#------------------------------------------------------------------------------
#$Date: 2020-11-29 02:09:07 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259278 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038934.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_4038934
loop_
_publ_author_name
'Hempe, Matthias'
'Harrison, Alastair K.'
'Ward, Jonathan S.'
'Batsanov, Andrei S.'
'Fox, Mark A.'
'Dias, Fernando B.'
'Bryce, Martin R.'
_publ_section_title
;
 Cyclophane Molecules Exhibiting Thermally Activated Delayed Fluorescence:
 Linking Donor Units to Influence Molecular Conformation
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02174
_journal_year                    2020
_chemical_formula_moiety         'C44 H34 N2 O4 S3'
_chemical_formula_sum            'C44 H34 N2 O4 S3'
_chemical_formula_weight         750.91
_chemical_melting_point          393.7(15)
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.142(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.751(3)
_cell_length_b                   12.365(3)
_cell_length_c                   20.967(6)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.19
_cell_measurement_theta_min      2.25
_cell_volume                     3457.0(15)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_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  0.0492
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26065
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS-2016/2 (Krause et al., 2015) was used for absorption correction. wR2(int) 
 was 0.1475 before and 0.0709 after correction. The Ratio of minimum to maximum 
 transmission is 0.8753. The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       lathe
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.236
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015a)'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0646
_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)+(0.0229P)²+18.1441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2740
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1c.cif
_cod_data_source_block           1c_18s477
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '393.7(1.5)' was changed to
'393.7(15)' -- precision was estimated.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        3456.8(16)
_cod_database_code               4038934
_shelx_shelxl_version_number     2018/3
_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   0.940
_shelx_estimated_absorpt_t_min   0.851
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O2A-C20B \\sim O2B-C20A
 with sigma of 0.02
 O2A-C19 \\sim O2B-C19
 with sigma of 0.02
 O2A-C20A \\sim O2B-C20B
 with sigma of 0.02
 C21-C20A \\sim C20B-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C20A) = Uanis(C20B)
4. Others
 Fixed Sof: O2A(0.75) O2B(0.25) H19A(0.75) H19B(0.75) H19C(0.25) H19D(0.25)
 H21(0.75) H21A(0.25) C20A(0.75) H20A(0.75) H20B(0.75) C20B(0.25) H20C(0.25)
 H20D(0.25)
5.a Riding coordinates:
 C22(H22A,H22B)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C19(H19C,H19D), C20A(H20A,H20B), C20B(H20C,H20D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C18(H18), C21(H21), C21(H21A)
;
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.750000 0.73837(9) 0.500000 0.0276(3) Uani 1 2 d S T P . .
S2 S 0.49873(9) 0.27907(10) 0.25097(5) 0.0520(4) Uani 1 1 d . . . . .
O1 O 0.7170(2) 0.79949(19) 0.54910(12) 0.0404(7) Uani 1 1 d . . . . .
O2A O 0.5711(3) 0.1161(3) 0.56296(18) 0.0489(10) Uani 0.75 1 d D . . A 1
O2B O 0.6446(9) 0.1442(9) 0.5595(5) 0.046(3) Uiso 0.25 1 d D . . A 2
N N 0.4896(2) 0.3757(2) 0.37683(12) 0.0259(6) Uani 1 1 d . . . . .
C1 C 0.6617(2) 0.6399(2) 0.46267(14) 0.0228(7) Uani 1 1 d . . . . .
C2 C 0.5690(2) 0.6574(3) 0.42049(15) 0.0264(7) Uani 1 1 d . . . . .
H2 H 0.544676 0.728904 0.410576 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5122(2) 0.5694(3) 0.39286(15) 0.0256(7) Uani 1 1 d . . . . .
H3 H 0.448358 0.581000 0.363747 0.031 Uiso 1 1 calc R . . . .
C4 C 0.5469(2) 0.4633(2) 0.40692(14) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.6420(2) 0.4475(2) 0.45013(14) 0.0213(6) Uani 1 1 d . . . . .
H5 H 0.666838 0.376234 0.460338 0.026 Uiso 1 1 calc R . . . .
C6 C 0.6989(2) 0.5355(2) 0.47763(13) 0.0197(6) Uani 1 1 d . . . . .
