# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Methyle
_database_code_depnum_ccdc_archive 'CCDC 999722'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C22 H23 N5 S2'
_chemical_formula_sum            'C22 H23 N5 S2'
_chemical_formula_weight         421.59
_chemical_oxdiff_formula         C22H23N5S2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   9.5447(4)
_cell_length_b                   14.8256(5)
_cell_length_c                   15.3905(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.452(4)
_cell_angle_gamma                90
_cell_volume                     2126.61(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2482
_cell_measurement_temperature    295.73(10)
_cell_measurement_theta_max      26.7440
_cell_measurement_theta_min      2.5780
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3167
_exptl_crystal_description       plate
_exptl_crystal_F_000             889.2461
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7193
_diffrn_reflns_theta_full        26.996159
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.93
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.73(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9160
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9845
_diffrn_measured_fraction_theta_max 0.9845
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   57.00   95.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074 -128.0000  153.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   50.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -38.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   63.00   1.0000   40.8500
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -57.0000   30.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0297867000
_diffrn_orient_matrix_UB_12      0.0016859000
_diffrn_orient_matrix_UB_13      -0.0463654000
_diffrn_orient_matrix_UB_21      0.0685806000
_diffrn_orient_matrix_UB_22      0.0102193000
_diffrn_orient_matrix_UB_23      -0.0082165000
_diffrn_orient_matrix_UB_31      0.0139232000
_diffrn_orient_matrix_UB_32      -0.0467069000
_diffrn_orient_matrix_UB_33      -0.0034562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -8
_reflns_number_gt                3011
_reflns_number_total             4473
_reflns_odcompleteness_completeness 98.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.307021
_refine_diff_density_min         -0.454207
_refine_diff_density_rms         0.075553
_refine_ls_d_res_high            0.782862
_refine_ls_d_res_low             10.554282
_refine_ls_goodness_of_fit_ref   1.075578
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.086826
_refine_ls_R_factor_gt           0.058301
_refine_ls_restrained_S_all      1.075578
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.156560
_atom_sites_solution_primary     direct
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_refinement_flags_posn
C1 C 0.0016(3) 0.2802(2) 0.2527(2) 0.0598(8) Uani 1.000000 .
H1a H -0.0812(3) 0.2841(2) 0.2797(2) 0.0717(9) Uiso 1.000000 R
H1b H -0.0027(3) 0.2227(2) 0.2221(2) 0.0717(9) Uiso 1.000000 R
C2 C -0.0046(3) 0.3558(2) 0.1860(2) 0.0633(8) Uani 1.000000 .
H2a H 0.0090(3) 0.4129(2) 0.2175(2) 0.0760(10) Uiso 1.000000 R
H2b H 0.0733(3) 0.3485(2) 0.1553(2) 0.0760(10) Uiso 1.000000 R
C3 C -0.1455(3) 0.3582(2) 0.1182(2) 0.0609(8) Uani 1.000000 .
H3a H -0.1658(3) 0.2983(2) 0.0933(2) 0.0731(9) Uiso 1.000000 R
H3b H -0.2216(3) 0.3741(2) 0.1482(2) 0.0731(9) Uiso 1.000000 R
C4 C -0.1470(3) 0.4243(2) 0.0430(2) 0.0624(8) Uani 1.000000 .
H4a H -0.1219(3) 0.4837(2) 0.0679(2) 0.0748(10) Uiso 1.000000 R
H4b H -0.0744(3) 0.4066(2) 0.0109(2) 0.0748(10) Uiso 1.000000 R
C5 C -0.2903(4) 0.4295(2) -0.0215(2) 0.0755(10) Uani 1.000000 .
H5a H -0.3173(4) 0.3695(2) -0.0442(2) 0.0906(12) Uiso 1.000000 R
H5b H -0.3620(4) 0.4497(2) 0.0103(2) 0.0906(12) Uiso 1.000000 R
C6 C -0.2917(5) 0.4915(3) -0.0983(3) 0.1142(16) Uani 1.000000 .
H6a H -0.227(3) 0.4692(13) -0.1331(13) 0.171(2) Uiso 1.000000 G
H6b H -0.3869(10) 0.4943(19) -0.1346(13) 0.171(2) Uiso 1.000000 G
H6c H -0.262(4) 0.5507(7) -0.0765(3) 0.171(2) Uiso 1.000000 G
C7 C 0.7771(4) 0.1130(2) 0.3252(2) 0.0718(9) Uani 1.000000 .
H7 H 0.8308(4) 0.0754(2) 0.2966(2) 0.0862(11) Uiso 1.000000 R
C8 C 0.8339(4) 0.1553(2) 0.4028(2) 0.0689(9) Uani 1.000000 .
H8 H 0.9289(4) 0.1506(2) 0.4336(2) 0.0827(11) Uiso 1.000000 R
C9 C 0.7267(3) 0.20801(19) 0.43031(19) 0.0537(7) Uani 1.000000 .
C10 C 0.5947(3) 0.20269(18) 0.37387(18) 0.0508(7) Uani 1.000000 .
C11 C 0.4983(3) 0.25669(17) 0.40969(17) 0.0469(6) Uani 1.000000 .
C12 C 0.5802(3) 0.29643(18) 0.48866(17) 0.0465(6) Uani 1.000000 .
C13 C 0.5113(3) 0.36046(17) 0.53666(16) 0.0471(7) Uani 1.000000 .
C14 C 0.3612(3) 0.37379(17) 0.51149(17) 0.0477(7) Uani 1.000000 .
C15 C 0.3263(3) 0.44048(18) 0.56869(18) 0.0528(7) Uani 1.000000 .
C16 C 0.4523(4) 0.46805(18) 0.62423(17) 0.0536(7) Uani 1.000000 .
C17 C 0.4354(4) 0.5423(2) 0.67989(19) 0.0643(9) Uani 1.000000 .
H17 H 0.5095(4) 0.5697(2) 0.72050(19) 0.0771(11) Uiso 1.000000 R
C18 C 0.2963(4) 0.5671(2) 0.6651(2) 0.0725(10) Uani 1.000000 .
H18 H 0.2641(4) 0.6143(2) 0.6954(2) 0.0870(12) Uiso 1.000000 R
C19 C 0.2811(3) 0.33019(18) 0.43428(17) 0.0475(6) Uani 1.000000 .
C20 C 0.3505(3) 0.27474(17) 0.38252(17) 0.0462(6) Uani 1.000000 .
C21 C 0.8403(4) 0.2710(3) 0.5776(2) 0.0780(10) Uani 1.000000 .
