sample_data_collection 2019-08-01
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.600
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
S1 S 0.31062(4) 0.53186(6) 0.52579(5) 0.01773(14) Uani 1 1 d . . . . .
N1 N 0.28169(14) 0.67819(19) 0.69955(15) 0.0161(4) Uani 1 1 d . . . . .
N2 N 0.44244(14) 0.69262(19) 0.71343(15) 0.0162(4) Uani 1 1 d . . . . .
C1 C 0.34523(16) 0.6365(2) 0.64655(18) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.33957(17) 0.7600(2) 0.79783(18) 0.0186(5) Uani 1 1 d . . . . .
H2 H 0.313663 0.802005 0.849678 0.022 Uiso 1 1 calc R . . . .
C3 C 0.43858(17) 0.7690(2) 0.80655(19) 0.0191(5) Uani 1 1 d . . . . .
H3 H 0.495736 0.818655 0.865639 0.023 Uiso 1 1 calc R . . . .
C4 C 0.53512(16) 0.6881(2) 0.68551(18) 0.0170(5) Uani 1 1 d . . . . .
H4 H 0.522314 0.612339 0.624073 0.020 Uiso 1 1 calc R . . . .
C5 C 0.63390(17) 0.6451(2) 0.79276(19) 0.0191(5) Uani 1 1 d . . . . .
H5A H 0.644888 0.714529 0.856910 0.023 Uiso 1 1 calc R . . . .
H5B H 0.624498 0.546316 0.818847 0.023 Uiso 1 1 calc R . . . .
C6 C 0.73019(17) 0.6464(2) 0.7642(2) 0.0207(5) Uani 1 1 d . . . . .
H6A H 0.794009 0.620812 0.834777 0.025 Uiso 1 1 calc R . . . .
H6B H 0.721117 0.572061 0.703830 0.025 Uiso 1 1 calc R . . . .
C7 C 0.74499(18) 0.7954(3) 0.7207(2) 0.0225(5) Uani 1 1 d . . . . .
H7A H 0.807362 0.793490 0.701920 0.027 Uiso 1 1 calc R . . . .
H7B H 0.757872 0.869099 0.782486 0.027 Uiso 1 1 calc R . . . .
C8 C 0.64697(17) 0.8379(2) 0.61217(19) 0.0218(5) Uani 1 1 d . . . . .
H8A H 0.637754 0.768809 0.548321 0.026 Uiso 1 1 calc R . . . .
H8B H 0.656698 0.936887 0.586682 0.026 Uiso 1 1 calc R . . . .
C9 C 0.54802(17) 0.8358(2) 0.63654(19) 0.0195(5) Uani 1 1 d . . . . .
H9A H 0.553240 0.913753 0.693013 0.023 Uiso 1 1 calc R . . . .
H9B H 0.485035 0.855724 0.563492 0.023 Uiso 1 1 calc R . . . .
C10 C 0.16597(17) 0.6636(2) 0.64423(19) 0.0179(5) Uani 1 1 d . . . . .
H10 H 0.148174 0.569257 0.600340 0.021 Uiso 1 1 calc R . . . .
C11 C 0.11900(17) 0.7876(2) 0.5575(2) 0.0221(5) Uani 1 1 d . . . . .
H11A H 0.148711 0.784844 0.498577 0.026 Uiso 1 1 calc R . . . .
H11B H 0.138473 0.882288 0.598805 0.026 Uiso 1 1 calc R . . . .
C12 C -0.00104(18) 0.7752(3) 0.4968(2) 0.0265(6) Uani 1 1 d . . . . .
H12A H -0.020227 0.686705 0.447279 0.032 Uiso 1 1 calc R . . . .
H12B H -0.029763 0.861015 0.445618 0.032 Uiso 1 1 calc R . . . .
C13 C -0.05079(18) 0.7668(3) 0.5840(2) 0.0285(6) Uani 1 1 d . . . . .
H13A H -0.040779 0.861071 0.625554 0.034 Uiso 1 1 calc R . . . .
