# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PSe-18s309
_database_code_depnum_ccdc_archive 'CCDC 1873559'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2018-10-16 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PSe-18s309          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.742 Why?
RESPONSE: Non-merohedral twinning with partial overlap of reflections, data merged into HKLF5 format 
;
_vrf_PLAT911_PSe-18s309          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        452 Report
RESPONSE: Non-merohedral twinning with partial overlap of reflections, data merged into HKLF5 format 
;
# Added during the CSD deposition process: Tuesday 16 October 2018 01:23 PM
# end Validation Reply Form

_audit_creation_date             2018-07-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N Se'
_chemical_formula_sum            'C12 H9 N Se'
_chemical_formula_weight         246.16
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   5.9066(4)
_cell_length_b                   7.9984(5)
_cell_length_c                   20.6824(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.912(2)
_cell_angle_gamma                90
_cell_volume                     974.83(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6868
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.53
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.438
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
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

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 340 narrow-frame ω-scans (scan 
width 0.5°, 10s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
   The crystal was a non-merohedral twin, deconvoluted using CELL_NOW 
 v. 2008/4. The components are related by a 180° rotation about the 
 reciprocal axis (0 0 1) and direct axis [0.232 0 1]. Twin law: 
 -1 0 0 
0 -1 0 
0.465 0 1. 
 1061 data ( 215 unique) involve domain 1 only, mean I/σ(I) 31.0
 1050 data ( 210 unique) involve domain 2 only, mean I/σ(I) 24.7
 9156 data (2157 unique) involve   2 domains,  mean I/σ(I)  10.2
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1778
_reflns_number_total             1905
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only. 
    Final refinement against combined all data from both domains, 
 in HKLF5 format.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.013
_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
_refine_special_details          
;Refined as a 2-component twin. Amino H atom - refxyz, other H atoms - riding 
(constr).,Twin
;
_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)
;

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

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_
_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
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) . . ?

_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'

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PTZ-293K
_database_code_depnum_ccdc_archive 'CCDC 1902674'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;

_ccdc_comments                   'same as PHESAZ01'

_audit_creation_date             2019-03-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            phenothiazine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
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'

_cell_length_a                   7.9000(8)
_cell_length_b                   20.937(2)
_cell_length_c                   5.8824(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     972.97(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2551
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.34
_cell_measurement_theta_min      3.60
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.714
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             416
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

_exptl_crystal_size_max          1.264
_exptl_crystal_size_mid          1.109
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
  space was nominally covered by 4 runs of 170 narrow-frame ω-scans 
  (scan width 1.0°, 3s exposure), every run at a different φ angle. 
  Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                622
_reflns_number_total             877
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.066
_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
_refine_special_details          
;
 Amino H atom - refall, other H atoms - riding.
;
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
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_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
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_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

_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'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PTZ-120K
_database_code_depnum_ccdc_archive 'CCDC 1902673'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTZ-120K            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.792 Why?
RESPONSE: Non-merohedral twinning with partial overlap of reflections, data merged into HKLF5 format 
;
_vrf_PLAT911_PTZ-120K            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        348 Report
RESPONSE: Twin data
;
# Added during the CSD deposition process: Tuesday 12 March 2019 01:17 AM
# end Validation Reply Form

_ccdc_comments                   'presumably same as PHESAZ03'

_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            phenothiazine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   5.8254(11)
_cell_length_b                   7.7897(14)
_cell_length_c                   20.803(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.929(5)
_cell_angle_gamma                90
_cell_volume                     940.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1341
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.116
_cell_measurement_theta_min      3.563
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 8181 reflections, Rint = 0.0633
 (3386 with I > 3sig(I), Rint = 0.0582)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
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 0.00 0.177
0.00 -1.00 0.00 0.173
-1.00 0.00 0.00 0.188
1.00 -1.00 1.00 0.224
2.00 1.00 -1.00 0.193
0.00 0.00 -1.00 0.064
0.00 0.00 1.00 0.030

_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.128
_exptl_special_details           
; Low-temperature phase, the transition between 250 and 240 K.
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of 340 narrow-frame ω-scans (scan 
width 0.5°, 6s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm. 
    The crystal was a non-merohedral twin, deconvoluted using CELL_NOW 2008/4 
program. Twinning by 180° rotation about the real axis x, reciprocal 
axis [1 0 -0.28]. Twin law: 
     1    0   0 
     0   -1   0
   0.607  0  -1
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.723
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8188
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.134
_diffrn_reflns_theta_min         2.793
_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 0.792
_diffrn_measured_fraction_theta_max 0.723
_diffrn_measurement_device       '3-circle area detector diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1902
_reflns_number_total             2268
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.096
_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)+(0.0481P)²+1.4082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1380
_refine_special_details          
'Refined as a 2-component twin, against merged reflections in HKLF5 format.,SQUEEZE'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7871(17)
 0.2129(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C3(H3), C10(H10), C4(H4), C12(H12), C11(H11), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S S 0.28362(15) 0.85940(12) 0.74020(4) 0.0226(2) Uani 1 1 d . . . . .
N N 0.7362(5) 0.6654(4) 0.76025(14) 0.0220(6) Uani 1 1 d . . . . .
C2 C 0.6093(6) 0.6721(4) 0.81411(15) 0.0175(7) Uani 1 1 d . . . . .
C8 C 0.6392(6) 0.6708(4) 0.69672(15) 0.0183(7) Uani 1 1 d . . . . .
C7 C 0.4247(6) 0.7475(4) 0.68095(16) 0.0199(7) Uani 1 1 d . . . . .
C9 C 0.7582(6) 0.6025(4) 0.64699(16) 0.0225(7) Uani 1 1 d . . . . .
H9 H 0.904451 0.550440 0.656893 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3955(6) 0.7544(4) 0.81117(15) 0.0195(7) Uani 1 1 d . . . . .
C6 C 0.2761(6) 0.7645(4) 0.86585(17) 0.0243(8) Uani 1 1 d . . . . .
H6 H 0.128991 0.817979 0.863291 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6994(6) 0.6005(4) 0.87253(16) 0.0212(7) Uani 1 1 d . . . . .
H3 H 0.842503 0.541396 0.874974 0.025 Uiso 1 1 calc R . . . .
C10 C 0.6654(7) 0.6100(5) 0.58357(17) 0.0277(8) Uani 1 1 d . . . . .
H10 H 0.749595 0.564934 0.550237 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5784(6) 0.6161(5) 0.92715(16) 0.0256(8) Uani 1 1 d . . . . .
H4 H 0.641970 0.569731 0.967006 0.031 Uiso 1 1 calc R . . . .
C12 C 0.3303(6) 0.7506(4) 0.61738(16) 0.0244(8) Uani 1 1 d . . . . .
H12 H 0.182172 0.799473 0.607249 0.029 Uiso 1 1 calc R . . . .
C11 C 0.4509(7) 0.6825(5) 0.56837(17) 0.0290(9) Uani 1 1 d . . . . .
H11 H 0.386493 0.685932 0.524854 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3683(7) 0.6978(5) 0.92425(17) 0.0282(9) Uani 1 1 d . . . . .
H5 H 0.287441 0.708323 0.961809 0.034 Uiso 1 1 calc R . . . .
H H 0.860(7) 0.613(5) 0.7657(18) 0.028(11) Uiso 1 1 d . . . . .

