#------------------------------------------------------------------------------
#$Date: 2017-03-05 09:45:04 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193976 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/07/2020709.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_2020709
loop_
_publ_author_name
'Tan, Xiong-Wen'
'Li, Heng-Feng'
'Li, Chang-Hong'
_publ_section_title
;
 Two new isomeric zinc(II) metal--organic frameworks based on
 1,5-bis(2-methyl-1H-imidazol-1-yl)pentane and 5-methylisophthalate
 ligands
;
_journal_coeditor_code           FM3047
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              78
_journal_page_last               83
_journal_paper_doi               10.1107/S2053229616020520
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          '[Zn (C9 H6 O4) (C13 H20 N4)]'
_chemical_formula_moiety         'C22 H26 N4 O4 Zn'
_chemical_formula_sum            'C22 H26 N4 O4 Zn'
_chemical_formula_weight         475.84
_chemical_name_systematic
Poly[[μ-1,5-bis(2-methyl-1H-imidazol-1-yl)pentane-κ²N³:N^3'^](μ-5-methylisophthalato-κ²O¹:O³)zinc(II)]
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 101.315(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4910(12)
_cell_length_b                   18.7233(13)
_cell_length_c                   11.9855(17)
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.11
_cell_volume                     2088.5(4)
_computing_cell_refinement
;
SMART (Bruker, 2008)
;
_computing_data_collection
;
SMART (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2008)
;
_computing_publication_material
;
SHELXTL (Bruker, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXTL (Bruker, 2008)
;
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19462
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         2.046
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.674
_refine_diff_density_min         -1.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5131
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                3145
_reflns_number_total             5131
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fm3047sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2020709--2020710.cif.'
_cod_database_code               2020709
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.829
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_occupancy
C C1 0.6251(3) 0.85279(16) 0.2830(2) 0.0365(7) Uani d 1
C C2 0.5166(3) 0.80305(15) 0.2781(2) 0.0353(7) Uani d 1
H H2 0.4602 0.7907 0.2083 0.042 Uiso calc 1
C C3 0.4918(3) 0.77169(16) 0.3763(2) 0.0329(7) Uani d 1
C C4 0.5812(3) 0.78604(16) 0.4799(2) 0.0364(7) Uani d 1
