# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1891006'
loop_
_audit_author_name
_audit_author_address
'Matthew P Akerman' 'University of KwaZulu-Natal'
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N3 O'
_chemical_formula_sum            'C15 H19 N3 O'
_chemical_formula_weight         257.33

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   36.239(6)
_cell_length_b                   7.1570(12)
_cell_length_c                   11.2151(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.478(3)
_cell_angle_gamma                90
_cell_volume                     2816.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2952
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      28.2

_exptl_crystal_description       planar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29656
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.161
_diffrn_reflns_theta_max         28.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3453
_reflns_number_gt                2952
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_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)+(0.0473P)²+5.2899P] 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         3453
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.28483(3) 0.36320(17) 0.42046(10) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.32968(4) 0.19048(19) 0.89163(12) 0.0168(3) Uani 1 1 d . . . . .
N3 N 0.34433(4) 0.25741(19) 0.64122(12) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.26973(4) 0.1385(2) 0.78917(12) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.37042(5) 0.2328(2) 0.92219(15) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.3788 0.2487 0.8462 0.030 Uiso 1 1 calc R U . . .
H3B H 0.3846 0.1298 0.9703 0.030 Uiso 1 1 calc R U . . .
H3C H 0.3752 0.3482 0.9706 0.030 Uiso 1 1 calc R U . . .
C4 C 0.30454(4) 0.1872(2) 0.77882(14) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.31121(4) 0.2241(2) 0.65822(14) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.2900 0.2234 0.5886 0.021 Uiso 1 1 calc R U . . .
C6 C 0.34936(4) 0.2819(2) 0.52056(14) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.38721(4) 0.2608(2) 0.51119(14) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.4065 0.2372 0.5842 0.021 Uiso 1 1 calc R U . . .
C10 C 0.39767(4) 0.2727(2) 0.39990(15) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.43908(5) 0.2553(2) 0.38979(16) 0.0228(4) Uani 1 1 d . . . . .
C15 C 0.46645(5) 0.2085(3) 0.51424(18) 0.0343(5) Uani 1 1 d . . . . .
H15C H 0.4925 0.1999 0.5044 0.051 Uiso 1 1 calc R U . . .
H15B H 0.4592 0.0887 0.5440 0.051 Uiso 1 1 calc R U . . .
H15A H 0.4652 0.3069 0.5738 0.051 Uiso 1 1 calc R U . . .
C13 C 0.44223(6) 0.0990(3) 0.29823(19) 0.0362(5) Uani 1 1 d . . . . .
H13A H 0.4687 0.0893 0.2923 0.054 Uiso 1 1 calc R U . . .
H13B H 0.4257 0.1284 0.2170 0.054 Uiso 1 1 calc R U . . .
H13C H 0.4343 -0.0200 0.3272 0.054 Uiso 1 1 calc R U . . .
C9 C 0.36841(5) 0.3086(2) 0.29474(14) 0.0191(3) Uani 1 1 d . . . . .
H9 H 0.3743 0.3149 0.2169 0.023 Uiso 1 1 calc R U . . .
C8 C 0.33111(5) 0.3353(2) 0.30091(14) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.3121 0.3605 0.2275 0.023 Uiso 1 1 calc R U . . .
C7 C 0.32084(4) 0.3260(2) 0.41317(14) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.30972(5) 0.1426(2) 0.97630(14) 0.0193(3) Uani 1 1 d . . . . .
H2 H 0.3196 0.1333 1.0629 0.023 Uiso 1 1 calc R U . . .
C1 C 0.27299(5) 0.1109(2) 0.91241(15) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.2528 0.0752 0.9477 0.024 Uiso 1 1 calc R U . . .
C14 C 0.45146(6) 0.4415(3) 0.3441(2) 0.0422(5) Uani 1 1 d . . . . .
H14B H 0.4498 0.5408 0.4027 0.063 Uiso 1 1 calc R U . . .
H14C H 0.4347 0.4716 0.2633 0.063 Uiso 1 1 calc R U . . .
H14A H 0.4778 0.4311 0.3369 0.063 Uiso 1 1 calc R U . . .
H101 H 0.2675(8) 0.357(4) 0.338(3) 0.065(9) Uiso 1 1 d . . . . .


_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 C7 1.3541(19) . ?
O1 H101 0.98(3) . ?
N2 C4 1.3619(19) . ?
N2 C2 1.373(2) . ?
N2 C3 1.461(2) . ?
N3 C5 1.284(2) . ?
N3 C6 1.4208(19) . ?
N1 C4 1.342(2) . ?
N1 C1 1.372(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.456(2) . ?
C5 H5 0.9500 . ?
C6 C11 1.410(2) . ?
C6 C7 1.413(2) . ?
C11 C10 1.395(2) . ?
C11 H11 0.9500 . ?
C10 C9 1.399(2) . ?
C10 C12 1.538(2) . ?
C12 C15 1.534(3) . ?
C12 C14 1.535(3) . ?
C12 C13 1.542(3) . ?
C15 H15C 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15A 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C9 C8 1.384(2) . ?
C9 H9 0.9500 . ?
C8 C7 1.401(2) . ?
C8 H8 0.9500 . ?
C2 C1 1.364(2) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14A 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
C7 O1 H101 109.4(16) . . ?
C4 N2 C2 107.00(13) . . ?
C4 N2 C3 128.57(13) . . ?
C2 N2 C3 124.43(13) . . ?
C5 N3 C6 120.79(13) . . ?
C4 N1 C1 106.17(13) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 N2 110.44(13) . . ?
N1 C4 C5 120.35(14) . . ?
N2 C4 C5 129.20(14) . . ?
N3 C5 C4 123.36(14) . . ?
N3 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C11 C6 C7 118.60(14) . . ?
C11 C6 N3 114.63(13) . . ?
C7 C6 N3 126.77(14) . . ?
C10 C11 C6 123.18(14) . . ?
C10 C11 H11 118.4 . . ?
C6 C11 H11 118.4 . . ?
C11 C10 C9 116.58(14) . . ?
C11 C10 C12 123.33(14) . . ?
C9 C10 C12 120.05(14) . . ?
C15 C12 C14 108.50(16) . . ?
C15 C12 C10 111.83(14) . . ?
C14 C12 C10 109.05(14) . . ?
C15 C12 C13 107.98(16) . . ?
C14 C12 C13 109.33(16) . . ?
C10 C12 C13 110.12(14) . . ?
