#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:04:57 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179466 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/63/4336368.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_4336368
loop_
_publ_author_name
'Li-Cheng Song'
'Jia-Peng Li'
'Zhao-Jun Xie'
'Hai-Bin Song'
_publ_section_title
;
 Synthesis, Structural Characterization, and Electrochemical Properties of
 Dinuclear Ni/Mn Model Complexes for the Active Site of
 [NiFe]-Hydrogenases
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11618
_journal_page_last               11626
_journal_paper_doi               10.1021/ic401978h
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C28 H27 N O2 P2'
_chemical_formula_weight         471.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 117.471(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.665(4)
_cell_length_b                   14.527(5)
_cell_length_c                   9.866(4)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.3
_cell_volume                     1229.0(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15822
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5839
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0590
_reflns_number_gt                4925
_reflns_number_total             5839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic401978h_si_003_2.cif
_cod_data_source_block           2
_cod_original_cell_volume        1229.0(9)
_cod_database_code               4336368
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.15968(4) 0.17197(3) 0.33044(4) 0.01506(8) Uani 1 1 d .
P2 P 0.23331(4) -0.01621(3) 0.24581(4) 0.01506(9) Uani 1 1 d .
O1 O -0.06113(11) 0.02143(8) 0.40295(11) 0.0232(2) Uani 1 1 d .
O2 O -0.28321(11) 0.00899(8) 0.18290(12) 0.0246(3) Uani 1 1 d .
N1 N 0.10482(13) 0.06812(8) 0.23686(13) 0.0143(3) Uani 1 1 d .
C1 C 0.32473(17) 0.14448(9) 0.51610(16) 0.0157(3) Uani 1 1 d .
C2 C 0.47644(16) 0.17372(11) 0.56179(16) 0.0208(3) Uani 1 1 d .
H2 H 0.5025 0.2019 0.4897 0.025 Uiso 1 1 calc R
C3 C 0.59093(17) 0.16225(12) 0.71208(17) 0.0245(3) Uani 1 1 d .
H3 H 0.6946 0.1822 0.7419 0.029 Uiso 1 1 calc R
C4 C 0.55367(18) 0.12160(11) 0.81838(18) 0.0238(4) Uani 1 1 d .
H4 H 0.6308 0.1158 0.9218 0.029 Uiso 1 1 calc R
C5 C 0.40402(18) 0.08959(11) 0.77341(17) 0.0234(4) Uani 1 1 d .
H5 H 0.3792 0.0597 0.8450 0.028 Uiso 1 1 calc R
C6 C 0.29033(18) 0.10126(11) 0.62366(17) 0.0203(3) Uani 1 1 d .
H6 H 0.1875 0.0796 0.5936 0.024 Uiso 1 1 calc R
C7 C 0.25757(16) 0.23583(11) 0.23820(16) 0.0175(3) Uani 1 1 d .
C8 C 0.32681(17) 0.19909(11) 0.15439(17) 0.0228(4) Uani 1 1 d .
H8 H 0.3257 0.1344 0.1398 0.027 Uiso 1 1 calc R
C9 C 0.39795(19) 0.25629(12) 0.09146(18) 0.0269(4) Uani 1 1 d .
H9 H 0.4426 0.2306 0.0321 0.032 Uiso 1 1 calc R
C10 C 0.40382(19) 0.35044(12) 0.11516(19) 0.0273(4) Uani 1 1 d .
H10 H 0.4551 0.3892 0.0748 0.033 Uiso 1 1 calc R
C11 C 0.33442(19) 0.38792(12) 0.19815(18) 0.0269(4) Uani 1 1 d .
H11 H 0.3377 0.4525 0.2144 0.032 Uiso 1 1 calc R
C12 C 0.26017(17) 0.33109(11) 0.25758(18) 0.0234(4) Uani 1 1 d .
H12 H 0.2106 0.3574 0.3121 0.028 Uiso 1 1 calc R
C13 C 0.16760(16) -0.04376(10) 0.04412(16) 0.0161(3) Uani 1 1 d .
