# Supplementary Information (SI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_at1128
_audit_block_doi                 10.5517/ccdc.csd.cc1zznvg
_database_code_depnum_ccdc_archive 'CCDC 1846727'
loop_
_audit_author_name
_audit_author_address
'Brian Skelton'
;University of Western Australia
Australia
;
_audit_update_record             
;
2018-06-01 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_date             2018-06-01T17:49:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C14 H19 N5 O2'
_chemical_formula_moiety         'C14 H19 N5 O2'
_chemical_formula_weight         289.34

#----------------------------------------------------------------------------#
#                   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                   13.8479(6)
_cell_length_b                   11.5901(4)
_cell_length_c                   9.8993(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.077(5)
_cell_angle_gamma                90
_cell_volume                     1510.40(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4916
_cell_measurement_theta_min      2.7831
_cell_measurement_theta_max      32.1913

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_exptl_absorpt_correction_T_min  0.97156
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      0.0256799
_diffrn_orient_matrix_ub_12      -0.0531372
_diffrn_orient_matrix_ub_13      0.0212264
_diffrn_orient_matrix_ub_21      -0.046017
_diffrn_orient_matrix_ub_22      -0.0302137
_diffrn_orient_matrix_ub_23      -0.0317424
_diffrn_orient_matrix_ub_31      0.0114305
_diffrn_orient_matrix_ub_32      -0.0025211
_diffrn_orient_matrix_ub_33      -0.0650056
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_number            16149
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         32.263
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_reflns_Friedel_coverage         0
_reflns_number_total             4989
_reflns_number_gt                3987
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;

_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'


