# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 2005360'
loop_
_audit_author_name
_audit_author_address
'Prabusankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2020-06-19 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.05.13 svn.r35546bd3 for OlexSys, GUI svn.r5830)
;
_chemical_formula_moiety         'C22 H26 N4 Se2, 1[H2O]'
_chemical_formula_sum            'C22 H28 N4 O1 Se2 '
_chemical_formula_weight         522.413
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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'
Se -0.08110 2.30834 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'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 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'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/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

_symmetry_Int_Tables_number      14
_cell_length_a                   12.244(5)
_cell_length_b                   15.559(5)
_cell_length_c                   13.831(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.152(5)
_cell_angle_gamma                90
_cell_volume                     2422.7(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2299
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.7930
_cell_measurement_theta_min      3.5780
_exptl_absorpt_coefficient_mu    3.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056.176
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.065
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18224
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9981
_diffrn_reflns_theta_full        24.9954
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0309
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  86.00   1.00   22.00    --   17.11  37.00   0.00   95
  2  ω      8.00  59.00   1.00   22.00    --   17.11 -99.00  30.00   51
  3  ω     43.00  73.00   1.00   22.00    --   17.11 178.00-180.00   30
  4  ω     52.00  77.00   1.00   22.00    --   17.11 178.00 120.00   25
  5  ω     38.00  64.00   1.00   22.00    --   17.11 178.00-150.00   26
  6  ω    -52.00  43.00   1.00   22.00    --   17.11 -37.00-180.00   95
  7  ω    -26.00   7.00   1.00   22.00    --  -19.06 -77.00-150.00   33
  8  ω    -84.00 -31.00   1.00   22.00    --  -19.06 138.00  72.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2112
_reflns_number_total             4263
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-dev (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5650
_refine_diff_density_min         -0.6818
_refine_diff_density_rms         0.1205
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             6.4962
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0311
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.0311
_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)+(0.0760P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1898
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C16(H16), C18(H18), C3(H3), C5(H5), C17(H17), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C10(H10a,H10b,H10c), C22(H22a,H22b,H22c), C9(H9a,H9b,H9c)
;
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
Se2 Se -0.17110(7) 0.38057(4) -0.03062(6) 0.0971(4) Uani 1.000000 .
Se1 Se 0.42673(8) 0.36041(6) 0.25809(7) 0.1142(4) Uani 1.000000 .
N3 N 0.0530(4) 0.3055(3) 0.0017(3) 0.0614(12) Uani 1.000000 .
N4 N -0.0956(4) 0.2194(3) -0.0844(3) 0.0664(13) Uani 1.000000 .
C2 C 0.2285(6) 0.1669(4) 0.2958(4) 0.0660(16) Uani 1.000000 .
N2 N 0.1977(4) 0.2977(3) 0.2257(3) 0.0633(12) Uani 1.000000 .
N1 N 0.3366(5) 0.2034(3) 0.3079(4) 0.0761(14) Uani 1.000000 .
C7 C 0.1385(5) 0.2262(3) 0.2425(4) 0.0594(14) Uani 1.000000 .
C14 C 0.0094(6) 0.1762(4) -0.0719(4) 0.0626(15) Uani 1.000000 .
C19 C 0.1032(6) 0.2318(3) -0.0179(4) 0.0592(14) Uani 1.000000 .
C12 C 0.1194(6) 0.3798(3) 0.0594(5) 0.0709(17) Uani 1.000000 .
H12a H 0.1959(6) 0.3818(3) 0.0539(5) 0.085(2) Uiso 1.000000 R
H12b H 0.0765(6) 0.4319(3) 0.0280(5) 0.085(2) Uiso 1.000000 R
C11 C 0.1381(6) 0.3766(3) 0.1740(4) 0.0714(18) Uani 1.000000 .
H11a H 0.0617(6) 0.3807(3) 0.1796(4) 0.086(2) Uiso 1.000000 R
H11b H 0.1853(6) 0.4257(3) 0.2101(4) 0.086(2) Uiso 1.000000 R
C6 C 0.0212(6) 0.2105(4) 0.2181(4) 0.0735(17) Uani 1.000000 .
