# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_w
_database_code_depnum_ccdc_archive 'CCDC 1588477'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
_audit_creation_date             2017-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08
_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'
O O 0.0106 0.0060 '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/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                   7.9873(10)
_cell_length_b                   7.9532(10)
_cell_length_c                   12.6983(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.639(3)
_cell_angle_gamma                90.00
_cell_volume                     806.60(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5856
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.55
_exptl_absorpt_coefficient_mu    4.611
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1176 before and 0.0453 after correction. The Ratio of minimum to maximum transmission is 0.4200. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10960
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.55
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1633
_reflns_number_total             1986
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0250P)²+0.3220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0602
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se 0.15866(3) 0.13266(3) 0.100118(16) 0.05093(9) Uani 1 d . . .
C6 C 0.2272(2) 0.3333(2) 0.02879(15) 0.0373(4) Uani 1 d . . .
C7 C 0.0533(3) 0.2433(3) 0.21038(17) 0.0522(5) Uani 1 d . . .
C2 C 0.3639(3) 0.4633(3) -0.12119(16) 0.0478(5) Uani 1 d . . .
H2 H 0.4222 0.4519 -0.1838 0.057 Uiso 1 calc . . R
C5 C 0.1910(3) 0.4935(3) 0.06581(16) 0.0448(5) Uani 1 d . . .
H5 H 0.1335 0.5062 0.1286 0.054 Uiso 1 calc . . R
N2 N -0.0122(3) 0.3029(3) 0.27953(17) 0.0714(6) Uani 1 d . . .
C1 C 0.3150(2) 0.3226(2) -0.06511(16) 0.0395(4) Uani 1 d . . .
C3 C 0.3252(3) 0.6198(3) -0.08292(18) 0.0508(5) Uani 1 d . . .
H3 H 0.3565 0.7158 -0.1196 0.061 Uiso 1 calc . . R
C4 C 0.2394(3) 0.6336(2) 0.01030(18) 0.0506(5) Uani 1 d . . .
H4 H 0.2138 0.7398 0.0362 0.061 Uiso 1 calc . . R
N1 N 0.3600(3) 0.1591(2) -0.10696(14) 0.0542(5) Uani 1 d . . .
O2 O 0.3158(3) 0.0347(2) -0.05903(15) 0.0774(6) Uani 1 d . . .
O1 O 0.4390(3) 0.1523(2) -0.18815(16) 0.0860(7) Uani 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
Se1 0.07009(16) 0.03315(12) 0.04995(14) 0.00331(9) 0.01860(10) -0.00235(9)
C6 0.0409(9) 0.0310(9) 0.0402(9) 0.0013(7) 0.0063(8) -0.0011(7)
C7 0.0584(13) 0.0497(12) 0.0486(12) 0.0080(10) 0.0121(10) -0.0006(10)
C2 0.0535(12) 0.0476(11) 0.0423(10) 0.0063(9) 0.0075(9) -0.0051(9)
C5 0.0497(11) 0.0374(10) 0.0478(11) -0.0031(8) 0.0140(9) -0.0002(8)
N2 0.0877(15) 0.0707(14) 0.0566(12) 0.0044(11) 0.0288(11) 0.0074(12)
C1 0.0453(10) 0.0341(9) 0.0392(9) -0.0024(8) 0.0066(8) 0.0022(8)
C3 0.0571(12) 0.0385(11) 0.0569(13) 0.0086(9) 0.0052(10) -0.0050(9)
C4 0.0583(12) 0.0294(9) 0.0643(13) -0.0010(9) 0.0057(10) 0.0010(9)
N1 0.0693(12) 0.0433(10) 0.0504(11) -0.0067(8) 0.0176(9) 0.0046(8)
O2 0.1217(15) 0.0340(8) 0.0773(12) -0.0024(8) 0.0403(11) 0.0054(9)
O1 0.1244(17) 0.0640(12) 0.0708(12) -0.0105(9) 0.0550(12) 0.0116(11)

_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
Se1 C6 1.9178(18) . ?
Se1 C7 1.863(2) . ?
C6 C5 1.390(3) . ?
C6 C1 1.393(3) . ?
C7 N2 1.131(3) . ?
C2 C1 1.385(3) . ?
C2 C3 1.373(3) . ?
C5 C4 1.376(3) . ?
C1 N1 1.451(3) . ?
C3 C4 1.379(3) . ?
N1 O2 1.217(3) . ?
N1 O1 1.216(2) . ?

