#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:44:03 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256109 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705119.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_7705119
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 Au Cl N2 Se'
_chemical_formula_sum            'C15 H24 Au Cl N2 Se'
_chemical_formula_weight         543.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 107.901(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5976(3)
_cell_length_b                   14.8217(3)
_cell_length_c                   19.8001(5)
_cell_measurement_reflns_used    13230
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      29.4690
_cell_measurement_theta_min      2.6400
_cell_volume                     3797.32(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_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  85.00   1.00  178.25    --   10.40  38.00  30.00   99
  2  ω    -20.00  51.00   1.00  178.25    --   10.40 -99.00  90.00   71
  3  ω    -31.00  90.00   1.00  178.25    --   10.40  19.00 -60.00  121
  4  ω    -18.00  29.00   1.00  178.25    --   10.40  57.00 120.00   47
  5  ω    -20.00  51.00   1.00  178.25    --   10.40 -99.00 -90.00   71
;
_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      -0.0071473000
_diffrn_orient_matrix_UB_12      0.0324053000
_diffrn_orient_matrix_UB_13      -0.0274625000
_diffrn_orient_matrix_UB_21      0.0470452000
_diffrn_orient_matrix_UB_22      0.0212305000
_diffrn_orient_matrix_UB_23      0.0191965000
_diffrn_orient_matrix_UB_31      0.0271975000
_diffrn_orient_matrix_UB_32      -0.0281074000
_diffrn_orient_matrix_UB_33      -0.0171460000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21743
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.728
_diffrn_reflns_theta_min         2.636
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    9.799
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0173
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0147P)²+2.0416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0361
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4401
_reflns_number_total             4868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02558e2.cif
_cod_data_source_block           ms33
_cod_depositor_comments
'Adding full bibliography for 7705109--7705119.cif.'
_cod_database_code               7705119
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H24SeAuClN2
_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 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 2019-04-02
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.649
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
Au1 Au 0.50226(2) 0.12310(2) 0.71301(2) 0.01654(3) Uani 1 1 d . . . . .
Se1 Se 0.52908(2) 0.11845(2) 0.83710(2) 0.01671(5) Uani 1 1 d . . . . .
Cl1 Cl 0.47330(5) 0.12015(3) 0.59299(3) 0.02661(12) Uani 1 1 d . . . . .
N1 N 0.55242(12) 0.31093(10) 0.86170(9) 0.0145(3) Uani 1 1 d . . . . .
N2 N 0.70052(12) 0.24413(10) 0.87932(9) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.59751(14) 0.23050(13) 0.85979(10) 0.0142(4) Uani 1 1 d . . . . .
C2 C 0.62832(16) 0.37681(13) 0.88122(12) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.617672 0.439495 0.886142 0.022 Uiso 1 1 calc R . . . .
C3 C 0.72022(16) 0.33520(13) 0.89193(11) 0.0193(4) Uani 1 1 d . . . . .
H3 H 0.786226 0.363270 0.905594 0.023 Uiso 1 1 calc R . . . .
C4 C 0.77955(15) 0.17326(13) 0.88673(11) 0.0156(4) Uani 1 1 d . . . . .
H4 H 0.746149 0.113672 0.888869 0.019 Uiso 1 1 calc R . . . .
C5 C 0.81923(15) 0.17201(14) 0.82271(11) 0.0181(4) Uani 1 1 d . . . . .
H5A H 0.849033 0.231586 0.817509 0.022 Uiso 1 1 calc R . . . .
H5B H 0.761244 0.159965 0.779122 0.022 Uiso 1 1 calc R . . . .
C6 C 0.90190(16) 0.09871(15) 0.83223(12) 0.0230(5) Uani 1 1 d . . . . .
H6A H 0.869933 0.038716 0.832331 0.028 Uiso 1 1 calc R . . . .
H6B H 0.930127 0.100735 0.791744 0.028 Uiso 1 1 calc R . . . .
C7 C 0.98989(16) 0.11131(14) 0.90147(12) 0.0224(5) Uani 1 1 d . . . . .
H7A H 1.040760 0.061904 0.906978 0.027 Uiso 1 1 calc R . . . .
H7B H 1.025609 0.169159 0.900069 0.027 Uiso 1 1 calc R . . . .
C8 C 0.94773(18) 0.11117(16) 0.96388(13) 0.0290(5) Uani 1 1 d . . . . .
H8A H 1.005086 0.120507 1.008335 0.035 Uiso 1 1 calc R . . . .
H8B H 0.915895 0.051851 0.966915 0.035 Uiso 1 1 calc R . . . .
C9 C 0.86707(16) 0.18560(16) 0.95611(11) 0.0245(5) Uani 1 1 d . . . . .
H9A H 0.838957 0.183262 0.996646 0.029 Uiso 1 1 calc R . . . .
H9B H 0.899811 0.245316 0.956383 0.029 Uiso 1 1 calc R . . . .
C10 C 0.43948(14) 0.32793(13) 0.84286(11) 0.0162(4) Uani 1 1 d . . . . .
H10 H 0.403493 0.268424 0.838948 0.019 Uiso 1 1 calc R . . . .
C11 C 0.41614(17) 0.38231(15) 0.90163(12) 0.0223(5) Uani 1 1 d . . . . .