H21a H 0.8916(16) 0.3261(8) 0.5740(8) 0.1170(15) Uiso 1.000000 G
H21b H 0.8045(4) 0.2709(16) 0.6313(2) 0.1170(15) Uiso 1.000000 G
H21c H 0.9036(14) 0.2207(9) 0.5780(9) 0.1170(15) Uiso 1.000000 G
C22 C 0.7136(3) 0.4426(2) 0.6463(2) 0.0644(8) Uani 1.000000 .
H22a H 0.7515(8) 0.4001(9) 0.6925(10) 0.0966(12) Uiso 1.000000 G
H22b H 0.7700(6) 0.4409(14) 0.6017(4) 0.0966(12) Uiso 1.000000 G
H22c H 0.7168(4) 0.5021(6) 0.6711(13) 0.0966(12) Uiso 1.000000 G
N1 N 0.2539(3) 0.24653(15) 0.31038(15) 0.0516(6) Uani 1.000000 .
N2 N 0.1315(3) 0.28398(16) 0.32182(15) 0.0529(6) Uani 1.000000 .
N3 N 0.1406(3) 0.33572(16) 0.39425(15) 0.0539(6) Uani 1.000000 .
N4 N 0.5666(3) 0.41919(15) 0.60654(14) 0.0516(6) Uani 1.000000 .
N5 N 0.7204(3) 0.26416(16) 0.50102(15) 0.0530(6) Uani 1.000000 .
S1 S 0.59820(9) 0.13408(5) 0.28379(5) 0.0640(3) Uani 1.000000 .
S2 S 0.18278(10) 0.50397(6) 0.58510(5) 0.0679(3) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1a 0.9700 .
C1 H1b 0.9700 .
C1 C2 1.512(4) .
C1 N2 1.451(4) .
C2 H2a 0.9700 .
C2 H2b 0.9700 .
C2 C3 1.514(4) .
C3 H3a 0.9700 .
C3 H3b 0.9700 .
C3 C4 1.514(4) .
C4 H4a 0.9700 .
C4 H4b 0.9700 .
C4 C5 1.509(4) .
C5 H5a 0.9700 .
C5 H5b 0.9700 .
C5 C6 1.495(5) .
C6 H6a 0.9600 .
C6 H6b 0.9600 .
C6 H6c 0.9600 .
C7 H7 0.9300 .
C7 C8 1.355(5) .
C7 S1 1.718(4) .
C8 H8 0.9300 .
C8 C9 1.423(4) .
C9 C10 1.369(4) .
C9 N5 1.382(3) .
C10 C11 1.418(4) .
C10 S1 1.726(3) .
C11 C12 1.423(4) .
C11 C20 1.407(4) .
C12 C13 1.446(4) .
C12 N5 1.395(3) .
C13 C14 1.415(4) .
C13 N4 1.396(3) .
C14 C15 1.410(4) .
C14 C19 1.422(4) .
C15 C16 1.378(4) .
C15 S2 1.725(3) .
C16 C17 1.425(4) .
C16 N4 1.385(4) .
C17 H17 0.9300 .
C17 C18 1.349(5) .
C18 H18 0.9300 .
C18 S2 1.729(4) .
C19 C20 1.406(3) .
C19 N3 1.352(4) .
C20 N1 1.348(3) .
C21 H21a 0.9600 .
C21 H21b 0.9600 .
C21 H21c 0.9600 .
C21 N5 1.459(4) .
C22 H22a 0.9600 .
C22 H22b 0.9600 .
C22 H22c 0.9600 .
C22 N4 1.446(4) .
N1 N2 1.339(3) .
N2 N3 1.340(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
H1b C1 H1a 107.9 . .
C2 C1 H1a 109.26(17) . .
C2 C1 H1b 109.26(16) . .
N2 C1 H1a 109.26(15) . .
N2 C1 H1b 109.26(15) . .
N2 C1 C2 111.8(2) . .
H2a C2 C1 109.07(16) . .
H2b C2 C1 109.07(17) . .
H2b C2 H2a 107.8 . .
C3 C2 C1 112.6(3) . .
C3 C2 H2a 109.07(17) . .
C3 C2 H2b 109.07(17) . .
H3a C3 C2 108.80(17) . .
H3b C3 C2 108.80(17) . .
H3b C3 H3a 107.7 . .
C4 C3 C2 113.8(3) . .
C4 C3 H3a 108.80(17) . .
C4 C3 H3b 108.80(17) . .
H4a C4 C3 108.94(17) . .
H4b C4 C3 108.94(17) . .
H4b C4 H4a 107.8 . .
C5 C4 C3 113.2(3) . .
C5 C4 H4a 108.94(19) . .
C5 C4 H4b 108.94(18) . .
H5a C5 C4 108.80(19) . .
H5b C5 C4 108.80(18) . .
H5b C5 H5a 107.7 . .
C6 C5 C4 113.8(3) . .
C6 C5 H5a 108.8(2) . .
C6 C5 H5b 108.8(2) . .
H6a C6 C5 109.5 . .
H6b C6 C5 109.5 . .
H6b C6 H6a 109.5 . .
H6c C6 C5 109.5 . .
H6c C6 H6a 109.5 . .
H6c C6 H6b 109.5 . .
C8 C7 H7 122.60(19) . .
S1 C7 H7 122.60(11) . .
S1 C7 C8 114.8(2) . .
H8 C8 C7 125.06(19) . .
C9 C8 C7 109.9(3) . .
C9 C8 H8 125.1(2) . .
C10 C9 C8 113.7(3) . .
N5 C9 C8 136.2(3) . .
N5 C9 C10 110.1(2) . .
C11 C10 C9 107.8(2) . .
S1 C10 C9 111.7(2) . .
S1 C10 C11 140.5(2) . .
C12 C11 C10 106.4(3) . .
C20 C11 C10 133.2(3) . .
C20 C11 C12 120.4(2) . .
C13 C12 C11 118.8(3) . .
N5 C12 C11 108.0(2) . .
N5 C12 C13 133.2(3) . .
C14 C13 C12 119.8(2) . .
N4 C13 C12 131.7(3) . .
N4 C13 C14 108.5(2) . .
C15 C14 C13 106.7(2) . .
C19 C14 C13 119.7(2) . .
C19 C14 C15 133.1(3) . .
C16 C15 C14 107.7(3) . .
S2 C15 C14 140.8(3) . .
S2 C15 C16 111.2(2) . .
C17 C16 C15 113.9(3) . .
N4 C16 C15 110.0(2) . .
N4 C16 C17 135.9(3) . .
H17 C17 C16 124.9(2) . .
C18 C17 C16 110.1(3) . .
C18 C17 H17 124.94(19) . .
H18 C18 C17 122.72(19) . .
S2 C18 C17 114.6(2) . .
S2 C18 H18 122.72(12) . .
C20 C19 C14 120.3(3) . .
N3 C19 C14 130.9(2) . .
