#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200232.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_2200232
loop_
_publ_author_name
'Butler, Richard N.'
'McGinley, John M. G.'
'Mahon, Mary F.'
'Molloy, Kieran C.'
'NíBhrádaigh, Eithne P.'
_publ_section_title
;
 Diorthobenzenotetra(5',2'-tetrazolo)[5'-(2)-2'-(6)]cyclophane
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o195
_journal_page_last               o197
_journal_paper_doi               10.1107/S1600536801001398
_journal_volume                  57
_journal_year                    2001
_chemical_formula_sum            'C28 H32 N16'
_chemical_formula_weight         592.70
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                77.25(3)
_cell_angle_beta                 74.89(3)
_cell_angle_gamma                73.47(3)
_cell_formula_units_Z            1
_cell_length_a                   7.170(2)
_cell_length_b                   10.241(3)
_cell_length_c                   10.729(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.67
_cell_measurement_theta_min      13.87
_cell_volume                     719.9(4)
_computing_cell_refinement       'CELDIM in CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf-Nonius, 1992)'
_computing_data_reduction        'XCAD (McArdle & Higgins, 1995)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0102
_diffrn_reflns_av_sigmaI/netI    .0453
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2441
_diffrn_reflns_theta_max         23.96
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 80
_diffrn_standards_interval_time  150
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    .091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .30
_refine_diff_density_max         .166
_refine_diff_density_min         -.125
_refine_ls_extinction_coef       .061(7)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.080
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_restrained_S_obs      1.191
_refine_ls_R_factor_all          .0574
_refine_ls_R_factor_gt           .0370
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0714P)²+0.0022P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1047
_refine_ls_wR_factor_ref         .0983
_reflns_number_gt                1674
_reflns_number_total             2238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6001.cif
_cod_data_source_block           93kcm4
_cod_database_code               2200232
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .2292(2) .31148(15) .60411(13) .0527(4) Uani d . 1 . N
N2 .2397(2) .43564(15) .53809(14) .0559(4) Uani d . 1 . N
N3 .2452(2) .43014(14) .41642(14) .0498(4) Uani d . 1 . N
N4 .2409(2) .30851(14) .39627(13) .0501(4) Uani d . 1 . N
N5 .8191(2) .87060(13) .04860(12) .0450(4) Uani d . 1 . N
N6 .7094(2) .93678(14) .14675(13) .0456(4) Uani d . 1 . N
N7 1.0277(2) .86172(15) .15889(13) .0492(4) Uani d . 1 . N
N8 1.0089(2) .8249(2) .05300(13) .0516(4) Uani d . 1 . N
C1 .2314(2) .0877(2) .54015(15) .0398(4) Uani d . 1 . C
C2 .2699(2) .0224(2) .4327(2) .0477(4) Uani d . 1 . C
H2 .2921 .0728 .3490 .057 Uiso calc R 1 . H
