# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_g160613a
_database_code_depnum_ccdc_archive 'CCDC 1504130'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2017-01-02 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 Cl N3 Se, H2 O'
_chemical_formula_sum            'C14 H18 Cl N3 O Se'
_chemical_formula_weight         358.72
_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'
Cl Cl 0.1484 0.1585 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   25.4682(9)
_cell_length_b                   25.4682(9)
_cell_length_c                   12.3160(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6918.2(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      27.1970
_cell_measurement_theta_min      3.2020
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3276
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7022
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.77
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514    0.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00  -14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889   37.0000  120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0168718000
_diffrn_orient_matrix_UB_12      0.0154544000
_diffrn_orient_matrix_UB_13      0.0468003000
_diffrn_orient_matrix_UB_21      -0.0208493000
_diffrn_orient_matrix_UB_22      0.0101273000
_diffrn_orient_matrix_UB_23      0.0109738000
_diffrn_orient_matrix_UB_31      -0.0177393000
_diffrn_orient_matrix_UB_32      -0.0263166000
_diffrn_orient_matrix_UB_33      0.0317009000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2344
_reflns_number_total             3137
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.752
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.050
_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)+(0.0527P)²+13.3591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1206
_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., contain disordered crystal water
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(O1) = Uiso(O1A)
3. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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 0.638402(18) 0.007153(19) 0.32104(3) 0.04220(17) Uani 1 d . . .
Cl1 Cl 0.45169(6) 0.12055(6) -0.10133(9) 0.0581(3) Uani 1 d . . .
N1 N 0.52942(15) -0.07527(16) 0.4280(3) 0.0426(8) Uani 1 d . . .
H1 H 0.5536 -0.0798 0.4707 0.051 Uiso 1 calc . . R
N2 N 0.52451(13) -0.01873(13) 0.2825(2) 0.0311(7) Uani 1 d . . .
N3 N 0.62182(14) 0.04443(15) 0.2098(3) 0.0392(8) Uani 1 d . . .
C1 C 0.46452(18) -0.11275(19) 0.4479(3) 0.0399(10) Uani 1 d . . .
H1A H 0.4435 -0.0944 0.4112 0.048 Uiso 1 calc . . R
C2 C 0.4529(2) -0.1143(2) 0.5692(3) 0.0495(11) Uani 1 d . . .
H2A H 0.4654 -0.0737 0.5946 0.059 Uiso 1 calc . . R
H2B H 0.4769 -0.1285 0.6071 0.059 Uiso 1 calc . . R
C3 C 0.3856(2) -0.1563(2) 0.5952(4) 0.0643(14) Uani 1 d . . .
H3A H 0.3802 -0.1591 0.6734 0.077 Uiso 1 calc . . R
H3B H 0.3624 -0.1388 0.5659 0.077 Uiso 1 calc . . R
C4 C 0.3620(2) -0.2180(2) 0.5499(4) 0.0630(14) Uani 1 d . . .
H4A H 0.3187 -0.2416 0.5629 0.076 Uiso 1 calc . . R
H4B H 0.3811 -0.2377 0.5869 0.076 Uiso 1 calc . . R
C5 C 0.3739(2) -0.2165(2) 0.4297(4) 0.0627(13) Uani 1 d . . .
H5A H 0.3504 -0.2019 0.3915 0.075 Uiso 1 calc . . R
H5B H 0.3608 -0.2573 0.4044 0.075 Uiso 1 calc . . R
C6 C 0.4412(2) -0.1754(2) 0.4037(3) 0.0553(12) Uani 1 d . . .
H6A H 0.4642 -0.1926 0.4349 0.066 Uiso 1 calc . . R
H6B H 0.4470 -0.1732 0.3257 0.066 Uiso 1 calc . . R
C7 C 0.55391(16) -0.03489(17) 0.3493(3) 0.0330(8) Uani 1 d . . .
C8 C 0.56331(17) 0.02406(16) 0.2100(3) 0.0319(8) Uani 1 d . . .
C9 C 0.53676(16) 0.04861(16) 0.1320(3) 0.0316(8) Uani 1 d . . .
C10 C 0.48235(17) 0.04591(17) 0.1565(3) 0.0349(9) Uani 1 d . . .
H10 H 0.4629 0.0285 0.2216 0.042 Uiso 1 calc . . R
C11 C 0.45675(18) 0.06854(17) 0.0861(3) 0.0378(9) Uani 1 d . . .
H11 H 0.4205 0.0670 0.1034 0.045 Uiso 1 calc . . R
C12 C 0.48590(19) 0.09373(17) -0.0112(3) 0.0378(9) Uani 1 d . . .
C13 C 0.53928(19) 0.09682(18) -0.0373(3) 0.0410(10) Uani 1 d . . .
H13 H 0.5582 0.1137 -0.1030 0.049 Uiso 1 calc . . R
C14 C 0.56511(18) 0.07487(17) 0.0341(3) 0.0376(9) Uani 1 d . . .
H14 H 0.6019 0.0776 0.0169 0.045 Uiso 1 calc . . R
O1 O 0.4093(4) -0.2894(7) 0.1896(6) 0.0782(16) Uiso 0.542(12) d . 1 .
O1A O 0.3968(6) -0.3337(9) 0.1649(10) 0.0782(16) Uiso 0.458(12) d . 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
Se1 N3 1.833(3) . ?
Se1 C7 1.896(4) . ?
Cl1 C12 1.747(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.458(5) . ?
N1 C7 1.321(5) . ?
N2 C7 1.310(5) . ?
N2 C8 1.373(4) . ?
N3 C8 1.310(5) . ?
C1 H1A 0.9800 . ?
C1 C2 1.520(5) . ?
C1 C6 1.499(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.533(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.482(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.531(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.481(5) . ?
C9 C10 1.386(5) . ?
C9 C14 1.392(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(5) . ?
C12 C13 1.360(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(5) . ?
C14 H14 0.9300 . ?
O1 O1 1.775(10) 15_445 ?
O1 O1 1.775(10) 14 ?
O1A O1A 1.623(10) 14 ?
O1A O1A 1.623(10) 15_445 ?

