#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:27:08 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258037 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239747.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_7239747
loop_
_publ_author_name
'Wang, Renjie'
'Liang, Yunfei'
'Liu, Gang'
'Pu, Shouzhi'
_publ_section_title
;
 Aggregation-induced emission compounds based on
 9,10-diheteroarylanthracene and their applications in cell imaging
;
_journal_issue                   4
_journal_name_full               'RSC Advances'
_journal_page_first              2170
_journal_page_last               2179
_journal_paper_doi               10.1039/C9RA09290K
_journal_volume                  10
_journal_year                    2020
_chemical_formula_sum            'C22 H14 O2'
_chemical_formula_weight         310.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-10-22 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.284(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1632(14)
_cell_length_b                   8.9491(14)
_cell_length_c                   10.3448(16)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.39
_cell_volume                     790.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_min         3.106
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6990
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.066(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0608P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1330
_reflns_number_total             1748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra09290k2.cif
_cod_data_source_block           1_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7239744--7239747.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7239747
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.34107(14) 0.25440(12) 0.70407(11) 0.0659(4) Uani 1 1 d . .
C4 C 0.33487(15) 0.50376(13) 0.46312(12) 0.0399(3) Uani 1 1 d . .
C7 C 0.42091(15) 0.37923(13) 0.53432(12) 0.0407(3) Uani 1 1 d . .
C3 C 0.41525(15) 0.62652(13) 0.42919(12) 0.0401(3) Uani 1 1 d . .
C8 C 0.33935(16) 0.25387(15) 0.57251(14) 0.0461(4) Uani 1 1 d . .
C5 C 0.16824(16) 0.51220(16) 0.42184(15) 0.0501(4) Uani 1 1 d . .
H5 H 0.114050 0.432553 0.440944 0.060 Uiso 1 1 calc R U
C2 C 0.32492(18) 0.75309(15) 0.35988(15) 0.0504(4) Uani 1 1 d . .
H2 H 0.375311 0.834355 0.338526 0.060 Uiso 1 1 calc R U
C1 C 0.16722(18) 0.75663(17) 0.32482(17) 0.0567(4) Uani 1 1 d . .
H1 H 0.110962 0.840228 0.280356 0.068 Uiso 1 1 calc R U
C6 C 0.08779(18) 0.63416(17) 0.35537(17) 0.0572(4) Uani 1 1 d . .
H6 H -0.020523 0.637233 0.329688 0.069 Uiso 1 1 calc R U
C11 C 0.2602(2) 0.1287(2) 0.7156(2) 0.0730(6) Uani 1 1 d . .
H11 H 0.243156 0.100933 0.795650 0.088 Uiso 1 1 calc R U
C10 C 0.2110(2) 0.0542(2) 0.6009(2) 0.0808(6) Uani 1 1 d . .
H10 H 0.154008 -0.034323 0.583575 0.097 Uiso 1 1 calc R U
C9 C 0.2611(3) 0.1344(2) 0.5069(2) 0.0923(7) Uani 1 1 d . .
H9 H 0.242697 0.108113 0.415317 0.111 Uiso 1 1 calc R U
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'
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
C8 O1 C11 105.91(13) . .
C7 C4 C5 122.14(12) . .
C7 C4 C3 119.60(12) . .
C5 C4 C3 118.26(12) . .
C4 C7 C3 120.55(11) . 3_666
C4 C7 C8 119.91(11) . .
C3 C7 C8 119.54(11) 3_666 .
C7 C3 C2 121.91(12) 3_666 .
C7 C3 C4 119.84(11) 3_666 .
C2 C3 C4 118.24(12) . .
C9 C8 O1 108.87(13) . .
C9 C8 C7 134.85(14) . .
O1 C8 C7 116.28(11) . .
C6 C5 C4 121.25(13) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C1 C2 C3 121.21(13) . .
C1 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C2 C1 C6 120.48(13) . .
C2 C1 H1 119.8 . .
C6 C1 H1 119.8 . .
C5 C6 C1 120.54(14) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C10 C11 O1 111.16(15) . .
C10 C11 H11 124.4 . .
O1 C11 H11 124.4 . .
C11 C10 C9 106.18(16) . .
C11 C10 H10 126.9 . .
C9 C10 H10 126.9 . .
C8 C9 C10 107.87(18) . .
C8 C9 H9 126.1 . .
C10 C9 H9 126.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.3552(17) .
O1 C11 1.376(2) .
C4 C7 1.4087(18) .
C4 C5 1.4304(19) .
C4 C3 1.4353(17) .
C7 C3 1.4098(18) 3_666
C7 C8 1.4791(17) .
C3 C2 1.4323(18) .
C8 C9 1.329(2) .
C5 C6 1.356(2) .
C5 H5 0.9300 .
C2 C1 1.357(2) .
C2 H2 0.9300 .
C1 C6 1.413(2) .
C1 H1 0.9300 .
C6 H6 0.9300 .
C11 C10 1.292(3) .
C11 H11 0.9300 .
C10 C9 1.412(3) .
C10 H10 0.9300 .
C9 H9 0.9300 .
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
C5 C4 C7 C3 178.67(12) . 3_666
C3 C4 C7 C3 -0.82(19) . 3_666
C5 C4 C7 C8 -1.93(18) . .
C3 C4 C7 C8 178.58(11) . .
C7 C4 C3 C7 0.81(19) . 3_666
C5 C4 C3 C7 -178.70(11) . 3_666
C7 C4 C3 C2 -178.45(11) . .
C5 C4 C3 C2 2.04(17) . .
C11 O1 C8 C9 0.17(19) . .
C11 O1 C8 C7 -179.63(12) . .
C4 C7 C8 C9 82.7(2) . .
C3 C7 C8 C9 -97.8(2) 3_666 .
C4 C7 C8 O1 -97.53(15) . .
C3 C7 C8 O1 81.88(15) 3_666 .
C7 C4 C5 C6 178.90(13) . .
C3 C4 C5 C6 -1.6(2) . .
C7 C3 C2 C1 179.66(13) 3_666 .
C4 C3 C2 C1 -1.1(2) . .
C3 C2 C1 C6 -0.4(2) . .
C4 C5 C6 C1 0.1(2) . .
C2 C1 C6 C5 0.9(2) . .
C8 O1 C11 C10 -0.01(19) . .
O1 C11 C10 C9 -0.1(2) . .
O1 C8 C9 C10 -0.3(2) . .
C7 C8 C9 C10 179.48(16) . .
C11 C10 C9 C8 0.3(3) . .
