#------------------------------------------------------------------------------
#$Date: 2017-09-16 05:37:31 +0300 (Sat, 16 Sep 2017) $
#$Revision: 200951 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/42/7044237.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_7044237
loop_
_publ_author_name
'Lamprecht, Zandria'
'Radhakrishnan, Shankara'
'Hildebrandt, Alexander'
'Lang, Heinrich'
'Liles, David Charles'
'Weststrate, Nora-ann'
'Lotz, Simon'
'Bezuidenhout, Daniela Ina'
_publ_section_title
;
 Mono-, di- and tetrarhenium Fischer carbene complexes with
 thienothiophene substituents
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02969A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H9 Cl N O4 Re S2'
_chemical_formula_sum            'C13 H9 Cl N O4 Re S2'
_chemical_formula_weight         528.98
_chemical_name_systematic
Chloro-(dimethylamino-(thieno[2,3-b]thiophen-2-yl)-carbene)-tetracarbonyl-rhenium
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic-phasing
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-08 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.742(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5331(8)
_cell_length_b                   11.7969(16)
_cell_length_c                   10.8497(15)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.105
_cell_measurement_theta_min      2.551
_cell_volume                     835.80(19)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker kappa Photon CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17956
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         2.551
_diffrn_source                   ' I\mS  micro focus'
_exptl_absorpt_coefficient_mu    7.692
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'
_exptl_crystal_colour            pale-orange
_exptl_crystal_density_diffrn    2.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.101
_refine_diff_density_max         1.156
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.025(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0354
_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)+(0.0158P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2970
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt02969a2.cif
_cod_data_source_block           mo_ZL317x4_0m_c
_cod_database_code               7044237
_shelx_shelxl_version_number     2016/6
_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   0.284
_shelx_estimated_absorpt_t_max   0.510
loop_
_space_group_symop_operation_xyz
'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
Re1 Re 0.25386(5) 0.77024(10) 0.82365(3) 0.03804(12) Uani 1 1 d . . . . .
Cl1 Cl 0.3919(4) 0.8845(2) 0.6520(3) 0.0517(7) Uani 1 1 d . . . . .
O1 O 0.1021(16) 0.6277(9) 1.0362(9) 0.090(3) Uani 1 1 d . . . . .
O2 O 0.6764(16) 0.6439(8) 0.8296(8) 0.068(3) Uani 1 1 d . . . . .
O3 O 0.4391(17) 0.9509(9) 1.0020(9) 0.089(3) Uani 1 1 d . . . . .
O4 O -0.1511(17) 0.9070(10) 0.8371(11) 0.101(4) Uani 1 1 d . . . . .
N1 N 0.0115(13) 0.6672(8) 0.5918(8) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.1614(19) 0.6793(11) 0.9551(12) 0.057(3) Uani 1 1 d . . . . .
C2 C 0.5228(18) 0.6872(9) 0.8260(10) 0.042(3) Uani 1 1 d . . . . .
C3 C 0.3738(19) 0.8826(12) 0.9381(12) 0.055(3) Uani 1 1 d . . . . .
C4 C -0.009(2) 0.8572(12) 0.8270(12) 0.061(4) Uani 1 1 d . . . . .
C6 C 0.1344(15) 0.6486(9) 0.6849(10) 0.037(3) Uani 1 1 d . . . . .
C7 C 0.2135(13) 0.5311(7) 0.6977(8) 0.039(3) Uani 1 1 d D . . . .
