# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_iz4h4m2pFormI
_database_code_depnum_ccdc_archive 'CCDC 2133557'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;

_audit_creation_date             2021-09-02T14:28:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12 H17 N3 O2'
_chemical_formula_sum            'C12 H17 N3 O2'
_chemical_formula_weight         235.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.8108(4)
_cell_length_b                   7.0776(2)
_cell_length_c                   18.1625(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.465(3)
_cell_angle_gamma                90
_cell_volume                     2509.90(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3359
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      20.16
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.152
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_max          0.255
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.987

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_number            37052
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.967
_reflns_Friedel_coverage         0
_reflns_number_total             3065
_reflns_number_gt                1696
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3065
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.06

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.60221(9) 0.2622(3) 0.76509(11) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.611019 0.130905 0.775307 0.056 Uiso 1 1 calc R U . . .
C2 C 0.55179(8) 0.3160(2) 0.68884(10) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.526761 0.22371 0.648663 0.046 Uiso 1 1 calc R U . . .
C3 C 0.53841(7) 0.5058(2) 0.67205(9) 0.0274(4) Uani 1 1 d . . . . .
C4 C 0.57599(8) 0.6326(3) 0.73409(10) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.5683 0.764676 0.725735 0.048 Uiso 1 1 calc R U . . .
C5 C 0.62478(9) 0.5635(3) 0.80823(11) 0.0490(5) Uani 1 1 d . . . . .
H5 H 0.649798 0.65235 0.850124 0.059 Uiso 1 1 calc R U . . .
C6 C 0.48736(7) 0.5849(2) 0.59129(9) 0.0278(3) Uani 1 1 d . . . . .
C7 C 0.34125(7) 0.4196(2) 0.42602(9) 0.0258(3) Uani 1 1 d . . . . .
C8 C 0.29375(8) 0.4738(2) 0.33900(9) 0.0358(4) Uani 1 1 d . . . . .
H8A H 0.314879 0.573755 0.320683 0.054 Uiso 1 1 calc R U . . .
H8B H 0.25043 0.51962 0.336375 0.054 Uiso 1 1 calc R U . . .
H8C H 0.284987 0.363252 0.30319 0.054 Uiso 1 1 calc R U . . .
C9 C 0.31780(8) 0.26478(19) 0.46494(9) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.267575 0.251657 0.432658 0.032 Uiso 1 1 calc R U . . .
H9B H 0.326709 0.307145 0.520768 0.032 Uiso 1 1 calc R U . . .
C10 C 0.34978(7) 0.0681(2) 0.47271(9) 0.0276(4) Uani 1 1 d . . . . .
C11 C 0.35095(10) 0.0048(2) 0.39391(10) 0.0409(4) Uani 1 1 d . . . . .
H11A H 0.37811 0.094054 0.379291 0.061 Uiso 1 1 calc R U . . .
H11B H 0.304041 0.000716 0.349673 0.061 Uiso 1 1 calc R U . . .
H11C H 0.371449 -0.121274 0.401642 0.061 Uiso 1 1 calc R U . . .
C12 C 0.31135(9) -0.0719(2) 0.50013(11) 0.0394(4) Uani 1 1 d . . . . .
H12A H 0.332887 -0.196557 0.507687 0.059 Uiso 1 1 calc R U . . .
H12B H 0.263627 -0.079933 0.458187 0.059 Uiso 1 1 calc R U . . .
H12C H 0.31274 -0.029577 0.552228 0.059 Uiso 1 1 calc R U . . .
N1 N 0.63921(7) 0.3819(2) 0.82511(9) 0.0481(4) Uani 1 1 d . . . . .
N2 N 0.44071(6) 0.46296(19) 0.54094(8) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.39595(6) 0.51890(17) 0.46101(7) 0.0277(3) Uani 1 1 d . . . . .
O1 O 0.48910(5) 0.75362(14) 0.57574(7) 0.0400(3) Uani 1 1 d . . . . .
O2 O 0.41883(5) 0.08361(16) 0.53655(7) 0.0386(3) Uani 1 1 d . . . . .
H2A H 0.4411(9) 0.343(3) 0.5550(10) 0.044(5) Uiso 1 1 d . . . . .
H2B H 0.4381(11) -0.021(3) 0.5391(13) 0.063(7) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.332(2) . ?
C1 C2 1.384(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.387(2) . ?
C3 C6 1.500(2) . ?
C4 C5 1.381(2) . ?
C5 N1 1.326(3) . ?
C6 O1 1.2318(17) . ?
C6 N2 1.3365(19) . ?
C7 N3 1.2829(18) . ?
C7 C8 1.503(2) . ?
C7 C9 1.511(2) . ?
C9 C10 1.535(2) . ?
C10 O2 1.4382(17) . ?
C10 C11 1.511(2) . ?
C10 C12 1.518(2) . ?
N2 N3 1.3980(17) . ?

