# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2265781'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-05-27 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8352(8)
_cell_length_b                   23.420(2)
_cell_length_c                   5.8137(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.8340(10)
_cell_angle_gamma                90
_cell_volume                     1198.69(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15295
_cell_measurement_theta_min      3.717
_cell_measurement_theta_max      77.413

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.772
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24889
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.775
_diffrn_reflns_theta_max         77.816
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2531
_reflns_number_gt                2330
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.08P)²+0.8P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.76963(14) 0.48092(5) 0.4349(2) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.84806(17) 0.47364(6) 0.8226(2) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.832(3) 0.4853(9) 0.964(4) 0.030 Uiso 1 1 d . U . . .
C1 C 0.6622(2) 0.56643(7) 0.9201(3) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.7529 0.5888 0.9763 0.028 Uiso 1 1 calc R U . . .
H1B H 0.6466 0.5354 1.0315 0.028 Uiso 1 1 calc R U . . .
N2 N 0.67840(16) 0.54321(6) 0.6876(2) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.59490(19) 0.57599(7) 0.5031(3) 0.0222(4) Uani 1 1 d . . . . .
H3A H 0.5144 0.5525 0.4207 0.027 Uiso 1 1 calc R U . . .
H3B H 0.6641 0.5903 0.3906 0.027 Uiso 1 1 calc R U . . .
C3A C 0.52748(18) 0.62467(7) 0.6301(3) 0.0210(3) Uani 1 1 d . . . . .
C4 C 0.37904(19) 0.65415(7) 0.5569(3) 0.0230(4) Uani 1 1 d . . . . .
H4 H 0.2988 0.6404 0.4526 0.028 Uiso 1 1 calc R U . . .
C5 C 0.38502(19) 0.70359(7) 0.6701(3) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.3089 0.7323 0.6646 0.028 Uiso 1 1 calc R U . . .
C6 C 0.53811(19) 0.70473(7) 0.8098(3) 0.0225(4) Uani 1 1 d . . . . .
H6 H 0.5772 0.7436 0.8541 0.027 Uiso 1 1 calc R U . . .
C7 C 0.52736(19) 0.66221(7) 1.0143(3) 0.0234(4) Uani 1 1 d . . . . .
H7A H 0.6174 0.6649 1.1272 0.028 Uiso 1 1 calc R U . . .
H7B H 0.4343 0.6686 1.0944 0.028 Uiso 1 1 calc R U . . .
C7A C 0.52183(19) 0.60463(7) 0.8858(3) 0.0217(4) Uani 1 1 d . . . . .
H7C H 0.4265 0.5831 0.9083 0.026 Uiso 1 1 calc R U . . .
O8 O 0.63119(13) 0.67238(5) 0.66307(19) 0.0215(3) Uani 1 1 d . . . . .
C8 C 0.76559(18) 0.49824(7) 0.6353(3) 0.0220(3) Uani 1 1 d . . . . .
C9 C 0.91801(18) 0.41937(7) 0.8193(3) 0.0226(4) Uani 1 1 d . . . . .
C10 C 0.99874(18) 0.40119(8) 0.6362(3) 0.0243(4) Uani 1 1 d . . . . .
H10 H 1.0085 0.4255 0.5076 0.029 Uiso 1 1 calc R U . . .
C11 C 1.0646(2) 0.34735(8) 0.6432(3) 0.0275(4) Uani 1 1 d . . . . .
H11 H 1.1186 0.3348 0.5181 0.033 Uiso 1 1 calc R U . . .
C12 C 1.0522(2) 0.31154(8) 0.8318(3) 0.0291(4) Uani 1 1 d . . . . .
H12 H 1.0974 0.2747 0.8354 0.035 Uiso 1 1 calc R U . . .
C13 C 0.9734(2) 0.33013(8) 1.0146(3) 0.0304(4) Uani 1 1 d . . . . .
H13 H 0.9651 0.3059 1.1441 0.036 Uiso 1 1 calc R U . . .
C14 C 0.90676(19) 0.38363(8) 1.0095(3) 0.0265(4) Uani 1 1 d . . . . .
H14 H 0.8533 0.3961 1.1355 0.032 Uiso 1 1 calc R U . . .