S1 S 0.4017(8) 0.4955(4) 0.5916(5) 0.0500(17) Uani 0.663(10) 1 d D . P A 1
S2 S 0.5792(10) 0.2505(6) 0.6392(7) 0.069(3) Uani 0.663(10) 1 d D . P A 1
C8 C 0.183(4) 0.4492(16) 0.783(2) 0.060(4) Uani 0.663(10) 1 d D . P A 1
H8 H 0.092197 0.455913 0.847171 0.072 Uiso 0.663(10) 1 calc R U P A 1
C9 C 0.306(4) 0.3526(13) 0.763(2) 0.043(6) Uani 0.663(10) 1 d D U P A 1
C10 C 0.421(3) 0.3640(12) 0.6596(19) 0.039(6) Uani 0.663(10) 1 d D . P A 1
C11 C 0.324(5) 0.2424(15) 0.818(3) 0.074(4) Uani 0.663(10) 1 d D . P A 1
H11 H 0.244540 0.215830 0.881469 0.089 Uiso 0.663(10) 1 calc R U P A 1
C12 C 0.476(5) 0.1810(16) 0.762(2) 0.070(7) Uani 0.663(10) 1 d D . P A 1
H12 H 0.517925 0.109497 0.788696 0.084 Uiso 0.663(10) 1 calc R U P A 1
S1A S 0.0917(17) 0.4344(9) 0.7984(12) 0.060(4) Uani 0.337(10) 1 d D . P A 2
S2A S 0.310(3) 0.1946(11) 0.8170(16) 0.074(4) Uani 0.337(10) 1 d D . P A 2
C8A C 0.383(5) 0.481(2) 0.648(4) 0.0500(17) Uani 0.337(10) 1 d D . P A 2
H8A H 0.461898 0.516208 0.588809 0.060 Uiso 0.337(10) 1 calc R U P A 2
C9A C 0.425(7) 0.371(3) 0.694(6) 0.039(6) Uani 0.337(10) 1 d D . P A 2
C10A C 0.264(6) 0.3308(19) 0.763(5) 0.043(6) Uani 0.337(10) 1 d D U P A 2
C11A C 0.572(7) 0.285(3) 0.668(6) 0.069(3) Uani 0.337(10) 1 d D . P A 2
H11A H 0.690986 0.296135 0.625154 0.083 Uiso 0.337(10) 1 calc R U P A 2
C12A C 0.512(9) 0.182(3) 0.717(6) 0.070(7) Uani 0.337(10) 1 d D . P A 2
H12A H 0.572968 0.113729 0.698263 0.084 Uiso 0.337(10) 1 calc R U P A 2
C13 C -0.0728(14) 0.7773(17) 0.5582(9) 0.053(3) Uani 1 1 d . . . . .
H13A H 0.009838 0.835921 0.595771 0.080 Uiso 1 1 calc R U . . .
H13B H -0.210220 0.783025 0.586478 0.080 Uiso 1 1 calc R U . . .
H13C H -0.073621 0.785824 0.470198 0.080 Uiso 1 1 calc R U . . .
C14 C -0.0667(19) 0.5765(11) 0.5080(12) 0.063(4) Uani 1 1 d . . . . .
H14A H 0.003011 0.580160 0.431444 0.095 Uiso 1 1 calc R U . . .
H14B H -0.211026 0.586740 0.492573 0.095 Uiso 1 1 calc R U . . .
H14C H -0.042758 0.503862 0.545656 0.095 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Re1 C3 92.1(5)
C1 Re1 C4 89.0(5)
C3 Re1 C4 88.2(5)
C1 Re1 C2 90.7(5)
C3 Re1 C2 89.4(5)
C4 Re1 C2 177.6(5)
C1 Re1 C6 91.8(5)
C3 Re1 C6 175.8(5)
C4 Re1 C6 93.4(4)
C2 Re1 C6 89.0(4)
C1 Re1 Cl1 177.1(4)
C3 Re1 Cl1 87.8(4)
C4 Re1 Cl1 93.8(4)
C2 Re1 Cl1 86.4(3)
C6 Re1 Cl1 88.3(3)
C6 N1 C13 124.8(9)
C6 N1 C14 123.5(10)
C13 N1 C14 111.7(9)
O1 C1 Re1 177.6(12)
O2 C2 Re1 177.5(10)
O3 C3 Re1 177.3(12)
O4 C4 Re1 175.2(12)
N1 C6 C7 116.0(9)
N1 C6 Re1 128.6(8)
C7 C6 Re1 115.4(7)
C8 C7 C6 132.1(10)
C8A C7 C6 130.0(10)
C8 C7 S1 113.4(8)
C6 C7 S1 114.2(6)
C8A C7 S1A 110.2(9)
C6 C7 S1A 119.6(7)
