# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_13c
_database_code_depnum_ccdc_archive 'CCDC 2113094'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;


_chemical_name_common            
1,5-di(methylbenzene)-3-(4-nitro-thiophenyl-oxoverdazyl
_chemical_name_systematic        
1,5-di(methylbenzene)-3-(4-nitro-thiophenyl-oxoverdazyl
_chemical_formula_moiety         'C8 H11 N5 O3 S'
_chemical_formula_sum            'C8 H11 N5 O3 S'
_chemical_formula_weight         257.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H11 N5 O3 S'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'


_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
PLAT430_ALERT_2_B Short Inter                 D...A Contact O1 ..N5 . 2.79 Ang.

This is correct.
#-------------------------------------------------------------------------------
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.650 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 39 Note


#-------------------------------------------------------------------------------
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do !
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Info

No action taken.
#-------------------------------------------------------------------------------
;

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.73880(10)
_cell_length_b                   8.73770(10)
_cell_length_c                   15.3935(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.809(2)
_cell_angle_gamma                90
_cell_volume                     1130.94(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8557
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.0630
_cell_measurement_theta_min      5.8520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.033
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20676
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.258
_diffrn_reflns_theta_min         5.261
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  14.00   0.50    1.00    --  -46.07 102.00  92.00  190
  2  ω    -14.00  81.00   0.50    1.00    --   46.07-102.00 -10.00  190
  3  ω   -174.00 -85.00   0.50    5.00    -- -102.29-102.00 -10.00  178
  4  ω   -106.00 -30.00   0.50    5.00    -- -102.29 102.00  92.00  152
  5  ω     30.00 106.00   0.50    5.00    --  102.29-102.00 -10.00  152
  6  ω     85.00 174.00   0.50    5.00    --  102.29 102.00  92.00  178
  7  ω    -26.00  29.00   0.50    1.00    --  -46.07  19.00  30.00  110
  8  ω   -119.00 -73.00   0.50    1.00    --  -46.07-125.00  60.00   92
  9  ω     74.00 119.00   0.50    1.00    --   46.07 125.00  60.00   90
 10  ω     74.00 119.00   0.50    1.00    --   46.07 125.00  90.00   90
 11  ω     31.00 119.00   0.50    1.00    --   46.07  57.00-180.00  176
 12  ω     74.00 119.00   0.50    1.00    --   46.07 125.00   0.00   90
 13  ω   -174.00 -84.00   0.50    5.00    -- -102.29 -65.00   8.87  180
 14  ω    -71.00 -30.00   0.50    5.00    -- -102.29  61.00  60.00   82
 15  ω    -71.00 -30.00   0.50    5.00    -- -102.29  61.00-120.00   82
 16  ω   -121.00 -30.00   0.50    5.00    -- -102.29 138.00-102.67  182
 17  ω   -174.00 -86.00   0.50    5.00    -- -102.29 -62.00 -66.20  176
 18  ω    -71.00 -30.00   0.50    5.00    -- -102.29  61.00 120.00   82
 19  ω   -105.00 -30.00   0.50    5.00    -- -102.29  77.00-120.00  150
 20  ω   -174.00 -90.00   0.50    5.00    -- -102.29 -46.00 -98.30  168
 21  ω    -71.00 -30.00   0.50    5.00    -- -102.29  61.00 -60.00   82
 22  ω   -174.00 -80.00   0.50    5.00    -- -102.29 -77.00-120.00  188
 23  ω   -174.00 -85.00   0.50    5.00    -- -102.29 -64.00  29.91  178
 24  ω     30.00 111.00   0.50    5.00    --  102.29-125.00-150.00  162
 25  ω     30.00 105.00   0.50    5.00    --  102.29 -77.00 -30.00  150
 26  ω     30.00 111.00   0.50    5.00    --  102.29-125.00-120.00  162
 27  ω     30.00  71.00   0.50    5.00    --  102.29 -61.00  30.00   82
 28  ω     90.00 174.00   0.50    5.00    --  102.29  45.00-180.00  168
 29  ω     30.00  71.00   0.50    5.00    --  102.29 -61.00   0.00   82
 30  ω     30.00 105.00   0.50    5.00    --  102.29 -94.00 150.00  150
 31  ω     24.00 119.00   0.50    1.00    --   46.07  77.00 -60.00  190
 32  ω     24.00 119.00   0.50    1.00    --   46.07  77.00  60.00  190
 33  ω     31.00 119.00   0.50    1.00    --   46.07  57.00  30.00  176
 34  ω     24.00 119.00   0.50    1.00    --   46.07  77.00  90.00  190
 35  ω     24.00 119.00   0.50    1.00    --   46.07  77.00-180.00  190
 36  ω     24.00 119.00   0.50    1.00    --   46.07  77.00-120.00  190
 37  ω   -176.00-110.00   0.50    5.00    -- -102.29 -30.00  90.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2078
_reflns_number_total             2293
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.8363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.0937

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S1 S 0.77387(5) 0.53298(5) 0.43057(3) 0.02092(14) Uani 1 1 d . . . . .
O1 O 0.38545(15) 0.67321(16) 0.19564(9) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.83144(17) 0.21951(18) 0.49427(10) 0.0309(3) Uani 1 1 d . . . . .
O3 O 0.97529(16) 0.14896(16) 0.40613(10) 0.0297(3) Uani 1 1 d . . . . .
N3 N 0.60927(18) 0.81217(19) 0.20711(11) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.49600(18) 0.7953(2) 0.32781(11) 0.0233(3) Uani 1 1 d . . . . .
N5 N 0.89650(18) 0.24428(19) 0.43410(11) 0.0230(3) Uani 1 1 d . . . . .
N2 N 0.63804(18) 0.8480(2) 0.39230(11) 0.0222(3) Uani 1 1 d . . . . .
N4 N 0.74704(18) 0.8848(2) 0.26398(11) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.4928(2) 0.7553(2) 0.24188(12) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.7748(2) 0.8275(2) 0.35591(12) 0.0206(4) Uani 1 1 d . . . . .
H2A H 0.865961 0.886186 0.395181 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8816(2) 0.3938(2) 0.39512(12) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.9515(2) 0.4416(2) 0.33095(13) 0.0232(4) Uani 1 1 d . . . . .
H5 H 1.015050 0.378844 0.304211 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8235(2) 0.6616(2) 0.35812(12) 0.0202(4) Uani 1 1 d . . . . .
C4 C 0.9171(2) 0.5962(2) 0.30967(14) 0.0244(4) Uani 1 1 d . . . . .
H4A H 0.954875 0.650218 0.266073 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6273(3) 0.7509(3) 0.12283(13) 0.0309(5) Uani 1 1 d . . . . .
H8A H 0.688549 0.823016 0.096787 0.046 Uiso 1 1 calc R U . . .
H8B H 0.522151 0.735692 0.080541 0.046 Uiso 1 1 calc R U . . .
H8C H 0.683484 0.652784 0.134258 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3786(2) 0.7337(3) 0.36919(15) 0.0321(5) Uani 1 1 d . . . . .
H7A H 0.411431 0.631291 0.393013 0.048 Uiso 1 1 calc R U . . .
H7B H 0.275336 0.727379 0.323933 0.048 Uiso 1 1 calc R U . . .
H7C H 0.369773 0.800870 0.418582 0.048 Uiso 1 1 calc R U . . .
H2 H 0.628(3) 0.947(3) 0.3978(14) 0.018(5) Uiso 1 1 d . . . . .
H4 H 0.727(3) 0.982(3) 0.2651(14) 0.018(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.7155(19) . ?
S1 C3 1.7200(19) . ?
O1 C1 1.240(2) . ?
O2 N5 1.231(2) . ?
O3 N5 1.231(2) . ?
N3 N4 1.430(2) . ?
N3 C1 1.366(2) . ?
N3 C8 1.451(2) . ?
N1 N2 1.438(2) . ?
N1 C1 1.361(2) . ?
N1 C7 1.450(2) . ?
N5 C6 1.428(2) . ?
N2 C2 1.462(2) . ?
N2 H2 0.88(2) . ?
N4 C2 1.458(2) . ?
N4 H4 0.87(2) . ?
C2 H2A 1.0000 . ?
C2 C3 1.509(3) . ?
C6 C5 1.362(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.403(3) . ?
C3 C4 1.373(3) . ?
C4 H4A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C3 89.99(9) . . ?
N4 N3 C8 115.63(15) . . ?
C1 N3 N4 120.97(15) . . ?
C1 N3 C8 119.35(16) . . ?
N2 N1 C7 113.35(15) . . ?
C1 N1 N2 122.59(14) . . ?
C1 N1 C7 120.11(16) . . ?
O2 N5 C6 117.95(16) . . ?
O3 N5 O2 124.15(17) . . ?
O3 N5 C6 117.89(16) . . ?
N1 N2 C2 109.78(14) . . ?
N1 N2 H2 106.9(14) . . ?
C2 N2 H2 105.9(14) . . ?
N3 N4 C2 109.38(14) . . ?
N3 N4 H4 107.9(14) . . ?
C2 N4 H4 107.4(14) . . ?
O1 C1 N3 120.90(17) . . ?
O1 C1 N1 121.24(17) . . ?
N1 C1 N3 117.83(16) . . ?
N2 C2 H2A 107.8 . . ?
N2 C2 C3 111.31(15) . . ?
N4 C2 N2 113.12(15) . . ?
N4 C2 H2A 107.8 . . ?
N4 C2 C3 108.85(15) . . ?
C3 C2 H2A 107.8 . . ?
N5 C6 S1 120.67(14) . . ?
C5 C6 S1 114.01(14) . . ?
C5 C6 N5 125.29(17) . . ?
C6 C5 H5 124.6 . . ?
C6 C5 C4 110.79(17) . . ?
C4 C5 H5 124.6 . . ?
C2 C3 S1 121.54(13) . . ?
C4 C3 S1 111.91(15) . . ?
C4 C3 C2 126.43(17) . . ?
C5 C4 H4A 123.4 . . ?
C3 C4 C5 113.29(18) . . ?
C3 C4 H4A 123.4 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C6 C5 C4 0.0(2) . . . . ?
S1 C3 C4 C5 -0.6(2) . . . . ?
O2 N5 C6 S1 -0.8(2) . . . . ?
O2 N5 C6 C5 177.05(18) . . . . ?
O3 N5 C6 S1 -179.93(13) . . . . ?
O3 N5 C6 C5 -2.1(3) . . . . ?
N3 N4 C2 N2 -56.3(2) . . . . ?
N3 N4 C2 C3 67.98(17) . . . . ?
N1 N2 C2 N4 48.1(2) . . . . ?
N1 N2 C2 C3 -74.80(18) . . . . ?
N5 C6 C5 C4 -177.94(17) . . . . ?
N2 N1 C1 O1 160.30(17) . . . . ?
N2 N1 C1 N3 -21.6(3) . . . . ?
N2 C2 C3 S1 -22.1(2) . . . . ?
N2 C2 C3 C4 162.09(18) . . . . ?
N4 N3 C1 O1 -169.42(16) . . . . ?
N4 N3 C1 N1 12.5(3) . . . . ?
N4 C2 C3 S1 -147.48(13) . . . . ?
N4 C2 C3 C4 36.7(2) . . . . ?
C1 N3 N4 C2 25.3(2) . . . . ?
C1 N1 N2 C2 -8.9(2) . . . . ?
C2 C3 C4 C5 175.53(17) . . . . ?
C6 S1 C3 C2 -175.83(15) . . . . ?
C6 S1 C3 C4 0.51(15) . . . . ?
C6 C5 C4 C3 0.4(2) . . . . ?
C3 S1 C6 N5 177.77(15) . . . . ?
C3 S1 C6 C5 -0.32(15) . . . . ?
C8 N3 N4 C2 -131.90(17) . . . . ?
C8 N3 C1 O1 -13.0(3) . . . . ?
C8 N3 C1 N1 168.86(17) . . . . ?
C7 N1 N2 C2 148.73(17) . . . . ?
C7 N1 C1 O1 4.2(3) . . . . ?
C7 N1 C1 N3 -177.76(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 2113098'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H24 O N4'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.58380(10)
_cell_length_b                   9.81170(10)
_cell_length_c                   12.89680(10)
_cell_angle_alpha                102.5530(10)
_cell_angle_beta                 92.8410(10)
_cell_angle_gamma                111.3200(10)
_cell_volume                     863.837(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23822
_cell_measurement_temperature    101(1)
_cell_measurement_theta_max      75.3330
_cell_measurement_theta_min      3.5340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -8 0.0928
5 -4 -1 0.0813
1 -2 8 0.0664
-5 4 1 0.0642
-3 2 -6 0.0897
0 6 1 0.0608
1 -6 0 0.0392
-1 4 -7 0.0731
-3 -3 5 0.1013
4 0 -1 0.0714

_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.108
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9562 2.0035 -8.1205 0.4678 0.2237 -0.8551
4.5727 -4.2092 -0.7002 0.6940 0.3299 0.6400
1.1909 -2.2091 8.0076 -0.4265 -0.2040 0.8812
-4.5567 4.1461 1.0535 -0.7179 -0.3414 -0.6067
-3.0530 1.7685 -6.1907 0.2605 -0.2239 -0.9392
-0.2307 5.6780 0.7962 -0.7500 0.6410 -0.1633
0.6571 -6.0159 0.0478 0.7262 -0.6205 0.2960
-1.0350 4.4148 -7.1322 0.0912 0.4872 -0.8685
-2.8075 -2.9511 4.9582 -0.1800 -0.9677 0.1765
4.4712 0.3593 -0.8287 0.1624 0.8754 0.4553