_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
O1 C8 1.237(2) . ?
N1 C8 1.384(2) . ?
N1 C9 1.414(2) . ?
N1 H1 0.89(2) . ?
C1 N2 1.4751(19) . ?
C1 C7A 1.528(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C8 1.355(2) . ?
N2 C3 1.467(2) . ?
C3 C3A 1.508(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O8 1.4475(19) . ?
C3A C4 1.511(2) . ?
C3A C7A 1.563(2) . ?
C4 C5 1.331(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.518(2) . ?
C5 H5 0.9500 . ?
C6 O8 1.4477(18) . ?
C6 C7 1.560(2) . ?
C6 H6 1.0000 . ?
C7 C7A 1.541(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A H7C 1.0000 . ?
C9 C14 1.397(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C8 N1 C9 124.42(14) . . ?
C8 N1 H1 118.8(15) . . ?
C9 N1 H1 113.3(15) . . ?
N2 C1 C7A 103.68(12) . . ?
N2 C1 H1A 111.0 . . ?
C7A C1 H1A 111.0 . . ?
N2 C1 H1B 111.0 . . ?
C7A C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C8 N2 C3 120.20(13) . . ?
C8 N2 C1 126.41(14) . . ?
C3 N2 C1 113.30(13) . . ?
N2 C3 C3A 103.44(12) . . ?
N2 C3 H3A 111.1 . . ?
C3A C3 H3A 111.1 . . ?
N2 C3 H3B 111.1 . . ?
C3A C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
O8 C3A C3 112.13(13) . . ?
O8 C3A C4 102.08(13) . . ?
C3 C3A C4 125.21(14) . . ?
O8 C3A C7A 100.16(12) . . ?
C3 C3A C7A 106.51(13) . . ?
C4 C3A C7A 107.97(12) . . ?
C5 C4 C3A 105.12(14) . . ?
C5 C4 H4 127.4 . . ?
C3A C4 H4 127.4 . . ?
C4 C5 C6 106.04(14) . . ?
C4 C5 H5 127.0 . . ?
C6 C5 H5 127.0 . . ?
O8 C6 C5 101.56(12) . . ?
O8 C6 C7 100.91(12) . . ?
C5 C6 C7 106.73(13) . . ?
O8 C6 H6 115.3 . . ?
C5 C6 H6 115.3 . . ?
C7 C6 H6 115.3 . . ?
C7A C7 C6 100.97(12) . . ?
C7A C7 H7A 111.6 . . ?
C6 C7 H7A 111.6 . . ?
C7A C7 H7B 111.6 . . ?
C6 C7 H7B 111.6 . . ?
H7A C7 H7B 109.4 . . ?
C1 C7A C7 117.18(14) . . ?
C1 C7A C3A 102.08(12) . . ?
C7 C7A C3A 101.32(12) . . ?
C1 C7A H7C 111.8 . . ?
C7 C7A H7C 111.8 . . ?
C3A C7A H7C 111.8 . . ?
C3A O8 C6 95.58(11) . . ?
O1 C8 N2 121.91(15) . . ?
O1 C8 N1 123.34(15) . . ?
N2 C8 N1 114.75(14) . . ?
C14 C9 C10 119.71(16) . . ?
C14 C9 N1 117.87(15) . . ?
C10 C9 N1 122.41(15) . . ?
C11 C10 C9 119.60(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.70(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.44(17) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.47(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 120.08(16) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?

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
C7A C1 N2 C8 -165.15(15) . . . . ?
C7A C1 N2 C3 18.14(18) . . . . ?
C8 N2 C3 C3A -174.35(14) . . . . ?
C1 N2 C3 C3A 2.58(18) . . . . ?
N2 C3 C3A O8 86.56(15) . . . . ?
N2 C3 C3A C4 -149.15(15) . . . . ?
N2 C3 C3A C7A -22.06(16) . . . . ?
O8 C3A C4 C5 -33.18(15) . . . . ?
C3 C3A C4 C5 -161.68(15) . . . . ?
C7A C3A C4 C5 71.83(16) . . . . ?
C3A C4 C5 C6 0.82(16) . . . . ?
C4 C5 C6 O8 31.70(16) . . . . ?
C4 C5 C6 C7 -73.57(16) . . . . ?
O8 C6 C7 C7A -35.63(15) . . . . ?
C5 C6 C7 C7A 70.10(15) . . . . ?
N2 C1 C7A C7 -139.54(14) . . . . ?
N2 C1 C7A C3A -29.94(16) . . . . ?
C6 C7 C7A C1 109.07(15) . . . . ?
C6 C7 C7A C3A -0.97(15) . . . . ?
O8 C3A C7A C1 -84.04(14) . . . . ?
C3 C3A C7A C1 32.85(16) . . . . ?
C4 C3A C7A C1 169.60(13) . . . . ?
O8 C3A C7A C7 37.24(14) . . . . ?
C3 C3A C7A C7 154.13(13) . . . . ?
C4 C3A C7A C7 -69.11(15) . . . . ?
C3 C3A O8 C6 -172.92(13) . . . . ?
C4 C3A O8 C6 50.73(13) . . . . ?
C7A C3A O8 C6 -60.29(13) . . . . ?
C5 C6 O8 C3A -49.80(13) . . . . ?
C7 C6 O8 C3A 59.99(13) . . . . ?
C3 N2 C8 O1 -5.1(2) . . . . ?
C1 N2 C8 O1 178.40(15) . . . . ?
C3 N2 C8 N1 175.08(14) . . . . ?
C1 N2 C8 N1 -1.4(2) . . . . ?
C9 N1 C8 O1 -15.1(3) . . . . ?
C9 N1 C8 N2 164.74(15) . . . . ?
C8 N1 C9 C14 -137.80(17) . . . . ?
C8 N1 C9 C10 43.3(3) . . . . ?
C14 C9 C10 C11 1.2(2) . . . . ?
N1 C9 C10 C11 -179.89(15) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C10 C9 C14 C13 -1.0(3) . . . . ?
N1 C9 C14 C13 -179.96(16) . . . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_7p
_database_code_depnum_ccdc_archive 'CCDC 2265783'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-05-27 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Cl N2 O Se'
_chemical_formula_sum            'C15 H15 Cl N2 O Se'
_chemical_formula_weight         353.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.31793(12)
_cell_length_b                   9.33602(18)
_cell_length_c                   23.9880(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1414.92(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6961
_cell_measurement_theta_min      5.1
_cell_measurement_theta_max      79.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    5.300
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_T_max  0.612
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9337
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.685
_diffrn_reflns_theta_max         79.396
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2870
_reflns_number_gt                2771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.922