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 Se1 C6 95.49(8) . . ?
C5 C6 Se1 122.79(14) . . ?
C5 C6 C1 117.04(17) . . ?
C1 C6 Se1 120.16(14) . . ?
N2 C7 Se1 176.6(2) . . ?
C3 C2 C1 119.0(2) . . ?
C4 C5 C6 120.54(18) . . ?
C6 C1 N1 119.84(17) . . ?
C2 C1 C6 122.57(19) . . ?
C2 C1 N1 117.58(18) . . ?
C2 C3 C4 119.5(2) . . ?
C5 C4 C3 121.37(19) . . ?
O2 N1 C1 118.11(17) . . ?
O1 N1 C1 118.90(19) . . ?
O1 N1 O2 123.0(2) . . ?

_iucr_refine_instructions_details 
;
TITL W in P21/c #14
REM reset to P21/c #14
CELL 0.71073 7.9873 7.9532 12.6983 90 90.639 90
ZERR 4 0.001 0.001 0.0016 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O Se
UNIT 28 16 8 8 4
 
L.S. 4
PLAN  20
TEMP 0
BOND
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\W.hkl">
REM </olex2.extras>
 
WGHT    0.025000    0.322000
FVAR       0.25221
SE1   5    0.158656    0.132661    0.100118    11.00000    0.07009    0.03315 =
         0.04995    0.00331    0.01860   -0.00235
C6    1    0.227189    0.333319    0.028789    11.00000    0.04092    0.03100 =
         0.04022    0.00128    0.00629   -0.00110
C7    1    0.053281    0.243312    0.210384    11.00000    0.05844    0.04971 =
         0.04860    0.00799    0.01213   -0.00059
C2    1    0.363947    0.463276   -0.121193    11.00000    0.05351    0.04762 =
         0.04232    0.00631    0.00752   -0.00512
AFIX  43
H2    2    0.422174    0.451907   -0.183807    11.00000   -1.20000
AFIX   0
C5    1    0.190961    0.493509    0.065810    11.00000    0.04971    0.03738 =
         0.04775   -0.00306    0.01397   -0.00019
AFIX  43
H5    2    0.133508    0.506158    0.128615    11.00000   -1.20000
AFIX   0
N2    3   -0.012205    0.302902    0.279529    11.00000    0.08769    0.07070 =
         0.05658    0.00443    0.02879    0.00742
C1    1    0.315018    0.322581   -0.065113    11.00000    0.04535    0.03406 =
         0.03921   -0.00242    0.00663    0.00225
C3    1    0.325162    0.619815   -0.082918    11.00000    0.05715    0.03849 =
         0.05693    0.00862    0.00518   -0.00502
AFIX  43
H3    2    0.356506    0.715792   -0.119599    11.00000   -1.20000
AFIX   0
C4    1    0.239406    0.633607    0.010295    11.00000    0.05830    0.02936 =
         0.06433   -0.00104    0.00572    0.00097
AFIX  43
H4    2    0.213753    0.739788    0.036207    11.00000   -1.20000
AFIX   0
N1    3    0.360000    0.159133   -0.106961    11.00000    0.06926    0.04328 =
         0.05038   -0.00666    0.01760    0.00464
O2    4    0.315762    0.034671   -0.059029    11.00000    0.12172    0.03405 =
         0.07734   -0.00244    0.04030    0.00541
O1    4    0.438977    0.152328   -0.188146    11.00000    0.12439    0.06403 =
         0.07078   -0.01055    0.05504    0.01157
HKLF 4
 
REM  W in P21/c #14
REM R1 =  0.0240 for   1633 Fo > 4sig(Fo)  and  0.0340 for all   1986 data
REM    109 parameters refined using      0 restraints
 
