# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_izact+C6
_database_code_depnum_ccdc_archive 'CCDC 2290718'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2023-11-03 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_date             2023-05-04T09:46:14-00:00
_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         'C9  H11  N3  O, C3 H5 O2'
_chemical_formula_sum            'C12 H16 N3 O3'
_chemical_formula_weight         250.28

#----------------------------------------------------------------------------#
#                   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                   19.0668(10)
_cell_length_b                   8.1886(4)
_cell_length_c                   8.0487(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.561(3)
_cell_angle_gamma                90
_cell_volume                     1256.18(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2711
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.89
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.55
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532

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

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_number            11423
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3034
_reflns_number_gt                2189
_reflns_threshold_expression     'I > 2σ(I)'

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


_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

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

_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)+(0.0508P)²+0.4420P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   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 0.27067(8) 0.05082(19) 0.06307(18) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.22998(8) 0.16021(19) 0.14915(18) 0.0264(3) Uani 1 1 d . . . . .
H2 H 0.232094 0.27392 0.126423 0.032 Uiso 1 1 calc R U . . .
C3 C 0.18612(8) 0.1004(2) 0.26912(19) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.157817 0.175806 0.326873 0.034 Uiso 1 1 calc R U . . .
C4 C 0.22068(9) -0.1627(2) 0.2233(2) 0.0329(4) Uani 1 1 d . . . . .
H4 H 0.217786 -0.275674 0.24898 0.04 Uiso 1 1 calc R U . . .
C5 C 0.26512(8) -0.1138(2) 0.1002(2) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.291613 -0.192133 0.041607 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31860(8) 0.1015(2) -0.07289(19) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.39667(12) 0.5758(2) -0.0500(2) 0.0492(5) Uani 1 1 d . . . . .
H7A H 0.354938 0.540952 0.008994 0.074 Uiso 1 1 calc R U . . .
H7B H 0.386397 0.677181 -0.110527 0.074 Uiso 1 1 calc R U . . .
H7C H 0.435429 0.59429 0.030262 0.074 Uiso 1 1 calc R U . . .
C8 C 0.41678(8) 0.4465(2) -0.16943(19) 0.0311(4) Uani 1 1 d . . . . .
C9 C 0.46492(10) 0.4952(2) -0.3050(2) 0.0420(4) Uani 1 1 d . . . . .
H9A H 0.476801 0.398841 -0.370696 0.063 Uiso 1 1 calc R U . . .
H9B H 0.507892 0.542599 -0.255897 0.063 Uiso 1 1 calc R U . . .
H9C H 0.441535 0.576155 -0.377128 0.063 Uiso 1 1 calc R U . . .
C10 C 0.08725(9) -0.04476(18) 0.6717(2) 0.0292(4) Uani 1 1 d . . . . .
C11 C 0.02561(8) -0.0691(2) 0.78040(19) 0.0300(4) Uani 1 1 d . . . . .
H11A H 0.019119 -0.187684 0.798484 0.036 Uiso 1 1 calc R U . . .
H11B H -0.016977 -0.02776 0.721166 0.036 Uiso 1 1 calc R U . . .
C12 C 0.03204(8) 0.0146(2) 0.9482(2) 0.0292(4) Uani 1 1 d . . . . .
H12A H 0.038179 0.133441 0.931411 0.035 Uiso 1 1 calc R U . . .
H12B H 0.074211 -0.026961 1.008986 0.035 Uiso 1 1 calc R U . . .
N1 N 0.34901(7) 0.24933(17) -0.05292(16) 0.0286(3) Uani 1 1 d . . . . .
N2 N 0.18147(7) -0.05738(17) 0.30794(16) 0.0299(3) Uani 1 1 d . . . . .
N3 N 0.39528(7) 0.29874(17) -0.17364(16) 0.0314(3) Uani 1 1 d . . . . .
O1 O 0.32772(7) 0.01399(16) -0.19350(16) 0.0462(4) Uani 1 1 d . . . . .
O2 O 0.08185(6) -0.12682(15) 0.53056(14) 0.0368(3) Uani 1 1 d . . . . .
O3 O 0.13790(7) 0.03746(17) 0.70891(18) 0.0532(4) Uani 1 1 d . . . . .
H1 H 0.3483(10) 0.300(3) 0.043(3) 0.049(6) Uiso 1 1 d . . . . .
H2A H 0.1168(12) -0.104(3) 0.462(3) 0.055(6) 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 C2 1.383(2) . ?
C1 C5 1.385(2) . ?
C1 C6 1.503(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.95 . ?
C3 N2 1.333(2) . ?
C3 H3 0.95 . ?
C4 N2 1.340(2) . ?
C4 C5 1.380(2) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 O1 1.2230(19) . ?
C6 N1 1.350(2) . ?
C7 C8 1.487(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 N3 1.278(2) . ?
C8 C9 1.499(2) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O3 1.208(2) . ?
C10 O2 1.3217(19) . ?
C10 C11 1.497(2) . ?
C11 C12 1.517(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C12 1.517(3) 3_557 ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
N1 N3 1.3902(17) . ?
N1 H1 0.88(2) . ?
O2 H2A 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 118.34(14) . . ?
C2 C1 C6 123.10(14) . . ?
C5 C1 C6 118.52(14) . . ?
C1 C2 C3 118.55(15) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
N2 C3 C2 123.51(15) . . ?
N2 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N2 C4 C5 122.70(15) . . ?
N2 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C1 119.30(15) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
O1 C6 N1 123.38(15) . . ?
O1 C6 C1 121.23(15) . . ?
N1 C6 C1 115.39(13) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C7 127.08(15) . . ?
N3 C8 C9 115.79(15) . . ?
C7 C8 C9 117.06(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 122.64(15) . . ?
O3 C10 C11 124.36(15) . . ?
O2 C10 C11 112.97(14) . . ?
C10 C11 C12 114.47(13) . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C12 111.81(17) . 3_557 ?
C11 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 3_557 . ?
C11 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 3_557 . ?
H12A C12 H12B 107.9 . . ?
C6 N1 N3 117.16(13) . . ?
C6 N1 H1 120.6(13) . . ?
N3 N1 H1 120.3(13) . . ?
C3 N2 C4 117.59(13) . . ?
C8 N3 N1 117.79(14) . . ?
C10 O2 H2A 112.2(14) . . ?

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
C5 C1 C2 C3 0.5(2) . . . . ?
C6 C1 C2 C3 178.25(14) . . . . ?
C1 C2 C3 N2 0.8(2) . . . . ?
N2 C4 C5 C1 1.0(3) . . . . ?
C2 C1 C5 C4 -1.4(2) . . . . ?
C6 C1 C5 C4 -179.19(14) . . . . ?
C2 C1 C6 O1 -145.14(17) . . . . ?
C5 C1 C6 O1 32.6(2) . . . . ?
C2 C1 C6 N1 33.7(2) . . . . ?
C5 C1 C6 N1 -148.54(15) . . . . ?
O3 C10 C11 C12 -1.9(2) . . . . ?
O2 C10 C11 C12 176.31(14) . . . . ?
C10 C11 C12 C12 179.89(16) . . . 3_557 ?
O1 C6 N1 N3 -2.9(2) . . . . ?
C1 C6 N1 N3 178.22(13) . . . . ?
C2 C3 N2 C4 -1.3(2) . . . . ?
C5 C4 N2 C3 0.4(2) . . . . ?
C7 C8 N3 N1 -1.3(3) . . . . ?
C9 C8 N3 N1 -178.30(14) . . . . ?
C6 N1 N3 C8 170.35(15) . . . . ?

