#------------------------------------------------------------------------------
#$Date: 2021-06-05 20:56:31 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265921 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/03/1560368.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_1560368
loop_
_publ_author_name
'Yang, Yong'
'Ertem, Mehmed Z.'
'Duan, Lele'
_publ_section_title
;
 An amide-based second coordination sphere promotes the dimer pathway of
 Mn-catalyzed CO2-to-CO reduction at low overpotential
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4779
_journal_page_last               4788
_journal_paper_doi               10.1039/D0SC05679K
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C16 H13 Br Mn N3 O4'
_chemical_formula_sum            'C16 H13 Br Mn N3 O4'
_chemical_formula_weight         446.14
_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     dual
_audit_creation_date             2019-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-06 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5955(4)
_cell_length_b                   10.5011(4)
_cell_length_c                   15.0027(6)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.37
_cell_volume                     1665.10(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      100.03
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         2.279
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.219
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0794 before and 0.0496 after correction. The Ratio of minimum to maximum transmission is 0.8169. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0227
_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)+(0.0190P)²+1.4295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0515
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3407
_reflns_number_total             3848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05679k3.cif
_cod_data_source_block           cxy0649_0m
_cod_depositor_comments
'Adding full bibliography for 1560367--1560369.cif.'
_cod_database_code               1560368
_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_max   0.565
_shelx_estimated_absorpt_t_min   0.466
_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
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.53174(2) 0.69675(2) 0.29635(2) 0.01817(6) Uani 1 1 d . . . . .
Mn1 Mn 0.57111(2) 0.48414(2) 0.22272(2) 0.01316(7) Uani 1 1 d . . . . .
O1 O 0.41044(13) 0.57841(14) 0.06663(9) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.30345(13) 0.31371(12) 0.14047(9) 0.0205(3) Uani 1 1 d . . . . .
O3 O 0.60264(13) 0.24177(13) 0.12876(10) 0.0250(3) Uani 1 1 d . . . . .
O4 O 0.77954(14) 0.59741(15) 0.12866(10) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.68667(14) 0.43594(14) 0.33242(10) 0.0142(3) Uani 1 1 d . . . . .
N2 N 0.44205(13) 0.40731(13) 0.30713(9) 0.0130(3) Uani 1 1 d . . . . .
N3 N 0.17196(14) 0.47574(14) 0.17318(10) 0.0160(3) Uani 1 1 d . . . . .
C1 C 0.46686(17) 0.53899(17) 0.12867(12) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.62965(16) 0.39631(16) 0.40550(12) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.49150(16) 0.38191(16) 0.39156(12) 0.0136(3) Uani 1 1 d . . . . .
C4 C 0.31728(16) 0.38548(16) 0.28958(12) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.23916(17) 0.34157(17) 0.35341(12) 0.0165(4) Uani 1 1 d . . . . .
H5 H 0.151943 0.326486 0.337972 0.020 Uiso 1 1 calc R . . . .
C6 C 0.28953(17) 0.31991(17) 0.43989(12) 0.0173(4) Uani 1 1 d . . . . .
H6 H 0.237392 0.291939 0.485011 0.021 Uiso 1 1 calc R . . . .
C7 C 0.41775(17) 0.34009(17) 0.45882(12) 0.0155(4) Uani 1 1 d . . . . .
H7 H 0.455092 0.325449 0.517360 0.019 Uiso 1 1 calc R . . . .
C8 C 0.26425(16) 0.39088(17) 0.19342(12) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.10546(19) 0.47098(19) 0.08450(13) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.149146 0.411904 0.046554 0.034 Uiso 1 1 calc GR . . . .
H9B H 0.104184 0.556154 0.057755 0.034 Uiso 1 1 calc GR . . . .
H9C H 0.018481 0.441695 0.089742 0.034 Uiso 1 1 calc GR . . . .
C10 C 0.12581(19) 0.56639(18) 0.23663(13) 0.0218(4) Uani 1 1 d . . . . .
H10A H 0.060235 0.526028 0.269890 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.090140 0.640693 0.204351 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.195986 0.593489 0.278379 0.033 Uiso 1 1 calc GR . . . .
C11 C 0.69790(17) 0.36564(17) 0.48525(12) 0.0160(4) Uani 1 1 d . . . . .
H11 H 0.655306 0.339206 0.535724 0.019 Uiso 1 1 calc R . . . .
C12 C 0.82878(17) 0.37412(17) 0.49019(12) 0.0182(4) Uani 1 1 d . . . . .
H12 H 0.877411 0.353114 0.543795 0.022 Uiso 1 1 calc R . . . .
C13 C 0.88695(17) 0.41379(18) 0.41538(13) 0.0195(4) Uani 1 1 d . . . . .
H13 H 0.976491 0.420503 0.416891 0.023 Uiso 1 1 calc R . . . .
C14 C 0.81347(17) 0.44366(18) 0.33825(12) 0.0184(4) Uani 1 1 d . . . . .
H14 H 0.854529 0.470786 0.287262 0.022 Uiso 1 1 calc R . . . .
C15 C 0.59117(17) 0.33394(18) 0.16637(12) 0.0177(4) Uani 1 1 d . . . . .
C16 C 0.69797(18) 0.55397(18) 0.16528(12) 0.0193(4) Uani 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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'
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
N1 Mn1 Br1 88.56(4) . . ?
N1 Mn1 N2 78.28(6) . . ?