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+1.2993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.029(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.79406(6) 0.28658(5) 0.71586(2) 0.02223(14) Uani 1 1 d . . . . .
Cl1 Cl 0.28101(18) 0.28229(13) 0.83202(4) 0.0325(2) Uani 1 1 d . . . . .
N1 N 0.4925(6) 0.4853(4) 0.75294(15) 0.0229(7) Uani 1 1 d . . . . .
H1 H 0.392(9) 0.561(6) 0.748(2) 0.028 Uiso 1 1 d . U . . .
C1 C 0.5271(7) 0.3509(5) 0.60956(16) 0.0234(8) Uani 1 1 d . . . . .
H1A H 0.5130 0.2456 0.6125 0.028 Uiso 1 1 calc R U . . .
H1B H 0.6760 0.3750 0.6008 0.028 Uiso 1 1 calc R U . . .
N2 N 0.4577(5) 0.4218(4) 0.66118(13) 0.0201(7) Uani 1 1 d . . . . .
C2 C 0.5616(7) 0.4075(4) 0.70912(16) 0.0211(8) Uani 1 1 d . . . . .
C3 C 0.2611(6) 0.5077(5) 0.65392(16) 0.0241(9) Uani 1 1 d . . . . .
H3A H 0.2930 0.6115 0.6534 0.029 Uiso 1 1 calc R U . . .
H3B H 0.1586 0.4878 0.6842 0.029 Uiso 1 1 calc R U . . .
C3A C 0.1750(7) 0.4575(4) 0.59726(16) 0.0230(9) Uani 1 1 d . . . . .
H3C H 0.0736 0.3761 0.6016 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0869(7) 0.5737(5) 0.55754(18) 0.0251(9) Uani 1 1 d . . . . .
H4A H 0.0753 0.6679 0.5762 0.030 Uiso 1 1 calc R U . . .
H4B H -0.0526 0.5463 0.5420 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2624(7) 0.5736(5) 0.51202(15) 0.0256(9) Uani 1 1 d . . . . .
H5 H 0.2672 0.6617 0.4884 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2437(7) 0.4346(5) 0.47994(17) 0.0277(9) Uani 1 1 d . . . . .
H6 H 0.1901 0.4225 0.4432 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3170(7) 0.3334(4) 0.51329(17) 0.0256(8) Uani 1 1 d . . . . .
H7 H 0.3281 0.2338 0.5056 0.031 Uiso 1 1 calc R U . . .
C7A C 0.3795(7) 0.4102(5) 0.56627(17) 0.0228(8) Uani 1 1 d . . . . .
O8 O 0.4499(5) 0.5484(3) 0.54484(12) 0.0239(6) Uani 1 1 d . . . . .
C8 C 0.5861(7) 0.4764(5) 0.80627(17) 0.0230(8) Uani 1 1 d . . . . .
C9 C 0.5018(7) 0.3860(5) 0.84722(17) 0.0229(8) Uani 1 1 d . . . . .
C10 C 0.5941(7) 0.3771(5) 0.89943(17) 0.0257(9) Uani 1 1 d . . . . .
H10 H 0.5371 0.3142 0.9267 0.031 Uiso 1 1 calc R U . . .
C11 C 0.7690(8) 0.4596(4) 0.91181(17) 0.0266(9) Uani 1 1 d . . . . .
H11 H 0.8325 0.4534 0.9476 0.032 Uiso 1 1 calc R U . . .
C12 C 0.8525(8) 0.5520(5) 0.87184(19) 0.0299(10) Uani 1 1 d . . . . .
H12 H 0.9718 0.6099 0.8804 0.036 Uiso 1 1 calc R U . . .
C13 C 0.7601(7) 0.5590(5) 0.81950(18) 0.0290(10) Uani 1 1 d . . . . .
H13 H 0.8176 0.6217 0.7922 0.035 Uiso 1 1 calc R U . . .


_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 1.860(4) . ?
Cl1 C9 1.737(5) . ?
N1 C2 1.350(5) . ?
N1 C8 1.412(5) . ?
N1 H1 0.96(6) . ?
C1 N2 1.471(5) . ?
C1 C7A 1.502(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C2 1.331(5) . ?
N2 C3 1.488(5) . ?
C3 C3A 1.537(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A C4 1.547(6) . ?
C3A C7A 1.554(6) . ?
C3A H3C 1.0000 . ?
C4 C5 1.556(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O8 1.441(5) . ?
C5 C6 1.513(6) . ?
C5 H5 1.0000 . ?
C6 C7 1.322(6) . ?
C6 H6 0.9500 . ?
C7 C7A 1.512(6) . ?
C7 H7 0.9500 . ?
C7A O8 1.458(5) . ?
C8 C13 1.380(7) . ?
C8 C9 1.400(6) . ?
C9 C10 1.384(6) . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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 N1 C8 122.6(4) . . ?
C2 N1 H1 121(3) . . ?
C8 N1 H1 116(3) . . ?
N2 C1 C7A 103.4(3) . . ?
N2 C1 H1A 111.1 . . ?
C7A C1 H1A 111.1 . . ?
N2 C1 H1B 111.1 . . ?
C7A C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
C2 N2 C1 122.4(3) . . ?
C2 N2 C3 124.5(3) . . ?
C1 N2 C3 113.1(3) . . ?
N2 C2 N1 117.3(4) . . ?
N2 C2 Se1 121.7(3) . . ?
N1 C2 Se1 120.9(3) . . ?
N2 C3 C3A 103.6(3) . . ?
N2 C3 H3A 111.0 . . ?
C3A C3 H3A 111.0 . . ?
N2 C3 H3B 111.0 . . ?
C3A C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C3A C4 117.3(4) . . ?
C3 C3A C7A 102.4(3) . . ?
C4 C3A C7A 101.8(3) . . ?
C3 C3A H3C 111.5 . . ?
C4 C3A H3C 111.5 . . ?
C7A C3A H3C 111.5 . . ?
C3A C4 C5 100.1(3) . . ?
C3A C4 H4A 111.8 . . ?
C5 C4 H4A 111.8 . . ?
C3A C4 H4B 111.8 . . ?
C5 C4 H4B 111.8 . . ?
H4A C4 H4B 109.5 . . ?
O8 C5 C6 101.7(3) . . ?
O8 C5 C4 101.7(3) . . ?
C6 C5 C4 107.6(4) . . ?
O8 C5 H5 114.8 . . ?
C6 C5 H5 114.8 . . ?
C4 C5 H5 114.8 . . ?
C7 C6 C5 106.1(4) . . ?
C7 C6 H6 126.9 . . ?
C5 C6 H6 126.9 . . ?
C6 C7 C7A 105.1(4) . . ?
C6 C7 H7 127.4 . . ?
C7A C7 H7 127.4 . . ?
O8 C7A C1 112.4(3) . . ?
O8 C7A C7 101.7(3) . . ?
C1 C7A C7 124.6(4) . . ?
O8 C7A C3A 99.8(3) . . ?
C1 C7A C3A 106.9(3) . . ?
C7 C7A C3A 108.7(3) . . ?
C5 O8 C7A 95.0(3) . . ?
C13 C8 C9 118.6(4) . . ?
C13 C8 N1 120.6(4) . . ?
C9 C8 N1 120.8(4) . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 Cl1 119.7(3) . . ?
C8 C9 Cl1 119.6(3) . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C8 C13 C12 121.2(4) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?

