#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/04/1540468.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_1540468
loop_
_publ_author_name
'Xue, peng chong'
'Wang, Panpan'
'Chen, Peng'
'Yao, Boqi'
'Gong, Peng'
'sun, Jiabao'
'zhang, Zhenqi'
'Lu, Ran'
_publ_section_title
;
 Bright persistent luminescence from pure organic molecules through
 moderate intermolecular heavy atom effect
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C5SC03739E
_journal_year                    2015
_chemical_formula_sum            'C20 H16 Br N O'
_chemical_formula_weight         366.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1jpyx2
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-31 deposited with the CCDC.
2015-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6160(8)
_cell_length_b                   13.1439(19)
_cell_length_c                   22.937(2)
_cell_measurement_reflns_used    562
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.28
_cell_measurement_theta_min      4.07
_cell_volume                     1693.1(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2926
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    2.432
_exptl_absorpt_correction_T_max  0.649
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rodlike
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.0072(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0581P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                1525
_reflns_number_total             2246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03739e4.cif
_cod_data_source_block           e
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1540468
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.1826(3) 0.49989(10) -0.04517(4) 0.1485(7) Uani 1 1 d .
O1 O 0.4110(9) 0.2162(4) 0.1514(2) 0.0732(14) Uani 1 1 d .
N1 N 0.4437(10) 0.1068(5) 0.2584(3) 0.0667(17) Uani 1 1 d .
C1 C -0.0593(17) -0.0551(8) 0.2847(6) 0.102(3) Uani 1 1 d .
H1 H -0.1624 -0.0679 0.3156 0.122 Uiso 1 1 calc R
C2 C -0.082(2) -0.1072(8) 0.2339(7) 0.110(4) Uani 1 1 d .
H2 H -0.1988 -0.1569 0.2305 0.132 Uiso 1 1 calc R
C3 C 0.065(2) -0.0880(8) 0.1879(6) 0.108(3) Uani 1 1 d .
H3 H 0.0394 -0.1225 0.1531 0.130 Uiso 1 1 calc R
C4 C 0.2491(18) -0.0189(7) 0.1912(4) 0.090(3) Uani 1 1 d .
H4 H 0.3506 -0.0081 0.1597 0.108 Uiso 1 1 calc R
C5 C 0.2777(13) 0.0339(5) 0.2432(3) 0.0643(19) Uani 1 1 d .
C6 C 0.1235(15) 0.0194(6) 0.2904(3) 0.072(2) Uani 1 1 d .
C7 C 0.3965(15) 0.1380(6) 0.3140(4) 0.071(2) Uani 1 1 d .
C8 C 0.5200(18) 0.2105(7) 0.3471(4) 0.093(3) Uani 1 1 d .
H8 H 0.6533 0.2441 0.3326 0.111 Uiso 1 1 calc R
C9 C 0.432(3) 0.2293(9) 0.4026(6) 0.125(4) Uani 1 1 d .
H9 H 0.5116 0.2752 0.4266 0.150 Uiso 1 1 calc R
C10 C 0.232(3) 0.1822(10) 0.4228(5) 0.128(5) Uani 1 1 d .
H10 H 0.1773 0.1984 0.4599 0.153 Uiso 1 1 calc R
C11 C 0.111(2) 0.1132(9) 0.3912(4) 0.109(3) Uani 1 1 d .
H11 H -0.0261 0.0829 0.4057 0.130 Uiso 1 1 calc R
C12 C 0.1982(15) 0.0883(6) 0.3355(3) 0.070(2) Uani 1 1 d .
C13 C 0.6455(15) 0.1371(6) 0.2235(4) 0.082(2) Uani 1 1 d .
H13A H 0.6840 0.0826 0.1967 0.098 Uiso 1 1 calc R
H13B H 0.7817 0.1469 0.2489 0.098 Uiso 1 1 calc R
C14 C 0.6040(13) 0.2343(6) 0.1889(3) 0.075(2) Uani 1 1 d .
H14A H 0.5682 0.2903 0.2150 0.090 Uiso 1 1 calc R
H14B H 0.7451 0.2516 0.1666 0.090 Uiso 1 1 calc R
C15 C 0.1684(14) 0.2672(6) 0.0755(3) 0.068(2) Uani 1 1 d .
H15 H 0.0722 0.2117 0.0843 0.082 Uiso 1 1 calc R
C16 C 0.1136(15) 0.3302(7) 0.0301(3) 0.083(2) Uani 1 1 d .
H16 H -0.0198 0.3168 0.0073 0.099 Uiso 1 1 calc R
C17 C 0.2526(17) 0.4128(7) 0.0177(3) 0.081(3) Uani 1 1 d .
C18 C 0.4510(17) 0.4321(6) 0.0507(4) 0.083(2) Uani 1 1 d .
H18 H 0.5474 0.4874 0.0418 0.099 Uiso 1 1 calc R
C19 C 0.5089(14) 0.3698(6) 0.0972(3) 0.070(2) Uani 1 1 d .
H19 H 0.6408 0.3839 0.1203 0.084 Uiso 1 1 calc R
C20 C 0.3699(14) 0.2877(6) 0.1084(3) 0.0597(18) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 '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
C20 O1 C14 116.8(6)
C7 N1 C5 108.2(6)
C7 N1 C13 125.9(7)
C5 N1 C13 125.6(7)
C2 C1 C6 119.4(10)
C1 C2 C3 121.0(11)
C2 C3 C4 122.3(11)
C3 C4 C5 117.5(10)
N1 C5 C4 129.8(8)
N1 C5 C6 108.5(7)
C4 C5 C6 121.6(8)
C5 C6 C1 118.0(8)
C5 C6 C12 106.9(8)
C1 C6 C12 135.1(9)
N1 C7 C12 110.3(7)
N1 C7 C8 127.9(9)
C12 C7 C8 121.8(9)
C9 C8 C7 116.3(10)
C10 C9 C8 121.6(12)
C11 C10 C9 122.6(12)
C10 C11 C12 118.1(11)
C7 C12 C11 119.6(10)
C7 C12 C6 106.0(7)
C11 C12 C6 134.4(10)
N1 C13 C14 113.6(7)
O1 C14 C13 107.2(6)
C16 C15 C20 118.7(7)
C15 C16 C17 120.8(8)
C16 C17 C18 119.7(8)
C16 C17 Br1 121.5(7)
C18 C17 Br1 118.8(7)
C17 C18 C19 120.5(8)
C20 C19 C18 118.8(7)
C19 C20 O1 125.4(7)
C19 C20 C15 121.5(7)
O1 C20 C15 113.1(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C17 1.882(8)
O1 C20 1.383(8)
O1 C14 1.404(8)
N1 C7 1.365(10)
N1 C5 1.381(9)
N1 C13 1.443(9)
C1 C2 1.359(14)
C1 C6 1.424(12)
C2 C3 1.362(14)
C3 C4 1.379(13)
C4 C5 1.390(11)
C5 C6 1.399(10)
C6 C12 1.437(10)
C7 C12 1.383(10)
C7 C8 1.402(11)
C8 C9 1.389(15)
C9 C10 1.364(16)
C10 C11 1.346(15)
C11 C12 1.406(12)
C13 C14 1.523(10)
C15 C16 1.367(10)
C15 C20 1.386(10)
C16 C17 1.367(11)
C17 C18 1.370(11)
C18 C19 1.383(10)
C19 C20 1.355(10)