C3 .2757(3) -.1152(2) .4474(2) .0547(5) Uani d . 1 . C
H3 .2993 -.1565 .3739 .066 Uiso calc R 1 . H
C4 .2469(3) -.1926(2) .5705(2) .0556(5) Uani d . 1 . C
H4 .2513 -.2859 .5806 .067 Uiso calc R 1 . H
C5 .2115(2) -.1294(2) .6784(2) .0500(5) Uani d . 1 . C
H5 .1941 -.1815 .7614 .060 Uiso calc R 1 . H
C6 .2014(2) .0102(2) .6658(2) .0408(4) Uani d . 1 . C
C7 .2308(2) .2356(2) .51581(14) .0408(4) Uani d . 1 . C
C8 .2703(3) .5443(2) .3086(2) .0582(5) Uani d . 1 . C
H8A .2363 .6298 .3435 .070 Uiso calc R 1 . H
H8B .1807 .5534 .2516 .070 Uiso calc R 1 . H
C9 .4837(3) .5195(2) .2303(2) .0549(5) Uani d . 1 . C
H9A .5718 .5112 .2881 .066 Uiso calc R 1 . H
H9B .5173 .4326 .1981 .066 Uiso calc R 1 . H
C10 .5207(3) .6315(2) .1161(2) .0547(5) Uani d . 1 . C
H10A .4839 .7194 .1471 .066 Uiso calc R 1 . H
H10B .4380 .6376 .0555 .066 Uiso calc R 1 . H
C11 .7370(3) .6029(2) .0461(2) .0552(5) Uani d . 1 . C
H11A .7743 .5116 .0220 .066 Uiso calc R 1 . H
H11B .8171 .6014 .1069 .066 Uiso calc R 1 . H
C12 .7894(3) .7052(2) -.0763(2) .0589(5) Uani d . 1 . C
H12A .9314 .6781 -.1116 .071 Uiso calc R 1 . H
H12B .7215 .6990 -.1413 .071 Uiso calc R 1 . H
C13 .7366(3) .8532(2) -.0557(2) .0529(5) Uani d . 1 . C
H13A .7864 .9092 -.1364 .063 Uiso calc R 1 . H
H13B .5929 .8859 -.0345 .063 Uiso calc R 1 . H
C14 .1567(2) .0712(2) .78545(14) .0401(4) Uani d . 1 . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 -1 7
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
N2 N1 C7 . . 106.10(10) no
N3 N2 N1 . . 106.10(10) no
N2 N3 N4 . . 114.20(10) no
N2 N3 C8 . . 123.70(10) no
N4 N3 C8 . . 122.00(10) no
N3 N4 C7 . . 102.00(10) no
N8 N5 N6 . . 113.90(10) no
N8 N5 C13 . . 123.30(10) no
N6 N5 C13 . . 122.80(10) no
C14 N6 N5 2_666 . 101.90(10) no
N8 N7 C14 . 2_666 106.10(10) no
N5 N8 N7 . . 106.00(10) no
C2 C1 C6 . . 118.90(10) no
C2 C1 C7 . . 117.90(10) no
C6 C1 C7 . . 123.20(10) no
C3 C2 C1 . . 121.3(2) no
C2 C3 C4 . . 120.4(2) no
C3 C4 C5 . . 119.0(2) no
C4 C5 C6 . . 121.6(2) no
C5 C6 C1 . . 118.9(2) no
C5 C6 C14 . . 118.50(10) no
C1 C6 C14 . . 122.70(10) no
N4 C7 N1 . . 111.80(10) no
N4 C7 C1 . . 121.30(10) no
N1 C7 C1 . . 126.90(10) no
N3 C8 C9 . . 110.8(2) no
C10 C9 C8 . . 114.0(2) no
C9 C10 C11 . . 111.1(2) no
C10 C11 C12 . . 115.7(2) no
C13 C12 C11 . . 114.9(2) no
N5 C13 C12 . . 112.4(2) no
N6 C14 N7 2_666 2_666 112.10(10) no
N6 C14 C6 2_666 . 124.10(10) no
N7 C14 C6 2_666 . 123.80(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . . 1.324(2) no
N1 C7 . . 1.347(2) no
N2 N3 . . 1.309(2) no
N3 N4 . . 1.320(2) no
N3 C8 . . 1.467(2) no
N4 C7 . . 1.329(2) no
N5 N8 . . 1.318(2) no
N5 N6 . . 1.329(2) no
N5 C13 . . 1.458(2) no
N6 C14 2_666 . 1.323(2) no
N7 N8 . . 1.322(2) no
N7 C14 2_666 . 1.352(2) no
C1 C2 . . 1.387(2) no
C1 C6 . . 1.403(2) no
C1 C7 . . 1.479(2) no
C2 C3 . . 1.372(2) no
C3 C4 . . 1.380(3) no
C4 C5 . . 1.381(2) no
C5 C6 . . 1.388(2) no
C6 C14 . . 1.472(2) no
C8 C9 . . 1.522(2) no
C9 C10 . . 1.506(2) no
C10 C11 . . 1.512(2) no
C11 C12 . . 1.524(3) no
C12 C13 . . 1.506(3) no
C14 N6 2_666 . 1.323(2) no
C14 N7 2_666 . 1.352(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132994
