#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:58:06 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238681 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237870.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_7237870
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 Se'
_chemical_formula_sum            'C12 H9 N Se'
_chemical_formula_weight         246.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-16 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.912(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9066(4)
_cell_length_b                   7.9984(5)
_cell_length_c                   20.6824(12)
_cell_measurement_reflns_used    6868
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.53
_cell_volume                     974.83(11)
_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 multi-CPU version (Sheldrick, 2015a)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.742
_diffrn_measured_fraction_theta_max 0.666
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 0.742
_diffrn_reflns_Laue_measured_fraction_max 0.666
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2291
_diffrn_reflns_point_group_measured_fraction_full 0.742
_diffrn_reflns_point_group_measured_fraction_max 0.666
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         2.731
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.805
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
Component 1: wR2(int)=0.0751 before and 0.0229 after parameter 
refinement, component 2: 0.0778 and 0.0220, respectively.  
Final HKLF 4 output contains 11259 reflections, Rint = 0.0499
 (5162 with I > 3sig(I), Rint = 0.0360)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0333
_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)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1778
_reflns_number_total             1905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02477h2.cif
_cod_data_source_block           PSe-18s309
_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_database_code               7237870
_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   0.894
_shelx_estimated_absorpt_t_min   0.438
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5952(10)
 0.4048(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.3 times of:
  All N(H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_shelx_res_file
;
TITL 18srv309_a.res in P2(1)/n
    18srv309.res
    created by SHELXL-2018/3 at 16:47:02 on 27-Jul-2018
REM Old TITL 18srv309 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.207, Rweak 0.023, Alpha 0.083
REM <I/s> 2.075 for 118 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 Se
CELL 0.71073 5.9066 7.9984 20.6824 90 93.912 90
ZERR 4 0.0004 0.0005 0.0012 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N Se
UNIT 48 36 4 4
RIGU

L.S. 7 0 0
PLAN  7
SIZE 0.03 0.162 0.26
TEMP -153.15
BOND
list 8
fmap 2 53
acta 50
OMIT -3 60
OMIT 0 0 2
REM <olex2.extras>
REM <HklSrc "%.\\18srv309.hkl">
REM </olex2.extras>

WGHT    0.037900
BASF   0.40482
FVAR       0.63465
SE    4    0.274489    0.116775    0.740967    11.00000    0.01804    0.01575 =
         0.04953   -0.00054    0.00267   -0.00357
N     3    0.729643    0.318184    0.758082    11.00000    0.01188    0.02559 =
         0.03560   -0.00525    0.00435   -0.00459
H0    2    0.861027    0.365030    0.761710    11.00000   -1.30000
C1    1    0.423414    0.241680    0.677690    11.00000    0.01793    0.01172 =
         0.03508   -0.00614    0.00390    0.00449
C2    1    0.632602    0.315722    0.693984    11.00000    0.01950    0.01232 =
         0.03143   -0.00590    0.00541    0.00385
C3    1    0.750594    0.390497    0.645542    11.00000    0.02264    0.01964 =
         0.03423   -0.01354    0.00897   -0.00407
AFIX  43
H3    2    0.892138    0.443454    0.656299    11.00000   -1.20000
AFIX   0
C4    1    0.662113    0.387873    0.581690    11.00000    0.03852    0.02445 =
         0.03288   -0.00800    0.01154    0.00654
AFIX  43
H4    2    0.745521    0.435492    0.548588    11.00000   -1.20000
AFIX   0
C5    1    0.452646    0.316004    0.566206    11.00000    0.04199    0.02844 =
         0.03014   -0.01040   -0.00353    0.00595
AFIX  43
H5    2    0.390171    0.316063    0.522645    11.00000   -1.20000
AFIX   0
C6    1    0.335042    0.244288    0.614342    11.00000    0.02609    0.01876 =
         0.04564   -0.01076   -0.00160   -0.00092
AFIX  43
H6    2    0.190493    0.195794    0.603657    11.00000   -1.20000
AFIX   0
C7    1    0.398704    0.234144    0.815295    11.00000    0.01804    0.00814 =
         0.03886    0.00543    0.00649    0.00779
C8    1    0.608845    0.313732    0.813820    11.00000    0.01926    0.01094 =
         0.02928    0.00563    0.00459    0.01064
C9    1    0.702090    0.391481    0.870213    11.00000    0.02297    0.02119 =
         0.02921    0.00446    0.00003    0.00405
AFIX  43
H9    2    0.841510    0.450467    0.869539    11.00000   -1.20000
AFIX   0
C10   1    0.591068    0.382331    0.926886    11.00000    0.03284    0.02895 =
         0.02804    0.00945    0.00280    0.01218
AFIX  43
H10   2    0.657923    0.431509    0.965408    11.00000   -1.20000
AFIX   0
C11   1    0.384626    0.302671    0.928048    11.00000    0.03420    0.02965 =
         0.03407    0.01402    0.01627    0.00942
AFIX  43
H11   2    0.309182    0.297094    0.967114    11.00000   -1.20000
AFIX   0
C12   1    0.287623    0.230589    0.871702    11.00000    0.02281    0.01774 =
         0.04683    0.01019    0.01097    0.00623
AFIX  43
H12   2    0.143283    0.178328    0.872061    11.00000   -1.20000
AFIX   0
HKLF 5




