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

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

data_drr19_s1870
_database_code_depnum_ccdc_archive 'CCDC 1982904'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1870
_sydney_internal_submission_date 2019-08-26
_sydney_internal_submission_number s1870
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsana.anjum@sydney.edu.au
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richardson'
_sydney_internal_collection_date 2019-09-24
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-09-24
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-09-24
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-09-24
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-09-24
_sydney_internal_check_user      wlew0588
_refine_special_details          ?
_audit_creation_date             2019-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N3 O2'
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H15N3O2
_chemical_oxdiff_usercomment     SF-30
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                   9.5986(4)
_cell_length_b                   5.3235(2)
_cell_length_c                   29.7891(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.314(4)
_cell_angle_gamma                90
_cell_volume                     1520.92(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.2880
_cell_measurement_theta_min      4.5880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0061
-1 0 0 0.0311
0 0 -1 0.0726
0 0 1 0.0336
0 -1 -5 0.1408
-3 3 -2 0.1887
-5 -2 2 0.1035
2 3 -4 0.1966
-5 0 13 0.0394
5 0 -12 0.0399
2 -3 6 0.1412

_exptl_crystal_recrystallization_method 'crystallised from ethanol'
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.037
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
0.9997 0.0012 0.0026 -0.0105 0.1337 0.0883
-0.9997 -0.0012 -0.0026 0.0105 -0.1337 -0.0883
0.0001 0.0002 -0.9994 0.0501 0.0080 -0.0100
-0.0001 -0.0002 0.9994 -0.0501 -0.0080 0.0100
0.0052 -0.9975 -4.9927 0.3212 -0.1105 0.1862
-3.0127 2.9925 -2.0194 -0.0804 0.0663 -0.9939
-4.9892 -2.0032 1.9941 0.0934 -0.9857 0.0513
1.9859 2.9987 -4.0050 -0.0325 0.7510 -0.5725
-4.9997 -0.0084 12.9788 -0.5991 -0.7728 -0.3110
4.9996 0.0082 -11.9794 0.5490 0.7648 0.3211
2.0126 -2.9945 6.0142 -0.1096 -0.2321 0.9457

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            5244
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.522
_diffrn_reflns_theta_min         4.611
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  19.00   1.00    2.50    --  -39.19  38.00 120.00   39
  2  ω   -115.00 -14.00   1.00    2.50    --  -39.19 -57.00-120.00  101
  3  ω     -5.00  40.00   1.00    2.50    --  -39.19  19.00-180.00   45
  4  ω     14.00  42.00   1.00    2.50    --  -39.19  19.00  30.00   28
  5  ω      5.00  37.00   1.00    2.50    --  -39.19  19.00 -30.00   32
  6  ω    153.00 178.00   1.00   10.00    --  106.69  30.00-180.00   25
  7  ω     28.00  57.00   1.00   10.00    --  106.69 -30.00  30.00   29
  8  ω     29.00  57.00   1.00   10.00    --  106.69 -30.00   0.00   28
  9  ω     27.00  53.00   1.00   10.00    --  106.69 -30.00 -30.00   26
 10  ω     41.00  72.00   1.00   10.00    --  106.69 -45.00-120.00   31
 11  ω    106.00 177.00   1.00   10.00    --  106.69 111.00  90.00   71
 12  ω     73.00 138.00   1.00   10.00    --  106.69  30.00-180.00   65
 13  ω     39.00  71.00   1.00   10.00    --  106.69 -45.00  60.00   32
 14  ω     30.00  57.00   1.00   10.00    --  106.69 -30.00 -60.00   27
 15  ω     27.00  54.00   1.00   10.00    --  106.69 -30.00 150.00   27
 16  ω     78.00 153.00   1.00   10.00    --  106.69  45.00 -90.00   75
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0102468000
_diffrn_orient_matrix_UB_12      -0.0710381000
_diffrn_orient_matrix_UB_13      -0.0501568000
_diffrn_orient_matrix_UB_21      0.1336248000
_diffrn_orient_matrix_UB_22      0.1513040000
_diffrn_orient_matrix_UB_23      -0.0079676000
_diffrn_orient_matrix_UB_31      0.0885507000
_diffrn_orient_matrix_UB_32      -0.2362228000
_diffrn_orient_matrix_UB_33      0.0099934000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2478
_reflns_number_total             2952
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.028
_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)+(0.0510P)²+0.3806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1017
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.55041(10) 0.38049(19) 0.38919(3) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.32656(11) 0.8983(2) 0.41014(3) 0.0296(3) Uani 1 1 d . . . . .
N1 N 0.35503(13) 0.5202(2) 0.44632(4) 0.0245(3) Uani 1 1 d . . . . .
H1 H 0.3896(19) 0.361(4) 0.4449(6) 0.029 Uiso 1 1 d R . . . .
N2 N 0.26714(12) 0.5870(2) 0.47972(4) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.14441(13) 0.3409(2) 0.58116(4) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.25602(14) 0.4285(3) 0.51205(5) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.15348(14) 0.4981(3) 0.54634(5) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.04875(16) 0.3941(3) 0.61136(5) 0.0301(3) Uani 1 1 d . . . . .
H3 H 0.041369 0.284030 0.636253 0.036 Uiso 1 1 calc R . . . .
C4 C -0.03966(15) 0.5986(3) 0.60859(5) 0.0301(3) Uani 1 1 d . . . . .
H4 H -0.106567 0.626243 0.630708 0.036 Uiso 1 1 calc R . . . .
C5 C -0.02853(15) 0.7622(3) 0.57284(5) 0.0287(3) Uani 1 1 d . . . . .
H5 H -0.086665 0.906288 0.570096 0.034 Uiso 1 1 calc R . . . .
C6 C 0.06943(15) 0.7113(3) 0.54107(5) 0.0262(3) Uani 1 1 d . . . . .
H6 H 0.079239 0.819817 0.516085 0.031 Uiso 1 1 calc R . . . .
C7 C 0.33416(15) 0.1853(3) 0.51613(5) 0.0267(3) Uani 1 1 d . . . . .
H7A H 0.297453 0.067146 0.493359 0.040 Uiso 1 1 calc GR . . . .
H7B H 0.322797 0.114260 0.546115 0.040 Uiso 1 1 calc GR . . . .
H7C H 0.433331 0.215333 0.511589 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.37773(15) 0.6884(3) 0.41285(5) 0.0241(3) Uani 1 1 d . . . . .
C9 C 0.47491(14) 0.5960(3) 0.37933(5) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.63143(14) 0.3421(3) 0.35276(5) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.72670(15) 0.1450(3) 0.34883(5) 0.0239(3) Uani 1 1 d . . . . .
H11 H 0.741815 0.023603 0.371889 0.029 Uiso 1 1 calc R . . . .
C12 C 0.79703(14) 0.1380(3) 0.30957(5) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.862699 0.007293 0.305454 0.029 Uiso 1 1 calc R . . . .
C13 C 0.77519(14) 0.3193(3) 0.27480(5) 0.0233(3) Uani 1 1 d . . . . .
C14 C 0.84602(15) 0.3026(3) 0.23379(5) 0.0254(3) Uani 1 1 d . . . . .
H14 H 0.911609 0.171640 0.229845 0.030 Uiso 1 1 calc R . . . .
C15 C 0.82081(15) 0.4729(3) 0.20002(5) 0.0268(3) Uani 1 1 d . . . . .
H15 H 0.867634 0.456993 0.172669 0.032 Uiso 1 1 calc R . . . .
C16 C 0.72610(15) 0.6712(3) 0.20547(5) 0.0264(3) Uani 1 1 d . . . . .
H16 H 0.710204 0.789663 0.181970 0.032 Uiso 1 1 calc R . . . .
C17 C 0.65628(15) 0.6942(3) 0.24481(5) 0.0244(3) Uani 1 1 d . . . . .
H17 H 0.592581 0.828727 0.248322 0.029 Uiso 1 1 calc R . . . .
C18 C 0.67898(14) 0.5193(3) 0.27982(5) 0.0223(3) Uani 1 1 d . . . . .
C19 C 0.60623(14) 0.5265(3) 0.32093(5) 0.0223(3) Uani 1 1 d . . . . .
C20 C 0.50477(14) 0.6912(3) 0.33862(5) 0.0236(3) Uani 1 1 d . . . . .
H20 H 0.466127 0.837473 0.324729 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3823(18) . ?
O1 C10 1.3759(16) . ?
O2 C8 1.2221(19) . ?
N1 H1 0.91(2) . ?
N1 N2 1.3769(16) . ?
N1 C8 1.3642(19) . ?
N2 C1 1.2883(19) . ?
N3 C2 1.3385(19) . ?
N3 C3 1.3413(18) . ?
C1 C2 1.4935(18) . ?
C1 C7 1.499(2) . ?
C2 C6 1.398(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.4777(18) . ?
C9 C20 1.356(2) . ?
C10 C11 1.400(2) . ?
C10 C19 1.379(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3743(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.425(2) . ?
C13 C14 1.4245(19) . ?
C13 C18 1.421(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.368(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.407(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3786(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.409(2) . ?
C18 C19 1.4345(18) . ?
C19 C20 1.427(2) . ?
C20 H20 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
C10 O1 C9 105.30(11) . . ?
N2 N1 H1 120.6(11) . . ?
C8 N1 H1 120.4(11) . . ?
C8 N1 N2 118.64(12) . . ?
C1 N2 N1 116.26(12) . . ?
C2 N3 C3 117.09(14) . . ?
N2 C1 C2 115.18(13) . . ?
N2 C1 C7 124.78(12) . . ?
C2 C1 C7 120.02(12) . . ?
N3 C2 C1 116.12(13) . . ?
N3 C2 C6 122.65(13) . . ?
C6 C2 C1 121.21(13) . . ?
N3 C3 H3 117.9 . . ?
N3 C3 C4 124.21(14) . . ?
C4 C3 H3 117.9 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.43(13) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.52(15) . . ?
C6 C5 H5 120.7 . . ?
C2 C6 H6 120.5 . . ?
C5 C6 C2 119.10(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N1 124.95(13) . . ?
O2 C8 C9 121.51(13) . . ?
N1 C8 C9 113.53(13) . . ?
O1 C9 C8 118.19(12) . . ?
C20 C9 O1 111.87(12) . . ?
C20 C9 C8 129.94(14) . . ?
O1 C10 C11 124.70(13) . . ?
O1 C10 C19 110.33(12) . . ?
C19 C10 C11 124.97(12) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 C10 115.88(13) . . ?
C12 C11 H11 122.1 . . ?
C11 C12 H12 118.8 . . ?
C11 C12 C13 122.49(14) . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 121.31(13) . . ?
C18 C13 C12 120.53(12) . . ?
C18 C13 C14 118.15(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.85(14) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.53(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.22(14) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.30(14) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C19 116.80(13) . . ?
C17 C18 C13 119.93(12) . . ?
C17 C18 C19 123.25(13) . . ?
C10 C19 C18 119.33(13) . . ?
C10 C19 C20 106.68(12) . . ?
C20 C19 C18 133.99(14) . . ?
C9 C20 C19 105.82(13) . . ?
C9 C20 H20 127.1 . . ?
C19 C20 H20 127.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.91(2) 2.731(19) 3.4890(17) 141.4(15) 1_545 yes