N3 C19 C20 108.6(2) . .
C19 C20 C11 120.5(3) . .
N1 C20 C11 130.5(2) . .
N1 C20 C19 109.0(2) . .
H21b C21 H21a 109.5 . .
H21c C21 H21a 109.5 . .
H21c C21 H21b 109.5 . .
N5 C21 H21a 109.5 . .
N5 C21 H21b 109.5 . .
N5 C21 H21c 109.5 . .
H22b C22 H22a 109.5 . .
H22c C22 H22a 109.5 . .
H22c C22 H22b 109.5 . .
N4 C22 H22a 109.5 . .
N4 C22 H22b 109.5 . .
N4 C22 H22c 109.5 . .
N2 N1 C20 103.0(2) . .
N1 N2 C1 121.3(2) . .
N3 N2 C1 121.6(2) . .
N3 N2 N1 116.4(2) . .
N2 N3 C19 102.9(2) . .
C16 N4 C13 107.1(2) . .
C22 N4 C13 130.3(2) . .
C22 N4 C16 121.7(2) . .
C12 N5 C9 107.6(2) . .
C21 N5 C9 121.3(2) . .
C21 N5 C12 130.4(2) . .
C10 S1 C7 89.93(15) . .
C18 S2 C15 90.22(16) . .

_chemical_name_systematic        methylthienopyrrole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-DCM'
_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/. 
# 
# Audit and citation data items have may 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_setzme
_database_code_depnum_ccdc_archive 'CCDC 1021386'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        methylselenopyrrole
_chemical_formula_moiety         'C22 H23 N5 Se2'
_chemical_formula_sum            'C22 H23 N5 Se2'
_chemical_formula_weight         515.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H23N5Se2
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5962(4)
_cell_length_b                   14.5492(5)
_cell_length_c                   15.4086(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.721(4)
_cell_angle_gamma                90.00
_cell_volume                     2098.50(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3722
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      28.0090
_cell_measurement_theta_min      2.2950
_exptl_absorpt_coefficient_mu    3.543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8088
_diffrn_reflns_theta_full        28.14
_diffrn_reflns_theta_max         28.14
_diffrn_reflns_theta_min         1.95
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   43.00  112.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  178.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00  106.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   19.0000 -150.0000 158

#__ type_ start__ end____ width___ exp.time_
  3 omega   85.00  114.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074    0.0000 -120.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0358074000
_diffrn_orient_matrix_UB_12      -0.0276945000
_diffrn_orient_matrix_UB_13      -0.0359369000
_diffrn_orient_matrix_UB_21      0.0570079000
_diffrn_orient_matrix_UB_22      0.0066920000
_diffrn_orient_matrix_UB_23      -0.0218031000
_diffrn_orient_matrix_UB_31      0.0347026000
_diffrn_orient_matrix_UB_32      -0.0396179000
_diffrn_orient_matrix_UB_33      0.0213984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3710
_reflns_number_total             4595
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         2.029
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0599P)²+2.2551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1218
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4995(4) 0.7213(3) 0.2540(3) 0.0250(8) Uani 1 1 d . . .
H1A H 0.4930 0.7808 0.2248 0.030 Uiso 1 1 calc R . .
H1B H 0.4172 0.7147 0.2804 0.030 Uiso 1 1 calc R . .
C2 C 0.4973(4) 0.6457(3) 0.1852(3) 0.0258(9) Uani 1 1 d . . .
H2A H 0.5153 0.5870 0.2154 0.031 Uiso 1 1 calc R . .
H2B H 0.5730 0.6566 0.1540 0.031 Uiso 1 1 calc R . .
C3 C 0.3543(4) 0.6418(3) 0.1181(3) 0.0246(8) Uani 1 1 d . . .
H3A H 0.2804 0.6233 0.1486 0.029 Uiso 1 1 calc R . .
H3B H 0.3307 0.7028 0.0938 0.029 Uiso 1 1 calc R . .
C4 C 0.3558(4) 0.5750(3) 0.0421(2) 0.0256(9) Uani 1 1 d . . .
H4A H 0.3815 0.5143 0.0664 0.031 Uiso 1 1 calc R . .
H4B H 0.4282 0.5943 0.0107 0.031 Uiso 1 1 calc R . .
C5 C 0.2111(4) 0.5698(3) -0.0239(3) 0.0297(9) Uani 1 1 d . . .
H5A H 0.1400 0.5468 0.0066 0.036 Uiso 1 1 calc R . .
H5B H 0.1826 0.6311 -0.0453 0.036 Uiso 1 1 calc R . .
C6 C 0.2144(6) 0.5086(4) -0.1022(3) 0.0512(14) Uani 1 1 d . . .
H6A H 0.1210 0.5063 -0.1406 0.077 Uiso 1 1 calc R . .
H6B H 0.2430 0.4477 -0.0814 0.077 Uiso 1 1 calc R . .
H6C H 0.2814 0.5326 -0.1344 0.077 Uiso 1 1 calc R . .
C7 C 0.8066(4) 0.4206(3) 0.6730(2) 0.0257(4) Uani 1 1 d . . .
H7 H 0.7830 0.3714 0.7056 0.031 Uiso 1 1 calc R . .
C8 C 0.9405(5) 0.4522(3) 0.6821(3) 0.0257(4) Uani 1 1 d . . .
H8 H 1.0188 0.4271 0.7215 0.031 Uiso 1 1 calc R . .
C9 C 0.9509(5) 0.5284(3) 0.6252(3) 0.0257(4) Uani 1 1 d . . .
C10 C 0.8245(5) 0.5566(3) 0.5697(2) 0.0257(4) Uani 1 1 d . . .
C11 C 0.8586(4) 0.6257(3) 0.5135(2) 0.0210(8) Uani 1 1 d . . .
C12 C 1.0092(4) 0.6398(3) 0.5385(2) 0.0211(8) Uani 1 1 d . . .
C13 C 1.0767(4) 0.7057(3) 0.4909(2) 0.0213(8) Uani 1 1 d . . .
C14 C 0.9960(4) 0.7451(2) 0.4114(2) 0.0210(8) Uani 1 1 d . . .
C15 C 1.0907(4) 0.8001(3) 0.3756(2) 0.0218(8) Uani 1 1 d . . .
C16 C 1.2233(4) 0.7960(3) 0.4325(3) 0.0240(8) Uani 1 1 d . . .
C17 C 1.3344(4) 0.8472(3) 0.4078(3) 0.0277(9) Uani 1 1 d . . .
H17 H 1.4274 0.8497 0.4417 0.033 Uiso 1 1 calc R . .
C18 C 1.2901(4) 0.8920(3) 0.3296(3) 0.0295(9) Uani 1 1 d . . .
H18 H 1.3500 0.9288 0.3045 0.035 Uiso 1 1 calc R . .