H H4 0.5675 0.7636 0.5461 0.044 Uiso calc 1
C C5 0.6901(3) 0.83420(18) 0.4819(2) 0.0450(8) Uani d 1
C C6 0.7122(3) 0.86874(17) 0.3874(3) 0.0441(8) Uani d 1
H H6 0.7847 0.9027 0.3924 0.053 Uiso calc 1
C C7 0.6565(3) 0.8897(2) 0.1787(3) 0.0430(8) Uani d 1
C C8 0.3692(3) 0.72031(16) 0.3693(2) 0.0382(7) Uani d 1
C C9 0.7881(3) 0.85194(17) 0.5848(2) 0.0397(8) Uani d 1
H H9A 0.8785 0.8286 0.5858 0.060 Uiso calc 1
H H9B 0.7495 0.8364 0.6490 0.060 Uiso calc 1
H H9C 0.8023 0.9027 0.5888 0.060 Uiso calc 1
C C10 0.2054(3) 0.46156(18) 0.4539(3) 0.0473(8) Uani d 1
H H10 0.1294 0.4596 0.4925 0.057 Uiso calc 1
C C11 0.2649(4) 0.40483(19) 0.4114(3) 0.0491(9) Uani d 1
H H11 0.2387 0.3572 0.4163 0.059 Uiso calc 1
C C12 0.3771(3) 0.50386(16) 0.3723(2) 0.0349(7) Uani d 1
C C13 0.4778(3) 0.55067(17) 0.3287(3) 0.0439(8) Uani d 1
H H13A 0.5696 0.5276 0.3373 0.066 Uiso calc 1
H H13B 0.4881 0.5947 0.3705 0.066 Uiso calc 1
H H13C 0.4416 0.5604 0.2496 0.066 Uiso calc 1
C C14 0.4666(4) 0.38905(18) 0.3020(3) 0.0570(10) Uani d 1
H H14A 0.5026 0.3488 0.3501 0.068 Uiso calc 1
H H14B 0.5485 0.4182 0.2940 0.068 Uiso calc 1
C C15 0.3990(5) 0.3621(2) 0.1898(3) 0.0887(13) Uani d 1
H H15A 0.4607 0.3255 0.1681 0.106 Uiso calc 1
H H15B 0.3091 0.3394 0.1963 0.106 Uiso calc 1
C C16 0.3684(5) 0.4160(2) 0.0957(3) 0.1086(17) Uani d 1
H H16A 0.4561 0.4372 0.0809 0.130 Uiso calc 1
H H16B 0.3048 0.4533 0.1123 0.130 Uiso calc 1
C C17 0.2966(6) 0.3697(3) -0.0016(3) 0.131(2) Uani d 1
H H17A 0.3540 0.3275 -0.0073 0.157 Uiso calc 1
H H17B 0.2025 0.3548 0.0095 0.157 Uiso calc 1
C C18 0.2833(5) 0.4140(3) -0.1073(3) 0.1010(15) Uani d 1
H H18A 0.3759 0.4176 -0.1296 0.121 Uiso calc 1
H H18B 0.2515 0.4618 -0.0931 0.121 Uiso calc 1
C C19 0.2106(5) 0.3301(3) -0.2792(4) 0.0989(17) Uani d 1
H H19 0.2988 0.3075 -0.2755 0.119 Uiso calc 1
C C20 0.0942(4) 0.3218(2) -0.3591(3) 0.0635(10) Uani d 1
H H20 0.0848 0.2896 -0.4192 0.076 Uiso calc 1
C C21 0.0396(4) 0.40194(18) -0.2402(3) 0.0507(9) Uani d 1
C C22 -0.0341(4) 0.4556(2) -0.1836(3) 0.0589(10) Uani d 1
H H22A -0.0063 0.4502 -0.1026 0.088 Uiso calc 1
H H22B -0.1361 0.4494 -0.2062 0.088 Uiso calc 1
H H22C -0.0081 0.5025 -0.2050 0.088 Uiso calc 1
N N1 0.2760(3) 0.52360(13) 0.4309(2) 0.0394(6) Uani d 1
N N2 0.3730(3) 0.43095(14) 0.3588(2) 0.0423(6) Uani d 1
N N3 0.1754(4) 0.3791(2) -0.2014(3) 0.1005(14) Uani d 1
N N4 -0.0113(3) 0.36841(14) -0.3397(2) 0.0419(6) Uani d 1
O O1 0.7093(3) 0.94941(14) 0.18676(18) 0.0633(7) Uani d 1
O O2 0.6253(2) 0.85306(12) 0.08773(18) 0.0521(6) Uani d 1
O O3 0.2858(2) 0.71001(12) 0.27618(17) 0.0529(6) Uani d 1
O O4 0.3529(2) 0.68946(11) 0.46039(16) 0.0414(5) Uani d 1