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 O3 0.95 2.47 3.080(2) 121.7 4_565 yes
C3 H3 O3 0.95 2.56 3.139(2) 119.7 4_565 yes
C4 H4 O3 0.95 2.64 3.451(2) 143.1 4 yes
C7 H7A O1 0.98 2.5 3.272(2) 135 4_566 yes
N1 H1 N3 0.88(2) 2.56(2) 3.1789(19) 128.7(17) 4_566 yes
N1 H1 O1 0.88(2) 2.65(2) 3.515(2) 169.3(18) 4_566 yes
O2 H2A N2 0.89(2) 1.82(2) 2.7069(17) 175(2) . yes



# END of CIF
####################################################################### 
# 
# 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_izact+C7
_database_code_depnum_ccdc_archive 'CCDC 2290719'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2023-11-03 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_date             2022-10-21T12:47:36-00:00
_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_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C9 H11 N3 O), C7 H12 O4'
_chemical_formula_sum            'C25 H34 N6 O6'
_chemical_formula_weight         514.58

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                   47.130(4)
_cell_length_b                   5.0755(4)
_cell_length_c                   23.567(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.352(2)
_cell_angle_gamma                90
_cell_volume                     5250.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      28.16
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
        wR2(int) was 0.0801 before and 0.0755 after correction.
        The Ratio of minimum to maximum transmission is 0.9275.
        The λ/2 correction factor is Not present.
;
_exptl_absorpt_correction_T_min  0.6895
_exptl_absorpt_correction_T_max  0.7457

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

_diffrn_ambient_temperature      173.15
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_number            50090
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.726
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             6309
_reflns_number_gt                5014
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0115P)²+42.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6309
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.1988
_refine_ls_wR_factor_gt          0.1916
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   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
C1A C 0.16604(7) 0.2941(7) -0.02203(15) 0.0208(7) Uani 1 1 d . . . . .
C2A C 0.17811(7) 0.0806(7) -0.04220(16) 0.0247(7) Uani 1 1 d . . . . .
H2A H 0.16594 -0.017756 -0.076802 0.03 Uiso 1 1 calc R U . . .
C3A C 0.20835(8) 0.0133(7) -0.01078(17) 0.0282(8) Uani 1 1 d . . . . .
H3A H 0.216715 -0.131363 -0.025005 0.034 Uiso 1 1 calc R U . . .
C4A C 0.21444(8) 0.3484(8) 0.05753(16) 0.0282(8) Uani 1 1 d . . . . .
H4A H 0.227186 0.441975 0.09241 0.034 Uiso 1 1 calc R U . . .
C5A C 0.18464(7) 0.4320(7) 0.02901(16) 0.0249(7) Uani 1 1 d . . . . .
H5A H 0.177079 0.57968 0.043888 0.03 Uiso 1 1 calc R U . . .
C6A C 0.13418(7) 0.3931(7) -0.05441(15) 0.0202(6) Uani 1 1 d . . . . .
C7A C 0.07513(9) -0.1060(8) -0.17457(17) 0.0333(9) Uani 1 1 d . . . . .
H7AA H 0.09586 -0.083208 -0.174091 0.05 Uiso 1 1 calc R U . . .
H7AB H 0.061122 -0.136699 -0.216473 0.05 Uiso 1 1 calc R U . . .
H7AC H 0.074582 -0.257329 -0.14916 0.05 Uiso 1 1 calc R U . . .
C8A C 0.06578(8) 0.1344(7) -0.15040(15) 0.0240(7) Uani 1 1 d . . . . .
C9A C 0.03307(8) 0.2151(9) -0.17833(19) 0.0371(9) Uani 1 1 d . . . . .
H9AA H 0.030094 0.382208 -0.160408 0.056 Uiso 1 1 calc R U . . .
H9AB H 0.020202 0.079027 -0.170497 0.056 Uiso 1 1 calc R U . . .
H9AC H 0.027481 0.236958 -0.222385 0.056 Uiso 1 1 calc R U . . .
C1B C 0.58801(7) 0.6198(7) 0.53696(14) 0.0193(6) Uani 1 1 d . . . . .
C2B C 0.57646(7) 0.4045(7) 0.55752(16) 0.0222(7) Uani 1 1 d . . . . .
H2B H 0.588688 0.311481 0.592967 0.027 Uiso 1 1 calc R U . . .
C3B C 0.54661(8) 0.3273(7) 0.52520(16) 0.0256(7) Uani 1 1 d . . . . .
H3B H 0.53864 0.181473 0.539842 0.031 Uiso 1 1 calc R U . . .
C4B C 0.53988(8) 0.6592(7) 0.45590(16) 0.0264(7) Uani 1 1 d . . . . .
H4B H 0.527055 0.749045 0.420487 0.032 Uiso 1 1 calc R U . . .
C5B C 0.56912(8) 0.7531(7) 0.48525(15) 0.0236(7) Uani 1 1 d . . . . .
H5B H 0.576157 0.904374 0.470597 0.028 Uiso 1 1 calc R U . . .
C6B C 0.61964(7) 0.7230(7) 0.56911(15) 0.0199(6) Uani 1 1 d . . . . .
