#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:58:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178708 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/19/4081998.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_4081998
loop_
_publ_author_name
'Yoo, Changho'
'Kim, Jin'
'Lee, Yunho'
_publ_section_title
;
 Synthesis and Reactivity of Nickel(II) Hydroxycarbonyl Species,
 NiCOOH-\kC
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              7195
_journal_paper_doi               10.1021/om400881j
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         C27H41N1Ni1O2P2
_chemical_formula_sum            'C27 H41 N Ni O2 P2'
_chemical_formula_weight         532.26
_chemical_name_common            (PNP)NiOCHO
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.793(3)
_cell_length_b                   16.677(3)
_cell_length_c                   9.6628(17)
_cell_measurement_reflns_used    6640
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      1.72
_cell_measurement_theta_min      28.38
_cell_volume                     2706.1(8)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.1439
_diffrn_reflns_av_sigmaI/netI    0.2314
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19706
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.039(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         6640
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.715
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0505
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0788
_reflns_number_gt                3407
_reflns_number_total             6640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400881j_si_002.cif
_cod_data_source_block           lyh34-1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2706.2(8)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4081998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
Ni Ni 0.75685(3) 0.55067(3) 0.11998(7) 0.01301(13) Uani 1 1 d .
P1 P 0.84836(8) 0.58582(7) 0.27194(13) 0.0128(3) Uani 1 1 d .
P2 P 0.68866(8) 0.51947(7) -0.06592(13) 0.0140(3) Uani 1 1 d .
N N 0.7971(2) 0.6355(2) 0.0103(4) 0.0121(10) Uani 1 1 d .
O1 O 0.7153(2) 0.46453(18) 0.2251(3) 0.0188(9) Uani 1 1 d .
O2 O 0.6429(2) 0.5475(2) 0.3596(3) 0.0314(9) Uani 1 1 d .
C1 C 0.9081(3) 0.6510(3) 0.1650(4) 0.0123(12) Uani 1 1 d .
C2 C 0.8729(3) 0.6657(3) 0.0364(5) 0.0122(11) Uani 1 1 d .
C3 C 0.9221(3) 0.7049(2) -0.0637(5) 0.0146(11) Uani 1 1 d .
H3A H 0.9038 0.7118 -0.1538 0.017 Uiso 1 1 calc R
C4 C 0.9964(3) 0.7324(2) -0.0273(5) 0.0160(12) Uani 1 1 d .
H4A H 1.0266 0.7590 -0.0937 0.019 Uiso 1 1 calc R
C5 C 1.0284(3) 0.7224(2) 0.1039(6) 0.0137(11) Uani 1 1 d .
C6 C 0.9826(3) 0.6795(3) 0.1983(5) 0.0140(11) Uani 1 1 d .
H6A H 1.0028 0.6697 0.2863 0.017 Uiso 1 1 calc R
C7 C 1.1098(3) 0.7526(3) 0.1407(6) 0.0234(13) Uani 1 1 d .
H7A H 1.1321 0.7806 0.0631 0.035 Uiso 1 1 calc R
H7B H 1.1434 0.7081 0.1643 0.035 Uiso 1 1 calc R
H7C H 1.1060 0.7883 0.2184 0.035 Uiso 1 1 calc R
C8 C 0.6935(3) 0.6130(2) -0.1580(5) 0.0113(11) Uani 1 1 d .
C9 C 0.7510(3) 0.6644(3) -0.1011(4) 0.0144(11) Uani 1 1 d .
C10 C 0.7556(3) 0.7429(3) -0.1538(5) 0.0157(12) Uani 1 1 d .
H10A H 0.7923 0.7789 -0.1172 0.019 Uiso 1 1 calc R
C11 C 0.7059(3) 0.7665(3) -0.2594(5) 0.0149(12) Uani 1 1 d .
H11A H 0.7099 0.8187 -0.2924 0.018 Uiso 1 1 calc R
C13 C 0.6499(3) 0.7156(3) -0.3189(5) 0.0173(12) Uani 1 1 d .
C14 C 0.6448(3) 0.6379(3) -0.2646(5) 0.0120(11) Uani 1 1 d .