C19 C 0.8479(4) 0.7265(3) 0.3841(2) 0.0214(8) Uani 1 1 d . . .
C20 C 0.7784(4) 0.6705(3) 0.4356(2) 0.0209(8) Uani 1 1 d . . .
C21 C 1.2114(4) 0.5549(3) 0.6474(3) 0.0279(9) Uani 1 1 d . . .
H21A H 1.2499 0.5985 0.6931 0.042 Uiso 1 1 calc R . .
H21B H 1.2666 0.5560 0.6025 0.042 Uiso 1 1 calc R . .
H21C H 1.2149 0.4944 0.6728 0.042 Uiso 1 1 calc R . .
C22 C 1.3346(5) 0.7327(3) 0.5814(3) 0.0309(9) Uani 1 1 d . . .
H22A H 1.2981 0.7273 0.6344 0.046 Uiso 1 1 calc R . .
H22B H 1.3925 0.7870 0.5849 0.046 Uiso 1 1 calc R . .
H22C H 1.3913 0.6797 0.5756 0.046 Uiso 1 1 calc R . .
N1 N 0.6384(4) 0.6651(2) 0.3956(2) 0.0227(7) Uani 1 1 d . . .
N2 N 0.6292(4) 0.7177(2) 0.3235(2) 0.0225(7) Uani 1 1 d . . .
N3 N 0.7514(4) 0.7553(2) 0.3116(2) 0.0230(7) Uani 1 1 d . . .
N4 N 1.2157(3) 0.7390(2) 0.5041(2) 0.0235(7) Uani 1 1 d . . .
N5 N 1.0630(3) 0.5788(2) 0.6074(2) 0.0216(7) Uani 1 1 d . . .
Se1 Se 0.67030(5) 0.48565(3) 0.58728(3) 0.02650(13) Uani 1 1 d . . .
Se2 Se 1.09588(4) 0.87280(3) 0.27627(3) 0.02607(13) Uani 1 1 d . . .


_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
C1 C2 1.524(5) . ?
C1 N2 1.453(5) . ?
C2 C3 1.526(5) . ?
C3 C4 1.525(5) . ?
C4 C5 1.532(5) . ?
C5 C6 1.504(7) . ?
C7 C8 1.344(6) . ?
C7 Se1 1.895(4) . ?
C8 C9 1.430(5) . ?
C9 C10 1.384(6) . ?
C9 N5 1.379(5) . ?
C10 C11 1.412(5) . ?
C10 Se1 1.872(4) . ?
C11 C12 1.426(5) . ?
C11 C20 1.431(5) . ?
C12 C13 1.445(5) . ?
C12 N5 1.392(5) . ?
C13 C14 1.417(5) . ?
C13 N4 1.392(5) . ?
C14 C15 1.411(5) . ?
C14 C19 1.417(5) . ?
C15 C16 1.378(6) . ?
C15 Se2 1.870(4) . ?
C16 C17 1.419(5) . ?
C16 N4 1.395(5) . ?
C17 C18 1.353(6) . ?
C18 Se2 1.885(4) . ?
C19 C20 1.404(5) . ?
C19 N3 1.351(5) . ?
C20 N1 1.352(5) . ?
C21 N5 1.463(5) . ?
C22 N4 1.459(5) . ?
N1 N2 1.336(4) . ?
N2 N3 1.342(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
N2 C1 C2 111.4(3) . . ?
C1 C2 C3 111.8(3) . . ?
C4 C3 C2 112.7(3) . . ?
C3 C4 C5 112.4(3) . . ?
C6 C5 C4 112.7(4) . . ?
C8 C7 Se1 113.5(3) . . ?
C7 C8 C9 113.3(4) . . ?
C10 C9 C8 116.0(4) . . ?
N5 C9 C8 134.2(4) . . ?
N5 C9 C10 109.6(3) . . ?
C9 C10 C11 107.5(4) . . ?
C9 C10 Se1 111.1(3) . . ?
C11 C10 Se1 141.2(3) . . ?
C10 C11 C12 107.1(3) . . ?
C10 C11 C20 133.1(4) . . ?
C12 C11 C20 119.2(3) . . ?
C11 C12 C13 119.9(3) . . ?
N5 C12 C11 107.4(3) . . ?
N5 C12 C13 132.6(4) . . ?
C14 C13 C12 119.1(4) . . ?
N4 C13 C12 132.8(4) . . ?
N4 C13 C14 108.0(3) . . ?
C15 C14 C13 106.9(3) . . ?
C15 C14 C19 133.0(4) . . ?
C19 C14 C13 120.1(3) . . ?
C14 C15 Se2 140.9(3) . . ?
C16 C15 C14 108.1(3) . . ?
C16 C15 Se2 110.9(3) . . ?
C15 C16 C17 116.7(4) . . ?
C15 C16 N4 109.1(3) . . ?
N4 C16 C17 134.2(4) . . ?
C18 C17 C16 112.6(4) . . ?
C17 C18 Se2 113.8(3) . . ?
C20 C19 C14 120.9(3) . . ?
N3 C19 C14 130.3(4) . . ?
N3 C19 C20 108.8(3) . . ?
C19 C20 C11 120.2(4) . . ?
N1 C20 C11 130.7(3) . . ?
N1 C20 C19 108.9(3) . . ?
N2 N1 C20 102.9(3) . . ?
N1 N2 C1 121.5(3) . . ?
N1 N2 N3 116.5(3) . . ?
N3 N2 C1 121.1(3) . . ?
N2 N3 C19 102.8(3) . . ?
C13 N4 C16 107.8(3) . . ?
C13 N4 C22 130.5(3) . . ?
C16 N4 C22 121.0(3) . . ?
C9 N5 C12 108.4(3) . . ?
C9 N5 C21 121.3(3) . . ?
C12 N5 C21 129.5(3) . . ?
C10 Se1 C7 86.00(18) . . ?
C15 Se2 C18 85.91(18) . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-DCM'
_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/. 
