#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:00:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178764 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/18/4101825.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_4101825
loop_
_publ_author_name
'Omar K. Farha'
'Christos D. Malliakas'
'Mercouri G. Kanatzidis'
'Joseph T. Hupp'
_publ_contact_author             'Joseph T. Hupp'
_publ_contact_author_email       j-hupp@northwestern.edu
_publ_section_title
;
 Control over Catenation in Metal-Organic Frameworks via Rational Design
 of the Organic Building Block
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              950
_journal_page_last               952
_journal_paper_doi               10.1021/ja909519e
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C22 H13 N2 O4 Zn'
_chemical_formula_sum            'C22 H13 N2 O4 Zn'
_chemical_formula_weight         434.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           26
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2'
_symmetry_space_group_name_H-M   'P m c 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                   15.6540(10)
_cell_length_b                   15.9467(11)
_cell_length_c                   11.6268(8)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_volume                     2902.4(3)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  diamond
_diffrn_radiation_source         synchrotron
_diffrn_radiation_wavelength     0.41823
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23992
_diffrn_reflns_theta_full        14.69
_diffrn_reflns_theta_max         14.69
_diffrn_reflns_theta_min         5.42
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_density_diffrn    0.995
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             884
_platon_squeeze_details
;
;
_refine_diff_density_max         1.297
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.167
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.837
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5138
_refine_ls_number_restraints     258
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0802
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1529P)²+28.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2087
_refine_ls_wR_factor_ref         0.2204
_reflns_number_gt                4227
_reflns_number_total             5138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909519e_si_004.cif
_cod_data_source_block           13
_cod_database_code               4101825
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.42024(5) 0.85803(14) 0.0082(3) Uani 1 2 d SU . .
Zn2 Zn 0.0000 0.23809(5) 0.85703(13) 0.0098(3) Uani 1 2 d SU . .
O1 O 0.0994(4) 0.3963(4) 0.7508(5) 0.0220(14) Uani 1 1 d U . .
O2 O 0.0830(4) 0.3984(4) 0.9947(5) 0.0260(14) Uani 1 1 d U . .
O3 O 0.1022(4) 0.2624(4) 0.7583(6) 0.0304(15) Uani 1 1 d U . .
O4 O 0.0784(4) 0.2590(4) 0.9983(5) 0.0267(13) Uani 1 1 d U . .
N1 N 0.0000 0.5470(3) 0.8574(8) 0.0058(11) Uani 1 2 d SDU . .
N2 N 0.0000 0.8109(4) 0.8338(10) 0.062(4) Uani 1 2 d SDU . .
N3 N 0.0000 1.1140(5) 0.8727(10) 0.029(2) Uani 1 2 d SDU . .
N4 N 0.0000 0.8512(6) 0.9217(11) 0.083(5) Uani 1 2 d SDU . .
C1 C 0.0000 0.9405(7) 0.9013(9) 0.035(3) Uani 1 2 d SDU . .
C2 C 0.1950(7) 0.3271(5) 1.0836(10) 0.021(2) Uani 1 1 d U . .
C3 C 0.1214(6) 0.3241(5) 1.0086(8) 0.0133(19) Uani 1 1 d U . .
C4 C 0.1982(6) 0.3256(5) 0.6268(8) 0.011(2) Uani 1 1 d U . .
C5 C 0.1188(6) 0.3327(4) 0.7071(8) 0.0090(18) Uani 1 1 d U . .
C6 C 0.3441(6) 0.3229(5) 0.4847(8) 0.0121(19) Uani 1 1 d U . .
C7 C 0.0000 0.6735(4) 0.7514(7) 0.015(3) Uani 1 2 d SDU . .
H7 H 0.0000 0.6998 0.6800 0.018 Uiso 1 2 calc SR . .
C8 C 0.3379(7) 0.3177(6) 0.2244(9) 0.021(2) Uani 1 1 d U . .
C9 C 0.0000 0.5922(5) 0.9553(8) 0.019(3) Uani 1 2 d SDU . .
H9 H 0.0000 0.5644 1.0257 0.023 Uiso 1 2 calc SR . .
C10 C 0.0000 0.5888(5) 0.7582(8) 0.020(3) Uani 1 2 d SDU . .
H10 H 0.0000 0.5582 0.6901 0.024 Uiso 1 2 calc SR . .
C11 C 0.4205(7) 0.3197(6) 0.2916(8) 0.018(2) Uani 1 1 d U . .
C12 C 0.4221(7) 0.3149(6) 0.4101(8) 0.020(2) Uani 1 1 d U . .
C13 C 0.2582(6) 0.3890(6) 0.6387(7) 0.0318(18) Uani 1 1 d U . .
H13 H 0.2510 0.4312 0.6929 0.038 Uiso 1 1 calc R . .
C14 C 0.5000 0.3226(7) 0.2379(10) 0.013(3) Uani 1 2 d SU . .
H14 H 0.5000 0.3269 0.1582 0.016 Uiso 1 2 calc SR . .
C15 C 0.5000 0.3090(11) 0.4716(14) 0.034(4) Uani 1 2 d SU . .