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31912
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.872
_diffrn_reflns_theta_min         3.547
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 119.00   0.50    0.05    --   46.07  77.00 150.00  190
  2  ω     24.00 119.00   0.50    0.05    --   46.07  77.00  90.00  190
  3  ω     29.00 119.00   0.50    0.05    --   46.07  64.00  79.00  180
  4  ω     24.00 119.00   0.50    0.05    --   46.07  77.00  60.00  190
  5  ω     28.00 122.00   0.50    0.05    --   50.00  76.00-119.87  188
  6  ω     24.00 119.00   0.50    0.05    --   46.07  77.00-180.00  190
  7  ω     34.00 119.00   0.50    0.05    --   46.07  38.00-180.00  170
  8  ω     34.00 122.00   0.50    0.05    --   46.07  19.00-180.00  176
  9  ω     87.00 177.00   0.50    0.25    --  103.87  64.00  79.00  180
 10  ω     31.00 126.00   0.50    0.05    --   54.00  77.00 158.43  190
 11  ω     35.00 131.00   0.50    0.05    --   58.00  77.00  71.98  192
 12  ω     63.00 152.00   0.50    0.25    --   86.00  77.00  55.40  178
 13  ω     32.00 126.00   0.50    0.05    --   54.00  76.00 -34.48  188
 14  ω     74.00 100.00   0.50    0.05    --   66.00  77.00-104.74   52
 15  ω     44.00  70.00   0.50    0.05    --   66.00  77.00-104.74   52
 16  ω     40.00  66.00   0.50    0.05    --   62.00  77.00 -72.89   52
 17  ω     32.00 126.00   0.50    0.05    --   54.00  75.00 -80.86  188
 18  ω     41.00 128.00   0.50    0.05    --   62.00  73.00-114.66  174
 19  ω     32.00 126.00   0.50    0.05    --   54.00  76.00  16.09  188
 20  ω     42.00  68.00   0.50    0.05    --   62.00  75.00  25.41   52
 21  ω     43.00  68.00   0.50    0.05    --   62.00  76.00  90.21   50
 22  ω     14.00  43.00   0.50    0.05    --   42.00  88.00-117.61   58
 23  ω      5.00  43.00   0.50    0.05    --   34.00  90.00 -74.57   76
 24  ω    -16.00  22.00   0.50    0.05    --   18.00 100.00 -88.79   76
 25  ω    -21.00  14.00   0.50    0.05    --   14.00 102.00 -27.09   70
 26  ω     31.00  76.00   0.50    0.25    --  103.87 -64.00 -56.00   90
 27  ω     36.00  71.00   0.50    0.25    --  103.87 -61.00   0.00   70
 28  ω    -25.00  61.00   0.50    0.05    --   46.07 -57.00  90.00  172
 29  ω    -25.00  64.00   0.50    0.05    --   46.07 -64.00 -56.00  178
 30  ω     31.00  69.00   0.50    0.25    --  103.87 -61.00 -90.00   76
 31  ω     32.00  60.00   0.50    0.25    --  103.87 -94.00-120.00   56
 32  ω     73.00 111.00   0.50    0.25    --  103.87-125.00-150.00   76
 33  ω     38.00  67.00   0.50    0.25    --  103.87-125.00 -30.00   58
 34  ω     72.00 112.00   0.50    0.25    --  103.87-125.00 -30.00   80
 35  ω     85.00 112.00   0.50    0.25    --  103.87-125.00   0.00   54
 36  ω     33.00  97.00   0.50    0.25    --  103.87 -94.00 120.00  128
 37  ω     52.00 112.00   0.50    0.25    --  103.87-125.00  90.00  120
 38  ω     75.00 105.00   0.50    0.25    --  103.87 -94.00 150.00   60
 39  ω     46.00  72.00   0.50    0.25    --  103.87 -94.00 150.00   52
 40  ω     64.00  93.00   0.50    0.25    --  103.87 -94.00-120.00   58
 41  ω     38.00  69.00   0.50    0.25    --  103.87 -94.00-150.00   62
 42  ω     72.00 104.00   0.50    0.25    --  103.87 -94.00-150.00   64
 43  ω   -108.00 -41.00   0.50    0.25    -- -103.87 125.00  60.00  134
 44  ω   -107.00 -79.00   0.50    0.25    -- -103.87 125.00  30.00   56
 45  ω    -76.00 -50.00   0.50    0.25    -- -103.87 125.00  30.00   52
 46  ω    -87.00 -34.00   0.50    0.25    -- -103.87 125.00 -60.00  106
 47  ω    -64.00 -33.00   0.50    0.25    -- -103.87  61.00 -60.00   62
 48  ω    -70.00 -32.00   0.50    0.25    -- -103.87  61.00-150.00   76
 49  ω    -63.00  27.00   0.50    0.05    --  -46.07  64.00  79.00  180
 50  ω    -76.00 -31.00   0.50    0.25    -- -103.87  64.00  79.00   90
 51  ω   -174.00-143.00   0.50    0.25    -- -103.87 -45.00  30.00   62
 52  ω   -166.00 -80.00   0.50    0.25    -- -103.87 -79.00  11.04  172
 53  ω   -176.00 -80.00   0.50    0.25    -- -103.87 -79.00-100.74  192
 54  ω   -175.00-121.00   0.50    0.25    -- -103.87 -77.00-140.45  108
 55  ω   -113.00 -83.00   0.50    0.25    -- -103.87 -77.00-140.45   60
 56  ω   -126.00 -76.00   0.50    0.25    --  -98.00 -77.00 -81.99  100
 57  ω   -159.00-132.00   0.50    0.25    --  -98.00 -77.00 -81.99   54
 58  ω   -161.00-117.00   0.50    0.25    --  -94.00 -76.00  24.21   88
 59  ω   -100.00 -71.00   0.50    0.25    --  -94.00 -76.00  24.21   58
 60  ω   -166.00 -71.00   0.50    0.25    --  -94.00 -76.00 -13.58  190
 61  ω   -174.00-131.00   0.50    0.25    -- -103.87 -77.00 120.00   86
 62  ω   -118.00 -81.00   0.50    0.25    -- -103.87 -77.00 120.00   74
 63  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -76.00 149.33   52
 64  ω    -91.00 -64.00   0.50    0.25    --  -86.00 -75.00 138.32   54
 65  ω    -83.00 -52.00   0.50    0.05    --  -74.00 -75.00 103.98   62
 66  ω    -86.00 -51.00   0.50    0.05    --  -74.00 -76.00  18.54   70
 67  ω   -145.00-119.00   0.50    0.05    --  -74.00 -75.00 103.98   52
 68  ω   -138.00 -97.00   0.50    0.05    --  -74.00 -76.00  18.54   82
 69  ω    -82.00 -52.00   0.50    0.05    --  -74.00 -75.00  67.85   60
 70  ω   -115.00 -68.00   0.50    0.25    --  -90.00 -74.00 -75.26   94
 71  ω    -79.00 -54.00   0.50    0.05    --  -74.00 -74.00 -99.20   50
 72  ω   -155.00 -65.00   0.50    0.25    --  -86.00 -74.00-115.29  180
 73  ω   -153.00 -84.00   0.50    0.25    -- -103.87 -75.00-164.92  138
 74  ω    -91.00 -65.00   0.50    0.25    --  -86.00 -75.00-144.03   52
 75  ω    -78.00 -53.00   0.50    0.05    --  -74.00 -73.00 -68.75   50
 76  ω    -93.00 -65.00   0.50    0.25    --  -86.00 -73.00  27.28   56
 77  ω    -86.00 -61.00   0.50    0.25    --  -82.00 -72.00  83.92   50
 78  ω    -95.00 -67.00   0.50    0.25    --  -86.00 -72.00  64.45   56
 79  ω   -158.00-108.00   0.50    0.25    --  -86.00 -72.00  64.45  100
 80  ω   -150.00 -99.00   0.50    0.25    --  -82.00 -72.00 149.50  102
 81  ω    -93.00 -61.00   0.50    0.25    --  -82.00 -72.00 149.50   64
 82  ω    -82.00 -57.00   0.50    0.25    --  -78.00 -72.00 173.40   50
 83  ω   -142.00-115.00   0.50    0.25    --  -78.00 -72.00 173.40   54
 84  ω   -135.00 -42.00   0.50    0.05    --  -62.00 -70.00 168.16  186
 85  ω   -100.00 -66.00   0.50    0.25    --  -86.00 -71.00 114.06   68
 86  ω   -148.00 -85.00   0.50    0.25    -- -103.87 -68.00 152.03  126
 87  ω    -80.00 -54.00   0.50    0.05    --  -74.00 -69.00 -36.93   52
 88  ω    -79.00 -51.00   0.50    0.05    --  -70.00 -68.00 -57.76   56
 89  ω   -122.00 -80.00   0.50    0.25    --  -98.00 -70.00-146.75   84
 90  ω   -153.00-127.00   0.50    0.25    --  -98.00 -70.00-146.75   52
 91  ω    -94.00 -64.00   0.50    0.25    --  -82.00 -65.00 -66.81   60
 92  ω   -119.00 -29.00   0.50    0.05    --  -46.07 -64.00 -56.00  180
 93  ω   -109.00 -68.00   0.50    0.25    --  -86.00 -64.00 -11.71   82
 94  ω   -176.00 -86.00   0.50    0.25    -- -103.87 -64.00 -56.00  180
 95  ω   -139.00-114.00   0.50    0.25    --  -94.00 -65.00  73.31   50
 96  ω   -110.00 -76.00   0.50    0.25    --  -94.00 -65.00  73.31   68
 97  ω   -125.00 -76.00   0.50    0.25    --  -94.00 -64.00 178.84   98
 98  ω    -83.00 -57.00   0.50    0.05    --  -74.00 -66.00 115.42   52
 99  ω   -123.00 -87.00   0.50    0.25    -- -103.87 -62.00 118.44   72
100  ω    -90.00 -64.00   0.50    0.25    --  -78.00 -60.00 177.29   52
101  ω   -175.00-127.00   0.50    0.25    -- -103.87 -61.00  60.00   96
102  ω   -139.00 -93.00   0.50    0.25    -- -103.87 -45.00  30.00   92
103  ω   -110.00 -77.00   0.50    0.25    --  -94.00 -63.00 -71.29   66
104  ω   -117.00 -78.00   0.50    0.25    --  -94.00 -59.00 -65.78   78
105  ω   -152.00-120.00   0.50    0.25    --  -94.00 -59.00 -65.78   64
106  ω   -109.00 -69.00   0.50    0.25    --  -86.00 -62.00-150.27   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0291024000
_diffrn_orient_matrix_UB_12      -0.1182493000
_diffrn_orient_matrix_UB_13      -0.0902121000
_diffrn_orient_matrix_UB_21      0.1824438000
_diffrn_orient_matrix_UB_22      0.1229300000
_diffrn_orient_matrix_UB_23      -0.0186972000
_diffrn_orient_matrix_UB_31      0.1199523000
_diffrn_orient_matrix_UB_32      -0.0354389000
_diffrn_orient_matrix_UB_33      0.0824269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3352
_reflns_number_total             3484
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.1892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00B(H00B), C00F(H00F), C00G(H00G),
 C00J(H00K), C00K(H00L), C00M(H00P), C00O(H00T)
2.b Idealised Me refined as rotating group:
 C00H(H00C,H00D,H00E), C00I(H00H,H00I,H00J), C00L(H00M,H00N,H00O), C00N(H00Q,
 H00R,H00S)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.29494(9) 0.30936(7) 0.30198(5) 0.02501(16) Uani 1 1 d . . . . .
N002 N 0.52404(11) 0.36687(8) 0.19333(6) 0.02110(18) Uani 1 1 d . . . . .
N003 N 0.54884(11) 0.53899(9) 0.35628(6) 0.02239(18) Uani 1 1 d . . . . .
N004 N 0.63439(10) 0.48785(8) 0.15718(6) 0.01938(17) Uani 1 1 d . . . . .
N005 N 0.44080(11) 0.59746(9) 0.42080(6) 0.02250(18) Uani 1 1 d . . . . .
C006 C 0.68059(12) 0.46506(10) 0.06262(7) 0.01916(19) Uani 1 1 d . . . . .
H006 H 0.632664 0.366216 0.016016 0.023 Uiso 1 1 calc R U . . .
C007 C 0.80923(12) 0.59464(10) 0.02736(7) 0.01863(19) Uani 1 1 d . . . . .
C008 C 0.85967(12) 0.57453(10) -0.07662(7) 0.02008(19) Uani 1 1 d . . . . .
C009 C 0.52843(13) 0.72593(11) 0.48855(7) 0.0228(2) Uani 1 1 d . . . . .
H009 H 0.663120 0.775403 0.493542 0.027 Uiso 1 1 calc R U . . .
C00A C 0.88920(13) 0.73815(10) 0.09972(7) 0.02104(19) Uani 1 1 d . . . . .
H00A H 0.852298 0.752193 0.169335 0.025 Uiso 1 1 calc R U . . .
C00B C 1.02102(13) 0.85935(10) 0.07095(8) 0.0235(2) Uani 1 1 d . . . . .
H00B H 1.074131 0.955976 0.120460 0.028 Uiso 1 1 calc R U . . .
C00C C 0.44470(13) 0.39913(10) 0.28603(7) 0.02116(19) Uani 1 1 d . . . . .
C00D C 0.42205(13) 0.79693(11) 0.55837(7) 0.0225(2) Uani 1 1 d . . . . .
C00E C 0.51771(14) 0.94284(11) 0.62631(8) 0.0251(2) Uani 1 1 d . . . . .
C00F C 0.99390(13) 0.69837(11) -0.10364(8) 0.0233(2) Uani 1 1 d . . . . .
H00F H 1.030199 0.686016 -0.173450 0.028 Uiso 1 1 calc R U . . .
C00G C 1.07525(13) 0.83876(11) -0.03091(8) 0.0244(2) Uani 1 1 d . . . . .
H00G H 1.167954 0.920846 -0.050622 0.029 Uiso 1 1 calc R U . . .
C00H C 0.75720(13) 0.60639(11) 0.37655(8) 0.0259(2) Uani 1 1 d . . . . .
H00C H 0.802772 0.702550 0.356016 0.039 Uiso 1 1 calc R U . . .
H00D H 0.808685 0.537458 0.334235 0.039 Uiso 1 1 calc R U . . .
H00E H 0.800158 0.624439 0.453021 0.039 Uiso 1 1 calc R U . . .
C00I C 0.44827(13) 0.21304(10) 0.12598(8) 0.0238(2) Uani 1 1 d . . . . .
H00H H 0.357083 0.204694 0.066063 0.036 Uiso 1 1 calc R U . . .
H00I H 0.383316 0.142986 0.168509 0.036 Uiso 1 1 calc R U . . .
H00J H 0.553322 0.187726 0.097964 0.036 Uiso 1 1 calc R U . . .
C00J C 0.22609(14) 0.72053(11) 0.55864(8) 0.0259(2) Uani 1 1 d . . . . .
H00K H 0.161489 0.622397 0.512258 0.031 Uiso 1 1 calc R U . . .
C00K C 0.12479(15) 0.78550(13) 0.62532(8) 0.0303(2) Uani 1 1 d . . . . .
H00L H -0.007647 0.731810 0.625543 0.036 Uiso 1 1 calc R U . . .
C00L C 0.77250(14) 0.42432(10) -0.15891(7) 0.0242(2) Uani 1 1 d . . . . .
H00M H 0.809011 0.349308 -0.134276 0.036 Uiso 1 1 calc R U . . .
H00N H 0.818956 0.435196 -0.227403 0.036 Uiso 1 1 calc R U . . .
H00O H 0.632913 0.390915 -0.168476 0.036 Uiso 1 1 calc R U . . .
C00M C 0.41259(16) 1.00744(12) 0.69158(8) 0.0313(2) Uani 1 1 d . . . . .
H00P H 0.475031 1.106635 0.736819 0.038 Uiso 1 1 calc R U . . .
C00N C 0.72966(14) 1.02987(11) 0.63048(8) 0.0301(2) Uani 1 1 d . . . . .
H00Q H 0.801034 0.973988 0.654284 0.045 Uiso 1 1 calc R U . . .
H00R H 0.768383 1.129441 0.680956 0.045 Uiso 1 1 calc R U . . .
H00S H 0.756860 1.042564 0.558900 0.045 Uiso 1 1 calc R U . . .
C00O C 0.21893(16) 0.93000(13) 0.69186(8) 0.0333(2) Uani 1 1 d . . . . .
H00T H 0.150615 0.975801 0.737580 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.2176(11) . ?
N002 N004 1.3724(10) . ?
N002 C00C 1.3918(12) . ?
N002 C00I 1.4535(11) . ?
N003 N005 1.3764(11) . ?
N003 C00C 1.3886(12) . ?
N003 C00H 1.4583(12) . ?
N004 C006 1.2810(12) . ?
N005 C009 1.2840(12) . ?
C006 H006 0.9500 . ?
C006 C007 1.4726(12) . ?
C007 C008 1.4050(13) . ?
C007 C00A 1.4047(12) . ?
C008 C00F 1.3978(13) . ?
C008 C00L 1.5091(12) . ?
C009 H009 0.9500 . ?
C009 C00D 1.4679(13) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.3840(13) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.3908(14) . ?
C00D C00E 1.4072(13) . ?
C00D C00J 1.4007(13) . ?
C00E C00M 1.3957(14) . ?
C00E C00N 1.5130(14) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.3860(14) . ?
C00G H00G 0.9500 . ?
C00H H00C 0.9800 . ?
C00H H00D 0.9800 . ?
C00H H00E 0.9800 . ?
C00I H00H 0.9800 . ?
C00I H00I 0.9800 . ?
C00I H00J 0.9800 . ?
C00J H00K 0.9500 . ?
C00J C00K 1.3854(14) . ?
C00K H00L 0.9500 . ?
C00K C00O 1.3895(16) . ?
C00L H00M 0.9800 . ?
C00L H00N 0.9800 . ?
C00L H00O 0.9800 . ?
C00M H00P 0.9500 . ?
C00M C00O 1.3873(16) . ?
C00N H00Q 0.9800 . ?
C00N H00R 0.9800 . ?
C00N H00S 0.9800 . ?
C00O H00T 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N004 N002 C00C 116.81(7) . . ?
N004 N002 C00I 122.32(7) . . ?
C00C N002 C00I 118.80(7) . . ?
N005 N003 C00C 114.12(7) . . ?
N005 N003 C00H 121.11(8) . . ?
C00C N003 C00H 123.73(8) . . ?
C006 N004 N002 119.43(7) . . ?
C009 N005 N003 117.41(8) . . ?
N004 C006 H006 120.6 . . ?
N004 C006 C007 118.89(8) . . ?
C007 C006 H006 120.6 . . ?
C008 C007 C006 120.49(8) . . ?
C00A C007 C006 119.78(8) . . ?
C00A C007 C008 119.66(8) . . ?
C007 C008 C00L 121.88(8) . . ?
C00F C008 C007 118.41(8) . . ?
C00F C008 C00L 119.71(8) . . ?
N005 C009 H009 119.8 . . ?
N005 C009 C00D 120.49(8) . . ?
C00D C009 H009 119.8 . . ?
C007 C00A H00A 119.6 . . ?
C00B C00A C007 120.88(8) . . ?
C00B C00A H00A 119.6 . . ?
C00A C00B H00B 120.2 . . ?
C00A C00B C00G 119.57(9) . . ?
C00G C00B H00B 120.2 . . ?
O001 C00C N002 121.15(8) . . ?
O001 C00C N003 123.97(8) . . ?
N003 C00C N002 114.88(7) . . ?
C00E C00D C009 119.81(8) . . ?
C00J C00D C009 120.68(9) . . ?
C00J C00D C00E 119.51(9) . . ?
C00D C00E C00N 121.83(9) . . ?
C00M C00E C00D 118.47(9) . . ?
C00M C00E C00N 119.70(9) . . ?
C008 C00F H00F 119.2 . . ?
C00G C00F C008 121.51(9) . . ?
C00G C00F H00F 119.2 . . ?
C00B C00G H00G 120.0 . . ?
C00F C00G C00B 119.93(8) . . ?
C00F C00G H00G 120.0 . . ?
N003 C00H H00C 109.5 . . ?
N003 C00H H00D 109.5 . . ?
N003 C00H H00E 109.5 . . ?
H00C C00H H00D 109.5 . . ?
H00C C00H H00E 109.5 . . ?
H00D C00H H00E 109.5 . . ?
N002 C00I H00H 109.5 . . ?
N002 C00I H00I 109.5 . . ?
N002 C00I H00J 109.5 . . ?
H00H C00I H00I 109.5 . . ?
H00H C00I H00J 109.5 . . ?
H00I C00I H00J 109.5 . . ?
C00D C00J H00K 119.4 . . ?
C00K C00J C00D 121.19(9) . . ?
C00K C00J H00K 119.4 . . ?
C00J C00K H00L 120.3 . . ?
C00J C00K C00O 119.30(9) . . ?
C00O C00K H00L 120.3 . . ?
C008 C00L H00M 109.5 . . ?
C008 C00L H00N 109.5 . . ?
C008 C00L H00O 109.5 . . ?
H00M C00L H00N 109.5 . . ?
H00M C00L H00O 109.5 . . ?
H00N C00L H00O 109.5 . . ?
C00E C00M H00P 119.3 . . ?
C00O C00M C00E 121.45(10) . . ?
C00O C00M H00P 119.3 . . ?
C00E C00N H00Q 109.5 . . ?
C00E C00N H00R 109.5 . . ?
C00E C00N H00S 109.5 . . ?
H00Q C00N H00R 109.5 . . ?
H00Q C00N H00S 109.5 . . ?
H00R C00N H00S 109.5 . . ?
C00K C00O H00T 120.0 . . ?
C00M C00O C00K 120.06(9) . . ?
C00M C00O H00T 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 N004 C006 C007 -176.09(7) . . . . ?
N003 N005 C009 C00D 178.63(8) . . . . ?
N004 N002 C00C O001 151.43(8) . . . . ?
N004 N002 C00C N003 -28.44(11) . . . . ?
N004 C006 C007 C008 -178.60(8) . . . . ?
N004 C006 C007 C00A 4.37(13) . . . . ?
N005 N003 C00C O001 -25.76(13) . . . . ?
N005 N003 C00C N002 154.10(8) . . . . ?
N005 C009 C00D C00E -175.12(8) . . . . ?
N005 C009 C00D C00J 5.28(14) . . . . ?
C006 C007 C008 C00F -175.00(8) . . . . ?
C006 C007 C008 C00L 5.32(13) . . . . ?
C006 C007 C00A C00B 175.35(8) . . . . ?
C007 C008 C00F C00G -0.63(13) . . . . ?
C007 C00A C00B C00G -0.08(14) . . . . ?
C008 C007 C00A C00B -1.71(13) . . . . ?
C008 C00F C00G C00B -1.16(14) . . . . ?
C009 C00D C00E C00M 179.88(9) . . . . ?
C009 C00D C00E C00N -0.42(14) . . . . ?
C009 C00D C00J C00K 179.04(9) . . . . ?
C00A C007 C008 C00F 2.04(13) . . . . ?
C00A C007 C008 C00L -177.64(8) . . . . ?
C00A C00B C00G C00F 1.52(14) . . . . ?
C00C N002 N004 C006 -166.75(8) . . . . ?
C00C N003 N005 C009 179.28(8) . . . . ?
C00D C00E C00M C00O 1.17(15) . . . . ?
C00D C00J C00K C00O 1.01(15) . . . . ?
C00E C00D C00J C00K -0.56(15) . . . . ?
C00E C00M C00O C00K -0.73(16) . . . . ?
C00H N003 N005 C009 10.48(13) . . . . ?
C00H N003 C00C O001 142.70(10) . . . . ?
C00H N003 C00C N002 -37.43(12) . . . . ?
C00I N002 N004 C006 -3.33(12) . . . . ?
C00I N002 C00C O001 -12.60(13) . . . . ?
C00I N002 C00C N003 167.53(8) . . . . ?
C00J C00D C00E C00M -0.52(14) . . . . ?
C00J C00D C00E C00N 179.18(9) . . . . ?
C00J C00K C00O C00M -0.37(16) . . . . ?
C00L C008 C00F C00G 179.06(8) . . . . ?
C00N C00E C00M C00O -178.55(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.874
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2113099'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;

_chemical_name_common            
1,5-bis(3-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_chemical_name_systematic        
1,5-bis(3-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_chemical_formula_moiety         'C19 H22 N4 O3'
_chemical_formula_sum            'C19 H22 N4 O3'
_chemical_formula_weight         354.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H22 N4 O3'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'

_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
142_ALERT_4_G s.u. on b - Axis Small or Missing ..............     0.00010 Ang.
143_ALERT_4_G s.u. on c - Axis Small or Missing ..............     0.00020 Ang.

