#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216521.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2216521
loop_
_publ_author_name
'Rong-Xun Li'
'Shao-Xiang Li'
'Qi-Ye Wu'
'Guang-Ye Liu'
'Fa-Qian Liu'
_publ_section_title
catena-Poly[[bis(1-ethylimidazole-κN³)zinc(II)]-μ-phthalato-κ²O¹:O²]
_journal_coeditor_code           HG2326
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2875
_journal_page_last               m2875
_journal_paper_doi               10.1107/S1600536807053159
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Zn (C8 H4 O4) (C5 H8 N2)2]'
_chemical_formula_moiety         'C18 H18 N4 O4 Zn'
_chemical_formula_sum            'C18 H18 N4 O4 Zn'
_chemical_formula_weight         419.75
_chemical_name_systematic
catena-Poly[[bis(1-ethylimidazole-\kN³)zinc(II)]-μ-phthalato-κ²O¹:O²]
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c 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                   10.209(2)
_cell_length_b                   13.870(3)
_cell_length_c                   13.583(3)
_cell_measurement_reflns_used    3025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.53
_cell_volume                     1923.3(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001 and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'thin-slice ω'
_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  0.0118
_diffrn_reflns_av_sigmaI/netI    0.1128
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2616
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.47
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.307
_exptl_absorpt_correction_T_max  0.8804
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.912
_refine_ls_abs_structure_details 'Flack (1983), 145 Friedel pairs'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0962P)²+2.22P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1825
_reflns_number_gt                1404
_reflns_number_total             2125
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2326.cif
_cod_data_source_block           I
_cod_database_code               2216521
_cod_database_fobs_code          2216521
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Zn Zn 0.19333(9) 0.74668(7) 0.75914(15) 0.0293(3) Uani d . 1
O O1 0.3715(7) 0.7223(5) 0.5888(5) 0.0359(16) Uani d . 1
O O2 0.3432(6) 0.8244(5) 0.7131(5) 0.0346(15) Uani d . 1
O O3 0.1449(7) 0.8235(5) 0.8761(5) 0.0406(17) Uani d . 1
O O4 -0.0256(8) 0.7258(5) 0.8876(6) 0.0401(17) Uani d . 1
N N1 0.2555(9) 0.6214(5) 0.8137(7) 0.0377(17) Uani d U 1
N N2 0.3722(10) 0.4877(7) 0.8343(9) 0.060 Uani d U 1
N N3 0.0552(7) 0.7507(5) 0.6519(7) 0.0294(17) Uani d . 1
N N4 -0.1320(9) 0.7819(7) 0.5765(9) 0.055 Uani d . 1
C C1 0.4036(12) 0.4780(9) 1.0816(11) 0.060 Uani d . 1
H H1A 0.3777 0.4604 1.1471 0.090 Uiso calc R 1
H H1B 0.4203 0.5461 1.0790 0.090 Uiso calc R 1
H H1C 0.4817 0.4435 1.0640 0.090 Uiso calc R 1
C C2 0.2942(11) 0.4526(9) 1.0096(10) 0.055 Uani d . 1
H H2B 0.3016 0.3847 0.9935 0.066 Uiso calc R 1
H H2C 0.2110 0.4616 1.0429 0.066 Uiso calc R 1
C C3 0.2910(10) 0.5061(7) 0.9196(9) 0.041 Uani d U 1
C C4 0.3455(9) 0.5592(7) 0.7707(9) 0.045 Uani d U 1
H H4B 0.3814 0.5660 0.7082 0.054 Uiso calc R 1
C C5 0.2333(10) 0.5884(7) 0.9032(8) 0.042(2) Uani d U 1
