#------------------------------------------------------------------------------
#$Date: 2016-02-05 00:14:23 +0200 (Fri, 05 Feb 2016) $
#$Revision: 175942 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/33/7223335.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_7223335
loop_
_publ_author_name
'Fan, Guoling'
'Yang, Xiaogang'
'Liang, Ruizheng'
'Zhao, Jingwen'
'Li, Shuzhen'
'Yan, Dongpeng'
_publ_section_title
;
 Molecular cocrystals of diphenyloxazole with tunable fluorescence,
 up-conversion emission and dielectric properties
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              240
_journal_paper_doi               10.1039/C5CE02019K
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C36 H22 Br2 F4 N2 O2'
_chemical_formula_weight         750.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2015-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.874(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7528(5)
_cell_length_b                   22.874(8)
_cell_length_c                   11.463(6)
_cell_measurement_reflns_used    1607
_cell_measurement_temperature    100.1
_cell_measurement_theta_max      29.1962
_cell_measurement_theta_min      3.5577
_cell_volume                     1494.2(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'SHELXTL-V (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scan'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5743
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_T_max  0.6809
_exptl_absorpt_correction_T_min  0.5555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod-shaped
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.088
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0425
_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)+(0.0366P)²+1.7908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                2409
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce02019k2.cif
_cod_data_source_block           exp_1954
_cod_depositor_comments
'Adding full bibliography for 7223333--7223337.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7223335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br1 Br 0.79212(6) -0.061905(17) 0.80727(3) 0.02275(13) Uani 1 1 d .
C1 C 0.6116(6) 0.13682(17) 0.6916(3) 0.0236(8) Uani 1 1 d .
C2 C 0.4543(7) 0.12516(19) 0.7695(3) 0.0299(9) Uani 1 1 d .
C3 C 0.2722(7) 0.08610(19) 0.7395(4) 0.0313(9) Uani 1 1 d .
C4 C 0.2482(6) 0.05807(18) 0.6315(4) 0.0301(9) Uani 1 1 d .
C5 C 0.4037(6) 0.06975(16) 0.5522(3) 0.0246(8) Uani 1 1 d .
C6 C 0.5879(6) 0.10972(15) 0.5817(3) 0.0204(8) Uani 1 1 d .
C7 C 0.7482(6) 0.12327(15) 0.4983(3) 0.0197(8) Uani 1 1 d .
C8 C 0.7836(6) 0.10398(16) 0.3911(3) 0.0221(8) Uani 1 1 d .
C9 C 1.0349(6) 0.17211(16) 0.4374(3) 0.0191(8) Uani 1 1 d .
C10 C 1.2219(6) 0.21536(15) 0.4476(3) 0.0189(7) Uani 1 1 d .
C11 C 1.3695(6) 0.21990(16) 0.3605(3) 0.0228(8) Uani 1 1 d .
C12 C 1.5520(6) 0.26010(17) 0.3743(3) 0.0241(8) Uani 1 1 d .
C13 C 1.5906(6) 0.29507(17) 0.4732(3) 0.0243(8) Uani 1 1 d .
C14 C 1.4445(6) 0.29086(16) 0.5593(3) 0.0245(8) Uani 1 1 d .
C15 C 1.2604(6) 0.25152(16) 0.5465(3) 0.0216(8) Uani 1 1 d .
C16 C 0.6263(5) -0.02567(16) 0.9172(3) 0.0177(7) Uani 1 1 d .
C17 C 0.6884(5) 0.02829(16) 0.9652(3) 0.0184(8) Uani 1 1 d .
C18 C 0.5643(6) 0.05386(15) 1.0463(3) 0.0192(7) Uani 1 1 d .
F1 F 0.8707(3) 0.05756(9) 0.93186(18) 0.0253(5) Uani 1 1 d .
F2 F 0.6277(3) 0.10691(9) 1.08883(19) 0.0274(5) Uani 1 1 d .
H1 H 0.7325 0.1664 0.7081 0.033 Uiso 1 1 d R
H2 H 0.4663 0.1440 0.8462 0.033 Uiso 1 1 d R
H3 H 0.1674 0.0763 0.7960 0.033 Uiso 1 1 d R
H4 H 0.1146 0.0330 0.6072 0.033 Uiso 1 1 d R
H5 H 0.4024 0.0555 0.4723 0.033 Uiso 1 1 d R
H8 H 0.7089 0.0723 0.3432 0.033 Uiso 1 1 d R
H11 H 1.3496 0.1967 0.2883 0.033 Uiso 1 1 d R
H12 H 1.6298 0.2588 0.3039 0.033 Uiso 1 1 d R
H13 H 1.7397 0.3155 0.4801 0.033 Uiso 1 1 d R
H14 H 1.4608 0.3177 0.6256 0.033 Uiso 1 1 d R
H15 H 1.1633 0.2478 0.6086 0.033 Uiso 1 1 d R
N1 N 0.9663(5) 0.13522(14) 0.3524(3) 0.0220(7) Uani 1 1 d .
O1 O 0.9086(4) 0.16745(10) 0.5295(2) 0.0192(5) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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
C2 C1 C6 120.4(4) . .
C2 C1 H1 121.6 . .
C6 C1 H1 117.7 . .
C1 C2 C3 120.3(4) . .
C1 C2 H2 121.8 . .
C3 C2 H2 117.9 . .
C2 C3 C4 120.0(3) . .
C2 C3 H3 120.1 . .
C4 C3 H3 119.7 . .
C3 C4 C5 120.2(4) . .