C12 C15 H15C 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
C12 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C9 C10 121.83(15) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C8 C7 121.38(14) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
O1 C7 C8 121.44(14) . . ?
O1 C7 C6 120.21(14) . . ?
C8 C7 C6 118.33(14) . . ?
C1 C2 N2 106.97(14) . . ?
C1 C2 H2 126.5 . . ?
N2 C2 H2 126.5 . . ?
C2 C1 N1 109.42(14) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
H14C C14 H14A 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
C1 N1 C4 N2 0.23(18) . . . . ?
C1 N1 C4 C5 178.98(14) . . . . ?
C2 N2 C4 N1 -0.29(18) . . . . ?
C3 N2 C4 N1 178.83(15) . . . . ?
C2 N2 C4 C5 -178.90(16) . . . . ?
C3 N2 C4 C5 0.2(3) . . . . ?
C6 N3 C5 C4 176.41(14) . . . . ?
N1 C4 C5 N3 -174.57(15) . . . . ?
N2 C4 C5 N3 3.9(3) . . . . ?
C5 N3 C6 C11 -161.59(15) . . . . ?
C5 N3 C6 C7 19.1(2) . . . . ?
C7 C6 C11 C10 -3.1(2) . . . . ?
N3 C6 C11 C10 177.57(14) . . . . ?
C6 C11 C10 C9 0.4(2) . . . . ?
C6 C11 C10 C12 178.20(15) . . . . ?
C11 C10 C12 C15 4.4(2) . . . . ?
C9 C10 C12 C15 -177.79(16) . . . . ?
C11 C10 C12 C14 -115.54(19) . . . . ?
C9 C10 C12 C14 62.2(2) . . . . ?
C11 C10 C12 C13 124.50(18) . . . . ?
C9 C10 C12 C13 -57.7(2) . . . . ?
C11 C10 C9 C8 1.5(2) . . . . ?
C12 C10 C9 C8 -176.44(15) . . . . ?
C10 C9 C8 C7 -0.5(3) . . . . ?
C9 C8 C7 O1 175.96(15) . . . . ?
C9 C8 C7 C6 -2.2(2) . . . . ?
C11 C6 C7 O1 -174.31(14) . . . . ?
N3 C6 C7 O1 5.0(2) . . . . ?
C11 C6 C7 C8 3.9(2) . . . . ?
N3 C6 C7 C8 -176.83(15) . . . . ?
C4 N2 C2 C1 0.22(18) . . . . ?
C3 N2 C2 C1 -178.94(14) . . . . ?
N2 C2 C1 N1 -0.09(19) . . . . ?
C4 N1 C1 C2 -0.09(18) . . . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1891204'
loop_
_audit_author_name
_audit_author_address
'Matthew Akerman'
;University of KwaZulu-Natal
South Africa
;
_audit_update_record             
;
2019-01-16 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N3 O'
_chemical_formula_weight         215.25

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'
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'
H H 0.0000 0.0000 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.849(5)
_cell_length_b                   10.609(4)
_cell_length_c                   16.349(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.668(5)
_cell_angle_gamma                90
_cell_volume                     2213.5(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4440
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      29.1

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS, Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22148
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         29.059
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5907
_reflns_number_gt                4440
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_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)+(0.0733P)²+0.6579P] 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         5907
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1A O -0.10197(7) 0.13636(9) 0.74089(6) 0.0259(2) Uani 1 1 d . . . . .
O1B O 0.10254(7) -0.10459(9) 0.76393(6) 0.0261(2) Uani 1 1 d . . . . .
N3A N -0.22479(8) -0.03302(10) 0.62609(6) 0.0208(2) Uani 1 1 d . . . . .
N3B N 0.22849(8) 0.06768(11) 0.87423(6) 0.0214(2) Uani 1 1 d . . . . .
N1A N -0.02303(8) -0.26473(11) 0.67436(6) 0.0221(2) Uani 1 1 d . . . . .
N2A N -0.17929(8) -0.30614(10) 0.60728(6) 0.0208(2) Uani 1 1 d . . . . .
N2B N 0.18244(8) 0.34043(10) 0.89280(6) 0.0216(2) Uani 1 1 d . . . . .
N1B N 0.02350(8) 0.29710(11) 0.83137(6) 0.0221(2) Uani 1 1 d . . . . .
C6A C -0.24780(9) 0.09462(12) 0.64001(7) 0.0190(2) Uani 1 1 d . . . . .
C4B C 0.11637(9) 0.24854(12) 0.86010(7) 0.0192(2) Uani 1 1 d . . . . .
C6B C 0.25128(9) -0.06041(12) 0.86147(7) 0.0191(2) Uani 1 1 d . . . . .
C4A C -0.11392(9) -0.21487(12) 0.64194(7) 0.0198(3) Uani 1 1 d . . . . .
C11B C 0.34526(9) -0.10378(13) 0.90408(7) 0.0215(3) Uani 1 1 d . . . . .
H11B H 0.3858 -0.0469 0.9395 0.026 Uiso 1 1 calc R U . . .
C9A C -0.31798(10) 0.34163(13) 0.65764(8) 0.0239(3) Uani 1 1 d . . . . .
H9A H -0.3408 0.4259 0.6639 0.029 Uiso 1 1 calc R U . . .
C8B C 0.22893(10) -0.26738(13) 0.80033(8) 0.0236(3) Uani 1 1 d . . . . .
H8B H 0.1895 -0.3248 0.7645 0.028 Uiso 1 1 calc R U . . .
C9B C 0.32197(10) -0.30714(13) 0.84410(8) 0.0248(3) Uani 1 1 d . . . . .
H9B H 0.3451 -0.3913 0.8379 0.030 Uiso 1 1 calc R U . . .
C8A C -0.22649(10) 0.30052(12) 0.70293(8) 0.0225(3) Uani 1 1 d . . . . .
H8A H -0.1879 0.3571 0.7399 0.027 Uiso 1 1 calc R U . . .
C7A C -0.18988(9) 0.17795(12) 0.69541(7) 0.0200(3) Uani 1 1 d . . . . .
C10B C 0.38198(10) -0.22557(13) 0.89708(7) 0.0238(3) Uani 1 1 d . . . . .
C11A C -0.34050(9) 0.13939(12) 0.59611(7) 0.0214(3) Uani 1 1 d . . . . .
H11A H -0.3804 0.0832 0.5596 0.026 Uiso 1 1 calc R U . . .
C10A C -0.37700(9) 0.26134(13) 0.60315(7) 0.0229(3) Uani 1 1 d . . . . .