H6 H -0.0373(6) 0.2504(4) 0.1821(4) 0.088(2) Uiso 1.000000 R
C15 C 0.0314(7) 0.0962(4) -0.1045(5) 0.0777(19) Uani 1.000000 .
H15 H -0.0301(7) 0.0586(4) -0.1410(5) 0.093(2) Uiso 1.000000 R
C16 C 0.1486(8) 0.0748(4) -0.0804(5) 0.087(2) Uani 1.000000 .
H16 H 0.1658(8) 0.0217(4) -0.1018(5) 0.104(3) Uiso 1.000000 R
C18 C 0.2209(6) 0.2088(4) 0.0071(4) 0.0709(17) Uani 1.000000 .
H18 H 0.2830(6) 0.2457(4) 0.0444(4) 0.085(2) Uiso 1.000000 R
C3 C 0.1976(8) 0.0886(4) 0.3276(5) 0.084(2) Uani 1.000000 .
H3 H 0.2550(8) 0.0482(4) 0.3642(5) 0.100(2) Uiso 1.000000 R
C5 C -0.0062(7) 0.1321(4) 0.2496(5) 0.0818(19) Uani 1.000000 .
H5 H -0.0853(7) 0.1186(4) 0.2343(5) 0.098(2) Uiso 1.000000 R
C17 C 0.2415(7) 0.1296(4) -0.0256(5) 0.0819(19) Uani 1.000000 .
H17 H 0.3191(7) 0.1123(4) -0.0107(5) 0.098(2) Uiso 1.000000 R
C8 C 0.4556(6) 0.1638(5) 0.3577(5) 0.097(2) Uani 1.000000 .
H8 H 0.5127(6) 0.2039(5) 0.3488(5) 0.116(3) Uiso 1.000000 R
C4 C 0.0798(9) 0.0738(4) 0.3026(5) 0.088(2) Uani 1.000000 .
H4 H 0.0572(9) 0.0219(4) 0.3225(5) 0.106(3) Uiso 1.000000 R
C20 C -0.2166(6) 0.1869(4) -0.1359(5) 0.0789(18) Uani 1.000000 .
H20 H -0.2696(6) 0.2314(4) -0.1289(5) 0.095(2) Uiso 1.000000 R
C1 C 0.3182(6) 0.2836(4) 0.2657(5) 0.0742(17) Uani 1.000000 .
C21 C -0.2514(7) 0.1720(5) -0.2514(5) 0.114(3) Uani 1.000000 .
H21a H -0.242(5) 0.2242(11) -0.2840(9) 0.171(4) Uiso 1.000000 GR
H21b H -0.202(3) 0.128(3) -0.2615(5) 0.171(4) Uiso 1.000000 GR
H21c H -0.3330(15) 0.154(4) -0.2826(10) 0.171(4) Uiso 1.000000 GR
C10 C 0.4905(8) 0.1520(6) 0.4737(6) 0.136(3) Uani 1.000000 .
H10a H 0.490(6) 0.2067(8) 0.5056(10) 0.203(5) Uiso 1.000000 GR
H10b H 0.435(3) 0.114(3) 0.4854(6) 0.203(5) Uiso 1.000000 GR
H10c H 0.569(2) 0.128(4) 0.5043(11) 0.203(5) Uiso 1.000000 GR
C22 C -0.2335(7) 0.1071(5) -0.0786(6) 0.122(3) Uani 1.000000 .
H22a H -0.190(4) 0.0599(11) -0.091(4) 0.183(5) Uiso 1.000000 GR
H22b H -0.205(5) 0.1187(13) -0.0046(9) 0.183(5) Uiso 1.000000 GR
H22c H -0.3163(9) 0.093(2) -0.105(3) 0.183(5) Uiso 1.000000 GR
C9 C 0.4611(8) 0.0808(6) 0.3008(7) 0.152(4) Uani 1.000000 .
