#------------------------------------------------------------------------------
#$Date: 2016-06-30 09:51:28 +0300 (Thu, 30 Jun 2016) $
#$Revision: 184069 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/65/4086575.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_4086575
loop_
_publ_author_name
'Tondreau, Aaron M.'
'Boncella, James M.'
_publ_section_title
;
 1,2-Addition of Formic or Oxalic Acid to--N{CH2CH2(PiPr2)}2-Supported
 Mn(I) Dicarbonyl Complexes and the Manganese-Mediated Decomposition of
 Formic Acid
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2049
_journal_paper_doi               10.1021/acs.organomet.6b00274
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C19 H38 Mn N O4 P2'
_chemical_formula_weight         461.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.094(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.684(2)
_cell_length_b                   12.907(3)
_cell_length_c                   21.333(5)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.83
_cell_volume                     2387.6(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37722
_diffrn_reflns_theta_full        28.41
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.8598
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       0.0304(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.3432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                5230
_reflns_number_total             5982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om6b00274_si_002.cif
_cod_data_source_block           pnpmnformate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_original_cell_volume        2387.5(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4086575
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.13933(2) 0.190135(16) 0.114970(10) 0.02271(9) Uani 1 1 d . . .
P1 P 0.05083(5) 0.08609(3) 0.192656(18) 0.02981(11) Uani 1 1 d . . .
P2 P 0.24786(5) 0.25115(3) 0.026009(18) 0.02673(11) Uani 1 1 d . . .
N1 N 0.26385(14) 0.05619(10) 0.09277(6) 0.0264(3) Uani 1 1 d . . .
H1 H 0.2017 0.0223 0.0624 0.032 Uiso 1 1 calc R . .
O1 O -0.01983(12) 0.11706(9) 0.05603(5) 0.0310(2) Uani 1 1 d . . .
O2 O -0.24138(16) 0.11140(12) -0.00086(7) 0.0547(4) Uani 1 1 d . . .
O3 O 0.37944(16) 0.28553(12) 0.19700(6) 0.0479(3) Uani 1 1 d . . .
O4 O -0.03832(18) 0.37649(11) 0.14291(8) 0.0588(4) Uani 1 1 d . . .
C10 C 0.36899(19) 0.14152(13) 0.00363(7) 0.0325(3) Uani 1 1 d . . .
H10A H 0.3125 0.0982 -0.0283 0.039 Uiso 1 1 calc R . .
H10B H 0.4644 0.1674 -0.0144 0.039 Uiso 1 1 calc R . .
C9 C 0.40878(18) 0.07818(12) 0.06197(8) 0.0313(3) Uani 1 1 d . . .
H9A H 0.4593 0.0126 0.0505 0.038 Uiso 1 1 calc R . .
H9B H 0.4806 0.1173 0.0908 0.038 Uiso 1 1 calc R . .
C2 C 0.1373(2) -0.03953(14) 0.17344(9) 0.0420(4) Uani 1 1 d . . .
H2A H 0.1549 -0.0813 0.2121 0.050 Uiso 1 1 calc R . .
H2B H 0.0667 -0.0784 0.1440 0.050 Uiso 1 1 calc R . .
C1 C 0.2895(2) -0.02023(14) 0.14356(9) 0.0400(4) Uani 1 1 d . . .
H1A H 0.3668 0.0064 0.1754 0.048 Uiso 1 1 calc R . .
H1B H 0.3291 -0.0857 0.1264 0.048 Uiso 1 1 calc R . .
C14 C 0.3768(2) 0.36605(13) 0.02751(8) 0.0375(4) Uani 1 1 d . . .
H14 H 0.3866 0.3891 -0.0169 0.045 Uiso 1 1 calc R . .
C6 C 0.1083(3) 0.10841(18) 0.27617(8) 0.0509(5) Uani 1 1 d . . .
H6 H 0.0452 0.0610 0.3015 0.061 Uiso 1 1 calc R . .
C11 C 0.1195(2) 0.26751(17) -0.04518(8) 0.0429(4) Uani 1 1 d . . .
H11 H 0.0563 0.2029 -0.0490 0.052 Uiso 1 1 calc R . .
C3 C -0.1567(2) 0.05255(17) 0.19215(9) 0.0442(4) Uani 1 1 d . . .
H3 H -0.1862 0.0300 0.1483 0.053 Uiso 1 1 calc R . .