C14 C 0.21994(17) -0.12585(11) 0.00849(18) 0.0211(3) Uani 1 1 d .
H14 H 0.2802 -0.1678 0.0878 0.025 Uiso 1 1 calc R
C15 C 0.18483(18) -0.14649(11) -0.14103(19) 0.0244(4) Uani 1 1 d .
H15 H 0.2217 -0.2023 -0.1631 0.029 Uiso 1 1 calc R
C16 C 0.09627(18) -0.08636(11) -0.25893(18) 0.0229(4) Uani 1 1 d .
H16 H 0.0718 -0.1010 -0.3614 0.028 Uiso 1 1 calc R
C17 C 0.04371(17) -0.00456(11) -0.22561(17) 0.0205(3) Uani 1 1 d .
H17 H -0.0172 0.0369 -0.3056 0.025 Uiso 1 1 calc R
C18 C 0.08026(16) 0.01682(11) -0.07490(16) 0.0181(3) Uani 1 1 d .
H18 H 0.0453 0.0733 -0.0529 0.022 Uiso 1 1 calc R
C19 C 0.16868(16) -0.11899(10) 0.30796(16) 0.0153(3) Uani 1 1 d .
C20 C 0.26049(17) -0.14608(10) 0.45917(17) 0.0182(3) Uani 1 1 d .
H20 H 0.3517 -0.1120 0.5221 0.022 Uiso 1 1 calc R
C21 C 0.22083(18) -0.22183(11) 0.51889(17) 0.0221(4) Uani 1 1 d .
H21 H 0.2857 -0.2400 0.6215 0.027 Uiso 1 1 calc R
C22 C 0.08670(19) -0.27138(11) 0.42940(19) 0.0237(4) Uani 1 1 d .
H22 H 0.0579 -0.3224 0.4712 0.028 Uiso 1 1 calc R
C23 C -0.00492(19) -0.24603(11) 0.27878(19) 0.0234(4) Uani 1 1 d .
H23 H -0.0965 -0.2802 0.2172 0.028 Uiso 1 1 calc R
C24 C 0.03540(17) -0.17129(10) 0.21661(17) 0.0195(3) Uani 1 1 d .
H24 H -0.0271 -0.1555 0.1123 0.023 Uiso 1 1 calc R
C25 C -0.06285(16) 0.05278(10) 0.16031(16) 0.0161(3) Uani 1 1 d .
H25A H -0.0870 0.0038 0.0828 0.019 Uiso 1 1 calc R
H25B H -0.1150 0.1098 0.1058 0.019 Uiso 1 1 calc R
C26 C -0.13035(16) 0.02539(10) 0.26608(17) 0.0164(3) Uani 1 1 d .
C27 C -0.36780(18) -0.01610(14) 0.26782(19) 0.0299(4) Uani 1 1 d .
H27A H -0.4803 -0.0040 0.2034 0.036 Uiso 1 1 calc R
H27B H -0.3315 0.0232 0.3599 0.036 Uiso 1 1 calc R
C28 C -0.3456(2) -0.11484(13) 0.3152(2) 0.0333(4) Uani 1 1 d .