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
O1 C9 C20 C19 0.03(17) . . . . ?
O1 C10 C11 C12 179.51(13) . . . . ?
O1 C10 C19 C18 -179.15(12) . . . . ?
O1 C10 C19 C20 0.63(16) . . . . ?
O2 C8 C9 O1 166.96(13) . . . . ?
O2 C8 C9 C20 -12.8(2) . . . . ?
N1 N2 C1 C2 -176.38(11) . . . . ?
N1 N2 C1 C7 1.9(2) . . . . ?
N1 C8 C9 O1 -11.84(19) . . . . ?
N1 C8 C9 C20 168.46(15) . . . . ?
N2 N1 C8 O2 0.7(2) . . . . ?
N2 N1 C8 C9 179.41(12) . . . . ?
N2 C1 C2 N3 -177.41(13) . . . . ?
N2 C1 C2 C6 4.6(2) . . . . ?
N3 C2 C6 C5 -0.6(2) . . . . ?
N3 C3 C4 C5 -0.9(2) . . . . ?
C1 C2 C6 C5 177.22(13) . . . . ?
C2 N3 C3 C4 0.1(2) . . . . ?
C3 N3 C2 C1 -177.24(13) . . . . ?
C3 N3 C2 C6 0.7(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C2 -0.3(2) . . . . ?
C7 C1 C2 N3 4.27(19) . . . . ?
C7 C1 C2 C6 -173.71(13) . . . . ?
C8 N1 N2 C1 -175.73(13) . . . . ?
C8 C9 C20 C19 179.76(14) . . . . ?
C9 O1 C10 C11 178.86(13) . . . . ?
C9 O1 C10 C19 -0.60(15) . . . . ?
C10 O1 C9 C8 -179.42(12) . . . . ?
C10 O1 C9 C20 0.34(16) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C10 C19 C20 C9 -0.40(16) . . . . ?
C11 C10 C19 C18 1.4(2) . . . . ?
C11 C10 C19 C20 -178.83(14) . . . . ?
C11 C12 C13 C14 -177.83(14) . . . . ?
C11 C12 C13 C18 0.7(2) . . . . ?
C12 C13 C14 C15 177.78(14) . . . . ?
C12 C13 C18 C17 -178.70(13) . . . . ?
C12 C13 C18 C19 -0.4(2) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C13 C18 C19 C10 -0.6(2) . . . . ?
C13 C18 C19 C20 179.71(15) . . . . ?
C14 C13 C18 C17 -0.2(2) . . . . ?
C14 C13 C18 C19 178.16(13) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C13 0.6(2) . . . . ?
C16 C17 C18 C19 -177.63(14) . . . . ?
C17 C18 C19 C10 177.68(13) . . . . ?
C17 C18 C19 C20 -2.0(3) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C18 C19 C20 C9 179.33(16) . . . . ?
C19 C10 C11 C12 -1.1(2) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_submission    2019-08-26
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-30
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_drr19_s1873
_database_code_depnum_ccdc_archive 'CCDC 1982905'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1873
_sydney_internal_submission_date 2019-08-26
_sydney_internal_submission_number s1783
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richardson'
_sydney_internal_collection_date 2019-09-24
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-09-27
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-09-27
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-09-27
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-09-27
_sydney_internal_check_user      wlew0588
_refine_special_details          
;
The napthofuran ring is rotationally disordered over two orienations. The occupancies of the two 
compenents were refeind competitively , converging to a ratio of 0.87:0.13. 
Equivalent 1,2- and 1,3-distances of the disordered atoms were restrainted to be 
approximately equal. The minor component could not be sensibly refined 
anisotropically, so was refined isotropically with similarity restraints applied.
;
_audit_creation_date             2019-09-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N4 O2'
_chemical_formula_sum            'C24 H16 N4 O2'
_chemical_formula_weight         392.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H16N4O2
_chemical_oxdiff_usercomment     SF-36
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                   6.0168(5)
_cell_length_b                   18.9903(19)
_cell_length_c                   16.5285(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.923(8)
_cell_angle_gamma                90
_cell_volume                     1860.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1525
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.0070
_cell_measurement_theta_min      3.5650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
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    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 0 0.0024
0 0 0 0.0164
-2 0 3 0.2377
4 -3 -2 0.2729
0 1 0 0.0087
0 -1 0 0.0077

_exptl_crystal_recrystallization_method 
'diffusion of diethyl ether vapour into a chloroform solution'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.016
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
0.0003 -0.0004 -0.4997 -0.0327 -0.0178 -0.0293
-0.0003 0.0004 0.4997 0.0327 0.0178 0.0293
-1.9999 -0.0054 3.4996 -0.1170 -0.0474 0.5515
3.9998 -2.9852 -2.4977 0.6408 0.0402 -0.8344
-0.0012 1.0004 0.4982 -0.0049 0.0896 0.0275
0.0012 -1.0004 -0.4982 0.0049 -0.0896 -0.0275

