#------------------------------------------------------------------------------
#$Date: 2015-12-09 16:29:51 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171207 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/67/7036788.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_7036788
loop_
_publ_author_name
'Chan, Chung Ying'
'Barnard, Peter J.'
_publ_section_title
;
 Rhenium complexes of bidentate, bis-bidentate and tridentate
 N-heterocyclic carbene ligands.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              19126
_journal_page_last               19140
_journal_paper_doi               10.1039/c5dt03295d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C22 H25 Cl N5 O3 Re, C2 H3 N'
_chemical_formula_sum            'C24 H28 Cl N6 O3 Re'
_chemical_formula_weight         670.17
_chemical_name_systematic        18
_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
_atom_sites_solution_primary     heavy
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-08-20 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                102.922(3)
_cell_angle_beta                 100.733(3)
_cell_angle_gamma                98.285(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0075(3)
_cell_length_b                   12.8704(5)
_cell_length_c                   13.4782(5)
_cell_measurement_temperature    173.20
_cell_volume                     1304.94(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.20
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11684
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.830
_exptl_absorpt_coefficient_mu    4.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_description       block
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0192
_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)+(0.0156P)²+0.3103P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0408
_refine_ls_wR_factor_ref         0.0422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4925
_reflns_number_total             5314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03295d2.cif
_cod_data_source_block           18
_cod_depositor_comments
'Adding full bibliography for 7036787--7036794.cif.'
_cod_original_cell_volume        1304.93(9)
_cod_database_code               7036788
_shelxl_version_number           2013-2
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1A-C1A
 1.15 with sigma of 0.02
 C1-O1
 1.15 with sigma of 0.02
 C1A-Re1
 1.94 with sigma of 0.02
 C1-Re1
 1.94 with sigma of 0.02
 Re1-Cl1A
 2.51 with sigma of 0.02
 Re1-Cl1
 2.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C1) = Uanis(C1A)
Uanis(O1) = Uanis(O1A)
4. Others
 Fixed Sof: Cl1(0.7) C1(0.7) Cl1A(0.3) O1(0.7) C1A(0.3) O1A(0.3)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C16(H16A,H16B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C6(H6), C10(H10), C18(H18), C22(H22), C20(H20), C19(H19),
 C21(H21)
5.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2013-01-04
_olex2_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with Paratone oil on a glass slide. A suitable single crystal was mounted in Paratone oil on a glass fibre and cooled rapidly to 173 K in a stream of cold N2 using an Oxford low temperature device. '
_olex2_submission_special_instructions 'No special instructions were received'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.58072(2) 0.81714(2) 0.69285(2) 0.01989(4) Uani 1 1 d D . . .
Cl1 Cl 0.68608(16) 0.73177(10) 0.53588(9) 0.0280(2) Uani 0.7 1 d D P A 1
C1 C 0.5080(9) 0.8931(4) 0.8110(4) 0.0407(15) Uani 0.7 1 d D P A 1
N1 N 0.3846(3) 0.56853(17) 0.65300(15) 0.0209(5) Uani 1 1 d . . . .
N5 N 0.7550(3) 0.43261(18) 0.72404(15) 0.0225(5) Uani 1 1 d . . . .
O2 O 0.8298(3) 0.73843(19) 0.85133(15) 0.0400(5) Uani 1 1 d . . . .
N3 N 0.2704(3) 0.81153(18) 0.49605(16) 0.0237(5) Uani 1 1 d . . . .
C3 C 0.7672(4) 0.9406(2) 0.7166(2) 0.0300(7) Uani 1 1 d . . . .
N2 N 0.2063(3) 0.67546(19) 0.67914(16) 0.0237(5) Uani 1 1 d . . . .
C4 C 0.3756(3) 0.6767(2) 0.67349(18) 0.0199(5) Uani 1 1 d . . . .
C12 C 0.5379(3) 0.5219(2) 0.64233(19) 0.0207(5) Uani 1 1 d . . . .
H12A H 0.6290 0.5771 0.6327 0.025 Uiso 1 1 calc R . . .
H12B H 0.5083 0.4597 0.5796 0.025 Uiso 1 1 calc R . . .
C8 C 0.3931(4) 0.8704(2) 0.58315(19) 0.0227(6) Uani 1 1 d . . . .
C2 C 0.7362(4) 0.7653(2) 0.7901(2) 0.0260(6) Uani 1 1 d . . . .
N4 N 0.3621(3) 0.97328(18) 0.59277(17) 0.0271(5) Uani 1 1 d . . . .
C16 C 0.8814(4) 0.4469(2) 0.8236(2) 0.0271(6) Uani 1 1 d . . . .
H16A H 0.9281 0.5255 0.8539 0.032 Uiso 1 1 calc R . . .
H16B H 0.9792 0.4118 0.8083 0.032 Uiso 1 1 calc R . . .
C13 C 0.6074(4) 0.4834(2) 0.73840(19) 0.0243(6) Uani 1 1 d . . . .