H15 H 0.5000 0.3013 0.5509 0.041 Uiso 1 2 calc SR . .
C16 C 0.2758(5) 0.2609(5) 0.4735(7) 0.0297(18) Uani 1 1 d U . .
H16 H 0.2782 0.2198 0.4169 0.036 Uiso 1 1 calc R . .
C17 C 0.2077(6) 0.2646(5) 0.5489(7) 0.0299(18) Uani 1 1 d U . .
H17 H 0.1664 0.2228 0.5452 0.036 Uiso 1 1 calc R . .
C18 C 0.3241(6) 0.2531(6) 0.1461(8) 0.036(2) Uani 1 1 d U . .
H18 H 0.3605 0.2070 0.1436 0.044 Uiso 1 1 calc R . .
C19 C 0.0000 0.7211(4) 0.8516(9) 0.0196(17) Uani 1 2 d SDU . .
C20 C 0.2564(6) 0.2587(6) 0.0735(8) 0.035(2) Uani 1 1 d U . .
H20 H 0.2491 0.2183 0.0166 0.042 Uiso 1 1 calc R . .
C21 C 0.0000 0.6802(5) 0.9535(9) 0.030(3) Uani 1 2 d SDU . .
H21 H 0.0000 0.7103 1.0221 0.036 Uiso 1 2 calc SR . .
C22 C 0.3289(6) 0.3877(6) 0.5680(8) 0.035(2) Uani 1 1 d U . .
H22 H 0.3687 0.4307 0.5745 0.042 Uiso 1 1 calc R . .
C23 C 0.0000 0.9927(10) 0.9975(15) 0.34(6) Uani 1 2 d SDU . .
H23 H 0.0000 0.9719 1.0722 0.410 Uiso 1 2 calc SR . .
C24 C 0.0000 1.0768(12) 0.9744(14) 0.29(4) Uani 1 2 d SDU . .
H24 H 0.0000 1.1122 1.0379 0.347 Uiso 1 2 calc SR . .
C25 C 0.0000 1.0597(11) 0.7855(15) 0.125(11) Uani 1 2 d SDU . .
H25 H 0.0000 1.0826 0.7119 0.150 Uiso 1 2 calc SR . .
C26 C 0.2145(6) 0.3893(6) 1.1630(8) 0.0332(19) Uani 1 1 d U . .
H26 H 0.1789 0.4358 1.1674 0.040 Uiso 1 1 calc R . .
C27 C 0.0000 0.9727(11) 0.7924(13) 0.118(10) Uani 1 2 d SDU . .
H27 H 0.0000 0.9388 0.7273 0.141 Uiso 1 2 calc SR . .
C28 C 0.2847(5) 0.3857(5) 0.2363(7) 0.0291(18) Uani 1 1 d U . .
H28 H 0.2951 0.4272 0.2906 0.035 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3242 0.9375 '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
_geom_angle_publ_flag
N1 Zn1 O1 100.7(3) . . ?
N1 Zn1 O1 100.7(3) . 4 ?
O1 Zn1 O1 100.1(4) . 4 ?
N1 Zn1 O2 99.8(3) . . ?
O1 Zn1 O2 87.7(3) . . ?
O1 Zn1 O2 156.3(2) 4 . ?
N1 Zn1 O2 99.8(3) . 4 ?
O1 Zn1 O2 156.3(2) . 4 ?
O1 Zn1 O2 87.7(3) 4 4 ?
O2 Zn1 O2 77.2(4) . 4 ?
N1 Zn1 Zn2 179.6(3) . . ?
O1 Zn1 Zn2 79.00(19) . . ?
O1 Zn1 Zn2 79.00(19) 4 . ?
O2 Zn1 Zn2 80.55(19) . . ?
O2 Zn1 Zn2 80.55(19) 4 . ?
N3 Zn2 O3 104.2(3) 1_545 4 ?
N3 Zn2 O3 104.2(3) 1_545 . ?
O3 Zn2 O3 105.7(4) 4 . ?
N3 Zn2 O4 95.0(3) 1_545 . ?
O3 Zn2 O4 153.2(2) 4 . ?
O3 Zn2 O4 87.2(3) . . ?
N3 Zn2 O4 95.0(3) 1_545 4 ?
O3 Zn2 O4 87.2(3) 4 4 ?
O3 Zn2 O4 153.2(2) . 4 ?
O4 Zn2 O4 72.4(4) . 4 ?
N3 Zn2 Zn1 174.5(3) 1_545 . ?
O3 Zn2 Zn1 79.0(2) 4 . ?
O3 Zn2 Zn1 79.0(2) . . ?
O4 Zn2 Zn1 80.56(18) . . ?
O4 Zn2 Zn1 80.56(18) 4 . ?
C5 O1 Zn1 128.8(6) . . ?
C3 O2 Zn1 121.4(6) . . ?
C5 O3 Zn2 126.2(6) . . ?
C3 O4 Zn2 122.1(6) . . ?
C10 N1 C9 117.7(6) . . ?
C10 N1 Zn1 120.2(6) . . ?
C9 N1 Zn1 122.1(6) . . ?