END  
     
WGHT      0.0245      0.3224 
REM Highest difference peak  0.339,  deepest hole -0.371,  1-sigma level  0.049
Q1    1   0.2624  0.1704  0.1216  11.00000  0.05    0.34
Q2    1   0.0771  0.1433  0.0440  11.00000  0.05    0.27
Q3    1   0.2356  0.5519  0.0336  11.00000  0.05    0.21
Q4    1   0.1859  0.2740  0.0551  11.00000  0.05    0.21
Q5    1   0.2550  0.6141 -0.0390  11.00000  0.05    0.20
Q6    1   0.4999  0.1439 -0.1373  11.00000  0.05    0.18
Q7    1   0.2321  0.0539 -0.0592  11.00000  0.05    0.17
Q8    1   0.2451  0.6741  0.0183  11.00000  0.05    0.17
Q9    1   0.3565  0.5453 -0.1011  11.00000  0.05    0.16
Q10   1   0.0786  0.2050  0.1810  11.00000  0.05    0.16
Q11   1   0.0469  0.0241  0.0878  11.00000  0.05    0.16
Q12   1   0.2465  0.3255 -0.0210  11.00000  0.05    0.15
Q13   1   0.2128  0.4116  0.0498  11.00000  0.05    0.14
Q14   1   0.3374  0.2419 -0.0805  11.00000  0.05    0.14
Q15   1   0.3805  0.1028 -0.1979  11.00000  0.05    0.14
Q16   1   0.3044  0.1367  0.0183  11.00000  0.05    0.14
Q17   1   0.4601  0.0863 -0.0028  11.00000  0.05    0.14
Q18   1   0.2718  0.7561  0.0681  11.00000  0.05    0.14
Q19   1   0.3414  0.3882 -0.0934  11.00000  0.05    0.14
Q20   1   0.3786  0.1824 -0.1976  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0240 for 1633 Fo > 4sig(Fo) and 0.0340 for all 11505 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.34, deepest hole -0.37
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0340
  REM R1_gt = 0.0240
  REM wR_ref = 0.0602
  REM GOOF = 1.059
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 11505
  REM Reflections_gt = 1633
  REM Parameters = n/a
  REM Hole = -0.37
  REM Peak = 0.34
  REM Flack = n/a