These are correct.
#-------------------------------------------------------------------------------
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600   67     Note


#-------------------------------------------------------------------------------
795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C13 Note
796_ALERT_4_G O-Atom in CIF Coordinate List Out-of-Sequence ..          O1 Note
797_ALERT_4_G N-Atom in CIF Coordinate List Out-of-Sequence ..          N2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.    15   Info

No action taken.
#-------------------------------------------------------------------------------
;


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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.97880(10)
_cell_length_b                   14.73690(10)
_cell_length_c                   22.0879(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3573.68(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18553
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3570
_cell_measurement_theta_min      3.9780
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -7 0 0.0507
7 0 -2 0.0752
1 9 2 0.0606
-5 7 4 0.0624
-7 2 3 0.0575
2 -7 8 0.0722
3 -3 12 0.0720
3 4 12 0.0699
0 10 1 0.0568
-1 9 -4 0.0606
-3 -3 -12 0.0521

_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.125
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.6104 -7.2945 -0.4518 -0.4623 -0.4372 -0.7715
7.0191 0.4611 -2.4253 0.7252 0.6874 0.0408
1.1209 9.3180 2.3164 0.0972 0.0909 0.9911
-4.8900 6.5037 3.6858 -0.5189 -0.4928 0.6985
-6.8294 1.8495 3.0320 -0.7102 -0.6735 0.2051
2.4878 -7.2403 7.9172 0.6812 -0.3698 -0.6318
3.3001 -2.9790 11.8973 0.8700 -0.4729 -0.1395
2.8328 4.1168 11.6184 0.7130 -0.3881 0.5840
-0.2323 9.5283 1.1252 -0.1085 0.0581 0.9924
-1.4802 9.0197 -3.7182 -0.4292 0.2326 0.8727
-3.0488 -2.9353 -12.1893 -0.7749 0.4217 -0.4708

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31632
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.558
_diffrn_reflns_theta_min         4.003
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 118.00   0.50    0.06    --   46.32  57.00   0.00  172
  2  ω     90.00 174.00   0.50    0.45    --  102.29  45.00-120.00  168
  3  ω    -26.00  43.00   0.50    0.06    --   46.32 -38.00-180.00  138
  4  ω     30.00 105.00   0.50    0.45    --  102.29 -77.00 -60.00  150
  5  ω     30.00  71.00   0.50    0.45    --  102.29 -61.00 150.00   82
  6  ω     13.00  94.00   0.50    0.06    --   46.32-125.00 -90.00  162
  7  ω     30.00 111.00   0.50    0.45    --  102.29-125.00 150.00  162
  8  ω     30.00 108.00   0.50    0.45    --  102.29-113.00  77.00  156
  9  ω   -118.00 -24.00   0.50    0.06    --  -46.32 -77.00 150.00  188
 10  ω   -120.00 -32.00   0.50    0.06    --  -46.32 -14.00-133.00  176
 11  ω   -118.00 -79.00   0.50    0.06    --  -46.32 -57.00-150.00   78
 12  ω   -174.00 -80.00   0.50    0.45    -- -102.29 -77.00-180.00  188
 13  ω   -176.00 -88.00   0.50    0.45    -- -102.29 -14.00-133.00  176
 14  ω    -71.00 -30.00   0.50    0.45    -- -102.29  61.00 -90.00   82
 15  ω    -26.00  29.00   0.50    0.06    --  -46.32  19.00-180.00  110
 16  ω    -71.00 -30.00   0.50    0.45    -- -102.29  61.00-180.00   82
 17  ω   -116.00 -30.00   0.50    0.45    -- -102.29 131.00-111.00  172
 18  ω   -108.00 -30.00   0.50    0.45    -- -102.29 113.00 169.00  156
 19  ω   -176.00 -90.00   0.50    0.45    -- -102.29 -30.00  90.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1170889000
_diffrn_orient_matrix_UB_12      -0.0129511000
_diffrn_orient_matrix_UB_13      0.0374068000
_diffrn_orient_matrix_UB_21      0.0771114000
_diffrn_orient_matrix_UB_22      0.0147593000
_diffrn_orient_matrix_UB_23      -0.0574385000
_diffrn_orient_matrix_UB_31      0.0035586000
_diffrn_orient_matrix_UB_32      0.1027041000
_diffrn_orient_matrix_UB_33      0.0130014000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3296
_reflns_number_total             3642
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+1.0484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0850

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C12(H12), C8(H8), C7(H7), C3(H3), C14(H14), C5(H5), C4(H4),
 C16(H16), C15(H15)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.09497(7) 0.18670(5) 0.47233(3) 0.02300(17) Uani 1 1 d . . . . .
O1 O 0.31043(7) 0.46387(5) 0.39950(3) 0.02378(18) Uani 1 1 d . . . . .
O2 O 0.75633(7) 0.04340(5) 0.31727(4) 0.02759(19) Uani 1 1 d . . . . .
N1 N 0.49247(8) 0.16764(5) 0.31704(4) 0.01790(18) Uani 1 1 d . . . . .
N3 N 0.65416(8) 0.09193(6) 0.40049(4) 0.02035(19) Uani 1 1 d . . . . .
N2 N 0.56091(8) 0.09176(6) 0.30360(4) 0.02058(19) Uani 1 1 d . . . . .
N4 N 0.54045(8) 0.10208(6) 0.42586(4) 0.01855(18) Uani 1 1 d . . . . .
C17 C 0.20127(9) 0.16959(6) 0.50278(5) 0.0193(2) Uani 1 1 d . . . . .
C13 C 0.41346(9) 0.12964(6) 0.51103(5) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.32644(9) 0.26661(7) 0.29673(4) 0.0180(2) Uani 1 1 d . . . . .
C18 C 0.31137(9) 0.14850(6) 0.47509(5) 0.0185(2) Uani 1 1 d . . . . .
H18 H 0.317360 0.146879 0.432199 0.022 Uiso 1 1 calc R U . . .
C12 C 0.53253(9) 0.11168(7) 0.48341(5) 0.0197(2) Uani 1 1 d . . . . .
H12 H 0.603274 0.107189 0.507993 0.024 Uiso 1 1 calc R U . . .
C8 C 0.40089(9) 0.18618(7) 0.28304(5) 0.0196(2) Uani 1 1 d . . . . .
H8 H 0.381498 0.148475 0.249513 0.024 Uiso 1 1 calc R U . . .
C10 C 0.66307(9) 0.07478(7) 0.33938(5) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.35983(9) 0.32729(7) 0.34271(4) 0.0177(2) Uani 1 1 d . . . . .
H7 H 0.432876 0.317994 0.364920 0.021 Uiso 1 1 calc R U . . .
C2 C 0.28563(9) 0.40098(7) 0.35561(4) 0.0184(2) Uani 1 1 d . . . . .
C3 C 0.17789(9) 0.41537(7) 0.32324(5) 0.0206(2) Uani 1 1 d . . . . .
H3 H 0.127390 0.465920 0.332307 0.025 Uiso 1 1 calc R U . . .
C14 C 0.40378(10) 0.13105(7) 0.57390(5) 0.0225(2) Uani 1 1 d . . . . .
H14 H 0.472398 0.116309 0.598190 0.027 Uiso 1 1 calc R U . . .
C5 C 0.21931(10) 0.28121(7) 0.26428(5) 0.0214(2) Uani 1 1 d . . . . .
H5 H 0.196636 0.240561 0.232853 0.026 Uiso 1 1 calc R U . . .
C4 C 0.14555(10) 0.35528(7) 0.27786(5) 0.0228(2) Uani 1 1 d . . . . .
H4 H 0.072351 0.364661 0.255794 0.027 Uiso 1 1 calc R U . . .
C16 C 0.19329(10) 0.17446(7) 0.56603(5) 0.0226(2) Uani 1 1 d . . . . .
H16 H 0.118916 0.191768 0.584738 0.027 Uiso 1 1 calc R U . . .
C19 C 0.10151(10) 0.19075(7) 0.40777(5) 0.0236(2) Uani 1 1 d . . . . .
H19A H 0.019712 0.200191 0.391164 0.035 Uiso 1 1 calc R U . . .
H19B H 0.134905 0.133666 0.392192 0.035 Uiso 1 1 calc R U . . .
H19C H 0.154403 0.241157 0.395677 0.035 Uiso 1 1 calc R U . . .
C1 C 0.42511(10) 0.45595(7) 0.42947(5) 0.0256(2) Uani 1 1 d . . . . .
H1A H 0.490779 0.457305 0.399431 0.038 Uiso 1 1 calc R U . . .
H1B H 0.428103 0.398506 0.451774 0.038 Uiso 1 1 calc R U . . .
H1C H 0.435200 0.506596 0.457781 0.038 Uiso 1 1 calc R U . . .
C15 C 0.29393(11) 0.15401(7) 0.60116(5) 0.0245(2) Uani 1 1 d . . . . .
H15 H 0.287926 0.155652 0.644054 0.029 Uiso 1 1 calc R U . . .
C11 C 0.76351(10) 0.08512(7) 0.43759(5) 0.0247(2) Uani 1 1 d . . . . .
H11A H 0.773333 0.140863 0.461288 0.037 Uiso 1 1 calc R U . . .
H11B H 0.834660 0.076734 0.411393 0.037 Uiso 1 1 calc R U . . .
H11C H 0.756079 0.033180 0.465053 0.037 Uiso 1 1 calc R U . . .
C9 C 0.55699(11) 0.05108(7) 0.24337(5) 0.0263(2) Uani 1 1 d . . . . .
H9A H 0.474729 0.028251 0.235327 0.040 Uiso 1 1 calc R U . . .
H9B H 0.615239 0.000788 0.241325 0.040 Uiso 1 1 calc R U . . .
H9C H 0.578369 0.096905 0.213022 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C17 1.3704(13) . ?
O3 C19 1.4290(13) . ?
O1 C2 1.3686(12) . ?
O1 C1 1.4273(13) . ?
O2 C10 1.2249(13) . ?
N1 N2 1.3795(12) . ?
N1 C8 1.2843(14) . ?
N3 N4 1.3766(12) . ?
N3 C10 1.3769(14) . ?
N3 C11 1.4570(13) . ?
N2 C10 1.3946(14) . ?
N2 C9 1.4599(13) . ?
N4 C12 1.2819(14) . ?
C17 C18 1.3900(14) . ?
C17 C16 1.4016(14) . ?
C13 C18 1.4012(15) . ?
C13 C12 1.4666(14) . ?
C13 C14 1.3929(14) . ?
C6 C8 1.4712(14) . ?
C6 C7 1.4020(14) . ?
C6 C5 1.3941(14) . ?
C18 H18 0.9500 . ?
C12 H12 0.9500 . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C7 C2 1.3870(14) . ?
C2 C3 1.3983(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3837(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3898(16) . ?
C5 H5 0.9500 . ?
C5 C4 1.3920(15) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.3834(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C15 H15 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O3 C19 117.05(8) . . ?
C2 O1 C1 116.66(8) . . ?
C8 N1 N2 118.22(9) . . ?
N4 N3 C10 118.92(8) . . ?
N4 N3 C11 121.72(8) . . ?
C10 N3 C11 118.70(8) . . ?
N1 N2 C10 117.49(8) . . ?
N1 N2 C9 120.86(9) . . ?
C10 N2 C9 117.80(9) . . ?
C12 N4 N3 118.50(9) . . ?
O3 C17 C18 124.45(9) . . ?
O3 C17 C16 115.25(9) . . ?
C18 C17 C16 120.29(10) . . ?
C18 C13 C12 120.87(9) . . ?
C14 C13 C18 120.05(10) . . ?
C14 C13 C12 119.04(10) . . ?
C7 C6 C8 121.17(9) . . ?
C5 C6 C8 119.17(9) . . ?
C5 C6 C7 119.65(9) . . ?
C17 C18 C13 119.39(9) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
N4 C12 C13 119.53(9) . . ?
N4 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
N1 C8 C6 119.08(9) . . ?
N1 C8 H8 120.5 . . ?
C6 C8 H8 120.5 . . ?
O2 C10 N3 121.29(10) . . ?
O2 C10 N2 120.94(10) . . ?
N3 C10 N2 117.74(9) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 C6 119.64(9) . . ?
C2 C7 H7 120.2 . . ?
O1 C2 C7 123.97(9) . . ?
O1 C2 C3 115.33(9) . . ?
C7 C2 C3 120.70(9) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.37(10) . . ?
C4 C3 H3 120.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.12(10) . . ?
C15 C14 H14 119.9 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.07(9) . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 120.58(10) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.87(10) . . ?
C15 C16 H16 120.1 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.21(10) . . ?
C16 C15 H15 119.9 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C17 C18 C13 -178.11(9) . . . . ?
O3 C17 C16 C15 176.85(9) . . . . ?
O1 C2 C3 C4 179.86(9) . . . . ?
N1 N2 C10 O2 -143.25(9) . . . . ?
N1 N2 C10 N3 38.64(13) . . . . ?
N3 N4 C12 C13 175.29(8) . . . . ?
N2 N1 C8 C6 179.77(8) . . . . ?
N4 N3 C10 O2 -161.70(9) . . . . ?
N4 N3 C10 N2 16.40(13) . . . . ?
C17 C16 C15 C14 1.75(15) . . . . ?
C13 C14 C15 C16 0.79(15) . . . . ?
C6 C7 C2 O1 -179.93(9) . . . . ?
C6 C7 C2 C3 0.00(14) . . . . ?
C6 C5 C4 C3 0.44(16) . . . . ?
C18 C17 C16 C15 -3.05(15) . . . . ?
C18 C13 C12 N4 -8.63(14) . . . . ?
C18 C13 C14 C15 -2.06(15) . . . . ?
C12 C13 C18 C17 -176.86(9) . . . . ?
C12 C13 C14 C15 175.60(9) . . . . ?
C8 N1 N2 C10 177.31(9) . . . . ?
C8 N1 N2 C9 19.90(13) . . . . ?
C8 C6 C7 C2 -178.10(9) . . . . ?
C8 C6 C5 C4 177.91(9) . . . . ?
C10 N3 N4 C12 175.18(9) . . . . ?
C7 C6 C8 N1 5.62(14) . . . . ?
C7 C6 C5 C4 -0.51(15) . . . . ?
C7 C2 C3 C4 -0.08(15) . . . . ?
C2 C3 C4 C5 -0.15(15) . . . . ?
C14 C13 C18 C17 0.76(14) . . . . ?
C14 C13 C12 N4 173.73(9) . . . . ?
C5 C6 C8 N1 -172.79(9) . . . . ?
C5 C6 C7 C2 0.29(14) . . . . ?
C16 C17 C18 C13 1.79(14) . . . . ?
C19 O3 C17 C18 -5.74(14) . . . . ?
C19 O3 C17 C16 174.36(8) . . . . ?
C1 O1 C2 C7 5.62(14) . . . . ?
C1 O1 C2 C3 -174.32(9) . . . . ?
C11 N3 N4 C12 4.63(13) . . . . ?
C11 N3 C10 O2 9.13(14) . . . . ?
C11 N3 C10 N2 -172.77(9) . . . . ?
C9 N2 C10 O2 14.86(14) . . . . ?
C9 N2 C10 N3 -163.25(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.896
####################################################################### 
# 
# 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_11b
_database_code_depnum_ccdc_archive 'CCDC 2113101'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;


_chemical_name_common            
1,5-bis(thiophenyl)-2,4-dimethyl-carbohydrazide
_chemical_name_systematic        
1,5-bis(thiophenyl)-2,4-dimethyl-carbohydrazide
_chemical_formula_moiety         'C13 H14 N4 O S2'
_chemical_formula_sum            'C13 H14 N4 O S2'
_chemical_formula_weight         306.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H14 N4 O S2'
_chemical_oxdiff_usercomment     'Becky UTas'

_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 21 Note

#-------------------------------------------------------------------------------
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          18 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.       2 Info

No action taken.
#-------------------------------------------------------------------------------
;

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.32320(10)
_cell_length_b                   19.6029(2)
_cell_length_c                   10.4905(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.845(2)
_cell_angle_gamma                90
_cell_volume                     1433.52(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13876
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      75.1310
_cell_measurement_theta_min      4.4860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 0 0.0556
4 -4 0 0.0559
-3 10 0 0.0460
3 -10 -1 0.0470
-1 12 0 0.0441
0 -13 -1 0.0388
2 12 0 0.0437
-1 -12 0 0.0420
3 10 0 0.0535
-3 -10 0 0.0497
4 7 0 0.0571
-3 -7 -3 0.0741
-4 -4 0 0.0570
2 -1 -7 0.1311
-4 8 0 0.0513
4 -8 0 0.0552
-2 1 7 0.1197
-1 12 -1 0.0418
1 -12 0 0.0420
0 13 -1 0.0399
-2 -12 0 0.0456
2 12 -1 0.0456
3 6 -5 0.1035
4 1 -6 0.1130
4 4 0 0.0571

_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.086
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.6034 0.3038 0.4121 0.4265 -0.8955 -0.1277
4.3568 -4.1990 -0.4497 -0.6789 0.7163 0.1610
-2.5955 10.4005 -0.0459 0.9766 -0.1816 -0.1151
2.7517 -10.3377 -0.7740 -0.9559 0.1778 0.2338
-1.3485 12.1471 0.0184 0.9843 0.1290 -0.1204
0.1013 -12.6753 -0.5834 -0.8869 -0.4223 0.1872
1.5222 12.0298 -0.2871 0.7253 0.6876 -0.0344
-1.4357 -12.0588 -0.0328 -0.7233 -0.6857 0.0815
2.5986 10.2353 0.3661 0.4754 0.8744 -0.0975
-2.5822 -10.2376 -0.4211 -0.4750 -0.8736 0.1056
3.6022 7.3888 0.3484 0.1825 0.9815 -0.0575
-2.7803 -7.2823 -2.5058 -0.1696 -0.9109 0.3763
-4.2876 -3.7659 -0.1567 0.1300 -0.9915 -0.0090
1.7005 -1.3170 -6.7632 0.0032 -0.0085 1.0000
-3.5153 7.6032 -0.4640 0.8777 -0.4771 -0.0461
3.5638 -7.6301 0.2477 -0.8759 0.4761 0.0778
-1.7159 1.2206 6.7671 -0.0087 0.0024 -1.0000
-1.1626 12.0892 -0.7399 0.9915 0.1300 -0.0090
1.3142 -12.1483 0.1242 -0.9866 -0.1295 0.0995
0.2136 12.6654 -0.6333 0.9028 0.4301 -0.0090
-1.5673 -12.0031 0.4588 -0.7257 -0.6880 0.0090
1.6389 11.9429 -0.7400 0.7253 0.6876 0.0326
3.1726 6.0155 -5.1231 0.3280 0.6021 0.7279
3.5166 0.5938 -5.8952 -0.0594 0.4581 0.8869
4.3649 3.6970 -0.1711 -0.1298 0.9899 0.0575