H28A H -0.3767 -0.1540 0.2249 0.050 Uiso 1 1 calc R
H28B H -0.4100 -0.1295 0.3653 0.050 Uiso 1 1 calc R
H28C H -0.2356 -0.1259 0.3864 0.050 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 P1 C1 104.82(6)
N1 P1 C7 106.18(7)
C1 P1 C7 101.25(7)
N1 P2 C19 104.41(7)
N1 P2 C13 102.70(6)
C19 P2 C13 100.65(7)
C26 O2 C27 116.35(12)
C25 N1 P2 121.55(10)
C25 N1 P1 114.00(9)
P2 N1 P1 124.17(7)
C2 C1 C6 118.46(13)
C2 C1 P1 124.06(11)
C6 C1 P1 116.99(11)
C1 C2 C3 120.76(14)
C1 C2 H2 119.6
C3 C2 H2 119.6
C4 C3 C2 120.00(15)
C4 C3 H3 120.0
C2 C3 H3 120.0
C5 C4 C3 119.87(14)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 119.89(15)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 120.97(15)
C5 C6 H6 119.5
C1 C6 H6 119.5
C8 C7 C12 118.67(14)
C8 C7 P1 126.91(13)
C12 C7 P1 114.43(12)
C7 C8 C9 120.56(16)
C7 C8 H8 119.7
C9 C8 H8 119.7
C10 C9 C8 120.27(16)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 119.62(15)
C9 C10 H10 120.2
C11 C10 H10 120.2
C10 C11 C12 120.05(16)
C10 C11 H11 120.0
C12 C11 H11 120.0
C11 C12 C7 120.78(15)
C11 C12 H12 119.6
C7 C12 H12 119.6
C18 C13 C14 118.24(14)
C18 C13 P2 123.20(11)
C14 C13 P2 118.28(11)
C15 C14 C13 120.77(15)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.61(15)
C14 C15 H15 119.7
C16 C15 H15 119.7
C15 C16 C17 119.38(14)
C15 C16 H16 120.3
C17 C16 H16 120.3
C16 C17 C18 120.11(14)
C16 C17 H17 119.9
C18 C17 H17 119.9
C17 C18 C13 120.88(14)
C17 C18 H18 119.6
C13 C18 H18 119.6
C20 C19 C24 118.40(14)
C20 C19 P2 116.19(11)
C24 C19 P2 125.41(12)
C21 C20 C19 121.01(15)
C21 C20 H20 119.5
C19 C20 H20 119.5
C20 C21 C22 120.21(15)
C20 C21 H21 119.9
C22 C21 H21 119.9
C23 C22 C21 119.54(15)
C23 C22 H22 120.2
C21 C22 H22 120.2
C22 C23 C24 120.77(15)
C22 C23 H23 119.6
C24 C23 H23 119.6
C23 C24 C19 120.02(15)
C23 C24 H24 120.0
C19 C24 H24 120.0
N1 C25 C26 114.37(12)
N1 C25 H25A 108.7
C26 C25 H25A 108.7
N1 C25 H25B 108.7
C26 C25 H25B 108.7
H25A C25 H25B 107.6
O1 C26 O2 124.44(13)
O1 C26 C25 126.37(13)
O2 C26 C25 109.15(12)
O2 C27 C28 112.43(14)
O2 C27 H27A 109.1
C28 C27 H27A 109.1
O2 C27 H27B 109.1
C28 C27 H27B 109.1
H27A C27 H27B 107.9
C27 C28 H28A 109.5
C27 C28 H28B 109.5
H28A C28 H28B 109.5
C27 C28 H28C 109.5
H28A C28 H28C 109.5
H28B C28 H28C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N1 1.7198(13)
P1 C1 1.8340(15)
P1 C7 1.8380(15)
P2 N1 1.7174(13)
P2 C19 1.8300(16)
P2 C13 1.8323(17)
O1 C26 1.2004(18)
O2 C26 1.3395(17)
O2 C27 1.4612(17)
