#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/47/4504744.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_4504744
loop_
_publ_author_name
'Custelcean, Radu'
'Moyer, Bruce A.'
'Bryantsev, Vyacheslav S.'
'Hay, Benjamin P.'
_publ_section_title
;
 Anion Coordination in Metal−Organic Frameworks Functionalized with
 Urea Hydrogen-Bonding Groups
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              555
_journal_paper_doi               10.1021/cg0505057
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C22 H24 Cl N8 O8 Zn0.5'
_chemical_formula_weight         596.63
_chemical_name_common            6
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.543(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.905(5)
_cell_length_b                   13.712(3)
_cell_length_c                   15.538(3)
_cell_measurement_temperature    173(2)
_cell_volume                     5022.6(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30622
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.8369
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.175
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0749P)²+2.1732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                4844
_reflns_number_total             6238
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0505057si20050928_052814.cif
_cod_data_source_block           c:\frames\076\work\076s
_cod_original_cell_volume        5022.7(18)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C22 H24 Cl N8 O8 Zn0.50'
_cod_database_code               4504744
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 0.2500 0.2500 0.0000 0.02321(11) Uani 1 2 d S
Cl1 Cl 0.351791(19) -0.21382(4) 0.06969(3) 0.02291(13) Uani 1 1 d .
O1 O 0.13652(6) -0.17682(10) 0.18387(10) 0.0228(3) Uani 1 1 d .
O8 O 0.27952(7) 0.33652(11) 0.10945(10) 0.0271(3) Uani 1 1 d .
N4 N 0.21343(7) -0.53312(12) 0.18167(11) 0.0217(4) Uani 1 1 d .
O7 O 0.32570(7) 0.16405(12) 0.02924(12) 0.0296(4) Uani 1 1 d .
C9 C 0.14976(8) -0.46854(15) 0.27088(13) 0.0226(4) Uani 1 1 d .
H9 H 0.1245 -0.4802 0.3109 0.027 Uiso 1 1 calc R
N1 N 0.20779(7) -0.10640(12) 0.12262(11) 0.0204(3) Uani 1 1 d .
H1N H 0.2361 -0.1202 0.0951 0.024 Uiso 1 1 calc R
C8 C 0.17731(8) -0.54565(15) 0.23837(13) 0.0214(4) Uani 1 1 d .
H8 H 0.1704 -0.6099 0.2569 0.026 Uiso 1 1 calc R
C11 C 0.18141(8) -0.18376(14) 0.15615(13) 0.0184(4) Uani 1 1 d .
O4 O 0.32401(8) -0.12096(12) 0.05179(11) 0.0378(4) Uani 1 1 d .
C6 C 0.19648(8) -0.36003(14) 0.18576(13) 0.0184(4) Uani 1 1 d .
C1 C 0.19342(8) -0.00798(14) 0.12857(13) 0.0190(4) Uani 1 1 d .
N2 N 0.21188(7) -0.26846(12) 0.15598(12) 0.0211(4) Uani 1 1 d .
H2N H 0.2440 -0.2653 0.1354 0.025 Uiso 1 1 calc R
C10 C 0.15930(8) -0.37443(15) 0.24473(13) 0.0216(4) Uani 1 1 d .
H10 H 0.1409 -0.3207 0.2666 0.026 Uiso 1 1 calc R
N3 N 0.21081(7) 0.15458(12) 0.08128(11) 0.0226(4) Uani 1 1 d .
C2 C 0.21790(8) 0.05766(14) 0.07747(13) 0.0216(4) Uani 1 1 d .
H2 H 0.2407 0.0327 0.0380 0.026 Uiso 1 1 calc R
C7 C 0.22219(8) -0.44187(14) 0.15616(13) 0.0213(4) Uani 1 1 d .
H7 H 0.2474 -0.4324 0.1156 0.026 Uiso 1 1 calc R
O3 O 0.30912(7) -0.28956(12) 0.06272(12) 0.0354(4) Uani 1 1 d .
C3 C 0.17839(9) 0.18917(15) 0.13686(14) 0.0250(4) Uani 1 1 d .
H3 H 0.1734 0.2577 0.1404 0.030 Uiso 1 1 calc R
C4 C 0.15207(9) 0.12932(15) 0.18901(14) 0.0261(4) Uani 1 1 d .