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
C7A C1 N2 C2 -173.9(4) . . . . ?
C7A C1 N2 C3 6.8(5) . . . . ?
C1 N2 C2 N1 175.5(4) . . . . ?
C3 N2 C2 N1 -5.3(6) . . . . ?
C1 N2 C2 Se1 -4.1(5) . . . . ?
C3 N2 C2 Se1 175.1(3) . . . . ?
C8 N1 C2 N2 178.3(4) . . . . ?
C8 N1 C2 Se1 -2.1(6) . . . . ?
C2 N2 C3 C3A -165.4(4) . . . . ?
C1 N2 C3 C3A 13.8(4) . . . . ?
N2 C3 C3A C4 -138.0(4) . . . . ?
N2 C3 C3A C7A -27.6(4) . . . . ?
C3 C3A C4 C5 109.2(4) . . . . ?
C7A C3A C4 C5 -1.6(4) . . . . ?
C3A C4 C5 O8 -35.8(4) . . . . ?
C3A C4 C5 C6 70.6(4) . . . . ?
O8 C5 C6 C7 32.8(4) . . . . ?
C4 C5 C6 C7 -73.6(4) . . . . ?
C5 C6 C7 C7A 0.4(5) . . . . ?
N2 C1 C7A O8 83.7(4) . . . . ?
N2 C1 C7A C7 -152.8(4) . . . . ?
N2 C1 C7A C3A -24.8(4) . . . . ?
C6 C7 C7A O8 -33.1(4) . . . . ?
C6 C7 C7A C1 -161.1(4) . . . . ?
C6 C7 C7A C3A 71.6(4) . . . . ?
C3 C3A C7A O8 -83.9(3) . . . . ?
C4 C3A C7A O8 37.8(4) . . . . ?
C3 C3A C7A C1 33.2(4) . . . . ?
C4 C3A C7A C1 154.9(3) . . . . ?
C3 C3A C7A C7 170.1(3) . . . . ?
C4 C3A C7A C7 -68.2(4) . . . . ?
C6 C5 O8 C7A -50.5(3) . . . . ?
C4 C5 O8 C7A 60.4(3) . . . . ?
C1 C7A O8 C5 -173.5(3) . . . . ?
C7 C7A O8 C5 51.0(4) . . . . ?
C3A C7A O8 C5 -60.5(3) . . . . ?
C2 N1 C8 C13 85.8(6) . . . . ?
C2 N1 C8 C9 -95.5(5) . . . . ?
C13 C8 C9 C10 -1.5(6) . . . . ?
N1 C8 C9 C10 179.8(4) . . . . ?
C13 C8 C9 Cl1 179.3(3) . . . . ?
N1 C8 C9 Cl1 0.6(6) . . . . ?
C8 C9 C10 C11 1.0(6) . . . . ?
Cl1 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 -0.8(7) . . . . ?
C9 C8 C13 C12 0.8(7) . . . . ?
N1 C8 C13 C12 179.5(4) . . . . ?
C11 C12 C13 C8 0.3(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Se1 0.96(6) 2.56(6) 3.428(4) 150(4) 3_656

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.075

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_7g
_database_code_depnum_ccdc_archive 'CCDC 2265782'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2023-05-27 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2 Se'
_chemical_formula_sum            'C16 H18 N2 O2 Se'
_chemical_formula_weight         349.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0026 0.0018 '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 0.0069 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0121 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.2324 2.4192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5229(11)
_cell_length_b                   9.1181(15)
_cell_length_c                   24.346(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1448.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      30.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    2.934
_shelx_estimated_absorpt_T_min   0.684
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.74500
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28507
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         31.149
_diffrn_reflns_theta_full        26.551
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4019
_reflns_number_gt                3948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.993

_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.
;

