#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511278.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_4511278
loop_
_publ_author_name
'Ye, Han-Tao'
'Ren, Chang-Yue'
'Hou, Guang-Feng'
'Yu, Ying-Hui'
'Xu, Xin'
'Gao, Jin-Sheng'
'Yan, Peng-Fei'
'Ng, Seik-Weng'
_publ_section_title
;
 Syntheses, Structures, and Second-Order Nonlinear Optical Properties of
 Chiral Zinc(II) Coordination Polymers Based on
 (R)-4-(4-(1-Carboxyethoxy)phenoxy)-3-fluorobenzoic Acid and Effect of the
 Second Ligand with Imidazole Group
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3309
_journal_paper_doi               10.1021/cg500197v
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C16 H11 F O6 Zn'
_chemical_formula_sum            'C16 H11 F O6 Zn'
_chemical_formula_weight         383.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   4.9328(10)
_cell_length_b                   10.137(2)
_cell_length_c                   29.718(6)
_cell_measurement_reflns_used    10020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.40
_cell_volume                     1486.0(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11240
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.8263
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.902
_refine_diff_density_min         -1.287
_refine_diff_density_rms         0.225
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0989
_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)+(0.1954P)²+3.0606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2811
_refine_ls_wR_factor_ref         0.2981
_reflns_number_gt                2114
_reflns_number_total             2596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500197v_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4511278--4511282.cif.'
_cod_database_code               4511278
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'
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
C1 C 0.8193(17) 1.0686(8) 0.9601(3) 0.0248(17) Uani 1 1 d .
C2 C 0.9529(18) 0.9605(8) 0.9337(3) 0.0266(18) Uani 1 1 d .
H2 H 1.1074 0.9960 0.9169 0.032 Uiso 1 1 calc R
C3 C 1.052(3) 0.8517(10) 0.9669(4) 0.047(3) Uani 1 1 d .
H3A H 0.8977 0.8062 0.9792 0.070 Uiso 1 1 calc R
H3B H 1.1533 0.8916 0.9908 0.070 Uiso 1 1 calc R
H3C H 1.1646 0.7900 0.9511 0.070 Uiso 1 1 calc R
C4 C 0.684(2) 0.9651(8) 0.8670(3) 0.0273(18) Uani 1 1 d .
C5 C 0.467(2) 0.9043(10) 0.8435(3) 0.035(2) Uani 1 1 d .
H5 H 0.3888 0.8272 0.8543 0.042 Uiso 1 1 calc R
C6 C 0.377(2) 0.9596(10) 0.8055(3) 0.040(2) Uani 1 1 d .
H6 H 0.2378 0.9192 0.7896 0.048 Uiso 1 1 calc R
C7 C 0.490(2) 1.0779(10) 0.7890(3) 0.036(2) Uani 1 1 d .
C8 C 0.691(2) 1.1371(9) 0.8107(3) 0.040(2) Uani 1 1 d .
H8 H 0.7666 1.2137 0.7989 0.048 Uiso 1 1 calc R
C9 C 0.793(2) 1.0839(9) 0.8523(3) 0.037(2) Uani 1 1 d .
H9 H 0.9269 1.1272 0.8687 0.045 Uiso 1 1 calc R
C10 C 0.4047(18) 1.0742(8) 0.7105(3) 0.0265(17) Uani 1 1 d .
C11 C 0.5948(19) 0.9778(10) 0.7016(3) 0.036(2) Uani 1 1 d .
H11 H 0.7154 0.9519 0.7240 0.043 Uiso 1 1 calc R
C12 C 0.6071(19) 0.9200(10) 0.6599(3) 0.033(2) Uani 1 1 d .
H12 H 0.7348 0.8544 0.6544 0.040 Uiso 1 1 calc R
C13 C 0.4276(19) 0.9589(9) 0.6250(3) 0.0292(19) Uani 1 1 d .
C14 C 0.2390(19) 1.0573(9) 0.6338(3) 0.031(2) Uani 1 1 d .
H14 H 0.1217 1.0860 0.6114 0.037 Uiso 1 1 calc R
C15 C 0.2280(18) 1.1117(8) 0.6761(3) 0.0295(19) Uani 1 1 d .
C16 C 0.437(2) 0.8901(10) 0.5807(3) 0.035(2) Uani 1 1 d .
F1 F 0.0416(13) 1.2061(6) 0.68521(19) 0.0435(14) Uani 1 1 d .
Zn1 Zn 0.3343(3) 1.19249(17) 0.98930(5) 0.0653(6) Uani 1 1 d .
O1 O 0.5661(13) 1.0668(9) 0.9663(2) 0.0449(18) Uani 1 1 d .
O2 O 0.9672(13) 1.1612(6) 0.9746(2) 0.0343(15) Uani 1 1 d .
O3 O 0.7698(16) 0.8954(6) 0.9036(2) 0.0415(18) Uani 1 1 d .
O4 O 0.3783(16) 1.1382(7) 0.7506(2) 0.0404(17) Uani 1 1 d .
O5 O 0.2489(18) 0.9232(9) 0.5520(2) 0.052(2) Uani 1 1 d .
O6 O 0.6113(17) 0.8045(8) 0.5743(3) 0.055(2) 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'
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'
F F 0.0171 0.0103 '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 C1 O2 122.1(9) . .