H H5A 0.1822 0.6204 0.9495 0.051 Uiso calc R 1
C C6 -0.1131(13) 0.7339(10) 0.3451(11) 0.062(3) Uani d U 1
H H6A -0.0954 0.7436 0.2764 0.093 Uiso calc R 1
H H6B -0.2057 0.7378 0.3564 0.093 Uiso calc R 1
H H6C -0.0819 0.6715 0.3647 0.093 Uiso calc R 1
C C7 -0.0448(12) 0.8101(8) 0.4040(8) 0.049(3) Uani d U 1
H H7A 0.0423 0.8196 0.3771 0.059 Uiso calc R 1
H H7B -0.0922 0.8703 0.3968 0.059 Uiso calc R 1
C C8 -0.0330(10) 0.7880(7) 0.5088(8) 0.036 Uani d U 1
C C9 0.0760(10) 0.7683(6) 0.5575(8) 0.035(2) Uani d . 1
H H9A 0.1585 0.7670 0.5285 0.042 Uiso calc R 1
C C10 -0.0729(10) 0.7633(8) 0.6662(9) 0.045(3) Uani d . 1
H H10A -0.1156 0.7600 0.7266 0.054 Uiso calc R 1
C C11 0.3983(9) 0.7972(6) 0.6299(7) 0.031(2) Uani d . 1
C C12 0.0351(9) 0.7984(7) 0.9131(7) 0.031 Uani d . 1
C C13 -0.0231(8) 0.8647(5) 0.9879(6) 0.021 Uani d . 1
C C14 -0.1150(10) 0.9321(7) 0.9505(8) 0.042(2) Uani d . 1
H H14A -0.1335 0.9334 0.8835 0.050 Uiso calc R 1
C C15 -0.1767(11) 0.9953(8) 1.0126(10) 0.054(3) Uani d . 1
H H15A -0.2393 1.0377 0.9881 0.065 Uiso calc R 1
C C16 -0.1455(12) 0.9963(9) 1.1132(10) 0.056 Uani d . 1
H H16A -0.1861 1.0399 1.1553 0.067 Uiso calc R 1
C C17 -0.0560(10) 0.9333(7) 1.1485(7) 0.039(2) Uani d . 1
H H17A -0.0359 0.9345 1.2153 0.046 Uiso calc R 1
C C18 0.0063(8) 0.8675(6) 1.0892(7) 0.0271(18) Uani d . 1
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_site_symmetry_3
_geom_angle
O2 Zn O3 . 98.9(3)
O2 Zn N1 . 110.3(3)
O3 Zn N1 . 104.5(3)
O2 Zn N3 . 107.2(3)
O3 Zn N3 . 112.9(3)
N1 Zn N3 . 120.8(3)
C11 O2 Zn . 116.5(6)
C12 O3 Zn . 112.9(6)
C5 N1 C4 . 106.6(9)
C5 N1 Zn . 126.2(7)
C4 N1 Zn . 126.6(7)
C4 N2 C3 . 105.6(9)
C9 N3 C10 . 105.9(9)
C9 N3 Zn . 126.1(7)
C10 N3 Zn . 125.5(8)
C8 N4 C10 . 106.3(9)
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C3 C2 C1 . 116.4(10)
C3 C2 H2B . 108.2
C1 C2 H2B . 108.2
C3 C2 H2C . 108.2
C1 C2 H2C . 108.2
H2B C2 H2C . 107.3
C5 C3 C2 . 127.6(11)
C5 C3 N2 . 106.0(10)
C2 C3 N2 . 125.5(10)
N2 C4 N1 . 108.8(10)
N2 C4 H4B . 125.6
N1 C4 H4B . 125.6
C3 C5 N1 . 112.6(10)
C3 C5 H5A . 123.7
N1 C5 H5A . 123.7
C7 C6 H6A . 109.5
C7 C6 H6B . 109.5
H6A C6 H6B . 109.5
C7 C6 H6C . 109.5
H6A C6 H6C . 109.5
H6B C6 H6C . 109.5
C8 C7 C6 . 114.3(10)
C8 C7 H7A . 108.7
C6 C7 H7A . 108.7
C8 C7 H7B . 108.7
C6 C7 H7B . 108.7
H7A C7 H7B . 107.6
C9 C8 N4 . 105.8(10)
C9 C8 C7 . 126.9(10)
N4 C8 C7 . 127.3(10)
C8 C9 N3 . 112.8(10)
C8 C9 H9A . 123.6
N3 C9 H9A . 123.6
N3 C10 N4 . 108.9(10)
N3 C10 H10A . 125.5
N4 C10 H10A . 125.5
O1 C11 O2 . 123.0(8)
O1 C11 C18 4_554 122.7(9)
O2 C11 C18 4_554 114.3(8)
O4 C12 O3 . 123.6(9)
O4 C12 C13 . 119.6(8)
O3 C12 C13 . 116.7(8)
C18 C13 C14 . 118.2(8)
C18 C13 C12 . 126.6(8)
C14 C13 C12 . 115.2(8)
C15 C14 C13 . 120.4(10)
C15 C14 H14A . 119.8
C13 C14 H14A . 119.8
C14 C15 C16 . 120.1(11)
C14 C15 H15A . 120.0
C16 C15 H15A . 120.0
C17 C16 C15 . 119.5(12)
C17 C16 H16A . 120.2
C15 C16 H16A . 120.2
C16 C17 C18 . 122.3(10)
C16 C17 H17A . 118.9
C18 C17 H17A . 118.9
C17 C18 C13 . 119.5(8)
C17 C18 C11 4 121.4(8)
C13 C18 C11 4 119.0(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn O2 . 1.974(6) yes
Zn O3 . 1.976(7) yes
Zn N1 . 1.993(8) yes
Zn N3 . 2.028(8) yes
O1 C11 . 1.211(12) yes
O2 C11 . 1.318(12) yes
O3 C12 . 1.277(12) yes
O4 C12 . 1.232(12) yes
N1 C5 . 1.318(14) ?