_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+3.21P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.392(14)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4019
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.19302(6) 0.71056(4) 0.71458(2) 0.02206(15) Uani 1 1 d . . . . .
N1 N 0.4809(6) 0.4986(4) 0.74649(15) 0.0203(7) Uani 1 1 d . . . . .
H1 H 0.575(9) 0.440(6) 0.743(2) 0.024 Uiso 1 1 d . U . . .
C1 C 0.7065(7) 0.4922(4) 0.64981(15) 0.0205(7) Uani 1 1 d . . . . .
H1A H 0.6789 0.3854 0.6501 0.025 Uiso 1 1 calc R U . . .
H1B H 0.8077 0.5151 0.6789 0.025 Uiso 1 1 calc R U . . .
N2 N 0.5148(5) 0.5767(4) 0.65801(15) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.4169(6) 0.5853(4) 0.70589(16) 0.0198(7) Uani 1 1 d . . . . .
C3 C 0.4479(7) 0.6551(5) 0.60837(17) 0.0223(8) Uani 1 1 d . . . . .
H3A H 0.4679 0.7622 0.6123 0.027 Uiso 1 1 calc R U . . .
H3B H 0.3019 0.6352 0.6002 0.027 Uiso 1 1 calc R U . . .
C3A C 0.5845(7) 0.5935(5) 0.56455(18) 0.0215(8) Uani 1 1 d . . . . .
C4 C 0.6426(6) 0.6715(5) 0.51208(18) 0.0244(9) Uani 1 1 d . . . . .
H4 H 0.6355 0.7739 0.5050 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7054(8) 0.5677(5) 0.47800(16) 0.0242(8) Uani 1 1 d . . . . .
H5 H 0.7531 0.5798 0.4414 0.029 Uiso 1 1 calc R U . . .
C6 C 0.6853(8) 0.4250(5) 0.50982(16) 0.0229(7) Uani 1 1 d . . . . .
H6 H 0.6745 0.3349 0.4866 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8599(7) 0.4213(5) 0.55359(18) 0.0235(9) Uani 1 1 d . . . . .
H7A H 0.8687 0.3245 0.5719 0.028 Uiso 1 1 calc R U . . .
H7B H 0.9945 0.4462 0.5373 0.028 Uiso 1 1 calc R U . . .
C7A C 0.7845(7) 0.5419(4) 0.59340(16) 0.0204(7) Uani 1 1 d . . . . .
H7C H 0.8863 0.6235 0.5967 0.025 Uiso 1 1 calc R U . . .
O8 O 0.5094(5) 0.4541(3) 0.54368(13) 0.0226(6) Uani 1 1 d . . . . .
C9 C 0.4102(7) 0.5107(5) 0.80154(16) 0.0211(8) Uani 1 1 d . . . . .
C10 C 0.5149(7) 0.6029(4) 0.83779(18) 0.0212(8) Uani 1 1 d . . . . .
O10 O 0.6744(5) 0.6778(3) 0.81536(13) 0.0272(7) Uani 1 1 d . . . . .
C11 C 0.4512(7) 0.6138(5) 0.89203(18) 0.0235(8) Uani 1 1 d . . . . .
H11 H 0.5227 0.6754 0.9170 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2807(8) 0.5334(5) 0.90970(18) 0.0247(8) Uani 1 1 d . . . . .
H12 H 0.2359 0.5416 0.9467 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1767(8) 0.4420(5) 0.87368(18) 0.0267(8) Uani 1 1 d . . . . .
H13 H 0.0613 0.3873 0.8859 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2429(6) 0.4311(5) 0.81957(19) 0.0239(8) Uani 1 1 d . . . . .
H14 H 0.1725 0.3684 0.7948 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8077(8) 0.7550(5) 0.85126(19) 0.0288(9) Uani 1 1 d . . . . .
H15A H 0.9214 0.7969 0.8301 0.043 Uiso 1 1 calc R U . . .
H15B H 0.8620 0.6873 0.8790 0.043 Uiso 1 1 calc R U . . .
H15C H 0.7318 0.8339 0.8695 0.043 Uiso 1 1 calc R U . . .