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7361
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.520
_diffrn_reflns_theta_min         4.657
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  36.00   1.00   15.00    --  -39.07  57.00  90.00   72
  2  ω     -3.00  31.00   1.00   15.00    --  -39.07  19.00  60.00   34
  3  ω    -42.00  27.00   1.00   15.00    --  -39.07  57.00-180.00   69
  4  ω      3.00  29.00   1.00   15.00    --  -39.07  19.00 -30.00   26
  5  ω     97.00 130.00   1.00   15.00    --   39.07 178.00  30.00   33
  6  ω     97.00 124.00   1.00   15.00    --   39.07 178.00-180.00   27
  7  ω    104.00 137.00   1.00   60.00    --  106.69 112.00 150.00   33
  8  ω     50.00 107.00   1.00   60.00    --  106.69-112.00-180.00   57
  9  ω     34.00  62.00   1.00   60.00    --  106.69 -45.00  90.00   28
 10  ω     30.00  57.00   1.00   60.00    --  106.69 -30.00 150.00   27
 11  ω     27.00  52.00   1.00   60.00    --  106.69 -30.00  60.00   25
 12  ω     31.00  56.00   1.00   60.00    --  106.69 -30.00-150.00   25
 13  ω     27.00  54.00   1.00   60.00    --  106.69-112.00  90.00   27
 14  ω     84.00 109.00   1.00   60.00    --  106.69-112.00  90.00   25
 15  ω    140.00 178.00   1.00   60.00    --  106.69 112.00 150.00   38
 16  ω     42.00  91.00   1.00   60.00    --  106.69 -61.00-180.00   49
 17  ω     31.00  88.00   1.00   60.00    --  106.69 -95.00  90.00   57
 18  ω     77.00 176.00   1.00   60.00    --  106.69  30.00 -30.00   99
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1732695000
_diffrn_orient_matrix_UB_12      -0.0373495000
_diffrn_orient_matrix_UB_13      0.0655358000
_diffrn_orient_matrix_UB_21      0.0859960000
_diffrn_orient_matrix_UB_22      0.0718945000
_diffrn_orient_matrix_UB_23      0.0357034000
_diffrn_orient_matrix_UB_31      -0.1735098000
_diffrn_orient_matrix_UB_32      -0.0018548000
_diffrn_orient_matrix_UB_33      0.0584384000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2450
_reflns_number_total             3609
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0781
_refine_ls_restrained_S_all      1.134
_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)+(0.0434P)²+2.2506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1872
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
O1A \\sim C21A \\sim C19A \\sim C14A \\sim C23A \\sim C15A \\sim C20A \\sim
C16A \\sim C22A \\sim C17A \\sim C24A \\sim C18A: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
3. Same fragment restrains
{O1, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24} sigma for 1-2:
0.02, 1-3: 0.04
as in
{O1A, C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A}
4. Others
 Sof(O1A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=
 Sof(H21A)=Sof(C22A)=Sof(C23A)=Sof(C24A)=Sof(H24A)=1-FVAR(1)
 Sof(O1)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(C18)=
 Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=
 Sof(C23)=Sof(C24)=Sof(H24)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C15A(H15A),
 C16A(H16A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C24A(H24A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.3776(5) 0.84572(17) 0.50697(16) 0.0386(7) Uani 1 1 d . . . . .
N1 N 0.4596(5) 0.77709(18) 0.62187(19) 0.0292(7) Uani 1 1 d . . . . .
H1 H 0.427(7) 0.765(2) 0.675(3) 0.035 Uiso 1 1 d . U . . .
N2 N 0.6155(5) 0.73774(17) 0.59082(18) 0.0274(7) Uani 1 1 d . . . . .
N3 N 0.9403(5) 0.5864(2) 0.6277(2) 0.0359(8) Uani 1 1 d . . . . .
N4 N 0.5464(5) 0.70075(19) 0.7578(2) 0.0325(7) Uani 1 1 d . . . . .
C1 C 0.7347(6) 0.6939(2) 0.6391(2) 0.0271(8) Uani 1 1 d . . . . .
C2 C 0.9008(6) 0.6524(2) 0.6004(2) 0.0283(8) Uani 1 1 d . . . . .
C3 C 1.0942(7) 0.5496(2) 0.5967(3) 0.0399(10) Uani 1 1 d . . . . .
H3 H 1.125143 0.502834 0.615655 0.048 Uiso 1 1 calc R U . . .
C4 C 1.2119(7) 0.5762(2) 0.5380(3) 0.0408(10) Uani 1 1 d . . . . .
H4 H 1.322709 0.548417 0.518424 0.049 Uiso 1 1 calc R U . . .
C5 C 1.1651(6) 0.6436(3) 0.5088(2) 0.0382(10) Uani 1 1 d . . . . .
H5 H 1.241144 0.662818 0.468084 0.046 Uiso 1 1 calc R U . . .
C6 C 1.0047(6) 0.6826(2) 0.5402(2) 0.0309(8) Uani 1 1 d . . . . .
H6 H 0.966850 0.728938 0.520939 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7369(6) 0.6844(2) 0.7292(2) 0.0305(8) Uani 1 1 d . . . . .
C8 C 0.5503(7) 0.6956(2) 0.8395(2) 0.0364(9) Uani 1 1 d . . . . .
H8 H 0.416469 0.706716 0.859958 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7361(7) 0.6751(3) 0.8946(2) 0.0436(11) Uani 1 1 d . . . . .
H9 H 0.731300 0.672497 0.951654 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9311(7) 0.6584(3) 0.8648(3) 0.0440(11) Uani 1 1 d . . . . .
H10 H 1.062912 0.644045 0.901295 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9319(7) 0.6629(2) 0.7815(2) 0.0389(10) Uani 1 1 d . . . . .
H11 H 1.064045 0.651454 0.760005 0.047 Uiso 1 1 calc R U . . .
C12 C 0.3421(6) 0.8278(2) 0.5748(2) 0.0313(8) Uani 1 1 d . . . . .
C13 C 0.1620(6) 0.8591(2) 0.6125(2) 0.0328(9) Uani 1 1 d . . . . .
O1 O 0.0531(5) 0.91622(18) 0.56788(19) 0.0330(8) Uani 0.871(4) 1 d D . P A 1
C14 C -0.1109(7) 0.9372(3) 0.6125(3) 0.0300(10) Uani 0.871(4) 1 d D . P A 1
C15 C -0.2598(7) 0.9921(3) 0.5896(3) 0.0365(11) Uani 0.871(4) 1 d D . P A 1
H15 H -0.256749 1.018968 0.541261 0.044 Uiso 0.871(4) 1 calc R U P A 1
C16 C -0.4114(8) 1.0056(3) 0.6404(3) 0.0331(14) Uani 0.871(4) 1 d D . P A 1
H16 H -0.518284 1.042288 0.626355 0.040 Uiso 0.871(4) 1 calc R U P A 1
C17 C -0.4146(7) 0.9660(3) 0.7145(3) 0.0317(10) Uani 0.871(4) 1 d D . P A 1
C18 C -0.5730(11) 0.9807(4) 0.7661(5) 0.0342(14) Uani 0.871(4) 1 d D . P A 1
H18 H -0.678069 1.018011 0.752565 0.041 Uiso 0.871(4) 1 calc R U P A 1
C19 C -0.5761(7) 0.9416(3) 0.8356(3) 0.0372(11) Uani 0.871(4) 1 d D . P A 1
H19 H -0.683603 0.952049 0.869816 0.045 Uiso 0.871(4) 1 calc R U P A 1
C20 C -0.4225(8) 0.8863(3) 0.8569(3) 0.0383(11) Uani 0.871(4) 1 d D . P A 1
H20 H -0.427026 0.859339 0.905027 0.046 Uiso 0.871(4) 1 calc R U P A 1
C21 C -0.2651(14) 0.8710(5) 0.8080(4) 0.0313(16) Uani 0.871(4) 1 d D . P A 1
H21 H -0.159600 0.834089 0.823006 0.038 Uiso 0.871(4) 1 calc R U P A 1
C22 C -0.2596(6) 0.9100(2) 0.7356(3) 0.0279(9) Uani 0.871(4) 1 d D . P A 1
C23 C -0.1055(15) 0.8951(5) 0.6807(5) 0.0260(13) Uani 0.871(4) 1 d D . P A 1
C24 C 0.0768(7) 0.8465(3) 0.6799(3) 0.0285(10) Uani 0.871(4) 1 d D . P A 1
H24 H 0.127141 0.811739 0.720251 0.034 Uiso 0.871(4) 1 calc R U P A 1
O1A O 0.153(3) 0.8187(10) 0.7021(11) 0.021(4) Uiso 0.129(4) 1 d D U P A 2
C14A C -0.023(4) 0.8539(13) 0.7288(13) 0.027(5) Uiso 0.129(4) 1 d D U P A 2
C15A C -0.088(4) 0.8428(14) 0.8049(14) 0.032(6) Uiso 0.129(4) 1 d D U P A 2
H15A H -0.007211 0.811442 0.844171 0.038 Uiso 0.129(4) 1 calc R U P A 2
C16A C -0.272(11) 0.879(4) 0.821(3) 0.034(8) Uiso 0.129(4) 1 d D U P A 2
H16A H -0.325019 0.870639 0.870757 0.040 Uiso 0.129(4) 1 calc R U P A 2
C17A C -0.389(4) 0.9289(15) 0.7632(15) 0.038(6) Uiso 0.129(4) 1 d D U P A 2
C18A C -0.577(10) 0.967(4) 0.779(3) 0.037(8) Uiso 0.129(4) 1 d D U P A 2
H18A H -0.627864 0.961351 0.829892 0.045 Uiso 0.129(4) 1 calc R U P A 2
C19A C -0.687(5) 1.0133(17) 0.7217(16) 0.042(6) Uiso 0.129(4) 1 d D U P A 2
H19A H -0.813735 1.038691 0.733434 0.050 Uiso 0.129(4) 1 calc R U P A 2
C20A C -0.616(4) 1.0235(16) 0.6456(16) 0.037(6) Uiso 0.129(4) 1 d D U P A 2
H20A H -0.693012 1.055678 0.606572 0.045 Uiso 0.129(4) 1 calc R U P A 2
C21A C -0.433(6) 0.9861(19) 0.6287(19) 0.029(7) Uiso 0.129(4) 1 d D U P A 2
H21A H -0.387196 0.991435 0.576770 0.034 Uiso 0.129(4) 1 calc R U P A 2
C22A C -0.312(4) 0.9399(14) 0.6877(14) 0.031(5) Uiso 0.129(4) 1 d D U P A 2
C23A C -0.109(11) 0.906(4) 0.674(3) 0.029(7) Uiso 0.129(4) 1 d D U P A 2
C24A C 0.005(5) 0.8994(16) 0.6043(15) 0.032(6) Uiso 0.129(4) 1 d D U P A 2
H24A H -0.041321 0.925386 0.555160 0.038 Uiso 0.129(4) 1 calc R U P A 2


_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
O2 C12 1.225(5) . ?
N1 H1 0.97(4) . ?
N1 N2 1.367(4) . ?
N1 C12 1.358(5) . ?
N2 C1 1.283(5) . ?
N3 C2 1.339(5) . ?
N3 C3 1.330(5) . ?
N4 C7 1.349(5) . ?
N4 C8 1.349(5) . ?
C1 C2 1.499(5) . ?
C1 C7 1.498(5) . ?
C2 C6 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9500 . ?
C7 C11 1.393(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.466(5) . ?
C13 O1 1.409(5) . ?
C13 C24 1.326(6) . ?
C13 O1A 1.677(19) . ?
C13 C24A 1.21(3) . ?
O1 C14 1.388(5) . ?
C14 C15 1.386(6) . ?
C14 C23 1.378(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.440(7) . ?
C17 C18 1.412(6) . ?
C17 C22 1.417(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.372(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.403(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.412(7) . ?
C22 C23 1.432(6) . ?
C23 C24 1.436(6) . ?
C24 H24 0.9500 . ?
O1A C14A 1.389(17) . ?
C14A C15A 1.395(18) . ?
C14A C23A 1.38(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.37(2) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.437(19) . ?
C17A C18A 1.408(18) . ?
C17A C22A 1.420(17) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.37(2) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.409(19) . ?
C20A H20A 0.9500 . ?
C20A C21A 1.380(19) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.417(19) . ?
C22A C23A 1.433(17) . ?
C23A C24A 1.441(19) . ?
C24A H24A 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
N2 N1 H1 118(3) . . ?
C12 N1 H1 122(3) . . ?
C12 N1 N2 119.7(3) . . ?
C1 N2 N1 117.9(3) . . ?
C3 N3 C2 117.2(4) . . ?
C8 N4 C7 117.6(3) . . ?
N2 C1 C2 114.7(3) . . ?
N2 C1 C7 127.2(3) . . ?
C7 C1 C2 117.9(3) . . ?
N3 C2 C1 116.2(3) . . ?
N3 C2 C6 123.5(3) . . ?
C6 C2 C1 120.3(4) . . ?
N3 C3 H3 118.3 . . ?
N3 C3 C4 123.3(4) . . ?
C4 C3 H3 118.3 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C2 C6 H6 120.8 . . ?
C5 C6 C2 118.5(4) . . ?
C5 C6 H6 120.8 . . ?
N4 C7 C1 117.3(3) . . ?
N4 C7 C11 121.7(3) . . ?
C11 C7 C1 120.9(3) . . ?
N4 C8 H8 118.1 . . ?
N4 C8 C9 123.9(4) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C7 C11 H11 120.3 . . ?
C10 C11 C7 119.3(4) . . ?
C10 C11 H11 120.3 . . ?
O2 C12 N1 124.5(3) . . ?
O2 C12 C13 122.3(4) . . ?
N1 C12 C13 113.2(3) . . ?
C12 C13 O1A 109.3(6) . . ?
O1 C13 C12 113.6(3) . . ?
C24 C13 C12 134.9(4) . . ?
C24 C13 O1 111.5(4) . . ?
C24A C13 C12 146.4(12) . . ?
C24A C13 O1A 104.1(13) . . ?
C14 O1 C13 104.6(3) . . ?
C15 C14 O1 123.8(4) . . ?
C23 C14 O1 110.5(4) . . ?
C23 C14 C15 125.7(4) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 C14 116.2(4) . . ?
C16 C15 H15 121.9 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.3(5) . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 121.3(5) . . ?
C18 C17 C22 119.0(5) . . ?
C22 C17 C16 119.7(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(5) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C23 117.6(4) . . ?
C21 C22 C17 119.4(4) . . ?
C21 C22 C23 123.0(5) . . ?
C14 C23 C22 118.5(4) . . ?
C14 C23 C24 106.0(4) . . ?
C22 C23 C24 135.4(5) . . ?
C13 C24 C23 107.4(4) . . ?
C13 C24 H24 126.3 . . ?
C23 C24 H24 126.3 . . ?
C14A O1A C13 101.8(13) . . ?
O1A C14A C15A 124.0(17) . . ?
C23A C14A O1A 110.8(15) . . ?
C23A C14A C15A 124.9(18) . . ?
C14A C15A H15A 121.4 . . ?
C16A C15A C14A 117(2) . . ?
C16A C15A H15A 121.4 . . ?
C15A C16A H16A 119.1 . . ?
C15A C16A C17A 122(2) . . ?
C17A C16A H16A 119.1 . . ?
C18A C17A C16A 122.4(19) . . ?
C18A C17A C22A 118.9(18) . . ?
C22A C17A C16A 118.8(17) . . ?
C17A C18A H18A 119.7 . . ?
C19A C18A C17A 121(2) . . ?
C19A C18A H18A 119.7 . . ?
C18A C19A H19A 119.4 . . ?
C18A C19A C20A 121(2) . . ?
C20A C19A H19A 119.4 . . ?
C19A C20A H20A 120.4 . . ?
C21A C20A C19A 119(2) . . ?
C21A C20A H20A 120.4 . . ?
C20A C21A H21A 119.6 . . ?
C20A C21A C22A 121(2) . . ?
C22A C21A H21A 119.6 . . ?
C17A C22A C23A 119.3(17) . . ?
C21A C22A C17A 119.2(17) . . ?
C21A C22A C23A 121.4(18) . . ?
C14A C23A C22A 117(2) . . ?
C14A C23A C24A 106.9(18) . . ?
C22A C23A C24A 134(3) . . ?
C13 C24A C23A 115.8(19) . . ?
C13 C24A H24A 122.1 . . ?
C23A C24A H24A 122.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N4 0.97(4) 1.87(4) 2.649(5) 135(4) . yes