# 
# Audit and citation data items have may 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_sg_triazole
_database_code_depnum_ccdc_archive 'CCDC 1021387'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_audit_creation_date             2014-07-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        thienopyrrole
_chemical_formula_moiety         'C20 H19 N5 S2, C4 H8 O2'
_chemical_formula_sum            'C24 H27 N5 O2 S2'
_chemical_formula_weight         481.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H19N5S2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3225(2)
_cell_length_b                   15.3272(5)
_cell_length_c                   21.4586(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.056(3)
_cell_angle_gamma                90.00
_cell_volume                     2402.34(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3596
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.9630
_cell_measurement_theta_min      3.2690
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9430
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9160
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   45.00   1.0000   15.4450
omega____ theta____ kappa____ phi______ frames
    -       17.3548  -38.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   -5.00   1.0000   15.4450
omega____ theta____ kappa____ phi______ frames
    -      -15.4016   96.0000 -125.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00    7.00   1.0000   15.4450
omega____ theta____ kappa____ phi______ frames
    -       17.3548  -57.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   45.00   71.00   1.0000   15.4450
omega____ theta____ kappa____ phi______ frames
    -       17.3548 -178.0000 -120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0377528000
_diffrn_orient_matrix_UB_12      -0.0066853000
_diffrn_orient_matrix_UB_13      -0.0309954000
_diffrn_orient_matrix_UB_21      -0.0411108000
_diffrn_orient_matrix_UB_22      0.0419430000
_diffrn_orient_matrix_UB_23      0.0002429000
_diffrn_orient_matrix_UB_31      0.0793781000
_diffrn_orient_matrix_UB_32      0.0184626000
_diffrn_orient_matrix_UB_33      -0.0117219000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3696
_reflns_number_total             4852
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0321P)²+0.5001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33886(8) 0.06930(4) 0.71382(3) 0.02382(16) Uani 1 1 d . . .
S2 S 0.46391(8) 0.25712(4) 0.33213(3) 0.02314(16) Uani 1 1 d . . .
C1 C 0.3094(3) 0.11087(15) 0.29683(10) 0.0240(5) Uani 1 1 d . . .
H1 H 0.2591 0.0658 0.2722 0.029 Uiso 1 1 calc R . .
N2 N 0.5461(2) 0.30914(12) 0.51165(8) 0.0177(4) Uani 1 1 d . . .
C3 C 0.5074(3) 0.45891(15) 0.63069(10) 0.0245(5) Uani 1 1 d . . .
H3A H 0.4658 0.4261 0.6656 0.029 Uiso 1 1 calc R . .
H3B H 0.5660 0.5116 0.6471 0.029 Uiso 1 1 calc R . .
N4 N 0.2793(3) 0.05614(13) 0.41046(9) 0.0202(4) Uani 1 1 d . . .
N5 N 0.2344(2) -0.01125(12) 0.54732(9) 0.0189(4) Uani 1 1 d . . .
O6 O 0.05817(19) -0.21589(10) 0.36824(7) 0.0235(4) Uani 1 1 d . . .
O7 O 0.1279(2) -0.11174(10) 0.43914(7) 0.0246(4) Uani 1 1 d . . .
C2 C 0.3250(3) 0.11098(15) 0.36289(10) 0.0192(5) Uani 1 1 d . . .
C4 C 0.4053(3) 0.18584(14) 0.38926(10) 0.0187(5) Uani 1 1 d . . .
C5 C 0.4105(3) 0.17747(14) 0.45526(9) 0.0161(5) Uani 1 1 d . . .
C6 C 0.4688(3) 0.22909(14) 0.50847(10) 0.0162(5) Uani 1 1 d . . .
N1 N 0.5672(2) 0.32352(12) 0.57334(8) 0.0190(4) Uani 1 1 d . . .
C7 C 0.6466(3) 0.40485(14) 0.59848(10) 0.0219(5) Uani 1 1 d . . .
H7A H 0.6929 0.4386 0.5647 0.026 Uiso 1 1 calc R . .
H7B H 0.7490 0.3914 0.6281 0.026 Uiso 1 1 calc R . .
C8 C 0.3437(3) 0.48357(15) 0.58731(11) 0.0272(6) Uani 1 1 d . . .
H8A H 0.2834 0.4308 0.5717 0.033 Uiso 1 1 calc R . .
H8B H 0.3859 0.5149 0.5518 0.033 Uiso 1 1 calc R . .
C9 C 0.2053(3) 0.54003(16) 0.61882(11) 0.0295(6) Uani 1 1 d . . .
H9A H 0.1671 0.5099 0.6555 0.035 Uiso 1 1 calc R . .
H9B H 0.2636 0.5942 0.6325 0.035 Uiso 1 1 calc R . .
C10 C 0.0388(3) 0.56035(17) 0.57578(11) 0.0311(6) Uani 1 1 d . . .
H10A H -0.0226 0.5061 0.5640 0.037 Uiso 1 1 calc R . .
H10B H 0.0783 0.5871 0.5380 0.037 Uiso 1 1 calc R . .
C11 C -0.0972(3) 0.62084(18) 0.60447(12) 0.0374(7) Uani 1 1 d . . .
H11A H -0.1331 0.5961 0.6428 0.056 Uiso 1 1 calc R . .
H11B H -0.2032 0.6279 0.5759 0.056 Uiso 1 1 calc R . .
H11C H -0.0411 0.6766 0.6127 0.056 Uiso 1 1 calc R . .
C12 C 0.3785(3) 0.18628(16) 0.27433(10) 0.0249(5) Uani 1 1 d . . .
H12 H 0.3796 0.1985 0.2319 0.030 Uiso 1 1 calc R . .
C13 C 0.3318(3) 0.09553(14) 0.46649(10) 0.0171(5) Uani 1 1 d . . .
N13 N 0.5101(2) 0.26110(11) 0.61073(8) 0.0186(4) Uani 1 1 d . . .
C14 C 0.4466(3) 0.19931(14) 0.56971(9) 0.0155(5) Uani 1 1 d . . .
C15 C 0.3680(3) 0.11590(14) 0.58065(10) 0.0170(5) Uani 1 1 d . . .
C16 C 0.3108(3) 0.06555(14) 0.52828(10) 0.0174(5) Uani 1 1 d . . .
C17 C 0.2413(3) -0.01071(14) 0.61167(10) 0.0184(5) Uani 1 1 d . . .
C18 C 0.3235(3) 0.06634(14) 0.63307(10) 0.0176(5) Uani 1 1 d . . .
C19 C 0.2321(3) -0.03175(16) 0.71648(11) 0.0272(6) Uani 1 1 d . . .
H19 H 0.2081 -0.0592 0.7537 0.033 Uiso 1 1 calc R . .
C20 C 0.1868(3) -0.06707(15) 0.65943(10) 0.0229(5) Uani 1 1 d . . .
H20 H 0.1285 -0.1205 0.6526 0.027 Uiso 1 1 calc R . .
C21 C 0.1183(3) -0.2122(2) 0.26120(12) 0.0420(7) Uani 1 1 d . . .
H21A H 0.1946 -0.2629 0.2671 0.063 Uiso 1 1 calc R . .
H21B H 0.1610 -0.1772 0.2281 0.063 Uiso 1 1 calc R . .
H21C H -0.0057 -0.2299 0.2505 0.063 Uiso 1 1 calc R . .
C22 C 0.1262(3) -0.15993(16) 0.32026(10) 0.0263(5) Uani 1 1 d . . .