C2A C -0.12688(10) -0.41805(13) 0.61849(8) 0.0242(3) Uani 1 1 d . . . . .
H2A H -0.1523 -0.4989 0.6009 0.029 Uiso 1 1 calc R U . . .
C2B C 0.12793(10) 0.45134(13) 0.88451(8) 0.0254(3) Uani 1 1 d . . . . .
H2B H 0.1531 0.5323 0.9020 0.031 Uiso 1 1 calc R U . . .
C1A C -0.03105(10) -0.39117(13) 0.65985(8) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.0221 -0.4514 0.6761 0.030 Uiso 1 1 calc R U . . .
C7B C 0.19200(9) -0.14497(12) 0.80779(7) 0.0204(3) Uani 1 1 d . . . . .
C12A C -0.47789(11) 0.30401(15) 0.55474(9) 0.0327(3) Uani 1 1 d . . . . .
H12A H -0.4971 0.2454 0.5092 0.049 Uiso 1 1 calc R U . . .
H12B H -0.4685 0.3887 0.5327 0.049 Uiso 1 1 calc R U . . .
H12C H -0.5336 0.3058 0.5909 0.049 Uiso 1 1 calc R U . . .
C3A C -0.28513(10) -0.29177(14) 0.56490(8) 0.0262(3) Uani 1 1 d . . . . .
H3A H -0.3306 -0.2548 0.6027 0.039 Uiso 1 1 calc R U . . .
H3B H -0.3125 -0.3745 0.5465 0.039 Uiso 1 1 calc R U . . .
H3C H -0.2833 -0.2363 0.5172 0.039 Uiso 1 1 calc R U . . .
C5B C 0.13793(10) 0.11518(12) 0.85205(7) 0.0213(3) Uani 1 1 d . . . . .
H5B H 0.0830 0.0612 0.8295 0.026 Uiso 1 1 calc R U . . .
C5A C -0.13507(9) -0.08163(12) 0.64988(7) 0.0211(3) Uani 1 1 d . . . . .
H5A H -0.0804 -0.0282 0.6736 0.025 Uiso 1 1 calc R U . . .
C1B C 0.03078(10) 0.42347(13) 0.84639(8) 0.0250(3) Uani 1 1 d . . . . .
H1B H -0.0236 0.4830 0.8324 0.030 Uiso 1 1 calc R U . . .
C12B C 0.48447(11) -0.26677(16) 0.94393(9) 0.0330(3) Uani 1 1 d . . . . .
H22A H 0.5410 -0.2561 0.9091 0.049 Uiso 1 1 calc R U . . .
H22B H 0.4798 -0.3556 0.9594 0.049 Uiso 1 1 calc R U . . .
H22C H 0.4992 -0.2153 0.9937 0.049 Uiso 1 1 calc R U . . .
C3B C 0.29033(10) 0.32690(14) 0.93090(9) 0.0281(3) Uani 1 1 d . . . . .
H13A H 0.2930 0.2647 0.9754 0.042 Uiso 1 1 calc R U . . .
H13B H 0.3159 0.4083 0.9534 0.042 Uiso 1 1 calc R U . . .
H13C H 0.3345 0.2986 0.8895 0.042 Uiso 1 1 calc R U . . .
H101 H -0.0656(15) 0.199(2) 0.7719(12) 0.059(6) Uiso 1 1 d . . . . .
H102 H 0.0658(15) -0.1721(19) 0.7306(12) 0.057(6) Uiso 1 1 d . . . . .


_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
O1A C7A 1.3523(14) . ?
O1A H101 0.93(2) . ?
O1B C7B 1.3519(14) . ?
O1B H102 0.99(2) . ?
N3A C5A 1.2815(16) . ?
N3A C6A 1.4102(17) . ?
N3B C5B 1.2811(16) . ?
N3B C6B 1.4108(18) . ?
N1A C4A 1.3345(16) . ?
N1A C1A 1.3641(18) . ?
N2A C4A 1.3615(16) . ?
N2A C2A 1.3668(17) . ?
N2A C3A 1.4607(16) . ?
N2B C4B 1.3606(16) . ?
N2B C2B 1.3680(18) . ?
N2B C3B 1.4594(16) . ?
N1B C4B 1.3341(16) . ?
N1B C1B 1.3642(19) . ?
C6A C11A 1.4002(17) . ?
C6A C7A 1.4140(17) . ?
C4B C5B 1.4507(19) . ?
C6B C11B 1.3999(17) . ?
C6B C7B 1.4142(17) . ?
C4A C5A 1.4481(19) . ?
C11B C10B 1.3847(19) . ?
C11B H11B 0.9500 . ?
C9A C8A 1.3850(17) . ?
C9A C10A 1.3919(18) . ?
C9A H9A 0.9500 . ?
C8B C9B 1.3858(17) . ?
C8B C7B 1.3928(19) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3922(19) . ?
C9B H9B 0.9500 . ?
C8A C7A 1.3930(19) . ?
C8A H8A 0.9500 . ?
C10B C12B 1.5092(18) . ?
C11A C10A 1.3855(19) . ?
C11A H11A 0.9500 . ?
C10A C12A 1.5077(17) . ?
C2A C1A 1.3643(18) . ?
C2A H2A 0.9500 . ?
C2B C1B 1.3614(18) . ?
C2B H2B 0.9500 . ?
C1A H1A 0.9500 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3A H3C 0.9800 . ?
C5B H5B 0.9500 . ?
C5A H5A 0.9500 . ?
C1B H1B 0.9500 . ?
C12B H22A 0.9800 . ?
C12B H22B 0.9800 . ?
C12B H22C 0.9800 . ?
C3B H13A 0.9800 . ?
C3B H13B 0.9800 . ?
C3B H13C 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
C7A O1A H101 113.5(12) . . ?
C7B O1B H102 112.7(11) . . ?
C5A N3A C6A 122.39(11) . . ?
C5B N3B C6B 122.30(11) . . ?
C4A N1A C1A 106.00(11) . . ?
C4A N2A C2A 106.94(11) . . ?
C4A N2A C3A 128.22(11) . . ?
C2A N2A C3A 124.84(11) . . ?
C4B N2B C2B 106.76(11) . . ?
C4B N2B C3B 128.00(11) . . ?
C2B N2B C3B 125.23(11) . . ?
C4B N1B C1B 106.04(11) . . ?
C11A C6A N3A 115.14(11) . . ?
C11A C6A C7A 117.99(12) . . ?
