# 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 2023

####################################################################### 
# 
# 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_sh202
_database_code_depnum_ccdc_archive 'CCDC 2278313'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2023-06-30 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H7 N3 O'
_chemical_formula_sum            'C4 H7 N3 O'
_chemical_formula_weight         113.13

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.8785(19)
_cell_length_b                   8.749(2)
_cell_length_c                   9.943(4)
_cell_angle_alpha                106.629(7)
_cell_angle_beta                 97.777(7)
_cell_angle_gamma                106.062(5)
_cell_volume                     535.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1056
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      25.62

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5549
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         27.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2564
_reflns_number_gt                1734
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 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)+(0.0480P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2564
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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 -0.25553(17) 0.41245(14) 0.74899(12) 0.0219(3) Uani 1 1 d . . . . .
N1 N -0.3468(2) 0.46739(17) 0.86470(15) 0.0201(3) Uani 1 1 d . . . . .
N2 N -0.0550(2) 0.52276(17) 0.77548(15) 0.0205(3) Uani 1 1 d . . . . .
N3 N -0.2258(3) 0.6948(2) 1.08430(16) 0.0238(4) Uani 1 1 d . . . . .
H1 H -0.343(3) 0.664(2) 1.1066(19) 0.029(5) Uiso 1 1 d . . . . .
H2 H -0.134(3) 0.798(3) 1.136(2) 0.033(5) Uiso 1 1 d . . . . .
C1 C -0.2042(2) 0.6045(2) 0.95567(17) 0.0172(4) Uani 1 1 d . . . . .
C2 C -0.0208(2) 0.6389(2) 0.89896(17) 0.0171(4) Uani 1 1 d . . . . .
C3 C 0.1788(3) 0.7816(2) 0.96918(18) 0.0197(4) Uani 1 1 d . . . . .
H3A H 0.2230 0.7884 1.0703 0.024 Uiso 1 1 calc R U . . .
H3B H 0.1554 0.8888 0.9711 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3528(3) 0.7632(2) 0.89258(18) 0.0228(4) Uani 1 1 d . . . . .
H4A H 0.4819 0.8561 0.9468 0.034 Uiso 1 1 calc R U . . .
H4B H 0.3155 0.7665 0.7950 0.034 Uiso 1 1 calc R U . . .
H4C H 0.3730 0.6551 0.8867 0.034 Uiso 1 1 calc R U . . .
O1' O 0.23888(18) 0.13241(14) 0.26242(13) 0.0246(3) Uani 1 1 d . . . . .
N1' N 0.3407(2) 0.28702(17) 0.37605(15) 0.0214(3) Uani 1 1 d . . . . .
N2' N 0.0399(2) 0.06079(17) 0.27733(15) 0.0224(3) Uani 1 1 d . . . . .
N3' N 0.2397(3) 0.4383(2) 0.57471(17) 0.0285(4) Uani 1 1 d . . . . .
H1' H 0.359(3) 0.521(2) 0.6040(18) 0.024(5) Uiso 1 1 d . . . . .
H2' H 0.146(3) 0.451(2) 0.625(2) 0.028(5) Uiso 1 1 d . . . . .
C1' C 0.2047(3) 0.3062(2) 0.45461(18) 0.0183(4) Uani 1 1 d . . . . .
C2' C 0.0154(3) 0.16320(19) 0.39198(17) 0.0177(4) Uani 1 1 d . . . . .
C3' C -0.1795(3) 0.1324(2) 0.44608(18) 0.0200(4) Uani 1 1 d . . . . .
H3'A H -0.2330 0.2272 0.4500 0.024 Uiso 1 1 calc R U . . .
H3'B H -0.1460 0.1308 0.5456 0.024 Uiso 1 1 calc R U . . .
