#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/02/7220239.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_7220239
loop_
_publ_author_name
'Armaghan, Mahsa'
'Lu, Wei-Yu'
'Wu, Di'
'Wei, Yao'
'Yuan, Feng-Ling'
'Weng, Ng Seik'
'MOHHAMADPOUR AMINI, MOSTAFA'
'Zhang, Wen-Hua'
'Young, David James'
'Hor, Andy'
'Lang, Jian-Ping'
_publ_section_title
;
 Isolation of first row transition metal--carboxylate zwitterions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA05564D
_journal_year                    2015
_chemical_formula_moiety         'C14 H16 N2 Ni O8'
_chemical_formula_sum            'C14 H16 N2 Ni O8'
_chemical_formula_weight         399.00
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-07-10 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1353(4)
_cell_length_b                   13.2866(8)
_cell_length_c                   16.8095(10)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      42.90
_cell_measurement_theta_min      3.066
_cell_volume                     1593.61(16)
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker ApexII'
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            45407
_diffrn_reflns_theta_full        40.25
_diffrn_reflns_theta_max         40.25
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         5008
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0322
_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)+(0.0411P)²+0.4543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                3552
_reflns_number_total             5008
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra05564d2.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7220239
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
Ni1 Ni 1.0000 0.0000 0.5000 0.02100(5) Uani 1 2 d S
O1 O 0.91687(13) 0.14849(5) 0.49016(4) 0.02869(15) Uani 1 1 d D
H1 H 0.926(3) 0.1838(13) 0.4488(9) 0.059(5) Uiso 1 1 d D
O2 O 0.9469(2) 0.25497(7) 0.85978(5) 0.0666(4) Uani 1 1 d .
O3 O 1.00482(12) 0.10512(7) 0.91076(4) 0.03420(17) Uani 1 1 d .
O1W O 1.27108(12) 0.04420(6) 0.47071(5) 0.03114(15) Uani 1 1 d D
H2W H 1.334(2) -0.0049(11) 0.4539(11) 0.051(5) Uiso 1 1 d D
H1W H 1.329(2) 0.0632(14) 0.5089(9) 0.049(5) Uiso 1 1 d D
N1 N 1.02401(12) 0.04777(6) 0.61662(4) 0.02321(14) Uani 1 1 d .
C1 C 0.95406(19) 0.20973(7) 0.55726(5) 0.0314(2) Uani 1 1 d .
H1A H 0.8489 0.2544 0.5667 0.038 Uiso 1 1 calc R
H1B H 1.0642 0.2507 0.5473 0.038 Uiso 1 1 calc R
C2 C 0.98607(13) 0.14499(6) 0.62913(5) 0.02235(15) Uani 1 1 d .
C3 C 0.97599(15) 0.18526(7) 0.70536(5) 0.02617(18) Uani 1 1 d .
H3 H 0.9501 0.2533 0.7125 0.031 Uiso 1 1 calc R
C4 C 1.00473(13) 0.12360(7) 0.77049(5) 0.02259(15) Uani 1 1 d .
C5 C 1.04595(17) 0.02286(7) 0.75715(5) 0.02851(18) Uani 1 1 d .
H5 H 1.0675 -0.0204 0.7996 0.034 Uiso 1 1 calc R
C6 C 1.0544(2) -0.01210(7) 0.67986(6) 0.0306(2) Uani 1 1 d .