H13A H 0.6428 0.5461 0.8008 0.029 Uiso 1 1 calc R . . .
H13B H 0.5150 0.4307 0.7501 0.029 Uiso 1 1 calc R . . .
O3 O 0.8839(3) 1.0106(2) 0.73680(18) 0.0532(7) Uani 1 1 d . . . .
C14 C 0.2459(4) 0.6959(2) 0.44364(19) 0.0234(6) Uani 1 1 d . . . .
H14A H 0.1231 0.6610 0.4331 0.028 Uiso 1 1 calc R . . .
H14B H 0.3181 0.6601 0.4883 0.028 Uiso 1 1 calc R . . .
C15 C 0.7042(4) 0.3192(2) 0.6614(2) 0.0294(6) Uani 1 1 d . . . .
H15A H 0.5773 0.2956 0.6497 0.035 Uiso 1 1 calc R . . .
H15B H 0.7607 0.2724 0.7007 0.035 Uiso 1 1 calc R . . .
C5 C 0.2270(4) 0.5043(2) 0.6462(2) 0.0293(6) Uani 1 1 d . . . .
H5 H 0.2019 0.4273 0.6324 0.035 Uiso 1 1 calc R . . .
C17 C 0.8097(4) 0.4008(2) 0.9051(2) 0.0286(6) Uani 1 1 d . . . .
C9 C 0.1664(4) 0.8759(3) 0.4563(2) 0.0364(7) Uani 1 1 d . . . .
H9 H 0.0714 0.8527 0.3974 0.044 Uiso 1 1 calc R . . .
C7 C 0.1254(4) 0.7698(3) 0.7036(2) 0.0328(7) Uani 1 1 d . . . .
H7A H 0.1099 0.7820 0.7755 0.049 Uiso 1 1 calc GR . . .
H7B H 0.0123 0.7567 0.6553 0.049 Uiso 1 1 calc GR . . .
H7C H 0.1997 0.8340 0.6966 0.049 Uiso 1 1 calc GR . . .
C6 C 0.1167(4) 0.5714(2) 0.6628(2) 0.0315(7) Uani 1 1 d . . . .
H6 H -0.0020 0.5510 0.6632 0.038 Uiso 1 1 calc R . . .
C10 C 0.2249(4) 0.9774(3) 0.5167(2) 0.0371(8) Uani 1 1 d . . . .
H10 H 0.1800 1.0401 0.5084 0.045 Uiso 1 1 calc R . . .
C18 C 0.7434(4) 0.4672(3) 0.9784(2) 0.0377(8) Uani 1 1 d . . . .
H18 H 0.7462 0.5411 0.9781 0.045 Uiso 1 1 calc R . . .
C11 C 0.4605(5) 1.0701(2) 0.6715(2) 0.0391(8) Uani 1 1 d . . . .
H11A H 0.4633 1.0587 0.7412 0.059 Uiso 1 1 calc GR . . .
H11B H 0.4056 1.1322 0.6646 0.059 Uiso 1 1 calc GR . . .
H11C H 0.5791 1.0846 0.6617 0.059 Uiso 1 1 calc GR . . .
C23 C 0.2154(5) 0.2209(4) 0.8256(3) 0.0580(11) Uani 1 1 d . . . .
Cl1A Cl 0.4924(5) 0.9143(3) 0.8488(3) 0.0280(2) Uani 0.3 1 d D P A 2
C22 C 0.8074(5) 0.2938(3) 0.9087(2) 0.0412(8) Uani 1 1 d . . . .
H22 H 0.8546 0.2476 0.8605 0.049 Uiso 1 1 calc R . . .
C20 C 0.6692(5) 0.3209(4) 1.0535(3) 0.0565(11) Uani 1 1 d . . . .
H20 H 0.6200 0.2933 1.1036 0.068 Uiso 1 1 calc R . . .
C19 C 0.6734(5) 0.4264(4) 1.0515(2) 0.0526(10) Uani 1 1 d . . . .
H19 H 0.6280 0.4725 1.1009 0.063 Uiso 1 1 calc R . . .
C21 C 0.7365(5) 0.2538(3) 0.9825(3) 0.0571(11) Uani 1 1 d . . . .
H21 H 0.7343 0.1802 0.9841 0.069 Uiso 1 1 calc R . . .
N6 N 0.1944(5) 0.2638(3) 0.7603(3) 0.0741(11) Uani 1 1 d . . . .
C24 C 0.2396(6) 0.1609(4) 0.9067(3) 0.0780(14) Uani 1 1 d . . . .
H24A H 0.3233 0.2070 0.9691 0.117 Uiso 1 1 calc GR . . .
H24B H 0.2830 0.0951 0.8803 0.117 Uiso 1 1 calc GR . . .
H24C H 0.1285 0.1406 0.9247 0.117 Uiso 1 1 calc GR . . .