C4' C -0.3497(3) -0.0334(2) 0.35243(19) 0.0250(4) Uani 1 1 d . . . . .
H4'A H -0.4759 -0.0430 0.3895 0.037 Uiso 1 1 calc R U . . .
H4'B H -0.3026 -0.1287 0.3549 0.037 Uiso 1 1 calc R U . . .
H4'C H -0.3800 -0.0349 0.2528 0.037 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 N2 1.3869(17) . ?
O1 N1 1.4123(17) . ?
N1 C1 1.307(2) . ?
N2 C2 1.293(2) . ?
N3 C1 1.349(2) . ?
N3 H1 0.86(2) . ?
N3 H2 0.90(2) . ?
C1 C2 1.442(2) . ?
C2 C3 1.491(2) . ?
C3 C4 1.524(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O1' N2' 1.3859(17) . ?
O1' N1' 1.4085(17) . ?
N1' C1' 1.313(2) . ?
N2' C2' 1.297(2) . ?
N3' C1' 1.341(2) . ?
N3' H1' 0.88(2) . ?
N3' H2' 0.88(2) . ?
C1' C2' 1.443(2) . ?
C2' C3' 1.496(2) . ?
C3' C4' 1.528(2) . ?
C3' H3'A 0.9900 . ?
C3' H3'B 0.9900 . ?
C4' H4'A 0.9800 . ?
C4' H4'B 0.9800 . ?
C4' H4'C 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
N2 O1 N1 109.73(12) . . ?
C1 N1 O1 105.22(13) . . ?
C2 N2 O1 107.02(13) . . ?
C1 N3 H1 118.2(13) . . ?
C1 N3 H2 121.2(12) . . ?
H1 N3 H2 118.8(17) . . ?
N1 C1 N3 124.51(15) . . ?
N1 C1 C2 109.34(14) . . ?
N3 C1 C2 126.12(15) . . ?
N2 C2 C1 108.69(14) . . ?
N2 C2 C3 124.43(15) . . ?
C1 C2 C3 126.87(15) . . ?
C2 C3 C4 113.07(14) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2' O1' N1' 109.91(11) . . ?
C1' N1' O1' 105.17(13) . . ?
C2' N2' O1' 107.12(13) . . ?
C1' N3' H1' 119.9(12) . . ?
C1' N3' H2' 123.5(13) . . ?
H1' N3' H2' 116.5(17) . . ?
N1' C1' N3' 124.60(16) . . ?
N1' C1' C2' 109.33(15) . . ?
N3' C1' C2' 126.07(15) . . ?
N2' C2' C1' 108.46(15) . . ?
N2' C2' C3' 124.06(15) . . ?
C1' C2' C3' 127.48(15) . . ?
C2' C3' C4' 113.26(14) . . ?
C2' C3' H3'A 108.9 . . ?
C4' C3' H3'A 108.9 . . ?
C2' C3' H3'B 108.9 . . ?
C4' C3' H3'B 108.9 . . ?
H3'A C3' H3'B 107.7 . . ?
C3' C4' H4'A 109.5 . . ?
C3' C4' H4'B 109.5 . . ?
H4'A C4' H4'B 109.5 . . ?
C3' C4' H4'C 109.5 . . ?
H4'A C4' H4'C 109.5 . . ?
H4'B C4' H4'C 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
N2 O1 N1 C1 -0.21(16) . . . . ?
N1 O1 N2 C2 0.18(16) . . . . ?
O1 N1 C1 N3 -177.74(14) . . . . ?
O1 N1 C1 C2 0.16(17) . . . . ?
O1 N2 C2 C1 -0.08(17) . . . . ?
O1 N2 C2 C3 178.96(14) . . . . ?
N1 C1 C2 N2 -0.05(18) . . . . ?
N3 C1 C2 N2 177.81(15) . . . . ?
N1 C1 C2 C3 -179.06(16) . . . . ?
N3 C1 C2 C3 -1.2(3) . . . . ?
N2 C2 C3 C4 -9.0(2) . . . . ?
C1 C2 C3 C4 169.82(15) . . . . ?
N2' O1' N1' C1' -0.51(16) . . . . ?
N1' O1' N2' C2' 0.49(16) . . . . ?
O1' N1' C1' N3' 179.85(15) . . . . ?
O1' N1' C1' C2' 0.34(17) . . . . ?
O1' N2' C2' C1' -0.27(17) . . . . ?
O1' N2' C2' C3' 179.86(14) . . . . ?
N1' C1' C2' N2' -0.05(19) . . . . ?
N3' C1' C2' N2' -179.55(16) . . . . ?
N1' C1' C2' C3' 179.82(15) . . . . ?
N3' C1' C2' C3' 0.3(3) . . . . ?
N2' C2' C3' C4' 0.0(2) . . . . ?
C1' C2' C3' C4' -179.83(16) . . . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh244
_database_code_depnum_ccdc_archive 'CCDC 2278316'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2023-06-30 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H6 N4 O'
_chemical_formula_sum            'C7 H6 N4 O'
_chemical_formula_weight         162.16