N3A C6A C7A 126.81(11) . . ?
N1B C4B N2B 110.70(11) . . ?
N1B C4B C5B 121.14(11) . . ?
N2B C4B C5B 128.12(11) . . ?
C11B C6B N3B 115.15(11) . . ?
C11B C6B C7B 118.14(12) . . ?
N3B C6B C7B 126.64(11) . . ?
N1A C4A N2A 110.65(11) . . ?
N1A C4A C5A 121.06(11) . . ?
N2A C4A C5A 128.20(11) . . ?
C10B C11B C6B 123.23(12) . . ?
C10B C11B H11B 118.4 . . ?
C6B C11B H11B 118.4 . . ?
C8A C9A C10A 121.00(12) . . ?
C8A C9A H9A 119.5 . . ?
C10A C9A H9A 119.5 . . ?
C9B C8B C7B 121.38(12) . . ?
C9B C8B H8B 119.3 . . ?
C7B C8B H8B 119.3 . . ?
C8B C9B C10B 120.95(13) . . ?
C8B C9B H9B 119.5 . . ?
C10B C9B H9B 119.5 . . ?
C9A C8A C7A 121.41(12) . . ?
C9A C8A H8A 119.3 . . ?
C7A C8A H8A 119.3 . . ?
O1A C7A C8A 121.68(11) . . ?
O1A C7A C6A 119.48(11) . . ?
C8A C7A C6A 118.82(11) . . ?
C11B C10B C9B 117.51(12) . . ?
C11B C10B C12B 120.92(12) . . ?
C9B C10B C12B 121.55(13) . . ?
C10A C11A C6A 123.38(12) . . ?
C10A C11A H11A 118.3 . . ?
C6A C11A H11A 118.3 . . ?
C11A C10A C9A 117.39(11) . . ?
C11A C10A C12A 121.03(12) . . ?
C9A C10A C12A 121.57(12) . . ?
C1A C2A N2A 106.69(12) . . ?
C1A C2A H2A 126.7 . . ?
N2A C2A H2A 126.7 . . ?
C1B C2B N2B 106.88(12) . . ?
C1B C2B H2B 126.6 . . ?
N2B C2B H2B 126.6 . . ?
N1A C1A C2A 109.72(12) . . ?
N1A C1A H1A 125.1 . . ?
C2A C1A H1A 125.1 . . ?
O1B C7B C8B 121.76(11) . . ?
O1B C7B C6B 119.45(11) . . ?
C8B C7B C6B 118.78(11) . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N2A C3A H3A 109.5 . . ?
N2A C3A H3B 109.5 . . ?
H3A C3A H3B 109.5 . . ?
N2A C3A H3C 109.5 . . ?
H3A C3A H3C 109.5 . . ?
H3B C3A H3C 109.5 . . ?
N3B C5B C4B 122.32(12) . . ?
N3B C5B H5B 118.8 . . ?
C4B C5B H5B 118.8 . . ?
N3A C5A C4A 122.49(11) . . ?
N3A C5A H5A 118.8 . . ?
C4A C5A H5A 118.8 . . ?
C2B C1B N1B 109.62(12) . . ?
C2B C1B H1B 125.2 . . ?
N1B C1B H1B 125.2 . . ?
C10B C12B H22A 109.5 . . ?
C10B C12B H22B 109.5 . . ?
H22A C12B H22B 109.5 . . ?
C10B C12B H22C 109.5 . . ?
H22A C12B H22C 109.5 . . ?
H22B C12B H22C 109.5 . . ?
N2B C3B H13A 109.5 . . ?
N2B C3B H13B 109.5 . . ?
H13A C3B H13B 109.5 . . ?
N2B C3B H13C 109.5 . . ?
H13A C3B H13C 109.5 . . ?
H13B C3B H13C 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
C5A N3A C6A C11A 167.46(11) . . . . ?
C5A N3A C6A C7A -15.43(19) . . . . ?
C1B N1B C4B N2B -0.10(14) . . . . ?
C1B N1B C4B C5B -178.06(11) . . . . ?
C2B N2B C4B N1B 0.39(14) . . . . ?
C3B N2B C4B N1B 179.57(11) . . . . ?
C2B N2B C4B C5B 178.17(12) . . . . ?
C3B N2B C4B C5B -2.6(2) . . . . ?
C5B N3B C6B C11B -167.04(11) . . . . ?
C5B N3B C6B C7B 16.30(19) . . . . ?
C1A N1A C4A N2A -0.02(13) . . . . ?
C1A N1A C4A C5A 176.76(11) . . . . ?
C2A N2A C4A N1A -0.03(14) . . . . ?
C3A N2A C4A N1A -179.46(11) . . . . ?
C2A N2A C4A C5A -176.53(12) . . . . ?
C3A N2A C4A C5A 4.0(2) . . . . ?
N3B C6B C11B C10B -177.93(11) . . . . ?
C7B C6B C11B C10B -0.97(18) . . . . ?
C7B C8B C9B C10B -0.1(2) . . . . ?
C10A C9A C8A C7A 0.33(19) . . . . ?
C9A C8A C7A O1A -178.40(11) . . . . ?
C9A C8A C7A C6A 0.19(19) . . . . ?
C11A C6A C7A O1A 177.69(11) . . . . ?
N3A C6A C7A O1A 0.66(19) . . . . ?
C11A C6A C7A C8A -0.93(17) . . . . ?
N3A C6A C7A C8A -177.96(11) . . . . ?
C6B C11B C10B C9B 0.70(19) . . . . ?
C6B C11B C10B C12B 179.41(12) . . . . ?
C8B C9B C10B C11B -0.13(19) . . . . ?
C8B C9B C10B C12B -178.83(12) . . . . ?
N3A C6A C11A C10A 178.61(11) . . . . ?
C7A C6A C11A C10A 1.24(18) . . . . ?
C6A C11A C10A C9A -0.73(19) . . . . ?
C6A C11A C10A C12A -179.54(12) . . . . ?
C8A C9A C10A C11A -0.07(19) . . . . ?
C8A C9A C10A C12A 178.74(12) . . . . ?
C4A N2A C2A C1A 0.08(14) . . . . ?
C3A N2A C2A C1A 179.52(11) . . . . ?
C4B N2B C2B C1B -0.52(14) . . . . ?
C3B N2B C2B C1B -179.73(11) . . . . ?
C4A N1A C1A C2A 0.07(14) . . . . ?
N2A C2A C1A N1A -0.09(14) . . . . ?
