#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208500.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_7208500
loop_
_publ_author_name
'Lim, Jaebum'
'Osowska, Karolina'
'Armitage, Jacob A.'
'Martin, Benjamin R.'
'Miljanić, Ognjen Š.'
_publ_section_title
;
 Critical role of weak [C--H⋯O] hydrogen bonds in the assembly of
 benzo[1,2-d:4,5-d′]bisoxazole cruciforms into supramolecular
 sheets
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              6152
_journal_paper_doi               10.1039/c2ce25485a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C36 H28 N2 O10, 2 (C2 H3 N)'
_chemical_formula_sum            'C40 H34 N4 O10'
_chemical_formula_weight         730.71
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.088(2)
_cell_angle_beta                 98.465(2)
_cell_angle_gamma                92.660(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5375(11)
_cell_length_b                   8.5549(12)
_cell_length_c                   14.7035(21)
_cell_measurement_reflns_used    1455
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      2.43
_cell_volume                     917.6(2)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       CCD
_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  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4097
_diffrn_reflns_theta_full        23.54
_diffrn_reflns_theta_max         23.54
_diffrn_reflns_theta_min         2.43
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SAINT v7.12A'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             382
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.369
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.6643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                1515
_reflns_number_total             2699
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            c2ce25485a.txt
_cod_data_source_block           k1215
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' 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_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7208500
loop_
_symmetry_equiv_pos_as_xyz
'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
O1 O 0.2909(3) 0.5905(2) 0.35639(16) 0.0486(6) Uani 1 1 d . . .
O2 O 0.0974(4) 0.5476(3) 0.17789(19) 0.0727(8) Uani 1 1 d . . .
O3 O 0.2252(4) 0.3178(3) 0.13967(19) 0.0714(8) Uani 1 1 d . . .
O4 O 0.0459(3) 1.6548(2) 0.65005(17) 0.0529(7) Uani 1 1 d . . .
O5 O 0.2504(3) 1.6591(2) 0.77700(18) 0.0543(6) Uani 1 1 d . . .
N1 N 0.3861(3) 0.3450(3) 0.32006(18) 0.0351(6) Uani 1 1 d . . .
C1 C 0.4364(4) 0.6623(3) 0.5232(2) 0.0366(8) Uani 1 1 d . . .
C2 C 0.3937(4) 0.5606(3) 0.4358(2) 0.0363(7) Uani 1 1 d . . .
C3 C 0.2940(4) 0.4560(4) 0.2915(2) 0.0460(8) Uani 1 1 d . . .
C4 C 0.4529(4) 0.4074(3) 0.4131(2) 0.0374(8) Uani 1 1 d . . .
C5 C 0.1946(4) 0.4493(4) 0.1973(3) 0.0504(9) Uani 1 1 d . . .
C6 C 0.1361(7) 0.2941(6) 0.0428(3) 0.0869(14) Uani 1 1 d . . .
H6A H 0.0175 0.3368 0.0407 0.104 Uiso 1 1 calc R . .
H6B H 0.1191 0.1796 0.0151 0.104 Uiso 1 1 calc R . .
C7 C 0.2470(8) 0.3764(7) -0.0110(4) 0.126(2) Uani 1 1 d . . .
H7A H 0.1876 0.3609 -0.0756 0.189 Uiso 1 1 calc R . .
H7B H 0.3637 0.3328 -0.0093 0.189 Uiso 1 1 calc R . .
H7C H 0.2626 0.4897 0.0165 0.189 Uiso 1 1 calc R . .
C8 C 0.3781(4) 0.8184(3) 0.5471(2) 0.0413(8) Uani 1 1 d . . .
C9 C 0.3328(4) 0.9502(4) 0.5708(2) 0.0411(8) Uani 1 1 d . . .
C10 C 0.2844(4) 1.1095(3) 0.6029(2) 0.0391(8) Uani 1 1 d . . .
C11 C 0.1669(4) 1.1833(3) 0.5453(2) 0.0406(8) Uani 1 1 d . . .
H11 H 0.1162 1.1282 0.4847 0.049 Uiso 1 1 calc R . .