C7B C 0.68041(9) 0.2320(8) 0.68869(18) 0.0348(9) Uani 1 1 d . . . . .
H7BA H 0.661109 0.261458 0.694553 0.052 Uiso 1 1 calc R U . . .
H7BB H 0.696308 0.187387 0.727826 0.052 Uiso 1 1 calc R U . . .
H7BC H 0.678014 0.086769 0.659912 0.052 Uiso 1 1 calc R U . . .
C8B C 0.68923(8) 0.4763(7) 0.66398(16) 0.0247(7) Uani 1 1 d . . . . .
C9B C 0.72188(8) 0.5627(8) 0.69123(18) 0.0347(9) Uani 1 1 d . . . . .
H9BA H 0.724691 0.72304 0.670705 0.052 Uiso 1 1 calc R U . . .
H9BB H 0.735076 0.422961 0.686039 0.052 Uiso 1 1 calc R U . . .
H9BC H 0.727186 0.598591 0.734741 0.052 Uiso 1 1 calc R U . . .
N1B N 0.64089(6) 0.5380(6) 0.59583(13) 0.0232(6) Uani 1 1 d . . . . .
H1B H 0.63594 0.371341 0.596833 0.028 Uiso 1 1 calc R U . . .
N2B N 0.52866(6) 0.4478(6) 0.47478(13) 0.0250(6) Uani 1 1 d . . . . .
N3B N 0.67135(6) 0.6234(6) 0.62203(14) 0.0253(6) Uani 1 1 d . . . . .
O1B O 0.62506(5) 0.9599(5) 0.57149(12) 0.0272(6) Uani 1 1 d . . . . .
C10 C 0.29771(8) 0.1062(7) 0.14545(16) 0.0259(7) Uani 1 1 d . . . . .
C11 C 0.32970(7) 0.0036(8) 0.17299(15) 0.0259(7) Uani 1 1 d . . . . .
H11A H 0.337869 -0.01937 0.140103 0.031 Uiso 1 1 calc R U . . .
H11B H 0.329123 -0.172348 0.190671 0.031 Uiso 1 1 calc R U . . .
C12 C 0.35154(7) 0.1781(8) 0.22227(16) 0.0267(7) Uani 1 1 d . . . . .
H12A H 0.352473 0.354276 0.20502 0.032 Uiso 1 1 calc R U . . .
H12B H 0.343756 0.200478 0.255742 0.032 Uiso 1 1 calc R U . . .
C13 C 0.38333(8) 0.0607(8) 0.24760(16) 0.0279(8) Uani 1 1 d . . . . .
H13A H 0.390609 0.032828 0.213596 0.034 Uiso 1 1 calc R U . . .
H13B H 0.382226 -0.113843 0.265432 0.034 Uiso 1 1 calc R U . . .
C14 C 0.40645(7) 0.2297(7) 0.29589(16) 0.0258(7) Uani 1 1 d . . . . .
H14A H 0.39944 0.257598 0.330253 0.031 Uiso 1 1 calc R U . . .
H14B H 0.407892 0.404148 0.27832 0.031 Uiso 1 1 calc R U . . .
C15 C 0.43777(8) 0.1012(8) 0.31946(19) 0.0359(9) Uani 1 1 d . . . . .
H15A H 0.437137 -0.054945 0.344154 0.043 Uiso 1 1 calc R U . . .
H15B H 0.442762 0.03934 0.284346 0.043 Uiso 1 1 calc R U . . .
C16 C 0.46264(8) 0.2842(7) 0.35768(17) 0.0260(7) Uani 1 1 d . . . . .
N1A N 0.11340(6) 0.2043(6) -0.08097(13) 0.0227(6) Uani 1 1 d . . . . .
H1A H 0.118773 0.038327 -0.081136 0.027 Uiso 1 1 calc R U . . .
N2A N 0.22607(6) 0.1426(6) 0.03829(14) 0.0268(6) Uani 1 1 d . . . . .
N3A N 0.08291(6) 0.2835(6) -0.10832(13) 0.0245(6) Uani 1 1 d . . . . .
O1A O 0.12849(5) 0.6276(5) -0.05730(12) 0.0275(6) Uani 1 1 d . . . . .
O2 O 0.28182(6) -0.0242(6) 0.09593(12) 0.0362(7) Uani 1 1 d . . . . .
H2 H 0.264082 0.037397 0.08151 0.054 Uiso 1 1 calc R U . . .
O3 O 0.28764(6) 0.2849(7) 0.16622(14) 0.0469(8) Uani 1 1 d . . . . .
O4 O 0.47927(6) 0.1821(5) 0.41117(11) 0.0304(6) Uani 1 1 d . . . . .
H4 H 0.492748 0.290568 0.430722 0.046 Uiso 1 1 calc R U . . .
O5 O 0.46725(6) 0.4969(6) 0.34046(13) 0.0368(7) Uani 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
C1A C2A 1.386(5) . ?
C1A C5A 1.392(5) . ?
C1A C6A 1.501(4) . ?
C2A H2A 0.95 . ?
C2A C3A 1.389(5) . ?
C3A H3A 0.95 . ?
C3A N2A 1.327(5) . ?
C4A H4A 0.95 . ?
C4A C5A 1.385(5) . ?
C4A N2A 1.334(5) . ?
C5A H5A 0.95 . ?
C6A N1A 1.350(4) . ?
C6A O1A 1.216(4) . ?
C7A H7AA 0.98 . ?
C7A H7AB 0.98 . ?
C7A H7AC 0.98 . ?
C7A C8A 1.480(5) . ?
C8A C9A 1.497(5) . ?
C8A N3A 1.274(4) . ?
C9A H9AA 0.98 . ?
C9A H9AB 0.98 . ?
C9A H9AC 0.98 . ?
C1B C2B 1.385(5) . ?
C1B C5B 1.395(5) . ?
C1B C6B 1.499(4) . ?
C2B H2B 0.95 . ?
C2B C3B 1.390(5) . ?
C3B H3B 0.95 . ?
C3B N2B 1.330(5) . ?
C4B H4B 0.95 . ?
C4B C5B 1.382(5) . ?
C4B N2B 1.342(5) . ?
C5B H5B 0.95 . ?
C6B N1B 1.350(4) . ?
C6B O1B 1.227(4) . ?
C7B H7BA 0.98 . ?
C7B H7BB 0.98 . ?
C7B H7BC 0.98 . ?
C7B C8B 1.492(5) . ?
C8B C9B 1.501(5) . ?
C8B N3B 1.280(5) . ?
C9B H9BA 0.98 . ?
C9B H9BB 0.98 . ?
C9B H9BC 0.98 . ?
N1B H1B 0.88 . ?
N1B N3B 1.409(4) . ?
C10 C11 1.501(5) . ?
C10 O2 1.313(4) . ?
C10 O3 1.207(5) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 C12 1.524(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 C13 1.518(5) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C14 1.522(5) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C14 C15 1.522(5) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C15 C16 1.510(5) . ?
C16 O4 1.324(4) . ?
C16 O5 1.201(5) . ?
N1A H1A 0.88 . ?
N1A N3A 1.403(4) . ?
O2 H2 0.84 . ?
O4 H4 0.84 . ?

