#------------------------------------------------------------------------------
#$Date: 2021-07-31 02:58:45 +0300 (Sat, 31 Jul 2021) $
#$Revision: 267831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/05/8000524.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_8000524
loop_
_publ_author_name
'Liu, Xiaoqing'
'Pan, Yanyan'
'Lei, Yunxiang'
'Liu, Nannan'
'Dai, Wenbo'
'Liu, Miaochang'
'Cai, Zhengxu'
'Wu, Huayue'
'Huang, Xiaobo'
'Dong, Yuping'
_publ_section_title
;
 Influence of Guest/Host Morphology on Room Temperature Phosphorescence
 Properties of Pure Organic Doped Systems.
;
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              7357
_journal_page_last               7364
_journal_paper_doi               10.1021/acs.jpclett.1c01893
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_sum            'C12 H9 N O'
_chemical_formula_weight         183.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.556(3)
_cell_length_b                   7.6031(12)
_cell_length_c                   6.1035(9)
_cell_measurement_reflns_used    1731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.752
_cell_measurement_theta_min      5.713
_cell_volume                     953.9(2)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4035
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         2.856
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0660
_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)+(0.1132P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1737
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1294
_reflns_number_total             1748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz1c01893_si_010.cif
_cod_data_source_block           mo_dd21182_0m
_cod_database_code               8000524
_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   0.984
_shelx_estimated_absorpt_t_max   0.995
_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'
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 0.75126(12) 0.4181(5) 0.8071(6) 0.0797(13) Uani 1 1 d . . . . .
N1 N 0.92576(16) 0.5008(6) 0.4924(7) 0.0682(11) Uani 1 1 d . . . . .
C1 C 0.6756(2) 0.4899(5) 0.2888(6) 0.0490(10) Uani 1 1 d . . . . .
H1 H 0.7105 0.5391 0.2134 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6140(2) 0.4928(6) 0.1968(7) 0.0622(13) Uani 1 1 d . . . . .
H2 H 0.6072 0.5469 0.0620 0.075 Uiso 1 1 calc R U . . .
C3 C 0.5628(2) 0.4152(6) 0.3061(9) 0.0665(12) Uani 1 1 d . . . . .
H3 H 0.5217 0.4145 0.2426 0.080 Uiso 1 1 calc R U . . .
C4 C 0.57193(19) 0.3391(6) 0.5071(8) 0.0641(13) Uani 1 1 d . . . . .
H4 H 0.5370 0.2877 0.5800 0.077 Uiso 1 1 calc R U . . .
C5 C 0.6329(2) 0.3388(5) 0.6014(6) 0.0539(10) Uani 1 1 d . . . . .
H5 H 0.6389 0.2880 0.7386 0.065 Uiso 1 1 calc R U . . .
C6 C 0.68568(17) 0.4137(5) 0.4933(7) 0.0447(9) Uani 1 1 d . . . . .
C7 C 0.74945(16) 0.4189(5) 0.6079(7) 0.0473(10) Uani 1 1 d . . . . .
C8 C 0.81206(17) 0.4218(4) 0.4840(7) 0.0439(9) Uani 1 1 d . . . . .
C9 C 0.8663(2) 0.4970(6) 0.5829(7) 0.0578(11) Uani 1 1 d . . . . .
H9 H 0.8610 0.5479 0.7204 0.069 Uiso 1 1 calc R U . . .
C10 C 0.9320(2) 0.4228(6) 0.2980(9) 0.0654(13) Uani 1 1 d . . . . .
H10 H 0.9729 0.4214 0.2335 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8817(2) 0.3444(6) 0.1871(7) 0.0593(12) Uani 1 1 d . . . . .
H11 H 0.8887 0.2919 0.0516 0.071 Uiso 1 1 calc R U . . .
C12 C 0.82007(19) 0.3448(5) 0.2805(6) 0.0496(10) Uani 1 1 d . . . . .
H12 H 0.7850 0.2943 0.2078 0.059 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'
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
_geom_angle_publ_flag
C10 N1 C9 116.4(4) . . ?
C2 C1 C6 120.4(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 C7 118.4(4) . . ?
C1 C6 C7 122.8(3) . . ?
O1 C7 C6 119.8(3) . . ?
O1 C7 C8 118.7(3) . . ?
C6 C7 C8 121.5(3) . . ?
C12 C8 C9 117.9(3) . . ?
C12 C8 C7 123.4(3) . . ?
C9 C8 C7 118.5(4) . . ?
N1 C9 C8 124.1(4) . . ?
N1 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
N1 C10 C11 124.1(4) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C8 C12 C11 118.5(4) . . ?
C8 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
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 C7 1.217(5) . ?
N1 C10 1.332(7) . ?
N1 C9 1.342(5) . ?
C1 C2 1.386(6) . ?
C1 C6 1.391(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(5) . ?
C7 C8 1.493(5) . ?
C8 C12 1.383(6) . ?
C8 C9 1.391(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 N1 0.93 2.62 3.517(5) 163.0 2_764
C10 H10 N1 0.93 2.62 3.517(5) 163.0 2_764
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
C6 C1 C2 C3 -1.9(6) . . . . ?
C1 C2 C3 C4 1.7(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
C3 C4 C5 C6 -0.6(7) . . . . ?
C4 C5 C6 C1 0.4(6) . . . . ?
C4 C5 C6 C7 176.5(4) . . . . ?
C2 C1 C6 C5 0.9(6) . . . . ?
C2 C1 C6 C7 -175.1(4) . . . . ?
C5 C6 C7 O1 -25.6(5) . . . . ?
C1 C6 C7 O1 150.4(4) . . . . ?
C5 C6 C7 C8 153.2(4) . . . . ?
C1 C6 C7 C8 -30.8(5) . . . . ?
O1 C7 C8 C12 149.0(4) . . . . ?
C6 C7 C8 C12 -29.8(5) . . . . ?
O1 C7 C8 C9 -27.3(5) . . . . ?
C6 C7 C8 C9 153.9(4) . . . . ?
C10 N1 C9 C8 -1.7(7) . . . . ?
C12 C8 C9 N1 0.6(6) . . . . ?
C7 C8 C9 N1 177.0(4) . . . . ?
C9 N1 C10 C11 1.4(7) . . . . ?
N1 C10 C11 C12 -0.1(7) . . . . ?
C9 C8 C12 C11 0.8(6) . . . . ?
C7 C8 C12 C11 -175.4(3) . . . . ?
C10 C11 C12 C8 -1.1(6) . . . . ?
