#------------------------------------------------------------------------------
#$Date: 2022-09-06 12:58:49 +0300 (Tue, 06 Sep 2022) $
#$Revision: 277665 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/73/1567309.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_1567309
loop_
_publ_author_name
'Reid, Amelia G.'
'Moreno, Juan J.'
'Hooe, Shelby L.'
'Baugh, Kira R.'
'Thomas, Isobel H.'
'Dickie, Diane A.'
'Machan, Charles W.'
_publ_section_title
;
 Inverse potential scaling in co-electrocatalytic activity for CO2
 reduction through redox mediator tuning and catalyst design
;
_journal_issue                   33
_journal_name_full               'Chemical Science'
_journal_page_first              9595
_journal_page_last               9606
_journal_paper_doi               10.1039/D2SC03258A
_journal_volume                  13
_journal_year                    2022
_chemical_formula_sum            'C38 H48 N2 O2'
_chemical_formula_weight         564.78
_chemical_name_common            MnNRC8
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2020-02-18 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                106.415(5)
_cell_angle_beta                 93.806(5)
_cell_angle_gamma                97.936(6)
_cell_formula_units_Z            1
_cell_length_a                   6.142(2)
_cell_length_b                   9.094(3)
_cell_length_c                   15.431(5)
_cell_measurement_reflns_used    1572
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.9803
_cell_measurement_theta_min      2.7692
_cell_volume                     813.8(5)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Kappa APEXII Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3031
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.589
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0815
_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)+(0.1363P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2350
_reflns_number_gt                2146
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03258a3.cif
_cod_data_source_block           tbudhbpy02
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567306--1567312.cif.
;
_cod_database_code               1567309
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2634(4) 0.3610(3) 0.27422(18) 0.0297(7) Uani d . . . 1 . .
H H1 0.221(8) 0.388(6) 0.331(3) 0.048(13) Uiso d . . . 1 . .
N N1 0.2129(5) 0.5364(4) 0.4303(2) 0.0235(8) Uani d . . . 1 . .
C C1 0.1077(6) 0.5528(5) 0.5052(2) 0.0248(9) Uani d . . . 1 . .
C C2 0.1956(6) 0.6613(5) 0.5869(3) 0.0300(10) Uani d . . . 1 . .
H H2 0.119032 0.6723 0.639259 0.036 Uiso calc U . R 1 . .
C C3 0.3965(7) 0.7530(5) 0.5908(3) 0.0332(10) Uani d . . . 1 . .
H H3 0.460203 0.827678 0.646367 0.04 Uiso calc U . R 1 . .
C C4 0.5054(7) 0.7363(5) 0.5139(3) 0.0305(10) Uani d . . . 1 . .
H H4 0.644439 0.798642 0.516301 0.037 Uiso calc U . R 1 . .
C C5 0.4090(6) 0.6272(5) 0.4330(2) 0.0255(9) Uani d . . . 1 . .
C C6 0.5109(6) 0.6012(5) 0.3466(2) 0.0249(9) Uani d . . . 1 . .
C C7 0.4369(6) 0.4702(4) 0.2707(2) 0.0233(9) Uani d . . . 1 . .
C C8 0.5395(6) 0.4480(4) 0.1898(2) 0.0223(8) Uani d . . . 1 . .
C C9 0.7147(6) 0.5615(4) 0.1878(2) 0.0208(8) Uani d . . . 1 . .
H H9 0.786001 0.547295 0.133902 0.025 Uiso calc U . R 1 . .
C C10 0.7924(6) 0.6961(4) 0.2608(2) 0.0235(9) Uani d . . . 1 . .
C C11 0.6890(6) 0.7118(4) 0.3389(2) 0.0225(8) Uani d . . . 1 . .
H H11 0.739453 0.800691 0.389621 0.027 Uiso calc U . R 1 . .
C C12 0.9735(6) 0.8232(4) 0.2525(2) 0.0247(9) Uani d . . . 1 . .
C C13 0.8643(7) 0.9346(5) 0.2130(3) 0.0351(10) Uani d . . . 1 . .
H H13A 0.782998 0.877129 0.153532 0.053 Uiso calc U . R 1 . .
H H13B 0.97813 1.015926 0.205984 0.053 Uiso calc U . R 1 . .
