#------------------------------------------------------------------------------
#$Date: 2021-07-31 02:59:06 +0300 (Sat, 31 Jul 2021) $
#$Revision: 267832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/05/8000525.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_8000525
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_formula_sum            'C19 H23 N3 O'
_chemical_formula_weight         309.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.778(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2755(5)
_cell_length_b                   13.7706(9)
_cell_length_c                   17.4597(13)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.498
_cell_measurement_theta_min      5.596
_cell_volume                     1718.4(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12309
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.375
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.020(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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0484P)²+0.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2091
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz1c01893_si_006.cif
_cod_data_source_block           mo_dd21116_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8000525
_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   0.995
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.3101(2) 0.29431(10) 0.24132(9) 0.0596(5) Uani 1 1 d . . . . .
N1 N 0.6881(2) 0.45475(12) 0.41523(10) 0.0534(5) Uani 1 1 d . . . . .
N2 N -0.1290(3) 0.31646(18) 0.13818(15) 0.0901(8) Uani 1 1 d . . . . .
N3 N 0.6242(2) 0.29885(11) 0.37282(11) 0.0516(5) Uani 1 1 d . . . . .
C1 C 0.6340(3) 0.54678(15) 0.42887(13) 0.0549(6) Uani 1 1 d . . . . .
C2 C 0.4549(3) 0.57765(15) 0.40656(13) 0.0578(6) Uani 1 1 d . . . . .
H2 H 0.4186 0.6375 0.4234 0.069 Uiso 1 1 calc R U . . .
C3 C 0.3243(3) 0.51884(14) 0.35792(13) 0.0510(6) Uani 1 1 d . . . . .
C4 C 0.1414(3) 0.55255(16) 0.32742(14) 0.0593(6) Uani 1 1 d . . . . .
H4 H 0.1035 0.6119 0.3445 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0196(3) 0.50151(16) 0.27420(14) 0.0578(6) Uani 1 1 d . . . . .
C6 C 0.0837(3) 0.41298(15) 0.24664(13) 0.0530(6) Uani 1 1 d . . . . .
C7 C 0.2610(3) 0.37767(14) 0.27546(13) 0.0494(5) Uani 1 1 d . . . . .
C8 C 0.3826(3) 0.42579(13) 0.33617(12) 0.0453(5) Uani 1 1 d . . . . .
C9 C 0.5655(3) 0.39348(14) 0.37573(12) 0.0467(5) Uani 1 1 d . . . . .
C10 C 0.7872(4) 0.61048(17) 0.47228(15) 0.0738(8) Uani 1 1 d . . . . .
H10A H 0.8487 0.5776 0.5185 0.111 Uiso 1 1 calc R U . . .
H10B H 0.7343 0.6702 0.4864 0.111 Uiso 1 1 calc R U . . .
H10C H 0.8764 0.6242 0.4395 0.111 Uiso 1 1 calc R U . . .
C11 C -0.1753(3) 0.53788(19) 0.24230(17) 0.0768(8) Uani 1 1 d . . . . .
H11A H -0.1978 0.5354 0.1864 0.115 Uiso 1 1 calc R U . . .
H11B H -0.1872 0.6037 0.2589 0.115 Uiso 1 1 calc R U . . .
H11C H -0.2649 0.4978 0.2613 0.115 Uiso 1 1 calc R U . . .
C12 C -0.0333(3) 0.35894(18) 0.18589(16) 0.0632(7) Uani 1 1 d . . . . .
C13 C 0.4429(5) 0.3063(2) 0.19188(19) 0.0926(9) Uani 1 1 d . . . . .
H13A H 0.3852 0.3393 0.1451 0.139 Uiso 1 1 calc R U . . .
H13B H 0.4867 0.2438 0.1788 0.139 Uiso 1 1 calc R U . . .
H13C H 0.5466 0.3440 0.2183 0.139 Uiso 1 1 calc R U . . .
C14 C 0.4967(3) 0.21887(15) 0.38164(15) 0.0622(7) Uani 1 1 d . . . . .
H14A H 0.4809 0.1791 0.3350 0.075 Uiso 1 1 calc R U . . .
H14B H 0.3754 0.2462 0.3847 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5567(4) 0.15427(18) 0.45124(17) 0.0794(8) Uani 1 1 d . . . . .
H15A H 0.4460 0.1263 0.4659 0.095 Uiso 1 1 calc R U . . .
H15B H 0.6181 0.1939 0.4945 0.095 Uiso 1 1 calc R U . . .
C16 C 0.6882(4) 0.07232(18) 0.4387(2) 0.0944(10) Uani 1 1 d . . . . .
H16A H 0.6978 0.0275 0.4822 0.113 Uiso 1 1 calc R U . . .
H16B H 0.6325 0.0373 0.3919 0.113 Uiso 1 1 calc R U . . .
C17 C 0.8825(4) 0.10289(19) 0.43109(19) 0.0883(9) Uani 1 1 d . . . . .
H17A H 0.9475 0.0469 0.4155 0.106 Uiso 1 1 calc R U . . .
H17B H 0.9492 0.1233 0.4819 0.106 Uiso 1 1 calc R U . . .
C18 C 0.8910(4) 0.18409(18) 0.37348(17) 0.0771(8) Uani 1 1 d . . . . .
H18A H 1.0192 0.1906 0.3660 0.093 Uiso 1 1 calc R U . . .
H18B H 0.8154 0.1660 0.3237 0.093 Uiso 1 1 calc R U . . .
