#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:00:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178764 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/18/4101829.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_4101829
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         'C29 H14 Br N2 O6 Zn'
_chemical_formula_sum            'C29 H14 Br N2 O6 Zn'
_chemical_formula_weight         631.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           47
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2 2'
_symmetry_space_group_name_H-M   'P m m m'
_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            2
_cell_length_a                   10.1617(13)
_cell_length_b                   16.451(2)
_cell_length_c                   22.313(3)
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      49.94
_cell_measurement_theta_min      3.96
_cell_volume                     3730.1(8)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1363
_diffrn_reflns_av_sigmaI/netI    0.1257
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8141
_diffrn_reflns_theta_full        50.39
_diffrn_reflns_theta_max         50.39
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    1.227
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_T_min  0.7589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             630
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.410
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0906
_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)+(0.1437P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2368
_reflns_number_gt                1415
_reflns_number_total             2195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909519e_si_008.cif
_cod_data_source_block           18
_cod_original_cell_volume        3730.0(9)
_cod_database_code               4101829
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-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 0.5000 0.5000 0.56549(7) 0.0215(6) Uani 1 4 d SU . .
Br1 Br 0.6801(2) 0.0000 0.5000 0.1317(12) Uani 1 4 d SU . .
O1 O 0.6319(6) 0.4150(4) 0.5504(2) 0.099(2) Uani 1 1 d U . .
C1 C 0.6631(14) 0.3856(9) 0.5000 0.096(4) Uani 1 2 d SU . .
C2 C 0.7359(14) 0.3082(8) 0.5000 0.092(4) Uani 1 2 d SU . .
C3 C 0.7638(11) 0.2642(7) 0.4481(3) 0.105(3) Uani 1 1 d U . .
H3A H 0.7379 0.2866 0.4107 0.126 Uiso 1 1 calc R . .
C4 C 0.8251(9) 0.1920(6) 0.4482(3) 0.091(3) Uani 1 1 d U . .
H4A H 0.8419 0.1649 0.4114 0.109 Uiso 1 1 calc R . .
C5 C 0.8628(12) 0.1581(8) 0.5000 0.079(3) Uani 1 2 d SU . .
C8 C 0.9316(9) 0.0761(6) 0.5000 0.053(2) Uani 1 2 d SU . .
C9 C 0.8684(14) 0.0000 0.5000 0.062(4) Uani 1 4 d SU . .
N1 N 0.5000 0.5000 0.6512(4) 0.033(2) Uani 1 4 d SDU . .
N2 N 0.5000 0.5000 0.8434(5) 0.078(4) Uani 1 4 d SU . .
O2 O 0.3904(19) 0.6167(12) 0.8427(6) 0.163(7) Uani 0.50 1 d PU . .
C10 C 0.4070(11) 0.5309(7) 0.6868(4) 0.053(4) Uani 0.50 1 d PDU . .
H10A H 0.3358 0.5564 0.6666 0.064 Uiso 0.50 1 calc PR . .
C11 C 0.3987(12) 0.5314(9) 0.7485(4) 0.075(5) Uani 0.50 1 d PDU . .
H11A H 0.3231 0.5535 0.7676 0.090 Uiso 0.50 1 calc PR . .
C12 C 0.5000 0.5000 0.7825(7) 0.084(5) Uani 1 4 d SDU . .
C13 C 0.4481(17) 0.5734(13) 0.8710(7) 0.092(5) Uani 0.50 1 d PU . .
C14 C 0.4434(16) 0.5626(14) 0.9388(7) 0.096(5) Uani 0.50 1 d PU . .
C15 C 0.389(2) 0.6277(17) 0.9686(8) 0.112(6) Uani 0.50 1 d PU . .
H15A H 0.3514 0.6719 0.9470 0.135 Uiso 0.50 1 calc PR . .
C16 C 0.5000 0.5000 0.9651(7) 0.081(5) Uani 1 4 d SU . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 99.85(14) . 8_655 ?
N1 Zn1 O1 99.85(14) . 7_565 ?
O1 Zn1 O1 160.3(3) 8_655 7_565 ?
N1 Zn1 O1 99.85(14) . 2_665 ?
O1 Zn1 O1 90.7(5) 8_655 2_665 ?
O1 Zn1 O1 85.9(5) 7_565 2_665 ?
N1 Zn1 O1 99.85(14) . . ?
O1 Zn1 O1 85.9(5) 8_655 . ?
O1 Zn1 O1 90.7(5) 7_565 . ?