Zn Zn1 0.19652(4) 0.62010(2) 0.45205(3) 0.03624(12) 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_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 119.3(3)
C2 C1 C7 . . 122.8(3)
C6 C1 C7 . . 117.9(3)
C1 C2 C3 . . 120.2(3)
C1 C2 H2 . . 119.9
C3 C2 H2 . . 119.9
C4 C3 C2 . . 120.4(3)
C4 C3 C8 . . 120.5(3)
C2 C3 C8 . . 119.1(3)
C5 C4 C3 . . 118.2(3)
C5 C4 H4 . . 120.9
C3 C4 H4 . . 120.9
C6 C5 C4 . . 122.6(3)
C6 C5 C9 . . 115.4(3)
C4 C5 C9 . . 122.0(3)
C5 C6 C1 . . 119.2(3)
C5 C6 H6 . . 120.4
C1 C6 H6 . . 120.4
O1 C7 O2 . . 125.7(3)
O1 C7 C1 . . 120.0(3)
O2 C7 C1 . . 114.3(3)
O3 C8 O4 . . 122.3(3)
O3 C8 C3 . . 119.8(3)
O4 C8 C3 . . 117.8(3)
C5 C9 H9A . . 109.5
C5 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C5 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C11 C10 N1 . . 109.1(3)
C11 C10 H10 . . 125.4
N1 C10 H10 . . 125.4
C10 C11 N2 . . 107.1(3)
C10 C11 H11 . . 126.4
N2 C11 H11 . . 126.4
N1 C12 N2 . . 109.1(3)
N1 C12 C13 . . 127.1(3)
N2 C12 C13 . . 123.8(3)
C12 C13 H13A . . 109.5
C12 C13 H13B . . 109.5
H13A C13 H13B . . 109.5
C12 C13 H13C . . 109.5
H13A C13 H13C . . 109.5
H13B C13 H13C . . 109.5
N2 C14 C15 . . 114.8(3)
N2 C14 H14A . . 108.6
C15 C14 H14A . . 108.6
N2 C14 H14B . . 108.6
C15 C14 H14B . . 108.6
H14A C14 H14B . . 107.5
C16 C15 C14 . . 116.5(3)
C16 C15 H15A . . 108.2
C14 C15 H15A . . 108.2
C16 C15 H15B . . 108.2
C14 C15 H15B . . 108.2
H15A C15 H15B . . 107.3
C15 C16 C17 . . 100.8(3)
C15 C16 H16A . . 111.6
C17 C16 H16A . . 111.6
C15 C16 H16B . . 111.6
C17 C16 H16B . . 111.6
H16A C16 H16B . . 109.4
C18 C17 C16 . . 106.7(3)
C18 C17 H17A . . 110.4
C16 C17 H17A . . 110.4
C18 C17 H17B . . 110.4
C16 C17 H17B . . 110.4
H17A C17 H17B . . 108.6
C17 C18 N3 . . 108.9(4)
C17 C18 H18A . . 109.9
N3 C18 H18A . . 109.9
C17 C18 H18B . . 109.9
N3 C18 H18B . . 109.9
H18A C18 H18B . . 108.3
C20 C19 N3 . . 106.6(4)
C20 C19 H19 . . 126.7
N3 C19 H19 . . 126.7
C19 C20 N4 . . 109.5(3)
C19 C20 H20 . . 125.2
N4 C20 H20 . . 125.2
N4 C21 N3 . . 108.0(3)
N4 C21 C22 . . 127.4(3)
N3 C21 C22 . . 124.6(3)
C21 C22 H22A . . 109.5
C21 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C21 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C12 N1 C10 . . 107.1(3)
C12 N1 Zn1 . . 129.9(2)
C10 N1 Zn1 . . 121.4(2)
C12 N2 C11 . . 107.5(3)
C12 N2 C14 . . 125.9(3)
C11 N2 C14 . . 126.5(3)
C21 N3 C19 . . 108.4(3)
C21 N3 C18 . . 125.4(4)
C19 N3 C18 . . 124.5(4)
C21 N4 C20 . . 107.3(3)
C21 N4 Zn1 . 3_565 131.2(2)
C20 N4 Zn1 . 3_565 121.5(2)
C7 O2 Zn1 . 4_675 121.1(2)
C8 O4 Zn1 . . 118.41(19)
O2 Zn1 O4 4_576 . 99.79(9)
O2 Zn1 N1 4_576 . 122.87(10)
O4 Zn1 N1 . . 107.78(9)
O2 Zn1 N4 4_576 3_565 97.55(10)
O4 Zn1 N4 . 3_565 121.22(9)
N1 Zn1 N4 . 3_565 108.39(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.381(4)
