#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:34:26 +0200 (Thu, 07 Nov 2019) $
#$Revision: 224049 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/10/7701025.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_7701025
loop_
_publ_author_name
'Kumar, Amit'
'Daw, Prosenjit'
'Espinosa-Jalapa, Noel Angel'
'Leitus, Gregory'
'Shimon, Linda J. W.'
'Ben-David, Yehoshoa'
'Milstein, David'
_publ_section_title
;
 CO₂ activation by manganese pincer complexes through different
 modes of metal-ligand cooperation.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14580
_journal_page_last               14584
_journal_paper_doi               10.1039/c9dt03088c
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C22 H36 Mn N2 O4 P'
_chemical_formula_sum            'C22 H36 Mn N2 O4 P'
_chemical_formula_weight         478.44
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-08-27 deposited with the CCDC.    2019-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.34(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.713(3)
_cell_length_b                   14.096(3)
_cell_length_c                   13.603(3)
_cell_measurement_reflns_used    61998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.8074
_cell_measurement_theta_min      2.1876
_cell_volume                     2381.4(10)
_computing_cell_refinement       'Software Bruker KappaApex CCD'
_computing_data_collection       'Software Bruker KappaApex CCD'
_computing_data_reduction        'Software Bruker KappaApex CCD'
_computing_molecular_graphics    'Mercury 3.7''
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker KappaApex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            60055
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         3.272
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker KappaApex2'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0357P)²+0.9343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4333
_reflns_number_total             5257
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03088c2.cif
_cod_data_source_block           Complex_5'
_cod_depositor_comments
'Adding full bibliography for 7701025--7701028.cif.'
_cod_original_cell_volume        2381.3(9)
_cod_database_code               7701025
_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   0.956
_shelx_estimated_absorpt_t_max   0.992
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
Mn1 Mn 0.37589(2) 0.75050(2) 0.56641(2) 0.00904(7) Uani 1 1 d . .
P1 P 0.19622(3) 0.73422(3) 0.57179(3) 0.00989(9) Uani 1 1 d . .
O1 O 0.32590(10) 0.90250(8) 0.41626(9) 0.0216(3) Uani 1 1 d . .
O2 O 0.42881(9) 0.89951(8) 0.72067(9) 0.0231(3) Uani 1 1 d . .
O3 O 0.42252(8) 0.63575(7) 0.65573(8) 0.0123(2) Uani 1 1 d . .
O4 O 0.50705(10) 0.57876(8) 0.80494(8) 0.0220(3) Uani 1 1 d . .
N1 N 0.33061(10) 0.66095(8) 0.44775(9) 0.0103(3) Uani 1 1 d . .
N2 N 0.53504(10) 0.72379(9) 0.52666(10) 0.0126(3) Uani 1 1 d . .
C1 C 0.14496(12) 0.70842(11) 0.43633(11) 0.0136(3) Uani 1 1 d . .
H1A H 0.0770 0.6719 0.4272 0.016 Uiso 1 1 calc R U
H1B H 0.1298 0.7686 0.3984 0.016 Uiso 1 1 calc R U
C2 C 0.22753(13) 0.65212(10) 0.39680(11) 0.0126(3) Uani 1 1 d . .
C3 C 0.20163(14) 0.59419(11) 0.31205(12) 0.0170(3) Uani 1 1 d . .
H3 H 0.1287 0.5861 0.2781 0.020 Uiso 1 1 calc R U
C4 C 0.28344(14) 0.54854(11) 0.27776(12) 0.0195(4) Uani 1 1 d . .
H4 H 0.2670 0.5092 0.2198 0.023 Uiso 1 1 calc R U
C5 C 0.38938(14) 0.56052(11) 0.32843(12) 0.0166(3) Uani 1 1 d . .
H5 H 0.4465 0.5313 0.3047 0.020 Uiso 1 1 calc R U
C6 C 0.41020(13) 0.61607(10) 0.41455(11) 0.0124(3) Uani 1 1 d . .
C7 C 0.52001(12) 0.62717(10) 0.48032(12) 0.0131(3) Uani 1 1 d . .
H7A H 0.5305 0.5787 0.5342 0.016 Uiso 1 1 calc R U
H7B H 0.5750 0.6165 0.4398 0.016 Uiso 1 1 calc R U
C8 C 0.15281(13) 0.62382(11) 0.63393(12) 0.0148(3) Uani 1 1 d . .
C9 C 0.19365(13) 0.53632(11) 0.58545(12) 0.0166(3) Uani 1 1 d . .
H9A H 0.1792 0.4789 0.6211 0.025 Uiso 1 1 calc R U
H9B H 0.2713 0.5423 0.5898 0.025 Uiso 1 1 calc R U
H9C H 0.1564 0.5321 0.5146 0.025 Uiso 1 1 calc R U
C10 C 0.03016(13) 0.61338(12) 0.62076(14) 0.0234(4) Uani 1 1 d . .
