#------------------------------------------------------------------------------
#$Date: 2019-04-10 01:25:41 +0300 (Wed, 10 Apr 2019) $
#$Revision: 214571 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/08/1550866.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_1550866
loop_
_publ_author_name
'Yuan, Jie'
'Chen, Run-Feng'
'Tang, Xingxing'
'Tao, Ye'
'Xu, Shen'
'Jin, Lu'
'Chen, Cailin'
'Zhou, Xinhui'
'Zheng, Chao'
'Huang, Wei'
_publ_section_title
;
 Direct Populating Triplet Excited States through Singlet-Triplet
 Transition for Visible-Light Excitable Organic Afterglow
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05198D
_journal_year                    2019
_chemical_formula_sum            'C18 H12 Br N'
_chemical_formula_weight         322.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-09-11 deposited with the CCDC.    2019-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.3042(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5054(6)
_cell_length_b                   20.5271(17)
_cell_length_c                   8.6640(7)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1
_cell_measurement_theta_min      1.7
_cell_volume                     1436.1(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12467
_diffrn_reflns_theta_full        28.51
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    2.850
_exptl_absorpt_correction_T_max  0.7636
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0426P)²+1.6642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                2640
_reflns_number_total             3610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc05198d3.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1436.12(19)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1550866
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.34511(6) 0.46475(3) 0.59665(5) 0.0862(2) Uani 1 1 d .
C1 C 0.0950(4) 0.64823(14) 1.1524(3) 0.0407(6) Uani 1 1 d .
C2 C 0.2625(4) 0.64760(16) 1.2408(4) 0.0495(7) Uani 1 1 d .
H2 H 0.3395 0.6273 1.2008 0.059 Uiso 1 1 calc R
C3 C 0.3099(5) 0.67814(18) 1.3892(4) 0.0609(9) Uani 1 1 d .
H3 H 0.4215 0.6785 1.4504 0.073 Uiso 1 1 calc R
C4 C 0.1970(5) 0.70828(18) 1.4504(4) 0.0674(10) Uani 1 1 d .
H4 H 0.2334 0.7281 1.5520 0.081 Uiso 1 1 calc R
C5 C 0.0312(5) 0.70937(16) 1.3628(4) 0.0586(9) Uani 1 1 d .
H5 H -0.0443 0.7300 1.4043 0.070 Uiso 1 1 calc R
C6 C -0.0219(4) 0.67927(13) 1.2116(4) 0.0443(6) Uani 1 1 d .
C7 C -0.1808(4) 0.67222(14) 1.0880(4) 0.0470(7) Uani 1 1 d .
C8 C -0.3425(4) 0.68971(17) 1.0783(5) 0.0614(9) Uani 1 1 d .
H8 H -0.3633 0.7128 1.1621 0.074 Uiso 1 1 calc R
C9 C -0.4698(4) 0.67218(19) 0.9429(5) 0.0676(10) Uani 1 1 d .
H9 H -0.5778 0.6834 0.9356 0.081 Uiso 1 1 calc R
C10 C -0.4406(4) 0.63820(19) 0.8173(5) 0.0630(9) Uani 1 1 d .
H10 H -0.5296 0.6271 0.7271 0.076 Uiso 1 1 calc R
C11 C -0.2828(4) 0.62027(17) 0.8217(4) 0.0517(7) Uani 1 1 d .
H11 H -0.2639 0.5975 0.7365 0.062 Uiso 1 1 calc R
C12 C -0.1535(3) 0.63768(14) 0.9590(4) 0.0417(6) Uani 1 1 d .
C13 C 0.0897(3) 0.58569(14) 0.9036(3) 0.0389(6) Uani 1 1 d .
C14 C 0.0628(4) 0.60136(16) 0.7418(4) 0.0478(7) Uani 1 1 d .
H14 H -0.0032 0.6369 0.6958 0.057 Uiso 1 1 calc R
C15 C 0.1346(4) 0.56401(18) 0.6484(4) 0.0538(8) Uani 1 1 d .
H15 H 0.1143 0.5734 0.5389 0.065 Uiso 1 1 calc R
C16 C 0.1907(4) 0.53368(14) 0.9724(4) 0.0447(6) Uani 1 1 d .
H16 H 0.2077 0.5229 1.0807 0.054 Uiso 1 1 calc R
C17 C 0.2667(4) 0.49762(16) 0.8814(4) 0.0491(7) Uani 1 1 d .
H17 H 0.3375 0.4635 0.9286 0.059 Uiso 1 1 calc R
C18 C 0.2361(4) 0.51285(16) 0.7196(4) 0.0496(7) Uani 1 1 d .
N1 N 0.0148(3) 0.62328(12) 0.9989(3) 0.0416(5) 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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 129.4(3)
N1 C1 C6 109.0(3)
C2 C1 C6 121.6(3)
C3 C2 C1 117.4(3)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 121.9(3)
C2 C3 H3 119.0
C4 C3 H3 119.0
C5 C4 C3 120.8(3)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 119.1(3)
C4 C5 H5 120.5
C6 C5 H5 120.5
C5 C6 C1 119.2(3)
C5 C6 C7 134.0(3)
C1 C6 C7 106.8(3)
C8 C7 C12 119.2(3)
C8 C7 C6 133.9(3)
C12 C7 C6 106.9(3)
C9 C8 C7 118.8(3)
C9 C8 H8 120.6
C7 C8 H8 120.6
C8 C9 C10 121.2(3)
C8 C9 H9 119.4
C10 C9 H9 119.4
C9 C10 C11 121.8(3)
C9 C10 H10 119.1
C11 C10 H10 119.1
C10 C11 C12 117.2(3)
C10 C11 H11 121.4
C12 C11 H11 121.4
C11 C12 N1 129.2(3)
C11 C12 C7 121.8(3)
N1 C12 C7 108.9(3)
C16 C13 C14 119.9(3)
C16 C13 N1 120.0(2)
C14 C13 N1 120.1(3)
C13 C14 C15 119.9(3)
C13 C14 H14 120.0
C15 C14 H14 120.0
C18 C15 C14 119.3(3)
C18 C15 H15 120.4
C14 C15 H15 120.4
C17 C16 C13 120.4(3)
C17 C16 H16 119.8
C13 C16 H16 119.8
C18 C17 C16 119.1(3)
C18 C17 H17 120.5
C16 C17 H17 120.5
C15 C18 C17 121.4(3)
C15 C18 Br1 119.6(2)
C17 C18 Br1 118.9(2)
C1 N1 C12 108.4(2)
C1 N1 C13 125.7(2)
C12 N1 C13 125.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C18 1.894(3)
C1 N1 1.388(4)
C1 C2 1.390(4)
C1 C6 1.406(4)
C2 C3 1.372(5)
C2 H2 0.9300
C3 C4 1.381(5)
C3 H3 0.9300
C4 C5 1.376(6)
C4 H4 0.9300
C5 C6 1.390(5)
C5 H5 0.9300
C6 C7 1.444(4)
C7 C8 1.398(4)
C7 C12 1.403(4)
C8 C9 1.372(6)
C8 H8 0.9300
C9 C10 1.379(6)
C9 H9 0.9300
C10 C11 1.380(5)
C10 H10 0.9300
C11 C12 1.390(4)
C11 H11 0.9300
C12 N1 1.394(4)
C13 C16 1.383(4)
C13 C14 1.386(4)
C13 N1 1.419(3)
C14 C15 1.387(4)
C14 H14 0.9300
C15 C18 1.376(5)
C15 H15 0.9300
C16 C17 1.381(4)
C16 H16 0.9300
C17 C18 1.379(5)
C17 H17 0.9300