H6 H 1.0822 -0.0796 0.6712 0.037 Uiso 1 1 calc R
C7 C 0.98536(15) 0.16440(7) 0.85409(5) 0.02745(18) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.03349(9) 0.01829(7) 0.01123(6) -0.00188(4) -0.00018(5) 0.00209(5)
O1 0.0517(5) 0.0211(3) 0.0132(2) 0.0010(2) -0.0016(2) 0.0043(3)
O2 0.1572(12) 0.0258(4) 0.0166(3) -0.0051(3) -0.0016(5) 0.0189(6)
O3 0.0510(5) 0.0362(4) 0.0153(3) 0.0066(3) 0.0025(3) 0.0071(3)
O1W 0.0351(4) 0.0319(4) 0.0263(3) -0.0066(3) 0.0000(3) -0.0007(3)
N1 0.0370(4) 0.0192(3) 0.0135(2) -0.0020(2) -0.0007(2) 0.0027(3)
C1 0.0603(6) 0.0194(3) 0.0146(3) 0.0013(3) -0.0001(4) 0.0021(4)
C2 0.0363(4) 0.0179(3) 0.0128(3) -0.0001(2) 0.0009(3) 0.0006(3)
C3 0.0471(5) 0.0181(3) 0.0134(3) -0.0013(2) 0.0005(3) 0.0022(3)
C4 0.0348(4) 0.0203(3) 0.0128(3) -0.0009(2) -0.0002(3) -0.0002(3)
C5 0.0491(5) 0.0207(3) 0.0157(3) 0.0004(3) -0.0032(3) 0.0045(4)
C6 0.0546(6) 0.0201(3) 0.0170(3) -0.0016(3) -0.0038(4) 0.0080(4)
C7 0.0462(6) 0.0236(4) 0.0125(3) -0.0008(3) -0.0005(3) 0.0011(3)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Ni1 O1 180.00(3) 5_756 .
O1 Ni1 N1 78.85(3) 5_756 5_756
O1 Ni1 N1 101.15(3) . 5_756
O1 Ni1 N1 101.15(3) 5_756 .
O1 Ni1 N1 78.85(3) . .
N1 Ni1 N1 180.0 5_756 .
O1 Ni1 O1W 91.24(3) 5_756 .
O1 Ni1 O1W 88.76(3) . .
N1 Ni1 O1W 86.52(3) 5_756 .
N1 Ni1 O1W 93.48(3) . .
O1 Ni1 O1W 88.76(3) 5_756 5_756
O1 Ni1 O1W 91.24(3) . 5_756
N1 Ni1 O1W 93.48(3) 5_756 5_756
N1 Ni1 O1W 86.52(3) . 5_756
O1W Ni1 O1W 180.0 . 5_756
C1 O1 Ni1 115.53(6) . .
C1 O1 H1 108.8(13) . .
Ni1 O1 H1 125.2(13) . .
Ni1 O1W H2W 110.8(12) . .
Ni1 O1W H1W 112.1(13) . .
H2W O1W H1W 103.9(19) . .
C2 N1 C6 118.68(7) . .
C2 N1 Ni1 115.41(6) . .
C6 N1 Ni1 125.52(6) . .
O1 C1 C2 109.91(7) . .
O1 C1 H1A 109.7 . .
C2 C1 H1A 109.7 . .
O1 C1 H1B 109.7 . .
C2 C1 H1B 109.7 . .
H1A C1 H1B 108.2 . .
N1 C2 C3 121.83(8) . .
N1 C2 C1 117.27(7) . .
C3 C2 C1 120.90(8) . .
C4 C3 C2 119.60(8) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 118.33(8) . .
C3 C4 C7 120.64(8) . .
C5 C4 C7 120.99(8) . .
C6 C5 C4 119.04(8) . .
C6 C5 H5 120.5 . .
C4 C5 H5 120.5 . .
N1 C6 C5 122.50(8) . .
N1 C6 H6 118.7 . .
C5 C6 H6 118.7 . .
O2 C7 O3 125.53(9) . .
O2 C7 C4 116.13(8) . .
O3 C7 C4 118.32(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0669(7) 5_756
Ni1 O1 2.0669(7) .
Ni1 N1 2.0677(7) 5_756
Ni1 N1 2.0677(7) .
Ni1 O1W 2.0805(9) .
Ni1 O1W 2.0805(9) 5_756
O1 C1 1.4158(12) .
O1 H1 0.841(14) .
O2 C7 1.2379(13) .
O3 C7 1.2437(12) .
O1W H2W 0.839(13) .
O1W H1W 0.803(13) .
N1 C2 1.3364(11) .
N1 C6 1.3454(12) .
C1 C2 1.5006(12) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.3906(12) .
C3 C4 1.3827(12) .
C3 H3 0.9300 .
C4 C5 1.3886(13) .
C4 C7 1.5125(12) .
C5 C6 1.3810(13) .
C5 H5 0.9300 .
C6 H6 0.9300 .