H H13C 0.761611 0.982155 0.25408 0.053 Uiso calc U . R 1 . .
C C14 1.1018(7) 0.9150(6) 0.3447(3) 0.0408(12) Uani d . . . 1 . .
H H14A 1.002233 0.970712 0.384095 0.061 Uiso calc U . R 1 . .
H H14B 1.223161 0.989745 0.3361 0.061 Uiso calc U . R 1 . .
H H14C 1.162085 0.843285 0.373099 0.061 Uiso calc U . R 1 . .
C C15 1.1417(6) 0.7560(5) 0.1893(3) 0.0324(10) Uani d . . . 1 . .
H H15A 1.205116 0.678333 0.211285 0.049 Uiso calc U . R 1 . .
H H15B 1.259848 0.839807 0.188635 0.049 Uiso calc U . R 1 . .
H H15C 1.067153 0.707031 0.127578 0.049 Uiso calc U . R 1 . .
C C16 0.4570(6) 0.3042(4) 0.1078(2) 0.0238(9) Uani d . . . 1 . .
C C17 0.2143(6) 0.3011(5) 0.0747(3) 0.0289(10) Uani d . . . 1 . .
H H17A 0.12364 0.303024 0.124775 0.043 Uiso calc U . R 1 . .
H H17B 0.161934 0.2062 0.024485 0.043 Uiso calc U . R 1 . .
H H17C 0.202582 0.392077 0.05363 0.043 Uiso calc U . R 1 . .
C C18 0.4825(7) 0.1559(5) 0.1335(3) 0.0322(10) Uani d . . . 1 . .
H H18A 0.63939 0.155808 0.149903 0.048 Uiso calc U . R 1 . .
H H18B 0.424228 0.064797 0.081669 0.048 Uiso calc U . R 1 . .
H H18C 0.400314 0.152479 0.185383 0.048 Uiso calc U . R 1 . .
C C19 0.5924(6) 0.3043(5) 0.0271(2) 0.0261(9) Uani d . . . 1 . .
H H19A 0.576856 0.396194 0.007561 0.039 Uiso calc U . R 1 . .
H H19B 0.53786 0.21027 -0.023383 0.039 Uiso calc U . R 1 . .
H H19C 0.748645 0.30638 0.045993 0.039 Uiso calc U . R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1 . . 108.(3) ?
C1 N1 C5 . . 120.4(3) ?
N1 C1 C2 . . 121.5(3) ?
N1 C1 C1 . 2_566 116.1(4) ?
C2 C1 C1 . 2_566 122.4(4) ?
C3 C2 C1 . . 118.7(3) ?
C3 C2 H2 . . 120.6 ?
C1 C2 H2 . . 120.6 ?
C2 C3 C4 . . 120.0(4) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C3 C4 C5 . . 119.2(4) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
N1 C5 C4 . . 120.2(3) ?
N1 C5 C6 . . 116.3(3) ?
C4 C5 C6 . . 123.5(3) ?
C7 C6 C11 . . 118.0(3) ?
C7 C6 C5 . . 122.7(3) ?
C11 C6 C5 . . 119.3(3) ?
O1 C7 C6 . . 120.3(3) ?
O1 C7 C8 . . 118.4(3) ?
C6 C7 C8 . . 121.2(3) ?
C9 C8 C7 . . 117.3(3) ?
C9 C8 C16 . . 122.2(3) ?
C7 C8 C16 . . 120.5(3) ?
C8 C9 C10 . . 123.9(3) ?
C8 C9 H9 . . 118.1 ?
C10 C9 H9 . . 118.1 ?
C11 C10 C9 . . 116.7(3) ?
C11 C10 C12 . . 121.4(3) ?
C9 C10 C12 . . 121.8(3) ?
C10 C11 C6 . . 122.8(3) ?
C10 C11 H11 . . 118.6 ?
C6 C11 H11 . . 118.6 ?
C13 C12 C10 . . 108.2(3) ?
C13 C12 C14 . . 108.8(3) ?
C10 C12 C14 . . 111.9(3) ?
C13 C12 C15 . . 108.5(3) ?
C10 C12 C15 . . 111.8(3) ?