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21491
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.509
_diffrn_reflns_theta_min         4.511
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid photon'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 118.00   0.50    0.05    --   46.20  77.00  60.00  188
  2  ω     24.00 118.00   0.50    0.05    --   46.20  77.00 120.00  188
  3  ω     31.00 118.00   0.50    0.05    --   46.20  57.00  90.00  174
  4  ω     24.00 118.00   0.50    0.05    --   46.20  77.00   0.00  188
  5  ω     34.00 121.00   0.50    0.05    --   46.20  19.00  90.00  174
  6  ω     31.00 118.00   0.50    0.05    --   46.20  57.00   0.00  174
  7  ω     31.00 118.00   0.50    0.05    --   46.20  57.00 -60.00  174
  8  ω     31.00 118.00   0.50    0.05    --   46.20  57.00-120.00  174
  9  ω     24.00 118.00   0.50    0.05    --   46.20  77.00-150.00  188
 10  ω     56.00 118.00   0.50    0.05    --   46.20 151.00-133.00  124
 11  ω     56.00 164.00   0.50    0.08    --  102.41 151.00-133.00  216
 12  ω     86.00 175.00   0.50    0.08    --  102.41  61.00-150.00  178
 13  ω     76.00 175.00   0.50    0.08    --  102.41 122.00  65.00  198
 14  ω     74.00 175.00   0.50    0.08    --  102.41 125.00 120.00  202
 15  ω     90.00 177.00   0.50    0.08    --  102.41  30.00 150.00  174
 16  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00 120.00  108
 17  ω     30.00  71.00   0.50    0.08    --  102.41 -61.00 120.00   82
 18  ω     30.00  71.00   0.50    0.08    --  102.41 -61.00  30.00   82
 19  ω     30.00  71.00   0.50    0.08    --  102.41 -61.00   0.00   82
 20  ω     30.00  71.00   0.50    0.08    --  102.41 -61.00 -30.00   82
 21  ω     30.00 105.00   0.50    0.08    --  102.41 -77.00-180.00  150
 22  ω     30.00 105.00   0.50    0.08    --  102.41 -94.00-180.00  150
 23  ω     26.00 109.00   0.50    0.05    --   46.20-151.00-177.00  166
 24  ω     30.00 130.00   0.50    0.08    --  102.41-151.00-177.00  200
 25  ω     30.00 111.00   0.50    0.08    --  102.41-125.00-120.00  162
 26  ω     30.00 111.00   0.50    0.08    --  102.41-125.00  90.00  162
 27  ω     11.00  92.00   0.50    0.05    --   46.20-122.00 -15.00  162
 28  ω     30.00 109.00   0.50    0.08    --  102.41-122.00 -15.00  158
 29  ω     30.00 105.00   0.50    0.08    --  102.41 -94.00   0.00  150
 30  ω   -130.00 -30.00   0.50    0.08    -- -102.41 151.00-133.00  200
 31  ω   -111.00 -30.00   0.50    0.08    -- -102.41 125.00 150.00  162
 32  ω   -109.00 -30.00   0.50    0.08    -- -102.41 122.00  65.00  158
 33  ω    -92.00 -11.00   0.50    0.05    --  -46.20 122.00  65.00  162
 34  ω   -107.00 -30.00   0.50    0.08    -- -102.41 107.00-152.30  154
 35  ω   -175.00-123.00   0.50    0.08    -- -102.41 -80.00 120.37  104
 36  ω   -175.00 -79.00   0.50    0.08    -- -102.41 -79.00  18.53  192
 37  ω   -175.00 -80.00   0.50    0.08    -- -102.41 -77.00   0.00  190
 38  ω   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00 -90.00  190
 39  ω   -175.00 -80.00   0.50    0.08    -- -102.41 -77.00-180.00  190
 40  ω   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00-180.00  190
 41  ω   -175.00 -80.00   0.50    0.08    -- -102.41 -75.00 143.81  190
 42  ω   -175.00 -81.00   0.50    0.08    -- -102.41 -74.00 -62.19  188
 43  ω   -175.00 -84.00   0.50    0.08    -- -102.41 -65.00-158.59  182
 44  ω   -175.00 -86.00   0.50    0.08    -- -102.41 -62.00  24.34  178
 45  ω   -175.00 -86.00   0.50    0.08    -- -102.41 -61.00  60.00  178
 46  ω   -175.00 -89.00   0.50    0.08    -- -102.41 -51.00  72.72  172
 47  ω   -174.00 -90.00   0.50    0.08    -- -102.41 -45.00  90.00  168
 48  ω   -174.00 -90.00   0.50    0.08    -- -102.41 -45.00 -60.00  168
 49  ω   -177.00 -90.00   0.50    0.08    -- -102.41 -30.00-120.00  174
 50  ω   -118.00 -55.00   0.50    0.05    --  -46.20-151.00-177.00  126
 51  ω   -164.00 -55.00   0.50    0.08    -- -102.41-151.00-177.00  218
 52  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00  30.00   90
 53  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00-150.00   90
 54  ω   -175.00 -75.00   0.50    0.08    -- -102.41-122.00 -15.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0912886000
_diffrn_orient_matrix_UB_12      0.0709547000
_diffrn_orient_matrix_UB_13      -0.0372384000
_diffrn_orient_matrix_UB_21      0.2007438000
_diffrn_orient_matrix_UB_22      0.0328367000
_diffrn_orient_matrix_UB_23      0.0453401000
_diffrn_orient_matrix_UB_31      0.0144310000
_diffrn_orient_matrix_UB_32      -0.0080908000
_diffrn_orient_matrix_UB_33      -0.1426495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1426
_reflns_number_total             1468
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1228

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C00A(H00D), C00B(H00E)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S001 S 0.21761(4) 0.58117(2) 0.66756(3) 0.0201(2) Uani 1 1 d . . . . .
O002 O 0.500000 0.27419(6) 0.750000 0.0225(3) Uani 1 2 d S T P . .
N003 N 0.42415(14) 0.37300(5) 0.63234(9) 0.0166(3) Uani 1 1 d . . . . .
N004 N 0.35780(13) 0.43848(5) 0.63712(10) 0.0161(3) Uani 1 1 d . . . . .
C005 C 0.29859(15) 0.47142(6) 0.52604(12) 0.0165(3) Uani 1 1 d . . . . .
H005 H 0.300693 0.450762 0.446698 0.020 Uiso 1 1 calc R U . . .
C006 C 0.22869(16) 0.54056(6) 0.52423(11) 0.0157(3) Uani 1 1 d . . . . .
C007 C 0.500000 0.33696(8) 0.750000 0.0163(4) Uani 1 2 d S T P . .
C008 C 0.17005(17) 0.58316(6) 0.41545(14) 0.0185(3) Uani 1 1 d . . . . .
H008 H 0.165428 0.570370 0.329151 0.022 Uiso 1 1 calc R U . . .
C009 C 0.39125(19) 0.33720(6) 0.50512(13) 0.0191(3) Uani 1 1 d . . . . .
H00A H 0.257201 0.338767 0.455674 0.029 Uiso 1 1 calc R U . . .
H00B H 0.431181 0.290549 0.522009 0.029 Uiso 1 1 calc R U . . .
H00C H 0.463752 0.358776 0.454082 0.029 Uiso 1 1 calc R U . . .
C00A C 0.11730(18) 0.64878(7) 0.44886(14) 0.0222(3) Uani 1 1 d . . . . .
H00D H 0.074257 0.683706 0.386917 0.027 Uiso 1 1 calc R U . . .
C00B C 0.13654(18) 0.65503(6) 0.58138(14) 0.0223(3) Uani 1 1 d . . . . .
H00E H 0.108998 0.694673 0.620616 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C006 1.7251(12) . ?
S001 C00B 1.7138(13) . ?
O002 C007 1.230(2) . ?
N003 N004 1.3789(14) . ?
N003 C007 1.3824(13) . ?
N003 C009 1.4610(15) . ?
N004 C005 1.2857(16) . ?
C005 H005 0.9300 . ?
C005 C006 1.4468(16) . ?
C006 C008 1.3726(18) . ?
C008 H008 0.9300 . ?
C008 C00A 1.4175(16) . ?
C009 H00A 0.9600 . ?
C009 H00B 0.9600 . ?
C009 H00C 0.9600 . ?
C00A H00D 0.9300 . ?
C00A C00B 1.359(2) . ?
C00B H00E 0.9300 . ?

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
C00B S001 C006 91.80(6) . . ?
N004 N003 C007 119.53(10) . . ?
N004 N003 C009 121.27(9) . . ?
C007 N003 C009 118.61(11) . . ?
C005 N004 N003 117.34(10) . . ?
N004 C005 H005 119.9 . . ?
N004 C005 C006 120.13(11) . . ?
C006 C005 H005 119.9 . . ?
C005 C006 S001 122.13(9) . . ?
C008 C006 S001 110.95(9) . . ?
C008 C006 C005 126.89(11) . . ?
O002 C007 N003 120.74(7) . 2_656 ?
O002 C007 N003 120.74(7) . . ?
N003 C007 N003 118.53(15) . 2_656 ?
C006 C008 H008 123.6 . . ?
C006 C008 C00A 112.71(12) . . ?
C00A C008 H008 123.6 . . ?
N003 C009 H00A 109.5 . . ?
N003 C009 H00B 109.5 . . ?
N003 C009 H00C 109.5 . . ?
H00A C009 H00B 109.5 . . ?
H00A C009 H00C 109.5 . . ?
H00B C009 H00C 109.5 . . ?
C008 C00A H00D 123.7 . . ?
C00B C00A C008 112.58(12) . . ?
C00B C00A H00D 123.7 . . ?
S001 C00B H00E 124.0 . . ?
C00A C00B S001 111.96(10) . . ?
C00A C00B H00E 124.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 C006 C008 C00A 0.33(14) . . . . ?
N003 N004 C005 C006 -179.47(9) . . . . ?
N004 N003 C007 O002 155.22(7) . . . . ?
N004 N003 C007 N003 -24.78(7) . . . 2_656 ?
N004 C005 C006 S001 -1.06(15) . . . . ?
N004 C005 C006 C008 176.54(12) . . . . ?
C005 C006 C008 C00A -177.49(11) . . . . ?
C006 S001 C00B C00A 0.48(11) . . . . ?
C006 C008 C00A C00B 0.03(17) . . . . ?
C007 N003 N004 C005 176.15(9) . . . . ?
C008 C00A C00B S001 -0.38(15) . . . . ?
C009 N003 N004 C005 -12.77(16) . . . . ?
C009 N003 C007 O002 -16.10(11) . . . . ?
C009 N003 C007 N003 163.90(11) . . . 2_656 ?
C00B S001 C006 C005 177.48(10) . . . . ?
C00B S001 C006 C008 -0.46(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.385
_oxdiff_exptl_absorpt_empirical_full_min 0.653
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2113095'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-09-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;


_chemical_name_common            
1,5-bis(2-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_chemical_name_systematic        
1,5-bis(2-methoxybenzyl)-2,4-dimethyl-carbohydrazide
_chemical_formula_moiety         'C19 H22 N4 O3'
_chemical_formula_sum            'C19 H22 N4 O3'
_chemical_formula_weight         354.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H22 N4 O3'
_chemical_oxdiff_usercomment     'UTas Becky'


_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600   10    Report

Data are 99.9% complete.
TABLE HERE
#-------------------------------------------------------------------------------
PLAT975_ALERT_2_C Check Calcd Resid. Dens. 1.09A From O001           0.45 eA-3

This atom assignment appears correct. Geometry of site indicates a
 C=O bond (bond length = 1.219 Angstroms).
#-------------------------------------------------------------------------------
RINTA01_ALERT_3_C The value of Rint is greater than 0.12
                                                               Rint given 0.126
020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........     0.126 Report
072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large      0.15 Report
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          48 Note

No action taken.
#-------------------------------------------------------------------------------
;




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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5045(3)
_cell_length_b                   9.7970(4)
_cell_length_c                   11.9453(5)
_cell_angle_alpha                108.084(4)
_cell_angle_beta                 100.023(3)
_cell_angle_gamma                101.754(3)
_cell_volume                     895.65(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10860
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      73.0060
_cell_measurement_theta_min      4.9460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 5 2 0.0315
4 -5 2 0.0267
-5 5 0 0.0272
-4 5 -2 0.0323
-2 -1 8 0.0684
-5 2 -2 0.0266
4 -2 4 0.0277
2 1 -8 0.0475
0 3 5 0.0312
-2 -5 0 0.0380
-4 5 1 0.0318
3 -6 3 0.0309
-5 4 -2 0.0266
4 -4 4 0.0240
-4 0 -3 0.0347
3 0 5 0.0274

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.062
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.6766 4.8835 1.7909 0.5533 -0.7224 0.4147
3.9966 -5.0328 2.3073 -0.8212 0.5649 0.0803
-4.5206 4.6243 -0.1575 0.8070 -0.5554 0.2007
-4.1609 4.9665 -1.7752 0.8238 -0.5668 -0.0090
-2.1649 -1.1188 7.5313 0.0084 -0.0033 1.0000
-5.0759 1.7786 -1.7377 0.9996 0.0257 -0.0090
4.2850 -2.0217 3.7400 -0.9587 -0.0249 0.2834
2.1393 1.1987 -7.5465 -0.0034 -0.0084 -1.0000
-0.1461 3.3493 4.6072 -0.2234 -0.7547 0.6169
-1.5663 -5.2012 0.3693 0.2843 0.9579 0.0409
-3.5787 5.2528 0.9154 0.5792 -0.7552 0.3069
2.6544 -6.0037 2.7726 -0.5988 0.7814 0.1754
-4.8954 3.5247 -1.7068 0.9586 -0.2845 0.0090
3.9868 -3.7205 4.0110 -0.9121 0.2709 0.3076
-4.4271 0.0106 -2.5570 0.9314 0.3292 -0.1555
2.8703 -0.4909 5.3025 -0.7893 -0.2786 0.5472

