#------------------------------------------------------------------------------
#$Date: 2019-11-24 05:57:08 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236879 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/76/4087614.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_4087614
loop_
_publ_author_name
'Machan, Charles W.'
'Chabolla, Steven A.'
'Kubiak, Clifford P.'
_publ_section_title
;
 Reductive Disproportionation of Carbon Dioxide by an Alkyl-Functionalized
 Pyridine Monoimine Re(I) fac-Tricarbonyl Electrocatalyst
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4678
_journal_paper_doi               10.1021/acs.organomet.5b00406
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C16 H18 Cl N2 O3 Re'
_chemical_formula_sum            'C16 H18 Cl N2 O3 Re'
_chemical_formula_weight         507.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2014-06-05 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 102.154(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0949(8)
_cell_length_b                   8.8224(6)
_cell_length_c                   17.5025(12)
_cell_measurement_reflns_used    7365
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      3.06
_cell_volume                     1674.8(2)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10554
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.509
_diffrn_reflns_theta_min         2.597
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.430
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1362 before and 0.0357 after correction.
The Ratio of minimum to maximum transmission is 0.6191.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_recrystallization_method
'grown by layering pentane on top of a dichloromethane solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0154
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+1.5962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0356
_refine_ls_wR_factor_ref         0.0362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             3346
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00406_si_002.cif
_cod_data_source_block           ReMeCy_1
_cod_database_code               4087614
_shelxl_version_number           2013-4
_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.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Re1 Re 0.33803(2) 0.74372(2) 0.58156(2) 0.00909(4) Uani 1 1 d .
Cl1 Cl 0.13228(5) 0.82104(6) 0.60183(3) 0.01427(11) Uani 1 1 d .
O1 O 0.39419(15) 1.06661(18) 0.53498(11) 0.0189(4) Uani 1 1 d .
C2 C 0.3522(2) 0.7663(2) 0.37954(15) 0.0155(5) Uani 1 1 d .
H2A H 0.4042 0.8175 0.4252 0.019 Uiso 1 1 calc R
H2B H 0.3900 0.6668 0.3730 0.019 Uiso 1 1 calc R
N4 N 0.28233(17) 0.5174(2) 0.60512(11) 0.0115(4) Uani 1 1 d .
C1 C 0.1663(2) 0.2986(3) 0.55389(13) 0.0143(4) Uani 1 1 d .
H1 H 0.1125 0.2498 0.5117 0.017 Uiso 1 1 calc R
C10 C 0.3738(2) 0.9453(3) 0.55211(13) 0.0130(4) Uani 1 1 d .
C11 C 0.4169(2) 0.7995(3) 0.68536(14) 0.0141(4) Uani 1 1 d .
O8 O 0.58924(16) 0.63447(19) 0.55885(11) 0.0224(4) Uani 1 1 d .
C3 C 0.2034(2) 0.2250(3) 0.62484(16) 0.0169(5) Uani 1 1 d .
H3 H 0.1766 0.1246 0.6316 0.020 Uiso 1 1 calc R
N7 N 0.23442(16) 0.6575(2) 0.46965(10) 0.0099(3) Uani 1 1 d .
C16 C 0.4938(2) 0.6758(2) 0.56585(13) 0.0147(4) Uani 1 1 d .
C4 C 0.2797(2) 0.2997(3) 0.68549(14) 0.0179(5) Uani 1 1 d .
H4 H 0.3068 0.2514 0.7346 0.021 Uiso 1 1 calc R
C9 C 0.3162(2) 0.4458(3) 0.67364(14) 0.0156(5) Uani 1 1 d .
H9 H 0.3674 0.4977 0.7159 0.019 Uiso 1 1 calc R
C6 C 0.1039(2) 0.4513(3) 0.40085(14) 0.0199(5) Uani 1 1 d .
H6A H 0.0599 0.5281 0.3651 0.030 Uiso 1 1 calc GR
H6B H 0.0441 0.3851 0.4184 0.030 Uiso 1 1 calc GR
H6C H 0.1560 0.3907 0.3738 0.030 Uiso 1 1 calc GR
O3 O 0.46567(16) 0.8332(2) 0.74754(10) 0.0231(4) Uani 1 1 d .