H22A H 0.2511 -0.1421 0.3319 0.032 Uiso 1 1 calc R . .
H22B H 0.0508 -0.1081 0.3148 0.032 Uiso 1 1 calc R . .
C23 C 0.0689(3) -0.18411(15) 0.42608(10) 0.0203(5) Uani 1 1 d . . .
C24 C 0.0071(3) -0.24761(15) 0.47269(11) 0.0268(6) Uani 1 1 d . . .
H24A H 0.1119 -0.2723 0.4957 0.040 Uiso 1 1 calc R . .
H24B H -0.0622 -0.2932 0.4515 0.040 Uiso 1 1 calc R . .
H24C H -0.0681 -0.2182 0.5010 0.040 Uiso 1 1 calc R . .
H4 H 0.238(3) 0.0058(15) 0.4074(10) 0.019(6) Uiso 1 1 d . . .
H5 H 0.190(3) -0.0526(16) 0.5221(11) 0.032(7) Uiso 1 1 d . . .


_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
S1 C18 1.729(2) . ?
S1 C19 1.738(2) . ?
S2 C4 1.719(2) . ?
S2 C12 1.732(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.414(3) . ?
C1 C12 1.363(3) . ?
N2 C6 1.351(3) . ?
N2 N1 1.340(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C7 1.518(3) . ?
C3 C8 1.513(3) . ?
N4 C2 1.382(3) . ?
N4 C13 1.376(3) . ?
N4 H4 0.83(2) . ?
N5 C16 1.378(3) . ?
N5 C17 1.378(3) . ?
N5 H5 0.88(2) . ?
O6 C22 1.455(3) . ?
O6 C23 1.330(3) . ?
O7 C23 1.216(3) . ?
C2 C4 1.391(3) . ?
C4 C5 1.420(3) . ?
C5 C6 1.429(3) . ?
C5 C13 1.410(3) . ?
C6 C14 1.411(3) . ?
N1 C7 1.463(3) . ?
N1 N13 1.335(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.522(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 C16 1.422(3) . ?
N13 C14 1.353(3) . ?
C14 C15 1.428(3) . ?
C15 C16 1.402(3) . ?
C15 C18 1.414(3) . ?
C17 C18 1.389(3) . ?
C17 C20 1.419(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 C22 1.497(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.489(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C18 S1 C19 90.69(11) . . ?
C4 S2 C12 90.95(11) . . ?
C2 C1 H1 124.8 . . ?
C12 C1 H1 124.8 . . ?
C12 C1 C2 110.4(2) . . ?
N1 N2 C6 102.59(17) . . ?
H3A C3 H3B 107.8 . . ?
C7 C3 H3A 109.1 . . ?
C7 C3 H3B 109.1 . . ?
C8 C3 H3A 109.1 . . ?
C8 C3 H3B 109.1 . . ?
C8 C3 C7 112.62(18) . . ?
C2 N4 H4 127.8(16) . . ?
C13 N4 C2 108.14(18) . . ?
C13 N4 H4 123.7(16) . . ?
C16 N5 C17 107.76(18) . . ?
C16 N5 H5 125.0(16) . . ?
C17 N5 H5 127.3(16) . . ?
C23 O6 C22 116.35(17) . . ?
N4 C2 C1 137.2(2) . . ?
N4 C2 C4 108.59(19) . . ?
C4 C2 C1 114.2(2) . . ?
C2 C4 S2 110.71(16) . . ?
C2 C4 C5 108.17(19) . . ?
C5 C4 S2 141.12(18) . . ?
C4 C5 C6 137.1(2) . . ?
C13 C5 C4 105.58(18) . . ?
C13 C5 C6 117.35(18) . . ?
N2 C6 C5 130.06(19) . . ?
N2 C6 C14 108.79(18) . . ?
C14 C6 C5 121.14(19) . . ?
N2 N1 C7 121.31(18) . . ?
N13 N1 N2 117.18(17) . . ?
N13 N1 C7 121.50(17) . . ?
C3 C7 H7A 109.3 . . ?
C3 C7 H7B 109.3 . . ?
N1 C7 C3 111.77(17) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C3 C8 H8A 109.0 . . ?
C3 C8 H8B 109.0 . . ?
C3 C8 C9 113.03(19) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.27(19) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 113.7(2) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S2 C12 H12 123.1 . . ?
C1 C12 S2 113.72(17) . . ?
C1 C12 H12 123.1 . . ?
N4 C13 C5 109.52(18) . . ?
N4 C13 C16 129.1(2) . . ?
C5 C13 C16 121.31(19) . . ?
N1 N13 C14 102.62(17) . . ?
C6 C14 C15 121.12(19) . . ?
N13 C14 C6 108.82(18) . . ?
N13 C14 C15 130.07(19) . . ?
C16 C15 C14 117.50(19) . . ?
C16 C15 C18 105.62(18) . . ?
C18 C15 C14 136.86(19) . . ?
N5 C16 C13 128.72(19) . . ?
N5 C16 C15 109.70(18) . . ?
C15 C16 C13 121.57(19) . . ?
N5 C17 C18 108.71(19) . . ?
N5 C17 C20 136.7(2) . . ?
C18 C17 C20 114.6(2) . . ?
C15 C18 S1 141.32(17) . . ?
C17 C18 S1 110.47(16) . . ?
C17 C18 C15 108.21(19) . . ?
S1 C19 H19 123.0 . . ?
C20 C19 S1 114.04(18) . . ?
C20 C19 H19 123.0 . . ?
C17 C20 H20 124.9 . . ?
C19 C20 C17 110.2(2) . . ?
C19 C20 H20 124.9 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
O6 C22 C21 106.81(19) . . ?
O6 C22 H22A 110.4 . . ?
O6 C22 H22B 110.4 . . ?
C21 C22 H22A 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
O6 C23 C24 112.8(2) . . ?
O7 C23 O6 123.1(2) . . ?
O7 C23 C24 124.2(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane- ethylacetate'
_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/. 