C7 C 0.3981(2) 0.3883(3) 0.32696(16) 0.0290(8) Uani 1 1 d . . . . .
C8 C 0.3932(3) 0.3458(3) 0.26501(17) 0.0393(9) Uani 1 1 d . . . . .
C9 C 0.3030(4) 0.3519(4) 0.21662(19) 0.0552(13) Uani 1 1 d . . . . .
H9 H 0.298805 0.324067 0.173798 0.066 Uiso 1 1 calc R . . . .
C10 C 0.2208(3) 0.3982(4) 0.2314(3) 0.0655(16) Uani 1 1 d . . . . .
H10 H 0.159619 0.401891 0.198539 0.079 Uiso 1 1 calc R . . . .
C11 C 0.2250(3) 0.4395(4) 0.2928(2) 0.0534(12) Uani 1 1 d . . . . .
H11 H 0.167507 0.472137 0.302105 0.064 Uiso 1 1 calc R . . . .
C12 C 0.3136(3) 0.4331(3) 0.34082(19) 0.0391(9) Uani 1 1 d . . . . .
H12 H 0.316435 0.459751 0.383732 0.047 Uiso 1 1 calc R . . . .
C13 C 0.5263(2) 0.2679(3) 0.38375(17) 0.0288(7) Uani 1 1 d . . . . .
C14 C 0.5350(3) 0.2124(3) 0.32780(19) 0.0381(9) Uani 1 1 d . . . . .
C15 C 0.5690(3) 0.1068(3) 0.3336(2) 0.0481(11) Uani 1 1 d . . . . .
H15 H 0.573163 0.067292 0.295500 0.058 Uiso 1 1 calc R . . . .
C16 C 0.5967(3) 0.0591(3) 0.3944(3) 0.0493(12) Uani 1 1 d . . . . .
H16 H 0.622615 -0.012490 0.398079 0.059 Uiso 1 1 calc R . . . .
C17 C 0.5876(3) 0.1134(3) 0.4510(2) 0.0407(9) Uani 1 1 d . . . . .
C18 C 0.5496(2) 0.2177(3) 0.44448(19) 0.0326(8) Uani 1 1 d . . . . .
H18 H 0.539576 0.254895 0.481990 0.039 Uiso 1 1 calc R . . . .
C19 C 0.6190(3) 0.0633(3) 0.5177(2) 0.0515(11) Uani 1 1 d D . . . .
H19A H 0.600977 -0.014414 0.514753 0.062 Uiso 0.75 1 calc R . . A 1
H19B H 0.692722 0.068924 0.534123 0.062 Uiso 0.75 1 calc R . . A 1
H19C H 0.563019 0.021549 0.527604 0.062 Uiso 0.25 1 calc R . . A 2
H19D H 0.676579 0.013961 0.520253 0.062 Uiso 0.25 1 calc R . . A 2
C21 C 0.6923(3) 0.1842(4) 0.6615(2) 0.0506(11) Uani 1 1 d D . . . .
H21 H 0.729072 0.170504 0.705351 0.061 Uiso 0.75 1 calc R . . B 1
H21A H 0.702726 0.178340 0.707861 0.061 Uiso 0.25 1 calc R . . C 2
C22 C 0.7094(3) 0.2755(4) 0.6353(3) 0.0691(15) Uani 1 1 d . . . . .
H22A H 0.683986 0.296455 0.590248 0.083 Uiso 1 1 d R . . . .
H22B H 0.753356 0.325365 0.663568 0.083 Uiso 1 1 d R . . . .
C20A C 0.6212(5) 0.1002(5) 0.6294(3) 0.061(2) Uani 0.75 1 d D . . A 1
H20A H 0.658095 0.030900 0.632703 0.073 Uiso 0.75 1 calc R . . A 1
H20B H 0.569806 0.092080 0.654924 0.073 Uiso 0.75 1 calc R . . A 1
C20B C 0.657(2) 0.0905(15) 0.6195(8) 0.061(2) Uani 0.25 1 d D . . A 2
H20C H 0.707778 0.032267 0.625273 0.073 Uiso 0.25 1 calc R . . A 2
H20D H 0.593048 0.061241 0.626049 0.073 Uiso 0.25 1 calc R . . A 2
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 0.00 1.00 0.1180
0.00 0.00 -1.00 0.0750
-1.00 0.00 1.00 0.1440
1.00 0.00 -1.00 0.1310
0.00 1.00 -1.00 0.2460
0.00 -1.00 1.00 0.2390
2.00 -1.00 0.00 0.2090
1.00 2.00 1.00 0.2340
0.00 -2.00 -1.00 0.2670
2.00 -1.00 -1.00 0.1900
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
_geom_angle_publ_flag
O1 S1 O1 116.6(2) . 2_656 ?