H9a H 0.409(5) 0.0390(17) 0.311(5) 0.228(6) Uiso 1.000000 GR
H9b H 0.437(6) 0.0923(11) 0.2271(12) 0.228(6) Uiso 1.000000 GR
H9c H 0.5409(15) 0.059(3) 0.329(4) 0.228(6) Uiso 1.000000 GR
C13 C -0.0679(6) 0.2981(3) -0.0392(4) 0.0692(17) Uani 1.000000 .


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
Se2 C13 1.837(6) . ?
Se1 C1 1.821(6) . ?
N3 C19 1.377(6) . ?
N3 C12 1.457(6) . ?
N3 C13 1.366(7) . ?
N4 C14 1.399(7) . ?
N4 C20 1.458(7) . ?
N4 C13 1.357(6) . ?
C2 N1 1.390(7) . ?
C2 C7 1.404(7) . ?
C2 C3 1.396(8) . ?
N2 C7 1.397(6) . ?
N2 C11 1.463(6) . ?
N2 C1 1.374(7) . ?
N1 C8 1.479(8) . ?
N1 C1 1.358(7) . ?
C7 C6 1.362(8) . ?
C14 C19 1.397(7) . ?
C14 C15 1.386(8) . ?
C19 C18 1.390(7) . ?
C12 C11 1.511(8) . ?
C6 C5 1.380(8) . ?
C15 C16 1.380(9) . ?
C16 C17 1.384(9) . ?
C18 C17 1.371(8) . ?
C3 C4 1.364(9) . ?
C5 C4 1.364(9) . ?
C8 C10 1.500(9) . ?
C8 C9 1.527(10) . ?
C20 C21 1.501(8) . ?
C20 C22 1.529(8) . ?

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
C12 N3 C19 125.0(5) . . ?
C13 N3 C19 110.0(4) . . ?
C13 N3 C12 125.0(5) . . ?
C20 N4 C14 127.0(5) . . ?
C13 N4 C14 109.0(5) . . ?
C13 N4 C20 124.0(6) . . ?
C7 C2 N1 107.9(5) . . ?
C3 C2 N1 133.0(6) . . ?
C3 C2 C7 119.0(6) . . ?
C11 N2 C7 123.9(5) . . ?
C1 N2 C7 110.5(5) . . ?
C1 N2 C11 125.6(5) . . ?
C8 N1 C2 127.1(6) . . ?
C1 N1 C2 109.6(5) . . ?
C1 N1 C8 123.4(6) . . ?
N2 C7 C2 105.0(5) . . ?
C6 C7 C2 123.0(6) . . ?
C6 C7 N2 131.9(5) . . ?
C19 C14 N4 106.9(5) . . ?
C15 C14 N4 132.6(6) . . ?
C15 C14 C19 120.4(6) . . ?
C14 C19 N3 106.5(5) . . ?
C18 C19 N3 131.6(5) . . ?
C18 C19 C14 121.9(5) . . ?
C11 C12 N3 111.7(4) . . ?
C12 C11 N2 112.4(4) . . ?
C5 C6 C7 116.3(6) . . ?
C16 C15 C14 117.0(6) . . ?
C17 C16 C15 122.5(6) . . ?
C17 C18 C19 117.1(6) . . ?
C4 C3 C2 117.2(6) . . ?
C4 C5 C6 121.7(7) . . ?
C18 C17 C16 121.1(7) . . ?
C10 C8 N1 111.3(6) . . ?
C9 C8 N1 110.3(6) . . ?
C9 C8 C10 113.3(7) . . ?
C5 C4 C3 122.7(6) . . ?
C21 C20 N4 112.5(5) . . ?
C22 C20 N4 110.3(5) . . ?
C22 C20 C21 112.7(6) . . ?
N2 C1 Se1 124.3(5) . . ?
N1 C1 Se1 128.8(5) . . ?
N1 C1 N2 106.9(5) . . ?
N3 C13 Se2 125.1(4) . . ?
N4 C13 Se2 127.4(5) . . ?
N4 C13 N3 107.5(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se2 C13 N3 C19 179.4(4) . . . . ?
Se2 C13 N3 C12 0.5(6) . . . . ?
Se2 C13 N4 C14 -178.9(5) . . . . ?
Se2 C13 N4 C20 0.4(6) . . . . ?