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
N1 C1 C2 124.41(17) . . ?
C3 C2 C1 119.02(16) . . ?
C2 C3 C4 117.40(14) . . ?
C2 C3 C6 124.85(13) . . ?
C4 C3 C6 117.74(14) . . ?
C5 C4 C3 118.84(17) . . ?
N1 C5 C4 124.68(16) . . ?
O1 C6 N2 124.12(14) . . ?
O1 C6 C3 120.05(13) . . ?
N2 C6 C3 115.80(13) . . ?
N3 C7 C8 115.72(13) . . ?
N3 C7 C9 126.83(13) . . ?
C8 C7 C9 117.31(13) . . ?
C7 C9 C10 117.77(13) . . ?
O2 C10 C11 109.43(14) . . ?
O2 C10 C12 108.56(12) . . ?
C11 C10 C12 111.25(13) . . ?
O2 C10 C9 105.92(11) . . ?
C11 C10 C9 112.36(12) . . ?
C12 C10 C9 109.12(13) . . ?
C5 N1 C1 115.63(15) . . ?
C6 N2 N3 119.61(13) . . ?
C7 N3 N2 115.10(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
N1 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C2 C3 C6 177.50(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C6 C3 C4 C5 -178.08(16) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
C2 C3 C6 O1 -164.22(16) . . . . ?
C4 C3 C6 O1 14.5(2) . . . . ?
C2 C3 C6 N2 17.6(2) . . . . ?
C4 C3 C6 N2 -163.74(15) . . . . ?
N3 C7 C9 C10 -80.9(2) . . . . ?
C8 C7 C9 C10 103.71(15) . . . . ?
C7 C9 C10 O2 72.41(16) . . . . ?
C7 C9 C10 C11 -47.03(18) . . . . ?
C7 C9 C10 C12 -170.90(13) . . . . ?
C4 C5 N1 C1 -1.0(3) . . . . ?
C2 C1 N1 C5 0.4(3) . . . . ?
O1 C6 N2 N3 8.9(2) . . . . ?
C3 C6 N2 N3 -173.01(13) . . . . ?
C8 C7 N3 N2 -177.96(13) . . . . ?
C9 C7 N3 N2 6.6(2) . . . . ?
C6 N2 N3 C7 -159.91(14) . . . . ?

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
C2 H2 O2 0.95 2.53 3.4084(19) 153.9 . yes
C9 H9B N1 0.99 2.61 3.594(2) 172.7 2_656 yes
N2 H2A O2 0.888(19) 1.888(19) 2.7220(18) 155.7(16) . yes
O2 H2B O1 0.84(2) 1.89(2) 2.7088(15) 164(2) 1_545 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_iz4h4m2pFormII
_database_code_depnum_ccdc_archive 'CCDC 2133558'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;

_audit_creation_date             2021-05-19T13:08:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C12  H17  N3  O2'
_chemical_formula_sum            'C12 H17 N3 O2'
_chemical_formula_weight         235.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2041(2)
_cell_length_b                   11.1274(3)
_cell_length_c                   11.9383(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.3570(10)
_cell_angle_gamma                90
_cell_volume                     1221.66(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.88
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.495
_exptl_crystal_size_min          0.228
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.98