REM  18srv309_a.res in P2(1)/n
REM wR2 = 0.0696, GooF = S = 1.035, Restrained GooF = 1.013 for all data
REM R1 = 0.0333 for 1778 Fo > 4sig(Fo) and 0.0571 for all 2291 data
REM 131 parameters refined using 108 restraints

END

WGHT      0.0378      0.0000

REM Highest difference peak  0.662,  deepest hole -0.536,  1-sigma level  0.087
Q1    1   0.1828  0.1186  0.7815  11.00000  0.05    0.66
Q2    1   0.3461  0.1125  0.7836  11.00000  0.05    0.46
Q3    1   0.3780  0.1231  0.6977  11.00000  0.05    0.35
Q4    1   0.5911  0.3741  0.6935  11.00000  0.05    0.32
Q5    1   0.7792  0.1142  0.7410  11.00000  0.05    0.32
Q6    1   0.6240  0.3951  0.8373  11.00000  0.05    0.30
Q7    1   0.1347  0.1075  0.7191  11.00000  0.05    0.30
;
_shelx_res_checksum              21150
_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+1/2, -z+1/2'
'-x, -y, -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
Se Se 0.27449(7) 0.11678(4) 0.74097(2) 0.02776(14) Uani 1 1 d . U
N N 0.7296(6) 0.3182(4) 0.75808(18) 0.0242(7) Uani 1 1 d . U
H0 H 0.861(6) 0.365(4) 0.7617(18) 0.032 Uiso 1 1 d R .
C1 C 0.4234(7) 0.2417(4) 0.67769(18) 0.0215(9) Uani 1 1 d . U
C2 C 0.6326(7) 0.3157(4) 0.69398(18) 0.0209(9) Uani 1 1 d . U
C3 C 0.7506(7) 0.3905(4) 0.64554(18) 0.0252(9) Uani 1 1 d . U
H3 H 0.892138 0.443454 0.656299 0.030 Uiso 1 1 calc R .
C4 C 0.6621(8) 0.3879(4) 0.58169(19) 0.0315(11) Uani 1 1 d . U
H4 H 0.745521 0.435492 0.548588 0.038 Uiso 1 1 calc R .
C5 C 0.4526(8) 0.3160(4) 0.56621(19) 0.0338(11) Uani 1 1 d . U
H5 H 0.390171 0.316063 0.522645 0.041 Uiso 1 1 calc R .
C6 C 0.3350(7) 0.2443(4) 0.61434(18) 0.0303(10) Uani 1 1 d . U
H6 H 0.190493 0.195794 0.603657 0.036 Uiso 1 1 calc R .
C7 C 0.3987(7) 0.2341(4) 0.81529(18) 0.0215(9) Uani 1 1 d . U
C8 C 0.6088(7) 0.3137(4) 0.81382(18) 0.0197(9) Uani 1 1 d . U
C9 C 0.7021(7) 0.3915(4) 0.87021(17) 0.0245(9) Uani 1 1 d . U
H9 H 0.841510 0.450467 0.869539 0.029 Uiso 1 1 calc R .
C10 C 0.5911(7) 0.3823(4) 0.92689(19) 0.0299(10) Uani 1 1 d . U
H10 H 0.657923 0.431509 0.965408 0.036 Uiso 1 1 calc R .
C11 C 0.3846(8) 0.3027(4) 0.9280(2) 0.0320(11) Uani 1 1 d . U
H11 H 0.309182 0.297094 0.967114 0.038 Uiso 1 1 calc R .
