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#$Date: 2021-07-24 02:44:22 +0300 (Sat, 24 Jul 2021) $
#$Revision: 267725 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564246.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_1564246
loop_
_publ_author_name
'Xiao, Fuming'
'Liu, Xiaoqing'
'Lin, Kangkang'
'Zhou, Yunbing'
'Gao, Wenxia'
'Lei, Yunxiang'
'Liu, Miaochang'
'Huang, Xiaobo'
'Wu, Huayue'
_publ_section_title
;
 Pyranone--Arylbenzene Molecules Controlled by the Competition of Local
 Excited State and Twisted Intramolecular Charge-Transfer State:
 Dual-State Emission, Polymorphism, and Mechanofluorochromism
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.1c04340
_journal_year                    2021
_chemical_formula_sum            'C31 H24 O2'
_chemical_formula_weight         428.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 125.856(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8917(11)
_cell_length_b                   16.2765(14)
_cell_length_c                   11.8457(16)
_cell_measurement_reflns_used    2840
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.672
_cell_measurement_theta_min      7.106
_cell_volume                     2327.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5679
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         3.553
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0559P)²+0.9793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1264
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1837
_reflns_number_total             2275
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c04340_si_002.cif
_cod_data_source_block           dd19211
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1564246
_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   0.985
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0000 0.60614(10) 0.2500 0.0744(6) Uani 1 2 d S T P . .
O2 O 0.0000 0.35911(9) 0.2500 0.0552(4) Uani 1 2 d S T P . .
C1 C 0.0000 0.53073(13) 0.2500 0.0471(5) Uani 1 2 d S T P . .
C2 C 0.08246(11) 0.48291(9) 0.37261(14) 0.0437(3) Uani 1 1 d . . . . .
C3 C 0.08095(12) 0.40045(9) 0.36580(15) 0.0484(4) Uani 1 1 d . . . . .
C4 C 0.16394(14) 0.34197(11) 0.47326(18) 0.0673(5) Uani 1 1 d . . . . .
H4A H 0.1290 0.3069 0.5021 0.101 Uiso 1 1 calc R U . . .
H4B H 0.2228 0.3721 0.5521 0.101 Uiso 1 1 calc R U . . .
H4C H 0.1936 0.3091 0.4349 0.101 Uiso 1 1 calc R U . . .
C5 C 0.16819(12) 0.52676(9) 0.50302(14) 0.0445(4) Uani 1 1 d . . . . .
C6 C 0.17562(13) 0.51590(10) 0.62434(15) 0.0515(4) Uani 1 1 d . . . . .
H6 H 0.1258 0.4811 0.6237 0.062 Uiso 1 1 calc R U . . .
C7 C 0.25565(13) 0.55582(10) 0.74614(16) 0.0519(4) Uani 1 1 d . . . . .
H7 H 0.2587 0.5473 0.8260 0.062 Uiso 1 1 calc R U . . .
C8 C 0.33156(12) 0.60836(9) 0.75151(15) 0.0468(4) Uani 1 1 d . . . . .
C9 C 0.32216(13) 0.62022(10) 0.62862(16) 0.0555(4) Uani 1 1 d . . . . .
H9 H 0.3713 0.6556 0.6287 0.067 Uiso 1 1 calc R U . . .
C10 C 0.24186(13) 0.58088(10) 0.50687(16) 0.0534(4) Uani 1 1 d . . . . .
H10 H 0.2370 0.5908 0.4261 0.064 Uiso 1 1 calc R U . . .
C11 C 0.42129(12) 0.64868(10) 0.88363(15) 0.0506(4) Uani 1 1 d . . . . .
C12 C 0.46911(15) 0.60951(12) 1.01089(17) 0.0667(5) Uani 1 1 d . . . . .
H12 H 0.4415 0.5590 1.0143 0.080 Uiso 1 1 calc R U . . .
C13 C 0.55737(18) 0.64469(14) 1.1328(2) 0.0824(6) Uani 1 1 d . . . . .
H13 H 0.5883 0.6178 1.2173 0.099 Uiso 1 1 calc R U . . .