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

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#
_refine_special_details          
;
The N-H distance was restrained to its ideal value.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.3010P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4989
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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 0.14721(8) 0.48200(8) 0.59458(10) 0.01726(19) Uani 1 1 d . . . . .
C11 C 0.12116(8) 0.55166(9) 0.70222(11) 0.0190(2) Uani 1 1 d . . . . .
C12 C 0.03871(8) 0.52159(9) 0.74770(11) 0.0212(2) Uani 1 1 d . . . . .
H12 H -0.00144 0.456084 0.70846 0.025 Uiso 1 1 calc R U . . .
C13 C 0.01551(9) 0.58771(11) 0.85053(12) 0.0281(2) Uani 1 1 d . . . . .
H13 H -0.040558 0.567282 0.881671 0.034 Uiso 1 1 calc R U . . .
C14 C 0.07398(10) 0.68350(11) 0.90788(13) 0.0333(3) Uani 1 1 d . . . . .
H14 H 0.057946 0.728441 0.978294 0.04 Uiso 1 1 calc R U . . .
C15 C 0.15577(10) 0.71371(11) 0.86254(14) 0.0326(3) Uani 1 1 d . . . . .
H15 H 0.195712 0.779333 0.901908 0.039 Uiso 1 1 calc R U . . .
C16 C 0.17937(9) 0.64819(10) 0.75971(12) 0.0259(2) Uani 1 1 d . . . . .
H16 H 0.235274 0.669189 0.728495 0.031 Uiso 1 1 calc R U . . .
N2 N 0.11710(7) 0.37319(7) 0.56336(9) 0.01755(17) Uani 1 1 d . . . . .
N3 N 0.15939(6) 0.34832(7) 0.46299(9) 0.01714(17) Uani 1 1 d . . . . .
C31 C 0.15670(8) 0.23359(9) 0.40210(11) 0.0201(2) Uani 1 1 d . . . . .
H31A H 0.16907 0.239264 0.30905 0.024 Uiso 1 1 calc R U . . .
H31B H 0.088677 0.199103 0.386319 0.024 Uiso 1 1 calc R U . . .
C32 C 0.23747(8) 0.15630(9) 0.50160(11) 0.0185(2) Uani 1 1 d . . . . .
H32A H 0.222666 0.147514 0.592687 0.022 Uiso 1 1 calc R U . . .
H32B H 0.234626 0.078821 0.458441 0.022 Uiso 1 1 calc R U . . .
N33 N 0.33842(7) 0.20345(8) 0.52890(9) 0.01761(17) Uani 1 1 d D . . . .
C34 C 0.38086(8) 0.26946(8) 0.64555(10) 0.01644(19) Uani 1 1 d . . . . .
O34 O 0.34639(6) 0.27873(7) 0.74454(7) 0.02104(17) Uani 1 1 d . . . . .
O35 O 0.46584(6) 0.31958(7) 0.63609(8) 0.02093(16) Uani 1 1 d . . . . .
C36 C 0.52708(8) 0.39617(10) 0.74991(11) 0.0226(2) Uani 1 1 d . . . . .
C37 C 0.57573(9) 0.32594(11) 0.88355(12) 0.0285(2) Uani 1 1 d . . . . .
H37A H 0.522615 0.294778 0.919493 0.043 Uiso 1 1 calc R U . . .
H37B H 0.62111 0.375534 0.956039 0.043 Uiso 1 1 calc R U . . .
H37C H 0.614793 0.262267 0.861223 0.043 Uiso 1 1 calc R U . . .
C38 C 0.60802(10) 0.44001(13) 0.68761(13) 0.0338(3) Uani 1 1 d . . . . .
H38A H 0.644167 0.374277 0.663719 0.051 Uiso 1 1 calc R U . . .
H38B H 0.656262 0.488996 0.757489 0.051 Uiso 1 1 calc R U . . .
H38C H 0.575657 0.484931 0.60158 0.051 Uiso 1 1 calc R U . . .
C39 C 0.46302(10) 0.49559(10) 0.77451(14) 0.0307(3) Uani 1 1 d . . . . .
H39A H 0.426444 0.531334 0.683249 0.046 Uiso 1 1 calc R U . . .
H39B H 0.507182 0.553017 0.836455 0.046 Uiso 1 1 calc R U . . .
H39C H 0.414099 0.466534 0.819696 0.046 Uiso 1 1 calc R U . . .
N4 N 0.21266(7) 0.43401(8) 0.43307(10) 0.02109(19) Uani 1 1 d . . . . .
N5 N 0.20574(7) 0.52055(8) 0.51647(10) 0.02168(19) Uani 1 1 d . . . . .
H33 H 0.3614(10) 0.2142(12) 0.4565(12) 0.028(4) Uiso 1 1 d 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 N2 1.3340(13) . ?
C1 N5 1.3578(13) . ?
C1 C11 1.4683(14) . ?
C11 C16 1.3931(16) . ?
C11 C12 1.3952(15) . ?
C12 C13 1.3891(15) . ?
C12 H12 0.95 . ?
C13 C14 1.3875(19) . ?
C13 H13 0.95 . ?
C14 C15 1.387(2) . ?
C14 H14 0.95 . ?
C15 C16 1.3878(16) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
N2 N3 1.3320(11) . ?
N3 N4 1.3244(12) . ?
N3 C31 1.4557(13) . ?
C31 C32 1.5297(15) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 N33 1.4463(13) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
N33 C34 1.3576(13) . ?
N33 H33 0.879(8) . ?
C34 O34 1.2206(11) . ?
C34 O35 1.3414(12) . ?
O35 C36 1.4777(13) . ?
C36 C39 1.5192(17) . ?
C36 C37 1.5210(16) . ?
C36 C38 1.5243(15) . ?
C37 H37A 0.98 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C38 H38A 0.98 . ?
C38 H38B 0.98 . ?
C38 H38C 0.98 . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
N4 N5 1.3213(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 112.21(9) . . ?
N2 C1 C11 123.95(9) . . ?
N5 C1 C11 123.84(9) . . ?
C16 C11 C12 119.77(10) . . ?
C16 C11 C1 119.79(10) . . ?
C12 C11 C1 120.45(10) . . ?
C13 C12 C11 119.81(11) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.20(11) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.08(11) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C14 C15 C16 120.08(12) . . ?
C14 C15 H15 120 . . ?
C16 C15 H15 120 . . ?
C15 C16 C11 120.07(11) . . ?
C15 C16 H16 120 . . ?
C11 C16 H16 120 . . ?
N3 N2 C1 101.49(8) . . ?
N4 N3 N2 114.13(8) . . ?
N4 N3 C31 122.47(8) . . ?
N2 N3 C31 123.08(8) . . ?
N3 C31 C32 110.41(8) . . ?
N3 C31 H31A 109.6 . . ?
C32 C31 H31A 109.6 . . ?
N3 C31 H31B 109.6 . . ?
C32 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
N33 C32 C31 111.73(8) . . ?
N33 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
N33 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 N33 C32 120.67(8) . . ?
C34 N33 H33 116.3(9) . . ?
C32 N33 H33 118.4(9) . . ?
O34 C34 O35 126.01(9) . . ?
O34 C34 N33 123.96(9) . . ?
O35 C34 N33 110.01(8) . . ?
C34 O35 C36 121.01(8) . . ?
O35 C36 C39 110.63(9) . . ?
O35 C36 C37 109.64(9) . . ?
C39 C36 C37 112.92(9) . . ?
O35 C36 C38 102.23(8) . . ?
C39 C36 C38 110.57(10) . . ?
C37 C36 C38 110.33(10) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N5 N4 N3 106.02(8) . . ?
N4 N5 C1 106.14(8) . . ?