  
;
_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_w_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1588478'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
_audit_creation_date             2017-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08
_chemical_absolute_configuration ad
_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'
O O 0.0106 0.0060 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   3.9678(4)
_cell_length_b                   6.9334(7)
_cell_length_c                   14.5948(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.469(2)
_cell_angle_gamma                90.00
_cell_volume                     400.29(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4427
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.174
_cell_measurement_theta_min      2.800
_exptl_absorpt_coefficient_mu    4.645
_exptl_absorpt_correction_T_max  0.4885
_exptl_absorpt_correction_T_min  0.4421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1176 before and 0.0453 after correction. The Ratio of minimum to maximum transmission is 0.4200. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4056
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         4.20
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1405
_reflns_number_total             1434
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.061(13)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1434
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0206
_refine_ls_restrained_S_all      1.136
_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)+(0.0140P)²+0.0530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0530
_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. 
;
_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), C5(H5), C4(H4), C2(H2)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se -0.45157(6) -0.33530(5) -0.846266(14) 0.04021(11) Uani 1 d . . .
C3 C -0.0024(7) 0.1875(5) -0.7562(2) 0.0446(7) Uani 1 d . . .
H3 H 0.0906 0.2944 -0.7833 0.053 Uiso 1 calc . . R
C1 C -0.2733(6) -0.1237(4) -0.77339(18) 0.0314(5) Uani 1 d . . .
C5 C -0.1484(8) 0.0205(5) -0.6220(2) 0.0454(7) Uani 1 d . . .
H5 H -0.1548 0.0124 -0.5586 0.055 Uiso 1 calc . . R
C6 C -0.2773(7) -0.1261(4) -0.67786(19) 0.0356(6) Uani 1 d . . .
C4 C -0.0085(7) 0.1810(9) -0.66172(18) 0.0473(8) Uani 1 d . . .
H4 H 0.0792 0.2821 -0.6254 0.057 Uiso 1 calc . . R
C2 C -0.1316(7) 0.0384(4) -0.81148(19) 0.0391(6) Uani 1 d . . .
H2 H -0.1236 0.0467 -0.8749 0.047 Uiso 1 calc . . R
C7 C -0.3282(8) -0.2402(5) -0.9575(2) 0.0471(7) Uani 1 d . . .
N2 N -0.2583(9) -0.1893(5) -1.0282(2) 0.0678(9) Uani 1 d . . .
O1 O -0.4184(9) -0.2950(6) -0.54995(16) 0.0985(14) Uani 1 d . . .
N1 N -0.4307(8) -0.2886(4) -0.63376(19) 0.0503(7) Uani 1 d . . .
O2 O -0.5700(7) -0.4133(4) -0.6829(2) 0.0644(7) Uani 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
Se1 0.04368(16) 0.03850(14) 0.03829(15) -0.00616(15) 0.00211(9) -0.00607(15)
C3 0.0511(15) 0.0302(16) 0.0528(14) 0.0014(14) 0.0063(11) -0.0077(15)
C1 0.0314(13) 0.0311(12) 0.0316(13) 0.0021(10) 0.0022(10) 0.0038(10)
C5 0.0560(18) 0.0472(16) 0.0332(14) -0.0028(13) 0.0038(13) -0.0023(14)
C6 0.0399(15) 0.0354(13) 0.0321(13) 0.0042(11) 0.0067(10) 0.0006(11)
C4 0.0590(16) 0.034(2) 0.0485(14) -0.0067(16) -0.0006(12) -0.0046(15)
C2 0.0471(16) 0.0383(15) 0.0321(13) 0.0040(11) 0.0050(11) -0.0025(12)
C7 0.0550(19) 0.0510(16) 0.0342(16) -0.0087(13) -0.0029(13) 0.0083(14)
N2 0.095(2) 0.072(2) 0.0361(16) -0.0023(14) 0.0065(15) 0.0078(18)
O1 0.158(3) 0.099(3) 0.0383(12) 0.0159(15) 0.0119(15) -0.053(3)
N1 0.0644(16) 0.049(2) 0.0391(12) 0.0107(11) 0.0102(12) -0.0099(12)
O2 0.090(2) 0.0512(13) 0.0533(14) 0.0017(12) 0.0136(12) -0.0308(12)

_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
Se1 C1 1.915(3) . ?
Se1 C7 1.853(3) . ?
C3 C4 1.382(4) . ?
C3 C2 1.385(4) . ?
C1 C6 1.396(4) . ?
C1 C2 1.392(4) . ?
C5 C6 1.377(4) . ?
C5 C4 1.390(6) . ?
C6 N1 1.454(4) . ?
C7 N2 1.145(4) . ?
O1 N1 1.221(4) . ?
N1 O2 1.227(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
C7 Se1 C1 95.89(13) . . ?
C4 C3 C2 121.5(4) . . ?
C6 C1 Se1 120.87(19) . . ?
C2 C1 Se1 122.7(2) . . ?
C2 C1 C6 116.4(3) . . ?
C6 C5 C4 119.1(3) . . ?
C1 C6 N1 119.3(3) . . ?
C5 C6 C1 123.4(3) . . ?
C5 C6 N1 117.3(3) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C2 C1 120.9(3) . . ?
N2 C7 Se1 176.7(3) . . ?
O1 N1 C6 119.1(3) . . ?
O1 N1 O2 122.7(3) . . ?
O2 N1 C6 118.2(2) . . ?