C14 C 0.59937(17) 0.71893(14) 1.1296(2) 0.0819(6) Uani 1 1 d . . . . .
H14 H 0.6598 0.7418 1.2113 0.098 Uiso 1 1 calc R U . . .
C15 C 0.55169(16) 0.75924(12) 1.0050(2) 0.0719(5) Uani 1 1 d . . . . .
H15 H 0.5792 0.8100 1.0027 0.086 Uiso 1 1 calc R U . . .
C16 C 0.46326(14) 0.72484(10) 0.88323(17) 0.0579(4) Uani 1 1 d . . . . .
H16 H 0.4313 0.7530 0.7997 0.069 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
_geom_angle_publ_flag
C3 O2 C3 120.71(16) 2 . ?
O1 C1 C2 122.20(9) . 2 ?
O1 C1 C2 122.19(9) . . ?
C2 C1 C2 115.61(17) 2 . ?
C3 C2 C1 119.84(13) . . ?
C3 C2 C5 121.01(13) . . ?
C1 C2 C5 119.14(13) . . ?
C2 C3 O2 121.89(13) . . ?
C2 C3 C4 127.70(14) . . ?
O2 C3 C4 110.36(13) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 117.75(13) . . ?
C6 C5 C2 120.92(13) . . ?
C10 C5 C2 121.32(13) . . ?
C7 C6 C5 121.24(14) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.22(14) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 117.19(14) . . ?
C7 C8 C11 121.67(13) . . ?
C9 C8 C11 121.12(13) . . ?
C10 C9 C8 121.60(14) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C5 120.95(14) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C16 117.88(15) . . ?
C12 C11 C8 120.84(15) . . ?
C16 C11 C8 121.22(14) . . ?
C13 C12 C11 120.81(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 120.33(19) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.60(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.38(18) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.96(17) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
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
O1 C1 1.227(3) . ?
O2 C3 1.3602(16) 2 ?
O2 C3 1.3603(16) . ?
C1 C2 1.4608(17) 2 ?
C1 C2 1.4608(17) . ?
C2 C3 1.344(2) . ?
C2 C5 1.4883(19) . ?
C3 C4 1.487(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.386(2) . ?
C5 C10 1.387(2) . ?
C6 C7 1.382(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(2) . ?
C8 C11 1.489(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.389(2) . ?
C11 C16 1.390(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9300 . ?
C16 H16 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.86(10) . . . . ?
C2 C1 C2 C3 2.13(10) 2 . . . ?
O1 C1 C2 C5 1.24(14) . . . . ?
C2 C1 C2 C5 -178.77(14) 2 . . . ?
C1 C2 C3 O2 -4.4(2) . . . . ?
C5 C2 C3 O2 176.54(11) . . . . ?
C1 C2 C3 C4 172.95(14) . . . . ?
C5 C2 C3 C4 -6.1(2) . . . . ?
C3 O2 C3 C2 2.28(11) 2 . . . ?
C3 O2 C3 C4 -175.46(15) 2 . . . ?
C3 C2 C5 C6 -62.3(2) . . . . ?
C1 C2 C5 C6 118.59(15) . . . . ?
C3 C2 C5 C10 118.88(17) . . . . ?
C1 C2 C5 C10 -60.21(18) . . . . ?
C10 C5 C6 C7 -1.8(2) . . . . ?
C2 C5 C6 C7 179.39(14) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C6 C7 C8 C11 -177.15(14) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C11 C8 C9 C10 177.63(15) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
C6 C5 C10 C9 2.2(2) . . . . ?
C2 C5 C10 C9 -178.94(14) . . . . ?
C7 C8 C11 C12 32.5(2) . . . . ?
C9 C8 C11 C12 -145.74(17) . . . . ?
C7 C8 C11 C16 -150.37(16) . . . . ?
C9 C8 C11 C16 31.3(2) . . . . ?
C16 C11 C12 C13 -1.4(3) . . . . ?
C8 C11 C12 C13 175.79(16) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 1.8(2) . . . . ?
C8 C11 C16 C15 -175.33(15) . . . . ?
