# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1906221'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-14 downloaded from the CCDC.
;

_audit_creation_date             2019-03-28T17:29:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C9 H7 Cl1 O2'
_chemical_formula_sum            'C9 H7 Cl O2'
_chemical_formula_weight         182.6
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   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                   5.6807(5)
_cell_length_b                   11.3724(9)
_cell_length_c                   11.9319(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.979(8)
_cell_angle_gamma                90
_cell_volume                     761.39(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1009
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      27.33
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

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

_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.019999
_diffrn_orient_matrix_ub_12      -0.025842
_diffrn_orient_matrix_ub_13      -0.05476
_diffrn_orient_matrix_ub_21      0.076613
_diffrn_orient_matrix_ub_22      -0.047257
_diffrn_orient_matrix_ub_23      0.020243
_diffrn_orient_matrix_ub_31      -0.098388
_diffrn_orient_matrix_ub_32      -0.031511
_diffrn_orient_matrix_ub_33      0.014759
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_number            2553
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.457
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             1335
_reflns_number_gt                1055
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1335
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.054
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.3052(4) 0.2448(2) 0.37028(19) 0.0198(6) Uani 1 1 d . . . . .
C2 C 0.4222(4) 0.1195(2) 0.3803(2) 0.0219(6) Uani 1 1 d . . . . .
H2 H 0.563871 0.096342 0.436683 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1680(4) 0.0634(2) 0.3709(2) 0.0275(6) Uani 1 1 d . . . . .
H3 H 0.122744 -0.001014 0.420433 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0527(4) 0.1885(2) 0.3595(2) 0.0284(6) Uani 1 1 d . . . . .
H4 H -0.077993 0.216007 0.400333 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0365(4) 0.1811(2) 0.2275(2) 0.0313(6) Uani 1 1 d . . . . .
H5 H -0.1046 0.204466 0.170892 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1525(4) 0.0558(2) 0.2388(2) 0.0289(6) Uani 1 1 d . . . . .
H6 H 0.095544 -0.013935 0.191067 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4056(4) 0.1116(2) 0.2487(2) 0.0235(6) Uani 1 1 d . . . . .
H7 H 0.535832 0.084094 0.207484 0.028 Uiso 1 1 calc R U . . .
C8 C 0.2891(4) 0.2353(2) 0.23740(19) 0.0228(6) Uani 1 1 d . . . . .
C9 C 0.3897(4) 0.3518(2) 0.43346(19) 0.0196(5) Uani 1 1 d . . . . .
O1 O 0.2444(3) 0.42373(16) 0.46182(15) 0.0327(5) Uani 1 1 d . . . . .
O2 O 0.6175(3) 0.36641(15) 0.45321(17) 0.0324(5) Uani 1 1 d . . . . .
H2A H 0.648882 0.432798 0.482644 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36856(12) 0.34985(6) 0.15239(5) 0.0381(3) 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 C9 1.472(3) . ?
C1 C4 1.557(3) . ?
C1 C2 1.569(3) . ?
C1 C8 1.578(3) . ?
C2 C7 1.561(3) . ?
C2 C3 1.566(3) . ?
C3 C4 1.563(4) . ?
C3 C6 1.567(3) . ?
C4 C5 1.565(4) . ?
C5 C8 1.550(3) . ?
C5 C6 1.567(4) . ?
C6 C7 1.560(3) . ?
C7 C8 1.552(3) . ?
C8 Cl1 1.753(2) . ?
C9 O1 1.246(3) . ?
C9 O2 1.289(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
C9 C1 C4 127.21(19) . . ?
C9 C1 C2 127.69(19) . . ?
C4 C1 C2 90.38(18) . . ?
C9 C1 C8 122.3(2) . . ?
C4 C1 C8 88.90(16) . . ?
C2 C1 C8 88.41(17) . . ?
C7 C2 C3 89.66(17) . . ?
C7 C2 C1 90.96(17) . . ?
C3 C2 C1 89.40(16) . . ?
C4 C3 C2 90.27(18) . . ?
C4 C3 C6 90.3(2) . . ?
C2 C3 C6 90.09(17) . . ?
C1 C4 C3 89.94(17) . . ?
C1 C4 C5 90.82(17) . . ?
C3 C4 C5 89.83(19) . . ?
C8 C5 C4 89.64(17) . . ?
C8 C5 C6 89.03(18) . . ?
C4 C5 C6 90.3(2) . . ?
C7 C6 C5 90.39(18) . . ?
C7 C6 C3 89.69(17) . . ?
C5 C6 C3 89.60(19) . . ?
C8 C7 C6 89.23(17) . . ?
C8 C7 C2 89.62(17) . . ?
C6 C7 C2 90.56(17) . . ?
C5 C8 C7 91.35(19) . . ?
C5 C8 C1 90.64(17) . . ?
C7 C8 C1 91.01(17) . . ?
C5 C8 Cl1 124.79(18) . . ?
C7 C8 Cl1 125.40(17) . . ?
C1 C8 Cl1 123.45(17) . . ?
O1 C9 O2 123.7(2) . . ?
O1 C9 C1 120.3(2) . . ?
O2 C9 C1 115.9(2) . . ?



# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1906224'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-14 downloaded from the CCDC.
;

_audit_creation_date             2019-03-28T16:32:39-00:00
_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_sum            'C24 H27 N O3'
_chemical_formula_weight         377.46
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.7132(3)
_cell_length_b                   14.1931(5)
_cell_length_c                   14.3361(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1976.38(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2601
_cell_measurement_theta_min      5.45
_cell_measurement_theta_max      61.5
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

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

_exptl_absorpt_coefficient_mu    0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.707
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.019963
_diffrn_orient_matrix_ub_12      -0.045014
_diffrn_orient_matrix_ub_13      -0.096886
_diffrn_orient_matrix_ub_21      -0.105787
_diffrn_orient_matrix_ub_22      -0.076768
_diffrn_orient_matrix_ub_23      0.024929
_diffrn_orient_matrix_ub_31      -0.116421
_diffrn_orient_matrix_ub_32      0.062084
_diffrn_orient_matrix_ub_33      -0.0394
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.042
_diffrn_reflns_number            5200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.384
_diffrn_reflns_theta_max         61.573
_diffrn_reflns_theta_full        61.573
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.864
_reflns_Friedel_fraction_full    0.691
_reflns_Friedel_fraction_max     0.691
_reflns_Friedel_coverage         0.513
_reflns_number_total             2655
_reflns_number_gt                2524
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1180(3) 1.00951(19) -0.1855(2) 0.0349(7) Uani 1 1 d . . . . .
C2 C 0.1999(3) 0.9162(2) -0.2023(3) 0.0492(9) Uani 1 1 d . . . . .
H2 H 0.273699 0.907418 -0.250139 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2201(3) 0.9061(2) -0.0949(3) 0.0516(10) Uani 1 1 d . . . . .
H3 H 0.308857 0.890159 -0.063223 0.062 Uiso 1 1 calc R U . . .
C4 C 0.0853(3) 0.84640(18) -0.08965(18) 0.0285(6) Uani 1 1 d . . . . .
C5 C 0.0011(4) 0.9391(2) -0.0746(2) 0.0426(7) Uani 1 1 d . . . . .
H5 H -0.073582 0.947592 -0.027371 0.051 Uiso 1 1 calc R U . . .
C6 C -0.0168(3) 0.9500(2) -0.1807(2) 0.0421(7) Uani 1 1 d . . . . .
H6 H -0.10512 0.966674 -0.212589 0.051 Uiso 1 1 calc R U . . .
C7 C 0.0649(4) 0.8590(2) -0.1972(2) 0.0417(7) Uani 1 1 d . . . . .
H7 H 0.03793 0.807769 -0.241412 0.05 Uiso 1 1 calc R U . . .
C8 C 0.1355(4) 0.9972(2) -0.0788(2) 0.0509(9) Uani 1 1 d . . . . .
H8 H 0.160945 1.048692 -0.034418 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1262(3) 1.0979(2) -0.2407(2) 0.0385(7) Uani 1 1 d . . . . .
C10 C 0.0529(3) 0.75752(17) -0.03992(18) 0.0269(6) Uani 1 1 d . . . . .
C11 C 0.1341(3) 0.63405(19) 0.06521(18) 0.0276(6) Uani 1 1 d . . . . .
C12 C 0.1437(3) 0.6376(2) 0.16137(19) 0.0313(6) Uani 1 1 d . . . . .
H12 H 0.161788 0.695445 0.192293 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1266(3) 0.5555(2) 0.21160(19) 0.0328(6) Uani 1 1 d . . . . .
H13 H 0.129398 0.558496 0.277769 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1054(3) 0.46838(19) 0.16912(19) 0.0290(6) Uani 1 1 d . . . . .
C15 C 0.0931(3) 0.3802(2) 0.2307(2) 0.0386(7) Uani 1 1 d . . . . .
C16 C 0.0394(3) 0.2976(2) 0.1733(2) 0.0433(8) Uani 1 1 d . . . . .
H16A H 0.050896 0.238774 0.209558 0.052 Uiso 1 1 calc R U . . .
H16B H -0.06028 0.3065 0.161776 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1125(4) 0.2872(2) 0.0807(2) 0.0491(9) Uani 1 1 d . . . . .
H17A H 0.07924 0.229426 0.049217 0.059 Uiso 1 1 calc R U . . .
H17B H 0.212477 0.279715 0.09201 0.059 Uiso 1 1 calc R U . . .
C18 C 0.0893(3) 0.3719(2) 0.0162(2) 0.0389(7) Uani 1 1 d . . . . .
C19 C 0.1018(3) 0.46482(19) 0.07139(19) 0.0294(6) Uani 1 1 d . . . . .
C20 C 0.1119(3) 0.54878(19) 0.02150(18) 0.0303(6) Uani 1 1 d . . . . .
H20 H 0.103156 0.547282 -0.044486 0.036 Uiso 1 1 calc R U . . .
C21 C -0.0057(5) 0.3976(3) 0.3114(2) 0.0657(11) Uani 1 1 d . . . . .
H21A H 0.029721 0.448902 0.350399 0.099 Uiso 1 1 calc R U . . .
H21B H -0.013971 0.340195 0.348879 0.099 Uiso 1 1 calc R U . . .
H21C H -0.096297 0.415055 0.286773 0.099 Uiso 1 1 calc R U . . .
C22 C 0.2363(4) 0.3564(3) 0.2700(3) 0.0751(14) Uani 1 1 d . . . . .
H22A H 0.301484 0.348517 0.218395 0.113 Uiso 1 1 calc R U . . .
H22B H 0.231137 0.297758 0.30594 0.113 Uiso 1 1 calc R U . . .
H22C H 0.267413 0.407645 0.3106 0.113 Uiso 1 1 calc R U . . .
C23 C -0.0533(4) 0.3664(3) -0.0290(3) 0.0588(9) Uani 1 1 d . . . . .
H23A H -0.123984 0.364341 0.019752 0.088 Uiso 1 1 calc R U . . .
H23B H -0.059297 0.309298 -0.067258 0.088 Uiso 1 1 calc R U . . .
H23C H -0.067913 0.421892 -0.068405 0.088 Uiso 1 1 calc R U . . .
C24 C 0.1987(5) 0.3688(3) -0.0603(3) 0.0657(11) Uani 1 1 d . . . . .
H24A H 0.178636 0.417159 -0.107136 0.099 Uiso 1 1 calc R U . . .
H24B H 0.198185 0.30657 -0.089856 0.099 Uiso 1 1 calc R U . . .
H24C H 0.28951 0.380696 -0.032874 0.099 Uiso 1 1 calc R U . . .
N1 N 0.1522(2) 0.71860(15) 0.01251(15) 0.0287(5) Uani 1 1 d . . . . .
H1 H 0.232866 0.746691 0.014562 0.034 Uiso 1 1 calc R U . . .
O1 O -0.06389(18) 0.72189(12) -0.04721(13) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.1077(3) 1.08139(15) -0.33065(15) 0.0511(6) Uani 1 1 d . . . . .
H2A H 0.10809 1.132643 -0.359947 0.077 Uiso 1 1 calc R U . . .
O3 O 0.1449(3) 1.17479(16) -0.20872(18) 0.0686(8) 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 C9 1.485(4) . ?
C1 C8 1.548(4) . ?
C1 C6 1.560(4) . ?
C1 C2 1.564(4) . ?
C2 C7 1.544(5) . ?
C2 C3 1.558(5) . ?
C3 C8 1.550(5) . ?
C3 C4 1.562(4) . ?
C4 C10 1.483(4) . ?
C4 C5 1.563(4) . ?
C4 C7 1.565(4) . ?
C5 C6 1.539(5) . ?
C5 C8 1.546(5) . ?
C6 C7 1.534(5) . ?
C9 O3 1.198(4) . ?
C9 O2 1.323(4) . ?
C10 O1 1.247(3) . ?
C10 N1 1.341(3) . ?
C11 C20 1.380(4) . ?
C11 C12 1.383(4) . ?
C11 N1 1.429(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.394(4) . ?
C14 C19 1.402(4) . ?
C14 C15 1.536(4) . ?
C15 C21 1.523(5) . ?
C15 C16 1.525(4) . ?
C15 C22 1.538(5) . ?
C16 C17 1.513(5) . ?
C17 C18 1.534(4) . ?
C18 C24 1.528(5) . ?
C18 C23 1.532(5) . ?
C18 C19 1.542(4) . ?
C19 C20 1.393(4) . ?

