#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:58:06 +0100 (dom 24 de nov de 2019) $
#$Revision: 238681 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/78/7237871.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_7237871
loop_
_publ_author_name
'de Sa Pereira, Daniel'
'Lee, Dong Ryun'
'Kukhta, Nadzeya A.'
'Lee, Kyung Hyung'
'Kim, Cho Long'
'Batsanov, Andrei S.'
'Lee, Jun Yeob'
'Monkman, Andrew P.'
_publ_section_title
;
 The effect of a heavy atom on the radiative pathways of an emitter with
 dual conformation, thermally-activated delayed fluorescence and room
 temperature phosphorescence
;
_journal_issue                   34
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10481
_journal_paper_doi               10.1039/C9TC02477H
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_chemical_name_common            phenothiazine
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-12 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9000(8)
_cell_length_b                   20.937(2)
_cell_length_c                   5.8824(6)
_cell_measurement_reflns_used    2551
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      3.60
_cell_volume                     972.96(17)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS, 2005-2017)'
_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 multi-CPU (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_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       ω-scan
_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  0.0841
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.598
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) 
  was 0.1829 before and 0.0982 after correction. The Ratio of minimum to 
  maximum transmission is 0.5147. The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       tablet
_exptl_crystal_F_000             416
_exptl_crystal_size_max          1.264
_exptl_crystal_size_mid          1.109
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0442
_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)+(0.0269P)²+0.4518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1258
_reflns_Friedel_coverage         0.000
_reflns_number_gt                622
_reflns_number_total             877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02477h2.cif
_cod_data_source_block           PTZ-293K
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        972.97(17)
_cod_database_code               7237871
_ccdc_comments                   'same as PHESAZ01'
_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   0.932
_shelx_estimated_absorpt_t_min   0.714
_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)
;
_shelx_res_file
;
TITL 19s026rt in Pnma
    19s026rt.res
    created by SHELXL-2018/3 at 19:30:07 on 11-Mar-2019
CELL 0.71073 7.9 20.9371 5.8824 90 90 90
ZERR 4 0.0008 0.0021 0.0006 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H N S
UNIT 48 36 4 4
EQIV $1 0.5+X,0.5-Y,-0.5-Z

L.S. 7 0 0
PLAN  6
SIZE 0.25 1.109 1.264
TEMP 20
HTAB N S_$1
fmap 2 53
acta 50
OMIT 1 9 1
REM <olex2.extras>
REM <HklSrc "%.\\19s026rt.hkl">
REM </olex2.extras>

WGHT    0.026900    0.451800
EXTI    0.023465
FVAR       0.26714
S     4    0.135022    0.250000    0.208335    10.50000    0.04320    0.18066 =
         0.04064    0.00000    0.01014    0.00000
N     3    0.332781    0.250000   -0.228492    10.50000    0.06316    0.12016 =
         0.03221    0.00000    0.01158    0.00000
H     2    0.380697    0.250000   -0.343872    10.50000    0.06360
C1    1    0.245240    0.315004    0.088928    11.00000    0.03336    0.13878 =
         0.04216   -0.00994   -0.00537    0.02004
C2    1    0.326743    0.308827   -0.120946    11.00000    0.03664    0.11097 =
         0.03962   -0.00388   -0.00336    0.01598
C3    1    0.398512    0.362565   -0.216887    11.00000    0.05055    0.11019 =
         0.06353    0.01054    0.00218    0.02397
AFIX  43
H3    2    0.455793    0.359027   -0.354433    11.00000   -1.20000
AFIX   0
C4    1    0.386979    0.420831   -0.113609    11.00000    0.07289    0.09759 =
         0.11052    0.00253   -0.00732    0.03163
AFIX  43
H4    2    0.432561    0.456791   -0.183364    11.00000   -1.20000
AFIX   0
C5    1    0.307813    0.426216    0.093778    11.00000    0.07649    0.12890 =
         0.11670   -0.03163   -0.01362    0.04412
AFIX  43
H5    2    0.301191    0.465704    0.165631    11.00000   -1.20000
AFIX   0
C6    1    0.238890    0.373342    0.193959    11.00000    0.05637    0.16143 =
         0.06604   -0.02926   -0.00455    0.03495
AFIX  43
H6    2    0.187015    0.377034    0.335271    11.00000   -1.20000
AFIX   0
HKLF 4




