#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/95/2209568.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_2209568
loop_
_publ_author_name
'Yun-Cheng Cui'
'Jia-Jun Wang'
'Guang-Bo Che'
'Chun-Bo Liu'
'Chuan-Bi Li'
_publ_section_title
μ-Benzene-1,4-dicarboxylato-bis[aquachloro(2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene)zinc(II)]
_journal_coeditor_code           JH2021
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1633
_journal_page_last               m1634
_journal_paper_doi               10.1107/S1600536806023439
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Zn2 (C8 H4 O4) Cl2 (C19 H12 N4)2 (H2 O)2]'
_chemical_formula_moiety         'C46 H32 Cl2 N8 O6 Zn2'
_chemical_formula_sum            'C46 H32 Cl2 N8 O6 Zn2'
_chemical_formula_weight         994.44
_chemical_name_systematic
;
μ-benzene-1,4-dicarboxylato-bis[aquachloro(2-phenyl-1H-1,3,7,8-
tetraazacyclopenta[l]phenanthrene)zinc(II)]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.54(3)
_cell_angle_beta                 98.01(3)
_cell_angle_gamma                100.49(3)
_cell_formula_units_Z            1
_cell_length_a                   9.0702(18)
_cell_length_b                   9.1815(18)
_cell_length_c                   12.642(3)
_cell_measurement_reflns_used    total
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.12
_cell_volume                     988.0(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXTL-Plus (Siemens, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotor target'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_sigmaI/netI    0.1327
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9673
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.853
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0710
_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)+(0.1295P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1713
_refine_ls_wR_factor_ref         0.2354
_reflns_number_gt                2309
_reflns_number_total             4441
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2021.cif
_cod_data_source_block           I
_cod_database_code               2209568
_cod_database_fobs_code          2209568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.4333(8) 1.3218(8) 0.8274(7) 0.0411(18) Uani d . 1
H H1 0.5154 1.2865 0.8568 0.049 Uiso calc R 1
C C2 0.4645(9) 1.4548(9) 0.7928(7) 0.051(2) Uani d . 1
H H2 0.5648 1.5064 0.7987 0.062 Uiso calc R 1
C C3 0.3443(8) 1.5088(8) 0.7497(6) 0.0389(17) Uani d . 1
H H3 0.3620 1.5993 0.7277 0.047 Uiso calc R 1
C C4 0.1962(8) 1.4267(8) 0.7393(5) 0.0343(15) Uani d . 1
C C5 0.1753(8) 1.2920(7) 0.7762(5) 0.0323(15) Uani d . 1
C C6 0.0254(8) 1.2004(7) 0.7681(5) 0.0316(14) Uani d . 1
C C7 -0.1063(8) 1.2414(8) 0.7245(6) 0.0362(16) Uani d . 1
C C8 -0.2481(8) 1.1499(8) 0.7225(6) 0.0395(17) Uani d . 1
H H8 -0.3378 1.1749 0.6946 0.047 Uiso calc R 1
C C9 -0.2533(9) 1.0233(9) 0.7618(6) 0.0421(17) Uani d . 1
H H9 -0.3470 0.9602 0.7596 0.050 Uiso calc R 1