_iucr_refine_instructions_details 
;
TITL w in P21 #4
REM reset to P21 #4
CELL 0.71073 3.9678 6.9334 14.5948 90 94.469 90
ZERR 2 0.0004 0.0007 0.0014 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O Se
UNIT 14 8 4 4 2
 
L.S. 4
PLAN  20
SIZE 0.21 0.19 0.18
TEMP 0
fmap 2
acta
SHEL 999 0.83
REM <olex2.extras>
REM <HklSrc "%.\\w.hkl">
REM </olex2.extras>
 
WGHT    0.014000    0.053000
FVAR       0.68257
SE1   5   -0.451570   -0.335300   -0.846266    11.00000    0.04368    0.03850 =
         0.03829   -0.00616    0.00211   -0.00607
C3    1   -0.002419    0.187478   -0.756217    11.00000    0.05106    0.03020 =
         0.05275    0.00139    0.00633   -0.00766
AFIX  43
H3    2    0.090590    0.294406   -0.783308    11.00000   -1.20000
AFIX   0
C1    1   -0.273278   -0.123685   -0.773394    11.00000    0.03143    0.03107 =
         0.03165    0.00213    0.00220    0.00376
C5    1   -0.148399    0.020533   -0.622007    11.00000    0.05601    0.04721 =
         0.03317   -0.00283    0.00380   -0.00229
AFIX  43
H5    2   -0.154828    0.012354   -0.558564    11.00000   -1.20000
AFIX   0
C6    1   -0.277264   -0.126124   -0.677860    11.00000    0.03991    0.03540 =
         0.03210    0.00421    0.00669    0.00065
C4    1   -0.008536    0.181015   -0.661722    11.00000    0.05896    0.03376 =
         0.04850   -0.00667   -0.00056   -0.00465
AFIX  43
H4    2    0.079249    0.282108   -0.625397    11.00000   -1.20000
AFIX   0
C2    1   -0.131592    0.038405   -0.811485    11.00000    0.04709    0.03826 =
         0.03212    0.00401    0.00503   -0.00252
AFIX  43
H2    2   -0.123567    0.046701   -0.874877    11.00000   -1.20000
AFIX   0
C7    1   -0.328175   -0.240231   -0.957470    11.00000    0.05501    0.05101 =
         0.03425   -0.00869   -0.00292    0.00826
N2    3   -0.258320   -0.189324   -1.028170    11.00000    0.09500    0.07236 =
         0.03615   -0.00228    0.00651    0.00775
O1    4   -0.418447   -0.294983   -0.549950    11.00000    0.15848    0.09935 =
         0.03830    0.01594    0.01193   -0.05298
N1    3   -0.430741   -0.288599   -0.633758    11.00000    0.06439    0.04856 =
         0.03906    0.01066    0.01022   -0.00988
O2    4   -0.570033   -0.413304   -0.682855    11.00000    0.08982    0.05125 =
         0.05328    0.00167    0.01362   -0.03075
HKLF 4
 
REM  w in P21 #4
REM R1 =  0.0206 for   1405 Fo > 4sig(Fo)  and  0.0211 for all   1434 data
REM    109 parameters refined using      1 restraints
 
END  
     
WGHT      0.0137      0.0535 
REM Highest difference peak  0.347,  deepest hole -0.453,  1-sigma level  0.077
Q1    1  -0.2464 -0.3313 -0.9228  11.00000  0.05    0.35
Q2    1  -0.6190 -0.3271 -0.5687  11.00000  0.05    0.29
Q3    1  -0.6972 -0.3447 -0.7888  11.00000  0.05    0.28
Q4    1  -0.4906 -0.3786 -0.7416  11.00000  0.05    0.27
Q5    1  -0.6021 -0.3413 -0.7578  11.00000  0.05    0.27
Q6    1  -0.4568 -0.1994 -0.9273  11.00000  0.05    0.25
Q7    1  -0.4584 -0.4803 -0.9270  11.00000  0.05    0.25
Q8    1  -0.4044 -0.2883 -0.7449  11.00000  0.05    0.25
Q9    1  -0.4809 -0.4327 -0.9368  11.00000  0.05    0.23
Q10   1  -0.4383 -0.1974 -0.7744  11.00000  0.05    0.22
Q11   1  -0.1862 -0.3380 -0.8408  11.00000  0.05    0.21
Q12   1   0.2919  0.1488 -0.8151  11.00000  0.05    0.18
Q13   1  -0.1114  0.4157 -0.7847  11.00000  0.05    0.17
Q14   1  -0.4377  0.0211 -0.8662  11.00000  0.05    0.16
Q15   1  -0.2600  0.3668 -0.7985  11.00000  0.05    0.16
Q16   1  -0.0929 -0.0995 -0.7762  11.00000  0.05    0.15
Q17   1  -0.3409 -0.5848 -0.6024  11.00000  0.05    0.14
Q18   1   0.1229 -0.0673 -0.9734  11.00000  0.05    0.14
Q19   1  -0.6200 -0.6184 -0.6586  11.00000  0.05    0.14
Q20   1  -0.1626 -0.3357 -0.6665  11.00000  0.05    0.13

