#------------------------------------------------------------------------------
#$Date: 2019-06-04 03:05:12 +0300 (Tue, 04 Jun 2019) $
#$Revision: 215667 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/35/7123586.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_7123586
loop_
_publ_author_name
'Coulson, Ben'
'Issacs, Mark'
'Lari, Leonardo'
'Douthwaite, Richard E. E.'
'Duhme-klair, Anne-Kathrin'
_publ_section_title
;
 Carbon Nitride as a Ligand: Edge-Site Coordination of ReCl(CO)3-fragments
 to g-C3N4
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02197C
_journal_year                    2019
_chemical_formula_moiety         'C13 H11 Cl N3 O3 Re, 0.59(H2 O)'
_chemical_formula_sum            'C13 H12.18 Cl N3 O3.59 Re'
_chemical_formula_weight         489.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-15 deposited with the CCDC.    2019-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.6764(2)
_cell_length_b                   12.05740(10)
_cell_length_c                   20.0284(2)
_cell_measurement_reflns_used    8829
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      31.7720
_cell_measurement_theta_min      3.9410
_cell_volume                     3049.38(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  70.00   1.00   50.00    --   25.54 -19.00  90.00  117
  2  ω    -20.00  67.00   1.00   50.00    --   25.54 -99.00 -90.00   87
  3  ω    -97.00 -35.00   1.00   50.00    --  -25.86 147.00  47.00   62
  4  ω      4.00  94.00   1.00   50.00    --   25.54  57.00  90.00   90
  5  ω     35.00 101.00   1.00   50.00    --   25.54 178.00 120.00   66
  6  ω      4.00  29.00   1.00   50.00    --   25.54  57.00 -60.00   25
  7  ω      4.00  94.00   1.00   50.00    --   25.54  57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196795000
_diffrn_orient_matrix_UB_12      0.0539530000
_diffrn_orient_matrix_UB_13      -0.0055502000
_diffrn_orient_matrix_UB_21      -0.0499355000
_diffrn_orient_matrix_UB_22      0.0228577000
_diffrn_orient_matrix_UB_23      0.0058344000
_diffrn_orient_matrix_UB_31      0.0166079000
_diffrn_orient_matrix_UB_32      0.0048251000
_diffrn_orient_matrix_UB_33      0.0346392000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19729
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.088
_diffrn_reflns_theta_min         3.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.132
_exptl_crystal_description       plate
_exptl_crystal_F_000             1855
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.017
_refine_diff_density_max         1.516
_refine_diff_density_min         -2.003
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0136P)²+14.4651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4563
_reflns_number_total             4946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc02197c2.cif
_cod_data_source_block           ReCl(CO)3DMNA
_cod_database_code               7123586
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 H12.2 N3 O3.6 Cl Re'
_chemical_oxdiff_usercomment     'Ben Coulson BC269'
_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   0.874
_shelx_estimated_absorpt_t_min   0.368
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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, All O(H,H) groups
2. Others
 Sof(O5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(O4)=Sof(H4A)=Sof(H4B)=FVAR(2)
3.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C4(H4)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_olex2_date_sample_data_collection 2017-08-08
_olex2_exptl_crystal_mounting_method 'oil on 75 micrometre micromount'
_olex2_submission_original_sample_id BC269
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.786
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.29208(2) 0.54075(2) 0.59840(2) 0.01857(4) Uani 1 1 d . . . .
Cl1 Cl 0.21668(7) 0.51367(8) 0.70811(4) 0.0351(2) Uani 1 1 d . . . .
N1 N 0.43104(19) 0.44777(18) 0.64334(11) 0.0153(4) Uani 1 1 d . . . .
O3 O 0.3942(2) 0.5671(2) 0.46704(12) 0.0340(6) Uani 1 1 d . . . .
N2 N 0.28872(19) 0.3568(2) 0.59893(11) 0.0179(5) Uani 1 1 d . . . .
O1 O 0.0836(2) 0.6132(3) 0.52221(13) 0.0403(7) Uani 1 1 d . . . .
C12 C 0.3177(3) 0.6937(3) 0.61465(18) 0.0324(8) Uani 1 1 d . . . .
C13 C 0.3558(3) 0.5559(2) 0.51654(15) 0.0224(6) Uani 1 1 d . . . .
C11 C 0.1607(3) 0.5856(3) 0.55201(16) 0.0285(7) Uani 1 1 d . . . .
O2 O 0.3329(3) 0.7856(2) 0.62519(18) 0.0550(9) Uani 1 1 d . . . .
C1 C 0.3884(2) 0.3461(2) 0.62946(13) 0.0142(5) Uani 1 1 d . . . .
N3 N 0.5737(3) 0.5530(2) 0.68573(14) 0.0252(6) Uani 1 1 d . . . .