O1 O 0.4743(6) 0.9407(4) 0.8846(3) 0.0611(14) Uani 0.7 1 d D P A 1
C1A C 0.675(2) 0.7544(11) 0.5783(10) 0.0407(15) Uani 0.3 1 d D P A 2
O1A O 0.7371(16) 0.7197(9) 0.5039(7) 0.0611(14) Uani 0.3 1 d D P A 2
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C1 Re1 Cl1 175.46(18) .
C1 Re1 C3 88.9(2) .
C1 Re1 C4 89.81(19) .
C1 Re1 C8 92.4(2) .
C1 Re1 C2 86.8(2) .
C3 Re1 Cl1 87.07(9) .
C3 Re1 C4 177.22(10) .
C3 Re1 C8 96.11(11) .
C3 Re1 Cl1A 88.59(13) .
C4 Re1 Cl1 94.31(7) .
C4 Re1 C8 86.41(10) .
C4 Re1 Cl1A 90.05(12) .
C8 Re1 Cl1 85.97(7) .
C8 Re1 Cl1A 93.82(12) .
C2 Re1 Cl1 94.98(8) .
C2 Re1 C3 86.62(12) .
C2 Re1 C4 90.85(10) .
C2 Re1 C8 177.16(10) .
C2 Re1 Cl1A 85.44(13) .
C1A Re1 C3 84.7(4) .
C1A Re1 C4 96.6(4) .
C1A Re1 C8 88.8(5) .
C1A Re1 C2 92.3(5) .
C1A Re1 Cl1A 173.1(5) .
O1 C1 Re1 176.0(5) .
C4 N1 C12 126.8(2) .
C4 N1 C5 111.6(2) .
C5 N1 C12 121.6(2) .
C13 N5 C16 112.57(19) .
C13 N5 C15 112.9(2) .
C15 N5 C16 113.2(2) .
C8 N3 C14 128.0(2) .
C8 N3 C9 111.5(2) .
C9 N3 C14 120.5(2) .
O3 C3 Re1 174.7(3) .
C4 N2 C7 126.6(2) .
C4 N2 C6 111.5(2) .
C6 N2 C7 121.8(2) .
N1 C4 Re1 128.79(18) .
N2 C4 Re1 128.40(19) .
N2 C4 N1 102.8(2) .
N1 C12 C13 111.23(19) .
N3 C8 Re1 130.50(19) .
N4 C8 Re1 126.53(19) .
N4 C8 N3 102.7(2) .
O2 C2 Re1 177.1(2) .
C8 N4 C10 112.0(2) .
C8 N4 C11 126.0(2) .
C10 N4 C11 122.0(2) .
N5 C16 C17 115.1(2) .
N5 C13 C12 110.32(19) .
N3 C14 C15 110.8(2) 2_666
N5 C15 C14 112.3(2) 2_666
C6 C5 N1 106.7(3) .
C18 C17 C16 119.6(3) .
C22 C17 C16 122.0(3) .
C22 C17 C18 118.4(3) .
C10 C9 N3 106.9(3) .
C5 C6 N2 107.4(3) .
C9 C10 N4 106.8(3) .
C19 C18 C17 120.6(3) .
N6 C23 C24 177.5(5) .
C17 C22 C21 120.4(3) .
C19 C20 C21 119.9(3) .
C20 C19 C18 120.6(3) .
C20 C21 C22 120.1(4) .
O1A C1A Re1 176.5(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Re1 Cl1 2.5075(13) .
Re1 C1 1.909(6) .
Re1 C3 1.941(3) .
Re1 C4 2.192(3) .
Re1 C8 2.199(3) .
Re1 C2 1.933(3) .
Re1 Cl1A 2.473(4) .
Re1 C1A 1.912(11) .
C1 O1 1.142(5) .
N1 C4 1.372(3) .
N1 C12 1.458(3) .
N1 C5 1.381(3) .
N5 C16 1.479(3) .
N5 C13 1.454(3) .
N5 C15 1.469(3) .
O2 C2 1.155(3) .
N3 C8 1.369(3) .
N3 C14 1.465(3) .
N3 C9 1.377(4) .
C3 O3 1.145(3) .
N2 C4 1.370(3) .
N2 C7 1.459(4) .
N2 C6 1.374(4) .
C12 C13 1.526(3) .
C8 N4 1.364(3) .
N4 C10 1.372(4) .
N4 C11 1.454(4) .
C16 C17 1.522(4) .
C14 C15 1.520(3) 2_666
C15 C14 1.520(3) 2_666
C5 C6 1.336(4) .
C17 C18 1.390(4) .
C17 C22 1.387(4) .
C9 C10 1.340(4) .
C18 C19 1.384(4) .
C23 N6 1.139(5) .
C23 C24 1.474(6) .
C22 C21 1.390(4) .
C20 C19 1.360(6) .
C20 C21 1.382(5) .
C1A O1A 1.226(11) .