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0206 for 1405 Fo > 4sig(Fo) and 0.0211 for all 5106 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.35, deepest hole -0.45
  REM Mean Shift 0, Max Shift 0.001.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0211
  REM R1_gt = 0.0206
  REM wR_ref = 0.0530
  REM GOOF = 1.137
  REM Shift_max = 0.001
  REM Shift_mean = 0
  REM Reflections_all = 5106
  REM Reflections_gt = 1405
  REM Parameters = n/a
  REM Hole = -0.45
  REM Peak = 0.35
  REM Flack = 0.060(13)

  
;
_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_w_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1588479'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
_audit_creation_date             2017-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 N2 O2 Se'
_chemical_formula_sum            'C7 H4 N2 O2 Se'
_chemical_formula_weight         227.08
_chemical_absolute_configuration ad
_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'
O O 0.0106 0.0060 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   3.9951(3)
_cell_length_b                   6.9821(6)
_cell_length_c                   14.3544(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.940(2)
_cell_angle_gamma                90.00
_cell_volume                     400.17(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3761
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.84
_exptl_absorpt_coefficient_mu    4.647
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0719 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.7793. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3773
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1401
_reflns_number_total             1424
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(16)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0173
_refine_ls_restrained_S_all      1.297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0769
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C5(H5), C1(H1)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Se1 Se -0.49602(7) -0.13257(11) -0.837622(18) 0.04449(15) Uani 1 d . . .
C6 C -0.6409(7) 0.0906(5) -0.7724(2) 0.0349(7) Uani 1 d . . .
C4 C -0.9083(8) 0.3963(6) -0.7644(2) 0.0406(8) Uani 1 d . . .
H4 H -1.0227 0.4981 -0.7926 0.049 Uiso 1 calc . . R
C2 C -0.6636(9) 0.2516(6) -0.6252(2) 0.0429(8) Uani 1 d . . .
H2 H -0.6128 0.2569 -0.5615 0.051 Uiso 1 calc . . R
C5 C -0.8110(9) 0.2409(5) -0.8168(2) 0.0388(7) Uani 1 d . . .
H5 H -0.8584 0.2369 -0.8806 0.047 Uiso 1 calc . . R
C1 C -0.5698(9) 0.0956(6) -0.6771(3) 0.0427(8) Uani 1 d . . .
H1 H -0.4587 -0.0065 -0.6482 0.051 Uiso 1 calc . . R
C3 C -0.8329(8) 0.3986(5) -0.6689(2) 0.0377(8) Uani 1 d . . .
N1 N -0.9373(8) 0.5629(5) -0.6147(2) 0.0499(8) Uani 1 d . . .
O2 O -0.8395(10) 0.5709(6) -0.5331(2) 0.0810(11) Uani 1 d . . .
O1 O -1.1156(13) 0.6833(6) -0.6516(3) 0.0806(11) Uani 1 d . . .
C7 C -0.6249(10) -0.0518(6) -0.9553(3) 0.0476(8) Uani 1 d . . .
N2 N -0.7009(13) -0.0024(7) -1.0280(3) 0.0749(12) Uani 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
Se1 0.0488(2) 0.0396(2) 0.0450(2) -0.00404(17) 0.00006(13) 0.00761(19)
C6 0.0332(14) 0.0335(16) 0.0380(17) 0.0006(13) 0.0016(12) -0.0022(14)
C4 0.0471(15) 0.034(2) 0.0399(16) 0.0049(14) -0.0057(12) 0.0026(17)
C2 0.0468(19) 0.050(2) 0.0316(16) 0.0035(14) -0.0054(14) 0.0016(17)
C5 0.0479(18) 0.0381(18) 0.0299(16) 0.0036(13) -0.0042(13) -0.0007(14)
C1 0.0459(16) 0.041(2) 0.0411(19) 0.0033(15) -0.0060(14) 0.0077(18)
C3 0.0418(16) 0.033(2) 0.0379(15) 0.0002(14) 0.0029(12) -0.0022(16)
N1 0.0563(19) 0.0458(19) 0.048(2) -0.0099(14) 0.0026(14) -0.0013(15)
O2 0.110(3) 0.084(3) 0.0484(19) -0.0272(17) -0.0128(17) 0.020(2)
O1 0.118(3) 0.055(2) 0.068(2) -0.0127(16) -0.0123(18) 0.039(2)
C7 0.055(2) 0.0467(18) 0.041(2) -0.0090(16) 0.0008(15) -0.0013(17)
N2 0.110(3) 0.069(3) 0.045(2) -0.007(2) -0.005(2) 0.004(3)