REM  19s026rt in Pnma
REM wR2 = 0.1258, GooF = S = 1.066, Restrained GooF = 1.066 for all data
REM R1 = 0.0442 for 622 Fo > 4sig(Fo) and 0.0692 for all 877 data
REM 71 parameters refined using 0 restraints

END

WGHT      0.0256      0.4572

REM Highest difference peak  0.160,  deepest hole -0.181,  1-sigma level  0.037
Q1    1   0.1943  0.2067  0.2322  11.00000  0.05    0.16
Q2    1   0.4243  0.2500 -0.0952  10.50000  0.05    0.14
Q3    1   0.2819  0.2500  0.1661  10.50000  0.05    0.13
Q4    1   0.2651  0.2500  0.2944  10.50000  0.05    0.12
Q5    1   0.1590  0.2813  0.3607  11.00000  0.05    0.11
Q6    1   0.5828  0.4452 -0.4393  11.00000  0.05    0.11
;
_shelx_res_checksum              25502
_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
S S 0.13502(11) 0.250000 0.20833(15) 0.0882(6) Uani 1 2 d S T P
N N 0.3328(4) 0.250000 -0.2285(6) 0.0718(11) Uani 1 2 d S T P
H H 0.381(4) 0.250000 -0.344(7) 0.064(12) Uiso 1 2 d S T P
C1 C 0.2452(3) 0.31500(16) 0.0889(4) 0.0714(9) Uani 1 1 d . . .
C2 C 0.3267(3) 0.30883(15) -0.1209(4) 0.0624(8) Uani 1 1 d . . .
C3 C 0.3985(3) 0.36257(17) -0.2169(5) 0.0748(9) Uani 1 1 d . . .
H3 H 0.455793 0.359027 -0.354433 0.090 Uiso 1 1 calc R . .
C4 C 0.3870(4) 0.42083(18) -0.1136(7) 0.0937(11) Uani 1 1 d . . .
H4 H 0.432561 0.456791 -0.183364 0.112 Uiso 1 1 calc R . .
C5 C 0.3078(5) 0.4262(2) 0.0938(7) 0.1074(13) Uani 1 1 d . . .
H5 H 0.301191 0.465704 0.165631 0.129 Uiso 1 1 calc R . .
C6 C 0.2389(4) 0.3733(2) 0.1940(5) 0.0946(12) Uani 1 1 d . . .
H6 H 0.187015 0.377034 0.335271 0.114 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0432(6) 0.1807(14) 0.0406(6) 0.000 0.0101(4) 0.000
N 0.063(2) 0.120(3) 0.0322(16) 0.000 0.0116(15) 0.000
C1 0.0334(12) 0.139(3) 0.0422(13) -0.0099(16) -0.0054(10) 0.0200(14)
C2 0.0366(12) 0.111(2) 0.0396(13) -0.0039(16) -0.0034(10) 0.0160(13)
C3 0.0505(16) 0.110(2) 0.0635(17) 0.0105(19) 0.0022(13) 0.0240(16)
C4 0.073(2) 0.098(3) 0.111(3) 0.003(2) -0.0073(19) 0.0316(18)
C5 0.076(2) 0.129(3) 0.117(3) -0.032(3) -0.014(2) 0.044(2)
C6 0.0564(19) 0.161(4) 0.066(2) -0.029(3) -0.0046(15) 0.035(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'
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
1.00 -1.00 1.00 0.4310
-1.00 1.00 -1.00 0.5130
1.00 0.00 -1.00 0.4220
-1.00 0.00 1.00 0.4480
0.00 1.00 0.00 0.1090
0.00 -1.00 0.00 0.1250
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_3
C1 S C1 101.16(19) 7_565
C2 N C2 125.5(3) 7_565
C2 C1 S 120.5(3) .
C6 C1 S 119.4(2) .
C6 C1 C2 119.8(3) .
N C2 C1 120.1(3) .
C3 C2 N 121.6(2) .
C3 C2 C1 118.3(3) .
C4 C3 C2 121.2(3) .
C3 C4 C5 119.9(4) .
C6 C5 C4 119.8(4) .
C5 C6 C1 120.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C1 1.762(3) .
S C1 1.762(3) 7_565
N C2 1.386(3) 7_565
N C2 1.385(3) .
C1 C2 1.398(4) .
C1 C6 1.370(4) .
C2 C3 1.381(4) .
C3 C4 1.366(5) .
C4 C5 1.376(5) .
C5 C6 1.367(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N H S 0.78(4) 2.94(4) 3.697(4) 166(3) 4_554 yes
