#------------------------------------------------------------------------------
#$Date: 2016-02-04 23:19:26 +0200 (Thu, 04 Feb 2016) $
#$Revision: 175873 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/83/7118395.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_7118395
loop_
_publ_author_name
'Ward, Jonathan S.'
'Nobuyasu, Roberto S.'
'Batsanov, Andrei S.'
'Data, Przemyslaw'
'Monkman, Andrew P.'
'Dias, Fernando B.'
'Bryce, Martin R.'
_publ_section_title
;
 The interplay of thermally activated delayed fluorescence (TADF) and room
 temperature organic phosphorescence in sterically-constrained
 donor-acceptor charge-transfer molecules.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2612
_journal_page_last               2615
_journal_paper_doi               10.1039/c5cc09645f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C42 H34 N2 O2 S3'
_chemical_formula_sum            'C42 H34 N2 O2 S3'
_chemical_formula_weight         694.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2015-11-17 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.962(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7719(10)
_cell_length_b                   13.6832(10)
_cell_length_c                   19.915(2)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.20
_cell_volume                     3437.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'ShelXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.119
_diffrn_reflns_theta_min         2.196
_diffrn_source                   'ImuS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0854 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.9710.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, hexane'
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0400
_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)+(0.0600P)²+3.2350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4454
_reflns_number_total             5057
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc09645f2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7118393--7118396.cif.
;
_cod_original_cell_volume        3437.8(5)
_cod_database_code               7118395
_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_max   0.961
_shelx_estimated_absorpt_t_min   0.928
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Uiso(H20A)=Uiso(H20B)=Uiso(H20C)=FVAR(1)
 Uiso(H21A)=Uiso(H21B)=Uiso(H21C)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C19(H19)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
S1 S 0.2500 0.20113(3) 0.5000 0.03353(15) Uani 1 2 d S T P
S2 S -0.04561(3) 0.59719(3) 0.28388(2) 0.02564(10) Uani 1 1 d . . .
O1 O 0.15371(14) 0.14554(9) 0.49716(6) 0.0584(5) Uani 1 1 d . . .
N1 N 0.17698(8) 0.53492(7) 0.30942(5) 0.01634(19) Uani 1 1 d . . .
C1 C 0.23493(11) 0.28961(8) 0.43488(6) 0.0205(2) Uani 1 1 d . . .
C2 C 0.23878(9) 0.38313(8) 0.46266(5) 0.0154(2) Uani 1 1 d . . .
C3 C 0.21912(9) 0.46412(8) 0.42136(6) 0.0152(2) Uani 1 1 d . . .
H3 H 0.2213 0.5277 0.4407 0.018 Uiso 1 1 calc R . .
C4 C 0.19589(9) 0.45230(8) 0.35056(6) 0.0146(2) Uani 1 1 d . . .
C5 C 0.19305(10) 0.35713(9) 0.32309(6) 0.0186(2) Uani 1 1 d . . .
H5 H 0.1778 0.3485 0.2752 0.022 Uiso 1 1 calc R . .
C6 C 0.21215(11) 0.27594(9) 0.36496(6) 0.0220(2) Uani 1 1 d . . .
H6 H 0.2097 0.2120 0.3461 0.026 Uiso 1 1 calc R . .
C7 C 0.13179(10) 0.52785(8) 0.23948(6) 0.0177(2) Uani 1 1 d . . .
C8 C 0.02635(10) 0.55526(9) 0.22053(6) 0.0205(2) Uani 1 1 d . . .
C9 C -0.01854(11) 0.55345(10) 0.15195(7) 0.0265(3) Uani 1 1 d . . .
H9 H -0.0904 0.5723 0.1386 0.032 Uiso 1 1 calc R . .
C10 C 0.04173(13) 0.52425(10) 0.10364(7) 0.0288(3) Uani 1 1 d . . .
H10 H 0.0108 0.5222 0.0571 0.035 Uiso 1 1 calc R . .
C11 C 0.14716(13) 0.49790(10) 0.12251(6) 0.0279(3) Uani 1 1 d . . .
H11 H 0.1880 0.4777 0.0890 0.033 Uiso 1 1 calc R . .
C12 C 0.19278(11) 0.50115(9) 0.19049(6) 0.0231(3) Uani 1 1 d . . .
H12 H 0.2655 0.4852 0.2034 0.028 Uiso 1 1 calc R . .
C13 C 0.16093(9) 0.62775(8) 0.33981(6) 0.0161(2) Uani 1 1 d . . .
C14 C 0.05749(10) 0.66328(9) 0.33363(6) 0.0202(2) Uani 1 1 d . . .
C15 C 0.03691(12) 0.75113(11) 0.36449(7) 0.0283(3) Uani 1 1 d . . .
H15 H -0.0333 0.7759 0.3604 0.034 Uiso 1 1 calc R . .
C16 C 0.12101(13) 0.80172(10) 0.40125(8) 0.0318(3) Uani 1 1 d . . .
H16 H 0.1077 0.8601 0.4244 0.038 Uiso 1 1 calc R . .