# 
# Audit and citation data items have may 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_ssz_sg_setr
_database_code_depnum_ccdc_archive 'CCDC 1021388'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_audit_creation_date             2014-07-29
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        selenopyrrole
_chemical_formula_moiety         'C20 H19 N5 Se2, C4 H8 O2'
_chemical_formula_sum            'C24 H27 N5 O2 Se2'
_chemical_formula_weight         575.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H19N5Se2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.2332(3)
_cell_length_b                   15.9927(6)
_cell_length_c                   21.3756(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.932(3)
_cell_angle_gamma                90.00
_cell_volume                     2459.45(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5530
_cell_measurement_temperature    100.03(10)
_cell_measurement_theta_max      66.3150
_cell_measurement_theta_min      3.4550
_exptl_absorpt_coefficient_mu    4.009
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.4129
_exptl_crystal_size_mid          0.0931
_exptl_crystal_size_min          0.0701
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9009
_diffrn_reflns_theta_full        66.62
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9604
_diffrn_measured_fraction_theta_max 0.9604
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9359   57.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  101.00  144.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680  111.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  104.00  150.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680  111.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  133.00  159.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  118.00  145.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  101.00  138.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680  111.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega  103.00  132.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega  118.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   95.00  135.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega  100.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680  111.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  113.00  143.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680  111.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 12 omega  104.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   65.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  143.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   50.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   51.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega   62.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 20 omega   35.00  139.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680   30.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
 21 omega   46.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 22 omega   28.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -43.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega   62.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 25 omega   26.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
 26 omega   22.00  133.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -88.0000  -28.0358 111

#__ type_ start__ end____ width___ exp.time_
 27 omega   57.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680 -111.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 28 omega   17.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       67.4680 -111.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 29 omega   -9.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9359   57.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
 30 omega  -11.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9359   57.0000 -150.0000 38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0375315000
_diffrn_orient_matrix_UB_12      0.0455728000
_diffrn_orient_matrix_UB_13      0.0635233000
_diffrn_orient_matrix_UB_21      0.0536216000
_diffrn_orient_matrix_UB_22      0.0796459000
_diffrn_orient_matrix_UB_23      -0.0344612000
_diffrn_orient_matrix_UB_31      -0.2038998000
_diffrn_orient_matrix_UB_32      0.0292824000
_diffrn_orient_matrix_UB_33      -0.0051760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4015
_reflns_number_total             4232
_reflns_odcompleteness_completeness 96.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.423
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0734P)²+0.7391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1082
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4036(4) 0.88335(17) 0.36791(13) 0.0255(5) Uani 1 1 d . . .
H1A H 0.2721 0.8878 0.3729 0.031 Uiso 1 1 calc R . .
H1B H 0.4165 0.8791 0.3233 0.031 Uiso 1 1 calc R . .
C2 C 0.5023(4) 0.96165(16) 0.39389(13) 0.0253(6) Uani 1 1 d . . .
H2A H 0.4924 0.9649 0.4387 0.030 Uiso 1 1 calc R . .
H2B H 0.4407 1.0103 0.3743 0.030 Uiso 1 1 calc R . .
C3 C 0.7061(4) 0.96341(17) 0.38269(14) 0.0258(6) Uani 1 1 d . . .
H3A H 0.7155 0.9654 0.3378 0.031 Uiso 1 1 calc R . .
H3B H 0.7648 0.9121 0.3988 0.031 Uiso 1 1 calc R . .
C4 C 0.8104(4) 1.03758(17) 0.41382(14) 0.0272(6) Uani 1 1 d . . .
H4A H 0.7911 1.0384 0.4581 0.033 Uiso 1 1 calc R . .
H4B H 0.7583 1.0887 0.3950 0.033 Uiso 1 1 calc R . .
C5 C 1.0184(4) 1.03634(17) 0.40801(14) 0.0283(6) Uani 1 1 d . . .
H5A H 1.0703 0.9844 0.4255 0.034 Uiso 1 1 calc R . .
H5B H 1.0383 1.0379 0.3638 0.034 Uiso 1 1 calc R . .
C6 C 1.1201(5) 1.1092(2) 0.44148(16) 0.0348(7) Uani 1 1 d . . .
H6A H 1.0746 1.1607 0.4227 0.052 Uiso 1 1 calc R . .
H6B H 1.2508 1.1043 0.4378 0.052 Uiso 1 1 calc R . .
H6C H 1.0992 1.1086 0.4851 0.052 Uiso 1 1 calc R . .
C7 C 0.8107(4) 0.43897(19) 0.28377(14) 0.0291(6) Uani 1 1 d . . .
H7 H 0.8461 0.4062 0.2511 0.035 Uiso 1 1 calc R . .
C8 C 0.8361(4) 0.41535(18) 0.34470(13) 0.0258(6) Uani 1 1 d . . .
H8 H 0.8889 0.3647 0.3583 0.031 Uiso 1 1 calc R . .
C9 C 0.7725(4) 0.47712(17) 0.38592(13) 0.0219(5) Uani 1 1 d . . .
C10 C 0.7001(4) 0.54948(16) 0.35860(13) 0.0217(5) Uani 1 1 d . . .
C11 C 0.6520(3) 0.60350(16) 0.40712(12) 0.0194(5) Uani 1 1 d . . .
C12 C 0.6983(4) 0.55922(16) 0.46364(13) 0.0204(5) Uani 1 1 d . . .
C13 C 0.6712(3) 0.59422(16) 0.52297(12) 0.0193(5) Uani 1 1 d . . .
C14 C 0.6003(3) 0.67568(16) 0.52807(12) 0.0189(5) Uani 1 1 d . . .
C15 C 0.5984(3) 0.69013(16) 0.59348(12) 0.0196(5) Uani 1 1 d . . .
C16 C 0.6661(3) 0.61948(16) 0.62520(12) 0.0204(5) Uani 1 1 d . . .
C17 C 0.6803(4) 0.62212(17) 0.69217(12) 0.0245(5) Uani 1 1 d . . .
H17 H 0.7244 0.5779 0.7177 0.029 Uiso 1 1 calc R . .
C18 C 0.6228(4) 0.69604(18) 0.71475(13) 0.0274(6) Uani 1 1 d . . .
H18 H 0.6242 0.7079 0.7574 0.033 Uiso 1 1 calc R . .
C19 C 0.5541(3) 0.72119(16) 0.47103(12) 0.0183(5) Uani 1 1 d . . .
C20 C 0.5808(3) 0.68599(16) 0.41210(12) 0.0188(5) Uani 1 1 d . . .
C21 C 0.9667(4) 0.25976(18) 0.54485(15) 0.0298(6) Uani 1 1 d . . .
H21A H 0.8605 0.2323 0.5233 0.045 Uiso 1 1 calc R . .
H21B H 1.0391 0.2200 0.5706 0.045 Uiso 1 1 calc R . .
H21C H 1.0413 0.2832 0.5146 0.045 Uiso 1 1 calc R . .
C22 C 0.9034(3) 0.32797(16) 0.58539(13) 0.0221(5) Uani 1 1 d . . .
C23 C 0.8388(4) 0.3662(2) 0.68775(14) 0.0305(6) Uani 1 1 d . . .
H23A H 0.7107 0.3809 0.6745 0.037 Uiso 1 1 calc R . .
H23B H 0.9138 0.4165 0.6883 0.037 Uiso 1 1 calc R . .
C24 C 0.8542(6) 0.3271(3) 0.75167(16) 0.0502(9) Uani 1 1 d . . .