C19 C 0.8248(3) 0.28180(16) 0.39730(16) 0.0624(7) Uani 1 1 d . . . . .
H19A H 0.8566 0.2872 0.4536 0.075 Uiso 1 1 calc R U . . .
H19B H 0.8921 0.3324 0.3754 0.075 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
C7 O1 C13 115.39(18) . . ?
C9 N1 C1 119.72(18) . . ?
C9 N3 C19 116.21(16) . . ?
C9 N3 C14 120.06(17) . . ?
C19 N3 C14 117.74(16) . . ?
C2 C1 N1 122.35(19) . . ?
C2 C1 C10 122.9(2) . . ?
N1 C1 C10 114.8(2) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 C8 118.6(2) . . ?
C4 C3 C8 120.0(2) . . ?
C5 C4 C3 122.4(2) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 117.6(2) . . ?
C4 C5 C11 122.0(2) . . ?
C6 C5 C11 120.3(2) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 C12 118.0(2) . . ?
C5 C6 C12 120.5(2) . . ?
O1 C7 C6 115.96(19) . . ?
O1 C7 C8 122.77(18) . . ?
C6 C7 C8 121.3(2) . . ?
C7 C8 C3 116.51(18) . . ?
C7 C8 C9 127.15(18) . . ?
C3 C8 C9 116.23(18) . . ?
N1 C9 N3 116.06(18) . . ?
N1 C9 C8 121.43(18) . . ?
N3 C9 C8 122.48(17) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C6 178.8(3) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 115.80(19) . . ?
N3 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
N3 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 114.7(3) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C15 115.6(2) . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 114.9(2) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 114.8(2) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
N3 C19 C18 114.48(19) . . ?
N3 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
N3 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
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 1.371(2) . ?
O1 C13 1.421(3) . ?
N1 C9 1.324(2) . ?
N1 C1 1.361(3) . ?
N2 C12 1.142(3) . ?
N3 C9 1.375(2) . ?
N3 C19 1.462(3) . ?
N3 C14 1.466(3) . ?
C1 C2 1.356(3) . ?
C1 C10 1.507(3) . ?
C2 C3 1.406(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(3) . ?
C3 C8 1.423(3) . ?
C4 C5 1.355(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.421(3) . ?
C5 C11 1.509(3) . ?
C6 C7 1.382(3) . ?
C6 C12 1.437(3) . ?
C7 C8 1.413(3) . ?
C8 C9 1.450(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.503(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.505(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.513(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.513(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
C9 N1 C1 C2 3.2(3) . . . . ?
C9 N1 C1 C10 -178.2(2) . . . . ?
N1 C1 C2 C3 -9.5(3) . . . . ?
C10 C1 C2 C3 172.1(2) . . . . ?
C1 C2 C3 C4 -173.8(2) . . . . ?
C1 C2 C3 C8 2.8(3) . . . . ?
C2 C3 C4 C5 173.0(2) . . . . ?
C8 C3 C4 C5 -3.6(3) . . . . ?
C3 C4 C5 C6 -2.6(3) . . . . ?
C3 C4 C5 C11 179.7(2) . . . . ?
C4 C5 C6 C7 2.9(3) . . . . ?
C11 C5 C6 C7 -179.4(2) . . . . ?
C4 C5 C6 C12 -175.3(2) . . . . ?
C11 C5 C6 C12 2.5(3) . . . . ?
C13 O1 C7 C6 107.5(2) . . . . ?
C13 O1 C7 C8 -72.2(3) . . . . ?
C5 C6 C7 O1 -176.65(19) . . . . ?
C12 C6 C7 O1 1.5(3) . . . . ?
C5 C6 C7 C8 3.0(3) . . . . ?
C12 C6 C7 C8 -178.8(2) . . . . ?
O1 C7 C8 C3 170.82(19) . . . . ?
C6 C7 C8 C3 -8.8(3) . . . . ?
O1 C7 C8 C9 -5.3(3) . . . . ?
C6 C7 C8 C9 175.1(2) . . . . ?
C2 C3 C8 C7 -167.60(19) . . . . ?
C4 C3 C8 C7 9.1(3) . . . . ?
C2 C3 C8 C9 8.9(3) . . . . ?
C4 C3 C8 C9 -174.42(19) . . . . ?
C1 N1 C9 N3 -172.15(19) . . . . ?
C1 N1 C9 C8 9.6(3) . . . . ?
C19 N3 C9 N1 -13.8(3) . . . . ?
C14 N3 C9 N1 138.4(2) . . . . ?
C19 N3 C9 C8 164.4(2) . . . . ?
C14 N3 C9 C8 -43.4(3) . . . . ?
C7 C8 C9 N1 160.6(2) . . . . ?
C3 C8 C9 N1 -15.5(3) . . . . ?
C7 C8 C9 N3 -17.5(3) . . . . ?
C3 C8 C9 N3 166.4(2) . . . . ?
C9 N3 C14 C15 -117.4(2) . . . . ?
C19 N3 C14 C15 34.4(3) . . . . ?
N3 C14 C15 C16 -85.3(3) . . . . ?
C14 C15 C16 C17 69.9(3) . . . . ?
C15 C16 C17 C18 -49.6(4) . . . . ?
C16 C17 C18 C19 68.2(3) . . . . ?
C9 N3 C19 C18 -164.4(2) . . . . ?
C14 N3 C19 C18 42.7(3) . . . . ?
C17 C18 C19 N3 -88.4(3) . . . . ?