_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
Se1 C6 1.917(3) . ?
Se1 C7 1.837(4) . ?
C6 C5 1.394(5) . ?
C6 C1 1.388(5) . ?
C4 C5 1.383(5) . ?
C4 C3 1.394(4) . ?
C2 C1 1.378(5) . ?
C2 C3 1.370(5) . ?
C3 N1 1.455(5) . ?
N1 O2 1.224(4) . ?
N1 O1 1.212(5) . ?
C7 N2 1.131(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 Se1 C6 96.87(15) . . ?
C5 C6 Se1 122.6(2) . . ?
C1 C6 Se1 116.5(3) . . ?
C1 C6 C5 120.8(3) . . ?
C5 C4 C3 119.2(3) . . ?
C3 C2 C1 118.9(3) . . ?
C4 C5 C6 119.0(3) . . ?
C2 C1 C6 120.2(3) . . ?
C4 C3 N1 118.6(3) . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 N1 119.5(3) . . ?
O2 N1 C3 117.4(3) . . ?
O1 N1 C3 119.2(3) . . ?
O1 N1 O2 123.4(3) . . ?
N2 C7 Se1 179.3(4) . . ?

_iucr_refine_instructions_details 
;
TITL w in P21 #4
REM reset to P21 #4
CELL 0.71073 3.9951 6.9821 14.3544 90 91.94 90
ZERR 2 0.0003 0.0006 0.0013 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O Se
UNIT 14 8 4 4 2
 
L.S. 50
PLAN  20
TEMP 0
BOND
fmap 2
acta
SHEL 999 0.83
REM <olex2.extras>
REM <HklSrc "%.\\w.hkl">
REM </olex2.extras>
 
