#------------------------------------------------------------------------------
#$Date: 2017-01-14 13:44:23 +0200 (Sat, 14 Jan 2017) $
#$Revision: 190520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/94/7119488.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_7119488
loop_
_publ_author_name
Gyandshwar
Kumar
Rao
Wendy
Pell
Ilia
Korobkov
Darrin
Richeson
_publ_section_title
;
 Electrocatalytic reduction of CO2 using Mn complexes with unconventional
 coordination environments
;
_journal_name_full               Chem.Commun.
_journal_page_first              8010
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C21 H17 Br Mn N2 O3 P'
_chemical_formula_weight         511.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-06 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.6715(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3120(2)
_cell_length_b                   11.1704(3)
_cell_length_c                   11.8045(4)
_cell_measurement_reflns_used    7022
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.58
_cell_volume                     1038.34(5)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8709
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.349
_diffrn_reflns_theta_min         1.821
_exptl_absorpt_coefficient_mu    2.662
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.056(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4779
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0240
_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)+(0.0088P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4564
_reflns_number_total             4779
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc03827a2.cif
_cod_data_source_block           dr171
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_database_code               7119488
_shelx_shelxl_version_number     2014/7
_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   0.523
_shelx_estimated_absorpt_t_max   0.618
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.54455(6) 0.20736(4) 0.73776(4) 0.02147(11) Uani 1 1 d D . . . .
Br1 Br 0.37697(4) 0.08470(3) 0.56183(3) 0.02580(9) Uani 0.93 1 d . . P A 1
C19 C 0.6611(10) 0.3020(5) 0.8539(6) 0.0410(8) Uani 0.93 1 d D . P A 1
O1 O 0.7363(5) 0.3679(3) 0.9324(3) 0.0410(8) Uani 0.93 1 d D . P A 1
Br1' Br 0.6823(9) 0.3466(9) 0.8774(7) 0.046(2) Uani 0.07 1 d . . P A 2
O1' O 0.326(6) 0.054(4) 0.528(3) 0.0410(8) Uani 0.07 1 d D . P A 2
C19' C 0.428(7) 0.113(5) 0.613(4) 0.0410(8) Uani 0.07 1 d D . P A 2
P1 P 0.68845(10) 0.03745(7) 0.81586(7) 0.02161(16) Uani 1 1 d . . . . .
O2 O 0.2943(4) 0.1708(3) 0.8632(2) 0.0463(7) Uani 1 1 d . . . . .
O3 O 0.3368(4) 0.4105(3) 0.6065(3) 0.0491(7) Uani 1 1 d . . . . .
N1 N 0.8289(4) 0.0260(3) 0.7391(2) 0.0259(6) Uani 1 1 d . . . . .
N2 N 0.7296(3) 0.2119(3) 0.6545(2) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.8382(4) 0.1195(3) 0.6650(3) 0.0229(6) Uani 1 1 d . . . . .
C2 C 0.9598(5) 0.1206(3) 0.6055(3) 0.0314(8) Uani 1 1 d . . . . .
H2A H 1.0359 0.0552 0.6141 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9682(5) 0.2163(4) 0.5348(3) 0.0351(8) Uani 1 1 d . . . . .
H3A H 1.0493 0.2173 0.4935 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8574(5) 0.3114(4) 0.5242(3) 0.0338(8) Uani 1 1 d . . . . .
H4A H 0.8622 0.3792 0.4769 0.041 Uiso 1 1 calc R U . . .
C5 C 0.7404(4) 0.3050(3) 0.5842(3) 0.0266(7) Uani 1 1 d . . . . .
H5A H 0.6630 0.3696 0.5757 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9639(5) -0.0642(3) 0.7698(3) 0.0367(8) Uani 1 1 d . . . . .
H6A H 0.9400 -0.1244 0.8226 0.055 Uiso 1 1 calc R U . . .
H6B H 0.9692 -0.1030 0.6965 0.055 Uiso 1 1 calc R U . . .
H6C H 1.0730 -0.0256 0.8106 0.055 Uiso 1 1 calc R U . . .
C7 C 0.5730(4) -0.1035(3) 0.7933(3) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.5867(4) -0.1874(3) 0.7094(3) 0.0259(6) Uani 1 1 d . . . . .
H8A H 0.6600 -0.1723 0.6636 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4941(5) -0.2927(3) 0.6925(3) 0.0322(7) Uani 1 1 d . . . . .
H9A H 0.5051 -0.3500 0.6360 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3855(5) -0.3146(3) 0.7578(3) 0.0376(8) Uani 1 1 d . . . . .