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
N33 H33 O34 0.879(8) 2.044(10) 2.8586(11) 153.5(13) 4_565 yes


#===END

####################################################################### 
# 
# 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_at120
_audit_block_doi                 10.5517/ccdc.csd.cc1zzq8y
_database_code_depnum_ccdc_archive 'CCDC 1846771'
loop_
_audit_author_name
_audit_author_address
'Brian Skelton'
;University of Western Australia
Australia
;
_audit_update_record             
;
2018-06-01 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_date             2018-06-01T19:49:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C12 H13 F3 N4 O2'
_chemical_formula_moiety         'C10 H13 N4, C2 F3 O2'
_chemical_formula_weight         302.26
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.59850(10)
_cell_length_b                   7.6657(2)
_cell_length_c                   15.0325(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.928(2)
_cell_angle_gamma                90
_cell_volume                     640.43(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3569
_cell_measurement_theta_min      2.9588
_cell_measurement_theta_max      67.1956

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             312

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

_exptl_absorpt_coefficient_mu    1.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.35.21 

;
_exptl_absorpt_correction_T_min  0.92551
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      -0.1713581
_diffrn_orient_matrix_ub_12      0.1067271
_diffrn_orient_matrix_ub_13      0.0516943
_diffrn_orient_matrix_ub_21      0.1434145
_diffrn_orient_matrix_ub_22      -0.0563824
_diffrn_orient_matrix_ub_23      0.0893106
_diffrn_orient_matrix_ub_31      0.1640747
_diffrn_orient_matrix_ub_32      0.160672
_diffrn_orient_matrix_ub_33      -0.0030016
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_number            4496
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.961
_diffrn_reflns_theta_max         67.302
_diffrn_reflns_theta_full        67.302
_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 0.701
_diffrn_reflns_point_group_measured_fraction_max 0.701
_reflns_Friedel_fraction_full    0.352
_reflns_Friedel_fraction_max     0.352
_reflns_Friedel_coverage         0.3
_reflns_number_total             1606
_reflns_number_gt                1560
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;


__computing_structure_solution   'SIR92 (Altomare <i>et al.</i>, 1994)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'