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'

_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                   3.8205(2)
_cell_length_b                   15.6562(10)
_cell_length_c                   12.1910(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.4960(10)
_cell_angle_gamma                90
_cell_volume                     726.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2943
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.88

_exptl_crystal_description       prizm
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7967
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1741
_reflns_number_gt                1486
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 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)+(0.0402P)²+0.2176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1741
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 -0.0750(2) 0.57397(5) 0.74906(7) 0.0275(2) Uani 1 1 d . . . . .
N1 N -0.0217(3) 0.53730(7) 0.85462(9) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.0595(3) 0.52214(6) 0.67170(9) 0.0254(2) Uani 1 1 d . . . . .
N3 N 0.2399(4) 0.40895(8) 0.91969(10) 0.0336(3) Uani 1 1 d . . . . .
H1 H 0.209(4) 0.4218(10) 0.9874(14) 0.035(4) Uiso 1 1 d . . . . .
H2 H 0.350(4) 0.3635(11) 0.9010(13) 0.038(4) Uiso 1 1 d . . . . .
N4 N 0.4726(3) 0.32001(7) 0.73408(8) 0.0244(2) Uani 1 1 d . . . . .
C1 C 0.1408(3) 0.46483(8) 0.83959(10) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.1908(3) 0.45560(7) 0.72400(10) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.3540(3) 0.38424(7) 0.66824(10) 0.0208(3) Uani 1 1 d . . . . .
C4 C 0.3787(3) 0.38461(8) 0.55483(10) 0.0262(3) Uani 1 1 d . . . . .
H4A H 0.2930 0.4314 0.5110 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5315(4) 0.31489(9) 0.50778(11) 0.0303(3) Uani 1 1 d . . . . .
H5A H 0.5530 0.3131 0.4307 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6525(3) 0.24793(9) 0.57404(11) 0.0289(3) Uani 1 1 d . . . . .
H6A H 0.7567 0.1992 0.5434 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6189(3) 0.25333(8) 0.68574(11) 0.0282(3) Uani 1 1 d . . . . .
H7A H 0.7041 0.2072 0.7310 0.034 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 N2 1.3740(14) . ?
O1 N1 1.4093(13) . ?
N1 C1 1.3131(16) . ?
N2 C2 1.3013(15) . ?
N3 C1 1.3432(16) . ?
N4 C7 1.3422(16) . ?
N4 C3 1.3431(15) . ?
C1 C2 1.4440(16) . ?
C2 C3 1.4715(16) . ?
C3 C4 1.3932(17) . ?
C4 C5 1.3834(19) . ?
C5 C6 1.381(2) . ?
C6 C7 1.3803(18) . ?

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
N2 O1 N1 110.56(8) . . ?
C1 N1 O1 105.11(10) . . ?
C2 N2 O1 106.67(10) . . ?
C7 N4 C3 116.91(11) . . ?
N1 C1 N3 124.80(12) . . ?
N1 C1 C2 108.83(10) . . ?
N3 C1 C2 126.37(11) . . ?
N2 C2 C1 108.83(11) . . ?
N2 C2 C3 122.85(11) . . ?
C1 C2 C3 128.31(10) . . ?
N4 C3 C4 123.39(11) . . ?
N4 C3 C2 115.32(10) . . ?
C4 C3 C2 121.29(11) . . ?
C5 C4 C3 118.15(12) . . ?
C6 C5 C4 119.30(12) . . ?
C7 C6 C5 118.54(12) . . ?
N4 C7 C6 123.71(12) . . ?

