#------------------------------------------------------------------------------
#$Date: 2017-09-12 07:03:19 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200733 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/63/1546353.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_1546353
loop_
_publ_author_name
'Bruneau-Voisine, Antoine'
'Wang, Ding'
'Dorcet, Vincent'
'Roisnel, Thierry'
'Darcel, Christophe'
'Sortais, Jean-Baptiste'
_publ_section_title
;
 Transfer Hydrogenation of Carbonyl Derivatives Catalyzed by an
 Inexpensive Phosphine-Free Manganese Precatalyst.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3656
_journal_page_last               3659
_journal_paper_doi               10.1021/acs.orglett.7b01657
_journal_volume                  19
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H14 Mn2 N4 O6'
_chemical_formula_sum            'C18 H14 Mn2 N4 O6'
_chemical_formula_weight         492.21
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                106.422(3)
_cell_angle_beta                 100.106(4)
_cell_angle_gamma                113.184(3)
_cell_formula_units_Z            1
_cell_length_a                   7.2912(9)
_cell_length_b                   8.1947(10)
_cell_length_c                   9.5912(11)
_cell_measurement_reflns_used    9103
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.96
_cell_measurement_wavelength     0.71073
_cell_volume                     477.83(10)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9005
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.935
_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_description       prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.373
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.373
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0595P)²+0.2003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2132
_reflns_number_total             2189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01657_si_003.cif
_cod_data_source_block           ABV466
_cod_depositor_comments          'Adding full bibliography for 1546353.cif.'
_cod_database_code               1546353
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Mn1 Mn 0.85749(4) 0.53131(3) 0.37626(3) 0.00998(14) Uani 1 1 d . .
C1 C 0.8801(3) 0.7533(3) 0.5034(2) 0.0146(4) Uani 1 1 d . .
O2 O 0.8701(3) 0.8839(2) 0.58025(19) 0.0225(3) Uani 1 1 d . .
C3 C 0.9242(3) 0.6292(3) 0.2336(2) 0.0189(4) Uani 1 1 d . .
O4 O 0.9709(4) 0.6921(3) 0.1451(2) 0.0363(5) Uani 1 1 d . .
C5 C 0.5853(3) 0.4725(3) 0.3001(2) 0.0154(4) Uani 1 1 d . .
O6 O 0.4161(2) 0.4489(2) 0.25101(19) 0.0259(4) Uani 1 1 d . .
N7 N 0.8328(3) 0.4121(2) 0.53660(19) 0.0107(3) Uani 1 1 d . .
H7 H 0.800(4) 0.471(4) 0.613(3) 0.013 Uiso 1 1 d . U
C8 C 0.6686(3) 0.2097(3) 0.4610(2) 0.0142(4) Uani 1 1 d . .
H8A H 0.527153 0.201998 0.446312 0.017 Uiso 1 1 calc R U
H8B H 0.685297 0.137890 0.525543 0.017 Uiso 1 1 calc R U
C9 C 0.6900(3) 0.1233(3) 0.3079(2) 0.0139(4) Uani 1 1 d . .
C10 C 0.6142(3) -0.0729(3) 0.2311(3) 0.0192(4) Uani 1 1 d . .
H10 H 0.542222 -0.161135 0.273314 0.023 Uiso 1 1 calc R U
C11 C 0.6452(4) -0.1385(3) 0.0913(3) 0.0233(4) Uani 1 1 d . .
H11 H 0.592158 -0.272448 0.035468 0.028 Uiso 1 1 calc R U
C12 C 0.7543(3) -0.0060(3) 0.0344(2) 0.0221(4) Uani 1 1 d . .
H12 H 0.781231 -0.047406 -0.059282 0.027 Uiso 1 1 calc R U
C13 C 0.8235(3) 0.1872(3) 0.1159(2) 0.0172(4) Uani 1 1 d . .
H13 H 0.896582 0.277718 0.075928 0.021 Uiso 1 1 calc R U
N14 N 0.7909(3) 0.2522(2) 0.25065(19) 0.0127(3) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 Mn1 C1 83.89(9) . .
C5 Mn1 C3 91.19(10) . .
C1 Mn1 C3 92.91(9) . .