O1 S1 C1 110.45(14) . 2_656 ?
O1 S1 C1 112.16(15) 2_656 2_656 ?
O1 S1 C1 112.16(15) . . ?
O1 S1 C1 110.45(14) 2_656 . ?
C1 S1 C1 92.6(2) . 2_656 ?
C8 S2 C14 97.29(17) . . ?
C20A O2A C19 113.4(4) . . ?
C19 O2B C20B 101.1(10) . . ?
C4 N C7 122.8(3) . . ?
C4 N C13 122.3(3) . . ?
C13 N C7 113.8(3) . . ?
C2 C1 S1 127.2(2) . . ?
C2 C1 C6 121.4(3) . . ?
C6 C1 S1 111.3(2) . . ?
C1 C2 C3 119.0(3) . . ?
C2 C3 C4 121.3(3) . . ?
N C4 C3 120.3(3) . . ?
N C4 C5 121.0(3) . . ?
C3 C4 C5 118.7(3) . . ?
C6 C5 C4 120.0(3) . . ?
C1 C6 C6 112.34(17) . 2_656 ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C6 127.96(18) . 2_656 ?
C8 C7 N 118.3(3) . . ?
C12 C7 N 121.6(3) . . ?
C12 C7 C8 119.9(3) . . ?
C7 C8 S2 118.9(3) . . ?
C7 C8 C9 119.3(4) . . ?
C9 C8 S2 121.8(3) . . ?
C10 C9 C8 119.5(4) . . ?
C9 C10 C11 121.4(4) . . ?
C10 C11 C12 119.4(4) . . ?
C11 C12 C7 120.5(4) . . ?
C14 C13 N 118.6(3) . . ?
C18 C13 N 120.8(3) . . ?
C18 C13 C14 120.5(3) . . ?
C13 C14 S2 118.4(3) . . ?
C15 C14 S2 122.3(3) . . ?
C15 C14 C13 119.3(4) . . ?
C16 C15 C14 120.0(4) . . ?
C15 C16 C17 121.4(4) . . ?
C16 C17 C19 122.0(4) . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 C19 119.6(4) . . ?
C13 C18 C17 120.4(4) . . ?
O2A C19 C17 110.8(3) . . ?
O2B C19 C17 106.0(6) . . ?
C22 C21 C20A 126.0(5) . . ?
C22 C21 C20B 120.0(8) . . ?
O2A C20A C21 117.6(5) . . ?
O2B C20B C21 96.6(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.437(3) . ?
S1 O1 1.437(3) 2_656 ?
S1 C1 1.762(3) . ?
S1 C1 1.762(3) 2_656 ?
S2 C8 1.755(4) . ?
S2 C14 1.770(4) . ?
O2A C19 1.437(6) . ?
O2A C20A 1.409(7) . ?
O2B C19 1.320(11) . ?
O2B C20B 1.397(17) . ?
N C4 1.397(4) . ?
N C7 1.434(4) . ?
N C13 1.420(4) . ?
C1 C2 1.379(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.402(4) . ?
C4 C5 1.410(4) . ?
C5 C6 1.382(4) . ?
C6 C6 1.487(6) 2_656 ?
C7 C8 1.388(5) . ?
C7 C12 1.380(5) . ?
C8 C9 1.400(6) . ?
C9 C10 1.368(7) . ?
C10 C11 1.372(7) . ?
C11 C12 1.380(5) . ?
C13 C14 1.389(5) . ?
C13 C18 1.382(5) . ?
C14 C15 1.382(6) . ?
C15 C16 1.372(6) . ?
C16 C17 1.395(6) . ?
C17 C18 1.385(5) . ?
C17 C19 1.494(6) . ?
C21 C22 1.302(6) . ?
C21 C20A 1.471(8) . ?
C21 C20B 1.464(17) . ?