C10 S1 C7 88.8(5)
C10 S2 C12 91.1(7)
C7 C8 C9 112.0(11)
C7 C8 H8 124.0
C9 C8 H8 124.0
C10 C9 C8 111.8(10)
C10 C9 C11 112.6(11)
C8 C9 C11 135.2(13)
C9 C10 S2 112.1(8)
C9 C10 S1 113.7(8)
S2 C10 S1 133.5(9)
C12 C11 C9 110.3(12)
C12 C11 H11 124.8
C9 C11 H11 124.8
C11 C12 S2 113.1(10)
C11 C12 H12 123.4
S2 C12 H12 123.4
C10A S1A C7 90.7(7)
C10A S2A C12A 89.6(10)
C7 C8A C9A 113.5(13)
C7 C8A H8A 123.3
C9A C8A H8A 123.3
C10A C9A C8A 111.4(14)
C10A C9A C11A 112.8(13)
C8A C9A C11A 135(2)
C9A C10A S1A 112.9(11)
C9A C10A S2A 111.9(11)
S1A C10A S2A 134.0(14)
C12A C11A C9A 110.0(14)
C12A C11A H11A 125.0
C9A C11A H11A 125.0
C11A C12A S2A 113.5(14)
C11A C12A H12A 123.3
S2A C12A H12A 123.3
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
N1 C14 H14A 109.5
N1 C14 H14B 109.5
H14A C14 H14B 109.5
N1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Re1 C1 1.897(15)
Re1 C3 1.963(15)
Re1 C4 2.002(14)
Re1 C2 2.011(13)
Re1 C6 2.205(11)
Re1 Cl1 2.490(3)
O1 C1 1.147(15)
O2 C2 1.126(13)
O3 C3 1.138(14)
O4 C4 1.107(14)
N1 C6 1.290(13)
N1 C13 1.453(19)
N1 C14 1.485(13)
C6 C7 1.485(13)
C7 C8 1.358(12)
C7 C8A 1.380(13)
C7 S1 1.761(8)
C7 S1A 1.784(11)
S1 C10 1.721(10)
S2 C10 1.709(10)
S2 C12 1.722(12)
C8 C9 1.414(12)
C8 H8 0.9300
C9 C10 1.382(12)
C9 C11 1.432(12)
C11 C12 1.382(13)
C11 H11 0.9300
C12 H12 0.9300
S1A C10A 1.713(12)
S2A C10A 1.732(12)
S2A C12A 1.740(14)
C8A C9A 1.420(13)
C8A H8A 0.9300
C9A C10A 1.389(13)
C9A C11A 1.434(13)
C11A C12A 1.379(14)
C11A H11A 0.9300
C12A H12A 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C13 N1 C6 C7 -176.0(9)
C14 N1 C6 C7 6.2(15)
C13 N1 C6 Re1 1.0(15)
C14 N1 C6 Re1 -176.8(8)
N1 C6 C7 C8 -113(2)
Re1 C6 C7 C8 69(2)
N1 C6 C7 C8A 87(3)
Re1 C6 C7 C8A -90(3)
N1 C6 C7 S1 74.4(10)
Re1 C6 C7 S1 -103.1(7)
N1 C6 C7 S1A -96.9(11)
Re1 C6 C7 S1A 85.7(9)
C8 C7 S1 C10 4.3(19)
C6 C7 S1 C10 178.3(12)
C6 C7 C8 C9 -174.7(17)
S1 C7 C8 C9 -2(3)
C7 C8 C9 C10 -2(3)
C7 C8 C9 C11 -175(3)
C8 C9 C10 S2 177(2)
C11 C9 C10 S2 -9(3)
C8 C9 C10 S1 5(3)
C11 C9 C10 S1 180(2)
C12 S2 C10 C9 5(2)
C12 S2 C10 S1 174(3)
C7 S1 C10 C9 -5(2)
C7 S1 C10 S2 -175(2)
C10 C9 C11 C12 9(4)
C8 C9 C11 C12 -179(4)
C9 C11 C12 S2 -5(4)
C10 S2 C12 C11 0(3)
C8A C7 S1A C10A -3(3)
C6 C7 S1A C10A -179(2)
C6 C7 C8A C9A 172(4)
S1A C7 C8A C9A -4(5)
C7 C8A C9A C10A 11(7)
C7 C8A C9A C11A 176(7)
C8A C9A C10A S1A -13(7)
C11A C9A C10A S1A 178(5)
C8A C9A C10A S2A 178(5)
C11A C9A C10A S2A 9(8)
C7 S1A C10A C9A 9(5)
C7 S1A C10A S2A 175(5)
C12A S2A C10A C9A -13(6)
C12A S2A C10A S1A -179(6)
C10A C9A C11A C12A 2(9)
C8A C9A C11A C12A -164(9)
C9A C11A C12A S2A -12(9)
C10A S2A C12A C11A 14(6)