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
N2 O1 N1 C1 -0.18(13) . . . . ?
N1 O1 N2 C2 0.28(13) . . . . ?
O1 N1 C1 N3 -179.52(12) . . . . ?
O1 N1 C1 C2 0.01(13) . . . . ?
O1 N2 C2 C1 -0.26(13) . . . . ?
O1 N2 C2 C3 178.75(10) . . . . ?
N1 C1 C2 N2 0.16(14) . . . . ?
N3 C1 C2 N2 179.68(13) . . . . ?
N1 C1 C2 C3 -178.78(11) . . . . ?
N3 C1 C2 C3 0.7(2) . . . . ?
C7 N4 C3 C4 -0.51(18) . . . . ?
C7 N4 C3 C2 179.15(11) . . . . ?
N2 C2 C3 N4 -179.22(11) . . . . ?
C1 C2 C3 N4 -0.41(17) . . . . ?
N2 C2 C3 C4 0.45(18) . . . . ?
C1 C2 C3 C4 179.25(12) . . . . ?
N4 C3 C4 C5 0.42(18) . . . . ?
C2 C3 C4 C5 -179.22(11) . . . . ?
C3 C4 C5 C6 0.11(19) . . . . ?
C4 C5 C6 C7 -0.51(19) . . . . ?
C3 N4 C7 C6 0.07(19) . . . . ?
C5 C6 C7 N4 0.4(2) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_sh243
_database_code_depnum_ccdc_archive 'CCDC 2278315'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2023-06-30 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N3 O S'
_chemical_formula_sum            'C6 H5 N3 O S'
_chemical_formula_weight         167.19

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'
S S 0.1246 0.1234 '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                   5.4688(7)
_cell_length_b                   6.1708(8)
_cell_length_c                   20.871(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     704.32(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2457
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      29.15

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.395
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker,2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8247
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         29.281
_diffrn_reflns_theta_full        25.242
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1930
_reflns_number_gt                1613
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 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)+(0.0414P)²+0.8380P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
;
 Flack x determined using 548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1930
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1198
_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
S1 S 0.8106(2) 0.1175(2) 0.04703(6) 0.0266(3) Uani 1 1 d . . . . .
O1 O 0.2220(6) 0.3455(5) 0.17210(17) 0.0274(8) Uani 1 1 d . . . . .
N1 N 0.1521(7) 0.1638(6) 0.20798(19) 0.0223(9) Uani 1 1 d . . . . .
N2 N 0.4177(8) 0.2995(6) 0.1329(2) 0.0240(9) Uani 1 1 d . . . . .
N3 N 0.3039(8) -0.1896(6) 0.2175(2) 0.0209(8) Uani 1 1 d . . . . .
H1 H 0.180(10) -0.228(8) 0.238(2) 0.018(13) Uiso 1 1 d . . . . .
H2 H 0.364(10) -0.276(8) 0.194(2) 0.018(14) Uiso 1 1 d . . . . .
C1 C 0.3048(9) 0.0119(7) 0.1910(2) 0.0180(8) Uani 1 1 d . . . . .
C2 C 0.4717(8) 0.0958(7) 0.1439(2) 0.0167(9) Uani 1 1 d . . . . .
C3 C 0.6717(8) -0.0105(7) 0.11047(19) 0.0155(8) Uani 1 1 d . . . . .
C4 C 0.7772(8) -0.2105(7) 0.1226(2) 0.0174(9) Uani 1 1 d . . . . .
H4A H 0.7257 -0.3060 0.1556 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9732(9) -0.2557(7) 0.0792(2) 0.0205(10) Uani 1 1 d . . . . .
H5A H 1.0680 -0.3846 0.0803 0.025 Uiso 1 1 calc R U . . .
C6 C 1.0082(9) -0.0930(8) 0.0363(2) 0.0246(10) Uani 1 1 d . . . . .
H6B H 1.1299 -0.0963 0.0039 0.030 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 C6 1.704(5) . ?
S1 C3 1.719(4) . ?
O1 N2 1.376(5) . ?
O1 N1 1.402(5) . ?
N1 C1 1.304(6) . ?
N2 C2 1.311(6) . ?
N3 C1 1.362(6) . ?
N3 H1 0.84(5) . ?
N3 H2 0.80(5) . ?
C1 C2 1.438(6) . ?
C2 C3 1.454(6) . ?
C3 C4 1.386(6) . ?
C4 C5 1.430(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.358(6) . ?
C5 H5A 0.9500 . ?
C6 H6B 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
C6 S1 C3 91.8(2) . . ?
N2 O1 N1 111.4(3) . . ?
C1 N1 O1 104.7(3) . . ?
C2 N2 O1 105.6(4) . . ?
C1 N3 H1 118(3) . . ?
C1 N3 H2 111(4) . . ?
H1 N3 H2 118(5) . . ?
N1 C1 N3 122.9(4) . . ?
N1 C1 C2 109.5(4) . . ?
N3 C1 C2 127.5(4) . . ?
N2 C2 C1 108.7(4) . . ?
N2 C2 C3 121.2(4) . . ?
C1 C2 C3 130.0(4) . . ?
C4 C3 C2 128.9(4) . . ?
C4 C3 S1 111.5(3) . . ?
C2 C3 S1 119.7(3) . . ?
C3 C4 C5 111.7(4) . . ?
C3 C4 H4A 124.1 . . ?
C5 C4 H4A 124.1 . . ?
C6 C5 C4 112.3(4) . . ?
C6 C5 H5A 123.9 . . ?
C4 C5 H5A 123.9 . . ?
C5 C6 S1 112.8(3) . . ?
C5 C6 H6B 123.6 . . ?
S1 C6 H6B 123.6 . . ?