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 0.0140(4) 0.0185(4) 0.0354(5) 0.0014(4) 0.0031(3) 0.0044(4)
N 0.0132(14) 0.0278(16) 0.0253(14) 0.0018(12) 0.0033(11) 0.0035(14)
C2 0.0153(17) 0.0138(16) 0.0238(15) -0.0011(12) 0.0040(13) -0.0039(13)
C8 0.0164(16) 0.0137(16) 0.0249(16) 0.0028(12) 0.0029(13) 0.0002(13)
C7 0.0178(17) 0.0156(16) 0.0264(16) 0.0024(13) 0.0030(14) -0.0031(14)
C9 0.0209(18) 0.0180(17) 0.0294(17) 0.0050(13) 0.0069(14) 0.0045(14)
C1 0.0144(17) 0.0146(15) 0.0296(17) -0.0025(13) 0.0031(13) -0.0019(13)
C6 0.0169(18) 0.0199(17) 0.0372(19) -0.0064(14) 0.0090(15) -0.0034(15)
C3 0.0164(17) 0.0206(18) 0.0265(17) -0.0002(13) 0.0010(14) -0.0029(14)
C10 0.032(2) 0.0248(19) 0.0271(18) 0.0022(14) 0.0096(16) 0.0000(17)
C4 0.027(2) 0.0250(19) 0.0240(17) 0.0003(14) 0.0011(15) -0.0074(15)
C12 0.0197(18) 0.0194(18) 0.0335(19) 0.0064(14) -0.0019(15) -0.0017(15)
C11 0.034(2) 0.028(2) 0.0247(17) 0.0054(14) -0.0033(16) -0.0044(17)
C5 0.031(2) 0.0254(19) 0.0303(18) -0.0080(14) 0.0123(16) -0.0073(16)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S C7 1.769(3) . ?
S C1 1.763(3) . ?
N C2 1.395(4) . ?
N C8 1.393(4) . ?
C2 C1 1.398(5) . ?
C2 C3 1.398(4) . ?
C8 C7 1.398(5) . ?
C8 C9 1.399(4) . ?
C7 C12 1.388(5) . ?
C9 C10 1.383(5) . ?
C1 C6 1.385(4) . ?
C6 C5 1.387(5) . ?
C3 C4 1.393(5) . ?
C10 C11 1.383(5) . ?
C4 C5 1.376(5) . ?
C12 C11 1.392(5) . ?

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
C1 S C7 101.21(16) . . ?
C8 N C2 124.2(3) . . ?
N C2 C1 120.9(3) . . ?
N C2 C3 119.9(3) . . ?
C1 C2 C3 119.2(3) . . ?
N C8 C7 121.1(3) . . ?
N C8 C9 120.3(3) . . ?
C7 C8 C9 118.6(3) . . ?
C8 C7 S 120.4(3) . . ?
C12 C7 S 119.0(3) . . ?
C12 C7 C8 120.3(3) . . ?
C10 C9 C8 120.8(3) . . ?
C2 C1 S 120.9(3) . . ?
C6 C1 S 119.0(3) . . ?
C6 C1 C2 119.9(3) . . ?
C1 C6 C5 120.9(3) . . ?
C4 C3 C2 119.7(3) . . ?
C11 C10 C9 120.4(3) . . ?
C5 C4 C3 121.0(3) . . ?
C7 C12 C11 120.5(3) . . ?
C10 C11 C12 119.4(3) . . ?
C4 C5 C6 119.2(3) . . ?

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 0.7871(17) ref 1 0 0 0 1 0 0 0 1
2 0.2129(17) mt_II 1 0 0 0 -1 0 0.6058 0 -1

_shelx_res_file                  
;
TITL 19srv026_a.res in P2(1)/n
    19srv026.res
    created by SHELXL-2018/3 at 00:09:24 on 12-Mar-2019
REM Old TITL 19srv026 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.173, Rweak 0.033, Alpha 0.068
REM <I/s> 1.713 for 142 systematic absences, Orientation as input
REM Formula found by SHELXT: C12 N Cl
CELL 0.71073 5.8254 7.7897 20.8027 90 94.9288 90
ZERR 4 0.0011 0.0014 0.0038 0 0.005 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 48 36 4 4

L.S. 7 0 0
PLAN  20
SIZE 0.128 0.354 0.471
TEMP -153.15
BOND
list 4
fmap 2 53
acta 50
OMIT 0 0 2
OMIT -1 6 1
OMIT -3 4 2
OMIT 0 6 1
REM <olex2.extras>
REM <HklSrc "%.\\19srv026.hkl">
REM </olex2.extras>

