# 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_zhangqb_1114
_audit_block_doi                 10.5517/ccdc.csd.cc1pvh12
_database_code_depnum_ccdc_archive 'CCDC 1574584'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;
_audit_creation_date             2016-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O3 Se'
_chemical_formula_sum            'C16 H13 N O3 Se'
_chemical_formula_weight         346.23
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2923(5)
_cell_length_b                   11.1395(5)
_cell_length_c                   22.6048(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2843.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1506
_cell_measurement_temperature    292.87(10)
_cell_measurement_theta_max      26.1310
_cell_measurement_theta_min      3.6130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_temperature      292.87(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0228091000
_diffrn_orient_matrix_UB_12      -0.0238416000
_diffrn_orient_matrix_UB_13      -0.0267902000
_diffrn_orient_matrix_UB_21      -0.0231142000
_diffrn_orient_matrix_UB_22      0.0572697000
_diffrn_orient_matrix_UB_23      -0.0074516000
_diffrn_orient_matrix_UB_31      0.0538183000
_diffrn_orient_matrix_UB_32      0.0144652000
_diffrn_orient_matrix_UB_33      -0.0144916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1890
_reflns_number_total             2791
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.019
_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)+(0.0252P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.81194(3) 0.12566(3) 0.52923(2) 0.04265(15) Uani 1 1 d . . . . .
O1 O 0.8043(2) -0.0807(2) 0.77134(10) 0.0430(6) Uani 1 1 d . . . . .
O2 O 0.3638(2) 0.0255(2) 0.58095(11) 0.0491(7) Uani 1 1 d . . . . .
O3 O 0.3150(2) 0.2159(2) 0.61398(11) 0.0506(7) Uani 1 1 d . . . . .
N1 N 1.0487(2) 0.2621(2) 0.64636(12) 0.0408(7) Uani 1 1 d . . . . .
H1 H 1.1065 0.3091 0.6552 0.049 Uiso 1 1 calc R . . . .
C1 C 0.9938(3) 0.2567(3) 0.59319(15) 0.0398(9) Uani 1 1 d . . . . .
H1A H 1.0135 0.3031 0.5605 0.048 Uiso 1 1 calc R . . . .
C2 C 0.9052(3) 0.1733(3) 0.59450(14) 0.0326(8) Uani 1 1 d . . . . .
C3 C 0.9059(3) 0.1221(3) 0.65294(13) 0.0283(7) Uani 1 1 d . . . . .
C4 C 0.9970(3) 0.1799(3) 0.68419(15) 0.0333(8) Uani 1 1 d . . . . .
C5 C 1.0230(3) 0.1501(3) 0.74213(15) 0.0393(9) Uani 1 1 d . . . . .
H5 H 1.0838 0.1881 0.7626 0.047 Uiso 1 1 calc R . . . .
C6 C 0.9556(3) 0.0621(3) 0.76841(14) 0.0390(9) Uani 1 1 d . . . . .
H6 H 0.9721 0.0399 0.8072 0.047 Uiso 1 1 calc R . . . .
C7 C 0.8631(3) 0.0052(3) 0.73840(14) 0.0328(8) Uani 1 1 d . . . . .
C8 C 0.8362(3) 0.0346(3) 0.68045(13) 0.0301(8) Uani 1 1 d . . . . .
H8 H 0.7741 -0.0025 0.6605 0.036 Uiso 1 1 calc R . . . .
C9 C 0.7109(3) -0.1450(3) 0.74316(18) 0.0518(11) Uani 1 1 d . . . . .
H9A H 0.7400 -0.1812 0.7075 0.078 Uiso 1 1 calc GR . . . .
H9B H 0.6477 -0.0906 0.7337 0.078 Uiso 1 1 calc GR . . . .
H9C H 0.6821 -0.2063 0.7693 0.078 Uiso 1 1 calc GR . . . .
C10 C 0.6567(3) 0.1618(3) 0.55936(13) 0.0343(8) Uani 1 1 d . . . . .
C11 C 0.6274(3) 0.2757(3) 0.57866(15) 0.0469(10) Uani 1 1 d . . . . .
H11 H 0.6849 0.3355 0.5786 0.056 Uiso 1 1 calc R . . . .
C12 C 0.5131(4) 0.3028(3) 0.59820(16) 0.0509(10) Uani 1 1 d . . . . .
H12 H 0.4933 0.3790 0.6118 0.061 Uiso 1 1 calc R . . . .
C13 C 0.4322(3) 0.2125(3) 0.59642(14) 0.0378(8) Uani 1 1 d . . . . .
C14 C 0.4607(3) 0.0996(3) 0.57654(14) 0.0347(8) Uani 1 1 d . . . . .
C15 C 0.5725(3) 0.0711(3) 0.55858(13) 0.0350(8) Uani 1 1 d . . . . .
H15 H 0.5915 -0.0062 0.5463 0.042 Uiso 1 1 calc R . . . .
C16 C 0.2674(3) 0.1023(3) 0.59722(19) 0.0555(11) Uani 1 1 d . . . . .
H16A H 0.2136 0.1118 0.5641 0.067 Uiso 1 1 calc R . . . .