O1 C1 C2 120.0(8) . .
O2 C1 C2 117.9(7) . .
O3 C2 C1 112.7(7) . .
O3 C2 C3 105.5(7) . .
C1 C2 C3 108.9(8) . .
O3 C2 H2 109.9 . .
C1 C2 H2 109.9 . .
C3 C2 H2 109.9 . .
C2 C3 H3A 109.5 . .
C2 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C2 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O3 C4 C9 125.3(8) . .
O3 C4 C5 113.7(8) . .
C9 C4 C5 121.0(9) . .
C6 C5 C4 118.9(9) . .
C6 C5 H5 120.5 . .
C4 C5 H5 120.5 . .
C5 C6 C7 121.4(9) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C8 C7 O4 119.3(9) . .
C8 C7 C6 120.7(9) . .
O4 C7 C6 119.9(9) . .
C7 C8 C9 120.7(9) . .
C7 C8 H8 119.7 . .
C9 C8 H8 119.7 . .
C4 C9 C8 117.2(9) . .
C4 C9 H9 121.4 . .
C8 C9 H9 121.4 . .
O4 C10 C11 124.7(8) . .
O4 C10 C15 116.8(8) . .
C11 C10 C15 118.5(8) . .
C12 C11 C10 120.4(8) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C13 120.9(9) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C14 C13 C12 118.6(8) . .
C14 C13 C16 121.6(8) . .
C12 C13 C16 119.7(9) . .
C15 C14 C13 119.2(8) . .
C15 C14 H14 120.4 . .
C13 C14 H14 120.4 . .
F1 C15 C14 119.5(8) . .
F1 C15 C10 118.1(8) . .
C14 C15 C10 122.4(8) . .
O6 C16 O5 125.0(9) . .
O6 C16 C13 119.2(9) . .
O5 C16 C13 115.7(9) . .
O1 Zn1 O2 113.1(3) . 1_455
O1 Zn1 O2 121.5(3) . 4_477
O2 Zn1 O2 125.4(3) 1_455 4_477
O1 Zn1 O6 87.9(3) . 3_656
O2 Zn1 O6 90.3(3) 1_455 3_656
O2 Zn1 O6 92.2(3) 4_477 3_656
O1 Zn1 O5 93.5(3) . 2_575
O2 Zn1 O5 85.9(3) 1_455 2_575
O2 Zn1 O5 90.1(3) 4_477 2_575
O6 Zn1 O5 176.2(3) 3_656 2_575
O1 Zn1 Zn1 80.0(3) . 4_577
O2 Zn1 Zn1 165.0(2) 1_455 4_577
O2 Zn1 Zn1 42.3(2) 4_477 4_577
O6 Zn1 Zn1 82.8(2) 3_656 4_577
O5 Zn1 Zn1 101.0(2) 2_575 4_577
O1 Zn1 Zn1 156.6(3) . 4_477
O2 Zn1 Zn1 43.81(18) 1_455 4_477
O2 Zn1 Zn1 81.6(2) 4_477 4_477
O6 Zn1 Zn1 95.0(2) 3_656 4_477
O5 Zn1 Zn1 82.4(3) 2_575 4_477
Zn1 Zn1 Zn1 123.40(12) 4_577 4_477
C1 O1 Zn1 131.1(8) . .
C1 O2 Zn1 139.1(6) . 1_655
C1 O2 Zn1 124.1(6) . 4_577
Zn1 O2 Zn1 93.9(3) 1_655 4_577
C4 O3 C2 117.2(7) . .
C10 O4 C7 117.8(7) . .
C16 O5 Zn1 122.6(7) . 2_574
C16 O6 Zn1 125.1(7) . 3_646
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.263(11) .
C1 O2 1.265(11) .
C1 C2 1.500(12) .
C2 O3 1.434(10) .
C2 C3 1.556(12) .
C2 H2 0.9800 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C4 O3 1.365(11) .
C4 C9 1.390(13) .
C4 C5 1.417(13) .
C5 C6 1.336(15) .
C5 H5 0.9300 .
C6 C7 1.409(15) .
C6 H6 0.9300 .
C7 C8 1.328(15) .
C7 O4 1.407(12) .
C8 C9 1.440(14) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 O4 1.363(11) .
C10 C11 1.380(13) .
C10 C15 1.394(13) .
C11 C12 1.371(14) .
C11 H11 0.9300 .
C12 C13 1.420(13) .
C12 H12 0.9300 .
C13 C14 1.389(13) .
C13 C16 1.490(13) .
C14 C15 1.375(14) .
C14 H14 0.9300 .
C15 F1 1.354(10) .
C16 O6 1.236(13) .
C16 O5 1.305(13) .
Zn1 O1 1.844(8) .
Zn1 O2 1.889(7) 1_455
Zn1 O2 1.944(6) 4_477
Zn1 O6 2.220(7) 3_656
Zn1 O5 2.240(7) 2_575
Zn1 Zn1 2.8012(16) 4_577
Zn1 Zn1 2.8012(16) 4_477
O2 Zn1 1.889(7) 1_655
O2 Zn1 1.944(6) 4_577
O5 Zn1 2.240(7) 2_574
O6 Zn1 2.220(7) 3_646
