#------------------------------------------------------------------------------
#$Date: 2018-09-10 01:01:50 +0300 (Mon, 10 Sep 2018) $
#$Revision: 210696 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/38/7103811.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_7103811
loop_
_publ_author_name
'Warriner, Colin N.'
'Gale, Philip A.'
'Light, Mark E.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Pentapyrrolic calix[4]pyrrole
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   15
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1810
_journal_page_last               1811
_journal_paper_doi               10.1039/b303959e
_journal_year                    2003
_chemical_formula_sum            'C14 H12 Br3 N3'
_chemical_formula_weight         462.00
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 114.25(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.13(4)
_cell_length_b                   10.965(8)
_cell_length_c                   17.450(15)
_cell_measurement_temperature    120(2)
_cell_volume                     2989(7)
_computing_cell_refinement       'EVALCCD '
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'EVALCCD, COLLECT)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '9.091 pixels mm^1^'
_diffrn_measured_fraction_theta_full 0.657
_diffrn_measured_fraction_theta_max 0.657
_diffrn_measurement_device_type  'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method       'φ and ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13791
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.90
_exptl_absorpt_coefficient_mu    8.090
_exptl_absorpt_correction_T_max  0.7934
_exptl_absorpt_correction_T_min  0.4984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1997)'
_exptl_crystal_density_diffrn    2.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.835
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.00032(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0480
_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)+(0.0488P)²+2.3714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2351
_reflns_number_total             3468
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b303959e.txt
_cod_data_source_block           s92
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'Multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7103811
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.09245(7) -0.09399(9) -0.03799(6) 0.0439(3) Uani 1 1 d . . .
Br2 Br 0.09172(7) -0.38805(8) 0.06020(6) 0.0392(3) Uani 1 1 d . . .
Br3 Br 0.13529(6) -0.32371(7) 0.27499(6) 0.0302(3) Uani 1 1 d . . .
N1 N 0.1236(4) -0.0354(6) 0.1292(4) 0.0178(15) Uani 1 1 d . . .
H1 H 0.1256 0.0428 0.1188 0.021 Uiso 1 1 calc R . .
N2 N 0.2206(5) -0.0175(7) 0.4356(5) 0.044(2) Uani 1 1 d . . .
H2 H 0.1827 0.0262 0.4456 0.053 Uiso 1 1 calc R . .
N3 N 0.2358(4) 0.1743(5) 0.2742(4) 0.0208(17) Uani 1 1 d . . .
H3 H 0.2836 0.1319 0.2944 0.025 Uiso 1 1 calc R . .
C1 C 0.1090(5) -0.1256(8) 0.0712(5) 0.027(2) Uani 1 1 d . . .
C2 C 0.1107(5) -0.2338(7) 0.1109(5) 0.021(2) Uani 1 1 d . . .
C3 C 0.1272(5) -0.2060(6) 0.1943(5) 0.0169(18) Uani 1 1 d . . .
C4 C 0.1348(5) -0.0818(7) 0.2051(5) 0.0199(19) Uani 1 1 d . . .
C5 C 0.1436(5) -0.0010(7) 0.2781(5) 0.0201(19) Uani 1 1 d . . .
C6 C 0.0584(5) -0.0138(7) 0.2881(5) 0.027(2) Uani 1 1 d . . .
H6A H 0.0106 0.0091 0.2354 0.040 Uiso 1 1 calc R . .
H6B H 0.0593 0.0399 0.3334 0.040 Uiso 1 1 calc R . .
H6C H 0.0512 -0.0985 0.3020 0.040 Uiso 1 1 calc R . .
C7 C 0.2169(5) -0.0438(7) 0.3573(5) 0.022(2) Uani 1 1 d . . .
C8 C 0.2911(8) -0.0689(10) 0.4948(7) 0.059(3) Uani 1 1 d . . .
H8 H 0.3087 -0.0623 0.5538 0.071 Uiso 1 1 calc R . .
C9 C 0.3319(6) -0.1300(8) 0.4569(7) 0.051(3) Uani 1 1 d . . .
H9 H 0.3824 -0.1770 0.4840 0.061 Uiso 1 1 calc R . .
C10 C 0.2863(5) -0.1129(7) 0.3669(6) 0.030(2) Uani 1 1 d . . .
H10 H 0.3016 -0.1434 0.3240 0.036 Uiso 1 1 calc R . .
C11 C 0.1563(5) 0.1300(7) 0.2602(5) 0.0169(18) Uani 1 1 d . . .
C12 C 0.0990(6) 0.2245(7) 0.2283(5) 0.024(2) Uani 1 1 d . . .
H12 H 0.0389 0.2209 0.2118 0.028 Uiso 1 1 calc R . .