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

_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)+(0.0415P)²+0.0985P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1606
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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'
F F 0.0727 0.0534 '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
N11 N 0.3745(3) 0.6340(3) 0.07872(11) 0.0217(4) Uani 1 1 d . . . . .
H11A H 0.318679 0.526209 0.061476 0.033 Uiso 1 1 calc R U . . .
H11B H 0.429854 0.688642 0.031517 0.033 Uiso 1 1 calc R U . . .
H11C H 0.253048 0.697815 0.097584 0.033 Uiso 1 1 calc R U . . .
C1 C 0.5739(4) 0.6166(3) 0.15337(14) 0.0214(5) Uani 1 1 d . . . . .
H1A H 0.701547 0.540353 0.134642 0.026 Uiso 1 1 calc R U . . .
H1B H 0.512714 0.562952 0.206085 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6765(4) 0.7963(3) 0.17788(15) 0.0228(5) Uani 1 1 d . . . . .
H2A H 0.736412 0.850167 0.124959 0.027 Uiso 1 1 calc R U . . .
H2B H 0.548739 0.872271 0.1968 0.027 Uiso 1 1 calc R U . . .
N1 N 0.8732(3) 0.7809(3) 0.25067(12) 0.0213(4) Uani 1 1 d . . . . .
N2 N 1.0935(3) 0.7328(3) 0.23327(13) 0.0233(4) Uani 1 1 d . . . . .
N3 N 1.2315(3) 0.7246(3) 0.30984(13) 0.0237(4) Uani 1 1 d . . . . .
C4 C 1.1004(3) 0.7681(3) 0.37739(15) 0.0214(4) Uani 1 1 d . . . . .
C5 C 0.8692(4) 0.8041(3) 0.33924(15) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.736104 0.837949 0.368973 0.027 Uiso 1 1 calc R U . . .
C41 C 1.2019(3) 0.7669(3) 0.47213(15) 0.0214(4) Uani 1 1 d . . . . .
C42 C 1.4200(4) 0.6820(3) 0.49995(15) 0.0239(5) Uani 1 1 d . . . . .
H42 H 1.505419 0.62581 0.457155 0.029 Uiso 1 1 calc R U . . .
C43 C 1.5109(4) 0.6800(3) 0.58987(16) 0.0265(5) Uani 1 1 d . . . . .
H43 H 1.660337 0.624277 0.608191 0.032 Uiso 1 1 calc R U . . .
C44 C 1.3861(4) 0.7587(4) 0.65348(15) 0.0271(5) Uani 1 1 d . . . . .
H44 H 1.448635 0.755691 0.715083 0.033 Uiso 1 1 calc R U . . .
C45 C 1.1689(4) 0.8420(3) 0.62637(15) 0.0275(5) Uani 1 1 d . . . . .
H45 H 1.082789 0.895944 0.669642 0.033 Uiso 1 1 calc R U . . .
C46 C 1.0775(4) 0.8467(3) 0.53660(15) 0.0236(5) Uani 1 1 d . . . . .
H46 H 0.929368 0.904466 0.518622 0.028 Uiso 1 1 calc R U . . .
F1 F 0.1403(3) 0.1076(2) 0.21784(9) 0.0321(3) Uani 1 1 d . . . . .
F2 F -0.1702(2) 0.1775(2) 0.12632(10) 0.0343(4) Uani 1 1 d . . . . .
F3 F 0.0936(2) 0.37148(19) 0.17133(9) 0.0278(3) Uani 1 1 d . . . . .
C11 C 0.0661(4) 0.2050(3) 0.14564(15) 0.0234(5) Uani 1 1 d . . . . .
C12 C 0.2067(4) 0.1571(3) 0.06609(15) 0.0249(5) Uani 1 1 d . . . . .
O1 O 0.3387(3) 0.2748(2) 0.04229(10) 0.0262(4) Uani 1 1 d . . . . .
O2 O 0.1719(4) 0.0076(3) 0.03768(14) 0.0438(5) 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
N11 C1 1.491(3) . ?
N11 H11A 0.91 . ?
N11 H11B 0.91 . ?
N11 H11C 0.91 . ?
C1 C2 1.521(3) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 N1 1.461(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
N1 N2 1.343(3) . ?
N1 C5 1.346(3) . ?
N2 N3 1.308(3) . ?
N3 C4 1.364(3) . ?
C4 C5 1.379(3) . ?
C4 C41 1.468(3) . ?
C5 H5 0.95 . ?
C41 C46 1.401(3) . ?
C41 C42 1.402(3) . ?
C42 C43 1.386(3) . ?
C42 H42 0.95 . ?
C43 C44 1.388(3) . ?
C43 H43 0.95 . ?
C44 C45 1.390(3) . ?
C44 H44 0.95 . ?
C45 C46 1.385(3) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
F1 C11 1.341(3) . ?
F2 C11 1.336(3) . ?
F3 C11 1.337(3) . ?
C11 C12 1.553(3) . ?
C12 O2 1.230(3) . ?
C12 O1 1.246(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
C1 N11 H11A 109.5 . . ?
C1 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C1 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
N11 C1 C2 109.15(18) . . ?
N11 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N11 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N1 C2 C1 109.68(18) . . ?
N1 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N2 N1 C5 110.74(17) . . ?
N2 N1 C2 120.23(18) . . ?
C5 N1 C2 129.01(17) . . ?
N3 N2 N1 107.50(17) . . ?
N2 N3 C4 109.22(17) . . ?
N3 C4 C5 107.56(19) . . ?
N3 C4 C41 122.70(19) . . ?
C5 C4 C41 129.71(19) . . ?
N1 C5 C4 104.97(18) . . ?
N1 C5 H5 127.5 . . ?
C4 C5 H5 127.5 . . ?
C46 C41 C42 119.0(2) . . ?
C46 C41 C4 120.10(19) . . ?
C42 C41 C4 120.9(2) . . ?
C43 C42 C41 120.0(2) . . ?
C43 C42 H42 120 . . ?
C41 C42 H42 120 . . ?
C42 C43 C44 120.7(2) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C43 C44 C45 119.5(2) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 120.3(2) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C45 C46 C41 120.4(2) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
F2 C11 F3 106.86(19) . . ?
F2 C11 F1 106.87(18) . . ?
F3 C11 F1 106.50(18) . . ?
F2 C11 C12 112.08(17) . . ?
F3 C11 C12 113.33(19) . . ?
F1 C11 C12 110.81(19) . . ?
O2 C12 O1 130.5(2) . . ?
O2 C12 C11 114.4(2) . . ?
O1 C12 C11 115.1(2) . . ?