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
O2 C12 C13 O1 -6.7(6) . . . . ?
O2 C12 C13 C24 173.9(5) . . . . ?
O2 C12 C13 O1A 176.7(8) . . . . ?
O2 C12 C13 C24A 4(3) . . . . ?
N1 N2 C1 C2 179.6(3) . . . . ?
N1 N2 C1 C7 -5.3(6) . . . . ?
N1 C12 C13 O1 174.3(3) . . . . ?
N1 C12 C13 C24 -5.2(7) . . . . ?
N1 C12 C13 O1A -2.4(8) . . . . ?
N1 C12 C13 C24A -175(3) . . . . ?
N2 N1 C12 O2 -6.4(6) . . . . ?
N2 N1 C12 C13 172.6(3) . . . . ?
N2 C1 C2 N3 -146.5(4) . . . . ?
N2 C1 C2 C6 33.7(5) . . . . ?
N2 C1 C7 N4 27.7(6) . . . . ?
N2 C1 C7 C11 -149.0(4) . . . . ?
N3 C2 C6 C5 -2.8(6) . . . . ?
N3 C3 C4 C5 -1.3(7) . . . . ?
N4 C7 C11 C10 -0.2(7) . . . . ?
N4 C8 C9 C10 -0.4(7) . . . . ?
C1 C2 C6 C5 177.0(3) . . . . ?
C1 C7 C11 C10 176.4(4) . . . . ?
C2 N3 C3 C4 -0.5(6) . . . . ?
C2 C1 C7 N4 -157.3(3) . . . . ?
C2 C1 C7 C11 25.9(6) . . . . ?
C3 N3 C2 C1 -177.2(4) . . . . ?
C3 N3 C2 C6 2.6(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C2 0.9(6) . . . . ?
C7 N4 C8 C9 0.4(7) . . . . ?
C7 C1 C2 N3 38.0(5) . . . . ?
C7 C1 C2 C6 -141.8(4) . . . . ?
C8 N4 C7 C1 -176.8(4) . . . . ?
C8 N4 C7 C11 -0.1(6) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C7 0.2(7) . . . . ?
C12 N1 N2 C1 175.0(3) . . . . ?
C12 C13 O1 C14 179.1(3) . . . . ?
C12 C13 C24 C23 -178.1(7) . . . . ?
C12 C13 O1A C14A -179.8(14) . . . . ?
C12 C13 C24A C23A -179(5) . . . . ?
C13 O1 C14 C15 -179.4(4) . . . . ?
C13 O1 C14 C23 -0.4(7) . . . . ?
C13 O1A C14A C15A -175(3) . . . . ?
C13 O1A C14A C23A -1(5) . . . . ?
O1 C13 C24 C23 2.4(7) . . . . ?
O1 C14 C15 C16 179.7(5) . . . . ?
O1 C14 C23 C22 178.4(7) . . . . ?
O1 C14 C23 C24 1.8(10) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C14 C23 C24 C13 -2.5(10) . . . . ?
C15 C14 C23 C22 -2.6(14) . . . . ?
C15 C14 C23 C24 -179.2(5) . . . . ?
C15 C16 C17 C18 -179.9(6) . . . . ?
C15 C16 C17 C22 -1.3(8) . . . . ?
C16 C17 C18 C19 178.8(6) . . . . ?
C16 C17 C22 C21 -179.5(7) . . . . ?
C16 C17 C22 C23 -0.4(8) . . . . ?
C17 C18 C19 C20 0.0(10) . . . . ?
C17 C22 C23 C14 2.2(13) . . . . ?
C17 C22 C23 C24 177.6(11) . . . . ?
C18 C17 C22 C21 -0.8(9) . . . . ?
C18 C17 C22 C23 178.2(8) . . . . ?
C18 C19 C20 C21 0.4(9) . . . . ?
C19 C20 C21 C22 -1.1(12) . . . . ?
C20 C21 C22 C17 1.3(12) . . . . ?
C20 C21 C22 C23 -177.7(9) . . . . ?
C21 C22 C23 C14 -178.8(8) . . . . ?
C21 C22 C23 C24 -3.3(18) . . . . ?
C22 C17 C18 C19 0.2(10) . . . . ?
C22 C23 C24 C13 -178.4(12) . . . . ?
C23 C14 C15 C16 0.9(10) . . . . ?
C24 C13 O1 C14 -1.3(5) . . . . ?
O1A C13 C24A C23A 8(5) . . . . ?
O1A C14A C15A C16A -177(5) . . . . ?
O1A C14A C23A C22A 172(6) . . . . ?
O1A C14A C23A C24A 5(8) . . . . ?
C14A C15A C16A C17A -3(10) . . . . ?
C14A C23A C24A C13 -9(9) . . . . ?
C15A C14A C23A C22A -15(11) . . . . ?
C15A C14A C23A C24A 179(4) . . . . ?
C15A C16A C17A C18A -179(7) . . . . ?
C15A C16A C17A C22A 1(10) . . . . ?
C16A C17A C18A C19A -178(7) . . . . ?
C16A C17A C22A C21A 176(5) . . . . ?
C16A C17A C22A C23A -6(8) . . . . ?
C17A C18A C19A C20A 0(10) . . . . ?
C17A C22A C23A C14A 12(10) . . . . ?
C17A C22A C23A C24A 173(8) . . . . ?
C18A C17A C22A C21A -3(6) . . . . ?
C18A C17A C22A C23A 175(7) . . . . ?
C18A C19A C20A C21A 0(7) . . . . ?
C19A C20A C21A C22A -2(6) . . . . ?
C20A C21A C22A C17A 4(6) . . . . ?
C20A C21A C22A C23A -174(6) . . . . ?
C21A C22A C23A C14A -170(5) . . . . ?
C21A C22A C23A C24A -9(13) . . . . ?
C22A C17A C18A C19A 2(9) . . . . ?
C22A C23A C24A C13 -172(8) . . . . ?
C23A C14A C15A C16A 10(8) . . . . ?
C24A C13 O1A C14A -4(2) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_data_collection 2019-09-24
_olex2_date_sample_submission    2019-08-26
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-36
_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 1.351
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_drr19_s1885
_database_code_depnum_ccdc_archive 'CCDC 1982908'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1885
_sydney_internal_submission_date 2019-09-03
_sydney_internal_submission_number s1885
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richardson'
_sydney_internal_collection_date 2019-10-03
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-10-03
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-10-03
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-10-03
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-10-03
_sydney_internal_check_user      wlew0588
_refine_special_details          ?
_audit_creation_date             2019-10-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 N4 O S'
_chemical_formula_sum            'C13 H16 N4 O S'
_chemical_formula_weight         276.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H16N4OS
_chemical_oxdiff_usercomment     SF-54
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                   11.9480(4)
_cell_length_b                   8.2148(3)
_cell_length_c                   14.0992(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.638(4)
_cell_angle_gamma                90
_cell_volume                     1338.92(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3134
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.1740
_cell_measurement_theta_min      6.3220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0530
4 4 1 0.1547
-1 0 1 0.0894
0 0 1 0.1032
0 0 -1 0.1011
0 -1 0 0.1807
0 1 0 0.1807
-1 0 0 0.0660
1 0 -1 0.0675

_exptl_crystal_recrystallization_method 'crystallised from dichloromethane'
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.119
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
1.0001 0.0004 -0.0009 0.0144 0.0071 -0.1323
3.9980 4.0067 1.0441 -0.2624 -0.6537 -0.6310
-0.9994 0.0029 1.0062 -0.1161 0.0259 0.0941
0.0001 0.0003 1.0038 -0.1014 0.0335 -0.0380
-0.0001 -0.0003 -1.0038 0.1014 -0.0335 0.0380
-0.0008 -1.0004 -0.0008 0.0536 0.1791 0.0158
0.0008 1.0004 0.0008 -0.0536 -0.1791 -0.0158
-1.0001 -0.0004 0.0009 -0.0144 -0.0071 0.1323
0.9994 -0.0029 -1.0062 0.1161 -0.0259 -0.0941