C5 C 0.2231(2) 0.7419(2) 0.39485(14) 0.0135(5) Uani 1 1 d .
H5 H 0.1760 0.6770 0.3519 0.016 Uiso 1 1 calc R
C12 C 0.20848(19) 0.4442(2) 0.54498(13) 0.0108(4) Uani 1 1 d .
C13 C 0.1825(2) 0.5275(2) 0.46988(13) 0.0112(4) Uani 1 1 d .
C7 C 0.1516(2) 0.8889(3) 0.39630(14) 0.0169(5) Uani 1 1 d .
H7A H 0.1901 0.9491 0.4428 0.020 Uiso 1 1 calc R
H7B H 0.0659 0.8654 0.4002 0.020 Uiso 1 1 calc R
C8 C 0.1508(2) 0.9811(3) 0.32239(15) 0.0221(5) Uani 1 1 d .
H8A H 0.1042 0.9253 0.2765 0.027 Uiso 1 1 calc R
H8B H 0.1086 1.0789 0.3258 0.027 Uiso 1 1 calc R
C14 C 0.2814(2) 1.0108(3) 0.31155(16) 0.0230(5) Uani 1 1 d .
H14A H 0.2783 1.0701 0.2631 0.028 Uiso 1 1 calc R
H14B H 0.3269 1.0711 0.3561 0.028 Uiso 1 1 calc R
C15 C 0.3485(2) 0.8622(3) 0.30648(14) 0.0199(5) Uani 1 1 d .
H15A H 0.4338 0.8834 0.3007 0.024 Uiso 1 1 calc R
H15B H 0.3061 0.8051 0.2598 0.024 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'
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
N4 Re1 Cl1 85.28(5)
N4 Re1 N7 74.42(7)
C10 Re1 Cl1 91.84(6)
C10 Re1 N4 174.33(8)
C10 Re1 N7 100.45(8)
C11 Re1 Cl1 92.53(7)
C11 Re1 N4 98.58(9)
C11 Re1 C10 86.42(10)
C11 Re1 N7 172.43(8)
N7 Re1 Cl1 84.13(5)
C16 Re1 Cl1 177.61(7)
C16 Re1 N4 92.39(8)
C16 Re1 C10 90.45(9)
C16 Re1 C11 88.31(10)
C16 Re1 N7 94.77(8)
C15 C2 C5 111.4(2)
C9 N4 Re1 124.86(16)
C9 N4 C12 118.76(19)
C12 N4 Re1 116.38(15)
C3 C1 C12 119.5(2)
O1 C10 Re1 179.2(2)
O3 C11 Re1 179.2(2)
C4 C3 C1 119.0(2)
C5 N7 Re1 122.99(13)
C13 N7 Re1 117.35(15)
C13 N7 C5 119.66(19)
O8 C16 Re1 177.9(2)
C3 C4 C9 118.9(2)
N4 C9 C4 122.7(2)
N7 C5 C2 108.43(19)
N7 C5 C7 111.07(19)
C7 C5 C2 113.19(18)
N4 C12 C1 121.2(2)
N4 C12 C13 115.22(18)
C1 C12 C13 123.5(2)
N7 C13 C6 125.9(2)
N7 C13 C12 116.3(2)
C12 C13 C6 117.81(19)
C5 C7 C8 110.5(2)
C14 C8 C7 111.2(2)
C15 C14 C8 110.4(2)
C14 C15 C2 110.85(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Re1 Cl1 2.4786(5)
Re1 N4 2.1552(18)
Re1 C10 1.916(2)
Re1 C11 1.907(2)
Re1 N7 2.1883(18)
Re1 C16 1.903(2)
O1 C10 1.147(3)
C2 C5 1.527(3)
C2 C15 1.526(3)
N4 C9 1.337(3)
N4 C12 1.354(3)
C1 C3 1.385(3)
C1 C12 1.386(3)
C11 O3 1.148(3)
O8 C16 1.151(3)
C3 C4 1.378(4)
N7 C5 1.489(3)
N7 C13 1.284(3)
C4 C9 1.380(3)
C6 C13 1.493(3)
C5 C7 1.522(3)
C12 C13 1.480(3)
C7 C8 1.527(3)
C8 C14 1.523(4)
C14 C15 1.520(3)