C9B C8B C7B O1B 178.49(11) . . . . ?
C9B C8B C7B C6B -0.13(19) . . . . ?
C11B C6B C7B O1B -178.00(11) . . . . ?
N3B C6B C7B O1B -1.42(19) . . . . ?
C11B C6B C7B C8B 0.65(17) . . . . ?
N3B C6B C7B C8B 177.23(11) . . . . ?
C6B N3B C5B C4B -175.76(11) . . . . ?
N1B C4B C5B N3B 175.33(11) . . . . ?
N2B C4B C5B N3B -2.3(2) . . . . ?
C6A N3A C5A C4A 174.63(11) . . . . ?
N1A C4A C5A N3A -173.49(11) . . . . ?
N2A C4A C5A N3A 2.7(2) . . . . ?
N2B C2B C1B N1B 0.47(15) . . . . ?
C4B N1B C1B C2B -0.23(14) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1891008'
loop_
_audit_author_name
_audit_author_address
'Matthew P Akerman' 'University of KwaZulu-Natal'
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N3 O'
_chemical_formula_sum            'C11 H11 N3 O'
_chemical_formula_weight         201.23

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                   11.5123(13)
_cell_length_b                   9.0527(8)
_cell_length_c                   19.5365(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.232(4)
_cell_angle_gamma                90
_cell_volume                     2024.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4559
_cell_measurement_theta_min      0.026
_cell_measurement_theta_max      28.9

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS, Bruker 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19110
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         28.948
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5328
_reflns_number_gt                4559
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_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)+(0.0461P)²+0.9527P] 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         5328
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1A O 0.42965(8) 0.98707(10) 0.10721(4) 0.02079(19) Uani 1 1 d . . . . .
O1B O 0.07817(8) 0.62100(10) 0.06820(4) 0.02125(19) Uani 1 1 d . . . . .
N3A N 0.23371(8) 1.09157(11) 0.02015(5) 0.0177(2) Uani 1 1 d . . . . .
N2A N 0.16936(8) 0.90121(11) -0.10280(5) 0.0173(2) Uani 1 1 d . . . . .
N3B N -0.14786(8) 0.63986(11) 0.12517(5) 0.0170(2) Uani 1 1 d . . . . .
N2B N -0.36378(8) 0.46590(11) 0.08251(5) 0.0179(2) Uani 1 1 d . . . . .
N1B N -0.26902(9) 0.37594(11) -0.00164(5) 0.0186(2) Uani 1 1 d . . . . .
C9A C 0.35228(11) 1.31525(14) 0.20477(6) 0.0217(2) Uani 1 1 d . . . . .
H1 H 0.3775 1.3650 0.2465 0.026 Uiso 1 1 calc R U . . .
C10A C 0.25855(11) 1.37031(14) 0.16106(6) 0.0218(2) Uani 1 1 d . . . . .
H9 H 0.2204 1.4585 0.1725 0.026 Uiso 1 1 calc R U . . .
C11A C 0.22121(10) 1.29483(14) 0.10038(6) 0.0194(2) Uani 1 1 d . . . . .
H6 H 0.1555 1.3305 0.0715 0.023 Uiso 1 1 calc R U . . .
C6A C 0.27874(10) 1.16775(13) 0.08123(6) 0.0161(2) Uani 1 1 d . . . . .
C5A C 0.30242(10) 1.06792(13) -0.02582(6) 0.0168(2) Uani 1 1 d . . . . .
H10 H 0.3791 1.1080 -0.0191 0.020 Uiso 1 1 calc R U . . .
C4A C 0.26896(9) 0.98241(13) -0.08819(6) 0.0156(2) Uani 1 1 d . . . . .
C2A C 0.17781(11) 0.83115(14) -0.16432(6) 0.0204(2) Uani 1 1 d . . . . .
H2 H 0.1217 0.7670 -0.1879 0.024 Uiso 1 1 calc R U . . .
C3A C 0.06819(11) 0.89094(16) -0.06375(7) 0.0243(3) Uani 1 1 d . . . . .
H12 H 0.0948 0.8734 -0.0151 0.036 Uiso 1 1 calc R U . . .
H3 H 0.0181 0.8091 -0.0816 0.036 Uiso 1 1 calc R U . . .
H11 H 0.0239 0.9835 -0.0684 0.036 Uiso 1 1 calc R U . . .
N1A N 0.34001(8) 0.96614(11) -0.13771(5) 0.0180(2) Uani 1 1 d . . . . .
C1A C 0.28283(11) 0.87172(14) -0.18514(6) 0.0201(2) Uani 1 1 d . . . . .
H4 H 0.3120 0.8395 -0.2263 0.024 Uiso 1 1 calc R U . . .
C8A C 0.40890(10) 1.18687(14) 0.18701(6) 0.0194(2) Uani 1 1 d . . . . .
H8 H 0.4718 1.1488 0.2174 0.023 Uiso 1 1 calc R U . . .
C7A C 0.37460(10) 1.11322(13) 0.12506(6) 0.0165(2) Uani 1 1 d . . . . .
C9B C 0.13373(11) 0.92142(14) 0.19461(6) 0.0207(2) Uani 1 1 d . . . . .
H13 H 0.1943 0.9882 0.2105 0.025 Uiso 1 1 calc R U . . .
C8B C 0.15133(10) 0.81911(13) 0.14333(6) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.2246 0.8158 0.1252 0.023 Uiso 1 1 calc R U . . .
C7B C 0.06215(10) 0.72082(13) 0.11812(6) 0.0164(2) Uani 1 1 d . . . . .
C6B C -0.04733(10) 0.72658(12) 0.14528(6) 0.0156(2) Uani 1 1 d . . . . .
C5B C -0.15635(10) 0.55270(13) 0.07321(6) 0.0175(2) Uani 1 1 d . . . . .
H20 H -0.0915 0.5430 0.0473 0.021 Uiso 1 1 calc R U . . .
C4BC C -0.26203(10) 0.46787(13) 0.05242(6) 0.0161(2) Uani 1 1 d . . . . .
C2B C -0.43696(10) 0.36703(14) 0.04615(6) 0.0207(2) Uani 1 1 d . . . . .
H14 H -0.5139 0.3414 0.0551 0.025 Uiso 1 1 calc R U . . .
C3B C -0.39224(11) 0.54753(16) 0.14336(7) 0.0268(3) Uani 1 1 d . . . . .
H23 H -0.3428 0.5123 0.1841 0.040 Uiso 1 1 calc R U . . .