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5093
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_min         3.824
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  30.00   2.00    2.00    --  -39.19  38.00 -30.00   20
  2  ω      4.00  30.00   2.00    2.00    --  -39.19  19.00-180.00   13
  3  ω     -5.00  25.00   2.00    2.00    --  -39.19  19.00  30.00   15
  4  ω      1.00  35.00   2.00    2.00    --  -39.19  19.00 -60.00   17
  5  ω   -125.00 -53.00   2.00    2.00    --  -39.19 178.00   0.00   36
  6  ω     80.00 124.00   2.00    2.00    --   39.19 178.00  30.00   22
  7  ω     41.00  87.00   2.00    2.00    --  106.69-111.00  30.00   23
  8  ω     30.00  56.00   2.00    2.00    --  106.69 -30.00-150.00   13
  9  ω     27.00  53.00   2.00    2.00    --  106.69 -30.00  30.00   13
 10  ω     29.00  57.00   2.00    2.00    --  106.69 -30.00 -90.00   14
 11  ω     27.00  53.00   2.00    2.00    --  106.69 -30.00 -60.00   13
 12  ω     75.00 107.00   2.00    2.00    --  106.69-111.00-150.00   16
 13  ω    124.00 176.00   2.00    2.00    --  106.69 111.00 -90.00   26
 14  ω     52.00 108.00   2.00    2.00    --  106.69-111.00 -60.00   28
 15  ω     29.00  57.00   2.00    2.00    --  106.69 -30.00   0.00   14
 16  ω    107.00 175.00   2.00    2.00    --  106.69 111.00   0.00   34
 17  ω     80.00 158.00   2.00    2.00    --  106.69  45.00-180.00   39
 18  ω     29.00  57.00   2.00    2.00    --  106.69 -30.00-120.00   14
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0143651000
_diffrn_orient_matrix_UB_12      -0.0535012000
_diffrn_orient_matrix_UB_13      -0.1009756000
_diffrn_orient_matrix_UB_21      0.0072097000
_diffrn_orient_matrix_UB_22      -0.1790605000
_diffrn_orient_matrix_UB_23      0.0334658000
_diffrn_orient_matrix_UB_31      -0.1323096000
_diffrn_orient_matrix_UB_32      -0.0156166000
_diffrn_orient_matrix_UB_33      -0.0378361000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2392
_reflns_number_total             2567
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.054
_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)+(0.0454P)²+0.4253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0840
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.37915(3) 0.20276(4) 0.61670(2) 0.01919(12) Uani 1 1 d . . . . .
O1 O 0.82236(8) 0.50379(12) 0.52024(7) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.55828(9) 0.30163(13) 0.52156(8) 0.0157(2) Uani 1 1 d . . . . .
N2 N 0.47166(10) 0.21018(14) 0.46349(8) 0.0165(2) Uani 1 1 d . . . . .
H2 H 0.4684(14) 0.198(2) 0.4054(13) 0.020 Uiso 1 1 d . U . . .
N3 N 0.30395(9) 0.06471(15) 0.43880(8) 0.0195(3) Uani 1 1 d . . . . .
N4 N 0.65018(11) 0.46810(17) 0.69603(9) 0.0237(3) Uani 1 1 d . . . . .
H4A H 0.5908(16) 0.408(2) 0.6666(13) 0.028 Uiso 1 1 d . U . . .
H4B H 0.6536(15) 0.513(2) 0.7509(14) 0.028 Uiso 1 1 d . U . . .
C1 C 0.38333(11) 0.15580(16) 0.50050(9) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.19849(12) 0.00858(19) 0.46272(11) 0.0243(3) Uani 1 1 d . . . . .
H2A H 0.202341 -0.109592 0.472543 0.037 Uiso 1 1 calc R U . . .
H2B H 0.131476 0.035524 0.408803 0.037 Uiso 1 1 calc R U . . .
H2C H 0.190831 0.062091 0.522882 0.037 Uiso 1 1 calc R U . . .
C3 C 0.31691(12) 0.01777(19) 0.34182(10) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.311917 0.114940 0.300639 0.036 Uiso 1 1 calc R U . . .
H3B H 0.255211 -0.058434 0.311246 0.036 Uiso 1 1 calc R U . . .
H3C H 0.392246 -0.034592 0.348745 0.036 Uiso 1 1 calc R U . . .
C4 C 0.63800(11) 0.35726(16) 0.48248(9) 0.0157(3) Uani 1 1 d . . . . .
C5 C 0.64467(13) 0.32946(19) 0.37884(10) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.652989 0.212738 0.367983 0.034 Uiso 1 1 calc R U . . .
H5B H 0.711557 0.387791 0.367305 0.034 Uiso 1 1 calc R U . . .
H5C H 0.573817 0.369705 0.333552 0.034 Uiso 1 1 calc R U . . .
C6 C 0.72484(11) 0.45120(16) 0.54965(9) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.88766(11) 0.58916(16) 0.59823(10) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.99463(12) 0.65921(18) 0.60255(11) 0.0225(3) Uani 1 1 d . . . . .
H8 H 1.029025 0.654740 0.548772 0.027 Uiso 1 1 calc R U . . .
C9 C 1.04847(12) 0.73609(18) 0.68979(12) 0.0247(3) Uani 1 1 d . . . . .
H9 H 1.121901 0.785478 0.696181 0.030 Uiso 1 1 calc R U . . .
C10 C 0.99692(12) 0.74255(19) 0.76884(11) 0.0238(3) Uani 1 1 d . . . . .
H10 H 1.036117 0.796566 0.827398 0.029 Uiso 1 1 calc R U . . .
C11 C 0.89029(12) 0.67202(17) 0.76336(10) 0.0199(3) Uani 1 1 d . . . . .
H11 H 0.855860 0.676999 0.817097 0.024 Uiso 1 1 calc R U . . .
C12 C 0.83455(11) 0.59283(16) 0.67585(10) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.72916(11) 0.50124(16) 0.64340(9) 0.0158(3) Uani 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 C1 1.6961(13) . ?
O1 C6 1.4001(15) . ?
O1 C7 1.3697(16) . ?
N1 N2 1.3702(16) . ?
N1 C4 1.2981(17) . ?
N2 H2 0.816(18) . ?
N2 C1 1.3653(17) . ?
N3 C1 1.3412(18) . ?
N3 C2 1.4591(17) . ?
N3 C3 1.4660(18) . ?
N4 H4A 0.880(19) . ?
N4 H4B 0.850(19) . ?
N4 C13 1.3672(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.5009(17) . ?
C4 C6 1.4396(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C13 1.3727(18) . ?
C7 C8 1.3889(19) . ?
C7 C12 1.3972(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.4049(19) . ?
C12 C13 1.4387(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C6 105.55(10) . . ?
C4 N1 N2 117.63(11) . . ?
N1 N2 H2 120.3(12) . . ?
C1 N2 N1 119.42(11) . . ?
C1 N2 H2 119.8(12) . . ?
C1 N3 C2 122.46(12) . . ?
C1 N3 C3 121.85(12) . . ?
C2 N3 C3 115.68(11) . . ?
H4A N4 H4B 121.6(17) . . ?
C13 N4 H4A 116.2(12) . . ?
C13 N4 H4B 121.7(12) . . ?
N2 C1 S1 120.59(10) . . ?
N3 C1 S1 124.39(10) . . ?
N3 C1 N2 115.02(12) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 125.80(12) . . ?
N1 C4 C6 113.18(11) . . ?
C6 C4 C5 121.01(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 C4 119.08(11) . . ?
C13 C6 O1 111.17(11) . . ?
C13 C6 C4 129.75(12) . . ?
O1 C7 C8 125.34(13) . . ?
O1 C7 C12 111.13(11) . . ?
C8 C7 C12 123.49(13) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 C7 116.27(13) . . ?
C9 C8 H8 121.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.52(13) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.48(14) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 117.93(13) . . ?
C12 C11 H11 121.0 . . ?
C7 C12 C11 119.31(12) . . ?
C7 C12 C13 105.89(12) . . ?
C11 C12 C13 134.75(13) . . ?
N4 C13 C6 126.86(13) . . ?
N4 C13 C12 126.88(12) . . ?
C6 C13 C12 106.25(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4A N1 0.880(19) 2.165(19) 2.7860(17) 127.1(15) . yes
N4 H4B S1 0.850(19) 2.54(2) 3.3583(13) 163.2(16) 2_656 yes

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
O1 C6 C13 N4 -178.18(13) . . . . ?
O1 C6 C13 C12 0.72(14) . . . . ?
O1 C7 C8 C9 -177.93(13) . . . . ?
O1 C7 C12 C11 178.54(11) . . . . ?
O1 C7 C12 C13 0.64(14) . . . . ?
N1 N2 C1 S1 0.89(17) . . . . ?
N1 N2 C1 N3 -178.75(11) . . . . ?
N1 C4 C6 O1 173.26(11) . . . . ?
N1 C4 C6 C13 -6.6(2) . . . . ?
N2 N1 C4 C5 -0.48(19) . . . . ?
N2 N1 C4 C6 -179.85(11) . . . . ?
C2 N3 C1 S1 5.99(19) . . . . ?
C2 N3 C1 N2 -174.38(12) . . . . ?
C3 N3 C1 S1 -175.19(10) . . . . ?
C3 N3 C1 N2 4.43(19) . . . . ?
C4 N1 N2 C1 -176.98(11) . . . . ?
C4 C6 C13 N4 1.7(2) . . . . ?
C4 C6 C13 C12 -179.37(13) . . . . ?
C5 C4 C6 O1 -6.14(18) . . . . ?
C5 C4 C6 C13 173.95(13) . . . . ?
C6 O1 C7 C8 177.76(13) . . . . ?
C6 O1 C7 C12 -0.21(14) . . . . ?
C7 O1 C6 C4 179.74(11) . . . . ?
C7 O1 C6 C13 -0.34(14) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C7 C12 C13 N4 178.10(13) . . . . ?
C7 C12 C13 C6 -0.81(14) . . . . ?
C8 C7 C12 C11 0.5(2) . . . . ?
C8 C7 C12 C13 -177.38(13) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C7 -0.45(19) . . . . ?
C10 C11 C12 C13 176.70(14) . . . . ?
C11 C12 C13 N4 0.7(2) . . . . ?
C11 C12 C13 C6 -178.23(15) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_submission    2019-09-03
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-54
_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 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.878
####################################################################### 
# 
# 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_cu_2402znl11
_database_code_depnum_ccdc_archive 'CCDC 2424290'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2025-02-17 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;