N1 C25 1.4550(19)
C1 C2 1.387(2)
C1 C6 1.399(2)
C2 C3 1.392(2)
C2 H2 0.9500
C3 C4 1.388(2)
C3 H3 0.9500
C4 C5 1.383(2)
C4 H4 0.9500
C5 C6 1.386(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.388(2)
C7 C12 1.396(2)
C8 C9 1.394(2)
C8 H8 0.9500
C9 C10 1.384(2)
C9 H9 0.9500
C10 C11 1.387(2)
C10 H10 0.9500
C11 C12 1.389(2)
C11 H11 0.9500
C12 H12 0.9500
C13 C18 1.397(2)
C13 C14 1.402(2)
C14 C15 1.385(2)
C14 H14 0.9500
C15 C16 1.389(2)
C15 H15 0.9500
C16 C17 1.390(2)
C16 H16 0.9500
C17 C18 1.396(2)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.3952(19)
C19 C24 1.406(2)
C20 C21 1.383(2)
C20 H20 0.9500
C21 C22 1.386(2)
C21 H21 0.9500
C22 C23 1.383(2)
C22 H22 0.9500
C23 C24 1.388(2)
C23 H23 0.9500
C24 H24 0.9500
C25 C26 1.517(2)
C25 H25A 0.9900
C25 H25B 0.9900
C27 C28 1.493(3)
C27 H27A 0.9900
C27 H27B 0.9900
C28 H28A 0.9800
C28 H28B 0.9800
C28 H28C 0.9800
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
C19 P2 N1 C25 -48.04(12)
C13 P2 N1 C25 56.64(12)
C19 P2 N1 P1 125.42(9)
C13 P2 N1 P1 -129.90(8)
C1 P1 N1 C25 135.36(10)
C7 P1 N1 C25 -117.97(10)
C1 P1 N1 P2 -38.55(10)
C7 P1 N1 P2 68.12(10)
N1 P1 C1 C2 113.36(13)
C7 P1 C1 C2 3.09(14)
N1 P1 C1 C6 -74.87(12)
C7 P1 C1 C6 174.86(12)
C6 C1 C2 C3 -1.5(2)
P1 C1 C2 C3 170.17(12)
C1 C2 C3 C4 -0.3(2)
C2 C3 C4 C5 2.3(2)
C3 C4 C5 C6 -2.4(2)
C4 C5 C6 C1 0.5(2)
C2 C1 C6 C5 1.4(2)
P1 C1 C6 C5 -170.83(12)
N1 P1 C7 C8 -22.32(15)
C1 P1 C7 C8 86.91(14)
N1 P1 C7 C12 157.82(11)
C1 P1 C7 C12 -92.95(12)
C12 C7 C8 C9 0.2(2)
P1 C7 C8 C9 -179.62(12)
C7 C8 C9 C10 1.6(2)
C8 C9 C10 C11 -1.9(2)
C9 C10 C11 C12 0.3(2)
C10 C11 C12 C7 1.6(2)
C8 C7 C12 C11 -1.9(2)
P1 C7 C12 C11 178.01(12)
N1 P2 C13 C18 22.30(13)
C19 P2 C13 C18 129.87(13)
N1 P2 C13 C14 -163.96(11)
C19 P2 C13 C14 -56.39(13)
C18 C13 C14 C15 -0.5(2)
P2 C13 C14 C15 -174.52(12)
C13 C14 C15 C16 -0.3(2)
C14 C15 C16 C17 0.5(2)
C15 C16 C17 C18 0.2(2)
C16 C17 C18 C13 -1.0(2)
C14 C13 C18 C17 1.1(2)
P2 C13 C18 C17 174.87(11)
N1 P2 C19 C20 -105.66(12)
C13 P2 C19 C20 148.13(11)
N1 P2 C19 C24 73.92(14)
C13 P2 C19 C24 -32.29(14)
C24 C19 C20 C21 -0.8(2)
P2 C19 C20 C21 178.83(11)
C19 C20 C21 C22 -1.1(2)
C20 C21 C22 C23 1.7(2)
C21 C22 C23 C24 -0.4(2)
C22 C23 C24 C19 -1.5(2)
C20 C19 C24 C23 2.1(2)
P2 C19 C24 C23 -177.46(12)
P2 N1 C25 C26 96.79(13)
P1 N1 C25 C26 -77.29(14)
C27 O2 C26 O1 -0.6(2)
C27 O2 C26 C25 -178.47(13)
N1 C25 C26 O1 5.0(2)
N1 C25 C26 O2 -177.15(12)
C26 O2 C27 C28 -79.67(18)
