#------------------------------------------------------------------------------
#$Date: 2017-07-11 14:26:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198632 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/56/4085605.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_4085605
loop_
_publ_author_name
'Boselli, Luca'
'Carraz, Maëlle'
'Mazères, Serge'
'Paloque, Lucie'
'González, Germán'
'Benoit-Vical, Françoise'
'Valentin, Alexis'
'Hemmert, Catherine'
'Gornitzka, Heinz'
_publ_section_title
;
 Synthesis, Structures, and Biological Studies of Heterobimetallic
 Au(I)--Ru(II) Complexes Involving N-Heterocyclic Carbene-Based
 Multidentate Ligands
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1046
_journal_paper_doi               10.1021/om501158m
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C18 H21 Br N4'
_chemical_formula_weight         373.30
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                70.418(2)
_cell_angle_beta                 78.963(2)
_cell_angle_gamma                73.532(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1046(3)
_cell_length_b                   9.1978(4)
_cell_length_c                   12.9086(5)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      2.42
_cell_volume                     864.45(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43122
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         5.114
_exptl_absorpt_coefficient_mu    2.383
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0445P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3603
_reflns_number_total             4107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om501158m_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;Adding full bibliography for 4085605--4085609.cif.

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               4085605
#BEGIN Tags that were not found in dictionaries:
_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_min   0.449
_shelx_estimated_absorpt_t_max   0.797
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.22805(2) 0.75835(2) 0.04930(2) 0.03760(8) Uani 1 1 d . .
C1 C 0.1849(2) 0.1570(2) 0.02533(14) 0.0287(3) Uani 1 1 d . .
H1 H 0.1585 0.0606 0.0300 0.034 Uiso 1 1 calc R U
N1 N 0.29721(18) 0.22660(17) -0.04998(11) 0.0304(3) Uani 1 1 d . .
N2 N 0.11557(18) 0.24498(16) 0.09308(11) 0.0255(3) Uani 1 1 d . .
C2 C 0.2971(2) 0.3652(2) -0.03026(16) 0.0345(4) Uani 1 1 d . .
H2 H 0.3646 0.4390 -0.0721 0.041 Uiso 1 1 calc R U
C3 C 0.1841(2) 0.3764(2) 0.05898(15) 0.0303(4) Uani 1 1 d . .
H3 H 0.1567 0.4592 0.0923 0.036 Uiso 1 1 calc R U
C4 C -0.0048(2) 0.1995(2) 0.19241(14) 0.0323(4) Uani 1 1 d . .
H4A H -0.0762 0.1370 0.1796 0.039 Uiso 1 1 calc R U
H4B H -0.0833 0.2963 0.2072 0.039 Uiso 1 1 calc R U
C5 C 0.0929(2) 0.1021(2) 0.29139(14) 0.0278(3) Uani 1 1 d . .
C6 C 0.0991(3) 0.1631(2) 0.37457(16) 0.0354(4) Uani 1 1 d . .
H6 H 0.0377 0.2687 0.3719 0.042 Uiso 1 1 calc R U
C7 C 0.1945(2) 0.0705(2) 0.46144(14) 0.0321(4) Uani 1 1 d . .
H7 H 0.2005 0.1120 0.5185 0.039 Uiso 1 1 calc R U
C8 C 0.2811(2) -0.0828(2) 0.46452(13) 0.0266(3) Uani 1 1 d . .
C9 C 0.3837(2) -0.1878(2) 0.55772(14) 0.0286(3) Uani 1 1 d . .
C10 C 0.4882(3) -0.3334(2) 0.55266(16) 0.0379(4) Uani 1 1 d . .
H10 H 0.4983 -0.3661 0.4888 0.045 Uiso 1 1 calc R U
C11 C 0.5778(3) -0.4309(3) 0.64164(19) 0.0461(5) Uani 1 1 d . .
H11 H 0.6503 -0.5315 0.6398 0.055 Uiso 1 1 calc R U
C12 C 0.5605(3) -0.3803(3) 0.73293(17) 0.0441(5) Uani 1 1 d . .
