#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/31/7233184.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_7233184
loop_
_publ_author_name
'Brodie L. Reid'
'Steven B. Briggs'
'Louise E. Karagiannidis'
'Sara Muzzioli'
'Paolo Raiteri'
'Mark E. Light'
'Stefano Stagni'
'Pierpaolo Brulatti'
'Philip A. Gale'
'Mark I. Ogdena'
'Massimiliano Massi'
_publ_section_title
;
 Blue emitting C2-symmetrical dibenzothiazolyl substituted pyrrole, furan
 and thiophene
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2209
_journal_page_last               2216
_journal_paper_doi               10.1039/C3TC00760J
_journal_volume                  1
_journal_year                    2013
_chemical_formula_sum            'C30 H18 N2 O S2'
_chemical_formula_weight         486.58
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 105.696(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.3406(14)
_cell_length_b                   9.3058(5)
_cell_length_c                   19.5502(9)
_cell_measurement_reflns_used    47237
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     4613.5(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1214
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28906
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.065
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1960
_refine_ls_R_factor_gt           0.1334
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+65.4428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2508
_refine_ls_wR_factor_ref         0.2863
_reflns_number_gt                2554
_reflns_number_total             4070
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7233184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12A C -0.1677(3) 0.8873(13) -0.0196(6) 0.0626(6) Uani 0.495(4) 1 d PD A 1
S2A S -0.22589(15) 0.8245(5) -0.0787(2) 0.0626(6) Uani 0.495(4) 1 d PD A 1
C13A C -0.2596(2) 0.9467(7) -0.0400(4) 0.0626(6) Uani 0.495(4) 1 d PGD A 1
C14A C -0.3131(2) 0.9786(9) -0.0566(4) 0.0626(6) Uani 0.495(4) 1 d PG A 1
H14A H -0.3375 0.9233 -0.0913 0.075 Uiso 0.495(4) 1 calc PR A 1
C15A C -0.3308(2) 1.0912(10) -0.0225(5) 0.0626(6) Uani 0.495(4) 1 d PG A 1
H15A H -0.3674 1.1130 -0.0338 0.075 Uiso 0.495(4) 1 calc PR A 1
C16A C -0.2951(3) 1.1721(9) 0.0283(4) 0.0626(6) Uani 0.495(4) 1 d PG A 1
H16A H -0.3072 1.2491 0.0516 0.075 Uiso 0.495(4) 1 calc PR A 1
C18A C -0.2415(3) 1.1402(8) 0.0449(4) 0.0626(6) Uani 0.495(4) 1 d PG A 1
H18A H -0.2171 1.1955 0.0796 0.075 Uiso 0.495(4) 1 calc PR A 1
C19A C -0.2238(2) 1.0276(8) 0.0107(4) 0.0626(6) Uani 0.495(4) 1 d PGD A 1
N2A N -0.1706(3) 0.9954(11) 0.0243(5) 0.0626(6) Uani 0.495(4) 1 d PD A 1
C12B C -0.1697(3) 0.8828(14) -0.0253(6) 0.0626(6) Uani 0.505(4) 1 d PD A 2
S2B S -0.22568(16) 0.8493(5) -0.0971(2) 0.0626(6) Uani 0.505(4) 1 d PD A 2
C13B C -0.2630(2) 0.9246(8) -0.0477(3) 0.0626(6) Uani 0.505(4) 1 d PGD A 2
C14B C -0.3173(2) 0.9439(9) -0.0655(4) 0.0626(6) Uani 0.505(4) 1 d PG A 2
H14B H -0.3388 0.9056 -0.1087 0.075 Uiso 0.505(4) 1 calc PR A 2
C15B C -0.3402(2) 1.0193(10) -0.0201(4) 0.0626(6) Uani 0.505(4) 1 d PG A 2
H15B H -0.3773 1.0326 -0.0322 0.075 Uiso 0.505(4) 1 calc PR A 2
C16B C -0.3087(3) 1.0754(10) 0.0431(4) 0.0626(6) Uani 0.505(4) 1 d PG A 2
H16B H -0.3243 1.1269 0.0742 0.075 Uiso 0.505(4) 1 calc PR A 2
C18B C -0.2543(3) 1.0561(10) 0.0609(3) 0.0626(6) Uani 0.505(4) 1 d PG A 2
H18B H -0.2328 1.0944 0.1041 0.075 Uiso 0.505(4) 1 calc PR A 2
C19B C -0.2315(2) 0.9807(9) 0.0155(3) 0.0626(6) Uani 0.505(4) 1 d PGD A 2
N2B N -0.1775(3) 0.9541(12) 0.0281(5) 0.0626(6) Uani 0.505(4) 1 d PD A 2
S1 S 0.07816(6) 0.7998(2) 0.05792(9) 0.0608(5) Uani 1 1 d . . .