C13 C 0.1467(6) 0.3274(7) 0.2250(5) 0.024(2) Uani 1 1 d . . .
H13 H 0.1243 0.4066 0.2068 0.029 Uiso 1 1 calc R . .
C14 C 0.2294(7) 0.2944(7) 0.2522(5) 0.025(2) Uani 1 1 d . . .
H14 H 0.2754 0.3457 0.2555 0.029 Uiso 1 1 calc R . .
Br4 Br 0.32169(7) -0.07851(10) 0.15017(7) 0.0480(3) Uani 1 1 d . . .
Br5 Br 0.53109(6) -0.08626(8) 0.31463(5) 0.0325(3) Uani 1 1 d . . .
Br6 Br 0.66315(6) 0.11606(8) 0.25310(6) 0.0320(3) Uani 1 1 d . . .
N4 N 0.4986(4) 0.1328(5) 0.1199(4) 0.0201(16) Uani 1 1 d . . .
H4 H 0.5175 0.1832 0.0922 0.024 Uiso 1 1 calc R . .
N5 N 0.1970(4) 0.1852(6) -0.0695(4) 0.0222(18) Uani 1 1 d . . .
H5 H 0.1912 0.1630 -0.1200 0.027 Uiso 1 1 calc R . .
N6 N 0.3897(4) 0.3235(6) -0.0348(4) 0.0234(16) Uani 1 1 d . . .
H6 H 0.3651 0.3636 -0.0070 0.028 Uiso 1 1 calc R . .
C15 C 0.5454(5) 0.0865(7) 0.1968(5) 0.0199(19) Uani 1 1 d . . .
C16 C 0.4955(5) 0.0109(7) 0.2190(5) 0.023(2) Uani 1 1 d . . .
C17 C 0.4135(5) 0.0145(7) 0.1521(5) 0.0200(19) Uani 1 1 d . . .
C18 C 0.4157(5) 0.0880(6) 0.0916(5) 0.0167(18) Uani 1 1 d . . .
C19 C 0.3509(5) 0.1157(6) 0.0016(5) 0.0181(18) Uani 1 1 d . . .
C20 C 0.3283(5) -0.0059(7) -0.0463(5) 0.026(2) Uani 1 1 d . . .
H20A H 0.3070 -0.0633 -0.0163 0.039 Uiso 1 1 calc R . .
H20B H 0.3795 -0.0398 -0.0502 0.039 Uiso 1 1 calc R . .
H20C H 0.2840 0.0078 -0.1030 0.039 Uiso 1 1 calc R . .
C21 C 0.2711(5) 0.1734(7) 0.0031(5) 0.0219(19) Uani 1 1 d . . .
C22 C 0.2546(6) 0.2195(8) 0.0677(6) 0.032(2) Uani 1 1 d . . .
H22 H 0.2939 0.2247 0.1250 0.038 Uiso 1 1 calc R . .
C23 C 0.1673(6) 0.2586(8) 0.0332(5) 0.029(2) Uani 1 1 d . . .
H23 H 0.1372 0.2938 0.0629 0.034 Uiso 1 1 calc R . .
C24 C 0.1357(5) 0.2349(7) -0.0516(5) 0.025(2) Uani 1 1 d . . .
H24 H 0.0791 0.2515 -0.0912 0.030 Uiso 1 1 calc R . .
C25 C 0.3918(5) 0.2007(6) -0.0409(5) 0.0187(19) Uani 1 1 d . . .
C26 C 0.4364(5) 0.1731(7) -0.0870(5) 0.0207(19) Uani 1 1 d . . .
H26 H 0.4487 0.0935 -0.1005 0.025 Uiso 1 1 calc R . .
C27 C 0.4616(5) 0.2847(7) -0.1118(5) 0.029(2) Uani 1 1 d . . .
H27 H 0.4933 0.2937 -0.1452 0.034 Uiso 1 1 calc R . .
C28 C 0.4315(5) 0.3761(7) -0.0785(5) 0.025(2) Uani 1 1 d . . .
H28 H 0.4384 0.4611 -0.0844 0.031 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 0.0033 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'
Br Br -0.2901 2.4595 '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
C4 N1 C1 111.3(7) . . ?
C8 N2 C7 109.6(9) . . ?
C14 N3 C11 109.5(7) . . ?
N1 C1 C2 107.0(7) . . ?
N1 C1 Br1 122.4(6) . . ?
C2 C1 Br1 130.6(6) . . ?
C1 C2 C3 106.9(6) . . ?
C1 C2 Br2 125.4(6) . . ?
C3 C2 Br2 127.7(6) . . ?
C4 C3 C2 109.1(7) . . ?