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
C9 C1 C8 128.0(3) . . ?
C9 C1 C6 121.7(2) . . ?
C8 C1 C6 89.3(2) . . ?
C9 C1 C2 127.3(3) . . ?
C8 C1 C2 90.1(2) . . ?
C6 C1 C2 88.6(2) . . ?
C7 C2 C3 90.7(2) . . ?
C7 C2 C1 90.3(2) . . ?
C3 C2 C1 89.4(3) . . ?
C8 C3 C2 90.2(2) . . ?
C8 C3 C4 90.0(2) . . ?
C2 C3 C4 89.5(2) . . ?
C10 C4 C3 131.5(2) . . ?
C10 C4 C5 122.6(2) . . ?
C3 C4 C5 89.4(2) . . ?
C10 C4 C7 123.0(2) . . ?
C3 C4 C7 89.8(2) . . ?
C5 C4 C7 88.5(2) . . ?
C6 C5 C8 90.2(2) . . ?
C6 C5 C4 90.5(2) . . ?
C8 C5 C4 90.1(2) . . ?
C7 C6 C5 90.5(2) . . ?
C7 C6 C1 90.8(2) . . ?
C5 C6 C1 90.1(2) . . ?
C6 C7 C2 90.2(2) . . ?
C6 C7 C4 90.6(2) . . ?
C2 C7 C4 90.0(2) . . ?
C5 C8 C1 90.4(2) . . ?
C5 C8 C3 90.5(2) . . ?
C1 C8 C3 90.3(3) . . ?
O3 C9 O2 123.7(3) . . ?
O3 C9 C1 125.0(3) . . ?
O2 C9 C1 111.3(3) . . ?
O1 C10 N1 122.3(2) . . ?
O1 C10 C4 119.8(2) . . ?
N1 C10 C4 117.9(2) . . ?
C20 C11 C12 119.7(3) . . ?
C20 C11 N1 121.0(2) . . ?
C12 C11 N1 119.3(2) . . ?
C13 C12 C11 118.8(3) . . ?
C12 C13 C14 122.6(2) . . ?
C13 C14 C19 118.2(2) . . ?
C13 C14 C15 118.9(2) . . ?
C19 C14 C15 122.9(2) . . ?
C21 C15 C16 108.6(3) . . ?
C21 C15 C14 110.7(3) . . ?
C16 C15 C14 110.0(2) . . ?
C21 C15 C22 109.1(3) . . ?
C16 C15 C22 109.7(3) . . ?
C14 C15 C22 108.6(2) . . ?
C17 C16 C15 112.8(3) . . ?
C16 C17 C18 112.5(3) . . ?
C24 C18 C23 108.9(3) . . ?
C24 C18 C17 107.9(3) . . ?
C23 C18 C17 110.3(3) . . ?
C24 C18 C19 109.8(2) . . ?
C23 C18 C19 109.4(3) . . ?
C17 C18 C19 110.5(2) . . ?
C20 C19 C14 118.7(2) . . ?
C20 C19 C18 118.2(2) . . ?
C14 C19 C18 123.0(2) . . ?
C11 C20 C19 121.9(2) . . ?
C10 N1 C11 123.6(2) . . ?



# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1906222'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-14 downloaded from the CCDC.
;

_audit_creation_date             2019-03-28T17:37:54-00:00
_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         'C17 H12 Cl1 F3 N2 O3'
_chemical_formula_sum            'C17 H12 Cl F3 N2 O3'
_chemical_formula_weight         384.74
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   14.9260(10)
_cell_length_b                   6.8613(4)
_cell_length_c                   17.1430(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.037(8)
_cell_angle_gamma                90
_cell_volume                     1638.63(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1324
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      25.18
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.56
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784

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

_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      0.032172
_diffrn_orient_matrix_ub_12      -0.045918
_diffrn_orient_matrix_ub_13      -0.016231
_diffrn_orient_matrix_ub_21      0.039412
_diffrn_orient_matrix_ub_22      0.041989
_diffrn_orient_matrix_ub_23      0.032396
_diffrn_orient_matrix_ub_31      0.002179
_diffrn_orient_matrix_ub_32      -0.082496
_diffrn_orient_matrix_ub_33      0.025556
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_number            6371
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             2874
_reflns_number_gt                2185
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.37.35 (Agilent Technologies, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+1.5939P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.091
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.7280(2) 0.4340(4) 0.9550(2) 0.0304(7) Uani 1 1 d . . . . .
C2 C 0.6339(3) 0.3639(5) 0.9659(3) 0.0432(9) Uani 1 1 d . . . . .
H2 H 0.613214 0.224815 0.964196 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6543(3) 0.5016(5) 1.0420(3) 0.0449(9) Uani 1 1 d . . . . .
H3 H 0.648947 0.464082 1.096553 0.054 Uiso 1 1 calc R U . . .
C4 C 0.7486(2) 0.5744(5) 1.0309(2) 0.0331(8) Uani 1 1 d . . . . .
H4 H 0.81213 0.59161 1.077033 0.04 Uiso 1 1 calc R U . . .
C5 C 0.6894(2) 0.7398(5) 0.9725(2) 0.0328(8) Uani 1 1 d . . . . .
H5 H 0.709588 0.879242 0.974494 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5956(3) 0.6657(5) 0.9839(2) 0.0431(9) Uani 1 1 d . . . . .
H6 H 0.547076 0.750164 0.99525 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5750(2) 0.5274(5) 0.9068(3) 0.0440(9) Uani 1 1 d . . . . .
H7 H 0.511506 0.51012 0.860608 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6687(2) 0.6027(5) 0.8966(2) 0.0314(7) Uani 1 1 d . . . . .
C9 C 0.7904(2) 0.2966(4) 0.9305(2) 0.0308(7) Uani 1 1 d . . . . .
C10 C 0.9576(2) 0.2392(5) 0.93648(18) 0.0268(7) Uani 1 1 d . . . . .
C12 C 0.9837(2) -0.0603(5) 0.86719(19) 0.0301(7) Uani 1 1 d . . . . .
C13 C 0.9361(3) -0.2262(5) 0.8269(2) 0.0419(9) Uani 1 1 d . . . . .
H13 H 0.871322 -0.247063 0.821927 0.05 Uiso 1 1 calc R U . . .
C14 C 0.9806(3) -0.3601(5) 0.7943(3) 0.0461(10) Uani 1 1 d . . . . .
H14 H 0.947289 -0.473021 0.766695 0.055 Uiso 1 1 calc R U . . .
C15 C 1.0732(3) -0.3296(5) 0.8019(2) 0.0438(9) Uani 1 1 d . . . . .
C16 C 1.1228(3) -0.1697(6) 0.8426(2) 0.0494(10) Uani 1 1 d . . . . .
H16 H 1.188042 -0.152757 0.848488 0.059 Uiso 1 1 calc R U . . .
C17 C 1.0781(2) -0.0324(5) 0.8753(2) 0.0412(9) Uani 1 1 d . . . . .
H17 H 1.112054 0.079869 0.902974 0.049 Uiso 1 1 calc R U . . .
C18 C 1.1112(3) -0.4852(8) 0.6973(3) 0.0646(13) Uani 1 1 d . . . . .
N1 N 0.88486(18) 0.3451(4) 0.95217(17) 0.0289(6) Uani 1 1 d . . . . .
H1 H 0.90254 0.4559 0.979222 0.035 Uiso 1 1 calc R U . . .
N3 N 0.92975(18) 0.0698(4) 0.89691(16) 0.0289(6) Uani 1 1 d . . . . .
H3A H 0.870241 0.034635 0.888211 0.035 Uiso 1 1 calc R U . . .
O1 O 0.75519(17) 0.1491(3) 0.89081(18) 0.0485(7) Uani 1 1 d . . . . .
O2 O 1.03920(16) 0.3062(3) 0.95973(16) 0.0375(6) Uani 1 1 d . . . . .
O3 O 1.1225(2) -0.4763(4) 0.77399(18) 0.0621(9) Uani 1 1 d . . . . .
F1 F 1.1510(5) -0.3228(6) 0.6763(3) 0.158(2) Uani 1 1 d . . . . .
F2 F 1.0232(2) -0.4856(6) 0.64362(18) 0.1202(15) Uani 1 1 d . . . . .
F3 F 1.1564(2) -0.6283(5) 0.67877(19) 0.0909(10) Uani 1 1 d . . . . .
Cl1 Cl 0.68114(7) 0.66807(14) 0.80250(5) 0.0485(3) 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 C9 1.488(4) . ?
C1 C4 1.558(5) . ?
C1 C2 1.559(4) . ?
C1 C8 1.578(4) . ?
C2 C3 1.550(6) . ?
C2 C7 1.555(5) . ?
C3 C6 1.549(5) . ?
C3 C4 1.568(5) . ?
C4 C5 1.561(5) . ?
C5 C8 1.544(5) . ?
C5 C6 1.566(5) . ?
C6 C7 1.566(5) . ?
C7 C8 1.559(5) . ?
C8 Cl1 1.747(3) . ?
C9 O1 1.227(4) . ?
C9 N1 1.364(4) . ?
C10 O2 1.227(4) . ?
C10 N3 1.335(4) . ?
C10 N1 1.410(4) . ?
C12 C17 1.379(5) . ?
C12 C13 1.388(5) . ?
C12 N3 1.414(4) . ?
C13 C14 1.366(5) . ?
C14 C15 1.356(5) . ?
C15 C16 1.367(5) . ?
C15 O3 1.427(4) . ?
C16 C17 1.384(5) . ?
C18 O3 1.265(5) . ?
C18 F3 1.293(5) . ?
C18 F2 1.306(5) . ?
C18 F1 1.370(6) . ?