C15 C 0.5383(2) 0.34311(18) 0.05533(12) 0.0534(5) Uani 1 1 d . . .
H15A H 0.5321 0.3184 0.0986 0.080 Uiso 1 1 calc R . .
H15B H 0.6006 0.4064 0.0552 0.080 Uiso 1 1 calc R . .
H15C H 0.5863 0.2898 0.0302 0.080 Uiso 1 1 calc R . .
C13 C 0.0053(3) 0.3562(2) -0.03874(11) 0.0702(8) Uani 1 1 d . . .
H13A H -0.0313 0.3567 0.0039 0.105 Uiso 1 1 calc R . .
H13B H -0.0825 0.3468 -0.0690 0.105 Uiso 1 1 calc R . .
H13C H 0.0563 0.4222 -0.0470 0.105 Uiso 1 1 calc R . .
C12 C 0.2027(3) 0.2765(2) -0.10615(9) 0.0664(7) Uani 1 1 d . . .
H12B H 0.2597 0.3420 -0.1064 0.100 Uiso 1 1 calc R . .
H12A H 0.1270 0.2748 -0.1419 0.100 Uiso 1 1 calc R . .
H12C H 0.2748 0.2186 -0.1093 0.100 Uiso 1 1 calc R . .
C7 C 0.0728(3) 0.2192(2) 0.29599(11) 0.0716(8) Uani 1 1 d . . .
H7A H 0.1399 0.2675 0.2748 0.107 Uiso 1 1 calc R . .
H7B H 0.0911 0.2259 0.3415 0.107 Uiso 1 1 calc R . .
H7C H -0.0353 0.2353 0.2844 0.107 Uiso 1 1 calc R . .
C4 C -0.1940(3) -0.0390(2) 0.23434(13) 0.0702(7) Uani 1 1 d . . .
H4A H -0.1276 -0.0978 0.2250 0.105 Uiso 1 1 calc R . .
H4B H -0.3023 -0.0588 0.2266 0.105 Uiso 1 1 calc R . .
H4C H -0.1759 -0.0190 0.2784 0.105 Uiso 1 1 calc R . .
C16 C 0.3068(3) 0.45566(15) 0.06320(13) 0.0583(6) Uani 1 1 d . . .
H16A H 0.2026 0.4701 0.0454 0.088 Uiso 1 1 calc R . .
H16B H 0.3712 0.5175 0.0596 0.088 Uiso 1 1 calc R . .
H16C H 0.3018 0.4369 0.1076 0.088 Uiso 1 1 calc R . .
C8 C 0.2780(3) 0.0822(2) 0.29153(10) 0.0684(7) Uani 1 1 d . . .
H8A H 0.2963 0.0091 0.2820 0.103 Uiso 1 1 calc R . .
H8B H 0.3033 0.0950 0.3362 0.103 Uiso 1 1 calc R . .
H8C H 0.3432 0.1258 0.2662 0.103 Uiso 1 1 calc R . .
C5 C -0.2595(2) 0.1453(2) 0.20502(12) 0.0617(6) Uani 1 1 d . . .
H5A H -0.2455 0.1649 0.2493 0.093 Uiso 1 1 calc R . .
H5B H -0.3676 0.1267 0.1954 0.093 Uiso 1 1 calc R . .
H5C H -0.2314 0.2037 0.1786 0.093 Uiso 1 1 calc R . .
C18 C 0.0282(2) 0.30209(13) 0.13109(8) 0.0340(4) Uani 1 1 d . . .
C19 C 0.28607(19) 0.24503(12) 0.16409(7) 0.0307(3) Uani 1 1 d . . .
C17 C -0.15238(19) 0.14867(15) 0.03878(8) 0.0378(4) Uani 1 1 d . . .
H17 H -0.1871 0.2090 0.0592 0.045 Uiso 1 1 calc R . .
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'
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'
N N 0.0061 0.0033 '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 C18 86.60(8) . .
C19 Mn1 O1 175.48(6) . .
C18 Mn1 O1 97.90(7) . .
C19 Mn1 N1 95.77(6) . .
C18 Mn1 N1 177.56(7) . .
O1 Mn1 N1 79.72(5) . .
C19 Mn1 P1 93.76(5) . .
C18 Mn1 P1 97.41(6) . .
O1 Mn1 P1 86.14(4) . .