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
N11 H11A O1 0.91 1.95 2.810(3) 156.1 . yes
N11 H11B O1 0.91 1.92 2.785(2) 157.7 2_655 yes
N11 H11C N2 0.91 2.34 3.054(3) 135.4 1_455 yes


#===END
####################################################################### 
# 
# 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_at130
_audit_block_doi                 10.5517/ccdc.csd.cc1zzsmc
_database_code_depnum_ccdc_archive 'CCDC 1846844'
loop_
_audit_author_name
_audit_author_address
'Brian Skelton'
;University of Western Australia
Australia
;
_audit_update_record             
;
2018-06-02 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_date             2018-06-02T11:40:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C10 H13 Cl N4'
_chemical_formula_moiety         'C10 H13 N4, Cl'
_chemical_formula_weight         224.69
_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                   5.36630(10)
_cell_length_b                   5.40550(10)
_cell_length_c                   39.3933(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1142.70(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4487
_cell_measurement_theta_min      3.0975
_cell_measurement_theta_max      29.3882

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             472

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

_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
     CrysAlisPro, Agilent Technologies, Version 1.171.35.21
;
_exptl_absorpt_correction_T_min  0.9913
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.0009
_diffrn_orient_matrix_ub_11      -0.0851609
_diffrn_orient_matrix_ub_12      0.0762813
_diffrn_orient_matrix_ub_13      -0.0089499
_diffrn_orient_matrix_ub_21      -0.099574
_diffrn_orient_matrix_ub_22      -0.0780527
_diffrn_orient_matrix_ub_23      0.0050677
_diffrn_orient_matrix_ub_31      -0.0174058
_diffrn_orient_matrix_ub_32      0.0728744
_diffrn_orient_matrix_ub_33      0.0147929
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_number            10374
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         3.103
_diffrn_reflns_theta_max         29.442
_diffrn_reflns_theta_full        28.5
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_coverage         0.66
_reflns_number_total             2977
_reflns_number_gt                2637
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'