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
C9 C1 C4 132.3(3) . . ?
C9 C1 C2 121.4(3) . . ?
C4 C1 C2 90.4(3) . . ?
C9 C1 C8 123.4(3) . . ?
C4 C1 C8 88.5(2) . . ?
C2 C1 C8 88.7(2) . . ?
C3 C2 C7 90.2(3) . . ?
C3 C2 C1 90.0(3) . . ?
C7 C2 C1 91.3(3) . . ?
C6 C3 C2 90.4(3) . . ?
C6 C3 C4 90.9(3) . . ?
C2 C3 C4 90.3(3) . . ?
C1 C4 C5 91.0(2) . . ?
C1 C4 C3 89.3(3) . . ?
C5 C4 C3 89.0(3) . . ?
C8 C5 C4 89.6(2) . . ?
C8 C5 C6 89.5(2) . . ?
C4 C5 C6 90.5(3) . . ?
C3 C6 C7 89.8(3) . . ?
C3 C6 C5 89.6(3) . . ?
C7 C6 C5 90.3(3) . . ?
C2 C7 C8 89.5(2) . . ?
C2 C7 C6 89.6(3) . . ?
C8 C7 C6 88.9(3) . . ?
C5 C8 C7 91.3(3) . . ?
C5 C8 C1 90.9(2) . . ?
C7 C8 C1 90.4(2) . . ?
C5 C8 Cl1 124.5(2) . . ?
C7 C8 Cl1 125.8(2) . . ?
C1 C8 Cl1 123.6(2) . . ?
O1 C9 N1 123.2(3) . . ?
O1 C9 C1 119.5(3) . . ?
N1 C9 C1 117.3(3) . . ?
O2 C10 N3 125.7(3) . . ?
O2 C10 N1 119.2(3) . . ?
N3 C10 N1 115.1(3) . . ?
C17 C12 C13 119.1(3) . . ?
C17 C12 N3 124.7(3) . . ?
C13 C12 N3 116.2(3) . . ?
C14 C13 C12 121.2(3) . . ?
C15 C14 C13 119.0(3) . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 O3 119.2(3) . . ?
C16 C15 O3 119.2(3) . . ?
C15 C16 C17 120.1(3) . . ?
C12 C17 C16 119.2(3) . . ?
O3 C18 F3 113.9(4) . . ?
O3 C18 F2 117.2(4) . . ?
F3 C18 F2 107.9(4) . . ?
O3 C18 F1 108.9(4) . . ?
F3 C18 F1 103.9(4) . . ?
F2 C18 F1 103.8(5) . . ?
C9 N1 C10 127.8(3) . . ?
C10 N3 C12 128.3(3) . . ?
C18 O3 C15 119.4(3) . . ?



# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1906223'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-06-14 downloaded from the CCDC.
;

_audit_creation_date             2019-03-28T17:10:57-00:00
_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_sum            'C14 H14 N4 O3'
_chemical_formula_weight         286.29

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   16.3369(14)
_cell_length_b                   9.5786(8)
_cell_length_c                   16.6878(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.900(9)
_cell_angle_gamma                90
_cell_volume                     2579.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1707
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      22.93
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200

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

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.011642
_diffrn_orient_matrix_ub_12      0.070749
_diffrn_orient_matrix_ub_13      -0.007324
_diffrn_orient_matrix_ub_21      0.000784
_diffrn_orient_matrix_ub_22      0.010454
_diffrn_orient_matrix_ub_23      0.04218
_diffrn_orient_matrix_ub_31      0.042393
_diffrn_orient_matrix_ub_32      0.019151
_diffrn_orient_matrix_ub_33      0.004125
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_number            9986
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4541
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4541
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.27
_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 0.12817(17) 0.4590(3) 0.51013(16) 0.0329(7) Uani 1 1 d . . . . .
H1A H 0.128381 0.451671 0.569936 0.039 Uiso 1 1 calc R U . . .
C2 C 0.20611(18) 0.4903(3) 0.46844(16) 0.0325(7) Uani 1 1 d . . . . .
H2 H 0.263621 0.506146 0.497514 0.039 Uiso 1 1 calc R U . . .
C3 C 0.07707(18) 0.5661(3) 0.45302(16) 0.0311(7) Uani 1 1 d . . . . .
H3 H 0.039041 0.638012 0.470347 0.037 Uiso 1 1 calc R U . . .
C4 C 0.10199(18) 0.3403(3) 0.44742(17) 0.0364(7) Uani 1 1 d . . . . .
H4 H 0.082851 0.245182 0.46079 0.044 Uiso 1 1 calc R U . . .
C5 C 0.15404(17) 0.5975(3) 0.41111(15) 0.0289(7) Uani 1 1 d . . . . .
H5 H 0.173108 0.692611 0.397564 0.035 Uiso 1 1 calc R U . . .
C6 C 0.05057(18) 0.4466(3) 0.39061(16) 0.0331(7) Uani 1 1 d . . . . .
H6 H -0.006983 0.430691 0.361677 0.04 Uiso 1 1 calc R U . . .
C7 C 0.17959(17) 0.3719(3) 0.40618(16) 0.0305(7) Uani 1 1 d . . . . .
H7 H 0.217564 0.299845 0.388855 0.037 Uiso 1 1 calc R U . . .
C8 C 0.12775(16) 0.4784(3) 0.34862(15) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.12688(17) 0.4913(3) 0.25888(15) 0.0284(7) Uani 1 1 d . . . . .
H9A H 0.114667 0.399202 0.232877 0.034 Uiso 1 1 calc R U . . .
H9B H 0.082652 0.557011 0.235803 0.034 Uiso 1 1 calc R U . . .
C10 C 0.26711(16) 0.4575(3) 0.22722(14) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.34526(16) 0.5346(3) 0.21414(16) 0.0291(7) Uani 1 1 d . . . . .
H11A H 0.33574 0.579925 0.160177 0.035 Uiso 1 1 calc R U . . .
H11B H 0.357059 0.608933 0.255549 0.035 Uiso 1 1 calc R U . . .
C12 C 0.45904(18) 0.4185(3) 0.15632(17) 0.0390(8) Uani 1 1 d . . . . .
H12 H 0.447813 0.457915 0.103521 0.047 Uiso 1 1 calc R U . . .
C13 C 0.52036(19) 0.3265(3) 0.18389(19) 0.0465(9) Uani 1 1 d . . . . .