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            31657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.621
_diffrn_reflns_theta_min         4.026
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 118.00   0.50    0.24    --   46.20  77.00  60.00  188
  2  ω     90.00 176.00   0.50    1.00    --  102.41  37.00 116.00  172
  3  ω    141.00 167.00   0.50    1.00    --  102.41  45.00  60.00   52
  4  ω     80.00 105.00   0.50    1.00    --  102.41 -94.00   0.00   50
  5  ω     76.00 111.00   0.50    1.00    --  102.41-125.00  30.00   70
  6  ω     45.00 103.00   0.50    1.00    --  102.41 -94.00 150.00  116
  7  ω     40.00  88.00   0.50    1.00    --  102.41 -77.00  90.00   96
  8  ω     39.00 116.00   0.50    1.00    --  102.41-130.00 -17.13  154
  9  ω     58.00  99.00   0.50    1.00    --  102.41 -94.00-120.00   82
 10  ω     30.00  82.00   0.50    1.00    --  102.41 -77.00 -30.00  104
 11  ω     30.00  99.00   0.50    1.00    --  102.41 -94.00  60.00  138
 12  ω     34.00  72.00   0.50    1.00    --  102.41 -94.00   0.00   76
 13  ω     34.00 119.00   0.50    0.24    --   46.20  37.00 116.00  170
 14  ω     38.00 135.00   0.50    0.24    --   62.00  79.00  -8.53  194
 15  ω     41.00 135.00   0.50    0.24    --   62.00  72.00-119.49  188
 16  ω     42.00 129.00   0.50    0.24    --   66.00  79.00-104.43  174
 17  ω     34.00 119.00   0.50    0.24    --   46.20  38.00-180.00  170
 18  ω     36.00 131.00   0.50    0.24    --   58.00  75.00 -59.23  190
 19  ω     39.00 135.00   0.50    0.24    --   62.00  78.00  84.23  192
 20  ω     43.00  69.00   0.50    0.24    --   66.00  77.00 -51.75   52
 21  ω     43.00  69.00   0.50    0.24    --   66.00  78.00 -27.99   52
 22  ω     34.00 131.00   0.50    0.24    --   58.00  79.00  45.05  194
 23  ω     39.00 135.00   0.50    0.24    --   62.00  77.00 142.37  192
 24  ω     44.00  70.00   0.50    0.24    --   66.00  77.00 116.12   52
 25  ω     26.00 122.00   0.50    0.24    --   50.00  80.00 125.72  192
 26  ω     35.00 131.00   0.50    0.24    --   58.00  77.00 159.06  192
 27  ω     24.00 118.00   0.50    0.24    --   46.20  77.00   0.00  188
 28  ω     24.00 118.00   0.50    0.24    --   46.20  77.00-120.00  188
 29  ω     24.00 118.00   0.50    0.24    --   46.20  77.00 -90.00  188
 30  ω     24.00 118.00   0.50    0.24    --   46.20  77.00-180.00  188
 31  ω     34.00 131.00   0.50    0.24    --   58.00  79.00-164.01  194
 32  ω      7.00  34.00   0.50    0.24    --   38.00  94.00 -33.48   54
 33  ω    -21.00  34.00   0.50    0.24    --   10.00  94.00 -26.81  110
 34  ω    -17.00  14.00   0.50    0.24    --   18.00 102.00 -90.74   62
 35  ω     10.00  43.00   0.50    0.24    --   38.00  88.00 106.31   66
 36  ω    -42.00  27.00   0.50    0.24    --  -46.20  37.00 116.00  138
 37  ω    -27.00  42.00   0.50    0.24    --   46.20 -37.00 -39.00  138
 38  ω    -25.00  69.00   0.50    0.24    --   46.20 -77.00-180.00  188
 39  ω     13.00  94.00   0.50    0.24    --   46.20-125.00-180.00  162
 40  ω    -65.00 -36.00   0.50    1.00    -- -102.41  61.00  30.00   58
 41  ω    -76.00 -50.00   0.50    1.00    -- -102.41 125.00  60.00   52
 42  ω    -69.00 -42.00   0.50    1.00    -- -102.41 125.00 150.00   54
 43  ω   -109.00 -81.00   0.50    1.00    -- -102.41 125.00  60.00   56
 44  ω   -111.00 -85.00   0.50    1.00    -- -102.41 125.00 150.00   52
 45  ω   -119.00 -34.00   0.50    0.24    --  -46.20 -37.00 -39.00  170
 46  ω    -80.00 -54.00   0.50    0.24    --  -74.00 -69.00  67.49   52
 47  ω    -77.00 -51.00   0.50    0.24    --  -74.00 -78.00  14.23   52
 48  ω    -82.00 -56.00   0.50    0.24    --  -74.00 -66.00  34.64   52
 49  ω    -85.00 -59.00   0.50    0.24    --  -74.00 -62.00  13.00   52
 50  ω    -86.00 -61.00   0.50    1.00    --  -82.00 -73.00  34.68   50
 51  ω    -92.00 -65.00   0.50    1.00    --  -82.00 -64.00  42.09   54
 52  ω    -90.00 -64.00   0.50    1.00    --  -82.00 -64.00  86.87   52
 53  ω    -85.00 -59.00   0.50    0.24    --  -74.00 -60.00 141.93   52
 54  ω    -82.00 -56.00   0.50    1.00    --  -78.00 -75.00 154.76   52
 55  ω    -87.00 -61.00   0.50    1.00    --  -82.00 -72.00 134.80   52
 56  ω    -90.00 -65.00   0.50    1.00    --  -86.00 -72.00 163.20   50
 57  ω    -94.00 -65.00   0.50    1.00    --  -82.00 -61.00 173.61   58
 58  ω    -93.00 -67.00   0.50    1.00    --  -90.00 -79.00 101.69   52
 59  ω   -108.00 -80.00   0.50    1.00    --  -90.00 -64.00  20.06   56
 60  ω    -95.00 -69.00   0.50    1.00    --  -90.00 -73.00   2.34   52
 61  ω    -93.00 -68.00   0.50    1.00    --  -90.00 -74.00 -39.25   50
 62  ω    -98.00 -64.00   0.50    1.00    --  -78.00 -58.00 -63.84   68
 63  ω    -87.00 -62.00   0.50    1.00    --  -78.00 -59.00-111.11   50
 64  ω    -92.00 -67.00   0.50    1.00    --  -82.00 -61.00-138.41   50
 65  ω    -93.00 -62.00   0.50    1.00    --  -82.00 -71.00-104.07   62
 66  ω    -94.00 -68.00   0.50    1.00    --  -86.00 -65.00-151.40   52
 67  ω   -106.00 -75.00   0.50    1.00    --  -94.00 -67.00 -64.48   62
 68  ω   -104.00 -68.00   0.50    1.00    --  -90.00 -74.00  -8.16   72
 69  ω   -103.00 -77.00   0.50    1.00    --  -94.00 -64.00  30.81   52
 70  ω   -113.00 -83.00   0.50    1.00    -- -102.41 -69.00  28.56   60
 71  ω   -114.00 -80.00   0.50    1.00    -- -102.41 -77.00 -60.00   68
 72  ω   -109.00 -80.00   0.50    1.00    -- -102.41 -77.00 -90.00   58
 73  ω   -115.00 -72.00   0.50    1.00    --  -94.00 -76.00-115.70   86
 74  ω   -126.00 -31.00   0.50    0.24    --  -54.00 -78.00-126.47  190
 75  ω   -123.00 -83.00   0.50    1.00    -- -102.41 -76.00 -11.82   80
 76  ω   -139.00 -79.00   0.50    1.00    --  -94.00 -58.00-108.60  120
 77  ω   -134.00 -72.00   0.50    1.00    --  -94.00 -76.00-160.20  124
 78  ω   -151.00-125.00   0.50    1.00    --  -90.00 -74.00  -8.16   52
 79  ω   -130.00 -79.00   0.50    1.00    --  -94.00 -61.00   3.82  102
 80  ω   -129.00 -82.00   0.50    1.00    -- -102.41 -70.00  91.45   94
 81  ω   -101.00 -69.00   0.50    1.00    --  -90.00 -72.00 143.10   64
 82  ω   -113.00 -73.00   0.50    1.00    --  -94.00 -72.00 169.78   80
 83  ω   -113.00 -71.00   0.50    1.00    --  -94.00 -76.00 138.58   84
 84  ω   -139.00 -47.00   0.50    0.24    --  -66.00 -67.00 164.08  184
 85  ω   -158.00-100.00   0.50    1.00    --  -86.00 -72.00 163.20  116
 86  ω   -160.00-123.00   0.50    1.00    --  -90.00 -79.00 101.69   74
 87  ω   -162.00-112.00   0.50    1.00    --  -90.00 -64.00  20.06  100
 88  ω   -161.00-116.00   0.50    1.00    --  -90.00 -74.00 -39.25   90
 89  ω   -167.00-115.00   0.50    1.00    --  -94.00 -67.00 -64.48  104
 90  ω   -167.00-121.00   0.50    1.00    --  -94.00 -76.00-115.70   92
 91  ω   -156.00 -77.00   0.50    1.00    --  -94.00 -63.00-155.74  158
 92  ω   -175.00 -90.00   0.50    1.00    -- -102.41 -37.00 -39.00  170
 93  ω   -173.00-130.00   0.50    1.00    -- -102.41 -76.00 -11.82   86
 94  ω   -174.00-115.00   0.50    1.00    -- -102.41 -77.00 -90.00  118
 95  ω   -174.00-117.00   0.50    1.00    -- -102.41 -69.00  28.56  114
 96  ω   -163.00-118.00   0.50    1.00    --  -94.00 -76.00 138.58   90
 97  ω   -175.00-134.00   0.50    1.00    -- -102.41 -70.00  91.45   82
 98  ω   -167.00 -83.00   0.50    1.00    -- -102.41 -69.00  69.43  168
 99  ω   -173.00-138.00   0.50    1.00    -- -102.41 -77.00 -60.00   70
100  ω   -105.00 -37.00   0.50    1.00    -- -102.41  77.00 -90.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1807026000
_diffrn_orient_matrix_UB_12      -0.0038875000
_diffrn_orient_matrix_UB_13      -0.0513994000
_diffrn_orient_matrix_UB_21      -0.0512697000
_diffrn_orient_matrix_UB_22      -0.1716119000
_diffrn_orient_matrix_UB_23      -0.0406752000
_diffrn_orient_matrix_UB_31      -0.0365037000
_diffrn_orient_matrix_UB_32      0.0119366000
_diffrn_orient_matrix_UB_33      0.1240538000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2984
_reflns_number_total             3558
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1462P)²+0.0814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2014

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00N(H00N), C00P(H00R)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00C,H00F), C00M(H00G,H00H,H00M), C00O(H00O,H00P,H00Q), C00Q(H00S,
 H00T,H00U)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.17286(14) 0.08022(13) 0.15298(12) 0.0347(4) Uani 1 1 d . . . . .
O002 O 0.82538(14) 0.61611(14) 0.13503(12) 0.0340(4) Uani 1 1 d . . . . .
O003 O -0.19842(15) 0.61179(15) 0.43313(13) 0.0384(4) Uani 1 1 d . . . . .
N004 N 0.13785(17) 0.43317(16) 0.29104(13) 0.0290(4) Uani 1 1 d . . . . .
N005 N 0.38808(16) 0.42961(16) 0.18010(13) 0.0278(4) Uani 1 1 d . . . . .
N006 N 0.36888(17) 0.30330(16) 0.20947(14) 0.0285(4) Uani 1 1 d . . . . .
N007 N 0.08868(17) 0.29285(16) 0.20228(14) 0.0296(4) Uani 1 1 d . . . . .
C008 C 0.2077(2) 0.21595(19) 0.18546(16) 0.0281(4) Uani 1 1 d . . . . .
C009 C 0.53380(19) 0.49578(19) 0.17849(16) 0.0282(4) Uani 1 1 d . . . . .
H009 H 0.623180 0.458046 0.195901 0.034 Uiso 1 1 calc R U . . .
C00A C 0.55731(19) 0.63105(19) 0.14896(16) 0.0279(4) Uani 1 1 d . . . . .
C00B C 0.7302(2) 0.81834(19) 0.09622(17) 0.0306(4) Uani 1 1 d . . . . .
H00B H 0.830150 0.858054 0.081505 0.037 Uiso 1 1 calc R U . . .
C00C C 0.7081(2) 0.6914(2) 0.12617(16) 0.0284(4) Uani 1 1 d . . . . .
C00D C 0.0259(2) 0.4943(2) 0.32462(17) 0.0310(4) Uani 1 1 d . . . . .
H00D H -0.086028 0.443666 0.291030 0.037 Uiso 1 1 calc R U . . .
C00E C 0.4324(2) 0.7036(2) 0.14215(17) 0.0322(4) Uani 1 1 d . . . . .
H00E H 0.332878 0.665935 0.158435 0.039 Uiso 1 1 calc R U . . .
C00F C 0.0767(2) 0.6449(2) 0.41642(17) 0.0314(4) Uani 1 1 d . . . . .
C00G C -0.0403(2) 0.7050(2) 0.47115(17) 0.0340(4) Uani 1 1 d . . . . .
C00H C 0.5059(2) 0.2394(2) 0.23275(18) 0.0331(4) Uani 1 1 d . . . . .
H00A H 0.549289 0.214276 0.162273 0.050 Uiso 1 1 calc R U . . .
H00C H 0.466968 0.150993 0.250093 0.050 Uiso 1 1 calc R U . . .
H00F H 0.591923 0.310867 0.301226 0.050 Uiso 1 1 calc R U . . .
C00I C 0.6022(2) 0.8864(2) 0.08817(17) 0.0323(4) Uani 1 1 d . . . . .
H00I H 0.616714 0.970697 0.066673 0.039 Uiso 1 1 calc R U . . .
C00J C 0.4533(2) 0.8301(2) 0.11179(18) 0.0346(5) Uani 1 1 d . . . . .
H00J H 0.368764 0.876831 0.107258 0.042 Uiso 1 1 calc R U . . .
C00K C 0.2403(2) 0.7352(2) 0.44974(18) 0.0358(4) Uani 1 1 d . . . . .
H00K H 0.318499 0.698381 0.413185 0.043 Uiso 1 1 calc R U . . .
C00L C 0.0073(3) 0.8478(2) 0.55766(18) 0.0403(5) Uani 1 1 d . . . . .
H00L H -0.069970 0.886163 0.594427 0.048 Uiso 1 1 calc R U . . .
C00M C -0.0858(2) 0.2105(2) 0.14845(18) 0.0327(4) Uani 1 1 d . . . . .
H00G H -0.134050 0.187499 0.209578 0.049 Uiso 1 1 calc R U . . .
H00H H -0.094619 0.119524 0.083828 0.049 Uiso 1 1 calc R U . . .
H00M H -0.143560 0.270334 0.116480 0.049 Uiso 1 1 calc R U . . .
C00N C 0.2874(2) 0.8776(2) 0.5356(2) 0.0407(5) Uani 1 1 d . . . . .
H00N H 0.396824 0.935634 0.557326 0.049 Uiso 1 1 calc R U . . .
C00O C -0.3241(3) 0.6705(3) 0.4793(2) 0.0442(5) Uani 1 1 d . . . . .
H00O H -0.429407 0.596430 0.443246 0.066 Uiso 1 1 calc R U . . .
H00P H -0.329401 0.757532 0.459489 0.066 Uiso 1 1 calc R U . . .
H00Q H -0.297929 0.697114 0.566098 0.066 Uiso 1 1 calc R U . . .
C00P C 0.1712(3) 0.9339(2) 0.58947(19) 0.0428(5) Uani 1 1 d . . . . .
H00R H 0.202948 1.029991 0.647372 0.051 Uiso 1 1 calc R U . . .
C00Q C 0.9796(2) 0.6738(3) 0.1127(2) 0.0465(6) Uani 1 1 d . . . . .
H00S H 0.960979 0.672801 0.030745 0.070 Uiso 1 1 calc R U . . .
H00T H 1.052337 0.613177 0.123429 0.070 Uiso 1 1 calc R U . . .
H00U H 1.029644 0.774502 0.168686 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.219(2) . ?
O002 C00C 1.365(2) . ?
O002 C00Q 1.423(2) . ?
O003 C00G 1.370(2) . ?
O003 C00O 1.427(2) . ?
N004 N007 1.377(2) . ?
N004 C00D 1.281(2) . ?
N005 N006 1.374(2) . ?
N005 C009 1.283(2) . ?
N006 C008 1.388(2) . ?
N006 C00H 1.456(2) . ?
N007 C008 1.386(2) . ?
N007 C00M 1.457(2) . ?
C009 H009 0.9300 . ?
C009 C00A 1.459(2) . ?
C00A C00C 1.408(2) . ?
C00A C00E 1.398(2) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.383(3) . ?
C00B C00I 1.392(2) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.461(3) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.382(3) . ?
C00F C00G 1.411(3) . ?
C00F C00K 1.401(3) . ?
C00G C00L 1.384(3) . ?
C00H H00A 0.9600 . ?
C00H H00C 0.9600 . ?
C00H H00F 0.9600 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.387(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00N 1.378(3) . ?
C00L H00L 0.9300 . ?
C00L C00P 1.391(3) . ?
C00M H00G 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00M 0.9600 . ?
C00N H00N 0.9300 . ?
C00N C00P 1.385(3) . ?
C00O H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00P H00R 0.9300 . ?
C00Q H00S 0.9600 . ?
C00Q H00T 0.9600 . ?
C00Q H00U 0.9600 . ?

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
C00C O002 C00Q 117.19(14) . . ?
C00G O003 C00O 117.46(16) . . ?
C00D N004 N007 118.61(14) . . ?
C009 N005 N006 118.15(14) . . ?
N005 N006 C008 117.03(13) . . ?
N005 N006 C00H 122.21(13) . . ?
C008 N006 C00H 118.71(14) . . ?
N004 N007 C008 117.58(13) . . ?
N004 N007 C00M 122.10(14) . . ?
C008 N007 C00M 118.57(14) . . ?
O001 C008 N006 122.30(15) . . ?
O001 C008 N007 121.90(15) . . ?
N007 C008 N006 115.80(14) . . ?
N005 C009 H009 120.5 . . ?
N005 C009 C00A 119.05(15) . . ?
C00A C009 H009 120.5 . . ?
C00C C00A C009 120.15(15) . . ?
C00E C00A C009 121.50(15) . . ?
C00E C00A C00C 118.35(16) . . ?
C00C C00B H00B 120.1 . . ?
C00C C00B C00I 119.75(16) . . ?
C00I C00B H00B 120.1 . . ?
O002 C00C C00A 115.53(15) . . ?
O002 C00C C00B 124.04(15) . . ?
C00B C00C C00A 120.42(15) . . ?
N004 C00D H00D 120.5 . . ?
N004 C00D C00F 119.07(16) . . ?
C00F C00D H00D 120.5 . . ?
C00A C00E H00E 119.2 . . ?
C00J C00E C00A 121.54(16) . . ?
C00J C00E H00E 119.2 . . ?
C00G C00F C00D 120.41(16) . . ?
C00K C00F C00D 121.43(17) . . ?
C00K C00F C00G 118.12(17) . . ?
O003 C00G C00F 115.16(16) . . ?
O003 C00G C00L 124.34(17) . . ?
C00L C00G C00F 120.49(18) . . ?
N006 C00H H00A 109.5 . . ?
N006 C00H H00C 109.5 . . ?
N006 C00H H00F 109.5 . . ?
H00A C00H H00C 109.5 . . ?
H00A C00H H00F 109.5 . . ?
H00C C00H H00F 109.5 . . ?
C00B C00I H00I 119.6 . . ?
C00J C00I C00B 120.90(17) . . ?
C00J C00I H00I 119.6 . . ?
C00E C00J C00I 119.02(16) . . ?
C00E C00J H00J 120.5 . . ?
C00I C00J H00J 120.5 . . ?
C00F C00K H00K 119.4 . . ?
C00N C00K C00F 121.29(18) . . ?
C00N C00K H00K 119.4 . . ?
C00G C00L H00L 120.1 . . ?
C00G C00L C00P 119.83(18) . . ?
C00P C00L H00L 120.1 . . ?
N007 C00M H00G 109.5 . . ?
N007 C00M H00H 109.5 . . ?
N007 C00M H00M 109.5 . . ?
H00G C00M H00H 109.5 . . ?
H00G C00M H00M 109.5 . . ?
H00H C00M H00M 109.5 . . ?
C00K C00N H00N 120.2 . . ?
C00K C00N C00P 119.70(19) . . ?
C00P C00N H00N 120.2 . . ?
O003 C00O H00O 109.5 . . ?
O003 C00O H00P 109.5 . . ?
O003 C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
C00L C00P H00R 119.7 . . ?
C00N C00P C00L 120.54(19) . . ?
C00N C00P H00R 119.7 . . ?
O002 C00Q H00S 109.5 . . ?
O002 C00Q H00T 109.5 . . ?
O002 C00Q H00U 109.5 . . ?
H00S C00Q H00T 109.5 . . ?
H00S C00Q H00U 109.5 . . ?
H00T C00Q H00U 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O003 C00G C00L C00P -179.66(17) . . . . ?
N004 N007 C008 O001 147.96(18) . . . . ?
N004 N007 C008 N006 -31.2(2) . . . . ?
N004 C00D C00F C00G -168.65(17) . . . . ?
N004 C00D C00F C00K 13.5(3) . . . . ?
N005 N006 C008 O001 145.15(18) . . . . ?
N005 N006 C008 N007 -35.7(2) . . . . ?
N005 C009 C00A C00C -169.16(16) . . . . ?
N005 C009 C00A C00E 10.7(3) . . . . ?
N006 N005 C009 C00A -179.28(15) . . . . ?
N007 N004 C00D C00F -178.39(15) . . . . ?
C009 N005 N006 C008 -166.46(16) . . . . ?
C009 N005 N006 C00H -3.0(2) . . . . ?
C009 C00A C00C O002 -0.6(2) . . . . ?
C009 C00A C00C C00B 178.96(16) . . . . ?
C009 C00A C00E C00J -178.68(17) . . . . ?
C00A C00E C00J C00I -0.3(3) . . . . ?
C00B C00I C00J C00E -0.8(3) . . . . ?
C00C C00A C00E C00J 1.1(3) . . . . ?
C00C C00B C00I C00J 1.1(3) . . . . ?
C00D N004 N007 C008 -166.65(16) . . . . ?
C00D N004 N007 C00M -1.9(2) . . . . ?
C00D C00F C00G O003 1.0(3) . . . . ?
C00D C00F C00G C00L -179.67(17) . . . . ?
C00D C00F C00K C00N 179.45(18) . . . . ?
C00E C00A C00C O002 179.57(16) . . . . ?
C00E C00A C00C C00B -0.9(3) . . . . ?
C00F C00G C00L C00P 1.1(3) . . . . ?
C00F C00K C00N C00P -0.7(3) . . . . ?
C00G C00F C00K C00N 1.5(3) . . . . ?
C00G C00L C00P C00N -0.3(3) . . . . ?
C00H N006 C008 O001 -18.9(3) . . . . ?
C00H N006 C008 N007 160.24(16) . . . . ?
C00I C00B C00C O002 179.30(17) . . . . ?
C00I C00B C00C C00A -0.2(3) . . . . ?
C00K C00F C00G O003 178.98(15) . . . . ?
C00K C00F C00G C00L -1.7(3) . . . . ?
C00K C00N C00P C00L 0.1(3) . . . . ?
C00M N007 C008 O001 -17.3(3) . . . . ?
C00M N007 C008 N006 163.50(16) . . . . ?
C00O O003 C00G C00F -175.80(17) . . . . ?
C00O O003 C00G C00L 4.9(3) . . . . ?
C00Q O002 C00C C00A -179.97(17) . . . . ?
C00Q O002 C00C C00B 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.300
_oxdiff_exptl_absorpt_empirical_full_min 0.441
####################################################################### 
# 
# 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_9c
_database_code_depnum_ccdc_archive 'CCDC 2113102'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;