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
C2A C1A C5A 118.8(3) . . ?
C2A C1A C6A 123.1(3) . . ?
C5A C1A C6A 118.0(3) . . ?
C1A C2A H2A 120.7 . . ?
C1A C2A C3A 118.6(3) . . ?
C3A C2A H2A 120.7 . . ?
C2A C3A H3A 118.6 . . ?
N2A C3A C2A 122.7(3) . . ?
N2A C3A H3A 118.6 . . ?
C5A C4A H4A 118.5 . . ?
N2A C4A H4A 118.5 . . ?
N2A C4A C5A 123.0(3) . . ?
C1A C5A H5A 120.9 . . ?
C4A C5A C1A 118.3(3) . . ?
C4A C5A H5A 120.9 . . ?
N1A C6A C1A 114.9(3) . . ?
O1A C6A C1A 121.0(3) . . ?
O1A C6A N1A 124.1(3) . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C8A C7A H7AA 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
C8A C7A H7AC 109.5 . . ?
C7A C8A C9A 117.4(3) . . ?
N3A C8A C7A 126.6(3) . . ?
N3A C8A C9A 116.0(3) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C2B C1B C5B 118.8(3) . . ?
C2B C1B C6B 123.0(3) . . ?
C5B C1B C6B 118.2(3) . . ?
C1B C2B H2B 120.7 . . ?
C1B C2B C3B 118.6(3) . . ?
C3B C2B H2B 120.7 . . ?
C2B C3B H3B 118.4 . . ?
N2B C3B C2B 123.2(3) . . ?
N2B C3B H3B 118.4 . . ?
C5B C4B H4B 118.3 . . ?
N2B C4B H4B 118.3 . . ?
N2B C4B C5B 123.4(3) . . ?
C1B C5B H5B 120.9 . . ?
C4B C5B C1B 118.2(3) . . ?
C4B C5B H5B 120.9 . . ?
N1B C6B C1B 115.2(3) . . ?
O1B C6B C1B 121.2(3) . . ?
O1B C6B N1B 123.6(3) . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C8B C7B H7BA 109.5 . . ?
C8B C7B H7BB 109.5 . . ?
C8B C7B H7BC 109.5 . . ?
C7B C8B C9B 117.6(3) . . ?
N3B C8B C7B 126.0(3) . . ?
N3B C8B C9B 116.3(3) . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C6B N1B H1B 121.5 . . ?
C6B N1B N3B 117.1(3) . . ?
N3B N1B H1B 121.5 . . ?
C3B N2B C4B 117.7(3) . . ?
C8B N3B N1B 116.0(3) . . ?
O2 C10 C11 111.6(3) . . ?
O3 C10 C11 124.5(3) . . ?
O3 C10 O2 123.9(3) . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C10 C11 C12 114.9(3) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108 . . ?
C13 C12 C11 111.6(3) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C12 C13 C14 114.1(3) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C13 C14 C15 111.5(3) . . ?
H14A C14 H14B 108 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 113.1(3) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
O4 C16 C15 112.9(3) . . ?
O5 C16 C15 123.2(3) . . ?
O5 C16 O4 123.8(3) . . ?
C6A N1A H1A 121.4 . . ?
C6A N1A N3A 117.3(3) . . ?
N3A N1A H1A 121.4 . . ?
C3A N2A C4A 118.5(3) . . ?
C8A N3A N1A 116.1(3) . . ?
C10 O2 H2 109.5 . . ?
C16 O4 H4 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
C1A C2A C3A N2A 1.0(6) . . . . ?
C1A C6A N1A N3A 175.8(3) . . . . ?
C2A C1A C5A C4A -0.2(5) . . . . ?
C2A C1A C6A N1A 34.7(5) . . . . ?
C2A C1A C6A O1A -143.1(4) . . . . ?
C2A C3A N2A C4A -1.2(6) . . . . ?
C5A C1A C2A C3A -0.3(5) . . . . ?
C5A C1A C6A N1A -148.4(3) . . . . ?
C5A C1A C6A O1A 33.8(5) . . . . ?
C5A C4A N2A C3A 0.6(6) . . . . ?
C6A C1A C2A C3A 176.6(3) . . . . ?
C6A C1A C5A C4A -177.3(3) . . . . ?
C6A N1A N3A C8A 155.7(3) . . . . ?
C7A C8A N3A N1A -2.5(5) . . . . ?
C9A C8A N3A N1A 178.4(3) . . . . ?
C1B C2B C3B N2B 1.1(5) . . . . ?
C1B C6B N1B N3B 174.7(3) . . . . ?
C2B C1B C5B C4B -1.7(5) . . . . ?
C2B C1B C6B N1B 34.7(4) . . . . ?
C2B C1B C6B O1B -143.6(4) . . . . ?
C2B C3B N2B C4B -2.3(5) . . . . ?
C5B C1B C2B C3B 1.0(5) . . . . ?
C5B C1B C6B N1B -147.6(3) . . . . ?
C5B C1B C6B O1B 34.0(5) . . . . ?
C5B C4B N2B C3B 1.5(5) . . . . ?
C6B C1B C2B C3B 178.6(3) . . . . ?
C6B C1B C5B C4B -179.5(3) . . . . ?
C6B N1B N3B C8B 156.6(3) . . . . ?
C7B C8B N3B N1B -2.5(5) . . . . ?
C9B C8B N3B N1B 178.7(3) . . . . ?
N2B C4B C5B C1B 0.5(5) . . . . ?
O1B C6B N1B N3B -7.0(5) . . . . ?
C10 C11 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 C14 178.4(3) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C13 C14 C15 C16 168.4(3) . . . . ?
C14 C15 C16 O4 128.0(4) . . . . ?
C14 C15 C16 O5 -53.9(5) . . . . ?
N2A C4A C5A C1A 0.1(6) . . . . ?
O1A C6A N1A N3A -6.6(5) . . . . ?
O2 C10 C11 C12 167.6(3) . . . . ?
O3 C10 C11 C12 -12.9(6) . . . . ?