C4 C3 Br3 127.3(6) . . ?
C2 C3 Br3 123.6(5) . . ?
N1 C4 C3 105.6(7) . . ?
N1 C4 C5 122.0(7) . . ?
C3 C4 C5 132.1(8) . . ?
C11 C5 C4 111.0(7) . . ?
C11 C5 C7 110.4(6) . . ?
C4 C5 C7 110.3(6) . . ?
C11 C5 C6 109.5(6) . . ?
C4 C5 C6 105.8(6) . . ?
C7 C5 C6 109.7(7) . . ?
C10 C7 N2 108.3(8) . . ?
C10 C7 C5 130.0(8) . . ?
N2 C7 C5 121.8(8) . . ?
C9 C8 N2 108.6(10) . . ?
C8 C9 C10 108.4(9) . . ?
C7 C10 C9 105.1(8) . . ?
N3 C11 C12 107.2(7) . . ?
N3 C11 C5 121.4(7) . . ?
C12 C11 C5 131.4(7) . . ?
C11 C12 C13 106.8(8) . . ?
C14 C13 C12 108.3(8) . . ?
C13 C14 N3 108.0(9) . . ?
C15 N4 C18 109.0(6) . . ?
C24 N5 C21 109.9(7) . . ?
C25 N6 C28 109.8(7) . . ?
N4 C15 C16 109.0(7) . . ?
N4 C15 Br6 122.0(6) . . ?
C16 C15 Br6 128.7(6) . . ?
C15 C16 C17 106.1(7) . . ?
C15 C16 Br5 126.4(6) . . ?
C17 C16 Br5 127.3(6) . . ?
C18 C17 C16 109.2(7) . . ?
C18 C17 Br4 127.6(6) . . ?
C16 C17 Br4 123.1(6) . . ?
C17 C18 N4 106.7(7) . . ?
C17 C18 C19 133.1(7) . . ?
N4 C18 C19 119.8(6) . . ?
C21 C19 C25 110.5(6) . . ?
C21 C19 C18 110.0(6) . . ?
C25 C19 C18 109.6(6) . . ?
C21 C19 C20 110.1(6) . . ?
C25 C19 C20 109.2(6) . . ?
C18 C19 C20 107.4(6) . . ?
C22 C21 N5 107.3(8) . . ?
C22 C21 C19 131.4(8) . . ?
N5 C21 C19 121.3(7) . . ?
C21 C22 C23 107.4(8) . . ?
C24 C23 C22 106.1(8) . . ?
N5 C24 C23 109.3(7) . . ?
N6 C25 C26 108.0(7) . . ?
N6 C25 C19 122.5(7) . . ?
C26 C25 C19 129.5(7) . . ?
C25 C26 C27 107.8(7) . . ?
C28 C27 C26 106.7(7) . . ?
C27 C28 N6 107.7(7) . . ?
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
Br1 C1 1.840(9) . ?
Br2 C2 1.874(7) . ?
Br3 C3 1.873(7) . ?
N1 C4 1.357(10) . ?
N1 C1 1.363(10) . ?
N2 C8 1.349(13) . ?
N2 C7 1.372(10) . ?
N3 C14 1.363(10) . ?
N3 C11 1.369(10) . ?
C1 C2 1.369(10) . ?
C2 C3 1.397(10) . ?
C3 C4 1.374(10) . ?
C4 C5 1.506(11) . ?
C5 C11 1.505(10) . ?
C5 C7 1.511(10) . ?
C5 C6 1.547(11) . ?
C7 C10 1.360(11) . ?
C8 C9 1.323(15) . ?
C9 C10 1.450(13) . ?
C11 C12 1.378(10) . ?
C12 C13 1.408(11) . ?
C13 C14 1.347(12) . ?
Br4 C17 1.864(8) . ?
Br5 C16 1.859(8) . ?
Br6 C15 1.874(9) . ?
N4 C15 1.347(9) . ?
N4 C18 1.388(10) . ?
N5 C24 1.328(10) . ?
N5 C21 1.383(10) . ?
N6 C25 1.352(9) . ?
N6 C28 1.371(10) . ?
C15 C16 1.357(10) . ?
C16 C17 1.411(11) . ?
C17 C18 1.340(10) . ?
C18 C19 1.536(11) . ?
C19 C21 1.517(11) . ?
C19 C25 1.527(10) . ?
C19 C20 1.537(10) . ?
C21 C22 1.367(11) . ?
C22 C23 1.429(12) . ?
C23 C24 1.376(11) . ?
C25 C26 1.353(10) . ?
C26 C27 1.424(11) . ?
C27 C28 1.362(11) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6 Br5 0.88 3.13 3.646(7) 119.3 2_655