N1 Mn1 P1 83.01(4) . .
C19 Mn1 P2 92.17(5) . .
C18 Mn1 P2 97.57(6) . .
O1 Mn1 P2 86.80(4) . .
N1 Mn1 P2 81.81(4) . .
P1 Mn1 P2 164.175(18) . .
C2 P1 C6 105.05(10) . .
C2 P1 C3 101.61(9) . .
C6 P1 C3 104.73(9) . .
C2 P1 Mn1 101.40(6) . .
C6 P1 Mn1 121.42(7) . .
C3 P1 Mn1 119.71(7) . .
C10 P2 C11 101.68(8) . .
C10 P2 C14 105.42(8) . .
C11 P2 C14 105.02(9) . .
C10 P2 Mn1 102.46(5) . .
C11 P2 Mn1 117.47(7) . .
C14 P2 Mn1 122.13(6) . .
C1 N1 C9 110.89(12) . .
C1 N1 Mn1 116.32(10) . .
C9 N1 Mn1 113.70(9) . .
C17 O1 Mn1 127.38(11) . .
C9 C10 P2 108.07(10) . .
N1 C9 C10 107.89(12) . .
C1 C2 P1 108.88(12) . .
N1 C1 C2 108.53(14) . .
C15 C14 C16 109.61(18) . .
C15 C14 P2 113.16(13) . .
C16 C14 P2 110.94(13) . .
C7 C6 C8 110.7(2) . .
C7 C6 P1 111.40(16) . .
C8 C6 P1 112.28(15) . .
C12 C11 C13 111.06(19) . .
C12 C11 P2 114.69(15) . .
C13 C11 P2 112.22(14) . .
C5 C3 C4 110.80(19) . .
C5 C3 P1 113.19(14) . .
C4 C3 P1 114.43(16) . .
O4 C18 Mn1 177.04(17) . .
O3 C19 Mn1 176.88(15) . .
O2 C17 O1 127.86(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 C19 1.7548(16) .
Mn1 C18 1.7815(16) .
Mn1 O1 2.0478(11) .
Mn1 N1 2.1065(13) .
Mn1 P1 2.2973(6) .
Mn1 P2 2.3028(6) .
P1 C2 1.8425(19) .
P1 C6 1.8467(18) .
P1 C3 1.8529(19) .
P2 C10 1.8414(15) .
P2 C11 1.8466(18) .
P2 C14 1.8573(18) .
N1 C1 1.473(2) .
N1 C9 1.478(2) .
O1 C17 1.257(2) .
O2 C17 1.214(2) .
O3 C19 1.167(2) .
O4 C18 1.155(2) .
C10 C9 1.513(2) .
C2 C1 1.519(3) .
C14 C15 1.523(3) .
C14 C16 1.529(3) .
C6 C7 1.527(4) .
C6 C8 1.530(3) .
C11 C12 1.526(3) .
C11 C13 1.526(3) .
C3 C5 1.527(3) .
C3 C4 1.530(3) .
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
C19 Mn1 P1 C2 -100.82(9) . . . .
C18 Mn1 P1 C2 172.13(9) . . . .
O1 Mn1 P1 C2 74.65(8) . . . .
N1 Mn1 P1 C2 -5.45(7) . . . .
P2 Mn1 P1 C2 10.96(10) . . . .
C19 Mn1 P1 C6 14.88(11) . . . .
C18 Mn1 P1 C6 -72.18(11) . . . .
O1 Mn1 P1 C6 -169.66(10) . . . .
N1 Mn1 P1 C6 110.24(10) . . . .
P2 Mn1 P1 C6 126.65(11) . . . .
C19 Mn1 P1 C3 148.62(9) . . . .
C18 Mn1 P1 C3 61.56(10) . . . .
O1 Mn1 P1 C3 -35.91(8) . . . .
N1 Mn1 P1 C3 -116.02(9) . . . .
P2 Mn1 P1 C3 -99.61(10) . . . .
C19 Mn1 P2 C10 92.96(8) . . . .
C18 Mn1 P2 C10 179.82(8) . . . .
O1 Mn1 P2 C10 -82.63(7) . . . .
N1 Mn1 P2 C10 -2.57(7) . . . .
P1 Mn1 P2 C10 -19.02(9) . . . .
C19 Mn1 P2 C11 -156.64(9) . . . .
C18 Mn1 P2 C11 -69.78(9) . . . .