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
C4A H4A O3 0.95 2.86 3.483(4) 124.3 . yes
C4B H4B O5 0.95 3.04 3.608(4) 119.5 . yes
N1B H1B O1B 0.88 2.18 3.030(4) 162 1_545 yes
N1A H1A O1A 0.88 2.16 3.016(4) 162.7 1_545 yes
O2 H2 N2A 0.84 1.79 2.620(4) 169.7 . yes
O4 H4 N2B 0.84 1.82 2.635(4) 164.3 . yes



# END of CIF
####################################################################### 
# 
# 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_izact+C8
_database_code_depnum_ccdc_archive 'CCDC 2290720'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_date             2023-03-17T10:02:45-00:00
_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         'C9 H11 N3 O, C4 H7 O2'
_chemical_formula_sum            'C13 H18 N3 O3'
_chemical_formula_weight         264.3

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                   19.888(4)
_cell_length_b                   8.2744(15)
_cell_length_c                   8.3942(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.316(6)
_cell_angle_gamma                90
_cell_volume                     1373.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    3295
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.59
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.082
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.168
-1 -1 -1 0.159
1 1 -1 0.095
1 -1 0 0.054
-1 1 0 0.032
1 1 0 0.003
1 0 0 0.019
-1 0 0 0.041
0 0 1 0.087
1 1 1 0.048
-1 -1 1 0.106


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

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
        wR2(int) was 0.1306 before and 0.0744 after correction.
        The Ratio of minimum to maximum transmission is 0.7720.
        The λ/2 correction factor is Not present.
;
_exptl_absorpt_correction_T_min  0.5757
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.992

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

_diffrn_ambient_temperature      173
_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  0.1042
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_number            27737
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_Friedel_coverage         0
_reflns_number_total             3282
_reflns_number_gt                1969
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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)+(0.0747P)²+0.5847P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.010(3)
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1913
_refine_ls_wR_factor_gt          0.1659
_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
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   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 0.29447(12) 0.3995(3) 0.8104(3) 0.0391(6) Uani 1 1 d . . . . .
H1 H 0.321784 0.32231 0.763836 0.047 Uiso 1 1 calc R U . . .
C2 C 0.25433(12) 0.3464(3) 0.9240(3) 0.0367(5) Uani 1 1 d . . . . .
H2 H 0.253395 0.235483 0.953013 0.044 Uiso 1 1 calc R U . . .
C3 C 0.21537(11) 0.4594(3) 0.9946(3) 0.0363(5) Uani 1 1 d . . . . .
C4 C 0.21911(12) 0.6188(3) 0.9476(3) 0.0412(6) Uani 1 1 d . . . . .
H4 H 0.193692 0.699382 0.995008 0.049 Uiso 1 1 calc R U . . .
C5 C 0.25982(13) 0.6605(3) 0.8317(3) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.261394 0.770486 0.799856 0.052 Uiso 1 1 calc R U . . .
C6 C 0.17065(12) 0.4153(3) 1.1204(3) 0.0399(6) Uani 1 1 d . . . . .
C7 C 0.07830(12) 0.0709(3) 1.1983(3) 0.0414(6) Uani 1 1 d . . . . .
C8 C 0.09487(16) -0.0516(4) 1.0775(4) 0.0580(8) Uani 1 1 d . . . . .
H8A H 0.080016 -0.011712 0.969393 0.087 Uiso 1 1 calc R U . . .
H8B H 0.071606 -0.153242 1.095619 0.087 Uiso 1 1 calc R U . . .
H8C H 0.143833 -0.069988 1.088313 0.087 Uiso 1 1 calc R U . . .
C9 C 0.03337(14) 0.0156(3) 1.3201(4) 0.0515(7) Uani 1 1 d . . . . .
H9A H 0.05541 -0.072911 1.383511 0.077 Uiso 1 1 calc R U . . .
H9B H -0.009812 -0.022157 1.265252 0.077 Uiso 1 1 calc R U . . .
H9C H 0.025193 0.105828 1.391147 0.077 Uiso 1 1 calc R U . . .
C10 C 0.38285(13) 0.5473(3) 0.4189(3) 0.0406(6) Uani 1 1 d . . . . .
C11 C 0.43928(13) 0.5889(3) 0.3227(3) 0.0418(6) Uani 1 1 d . . . . .
H11A H 0.482755 0.567164 0.388544 0.05 Uiso 1 1 calc R U . . .
H11B H 0.437342 0.706121 0.299197 0.05 Uiso 1 1 calc R U . . .
C12 C 0.43859(13) 0.4976(3) 0.1657(3) 0.0435(6) Uani 1 1 d . . . . .
H12A H 0.396782 0.524208 0.095467 0.052 Uiso 1 1 calc R U . . .
H12B H 0.438612 0.379891 0.187 0.052 Uiso 1 1 calc R U . . .
C13 C 0.49987(13) 0.5412(3) 0.0813(3) 0.0425(6) Uani 1 1 d . . . . .
H13A H 0.541395 0.510227 0.150546 0.051 Uiso 1 1 calc R U . . .
H13B H 0.500882 0.659773 0.066016 0.051 Uiso 1 1 calc R U . . .
N1 N 0.29720(10) 0.5529(2) 0.7621(3) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.14329(10) 0.2657(2) 1.1032(3) 0.0391(5) Uani 1 1 d . . . . .
H2A H 0.152284 0.202308 1.024095 0.047 Uiso 1 1 calc R U . . .
N3 N 0.10063(10) 0.2147(3) 1.2138(3) 0.0409(5) Uani 1 1 d . . . . .
O1 O 0.16053(11) 0.5083(2) 1.2278(3) 0.0618(6) Uani 1 1 d . . . . .
O2 O 0.38881(9) 0.6205(2) 0.5592(2) 0.0541(5) Uani 1 1 d . . . . .
H2B H 0.354422 0.601438 0.605955 0.081 Uiso 1 1 calc R U . . .
O3 O 0.33552(11) 0.4622(3) 0.3733(3) 0.0701(7) Uani 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 H1 0.95 . ?
C1 C2 1.381(3) . ?
C1 N1 1.335(3) . ?
C2 H2 0.95 . ?
C2 C3 1.389(3) . ?
C3 C4 1.381(3) . ?
C3 C6 1.499(3) . ?
C4 H4 0.95 . ?
C4 C5 1.376(3) . ?
C5 H5 0.95 . ?
C5 N1 1.335(3) . ?
C6 N2 1.353(3) . ?
C6 O1 1.219(3) . ?
C7 C8 1.496(4) . ?
C7 C9 1.502(3) . ?
C7 N3 1.272(3) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.493(3) . ?
C10 O2 1.318(3) . ?
C10 O3 1.204(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 C12 1.517(4) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 C13 1.519(3) . ?
C13 C13 1.526(5) 3_665 ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
N2 H2A 0.88 . ?
N2 N3 1.390(3) . ?
O2 H2B 0.84 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118 . . ?
N1 C1 H1 118 . . ?
N1 C1 C2 123.9(2) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C6 122.6(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 C6 119.3(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 118.6 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 H5 118.6 . . ?
N2 C6 C3 114.2(2) . . ?
O1 C6 C3 121.8(2) . . ?
O1 C6 N2 124.0(2) . . ?
C8 C7 C9 116.6(2) . . ?
N3 C7 C8 127.1(2) . . ?
N3 C7 C9 116.3(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 112.2(2) . . ?
O3 C10 C11 124.8(3) . . ?
O3 C10 O2 122.9(2) . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C10 C11 C12 114.8(2) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 C13 110.8(2) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C12 C13 C13 113.1(3) . 3_665 ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C13 C13 H13A 108.9 3_665 . ?
C13 C13 H13B 108.9 3_665 . ?
H13A C13 H13B 107.8 . . ?
C1 N1 C5 117.2(2) . . ?
C6 N2 H2A 120.9 . . ?
C6 N2 N3 118.3(2) . . ?
N3 N2 H2A 120.9 . . ?
C7 N3 N2 116.6(2) . . ?
C10 O2 H2B 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 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C6 -179.3(3) . . . . ?
C2 C1 N1 C5 1.7(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C6 N2 -32.7(4) . . . . ?
C2 C3 C6 O1 147.3(3) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C6 N2 N3 -179.5(2) . . . . ?
C4 C3 C6 N2 148.2(2) . . . . ?
C4 C3 C6 O1 -31.8(4) . . . . ?
C4 C5 N1 C1 -0.7(4) . . . . ?
C6 C3 C4 C5 -179.7(3) . . . . ?
C6 N2 N3 C7 -176.9(2) . . . . ?
C8 C7 N3 N2 2.3(4) . . . . ?
C9 C7 N3 N2 178.8(2) . . . . ?
C10 C11 C12 C13 -176.9(2) . . . . ?
C11 C12 C13 C13 -177.3(3) . . . 3_665 ?
N1 C1 C2 C3 -1.3(4) . . . . ?
O1 C6 N2 N3 0.5(4) . . . . ?
O2 C10 C11 C12 175.1(2) . . . . ?
O3 C10 C11 C12 -7.7(4) . . . . ?