_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 1.866(4) . ?
N1 C2 1.333(5) . ?
N1 C9 1.422(5) . ?
N1 H1 0.82(6) . ?
C1 N2 1.482(5) . ?
C1 C7A 1.533(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C2 1.331(5) . ?
N2 C3 1.470(5) . ?
C3 C3A 1.499(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3A O8 1.454(5) . ?
C3A C4 1.511(6) . ?
C3A C7A 1.555(6) . ?
C4 C5 1.324(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.520(6) . ?
C5 H5 0.9500 . ?
C6 O8 1.438(5) . ?
C6 C7 1.560(6) . ?
C6 H6 1.0000 . ?
C7 C7A 1.546(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7A H7C 1.0000 . ?
C9 C14 1.382(6) . ?
C9 C10 1.397(6) . ?
C10 O10 1.359(5) . ?
C10 C11 1.388(6) . ?
O10 C15 1.419(5) . ?
C11 C12 1.399(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 N1 C9 123.5(4) . . ?
C2 N1 H1 123(4) . . ?
C9 N1 H1 113(4) . . ?
N2 C1 C7A 104.3(3) . . ?
N2 C1 H1A 110.9 . . ?
C7A C1 H1A 110.9 . . ?
N2 C1 H1B 110.9 . . ?
C7A C1 H1B 110.9 . . ?
H1A C1 H1B 108.9 . . ?
C2 N2 C3 123.3(4) . . ?
C2 N2 C1 123.6(3) . . ?
C3 N2 C1 113.1(3) . . ?
N2 C2 N1 117.7(4) . . ?
N2 C2 Se1 120.7(3) . . ?
N1 C2 Se1 121.6(3) . . ?
N2 C3 C3A 103.1(3) . . ?
N2 C3 H3A 111.1 . . ?
C3A C3 H3A 111.1 . . ?
N2 C3 H3B 111.1 . . ?
C3A C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
O8 C3A C3 112.1(4) . . ?
O8 C3A C4 101.6(3) . . ?
C3 C3A C4 125.1(4) . . ?
O8 C3A C7A 100.2(3) . . ?
C3 C3A C7A 106.9(3) . . ?
C4 C3A C7A 108.3(4) . . ?
C5 C4 C3A 105.7(4) . . ?
C5 C4 H4 127.2 . . ?
C3A C4 H4 127.2 . . ?
C4 C5 C6 105.4(4) . . ?
C4 C5 H5 127.3 . . ?
C6 C5 H5 127.3 . . ?
O8 C6 C5 101.7(3) . . ?
O8 C6 C7 101.2(3) . . ?
C5 C6 C7 107.7(4) . . ?
O8 C6 H6 114.9 . . ?
C5 C6 H6 114.9 . . ?
C7 C6 H6 114.9 . . ?
C7A C7 C6 100.4(3) . . ?
C7A C7 H7A 111.7 . . ?
C6 C7 H7A 111.7 . . ?
C7A C7 H7B 111.7 . . ?
C6 C7 H7B 111.7 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7A C7 117.2(3) . . ?
C1 C7A C3A 102.5(3) . . ?
C7 C7A C3A 101.5(3) . . ?
C1 C7A H7C 111.6 . . ?
C7 C7A H7C 111.6 . . ?
C3A C7A H7C 111.6 . . ?
C6 O8 C3A 95.3(3) . . ?
C14 C9 C10 120.1(4) . . ?
C14 C9 N1 121.0(4) . . ?
C10 C9 N1 118.9(4) . . ?
O10 C10 C11 125.1(4) . . ?
O10 C10 C9 115.0(4) . . ?
C11 C10 C9 119.8(4) . . ?
C10 O10 C15 118.1(3) . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 120.6(4) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O10 C15 H15A 109.5 . . ?
O10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C7A C1 N2 C2 -167.9(4) . . . . ?
C7A C1 N2 C3 9.7(4) . . . . ?
C3 N2 C2 N1 173.9(4) . . . . ?
C1 N2 C2 N1 -8.7(6) . . . . ?
C3 N2 C2 Se1 -4.3(6) . . . . ?
C1 N2 C2 Se1 173.1(3) . . . . ?
C9 N1 C2 N2 170.9(4) . . . . ?
C9 N1 C2 Se1 -11.0(6) . . . . ?
C2 N2 C3 C3A -171.8(4) . . . . ?
C1 N2 C3 C3A 10.6(5) . . . . ?
N2 C3 C3A O8 82.2(4) . . . . ?
N2 C3 C3A C4 -154.5(4) . . . . ?
N2 C3 C3A C7A -26.6(4) . . . . ?
O8 C3A C4 C5 -32.6(5) . . . . ?
C3 C3A C4 C5 -160.4(4) . . . . ?
C7A C3A C4 C5 72.3(5) . . . . ?
C3A C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 O8 32.9(5) . . . . ?
C4 C5 C6 C7 -73.1(5) . . . . ?
O8 C6 C7 C7A -36.1(4) . . . . ?
C5 C6 C7 C7A 70.2(4) . . . . ?
N2 C1 C7A C7 -135.0(4) . . . . ?
N2 C1 C7A C3A -25.0(4) . . . . ?
C6 C7 C7A C1 109.6(4) . . . . ?
C6 C7 C7A C3A -1.0(4) . . . . ?
O8 C3A C7A C1 -84.3(4) . . . . ?
C3 C3A C7A C1 32.7(4) . . . . ?
C4 C3A C7A C1 169.8(3) . . . . ?
O8 C3A C7A C7 37.2(4) . . . . ?
C3 C3A C7A C7 154.1(3) . . . . ?
C4 C3A C7A C7 -68.8(4) . . . . ?
C5 C6 O8 C3A -50.6(4) . . . . ?
C7 C6 O8 C3A 60.3(3) . . . . ?
C3 C3A O8 C6 -173.5(3) . . . . ?
C4 C3A O8 C6 50.8(4) . . . . ?
C7A C3A O8 C6 -60.5(3) . . . . ?
C2 N1 C9 C14 91.3(5) . . . . ?
C2 N1 C9 C10 -89.9(5) . . . . ?
C14 C9 C10 O10 -178.8(4) . . . . ?
N1 C9 C10 O10 2.3(6) . . . . ?
C14 C9 C10 C11 0.3(6) . . . . ?
N1 C9 C10 C11 -178.6(4) . . . . ?
C11 C10 O10 C15 10.9(6) . . . . ?
C9 C10 O10 C15 -170.1(4) . . . . ?
O10 C10 C11 C12 178.3(4) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 C13 0.7(7) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C10 C9 C14 C13 0.2(7) . . . . ?
N1 C9 C14 C13 179.0(4) . . . . ?
C12 C13 C14 C9 -0.2(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Se1 0.82(6) 2.78(6) 3.510(4) 150(5) 3_646
C14 H14 Se1 0.95 2.79 3.580(4) 141 3_546

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.098

_shelxl_version_number           2013-4


####################################################################### 
# 
# 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_lc167
_database_code_depnum_ccdc_archive 'CCDC 2283074'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F N2 O S'
_chemical_formula_weight         290.35