O1 Zn1 O1 160.3(3) 2_665 . ?
N1 Zn1 Zn1 180.000(1) . 5_666 ?
O1 Zn1 Zn1 80.15(14) 8_655 5_666 ?
O1 Zn1 Zn1 80.15(14) 7_565 5_666 ?
O1 Zn1 Zn1 80.15(14) 2_665 5_666 ?
O1 Zn1 Zn1 80.15(14) . 5_666 ?
C1 O1 Zn1 126.5(6) . . ?
O1 C1 O1 125.6(10) 6_556 . ?
O1 C1 C2 117.2(5) 6_556 . ?
O1 C1 C2 117.2(5) . . ?
C3 C2 C3 112.3(11) . 6_556 ?
C3 C2 C1 123.4(6) . . ?
C3 C2 C1 123.4(6) 6_556 . ?
C4 C3 C2 123.5(8) . . ?
C4 C3 H3A 118.2 . . ?
C2 C3 H3A 118.2 . . ?
C5 C4 C3 120.2(8) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C4 119.3(11) . 6_556 ?
C4 C5 C8 120.1(6) . . ?
C4 C5 C8 120.1(6) 6_556 . ?
C8 C8 C9 117.2(6) 3_756 . ?
C8 C8 C5 117.4(6) 3_756 . ?
C9 C8 C5 125.5(9) . . ?
C8 C9 C8 125.7(13) 7 . ?
C8 C9 Br1 117.2(6) 7 . ?
C8 C9 Br1 117.2(6) . . ?
C10 N1 C10 44.7(10) 8_655 2_665 ?
C10 N1 C10 106.9(12) 8_655 7_565 ?
C10 N1 C10 90.1(13) 2_665 7_565 ?
C10 N1 C10 90.1(13) 8_655 . ?
C10 N1 C10 106.9(12) 2_665 . ?
C10 N1 C10 44.7(10) 7_565 . ?
C10 N1 Zn1 126.5(6) 8_655 . ?
C10 N1 Zn1 126.5(6) 2_665 . ?
C10 N1 Zn1 126.5(6) 7_565 . ?
C10 N1 Zn1 126.5(6) . . ?
C12 N2 C13 115.0(8) . 7_565 ?
C12 N2 C13 115.0(8) . 2_665 ?
C13 N2 C13 42.6(14) 7_565 2_665 ?
C12 N2 C13 115.0(8) . 8_655 ?
C13 N2 C13 129.9(16) 7_565 8_655 ?
C13 N2 C13 112.2(15) 2_665 8_655 ?
C12 N2 C13 115.0(8) . . ?
C13 N2 C13 112.2(15) 7_565 . ?
C13 N2 C13 129.9(16) 2_665 . ?
C13 N2 C13 42.6(14) 8_655 . ?
N1 C10 C11 129.8(11) . . ?
N1 C10 H10A 115.1 . . ?
C11 C10 H10A 115.1 . . ?
C12 C11 C10 120.0(13) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
N2 C12 C11 123.3(8) . 7_565 ?
N2 C12 C11 123.3(8) . . ?
C11 C12 C11 44.0(13) 7_565 . ?
N2 C12 C11 123.3(8) . 8_655 ?
C11 C12 C11 113.3(15) 7_565 8_655 ?
C11 C12 C11 96.6(14) . 8_655 ?
N2 C12 C11 123.3(8) . 2_665 ?
C11 C12 C11 96.6(14) 7_565 2_665 ?
C11 C12 C11 113.3(15) . 2_665 ?
C11 C12 C11 44.0(13) 8_655 2_665 ?
O2 C13 N2 118.7(16) . . ?
O2 C13 C14 128.2(18) . . ?
N2 C13 C14 109.6(15) . . ?
C16 C14 C15 124.7(16) . . ?
C16 C14 C13 121.3(17) . . ?
C15 C14 C13 113.7(18) . . ?
C14 C15 C15 118.9(12) . 6_557 ?
C14 C15 H15A 120.6 . . ?
C15 C15 H15A 120.6 6_557 . ?
C14 C16 C14 51.8(16) 8_655 . ?
C14 C16 C14 127(2) 8_655 7_565 ?
C14 C16 C14 103(2) . 7_565 ?
C14 C16 C14 103(2) 8_655 2_665 ?
C14 C16 C14 127(2) . 2_665 ?
C14 C16 C14 51.8(16) 7_565 2_665 ?
C14 C16 C16 116.4(10) 8_655 5_667 ?