H13 H 0.559781 0.291712 0.152598 0.056 Uiso 1 1 calc R U . . .
C14 C 0.45480(18) 0.3634(3) 0.28026(17) 0.0301(7) Uani 1 1 d . . . . .
C15 C 0.49294(19) 0.7180(3) 0.37685(17) 0.0370(8) Uani 1 1 d . . . . .
H15 H 0.433737 0.70035 0.38235 0.044 Uiso 1 1 calc R U . . .
C16 C 0.56684(19) 0.6182(3) 0.40633(17) 0.0396(8) Uani 1 1 d . . . . .
H16 H 0.562406 0.526405 0.433847 0.048 Uiso 1 1 calc R U . . .
C17 C 0.52662(18) 0.7401(3) 0.29541(17) 0.0315(7) Uani 1 1 d . . . . .
H17 H 0.492065 0.738387 0.240445 0.038 Uiso 1 1 calc R U . . .
C18 C 0.54587(18) 0.8450(3) 0.41354(17) 0.0368(7) Uani 1 1 d . . . . .
H18 H 0.525778 0.921059 0.446629 0.044 Uiso 1 1 calc R U . . .
C19 C 0.61942(18) 0.7447(3) 0.44340(17) 0.0366(8) Uani 1 1 d . . . . .
H19 H 0.653617 0.746686 0.49854 0.044 Uiso 1 1 calc R U . . .
C20 C 0.60022(18) 0.6395(3) 0.32427(16) 0.0309(7) Uani 1 1 d . . . . .
H20 H 0.62019 0.563669 0.290943 0.037 Uiso 1 1 calc R U . . .
C21 C 0.57918(17) 0.8666(3) 0.33195(16) 0.0309(7) Uani 1 1 d . . . . .
H21 H 0.5835 0.958345 0.304363 0.037 Uiso 1 1 calc R U . . .
C22 C 0.65331(18) 0.7669(3) 0.36207(16) 0.0282(7) Uani 1 1 d . . . . .
C23 C 0.74255(18) 0.7909(3) 0.35758(16) 0.0324(7) Uani 1 1 d . . . . .
H23A H 0.763821 0.865906 0.396074 0.039 Uiso 1 1 calc R U . . .
H23B H 0.774071 0.70476 0.37432 0.039 Uiso 1 1 calc R U . . .
C24 C 0.77521(17) 0.7388(3) 0.22273(16) 0.0263(6) Uani 1 1 d . . . . .
C25 C 0.78794(18) 0.8036(3) 0.14289(15) 0.0314(7) Uani 1 1 d . . . . .
H25A H 0.747811 0.880723 0.129647 0.038 Uiso 1 1 calc R U . . .
H25B H 0.844369 0.843792 0.1487 0.038 Uiso 1 1 calc R U . . .
C26 C 0.83943(19) 0.6630(3) 0.03551(17) 0.0400(8) Uani 1 1 d . . . . .
H26 H 0.89538 0.693773 0.044829 0.048 Uiso 1 1 calc R U . . .
C27 C 0.8054(2) 0.5696(3) -0.02127(17) 0.0422(8) Uani 1 1 d . . . . .
H27 H 0.834793 0.524703 -0.058912 0.051 Uiso 1 1 calc R U . . .
C28 C 0.71041(17) 0.6305(3) 0.04203(16) 0.0287(7) Uani 1 1 d . . . . .
N1 N 0.20656(13) 0.5416(2) 0.24177(12) 0.0245(5) Uani 1 1 d . . . . .
H1 H 0.214954 0.632298 0.241052 0.029 Uiso 1 1 calc R U . . .
N2 N 0.41701(14) 0.4430(2) 0.21899(13) 0.0276(5) Uani 1 1 d . . . . .
N3 N 0.51758(15) 0.2910(3) 0.26245(16) 0.0419(7) Uani 1 1 d . . . . .
N4 N 0.43081(16) 0.3578(3) 0.35896(15) 0.0420(7) Uani 1 1 d . . . . .
N5 N 0.75642(14) 0.8300(2) 0.27647(13) 0.0288(6) Uani 1 1 d . . . . .
H5A H 0.752082 0.918581 0.262538 0.035 Uiso 1 1 calc R U . . .
N6 N 0.77770(14) 0.7039(2) 0.07643(13) 0.0299(6) Uani 1 1 d . . . . .
N7 N 0.72382(16) 0.5486(2) -0.01719(13) 0.0358(6) Uani 1 1 d . . . . .
N8 N 0.63170(16) 0.6412(3) 0.06949(14) 0.0383(7) Uani 1 1 d . . . . .
O1 O 0.26112(11) 0.32977(17) 0.22145(11) 0.0300(5) Uani 1 1 d . . . . .
O2 O 0.37554(13) 0.4365(2) 0.37278(11) 0.0422(5) Uani 1 1 d . . . . .
O3 O 0.46721(15) 0.2759(3) 0.40782(14) 0.0773(9) Uani 1 1 d . . . . .
O4 O 0.78496(12) 0.61341(18) 0.23545(11) 0.0360(5) Uani 1 1 d . . . . .
O5 O 0.62332(13) 0.7286(2) 0.12083(13) 0.0495(6) Uani 1 1 d . . . . .
O6 O 0.57701(14) 0.5608(3) 0.03968(13) 0.0653(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 C3 1.553(4) . ?
C1 C4 1.559(4) . ?
C1 C2 1.572(4) . ?
C2 C7 1.554(4) . ?
C2 C5 1.562(4) . ?
C3 C5 1.560(4) . ?
C3 C6 1.563(4) . ?
