#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:30:17 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/77/7237743.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_7237743
loop_
_publ_author_name
'Chen, Cheng'
'Lu, Hai-Yan'
'Wang, Yin-Feng'
'Li, Meng'
'Shen, Yi-Fan'
'Chen, Chuan-Feng'
_publ_section_title
;
 Naphthyridine-based thermally activated delayed fluorescence emitters for
 multi-color organic light-emitting diodes with low efficiency roll-off
;
_journal_issue                   16
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4673
_journal_paper_doi               10.1039/C9TC00503J
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C32 H20 N4 S2'
_chemical_formula_sum            'C32 H20 N4 S2'
_chemical_formula_weight         524.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-24 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.18250(10)
_cell_length_b                   27.5249(2)
_cell_length_c                   12.85110(10)
_cell_measurement_reflns_used    22136
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      75.2500
_cell_measurement_theta_min      3.2160
_cell_volume                     2894.36(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.577
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7169
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.311
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0418
_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)+(0.0498P)²+2.7974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2942
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc00503j2.cif
_cod_data_source_block           tx279a_sq
_cod_database_code               7237743
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
S1 S 0.15967(5) 0.44977(2) 0.39057(3) 0.02121(12) Uani 1 1 d . . .
N1 N 0.41079(18) 0.37605(5) 0.43213(11) 0.0204(3) Uani 1 1 d . . .
N2 N 0.41281(17) 0.29179(5) 0.42400(11) 0.0195(3) Uani 1 1 d . . .
C1 C 0.3722(2) 0.46017(6) 0.38138(12) 0.0171(3) Uani 1 1 d . . .
C2 C 0.4779(2) 0.42197(6) 0.40325(12) 0.0180(3) Uani 1 1 d . . .
C3 C 0.6460(2) 0.42952(6) 0.40104(14) 0.0216(4) Uani 1 1 d . . .
H3 H 0.718613 0.403883 0.418670 0.026 Uiso 1 1 calc R . .
C4 C 0.7071(2) 0.47480(7) 0.37287(13) 0.0227(4) Uani 1 1 d . . .
H4 H 0.821854 0.479858 0.369821 0.027 Uiso 1 1 calc R . .
C5 C 0.6015(2) 0.51258(6) 0.34923(13) 0.0212(3) Uani 1 1 d . . .
H5 H 0.644129 0.543269 0.329038 0.025 Uiso 1 1 calc R . .
C6 C 0.4337(2) 0.50576(6) 0.35495(13) 0.0200(3) Uani 1 1 d . . .
H6 H 0.361327 0.531948 0.340977 0.024 Uiso 1 1 calc R . .
C7 C 0.16311(19) 0.41143(6) 0.50114(13) 0.0188(3) Uani 1 1 d . . .
C8 C 0.2888(2) 0.37745(6) 0.51178(13) 0.0187(3) Uani 1 1 d . . .
C9 C 0.2964(2) 0.34849(6) 0.60056(13) 0.0233(4) Uani 1 1 d . . .
H9 H 0.383600 0.326095 0.609477 0.028 Uiso 1 1 calc R . .
C10 C 0.1753(2) 0.35260(7) 0.67611(15) 0.0290(4) Uani 1 1 d . . .
H10 H 0.179152 0.332585 0.736288 0.035 Uiso 1 1 calc R . .
C11 C 0.0488(2) 0.38579(7) 0.66402(15) 0.0307(4) Uani 1 1 d . . .
H11 H -0.034336 0.387985 0.715436 0.037 Uiso 1 1 calc R . .
C12 C 0.0431(2) 0.41568(7) 0.57747(15) 0.0261(4) Uani 1 1 d . . .
H12 H -0.041951 0.438916 0.570185 0.031 Uiso 1 1 calc R . .
C13 C 0.4537(2) 0.33342(6) 0.37975(13) 0.0191(3) Uani 1 1 d . . .