C2 C 0.5293(2) 0.4539(2) 0.67155(13) 0.0154(5) Uani 1 1 d . . . .
C3 C 0.5893(2) 0.3548(2) 0.68645(13) 0.0170(5) Uani 1 1 d . . . .
H3 H 0.6605 0.3600 0.7054 0.020 Uiso 1 1 calc R . . .
C7 C 0.2315(2) 0.2663(3) 0.58583(14) 0.0202(6) Uani 1 1 d . . . .
C8 C 0.4389(2) 0.2452(2) 0.64440(13) 0.0140(5) Uani 1 1 d . . . .
C6 C 0.2759(2) 0.1622(3) 0.60106(14) 0.0219(6) Uani 1 1 d . . . .
H6 H 0.2336 0.0980 0.5917 0.026 Uiso 1 1 calc R . . .
C4 C 0.5454(2) 0.2538(2) 0.67374(13) 0.0161(5) Uani 1 1 d . . . .
H4 H 0.5854 0.1886 0.6843 0.019 Uiso 1 1 calc R . . .
C5 C 0.3787(2) 0.1486(2) 0.62926(14) 0.0187(5) Uani 1 1 d . . . .
C10 C 0.1199(3) 0.2813(4) 0.55689(17) 0.0337(8) Uani 1 1 d . . . .
H10A H 0.0765 0.3072 0.5919 0.051 Uiso 1 1 calc GR . . .
H10B H 0.0921 0.2103 0.5391 0.051 Uiso 1 1 calc GR . . .
H10C H 0.1177 0.3361 0.5207 0.051 Uiso 1 1 calc GR . . .
C9 C 0.4234(3) 0.0352(2) 0.64322(17) 0.0271(7) Uani 1 1 d . . . .
H9A H 0.4664 0.0134 0.6071 0.041 Uiso 1 1 calc GR . . .
H9B H 0.3653 -0.0179 0.6458 0.041 Uiso 1 1 calc GR . . .
H9C H 0.4676 0.0359 0.6859 0.041 Uiso 1 1 calc GR . . .
O4 O 0.5338(8) 0.7770(5) 0.7301(6) 0.076(5) Uani 0.458(12) 1 d . P A 1
H4A H 0.4787 0.8174 0.7257 0.114 Uiso 0.458(12) 1 d G P A 1
H4B H 0.5850 0.8225 0.7307 0.114 Uiso 0.458(12) 1 d G P A 1
O5 O 0.6439(19) 0.786(2) 0.7325(9) 0.036(7) Uani 0.130(10) 1 d . P B 2
H5A H 0.6907 0.7727 0.7644 0.055 Uiso 0.130(10) 1 d G P B 2
H5B H 0.5897 0.8069 0.7513 0.055 Uiso 0.130(10) 1 d G P B 2
H3A H 0.539(3) 0.604(4) 0.681(2) 0.026(11) Uiso 1 1 d . . . .
H3B H 0.633(5) 0.553(4) 0.711(3) 0.058(16) Uiso 1 1 d . . . .
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'
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 1 0.0132
3 -2 1 0.0902
-3 2 -1 0.0585
-2 2 3 0.0549
2 -2 -3 0.0689
0 0 -1 0.0384
0 0 1 0.0504
1 1 -1 0.0042
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
N1 Re1 Cl1 85.89(6) .
N1 Re1 N2 60.41(9) .
N2 Re1 Cl1 81.71(6) .
C12 Re1 Cl1 92.82(12) .
C12 Re1 N1 107.77(13) .
C12 Re1 N2 167.14(13) .
C12 Re1 C13 88.58(15) .
C12 Re1 C11 86.37(16) .
C13 Re1 Cl1 176.77(10) .
C13 Re1 N1 90.91(11) .
C13 Re1 N2 96.32(11) .
C13 Re1 C11 88.39(14) .
C11 Re1 Cl1 94.61(10) .
C11 Re1 N1 165.82(13) .
C11 Re1 N2 105.59(13) .
C1 N1 Re1 94.89(17) .
C2 N1 Re1 146.24(19) .
C2 N1 C1 118.7(2) .
C1 N2 Re1 94.55(17) .
C7 N2 Re1 146.5(2) .
C7 N2 C1 118.8(3) .
O2 C12 Re1 179.2(4) .
O3 C13 Re1 178.8(3) .
O1 C11 Re1 177.6(3) .
N1 C1 N2 110.1(2) .
N1 C1 C8 125.1(3) .
N2 C1 C8 124.7(3) .
C2 N3 H3A 118(3) .
C2 N3 H3B 117(3) .
H3A N3 H3B 123(5) .
N1 C2 N3 120.1(3) .