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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion twin.
One reflection with poor agreement was omitted from the refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.25(10)
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.157
_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'
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
N11 N 0.2422(4) 0.4686(4) 0.71307(5) 0.0335(5) Uani 1 1 d . . . . .
H11A H 0.379482 0.386027 0.705629 0.05 Uiso 1 1 calc R U . . .
H11B H 0.106547 0.368162 0.711513 0.05 Uiso 1 1 calc R U . . .
H11C H 0.264676 0.514596 0.735077 0.05 Uiso 1 1 calc R U . . .
N1 N 0.2911(5) 0.4993(4) 0.63611(5) 0.0322(5) Uani 1 1 d . . . . .
N2 N 0.3277(4) 0.2547(4) 0.63893(6) 0.0360(6) Uani 1 1 d . . . . .
N3 N 0.5092(4) 0.1958(4) 0.61781(5) 0.0344(5) Uani 1 1 d . . . . .
C1 C 0.2027(5) 0.6917(5) 0.69187(7) 0.0365(6) Uani 1 1 d . . . . .
H1A H 0.362205 0.782194 0.689528 0.044 Uiso 1 1 calc R U . . .
H1B H 0.082056 0.802666 0.70326 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1053(5) 0.6247(6) 0.65689(7) 0.0383(6) Uani 1 1 d . . . . .
H2A H -0.042075 0.516124 0.659383 0.046 Uiso 1 1 calc R U . . .
H2B H 0.051125 0.777434 0.645143 0.046 Uiso 1 1 calc R U . . .
C4 C 0.5869(5) 0.4041(5) 0.60128(6) 0.0296(6) Uani 1 1 d . . . . .
C5 C 0.4491(5) 0.5981(5) 0.61330(6) 0.0328(6) Uani 1 1 d . . . . .
H5 H 0.462173 0.767065 0.606898 0.039 Uiso 1 1 calc R U . . .
C41 C 0.7812(5) 0.3983(4) 0.57527(6) 0.0295(5) Uani 1 1 d . . . . .
C42 C 0.9515(5) 0.2049(5) 0.57346(7) 0.0347(6) Uani 1 1 d . . . . .
H42 H 0.942372 0.073339 0.589403 0.042 Uiso 1 1 calc R U . . .
C43 C 1.1339(5) 0.2020(5) 0.54872(7) 0.0392(7) Uani 1 1 d . . . . .
H43 H 1.248048 0.067912 0.547699 0.047 Uiso 1 1 calc R U . . .
C44 C 1.1519(5) 0.3925(6) 0.52543(7) 0.0392(7) Uani 1 1 d . . . . .
H44 H 1.278162 0.39052 0.508533 0.047 Uiso 1 1 calc R U . . .
C45 C 0.9842(5) 0.5856(6) 0.52703(7) 0.0394(7) Uani 1 1 d . . . . .
H45 H 0.995897 0.717637 0.511193 0.047 Uiso 1 1 calc R U . . .
C46 C 0.7994(5) 0.5890(5) 0.55143(7) 0.0350(6) Uani 1 1 d . . . . .
H46 H 0.683708 0.721964 0.552013 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.74052(12) 0.16348(12) 0.71184(2) 0.03517(17) 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
N11 C1 1.482(3) . ?
N11 H11A 0.91 . ?
N11 H11B 0.91 . ?
N11 H11C 0.91 . ?
N1 N2 1.341(3) . ?
N1 C5 1.346(3) . ?
N1 C2 1.457(3) . ?
N2 N3 1.320(3) . ?
N3 C4 1.366(3) . ?
C1 C2 1.518(4) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C4 C5 1.368(4) . ?
C4 C41 1.462(4) . ?
C5 H5 0.95 . ?
C41 C42 1.391(4) . ?
C41 C46 1.398(3) . ?
C42 C43 1.381(4) . ?
C42 H42 0.95 . ?
C43 C44 1.383(4) . ?
C43 H43 0.95 . ?
C44 C45 1.380(4) . ?
C44 H44 0.95 . ?
C45 C46 1.381(4) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?

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
C1 N11 H11A 109.5 . . ?
C1 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C1 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
N2 N1 C5 110.8(2) . . ?
N2 N1 C2 120.8(2) . . ?
C5 N1 C2 128.4(2) . . ?
N3 N2 N1 107.1(2) . . ?
N2 N3 C4 109.1(2) . . ?
N11 C1 C2 111.5(2) . . ?
N11 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N11 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108 . . ?
N1 C2 C1 112.7(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C4 C5 107.6(2) . . ?
N3 C4 C41 122.3(2) . . ?
C5 C4 C41 130.1(2) . . ?
N1 C5 C4 105.5(2) . . ?
N1 C5 H5 127.3 . . ?
C4 C5 H5 127.3 . . ?
C42 C41 C46 118.3(2) . . ?
C42 C41 C4 121.4(2) . . ?
C46 C41 C4 120.3(2) . . ?
C43 C42 C41 120.7(3) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 120.6(3) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C45 C44 C43 119.2(3) . . ?
C45 C44 H44 120.4 . . ?
C43 C44 H44 120.4 . . ?
C44 C45 C46 120.7(3) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C41 120.5(3) . . ?
C45 C46 H46 119.7 . . ?
C41 C46 H46 119.7 . . ?

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
N11 H11A Cl1 0.91 2.29 3.142(2) 155.1 . yes
N11 H11B Cl1 0.91 2.25 3.157(2) 171.6 1_455 yes
N11 H11C Cl1 0.91 2.24 3.141(2) 170.3 4_656 yes


#===END
####################################################################### 
# 
# 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_at240
_audit_block_doi                 10.5517/ccdc.csd.cc1zzth8
_database_code_depnum_ccdc_archive 'CCDC 1846871'
loop_
_audit_author_name
_audit_author_address
'Brian Skelton'
;University of Western Australia
Australia
;
_audit_update_record             
;
2018-06-02 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_date             2018-06-02T20:47:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C15 H20 N4 O2'
_chemical_formula_moiety         'C15 H20 N4 O2'
_chemical_formula_weight         288.35