C3 C4 H4 120.6 . .
C5 C4 H4 118.9 . .
C4 C5 C6 120.0(4) . .
C4 C5 H5 129.2 . .
C6 C5 H5 110.7 . .
C1 C6 C5 118.9(3) . .
C1 C6 C7 120.6(3) . .
C5 C6 C7 120.5(3) . .
C8 C7 O1 107.2(3) . .
C8 C7 C6 136.1(3) . .
O1 C7 C6 116.6(3) . .
C7 C8 N1 109.7(3) . .
C7 C8 H8 130.4 . .
N1 C8 H8 119.8 . .
N1 C9 O1 112.8(3) . .
N1 C9 C10 130.0(3) . .
O1 C9 C10 117.2(3) . .
C15 C10 C11 119.4(3) . .
C15 C10 C9 120.1(3) . .
C11 C10 C9 120.5(3) . .
C12 C11 C10 119.4(3) . .
C12 C11 H11 117.1 . .
C10 C11 H11 123.5 . .
C13 C12 C11 120.8(3) . .
C13 C12 H12 131.1 . .
C11 C12 H12 108.1 . .
C12 C13 C14 120.0(3) . .
C12 C13 H13 112.8 . .
C14 C13 H13 126.3 . .
C15 C14 C13 120.0(3) . .
C15 C14 H14 119.0 . .
C13 C14 H14 120.7 . .
C14 C15 C10 120.4(3) . .
C14 C15 H15 119.4 . .
C10 C15 H15 120.1 . .
C17 C16 C18 118.0(3) . 3_657
C17 C16 Br1 122.4(3) . .
C18 C16 Br1 119.6(3) 3_657 .
F1 C17 C18 118.5(3) . .
F1 C17 C16 120.2(3) . .
C18 C17 C16 121.3(3) . .
F2 C18 C17 119.4(3) . .
F2 C18 C16 119.9(3) . 3_657
C17 C18 C16 120.7(3) . 3_657
C9 N1 C8 105.0(3) . .
C9 O1 C7 105.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C16 1.875(3) .
C1 C2 1.382(5) .
C1 C6 1.394(5) .
C1 H1 0.9700 .
C2 C3 1.384(6) .
C2 H2 0.9723 .
C3 C4 1.384(6) .
C3 H3 0.9699 .
C4 C5 1.386(5) .
C4 H4 0.9691 .
C5 C6 1.405(5) .
C5 H5 0.9711 .
C6 C7 1.450(5) .
C7 C8 1.348(5) .
C7 O1 1.382(4) .
C8 N1 1.392(4) .
C8 H8 0.9725 .
C9 N1 1.308(5) .
C9 O1 1.365(4) .
C9 C10 1.454(5) .
C10 C15 1.396(5) .
C10 C11 1.400(5) .
C11 C12 1.388(5) .
C11 H11 0.9763 .
C12 C13 1.381(5) .
C12 H12 0.9750 .
C13 C14 1.385(5) .
C13 H13 0.9701 .
C14 C15 1.382(5) .
C14 H14 0.9711 .
C15 H15 0.9676 .
C16 C17 1.378(5) .
C16 C18 1.385(5) 3_657
C17 F1 1.343(4) .
C17 C18 1.377(5) .
C18 F2 1.340(4) .
C18 C16 1.385(5) 3_657
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
C6 C1 C2 C3 0.4(6) . .
C1 C2 C3 C4 0.6(6) . .
C2 C3 C4 C5 -1.2(6) . .
C3 C4 C5 C6 0.7(6) . .
C2 C1 C6 C5 -0.9(5) . .
C2 C1 C6 C7 178.0(3) . .
C4 C5 C6 C1 0.4(5) . .
C4 C5 C6 C7 -178.6(3) . .
C1 C6 C7 C8 175.8(4) . .
C5 C6 C7 C8 -5.2(6) . .
C1 C6 C7 O1 -5.6(5) . .
C5 C6 C7 O1 173.4(3) . .
O1 C7 C8 N1 0.1(4) . .
C6 C7 C8 N1 178.9(4) . .
N1 C9 C10 C15 178.4(3) . .
O1 C9 C10 C15 -2.4(5) . .
N1 C9 C10 C11 -3.7(6) . .
O1 C9 C10 C11 175.5(3) . .
C15 C10 C11 C12 0.3(5) . .
C9 C10 C11 C12 -177.7(3) . .
C10 C11 C12 C13 0.7(5) . .
C11 C12 C13 C14 -0.9(6) . .
C12 C13 C14 C15 0.2(6) . .
C13 C14 C15 C10 0.7(5) . .
C11 C10 C15 C14 -1.0(5) . .
C9 C10 C15 C14 177.0(3) . .
C18 C16 C17 F1 -179.4(3) 3_657 .
Br1 C16 C17 F1 1.4(4) . .
C18 C16 C17 C18 -0.5(5) 3_657 .
Br1 C16 C17 C18 -179.7(3) . .
F1 C17 C18 F2 0.3(5) . .
C16 C17 C18 F2 -178.6(3) . .
F1 C17 C18 C16 179.5(3) . 3_657
C16 C17 C18 C16 0.5(6) . 3_657
O1 C9 N1 C8 -0.3(4) . .
C10 C9 N1 C8 179.0(3) . .
C7 C8 N1 C9 0.1(4) . .
N1 C9 O1 C7 0.4(4) . .
C10 C9 O1 C7 -179.0(3) . .
C8 C7 O1 C9 -0.3(4) . .
C6 C7 O1 C9 -179.3(3) . .
