#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/11/2231192.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_2231192
loop_
_publ_author_name
'Hagos, Tesfamariam K.'
'Nogai, Stefan D.'
'Dobrzańska, Liliana'
'Cronje, Stephanie'
'Raubenheimer, Helgard G.'
_publ_section_title
;
 1,1,2,2-Tetrakis(1,3-benzoxazol-2-yl)ethene
;
_journal_coeditor_code           KP2340
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2014
_journal_paper_doi               10.1107/S1600536811026924
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C30 H16 N4 O4'
_chemical_formula_moiety         'C30 H16 N4 O4'
_chemical_formula_sum            'C30 H16 N4 O4'
_chemical_formula_weight         496.47
_chemical_name_systematic
;
1,1,2,2-Tetrakis(1,3-benzoxazol-2-yl)ethene
;
_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                 104.395(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2697(9)
_cell_length_b                   16.1943(16)
_cell_length_c                   8.0332(8)
_cell_measurement_reflns_used    3523
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.271
_cell_measurement_theta_min      2.516
_cell_volume                     1168.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6999
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0485
_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)+(0.0513P)²+0.8168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                2458
_reflns_number_total             2717
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2340.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231192
_cod_database_fobs_code          2231192
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.02783(16) 0.46822(9) 0.55330(19) 0.0186(3) Uani d . 1 1
C C2 -0.02821(16) 0.44239(9) 0.69934(19) 0.0199(3) Uani d . 1 1
N N3 0.01487(14) 0.37588(8) 0.78861(16) 0.0197(3) Uani d . 1 1
C C4 -0.06473(16) 0.37680(9) 0.91493(19) 0.0196(3) Uani d . 1 1
C C5 -0.06558(18) 0.32189(10) 1.0482(2) 0.0240(3) Uani d . 1 1
H H5 -0.0059 0.2749 1.0664 0.029 Uiso calc R 1 1
C C6 -0.15995(18) 0.34088(10) 1.1524(2) 0.0258(3) Uani d . 1 1
H H6 -0.1640 0.3055 1.2423 0.031 Uiso calc R 1 1
C C7 -0.24923(18) 0.41171(10) 1.1263(2) 0.0262(4) Uani d . 1 1
H H7 -0.3114 0.4218 1.1988 0.031 Uiso calc R 1 1
C C8 -0.24768(18) 0.46738(10) 0.9955(2) 0.0246(3) Uani d . 1 1
H H8 -0.3060 0.5148 0.9782 0.029 Uiso calc R 1 1
C C9 -0.15338(16) 0.44734(9) 0.89261(19) 0.0199(3) Uani d . 1 1
O O10 -0.12962(12) 0.48989(7) 0.75253(14) 0.0217(3) Uani d . 1 1
C C11 0.15956(17) 0.42084(10) 0.53413(19) 0.0217(3) Uani d . 1 1
N N12 0.29464(13) 0.44984(7) 0.58136(16) 0.0179(3) Uani d . 1 1
C C13 0.38086(17) 0.38841(9) 0.53122(19) 0.0194(3) Uani d . 1 1
C C14 0.53275(17) 0.38556(10) 0.5437(2) 0.0251(3) Uani d . 1 1
H H14 0.5959 0.4286 0.5920 0.030 Uiso calc R 1 1
C C15 0.58507(18) 0.31551(11) 0.4807(2) 0.0284(4) Uani d . 1 1
H H15 0.6863 0.3111 0.4872 0.034 Uiso calc R 1 1
C C16 0.4904(2) 0.25091(11) 0.4074(2) 0.0309(4) Uani d . 1 1
H H16 0.5307 0.2048 0.3666 0.037 Uiso calc R 1 1
C C17 0.33806(19) 0.25342(10) 0.3935(2) 0.0284(4) Uani d . 1 1
H H17 0.2746 0.2106 0.3450 0.034 Uiso calc R 1 1
C C18 0.28725(16) 0.32445(9) 0.45730(19) 0.0205(3) Uani d . 1 1
O O19 0.14322(12) 0.34621(7) 0.46062(15) 0.0258(3) Uani d . 1 1