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
N3 Se1 C7 86.51(15) . . ?
C1 N1 H1 117.5 . . ?
C7 N1 H1 117.5 . . ?
C7 N1 C1 124.9(3) . . ?
C7 N2 C8 111.1(3) . . ?
C8 N3 Se1 107.7(3) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 C2 108.9(3) . . ?
N1 C1 C6 110.6(3) . . ?
C2 C1 H1A 108.7 . . ?
C6 C1 H1A 108.7 . . ?
C6 C1 C2 111.1(3) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.0(4) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.3(4) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 111.9(4) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.4(4) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 C5 111.3(4) . . ?
C1 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 Se1 122.3(3) . . ?
N2 C7 Se1 111.9(3) . . ?
N2 C7 N1 125.7(3) . . ?
N2 C8 C9 117.2(3) . . ?
N3 C8 N2 122.7(3) . . ?
N3 C8 C9 120.0(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 C14 118.5(3) . . ?
C14 C9 C8 121.9(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.9(4) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 Cl1 118.3(3) . . ?
C13 C12 Cl1 120.5(3) . . ?
C13 C12 C11 121.3(4) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
O1 O1 O1 110.4(4) 14 15_445 ?
O1A O1A O1A 119.92(8) 14 15_445 ?

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
Se1 N3 C8 N2 -1.3(4) . . . . ?
Se1 N3 C8 C9 176.8(3) . . . . ?
Cl1 C12 C13 C14 -179.3(3) . . . . ?
N1 C1 C2 C3 -176.6(4) . . . . ?
N1 C1 C6 C5 176.7(3) . . . . ?
N2 C8 C9 C10 22.9(5) . . . . ?
N2 C8 C9 C14 -157.4(3) . . . . ?
N3 Se1 C7 N1 179.3(3) . . . . ?
N3 Se1 C7 N2 -0.8(3) . . . . ?
N3 C8 C9 C10 -155.3(4) . . . . ?
N3 C8 C9 C14 24.4(5) . . . . ?
C1 N1 C7 Se1 -174.5(3) . . . . ?
C1 N1 C7 N2 5.7(6) . . . . ?
C1 C2 C3 C4 53.9(5) . . . . ?
C2 C1 C6 C5 55.6(5) . . . . ?
C2 C3 C4 C5 -54.0(6) . . . . ?
C3 C4 C5 C6 54.3(6) . . . . ?
C4 C5 C6 C1 -55.2(6) . . . . ?
C6 C1 C2 C3 -54.5(5) . . . . ?
C7 Se1 N3 C8 1.1(3) . . . . ?
C7 N1 C1 C2 -136.9(4) . . . . ?
C7 N1 C1 C6 100.7(4) . . . . ?
C7 N2 C8 N3 0.6(5) . . . . ?
C7 N2 C8 C9 -177.5(3) . . . . ?
C8 N2 C7 Se1 0.4(4) . . . . ?
C8 N2 C7 N1 -179.8(4) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
C8 C9 C14 C13 179.4(3) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C9 C14 C13 -0.9(6) . . . . ?
C10 C11 C12 Cl1 178.4(3) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C9 1.1(6) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?

_olex2_date_sample_data_collection 2016-06-13
_olex2_submission_special_instructions 'No special instructions were received'