H4 H 0.1288 0.1564 0.2269 0.031 Uiso 1 1 calc R
O6 O 0.38892(7) -0.23303(12) 0.00734(11) 0.0322(4) Uani 1 1 d .
C5 C 0.15974(9) 0.02921(15) 0.18592(14) 0.0238(4) Uani 1 1 d .
H5 H 0.1424 -0.0131 0.2221 0.029 Uiso 1 1 calc R
O2 O 0.45474(6) 0.15443(12) 0.15075(11) 0.0320(4) Uani 1 1 d .
N6 N 0.54039(7) 0.12524(14) 0.10730(13) 0.0297(4) Uani 1 1 d .
H6N H 0.5698 0.1550 0.0918 0.036 Uiso 1 1 calc R
C17 C 0.54065(8) 0.02372(16) 0.10341(14) 0.0250(4) Uani 1 1 d .
C22 C 0.49949(8) 0.18437(17) 0.13251(14) 0.0260(4) Uani 1 1 d .
N5 N 0.51504(7) 0.28111(15) 0.13324(14) 0.0329(4) Uani 1 1 d .
H5N H 0.5515 0.2939 0.1373 0.040 Uiso 1 1 calc R
N7 N 0.38465(8) 0.42931(15) 0.11551(14) 0.0365(5) Uani 1 1 d .
C12 C 0.47822(9) 0.36095(17) 0.12814(15) 0.0296(5) Uani 1 1 d .
N8 N 0.58890(8) -0.11498(15) 0.05551(13) 0.0305(4) Uani 1 1 d .
C18 C 0.58233(9) -0.01959(17) 0.06214(14) 0.0280(5) Uani 1 1 d .
H18 H 0.6073 0.0220 0.0375 0.034 Uiso 1 1 calc R
C21 C 0.50420(9) -0.03780(18) 0.13881(15) 0.0307(5) Uani 1 1 d .
H21 H 0.4754 -0.0120 0.1677 0.037 Uiso 1 1 calc R
C20 C 0.51087(10) -0.13755(19) 0.13090(17) 0.0366(6) Uani 1 1 d .
H20 H 0.4862 -0.1810 0.1541 0.044 Uiso 1 1 calc R
C19 C 0.55307(10) -0.17378(19) 0.08956(17) 0.0347(5) Uani 1 1 d .
H19 H 0.5571 -0.2424 0.0849 0.042 Uiso 1 1 calc R
C13 C 0.42030(10) 0.35304(19) 0.12670(19) 0.0389(6) Uani 1 1 d .
H13 H 0.4050 0.2902 0.1340 0.047 Uiso 1 1 calc R
C14 C 0.40543(12) 0.5166(2) 0.1069(2) 0.0529(8) Uani 1 1 d .
H14 H 0.3804 0.5709 0.0986 0.064 Uiso 1 1 calc R
C16 C 0.49952(12) 0.4526(2) 0.1200(3) 0.0760(13) Uani 1 1 d .
H16 H 0.5390 0.4620 0.1214 0.091 Uiso 1 1 calc R
C15 C 0.46277(14) 0.5314(2) 0.1096(4) 0.0995(18) Uani 1 1 d .
H15 H 0.4770 0.5955 0.1044 0.119 Uiso 1 1 calc R
O5 O 0.38370(7) -0.21433(14) 0.15629(11) 0.0372(4) Uani 1 1 d .
H3O H 0.2543(16) 0.373(3) 0.133(2) 0.071(11) Uiso 1 1 d .
H1O H 0.3350(14) 0.155(2) 0.082(2) 0.054(10) Uiso 1 1 d .
H2O H 0.3580(15) 0.153(2) -0.001(2) 0.062(9) Uiso 1 1 d .
H4O H 0.3111(15) 0.373(2) 0.106(2) 0.058(9) Uiso 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'
Cl Cl 0.1484 0.1585 '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
O8 Zn1 O8 180.0 . 7
O8 Zn1 N3 89.35(7) . .
O8 Zn1 N3 90.65(7) 7 .
O8 Zn1 N3 90.65(7) . 7
O8 Zn1 N3 89.35(7) 7 7
N3 Zn1 N3 180.00(7) . 7
O8 Zn1 O7 91.12(6) . 7
O8 Zn1 O7 88.88(6) 7 7
N3 Zn1 O7 91.40(6) . 7
N3 Zn1 O7 88.60(6) 7 7
O8 Zn1 O7 88.88(6) . .