C12 C 0.1249(4) 1.3368(3) 0.5771(2) 0.0409(8) Uani 1 1 d . . .
H12 H 0.0446 1.3857 0.5381 0.049 Uiso 1 1 calc R . .
C13 C 0.1995(4) 1.4207(3) 0.6660(2) 0.0364(8) Uani 1 1 d . . .
C14 C 0.3143(4) 1.3463(3) 0.7241(2) 0.0408(8) Uani 1 1 d . . .
H14 H 0.3639 1.4015 0.7849 0.049 Uiso 1 1 calc R . .
C15 C 0.3559(4) 1.1925(3) 0.6932(2) 0.0421(8) Uani 1 1 d . . .
H15 H 0.4330 1.1427 0.7332 0.051 Uiso 1 1 calc R . .
C16 C 0.1538(4) 1.5893(4) 0.6951(3) 0.0427(8) Uani 1 1 d . . .
C17 C 0.2267(5) 1.8280(4) 0.8089(3) 0.0635(11) Uani 1 1 d . . .
H17A H 0.2417 1.8868 0.7592 0.076 Uiso 1 1 calc R . .
H17B H 0.1058 1.8412 0.8247 0.076 Uiso 1 1 calc R . .
C18 C 0.3614(6) 1.8889(5) 0.8913(3) 0.0895(14) Uani 1 1 d . . .
H18A H 0.3490 2.0016 0.9135 0.134 Uiso 1 1 calc R . .
H18B H 0.4806 1.8748 0.8750 0.134 Uiso 1 1 calc R . .
H18C H 0.3444 1.8310 0.9403 0.134 Uiso 1 1 calc R . .
C19 C 0.1614(12) 0.9526(10) 0.2929(4) 0.059(3) Uiso 0.65 1 d PG A 1
H19A H 0.2793 0.9700 0.3299 0.071 Uiso 0.65 1 d PG A 1
H19B H 0.0943 1.0435 0.3100 0.071 Uiso 0.65 1 d PG A 1
H19C H 0.1003 0.8590 0.3043 0.071 Uiso 0.65 1 d PG A 1
C20 C 0.1763(6) 0.9311(5) 0.1968(4) 0.0612(18) Uiso 0.65 1 d PG A 1
N2 N 0.1893(8) 0.9148(7) 0.1195(4) 0.098(2) Uiso 0.65 1 d PG A 1
C21 C 0.135(3) 0.929(2) 0.2779(9) 0.079(7) Uiso 0.35 1 d PG B 2
H21A H 0.0061 0.9160 0.2635 0.094 Uiso 0.35 1 d PG B 2
H21B H 0.1769 0.8576 0.3179 0.094 Uiso 0.35 1 d PG B 2
H21C H 0.1720 1.0372 0.3094 0.094 Uiso 0.35 1 d PG B 2
C22 C 0.2103(14) 0.8936(11) 0.1918(7) 0.085(5) Uiso 0.35 1 d PG B 2
N3 N 0.2622(15) 0.8628(13) 0.1217(8) 0.095(4) Uiso 0.35 1 d PG B 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C3 O1 C2 103.8(2) . .
C5 O3 C6 116.9(3) . .
C16 O5 C17 115.9(3) . .
C3 N1 C4 104.8(3) . .
C2 C1 C4 111.6(2) . 2_666
C2 C1 C8 125.5(3) . .
C4 C1 C8 122.9(3) 2_666 .
O1 C2 C1 127.5(2) . .
O1 C2 C4 107.6(3) . .
C1 C2 C4 124.9(3) . .
N1 C3 O1 115.7(3) . .
N1 C3 C5 126.8(3) . .
O1 C3 C5 117.5(3) . .
N1 C4 C2 108.0(3) . .
N1 C4 C1 128.4(3) . 2_666
C2 C4 C1 123.5(3) . 2_666
O2 C5 O3 126.1(4) . .
O2 C5 C3 123.6(3) . .
O3 C5 C3 110.3(3) . .
O3 C6 C7 109.4(4) . .