N4 N2 C19 114.0(9) . . ?
C24 N3 C25 112.9(18) . . ?
C24 N3 Zn2 121.9(11) . 1_565 ?
C25 N3 Zn2 125.2(11) . 1_565 ?
N2 N4 C1 112.7(9) . . ?
C27 C1 C23 121.2(16) . . ?
C27 C1 N4 121.6(10) . . ?
C23 C1 N4 117.2(10) . . ?
C26 C2 C3 126.9(9) . . ?
C26 C2 C20 116.2(9) . 1_556 ?
C3 C2 C20 116.8(8) . 1_556 ?
O4 C3 O2 118.9(9) . . ?
O4 C3 C2 121.2(8) . . ?
O2 C3 C2 113.7(7) . . ?
C17 C4 C13 121.5(9) . . ?
C17 C4 C5 123.1(8) . . ?
C13 C4 C5 115.3(7) . . ?
O1 C5 O3 119.8(8) . . ?
O1 C5 C4 121.9(7) . . ?
O3 C5 C4 111.9(6) . . ?
C22 C6 C16 115.2(8) . . ?
C22 C6 C12 125.7(8) . . ?
C16 C6 C12 119.0(8) . . ?
C10 C7 C19 119.7(7) . . ?
C28 C8 C18 123.7(9) . . ?
C28 C8 C11 116.8(9) . . ?
C18 C8 C11 119.1(9) . . ?
N1 C9 C21 121.5(7) . . ?
N1 C10 C7 123.4(7) . . ?
C12 C11 C14 115.6(11) . . ?
C12 C11 C8 122.1(11) . . ?
C14 C11 C8 122.2(9) . . ?
C11 C12 C15 121.6(12) . . ?
C11 C12 C6 123.7(12) . . ?
C15 C12 C6 114.4(9) . . ?
C22 C13 C4 118.3(8) . . ?
C11 C14 C11 126.7(12) 4_655 . ?
C12 C15 C12 118.7(14) 4_655 . ?
C17 C16 C6 118.6(8) . . ?
C4 C17 C16 123.1(9) . . ?
C20 C18 C8 118.7(9) . . ?
C21 C19 C7 118.1(6) . . ?
C21 C19 N2 127.1(7) . . ?
C7 C19 N2 114.8(7) . . ?
C18 C20 C2 120.9(9) . 1_554 ?
C19 C21 C9 119.7(7) . . ?
C13 C22 C6 123.1(8) . . ?
C24 C23 C1 115.3(18) . . ?
N3 C24 C23 128.0(19) . . ?
N3 C25 C27 127.2(19) . . ?
C2 C26 C28 123.5(9) . 1_556 ?
C1 C27 C25 115.4(18) . . ?
C8 C28 C26 116.7(8) . 1_554 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.021(5) . ?
Zn1 O1 2.030(5) . ?
Zn1 O1 2.030(5) 4 ?
Zn1 O2 2.081(6) . ?
Zn1 O2 2.081(6) 4 ?
Zn1 Zn2 2.9047(11) . ?
Zn2 N3 1.988(8) 1_545 ?
Zn2 O3 2.007(6) 4 ?
Zn2 O3 2.007(6) . ?
Zn2 O4 2.077(6) . ?
Zn2 O4 2.077(6) 4 ?
O1 C5 1.174(10) . ?
O2 C3 1.339(11) . ?
O3 C5 1.296(10) . ?
O4 C3 1.243(10) . ?
N1 C10 1.331(8) . ?
N1 C9 1.347(8) . ?
N2 N4 1.209(9) . ?
N2 C19 1.447(7) . ?
N3 C24 1.323(10) . ?
N3 C25 1.332(9) . ?
N3 Zn2 1.987(8) 1_565 ?
N4 C1 1.443(9) . ?
C1 C27 1.367(9) . ?
C1 C23 1.395(9) . ?
C2 C26 1.389(14) . ?
C2 C3 1.445(16) . ?
C2 C20 1.459(13) 1_556 ?
C4 C17 1.338(12) . ?
C4 C13 1.386(12) . ?
C4 C5 1.559(14) . ?
C6 C22 1.435(13) . ?
C6 C16 1.461(12) . ?
C6 C12 1.504(14) . ?
C7 C10 1.353(8) . ?
C7 C19 1.390(8) . ?
C8 C28 1.373(13) . ?
C8 C18 1.392(14) . ?
C8 C11 1.510(15) . ?
C9 C21 1.404(8) . ?
C11 C12 1.381(10) . ?
C11 C14 1.393(12) . ?
C12 C15 1.416(14) . ?
C13 C22 1.379(13) . ?
C14 C11 1.393(12) 4_655 ?
C15 C12 1.416(14) 4_655 ?
C16 C17 1.382(12) . ?
C18 C20 1.358(13) . ?
C19 C21 1.352(8) . ?
C20 C2 1.459(13) 1_554 ?
C23 C24 1.367(10) . ?
C25 C27 1.390(10) . ?
C26 C28 1.391(12) 1_556 ?
C28 C26 1.391(12) 1_554 ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.998 0.029 1393 589 ' '