_chemical_name_common            1,5-dimethyl-3-pyridyl-oxoverdazyl
_chemical_name_systematic        1,5-dimethyl-3-pyridyl-oxoverdazyl
_chemical_formula_moiety         'C9 H13 N5 O'
_chemical_formula_sum            'C9 H13 N5 O'
_chemical_formula_weight         207.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H13 N5 O'
_chemical_oxdiff_usercomment     'Becky UTas'

_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600       43 Note

#-------------------------------------------------------------------------------
007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............         2 Report
128_ALERT_4_G Alternate Setting for Input Space Group     C2/c        I2/a Note
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          28 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.      4  Info

No action taken.
#-------------------------------------------------------------------------------
;

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.7981(3)
_cell_length_b                   7.60210(10)
_cell_length_c                   16.1604(3)
_cell_angle_alpha                90
_cell_angle_beta                 124.601(2)
_cell_angle_gamma                90
_cell_volume                     2002.05(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17950
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      74.0140
_cell_measurement_theta_min      3.2810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 3 2 0.1116
1 5 1 0.1217
-7 4 0 0.0772
-2 -5 -1 0.0153
-1 0 9 0.0548
12 -1 -9 0.0824
1 0 -9 0.0574
-12 1 8 0.0407

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.113
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.2175 2.9605 1.5756 0.6708 -0.2776 -0.6877
1.2207 4.7855 1.3775 0.9223 -0.3825 -0.0559
-7.2333 3.6407 0.1342 0.5750 -0.2392 0.7824
-1.9704 -4.6882 -1.4362 -0.9155 0.3796 0.1330
-1.3426 -0.0533 9.2078 -0.1534 -0.8229 -0.5472
11.5133 -0.7750 -8.9213 0.1632 0.8800 -0.4461
1.2274 0.0618 -9.1620 0.1525 0.8179 0.5548
-12.3119 0.8617 7.6646 -0.1436 -0.7756 0.6146

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.623
_diffrn_reflns_theta_min         5.429
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 118.00   0.50    0.05    --   46.20  77.00 -90.00  188
  2  ω     24.00 118.00   0.50    0.05    --   46.20  77.00-150.00  188
  3  ω     24.00 118.00   0.50    0.05    --   46.20  77.00 -60.00  188
  4  ω     24.00 118.00   0.50    0.05    --   46.20  77.00   0.00  188
  5  ω     34.00 119.00   0.50    0.05    --   46.20  38.00 -60.00  170
  6  ω     24.00 118.00   0.50    0.05    --   46.20  77.00  60.00  188
  7  ω     31.00 118.00   0.50    0.05    --   46.20  57.00 120.00  174
  8  ω     24.00 118.00   0.50    0.05    --   46.20  77.00 150.00  188
  9  ω     34.00 119.00   0.50    0.05    --   46.20  38.00  90.00  170
 10  ω     34.00 121.00   0.50    0.05    --   46.20  19.00-120.00  174
 11  ω    -71.00 -30.00   0.50    0.17    -- -102.41  61.00   0.00   82
 12  ω    -71.00 -30.00   0.50    0.17    -- -102.41  61.00-120.00   82
 13  ω    -71.00 -30.00   0.50    0.17    -- -102.41  61.00-180.00   82
 14  ω     90.00 174.00   0.50    0.17    --  102.41  45.00-180.00  168
 15  ω     80.00 175.00   0.50    0.17    --  102.41 115.00-151.00  190
 16  ω     46.00 118.00   0.50    0.05    --   46.20 168.00  -7.00  144
 17  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00 -90.00  108
 18  ω     30.00 105.00   0.50    0.17    --  102.41 -77.00 -90.00  150
 19  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00  90.00  108
 20  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00 150.00  108
 21  ω     30.00  71.00   0.50    0.17    --  102.41 -61.00 120.00   82
 22  ω     30.00 105.00   0.50    0.17    --  102.41 -94.00 120.00  150
 23  ω     30.00 108.00   0.50    0.17    --  102.41-115.00 119.00  156
 24  ω      6.00  89.00   0.50    0.05    --   46.20-115.00 119.00  166
 25  ω     35.00 142.00   0.50    0.17    --  102.41-168.00 -25.00  214
 26  ω     30.00 105.00   0.50    0.17    --  102.41 -94.00-180.00  150
 27  ω   -141.00 -34.00   0.50    0.17    -- -102.41 168.00  -7.00  214
 28  ω   -111.00 -30.00   0.50    0.17    -- -102.41 125.00   0.00  162
 29  ω   -108.00 -30.00   0.50    0.17    -- -102.41 115.00-151.00  156
 30  ω   -108.00 -30.00   0.50    0.17    -- -102.41 110.00 -70.58  156
 31  ω    -89.00  -6.00   0.50    0.05    --  -46.20 115.00-151.00  166
 32  ω   -174.00 -90.00   0.50    0.17    -- -102.41 -45.00 -60.00  168
 33  ω   -175.00 -80.00   0.50    0.17    -- -102.41 -77.00 -60.00  190
 34  ω   -175.00 -80.00   0.50    0.17    -- -102.41 -77.00-150.00  190
 35  ω   -175.00 -80.00   0.50    0.17    -- -102.41 -75.00  34.71  190
 36  ω   -175.00 -81.00   0.50    0.17    -- -102.41 -74.00-127.16  188
 37  ω   -175.00 -83.00   0.50    0.17    -- -102.41 -68.00 150.46  184
 38  ω   -175.00 -85.00   0.50    0.17    -- -102.41 -63.00 -96.71  180
 39  ω   -175.00 -86.00   0.50    0.17    -- -102.41 -62.00   9.94  178
 40  ω   -175.00 -86.00   0.50    0.17    -- -102.41 -61.00  60.00  178
 41  ω   -175.00 -86.00   0.50    0.17    -- -102.41 -61.00 120.00  178
 42  ω   -175.00 -86.00   0.50    0.17    -- -102.41 -61.00 -30.00  178
 43  ω   -175.00 -86.00   0.50    0.17    -- -102.41 -61.00-180.00  178
 44  ω   -175.00-143.00   0.50    0.17    -- -102.41 -58.00  80.01   64
 45  ω   -175.00 -89.00   0.50    0.17    -- -102.41 -50.00 140.24  172
 46  ω   -175.00 -88.00   0.50    0.17    -- -102.41 -48.00 -24.21  174
 47  ω   -175.00 -90.00   0.50    0.17    -- -102.41 -46.00  81.89  170
 48  ω   -174.00 -90.00   0.50    0.17    -- -102.41 -45.00  30.00  168
 49  ω   -174.00 -90.00   0.50    0.17    -- -102.41 -45.00-130.87  168
 50  ω   -118.00 -46.00   0.50    0.05    --  -46.20-168.00 -25.00  144
 51  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00 -30.00   90
 52  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00-150.00   90
 53  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00-180.00   90
 54  ω   -175.00 -80.00   0.50    0.17    -- -102.41-115.00 119.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169793000
_diffrn_orient_matrix_UB_12      0.1921504000
_diffrn_orient_matrix_UB_13      -0.0130707000
_diffrn_orient_matrix_UB_21      0.0036337000
_diffrn_orient_matrix_UB_22      -0.0551930000
_diffrn_orient_matrix_UB_23      -0.0891551000
_diffrn_orient_matrix_UB_31      -0.0929207000
_diffrn_orient_matrix_UB_32      0.0329782000
_diffrn_orient_matrix_UB_33      -0.0727806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1937
_reflns_number_total             2042
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00074(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+1.7124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1050

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N003(H003), N005(H005)
2.b Ternary CH refined with riding coordinates:
 C00A(H00A)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D)
2.d Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00G), C00F(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.64154(5) 0.65347(12) 0.69564(7) 0.0266(2) Uani 1 1 d . . . . .
N002 N 0.59936(6) 0.36972(14) 0.67541(8) 0.0216(3) Uani 1 1 d . . . . .
N003 N 0.53575(6) 0.24493(13) 0.64537(8) 0.0193(2) Uani 1 1 d . . . . .
H003 H 0.539434 0.191920 0.694790 0.023 Uiso 1 1 d R U . . .
N004 N 0.38864(6) 0.15763(14) 0.63439(8) 0.0208(2) Uani 1 1 d . . . . .
N005 N 0.44357(6) 0.48858(13) 0.61302(8) 0.0215(3) Uani 1 1 d . . . . .
H005 H 0.427136 0.471418 0.651509 0.026 Uiso 1 1 d R U . . .
N006 N 0.51363(6) 0.60134(14) 0.65631(8) 0.0237(3) Uani 1 1 d . . . . .
C007 C 0.38945(7) 0.19806(15) 0.55415(9) 0.0188(3) Uani 1 1 d . . . . .
C008 C 0.33344(8) 0.13122(16) 0.45884(9) 0.0226(3) Uani 1 1 d . . . . .
H008 H 0.336718 0.160402 0.405326 0.027 Uiso 1 1 calc R U . . .
C009 C 0.58754(7) 0.54621(16) 0.67626(8) 0.0200(3) Uani 1 1 d . . . . .
C00A C 0.45594(7) 0.32558(15) 0.57506(9) 0.0187(3) Uani 1 1 d . . . . .
H00A H 0.450414 0.350744 0.511997 0.022 Uiso 1 1 calc R U . . .
C00B C 0.32942(8) 0.04907(17) 0.61976(10) 0.0237(3) Uani 1 1 d . . . . .
H00B H 0.328236 0.019484 0.674759 0.028 Uiso 1 1 calc R U . . .
C00C C 0.26994(7) -0.02125(17) 0.52694(10) 0.0239(3) Uani 1 1 d . . . . .
H00C H 0.229249 -0.094408 0.519702 0.029 Uiso 1 1 calc R U . . .
C00D C 0.27227(8) 0.01957(17) 0.44510(10) 0.0246(3) Uani 1 1 d . . . . .
H00D H 0.233540 -0.026945 0.381992 0.030 Uiso 1 1 calc R U . . .
C00E C 0.66820(8) 0.30520(19) 0.67465(11) 0.0288(3) Uani 1 1 d . . . . .
H00E H 0.690085 0.201131 0.715271 0.043 Uiso 1 1 calc R U . . .
H00F H 0.710031 0.393952 0.701250 0.043 Uiso 1 1 calc R U . . .
H00G H 0.649892 0.277951 0.606925 0.043 Uiso 1 1 calc R U . . .
C00F C 0.49219(9) 0.78661(17) 0.63231(12) 0.0345(3) Uani 1 1 d . . . . .
H00H H 0.475527 0.808923 0.564711 0.052 Uiso 1 1 calc R U . . .
H00I H 0.539008 0.858003 0.678007 0.052 Uiso 1 1 calc R U . . .
H00J H 0.447937 0.814858 0.638407 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.2351(15) . ?
N002 N003 1.4239(14) . ?
N002 C009 1.3633(16) . ?
N002 C00E 1.4549(15) . ?
N003 H003 0.8599 . ?
N003 C00A 1.4577(15) . ?
N004 C007 1.3414(16) . ?
N004 C00B 1.3405(16) . ?
N005 H005 0.8600 . ?
N005 N006 1.4304(14) . ?
N005 C00A 1.4637(15) . ?
N006 C009 1.3731(16) . ?
N006 C00F 1.4585(17) . ?
C007 C008 1.3859(17) . ?
C007 C00A 1.5105(16) . ?
C008 H008 0.9300 . ?
C008 C00D 1.3897(18) . ?
C00A H00A 0.9800 . ?
C00B H00B 0.9300 . ?
C00B C00C 1.3844(18) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.3845(19) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9600 . ?
C00E H00F 0.9600 . ?
C00E H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00F H00I 0.9600 . ?
C00F H00J 0.9600 . ?

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
N003 N002 C00E 115.08(10) . . ?
C009 N002 N003 122.38(10) . . ?
C009 N002 C00E 119.92(11) . . ?
N002 N003 H003 113.8 . . ?
N002 N003 C00A 110.05(9) . . ?
C00A N003 H003 113.8 . . ?
C00B N004 C007 117.38(10) . . ?
N006 N005 H005 113.4 . . ?
N006 N005 C00A 111.45(9) . . ?
C00A N005 H005 113.4 . . ?
N005 N006 C00F 113.19(10) . . ?
C009 N006 N005 122.69(10) . . ?
C009 N006 C00F 117.87(11) . . ?
N004 C007 C008 123.31(11) . . ?
N004 C007 C00A 114.72(10) . . ?
C008 C007 C00A 121.97(11) . . ?
C007 C008 H008 120.8 . . ?
C007 C008 C00D 118.44(11) . . ?
C00D C008 H008 120.8 . . ?
O001 C009 N002 121.56(11) . . ?
O001 C009 N006 120.77(11) . . ?
N002 C009 N006 117.66(11) . . ?
N003 C00A N005 113.25(10) . . ?
N003 C00A C007 109.00(9) . . ?
N003 C00A H00A 108.9 . . ?
N005 C00A C007 107.76(9) . . ?
N005 C00A H00A 108.9 . . ?
C007 C00A H00A 108.9 . . ?
N004 C00B H00B 118.3 . . ?
N004 C00B C00C 123.34(11) . . ?
C00C C00B H00B 118.3 . . ?
C00B C00C H00C 120.7 . . ?
C00B C00C C00D 118.63(11) . . ?
C00D C00C H00C 120.7 . . ?
C008 C00D H00D 120.6 . . ?
C00C C00D C008 118.89(11) . . ?
C00C C00D H00D 120.6 . . ?
N002 C00E H00E 109.5 . . ?
N002 C00E H00F 109.5 . . ?
N002 C00E H00G 109.5 . . ?
H00E C00E H00F 109.5 . . ?
H00E C00E H00G 109.5 . . ?
H00F C00E H00G 109.5 . . ?
N006 C00F H00H 109.5 . . ?
N006 C00F H00I 109.5 . . ?
N006 C00F H00J 109.5 . . ?
H00H C00F H00I 109.5 . . ?
H00H C00F H00J 109.5 . . ?
H00I C00F H00J 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 N003 C00A N005 -53.27(13) . . . . ?
N002 N003 C00A C007 -173.21(9) . . . . ?
N003 N002 C009 O001 -174.80(10) . . . . ?
N003 N002 C009 N006 6.23(17) . . . . ?
N004 C007 C008 C00D 1.39(18) . . . . ?
N004 C007 C00A N003 63.49(13) . . . . ?
N004 C007 C00A N005 -59.78(13) . . . . ?
N004 C00B C00C C00D 1.21(19) . . . . ?
N005 N006 C009 O001 166.32(11) . . . . ?
N005 N006 C009 N002 -14.69(17) . . . . ?
N006 N005 C00A N003 45.97(13) . . . . ?
N006 N005 C00A C007 166.61(9) . . . . ?
C007 N004 C00B C00C -0.26(18) . . . . ?
C007 C008 C00D C00C -0.38(18) . . . . ?
C008 C007 C00A N003 -117.38(12) . . . . ?
C008 C007 C00A N005 119.35(12) . . . . ?
C009 N002 N003 C00A 27.14(15) . . . . ?
C00A N005 N006 C009 -11.62(15) . . . . ?
C00A N005 N006 C00F 139.93(12) . . . . ?
C00A C007 C008 C00D -177.66(11) . . . . ?
C00B N004 C007 C008 -1.07(17) . . . . ?
C00B N004 C007 C00A 178.05(10) . . . . ?
C00B C00C C00D C008 -0.84(18) . . . . ?
C00E N002 N003 C00A -134.45(11) . . . . ?
C00E N002 C009 O001 -14.06(18) . . . . ?
C00E N002 C009 N006 166.96(11) . . . . ?
C00F N006 C009 O001 16.02(17) . . . . ?
C00F N006 C009 N002 -165.00(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_bof21
_database_code_depnum_ccdc_archive 'CCDC 2113100'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N4 O S, 0.5(H4 O2)'
_chemical_formula_sum            'C20 H22 N4 O2 S'
_chemical_formula_weight         382.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 N4 O2 S'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, z+1/2'
'x, -y+1/2, z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z-1/2'
'-x, y-1/2, -z'
'x-1/2, y, -z-1/2'

_cell_length_a                   4.93100(10)
_cell_length_b                   19.1334(6)
_cell_length_c                   20.4301(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1927.51(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4610
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      64.4070
_cell_measurement_theta_min      4.3070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 2 0.0133
-3 -3 -3 0.0639
0 12 -2 0.0343
3 2 2 0.1466
0 3 13 0.0387
-3 -2 2 0.0695
0 -3 -13 0.0077

_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.046
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1589 -12.2915 1.7850 0.8455 0.5173 0.1324
-3.0345 -3.0627 -2.6595 0.0333 0.0194 0.9993
-0.0866 12.3110 -1.7146 -0.8426 -0.5156 -0.1554
3.0934 2.4768 2.1342 0.0281 -0.0382 -0.9989
-0.0053 3.3071 12.7880 -0.5890 0.7681 -0.2513
-3.1506 -1.5491 1.5867 -0.2018 0.2647 0.9430
0.0053 -3.3071 -12.7880 0.5890 -0.7681 0.2513