C14 C16 C16 116.4(10) . 5_667 ?
C14 C16 C16 116.4(10) 7_565 5_667 ?
C14 C16 C16 116.4(10) 2_665 5_667 ?
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 1.913(10) . ?
Zn1 O1 1.966(5) 8_655 ?
Zn1 O1 1.966(5) 7_565 ?
Zn1 O1 1.966(5) 2_665 ?
Zn1 O1 1.966(5) . ?
Zn1 Zn1 2.923(3) 5_666 ?
Br1 C9 1.913(14) . ?
O1 C1 1.265(7) . ?
C1 O1 1.265(7) 6_556 ?
C1 C2 1.472(16) . ?
C2 C3 1.394(11) . ?
C2 C3 1.394(11) 6_556 ?
C3 C4 1.341(12) . ?
C3 H3A 0.9500 . ?
C4 C5 1.339(10) . ?
C4 H4A 0.9500 . ?
C5 C4 1.339(10) 6_556 ?
C5 C8 1.520(16) . ?
C8 C8 1.391(18) 3_756 ?
C8 C9 1.406(12) . ?
C9 C8 1.406(12) 7 ?
N1 C10 1.335(5) 8_655 ?
N1 C10 1.335(5) 2_665 ?
N1 C10 1.335(5) 7_565 ?
N1 C10 1.335(5) . ?
N2 C12 1.36(2) . ?
N2 C13 1.45(2) 7_565 ?
N2 C13 1.45(2) 2_665 ?
N2 C13 1.45(2) 8_655 ?
N2 C13 1.45(2) . ?
O2 C13 1.118(19) . ?
C10 C11 1.379(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H11A 0.9500 . ?
C12 C11 1.379(5) 7_565 ?
C12 C11 1.379(5) 8_655 ?
C12 C11 1.379(5) 2_665 ?
C13 C14 1.52(2) . ?
C14 C16 1.32(2) . ?
C14 C15 1.38(3) . ?
C15 C15 1.40(3) 6_557 ?
C15 H15A 0.9500 . ?
C16 C14 1.32(2) 8_655 ?
C16 C14 1.32(2) 7_565 ?
C16 C14 1.32(2) 2_665 ?
C16 C16 1.56(3) 5_667 ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Zn1 O1 C1 174.0(11) . . . . ?
O1 Zn1 O1 C1 74.7(12) 8_655 . . . ?
O1 Zn1 O1 C1 -85.8(12) 7_565 . . . ?
O1 Zn1 O1 C1 -6.0(11) 2_665 . . . ?
Zn1 Zn1 O1 C1 -6.0(11) 5_666 . . . ?
Zn1 O1 C1 O1 13(2) . . . 6_556 ?
Zn1 O1 C1 C2 -163.6(10) . . . . ?
O1 C1 C2 C3 -4(2) 6_556 . . . ?
O1 C1 C2 C3 172.6(14) . . . . ?
O1 C1 C2 C3 -172.6(14) 6_556 . . 6_556 ?
O1 C1 C2 C3 4(2) . . . 6_556 ?
C3 C2 C3 C4 -8(2) 6_556 . . . ?
C1 C2 C3 C4 -177.0(14) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C4 8(2) . . . 6_556 ?
C3 C4 C5 C8 179.7(11) . . . . ?
C4 C5 C8 C8 94.1(11) . . . 3_756 ?
C4 C5 C8 C8 -94.1(11) 6_556 . . 3_756 ?
C4 C5 C8 C9 -85.9(11) . . . . ?
C4 C5 C8 C9 85.9(11) 6_556 . . . ?
C8 C8 C9 C8 0.0 3_756 . . 7 ?
C5 C8 C9 C8 180.0 . . . 7 ?
C8 C8 C9 Br1 180.0 3_756 . . . ?
C5 C8 C9 Br1 0.0 . . . . ?
O1 Zn1 N1 C10 162.0(7) 8_655 . . 8_655 ?
O1 Zn1 N1 C10 -18.0(7) 7_565 . . 8_655 ?
O1 Zn1 N1 C10 -105.5(7) 2_665 . . 8_655 ?
O1 Zn1 N1 C10 74.5(7) . . . 8_655 ?
Zn1 Zn1 N1 C10 103(100) 5_666 . . 8_655 ?
O1 Zn1 N1 C10 105.5(7) 8_655 . . 2_665 ?
O1 Zn1 N1 C10 -74.5(7) 7_565 . . 2_665 ?