O1 O -0.07625(14) 0.8564(4) 0.0323(2) 0.0452(10) Uani 1 1 d . . .
N1 N 0.01573(19) 0.8388(5) 0.1386(3) 0.0476(13) Uani 1 1 d . . .
C1 C 0.06641(11) 0.8375(3) 0.18339(13) 0.0490(17) Uani 1 1 d G . .
C2 C 0.07986(12) 0.8542(3) 0.25676(13) 0.065(2) Uani 1 1 d G . .
H2 H 0.0531 0.8676 0.2803 0.077 Uiso 1 1 calc R . .
C3 C 0.13252(13) 0.8513(4) 0.29563(13) 0.082(3) Uani 1 1 d G . .
H3 H 0.1417 0.8627 0.3458 0.099 Uiso 1 1 calc R . .
C4 C 0.17174(11) 0.8316(5) 0.26114(14) 0.107(3) Uani 1 1 d G . .
H4 H 0.2077 0.8296 0.2877 0.128 Uiso 1 1 calc R . .
C5 C 0.15829(10) 0.8149(4) 0.18777(14) 0.103(3) Uani 1 1 d G . .
H5 H 0.1851 0.8015 0.1642 0.124 Uiso 1 1 calc R . .
C6 C 0.10563(10) 0.8178(3) 0.14890(13) 0.065(2) Uani 1 1 d G . .
C7 C 0.0161(2) 0.8192(6) 0.0734(3) 0.0428(15) Uani 1 1 d . . .
C8 C -0.0315(2) 0.8102(6) 0.0151(3) 0.0420(15) Uani 1 1 d . . .
C9 C -0.0435(2) 0.7580(6) -0.0519(3) 0.0403(15) Uani 1 1 d . B .
C10 C -0.0993(2) 0.7689(6) -0.0790(3) 0.0449(16) Uani 1 1 d D . .
C11 C -0.11717(19) 0.8310(6) -0.0267(3) 0.0434(15) Uani 1 1 d D A .
C20 C -0.0078(2) 0.7021(6) -0.0920(3) 0.0432(15) Uani 1 1 d . . .
C21 C 0.0221(3) 0.7951(7) -0.1214(3) 0.0603(18) Uani 1 1 d . B .
H21 H 0.0205 0.8952 -0.1127 0.072 Uiso 1 1 calc R . .
C22 C 0.05359(15) 0.7483(5) -0.16216(13) 0.070(2) Uani 1 1 d G . .
H22 H 0.0732 0.8147 -0.1817 0.084 Uiso 1 1 calc R B .
C23 C 0.05632(15) 0.6017(5) -0.17435(14) 0.063(2) Uani 1 1 d G B .
H23 H 0.0780 0.5670 -0.2024 0.076 Uiso 1 1 calc R . .
C24 C 0.02726(17) 0.5059(4) -0.14550(15) 0.090(3) Uani 1 1 d G . .
H24 H 0.0291 0.4057 -0.1538 0.108 Uiso 1 1 calc R B .
C25 C -0.00452(15) 0.5567(4) -0.10445(15) 0.090(3) Uani 1 1 d G B .
H25 H -0.0242 0.4907 -0.0847 0.108 Uiso 1 1 calc R . .