H13B H -0.127652 0.749257 0.541739 0.034 Uiso 1 1 calc R . . . .
C14 C -0.00144(18) 0.6445(3) 0.6720(2) 0.0282(6) Uani 1 1 d . . . . .
H14A H -0.018911 0.549171 0.631492 0.034 Uiso 1 1 calc R . . . .
H14B H -0.031705 0.646034 0.730493 0.034 Uiso 1 1 calc R . . . .
C15 C 0.11863(18) 0.6607(3) 0.7339(2) 0.0225(5) Uani 1 1 d . . . . .
H15A H 0.136555 0.752274 0.779720 0.027 Uiso 1 1 calc R . . . .
H15B H 0.148700 0.577991 0.788138 0.027 Uiso 1 1 calc R . . . .
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'
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
-6 0 -3 0.0464
-3 5 0 0.0563
5 2 3 0.0779
3 -5 0 0.0248
-6 -1 7 0.0033
-4 -2 -5 0.0306
-9 1 4 0.0441
-2 3 7 0.0738
8 -2 -5 0.0177
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 N1 C2 109.63(18) . . ?
C1 N1 C10 123.06(18) . . ?
C2 N1 C10 126.08(17) . . ?
C1 N2 C3 109.69(17) . . ?
C1 N2 C4 125.73(17) . . ?
C3 N2 C4 124.25(18) . . ?
N1 C1 S1 126.83(16) . . ?
N2 C1 S1 127.53(15) . . ?
N2 C1 N1 105.61(18) . . ?
C3 C2 N1 107.63(18) . . ?
C2 C3 N2 107.44(19) . . ?
N2 C4 C5 110.51(17) . . ?
N2 C4 C9 109.51(17) . . ?
C5 C4 C9 111.91(18) . . ?
C6 C5 C4 110.12(17) . . ?
C7 C6 C5 110.94(18) . . ?
C6 C7 C8 110.40(18) . . ?
C7 C8 C9 111.05(18) . . ?
C4 C9 C8 111.03(17) . . ?
N1 C10 C11 109.35(17) . . ?
N1 C10 C15 111.95(18) . . ?
C11 C10 C15 110.90(18) . . ?
C10 C11 C12 111.03(19) . . ?
C11 C12 C13 111.8(2) . . ?
C14 C13 C12 111.17(19) . . ?
C13 C14 C15 111.49(19) . . ?
C10 C15 C14 109.84(19) . . ?
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
S1 C1 1.692(2) . ?
N1 C1 1.366(2) . ?
N1 C2 1.385(3) . ?
N1 C10 1.471(3) . ?
N2 C1 1.363(3) . ?
N2 C3 1.388(3) . ?
N2 C4 1.472(3) . ?
C2 C3 1.338(3) . ?
C4 C5 1.527(3) . ?
C4 C9 1.528(3) . ?
C5 C6 1.525(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.528(3) . ?
C8 C9 1.531(3) . ?
C10 C11 1.524(3) . ?
C10 C15 1.528(3) . ?
C11 C12 1.525(3) . ?
C12 C13 1.526(3) . ?
C13 C14 1.525(3) . ?
C14 C15 1.529(3) . ?
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
-6.0632 -0.4239 -3.2139 0.1501 0.0130 0.9886
-3.3710 5.4575 0.2712 0.9876 0.0785 0.1362
5.3190 2.0683 3.4327 0.1377 0.0098 -0.9904
3.2990 -5.4847 -0.3174 -0.9893 -0.0786 -0.1229
-6.4071 -1.1347 7.4700 0.0791 -0.9968 -0.0091
-3.7947 -1.8709 -4.9147 -0.1672 0.1974 0.9660
-8.7477 1.4141 3.8214 0.5588 -0.6524 0.5120
-1.8861 2.7022 7.1660 0.5157 -0.6042 -0.6074
8.3841 -1.7827 -4.7932 -0.6060 0.7079 -0.3628