H12 H 0.6193 -0.4456 0.7956 0.053 Uiso 1 1 calc R U
C13 C 0.4558(3) -0.2325(3) 0.73137(16) 0.0464(5) Uani 1 1 d . .
H13 H 0.4459 -0.1971 0.7940 0.056 Uiso 1 1 calc R U
C14 C 0.1832(2) -0.0534(2) 0.30111(15) 0.0349(4) Uani 1 1 d . .
H14 H 0.1791 -0.0973 0.2450 0.042 Uiso 1 1 calc R U
N3 N 0.2763(2) -0.14568(19) 0.38531(13) 0.0357(3) Uani 1 1 d . .
N4 N 0.3668(2) -0.1355(2) 0.64564(13) 0.0400(4) Uani 1 1 d . .
C15 C 0.3948(3) 0.1686(3) -0.14267(17) 0.0436(5) Uani 1 1 d . .
H15A H 0.4502 0.0541 -0.1143 0.052 Uiso 1 1 calc R U
H15B H 0.4874 0.2260 -0.1775 0.052 Uiso 1 1 calc R U
C16 C 0.2768(3) 0.1929(3) -0.22924(17) 0.0468(5) Uani 1 1 d . .
H16A H 0.3474 0.1525 -0.2898 0.056 Uiso 1 1 calc R U
H16B H 0.1905 0.1283 -0.1949 0.056 Uiso 1 1 calc R U
C17 C 0.1829(3) 0.3614(3) -0.27790(19) 0.0503(5) Uani 1 1 d . .
H17A H 0.2680 0.4279 -0.3100 0.060 Uiso 1 1 calc R U
H17B H 0.1065 0.4010 -0.2185 0.060 Uiso 1 1 calc R U
C18 C 0.0753(4) 0.3780(3) -0.3667(2) 0.0578(6) Uani 1 1 d . .
H18A H 0.1504 0.3387 -0.4256 0.087 Uiso 1 1 calc R U
H18B H 0.0182 0.4901 -0.3976 0.087 Uiso 1 1 calc R U
H18C H -0.0123 0.3160 -0.3346 0.087 Uiso 1 1 calc R U
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N1 C1 N2 108.41(15)
C1 N1 C2 108.48(15)
C1 N1 C15 124.61(16)
C2 N1 C15 126.79(16)
C1 N2 C3 108.86(14)
C1 N2 C4 124.18(15)
C3 N2 C4 126.81(15)
C3 C2 N1 107.28(15)
C2 C3 N2 106.95(16)
N2 C4 C5 110.74(14)
C6 C5 C14 117.15(16)
C6 C5 C4 122.30(16)
C14 C5 C4 120.53(16)
C7 C6 C5 119.93(17)
C8 C7 C6 119.18(16)
N3 C8 C7 122.23(16)
N3 C8 C9 116.81(15)
C7 C8 C9 120.96(15)
N4 C9 C10 122.62(17)
N4 C9 C8 117.12(16)
C10 C9 C8 120.25(16)
C9 C10 C11 119.20(19)
C12 C11 C10 119.0(2)
C11 C12 C13 118.50(18)
N4 C13 C12 123.5(2)
N3 C14 C5 123.80(16)
C14 N3 C8 117.71(16)
C9 N4 C13 117.14(18)
N1 C15 C16 111.26(16)
C17 C16 C15 114.78(19)
C16 C17 C18 112.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.326(2)
C1 N2 1.328(2)
N1 C2 1.381(2)
N1 C15 1.473(2)
N2 C3 1.376(2)
N2 C4 1.471(2)
C2 C3 1.341(3)
C4 C5 1.510(2)
C5 C6 1.382(2)
C5 C14 1.385(3)
C6 C7 1.378(3)
C7 C8 1.376(2)
C8 N3 1.344(2)
C8 C9 1.490(2)
C9 N4 1.344(2)
C9 C10 1.382(3)
C10 C11 1.382(3)
C11 C12 1.376(3)
C12 C13 1.379(3)
C13 N4 1.349(3)
C14 N3 1.343(2)
C15 C16 1.528(3)
C16 C17 1.496(3)
C17 C18 1.513(3)