Se1 C1 N2 C7 179.0(4) . . . . ?
Se1 C1 N2 C11 -2.0(6) . . . . ?
Se1 C1 N1 C2 -179.5(5) . . . . ?
Se1 C1 N1 C8 0.2(7) . . . . ?
N3 C19 C14 N4 0.8(4) . . . . ?
N3 C19 C14 C15 179.0(4) . . . . ?
N3 C19 C18 C17 -179.1(6) . . . . ?
N3 C12 C11 N2 56.4(5) . . . . ?
N3 C13 N4 C14 0.1(5) . . . . ?
N3 C13 N4 C20 179.3(4) . . . . ?
N4 C14 C19 C18 -179.6(4) . . . . ?
N4 C14 C15 C16 178.1(7) . . . . ?
C2 N1 C8 C10 -67.6(7) . . . . ?
C2 N1 C8 C9 59.1(7) . . . . ?
C2 N1 C1 N2 -0.6(4) . . . . ?
C2 C7 N2 C11 -178.6(4) . . . . ?
C2 C7 N2 C1 0.4(5) . . . . ?
C2 C7 C6 C5 0.6(6) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
N2 C7 C6 C5 -178.3(6) . . . . ?
N2 C1 N1 C8 179.1(4) . . . . ?
C7 C6 C5 C4 0.2(6) . . . . ?
C14 C19 C18 C17 1.4(6) . . . . ?
C14 C15 C16 C17 0.5(7) . . . . ?
C19 C18 C17 C16 -0.5(6) . . . . ?
C6 C5 C4 C3 -0.2(7) . . . . ?
C15 C16 C17 C18 -0.5(7) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 36 electrons were 
found in a volume of 326Å³ in 1 void per unit cell. 
This is consistent with the presence of 1[H2O] per Formula Unit 
which account for 40 electrons per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.500 0.500 162.5 18.4 '2 water'
2 0.500 0.000 0.000 162.5 18.4 '2 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2005361'
loop_
_audit_author_name
_audit_author_address
'Prabusankar Ganesan'
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-07
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 Br2 N4 O0.31 Se1.69 Zn'
_chemical_formula_sum            'C22 H26 Br2 N4 O0.31 Se1.69 Zn'
_chemical_formula_weight         710.06
_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'
Br Br -0.2901 2.4595 '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'
Zn Zn 0.2839 1.4301 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.2917(5)
_cell_length_b                   9.4210(4)
_cell_length_c                   16.2331(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.499(3)
_cell_angle_gamma                90
_cell_volume                     2639.53(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7787
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      28.8020
_cell_measurement_theta_min      3.3270
_shelx_estimated_absorpt_T_max   0.499
_shelx_estimated_absorpt_T_min   0.432
_exptl_absorpt_coefficient_mu    6.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20712
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  50.00   0.50   12.00    --    3.60  38.00-180.00  156
  2  ω    -49.00  76.00   0.50   12.00    --    3.60   0.00 -60.00  250
  3  ω    -84.00 -56.00   0.50   12.00    --    3.60   0.00 -60.00   56
  4  ω    -50.00 -24.00   0.50   12.00    --   -3.90 -57.00-180.00   52
  5  ω    -47.00  25.00   0.50   12.00    --   -3.90 -57.00 -60.00  144
  6  ω    -93.00 -63.00   0.50   12.00    --   -3.90 -57.00 -60.00   60
  7  ω    -55.00 -30.00   0.50   12.00    --   -3.90 -77.00 150.00   50
  8  ω    -58.00  -2.00   0.50   12.00    --   -3.90 -82.00 -90.00  112
  9  ω    -20.00   5.00   0.50   12.00    --   -3.90 -77.00 150.00   50
 10  ω     -3.00  22.00   0.50   12.00    --   -3.90 -57.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2671
_reflns_number_total             3006
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+8.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0647
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O1)=1-FVAR(1)
 Sof(Se1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.71031(2) 1.02376(4) 0.61750(2) 0.03727(11) Uani 1 1 d . . . . .
Zn1 Zn 0.750000 0.90109(5) 0.500000 0.02393(12) Uani 1 2 d S T P . .