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
C1 H1 O3 0.95 2.53 3.132(3) 121.3 4_566 yes
C2 H2 O3 0.95 2.46 3.075(3) 122.7 4_566 yes
C11 H11B O2 0.99 2.57 3.346(3) 134.9 4_575 yes
O2 H2B N1 0.84 1.87 2.686(3) 163 . yes


####################################################################### 
# 
# 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_izact+C10
_database_code_depnum_ccdc_archive 'CCDC 2290722'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_date             2022-10-13T09:21:15-00:00
_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         'C10 H18 O4, 2(C9 H11 N3 O)'
_chemical_formula_sum            'C28 H40 N6 O6'
_chemical_formula_weight         556.66

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9554(4)
_cell_length_b                   13.7715(8)
_cell_length_c                   14.6005(8)
_cell_angle_alpha                72.874(3)
_cell_angle_beta                 75.014(3)
_cell_angle_gamma                84.453(3)
_cell_volume                     1476.32(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6961
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.25
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.136
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596

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

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.988

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

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_number            54935
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.504
_diffrn_reflns_theta_max         28.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             7371
_reflns_number_gt                5203
_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)+(0.0596P)²+0.4622P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7371
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.149
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   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 1.7013(2) 0.90863(15) 0.55391(14) 0.0419(4) Uani 1 1 d . . . . .
H1 H 1.666267 0.961307 0.503235 0.05 Uiso 1 1 calc R U . . .
C2 C 1.8191(2) 0.93101(14) 0.59945(14) 0.0377(4) Uani 1 1 d . . . . .
H2A H 1.865866 0.997008 0.579254 0.045 Uiso 1 1 calc R U . . .
C3 C 1.8675(2) 0.85521(13) 0.67517(12) 0.0301(3) Uani 1 1 d . . . . .
C4 C 1.8001(2) 0.75938(13) 0.69955(13) 0.0323(4) Uani 1 1 d . . . . .
H4A H 1.831315 0.705441 0.750564 0.039 Uiso 1 1 calc R U . . .
C5 C 1.6862(2) 0.74381(14) 0.64799(13) 0.0351(4) Uani 1 1 d . . . . .
H5 H 1.642877 0.677458 0.663799 0.042 Uiso 1 1 calc R U . . .
C6 C 1.9942(2) 0.87581(13) 0.72727(13) 0.0319(4) Uani 1 1 d . . . . .
C7 C 1.9793(2) 0.85281(13) 0.97445(13) 0.0319(4) Uani 1 1 d . . . . .
C8 C 2.0960(2) 0.87116(14) 1.03336(14) 0.0388(4) Uani 1 1 d . . . . .
H8A H 2.204034 0.90161 0.98848 0.058 Uiso 1 1 calc R U . . .
H8B H 2.123156 0.806451 1.078093 0.058 Uiso 1 1 calc R U . . .
H8C H 2.037032 0.917406 1.071969 0.058 Uiso 1 1 calc R U . . .
C9 C 1.7993(3) 0.81997(19) 1.03013(15) 0.0523(5) Uani 1 1 d . . . . .
H9A H 1.717578 0.87745 1.017368 0.078 Uiso 1 1 calc R U . . .
H9B H 1.79414 0.796249 1.100995 0.078 Uiso 1 1 calc R U . . .
H9C H 1.767888 0.764617 1.008634 0.078 Uiso 1 1 calc R U . . .
C10 C 1.2790(2) 0.75095(14) 0.49547(13) 0.0348(4) Uani 1 1 d . . . . .
C11 C 1.1461(2) 0.67645(14) 0.50283(13) 0.0347(4) Uani 1 1 d . . . . .
H11A H 1.072551 0.657472 0.571178 0.042 Uiso 1 1 calc R U . . .
H11B H 1.207465 0.614045 0.489849 0.042 Uiso 1 1 calc R U . . .
C12 C 1.0294(2) 0.71651(14) 0.43201(13) 0.0352(4) Uani 1 1 d . . . . .
H12A H 1.102808 0.740034 0.363958 0.042 Uiso 1 1 calc R U . . .
H12B H 0.96097 0.775823 0.448142 0.042 Uiso 1 1 calc R U . . .
C13 C 0.9049(2) 0.63728(14) 0.43568(13) 0.0347(4) Uani 1 1 d . . . . .
H13A H 0.973234 0.578603 0.418042 0.042 Uiso 1 1 calc R U . . .
H13B H 0.833075 0.61265 0.504008 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7855(2) 0.67877(14) 0.36594(13) 0.0356(4) Uani 1 1 d . . . . .
H14A H 0.714665 0.735854 0.385443 0.043 Uiso 1 1 calc R U . . .
H14B H 0.858128 0.706286 0.298267 0.043 Uiso 1 1 calc R U . . .
C15 C 0.6638(2) 0.60110(14) 0.36406(14) 0.0367(4) Uani 1 1 d . . . . .
H15A H 0.733392 0.542542 0.346963 0.044 Uiso 1 1 calc R U . . .
H15B H 0.5863 0.57587 0.430731 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5536(2) 0.64558(14) 0.28995(14) 0.0369(4) Uani 1 1 d . . . . .
H16A H 0.487929 0.705544 0.306322 0.044 Uiso 1 1 calc R U . . .
H16B H 0.632367 0.669702 0.223521 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4251(2) 0.57333(13) 0.28533(13) 0.0350(4) Uani 1 1 d . . . . .
H17A H 0.344936 0.548816 0.351263 0.042 Uiso 1 1 calc R U . . .
H17B H 0.489234 0.513684 0.267406 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3200(2) 0.62510(14) 0.20988(14) 0.0367(4) Uani 1 1 d . . . . .
H18A H 0.267432 0.688903 0.223946 0.044 Uiso 1 1 calc R U . . .
H18B H 0.400197 0.643509 0.143368 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1780(2) 0.56158(13) 0.20859(13) 0.0351(4) Uani 1 1 d . . . . .
C20 C -0.2206(2) 0.50531(14) 0.05912(14) 0.0367(4) Uani 1 1 d . . . . .
H20 H -0.202245 0.568676 0.009722 0.044 Uiso 1 1 calc R U . . .
C21 C -0.3217(2) 0.43489(13) 0.04909(13) 0.0338(4) Uani 1 1 d . . . . .
H21 H -0.37245 0.450066 -0.00585 0.041 Uiso 1 1 calc R U . . .
C22 C -0.3484(2) 0.34158(12) 0.12028(12) 0.0297(3) Uani 1 1 d . . . . .
C23 C -0.2731(2) 0.32345(13) 0.19959(13) 0.0320(4) Uani 1 1 d . . . . .
H23 H -0.28867 0.260631 0.249885 0.038 Uiso 1 1 calc R U . . .
C24 C -0.1747(2) 0.39875(13) 0.20395(13) 0.0336(4) Uani 1 1 d . . . . .
H24 H -0.124081 0.386113 0.258682 0.04 Uiso 1 1 calc R U . . .
C25 C -0.4656(2) 0.26813(13) 0.11042(12) 0.0312(3) Uani 1 1 d . . . . .
C26 C -0.5189(2) 0.00512(13) 0.19094(13) 0.0332(4) Uani 1 1 d . . . . .
C27 C -0.3869(3) -0.03777(15) 0.24938(17) 0.0464(5) Uani 1 1 d . . . . .
H27A H -0.334287 0.017638 0.260953 0.07 Uiso 1 1 calc R U . . .
H27B H -0.296311 -0.075019 0.212688 0.07 Uiso 1 1 calc R U . . .
H27C H -0.443469 -0.084091 0.312881 0.07 Uiso 1 1 calc R U . . .
C28 C -0.6400(3) -0.06820(15) 0.18443(16) 0.0438(5) Uani 1 1 d . . . . .
H28A H -0.719119 -0.031328 0.143766 0.066 Uiso 1 1 calc R U . . .
H28B H -0.707735 -0.102047 0.250864 0.066 Uiso 1 1 calc R U . . .
H28C H -0.572302 -0.119146 0.15441 0.066 Uiso 1 1 calc R U . . .
N1 N 1.6343(2) 0.81669(13) 0.57762(11) 0.0397(4) Uani 1 1 d . . . . .
N2 N 1.93605(18) 0.84982(11) 0.82681(11) 0.0315(3) Uani 1 1 d . . . . .
N3 N 2.04288(17) 0.86673(11) 0.88203(11) 0.0318(3) Uani 1 1 d . . . . .
N4 N -0.14721(19) 0.48828(11) 0.13533(11) 0.0353(3) Uani 1 1 d . . . . .
N5 N -0.43562(18) 0.16915(11) 0.15383(11) 0.0315(3) Uani 1 1 d . . . . .
N6 N -0.54322(18) 0.09859(11) 0.14773(11) 0.0329(3) Uani 1 1 d . . . . .
O1 O 2.13730(17) 0.90974(11) 0.68242(10) 0.0473(3) Uani 1 1 d . . . . .
O2 O 1.37694(19) 0.71423(12) 0.55914(10) 0.0494(4) Uani 1 1 d . . . . .
O3 O 1.2984(2) 0.83357(11) 0.43697(11) 0.0538(4) Uani 1 1 d . . . . .
O4 O 0.07635(18) 0.61241(10) 0.15099(10) 0.0420(3) Uani 1 1 d . . . . .
O5 O 0.1549(2) 0.47469(11) 0.25590(14) 0.0656(5) Uani 1 1 d . . . . .
O6 O -0.58313(17) 0.29866(10) 0.06876(10) 0.0428(3) Uani 1 1 d . . . . .
H2B H 1.826(3) 0.8354(15) 0.8547(15) 0.043(6) Uiso 1 1 d . . . . .
H2 H 1.462(4) 0.764(2) 0.550(2) 0.084(9) Uiso 1 1 d . . . . .
H4 H -0.005(4) 0.569(2) 0.148(2) 0.080(8) Uiso 1 1 d . . . . .
H5A H -0.341(3) 0.1503(16) 0.1697(15) 0.043(6) 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 1.336(3) . ?
C1 C2 1.384(2) . ?
C1 H1 0.95 . ?
C2 C3 1.387(2) . ?
C2 H2A 0.95 . ?
C3 C4 1.385(2) . ?
C3 C6 1.502(2) . ?
C4 C5 1.385(2) . ?
C4 H4A 0.95 . ?
C5 N1 1.329(2) . ?
C5 H5 0.95 . ?
C6 O1 1.216(2) . ?
C6 N2 1.354(2) . ?
C7 N3 1.275(2) . ?
C7 C9 1.491(3) . ?
C7 C8 1.501(2) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O3 1.201(2) . ?
C10 O2 1.322(2) . ?
C10 C11 1.506(2) . ?
C11 C12 1.515(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.522(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.521(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C16 1.520(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.520(2) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.523(2) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.501(2) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 O5 1.197(2) . ?
C19 O4 1.322(2) . ?
C20 N4 1.338(2) . ?
C20 C21 1.380(2) . ?
C20 H20 0.95 . ?
C21 C22 1.389(2) . ?
C21 H21 0.95 . ?
C22 C23 1.386(2) . ?
C22 C25 1.500(2) . ?
C23 C24 1.383(2) . ?
C23 H23 0.95 . ?
C24 N4 1.335(2) . ?
C24 H24 0.95 . ?
C25 O6 1.2200(19) . ?
C25 N5 1.350(2) . ?
C26 N6 1.276(2) . ?
C26 C27 1.492(2) . ?
C26 C28 1.499(2) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
N2 N3 1.3891(17) . ?
N2 H2B 0.88(2) . ?
N5 N6 1.3915(18) . ?
N5 H5A 0.84(2) . ?
O2 H2 0.96(3) . ?
O4 H4 0.94(3) . ?