H14A H 0.6077 0.6023 -0.3012 0.014 Uiso 1 1 calc R
C15 C 0.5954(3) 0.7433(3) -0.4329(4) 0.0205(13) Uani 1 1 d .
H15A H 0.5950 0.7043 -0.5059 0.031 Uiso 1 1 calc R
H15B H 0.6139 0.7937 -0.4684 0.031 Uiso 1 1 calc R
H15C H 0.5424 0.7496 -0.3971 0.031 Uiso 1 1 calc R
C16 C 0.7720(3) 0.7166(3) 0.3723(5) 0.0245(15) Uani 1 1 d .
H16A H 0.7546 0.7481 0.4498 0.037 Uiso 1 1 calc R
H16B H 0.7267 0.6997 0.3194 0.037 Uiso 1 1 calc R
H16C H 0.8065 0.7483 0.3149 0.037 Uiso 1 1 calc R
C17 C 0.8170(3) 0.6435(2) 0.4240(5) 0.0131(11) Uani 1 1 d .
H17A H 0.7793 0.6103 0.4763 0.016 Uiso 1 1 calc R
C18 C 0.8839(3) 0.6675(3) 0.5223(5) 0.0214(13) Uani 1 1 d .
H18A H 0.8622 0.6973 0.5985 0.032 Uiso 1 1 calc R
H18B H 0.9219 0.7001 0.4737 0.032 Uiso 1 1 calc R
H18C H 0.9098 0.6202 0.5566 0.032 Uiso 1 1 calc R
C19 C 0.8781(3) 0.4541(3) 0.4408(5) 0.0238(12) Uani 1 1 d .
H19A H 0.9154 0.4141 0.4708 0.036 Uiso 1 1 calc R
H19B H 0.8324 0.4284 0.4005 0.036 Uiso 1 1 calc R
H19C H 0.8616 0.4858 0.5186 0.036 Uiso 1 1 calc R
C20 C 0.9175(3) 0.5082(3) 0.3331(5) 0.0149(12) Uani 1 1 d .
H20A H 0.9628 0.5350 0.3770 0.018 Uiso 1 1 calc R
C21 C 0.9487(3) 0.4597(3) 0.2106(5) 0.0273(14) Uani 1 1 d .
H21A H 0.9848 0.4193 0.2434 0.041 Uiso 1 1 calc R
H21B H 0.9760 0.4946 0.1476 0.041 Uiso 1 1 calc R
H21C H 0.9049 0.4345 0.1638 0.041 Uiso 1 1 calc R
C22 C 0.5337(3) 0.5441(3) 0.0254(5) 0.0253(13) Uani 1 1 d .
H22A H 0.4793 0.5264 0.0250 0.038 Uiso 1 1 calc R
H22B H 0.5367 0.5976 -0.0110 0.038 Uiso 1 1 calc R
H22C H 0.5536 0.5436 0.1186 0.038 Uiso 1 1 calc R
C23 C 0.5838(3) 0.4879(3) -0.0640(6) 0.0198(12) Uani 1 1 d .
H23A H 0.5637 0.4918 -0.1590 0.024 Uiso 1 1 calc R
C24 C 0.5745(3) 0.4012(3) -0.0181(5) 0.0330(16) Uani 1 1 d .
H24A H 0.5948 0.3952 0.0742 0.050 Uiso 1 1 calc R
H24B H 0.6038 0.3669 -0.0797 0.050 Uiso 1 1 calc R
H24C H 0.5192 0.3867 -0.0199 0.050 Uiso 1 1 calc R
C25 C 0.7049(3) 0.4300(3) -0.3130(4) 0.0267(14) Uani 1 1 d .
H25A H 0.7358 0.3905 -0.3617 0.040 Uiso 1 1 calc R
H25B H 0.7044 0.4791 -0.3649 0.040 Uiso 1 1 calc R
H25C H 0.6514 0.4109 -0.3018 0.040 Uiso 1 1 calc R
C26 C 0.7417(3) 0.4449(3) -0.1717(4) 0.0168(11) Uani 1 1 d .