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
N2 O1 N1 C1 0.5(5) . . . . ?
N1 O1 N2 C2 -0.5(5) . . . . ?
O1 N1 C1 N3 177.1(4) . . . . ?
O1 N1 C1 C2 -0.4(5) . . . . ?
O1 N2 C2 C1 0.2(5) . . . . ?
O1 N2 C2 C3 179.9(4) . . . . ?
N1 C1 C2 N2 0.1(5) . . . . ?
N3 C1 C2 N2 -177.2(5) . . . . ?
N1 C1 C2 C3 -179.6(4) . . . . ?
N3 C1 C2 C3 3.1(8) . . . . ?
N2 C2 C3 C4 169.2(4) . . . . ?
C1 C2 C3 C4 -11.1(7) . . . . ?
N2 C2 C3 S1 -10.0(6) . . . . ?
C1 C2 C3 S1 169.6(4) . . . . ?
C6 S1 C3 C4 0.0(3) . . . . ?
C6 S1 C3 C2 179.4(4) . . . . ?
C2 C3 C4 C5 -179.1(4) . . . . ?
S1 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 S1 0.4(5) . . . . ?
C3 S1 C6 C5 -0.3(4) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.083

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_131
_database_code_depnum_ccdc_archive 'CCDC 2278314'
loop_
_audit_author_name
_audit_author_address
'Kyrill Yu.  Suponitsky'
;A N Nesmeyanov Institute of Organoelement Compounds, Moscow, Russia
Russia
;
_audit_update_record             
;
2023-06-30 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N3 O3'
_chemical_formula_sum            'C12 H15 N3 O3'
_chemical_formula_weight         249.27

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'

_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                   12.3025(7)
_cell_length_b                   11.3020(7)
_cell_length_c                   10.0707(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.4710(10)
_cell_angle_gamma                90
_cell_volume                     1284.40(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8135
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      30.06