C1 C6 . 1.390(4)
C1 C7 . 1.508(4)
C2 C3 . 1.377(4)
C2 H2 . 0.9300
C3 C4 . 1.385(4)
C3 C8 . 1.499(4)
C4 C5 . 1.368(4)
C4 H4 . 0.9300
C5 C6 . 1.356(4)
C5 C9 . 1.431(4)
C6 H6 . 0.9300
C7 O1 . 1.220(4)
C7 O2 . 1.274(4)
C8 O3 . 1.250(3)
C8 O4 . 1.271(3)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 C11 . 1.349(4)
C10 N1 . 1.396(4)
C10 H10 . 0.9300
C11 N2 . 1.395(4)
C11 H11 . 0.9300
C12 N1 . 1.347(3)
C12 N2 . 1.374(4)
C12 C13 . 1.467(4)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C14 N2 . 1.451(4)
C14 C15 . 1.461(5)
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 C16 . 1.4979(10)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 C17 . 1.5048(10)
C16 H16A . 0.9700
C16 H16B . 0.9700
C17 C18 . 1.4979(10)
C17 H17A . 0.9700
C17 H17B . 0.9700
C18 N3 . 1.515(5)
C18 H18A . 0.9700
C18 H18B . 0.9700
C19 C20 . 1.322(5)
C19 N3 . 1.395(5)
C19 H19 . 0.9300
C20 N4 . 1.383(4)
C20 H20 . 0.9300
C21 N4 . 1.350(4)
C21 N3 . 1.351(4)
C21 C22 . 1.465(4)
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
N1 Zn1 . 1.993(2)
N4 Zn1 3_565 2.005(3)
O2 Zn1 4_675 1.946(2)
O4 Zn1 . 1.960(2)
Zn1 O2 4_576 1.946(2)
Zn1 N4 3_565 2.005(3)
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
C6 C1 C2 C3 . 2.5(4)
C7 C1 C2 C3 . -179.2(3)
C1 C2 C3 C4 . -4.4(4)
C1 C2 C3 C8 . 177.3(3)
C2 C3 C4 C5 . 2.7(4)
C8 C3 C4 C5 . -179.0(3)
C3 C4 C5 C6 . 0.9(5)
C3 C4 C5 C9 . -179.6(3)
C4 C5 C6 C1 . -2.8(5)
C9 C5 C6 C1 . 177.7(3)
C2 C1 C6 C5 . 1.1(5)
C7 C1 C6 C5 . -177.4(3)
C2 C1 C7 O1 . 151.7(3)
C6 C1 C7 O1 . -29.9(4)
C2 C1 C7 O2 . -29.2(4)
C6 C1 C7 O2 . 149.2(3)
C4 C3 C8 O3 . 177.1(3)
C2 C3 C8 O3 . -4.6(4)
C4 C3 C8 O4 . -1.7(4)
C2 C3 C8 O4 . 176.6(3)
N1 C10 C11 N2 . -1.1(3)
N2 C14 C15 C16 . 72.5(5)
C14 C15 C16 C17 . -178.1(4)
C15 C16 C17 C18 . -170.1(4)
C16 C17 C18 N3 . -163.7(4)
N3 C19 C20 N4 . 4.7(5)
N2 C12 N1 C10 . -0.5(3)
C13 C12 N1 C10 . 179.5(3)
N2 C12 N1 Zn1 . -165.74(19)
C13 C12 N1 Zn1 . 14.4(4)
C11 C10 N1 C12 . 1.0(3)
C11 C10 N1 Zn1 . 167.7(2)
N1 C12 N2 C11 . -0.1(3)
C13 C12 N2 C11 . 179.8(3)
N1 C12 N2 C14 . -178.9(3)
C13 C12 N2 C14 . 1.0(4)
C10 C11 N2 C12 . 0.7(3)
C10 C11 N2 C14 . 179.5(3)
C15 C14 N2 C12 . -106.0(4)
C15 C14 N2 C11 . 75.4(4)
N4 C21 N3 C19 . 0.2(5)
C22 C21 N3 C19 . -177.9(4)
N4 C21 N3 C18 . 165.9(4)
C22 C21 N3 C18 . -12.2(7)
C20 C19 N3 C21 . -3.1(6)
C20 C19 N3 C18 . -168.9(4)
C17 C18 N3 C21 . 104.7(6)
C17 C18 N3 C19 . -91.8(6)
N3 C21 N4 C20 . 2.6(4)
C22 C21 N4 C20 . -179.4(4)
N3 C21 N4 Zn1 3_565 -174.8(3)
C22 C21 N4 Zn1 3_565 3.2(5)
C19 C20 N4 C21 . -4.6(5)
C19 C20 N4 Zn1 3_565 173.1(3)
O1 C7 O2 Zn1 4_675 13.4(5)
C1 C7 O2 Zn1 4_675 -165.59(19)
O3 C8 O4 Zn1 . 2.9(4)
C3 C8 O4 Zn1 . -178.30(19)