H11A H 0.457400 0.438555 0.910190 0.027 Uiso 1 1 calc R . . . .
H11B H 0.435832 0.346816 0.946144 0.027 Uiso 1 1 calc R . . . .
C12 C 0.30108(17) 0.40556(16) 0.88069(12) 0.0245(5) Uani 1 1 d . . . . .
H12A H 0.260368 0.349397 0.877063 0.029 Uiso 1 1 calc R . . . .
H12B H 0.287796 0.443809 0.917950 0.029 Uiso 1 1 calc R . . . .
C13 C 0.26657(16) 0.45529(14) 0.80996(12) 0.0205(4) Uani 1 1 d . . . . .
H13A H 0.191781 0.468797 0.797192 0.025 Uiso 1 1 calc R . . . .
H13B H 0.304270 0.513214 0.814316 0.025 Uiso 1 1 calc R . . . .
C14 C 0.28743(16) 0.39842(15) 0.75191(12) 0.0228(5) Uani 1 1 d . . . . .
H14A H 0.265869 0.432172 0.706580 0.027 Uiso 1 1 calc R . . . .
H14B H 0.246124 0.342275 0.745469 0.027 Uiso 1 1 calc R . . . .
C15 C 0.40214(16) 0.37460(13) 0.77073(11) 0.0187(4) Uani 1 1 d . . . . .
H15A H 0.413154 0.334250 0.733863 0.022 Uiso 1 1 calc R . . . .
H15B H 0.442814 0.430291 0.771855 0.022 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 0.0033 0.0016 '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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
18 6 -5 0.0610
-11 14 18 0.0193
-12 -14 -5 0.0883
17 -3 4 0.0128
-7 12 22 0.0126
-11 -5 -16 0.0087
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
Cl1 Au1 Se1 177.061(14) . . ?
C1 Se1 Au1 97.38(6) . . ?
C1 N1 C2 108.96(16) . . ?
C1 N1 C10 125.97(16) . . ?
C2 N1 C10 125.02(16) . . ?
C1 N2 C3 108.92(16) . . ?
C1 N2 C4 125.56(16) . . ?
C3 N2 C4 125.52(16) . . ?
N1 C1 Se1 126.14(14) . . ?
N1 C1 N2 107.52(16) . . ?
N2 C1 Se1 126.30(14) . . ?
C3 C2 N1 107.20(17) . . ?
C2 C3 N2 107.37(17) . . ?
N2 C4 C5 111.04(16) . . ?
N2 C4 C9 110.25(16) . . ?
C5 C4 C9 111.89(16) . . ?
C4 C5 C6 109.90(17) . . ?
C7 C6 C5 111.47(17) . . ?
C8 C7 C6 110.09(18) . . ?
C7 C8 C9 110.90(19) . . ?
C4 C9 C8 109.91(18) . . ?
N1 C10 C11 109.81(16) . . ?
N1 C10 C15 109.42(15) . . ?
C15 C10 C11 112.74(16) . . ?
C10 C11 C12 110.32(18) . . ?
C13 C12 C11 111.01(17) . . ?
C14 C13 C12 110.51(17) . . ?
C13 C14 C15 110.92(18) . . ?
C10 C15 C14 110.70(17) . . ?
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
Au1 Se1 2.3714(2) . ?
Au1 Cl1 2.2867(6) . ?
Se1 C1 1.8891(19) . ?
N1 C1 1.346(2) . ?
N1 C2 1.387(2) . ?
N1 C10 1.486(2) . ?
N2 C1 1.349(2) . ?
N2 C3 1.384(2) . ?
N2 C4 1.477(2) . ?
C2 C3 1.351(3) . ?
C4 C5 1.523(3) . ?
C4 C9 1.527(3) . ?
C5 C6 1.533(3) . ?
C6 C7 1.529(3) . ?
C7 C8 1.514(3) . ?
C8 C9 1.530(3) . ?
C10 C11 1.527(3) . ?
C10 C15 1.526(3) . ?
C11 C12 1.530(3) . ?
C12 C13 1.523(3) . ?
C13 C14 1.521(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
18.0697 6.4752 -4.8439 0.2137 0.8946 0.3925
-11.1099 13.6342 17.9621 0.0279 0.1116 -0.9934
-11.7355 -14.2363 -5.3866 -0.2295 -0.9577 0.1733
16.8836 -2.9706 4.4662 -0.3396 0.8170 0.4661
-6.5480 12.4964 22.2001 -0.1579 0.3834 -0.9100
-10.7131 -4.5742 -16.4602 0.3804 -0.9171 0.1194
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.100 0.544 0.008 7.3 0.0 ?
2 0.100 0.956 0.508 7.3 0.0 ?
3 0.250 0.143 0.000 129.3 43.8 ?
4 0.250 0.357 0.500 129.3 43.7 ?
5 0.400 0.544 0.992 7.3 0.0 ?
6 0.400 0.956 0.492 7.3 0.0 ?
7 0.600 0.044 0.508 7.3 0.0 ?
8 0.600 0.456 0.008 7.3 0.0 ?
9 0.750 0.643 0.500 129.3 43.8 ?
10 0.750 0.857 0.000 129.3 43.7 ?
11 0.900 0.044 0.492 7.3 0.0 ?
12 0.900 0.456 0.992 7.3 0.0 ?