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13320
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.335
_diffrn_reflns_theta_max         67.335
_diffrn_reflns_theta_min         4.328
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  73.00   0.50    2.00    --   -2.66  22.00  61.00  176
  2  ω     11.00 108.00   0.50   30.00    --   83.35-111.00  64.00  194
  3  ω     82.00 155.00   0.50   30.00    --   83.35 111.00-108.00  146
  4  ω   -164.00 -76.00   0.50   30.00    --  -88.66 -22.00-104.00  176
  5  ω    -23.00  31.00   0.50    2.00    --   -2.66 -99.00 -90.00  108
  6  ω    -23.00  31.00   0.50    2.00    --   -2.66 -99.00-120.00  108
  7  ω     11.00  66.00   0.50   30.00    --   83.35 -57.00 150.00  110
  8  ω     11.00  43.00   0.50   30.00    --   83.35 -38.00-120.00   64
  9  ω     11.00  43.00   0.50   30.00    --   83.35 -38.00-150.00   64
 10  ω     11.00  43.00   0.50   30.00    --   83.35 -38.00 150.00   64
 11  ω     11.00  66.00   0.50   30.00    --   83.35 -57.00-150.00  110
 12  ω     11.00  43.00   0.50   30.00    --   83.35 -38.00 -30.00   64
 13  ω   -111.00 -16.00   0.50   30.00    --  -88.66 125.00  90.00  190
 14  ω    -66.00 -16.00   0.50   30.00    --  -88.66  57.00-180.00  100
 15  ω    -43.00 -16.00   0.50   30.00    --  -88.66  38.00  30.00   54
 16  ω    -43.00 -16.00   0.50   30.00    --  -88.66  38.00  60.00   54
 17  ω    -23.00  31.00   0.50    2.00    --   -2.66 -99.00  90.00  108
 18  ω    -74.00  12.00   0.50    2.00    --   -2.66 -57.00  90.00  172
 19  ω    -17.00  70.00   0.50    2.00    --   -2.66  57.00 -90.00  174
 20  ω     71.00 150.00   0.50   30.00    --   83.35  22.00  61.00  158
 21  ω     71.00 158.00   0.50   30.00    --   83.35  19.00 150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0854417000
_diffrn_orient_matrix_UB_12      -0.0716726000
_diffrn_orient_matrix_UB_13      -0.0274885000
_diffrn_orient_matrix_UB_21      -0.0335089000
_diffrn_orient_matrix_UB_22      -0.0325794000
_diffrn_orient_matrix_UB_23      0.0684736000
_diffrn_orient_matrix_UB_31      -0.2987659000
_diffrn_orient_matrix_UB_32      -0.0168682000
_diffrn_orient_matrix_UB_33      -0.0154098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1534
_reflns_number_total             1736
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1463
_refine_ls_R_factor_gt           0.1355
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+18.5821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2605
_refine_ls_wR_factor_ref         0.2648
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(S2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(S2) = Uanis(C2) = Uanis(C5) = Uanis(C6) = Uanis(C8)
3. Others
 Fixed Sof: H16B(0.5) S2(0.5) C2(0.5) H2(0.5) C5(0.5) H5A(0.5) C6(0.5) H6(0.5)
 C8(0.5)
4.a Riding coordinates:
 N5(H5)
4.b Free rotating group:
 O16(H16A,H16B), S2(C2,C5,C6,C8)
4.c Ternary CH refined with riding coordinates:
 C4(H4)
4.d Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.e Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C2(H2), C5(H5A), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C4 C 0.360(2) 0.750000 0.4511(4) 0.034(3) Uani 1 2 d S T P . .
H4 H 0.535411 0.750000 0.428513 0.041 Uiso 1 2 calc R U P A .
N5 N 0.3467(11) 0.6868(3) 0.4907(3) 0.0338(14) Uani 1 1 d . . . . .
H5 H 0.493869 0.677745 0.511616 0.041 Uiso 1 1 d R U . . .
N6 N 0.1114(11) 0.6896(3) 0.5316(2) 0.0270(13) Uani 1 1 d . . . . .
C7 C -0.006(2) 0.750000 0.5512(4) 0.029(2) Uani 1 2 d S T P . .
O8 O -0.2193(13) 0.750000 0.5828(3) 0.0289(15) Uani 1 2 d S T P . .
C9 C 0.0146(15) 0.6208(4) 0.5521(4) 0.0378(18) Uani 1 1 d . . . . .
H9A H -0.030930 0.593597 0.513548 0.045 Uiso 1 1 calc R U . . .
H9B H -0.149188 0.626410 0.577839 0.045 Uiso 1 1 calc R U . . .
C10 C 0.2233(13) 0.5816(3) 0.5920(3) 0.0296(15) Uani 1 1 d . . . . .
C11 C 0.3322(15) 0.6120(4) 0.6478(3) 0.0345(17) Uani 1 1 d . . . . .
H11 H 0.278443 0.656588 0.660317 0.041 Uiso 1 1 calc R U . . .
C12 C 0.5205(16) 0.5759(4) 0.6846(4) 0.044(2) Uani 1 1 d . . . . .
H12 H 0.590779 0.596071 0.722397 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6051(16) 0.5105(4) 0.6661(4) 0.046(2) Uani 1 1 d . . . . .
H13 H 0.732808 0.486421 0.690910 0.055 Uiso 1 1 calc R U . . .
C14 C 0.4995(18) 0.4811(4) 0.6108(5) 0.062(3) Uani 1 1 d . . . . .
H14 H 0.554629 0.436591 0.598260 0.075 Uiso 1 1 calc R U . . .
C15 C 0.3133(16) 0.5164(4) 0.5735(5) 0.054(2) Uani 1 1 d . . . . .
H15 H 0.247147 0.496076 0.535318 0.064 Uiso 1 1 calc R U . . .
O16 O -0.1879(16) 0.750000 0.7211(3) 0.048(2) Uani 1 2 d GS T P . .
H16A H -0.347633 0.749971 0.734955 0.073 Uiso 1 2 d G U P . .
H16B H -0.186380 0.759872 0.680509 0.073 Uiso 0.5 1 d G U P . .
S2 S 0.0227(11) 0.6795(3) 0.3666(2) 0.0496(10) Uani 0.5 1 d G U P A -1
C2 C -0.1925(12) 0.7239(5) 0.3142(3) 0.0496(10) Uani 0.5 1 d G U P A -1
H2 H -0.306812 0.702681 0.283993 0.060 Uiso 0.5 1 calc R U P A -1
C5 C -0.172(2) 0.7949(4) 0.3234(4) 0.0496(10) Uani 0.5 1 d G U P A -1
H5A H -0.272668 0.827507 0.300027 0.060 Uiso 0.5 1 calc R U P A -1
C6 C 0.020(3) 0.8130(3) 0.3722(6) 0.0496(10) Uani 0.5 1 d G U P A -1
H6 H 0.058824 0.858778 0.384161 0.060 Uiso 0.5 1 calc R U P A -1
C8 C 0.1405(16) 0.7564(4) 0.3995(4) 0.0496(10) Uani 0.5 1 d G U P A -1


_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
C4 H4 0.9800 . ?
C4 N5 1.456(8) 3_565 ?
C4 N5 1.456(8) . ?
C4 C8 1.517(11) . ?
N5 H5 0.8600 . ?
N5 N6 1.432(7) . ?
N6 C7 1.352(7) . ?
N6 C9 1.461(9) . ?
C7 O8 1.236(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(10) . ?
C10 C11 1.387(9) . ?
C10 C15 1.378(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(12) . ?
C15 H15 0.9300 . ?
O16 H16A 0.8371 . ?
O16 H16B 0.8499 . ?
O16 H16B 0.85(10) 3_565 ?
S2 C2 1.7305 . ?
S2 C8 1.7196 . ?
C2 H2 0.9300 . ?
C2 C5 1.3739 . ?
C5 H5A 0.9300 . ?
C5 C6 1.4167 . ?
C6 H6 0.9300 . ?
C6 C8 1.3555 . ?

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
N5 C4 H4 107.6 3_565 . ?
N5 C4 H4 107.6 . . ?
N5 C4 N5 112.4(7) . 3_565 ?
N5 C4 C8 106.6(6) 3_565 . ?
N5 C4 C8 114.9(6) . . ?
C8 C4 H4 107.6 . . ?
C4 N5 H5 113.9 . . ?
N6 N5 C4 109.3(6) . . ?
N6 N5 H5 113.6 . . ?
N5 N6 C9 113.5(6) . . ?
C7 N6 N5 123.4(6) . . ?
C7 N6 C9 123.1(6) . . ?
N6 C7 N6 117.5(8) 3_565 . ?
O8 C7 N6 121.2(4) . 3_565 ?
O8 C7 N6 121.2(4) . . ?
N6 C9 H9A 109.2 . . ?
N6 C9 H9B 109.2 . . ?
N6 C9 C10 112.2(6) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C11 C10 C9 119.9(6) . . ?
C15 C10 C9 121.4(7) . . ?
C15 C10 C11 118.7(7) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.9(7) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(7) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.2(8) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(8) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(8) . . ?
C14 C15 H15 119.7 . . ?
H16A O16 H16B 109.8 . 3_565 ?
H16A O16 H16B 109.8 . . ?
H16B O16 H16B 25.7 . 3_565 ?
C8 S2 C2 91.6 . . ?
S2 C2 H2 124.6 . . ?
C5 C2 S2 110.9 . . ?
C5 C2 H2 124.6 . . ?
C2 C5 H5A 123.6 . . ?
C2 C5 C6 112.8 . . ?
C6 C5 H5A 123.6 . . ?
C5 C6 H6 123.6 . . ?
C8 C6 C5 112.8 . . ?
C8 C6 H6 123.6 . . ?
C4 C8 S2 116.4(5) . . ?
C6 C8 C4 131.6(5) . . ?
C6 C8 S2 112.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N5 N6 C7 -25.9(9) . . . . ?
C4 N5 N6 C9 155.9(6) . . . . ?
N5 C4 N5 N6 53.6(9) 3_565 . . . ?
N5 C4 C8 S2 -31.1(11) . . . . ?
N5 C4 C8 S2 -156.3(7) 3_565 . . . ?
N5 C4 C8 C6 151.0(5) . . . . ?
N5 C4 C8 C6 25.8(9) 3_565 . . . ?
N5 N6 C7 N6 -1.3(12) . . . 3_565 ?
N5 N6 C7 O8 174.9(6) . . . . ?
N5 N6 C9 C10 61.5(7) . . . . ?
N6 C9 C10 C11 55.2(9) . . . . ?
N6 C9 C10 C15 -123.4(8) . . . . ?
C7 N6 C9 C10 -116.7(8) . . . . ?
C9 N6 C7 N6 176.7(5) . . . 3_565 ?
C9 N6 C7 O8 -7.1(12) . . . . ?
C9 C10 C11 C12 179.3(7) . . . . ?
C9 C10 C15 C14 -179.0(8) . . . . ?
C10 C11 C12 C13 1.1(12) . . . . ?
C11 C10 C15 C14 2.4(12) . . . . ?
C11 C12 C13 C14 -0.4(13) . . . . ?
C12 C13 C14 C15 0.7(14) . . . . ?
C13 C14 C15 C10 -1.7(14) . . . . ?
C15 C10 C11 C12 -2.0(11) . . . . ?
S2 C2 C5 C6 0.6 . . . . ?
C2 S2 C8 C4 -177.9(8) . . . . ?
C2 S2 C8 C6 0.4 . . . . ?
C2 C5 C6 C8 -0.3 . . . . ?
C5 C6 C8 C4 177.9(10) . . . . ?
C5 C6 C8 S2 -0.1 . . . . ?
C8 C4 N5 N6 -68.5(8) . . . . ?
C8 S2 C2 C5 -0.6 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.360
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_12b
_database_code_depnum_ccdc_archive 'CCDC 2113097'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;

_chemical_name_common            
1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide
_chemical_name_systematic        
1,5-bis(thiophenyl)-2,4-bis(methylbenzyl)-carbohydrazide
_chemical_formula_moiety         'C25 H22 N4 O S2'
_chemical_formula_sum            'C25 H22 N4 O S2'
_chemical_formula_weight         458.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H22 N4 O S2'
_chemical_oxdiff_usercomment     'Rebecca Fuller - Tasmania'

_refine_special_details          
;
#-------------------------------------------------------------------------------
CIF VALIDATION REPORT:
#-------------------------------------------------------------------------------
410_ALERT_2_C Short Intra H...H Contact  H7B      ..H9       .        1.94 Ang.
                                                      x,y,z  =      1_555 Check

This is correct.
#-------------------------------------------------------------------------------
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600       13 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600    87    Note


#-------------------------------------------------------------------------------
795_ALERT_4_G C-Atom in CIF Coordinate List Out-of-Sequence ..         C6 Note
941_ALERT_3_G Average HKL Measurement Multiplicity ...........         4.6 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.      7 Info

No action taken.
#-------------------------------------------------------------------------------
;


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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.9089(3)
_cell_length_b                   11.6130(2)
_cell_length_c                   10.5619(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.812(2)
_cell_angle_gamma                90
_cell_volume                     2319.05(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9210
_cell_measurement_theta_min      4.4390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.181
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10618
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.449
_diffrn_reflns_theta_min         4.468
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00 114.00   0.50    0.05    --   45.57  77.00  90.00  182
  2  ω     23.00 118.00   0.50    0.05    --   45.57  77.00 -30.00  190
  3  ω     34.00 119.00   0.50    0.05    --   45.57  38.00 -90.00  170
  4  ω     31.00 118.00   0.50    0.05    --   45.57  55.00-153.00  174
  5  ω     30.00  71.00   0.50    0.16    --  102.29 -61.00 -60.00   82
  6  ω     30.00  71.00   0.50    0.16    --  102.29 -61.00-120.00   82
  7  ω     30.00  71.00   0.50    0.16    --  102.29 -61.00-150.00   82
  8  ω     30.00  71.00   0.50    0.16    --  102.29 -61.00 -30.00   82
  9  ω     30.00  63.00   0.50    0.16    --  102.29 -55.00  63.00   66
 10  ω     30.00  71.00   0.50    0.16    --  102.29 -61.00  90.00   82
 11  ω     79.00 174.00   0.50    0.16    --  102.29  78.00  60.00  190
 12  ω     86.00 174.00   0.50    0.16    --  102.29  61.00   0.00  176
 13  ω     88.00 174.00   0.50    0.16    --  102.29  55.00-153.00  172
 14  ω    -26.00  30.00   0.50    0.05    --  -45.57  19.00 -30.00  112
 15  ω    -71.00 -30.00   0.50    0.16    -- -102.29  61.00  60.00   82
 16  ω    -71.00 -30.00   0.50    0.16    -- -102.29  61.00   0.00   82
 17  ω    -26.00  30.00   0.50    0.05    --  -45.57  19.00  60.00  112
 18  ω    -71.00 -30.00   0.50    0.16    -- -102.29  61.00 -30.00   82
 19  ω    -71.00 -30.00   0.50    0.16    -- -102.29  61.00-120.00   82
 20  ω    -63.00 -30.00   0.50    0.16    -- -102.29  55.00-153.00   66
 21  ω   -174.00 -83.00   0.50    0.16    -- -102.29 -93.00-162.00  182
 22  ω   -174.00 -90.00   0.50    0.16    -- -102.29 -45.00   0.00  168
 23  ω   -176.00 -89.00   0.50    0.16    -- -102.29 -15.00 120.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0687489000
_diffrn_orient_matrix_UB_12      -0.0614416000
_diffrn_orient_matrix_UB_13      -0.0414248000
_diffrn_orient_matrix_UB_21      0.0023469000
_diffrn_orient_matrix_UB_22      0.0621000000
_diffrn_orient_matrix_UB_23      -0.1286845000
_diffrn_orient_matrix_UB_31      0.0437225000
_diffrn_orient_matrix_UB_32      -0.0998798000
_diffrn_orient_matrix_UB_33      -0.0545843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2154
_reflns_number_total             2302
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+1.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0939

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C1(H1), C11(H11), C3(H3), C12(H12), C2(H2), C13(H13), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.38756(2) 0.62685(3) 0.70301(3) 0.02523(13) Uani 1 1 d . . . . .
O1 O 0.500000 0.11666(10) 0.750000 0.0241(3) Uani 1 2 d S T P . .
N1 N 0.48149(5) 0.28233(9) 0.64169(10) 0.0198(2) Uani 1 1 d . . . . .
N2 N 0.45137(6) 0.38968(9) 0.65413(10) 0.0193(2) Uani 1 1 d . . . . .
C8 C 0.500000 0.22145(15) 0.750000 0.0193(4) Uani 1 2 d S T P . .
C9 C 0.42868(6) 0.44047(11) 0.55359(12) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.433040 0.403930 0.473612 0.025 Uiso 1 1 calc R U . . .
C6 C 0.41290(7) 0.15722(10) 0.48916(12) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.48182(6) 0.21737(11) 0.52340(12) 0.0205(3) Uani 1 1 d . . . . .
H7A H 0.519745 0.158738 0.528988 0.025 Uiso 1 1 calc R U . . .
H7B H 0.493856 0.270672 0.453797 0.025 Uiso 1 1 calc R U . . .
C10 C 0.39644(6) 0.55332(11) 0.56163(12) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.35020(7) 0.17375(11) 0.55355(13) 0.0258(3) Uani 1 1 d . . . . .
H5 H 0.348664 0.226572 0.622140 0.031 Uiso 1 1 calc R U . . .
C1 C 0.41407(7) 0.07940(11) 0.38893(13) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.456726 0.067380 0.344350 0.030 Uiso 1 1 calc R U . . .
C11 C 0.36891(7) 0.61615(11) 0.46231(13) 0.0238(3) Uani 1 1 d . . . . .
H11 H 0.369129 0.590714 0.376831 0.029 Uiso 1 1 calc R U . . .
C3 C 0.29095(8) 0.03627(12) 0.41742(15) 0.0308(3) Uani 1 1 d . . . . .
H3 H 0.249366 -0.004285 0.392667 0.037 Uiso 1 1 calc R U . . .
C12 C 0.34016(7) 0.72293(12) 0.50109(14) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.318863 0.776639 0.444431 0.033 Uiso 1 1 calc R U . . .
C2 C 0.35351(8) 0.01917(12) 0.35345(14) 0.0313(3) Uani 1 1 d . . . . .
H2 H 0.354999 -0.033924 0.285110 0.038 Uiso 1 1 calc R U . . .
C13 C 0.34630(7) 0.74026(12) 0.62773(15) 0.0294(3) Uani 1 1 d . . . . .
H13 H 0.329769 0.807113 0.669867 0.035 Uiso 1 1 calc R U . . .
C4 C 0.28948(8) 0.11308(12) 0.51789(16) 0.0307(3) Uani 1 1 d . . . . .
H4 H 0.246831 0.124431 0.562702 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.7303(13) . ?
S1 C13 1.7199(14) . ?
O1 C8 1.217(2) . ?
N1 N2 1.3777(14) . ?
N1 C8 1.3855(14) . ?
N1 C7 1.4595(15) . ?
N2 C9 1.2832(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.4484(18) . ?
C6 C7 1.5178(16) . ?
C6 C5 1.3885(19) . ?
C6 C1 1.3924(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C11 1.3741(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3944(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.3889(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.4168(19) . ?
C3 H3 0.9500 . ?
C3 C2 1.385(2) . ?
C3 C4 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.356(2) . ?
C2 H2 0.9500 . ?
C13 H13 0.9500 . ?
C4 H4 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S1 C10 91.59(7) . . ?
N2 N1 C8 118.88(10) . . ?
N2 N1 C7 123.79(10) . . ?
C8 N1 C7 116.04(10) . . ?
C9 N2 N1 118.10(11) . . ?
O1 C8 N1 120.68(8) . . ?
O1 C8 N1 120.68(7) . 2_656 ?
N1 C8 N1 118.63(15) 2_656 . ?
N2 C9 H9 119.9 . . ?
N2 C9 C10 120.24(12) . . ?
C10 C9 H9 119.9 . . ?
C5 C6 C7 123.77(12) . . ?
C5 C6 C1 119.01(12) . . ?
C1 C6 C7 117.20(11) . . ?
N1 C7 C6 115.32(10) . . ?
N1 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C9 C10 S1 122.89(10) . . ?
C11 C10 S1 110.88(10) . . ?
C11 C10 C9 126.22(12) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.23(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.67(13) . . ?
C2 C1 H1 119.7 . . ?
C10 C11 H11 123.6 . . ?
C10 C11 C12 112.76(13) . . ?
C12 C11 H11 123.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.48(13) . . ?
C4 C3 H3 120.3 . . ?
C11 C12 H12 123.6 . . ?
C13 C12 C11 112.78(12) . . ?
C13 C12 H12 123.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(13) . . ?
C3 C2 H2 119.9 . . ?
S1 C13 H13 124.0 . . ?
C12 C13 S1 111.98(11) . . ?
C12 C13 H13 124.0 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.42(14) . . ?
C3 C4 H4 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C10 C11 C12 -0.57(15) . . . . ?
N1 N2 C9 C10 179.86(10) . . . . ?
N2 N1 C8 O1 150.98(7) . . . . ?
N2 N1 C8 N1 -29.02(7) . . . 2_656 ?
N2 N1 C7 C6 -78.22(14) . . . . ?
N2 C9 C10 S1 0.96(17) . . . . ?
N2 C9 C10 C11 -178.75(12) . . . . ?
C8 N1 N2 C9 -173.79(10) . . . . ?
C8 N1 C7 C6 88.60(12) . . . . ?
C9 C10 C11 C12 179.17(12) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C7 N1 N2 C9 -7.32(17) . . . . ?
C7 N1 C8 O1 -16.52(11) . . . . ?
C7 N1 C8 N1 163.48(11) . . . 2_656 ?
C7 C6 C5 C4 -178.52(12) . . . . ?
C7 C6 C1 C2 178.70(12) . . . . ?
C10 S1 C13 C12 -0.41(11) . . . . ?
C10 C11 C12 C13 0.27(17) . . . . ?
C5 C6 C7 N1 8.78(17) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C1 C6 C7 N1 -169.75(11) . . . . ?
C1 C6 C5 C4 0.0(2) . . . . ?
C11 C12 C13 S1 0.16(15) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C13 S1 C10 C9 -179.19(11) . . . . ?
C13 S1 C10 C11 0.56(10) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_9b
_database_code_depnum_ccdc_archive 'CCDC 2113096'
loop_
_audit_author_name
_audit_author_address
'Stephen Moggach'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2021-09-30 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3