C14 C12 C15 . . 107.5(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C12 C15 H15A . . 109.5 ?
C12 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C12 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C18 C16 C17 . . 110.4(3) ?
C18 C16 C8 . . 110.0(3) ?
C17 C16 C8 . . 110.5(3) ?
C18 C16 C19 . . 107.0(3) ?
C17 C16 C19 . . 107.3(3) ?
C8 C16 C19 . . 111.6(3) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.367(4) ?
O1 H1 . 0.91(5) ?
N1 C1 . 1.343(4) ?
N1 C5 . 1.354(5) ?
C1 C2 . 1.383(5) ?
C1 C1 2_566 1.494(8) ?
C2 C3 . 1.378(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.382(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.391(6) ?
C4 H4 . 0.95 ?
C5 C6 . 1.482(5) ?
C6 C7 . 1.410(5) ?
C6 C11 . 1.416(5) ?
C7 C8 . 1.412(5) ?
C8 C9 . 1.394(5) ?
C8 C16 . 1.538(5) ?
C9 C10 . 1.409(5) ?
C9 H9 . 0.95 ?
C10 C11 . 1.380(5) ?
C10 C12 . 1.529(5) ?
C11 H11 . 0.95 ?
C12 C13 . 1.527(6) ?
C12 C14 . 1.530(6) ?
C12 C15 . 1.537(5) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C18 . 1.534(6) ?
C16 C17 . 1.537(5) ?
C16 C19 . 1.542(5) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.91(5) 1.73(5) 2.550(4) 147.(5) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . -0.4(6) ?
C5 N1 C1 C1 . . . 2_566 179.8(4) ?
N1 C1 C2 C3 . . . . -0.5(6) ?
C1 C1 C2 C3 2_566 . . . 179.3(5) ?
C1 C2 C3 C4 . . . . 0.4(7) ?
C2 C3 C4 C5 . . . . 0.5(7) ?
C1 N1 C5 C4 . . . . 1.3(6) ?
C1 N1 C5 C6 . . . . -179.5(3) ?
C3 C4 C5 N1 . . . . -1.4(6) ?
C3 C4 C5 C6 . . . . 179.5(4) ?
N1 C5 C6 C7 . . . . -12.9(5) ?
C4 C5 C6 C7 . . . . 166.2(4) ?
N1 C5 C6 C11 . . . . 166.7(3) ?
C4 C5 C6 C11 . . . . -14.2(6) ?
C11 C6 C7 O1 . . . . -179.0(3) ?
C5 C6 C7 O1 . . . . 0.5(5) ?
C11 C6 C7 C8 . . . . 1.2(5) ?
C5 C6 C7 C8 . . . . -179.3(3) ?
O1 C7 C8 C9 . . . . 179.5(3) ?
C6 C7 C8 C9 . . . . -0.7(5) ?
O1 C7 C8 C16 . . . . 0.0(5) ?
C6 C7 C8 C16 . . . . 179.8(3) ?
C7 C8 C9 C10 . . . . -0.6(5) ?
C16 C8 C9 C10 . . . . 178.8(3) ?
C8 C9 C10 C11 . . . . 1.5(5) ?
C8 C9 C10 C12 . . . . -175.2(3) ?
C9 C10 C11 C6 . . . . -1.0(5) ?
C12 C10 C11 C6 . . . . 175.7(3) ?
C7 C6 C11 C10 . . . . -0.3(5) ?
C5 C6 C11 C10 . . . . -179.9(3) ?
C11 C10 C12 C13 . . . . -90.4(4) ?
C9 C10 C12 C13 . . . . 86.1(4) ?
C11 C10 C12 C14 . . . . 29.5(5) ?
C9 C10 C12 C14 . . . . -154.0(4) ?
C11 C10 C12 C15 . . . . 150.2(4) ?
C9 C10 C12 C15 . . . . -33.3(5) ?
C9 C8 C16 C18 . . . . 119.0(4) ?
C7 C8 C16 C18 . . . . -61.6(4) ?
C9 C8 C16 C17 . . . . -118.8(4) ?
C7 C8 C16 C17 . . . . 60.6(4) ?
C9 C8 C16 C19 . . . . 0.4(5) ?
C7 C8 C16 C19 . . . . 179.8(3) ?
