#------------------------------------------------------------------------------
#$Date: 2021-12-18 00:57:58 +0200 (Sat, 18 Dec 2021) $
#$Revision: 271508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/94/7129417.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_7129417
loop_
_publ_author_name
'Zhang, Xinyu'
'Wang, Dan'
'Lei, yunxiang'
'Liu, Miaochang'
'Cai, Zhengxu'
'Wu, Huayue'
'Shen, Guomin'
'Huang, Xiaobo'
'Dong, Yuping'
_publ_section_title
;
 Selenium atoms induce organic doped system to produce pure
 phosphorescence emission
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06380D
_journal_year                    2022
_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           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-11-11 deposited with the CCDC.	2021-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.055(4)
_cell_length_b                   10.096(6)
_cell_length_c                   11.687(5)
_cell_measurement_reflns_used    3887
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.213
_cell_measurement_theta_min      4.332
_cell_volume                     950.4(8)
_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 0.986
_diffrn_measured_fraction_theta_max 0.987
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         3.071
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.088
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
; 
 Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_coef       0.15(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0342
_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)+(0.0401P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1654
_reflns_number_total             1845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06380d2.cif
_cod_data_source_block           mo_dd21079_0m
_cod_original_cell_volume        950.5(9)
_cod_database_code               7129417
_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   0.991
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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 0.4064(2) 0.75008(17) 0.33934(12) 0.0848(6) Uani 1 1 d . . . . .
N1 N 0.4791(2) 0.74091(15) 0.62459(13) 0.0577(5) Uani 1 1 d . . . . .
C1 C 0.4991(3) 0.8216(2) 0.71409(17) 0.0635(6) Uani 1 1 d . . . . .
H1 H 0.5637 0.7918 0.7748 0.076 Uiso 1 1 calc R U . . .
C2 C 0.4306(3) 0.9453(2) 0.72212(19) 0.0667(6) Uani 1 1 d . . . . .
H2 H 0.4485 0.9977 0.7864 0.080 Uiso 1 1 calc R U . . .
C3 C 0.3352(3) 0.9899(2) 0.6335(2) 0.0803(7) Uani 1 1 d . . . . .
H3 H 0.2837 1.0722 0.6374 0.096 Uiso 1 1 calc R U . . .
C4 C 0.3167(3) 0.9112(2) 0.5383(2) 0.0725(6) Uani 1 1 d . . . . .
H4 H 0.2556 0.9407 0.4757 0.087 Uiso 1 1 calc R U . . .
C5 C 0.3897(2) 0.78821(18) 0.53713(16) 0.0527(5) Uani 1 1 d . . . . .
C6 C 0.3802(2) 0.7017(2) 0.43279(16) 0.0564(5) Uani 1 1 d . . . . .
C7 C 0.3372(2) 0.55900(19) 0.44617(15) 0.0499(5) Uani 1 1 d . . . . .
C8 C 0.3775(3) 0.4701(2) 0.35907(16) 0.0628(6) Uani 1 1 d . . . . .
H8 H 0.4387 0.4989 0.2963 0.075 Uiso 1 1 calc R U . . .
C9 C 0.3271(3) 0.3398(2) 0.36547(19) 0.0699(6) Uani 1 1 d . . . . .
H9 H 0.3550 0.2808 0.3075 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2352(3) 0.2972(2) 0.45781(19) 0.0726(6) Uani 1 1 d . . . . .
H10 H 0.1995 0.2097 0.4613 0.087 Uiso 1 1 calc R U . . .
C11 C 0.1962(3) 0.3832(2) 0.54475(17) 0.0653(6) Uani 1 1 d . . . . .
H11 H 0.1351 0.3536 0.6072 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2477(2) 0.51369(19) 0.53941(15) 0.0549(5) Uani 1 1 d . . . . .
H12 H 0.2220 0.5714 0.5988 0.066 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
C1 N1 C5 116.47(17) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 123.04(19) . . ?
N1 C5 C6 116.13(17) . . ?
C4 C5 C6 120.75(19) . . ?
O1 C6 C7 121.55(19) . . ?
O1 C6 C5 119.19(18) . . ?
C7 C6 C5 119.26(15) . . ?
C12 C7 C8 118.86(18) . . ?
C12 C7 C6 121.54(16) . . ?
C8 C7 C6 119.44(17) . . ?
C9 C8 C7 120.37(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.44(17) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
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 C6 1.215(2) . ?
N1 C1 1.336(2) . ?
N1 C5 1.338(2) . ?
C1 C2 1.369(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(3) . ?
C6 C7 1.490(3) . ?
C7 C12 1.385(2) . ?
C7 C8 1.395(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 H12 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
C5 N1 C1 C2 2.0(3) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -2.3(3) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C1 N1 C5 C4 -2.0(3) . . . . ?
C1 N1 C5 C6 174.85(17) . . . . ?
C3 C4 C5 N1 -0.1(3) . . . . ?
C3 C4 C5 C6 -176.8(2) . . . . ?
N1 C5 C6 O1 -131.7(2) . . . . ?
C4 C5 C6 O1 45.2(3) . . . . ?
N1 C5 C6 C7 48.8(2) . . . . ?
C4 C5 C6 C7 -134.3(2) . . . . ?
O1 C6 C7 C12 -154.8(2) . . . . ?
C5 C6 C7 C12 24.6(3) . . . . ?
O1 C6 C7 C8 20.5(3) . . . . ?
C5 C6 C7 C8 -160.06(17) . . . . ?
C12 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C8 C9 -174.72(18) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C6 C7 C12 C11 174.02(18) . . . . ?