_audit_creation_date             2025-02-17T09:00:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C25 H17 Cl2 N3 O2 Zn, C H2 Cl2'
_chemical_formula_sum            'C26 H19 Cl4 N3 O2 Zn'
_chemical_formula_weight         612.61

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

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

_cell_length_a                   11.6154(11)
_cell_length_b                   11.9297(12)
_cell_length_c                   11.8935(12)
_cell_angle_alpha                118.435(3)
_cell_angle_beta                 91.579(3)
_cell_angle_gamma                114.295(3)
_cell_volume                     1268.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      68.35
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620

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

_exptl_absorpt_coefficient_mu    5.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.6131
_exptl_absorpt_correction_T_max  0.7531
_shelx_estimated_absorpt_T_min   0.407
_shelx_estimated_absorpt_T_max   0.811

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

_diffrn_source_type              'INCOATEC I\mS DIAMONDII'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'PHOTON III CPAD'
_diffrn_orient_matrix_ub_11      -0.039543
_diffrn_orient_matrix_ub_12      -0.073139
_diffrn_orient_matrix_ub_13      -0.097828
_diffrn_orient_matrix_ub_21      0.042918
_diffrn_orient_matrix_ub_22      0.079371
_diffrn_orient_matrix_ub_23      -0.017912
_diffrn_orient_matrix_ub_31      0.079176
_diffrn_orient_matrix_ub_32      -0.014231
_diffrn_orient_matrix_ub_33      -0.004662
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.167
_diffrn_reflns_number            32185
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.349
_diffrn_reflns_theta_max         63.483
_diffrn_reflns_theta_full        63.484
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4140
_reflns_number_gt                3735
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+2.0476P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.041
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.802
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.125

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3676(3) 0.5230(3) 0.8110(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.2586(3) 0.4493(3) 0.8408(3) 0.0233(6) Uani 1 1 d . . . . .
H2 H 0.224713 0.348721 0.80754 0.028 Uiso 1 1 calc R U . . .
C3 C 0.1992(3) 0.5266(3) 0.9210(3) 0.0287(7) Uani 1 1 d . . . . .
H3 H 0.123573 0.47876 0.942589 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2514(3) 0.6721(3) 0.9684(3) 0.0292(7) Uani 1 1 d . . . . .
H4 H 0.21315 0.726461 1.024216 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3601(3) 0.7385(3) 0.9339(3) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.395094 0.83897 0.966019 0.03 Uiso 1 1 calc R U . . .
C6 C 0.4346(3) 0.4504(3) 0.7215(2) 0.0164(6) Uani 1 1 d . . . . .
C7 C 0.4114(3) 0.3037(3) 0.6844(3) 0.0175(6) Uani 1 1 d . . . . .
C8 C 0.3750(3) 0.1930(3) 0.5508(3) 0.0224(6) Uani 1 1 d . . . . .
H8 H 0.358021 0.208934 0.482535 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3639(3) 0.0605(3) 0.5179(3) 0.0272(7) Uani 1 1 d . . . . .
H9 H 0.338367 -0.014867 0.427019 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3898(3) 0.0369(3) 0.6173(3) 0.0269(7) Uani 1 1 d . . . . .
H10 H 0.384934 -0.053128 0.594463 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4226(3) 0.1453(3) 0.7497(3) 0.0274(7) Uani 1 1 d . . . . .
H11 H 0.438153 0.12849 0.817648 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4329(3) 0.2777(3) 0.7836(3) 0.0223(6) Uani 1 1 d . . . . .
H12 H 0.454759 0.351152 0.874561 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6869(3) 0.5863(3) 0.5919(2) 0.0165(6) Uani 1 1 d . . . . .
C14 C 0.7641(3) 0.5382(3) 0.5056(2) 0.0171(6) Uani 1 1 d . . . . .
C15 C 0.8720(3) 0.6123(3) 0.4784(3) 0.0193(6) Uani 1 1 d . . . . .
H15 H 0.915566 0.713538 0.511797 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9068(3) 0.5069(3) 0.3893(2) 0.0166(6) Uani 1 1 d . . . . .
C17 C 1.0106(3) 0.5138(3) 0.3258(2) 0.0198(6) Uani 1 1 d . . . . .
C18 C 1.1107(3) 0.6437(3) 0.3432(3) 0.0236(6) Uani 1 1 d . . . . .
H18 H 1.111467 0.733424 0.399327 0.028 Uiso 1 1 calc R U . . .
C19 C 1.2071(3) 0.6404(3) 0.2788(3) 0.0300(7) Uani 1 1 d . . . . .
H19 H 1.274026 0.727965 0.290548 0.036 Uiso 1 1 calc R U . . .
C20 C 1.2074(3) 0.5087(4) 0.1961(3) 0.0289(7) Uani 1 1 d . . . . .
H20 H 1.274915 0.507918 0.153011 0.035 Uiso 1 1 calc R U . . .
C21 C 1.1110(3) 0.3816(3) 0.1772(3) 0.0253(6) Uani 1 1 d . . . . .
H21 H 1.111928 0.293035 0.120241 0.03 Uiso 1 1 calc R U . . .
C22 C 1.0101(3) 0.3799(3) 0.2411(3) 0.0211(6) Uani 1 1 d . . . . .
C23 C 0.9095(3) 0.2470(3) 0.2223(3) 0.0252(6) Uani 1 1 d . . . . .
H23 H 0.910523 0.15893 0.163664 0.03 Uiso 1 1 calc R U . . .
C24 C 0.8129(3) 0.2412(3) 0.2844(3) 0.0257(7) Uani 1 1 d . . . . .
H24 H 0.747554 0.152446 0.272044 0.031 Uiso 1 1 calc R U . . .
C25 C 0.8154(3) 0.3748(3) 0.3684(3) 0.0195(6) Uani 1 1 d . . . . .
Cl1 Cl 0.74417(8) 0.84836(9) 0.98203(7) 0.0362(2) Uani 1 1 d . . . . .
Cl2 Cl 0.55743(8) 0.91525(7) 0.76830(7) 0.02816(18) Uani 1 1 d . . . . .
N1 N 0.4180(2) 0.6665(2) 0.8569(2) 0.0198(5) Uani 1 1 d . . . . .
N2 N 0.5162(2) 0.5298(2) 0.6847(2) 0.0162(5) Uani 1 1 d . . . . .
N3 N 0.5878(2) 0.4825(2) 0.6028(2) 0.0167(5) Uani 1 1 d . . . . .
H3A H 0.571188 0.391277 0.560001 0.02 Uiso 1 1 calc R U . . .
O1 O 0.70768(19) 0.71341(19) 0.65201(18) 0.0206(4) Uani 1 1 d . . . . .
O2 O 0.72657(19) 0.39131(19) 0.43919(18) 0.0201(4) Uani 1 1 d . . . . .
Zn1 Zn 0.58996(4) 0.76319(3) 0.80408(3) 0.01887(13) Uani 1 1 d . . . . .
C26 C 0.9750(4) 1.0352(4) 0.7738(4) 0.0503(10) Uani 1 1 d . . . . .
H26A H 0.895437 0.94055 0.740192 0.06 Uiso 1 1 calc R U . . .
H26B H 1.027066 1.064855 0.859679 0.06 Uiso 1 1 calc R U . . .
Cl3 Cl 1.06851(13) 1.01464(11) 0.65984(14) 0.0777(4) Uani 1 1 d . . . . .
Cl4 Cl 0.92810(12) 1.16455(12) 0.79952(13) 0.0646(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.356(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.487(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.372(5) . ?
C4 C5 1.381(4) . ?
C5 N1 1.337(4) . ?
C6 N2 1.291(3) . ?
C6 C7 1.483(4) . ?
C7 C12 1.395(4) . ?
C7 C8 1.398(4) . ?
C8 C9 1.382(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.386(4) . ?
C11 C12 1.380(4) . ?
C13 O1 1.236(3) . ?
C13 N3 1.365(3) . ?
C13 C14 1.449(4) . ?
C14 C15 1.356(4) . ?
C14 O2 1.386(3) . ?
C15 C16 1.428(4) . ?
C16 C25 1.381(4) . ?
C16 C17 1.436(4) . ?
C17 C18 1.412(4) . ?
C17 C22 1.423(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.402(5) . ?
C20 C21 1.367(4) . ?
C21 C22 1.413(4) . ?
C22 C23 1.432(4) . ?
C23 C24 1.357(4) . ?
C24 C25 1.408(4) . ?
C25 O2 1.367(3) . ?
Cl1 Zn1 2.2284(9) . ?
Cl2 Zn1 2.2147(8) . ?
N1 Zn1 2.140(2) . ?
N2 N3 1.367(3) . ?
N2 Zn1 2.169(2) . ?
O1 Zn1 2.2967(18) . ?
C26 Cl4 1.738(5) . ?
C26 Cl3 1.750(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.1(3) . . ?
N1 C1 C6 114.9(2) . . ?
C2 C1 C6 122.9(2) . . ?
C1 C2 C3 118.3(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 C5 119.2(3) . . ?
N1 C5 C4 122.4(3) . . ?
N2 C6 C7 124.7(2) . . ?
N2 C6 C1 113.1(2) . . ?
C7 C6 C1 122.1(2) . . ?
C12 C7 C8 119.4(3) . . ?
C12 C7 C6 119.9(2) . . ?
C8 C7 C6 120.6(2) . . ?
C9 C8 C7 120.0(3) . . ?
C8 C9 C10 120.3(3) . . ?
C11 C10 C9 119.7(3) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C7 120.1(3) . . ?
O1 C13 N3 121.1(2) . . ?
O1 C13 C14 122.6(2) . . ?
N3 C13 C14 116.3(2) . . ?
C15 C14 O2 111.6(2) . . ?
C15 C14 C13 131.7(2) . . ?
O2 C14 C13 116.7(2) . . ?
C14 C15 C16 106.0(2) . . ?
C25 C16 C15 106.4(2) . . ?
C25 C16 C17 119.5(2) . . ?
C15 C16 C17 134.1(2) . . ?
C18 C17 C22 119.6(3) . . ?
C18 C17 C16 123.9(3) . . ?
C22 C17 C16 116.5(2) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 120.5(3) . . ?
C21 C20 C19 120.4(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 C17 118.5(3) . . ?
C21 C22 C23 121.1(3) . . ?
C17 C22 C23 120.4(3) . . ?
C24 C23 C22 123.0(3) . . ?
C23 C24 C25 115.9(3) . . ?
O2 C25 C16 110.6(2) . . ?
O2 C25 C24 124.6(2) . . ?
C16 C25 C24 124.7(3) . . ?
C5 N1 C1 118.6(2) . . ?
C5 N1 Zn1 124.57(19) . . ?
C1 N1 Zn1 116.77(18) . . ?
C6 N2 N3 121.9(2) . . ?
C6 N2 Zn1 118.17(17) . . ?
N3 N2 Zn1 116.72(15) . . ?
C13 N3 N2 115.5(2) . . ?
C13 O1 Zn1 114.24(15) . . ?
C25 O2 C14 105.44(19) . . ?
N1 Zn1 N2 73.42(8) . . ?
N1 Zn1 Cl2 103.24(7) . . ?
N2 Zn1 Cl2 133.04(7) . . ?
N1 Zn1 Cl1 99.56(7) . . ?
N2 Zn1 Cl1 106.15(7) . . ?
Cl2 Zn1 Cl1 120.33(3) . . ?
N1 Zn1 O1 143.71(8) . . ?
N2 Zn1 O1 71.05(7) . . ?
Cl2 Zn1 O1 95.62(5) . . ?
Cl1 Zn1 O1 97.11(6) . . ?
Cl4 C26 Cl3 111.8(2) . . ?