C12 C 0.2876(7) 0.2306(4) 0.87170(18) 0.0287(10) Uani 1 1 d . U
H12 H 0.143283 0.178328 0.872061 0.034 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
Se 0.0180(2) 0.01575(18) 0.0495(3) -0.00054(19) 0.00267(19) -0.0036(2)
N 0.0119(17) 0.0256(16) 0.0356(19) -0.0052(15) 0.0044(16) -0.0046(16)
C1 0.018(2) 0.0117(18) 0.035(2) -0.0061(15) 0.004(2) 0.0045(18)
C2 0.019(2) 0.0123(17) 0.031(2) -0.0059(15) 0.0054(19) 0.0039(18)
C3 0.023(2) 0.0196(19) 0.034(2) -0.0135(16) 0.009(2) -0.004(2)
C4 0.039(3) 0.024(2) 0.033(2) -0.0080(18) 0.012(2) 0.007(2)
C5 0.042(3) 0.028(2) 0.030(2) -0.0104(18) -0.004(2) 0.006(2)
C6 0.026(3) 0.019(2) 0.046(3) -0.0108(17) -0.002(2) -0.001(2)
C7 0.018(2) 0.0081(17) 0.039(2) 0.0054(15) 0.006(2) 0.0078(17)
C8 0.019(2) 0.0109(17) 0.029(2) 0.0056(15) 0.0046(19) 0.0106(18)
C9 0.023(2) 0.0212(19) 0.029(2) 0.0045(17) 0.000(2) 0.004(2)
C10 0.033(3) 0.029(2) 0.028(2) 0.0095(19) 0.0028(19) 0.012(2)
C11 0.034(3) 0.030(2) 0.034(2) 0.0140(19) 0.016(2) 0.009(2)
C12 0.023(3) 0.018(2) 0.047(3) 0.0102(17) 0.011(2) 0.006(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'
Se Se -0.0929 2.2259 '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
2.00 1.00 -1.00 0.0960
2.00 -2.00 1.00 0.0670
-1.00 2.00 -1.00 0.0670
-2.00 1.00 0.00 0.0870
0.00 0.00 -1.00 0.0070
0.00 0.00 1.00 0.0150
-1.00 -2.00 2.00 0.0940
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 Se C1 97.20(16)
C8 N C2 125.3(3)
C2 C1 Se 120.0(3)
C6 C1 Se 119.9(3)
C6 C1 C2 119.8(4)
C1 C2 N 122.1(4)
C1 C2 C3 119.2(4)
C3 C2 N 118.6(4)
C4 C3 C2 120.2(4)
C5 C4 C3 120.0(4)
C6 C5 C4 119.6(4)
C1 C6 C5 121.1(4)
C8 C7 Se 120.1(3)
C12 C7 Se 119.6(3)
C12 C7 C8 120.2(4)
N C8 C7 122.3(4)
N C8 C9 118.8(4)
C7 C8 C9 118.9(4)
C10 C9 C8 120.0(4)
C11 C10 C9 120.7(4)
C10 C11 C12 119.5(4)
C7 C12 C11 120.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se C1 1.908(4)
Se C7 1.905(4)
N C2 1.408(5)
N C8 1.397(4)
C1 C2 1.391(5)
C1 C6 1.377(5)
C2 C3 1.394(5)
C3 C4 1.387(5)
C4 C5 1.382(5)
C5 C6 1.377(5)
C7 C8 1.397(5)
C7 C12 1.377(4)
C8 C9 1.401(5)
C9 C10 1.384(5)
C10 C11 1.377(5)
C11 C12 1.388(5)
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.5952(10) ref 1 0 0 0 1 0 0 0 1
2 0.4048(10) mt_II -1 0 0 0 -1 0 0.465 0 1