_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N6 O'
_chemical_formula_sum            'C15 H16 N6 O'
_chemical_formula_weight         296.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 C20 H20 O1'
_chemical_oxdiff_usercomment     'UTas sample'
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4529(3)
_cell_length_b                   10.4903(3)
_cell_length_c                   12.3136(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.940(2)
_cell_angle_gamma                90
_cell_volume                     1461.44(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12819
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      74.6590
_cell_measurement_theta_min      3.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  0.6814
_exptl_absorpt_correction_T_min  0.5382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.1138 after correction.
The Ratio of minimum to maximum transmission is 0.7898.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -3 -5 0.0903
-2 4 6 0.0953
-6 3 4 0.1049
-7 0 0 0.1163
0 -4 -6 0.0836
7 1 1 0.0857
0 5 -5 0.0418
-7 -1 -1 0.1125
-1 -5 5 0.0343

_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.084
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9586 -3.4823 -5.0628 -0.4847 0.7924 -0.3702
-1.9602 4.2178 6.1596 0.5201 -0.8495 -0.0888
-6.0726 2.8303 4.1010 0.4278 -0.6998 0.5721
-7.2930 -0.1252 -0.2328 0.1063 -0.1752 0.9788
-0.1719 -4.2188 -6.1756 -0.4849 0.7915 0.3720
6.9426 1.2919 1.2131 0.0486 0.0307 -0.9983
0.4853 5.2658 -5.0680 0.8523 0.5217 0.0364
-6.9476 -1.3858 -1.1214 -0.0639 -0.0401 0.9972
-1.1814 -5.3580 4.9092 -0.8511 -0.5210 0.0645

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25448
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.079
_diffrn_reflns_theta_min         3.907
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00   0.00  108
  2  ω     30.00 105.00   0.50    0.15    --  102.41 -77.00 -30.00  150
  3  ω     37.00  70.00   0.50    0.15    --  102.41 -61.00-180.00   66
  4  ω    -28.00  26.00   0.50    0.05    --   46.20 -19.00  90.00  108
  5  ω     86.00 175.00   0.50    0.15    --  102.41  61.00   0.00  178
  6  ω     49.00 118.00   0.50    0.05    --   46.20 162.00-172.00  138
  7  ω     30.00 109.00   0.50    0.15    --  102.41-117.00 -50.00  158
  8  ω     30.00 111.00   0.50    0.15    --  102.41-125.00 -90.00  162
  9  ω     36.00  75.00   0.50    0.15    --  102.41-125.00   0.00   78
 10  ω     81.00 111.00   0.50    0.15    --  102.41-125.00   0.00   60
 11  ω     32.00 118.00   0.50    0.05    --   46.20-162.00 159.00  172
 12  ω     32.00 136.00   0.50    0.15    --  102.41-162.00 159.00  208
 13  ω     36.00 105.00   0.50    0.15    --  102.41-125.00 150.00  138
 14  ω      7.00  90.00   0.50    0.05    --   46.20-117.00 -50.00  166
 15  ω   -109.00 -30.00   0.50    0.15    -- -102.41 117.00  37.00  158
 16  ω   -111.00 -30.00   0.50    0.15    -- -102.41 125.00 150.00  162
 17  ω   -123.00 -30.00   0.50    0.15    -- -102.41 141.00  41.65  186
 18  ω    -90.00  -7.00   0.50    0.05    --  -46.20 117.00  37.00  166
 19  ω   -117.00 -31.00   0.50    0.05    --  -46.20 162.00-172.00  172
 20  ω   -136.00 -31.00   0.50    0.15    -- -102.41 162.00-172.00  210
 21  ω    -71.00 -30.00   0.50    0.15    -- -102.41  61.00   0.00   82
 22  ω    -71.00 -30.00   0.50    0.15    -- -102.41  61.00  60.00   82
 23  ω   -105.00 -30.00   0.50    0.15    -- -102.41  77.00  60.00  150
 24  ω    -71.00 -30.00   0.50    0.15    -- -102.41  61.00-150.00   82
 25  ω    -71.00 -30.00   0.50    0.15    -- -102.41  61.00-120.00   82
 26  ω   -175.00 -90.00   0.50    0.15    -- -102.41 -46.00  39.76  170
 27  ω   -175.00 -84.00   0.50    0.15    -- -102.41 -65.00 176.91  182
 28  ω   -175.00 -89.00   0.50    0.15    -- -102.41 -52.00 101.86  172
 29  ω   -118.00 -23.00   0.50    0.05    --  -46.20 -77.00-120.00  190
 30  ω   -175.00 -80.00   0.50    0.15    -- -102.41 -77.00-112.23  190
 31  ω   -175.00 -88.00   0.50    0.15    -- -102.41 -54.00-139.96  174
 32  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00   0.00   90
 33  ω   -118.00 -73.00   0.50    0.05    --  -46.20-125.00  60.00   90
 34  ω   -118.00 -49.00   0.50    0.05    --  -46.20-162.00 159.00  138
 35  ω   -156.00 -49.00   0.50    0.15    -- -102.41-162.00 159.00  214
 36  ω   -175.00 -73.00   0.50    0.15    -- -102.41-125.00  90.00  204
 37  ω   -175.00 -78.00   0.50    0.15    -- -102.41-117.00 -50.00  194
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0164323000
_diffrn_orient_matrix_UB_12      0.1444264000
_diffrn_orient_matrix_UB_13      -0.0196920000
_diffrn_orient_matrix_UB_21      0.0280673000
_diffrn_orient_matrix_UB_22      -0.0166655000
_diffrn_orient_matrix_UB_23      -0.1175695000
_diffrn_orient_matrix_UB_31      -0.1324994000
_diffrn_orient_matrix_UB_32      -0.0212982000
_diffrn_orient_matrix_UB_33      -0.0419917000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2593
_reflns_number_total             2957
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0039(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1461P)²+0.2626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00O)
2.b Idealised Me refined as rotating group:
 C00J(H00B,H00C,H00J), C00L(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 1.01114(10) 0.38603(12) 0.11903(10) 0.0274(4) Uani 1 1 d . . . . .
N002 N 0.72703(12) 0.36395(13) 0.17512(12) 0.0220(4) Uani 1 1 d . . . . .
N003 N 0.88340(12) 0.39599(13) 0.35584(12) 0.0227(4) Uani 1 1 d . . . . .
N004 N 0.81730(12) 0.42150(14) 0.13276(12) 0.0233(4) Uani 1 1 d . . . . .
N005 N 0.95451(12) 0.34999(14) 0.28552(12) 0.0226(4) Uani 1 1 d . . . . .
N006 N 0.42044(13) 0.30849(14) 0.10324(13) 0.0257(4) Uani 1 1 d . . . . .
N007 N 0.87345(13) 0.39263(14) 0.64163(12) 0.0258(4) Uani 1 1 d . . . . .
C008 C 0.52520(14) 0.31119(15) 0.16984(14) 0.0224(4) Uani 1 1 d . . . . .
C009 C 0.90790(15) 0.36644(16) 0.45826(14) 0.0235(4) Uani 1 1 d . . . . .
H009 H 0.973536 0.316372 0.483487 0.028 Uiso 1 1 calc R U . . .
C00A C 0.62125(15) 0.37486(16) 0.12357(14) 0.0233(4) Uani 1 1 d . . . . .
H00A H 0.605536 0.421623 0.058781 0.028 Uiso 1 1 calc R U . . .
C00B C 0.93244(15) 0.38512(16) 0.17661(15) 0.0229(4) Uani 1 1 d . . . . .
C00C C 0.83137(15) 0.41244(16) 0.53465(15) 0.0242(4) Uani 1 1 d . . . . .
C00D C 0.45002(16) 0.19326(17) 0.30999(16) 0.0285(4) Uani 1 1 d . . . . .
H00D H 0.459459 0.156231 0.379428 0.034 Uiso 1 1 calc R U . . .
C00E C 0.54259(15) 0.25715(16) 0.27459(15) 0.0249(4) Uani 1 1 d . . . . .
H00E H 0.615302 0.264014 0.319841 0.030 Uiso 1 1 calc R U . . .
C00F C 0.34305(16) 0.18518(17) 0.24060(17) 0.0283(4) Uani 1 1 d . . . . .
H00F H 0.280172 0.139917 0.261159 0.034 Uiso 1 1 calc R U . . .
C00G C 0.69767(17) 0.49081(17) 0.68762(17) 0.0301(5) Uani 1 1 d . . . . .
H00G H 0.654480 0.516581 0.741777 0.036 Uiso 1 1 calc R U . . .
C00H C 0.80618(17) 0.43113(17) 0.71470(15) 0.0281(4) Uani 1 1 d . . . . .
H00H H 0.834031 0.416940 0.788753 0.034 Uiso 1 1 calc R U . . .
C00I C 0.33188(15) 0.24595(17) 0.14005(16) 0.0281(4) Uani 1 1 d . . . . .
H00I H 0.258718 0.243480 0.095107 0.034 Uiso 1 1 calc R U . . .
C00J C 0.79757(16) 0.47976(18) 0.02446(14) 0.0280(4) Uani 1 1 d . . . . .
H00B H 0.765639 0.417465 -0.029156 0.042 Uiso 1 1 calc R U . . .
H00C H 0.871168 0.511152 0.006996 0.042 Uiso 1 1 calc R U . . .
H00J H 0.742856 0.549164 0.023959 0.042 Uiso 1 1 calc R U . . .
C00K C 0.72212(16) 0.47047(17) 0.49944(16) 0.0286(4) Uani 1 1 d . . . . .
H00K H 0.694836 0.481607 0.424891 0.034 Uiso 1 1 calc R U . . .
C00L C 1.05781(15) 0.27122(18) 0.32268(16) 0.0289(5) Uani 1 1 d . . . . .
H00L H 1.114912 0.320050 0.370870 0.043 Uiso 1 1 calc R U . . .
H00M H 1.091999 0.243408 0.260311 0.043 Uiso 1 1 calc R U . . .
H00N H 1.034581 0.198310 0.361324 0.043 Uiso 1 1 calc R U . . .
C00M C 0.65545(16) 0.51092(18) 0.57706(17) 0.0312(5) Uani 1 1 d . . . . .
H00O H 0.583177 0.551136 0.555593 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.230(2) . ?
N002 N004 1.369(2) . ?
N002 C00A 1.282(2) . ?
N003 N005 1.366(2) . ?
N003 C009 1.287(2) . ?
N004 C00B 1.398(2) . ?
N004 C00J 1.452(2) . ?
N005 C00B 1.376(2) . ?
N005 C00L 1.457(2) . ?
N006 C008 1.344(2) . ?
N006 C00I 1.344(2) . ?
N007 C00C 1.347(2) . ?
N007 C00H 1.335(2) . ?
C008 C00A 1.475(2) . ?
C008 C00E 1.395(2) . ?
C009 H009 0.9300 . ?
C009 C00C 1.464(3) . ?
C00A H00A 0.9300 . ?
C00C C00K 1.398(3) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.381(3) . ?
C00D C00F 1.383(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.381(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.385(3) . ?
C00G C00M 1.388(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00B 0.9600 . ?
C00J H00C 0.9600 . ?
C00J H00J 0.9600 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.380(3) . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00M H00O 0.9300 . ?

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
C00A N002 N004 118.91(14) . . ?
C009 N003 N005 118.40(14) . . ?
N002 N004 C00B 117.09(14) . . ?
N002 N004 C00J 121.11(13) . . ?
C00B N004 C00J 118.18(15) . . ?
N003 N005 C00B 119.08(13) . . ?
N003 N005 C00L 122.44(14) . . ?
C00B N005 C00L 118.37(15) . . ?
C008 N006 C00I 116.95(16) . . ?
C00H N007 C00C 117.16(15) . . ?
N006 C008 C00A 114.99(15) . . ?
N006 C008 C00E 122.77(16) . . ?
C00E C008 C00A 122.24(15) . . ?
N003 C009 H009 120.3 . . ?
N003 C009 C00C 119.30(15) . . ?
C00C C009 H009 120.3 . . ?
N002 C00A C008 118.18(15) . . ?
N002 C00A H00A 120.9 . . ?
C008 C00A H00A 120.9 . . ?
O001 C00B N004 120.45(16) . . ?
O001 C00B N005 121.58(15) . . ?
N005 C00B N004 117.97(15) . . ?
N007 C00C C009 114.76(15) . . ?
N007 C00C C00K 122.51(17) . . ?
C00K C00C C009 122.72(16) . . ?
C00E C00D H00D 120.5 . . ?
C00E C00D C00F 118.98(17) . . ?
C00F C00D H00D 120.5 . . ?
C008 C00E H00E 120.6 . . ?
C00D C00E C008 118.88(15) . . ?
C00D C00E H00E 120.6 . . ?
C00D C00F H00F 120.8 . . ?
C00I C00F C00D 118.39(17) . . ?
C00I C00F H00F 120.8 . . ?
C00H C00G H00G 121.1 . . ?
C00H C00G C00M 117.87(18) . . ?
C00M C00G H00G 121.1 . . ?
N007 C00H C00G 124.38(17) . . ?
N007 C00H H00H 117.8 . . ?
C00G C00H H00H 117.8 . . ?
N006 C00I C00F 123.92(16) . . ?
N006 C00I H00I 118.0 . . ?
C00F C00I H00I 118.0 . . ?
N004 C00J H00B 109.5 . . ?
N004 C00J H00C 109.5 . . ?
N004 C00J H00J 109.5 . . ?
H00B C00J H00C 109.5 . . ?
H00B C00J H00J 109.5 . . ?
H00C C00J H00J 109.5 . . ?
C00C C00K H00K 120.5 . . ?
C00M C00K C00C 118.95(18) . . ?
C00M C00K H00K 120.5 . . ?
N005 C00L H00L 109.5 . . ?
N005 C00L H00M 109.5 . . ?
N005 C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
C00G C00M H00O 120.4 . . ?
C00K C00M C00G 119.12(18) . . ?
C00K C00M H00O 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 N004 C00B O001 148.83(16) . . . . ?
N002 N004 C00B N005 -31.8(2) . . . . ?
N003 N005 C00B O001 154.24(16) . . . . ?
N003 N005 C00B N004 -25.1(2) . . . . ?
N003 C009 C00C N007 -170.69(15) . . . . ?
N003 C009 C00C C00K 10.4(3) . . . . ?
N004 N002 C00A C008 179.43(14) . . . . ?
N005 N003 C009 C00C -178.69(13) . . . . ?
N006 C008 C00A N002 -169.48(16) . . . . ?
N006 C008 C00E C00D 2.9(3) . . . . ?
N007 C00C C00K C00M 1.0(3) . . . . ?
C008 N006 C00I C00F -0.3(3) . . . . ?
C009 N003 N005 C00B -177.28(15) . . . . ?
C009 N003 N005 C00L -1.2(2) . . . . ?
C009 C00C C00K C00M 179.91(16) . . . . ?
C00A N002 N004 C00B -166.27(16) . . . . ?
C00A N002 N004 C00J -8.1(2) . . . . ?
C00A C008 C00E C00D -176.60(16) . . . . ?
C00C N007 C00H C00G -0.8(3) . . . . ?
C00C C00K C00M C00G -1.2(3) . . . . ?
C00D C00F C00I N006 2.9(3) . . . . ?
C00E C008 C00A N002 10.0(2) . . . . ?
C00E C00D C00F C00I -2.5(3) . . . . ?
C00F C00D C00E C008 -0.1(3) . . . . ?
C00H N007 C00C C009 -179.03(15) . . . . ?
C00H N007 C00C C00K -0.1(3) . . . . ?
C00H C00G C00M C00K 0.4(3) . . . . ?
C00I N006 C008 C00A 176.86(15) . . . . ?
C00I N006 C008 C00E -2.7(2) . . . . ?
C00J N004 C00B O001 -10.0(2) . . . . ?
C00J N004 C00B N005 169.34(15) . . . . ?
C00L N005 C00B O001 -22.0(2) . . . . ?
C00L N005 C00B N004 158.72(15) . . . . ?
C00M C00G C00H N007 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.766
_oxdiff_exptl_absorpt_empirical_full_min 0.655