#----------------------------------------------------------------------------#
#                   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                   13.8888(13)
_cell_length_b                   11.5000(7)
_cell_length_c                   9.9679(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.959(8)
_cell_angle_gamma                90
_cell_volume                     1514.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      3.6234
_cell_measurement_theta_max      29.0996

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             616

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies, Version 1.171.35.21
;
_exptl_absorpt_correction_T_min  0.95682
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_ub_11      0.0458776
_diffrn_orient_matrix_ub_12      -0.0320609
_diffrn_orient_matrix_ub_13      0.0220172
_diffrn_orient_matrix_ub_21      0.0275932
_diffrn_orient_matrix_ub_22      0.0525005
_diffrn_orient_matrix_ub_23      0.0192956
_diffrn_orient_matrix_ub_31      -0.0044065
_diffrn_orient_matrix_ub_32      -0.0044135
_diffrn_orient_matrix_ub_33      0.0688137
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.05
_diffrn_reflns_av_unetI/netI     0.1316
_diffrn_reflns_number            11821
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.631
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        27
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_reflns_Friedel_coverage         0
_reflns_number_total             3390
_reflns_number_gt                2394
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.35.21 
;

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'



#----------------------------------------------------------------------------#
#                   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)+(0.0447P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.093
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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 0.15167(10) 0.48046(14) 0.59191(13) 0.0212(3) Uani 1 1 d . . . . .
C11 C 0.12350(11) 0.55216(13) 0.69620(14) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.04137(11) 0.52280(14) 0.74105(14) 0.0255(4) Uani 1 1 d . . . . .
H12 H 0.001323 0.456872 0.701908 0.031 Uiso 1 1 calc R U . . .
C13 C 0.01749(12) 0.58896(16) 0.84241(15) 0.0346(4) Uani 1 1 d . . . . .
H13 H -0.038425 0.568042 0.873231 0.042 Uiso 1 1 calc R U . . .
C14 C 0.07526(13) 0.68575(17) 0.89886(17) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.058882 0.731406 0.968232 0.048 Uiso 1 1 calc R U . . .
C15 C 0.15653(13) 0.71566(16) 0.85416(17) 0.0397(5) Uani 1 1 d . . . . .
H15 H 0.19598 0.78211 0.892844 0.048 Uiso 1 1 calc R U . . .
C16 C 0.18099(12) 0.64959(15) 0.75339(16) 0.0319(4) Uani 1 1 d . . . . .
H16 H 0.237124 0.670726 0.723159 0.038 Uiso 1 1 calc R U . . .
N2 N 0.11791(9) 0.37225(11) 0.56232(11) 0.0216(3) Uani 1 1 d . . . . .
N3 N 0.16208(8) 0.33929(11) 0.46421(11) 0.0206(3) Uani 1 1 d . . . . .
C31 C 0.15288(11) 0.22092(13) 0.41098(14) 0.0234(3) Uani 1 1 d . . . . .
H31A H 0.165168 0.219672 0.318295 0.028 Uiso 1 1 calc R U . . .
H31B H 0.083293 0.192315 0.39745 0.028 Uiso 1 1 calc R U . . .
C32 C 0.22852(10) 0.14112(14) 0.51322(14) 0.0225(3) Uani 1 1 d . . . . .
H32A H 0.211184 0.13529 0.602161 0.027 Uiso 1 1 calc R U . . .
H32B H 0.22405 0.062249 0.471924 0.027 Uiso 1 1 calc R U . . .
N33 N 0.33111(9) 0.18429(11) 0.54346(12) 0.0210(3) Uani 1 1 d D . . . .
C34 C 0.37590(10) 0.24518(13) 0.66318(13) 0.0195(3) Uani 1 1 d . . . . .
O34 O 0.34619(7) 0.24636(9) 0.76612(9) 0.0258(3) Uani 1 1 d . . . . .
