#------------------------------------------------------------------------------
#$Date: 2021-03-01 00:21:59 +0200 (Mon, 01 Mar 2021) $
#$Revision: 262321 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518511.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_4518511
loop_
_publ_author_name
'Massie, Allyssa A.'
'Schremmer, Claudia'
'Rüter, Isabelle'
'Dechert, Sebastian'
'Siewert, Inke'
'Meyer, Franc'
_publ_section_title
;
 Selective Electrocatalytic CO2 Reduction to CO by an NHC-Based
 Organometallic Heme Analogue
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3257
_journal_page_last               3267
_journal_paper_doi               10.1021/acscatal.0c04518
_journal_year                    2021
_chemical_formula_moiety         'C29 H39 Fe N9 O 2+, 2(C F3 O3 S -), C2 H3 N'
_chemical_formula_sum            'C33 H42 F6 Fe N10 O7 S2'
_chemical_formula_weight         924.73
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 125.760(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.072(5)
_cell_length_b                   14.465(4)
_cell_length_c                   15.452(4)
_cell_measurement_reflns_used    31110
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.966
_cell_measurement_theta_min      1.752
_cell_volume                     4366(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2015)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2015)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.966
_diffrn_reflns_theta_min         1.752
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_T_max  0.5745
_exptl_absorpt_correction_T_min  0.2823
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       block
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4666
_refine_ls_number_restraints     125
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1400P)²+0.5286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3510
_reflns_number_total             4666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c04518_si_002.cif
_cod_data_source_block           1CO-aam5
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4518511
_shelx_shelxl_version_number     2018/3
_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   0.781
_shelx_estimated_absorpt_t_max   0.834
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.500000 0.84320(4) 0.250000 0.0458(2) Uani 1 2 d S T P . .
O1 O 0.500000 1.0402(2) 0.250000 0.0820(10) Uani 1 2 d S T P . .
N1 N 0.66006(12) 0.86713(17) 0.41616(19) 0.0529(6) Uani 1 1 d . . . . .
N2 N 0.61088(11) 0.79848(16) 0.47655(19) 0.0491(5) Uani 1 1 d . . . . .
N3 N 0.50056(11) 0.80868(15) 0.43961(18) 0.0494(5) Uani 1 1 d . . . . .
N4 N 0.41973(12) 0.90211(16) 0.3375(2) 0.0535(6) Uani 1 1 d . . . . .
N5 N 0.500000 0.7060(2) 0.250000 0.0540(8) Uani 1 2 d S T P . .
C1 C 0.59736(13) 0.83647(18) 0.3851(2) 0.0486(6) Uani 1 1 d . . . . .
C2 C 0.71116(15) 0.8491(2) 0.5251(2) 0.0563(7) Uani 1 1 d . . . . .
C3 C 0.67967(14) 0.8065(2) 0.5632(2) 0.0535(7) Uani 1 1 d . . . . .
C4 C 0.78433(17) 0.8742(3) 0.5804(3) 0.0761(10) Uani 1 1 d . . . . .
H4A H 0.811720 0.839464 0.645460 0.114 Uiso 1 1 calc R U . . .
H4B H 0.790170 0.939043 0.596504 0.114 Uiso 1 1 calc R U . . .
H4C H 0.798404 0.860186 0.535192 0.114 Uiso 1 1 calc R U . . .
C5 C 0.70729(17) 0.7774(2) 0.6730(2) 0.0661(8) Uani 1 1 d . . . . .
H5A H 0.755817 0.787792 0.718395 0.099 Uiso 1 1 calc R U . . .
H5B H 0.698137 0.712862 0.673372 0.099 Uiso 1 1 calc R U . . .
H5C H 0.685857 0.812630 0.698646 0.099 Uiso 1 1 calc R U . . .
C6 C 0.56025(14) 0.7504(2) 0.4825(2) 0.0513(6) Uani 1 1 d . . . . .