C26A C -0.1305(3) 0.7304(9) -0.1521(3) 0.0580(11) Uani 0.468(5) 1 d PGD B 3
C27A C -0.1402(3) 0.5871(8) -0.1712(4) 0.0580(11) Uani 0.468(5) 1 d PG B 3
H27A H -0.1257 0.5133 -0.1381 0.070 Uiso 0.468(5) 1 calc PR B 3
C28A C -0.1710(4) 0.5518(8) -0.2388(4) 0.0580(11) Uani 0.468(5) 1 d PG B 3
H28A H -0.1776 0.4538 -0.2519 0.070 Uiso 0.468(5) 1 calc PR B 3
C29A C -0.1922(3) 0.6597(10) -0.2872(3) 0.0580(11) Uani 0.468(5) 1 d PG B 3
H29A H -0.2133 0.6356 -0.3334 0.070 Uiso 0.468(5) 1 calc PR B 3
C30A C -0.1826(3) 0.8031(9) -0.2681(4) 0.0580(11) Uani 0.468(5) 1 d PG B 3
H30A H -0.1970 0.8769 -0.3012 0.070 Uiso 0.468(5) 1 calc PR B 3
C31A C -0.1517(3) 0.8384(8) -0.2006(4) 0.0580(11) Uani 0.468(5) 1 d PG B 3
H31A H -0.1451 0.9364 -0.1875 0.070 Uiso 0.468(5) 1 calc PR B 3
C26B C -0.1325(2) 0.7186(8) -0.1481(3) 0.0580(11) Uani 0.532(5) 1 d PGD B 4
C27B C -0.1663(3) 0.6023(8) -0.1521(3) 0.0580(11) Uani 0.532(5) 1 d PG B 4
H27B H -0.1676 0.5528 -0.1101 0.070 Uiso 0.532(5) 1 calc PR B 4
C28B C -0.1983(3) 0.5584(8) -0.2176(4) 0.0580(11) Uani 0.532(5) 1 d PG B 4
H28B H -0.2213 0.4789 -0.2204 0.070 Uiso 0.532(5) 1 calc PR B 4
C29B C -0.1964(3) 0.6308(9) -0.2791(3) 0.0580(11) Uani 0.532(5) 1 d PG B 4
H29B H -0.2183 0.6008 -0.3239 0.070 Uiso 0.532(5) 1 calc PR B 4
C30B C -0.1626(3) 0.7471(9) -0.2751(3) 0.0580(11) Uani 0.532(5) 1 d PG B 4
H30B H -0.1614 0.7966 -0.3171 0.070 Uiso 0.532(5) 1 calc PR B 4
C31B C -0.1307(3) 0.7910(8) -0.2096(4) 0.0580(11) Uani 0.532(5) 1 d PG B 4
H31B H -0.1076 0.8705 -0.2069 0.070 Uiso 0.532(5) 1 calc PR B 4
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'
S S 0.1246 0.1234 '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
N2A C12A C11 122.6(8) . .
N2A C12A S2A 118.8(6) . .
C11 C12A S2A 118.2(7) . .
C13A S2A C12A 87.3(4) . .
C14A C13A C19A 120.0 . .
C14A C13A S2A 130.0(4) . .
C19A C13A S2A 109.7(4) . .
C15A C14A C13A 120.0 . .
C14A C15A C16A 120.0 . .
C18A C16A C15A 120.0 . .
C16A C18A C19A 120.0 . .
N2A C19A C18A 121.7(6) . .
N2A C19A C13A 118.3(6) . .
C18A C19A C13A 120.0 . .
C12A N2A C19A 105.7(7) . .
N2B C12B C11 122.4(8) . .
N2B C12B S2B 116.7(6) . .
C11 C12B S2B 121.0(7) . .
C13B S2B C12B 87.9(4) . .
C14B C13B C19B 120.0 . .
C14B C13B S2B 128.6(3) . .
C19B C13B S2B 111.2(4) . .
C13B C14B C15B 120.0 . .
C14B C15B C16B 120.0 . .
C18B C16B C15B 120.0 . .
C16B C18B C19B 120.0 . .
C18B C19B C13B 120.0 . .
C18B C19B N2B 124.9(5) . .
C13B C19B N2B 115.1(5) . .
C12B N2B C19B 108.8(7) . .
C6 S1 C7 87.9(2) . .
C11 O1 C8 105.7(4) . .
C7 N1 C1 111.1(5) . .
N1 C1 C2 125.8(2) . .
N1 C1 C6 114.2(2) . .
C2 C1 C6 120.0 . .
C1 C2 C3 120.0 . .
C4 C3 C2 120.0 . .
C5 C4 C3 120.0 . .