WGHT    0.048100    1.408200
BASF   0.21288
FVAR       0.71599
S     4    0.283623    0.859395    0.740204    11.00000    0.01405    0.01853 =
         0.03541    0.00140    0.00308    0.00441
N     3    0.736170    0.665364    0.760249    11.00000    0.01316    0.02776 =
         0.02527    0.00184    0.00329    0.00345
C2    1    0.609332    0.672137    0.814112    11.00000    0.01529    0.01384 =
         0.02384   -0.00113    0.00395   -0.00389
C8    1    0.639201    0.670776    0.696718    11.00000    0.01639    0.01374 =
         0.02491    0.00276    0.00292    0.00024
C7    1    0.424738    0.747472    0.680951    11.00000    0.01778    0.01563 =
         0.02637    0.00241    0.00299   -0.00311
C9    1    0.758217    0.602515    0.646994    11.00000    0.02094    0.01800 =
         0.02941    0.00504    0.00690    0.00450
AFIX  43
H9    2    0.904451    0.550440    0.656893    11.00000   -1.20000
AFIX   0
C1    1    0.395475    0.754373    0.811172    11.00000    0.01445    0.01463 =
         0.02956   -0.00246    0.00314   -0.00190
C6    1    0.276084    0.764543    0.865847    11.00000    0.01695    0.01993 =
         0.03720   -0.00637    0.00897   -0.00337
AFIX  43
H6    2    0.128991    0.817979    0.863291    11.00000   -1.20000
AFIX   0
C3    1    0.699377    0.600508    0.872535    11.00000    0.01644    0.02063 =
         0.02649   -0.00023    0.00099   -0.00288
AFIX  43
H3    2    0.842503    0.541396    0.874974    11.00000   -1.20000
AFIX   0
C10   1    0.665437    0.609959    0.583567    11.00000    0.03248    0.02475 =
         0.02710    0.00218    0.00964    0.00001
AFIX  43
H10   2    0.749595    0.564934    0.550237    11.00000   -1.20000
AFIX   0
C4    1    0.578449    0.616143    0.927145    11.00000    0.02738    0.02505 =
         0.02404    0.00031    0.00112   -0.00745
AFIX  43
H4    2    0.641970    0.569731    0.967006    11.00000   -1.20000
AFIX   0
C12   1    0.330261    0.750567    0.617376    11.00000    0.01965    0.01941 =
         0.03347    0.00635   -0.00187   -0.00168
AFIX  43
H12   2    0.182172    0.799473    0.607249    11.00000   -1.20000
AFIX   0
C11   1    0.450914    0.682542    0.568366    11.00000    0.03366    0.02772 =
         0.02466    0.00539   -0.00330   -0.00438
AFIX  43
H11   2    0.386493    0.685932    0.524854    11.00000   -1.20000
AFIX   0
C5    1    0.368325    0.697802    0.924249    11.00000    0.03060    0.02542 =
         0.03033   -0.00799    0.01234   -0.00728
AFIX  43
H5    2    0.287441    0.708323    0.961809    11.00000   -1.20000
AFIX   0
H     2    0.860342    0.612907    0.765672    11.00000    0.02837
HKLF 5




REM  19srv026_a.res in P2(1)/n
REM wR2 = 0.1380, GooF = S = 1.096, Restrained GooF = 1.096 for all data
REM R1 = 0.0581 for 1902 Fo > 4sig(Fo) and 0.0735 for all 2268 data
REM 132 parameters refined using 0 restraints

END

WGHT      0.0482      1.4147

REM Highest difference peak  0.448,  deepest hole -0.358,  1-sigma level  0.075
Q1    1   0.3023  0.8450  0.7838  11.00000  0.05    0.45
Q2    1   0.2827  0.8445  0.6934  11.00000  0.05    0.34
Q3    1   0.3470  0.7861  0.7034  11.00000  0.05    0.33
Q4    1   0.7056  0.6788  0.7220  11.00000  0.05    0.32
Q5    1   0.3550  0.7385  0.6570  11.00000  0.05    0.30
Q6    1   0.3583  0.7746  0.8386  11.00000  0.05    0.29
Q7    1   1.1655  0.5837  0.8020  11.00000  0.05    0.28
Q8    1   0.5411  0.6251  0.5840  11.00000  0.05    0.24
Q9    1   0.6646  0.6761  0.6638  11.00000  0.05    0.24
Q10   1   0.4212  0.7610  0.6422  11.00000  0.05    0.23
Q11   1   0.7021  0.3568  0.9211  11.00000  0.05    0.23
Q12   1   0.5334  0.9206  0.5158  11.00000  0.05    0.23
Q13   1   0.5337  0.7415  0.6826  11.00000  0.05    0.23
Q14   1   0.6169  0.5559  1.0181  11.00000  0.05    0.23
Q15   1   0.3466  0.9760  0.7177  11.00000  0.05    0.22
Q16   1   0.2363  0.9652  0.8029  11.00000  0.05    0.22
Q17   1   0.5108  0.6747  0.5009  11.00000  0.05    0.22
Q18   1   0.9094  0.5327  0.7411  11.00000  0.05    0.22
Q19   1   0.6576  0.5598  0.6218  11.00000  0.05    0.22
Q20   1   1.0651  0.6635  0.7874  11.00000  0.05    0.22
;
_shelx_res_checksum              25055
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PSeTRZ-18s310
_database_code_depnum_ccdc_archive 'CCDC 1873560'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2018-10-16 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H22 N4 Se'
_chemical_formula_sum            'C33 H22 N4 Se'
_chemical_formula_weight         553.50
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4469(9)
_cell_length_b                   19.0511(11)
_cell_length_c                   9.6130(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.035(2)
_cell_angle_gamma                90
_cell_volume                     2449.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_T_max  0.9555
_exptl_absorpt_correction_T_min  0.7720
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
; SADABS-2016/2 (Krause et al., 2015) was used for absorption correction. 
 wR2(int) was 0.0723 before and 0.0496 after correction. The Ratio of 
 minimum to maximum transmission is 0.8080. The λ/2 correction factor 
 is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 0.00 0.0510
1.00 0.00 0.00 0.0460
0.00 0.00 -1.00 0.0870
0.00 0.00 1.00 0.0850
0.00 1.00 0.00 0.0160
0.00 -1.00 0.00 0.0310