H6A H 0.547098 0.693314 0.442102 0.062 Uiso 1 1 calc R U . . .
H6B H 0.579616 0.735100 0.556103 0.062 Uiso 1 1 calc R U . . .
C7 C 0.46871(14) 0.84901(18) 0.3441(2) 0.0486(6) Uani 1 1 d . . . . .
C8 C 0.47337(16) 0.8357(2) 0.4952(2) 0.0561(7) Uani 1 1 d . . . . .
C9 C 0.42185(16) 0.8942(2) 0.4294(3) 0.0587(7) Uani 1 1 d . . . . .
C10 C 0.5003(2) 0.7998(3) 0.6036(3) 0.0709(9) Uani 1 1 d . . . . .
H10A H 0.470042 0.817690 0.622095 0.106 Uiso 1 1 calc R U . . .
H10B H 0.544977 0.825013 0.654642 0.106 Uiso 1 1 calc R U . . .
H10C H 0.503083 0.733595 0.603690 0.106 Uiso 1 1 calc R U . . .
C11 C 0.3748(2) 0.9455(3) 0.4463(3) 0.0860(12) Uani 1 1 d . . . . .
H11A H 0.385257 0.929563 0.514631 0.129 Uiso 1 1 calc R U . . .
H11B H 0.328230 0.929031 0.391333 0.129 Uiso 1 1 calc R U . . .
H11C H 0.380735 1.010851 0.443662 0.129 Uiso 1 1 calc R U . . .
C12 C 0.500000 0.9619(3) 0.250000 0.0543(9) Uani 1 2 d S T P . .
C13 C 0.68154(17) 0.9044(3) 0.3511(3) 0.0693(9) Uani 1 1 d . . . . .
H13A H 0.696388 0.853054 0.328916 0.083 Uiso 1 1 calc R U . . .
H13B H 0.721054 0.943794 0.396429 0.083 Uiso 1 1 calc R U . . .
C14 C 0.37042(16) 0.9586(2) 0.2463(3) 0.0606(7) Uani 1 1 d . . . . .
H14A H 0.394910 0.998694 0.228949 0.073 Uiso 1 1 calc R U . . .
H14B H 0.346689 0.997608 0.265981 0.073 Uiso 1 1 calc R U . . .
C15 C 0.500000 0.6283(3) 0.250000 0.0648(11) Uani 1 2 d S T P . .
C16 C 0.500000 0.5283(4) 0.250000 0.129(3) Uani 1 2 d S T P . .
H16A H 0.523392 0.506218 0.321856 0.193 Uiso 0.5 1 calc R U P . .
H16B H 0.522943 0.506218 0.219998 0.193 Uiso 0.5 1 calc R U P . .
H16C H 0.453665 0.506218 0.208146 0.193 Uiso 0.5 1 calc R U P . .
N11 N 0.6598(5) 0.8197(8) 0.8742(7) 0.111(3) Uani 0.5 1 d . . P . .
C31 C 0.6653(4) 0.7472(7) 0.8795(6) 0.077(2) Uani 0.5 1 d . . P . .
C32 C 0.6808(6) 0.6450(7) 0.8897(8) 0.111(3) Uani 0.5 1 d . . P . .
H32A H 0.729430 0.635735 0.935938 0.167 Uiso 0.5 1 calc R U P . .
H32B H 0.662912 0.619711 0.820638 0.167 Uiso 0.5 1 calc R U P . .
H32C H 0.659852 0.614566 0.919115 0.167 Uiso 0.5 1 calc R U P . .