O1 Zn1 N1 C10 -162.0(7) 2_665 . . 2_665 ?
O1 Zn1 N1 C10 18.0(7) . . . 2_665 ?
Zn1 Zn1 N1 C10 47(100) 5_666 . . 2_665 ?
O1 Zn1 N1 C10 -18.0(7) 8_655 . . 7_565 ?
O1 Zn1 N1 C10 162.0(7) 7_565 . . 7_565 ?
O1 Zn1 N1 C10 74.5(7) 2_665 . . 7_565 ?
O1 Zn1 N1 C10 -105.5(7) . . . 7_565 ?
Zn1 Zn1 N1 C10 -77(100) 5_666 . . 7_565 ?
O1 Zn1 N1 C10 -74.5(7) 8_655 . . . ?
O1 Zn1 N1 C10 105.5(7) 7_565 . . . ?
O1 Zn1 N1 C10 18.0(7) 2_665 . . . ?
O1 Zn1 N1 C10 -162.0(7) . . . . ?
Zn1 Zn1 N1 C10 -133(100) 5_666 . . . ?
C10 N1 C10 C11 -43.9(15) 8_655 . . . ?
C10 N1 C10 C11 -1.7(10) 2_665 . . . ?
C10 N1 C10 C11 70.5(13) 7_565 . . . ?
Zn1 N1 C10 C11 178.3(10) . . . . ?
N1 C10 C11 C12 3.4(19) . . . . ?
C13 N2 C12 C11 39.7(11) 7_565 . . 7_565 ?
C13 N2 C12 C11 87.0(11) 2_665 . . 7_565 ?
C13 N2 C12 C11 -140.3(11) 8_655 . . 7_565 ?
C13 N2 C12 C11 -93.0(11) . . . 7_565 ?
C13 N2 C12 C11 93.0(11) 7_565 . . . ?
C13 N2 C12 C11 140.3(11) 2_665 . . . ?
C13 N2 C12 C11 -87.0(11) 8_655 . . . ?
C13 N2 C12 C11 -39.7(11) . . . . ?
C13 N2 C12 C11 -140.3(11) 7_565 . . 8_655 ?
C13 N2 C12 C11 -93.0(11) 2_665 . . 8_655 ?
C13 N2 C12 C11 39.7(11) 8_655 . . 8_655 ?
C13 N2 C12 C11 87.0(11) . . . 8_655 ?
C13 N2 C12 C11 -87.0(11) 7_565 . . 2_665 ?
C13 N2 C12 C11 -39.7(11) 2_665 . . 2_665 ?
C13 N2 C12 C11 93.0(11) 8_655 . . 2_665 ?
C13 N2 C12 C11 140.3(11) . . . 2_665 ?
C10 C11 C12 N2 178.6(8) . . . . ?
C10 C11 C12 C11 -76.0(12) . . . 7_565 ?
C10 C11 C12 C11 41.0(16) . . . 8_655 ?
C10 C11 C12 C11 -1.4(8) . . . 2_665 ?
C12 N2 C13 O2 15(2) . . . . ?
C13 N2 C13 O2 -119.2(18) 7_565 . . . ?
C13 N2 C13 O2 -165(2) 2_665 . . . ?
C13 N2 C13 O2 115.3(19) 8_655 . . . ?
C12 N2 C13 C14 175.4(10) . . . . ?
C13 N2 C13 C14 41(2) 7_565 . . . ?
C13 N2 C13 C14 -4.6(10) 2_665 . . . ?
C13 N2 C13 C14 -84.1(13) 8_655 . . . ?
O2 C13 C14 C16 168(2) . . . . ?
N2 C13 C14 C16 10(2) . . . . ?
O2 C13 C14 C15 -18(3) . . . . ?
N2 C13 C14 C15 -176.7(16) . . . . ?
C16 C14 C15 C15 -2(2) . . . 6_557 ?
C13 C14 C15 C15 -174.9(10) . . . 6_557 ?
C15 C14 C16 C14 -102(2) . . . 8_655 ?
C13 C14 C16 C14 70.4(18) . . . 8_655 ?
C15 C14 C16 C14 130.4(19) . . . 7_565 ?
C13 C14 C16 C14 -57(2) . . . 7_565 ?
C15 C14 C16 C14 -178(2) . . . 2_665 ?
C13 C14 C16 C14 -5.6(12) . . . 2_665 ?
C15 C14 C16 C16 2(2) . . . 5_667 ?
C13 C14 C16 C16 174.4(12) . . . 5_667 ?