H15 H -0.4746 0.5317 0.1497 0.040 Uiso 1 1 calc R U . . .
H22 H -0.3783 0.6532 0.1369 0.040 Uiso 1 1 calc R U . . .
C1B C -0.37800(10) 0.31237(13) -0.00550(6) 0.0200(2) Uani 1 1 d . . . . .
H21 H -0.4077 0.2416 -0.0388 0.024 Uiso 1 1 calc R U . . .
C10B C 0.02757(11) 0.92578(14) 0.22247(6) 0.0202(2) Uani 1 1 d . . . . .
H18 H 0.0157 0.9945 0.2578 0.024 Uiso 1 1 calc R U . . .
C11B C -0.06106(10) 0.82843(13) 0.19808(6) 0.0181(2) Uani 1 1 d . . . . .
H17 H -0.1330 0.8310 0.2177 0.022 Uiso 1 1 calc R U . . .
H7 H 0.5049(15) 0.9960(18) 0.1217(8) 0.027 Uiso 1 1 d . U . . .
H16 H 0.1515(14) 0.6331(18) 0.0512(8) 0.027 Uiso 1 1 d . 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
O1A C7A 1.3694(14) . ?
O1A H7 0.886(17) . ?
O1B C7B 1.3567(14) . ?
O1B H16 0.947(17) . ?
N3A C5A 1.2776(15) . ?
N3A C6A 1.4262(14) . ?
N2A C4A 1.3659(14) . ?
N2A C2A 1.3717(15) . ?
N2A C3A 1.4629(15) . ?
N3B C5B 1.2810(15) . ?
N3B C6B 1.4183(14) . ?
N2B C4BC 1.3665(14) . ?
N2B C2B 1.3732(15) . ?
N2B C3B 1.4668(16) . ?
N1B C4BC 1.3401(15) . ?
N1B C1B 1.3749(15) . ?
C9A C10A 1.3935(18) . ?
C9A C8A 1.3946(18) . ?
C9A H1 0.9500 . ?
C10A C11A 1.3951(17) . ?
C10A H9 0.9500 . ?
C11A C6A 1.3985(17) . ?
C11A H6 0.9500 . ?
C6A C7A 1.4106(16) . ?
C5A C4A 1.4597(15) . ?
C5A H10 0.9500 . ?
C4A N1A 1.3410(15) . ?
C2A C1A 1.3670(17) . ?
C2A H2 0.9500 . ?
C3A H12 0.9800 . ?
C3A H3 0.9800 . ?
C3A H11 0.9800 . ?
N1A C1A 1.3748(15) . ?
C1A H4 0.9500 . ?
C8A C7A 1.4005(16) . ?
C8A H8 0.9500 . ?
C9B C10B 1.3914(18) . ?
C9B C8B 1.3953(17) . ?
C9B H13 0.9500 . ?
C8B C7B 1.4066(16) . ?
C8B H19 0.9500 . ?
C7B C6B 1.4206(16) . ?
C6B C11B 1.4052(16) . ?
C5B C4BC 1.4586(16) . ?
C5B H20 0.9500 . ?
C2B C1B 1.3685(17) . ?
C2B H14 0.9500 . ?
C3B H23 0.9800 . ?
C3B H15 0.9800 . ?
C3B H22 0.9800 . ?
C1B H21 0.9500 . ?
C10B C11B 1.3925(17) . ?
C10B H18 0.9500 . ?
C11B H17 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
C7A O1A H7 107.8(11) . . ?
C7B O1B H16 111.8(10) . . ?
C5A N3A C6A 118.21(10) . . ?
C4A N2A C2A 107.10(10) . . ?
C4A N2A C3A 128.54(10) . . ?
C2A N2A C3A 124.32(10) . . ?
C5B N3B C6B 123.38(10) . . ?
C4BC N2B C2B 107.00(10) . . ?
C4BC N2B C3B 128.28(10) . . ?
C2B N2B C3B 124.69(10) . . ?
C4BC N1B C1B 106.24(10) . . ?
C10A C9A C8A 119.82(11) . . ?
C10A C9A H1 120.1 . . ?
C8A C9A H1 120.1 . . ?
C9A C10A C11A 119.49(11) . . ?
C9A C10A H9 120.3 . . ?
C11A C10A H9 120.3 . . ?
C10A C11A C6A 121.26(11) . . ?
C10A C11A H6 119.4 . . ?
C6A C11A H6 119.4 . . ?
C11A C6A C7A 119.18(10) . . ?
C11A C6A N3A 118.81(10) . . ?
C7A C6A N3A 121.87(10) . . ?
N3A C5A C4A 123.25(10) . . ?
N3A C5A H10 118.4 . . ?
C4A C5A H10 118.4 . . ?
N1A C4A N2A 110.74(10) . . ?
N1A C4A C5A 122.28(10) . . ?
N2A C4A C5A 126.82(10) . . ?
C1A C2A N2A 106.60(10) . . ?
C1A C2A H2 126.7 . . ?
N2A C2A H2 126.7 . . ?
N2A C3A H12 109.5 . . ?
N2A C3A H3 109.5 . . ?
H12 C3A H3 109.5 . . ?
N2A C3A H11 109.5 . . ?
H12 C3A H11 109.5 . . ?
H3 C3A H11 109.5 . . ?
C4A N1A C1A 105.64(10) . . ?
C2A C1A N1A 109.92(11) . . ?
C2A C1A H4 125.0 . . ?
N1A C1A H4 125.0 . . ?
C9A C8A C7A 121.08(11) . . ?
C9A C8A H8 119.5 . . ?
C7A C8A H8 119.5 . . ?
O1A C7A C8A 121.48(10) . . ?
O1A C7A C6A 119.37(10) . . ?
C8A C7A C6A 119.11(11) . . ?
C10B C9B C8B 120.13(11) . . ?
C10B C9B H13 119.9 . . ?
C8B C9B H13 119.9 . . ?
C9B C8B C7B 120.93(11) . . ?
C9B C8B H19 119.5 . . ?
C7B C8B H19 119.5 . . ?
O1B C7B C8B 121.47(10) . . ?
O1B C7B C6B 119.23(10) . . ?
C8B C7B C6B 119.30(10) . . ?
C11B C6B N3B 114.40(10) . . ?
C11B C6B C7B 118.25(10) . . ?
N3B C6B C7B 127.35(10) . . ?
N3B C5B C4BC 122.31(10) . . ?