C4 C5 C6 120.0 . .
C5 C6 C1 120.0 . .
C5 C6 S1 129.45(10) . .
C1 C6 S1 110.55(10) . .
N1 C7 C8 123.3(5) . .
N1 C7 S1 116.2(4) . .
C8 C7 S1 120.5(4) . .
C9 C8 O1 111.0(4) . .
C9 C8 C7 135.0(5) . .
O1 C8 C7 113.8(5) . .
C8 C9 C10 106.3(5) . .
C8 C9 C20 128.9(5) . .
C10 C9 C20 124.8(5) . .
C11 C10 C9 106.4(5) . .
C11 C10 C26B 125.6(5) . .
C9 C10 C26B 128.0(6) . .
C11 C10 C26A 127.5(5) . .
C9 C10 C26A 125.9(6) . .
C26B C10 C26A 5.9(5) . .
C10 C11 O1 110.6(4) . .
C10 C11 C12A 136.5(6) . .
O1 C11 C12A 112.7(6) . .
C10 C11 C12B 132.0(6) . .
O1 C11 C12B 117.2(6) . .
C12A C11 C12B 4.6(7) . .
C25 C20 C21 117.8(5) . .
C25 C20 C9 121.2(5) . .
C21 C20 C9 120.9(5) . .
C22 C21 C20 122.8(6) . .
C21 C22 C23 118.7(3) . .
C24 C23 C22 120.0 . .
C23 C24 C25 120.0 . .
C20 C25 C24 120.7(3) . .
C27A C26A C31A 120.0 . .
C27A C26A C10 120.2(5) . .
C31A C26A C10 119.8(5) . .
C28A C27A C26A 120.0 . .
C29A C28A C27A 120.0 . .
C28A C29A C30A 120.0 . .
C31A C30A C29A 120.0 . .
C30A C31A C26A 120.0 . .
C27B C26B C31B 120.0 . .
C27B C26B C10 120.7(5) . .
C31B C26B C10 119.2(5) . .
C26B C27B C28B 120.0 . .
C29B C28B C27B 120.0 . .
C28B C29B C30B 120.0 . .
C31B C30B C29B 120.0 . .
C30B C31B C26B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C12A N2A 1.338(12) .
C12A C11 1.470(9) .
C12A S2A 1.752(10) .
S2A C13A 1.737(7) .
C13A C14A 1.3900 .
C13A C19A 1.3900 .
C14A C15A 1.3900 .
C15A C16A 1.3900 .
C16A C18A 1.3900 .
C18A C19A 1.3900 .
C19A N2A 1.387(9) .
C12B N2B 1.298(12) .
C12B C11 1.472(9) .
C12B S2B 1.767(10) .
S2B C13B 1.703(7) .
C13B C14B 1.3900 .
C13B C19B 1.3900 .
C14B C15B 1.3900 .
C15B C16B 1.3900 .
C16B C18B 1.3900 .
C18B C19B 1.3900 .
C19B N2B 1.399(9) .
S1 C6 1.737(3) .
S1 C7 1.751(6) .
O1 C11 1.369(6) .
O1 C8 1.379(7) .
N1 C7 1.291(7) .
N1 C1 1.384(5) .
C1 C2 1.3900 .
C1 C6 1.3900 .
C2 C3 1.3900 .
C3 C4 1.3900 .
C4 C5 1.3900 .
C5 C6 1.3900 .
C7 C8 1.450(7) .
C8 C9 1.351(8) .
C9 C10 1.425(7) .
C9 C20 1.473(8) .
C10 C11 1.364(8) .
C10 C26B 1.474(7) .
C10 C26A 1.488(7) .
C20 C25 1.382(7) .
C20 C21 1.393(9) .
C21 C22 1.368(7) .
C22 C23 1.3900 .
C23 C24 1.3900 .
C24 C25 1.3900 .
C26A C27A 1.3900 .
C26A C31A 1.3900 .
C27A C28A 1.3900 .
C28A C29A 1.3900 .
C29A C30A 1.3900 .
C30A C31A 1.3900 .
C26B C27B 1.3900 .
C26B C31B 1.3900 .
C27B C28B 1.3900 .
C28B C29B 1.3900 .
C29B C30B 1.3900 .
C30B C31B 1.3900 .