N1 C4 . 1.389(13) ?
N2 C4 . 1.343(15) ?
N2 C3 . 1.448(16) ?
N3 C9 . 1.323(14) ?
N3 C10 . 1.333(14) ?
N4 C8 . 1.369(14) ?
N4 C10 . 1.384(15) ?
C1 C2 . 1.526(17) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.430(17) ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 C5 . 1.305(14) ?
C4 H4B . 0.9300 ?
C5 H5A . 0.9300 ?
C6 C7 . 1.498(18) ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.461(16) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.322(14) ?
C9 H9A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C18 4_554 1.485(12) ?
C12 C13 . 1.493(12) ?
C13 C18 . 1.409(12) ?
C13 C14 . 1.419(13) ?
C14 C15 . 1.370(17) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.403(18) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.352(15) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.374(13) ?
C17 H17A . 0.9300 ?
C18 C11 4 1.485(12) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5A O1 4 0.93 2.42 3.309(13) 158.9 y
C7 H7A O2 4_554 0.97 2.52 3.317(13) 139.7 y
C9 H9A O1 ? 0.93 2.41 3.113(12) 133 y
C10 H10A O4 ? 0.93 2.42 3.090(15) 129 y
C16 H16A O2 2_575 0.93 2.59 3.478(14) 159.0 y
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_site_symmetry_4
_geom_torsion
O3 Zn O2 C11 . -176.2(6)
N1 Zn O2 C11 . 74.6(7)
N3 Zn O2 C11 . -58.8(6)
O2 Zn O3 C12 . 169.3(6)
N1 Zn O3 C12 . -76.9(7)
N3 Zn O3 C12 . 56.3(7)
O2 Zn N1 C5 . 122.8(9)
O3 Zn N1 C5 . 17.4(9)
N3 Zn N1 C5 . -111.1(9)
O2 Zn N1 C4 . -47.0(9)
O3 Zn N1 C4 . -152.4(8)
N3 Zn N1 C4 . 79.1(9)
O2 Zn N3 C9 . 23.5(8)
O3 Zn N3 C9 . 131.3(7)
N1 Zn N3 C9 . -104.1(8)
O2 Zn N3 C10 . -136.4(8)
O3 Zn N3 C10 . -28.6(9)
N1 Zn N3 C10 . 96.1(9)
C1 C2 C3 C5 . -87.3(16)
C1 C2 C3 N2 . 80.3(15)
C4 N2 C3 C5 . -5.0(13)
C4 N2 C3 C2 . -174.8(10)
C3 N2 C4 N1 . 1.7(12)
C5 N1 C4 N2 . 2.2(12)
Zn N1 C4 N2 . 173.6(7)
C2 C3 C5 N1 . 176.2(10)
N2 C3 C5 N1 . 6.8(13)
C4 N1 C5 C3 . -5.8(12)
Zn N1 C5 C3 . -177.2(7)
C10 N4 C8 C9 . 3.3(12)
C10 N4 C8 C7 . -177.7(11)
C6 C7 C8 C9 . 111.4(13)
C6 C7 C8 N4 . -67.4(15)
N4 C8 C9 N3 . -0.6(12)
C7 C8 C9 N3 . -179.6(10)
C10 N3 C9 C8 . -2.5(12)
Zn N3 C9 C8 . -165.5(7)
C9 N3 C10 N4 . 4.5(12)
Zn N3 C10 N4 . 167.7(7)
C8 N4 C10 N3 . -4.9(13)
Zn O2 C11 O1 . -9.0(12)
Zn O2 C11 C18 4_554 169.3(6)
Zn O3 C12 O4 . 9.5(12)
Zn O3 C12 C13 . -167.5(6)
O4 C12 C13 C18 . 99.1(12)
O3 C12 C13 C18 . -83.8(11)
O4 C12 C13 C14 . -82.3(11)
O3 C12 C13 C14 . 94.9(10)
C18 C13 C14 C15 . -2.5(14)
C12 C13 C14 C15 . 178.7(9)
C13 C14 C15 C16 . 2.4(17)
C14 C15 C16 C17 . -1.1(18)
C15 C16 C17 C18 . -0.1(17)
C16 C17 C18 C13 . 0.0(15)
C16 C17 C18 C11 4 -178.3(9)
C14 C13 C18 C17 . 1.3(13)
C12 C13 C18 C17 . 179.9(8)
C14 C13 C18 C11 4 179.6(8)
C12 C13 C18 C11 4 -1.7(13)