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.047
_exptl_special_details           
;
 Data were collected in shutterless mode. Full sphere of reciprocal 
space was nominally covered by 4 runs of narrow-frame ω-scans (3 x 340 + 221
scans of 0.5° width, 10s exposure), every run at a different φ angle.
Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49411
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         1.861
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5530
_reflns_number_total             7152
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.026
_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)+(0.0240P)²+2.0709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Se Se -0.03430(2) 0.39226(2) 0.39466(2) 0.01646(6) Uani 1 1 d . . . . .
N1 N 0.14721(11) 0.45446(8) 0.28180(16) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.52831(11) 0.45547(8) 0.73977(16) 0.0135(3) Uani 1 1 d . . . . .
N3 N 0.60473(11) 0.52463(8) 0.92659(16) 0.0145(3) Uani 1 1 d . . . . .
N4 N 0.46916(11) 0.57130(8) 0.77495(16) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.46553(13) 0.50933(9) 0.70762(18) 0.0121(3) Uani 1 1 d . . . . .
C2 C 0.59586(13) 0.46565(9) 0.84979(19) 0.0126(3) Uani 1 1 d . . . . .
C3 C 0.53959(13) 0.57566(9) 0.88426(18) 0.0129(3) Uani 1 1 d . . . . .
C4 C 0.38457(13) 0.49747(9) 0.59388(18) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.31999(13) 0.55086(9) 0.54138(18) 0.0129(3) Uani 1 1 d . . . . .
H5 H 0.329120 0.596114 0.576683 0.015 Uiso 1 1 calc R . . . .
C6 C 0.24257(13) 0.53773(9) 0.43775(19) 0.0127(3) Uani 1 1 d . . . . .
H6 H 0.201126 0.574307 0.403689 0.015 Uiso 1 1 calc R . . . .
C7 C 0.22608(13) 0.46977(9) 0.38366(18) 0.0122(3) Uani 1 1 d . . . . .
C8 C 0.29089(14) 0.41616(10) 0.4370(2) 0.0166(4) Uani 1 1 d . . . . .
H8 H 0.281405 0.370644 0.403187 0.020 Uiso 1 1 calc R . . . .
C9 C 0.36860(14) 0.43016(10) 0.5391(2) 0.0161(4) Uani 1 1 d . . . . .
H9 H 0.411115 0.393928 0.571943 0.019 Uiso 1 1 calc R . . . .
C10 C 0.13066(13) 0.38405(9) 0.23317(19) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.05024(14) 0.34634(9) 0.27433(19) 0.0147(4) Uani 1 1 d . . . . .
C12 C 0.03192(15) 0.27822(10) 0.2262(2) 0.0194(4) Uani 1 1 d . . . . .
H12 H -0.022280 0.253164 0.252951 0.023 Uiso 1 1 calc R . . . .
C13 C 0.09493(16) 0.24797(10) 0.1381(2) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.083948 0.202026 0.107527 0.025 Uiso 1 1 calc R . . . .
C14 C 0.17458(15) 0.28599(10) 0.0950(2) 0.0194(4) Uani 1 1 d . . . . .
H14 H 0.216112 0.265661 0.034800 0.023 Uiso 1 1 calc R . . . .
C15 C 0.19212(14) 0.35431(10) 0.14195(19) 0.0161(4) Uani 1 1 d . . . . .
H15 H 0.244816 0.379991 0.112349 0.019 Uiso 1 1 calc R . . . .
C16 C 0.06258(13) 0.49997(9) 0.25434(19) 0.0133(4) Uani 1 1 d . . . . .
C17 C -0.02858(14) 0.48027(9) 0.29979(18) 0.0132(3) Uani 1 1 d . . . . .
C18 C -0.11244(14) 0.52251(10) 0.2705(2) 0.0163(4) Uani 1 1 d . . . . .
H18 H -0.173011 0.509675 0.301707 0.020 Uiso 1 1 calc R . . . .
C19 C -0.10546(14) 0.58377(10) 0.1945(2) 0.0182(4) Uani 1 1 d . . . . .
H19 H -0.161199 0.612471 0.175778 0.022 Uiso 1 1 calc R . . . .
C20 C -0.01538(15) 0.60234(10) 0.1465(2) 0.0185(4) Uani 1 1 d . . . . .
H20 H -0.011291 0.643035 0.093969 0.022 Uiso 1 1 calc R . . . .
C21 C 0.06853(14) 0.56062(9) 0.1763(2) 0.0160(4) Uani 1 1 d . . . . .
H21 H 0.128766 0.573327 0.143839 0.019 Uiso 1 1 calc R . . . .
C22 C 0.66433(13) 0.40676(9) 0.89302(19) 0.0140(4) Uani 1 1 d . . . . .
C23 C 0.66982(14) 0.34878(10) 0.8061(2) 0.0180(4) Uani 1 1 d . . . . .
H23 H 0.631341 0.347511 0.719906 0.022 Uiso 1 1 calc R . . . .
C24 C 0.73216(16) 0.29289(10) 0.8470(2) 0.0225(4) Uani 1 1 d . . . . .
H24 H 0.735912 0.254524 0.787962 0.027 Uiso 1 1 calc R . . . .
C25 C 0.78905(15) 0.29425(11) 0.9763(2) 0.0226(4) Uani 1 1 d . . . . .
H25 H 0.830748 0.256728 1.003999 0.027 Uiso 1 1 calc R . . . .
C26 C 0.78362(15) 0.35148(11) 1.0638(2) 0.0207(4) Uani 1 1 d . . . . .
H26 H 0.821446 0.352220 1.150578 0.025 Uiso 1 1 calc R . . . .
C27 C 0.72186(14) 0.40781(10) 1.0226(2) 0.0169(4) Uani 1 1 d . . . . .
H27 H 0.718839 0.446319 1.081484 0.020 Uiso 1 1 calc R . . . .
C28 C 0.54639(14) 0.64172(9) 0.96645(19) 0.0136(3) Uani 1 1 d . . . . .
C29 C 0.61461(14) 0.64655(10) 1.0866(2) 0.0179(4) Uani 1 1 d . . . . .
H29 H 0.654662 0.608268 1.114806 0.021 Uiso 1 1 calc R . . . .
C30 C 0.62264(15) 0.70807(11) 1.1634(2) 0.0217(4) Uani 1 1 d . . . . .
H30 H 0.668123 0.711166 1.242968 0.026 Uiso 1 1 calc R . . . .
C31 C 0.56278(16) 0.76512(10) 1.1215(2) 0.0213(4) Uani 1 1 d . . . . .
H31 H 0.569131 0.806813 1.171956 0.026 Uiso 1 1 calc R . . . .
C32 C 0.49378(16) 0.76013(10) 1.0050(2) 0.0213(4) Uani 1 1 d . . . . .
H32 H 0.453073 0.798300 0.978225 0.026 Uiso 1 1 calc R . . . .
C33 C 0.48471(14) 0.69863(10) 0.92748(19) 0.0168(4) Uani 1 1 d . . . . .
H33 H 0.437566 0.695413 0.849711 0.020 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 0.01943(10) 0.01586(9) 0.01435(9) 0.00258(7) 0.00301(7) -0.00001(8)
N1 0.0101(7) 0.0109(7) 0.0176(8) -0.0020(6) -0.0041(6) 0.0013(6)
N2 0.0120(7) 0.0158(7) 0.0123(7) 0.0010(6) -0.0007(6) 0.0000(6)
N3 0.0131(8) 0.0166(8) 0.0136(7) -0.0011(6) 0.0003(6) -0.0013(6)
N4 0.0120(7) 0.0151(7) 0.0126(7) -0.0013(6) 0.0006(6) -0.0014(6)
C1 0.0108(8) 0.0141(8) 0.0113(9) 0.0006(6) 0.0012(7) -0.0022(6)
C2 0.0091(8) 0.0160(8) 0.0130(8) 0.0016(7) 0.0026(7) -0.0021(7)
C3 0.0115(8) 0.0158(9) 0.0119(8) -0.0001(7) 0.0027(7) -0.0025(7)
C4 0.0108(8) 0.0150(8) 0.0116(9) -0.0002(6) 0.0005(7) -0.0001(7)
C5 0.0135(9) 0.0122(8) 0.0129(8) -0.0008(6) 0.0012(7) -0.0018(7)
C6 0.0116(8) 0.0123(8) 0.0139(8) 0.0018(6) 0.0006(7) 0.0023(7)
C7 0.0104(8) 0.0147(8) 0.0115(8) -0.0002(6) 0.0006(7) -0.0012(7)
C8 0.0180(9) 0.0125(8) 0.0182(9) -0.0033(7) -0.0035(7) 0.0015(7)
C9 0.0152(9) 0.0148(9) 0.0172(9) -0.0012(7) -0.0036(7) 0.0039(7)
C10 0.0136(8) 0.0113(8) 0.0139(8) -0.0005(6) -0.0048(7) 0.0011(7)
C11 0.0160(9) 0.0146(8) 0.0129(9) 0.0007(7) -0.0017(7) 0.0021(7)
C12 0.0228(10) 0.0149(9) 0.0191(10) 0.0018(7) -0.0040(8) -0.0035(8)
C13 0.0288(11) 0.0134(9) 0.0187(10) -0.0014(7) -0.0072(8) 0.0010(8)
C14 0.0236(10) 0.0195(9) 0.0138(9) -0.0031(7) -0.0040(8) 0.0069(8)
C15 0.0143(9) 0.0182(9) 0.0150(9) 0.0005(7) -0.0017(7) 0.0022(7)
C16 0.0111(8) 0.0137(8) 0.0141(9) -0.0028(6) -0.0034(7) 0.0017(7)
C17 0.0148(9) 0.0142(8) 0.0099(8) -0.0003(6) -0.0021(7) 0.0000(7)
C18 0.0124(9) 0.0205(9) 0.0156(9) -0.0021(7) 0.0002(7) 0.0007(7)
C19 0.0145(9) 0.0185(9) 0.0205(10) 0.0003(7) -0.0038(8) 0.0054(7)
C20 0.0195(10) 0.0133(8) 0.0214(10) 0.0035(7) -0.0033(8) -0.0001(7)
C21 0.0128(9) 0.0159(9) 0.0188(9) 0.0012(7) -0.0001(7) -0.0018(7)
C22 0.0104(8) 0.0163(9) 0.0151(9) 0.0030(6) 0.0011(7) -0.0016(7)
C23 0.0164(9) 0.0207(9) 0.0160(9) 0.0006(7) -0.0025(7) -0.0006(7)
C24 0.0237(11) 0.0180(9) 0.0257(11) -0.0021(8) 0.0031(9) 0.0036(8)
C25 0.0186(10) 0.0207(10) 0.0280(11) 0.0070(8) -0.0008(8) 0.0045(8)
C26 0.0172(10) 0.0265(10) 0.0172(10) 0.0058(8) -0.0043(8) 0.0009(8)
C27 0.0137(9) 0.0208(10) 0.0161(9) 0.0008(7) 0.0002(7) -0.0006(7)
C28 0.0135(9) 0.0154(9) 0.0121(8) -0.0016(7) 0.0025(7) -0.0041(7)
C29 0.0161(9) 0.0213(10) 0.0160(9) -0.0013(7) 0.0002(7) -0.0025(8)
C30 0.0213(10) 0.0281(11) 0.0152(9) -0.0054(8) 0.0001(8) -0.0070(8)
C31 0.0300(11) 0.0173(9) 0.0183(10) -0.0056(7) 0.0101(8) -0.0078(8)
C32 0.0280(11) 0.0165(9) 0.0203(10) 0.0012(7) 0.0071(8) 0.0010(8)
C33 0.0173(9) 0.0195(9) 0.0138(9) 0.0002(7) 0.0023(7) -0.0011(7)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Se C11 1.9164(19) . ?
Se C17 1.9141(18) . ?
N1 C7 1.397(2) . ?
N1 C10 1.430(2) . ?
N1 C16 1.433(2) . ?
N2 C1 1.344(2) . ?
N2 C2 1.334(2) . ?
N3 C2 1.343(2) . ?
N3 C3 1.343(2) . ?
N4 C1 1.345(2) . ?
N4 C3 1.341(2) . ?
C1 C4 1.477(2) . ?
C2 C22 1.483(2) . ?
C3 C28 1.484(2) . ?
C4 C5 1.397(2) . ?
C4 C9 1.394(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.404(2) . ?
C7 C8 1.404(3) . ?
C8 C9 1.382(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.388(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.390(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.385(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.385(3) . ?
C22 C23 1.392(3) . ?
C22 C27 1.396(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.390(3) . ?
C25 C26 1.384(3) . ?
C26 C27 1.389(3) . ?
C28 C29 1.400(3) . ?
C28 C33 1.392(3) . ?
C29 C30 1.383(3) . ?
C30 C31 1.387(3) . ?
C31 C32 1.381(3) . ?
C32 C33 1.387(3) . ?