N3B C5B H20 118.8 . . ?
C4BC C5B H20 118.8 . . ?
N1B C4BC N2B 110.49(10) . . ?
N1B C4BC C5B 121.56(10) . . ?
N2B C4BC C5B 127.95(10) . . ?
C1B C2B N2B 106.95(10) . . ?
C1B C2B H14 126.5 . . ?
N2B C2B H14 126.5 . . ?
N2B C3B H23 109.5 . . ?
N2B C3B H15 109.5 . . ?
H23 C3B H15 109.5 . . ?
N2B C3B H22 109.5 . . ?
H23 C3B H22 109.5 . . ?
H15 C3B H22 109.5 . . ?
C2B C1B N1B 109.32(11) . . ?
C2B C1B H21 125.3 . . ?
N1B C1B H21 125.3 . . ?
C9B C10B C11B 119.36(11) . . ?
C9B C10B H18 120.3 . . ?
C11B C10B H18 120.3 . . ?
C10B C11B C6B 122.00(11) . . ?
C10B C11B H17 119.0 . . ?
C6B C11B H17 119.0 . . ?

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
C8A C9A C10A C11A 0.99(18) . . . . ?
C9A C10A C11A C6A -2.37(18) . . . . ?
C10A C11A C6A C7A 1.51(17) . . . . ?
C10A C11A C6A N3A 177.36(11) . . . . ?
C5A N3A C6A C11A 125.22(12) . . . . ?
C5A N3A C6A C7A -59.04(15) . . . . ?
C6A N3A C5A C4A 175.61(10) . . . . ?
C2A N2A C4A N1A -0.22(13) . . . . ?
C3A N2A C4A N1A -178.06(11) . . . . ?
C2A N2A C4A C5A -175.76(11) . . . . ?
C3A N2A C4A C5A 6.41(19) . . . . ?
N3A C5A C4A N1A 176.00(11) . . . . ?
N3A C5A C4A N2A -8.94(19) . . . . ?
C4A N2A C2A C1A 0.19(13) . . . . ?
C3A N2A C2A C1A 178.14(11) . . . . ?
N2A C4A N1A C1A 0.16(13) . . . . ?
C5A C4A N1A C1A 175.93(10) . . . . ?
N2A C2A C1A N1A -0.10(14) . . . . ?
C4A N1A C1A C2A -0.03(13) . . . . ?
C10A C9A C8A C7A 1.23(18) . . . . ?
C9A C8A C7A O1A -179.97(11) . . . . ?
C9A C8A C7A C6A -2.07(17) . . . . ?
C11A C6A C7A O1A 178.65(10) . . . . ?
N3A C6A C7A O1A 2.93(16) . . . . ?
C11A C6A C7A C8A 0.70(16) . . . . ?
N3A C6A C7A C8A -175.01(10) . . . . ?
C10B C9B C8B C7B 1.10(18) . . . . ?
C9B C8B C7B O1B 179.91(10) . . . . ?
C9B C8B C7B C6B 0.20(17) . . . . ?
C5B N3B C6B C11B 172.29(11) . . . . ?
C5B N3B C6B C7B -7.64(18) . . . . ?
O1B C7B C6B C11B 178.52(10) . . . . ?
C8B C7B C6B C11B -1.76(16) . . . . ?
O1B C7B C6B N3B -1.55(17) . . . . ?
C8B C7B C6B N3B 178.16(11) . . . . ?
C6B N3B C5B C4BC -178.19(10) . . . . ?
C1B N1B C4BC N2B -0.70(13) . . . . ?
C1B N1B C4BC C5B 178.56(10) . . . . ?
C2B N2B C4BC N1B 0.76(13) . . . . ?
C3B N2B C4BC N1B 178.80(11) . . . . ?
C2B N2B C4BC C5B -178.45(11) . . . . ?
C3B N2B C4BC C5B -0.4(2) . . . . ?
N3B C5B C4BC N1B -179.26(11) . . . . ?
N3B C5B C4BC N2B -0.13(19) . . . . ?
C4BC N2B C2B C1B -0.49(13) . . . . ?
C3B N2B C2B C1B -178.62(11) . . . . ?
N2B C2B C1B N1B 0.07(14) . . . . ?
C4BC N1B C1B C2B 0.38(13) . . . . ?
C8B C9B C10B C11B -0.78(18) . . . . ?
C9B C10B C11B C6B -0.86(18) . . . . ?
N3B C6B C11B C10B -177.81(10) . . . . ?
C7B C6B C11B C10B 2.12(17) . . . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1891599'
loop_
_audit_author_name
_audit_author_address
'Matthew Akerman'
;University of KwaZulu-Natal
South Africa
;
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H11 N3 O), H2 O'
_chemical_formula_sum            'C22 H24 N6 O3'
_chemical_formula_weight         420.463

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   22.5522(16)
_cell_length_b                   7.1022(5)
_cell_length_c                   13.4620(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.400(3)
_cell_angle_gamma                90
_cell_volume                     2021.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2384
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      29.0

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS, Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Incoatec microsource'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9162
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.229
_diffrn_reflns_theta_max         29.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2651
_reflns_number_gt                2384
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_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)+(0.0504P)²+2.6771P] 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         2651
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.13409(4) 1.00061(15) 0.27627(7) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.0000 0.9564(2) 0.2500 0.0217(3) Uani 1 2 d S T P . .
N1 N -0.05107(5) 0.72242(16) 0.06993(8) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.07217(5) 0.83648(15) 0.08817(8) 0.0139(2) Uani 1 1 d . . . . .
N3 N -0.07220(5) 0.64113(15) -0.09885(8) 0.0135(2) Uani 1 1 d . . . . .
C1 C -0.11079(6) 0.64856(19) 0.02955(10) 0.0180(3) Uani 1 1 d . . . . .
H1 H -0.1388 0.6353 0.0680 0.022 Uiso 1 1 calc R U . . .
C2 C -0.02848(5) 0.71640(17) -0.00954(9) 0.0128(2) Uani 1 1 d . . . . .
C3 C 0.03388(5) 0.78427(17) -0.00225(9) 0.0134(2) Uani 1 1 d . . . . .
H8 H 0.0458 0.7896 -0.0633 0.016 Uiso 1 1 calc R U . . .
C4 C 0.13306(5) 0.90831(17) 0.10303(9) 0.0128(2) Uani 1 1 d . . . . .
C5 C 0.16286(5) 0.99353(17) 0.20285(9) 0.0134(2) Uani 1 1 d . . . . .