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 123.29(18) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.70(17) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 118.38(15) . . ?
C4 C3 C6 120.85(15) . . ?
C2 C3 C6 120.75(15) . . ?
C3 C4 C5 118.62(16) . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 H4A 120.7 . . ?
N1 C5 C4 123.53(17) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1 C6 N2 124.42(15) . . ?
O1 C6 C3 121.78(15) . . ?
N2 C6 C3 113.76(14) . . ?
N3 C7 C9 126.27(15) . . ?
N3 C7 C8 117.25(15) . . ?
C9 C7 C8 116.48(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 123.09(16) . . ?
O3 C10 C11 124.44(16) . . ?
O2 C10 C11 112.44(16) . . ?
C10 C11 C12 113.96(15) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 112.94(15) . . ?
C11 C12 H12A 109 . . ?
C13 C12 H12A 109 . . ?
C11 C12 H12B 109 . . ?
C13 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 112.61(15) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 114.47(15) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 112.10(15) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 115.35(15) . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 C18 111.37(15) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108 . . ?
C19 C18 C17 114.28(15) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
O5 C19 O4 122.67(16) . . ?
O5 C19 C18 124.43(16) . . ?
O4 C19 C18 112.88(15) . . ?
N4 C20 C21 122.90(17) . . ?
N4 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C20 C21 C22 119.19(15) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 118.24(15) . . ?
C23 C22 C25 123.39(15) . . ?
C21 C22 C25 118.27(14) . . ?
C24 C23 C22 118.59(16) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
N4 C24 C23 123.51(16) . . ?
N4 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
O6 C25 N5 123.82(15) . . ?
O6 C25 C22 120.62(16) . . ?
N5 C25 C22 115.50(14) . . ?
N6 C26 C27 126.80(15) . . ?
N6 C26 C28 116.07(15) . . ?
C27 C26 C28 117.10(16) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C5 N1 C1 117.42(15) . . ?
C6 N2 N3 118.34(14) . . ?
C6 N2 H2B 120.4(14) . . ?
N3 N2 H2B 119.9(14) . . ?
C7 N3 N2 117.73(14) . . ?
C24 N4 C20 117.56(14) . . ?
C25 N5 N6 117.34(14) . . ?
C25 N5 H5A 120.3(14) . . ?
N6 N5 H5A 120.3(14) . . ?
C26 N6 N5 117.74(14) . . ?
C10 O2 H2 109.1(17) . . ?
C19 O4 H4 110.3(17) . . ?

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 -1.6(3) . . . . ?
C1 C2 C3 C4 2.2(3) . . . . ?
C1 C2 C3 C6 -179.70(16) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C6 C3 C4 C5 -178.78(15) . . . . ?
C3 C4 C5 N1 -1.7(3) . . . . ?
C4 C3 C6 O1 123.3(2) . . . . ?
C2 C3 C6 O1 -54.8(2) . . . . ?
C4 C3 C6 N2 -54.5(2) . . . . ?
C2 C3 C6 N2 127.45(18) . . . . ?
O3 C10 C11 C12 -2.8(3) . . . . ?
O2 C10 C11 C12 179.10(15) . . . . ?
C10 C11 C12 C13 175.88(15) . . . . ?
C11 C12 C13 C14 178.77(15) . . . . ?
C12 C13 C14 C15 177.67(16) . . . . ?
C13 C14 C15 C16 -177.49(16) . . . . ?
C14 C15 C16 C17 -178.60(16) . . . . ?
C15 C16 C17 C18 179.46(16) . . . . ?
C16 C17 C18 C19 -174.12(16) . . . . ?
C17 C18 C19 O5 -5.9(3) . . . . ?
C17 C18 C19 O4 172.51(16) . . . . ?
N4 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 0.7(2) . . . . ?
C20 C21 C22 C25 177.15(15) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C25 C22 C23 C24 -176.50(15) . . . . ?
C22 C23 C24 N4 -0.4(3) . . . . ?
C23 C22 C25 O6 148.36(18) . . . . ?
C21 C22 C25 O6 -27.9(2) . . . . ?
C23 C22 C25 N5 -29.0(2) . . . . ?
C21 C22 C25 N5 154.73(16) . . . . ?
C4 C5 N1 C1 2.3(3) . . . . ?
C2 C1 N1 C5 -0.7(3) . . . . ?
O1 C6 N2 N3 2.9(3) . . . . ?
C3 C6 N2 N3 -179.39(14) . . . . ?
C9 C7 N3 N2 -0.1(3) . . . . ?
C8 C7 N3 N2 179.91(15) . . . . ?
C6 N2 N3 C7 172.23(16) . . . . ?
C23 C24 N4 C20 0.5(3) . . . . ?
C21 C20 N4 C24 0.0(3) . . . . ?
O6 C25 N5 N6 1.8(3) . . . . ?
C22 C25 N5 N6 179.04(14) . . . . ?
C27 C26 N6 N5 0.8(3) . . . . ?
C28 C26 N6 N5 178.74(15) . . . . ?
C25 N5 N6 C26 -178.07(16) . . . . ?

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 H2B N6 0.88(2) 2.35(2) 3.088(2) 141.8(18) 2_666 yes
N2 H2B O6 0.88(2) 2.60(2) 3.384(2) 149.2(17) 2_666 yes
O2 H2 N1 0.96(3) 1.80(3) 2.706(2) 156(3) . yes
O4 H4 N4 0.94(3) 1.74(3) 2.6770(18) 176(3) . yes
N5 H5A N3 0.84(2) 2.31(2) 3.0476(19) 147.4(19) 2_766 yes



# END of CIF
####################################################################### 
# 
# 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_izact+C9
_database_code_depnum_ccdc_archive 'CCDC 2290721'
loop_
_audit_author_name
_audit_author_address
'Matthew Scheepers'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-12-06 downloaded from the CCDC.
;

_audit_creation_date             2022-10-19T13:41:56-00:00
_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         'C9 H11 N3 O, C4.5 H8 O2'
_chemical_formula_sum            'C13.50 H19 N3 O3'
_chemical_formula_weight         271.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                   22.0145(19)
_cell_length_b                   16.7461(15)
_cell_length_c                   7.9045(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.476(3)
_cell_angle_gamma                90
_cell_volume                     2865.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4709
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      26.1
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.005
-1 1 0 0.031
1 0 0 0.057
1 -1 1 0.139
1 -1 -1 0.061
1 -1 0 0.008


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

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
        wR2(int) was 0.0801 before and 0.0755 after correction.
        The Ratio of minimum to maximum transmission is 0.9275.
        The λ/2 correction factor is Not present.
;
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.995