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
C17 Se C11 93.22(8) . . ?
C7 N1 C10 120.37(14) . . ?
C7 N1 C16 122.19(15) . . ?
C10 N1 C16 114.46(14) . . ?
C2 N2 C1 115.48(15) . . ?
C3 N3 C2 114.95(15) . . ?
C3 N4 C1 114.73(15) . . ?
N2 C1 N4 124.72(16) . . ?
N2 C1 C4 116.72(15) . . ?
N4 C1 C4 118.50(16) . . ?
N2 C2 N3 124.84(16) . . ?
N2 C2 C22 117.60(16) . . ?
N3 C2 C22 117.54(16) . . ?
N3 C3 C28 116.81(16) . . ?
N4 C3 N3 125.24(16) . . ?
N4 C3 C28 117.95(16) . . ?
C5 C4 C1 122.54(16) . . ?
C9 C4 C1 119.51(16) . . ?
C9 C4 C5 117.91(16) . . ?
C6 C5 C4 121.32(16) . . ?
C5 C6 C7 120.66(16) . . ?
N1 C7 C6 122.07(16) . . ?
N1 C7 C8 120.03(16) . . ?
C8 C7 C6 117.89(16) . . ?
C9 C8 C7 120.84(17) . . ?
C8 C9 C4 121.37(17) . . ?
C11 C10 N1 119.39(16) . . ?
C15 C10 N1 120.47(17) . . ?
C15 C10 C11 120.11(16) . . ?
C10 C11 Se 117.67(13) . . ?
C10 C11 C12 120.22(18) . . ?
C12 C11 Se 122.09(15) . . ?
C13 C12 C11 119.57(19) . . ?
C12 C13 C14 120.31(18) . . ?
C15 C14 C13 120.04(19) . . ?
C10 C15 C14 119.72(18) . . ?
C17 C16 N1 119.11(16) . . ?
C21 C16 N1 120.97(17) . . ?
C21 C16 C17 119.79(17) . . ?
C16 C17 Se 117.73(13) . . ?
C18 C17 Se 122.10(14) . . ?
C18 C17 C16 120.10(17) . . ?
C19 C18 C17 119.76(18) . . ?
C18 C19 C20 120.03(18) . . ?
C21 C20 C19 120.39(18) . . ?
C16 C21 C20 119.90(18) . . ?
C23 C22 C2 120.19(16) . . ?
C23 C22 C27 119.20(17) . . ?
C27 C22 C2 120.59(17) . . ?
C24 C23 C22 120.54(18) . . ?
C23 C24 C25 119.93(19) . . ?
C26 C25 C24 119.96(18) . . ?
C25 C26 C27 120.22(18) . . ?
C26 C27 C22 120.15(18) . . ?
C29 C28 C3 119.56(17) . . ?
C33 C28 C3 121.04(16) . . ?
C33 C28 C29 119.39(17) . . ?
C30 C29 C28 120.22(19) . . ?
C29 C30 C31 119.92(18) . . ?
C32 C31 C30 120.10(18) . . ?
C31 C32 C33 120.50(19) . . ?
C32 C33 C28 119.81(18) . . ?