####################################################################### 
# 
# 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_drr19_s1874
_database_code_depnum_ccdc_archive 'CCDC 1982906'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1874
_sydney_internal_submission_date 2019-08-26
_sydney_internal_submission_number s1874
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richards'
_sydney_internal_collection_date 2019-09-27
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-09-27
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-09-30
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     3019-09-30
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-09-30
_sydney_internal_check_user      wlew0588
_refine_special_details          
;
The two molecules have a pseudo centre of symmetry between them, which has resulted 
in correlation of the thermal parameters of the psuedo-related atoms. Enhanced rigid 
bond and similarity restraints were applied to counteract this correlation.

The two amine H-atoms had their positions refined freely, however the bond distances 
were restrined to be approximately equal, to try to counteract any effects of 
correlation.
;
_vrf_PLAT340_drr19_s1874         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01175 Ang.  
RESPONSE: This is probaly due to slightly lower than ideal data to parameter ratio.
;
_vrf_PLAT915_drr19_s1874         
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         41 %     
RESPONSE: The crystal was assumed to be centrosymmetric when first collected, 
resulting in low completeness of the Friedel pair coverage. This does not 
affect the overall structure determination result.
;
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H14 N4 O2)'
_chemical_formula_sum            'C19 H14 N4 O2'
_chemical_formula_weight         330.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 N4 O2'
_chemical_oxdiff_usercomment     SF-53
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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   5.5860(4)
_cell_length_b                   9.8008(7)
_cell_length_c                   27.2637(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.122(6)
_cell_angle_gamma                90
_cell_volume                     1490.39(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3320
_cell_measurement_theta_min      4.5640
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.769
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019)
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    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0165
0 0 1 0.0105
-1 0 0 0.0968
4 0 -1 0.0865
0 -5 2 0.0824
0 5 -2 0.0824

_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.027
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
-0.0005 0.0006 -0.9990 -0.0086 0.0354 -0.0434
0.0005 -0.0006 0.9990 0.0086 -0.0354 0.0434
-0.9993 -0.0034 0.0053 0.2275 -0.0825 -0.1326
3.9967 0.0141 -1.0201 -0.9187 0.3653 0.4870
0.0081 -4.9942 1.9720 0.4326 0.4835 0.4540
-0.0081 4.9942 -1.9720 -0.4326 -0.4835 -0.4540