S1A S 0.35091(7) 0.48283(10) 0.37576(10) 0.0676(4) Uani 0.879(4) 1 d D . P A 1
O11A O 0.28195(15) 0.5068(3) 0.2884(3) 0.0995(13) Uani 0.879(4) 1 d D . P A 1
O12A O 0.3577(3) 0.4511(4) 0.4687(5) 0.1153(17) Uani 0.879(4) 1 d D . P A 1
O13A O 0.3893(2) 0.4303(3) 0.3485(3) 0.1034(12) Uani 0.879(4) 1 d D . P A 1
C21A C 0.3956(2) 0.5922(3) 0.4178(4) 0.0814(12) Uani 0.879(4) 1 d D . P A 1
F11A F 0.3632(2) 0.6543(3) 0.4339(4) 0.1395(16) Uani 0.879(4) 1 d D . P A 1
F12A F 0.4583(3) 0.5846(7) 0.5029(4) 0.1316(13) Uani 0.879(4) 1 d D . P A 1
F13A F 0.3991(3) 0.6304(4) 0.3443(3) 0.1394(17) Uani 0.879(4) 1 d D . P A 1
S1B S 0.3364(5) 0.5090(8) 0.3864(9) 0.0676(4) Uani 0.121(4) 1 d D . P A 2
O11B O 0.2982(13) 0.489(3) 0.2767(16) 0.0995(13) Uani 0.121(4) 1 d D . P A 2
O12B O 0.3003(14) 0.5698(16) 0.412(2) 0.1153(17) Uani 0.121(4) 1 d D . P A 2
O13B O 0.373(2) 0.443(2) 0.471(3) 0.1034(12) Uani 0.121(4) 1 d D . P A 2
C21B C 0.4019(12) 0.5831(18) 0.402(2) 0.0814(12) Uani 0.121(4) 1 d D . P A 2
F11B F 0.3735(18) 0.6651(16) 0.372(4) 0.1395(16) Uani 0.121(4) 1 d D . P A 2
F12B F 0.4590(18) 0.584(5) 0.495(3) 0.1316(13) Uani 0.121(4) 1 d D . P A 2
F13B F 0.4149(16) 0.568(2) 0.331(2) 0.1394(17) Uani 0.121(4) 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'
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'
F F 0.0171 0.0103 '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'
Fe Fe 0.3463 0.8444 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Fe1 N5 180.0 . . ?
C12 Fe1 C7 87.58(8) . 2_655 ?
N5 Fe1 C7 92.42(8) . 2_655 ?
C12 Fe1 C7 87.58(8) . . ?
N5 Fe1 C7 92.42(8) . . ?
C7 Fe1 C7 175.16(15) 2_655 . ?
C12 Fe1 C1 92.74(7) . 2_655 ?
N5 Fe1 C1 87.26(7) . 2_655 ?
C7 Fe1 C1 87.31(12) 2_655 2_655 ?
C7 Fe1 C1 92.92(12) . 2_655 ?
C12 Fe1 C1 92.74(7) . . ?
N5 Fe1 C1 87.26(7) . . ?
C7 Fe1 C1 92.92(12) 2_655 . ?
C7 Fe1 C1 87.32(12) . . ?
C1 Fe1 C1 174.52(15) 2_655 . ?
C1 N1 C2 111.9(2) . . ?
C1 N1 C13 129.5(3) . . ?
C2 N1 C13 118.1(2) . . ?
C1 N2 C3 112.9(2) . . ?
C1 N2 C6 123.8(2) . . ?
C3 N2 C6 123.2(2) . . ?
C7 N3 C8 112.5(2) . . ?
C7 N3 C6 122.3(2) . . ?
C8 N3 C6 125.0(2) . . ?
C7 N4 C9 111.3(2) . . ?
C7 N4 C14 124.9(2) . . ?
C9 N4 C14 123.8(2) . . ?
C15 N5 Fe1 180.0 . . ?
N1 C1 N2 102.8(2) . . ?
N1 C1 Fe1 136.0(2) . . ?
N2 C1 Fe1 121.04(19) . . ?
C3 C2 N1 106.5(3) . . ?
C3 C2 C4 129.7(3) . . ?
N1 C2 C4 123.7(3) . . ?
C2 C3 N2 105.8(3) . . ?
C2 C3 C5 129.9(3) . . ?