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8056(6)
_cell_length_b                   8.4418(5)
_cell_length_c                   11.6065(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.293(3)
_cell_angle_gamma                90
_cell_volume                     1348.87(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1878
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      22.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13238
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.112
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3079
_reflns_number_gt                1876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.1086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S1 S 0.52423(4) 0.86640(7) 0.79280(4) 0.04165(17) Uani 1 1 d . . . . .
F1 F 0.12052(9) 0.86895(18) 0.47524(12) 0.0696(4) Uani 1 1 d . . . . .
O8 O 0.85535(11) 0.79438(19) 0.66773(14) 0.0520(4) Uani 1 1 d . . . . .
N1 N 0.50864(13) 0.7471(2) 0.57957(15) 0.0355(4) Uani 1 1 d . . . . .
H1 H 0.5374(15) 0.722(3) 0.5211(19) 0.045(7) Uiso 1 1 d . . . . .
N2 N 0.65223(12) 0.6999(2) 0.68402(13) 0.0348(4) Uani 1 1 d . . . . .
C1 C 0.68956(15) 0.6054(3) 0.59068(18) 0.0432(5) Uani 1 1 d . . . . .
H1A H 0.695135 0.669643 0.522206 0.052 Uiso 1 1 calc R U . . .
H1B H 0.647006 0.516487 0.570947 0.052 Uiso 1 1 calc R U . . .
C3 C 0.72351(15) 0.7189(3) 0.78286(17) 0.0427(5) Uani 1 1 d . . . . .
H3A H 0.708233 0.651215 0.846545 0.051 Uiso 1 1 calc R U . . .
H3B H 0.726497 0.828041 0.809086 0.051 Uiso 1 1 calc R U . . .
C3A C 0.81638(15) 0.6701(3) 0.73541(18) 0.0398(5) Uani 1 1 d . . . . .
C4 C 0.90608(17) 0.6131(3) 0.8049(2) 0.0550(7) Uani 1 1 d . . . . .
H4A H 0.910038 0.573964 0.880051 0.066 Uiso 1 1 calc R U . . .
C5 C 0.97734(18) 0.6300(3) 0.7376(2) 0.0640(7) Uani 1 1 d . . . . .
H5A H 1.042328 0.604203 0.754718 0.077 Uiso 1 1 calc R U . . .
C6 C 0.93230(17) 0.6999(3) 0.6266(2) 0.0598(7) Uani 1 1 d . . . . .
H6A H 0.977445 0.757480 0.580550 0.072 Uiso 1 1 calc R U . . .
C7 C 0.87387(16) 0.5669(3) 0.5612(2) 0.0597(7) Uani 1 1 d . . . . .
H7A H 0.851539 0.599169 0.483514 0.072 Uiso 1 1 calc R U . . .
H7B H 0.911448 0.470125 0.557881 0.072 Uiso 1 1 calc R U . . .
C7A C 0.78889(14) 0.5481(3) 0.63885(17) 0.0413(5) Uani 1 1 d . . . . .
H7AA H 0.785757 0.440415 0.669848 0.050 Uiso 1 1 calc R U . . .
C9 C 0.56343(14) 0.7638(2) 0.68114(16) 0.0312(5) Uani 1 1 d . . . . .
C11 C 0.40908(14) 0.7870(2) 0.55903(16) 0.0319(5) Uani 1 1 d . . . . .
C12 C 0.38044(15) 0.8762(2) 0.46303(17) 0.0385(5) Uani 1 1 d . . . . .
H12A H 0.426877 0.917145 0.417168 0.046 Uiso 1 1 calc R U . . .
C13 C 0.28292(16) 0.9052(3) 0.43454(19) 0.0444(6) Uani 1 1 d . . . . .
H13A H 0.262958 0.964670 0.369608 0.053 Uiso 1 1 calc R U . . .
C14 C 0.21731(16) 0.8447(3) 0.5037(2) 0.0458(6) Uani 1 1 d . . . . .
C15 C 0.24321(16) 0.7578(3) 0.60123(19) 0.0476(6) Uani 1 1 d . . . . .
H15A H 0.196308 0.719705 0.647618 0.057 Uiso 1 1 calc R U . . .
C16 C 0.34039(15) 0.7286(3) 0.62865(17) 0.0407(5) Uani 1 1 d . . . . .
H16A H 0.359766 0.669599 0.694013 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.681(2) . ?
F1 C14 1.368(2) . ?
O8 C6 1.438(3) . ?
O8 C3A 1.439(2) . ?
N1 C9 1.360(2) . ?
N1 C11 1.418(3) . ?
N1 H1 0.84(2) . ?
N2 C9 1.338(2) . ?
N2 C3 1.463(2) . ?
N2 C1 1.469(2) . ?
C1 C7A 1.520(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C3A 1.491(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A C4 1.506(3) . ?
C3A C7A 1.548(3) . ?
C4 C5 1.309(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.508(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.548(4) . ?
C6 H6A 0.9800 . ?
C7 C7A 1.540(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7A H7AA 0.9800 . ?
C11 C12 1.378(3) . ?
C11 C16 1.382(3) . ?
C12 C13 1.384(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.354(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(3) . ?
C15 C16 1.378(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?