N2 Mn1 Br1 86.63(4) . . ?
C1 Mn1 Br1 87.12(6) . . ?
C1 Mn1 N1 175.67(7) . . ?
C1 Mn1 N2 101.79(7) . . ?
C15 Mn1 Br1 176.82(6) . . ?
C15 Mn1 N1 94.41(7) . . ?
C15 Mn1 N2 92.87(7) . . ?
C15 Mn1 C1 89.92(8) . . ?
C16 Mn1 Br1 90.07(6) . . ?
C16 Mn1 N1 93.50(7) . . ?
C16 Mn1 N2 171.21(7) . . ?
C16 Mn1 C1 86.16(8) . . ?
C16 Mn1 C15 90.87(8) . . ?
C2 N1 Mn1 116.86(11) . . ?
C14 N1 Mn1 125.25(12) . . ?
C14 N1 C2 117.86(15) . . ?
C3 N2 Mn1 114.44(11) . . ?
C4 N2 Mn1 128.41(12) . . ?
C4 N2 C3 117.08(15) . . ?
C8 N3 C9 118.69(15) . . ?
C8 N3 C10 124.02(15) . . ?
C10 N3 C9 117.08(15) . . ?
O1 C1 Mn1 173.98(17) . . ?
N1 C2 C3 114.37(15) . . ?
N1 C2 C11 122.20(16) . . ?
C11 C2 C3 123.35(16) . . ?
N2 C3 C2 115.17(15) . . ?
N2 C3 C7 122.53(16) . . ?
C7 C3 C2 122.25(16) . . ?
N2 C4 C5 123.07(16) . . ?
N2 C4 C8 118.22(15) . . ?
C5 C4 C8 118.11(16) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.42(17) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.31(17) . . ?
C7 C6 H6 120.8 . . ?
C3 C7 H7 120.2 . . ?
C6 C7 C3 119.55(17) . . ?
C6 C7 H7 120.2 . . ?
O2 C8 N3 124.49(17) . . ?
O2 C8 C4 118.22(16) . . ?
N3 C8 C4 117.17(16) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11 120.4 . . ?
C12 C11 C2 119.23(17) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.53(17) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.36(17) . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 122.81(17) . . ?
N1 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
O3 C15 Mn1 177.92(17) . . ?
O4 C16 Mn1 179.33(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
Br1 Mn1 2.5385(3) . ?
Mn1 N1 2.0444(15) . ?
Mn1 N2 2.0903(15) . ?
Mn1 C1 1.8228(19) . ?
Mn1 C15 1.809(2) . ?
Mn1 C16 1.803(2) . ?
O1 C1 1.147(2) . ?
O2 C8 1.228(2) . ?
O3 C15 1.131(2) . ?
O4 C16 1.151(2) . ?
N1 C2 1.354(2) . ?
N1 C14 1.343(2) . ?
N2 C3 1.363(2) . ?
N2 C4 1.349(2) . ?
N3 C8 1.342(2) . ?
N3 C9 1.462(2) . ?
N3 C10 1.455(2) . ?
C2 C3 1.472(2) . ?
C2 C11 1.391(2) . ?
C3 C7 1.390(2) . ?
C4 C5 1.388(3) . ?
C4 C8 1.512(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 N1 C2 C3 5.77(19) . . . . ?
Mn1 N1 C2 C11 -177.46(13) . . . . ?
Mn1 N1 C14 C13 177.73(14) . . . . ?
Mn1 N2 C3 C2 -7.88(18) . . . . ?
Mn1 N2 C3 C7 174.78(13) . . . . ?
Mn1 N2 C4 C5 -175.56(13) . . . . ?
Mn1 N2 C4 C8 13.5(2) . . . . ?
N1 C2 C3 N2 1.6(2) . . . . ?
N1 C2 C3 C7 178.92(16) . . . . ?
N1 C2 C11 C12 -0.9(3) . . . . ?
N2 C3 C7 C6 1.7(3) . . . . ?
N2 C4 C5 C6 0.8(3) . . . . ?
N2 C4 C8 O2 62.6(2) . . . . ?
N2 C4 C8 N3 -121.00(18) . . . . ?
C2 N1 C14 C13 -0.4(3) . . . . ?
C2 C3 C7 C6 -175.48(16) . . . . ?
C2 C11 C12 C13 0.4(3) . . . . ?
C3 N2 C4 C5 1.3(2) . . . . ?
C3 N2 C4 C8 -169.66(15) . . . . ?
C3 C2 C11 C12 175.61(17) . . . . ?
C4 N2 C3 C2 174.84(15) . . . . ?
C4 N2 C3 C7 -2.5(2) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C4 C8 O2 -108.8(2) . . . . ?
C5 C4 C8 N3 67.6(2) . . . . ?
C5 C6 C7 C3 0.5(3) . . . . ?
C8 C4 C5 C6 171.71(16) . . . . ?
C9 N3 C8 O2 5.1(3) . . . . ?
C9 N3 C8 C4 -170.99(16) . . . . ?
C10 N3 C8 O2 179.69(17) . . . . ?
C10 N3 C8 C4 3.6(3) . . . . ?
C11 C2 C3 N2 -175.15(16) . . . . ?
C11 C2 C3 C7 2.2(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 N1 0.0(3) . . . . ?
C14 N1 C2 C3 -175.91(15) . . . . ?
C14 N1 C2 C11 0.9(3) . . . . ?