N2 C3 C5 124.2(3) . . ?
N3 C6 N2 109.7(2) . . ?
N3 C7 N4 104.0(2) . . ?
N3 C7 Fe1 124.77(19) . . ?
N4 C7 Fe1 130.5(2) . . ?
C9 C8 N3 105.3(3) . . ?
C9 C8 C10 132.1(3) . . ?
N3 C8 C10 122.5(3) . . ?
C8 C9 N4 106.9(2) . . ?
C8 C9 C11 129.4(3) . . ?
N4 C9 C11 123.7(3) . . ?
O1 C12 Fe1 180.0 . . ?
N1 C13 C14 117.2(3) . 2_655 ?
N4 C14 C13 114.2(3) . 2_655 ?
N5 C15 C16 180.0 . . ?
N11 C31 C32 173.9(11) . . ?
O12A S1A O13A 114.3(3) . . ?
O12A S1A O11A 114.4(3) . . ?
O13A S1A O11A 116.0(3) . . ?
O12A S1A C21A 103.1(3) . . ?
O13A S1A C21A 102.6(3) . . ?
O11A S1A C21A 104.1(3) . . ?
F12A C21A F11A 109.5(6) . . ?
F12A C21A F13A 106.7(5) . . ?
F11A C21A F13A 102.9(5) . . ?
F12A C21A S1A 112.6(5) . . ?
F11A C21A S1A 111.9(4) . . ?
F13A C21A S1A 112.7(4) . . ?
O11B S1B O13B 125(2) . . ?
O11B S1B O12B 112.5(18) . . ?
O13B S1B O12B 107.5(18) . . ?
O11B S1B C21B 100.9(15) . . ?
O13B S1B C21B 104.7(18) . . ?
O12B S1B C21B 102.8(14) . . ?
F12B C21B F11B 112(3) . . ?
F12B C21B F13B 108(3) . . ?
F11B C21B F13B 101(2) . . ?
F12B C21B S1B 116(2) . . ?
F11B C21B S1B 104.7(19) . . ?
F13B C21B S1B 113.7(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C12 1.717(4) . ?
Fe1 N5 1.984(4) . ?
Fe1 C7 1.992(3) 2_655 ?
Fe1 C7 1.992(3) . ?
Fe1 C1 2.035(3) 2_655 ?
Fe1 C1 2.035(3) . ?
O1 C12 1.133(5) . ?
N1 C1 1.363(3) . ?
N1 C2 1.412(4) . ?
N1 C13 1.475(4) . ?
N2 C1 1.366(4) . ?
N2 C3 1.399(4) . ?
N2 C6 1.452(4) . ?
N3 C7 1.336(4) . ?
N3 C8 1.406(4) . ?
N3 C6 1.449(3) . ?
N4 C7 1.360(3) . ?
N4 C9 1.395(4) . ?
N4 C14 1.451(4) . ?
N5 C15 1.124(6) . ?
C2 C3 1.350(4) . ?
C2 C4 1.485(4) . ?
C3 C5 1.477(4) . ?
C8 C9 1.348(4) . ?
C8 C10 1.491(5) . ?
C9 C11 1.499(4) . ?
C13 C14 1.498(5) 2_655 ?
C15 C16 1.446(7) . ?
N11 C31 1.054(12) . ?
C31 C32 1.510(14) . ?
S1A O12A 1.423(5) . ?
S1A O13A 1.436(4) . ?
S1A O11A 1.442(3) . ?
S1A C21A 1.807(5) . ?
C21A F12A 1.304(5) . ?
C21A F11A 1.307(6) . ?
C21A F13A 1.309(6) . ?
S1B O11B 1.409(17) . ?
S1B O13B 1.432(18) . ?
S1B O12B 1.443(17) . ?
S1B C21B 1.802(16) . ?
C21B F12B 1.288(17) . ?
C21B F11B 1.310(19) . ?
C21B F13B 1.316(19) . ?