N1 N 0.51681(14) 0.8125(3) 0.53308(15) 0.0293(5) Uani 1 1 d . . . . .
C1 C 0.58314(17) 0.7411(3) 0.52281(18) 0.0286(6) Uani 1 1 d . . . . .
N2 N 0.59349(13) 0.6453(3) 0.58414(14) 0.0257(5) Uani 1 1 d . . . . .
C2 C 0.53031(17) 0.6523(3) 0.63408(18) 0.0280(6) Uani 1 1 d . . . . .
C3 C 0.5095(2) 0.5726(4) 0.7012(2) 0.0389(8) Uani 1 1 d . . . . .
H3 H 0.541110 0.500497 0.723200 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4399(2) 0.6050(4) 0.7337(2) 0.0480(9) Uani 1 1 d . . . . .
H4 H 0.424093 0.552712 0.778246 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3923(2) 0.7140(4) 0.7017(2) 0.0445(9) Uani 1 1 d . . . . .
H5 H 0.346076 0.733340 0.725974 0.053 Uiso 1 1 calc R U . . .
C6 C 0.41230(18) 0.7934(4) 0.6351(2) 0.0382(8) Uani 1 1 d . . . . .
H6 H 0.380686 0.865815 0.613363 0.046 Uiso 1 1 calc R U . . .
C7 C 0.48259(17) 0.7595(3) 0.60193(18) 0.0294(6) Uani 1 1 d . . . . .
C8 C 0.48582(19) 0.9287(3) 0.4817(2) 0.0349(7) Uani 1 1 d . . . . .
H8A H 0.429651 0.925735 0.478875 0.042 Uiso 1 1 calc R U . . .
H8B H 0.502789 0.918608 0.426115 0.042 Uiso 1 1 calc R U . . .
C9 C 0.66108(19) 0.5487(3) 0.5947(2) 0.0346(7) Uani 1 1 d . . . . .
H9 H 0.697467 0.575944 0.553466 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6356(3) 0.3973(4) 0.5753(3) 0.0597(11) Uani 1 1 d . . . . .
H10A H 0.600287 0.366434 0.615113 0.090 Uiso 1 1 calc R U . . .
H10B H 0.680057 0.336125 0.577596 0.090 Uiso 1 1 calc R U . . .
H10C H 0.610238 0.393620 0.521074 0.090 Uiso 1 1 calc R U . . .
C11 C 0.7023(2) 0.5690(5) 0.6785(2) 0.0495(9) Uani 1 1 d . . . . .
H11A H 0.713975 0.667786 0.686832 0.074 Uiso 1 1 calc R U . . .
H11B H 0.749479 0.515169 0.681644 0.074 Uiso 1 1 calc R U . . .
H11C H 0.669514 0.537031 0.720454 0.074 Uiso 1 1 calc R U . . .
Se1 Se 0.64120(2) 0.76302(4) 0.43120(2) 0.02544(14) Uani 0.845(2) 1 d . . P A 1
O1 O 0.6543(7) 0.7881(14) 0.4806(10) 0.024(3) Uiso 0.155(2) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.3673(4) . ?
Zn1 Se1 2.4944(4) 2_656 ?
Zn1 Se1 2.4944(4) . ?
Zn1 O1 1.977(13) 2_656 ?
Zn1 O1 1.977(13) . ?
N1 C1 1.349(4) . ?
N1 C7 1.389(4) . ?
N1 C8 1.458(4) . ?
C1 N2 1.348(4) . ?
C1 Se1 1.856(3) . ?
C1 O1 1.511(13) . ?
N2 C2 1.401(4) . ?
N2 C9 1.483(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.386(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(4) . ?
C8 C8 1.538(7) 5_676 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.520(5) . ?
C9 C11 1.510(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
Br1 Zn1 Br1 121.56(3) . 2_656 ?
Br1 Zn1 Se1 98.141(11) 2_656 . ?
Br1 Zn1 Se1 111.563(12) 2_656 2_656 ?
Br1 Zn1 Se1 111.562(12) . . ?
Br1 Zn1 Se1 98.141(11) . 2_656 ?