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18743
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.805
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3090
_reflns_number_gt                2522
_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       'APEX (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 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)+(0.0775P)²+0.2059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3090
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
O1 O 1.29741(8) -0.03002(10) 0.19731(10) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.77985(7) 0.00141(7) 0.25363(9) 0.0225(2) Uani 1 1 d . . . . .
O3 O 0.78929(7) -0.16392(7) 0.43019(9) 0.0252(2) Uani 1 1 d . . . . .
N1 N 1.37936(9) -0.03027(11) 0.34171(11) 0.0306(3) Uani 1 1 d . . . . .
N2 N 1.18435(9) -0.05130(11) 0.18988(12) 0.0329(3) Uani 1 1 d . . . . .
N3 N 1.36520(9) -0.06398(10) 0.56517(11) 0.0264(2) Uani 1 1 d . . . . .
H1 H 1.4398(15) -0.0394(13) 0.6083(17) 0.031(4) Uiso 1 1 d . . . . .
H2 H 1.3205(14) -0.0375(13) 0.6108(16) 0.030(4) Uiso 1 1 d . . . . .
C1 C 1.31748(10) -0.05200(10) 0.41841(13) 0.0241(3) Uani 1 1 d . . . . .
C2 C 1.19419(10) -0.06544(10) 0.32208(13) 0.0239(3) Uani 1 1 d . . . . .
C3 C 1.09155(10) -0.09123(10) 0.35733(12) 0.0219(2) Uani 1 1 d . . . . .
C4 C 1.09750(10) -0.17760(10) 0.45769(12) 0.0228(2) Uani 1 1 d . . . . .
H4A H 1.1701 -0.2177 0.5087 0.027 Uiso 1 1 calc R U . . .
C5 C 0.99767(10) -0.20621(10) 0.48451(12) 0.0221(2) Uani 1 1 d . . . . .
H5A H 1.0019 -0.2671 0.5514 0.027 Uiso 1 1 calc R U . . .
C6 C 0.89217(10) -0.14535(9) 0.41315(12) 0.0204(2) Uani 1 1 d . . . . .
C7 C 0.88681(9) -0.05486(9) 0.31435(12) 0.0198(2) Uani 1 1 d . . . . .
C8 C 0.98491(10) -0.02963(10) 0.28509(12) 0.0210(2) Uani 1 1 d . . . . .
H8A H 0.9803 0.0295 0.2160 0.025 Uiso 1 1 calc R U . . .
C9 C 0.76943(10) 0.09372(10) 0.15112(12) 0.0237(2) Uani 1 1 d . . . . .
H9A H 0.7899 0.0630 0.0719 0.028 Uiso 1 1 calc R U . . .
H9B H 0.8240 0.1596 0.1992 0.028 Uiso 1 1 calc R U . . .
C10 C 0.64291(11) 0.13639(12) 0.09150(15) 0.0331(3) Uani 1 1 d . . . . .
H10A H 0.6323 0.1980 0.0189 0.050 Uiso 1 1 calc R U . . .
H10B H 0.6244 0.1689 0.1703 0.050 Uiso 1 1 calc R U . . .
H10C H 0.5897 0.0700 0.0466 0.050 Uiso 1 1 calc R U . . .
C11 C 0.78735(11) -0.25685(11) 0.52707(14) 0.0300(3) Uani 1 1 d . . . . .
H11A H 0.8390 -0.2361 0.6282 0.036 Uiso 1 1 calc R U . . .
H11B H 0.8161 -0.3319 0.5019 0.036 Uiso 1 1 calc R U . . .
C12 C 0.66097(12) -0.26998(13) 0.51094(19) 0.0426(4) Uani 1 1 d . . . . .
H12A H 0.6566 -0.3307 0.5781 0.064 Uiso 1 1 calc R U . . .
H12B H 0.6113 -0.2934 0.4114 0.064 Uiso 1 1 calc R U . . .
H12C H 0.6327 -0.1944 0.5328 0.064 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 N2 1.3839(13) . ?