C17 C 0.22418(12) 0.76831(9) 0.40474(7) 0.0270(3) Uani 1 1 d . . .
H17 H 0.2806 0.8053 0.4291 0.032 Uiso 1 1 calc R . .
C18 C 0.24682(10) 0.68137(8) 0.37323(6) 0.0193(2) Uani 1 1 d . . .
C19 C 0.35917(10) 0.64743(10) 0.37159(7) 0.0230(2) Uani 1 1 d . . .
H19 H 0.3581 0.5745 0.3687 0.028 Uiso 1 1 calc R . .
C20 C 0.43778(13) 0.67595(14) 0.43458(9) 0.0399(4) Uani 1 1 d . . .
H20A H 0.4459 0.7472 0.4362 0.057(4) Uiso 1 1 calc GR . .
H20B H 0.5066 0.6455 0.4324 0.057(4) Uiso 1 1 calc GR . .
H20C H 0.4112 0.6534 0.4755 0.057(4) Uiso 1 1 calc GR . .
C21 C 0.39493(13) 0.68679(13) 0.30649(9) 0.0358(3) Uani 1 1 d . . .
H21A H 0.3466 0.6632 0.2667 0.047(3) Uiso 1 1 calc GR . .
H21B H 0.4670 0.6639 0.3041 0.047(3) Uiso 1 1 calc GR . .
H21C H 0.3940 0.7584 0.3071 0.047(3) Uiso 1 1 calc GR . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.0780
0.00 -1.00 1.00 0.0740
0.00 -1.00 -1.00 0.0850
0.00 1.00 1.00 0.0840
2.00 0.00 -1.00 0.1110
-3.00 0.00 1.00 0.1400
1.00 -1.00 0.00 0.0990
3.00 -1.00 -2.00 0.1060
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
O1 S1 O1 116.21(14) . 2_556
O1 S1 C1 112.74(8) 2_556 .
O1 S1 C1 109.83(6) . .
O1 S1 C1 112.74(8) . 2_556
O1 S1 C1 109.83(6) 2_556 2_556
C1 S1 C1 93.24(8) 2_556 .
C14 S2 C8 98.12(6) . .
C4 N1 C7 121.71(9) . .
C4 N1 C13 119.50(9) . .
C7 N1 C13 114.17(9) . .
C2 C1 S1 110.24(8) . .
C6 C1 S1 128.79(9) . .
C6 C1 C2 120.71(11) . .
C1 C2 C2 113.04(6) . 2_556
C3 C2 C1 120.63(10) . .
C3 C2 C2 126.29(6) . 2_556
C2 C3 C4 119.77(10) . .
N1 C4 C3 119.12(10) . .
N1 C4 C5 121.91(10) . .
C3 C4 C5 118.97(10) . .
C6 C5 C4 120.95(10) . .
C5 C6 C1 118.96(11) . .
C8 C7 N1 118.29(11) . .
C12 C7 N1 121.22(11) . .
C12 C7 C8 120.33(11) . .
C7 C8 S2 118.83(9) . .
C7 C8 C9 119.52(12) . .
C9 C8 S2 121.58(11) . .
C10 C9 C8 119.85(13) . .
C9 C10 C11 120.59(12) . .
C10 C11 C12 119.85(13) . .
C11 C12 C7 119.82(13) . .
C14 C13 N1 117.81(10) . .
C14 C13 C18 121.38(11) . .
C18 C13 N1 120.79(11) . .
C13 C14 S2 118.91(9) . .
C15 C14 S2 120.87(10) . .
C15 C14 C13 120.18(12) . .
C16 C15 C14 118.65(13) . .
C17 C16 C15 120.92(12) . .
C16 C17 C18 121.35(13) . .
C13 C18 C19 120.30(11) . .
C17 C18 C13 117.31(12) . .
C17 C18 C19 122.32(12) . .
C18 C19 C20 114.04(12) . .
C18 C19 C21 108.54(11) . .
C20 C19 C21 111.02(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4396(14) .
S1 O1 1.4397(14) 2_556
S1 C1 1.7625(12) 2_556
S1 C1 1.7625(12) .
S2 C8 1.7683(13) .
S2 C14 1.7683(13) .
N1 C4 1.3950(14) .
N1 C7 1.4254(14) .
N1 C13 1.4354(14) .
C1 C2 1.3920(15) .
C1 C6 1.3900(16) .
C2 C2 1.470(2) 2_556
C2 C3 1.3796(15) .
C3 C4 1.4041(15) .
C4 C5 1.4109(15) .
C5 C6 1.3876(16) .
C7 C8 1.3923(18) .
C7 C12 1.3889(17) .
C8 C9 1.3966(17) .
C9 C10 1.382(2) .
C10 C11 1.388(2) .
C11 C12 1.3886(18) .
C13 C14 1.3952(17) .
C13 C18 1.3990(17) .
C14 C15 1.3935(18) .
C15 C16 1.387(2) .
C16 C17 1.386(2) .
C17 C18 1.3961(17) .
C18 C19 1.5134(18) .
C19 C20 1.530(2) .
C19 C21 1.538(2) .