H16B H 0.2238 0.0674 0.6300 0.067 Uiso 1 1 calc R . . . .


_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 C2 1.888(3) . ?
Se1 C10 1.923(3) . ?
O1 C7 1.382(4) . ?
O1 C9 1.425(4) . ?
O2 C14 1.374(4) . ?
O2 C16 1.433(4) . ?
O3 C13 1.383(4) . ?
O3 C16 1.427(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.354(4) . ?
N1 C4 1.382(4) . ?
C1 H1A 0.9300 . ?
C1 C2 1.366(4) . ?
C2 C3 1.439(4) . ?
C3 C4 1.404(4) . ?
C3 C8 1.399(4) . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.399(4) . ?
C7 C8 1.384(4) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.382(5) . ?
C10 C15 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.397(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(5) . ?
C13 C14 1.373(4) . ?
C14 C15 1.364(5) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C2 Se1 C10 99.95(13) . . ?
C7 O1 C9 117.5(2) . . ?
C14 O2 C16 105.4(3) . . ?
C13 O3 C16 105.0(3) . . ?
C1 N1 H1 125.5 . . ?
C1 N1 C4 109.0(3) . . ?
C4 N1 H1 125.5 . . ?
N1 C1 H1A 124.9 . . ?
N1 C1 C2 110.3(3) . . ?
C2 C1 H1A 124.9 . . ?
C1 C2 Se1 125.6(3) . . ?
C1 C2 C3 106.6(3) . . ?
C3 C2 Se1 127.5(2) . . ?
C4 C3 C2 106.5(3) . . ?
C8 C3 C2 132.9(3) . . ?
C8 C3 C4 120.5(3) . . ?
N1 C4 C3 107.6(3) . . ?
N1 C4 C5 131.0(3) . . ?
C5 C4 C3 121.5(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
O1 C7 C6 114.3(3) . . ?
O1 C7 C8 124.7(3) . . ?
C8 C7 C6 121.0(3) . . ?
C3 C8 H8 121.2 . . ?
C7 C8 C3 117.5(3) . . ?
C7 C8 H8 121.2 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 Se1 121.5(3) . . ?
C11 C10 C15 120.5(3) . . ?
C15 C10 Se1 117.9(3) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(4) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 121.6 . . ?
C13 C12 C11 116.9(4) . . ?
C13 C12 H12 121.6 . . ?
C12 C13 O3 127.9(3) . . ?
C12 C13 C14 122.0(4) . . ?
C14 C13 O3 110.1(3) . . ?
C13 C14 O2 109.9(3) . . ?
C15 C14 O2 128.2(3) . . ?
C15 C14 C13 121.8(3) . . ?
C10 C15 H15 121.3 . . ?
C14 C15 C10 117.5(3) . . ?
C14 C15 H15 121.3 . . ?
O2 C16 H16A 110.1 . . ?
O2 C16 H16B 110.1 . . ?
O3 C16 O2 108.2(3) . . ?
O3 C16 H16A 110.1 . . ?
O3 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?

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 C2 C3 C4 174.6(2) . . . . ?
Se1 C2 C3 C8 -6.4(5) . . . . ?
Se1 C10 C11 C12 177.3(3) . . . . ?
Se1 C10 C15 C14 -176.0(2) . . . . ?
O1 C7 C8 C3 -178.7(3) . . . . ?
O2 C14 C15 C10 -178.4(3) . . . . ?
O3 C13 C14 O2 -0.6(4) . . . . ?
O3 C13 C14 C15 -177.6(3) . . . . ?
N1 C1 C2 Se1 -175.0(2) . . . . ?
N1 C1 C2 C3 -0.6(4) . . . . ?
N1 C4 C5 C6 -179.2(3) . . . . ?
C1 N1 C4 C3 -0.4(4) . . . . ?
C1 N1 C4 C5 178.5(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C8 179.3(3) . . . . ?
C2 C3 C4 N1 0.0(3) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C2 C3 C8 C7 179.2(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 N1 C1 C2 0.6(4) . . . . ?
C4 C3 C8 C7 -2.0(5) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 O1 -179.8(3) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C6 C7 C8 C3 0.8(5) . . . . ?
C8 C3 C4 N1 -179.1(3) . . . . ?
C8 C3 C4 C5 1.9(5) . . . . ?
C9 O1 C7 C6 -178.3(3) . . . . ?
C9 O1 C7 C8 1.2(5) . . . . ?
C10 Se1 C2 C1 -122.7(3) . . . . ?
C10 Se1 C2 C3 64.0(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C11 C10 C15 C14 1.0(5) . . . . ?
C11 C12 C13 O3 178.9(3) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 O2 178.4(3) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C13 O3 C16 O2 11.5(4) . . . . ?
C13 C14 C15 C10 -1.9(5) . . . . ?
C14 O2 C16 O3 -11.9(4) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C16 O2 C14 C13 7.7(4) . . . . ?
C16 O2 C14 C15 -175.5(3) . . . . ?
C16 O3 C13 C12 174.2(4) . . . . ?
C16 O3 C13 C14 -6.8(4) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-11-15
_olex2_submission_special_instructions 'No special instructions were received'