C14 C 0.4529(3) 0.250000 0.37336(19) 0.0191(5) Uani 1 2 d S T P
C15 C 0.5319(3) 0.250000 0.2755(2) 0.0237(5) Uani 1 2 d S T P
C16 C 0.5686(2) 0.20462(6) 0.22975(15) 0.0282(4) Uani 1 1 d . . .
H16 H 0.619091 0.203301 0.163235 0.034 Uiso 1 1 calc R . .
C17 C 0.5317(2) 0.16287(6) 0.28104(14) 0.0255(4) Uani 1 1 d . . .
H17 H 0.557137 0.132076 0.251844 0.031 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 S1 C7 97.74(8) . .
C2 N1 C8 115.51(13) . .
C13 N1 C2 121.45(14) . .
C13 N1 C8 122.87(13) . .
C13 N2 C14 117.75(15) . .
C2 C1 S1 118.46(13) . .
C2 C1 C6 120.36(15) . .
C6 C1 S1 121.17(13) . .
C1 C2 N1 118.88(15) . .
C1 C2 C3 119.87(15) . .
C3 C2 N1 121.19(15) . .
C2 C3 H3 120.2 . .
C4 C3 C2 119.64(16) . .
C4 C3 H3 120.2 . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.35(16) . .
C5 C4 H4 119.8 . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.25(16) . .
C6 C5 H5 119.9 . .
C1 C6 H6 120.3 . .
C5 C6 C1 119.46(16) . .
C5 C6 H6 120.3 . .
C8 C7 S1 119.30(12) . .
C12 C7 S1 120.27(13) . .
C12 C7 C8 120.42(16) . .
C7 C8 N1 117.51(15) . .
C9 C8 N1 122.66(15) . .
C9 C8 C7 119.73(15) . .
C8 C9 H9 120.2 . .
C10 C9 C8 119.55(17) . .
C10 C9 H9 120.2 . .
C9 C10 H10 119.8 . .
C11 C10 C9 120.39(17) . .
C11 C10 H10 119.8 . .
C10 C11 H11 119.8 . .
C12 C11 C10 120.36(17) . .
C12 C11 H11 119.8 . .
C7 C12 H12 120.2 . .
C11 C12 C7 119.51(17) . .
C11 C12 H12 120.2 . .
N1 C13 C17 118.79(15) . 7_565
N2 C13 N1 117.19(15) . .
N2 C13 C17 123.97(15) . 7_565
N2 C14 N2 115.3(2) . 7_565
N2 C14 C15 122.35(10) . .
N2 C14 C15 122.35(10) 7_565 .
C16 C15 C14 117.86(11) . .
C16 C15 C14 117.86(11) 7_565 .
C16 C15 C16 124.3(2) . 7_565
C15 C16 H16 120.0 . .
C17 C16 C15 119.90(17) . .
C17 C16 H16 120.0 . .
C13 C17 H17 120.9 7_565 .
C16 C17 C13 118.12(16) . 7_565
C16 C17 H17 120.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7663(17) .
S1 C7 1.7702(17) .
N1 C2 1.427(2) .
N1 C8 1.430(2) .
N1 C13 1.397(2) .
N2 C13 1.322(2) .
N2 C14 1.3617(19) .
C1 C2 1.390(2) .
C1 C6 1.394(2) .
C2 C3 1.391(2) .
C3 H3 0.9500 .
C3 C4 1.391(2) .
C4 H4 0.9500 .
C4 C5 1.386(3) .
C5 H5 0.9500 .
C5 C6 1.388(2) .
C6 H6 0.9500 .
C7 C8 1.397(2) .
C7 C12 1.393(2) .
C8 C9 1.393(2) .
C9 H9 0.9500 .
C9 C10 1.392(3) .
C10 H10 0.9500 .
C10 C11 1.390(3) .
C11 H11 0.9500 .
C11 C12 1.384(3) .
C12 H12 0.9500 .
C13 C17 1.424(2) 7_565
C14 C15 1.414(3) .
C15 C16 1.413(2) 7_565
C15 C16 1.413(2) .
C16 H16 0.9500 .
C16 C17 1.359(3) .
C17 H17 0.9500 .