C6 C 0.22215(5) 1.07732(18) 0.22729(9) 0.0156(2) Uani 1 1 d . . . . .
H11 H 0.2417 1.1365 0.2941 0.019 Uiso 1 1 calc R U . . .
C7 C 0.25258(6) 1.07394(19) 0.15349(10) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.2928 1.1324 0.1697 0.021 Uiso 1 1 calc R U . . .
C8 C -0.06508(6) 0.60260(19) -0.20084(9) 0.0182(3) Uani 1 1 d . . . . .
H6 H -0.0412 0.7051 -0.2182 0.027 Uiso 1 1 calc R U . . .
H5 H -0.1070 0.5932 -0.2561 0.027 Uiso 1 1 calc R U . . .
H4 H -0.0423 0.4837 -0.1966 0.027 Uiso 1 1 calc R U . . .
C9 C -0.12451(6) 0.59645(18) -0.07403(10) 0.0162(2) Uani 1 1 d . . . . .
H7 H -0.1626 0.5406 -0.1195 0.019 Uiso 1 1 calc R U . . .
C10 C 0.16492(6) 0.90340(18) 0.03023(9) 0.0160(2) Uani 1 1 d . . . . .
H10 H 0.1458 0.8441 -0.0366 0.019 Uiso 1 1 calc R U . . .
C11 C 0.22446(6) 0.98508(19) 0.05551(10) 0.0182(3) Uani 1 1 d . . . . .
H9 H 0.2460 0.9805 0.0062 0.022 Uiso 1 1 calc R U . . .
H102 H -0.0129(9) 0.880(3) 0.1941(15) 0.037(5) Uiso 1 1 d . . . . .
H101 H 0.0966(10) 0.967(3) 0.2494(16) 0.036(5) Uiso 1 1 d . . . . .


_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 C5 1.3593(14) . ?
O1 H101 0.83(2) . ?
O2 H102 0.89(2) . ?
N1 C2 1.3362(15) . ?
N1 C1 1.3689(16) . ?
N2 C3 1.2776(15) . ?
N2 C4 1.4122(14) . ?
N3 C2 1.3700(15) . ?
N3 C9 1.3708(15) . ?
N3 C8 1.4626(15) . ?
C1 C9 1.3697(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.4572(15) . ?
C3 H8 0.9500 . ?
C4 C10 1.4032(16) . ?
C4 C5 1.4121(16) . ?
C5 C6 1.3941(16) . ?
C6 C7 1.3908(17) . ?
C6 H11 0.9500 . ?
C7 C11 1.3989(17) . ?
C7 H2 0.9500 . ?
C8 H6 0.9800 . ?
C8 H5 0.9800 . ?
C8 H4 0.9800 . ?
C9 H7 0.9500 . ?
C10 C11 1.3917(17) . ?
C10 H10 0.9500 . ?
C11 H9 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
C5 O1 H101 110.1(13) . . ?
C2 N1 C1 105.46(10) . . ?
C3 N2 C4 122.74(10) . . ?
C2 N3 C9 107.07(10) . . ?
C2 N3 C8 128.03(10) . . ?
C9 N3 C8 124.81(10) . . ?
N1 C1 C9 110.47(11) . . ?
N1 C1 H1 124.8 . . ?
C9 C1 H1 124.8 . . ?
N1 C2 N3 110.89(10) . . ?
N1 C2 C3 124.32(10) . . ?
N3 C2 C3 124.78(10) . . ?
N2 C3 C2 118.44(10) . . ?
N2 C3 H8 120.8 . . ?
C2 C3 H8 120.8 . . ?
C10 C4 C5 119.05(10) . . ?
C10 C4 N2 126.97(10) . . ?
C5 C4 N2 113.98(10) . . ?
O1 C5 C6 118.31(10) . . ?
O1 C5 C4 121.22(10) . . ?
C6 C5 C4 120.45(11) . . ?
C7 C6 C5 119.70(11) . . ?
C7 C6 H11 120.1 . . ?
C5 C6 H11 120.1 . . ?
C6 C7 C11 120.45(11) . . ?
C6 C7 H2 119.8 . . ?
C11 C7 H2 119.8 . . ?
N3 C8 H6 109.5 . . ?
N3 C8 H5 109.5 . . ?
H6 C8 H5 109.5 . . ?
N3 C8 H4 109.5 . . ?
H6 C8 H4 109.5 . . ?
H5 C8 H4 109.5 . . ?
C1 C9 N3 106.10(11) . . ?
C1 C9 H7 126.9 . . ?
N3 C9 H7 126.9 . . ?
C11 C10 C4 120.27(11) . . ?
C11 C10 H10 119.9 . . ?
C4 C10 H10 119.9 . . ?
C10 C11 C7 120.03(11) . . ?
C10 C11 H9 120.0 . . ?
C7 C11 H9 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
C2 N1 C1 C9 0.39(15) . . . . ?
C1 N1 C2 N3 0.06(14) . . . . ?
C1 N1 C2 C3 179.00(12) . . . . ?
C9 N3 C2 N1 -0.48(14) . . . . ?
C8 N3 C2 N1 -177.05(11) . . . . ?
C9 N3 C2 C3 -179.41(11) . . . . ?
C8 N3 C2 C3 4.0(2) . . . . ?
C4 N2 C3 C2 -178.52(11) . . . . ?
N1 C2 C3 N2 7.07(19) . . . . ?
N3 C2 C3 N2 -174.13(11) . . . . ?
C3 N2 C4 C10 -12.0(2) . . . . ?
C3 N2 C4 C5 167.63(11) . . . . ?
C10 C4 C5 O1 -179.55(11) . . . . ?
N2 C4 C5 O1 0.77(16) . . . . ?
C10 C4 C5 C6 2.20(18) . . . . ?
N2 C4 C5 C6 -177.48(11) . . . . ?
O1 C5 C6 C7 -179.44(11) . . . . ?
C4 C5 C6 C7 -1.14(18) . . . . ?
C5 C6 C7 C11 -0.78(19) . . . . ?
N1 C1 C9 N3 -0.68(15) . . . . ?
C2 N3 C9 C1 0.69(14) . . . . ?
C8 N3 C9 C1 177.40(11) . . . . ?
C5 C4 C10 C11 -1.36(18) . . . . ?
N2 C4 C10 C11 178.28(12) . . . . ?
C4 C10 C11 C7 -0.53(19) . . . . ?
C6 C7 C11 C10 1.6(2) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.053