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

_diffrn_ambient_temperature      173
_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  0.1327
_diffrn_reflns_av_unetI/netI     0.048
_diffrn_reflns_number            54106
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.887
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3570
_reflns_number_gt                2161
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+2.4312P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3570
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.107
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   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 0.71915(10) 0.29233(13) 0.3049(2) 0.0389(5) Uani 1 1 d . . . . .
H1 H 0.718355 0.236946 0.33049 0.047 Uiso 1 1 calc R U . . .
C2 C 0.75513(10) 0.31768(13) 0.1901(2) 0.0360(5) Uani 1 1 d . . . . .
H2 H 0.777933 0.280328 0.136191 0.043 Uiso 1 1 calc R U . . .
C3 C 0.75763(8) 0.39855(12) 0.1542(2) 0.0293(4) Uani 1 1 d . . . . .
C4 C 0.72227(9) 0.45053(12) 0.2316(2) 0.0325(4) Uani 1 1 d . . . . .
H4 H 0.722435 0.506169 0.208262 0.039 Uiso 1 1 calc R U . . .
C5 C 0.68650(9) 0.41988(13) 0.3442(2) 0.0345(5) Uani 1 1 d . . . . .
H5 H 0.661941 0.455736 0.396189 0.041 Uiso 1 1 calc R U . . .
C6 C 0.79669(9) 0.42558(12) 0.0275(2) 0.0313(4) Uani 1 1 d . . . . .
C7 C 0.90351(9) 0.57800(13) 0.0089(2) 0.0340(4) Uani 1 1 d . . . . .
C8 C 0.90705(12) 0.62613(15) 0.1696(3) 0.0566(7) Uani 1 1 d . . . . .
H8A H 0.86587 0.629903 0.199667 0.085 Uiso 1 1 calc R U . . .
H8B H 0.922235 0.679833 0.150929 0.085 Uiso 1 1 calc R U . . .
H8C H 0.935349 0.600213 0.263621 0.085 Uiso 1 1 calc R U . . .
C9 C 0.94528(11) 0.60317(15) -0.1124(3) 0.0495(6) Uani 1 1 d . . . . .
H9A H 0.939327 0.567363 -0.212123 0.074 Uiso 1 1 calc R U . . .
H9B H 0.988389 0.600514 -0.053101 0.074 Uiso 1 1 calc R U . . .
H9C H 0.935348 0.658017 -0.15101 0.074 Uiso 1 1 calc R U . . .
C10 C 0.61025(9) 0.35313(13) 0.7327(2) 0.0345(4) Uani 1 1 d . . . . .
C11 C 0.58428(10) 0.32125(13) 0.8825(3) 0.0396(5) Uani 1 1 d . . . . .
H11A H 0.617908 0.293555 0.960832 0.048 Uiso 1 1 calc R U . . .
H11B H 0.552616 0.280696 0.838393 0.048 Uiso 1 1 calc R U . . .
C12 C 0.55539(9) 0.38161(12) 0.9872(2) 0.0327(4) Uani 1 1 d . . . . .
H12A H 0.522177 0.411087 0.911046 0.039 Uiso 1 1 calc R U . . .
H12B H 0.587012 0.420628 1.039956 0.039 Uiso 1 1 calc R U . . .
C13 C 0.52873(9) 0.33883(12) 1.1276(2) 0.0332(4) Uani 1 1 d . . . . .
H13A H 0.496887 0.300856 1.071408 0.04 Uiso 1 1 calc R U . . .
H13B H 0.562185 0.306964 1.196872 0.04 Uiso 1 1 calc R U . . .
C14 C 0.5 0.39063(17) 1.25 0.0339(6) Uani 1 2 d S T P . .
H14A H 0.4679 0.425337 1.18322 0.041 Uiso 0.5 1 calc R U P . .
H14B H 0.532102 0.425334 1.316783 0.041 Uiso 0.5 1 calc R U P . .
N1 N 0.68505(8) 0.34227(11) 0.3827(2) 0.0357(4) Uani 1 1 d . . . . .
N2 N 0.82980(7) 0.49279(11) 0.0726(2) 0.0325(4) Uani 1 1 d . . . . .
N3 N 0.86877(7) 0.51807(11) -0.03699(19) 0.0348(4) Uani 1 1 d . . . . .
O1 O 0.79654(7) 0.38875(9) -0.10645(17) 0.0436(4) Uani 1 1 d . . . . .
O2 O 0.62607(7) 0.29484(9) 0.63499(19) 0.0456(4) Uani 1 1 d . . . . .
O3 O 0.61604(8) 0.42282(10) 0.7021(2) 0.0537(5) Uani 1 1 d . . . . .
H2A H 0.8337(11) 0.5129(14) 0.179(3) 0.053(7) Uiso 1 1 d . . . . .
H2B H 0.6453(14) 0.3151(18) 0.540(4) 0.084(9) 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 H1 0.95 . ?
C1 C2 1.376(3) . ?
C1 N1 1.345(3) . ?
C2 H2 0.95 . ?
C2 C3 1.387(3) . ?
C3 C4 1.382(3) . ?
C3 C6 1.503(3) . ?
C4 H4 0.95 . ?
C4 C5 1.389(3) . ?
C5 H5 0.95 . ?
C5 N1 1.336(3) . ?
C6 N2 1.353(3) . ?
C6 O1 1.225(2) . ?
C7 C8 1.494(3) . ?
C7 C9 1.505(3) . ?
C7 N3 1.274(3) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.503(3) . ?
C10 O2 1.330(2) . ?
C10 O3 1.203(3) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 C12 1.517(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C12 C13 1.526(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C13 C14 1.520(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
N2 N3 1.391(2) . ?
N2 H2A 0.89(3) . ?
O2 H2B 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.5 . . ?
N1 C1 H1 118.5 . . ?
N1 C1 C2 123.1(2) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.04(19) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C6 118.63(17) . . ?
C4 C3 C2 118.53(17) . . ?
C4 C3 C6 122.79(18) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.77(19) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 118.5 . . ?
N1 C5 C4 123.01(19) . . ?
N1 C5 H5 118.5 . . ?
N2 C6 C3 114.90(16) . . ?
O1 C6 C3 120.82(18) . . ?
O1 C6 N2 124.27(17) . . ?
C8 C7 C9 116.57(19) . . ?
N3 C7 C8 127.07(18) . . ?
N3 C7 C9 116.36(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C11 111.97(18) . . ?
O3 C10 C11 124.91(19) . . ?
O3 C10 O2 123.12(18) . . ?
C10 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C10 C11 C12 116.74(18) . . ?
H11A C11 H11B 107.3 . . ?
C12 C11 H11A 108.1 . . ?
C12 C11 H11B 108.1 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C11 C12 C13 109.81(17) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C12 C13 H13A 108 . . ?
C12 C13 H13B 108 . . ?
H13A C13 H13B 107.3 . . ?
C14 C13 C12 117.05(18) . . ?
C14 C13 H13A 108 . . ?
C14 C13 H13B 108 . . ?
C13 C14 C13 110.4(2) . 2_657 ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 2_657 . ?
C13 C14 H14B 109.6 2_657 . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C5 N1 C1 117.53(17) . . ?
C6 N2 N3 116.92(16) . . ?
C6 N2 H2A 121.1(16) . . ?
N3 N2 H2A 120.3(16) . . ?
C7 N3 N2 117.94(16) . . ?
C10 O2 H2B 112.6(18) . . ?

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 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 C6 -179.53(18) . . . . ?
C2 C1 N1 C5 0.4(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C6 N2 -138.49(19) . . . . ?
C2 C3 C6 O1 42.7(3) . . . . ?
C3 C4 C5 N1 0.6(3) . . . . ?
C3 C6 N2 N3 177.20(16) . . . . ?
C4 C3 C6 N2 44.0(3) . . . . ?
C4 C3 C6 O1 -134.8(2) . . . . ?
C4 C5 N1 C1 -1.4(3) . . . . ?
C6 C3 C4 C5 178.54(17) . . . . ?
C6 N2 N3 C7 -175.25(18) . . . . ?
C8 C7 N3 N2 -0.7(3) . . . . ?
C9 C7 N3 N2 179.59(18) . . . . ?
C10 C11 C12 C13 177.25(18) . . . . ?
C11 C12 C13 C14 177.69(15) . . . . ?
C12 C13 C14 C13 175.5(2) . . . 2_657 ?
N1 C1 C2 C3 1.2(3) . . . . ?
O1 C6 N2 N3 -4.0(3) . . . . ?
O2 C10 C11 C12 -170.73(18) . . . . ?
O3 C10 C11 C12 8.8(3) . . . . ?

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
C4 H4 O1 0.95 2.65 3.285(3) 124.6 6_566 yes
C4 H4 O3 0.95 2.62 3.134(3) 114.5 6_565 yes
C5 H5 O3 0.95 2.64 3.158(3) 115.1 6_565 yes
C8 H8A O1 0.98 2.37 3.268(3) 151.7 6_566 yes
N2 H2A N3 0.89(3) 2.30(3) 3.054(2) 142(2) 6_566 yes
N2 H2A O1 0.89(3) 2.60(3) 3.403(2) 150(2) 6_566 yes
O2 H2B N1 0.99(3) 1.71(3) 2.690(2) 174(3) . yes