H10A H -0.0044 0.6211 0.5496 0.035 Uiso 1 1 calc R U
H10B H 0.0033 0.6620 0.6606 0.035 Uiso 1 1 calc R U
H10C H 0.0134 0.5503 0.6437 0.035 Uiso 1 1 calc R U
C11 C 0.20327(14) 0.62171(12) 0.74740(12) 0.0180(3) Uani 1 1 d . .
H11A H 0.1826 0.6791 0.7792 0.027 Uiso 1 1 calc R U
H11B H 0.2819 0.6190 0.7574 0.027 Uiso 1 1 calc R U
H11C H 0.1775 0.5657 0.7778 0.027 Uiso 1 1 calc R U
C12 C 0.11429(13) 0.83988(11) 0.59817(12) 0.0143(3) Uani 1 1 d . .
C13 C 0.15871(13) 0.93030(11) 0.55849(12) 0.0161(3) Uani 1 1 d . .
H13A H 0.1510 0.9254 0.4854 0.024 Uiso 1 1 calc R U
H13B H 0.2350 0.9376 0.5905 0.024 Uiso 1 1 calc R U
H13C H 0.1184 0.9855 0.5742 0.024 Uiso 1 1 calc R U
C14 C -0.00553(13) 0.83498(12) 0.54730(14) 0.0210(4) Uani 1 1 d . .
H14A H -0.0424 0.8914 0.5652 0.031 Uiso 1 1 calc R U
H14B H -0.0375 0.7780 0.5701 0.031 Uiso 1 1 calc R U
H14C H -0.0132 0.8325 0.4741 0.031 Uiso 1 1 calc R U
C15 C 0.12743(14) 0.85105(12) 0.71252(12) 0.0208(4) Uani 1 1 d . .
H15A H 0.1000 0.9132 0.7273 0.031 Uiso 1 1 calc R U
H15B H 0.2038 0.8461 0.7451 0.031 Uiso 1 1 calc R U
H15C H 0.0869 0.8010 0.7380 0.031 Uiso 1 1 calc R U
C16 C 0.55963(14) 0.79037(11) 0.44905(13) 0.0179(3) Uani 1 1 d . .
H16A H 0.4959 0.7944 0.3928 0.021 Uiso 1 1 calc R U
H16B H 0.6198 0.7639 0.4219 0.021 Uiso 1 1 calc R U
C17 C 0.58973(15) 0.89002(12) 0.48837(14) 0.0244(4) Uani 1 1 d . .
H17A H 0.5409 0.9102 0.5312 0.037 Uiso 1 1 calc R U
H17B H 0.5837 0.9339 0.4315 0.037 Uiso 1 1 calc R U
H17C H 0.6639 0.8901 0.5277 0.037 Uiso 1 1 calc R U
C18 C 0.62684(13) 0.72061(12) 0.61614(13) 0.0190(3) Uani 1 1 d . .
H18A H 0.6092 0.6738 0.6644 0.023 Uiso 1 1 calc R U
H18B H 0.6324 0.7835 0.6493 0.023 Uiso 1 1 calc R U
C19 C 0.73734(14) 0.69532(14) 0.59584(15) 0.0274(4) Uani 1 1 d . .
H19A H 0.7337 0.6330 0.5633 0.041 Uiso 1 1 calc R U
H19B H 0.7906 0.6935 0.6596 0.041 Uiso 1 1 calc R U
H19C H 0.7585 0.7432 0.5516 0.041 Uiso 1 1 calc R U
C20 C 0.34414(12) 0.84419(11) 0.47822(12) 0.0137(3) Uani 1 1 d . .
C21 C 0.41010(12) 0.83742(11) 0.66246(12) 0.0144(3) Uani 1 1 d . .
C22 C 0.46080(13) 0.64140(12) 0.74992(12) 0.0153(3) Uani 1 1 d . .