C C10 -0.1206(8) 0.9890(8) 0.8045(6) 0.0406(17) Uani d . 1
H H10 -0.1263 0.9036 0.8326 0.049 Uiso calc R 1
C C11 -0.0861(8) 1.3780(8) 0.6872(5) 0.0322(15) Uani d . 1
C C12 0.0590(8) 1.4667(8) 0.6974(5) 0.0337(15) Uani d . 1
C C13 -0.1185(8) 1.5686(8) 0.6249(6) 0.0357(16) Uani d . 1
C C14 -0.1940(8) 1.6731(8) 0.5743(6) 0.0367(16) Uani d . 1
C C15 -0.3510(9) 1.6566(9) 0.5651(7) 0.0465(19) Uani d . 1
H H15 -0.4060 1.5831 0.5929 0.056 Uiso calc R 1
C C16 -0.4261(9) 1.7476(9) 0.5154(7) 0.050(2) Uani d . 1
H H16 -0.5314 1.7347 0.5088 0.060 Uiso calc R 1
C C17 -0.3441(10) 1.8588(9) 0.4750(7) 0.051(2) Uani d . 1
H H17 -0.3939 1.9213 0.4417 0.061 Uiso calc R 1
C C18 -0.1882(10) 1.8757(9) 0.4849(6) 0.0470(19) Uani d . 1
H H18 -0.1337 1.9493 0.4570 0.056 Uiso calc R 1
C C19 -0.1110(9) 1.7857(9) 0.5354(6) 0.0431(18) Uani d . 1
H H19 -0.0055 1.8003 0.5432 0.052 Uiso calc R 1
C C20 0.1894(8) 0.7662(8) 0.9616(6) 0.0369(16) Uani d . 1
C C21 0.0900(8) 0.6275(7) 0.9801(5) 0.0324(15) Uani d . 1
C C22 -0.0673(8) 0.6070(8) 0.9625(6) 0.0371(16) Uani d . 1
H H22 -0.1129 0.6783 0.9369 0.044 Uiso calc R 1
C C23 -0.1575(8) 0.4809(8) 0.9826(6) 0.0370(16) Uani d . 1
H H23 -0.2631 0.4686 0.9713 0.044 Uiso calc R 1
N N1 0.2953(6) 1.2428(6) 0.8210(5) 0.0343(13) Uani d D 1
N N2 0.0160(7) 1.0738(7) 0.8072(5) 0.0377(14) Uani d . 1
N N3 0.0355(7) 1.5870(7) 0.6539(5) 0.0362(14) Uani d . 1
N N4 -0.1961(7) 1.4425(7) 0.6428(5) 0.0411(15) Uani d . 1
O O1 0.1222(6) 0.8466(6) 0.9111(4) 0.0458(13) Uani d . 1
O O2 0.3290(6) 0.7967(6) 0.9981(5) 0.0488(14) Uani d . 1
O O1W 0.3716(6) 1.1067(7) 1.0092(5) 0.0503(14) Uani d D 1
Zn Zn1 0.22662(10) 1.02332(9) 0.85475(7) 0.0368(3) Uani d . 1
Cl Cl1 0.3180(2) 0.8874(2) 0.71353(17) 0.0481(5) Uani d . 1
H HW11 0.368(9) 1.021(5) 1.023(7) 0.072 Uiso d D 1
H HW12 0.302(8) 1.147(9) 1.033(4) 0.072 Uiso d D 1
H H3B 0.101(12) 1.645(12) 0.637(8) 0.072 Uiso 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N1 C1 C2 . . 123.9(6) ?
N1 C1 H1 . . 118.0 ?
C2 C1 H1 . . 118.0 ?
C3 C2 C1 . . 118.6(7) ?
C3 C2 H2 . . 120.7 ?
C1 C2 H2 . . 120.7 ?
C2 C3 C4 . . 119.2(6) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C3 C4 C5 . . 118.2(6) ?
C3 C4 C12 . . 126.5(6) ?
C5 C4 C12 . . 115.2(6) ?
N1 C5 C4 . . 121.6(6) ?
N1 C5 C6 . . 116.8(6) ?
C4 C5 C6 . . 121.5(6) ?
N2 C6 C7 . . 120.8(6) ?
N2 C6 C5 . . 117.5(6) ?
C7 C6 C5 . . 121.6(6) ?
C6 C7 C8 . . 118.5(6) ?
C6 C7 C11 . . 117.2(6) ?
C8 C7 C11 . . 124.3(6) ?
C9 C8 C7 . . 119.1(7) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C8 C9 C10 . . 120.0(7) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
N2 C10 C9 . . 122.2(7) ?
N2 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
N4 C11 C12 . . 111.2(6) ?
N4 C11 C7 . . 128.2(6) ?
C12 C11 C7 . . 120.5(6) ?
N3 C12 C11 . . 104.9(6) ?
N3 C12 C4 . . 131.3(6) ?
C11 C12 C4 . . 123.8(6) ?
N4 C13 N3 . . 112.7(6) ?
N4 C13 C14 . . 122.6(6) ?
N3 C13 C14 . . 124.7(6) ?
C15 C14 C19 . . 119.7(6) ?
C15 C14 C13 . . 119.0(6) ?
C19 C14 C13 . . 121.3(7) ?