H10A H 0.3236 -0.3875 0.7473 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3674(5) -0.2303(3) 0.8382(3) 0.0355(8) Uani 1 1 d . . . . .
H11A H 0.2910 -0.2446 0.8817 0.043 Uiso 1 1 calc R U . . .
C12 C 0.4595(5) -0.1253(3) 0.8559(3) 0.0296(7) Uani 1 1 d . . . . .
H12A H 0.4454 -0.0676 0.9111 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8294(4) 0.0337(3) 0.9707(3) 0.0282(7) Uani 1 1 d . . . . .
C14 C 0.8132(5) -0.0443(4) 1.0579(3) 0.0384(8) Uani 1 1 d . . . . .
H14A H 0.7247 -0.1022 1.0383 0.046 Uiso 1 1 calc R U . . .
C15 C 0.9258(6) -0.0382(5) 1.1738(3) 0.0521(11) Uani 1 1 d . . . . .
H15A H 0.9141 -0.0918 1.2332 0.062 Uiso 1 1 calc R U . . .
C16 C 1.0547(6) 0.0458(5) 1.2025(4) 0.0540(12) Uani 1 1 d . . . . .
H16A H 1.1299 0.0513 1.2822 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0740(6) 0.1215(4) 1.1156(4) 0.0498(11) Uani 1 1 d . . . . .
H17A H 1.1653 0.1771 1.1347 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9603(5) 0.1166(3) 1.0003(3) 0.0396(9) Uani 1 1 d . . . . .
H18A H 0.9723 0.1704 0.9412 0.048 Uiso 1 1 calc R U . . .
C20 C 0.3900(5) 0.1846(3) 0.8133(3) 0.0288(7) Uani 1 1 d . . . . .
C21 C 0.4197(5) 0.3346(3) 0.6558(3) 0.0317(7) 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'
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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 '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
C19 Mn1 C20 90.1(3) . .
C20 Mn1 C19' 92.4(19) . .
C19 Mn1 C21 91.3(3) . .
C20 Mn1 C21 89.85(15) . .
C19' Mn1 C21 88(2) . .
C19 Mn1 N2 92.8(2) . .
C20 Mn1 N2 173.10(13) . .
C19' Mn1 N2 85.0(19) . .
C21 Mn1 N2 96.38(13) . .
C19 Mn1 P1 95.7(2) . .
C20 Mn1 P1 92.72(11) . .
C19' Mn1 P1 85(2) . .
C21 Mn1 P1 172.55(11) . .
N2 Mn1 P1 80.73(8) . .
C20 Mn1 Br1' 90.63(18) . .
C19' Mn1 Br1' 172.5(19) . .
C21 Mn1 Br1' 85.5(3) . .
N2 Mn1 Br1' 92.81(17) . .
P1 Mn1 Br1' 101.4(2) . .
C19 Mn1 Br1 175.8(2) . .
C20 Mn1 Br1 92.17(11) . .
C21 Mn1 Br1 85.20(11) . .
N2 Mn1 Br1 85.43(7) . .
P1 Mn1 Br1 87.73(3) . .
O1 C19 Mn1 178.3(7) . .
O1' C19' Mn1 171(6) . .
N1 P1 C7 106.13(14) . .
N1 P1 C13 101.65(15) . .
C7 P1 C13 105.42(15) . .
N1 P1 Mn1 102.05(10) . .
C7 P1 Mn1 118.60(11) . .
C13 P1 Mn1 120.62(11) . .
C1 N1 C6 118.9(3) . .
C1 N1 P1 118.0(2) . .
C6 N1 P1 121.6(2) . .
C1 N2 C5 118.1(3) . .
C1 N2 Mn1 120.8(2) . .
C5 N2 Mn1 121.0(2) . .
N2 C1 N1 117.7(3) . .
N2 C1 C2 121.0(3) . .
N1 C1 C2 121.3(3) . .
C3 C2 C1 119.8(3) . .
C2 C3 C4 119.4(3) . .
C5 C4 C3 118.2(3) . .
N2 C5 C4 123.5(3) . .
C12 C7 C8 118.8(3) . .
C12 C7 P1 119.3(2) . .
C8 C7 P1 121.8(2) . .
C9 C8 C7 120.3(3) . .
C10 C9 C8 120.2(3) . .
C11 C10 C9 119.8(3) . .
C10 C11 C12 120.5(3) . .
C11 C12 C7 120.3(3) . .
C18 C13 C14 119.2(3) . .
C18 C13 P1 115.9(3) . .
C14 C13 P1 124.9(3) . .