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
C6 O8 C3A 95.31(16) . . ?
C9 N1 C11 126.19(18) . . ?
C9 N1 H1 117.5(15) . . ?
C11 N1 H1 115.9(15) . . ?
C9 N2 C3 122.44(17) . . ?
C9 N2 C1 124.89(16) . . ?
C3 N2 C1 112.66(16) . . ?
N2 C1 C7A 104.95(16) . . ?
N2 C1 H1A 110.8 . . ?
C7A C1 H1A 110.8 . . ?
N2 C1 H1B 110.8 . . ?
C7A C1 H1B 110.8 . . ?
H1A C1 H1B 108.8 . . ?
N2 C3 C3A 103.09(16) . . ?
N2 C3 H3A 111.1 . . ?
C3A C3 H3A 111.1 . . ?
N2 C3 H3B 111.1 . . ?
C3A C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
O8 C3A C3 111.55(17) . . ?
O8 C3A C4 101.52(17) . . ?
C3 C3A C4 125.87(19) . . ?
O8 C3A C7A 99.86(16) . . ?
C3 C3A C7A 106.27(16) . . ?
C4 C3A C7A 108.80(18) . . ?
C5 C4 C3A 105.7(2) . . ?
C5 C4 H4A 127.2 . . ?
C3A C4 H4A 127.2 . . ?
C4 C5 C6 105.8(2) . . ?
C4 C5 H5A 127.1 . . ?
C6 C5 H5A 127.1 . . ?
O8 C6 C5 101.6(2) . . ?
O8 C6 C7 101.20(18) . . ?
C5 C6 C7 107.5(2) . . ?
O8 C6 H6A 114.9 . . ?
C5 C6 H6A 114.9 . . ?
C7 C6 H6A 114.9 . . ?
C7A C7 C6 100.34(19) . . ?
C7A C7 H7A 111.7 . . ?
C6 C7 H7A 111.7 . . ?
C7A C7 H7B 111.7 . . ?
C6 C7 H7B 111.7 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7A C7 117.24(19) . . ?
C1 C7A C3A 102.71(17) . . ?
C7 C7A C3A 101.47(18) . . ?
C1 C7A H7AA 111.5 . . ?
C7 C7A H7AA 111.5 . . ?
C3A C7A H7AA 111.5 . . ?
N2 C9 N1 115.41(17) . . ?
N2 C9 S1 122.40(14) . . ?
N1 C9 S1 122.11(15) . . ?
C12 C11 C16 119.98(19) . . ?
C12 C11 N1 118.79(18) . . ?
C16 C11 N1 121.06(18) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 118.3(2) . . ?
C14 C13 H13A 120.9 . . ?
C12 C13 H13A 120.9 . . ?
C13 C14 F1 119.0(2) . . ?
C13 C14 C15 123.0(2) . . ?
F1 C14 C15 117.9(2) . . ?
C14 C15 C16 118.3(2) . . ?
C14 C15 H15A 120.8 . . ?
C16 C15 H15A 120.8 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?

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
C9 N2 C1 C7A -175.10(18) . . . . ?
C3 N2 C1 C7A 5.3(2) . . . . ?
C9 N2 C3 C3A -164.66(18) . . . . ?
C1 N2 C3 C3A 14.9(2) . . . . ?
C6 O8 C3A C3 -172.84(18) . . . . ?
C6 O8 C3A C4 50.82(19) . . . . ?
C6 O8 C3A C7A -60.85(17) . . . . ?
N2 C3 C3A O8 78.9(2) . . . . ?
N2 C3 C3A C4 -157.7(2) . . . . ?
N2 C3 C3A C7A -29.0(2) . . . . ?
O8 C3A C4 C5 -33.4(2) . . . . ?
C3 C3A C4 C5 -161.0(2) . . . . ?
C7A C3A C4 C5 71.3(3) . . . . ?
C3A C4 C5 C6 0.8(3) . . . . ?
C3A O8 C6 C5 -50.3(2) . . . . ?
C3A O8 C6 C7 60.46(19) . . . . ?
C4 C5 C6 O8 32.0(3) . . . . ?
C4 C5 C6 C7 -73.8(3) . . . . ?
O8 C6 C7 C7A -35.5(2) . . . . ?
C5 C6 C7 C7A 70.7(2) . . . . ?
N2 C1 C7A C7 -132.7(2) . . . . ?
N2 C1 C7A C3A -22.5(2) . . . . ?
C6 C7 C7A C1 109.4(2) . . . . ?
C6 C7 C7A C3A -1.6(2) . . . . ?
O8 C3A C7A C1 -83.64(18) . . . . ?
C3 C3A C7A C1 32.4(2) . . . . ?
C4 C3A C7A C1 170.50(19) . . . . ?
O8 C3A C7A C7 38.0(2) . . . . ?
C3 C3A C7A C7 154.05(18) . . . . ?
C4 C3A C7A C7 -67.9(2) . . . . ?
C3 N2 C9 N1 174.57(17) . . . . ?
C1 N2 C9 N1 -5.0(3) . . . . ?
C3 N2 C9 S1 -2.3(3) . . . . ?
C1 N2 C9 S1 178.20(15) . . . . ?
C11 N1 C9 N2 171.95(18) . . . . ?
C11 N1 C9 S1 -11.2(3) . . . . ?
C9 N1 C11 C12 131.3(2) . . . . ?
C9 N1 C11 C16 -53.3(3) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
N1 C11 C12 C13 174.11(18) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 F1 -178.45(18) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
F1 C14 C15 C16 178.05(19) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
N1 C11 C16 C15 -174.42(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 S1 0.84(2) 2.75(2) 3.4855(19) 148.1(18) 4_575 yes
C4 H4A F1 0.93 2.47 3.321(3) 152.3 2_646 yes
C6 H6A F1 0.98 2.58 3.544(3) 168.8 1_655 yes
C13 H13A O8 0.93 2.62 3.338(3) 134.1 3_676 yes
C16 H16A S1 0.93 3.02 3.663(2) 128.0 2_646 yes

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.044