C16 C15 C14 . . 120.8(7) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 119.8(8) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C18 C17 C16 . . 119.3(7) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
C17 C18 C19 . . 121.6(8) ?
C17 C18 H18 . . 119.2 ?
C19 C18 H18 . . 119.2 ?
C18 C19 C14 . . 118.8(7) ?
C18 C19 H19 . . 120.6 ?
C14 C19 H19 . . 120.6 ?
O2 C20 O1 . . 124.3(6) ?
O2 C20 C21 . . 119.2(6) ?
O1 C20 C21 . . 116.5(6) ?
C22 C21 C23 . 2_567 119.3(6) ?
C22 C21 C20 . . 121.0(6) ?
C23 C21 C20 2_567 . 119.6(6) ?
C21 C22 C23 . . 120.5(6) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
C22 C23 C21 . 2_567 120.1(7) ?
C22 C23 H23 . . 119.9 ?
C21 C23 H23 2_567 . 119.9 ?
C1 N1 C5 . . 118.3(6) ?
C1 N1 Zn1 . . 128.7(4) ?
C5 N1 Zn1 . . 112.5(4) ?
C10 N2 C6 . . 119.3(6) ?
C10 N2 Zn1 . . 126.3(5) ?
C6 N2 Zn1 . . 114.2(5) ?
C13 N3 C12 . . 106.8(6) ?
C13 N3 H3B . . 127(7) ?
C12 N3 H3B . . 125(7) ?
C13 N4 C11 . . 104.4(6) ?
C20 O1 Zn1 . . 125.8(5) ?
Zn1 O1W HW11 . . 96(7) ?
Zn1 O1W HW12 . . 88(5) ?
HW11 O1W HW12 . . 111(8) ?
O1 Zn1 O1W . . 87.8(2) y
O1 Zn1 N2 . . 90.7(2) y
O1W Zn1 N2 . . 127.5(2) y
O1 Zn1 N1 . . 163.8(2) y
O1W Zn1 N1 . . 89.7(2) y
N2 Zn1 N1 . . 78.2(2) y
O1 Zn1 Cl1 . . 99.75(17) y
O1W Zn1 Cl1 . . 117.30(18) y
N2 Zn1 Cl1 . . 114.64(18) y
N1 Zn1 Cl1 . . 95.60(17) y
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
C1 N1 . 1.309(9) ?
C1 C2 . 1.386(10) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.375(10) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.387(10) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.412(9) ?
C4 C12 . 1.428(9) ?
C5 N1 . 1.354(8) ?
C5 C6 . 1.439(9) ?
C6 N2 . 1.359(8) ?
C6 C7 . 1.396(9) ?
C7 C8 . 1.396(10) ?
C7 C11 . 1.431(9) ?
C8 C9 . 1.363(10) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.369(11) ?
C9 H9 . 0.9300 ?
C10 N2 . 1.329(9) ?
C10 H10 . 0.9300 ?
C11 N4 . 1.370(8) ?
C11 C12 . 1.387(10) ?
C12 N3 . 1.380(8) ?
C13 N4 . 1.327(9) ?
C13 N3 . 1.363(9) ?
C13 C14 . 1.484(9) ?
C14 C15 . 1.390(11) ?
C14 C19 . 1.391(10) ?
C15 C16 . 1.375(10) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.389(11) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.379(12) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.383(10) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 O2 . 1.242(9) ?
C20 O1 . 1.265(8) ?
C20 C21 . 1.507(9) ?
C21 C22 . 1.384(10) ?
C21 C23 2_567 1.396(9) ?
C22 C23 . 1.388(9) ?
C22 H22 . 0.9300 ?
C23 C21 2_567 1.396(9) ?
C23 H23 . 0.9300 ?
N1 Zn1 . 2.157(5) y
N2 Zn1 . 2.088(6) y
N3 H3B . 0.81(11) ?
O1 Zn1 . 2.051(5) y
O1W Zn1 . 2.084(6) y
O1W HW11 . 0.84(6) ?
O1W HW12 . 0.84(7) ?
Zn1 Cl1 . 2.275(2) y
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
O1W HW11 O2 . 0.84(6) 1.96(4) 2.769(7) 160(9)
N3 H3B Cl1 1_565 0.81(11) 2.57(11) 3.264(6) 144(9)