O1 Mn1 P2 C11 27.77(8) . . . .
N1 Mn1 P2 C11 107.84(8) . . . .
P1 Mn1 P2 C11 91.38(10) . . . .
C19 Mn1 P2 C14 -24.45(8) . . . .
C18 Mn1 P2 C14 62.41(9) . . . .
O1 Mn1 P2 C14 159.96(7) . . . .
N1 Mn1 P2 C14 -119.97(8) . . . .
P1 Mn1 P2 C14 -136.43(8) . . . .
C19 Mn1 N1 C1 71.04(13) . . . .
C18 Mn1 N1 C1 -122.1(16) . . . .
O1 Mn1 N1 C1 -109.38(12) . . . .
P1 Mn1 N1 C1 -22.06(11) . . . .
P2 Mn1 N1 C1 162.41(12) . . . .
C19 Mn1 N1 C9 -59.62(11) . . . .
C18 Mn1 N1 C9 107.2(16) . . . .
O1 Mn1 N1 C9 119.95(11) . . . .
P1 Mn1 N1 C9 -152.72(10) . . . .
P2 Mn1 N1 C9 31.74(10) . . . .
C19 Mn1 O1 C17 -173.4(8) . . . .
C18 Mn1 O1 C17 0.65(16) . . . .
N1 Mn1 O1 C17 -178.80(15) . . . .
P1 Mn1 O1 C17 97.62(14) . . . .
P2 Mn1 O1 C17 -96.55(14) . . . .
C11 P2 C10 C9 -146.49(13) . . . .
C14 P2 C10 C9 104.15(13) . . . .
Mn1 P2 C10 C9 -24.61(12) . . . .
C1 N1 C9 C10 170.05(13) . . . .
Mn1 N1 C9 C10 -56.64(14) . . . .
P2 C10 C9 N1 50.55(15) . . . .
C6 P1 C2 C1 -96.24(14) . . . .
C3 P1 C2 C1 154.86(13) . . . .
Mn1 P1 C2 C1 30.98(14) . . . .
C9 N1 C1 C2 179.90(14) . . . .
Mn1 N1 C1 C2 47.92(18) . . . .
P1 C2 C1 N1 -50.07(18) . . . .
C10 P2 C14 C15 -39.88(16) . . . .
C11 P2 C14 C15 -146.82(14) . . . .
Mn1 P2 C14 C15 76.07(15) . . . .
C10 P2 C14 C16 -163.56(15) . . . .
C11 P2 C14 C16 89.50(16) . . . .
Mn1 P2 C14 C16 -47.61(17) . . . .
C2 P1 C6 C7 168.68(16) . . . .
C3 P1 C6 C7 -84.70(17) . . . .
Mn1 P1 C6 C7 54.85(18) . . . .
C2 P1 C6 C8 43.81(18) . . . .
C3 P1 C6 C8 150.43(16) . . . .
Mn1 P1 C6 C8 -70.02(18) . . . .
C10 P2 C11 C12 -51.8(2) . . . .
C14 P2 C11 C12 57.85(19) . . . .
Mn1 P2 C11 C12 -162.66(16) . . . .
C10 P2 C11 C13 -179.76(17) . . . .
C14 P2 C11 C13 -70.09(19) . . . .
Mn1 P2 C11 C13 69.40(19) . . . .
C2 P1 C3 C5 -178.23(15) . . . .
C6 P1 C3 C5 72.62(17) . . . .
Mn1 P1 C3 C5 -67.78(16) . . . .
C2 P1 C3 C4 53.54(18) . . . .
C6 P1 C3 C4 -55.61(19) . . . .
Mn1 P1 C3 C4 163.99(15) . . . .
C19 Mn1 C18 O4 7(3) . . . .
O1 Mn1 C18 O4 -173(3) . . . .
N1 Mn1 C18 O4 -160(3) . . . .
P1 Mn1 C18 O4 100(3) . . . .
P2 Mn1 C18 O4 -85(3) . . . .
C18 Mn1 C19 O3 -4(3) . . . .
O1 Mn1 C19 O3 170(2) . . . .
N1 Mn1 C19 O3 175(100) . . . .
P1 Mn1 C19 O3 -102(3) . . . .
P2 Mn1 C19 O3 93(3) . . . .
Mn1 O1 C17 O2 171.84(17) . . . .
