#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/02/7220248.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_7220248
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         'C26 H24 N2 O8 Zn'
_chemical_formula_sum            'C26 H24 N2 O8 Zn'
_chemical_formula_weight         557.84
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 107.7859(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.0244(9)
_cell_length_b                   7.5228(3)
_cell_length_c                   12.9729(5)
_cell_measurement_reflns_used    5734
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.84
_cell_volume                     2325.47(15)
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_molecular_graphics    'Ortep3 (Farrugia, 1997)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10557
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+2.4455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2433
_reflns_number_total             2666
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra05564d2.cif
_cod_data_source_block           13
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7220248
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'
'-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
Zn1 Zn 0.0000 0.68778(4) 0.2500 0.03120(11) Uani 1 2 d S
O1 O -0.01278(6) 0.6935(3) 0.08146(13) 0.0562(5) Uani 1 1 d D
H1 H -0.0424(10) 0.726(4) 0.036(2) 0.067 Uiso 1 1 d D
O2 O 0.39021(6) 0.7246(3) 0.44379(13) 0.0661(6) Uani 1 1 d .
O3 O 0.44219(6) 0.6838(2) 0.33632(12) 0.0425(3) Uani 1 1 d .
O1W O 0.0000 0.9632(4) 0.2500 0.0986(13) Uani 1 2 d SDU
H1W H 0.0126(18) 1.017(5) 0.208(3) 0.118 Uiso 1 1 d D
O2W O 0.0000 0.4095(3) 0.2500 0.0874(11) Uani 1 2 d SDU
H2W H -0.0169(17) 0.347(4) 0.281(3) 0.105 Uiso 1 1 d D
N1 N 0.08142(6) 0.6758(2) 0.24039(12) 0.0301(3) Uani 1 1 d .
C1 C 0.03472(7) 0.7343(3) 0.05004(15) 0.0407(5) Uani 1 1 d .
H1A H 0.0339 0.8589 0.0302 0.049 Uiso 1 1 calc R
H1B H 0.0347 0.6637 -0.0125 0.049 Uiso 1 1 calc R
C2 C 0.08701(7) 0.6959(2) 0.14220(14) 0.0294(4) Uani 1 1 d .
C3 C 0.13866(7) 0.6838(3) 0.12391(14) 0.0332(4) Uani 1 1 d .
H3A H 0.1412 0.7007 0.0545 0.040 Uiso 1 1 calc R
C4 C 0.18662(7) 0.6466(2) 0.20875(14) 0.0296(4) Uani 1 1 d .
C5 C 0.17972(7) 0.6242(3) 0.31004(15) 0.0390(4) Uani 1 1 d .
H5A H 0.2106 0.5981 0.3694 0.047 Uiso 1 1 calc R
C6 C 0.12761(8) 0.6402(3) 0.32306(15) 0.0395(5) Uani 1 1 d .
H6A H 0.1241 0.6259 0.3919 0.047 Uiso 1 1 calc R
C7 C 0.24247(7) 0.6284(3) 0.19245(14) 0.0296(3) Uani 1 1 d .
C8 C 0.24746(8) 0.5733(3) 0.09346(15) 0.0416(5) Uani 1 1 d .
H8A H 0.2154 0.5477 0.0365 0.050 Uiso 1 1 calc R
C9 C 0.29980(8) 0.5563(3) 0.07896(16) 0.0464(5) Uani 1 1 d .
H9A H 0.3026 0.5188 0.0125 0.056 Uiso 1 1 calc R
C10 C 0.34767(7) 0.5945(3) 0.16227(15) 0.0375(4) Uani 1 1 d .
H10A H 0.3827 0.5844 0.1517 0.045 Uiso 1 1 calc R
C11 C 0.34376(7) 0.6482(2) 0.26187(14) 0.0290(3) Uani 1 1 d .
C12 C 0.29120(7) 0.6649(2) 0.27612(14) 0.0295(4) Uani 1 1 d .
H12A H 0.2886 0.7013 0.3429 0.035 Uiso 1 1 calc R
C13 C 0.39578(7) 0.6890(3) 0.35438(15) 0.0340(4) 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'
Zn Zn 0.2839 1.4301 '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
O1W Zn1 N1 92.49(4) . .
O1W Zn1 N1 92.49(4) . 2
N1 Zn1 N1 175.02(9) . 2
O1W Zn1 O2W 180.000(1) . .
N1 Zn1 O2W 87.51(4) . .
N1 Zn1 O2W 87.51(4) 2 .
O1W Zn1 O1 88.84(6) . 2
N1 Zn1 O1 102.80(6) . 2
N1 Zn1 O1 77.31(6) 2 2
O2W Zn1 O1 91.16(6) . 2
O1W Zn1 O1 88.84(6) . .
N1 Zn1 O1 77.30(6) . .
N1 Zn1 O1 102.80(6) 2 .
O2W Zn1 O1 91.16(6) . .
O1 Zn1 O1 177.67(11) 2 .
C1 O1 Zn1 115.55(12) . .
C1 O1 H1 113(2) . .
Zn1 O1 H1 124(2) . .
Zn1 O1W H1W 120(3) . .
Zn1 O2W H2W 125(3) . .
C2 N1 C6 118.08(15) . .
C2 N1 Zn1 116.31(11) . .
C6 N1 Zn1 125.51(12) . .
O1 C1 C2 109.58(15) . .
O1 C1 H1A 109.8 . .
C2 C1 H1A 109.8 . .
O1 C1 H1B 109.8 . .
C2 C1 H1B 109.8 . .
H1A C1 H1B 108.2 . .
N1 C2 C3 122.13(16) . .
N1 C2 C1 117.47(15) . .