C13 C14 C15 120.3(4) . .
C16 C15 C14 120.0(4) . .
C17 C16 C15 120.0(4) . .
C16 C17 C18 120.1(4) . .
C13 C18 C17 120.5(4) . .
O2 C20 Mn1 178.7(3) . .
O3 C21 Mn1 176.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 C19 1.756(6) .
Mn1 C20 1.800(3) .
Mn1 C19' 1.82(3) .
Mn1 C21 1.841(4) .
Mn1 N2 2.075(2) .
Mn1 P1 2.2753(9) .
Mn1 Br1' 2.289(9) .
Mn1 Br1 2.5056(6) .
C19 O1 1.192(6) .
O1' C19' 1.27(3) .
P1 N1 1.696(3) .
P1 C7 1.819(3) .
P1 C13 1.829(3) .
O2 C20 1.142(4) .
O3 C21 1.130(5) .
N1 C1 1.380(4) .
N1 C6 1.465(5) .
N2 C1 1.350(4) .
N2 C5 1.352(4) .
C1 C2 1.404(4) .
C2 C3 1.371(5) .
C3 C4 1.385(6) .
C4 C5 1.375(5) .
C7 C12 1.394(4) .
C7 C8 1.394(4) .
C8 C9 1.385(5) .
C9 C10 1.383(5) .
C10 C11 1.379(5) .
C11 C12 1.379(5) .
C13 C18 1.386(5) .
C13 C14 1.388(5) .
C14 C15 1.390(5) .
C15 C16 1.382(7) .
C16 C17 1.378(7) .
C17 C18 1.388(6) .
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
C7 P1 N1 C1 131.8(3) . . . .
C13 P1 N1 C1 -118.1(3) . . . .
Mn1 P1 N1 C1 7.0(3) . . . .
C7 P1 N1 C6 -62.4(3) . . . .
C13 P1 N1 C6 47.6(3) . . . .
Mn1 P1 N1 C6 172.7(3) . . . .
C5 N2 C1 N1 178.6(3) . . . .
Mn1 N2 C1 N1 -4.1(4) . . . .
C5 N2 C1 C2 0.5(5) . . . .
Mn1 N2 C1 C2 177.8(2) . . . .
C6 N1 C1 N2 -168.9(3) . . . .
P1 N1 C1 N2 -2.8(4) . . . .
C6 N1 C1 C2 9.2(5) . . . .
P1 N1 C1 C2 175.3(3) . . . .
N2 C1 C2 C3 -0.4(5) . . . .
N1 C1 C2 C3 -178.4(3) . . . .
C1 C2 C3 C4 0.7(6) . . . .
C2 C3 C4 C5 -1.0(6) . . . .
C1 N2 C5 C4 -0.9(5) . . . .
Mn1 N2 C5 C4 -178.2(3) . . . .
C3 C4 C5 N2 1.2(6) . . . .
N1 P1 C7 C12 173.6(3) . . . .
C13 P1 C7 C12 66.3(3) . . . .
Mn1 P1 C7 C12 -72.5(3) . . . .
N1 P1 C7 C8 -10.5(3) . . . .
C13 P1 C7 C8 -117.9(3) . . . .
Mn1 P1 C7 C8 103.4(3) . . . .
C12 C7 C8 C9 -2.7(5) . . . .
P1 C7 C8 C9 -178.5(3) . . . .
C7 C8 C9 C10 0.8(5) . . . .
C8 C9 C10 C11 1.2(6) . . . .
C9 C10 C11 C12 -1.4(6) . . . .
C10 C11 C12 C7 -0.5(6) . . . .
C8 C7 C12 C11 2.5(5) . . . .
P1 C7 C12 C11 178.4(3) . . . .
N1 P1 C13 C18 53.6(3) . . . .
C7 P1 C13 C18 164.1(3) . . . .
Mn1 P1 C13 C18 -58.1(3) . . . .
N1 P1 C13 C14 -126.7(3) . . . .
C7 P1 C13 C14 -16.1(4) . . . .
Mn1 P1 C13 C14 121.6(3) . . . .
C18 C13 C14 C15 0.8(6) . . . .
P1 C13 C14 C15 -178.9(3) . . . .
C13 C14 C15 C16 -0.1(6) . . . .
C14 C15 C16 C17 -1.6(7) . . . .
C15 C16 C17 C18 2.4(7) . . . .
C14 C13 C18 C17 0.0(6) . . . .
P1 C13 C18 C17 179.8(3) . . . .
C16 C17 C18 C13 -1.7(6) . . . .