C9 C8 C1 177.4(4) . .
C8 C9 C10 177.5(4) . .
C11 C10 C15 119.1(3) . .
C11 C10 C9 121.1(3) . .
C15 C10 C9 119.8(3) . .
C12 C11 C10 119.9(3) . .
C11 C12 C13 120.9(3) . .
C12 C13 C14 119.2(3) . .
C12 C13 C16 118.3(3) . .
C14 C13 C16 122.5(3) . .
C15 C14 C13 120.3(3) . .
C14 C15 C10 120.5(3) . .
O4 C16 O5 124.0(3) . .
O4 C16 C13 124.8(3) . .
O5 C16 C13 111.2(3) . .
C18 C17 O5 108.0(3) . .
N2 C20 C19 179.4 . .
N3 C22 C21 176.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.350(4) .
O1 C2 1.377(4) .
O2 C5 1.189(4) .
O3 C5 1.324(4) .
O3 C6 1.454(5) .
O4 C16 1.200(4) .
O5 C16 1.328(4) .
O5 C17 1.458(4) .
N1 C3 1.300(4) .
N1 C4 1.379(4) .
C1 C2 1.391(4) .
C1 C4 1.399(4) 2_666
C1 C8 1.421(4) .
C2 C4 1.399(4) .
C3 C5 1.463(5) .
C4 C1 1.399(4) 2_666
C6 C7 1.475(6) .
C8 C9 1.195(4) .
C9 C10 1.436(4) .
C10 C11 1.392(4) .
C10 C15 1.397(4) .
C11 C12 1.375(4) .
C12 C13 1.388(4) .
C13 C14 1.388(4) .
C13 C16 1.495(4) .
C14 C15 1.374(4) .
C17 C18 1.454(6) .
C19 C20 1.4120 .
C20 N2 1.1369 .
C21 C22 1.4478 .
C22 N3 1.1446 .
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_4
C3 O1 C2 C1 178.9(3) . .
C3 O1 C2 C4 -0.1(3) . .
C4 C1 C2 O1 -178.8(2) 2_666 .
C8 C1 C2 O1 0.9(5) . .
C4 C1 C2 C4 0.0(4) 2_666 .
C8 C1 C2 C4 179.7(3) . .
C4 N1 C3 O1 0.1(3) . .
C4 N1 C3 C5 -179.7(3) . .
C2 O1 C3 N1 0.0(3) . .
C2 O1 C3 C5 179.8(2) . .
C3 N1 C4 C2 -0.1(3) . .
C3 N1 C4 C1 -178.9(3) . 2_666
O1 C2 C4 N1 0.1(3) . .
C1 C2 C4 N1 -178.9(2) . .
O1 C2 C4 C1 179.0(2) . 2_666
C1 C2 C4 C1 0.0(5) . 2_666
C6 O3 C5 O2 2.1(5) . .
C6 O3 C5 C3 -179.7(3) . .
N1 C3 C5 O2 171.7(3) . .
O1 C3 C5 O2 -8.1(5) . .
N1 C3 C5 O3 -6.5(4) . .
O1 C3 C5 O3 173.7(3) . .
C5 O3 C6 C7 86.1(4) . .
C15 C10 C11 C12 1.0(4) . .
C9 C10 C11 C12 -178.9(3) . .
C10 C11 C12 C13 0.6(4) . .
C11 C12 C13 C14 -1.6(4) . .
C11 C12 C13 C16 177.7(3) . .
C12 C13 C14 C15 1.1(4) . .
C16 C13 C14 C15 -178.2(3) . .
C13 C14 C15 C10 0.5(4) . .
C11 C10 C15 C14 -1.6(4) . .
C9 C10 C15 C14 178.4(3) . .
C17 O5 C16 O4 -3.5(4) . .
C17 O5 C16 C13 175.6(3) . .
C12 C13 C16 O4 6.1(4) . .
C14 C13 C16 O4 -174.5(3) . .
C12 C13 C16 O5 -172.9(2) . .
C14 C13 C16 O5 6.4(4) . .
C16 O5 C17 C18 -171.5(3) . .