H26A H 0.7391 0.3940 -0.1212 0.020 Uiso 1 1 calc R
C27 C 0.8306(3) 0.4680(3) -0.1812(5) 0.0242(14) Uani 1 1 d .
H27A H 0.8583 0.4291 -0.2364 0.036 Uiso 1 1 calc R
H27B H 0.8532 0.4693 -0.0900 0.036 Uiso 1 1 calc R
H27C H 0.8355 0.5199 -0.2232 0.036 Uiso 1 1 calc R
C28 C 0.6670(3) 0.4818(3) 0.3216(5) 0.0260(14) Uani 1 1 d .
H28A H 0.6470 0.4382 0.3706 0.031 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'
Ni Ni 0.3393 1.1124 '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
O1 Ni N 178.35(16)
O1 Ni P2 93.82(10)
N Ni P2 84.55(12)
O1 Ni P1 95.83(10)
N Ni P1 85.72(12)
P2 Ni P1 166.55(6)
C1 P1 C17 107.6(2)
C1 P1 C20 104.9(2)
C17 P1 C20 107.1(2)
C1 P1 Ni 99.59(16)
C17 P1 Ni 118.22(16)
C20 P1 Ni 117.87(16)
C8 P2 C23 107.3(2)
C8 P2 C26 106.8(2)
C23 P2 C26 106.0(2)
C8 P2 Ni 100.14(16)
C23 P2 Ni 124.06(19)
C26 P2 Ni 111.26(16)
C2 N C9 121.1(4)
C2 N Ni 119.7(3)
C9 N Ni 119.2(3)
C28 O1 Ni 117.2(3)
C6 C1 C2 122.2(4)
C6 C1 P1 125.4(4)
C2 C1 P1 112.2(4)
N C2 C1 119.0(4)
N C2 C3 124.8(4)
C1 C2 C3 115.9(4)
C4 C3 C2 120.2(5)
C3 C4 C5 123.1(5)
C4 C5 C6 116.5(4)
C4 C5 C7 122.0(5)
C6 C5 C7 121.4(5)
C1 C6 C5 121.8(4)
C14 C8 C9 121.1(4)
C14 C8 P2 127.2(4)
C9 C8 P2 111.6(4)
C8 C9 C10 117.7(4)
C8 C9 N 117.8(4)
C10 C9 N 124.4(4)
C11 C10 C9 120.1(4)
C10 C11 C13 122.8(4)
C11 C13 C14 116.9(4)
C11 C13 C15 121.7(4)
C14 C13 C15 121.4(5)
C8 C14 C13 121.5(4)
C16 C17 C18 111.1(4)
C16 C17 P1 107.5(3)
C18 C17 P1 115.1(3)
C21 C20 C19 111.3(4)
C21 C20 P1 110.0(3)
C19 C20 P1 111.2(3)
C24 C23 C22 111.2(4)
C24 C23 P2 111.9(3)
C22 C23 P2 110.9(3)
C25 C26 C27 112.3(4)
C25 C26 P2 114.4(4)
C27 C26 P2 109.4(3)
O2 C28 O1 129.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ni O1 1.893(3)
Ni N 1.892(4)
Ni P2 2.1929(15)
Ni P1 2.2047(14)
P1 C1 1.805(5)
P1 C17 1.834(5)
P1 C20 1.836(4)
P2 C8 1.797(4)
P2 C23 1.838(5)
P2 C26 1.840(5)
N C2 1.392(6)
N C9 1.410(5)
O1 C28 1.269(5)
O2 C28 1.225(6)
C1 C6 1.375(6)
C1 C2 1.398(6)
C2 C3 1.431(6)
C3 C4 1.375(6)
C4 C5 1.387(6)
C5 C6 1.392(6)
C5 C7 1.499(6)
C8 C14 1.380(6)
C8 C9 1.404(6)
C9 C10 1.407(5)
C10 C11 1.376(6)
C11 C13 1.391(6)
C13 C14 1.400(6)
C13 C15 1.506(6)
C16 C17 1.519(6)
C17 C18 1.525(6)
C19 C20 1.528(6)
C20 C21 1.527(6)
C22 C23 1.527(6)
C23 C24 1.521(6)
C25 C26 1.519(6)
C26 C27 1.545(6)