_shelx_res_file                  
;
TITL 18srv310_a.res in P2(1)/c
    18srv310.res
    created by SHELXL-2018/3 at 23:26:57 on 26-Jul-2018
REM Old TITL 18srv310 in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.077, Rweak 0.005, Alpha 0.021
REM <I/s> 0.397 for 169 systematic absences, Orientation as input
REM Formula found by SHELXT: C33 N4 Se
CELL 0.71073 13.4469 19.0511 9.613 90 96.035 90
ZERR 4 0.0009 0.0011 0.0006 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N Se
UNIT 132 88 16 4

L.S. 7
PLAN  6
SIZE 0.062 0.103 0.184
TEMP 0
BOND
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\18srv310.hkl">
REM </olex2.extras>

WGHT    0.024000    2.070900
FVAR       0.10480
SE    4   -0.034301    0.392262    0.394662    11.00000    0.01943    0.01586 =
         0.01435    0.00258    0.00301   -0.00001
N1    3    0.147214    0.454464    0.281796    11.00000    0.01012    0.01090 =
         0.01757   -0.00198   -0.00414    0.00126
N2    3    0.528307    0.455466    0.739766    11.00000    0.01204    0.01582 =
         0.01230    0.00099   -0.00069   -0.00002
N3    3    0.604731    0.524634    0.926585    11.00000    0.01309    0.01659 =
         0.01364   -0.00108    0.00027   -0.00132
N4    3    0.469155    0.571304    0.774953    11.00000    0.01203    0.01510 =
         0.01259   -0.00129    0.00057   -0.00145
C1    1    0.465529    0.509328    0.707622    11.00000    0.01081    0.01415 =
         0.01128    0.00065    0.00123   -0.00223
C2    1    0.595860    0.465646    0.849790    11.00000    0.00915    0.01599 =
         0.01304    0.00162    0.00260   -0.00215
C3    1    0.539592    0.575663    0.884262    11.00000    0.01147    0.01576 =
         0.01185   -0.00013    0.00273   -0.00246
C4    1    0.384571    0.497468    0.593879    11.00000    0.01080    0.01498 =
         0.01160   -0.00023    0.00048   -0.00006
C5    1    0.319985    0.550856    0.541381    11.00000    0.01355    0.01223 =
         0.01287   -0.00084    0.00119   -0.00182
AFIX  43
H5    2    0.329120    0.596114    0.576683    11.00000   -1.20000
AFIX   0
C6    1    0.242572    0.537734    0.437749    11.00000    0.01160    0.01227 =
         0.01395    0.00177    0.00059    0.00231
AFIX  43
H6    2    0.201126    0.574307    0.403689    11.00000   -1.20000
AFIX   0
C7    1    0.226084    0.469774    0.383655    11.00000    0.01035    0.01473 =
         0.01151   -0.00023    0.00055   -0.00115
C8    1    0.290887    0.416155    0.436989    11.00000    0.01796    0.01248 =
         0.01824   -0.00332   -0.00346    0.00150
AFIX  43
H8    2    0.281405    0.370644    0.403187    11.00000   -1.20000
AFIX   0
C9    1    0.368603    0.430157    0.539103    11.00000    0.01518    0.01475 =
         0.01721   -0.00116   -0.00363    0.00385
AFIX  43
H9    2    0.411115    0.393928    0.571943    11.00000   -1.20000
AFIX   0
C10   1    0.130664    0.384054    0.233171    11.00000    0.01363    0.01127 =
         0.01392   -0.00053   -0.00478    0.00111
C11   1    0.050245    0.346337    0.274326    11.00000    0.01603    0.01463 =
         0.01289    0.00069   -0.00168    0.00212
C12   1    0.031922    0.278223    0.226166    11.00000    0.02281    0.01488 =
         0.01914    0.00175   -0.00396   -0.00351
AFIX  43
H12   2   -0.022280    0.253164    0.252951    11.00000   -1.20000
AFIX   0
C13   1    0.094928    0.247968    0.138063    11.00000    0.02882    0.01339 =
         0.01872   -0.00138   -0.00717    0.00102
AFIX  43
H13   2    0.083948    0.202026    0.107527    11.00000   -1.20000
AFIX   0
C14   1    0.174583    0.285989    0.095018    11.00000    0.02361    0.01948 =
         0.01382   -0.00305   -0.00400    0.00689
AFIX  43
H14   2    0.216112    0.265661    0.034800    11.00000   -1.20000
AFIX   0
C15   1    0.192117    0.354310    0.141952    11.00000    0.01434    0.01822 =
         0.01496    0.00047   -0.00172    0.00224
AFIX  43
H15   2    0.244816    0.379991    0.112349    11.00000   -1.20000
AFIX   0
C16   1    0.062580    0.499973    0.254344    11.00000    0.01108    0.01367 =
         0.01413   -0.00278   -0.00343    0.00173
C17   1   -0.028585    0.480274    0.299789    11.00000    0.01484    0.01424 =
         0.00994   -0.00035   -0.00209   -0.00001
C18   1   -0.112435    0.522505    0.270465    11.00000    0.01245    0.02049 =
         0.01565   -0.00212    0.00017    0.00065
AFIX  43
H18   2   -0.173011    0.509675    0.301707    11.00000   -1.20000
AFIX   0
C19   1   -0.105457    0.583771    0.194542    11.00000    0.01455    0.01848 =
         0.02048    0.00027   -0.00379    0.00537
AFIX  43
H19   2   -0.161199    0.612471    0.175778    11.00000   -1.20000
AFIX   0
C20   1   -0.015383    0.602337    0.146488    11.00000    0.01953    0.01330 =
         0.02138    0.00345   -0.00329   -0.00014
AFIX  43
H20   2   -0.011291    0.643035    0.093969    11.00000   -1.20000
AFIX   0
C21   1    0.068526    0.560622    0.176252    11.00000    0.01283    0.01594 =
         0.01878    0.00122   -0.00013   -0.00184
AFIX  43
H21   2    0.128766    0.573327    0.143839    11.00000   -1.20000
AFIX   0
C22   1    0.664333    0.406761    0.893019    11.00000    0.01044    0.01626 =
         0.01513    0.00299    0.00106   -0.00160
C23   1    0.669816    0.348778    0.806116    11.00000    0.01640    0.02069 =
         0.01600    0.00063   -0.00253   -0.00055
AFIX  43
H23   2    0.631341    0.347511    0.719906    11.00000   -1.20000
AFIX   0
C24   1    0.732163    0.292888    0.847005    11.00000    0.02373    0.01800 =
         0.02574   -0.00208    0.00306    0.00361
AFIX  43
H24   2    0.735912    0.254524    0.787962    11.00000   -1.20000
AFIX   0
C25   1    0.789050    0.294252    0.976308    11.00000    0.01859    0.02067 =
         0.02796    0.00696   -0.00082    0.00453
AFIX  43
H25   2    0.830748    0.256728    1.003999    11.00000   -1.20000
AFIX   0
C26   1    0.783620    0.351477    1.063846    11.00000    0.01718    0.02646 =
         0.01720    0.00584   -0.00428    0.00094
AFIX  43
H26   2    0.821446    0.352220    1.150578    11.00000   -1.20000
AFIX   0
C27   1    0.721862    0.407813    1.022612    11.00000    0.01367    0.02076 =
         0.01608    0.00082    0.00015   -0.00062
AFIX  43
H27   2    0.718839    0.446319    1.081484    11.00000   -1.20000
AFIX   0
C28   1    0.546388    0.641717    0.966454    11.00000    0.01346    0.01540 =
         0.01209   -0.00163    0.00250   -0.00415
C29   1    0.614610    0.646549    1.086561    11.00000    0.01608    0.02129 =
         0.01599   -0.00133    0.00022   -0.00251
AFIX  43
H29   2    0.654662    0.608268    1.114806    11.00000   -1.20000
AFIX   0
C30   1    0.622639    0.708069    1.163352    11.00000    0.02126    0.02810 =
         0.01524   -0.00538    0.00008   -0.00702
AFIX  43
H30   2    0.668123    0.711166    1.242968    11.00000   -1.20000
AFIX   0
C31   1    0.562780    0.765124    1.121472    11.00000    0.02998    0.01732 =
         0.01829   -0.00562    0.01008   -0.00780
AFIX  43
H31   2    0.569131    0.806813    1.171956    11.00000   -1.20000
AFIX   0
C32   1    0.493782    0.760131    1.004960    11.00000    0.02802    0.01648 =
         0.02026    0.00119    0.00706    0.00101
AFIX  43
H32   2    0.453073    0.798300    0.978225    11.00000   -1.20000
AFIX   0
C33   1    0.484711    0.698630    0.927480    11.00000    0.01734    0.01949 =
         0.01381    0.00021    0.00230   -0.00106
AFIX  43
H33   2    0.437566    0.695413    0.849711    11.00000   -1.20000
AFIX   0
HKLF 4