C4 C6 1.547(4) . ?
C4 C7 1.563(4) . ?
C5 C8 1.560(3) . ?
C6 C8 1.564(4) . ?
C7 C8 1.559(4) . ?
C8 C9 1.501(3) . ?
C9 N1 1.457(3) . ?
C10 O1 1.230(3) . ?
C10 N1 1.327(3) . ?
C10 C11 1.520(3) . ?
C11 N2 1.457(3) . ?
C12 N2 1.357(3) . ?
C12 C13 1.360(4) . ?
C13 N3 1.362(4) . ?
C14 N3 1.310(3) . ?
C14 N2 1.346(3) . ?
C14 N4 1.428(3) . ?
C15 C17 1.558(4) . ?
C15 C16 1.558(4) . ?
C15 C18 1.561(4) . ?
C16 C19 1.557(4) . ?
C16 C20 1.564(4) . ?
C17 C21 1.553(4) . ?
C17 C20 1.558(4) . ?
C18 C21 1.556(4) . ?
C18 C19 1.559(4) . ?
C19 C22 1.558(4) . ?
C20 C22 1.571(4) . ?
C21 C22 1.563(4) . ?
C22 C23 1.489(4) . ?
C23 N5 1.455(3) . ?
C24 O4 1.226(3) . ?
C24 N5 1.321(3) . ?
C24 C25 1.513(3) . ?
C25 N6 1.453(3) . ?
C26 C27 1.358(4) . ?
C26 N6 1.360(3) . ?
C27 N7 1.360(4) . ?
C28 N7 1.306(3) . ?
C28 N6 1.356(3) . ?
C28 N8 1.434(4) . ?
N4 O3 1.218(3) . ?
N4 O2 1.225(3) . ?
N8 O5 1.221(3) . ?
N8 O6 1.225(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
C3 C1 C4 90.2(2) . . ?
C3 C1 C2 89.9(2) . . ?
C4 C1 C2 89.9(2) . . ?
C7 C2 C5 90.1(2) . . ?
C7 C2 C1 89.7(2) . . ?
C5 C2 C1 89.7(2) . . ?
C1 C3 C5 90.5(2) . . ?
C1 C3 C6 89.56(19) . . ?
C5 C3 C6 90.11(19) . . ?
C6 C4 C1 89.9(2) . . ?
C6 C4 C7 90.2(2) . . ?
C1 C4 C7 89.9(2) . . ?
C3 C5 C8 90.1(2) . . ?
C3 C5 C2 89.9(2) . . ?
C8 C5 C2 89.80(19) . . ?
C4 C6 C3 90.3(2) . . ?
C4 C6 C8 90.2(2) . . ?
C3 C6 C8 89.8(2) . . ?
C2 C7 C8 90.16(19) . . ?
C2 C7 C4 90.5(2) . . ?
C8 C7 C4 89.9(2) . . ?
C9 C8 C7 126.1(2) . . ?
C9 C8 C5 124.5(2) . . ?
C7 C8 C5 89.98(19) . . ?
C9 C8 C6 125.4(2) . . ?
C7 C8 C6 89.72(19) . . ?
C5 C8 C6 90.04(19) . . ?
N1 C9 C8 110.6(2) . . ?
O1 C10 N1 124.5(2) . . ?
O1 C10 C11 122.1(2) . . ?
N1 C10 C11 113.4(2) . . ?
N2 C11 C10 112.7(2) . . ?
N2 C12 C13 106.6(3) . . ?
C12 C13 N3 110.8(3) . . ?
N3 C14 N2 114.2(2) . . ?
N3 C14 N4 121.6(3) . . ?
N2 C14 N4 124.1(2) . . ?
C17 C15 C16 89.9(2) . . ?
C17 C15 C18 89.3(2) . . ?
C16 C15 C18 89.9(2) . . ?
C19 C16 C15 90.1(2) . . ?
C19 C16 C20 90.0(2) . . ?
C15 C16 C20 90.1(2) . . ?
C21 C17 C15 90.7(2) . . ?
C21 C17 C20 90.4(2) . . ?
C15 C17 C20 90.3(2) . . ?
C21 C18 C19 90.3(2) . . ?
C21 C18 C15 90.4(2) . . ?
C19 C18 C15 89.9(2) . . ?
C16 C19 C22 90.5(2) . . ?
C16 C19 C18 90.1(2) . . ?
C22 C19 C18 89.9(2) . . ?
C17 C20 C16 89.7(2) . . ?
C17 C20 C22 89.74(19) . . ?
C16 C20 C22 89.7(2) . . ?
C17 C21 C18 89.6(2) . . ?
C17 C21 C22 90.23(19) . . ?
C18 C21 C22 89.8(2) . . ?
C23 C22 C19 123.2(2) . . ?
C23 C22 C21 127.3(2) . . ?
C19 C22 C21 90.1(2) . . ?
C23 C22 C20 125.7(2) . . ?
C19 C22 C20 89.7(2) . . ?
C21 C22 C20 89.6(2) . . ?
N5 C23 C22 112.4(2) . . ?
O4 C24 N5 124.6(2) . . ?
O4 C24 C25 121.5(2) . . ?
N5 C24 C25 113.9(2) . . ?
N6 C25 C24 112.8(2) . . ?
C27 C26 N6 106.6(3) . . ?
C26 C27 N7 111.1(3) . . ?
N7 C28 N6 114.3(3) . . ?
N7 C28 N8 123.3(3) . . ?
N6 C28 N8 122.4(2) . . ?
C10 N1 C9 123.3(2) . . ?
C14 N2 C12 105.1(2) . . ?
C14 N2 C11 130.8(2) . . ?
C12 N2 C11 124.1(2) . . ?
C14 N3 C13 103.3(3) . . ?
O3 N4 O2 124.6(3) . . ?
O3 N4 C14 117.7(3) . . ?
O2 N4 C14 117.7(2) . . ?
C24 N5 C23 123.2(2) . . ?
C28 N6 C26 104.7(2) . . ?
C28 N6 C25 130.9(2) . . ?
C26 N6 C25 124.4(2) . . ?
C28 N7 C27 103.3(2) . . ?
O5 N8 O6 124.2(3) . . ?
O5 N8 C28 118.5(2) . . ?
O6 N8 C28 117.3(3) . . ?



# END of CIF