WGHT    0.044000
FVAR       0.62700
SE1   5   -0.496015   -0.132570   -0.837622    11.00000    0.04879    0.03955 =
         0.04502   -0.00404    0.00006    0.00761
C6    1   -0.640862    0.090552   -0.772375    11.00000    0.03317    0.03348 =
         0.03795    0.00064    0.00157   -0.00218
C4    1   -0.908327    0.396301   -0.764437    11.00000    0.04712    0.03436 =
         0.03992    0.00488   -0.00573    0.00259
AFIX  43
H4    2   -1.022726    0.498058   -0.792629    11.00000   -1.20000
AFIX   0
C2    1   -0.663636    0.251553   -0.625179    11.00000    0.04684    0.04975 =
         0.03164    0.00351   -0.00542    0.00155
AFIX  43
H2    2   -0.612837    0.256858   -0.561524    11.00000   -1.20000
AFIX   0
C5    1   -0.811025    0.240930   -0.816800    11.00000    0.04785    0.03811 =
         0.02995    0.00359   -0.00423   -0.00071
AFIX  43
H5    2   -0.858408    0.236874   -0.880649    11.00000   -1.20000
AFIX   0
C1    1   -0.569817    0.095586   -0.677078    11.00000    0.04589    0.04071 =
         0.04107    0.00333   -0.00597    0.00772
AFIX  43
H1    2   -0.458664   -0.006502   -0.648176    11.00000   -1.20000
AFIX   0
C3    1   -0.832937    0.398620   -0.668902    11.00000    0.04178    0.03343 =
         0.03789    0.00017    0.00285   -0.00216
N1    3   -0.937256    0.562889   -0.614694    11.00000    0.05632    0.04580 =
         0.04754   -0.00986    0.00265   -0.00133
O2    4   -0.839504    0.570902   -0.533071    11.00000    0.10974    0.08385 =
         0.04840   -0.02718   -0.01284    0.01980
O1    4   -1.115608    0.683313   -0.651593    11.00000    0.11792    0.05502 =
         0.06769   -0.01268   -0.01229    0.03922
C7    1   -0.624862   -0.051763   -0.955253    11.00000    0.05461    0.04673 =
         0.04129   -0.00900    0.00078   -0.00126
N2    3   -0.700948   -0.002432   -1.028000    11.00000    0.10973    0.06922 =
         0.04535   -0.00734   -0.00485    0.00410
HKLF 4
 
REM  w in P21 #4
REM R1 =  0.0173 for   1401 Fo > 4sig(Fo)  and  0.0199 for all   1424 data
REM    109 parameters refined using      1 restraints
 
END  
     
WGHT      0.0443      0.0000 
REM Highest difference peak  0.399,  deepest hole -0.435,  1-sigma level  0.143
Q1    1  -0.7118  0.3666 -0.5639  11.00000  0.05    0.40
Q2    1  -0.9162  0.3640 -0.4686  11.00000  0.05    0.32
Q3    1  -1.0731  0.5249 -0.5396  11.00000  0.05    0.30
Q4    1  -0.7901 -0.1827 -1.0152  11.00000  0.05    0.30
Q5    1  -0.5490  0.0521 -1.0047  11.00000  0.05    0.29
Q6    1  -1.1669  0.3807 -0.4771  11.00000  0.05    0.28
Q7    1  -0.7201  0.0771 -0.9763  11.00000  0.05    0.28
Q8    1  -0.9083  0.6968 -0.4669  11.00000  0.05    0.27
Q9    1  -0.4739 -0.2552 -0.9970  11.00000  0.05    0.27
Q10   1  -0.4556  0.5896 -0.5169  11.00000  0.05    0.26
Q11   1  -0.7020 -0.1342 -0.9254  11.00000  0.05    0.25
Q12   1  -0.4404  0.1891 -0.5363  11.00000  0.05    0.24
Q13   1  -0.4800  0.0021 -0.5397  11.00000  0.05    0.24
Q14   1  -0.2637  0.0247 -0.9963  11.00000  0.05    0.24
Q15   1  -0.6469  0.1811 -0.4628  11.00000  0.05    0.24
Q16   1  -0.8443  0.5905 -0.5030  11.00000  0.05    0.24
Q17   1  -0.4908 -0.0197 -0.9495  11.00000  0.05    0.24
Q18   1  -0.7450  0.6345 -0.5613  11.00000  0.05    0.24
Q19   1  -0.7242  0.2146 -1.0216  11.00000  0.05    0.24
Q20   1  -0.7346  0.3437 -0.9843  11.00000  0.05    0.24

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0173 for 1401 Fo > 4sig(Fo) and 0.0199 for all 4720 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.40, deepest hole -0.43
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0199
  REM R1_gt = 0.0173
  REM wR_ref = 0.0769
  REM GOOF = 1.298
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4720
  REM Reflections_gt = 1401
  REM Parameters = n/a
  REM Hole = -0.43
  REM Peak = 0.40
  REM Flack = 0.009(16)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