O1 N1 1.4012(14) . ?
O2 C7 1.3671(13) . ?
O2 C9 1.4371(13) . ?
O3 C6 1.3596(13) . ?
O3 C11 1.4402(14) . ?
N1 C1 1.3057(15) . ?
N2 C2 1.2978(16) . ?
N3 C1 1.3624(15) . ?
N3 H1 0.889(17) . ?
N3 H2 0.897(16) . ?
C1 C2 1.4467(16) . ?
C2 C3 1.4706(15) . ?
C3 C4 1.3859(16) . ?
C3 C8 1.4053(16) . ?
C4 C5 1.3964(15) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3896(15) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4100(15) . ?
C7 C8 1.3813(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.5071(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5048(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
N2 O1 N1 110.37(9) . . ?
C7 O2 C9 116.97(8) . . ?
C6 O3 C11 117.75(9) . . ?
C1 N1 O1 105.44(10) . . ?
C2 N2 O1 106.55(10) . . ?
C1 N3 H1 114.4(10) . . ?
C1 N3 H2 115.8(10) . . ?
H1 N3 H2 111.7(14) . . ?
N1 C1 N3 124.02(11) . . ?
N1 C1 C2 109.01(11) . . ?
N3 C1 C2 126.92(10) . . ?
N2 C2 C1 108.64(10) . . ?
N2 C2 C3 122.26(10) . . ?
C1 C2 C3 129.10(11) . . ?
C4 C3 C8 119.59(10) . . ?
C4 C3 C2 120.98(10) . . ?
C8 C3 C2 119.41(10) . . ?
C3 C4 C5 120.60(10) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 119.84(10) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
O3 C6 C5 125.66(10) . . ?
O3 C6 C7 114.63(9) . . ?
C5 C6 C7 119.70(10) . . ?
O2 C7 C8 125.15(10) . . ?
O2 C7 C6 114.79(9) . . ?
C8 C7 C6 120.06(10) . . ?
C7 C8 C3 120.14(10) . . ?
C7 C8 H8A 119.9 . . ?
C3 C8 H8A 119.9 . . ?
O2 C9 C10 107.51(9) . . ?
O2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C12 107.10(10) . . ?
O3 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O3 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N2 O1 N1 C1 0.48(14) . . . . ?
N1 O1 N2 C2 -0.58(14) . . . . ?
O1 N1 C1 N3 177.50(11) . . . . ?
O1 N1 C1 C2 -0.20(13) . . . . ?
O1 N2 C2 C1 0.44(14) . . . . ?
O1 N2 C2 C3 -179.30(10) . . . . ?
N1 C1 C2 N2 -0.15(15) . . . . ?
N3 C1 C2 N2 -177.77(12) . . . . ?
N1 C1 C2 C3 179.57(11) . . . . ?
N3 C1 C2 C3 1.9(2) . . . . ?
N2 C2 C3 C4 135.41(13) . . . . ?
C1 C2 C3 C4 -44.28(18) . . . . ?
N2 C2 C3 C8 -42.77(17) . . . . ?
C1 C2 C3 C8 137.54(13) . . . . ?
C8 C3 C4 C5 1.84(16) . . . . ?
C2 C3 C4 C5 -176.34(10) . . . . ?
C3 C4 C5 C6 -1.85(16) . . . . ?
C11 O3 C6 C5 -1.97(16) . . . . ?
C11 O3 C6 C7 178.65(10) . . . . ?
C4 C5 C6 O3 -179.52(10) . . . . ?
C4 C5 C6 C7 -0.16(16) . . . . ?
C9 O2 C7 C8 0.18(16) . . . . ?
C9 O2 C7 C6 -179.45(9) . . . . ?
O3 C6 C7 O2 1.26(14) . . . . ?
C5 C6 C7 O2 -178.16(9) . . . . ?
O3 C6 C7 C8 -178.40(9) . . . . ?
C5 C6 C7 C8 2.18(16) . . . . ?
O2 C7 C8 C3 178.18(10) . . . . ?
C6 C7 C8 C3 -2.20(16) . . . . ?
C4 C3 C8 C7 0.20(16) . . . . ?
C2 C3 C8 C7 178.41(10) . . . . ?
C7 O2 C9 C10 176.09(10) . . . . ?
C6 O3 C11 C12 -172.39(11) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