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_number            50485
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             3029
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.2553P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.35199(13) 0.42273(11) 0.52834(10) 0.0283(3) Uani 1 1 d . . . . .
H1 H 0.322046 0.50207 0.545596 0.034 Uiso 1 1 calc R U . . .
C2 C 0.43385(12) 0.36021(10) 0.60882(10) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.460686 0.3965 0.678671 0.03 Uiso 1 1 calc R U . . .
C3 C 0.47609(12) 0.24306(10) 0.58535(9) 0.0222(2) Uani 1 1 d . . . . .
C4 C 0.43223(12) 0.19421(10) 0.48212(9) 0.0240(3) Uani 1 1 d . . . . .
H4 H 0.45607 0.113658 0.463956 0.029 Uiso 1 1 calc R U . . .
C5 C 0.35355(12) 0.26491(11) 0.40669(10) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.326761 0.23152 0.335566 0.032 Uiso 1 1 calc R U . . .
C6 C 0.56296(12) 0.16687(10) 0.66779(9) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.82249(12) 0.24211(10) 0.87895(9) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.92894(14) 0.18050(11) 0.95841(11) 0.0335(3) Uani 1 1 d . . . . .
H8A H 0.933854 0.094931 0.939504 0.05 Uiso 1 1 calc R U . . .
H8B H 0.897176 0.189488 1.035312 0.05 Uiso 1 1 calc R U . . .
H8C H 1.025265 0.216849 0.952292 0.05 Uiso 1 1 calc R U . . .
C9 C 0.80512(12) 0.37672(10) 0.89049(9) 0.0250(3) Uani 1 1 d . . . . .
H9A H 0.840522 0.399976 0.966865 0.03 Uiso 1 1 calc R U . . .
H9B H 0.700012 0.395676 0.884238 0.03 Uiso 1 1 calc R U . . .
C10 C 0.88336(12) 0.45572(10) 0.80574(9) 0.0235(3) Uani 1 1 d . . . . .
C11 C 1.04238(13) 0.42113(11) 0.79780(11) 0.0323(3) Uani 1 1 d . . . . .
H11A H 1.049135 0.339025 0.768778 0.048 Uiso 1 1 calc R U . . .
H11B H 1.090713 0.425389 0.872389 0.048 Uiso 1 1 calc R U . . .
H11C H 1.089816 0.476676 0.747125 0.048 Uiso 1 1 calc R U . . .
C12 C 0.86915(15) 0.58701(11) 0.83792(11) 0.0329(3) Uani 1 1 d . . . . .
H12A H 0.917015 0.637196 0.782946 0.049 Uiso 1 1 calc R U . . .
H12B H 0.915264 0.600031 0.91238 0.049 Uiso 1 1 calc R U . . .
H12C H 0.766002 0.608575 0.839195 0.049 Uiso 1 1 calc R U . . .
N1 N 0.31264(11) 0.37794(9) 0.42779(9) 0.0292(2) Uani 1 1 d . . . . .
N2 N 0.65569(11) 0.23155(9) 0.73464(8) 0.0256(2) Uani 1 1 d . . . . .
N3 N 0.75076(10) 0.17317(9) 0.81029(8) 0.0266(2) Uani 1 1 d . . . . .
O1 O 0.54576(10) 0.05782(7) 0.67247(7) 0.0349(2) Uani 1 1 d . . . . .
O2 O 0.81228(10) 0.43582(7) 0.69760(7) 0.0289(2) Uani 1 1 d . . . . .
H2A H 0.6771(15) 0.3075(14) 0.7158(12) 0.037(4) Uiso 1 1 d . . . . .
H2B H 0.779(2) 0.5036(17) 0.6662(14) 0.064(5) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.3360(16) . ?
C1 C2 1.3840(16) . ?
C2 C3 1.3920(15) . ?
C3 C4 1.3916(15) . ?
C3 C6 1.5040(15) . ?
C4 C5 1.3787(16) . ?
C5 N1 1.3397(16) . ?
C6 O1 1.2252(13) . ?
C6 N2 1.3518(14) . ?
C7 N3 1.2852(15) . ?
C7 C8 1.5011(15) . ?
C7 C9 1.5132(16) . ?
C9 C10 1.5410(16) . ?
C10 O2 1.4403(13) . ?
C10 C12 1.5175(16) . ?
C10 C11 1.5201(17) . ?
N2 N3 1.3922(13) . ?

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
N1 C1 C2 123.78(11) . . ?
C1 C2 C3 118.66(10) . . ?
C4 C3 C2 118.09(10) . . ?
C4 C3 C6 119.10(10) . . ?
C2 C3 C6 122.79(10) . . ?
C5 C4 C3 118.75(11) . . ?
N1 C5 C4 123.85(11) . . ?
O1 C6 N2 125.45(10) . . ?
O1 C6 C3 121.46(10) . . ?
N2 C6 C3 113.07(9) . . ?
N3 C7 C8 115.80(10) . . ?
N3 C7 C9 126.55(10) . . ?
C8 C7 C9 117.59(10) . . ?
C7 C9 C10 116.80(9) . . ?
O2 C10 C12 109.52(9) . . ?
O2 C10 C11 107.95(9) . . ?
C12 C10 C11 110.66(10) . . ?
O2 C10 C9 107.07(9) . . ?
C12 C10 C9 109.60(10) . . ?
C11 C10 C9 111.94(9) . . ?
C1 N1 C5 116.83(10) . . ?
C6 N2 N3 119.95(9) . . ?
C7 N3 N2 115.33(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.19(18) . . . . ?
C1 C2 C3 C4 -0.68(16) . . . . ?
C1 C2 C3 C6 -178.96(11) . . . . ?
C2 C3 C4 C5 2.13(16) . . . . ?
C6 C3 C4 C5 -179.53(10) . . . . ?
C3 C4 C5 N1 -1.93(18) . . . . ?
C4 C3 C6 O1 -31.78(16) . . . . ?
C2 C3 C6 O1 146.48(12) . . . . ?
C4 C3 C6 N2 149.60(11) . . . . ?
C2 C3 C6 N2 -32.14(15) . . . . ?
N3 C7 C9 C10 -81.58(14) . . . . ?
C8 C7 C9 C10 101.38(12) . . . . ?
C7 C9 C10 O2 67.95(12) . . . . ?
C7 C9 C10 C12 -173.34(10) . . . . ?
C7 C9 C10 C11 -50.16(13) . . . . ?
C2 C1 N1 C5 1.47(18) . . . . ?
C4 C5 N1 C1 0.13(17) . . . . ?
O1 C6 N2 N3 5.75(18) . . . . ?
C3 C6 N2 N3 -175.69(10) . . . . ?
C8 C7 N3 N2 -178.06(10) . . . . ?
C9 C7 N3 N2 4.85(17) . . . . ?
C6 N2 N3 C7 -172.27(11) . . . . ?

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
N2 H2A O2 0.898(15) 1.913(15) 2.7370(13) 151.8(12) . yes
O2 H2B N1 0.892(19) 1.903(19) 2.7778(13) 166.0(16) 3_666 yes


# END of CIF

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