REM  18srv310_a.res in P2(1)/c
REM wR2 = 0.0811, GooF = S = 1.026, Restrained GooF = 1.026 for all data
REM R1 = 0.0372 for 5530 Fo > 4sig(Fo) and 0.0606 for all 7152 data
REM 343 parameters refined using 0 restraints

END

WGHT      0.0236      2.0927

REM Highest difference peak  0.471,  deepest hole -0.467,  1-sigma level  0.078
Q1    1   0.4257  0.5057  0.6456  11.00000  0.05    0.47
Q2    1   0.6979  0.3202  0.8395  11.00000  0.05    0.43
Q3    1   0.0192  0.4962  0.2815  11.00000  0.05    0.43
Q4    1   0.2908  0.5424  0.4842  11.00000  0.05    0.41
Q5    1   0.2612  0.4420  0.4002  11.00000  0.05    0.41
Q6    1  -0.0571  0.5821  0.1755  11.00000  0.05    0.40
;
_shelx_res_checksum              12339
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PTZ-250KPTZ-250K
_database_code_depnum_ccdc_archive 'CCDC 1902672'
loop_
_audit_author_name
_audit_author_address
'Andrei S. Batsanov'
;Durham University
United Kingdom
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-07-17 downloaded from the CCDC.
;
_ccdc_comments                   'same as PHESAZ01'

_audit_creation_date             2019-03-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            phenothiazine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N S'
_chemical_formula_sum            'C12 H9 N S'
_chemical_formula_weight         199.26
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   7.8739(8)
_cell_length_b                   20.921(2)
_cell_length_c                   5.8718(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     967.26(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4945
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      25.184
_cell_measurement_theta_min      3.606
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 
   0.1816 before and 0.0686 after correction. The Ratio of minimum to maximum 
   transmission is 0.8809. The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 0.00 0.1770
-1.00 0.00 0.00 0.1730
0.00 0.00 -1.00 0.1880
-1.00 1.00 1.00 0.2240
1.00 -1.00 2.00 0.1930
0.00 -1.00 0.00 0.0640
0.00 1.00 0.00 0.0300

_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.128
_exptl_special_details           
; Data were collected in shutterless mode. Full sphere of reciprocal 
  space was nominally covered by 3 runs of 340 narrow-frame ω-scans 
  (scan width 0.5°, 5s exposure), every run at a different φ angle. 
  Two runs of 358 φ-scans (scan width 1°, 1.5s exposure) were used for 
  scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9837
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         3.604
_diffrn_ambient_temperature      250
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                654
_reflns_number_total             876
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2013/1 (Sheldrick, 2008)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.015(8)
_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   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.076
_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)+(0.0561P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          
;
 Amino H atom - refall, other H atoms - riding.
;
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