H22 H 0.4524(16) 0.7063(14) 0.7819(14) 0.026(5) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 Mn1 C21 88.19(7)
C20 Mn1 N1 86.58(6)
C21 Mn1 N1 174.66(6)
C20 Mn1 O3 172.96(6)
C21 Mn1 O3 96.60(6)
N1 Mn1 O3 88.71(5)
C20 Mn1 N2 92.80(6)
C21 Mn1 N2 101.66(6)
N1 Mn1 N2 79.67(5)
O3 Mn1 N2 81.21(5)
C20 Mn1 P1 90.68(6)
C21 Mn1 P1 97.67(6)
N1 Mn1 P1 81.35(4)
O3 Mn1 P1 93.78(4)
N2 Mn1 P1 160.45(4)
C1 P1 C12 104.57(7)
C1 P1 C8 101.93(7)
C12 P1 C8 109.54(7)
C1 P1 Mn1 97.34(6)
C12 P1 Mn1 120.97(5)
C8 P1 Mn1 118.44(5)
C22 O3 Mn1 123.50(10)
C6 N1 C2 119.95(13)
C6 N1 Mn1 116.82(10)
C2 N1 Mn1 122.93(10)
C16 N2 C7 107.52(12)
C16 N2 C18 110.42(13)
C7 N2 C18 108.83(12)
C16 N2 Mn1 113.70(10)
C7 N2 Mn1 102.39(9)
C18 N2 Mn1 113.41(10)
C2 C1 P1 109.56(10)
C2 C1 H1A 109.8
P1 C1 H1A 109.8
C2 C1 H1B 109.8
P1 C1 H1B 109.8
H1A C1 H1B 108.2
N1 C2 C3 120.68(15)
N1 C2 C1 116.26(13)
C3 C2 C1 123.05(14)
C4 C3 C2 119.26(15)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 119.70(15)
C3 C4 H4 120.1
C5 C4 H4 120.1
C4 C5 C6 118.60(15)
C4 C5 H5 120.7
C6 C5 H5 120.7
N1 C6 C5 121.72(15)
N1 C6 C7 114.90(13)
C5 C6 C7 123.31(14)
N2 C7 C6 111.47(12)
N2 C7 H7A 109.3
C6 C7 H7A 109.3
N2 C7 H7B 109.3
C6 C7 H7B 109.3
H7A C7 H7B 108.0
C10 C8 C9 107.44(13)
C10 C8 C11 108.03(14)
C9 C8 C11 107.91(13)
C10 C8 P1 114.11(11)
C9 C8 P1 107.92(11)
C11 C8 P1 111.21(11)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C14 C12 C15 110.11(14)
C14 C12 C13 106.42(13)
C15 C12 C13 107.56(13)
C14 C12 P1 114.34(11)
C15 C12 P1 109.09(11)
C13 C12 P1 109.09(10)
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
N2 C16 C17 113.94(14)
N2 C16 H16A 108.8
C17 C16 H16A 108.8
N2 C16 H16B 108.8
C17 C16 H16B 108.8
H16A C16 H16B 107.7
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
N2 C18 C19 116.53(14)
N2 C18 H18A 108.2
C19 C18 H18A 108.2
N2 C18 H18B 108.2
C19 C18 H18B 108.2
H18A C18 H18B 107.3
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
O1 C20 Mn1 175.89(14)
O2 C21 Mn1 175.03(14)
O4 C22 O3 126.96(15)
O4 C22 H22 117.6(11)
O3 C22 H22 115.4(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Mn1 C20 1.7718(16)
Mn1 C21 1.7761(16)
Mn1 N1 2.0329(13)
Mn1 O3 2.0338(11)
Mn1 N2 2.2350(14)
Mn1 P1 2.3122(6)
P1 C1 1.8545(16)
P1 C12 1.8951(16)
P1 C8 1.9079(16)
O1 C20 1.1646(19)
O2 C21 1.1701(19)
O3 C22 1.2721(19)
O4 C22 1.2236(19)
N1 C6 1.350(2)
N1 C2 1.351(2)
N2 C16 1.495(2)
N2 C7 1.4958(19)
N2 C18 1.496(2)
C1 C2 1.504(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.394(2)
C3 C4 1.386(2)
C3 H3 0.9500
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.387(2)
C5 H5 0.9500
C6 C7 1.497(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C10 1.538(2)
C8 C9 1.540(2)
C8 C11 1.540(2)
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 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C14 1.534(2)
C12 C15 1.537(2)
C12 C13 1.538(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C17 1.523(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 C19 1.530(2)
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C22 H22 1.03(2)
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
C12 P1 C1 C2 159.10(10)
C8 P1 C1 C2 -86.82(11)
Mn1 P1 C1 C2 34.38(11)
C6 N1 C2 C3 2.4(2)
Mn1 N1 C2 C3 175.92(11)
C6 N1 C2 C1 -177.07(13)
Mn1 N1 C2 C1 -3.54(18)
P1 C1 C2 N1 -23.92(16)
P1 C1 C2 C3 156.63(13)
N1 C2 C3 C4 -2.7(2)
C1 C2 C3 C4 176.73(14)
C2 C3 C4 C5 0.5(2)
C3 C4 C5 C6 2.0(2)
C2 N1 C6 C5 0.1(2)
Mn1 N1 C6 C5 -173.77(11)
C2 N1 C6 C7 -176.91(13)
Mn1 N1 C6 C7 9.17(16)
C4 C5 C6 N1 -2.3(2)
C4 C5 C6 C7 174.48(14)
C16 N2 C7 C6 -79.77(15)
C18 N2 C7 C6 160.61(13)
Mn1 N2 C7 C6 40.29(13)
N1 C6 C7 N2 -35.85(18)
C5 C6 C7 N2 147.14(14)
C1 P1 C12 C14 41.06(13)
C8 P1 C12 C14 -67.54(13)
Mn1 P1 C12 C14 149.11(10)
C1 P1 C12 C15 164.83(11)
C8 P1 C12 C15 56.23(13)
Mn1 P1 C12 C15 -87.12(12)
C1 P1 C12 C13 -77.94(12)
C8 P1 C12 C13 173.46(10)
Mn1 P1 C12 C13 30.11(13)
C7 N2 C16 C17 -173.42(14)
C18 N2 C16 C17 -54.81(18)
Mn1 N2 C16 C17 73.98(16)
C16 N2 C18 C19 -55.44(18)
C7 N2 C18 C19 62.36(18)
Mn1 N2 C18 C19 175.61(12)
Mn1 O3 C22 O4 -166.54(13)