Se1 Zn1 Se1 117.14(3) . 2_656 ?
O1 Zn1 Br1 96.3(4) . . ?
O1 Zn1 Br1 114.6(4) 2_656 . ?
O1 Zn1 O1 114.8(7) 2_656 . ?
C1 N1 C7 109.1(2) . . ?
C1 N1 C8 126.1(3) . . ?
C7 N1 C8 124.8(3) . . ?
N1 C1 Se1 123.3(2) . . ?
N1 C1 O1 129.2(5) . . ?
N2 C1 N1 108.6(2) . . ?
N2 C1 Se1 127.8(2) . . ?
N2 C1 O1 117.1(6) . . ?
C1 N2 C2 108.8(2) . . ?
C1 N2 C9 124.4(2) . . ?
C2 N2 C9 126.8(2) . . ?
C3 C2 N2 132.6(3) . . ?
C7 C2 N2 106.5(2) . . ?
C7 C2 C3 120.8(3) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 121.8 . . ?
C5 C6 C7 116.4(3) . . ?
C7 C6 H6 121.8 . . ?
N1 C7 C6 130.7(3) . . ?
C2 C7 N1 107.0(3) . . ?
C2 C7 C6 122.3(3) . . ?
N1 C8 C8 109.7(3) . 5_676 ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C8 C8 H8A 109.7 5_676 . ?
C8 C8 H8B 109.7 5_676 . ?
H8A C8 H8B 108.2 . . ?
N2 C9 H9 107.2 . . ?
N2 C9 C10 109.6(3) . . ?
N2 C9 C11 110.6(3) . . ?
C10 C9 H9 107.2 . . ?
C11 C9 H9 107.2 . . ?
C11 C9 C10 114.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 Se1 Zn1 97.44(10) . . ?
C1 O1 Zn1 141.5(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 C2 1.9(3) . . . . ?
N1 C1 N2 C9 -178.7(3) . . . . ?
N1 C1 Se1 Zn1 106.6(3) . . . . ?
N1 C1 O1 Zn1 81.3(14) . . . . ?
C1 N1 C7 C2 0.0(3) . . . . ?
C1 N1 C7 C6 -176.5(3) . . . . ?
C1 N1 C8 C8 -92.4(4) . . . 5_676 ?
C1 N2 C2 C3 175.2(3) . . . . ?
C1 N2 C2 C7 -1.9(3) . . . . ?
C1 N2 C9 C10 -109.8(4) . . . . ?
C1 N2 C9 C11 122.7(3) . . . . ?
N2 C1 Se1 Zn1 -80.9(3) . . . . ?
N2 C1 O1 Zn1 -70.4(13) . . . . ?
N2 C2 C3 C4 -176.7(3) . . . . ?
N2 C2 C7 N1 1.1(3) . . . . ?
N2 C2 C7 C6 178.0(3) . . . . ?
C2 N2 C9 C10 69.5(4) . . . . ?
C2 N2 C9 C11 -58.0(4) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C2 C7 N1 -176.4(3) . . . . ?
C3 C2 C7 C6 0.5(5) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 N1 175.8(3) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C7 N1 C1 N2 -1.2(3) . . . . ?
C7 N1 C1 Se1 172.5(2) . . . . ?
C7 N1 C1 O1 -154.7(8) . . . . ?
C7 N1 C8 C8 86.4(4) . . . 5_676 ?
C7 C2 C3 C4 0.0(5) . . . . ?
C8 N1 C1 N2 177.7(3) . . . . ?
C8 N1 C1 Se1 -8.6(4) . . . . ?
C8 N1 C1 O1 24.2(9) . . . . ?
C8 N1 C7 C2 -179.0(3) . . . . ?
C8 N1 C7 C6 4.5(5) . . . . ?
C9 N2 C2 C3 -4.2(5) . . . . ?
C9 N2 C2 C7 178.7(3) . . . . ?
Se1 C1 N2 C2 -171.4(2) . . . . ?
Se1 C1 N2 C9 8.0(4) . . . . ?
O1 C1 N2 C2 159.1(7) . . . . ?
O1 C1 N2 C9 -21.5(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