O8 Zn1 O7 91.12(6) 7 .
N3 Zn1 O7 88.60(6) . .
N3 Zn1 O7 91.40(6) 7 .
O7 Zn1 O7 180.0 7 .
O5 Cl1 O4 110.00(11) . .
O5 Cl1 O6 109.80(10) . .
O4 Cl1 O6 110.29(10) . .
O5 Cl1 O3 109.01(11) . .
O4 Cl1 O3 108.84(11) . .
O6 Cl1 O3 108.86(10) . .
C7 N4 C8 117.57(17) . .
C10 C9 C8 119.58(18) . .
C11 N1 C1 125.73(16) . .
N4 C8 C9 122.56(18) . .
O1 C11 N2 124.29(17) . .
O1 C11 N1 123.72(17) . .
N2 C11 N1 111.98(16) . .
C10 C6 C7 117.88(18) . .
C10 C6 N2 124.95(18) . .
C7 C6 N2 117.13(17) . .
C2 C1 C5 118.07(18) . .
C2 C1 N1 117.06(17) . .
C5 C1 N1 124.72(18) . .
C11 N2 C6 125.94(17) . .
C9 C10 C6 118.68(18) . .
C3 N3 C2 118.03(17) . .
C3 N3 Zn1 121.40(13) . .
C2 N3 Zn1 120.57(13) . .
N3 C2 C1 123.16(18) . .
N4 C7 C6 123.73(18) . .
N3 C3 C4 122.57(19) . .
C3 C4 C5 119.58(19) . .
C4 C5 C1 118.58(19) . .
C22 N6 C17 127.55(18) . .
C21 C17 N6 125.6(2) . .
C21 C17 C18 117.6(2) . .
N6 C17 C18 116.83(19) . .
O2 C22 N6 124.0(2) . .
O2 C22 N5 124.5(2) . .
N6 C22 N5 111.48(18) . .
C22 N5 C12 125.94(18) . .
C14 N7 C13 118.8(2) . .
C16 C12 C13 117.1(2) . .
C16 C12 N5 118.9(2) . .
C13 C12 N5 123.9(2) . .
C18 N8 C19 118.0(2) . .
N8 C18 C17 123.8(2) . .
C20 C21 C17 118.4(2) . .
C19 C20 C21 120.2(2) . .
N8 C19 C20 122.0(2) . .
N7 C13 C12 123.5(2) . .
N7 C14 C15 121.5(3) . .
C12 C16 C15 119.2(3) . .
C14 C15 C16 119.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O8 2.0976(16) .
Zn1 O8 2.0976(16) 7
Zn1 N3 2.1394(17) .
Zn1 N3 2.1394(17) 7
Zn1 O7 2.1442(16) 7
Zn1 O7 2.1443(16) .
Cl1 O5 1.4326(17) .
Cl1 O4 1.4416(17) .
Cl1 O6 1.4426(15) .
Cl1 O3 1.4472(16) .
O1 C11 1.224(2) .
N4 C7 1.340(3) .
N4 C8 1.343(3) .
C9 C10 1.383(3) .
C9 C8 1.385(3) .
N1 C11 1.380(2) .
N1 C1 1.399(2) .
C11 N2 1.371(2) .
C6 C10 1.392(3) .
C6 C7 1.394(3) .
C6 N2 1.408(2) .
C1 C2 1.392(3) .
C1 C5 1.393(3) .
N3 C3 1.339(3) .
N3 C2 1.342(3) .
C3 C4 1.377(3) .
C4 C5 1.387(3) .
O2 C22 1.222(2) .
N6 C22 1.376(3) .
N6 C17 1.393(3) .
C17 C21 1.390(3) .
C17 C18 1.403(3) .
C22 N5 1.377(3) .
N5 C12 1.399(3) .
N7 C14 1.311(3) .
N7 C13 1.342(3) .
C12 C16 1.370(4) .
C12 C13 1.385(3) .
N8 C18 1.323(3) .
N8 C19 1.347(3) .
C21 C20 1.385(3) .
C20 C19 1.375(3) .
C14 C15 1.380(4) .
C16 C15 1.385(4) .