H24A H 0.7833 0.2762 0.7501 0.075 Uiso 1 1 calc R . .
H24B H 0.8070 0.3650 0.7810 0.075 Uiso 1 1 calc R . .
H24C H 0.9822 0.3148 0.7649 0.075 Uiso 1 1 calc R . .
N1 N 0.5317(3) 0.74255(14) 0.36680(10) 0.0211(4) Uani 1 1 d . . .
N2 N 0.4775(3) 0.80800(14) 0.39940(10) 0.0209(4) Uani 1 1 d . . .
N3 N 0.4872(3) 0.79965(14) 0.46183(10) 0.0201(4) Uani 1 1 d . . .
N4 N 0.7108(3) 0.56094(14) 0.58176(10) 0.0205(4) Uani 1 1 d . . .
H4 H 0.7557 0.5120 0.5902 0.025 Uiso 1 1 calc R . .
N5 N 0.7712(3) 0.48267(14) 0.44995(11) 0.0215(4) Uani 1 1 d . . .
H5 H 0.8093 0.4449 0.4769 0.026 Uiso 1 1 calc R . .
O1 O 0.8511(3) 0.39593(12) 0.56605(9) 0.0261(4) Uani 1 1 d . . .
O2 O 0.9050(3) 0.30489(12) 0.64492(10) 0.0274(4) Uani 1 1 d . . .
Se1 Se 0.69694(4) 0.544650(18) 0.270999(12) 0.02470(13) Uani 1 1 d . . .
Se2 Se 0.53965(4) 0.772027(17) 0.650356(13) 0.02513(13) Uani 1 1 d . . .


_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
C1 C2 1.518(4) . ?
C1 N2 1.455(3) . ?
C2 C3 1.518(4) . ?
C3 C4 1.522(4) . ?
C4 C5 1.523(4) . ?
C5 C6 1.517(4) . ?
C7 C8 1.350(4) . ?
C7 Se1 1.887(3) . ?
C8 C9 1.431(4) . ?
C9 C10 1.375(4) . ?
C9 N5 1.372(4) . ?
C10 C11 1.421(4) . ?
C10 Se1 1.872(3) . ?
C11 C12 1.411(4) . ?
C11 C20 1.424(4) . ?
C12 C13 1.418(4) . ?
C12 N5 1.376(3) . ?
C13 C14 1.408(4) . ?
C13 N4 1.367(3) . ?
C14 C15 1.418(4) . ?
C14 C19 1.430(4) . ?
C15 C16 1.381(4) . ?
C15 Se2 1.866(3) . ?
C16 C17 1.425(4) . ?
C16 N4 1.380(3) . ?
C17 C18 1.358(4) . ?
C18 Se2 1.887(3) . ?
C19 C20 1.411(4) . ?
C19 N3 1.352(3) . ?
C20 N1 1.346(4) . ?
C21 C22 1.494(4) . ?
C22 O1 1.210(3) . ?
C22 O2 1.324(3) . ?
C23 C24 1.496(5) . ?
C23 O2 1.456(3) . ?
N1 N2 1.338(3) . ?
N2 N3 1.336(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
N2 C1 C2 112.2(2) . . ?
C1 C2 C3 112.7(2) . . ?
C2 C3 C4 113.0(2) . . ?
C3 C4 C5 113.8(2) . . ?
C6 C5 C4 112.7(2) . . ?
C8 C7 Se1 113.8(2) . . ?
C7 C8 C9 112.4(3) . . ?
C10 C9 C8 116.9(3) . . ?
N5 C9 C8 134.0(3) . . ?
N5 C9 C10 109.1(2) . . ?
C9 C10 C11 108.2(2) . . ?
C9 C10 Se1 110.79(19) . . ?
C11 C10 Se1 141.0(2) . . ?
C10 C11 C20 137.4(2) . . ?
C12 C11 C10 105.4(2) . . ?
C12 C11 C20 117.2(2) . . ?
C11 C12 C13 121.7(2) . . ?
N5 C12 C11 109.1(2) . . ?
N5 C12 C13 129.3(2) . . ?
C14 C13 C12 121.3(2) . . ?
N4 C13 C12 129.3(2) . . ?
N4 C13 C14 109.4(2) . . ?
C13 C14 C15 105.5(2) . . ?
C13 C14 C19 117.4(2) . . ?
C15 C14 C19 137.1(2) . . ?
C14 C15 Se2 141.5(2) . . ?
C16 C15 C14 108.2(2) . . ?
C16 C15 Se2 110.33(19) . . ?
C15 C16 C17 117.0(2) . . ?
N4 C16 C15 108.7(2) . . ?
N4 C16 C17 134.3(2) . . ?
C18 C17 C16 112.9(2) . . ?
C17 C18 Se2 112.8(2) . . ?
C20 C19 C14 121.1(2) . . ?
N3 C19 C14 130.2(2) . . ?
N3 C19 C20 108.7(2) . . ?
C19 C20 C11 121.3(2) . . ?
N1 C20 C11 129.8(2) . . ?
N1 C20 C19 108.9(2) . . ?
O1 C22 C21 124.2(3) . . ?
O1 C22 O2 123.4(2) . . ?
O2 C22 C21 112.4(2) . . ?
O2 C23 C24 107.1(3) . . ?
N2 N1 C20 102.8(2) . . ?
N1 N2 C1 121.4(2) . . ?
N3 N2 C1 121.6(2) . . ?
N3 N2 N1 117.0(2) . . ?
N2 N3 C19 102.7(2) . . ?
C13 N4 C16 108.2(2) . . ?
C9 N5 C12 108.2(2) . . ?
C22 O2 C23 116.5(2) . . ?
C10 Se1 C7 86.11(12) . . ?
C15 Se2 C18 86.92(12) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 8 8 0.0215 -0.0153 8.0179 8.0833 0.8783 0.3592 0.1961
0 -8 -8 0.0655 0.0153 -8.0179 -8.0833 -0.8783 -0.3592 -0.1961
-5 1 -1 0.1480 -5.0079 0.9959 -0.9785 -0.2047 -0.1555 1.0553
4 0 3 0.2167 4.0055 0.0053 2.9965 0.3409 0.1119 -0.8321
0 -7 10 0.0533 0.0225 -7.0132 9.9921 0.3160 -0.9017 -0.2617
0 7 -10 0.0167 -0.0225 7.0132 -9.9921 -0.3160 0.9017 0.2617
0 4 13 0.0395 -0.0028 4.0103 13.0760 1.0133 -0.1314 0.0503
0 -10 4 0.0638 0.0267 -10.0203 3.9494 -0.2048 -0.9328 -0.3193

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-ethylacetae'
_exptl_crystal_preparation       Luminescent