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'
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
C1 C1 C2 3_566 124.77(17)
C1 C1 C11 3_566 121.42(17)
C2 C1 C11 . 113.75(12)
N3 C2 O10 . 115.83(13)
N3 C2 C1 . 124.01(14)
O10 C2 C1 . 120.14(13)
C2 N3 C4 . 104.29(12)
C9 C4 C5 . 120.43(14)
C9 C4 N3 . 108.48(13)
C5 C4 N3 . 131.09(14)
C6 C5 C4 . 116.56(15)
C6 C5 H5 . 121.7
C4 C5 H5 . 121.7
C5 C6 C7 . 121.96(15)
C5 C6 H6 . 119.0
C7 C6 H6 . 119.0
C8 C7 C6 . 121.95(15)
C8 C7 H7 . 119.0
C6 C7 H7 . 119.0
C9 C8 C7 . 115.30(15)
C9 C8 H8 . 122.4
C7 C8 H8 . 122.4
C8 C9 O10 . 128.44(14)
C8 C9 C4 . 123.79(14)
O10 C9 C4 . 107.77(13)
C2 O10 C9 . 103.63(11)
N12 C11 O19 . 116.73(13)
N12 C11 C1 . 122.70(14)
O19 C11 C1 . 120.53(13)
C11 N12 C13 . 103.70(12)
C18 C13 C14 . 121.47(14)
C18 C13 N12 . 108.27(13)
C14 C13 N12 . 130.25(14)
C15 C14 C13 . 116.37(15)
C15 C14 H14 . 121.8
C13 C14 H14 . 121.8
C14 C15 C16 . 121.96(15)
C14 C15 H15 . 119.0
C16 C15 H15 . 119.0
C17 C16 C15 . 122.06(15)
C17 C16 H16 . 119.0
C15 C16 H16 . 119.0
C18 C17 C16 . 115.22(15)
C18 C17 H17 . 122.4
C16 C17 H17 . 122.4
C13 C18 O19 . 107.75(13)
C13 C18 C17 . 122.92(14)
O19 C18 C17 . 129.34(14)
C11 O19 C18 . 103.54(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C1 3_566 1.356(3)
C1 C2 . 1.458(2)
C1 C11 . 1.482(2)
C2 N3 . 1.3006(19)
C2 O10 . 1.3628(18)
N3 C4 . 1.3952(19)
C4 C9 . 1.393(2)
C4 C5 . 1.394(2)
C5 C6 . 1.387(2)
C5 H5 . 0.9300
C6 C7 . 1.399(2)
C6 H6 . 0.9300
C7 C8 . 1.387(2)
C7 H7 . 0.9300
C8 C9 . 1.382(2)
C8 H8 . 0.9300
C9 O10 . 1.3830(18)
C11 N12 . 1.302(2)
C11 O19 . 1.3370(19)
N12 C13 . 1.3966(18)
C13 C18 . 1.386(2)
C13 C14 . 1.387(2)
C14 C15 . 1.379(2)
C14 H14 . 0.9300
C15 C16 . 1.398(3)
C15 H15 . 0.9300
C16 C17 . 1.389(2)
C16 H16 . 0.9300
C17 C18 . 1.388(2)
C17 H17 . 0.9300
C18 O19 . 1.3874(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7 N12 3_567 0.93 2.71 3.348(2) 127
C17 H17 N3 4_565 0.93 2.71 3.580(2) 153
C14 H14 N12 3_666 0.93 2.75 3.387(2) 127
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_site_symmetry_1
_geom_torsion
C1 C1 C2 N3 3_566 171.93(18)
C11 C1 C2 N3 . -11.0(2)
C1 C1 C2 O10 3_566 -9.6(3)
C11 C1 C2 O10 . 167.47(13)
O10 C2 N3 C4 . 0.47(17)
C1 C2 N3 C4 . 178.99(13)
C2 N3 C4 C9 . -0.45(15)
C2 N3 C4 C5 . -179.84(16)
C9 C4 C5 C6 . 1.1(2)
N3 C4 C5 C6 . -179.58(15)
C4 C5 C6 C7 . -0.4(2)
C5 C6 C7 C8 . -0.5(2)
C6 C7 C8 C9 . 0.7(2)
C7 C8 C9 O10 . 179.17(14)
C7 C8 C9 C4 . 0.0(2)
C5 C4 C9 C8 . -1.0(2)
N3 C4 C9 C8 . 179.59(14)
C5 C4 C9 O10 . 179.77(13)
N3 C4 C9 O10 . 0.30(16)
N3 C2 O10 C9 . -0.29(16)
C1 C2 O10 C9 . -178.87(13)
C8 C9 O10 C2 . -179.27(15)
C4 C9 O10 C2 . -0.03(15)
C1 C1 C11 N12 3_566 75.2(2)
C2 C1 C11 N12 . -102.04(16)
C1 C1 C11 O19 3_566 -102.5(2)
C2 C1 C11 O19 . 80.33(17)
O19 C11 N12 C13 . 1.25(17)
C1 C11 N12 C13 . -176.47(13)
C11 N12 C13 C18 . -0.89(16)
C11 N12 C13 C14 . 178.08(16)
C18 C13 C14 C15 . -0.7(2)
N12 C13 C14 C15 . -179.59(15)
C13 C14 C15 C16 . 0.3(2)
C14 C15 C16 C17 . 0.0(3)
C15 C16 C17 C18 . 0.1(3)
C14 C13 C18 O19 . -178.77(13)
N12 C13 C18 O19 . 0.32(16)
C14 C13 C18 C17 . 0.9(2)
N12 C13 C18 C17 . 180.00(14)
C16 C17 C18 C13 . -0.6(2)
C16 C17 C18 O19 . 179.05(15)
N12 C11 O19 C18 . -1.06(17)
C1 C11 O19 C18 . 176.71(13)
C13 C18 O19 C11 . 0.38(15)
C17 C18 O19 C11 . -179.28(16)