N1 C2 C3 120.3(2) .
N3 C2 C3 119.6(3) .
C2 C3 H3 119.7 .
C4 C3 C2 120.6(3) .
C4 C3 H3 119.7 .
N2 C7 C6 119.6(3) .
N2 C7 C10 117.5(3) .
C6 C7 C10 122.9(3) .
C1 C8 C4 115.1(2) .
C1 C8 C5 116.4(3) .
C5 C8 C4 128.5(3) .
C7 C6 H6 118.6 .
C5 C6 C7 122.7(3) .
C5 C6 H6 118.6 .
C3 C4 C8 120.1(2) .
C3 C4 H4 120.0 .
C8 C4 H4 120.0 .
C8 C5 C9 121.7(3) .
C6 C5 C8 117.6(3) .
C6 C5 C9 120.7(3) .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
C7 C10 H10C 109.5 .
H10A C10 H10B 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C5 C9 H9A 109.5 .
C5 C9 H9B 109.5 .
C5 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
O4 O4 H4A 56.7 2_656
O4 O4 H4B 124.8 2_656
H4A O4 H4B 104.5 .
H5A O5 H5B 105.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Re1 Cl1 2.4935(8) .
Re1 N1 2.212(2) .
Re1 N2 2.218(3) .
Re1 C12 1.896(4) .
Re1 C13 1.899(3) .
Re1 C11 1.912(3) .
N1 C1 1.358(3) .
N1 C2 1.324(4) .
O3 C13 1.150(4) .
N2 C1 1.360(4) .
N2 C7 1.324(4) .
O1 C11 1.149(4) .
C12 O2 1.141(4) .
C1 C8 1.395(4) .
N3 C2 1.340(4) .
N3 H3A 0.76(4) .
N3 H3B 0.87(6) .
C2 C3 1.433(4) .
C3 H3 0.9500 .
C3 C4 1.353(4) .
C7 C6 1.398(4) .
C7 C10 1.492(4) .
C8 C4 1.428(4) .
C8 C5 1.411(4) .
C6 H6 0.9500 .
C6 C5 1.384(4) .
C4 H4 0.9500 .
C5 C9 1.497(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
O4 O4 1.22(2) 2_656
O4 H4A 0.8493 .
O4 H4B 0.8503 .
O5 H5A 0.8498 .
O5 H5B 0.8501 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A O4 0.76(4) 2.31(4) 2.902(8) 136(4)
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
Re1 N1 C1 N2 -1.4(2)
Re1 N1 C1 C8 178.7(2)
Re1 N1 C2 N3 5.8(5)
Re1 N1 C2 C3 -173.6(2)
Re1 N2 C1 N1 1.4(2)
Re1 N2 C1 C8 -178.7(2)
Re1 N2 C7 C6 -176.5(2)
Re1 N2 C7 C10 1.6(5)
N1 C1 C8 C4 -3.0(4)
N1 C1 C8 C5 176.5(2)
N1 C2 C3 C4 -1.9(4)
N2 C1 C8 C4 177.2(2)
N2 C1 C8 C5 -3.3(4)
N2 C7 C6 C5 -0.5(4)
C1 N1 C2 N3 179.9(2)
C1 N1 C2 C3 0.5(4)
C1 N2 C7 C6 -2.5(4)
C1 N2 C7 C10 175.6(3)
C1 C8 C4 C3 1.4(4)
C1 C8 C5 C6 0.1(4)
C1 C8 C5 C9 -179.6(3)
N3 C2 C3 C4 178.7(3)
C2 N1 C1 N2 -178.1(2)
C2 N1 C1 C8 2.0(4)
C2 C3 C4 C8 0.8(4)
C7 N2 C1 N1 -175.3(2)
C7 N2 C1 C8 4.6(4)
C7 C6 C5 C8 1.7(4)
C7 C6 C5 C9 -178.6(3)
C4 C8 C5 C6 179.6(3)
C4 C8 C5 C9 -0.2(4)
C5 C8 C4 C3 -178.0(3)
C10 C7 C6 C5 -178.5(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
-1.0002 -1.0002 1.0003 -0.0792 0.0329 0.0132
2.9996 -2.0011 1.0009 -0.0545 -0.1897 0.0748
-2.9996 2.0011 -1.0009 0.0545 0.1897 -0.0748
-1.9993 2.0013 2.9996 0.0520 0.1631 0.0804
1.9993 -2.0013 -2.9996 -0.0520 -0.1631 -0.0804
-0.0001 -0.0001 -1.0001 0.0055 -0.0058 -0.0346
0.0001 0.0001 1.0001 -0.0055 0.0058 0.0346
1.0002 1.0002 -1.0003 0.0792 -0.0329 -0.0132