C3 C2 C1 120.40(16) . .
C2 C3 C4 120.23(16) . .
C2 C3 H3A 119.9 . .
C4 C3 H3A 119.9 . .
C3 C4 C5 116.65(16) . .
C3 C4 C7 122.03(16) . .
C5 C4 C7 121.31(15) . .
C6 C5 C4 120.31(16) . .
C6 C5 H5A 119.8 . .
C4 C5 H5A 119.8 . .
N1 C6 C5 122.60(16) . .
N1 C6 H6A 118.7 . .
C5 C6 H6A 118.7 . .
C12 C7 C8 118.37(15) . .
C12 C7 C4 120.72(15) . .
C8 C7 C4 120.91(16) . .
C9 C8 C7 120.55(17) . .
C9 C8 H8A 119.7 . .
C7 C8 H8A 119.7 . .
C10 C9 C8 120.42(17) . .
C10 C9 H9A 119.8 . .
C8 C9 H9A 119.8 . .
C9 C10 C11 120.05(16) . .
C9 C10 H10A 120.0 . .
C11 C10 H10A 120.0 . .
C10 C11 C12 119.35(16) . .
C10 C11 C13 120.78(15) . .
C12 C11 C13 119.87(15) . .
C11 C12 C7 121.25(16) . .
C11 C12 H12A 119.4 . .
C7 C12 H12A 119.4 . .
O2 C13 O3 123.87(18) . .
O2 C13 C11 118.18(16) . .
O3 C13 C11 117.95(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1W 2.072(3) .
Zn1 N1 2.0809(14) .
Zn1 N1 2.0810(14) 2
Zn1 O2W 2.094(3) .
Zn1 O1 2.1113(16) 2
Zn1 O1 2.1113(16) .
O1 C1 1.403(2) .
O1 H1 0.829(18) .
O2 C13 1.239(2) .
O3 C13 1.253(2) .
O1W H1W 0.811(19) .
O2W H2W 0.811(19) .
N1 C2 1.332(2) .
N1 C6 1.342(2) .
C1 C2 1.506(2) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.387(2) .
C3 C4 1.387(2) .
C3 H3A 0.9300 .
C4 C5 1.387(2) .
C4 C7 1.482(2) .
C5 C6 1.370(2) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 C12 1.390(2) .
C7 C8 1.391(2) .
C8 C9 1.385(3) .
C8 H8A 0.9300 .
C9 C10 1.377(3) .
C9 H9A 0.9300 .
C10 C11 1.385(2) .
C10 H10A 0.9300 .
C11 C12 1.389(2) .
C11 C13 1.508(2) .
C12 H12A 0.9300 .
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
O1 H1 O2 0.829(18) 1.784(19) 2.610(2) 174(3) 8_465
O1 H1 O3 0.829(18) 2.59(3) 3.170(2) 128(3) 8_465
O1W H1W O3 0.811(19) 1.90(2) 2.663(2) 157(4) 4
O2W H2W O3 0.811(19) 1.88(2) 2.687(2) 173(4) 3_445
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
O1W Zn1 O1 C1 76.52(16) .
N1 Zn1 O1 C1 -16.30(16) .
N1 Zn1 O1 C1 168.81(16) 2
O2W Zn1 O1 C1 -103.48(16) .
O1 Zn1 O1 C1 76.45(17) 2
O1W Zn1 N1 C2 -81.45(13) .
N1 Zn1 N1 C2 98.54(13) 2
O2W Zn1 N1 C2 98.55(13) .
O1 Zn1 N1 C2 -170.82(13) 2
O1 Zn1 N1 C2 6.80(13) .
O1W Zn1 N1 C6 102.36(17) .
N1 Zn1 N1 C6 -77.66(17) 2
O2W Zn1 N1 C6 -77.64(17) .
O1 Zn1 N1 C6 12.99(19) 2
O1 Zn1 N1 C6 -169.40(18) .
Zn1 O1 C1 C2 21.6(2) .
C6 N1 C2 C3 -0.9(3) .
Zn1 N1 C2 C3 -177.41(14) .
C6 N1 C2 C1 179.52(19) .
Zn1 N1 C2 C1 3.0(2) .
O1 C1 C2 N1 -16.2(3) .
O1 C1 C2 C3 164.27(19) .
N1 C2 C3 C4 1.1(3) .
C1 C2 C3 C4 -179.32(19) .
C2 C3 C4 C5 -0.4(3) .
C2 C3 C4 C7 178.62(17) .
C3 C4 C5 C6 -0.5(3) .
C7 C4 C5 C6 -179.5(2) .
C2 N1 C6 C5 0.0(3) .
Zn1 N1 C6 C5 176.13(17) .
C4 C5 C6 N1 0.7(4) .
C3 C4 C7 C12 152.95(19) .
C5 C4 C7 C12 -28.1(3) .
C3 C4 C7 C8 -27.5(3) .
C5 C4 C7 C8 151.4(2) .
C12 C7 C8 C9 -0.3(3) .
C4 C7 C8 C9 -179.8(2) .
C7 C8 C9 C10 -0.3(4) .
C8 C9 C10 C11 0.9(4) .
C9 C10 C11 C12 -0.8(3) .
C9 C10 C11 C13 179.4(2) .
C10 C11 C12 C7 0.2(3) .
C13 C11 C12 C7 179.95(17) .
C8 C7 C12 C11 0.4(3) .
C4 C7 C12 C11 179.90(17) .
C10 C11 C13 O2 -175.1(2) .
C12 C11 C13 O2 5.1(3) .
C10 C11 C13 O3 4.4(3) .
C12 C11 C13 O3 -175.34(17) .