C5 Mn1 N7 98.96(8) . .
C1 Mn1 N7 93.10(8) . .
C3 Mn1 N7 168.69(8) . .
C5 Mn1 N14 90.79(8) . .
C1 Mn1 N14 168.87(8) . .
C3 Mn1 N14 96.98(8) . .
N7 Mn1 N14 78.03(7) . .
C5 Mn1 N7 177.73(7) . 2_766
C1 Mn1 N7 97.81(8) . 2_766
C3 Mn1 N7 90.23(8) . 2_766
N7 Mn1 N7 79.48(7) . 2_766
N14 Mn1 N7 87.28(6) . 2_766
C5 Mn1 Mn1 139.09(7) . 2_766
C1 Mn1 Mn1 97.12(6) . 2_766
C3 Mn1 Mn1 129.39(7) . 2_766
N7 Mn1 Mn1 40.15(5) . 2_766
N14 Mn1 Mn1 80.52(5) . 2_766
N7 Mn1 Mn1 39.33(4) 2_766 2_766
O2 C1 Mn1 172.27(17) . .
O4 C3 Mn1 178.5(2) . .
O6 C5 Mn1 174.70(19) . .
C8 N7 Mn1 108.74(12) . .
C8 N7 Mn1 118.08(12) . 2_766
Mn1 N7 Mn1 100.52(7) . 2_766
C8 N7 H7 108.4(17) . .
Mn1 N7 H7 113.5(17) . .
Mn1 N7 H7 107.6(17) 2_766 .
N7 C8 C9 108.40(15) . .
N7 C8 H8A 110.0 . .
C9 C8 H8A 110.0 . .
N7 C8 H8B 110.0 . .
C9 C8 H8B 110.0 . .
H8A C8 H8B 108.4 . .
N14 C9 C10 122.12(18) . .
N14 C9 C8 114.70(16) . .
C10 C9 C8 123.18(18) . .
C9 C10 C11 118.8(2) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
C12 C11 C10 119.18(19) . .
C12 C11 H11 120.4 . .
C10 C11 H11 120.4 . .
C13 C12 C11 118.95(19) . .
C13 C12 H12 120.5 . .
C11 C12 H12 120.5 . .
N14 C13 C12 122.3(2) . .
N14 C13 H13 118.8 . .
C12 C13 H13 118.8 . .
C9 N14 C13 118.51(17) . .
C9 N14 Mn1 114.00(12) . .
C13 N14 Mn1 127.30(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 C5 1.801(2) .
Mn1 C1 1.807(2) .
Mn1 C3 1.817(2) .
Mn1 N7 2.0397(16) .
Mn1 N14 2.0686(17) .
Mn1 N7 2.0752(17) 2_766
Mn1 Mn1 3.1643(6) 2_766
C1 O2 1.152(3) .
C3 O4 1.145(3) .
C5 O6 1.156(3) .
N7 C8 1.470(2) .
N7 H7 0.88(3) .
C8 C9 1.503(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N14 1.348(2) .
C9 C10 1.386(3) .
C10 C11 1.391(3) .
C10 H10 0.9500 .
C11 C12 1.384(3) .
C11 H11 0.9500 .
C12 C13 1.380(3) .
C12 H12 0.9500 .
C13 N14 1.352(2) .
C13 H13 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O4 0.95 2.51 3.323(3) 143.2 2_765
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
Mn1 N7 C8 C9 40.93(17) .
Mn1 N7 C8 C9 -72.62(17) 2_766
N7 C8 C9 N14 -22.3(2) .
N7 C8 C9 C10 157.20(18) .
N14 C9 C10 C11 0.7(3) .
C8 C9 C10 C11 -178.83(19) .
C9 C10 C11 C12 1.3(3) .
C10 C11 C12 C13 -2.0(3) .
C11 C12 C13 N14 0.9(3) .
C10 C9 N14 C13 -1.8(3) .
C8 C9 N14 C13 177.71(17) .
C10 C9 N14 Mn1 173.51(15) .
C8 C9 N14 Mn1 -6.9(2) .
C12 C13 N14 C9 1.0(3) .
C12 C13 N14 Mn1 -173.61(15) .