O35 O 0.45825(7) 0.29941(9) 0.65113(9) 0.0248(3) Uani 1 1 d . . . . .
C36 C 0.52033(11) 0.37629(14) 0.76403(14) 0.0249(4) Uani 1 1 d . . . . .
C37 C 0.57053(12) 0.30510(15) 0.89554(15) 0.0320(4) Uani 1 1 d . . . . .
H37A H 0.518625 0.274457 0.933924 0.048 Uiso 1 1 calc R U . . .
H37B H 0.617368 0.354572 0.966193 0.048 Uiso 1 1 calc R U . . .
H37C H 0.607956 0.240369 0.871263 0.048 Uiso 1 1 calc R U . . .
C38 C 0.59937(12) 0.42058(17) 0.69939(16) 0.0371(4) Uani 1 1 d . . . . .
H38A H 0.635809 0.354485 0.676101 0.056 Uiso 1 1 calc R U . . .
H38B H 0.647292 0.471253 0.767033 0.056 Uiso 1 1 calc R U . . .
H38C H 0.565895 0.464543 0.61342 0.056 Uiso 1 1 calc R U . . .
C39 C 0.45642(12) 0.47553(15) 0.78922(16) 0.0330(4) Uani 1 1 d . . . . .
H39A H 0.420799 0.512735 0.699124 0.05 Uiso 1 1 calc R U . . .
H39B H 0.500105 0.532663 0.852349 0.05 Uiso 1 1 calc R U . . .
H39C H 0.40696 0.445438 0.832503 0.05 Uiso 1 1 calc R U . . .
C4 C 0.21908(11) 0.42589(14) 0.44147(14) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.257604 0.42213 0.37767 0.03 Uiso 1 1 calc R U . . .
N5 N 0.21489(9) 0.51749(11) 0.51932(12) 0.0252(3) Uani 1 1 d . . . . .
H33 H 0.3516(11) 0.2000(14) 0.4712(12) 0.025(4) Uiso 1 1 d 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 N2 1.3305(19) . ?
C1 N5 1.3666(17) . ?
C1 C11 1.471(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.95 . ?
C13 C14 1.386(3) . ?
C13 H13 0.95 . ?
C14 C15 1.379(2) . ?
C14 H14 0.95 . ?
C15 C16 1.383(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
N2 N3 1.3588(15) . ?
N3 C4 1.3344(18) . ?
N3 C31 1.4522(19) . ?
C31 C32 1.525(2) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 N33 1.4502(18) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
N33 C34 1.3578(18) . ?
N33 H33 0.871(9) . ?
C34 O34 1.2184(15) . ?
C34 O35 1.3402(16) . ?
O35 C36 1.4810(16) . ?
C36 C39 1.514(2) . ?
C36 C37 1.520(2) . ?
C36 C38 1.522(2) . ?
C37 H37A 0.98 . ?
C37 H37B 0.98 . ?
C37 H37C 0.98 . ?
C38 H38A 0.98 . ?
C38 H38B 0.98 . ?
C38 H38C 0.98 . ?
C39 H39A 0.98 . ?
C39 H39B 0.98 . ?
C39 H39C 0.98 . ?
C4 N5 1.3202(19) . ?
C4 H4 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N5 114.46(13) . . ?
N2 C1 C11 121.90(13) . . ?
N5 C1 C11 123.63(14) . . ?
C12 C11 C16 119.22(14) . . ?
C12 C11 C1 120.99(14) . . ?
C16 C11 C1 119.78(14) . . ?
C13 C12 C11 120.44(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.92(16) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C15 C14 C13 119.88(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.44(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.10(16) . . ?
C15 C16 H16 120 . . ?
C11 C16 H16 120 . . ?
C1 N2 N3 102.36(11) . . ?
C4 N3 N2 109.71(12) . . ?
C4 N3 C31 128.87(12) . . ?
N2 N3 C31 121.06(11) . . ?
N3 C31 C32 110.81(11) . . ?
N3 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N3 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
N33 C32 C31 111.30(12) . . ?
N33 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
N33 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108 . . ?
C34 N33 C32 120.91(12) . . ?
C34 N33 H33 116.2(10) . . ?
C32 N33 H33 116.8(10) . . ?
O34 C34 O35 126.18(12) . . ?
O34 C34 N33 124.31(13) . . ?
O35 C34 N33 109.48(11) . . ?
C34 O35 C36 121.51(10) . . ?
O35 C36 C39 110.02(12) . . ?
O35 C36 C37 109.78(13) . . ?
C39 C36 C37 113.55(12) . . ?
O35 C36 C38 101.83(11) . . ?
C39 C36 C38 110.75(14) . . ?
C37 C36 C38 110.27(13) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N5 C4 N3 111.08(12) . . ?
N5 C4 H4 124.5 . . ?
N3 C4 H4 124.5 . . ?
C4 N5 C1 102.39(13) . . ?

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
N33 H33 O34 0.871(9) 2.114(10) 2.9460(14) 159.4(13) 4_565 yes


#===END