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
S S 0.13402(9) 0.250000 0.20908(13) 0.0833(5) Uani 1 2 d S T P . .
N N 0.3328(4) 0.250000 -0.2293(5) 0.0661(9) Uani 1 2 d S T P . .
H H 0.387(4) 0.250000 -0.341(6) 0.055(9) Uiso 1 2 d S T P . .
C1 C 0.2450(2) 0.31468(13) 0.0898(3) 0.0671(7) Uani 1 1 d . . . . .
C2 C 0.3272(2) 0.30874(12) -0.1207(3) 0.0582(7) Uani 1 1 d . . . . .
C3 C 0.3985(3) 0.36275(14) -0.2171(4) 0.0689(7) Uani 1 1 d . . . . .
H3 H 0.455670 0.359184 -0.357030 0.083 Uiso 1 1 calc R . . . .
C4 C 0.3878(3) 0.42139(15) -0.1136(5) 0.0863(9) Uani 1 1 d . . . . .
H4 H 0.434409 0.457673 -0.184354 0.104 Uiso 1 1 calc R . . . .
C5 C 0.3082(4) 0.42687(18) 0.0952(6) 0.0986(10) Uani 1 1 d . . . . .
H5 H 0.301614 0.466750 0.168433 0.118 Uiso 1 1 calc R . . . .
C6 C 0.2389(3) 0.37357(19) 0.1947(4) 0.0888(10) Uani 1 1 d . . . . .
H6 H 0.185967 0.377306 0.337564 0.107 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 0.0356(5) 0.1819(12) 0.0325(5) 0.000 0.0084(3) 0.000
N 0.0542(16) 0.118(3) 0.0257(13) 0.000 0.0084(12) 0.000
C1 0.0306(10) 0.137(2) 0.0340(11) -0.0084(13) -0.0039(8) 0.0200(11)
C2 0.0330(10) 0.1092(18) 0.0325(10) -0.0036(12) -0.0029(8) 0.0143(11)
C3 0.0431(13) 0.1102(19) 0.0533(13) 0.0075(15) -0.0001(10) 0.0236(12)
C4 0.0616(16) 0.103(2) 0.094(2) 0.0011(18) -0.0066(14) 0.0346(14)
C5 0.0684(18) 0.130(3) 0.097(2) -0.029(2) -0.0113(17) 0.0424(19)
C6 0.0463(15) 0.165(3) 0.0551(15) -0.028(2) -0.0072(12) 0.0355(17)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S C1 1.756(3) . ?
S C1 1.757(3) 8_565 ?
N C2 1.385(2) . ?
N C2 1.385(2) 8_565 ?
C1 C2 1.401(3) . ?
C1 C6 1.378(4) . ?
C2 C3 1.383(3) . ?
C3 C4 1.372(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.372(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
_geom_angle_publ_flag
C1 S C1 100.77(15) . 8_565 ?
C2 N C2 125.0(3) 8_565 . ?
C2 C1 S 120.9(2) . . ?
C6 C1 S 119.5(2) . . ?
C6 C1 C2 119.3(2) . . ?
N C2 C1 120.0(2) . . ?
C3 C2 N 121.6(2) . . ?
C3 C2 C1 118.4(2) . . ?
C4 C3 C2 121.6(2) . . ?
C3 C4 C5 119.7(3) . . ?
C6 C5 C4 119.4(3) . . ?
C5 C6 C1 121.5(2) . . ?

_shelx_res_file                  
;
TITL 19srv026 in Pnma #62
    19srv026.res
    created by SHELXL-2018/3 at 20:43:44 on 18-Feb-2019
REM reset to Pnma #62
CELL 0.71073 7.8739 20.921 5.8718 90 90 90
ZERR 4 0.0008 0.002 0.0006 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C H N S
UNIT 48 36 4 4

L.S. 7 0 0
PLAN  6
SIZE 0.128 0.354 0.468
TEMP -23.15
BOND
fmap 2 53
acta 50
REM <olex2.extras>
REM <HklSrc "%.\\19srv026.hkl">
REM </olex2.extras>

WGHT    0.056100    0.281000
EXTI    0.015456
FVAR       0.35533
S     4    0.134021    0.250000    0.209081    10.50000    0.03559    0.18191 =
         0.03252    0.00000    0.00836    0.00000
N     3    0.332808    0.250000   -0.229322    10.50000    0.05416    0.11834 =
         0.02574    0.00000    0.00839    0.00000
H     2    0.386741    0.250000   -0.341041    10.50000    0.05523
C1    1    0.245039    0.314677    0.089845    11.00000    0.03060    0.13669 =
         0.03396   -0.00842   -0.00393    0.01996
C2    1    0.327189    0.308743   -0.120699    11.00000    0.03297    0.10916 =
         0.03253   -0.00361   -0.00290    0.01428
C3    1    0.398471    0.362745   -0.217088    11.00000    0.04312    0.11020 =
         0.05327    0.00749   -0.00009    0.02357
AFIX  43
H3    2    0.455670    0.359184   -0.357030    11.00000   -1.20000
AFIX   0
C4    1    0.387796    0.421391   -0.113574    11.00000    0.06157    0.10299 =
         0.09442    0.00106   -0.00656    0.03463
AFIX  43
H4    2    0.434409    0.457673   -0.184354    11.00000   -1.20000
AFIX   0
C5    1    0.308207    0.426873    0.095203    11.00000    0.06836    0.13009 =
         0.09736   -0.02879   -0.01131    0.04242
AFIX  43
H5    2    0.301614    0.466750    0.168433    11.00000   -1.20000
AFIX   0
C6    1    0.238872    0.373568    0.194674    11.00000    0.04630    0.16517 =
         0.05505   -0.02766   -0.00721    0.03551
AFIX  43
H6    2    0.185967    0.377306    0.337564    11.00000   -1.20000
AFIX   0
HKLF 4




REM  19srv026 in Pnma #62
REM wR2 = 0.1146, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0442 for 654 Fo > 4sig(Fo) and 0.0628 for all 876 data
REM 71 parameters refined using 0 restraints

END

WGHT      0.0562      0.2861

REM Highest difference peak  0.212,  deepest hole -0.249,  1-sigma level  0.034
Q1    1   0.2209  0.2852  0.2098  11.00000  0.05    0.21
Q2    1   0.0145  0.2500  0.2092  10.50000  0.05    0.15
Q3    1   0.2585  0.3136 -0.0090  11.00000  0.05    0.11
Q4    1   0.0998  0.3441  0.2198  11.00000  0.05    0.11
Q5    1   0.3230  0.4987  0.1026  11.00000  0.05    0.11
Q6    1   0.3111  0.3957  0.2047  11.00000  0.05    0.10
;
_shelx_res_checksum              74960
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_submission_special_instructions 'No special instructions were received'