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8533
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.698
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.369
_diffrn_reflns_theta_min         4.511
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  44.00   1.00    2.00    --  -39.07  19.00-120.00   49
  2  ω     -4.00  41.00   1.00    2.00    --  -39.07  19.00 150.00   45
  3  ω      4.00  36.00   1.00    2.00    --  -39.07  19.00 -60.00   32
  4  ω     -6.00  33.00   1.00    2.00    --  -39.07  38.00-180.00   39
  5  ω      8.00  38.00   1.00    2.00    --  -39.07  19.00 -90.00   30
  6  ω     78.00 122.00   1.00    2.00    --   39.07 178.00   0.00   44
  7  ω    105.00 173.00   1.00    8.00    --  106.69 112.00  30.00   68
  8  ω     27.00  53.00   1.00    8.00    --  106.69 -30.00 -30.00   26
  9  ω     31.00  83.00   1.00    8.00    --  106.69 -61.00 150.00   52
 10  ω     31.00  57.00   1.00    8.00    --  106.69 -30.00-180.00   26
 11  ω     33.00  72.00   1.00    8.00    --  106.69 -45.00 -60.00   39
 12  ω     29.00  56.00   1.00    8.00    --  106.69 -30.00-120.00   27
 13  ω     78.00 158.00   1.00    8.00    --  106.69  45.00 -30.00   80
 14  ω     44.00  71.00   1.00    8.00    --  106.69 -45.00  90.00   27
 15  ω    144.00 178.00   1.00    8.00    --  106.69 112.00   0.00   34
 16  ω     33.00 115.00   1.00    8.00    --  106.69 -77.00  30.00   82
 17  ω     -4.00  29.00   1.00    2.00    --  -39.07  19.00-150.00   33
 18  ω     -5.00  32.00   1.00    2.00    --  -39.07  19.00 120.00   37
 19  ω     -1.00  25.00   1.00    2.00    --  -39.07  19.00  90.00   26
 20  ω     80.00 124.00   1.00    2.00    --   39.07 178.00-120.00   44
 21  ω     66.00 107.00   1.00    8.00    --  106.69-111.00-180.00   41
 22  ω     48.00  96.00   1.00    8.00    --  106.69-111.00 -30.00   48
 23  ω     29.00 140.00   1.00    8.00    --  106.69  15.00 120.00  111
 24  ω     77.00 169.00   1.00    8.00    --  106.69  45.00 -90.00   92
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2273535000
_diffrn_orient_matrix_UB_12      -0.0835554000
_diffrn_orient_matrix_UB_13      0.0087120000
_diffrn_orient_matrix_UB_21      0.0827356000
_diffrn_orient_matrix_UB_22      -0.1106922000
_diffrn_orient_matrix_UB_23      -0.0354959000
_diffrn_orient_matrix_UB_31      0.1331606000
_diffrn_orient_matrix_UB_32      -0.0735943000
_diffrn_orient_matrix_UB_33      0.0432971000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.413
_reflns_Friedel_fraction_full    0.425
_reflns_Friedel_fraction_max     0.409
_reflns_number_gt                3577
_reflns_number_total             4095
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Flack x determined using 714 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         4095
_refine_ls_number_restraints     741
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0888
_refine_ls_restrained_S_all      0.998
_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)+(0.1192P)²+3.4256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.2520
_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. Restrained distances
 N1-H1 \\sim N5-H5a
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.008 and sigma
for terminal atoms of 0.016 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C33(H33),
  C34(H34), C35(H35), C36(H36), C39(H39)
5.b Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C26(H26a,H26b,H26c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.7235(10) 0.8126(6) 0.5488(2) 0.0297(12) Uani 1 1 d . U . . .
O2 O 0.2560(11) 0.8324(6) 0.6323(2) 0.0353(13) Uani 1 1 d . U . . .
N1 N 0.6229(12) 0.9408(8) 0.6300(3) 0.0296(14) Uani 1 1 d D U . . .
H1 H 0.765(15) 0.950(11) 0.613(4) 0.036 Uiso 1 1 d D U . . .
N2 N 0.5857(13) 1.0237(7) 0.6694(3) 0.0288(13) Uani 1 1 d . U . . .
N3 N 0.9117(13) 1.2732(8) 0.7383(3) 0.0322(14) Uani 1 1 d . U . . .
N4 N 0.5063(13) 1.2530(8) 0.7942(3) 0.0354(15) Uani 1 1 d . U . . .
C1 C 0.7559(14) 1.1069(8) 0.6798(3) 0.0248(14) Uani 1 1 d . U . . .
C2 C 0.7294(14) 1.1931(9) 0.7248(3) 0.0261(14) Uani 1 1 d . U . . .
C3 C 0.8907(16) 1.3436(10) 0.7809(3) 0.0360(17) Uani 1 1 d . U . . .
H3 H 1.018541 1.401356 0.792303 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6923(16) 1.3341(9) 0.8077(3) 0.0336(16) Uani 1 1 d . U . . .
H4 H 0.685444 1.386493 0.836915 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5281(15) 1.1822(9) 0.7533(3) 0.0319(16) Uani 1 1 d . U . . .
H5 H 0.402740 1.121599 0.742902 0.038 Uiso 1 1 calc R U . . .
C6 C 0.9799(15) 1.1248(9) 0.6520(3) 0.0315(17) Uani 1 1 d . U . . .
H6A H 0.938327 1.121524 0.616588 0.047 Uiso 1 1 calc R U . . .
H6B H 1.093346 1.051432 0.660801 0.047 Uiso 1 1 calc R U . . .
H6C H 1.053427 1.213130 0.660376 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4516(15) 0.8496(9) 0.6134(3) 0.0287(14) Uani 1 1 d . U . . .
C8 C 0.5160(15) 0.7728(9) 0.5700(3) 0.0291(14) Uani 1 1 d . U . . .
C9 C 0.7409(14) 0.7310(10) 0.5092(3) 0.0299(14) Uani 1 1 d . U . . .
C10 C 0.9237(14) 0.7419(9) 0.4752(3) 0.0302(14) Uani 1 1 d . U . . .
H10 H 1.050812 0.805943 0.479285 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9053(15) 0.6544(9) 0.4361(3) 0.0333(15) Uani 1 1 d . U . . .
H11 H 1.022999 0.658962 0.412249 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7190(15) 0.5575(9) 0.4295(3) 0.0300(14) Uani 1 1 d . U . . .
C13 C 0.7053(16) 0.4690(9) 0.3883(3) 0.0325(16) Uani 1 1 d . U . . .
H13 H 0.826745 0.472990 0.365240 0.039 Uiso 1 1 calc R U . . .
C14 C 0.5212(15) 0.3780(9) 0.3809(3) 0.0336(16) Uani 1 1 d . U . . .
H14 H 0.513718 0.320651 0.352817 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3423(15) 0.3700(10) 0.4155(3) 0.0329(16) Uani 1 1 d . U . . .
H15 H 0.214087 0.307087 0.410289 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3502(15) 0.4502(10) 0.4558(3) 0.0314(15) Uani 1 1 d . U . . .
H16 H 0.230693 0.440852 0.479089 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5360(15) 0.5489(10) 0.4638(3) 0.0292(14) Uani 1 1 d . U . . .
C18 C 0.5527(15) 0.6379(10) 0.5047(3) 0.0296(14) Uani 1 1 d . U . . .
C19 C 0.4065(15) 0.6689(9) 0.5451(3) 0.0292(14) Uani 1 1 d . U . . .
H19 H 0.261608 0.624943 0.552810 0.035 Uiso 1 1 calc R U . . .
O3 O 0.5650(10) 0.4334(6) 0.6423(2) 0.0295(12) Uani 1 1 d . U . . .
O4 O 1.0332(11) 0.4154(6) 0.5592(2) 0.0338(13) Uani 1 1 d . U . . .
N5 N 0.6659(12) 0.3115(8) 0.5597(3) 0.0309(14) Uani 1 1 d D U . . .
H5A H 0.528(16) 0.297(11) 0.577(4) 0.037 Uiso 1 1 d D U . . .
N6 N 0.7053(12) 0.2279(8) 0.5201(3) 0.0297(13) Uani 1 1 d . U . . .
N7 N 0.4212(13) -0.0318(8) 0.4493(3) 0.0322(14) Uani 1 1 d . U . . .
N8 N 0.8232(13) 0.0171(8) 0.3943(3) 0.0372(15) Uani 1 1 d . U . . .
C21 C 0.5415(14) 0.1421(9) 0.5074(3) 0.0267(14) Uani 1 1 d . U . . .
C22 C 0.5845(14) 0.0641(9) 0.4630(3) 0.0278(14) Uani 1 1 d . U . . .
C23 C 0.4610(16) -0.1005(9) 0.4082(3) 0.0347(16) Uani 1 1 d . U . . .
H23 H 0.348625 -0.167899 0.396953 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6613(16) -0.0767(9) 0.3813(3) 0.0337(16) Uani 1 1 d . U . . .
H24 H 0.682702 -0.129492 0.352680 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7849(16) 0.0861(9) 0.4349(3) 0.0327(16) Uani 1 1 d . U . . .
H25 H 0.898071 0.153686 0.445481 0.039 Uiso 1 1 calc R U . . .
C26 C 0.3140(15) 0.1217(9) 0.5333(3) 0.0311(17) Uani 1 1 d . U . . .
H26A H 0.210708 0.201802 0.528187 0.047 Uiso 1 1 calc R U . . .
H26B H 0.352037 0.109241 0.568525 0.047 Uiso 1 1 calc R U . . .
H26C H 0.230543 0.040566 0.520071 0.047 Uiso 1 1 calc R U . . .
C27 C 0.8394(14) 0.3983(8) 0.5771(3) 0.0290(14) Uani 1 1 d . U . . .
C28 C 0.7732(15) 0.4753(8) 0.6213(3) 0.0284(13) Uani 1 1 d . U . . .
C29 C 0.5443(14) 0.5186(8) 0.6818(3) 0.0275(14) Uani 1 1 d . U . . .
C30 C 0.3595(14) 0.5071(8) 0.7148(3) 0.0278(14) Uani 1 1 d . U . . .
H30 H 0.236747 0.440232 0.711100 0.033 Uiso 1 1 calc R U . . .
C31 C 0.3702(15) 0.5998(8) 0.7527(3) 0.0304(15) Uani 1 1 d . U . . .
H31 H 0.248824 0.597815 0.775820 0.036 Uiso 1 1 calc R U . . .
C32 C 0.5560(14) 0.6982(8) 0.7587(3) 0.0284(14) Uani 1 1 d . U . . .
C33 C 0.5563(16) 0.7930(9) 0.7980(3) 0.0323(16) Uani 1 1 d . U . . .
H33 H 0.430605 0.790956 0.820082 0.039 Uiso 1 1 calc R U . . .
C34 C 0.7350(15) 0.8870(9) 0.8044(3) 0.0325(15) Uani 1 1 d . U . . .
H34 H 0.732940 0.949865 0.830944 0.039 Uiso 1 1 calc R U . . .
C35 C 0.9230(15) 0.8916(8) 0.7719(3) 0.0304(15) Uani 1 1 d . U . . .
H35 H 1.048461 0.956334 0.777104 0.036 Uiso 1 1 calc R U . . .
C36 C 0.9259(14) 0.8035(8) 0.7330(3) 0.0283(15) Uani 1 1 d . U . . .
H36 H 1.052101 0.808010 0.711073 0.034 Uiso 1 1 calc R U . . .
C37 C 0.7438(14) 0.7069(8) 0.7254(3) 0.0250(13) Uani 1 1 d . U . . .
C38 C 0.7329(14) 0.6080(8) 0.6861(3) 0.0241(13) Uani 1 1 d . U . . .
C39 C 0.8827(15) 0.5792(8) 0.6455(3) 0.0290(14) Uani 1 1 d . U . . .
H39 H 1.026677 0.624043 0.637785 0.035 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
O1 C8 1.380(10) . ?
O1 C9 1.350(11) . ?
O2 C7 1.245(10) . ?
N1 H1 0.94(7) . ?
N1 N2 1.372(10) . ?
N1 C7 1.368(11) . ?
N2 C1 1.272(11) . ?
N3 C2 1.322(12) . ?
N3 C3 1.361(12) . ?
N4 C4 1.344(12) . ?
N4 C5 1.323(12) . ?
C1 C2 1.502(11) . ?
C1 C6 1.509(11) . ?
C2 C5 1.406(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(12) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.464(11) . ?
C8 C19 1.351(13) . ?
C9 C10 1.421(11) . ?
C9 C18 1.392(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.413(13) . ?
C12 C13 1.418(13) . ?
C12 C17 1.426(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.413(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.350(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.427(13) . ?
C17 C18 1.414(13) . ?
C18 C19 1.440(11) . ?
C19 H19 0.9500 . ?
O3 C28 1.386(10) . ?
O3 C29 1.373(10) . ?
O4 C27 1.224(10) . ?
N5 H5A 0.94(7) . ?
N5 N6 1.382(10) . ?
N5 C27 1.356(12) . ?
N6 C21 1.277(11) . ?
N7 C22 1.348(11) . ?
N7 C23 1.337(12) . ?
N8 C24 1.324(12) . ?
N8 C25 1.323(11) . ?
C21 C22 1.463(12) . ?
C21 C26 1.500(11) . ?
C22 C25 1.408(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(12) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.485(11) . ?
C28 C39 1.343(12) . ?
C29 C30 1.410(11) . ?
C29 C38 1.370(12) . ?
C30 H30 0.9500 . ?
C30 C31 1.375(12) . ?
C31 H31 0.9500 . ?
C31 C32 1.420(12) . ?
C32 C33 1.418(12) . ?
C32 C37 1.426(11) . ?
C33 H33 0.9500 . ?
C33 C34 1.363(13) . ?
C34 H34 0.9500 . ?
C34 C35 1.411(12) . ?
C35 H35 0.9500 . ?
C35 C36 1.370(12) . ?
C36 H36 0.9500 . ?
C36 C37 1.396(12) . ?
C37 C38 1.445(12) . ?
C38 C39 1.450(12) . ?
C39 H39 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
C9 O1 C8 105.4(7) . . ?
N2 N1 H1 119(7) . . ?
C7 N1 H1 120(7) . . ?
C7 N1 N2 120.9(7) . . ?
C1 N2 N1 114.3(7) . . ?
C2 N3 C3 116.0(7) . . ?
C5 N4 C4 115.8(7) . . ?
N2 C1 C2 115.9(7) . . ?
N2 C1 C6 126.3(8) . . ?
C2 C1 C6 117.8(7) . . ?
N3 C2 C1 117.0(7) . . ?
N3 C2 C5 121.1(8) . . ?
C5 C2 C1 121.8(8) . . ?
N3 C3 H3 118.9 . . ?
N3 C3 C4 122.2(9) . . ?
C4 C3 H3 118.9 . . ?
N4 C4 C3 122.2(9) . . ?
N4 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N4 C5 C2 122.6(9) . . ?
N4 C5 H5 118.7 . . ?
C2 C5 H5 118.7 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N1 124.5(8) . . ?
O2 C7 C8 121.6(8) . . ?
N1 C7 C8 113.9(7) . . ?
O1 C8 C7 116.3(7) . . ?
C19 C8 O1 111.7(7) . . ?
C19 C8 C7 132.0(8) . . ?
O1 C9 C10 124.3(8) . . ?
O1 C9 C18 111.9(7) . . ?
C18 C9 C10 123.8(8) . . ?
C9 C10 H10 122.1 . . ?
C11 C10 C9 115.9(8) . . ?
C11 C10 H10 122.1 . . ?
C10 C11 H11 118.5 . . ?
C10 C11 C12 123.0(7) . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C13 121.3(8) . . ?
C11 C12 C17 120.4(8) . . ?
C13 C12 C17 118.3(8) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(8) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.5(8) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(9) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(8) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 118.7(8) . . ?
C18 C17 C12 117.5(8) . . ?
C18 C17 C16 123.7(8) . . ?
C9 C18 C17 119.4(8) . . ?
C9 C18 C19 104.5(8) . . ?
C17 C18 C19 135.8(8) . . ?
C8 C19 C18 106.4(8) . . ?
C8 C19 H19 126.8 . . ?
C18 C19 H19 126.8 . . ?
C29 O3 C28 104.6(6) . . ?
N6 N5 H5A 119(7) . . ?
C27 N5 H5A 120(7) . . ?
C27 N5 N6 120.3(7) . . ?
C21 N6 N5 117.3(7) . . ?
C23 N7 C22 116.2(7) . . ?
C25 N8 C24 116.0(7) . . ?
N6 C21 C22 114.9(7) . . ?
N6 C21 C26 125.0(8) . . ?
C22 C21 C26 120.1(8) . . ?
N7 C22 C21 117.0(7) . . ?
N7 C22 C25 120.2(8) . . ?
C25 C22 C21 122.9(8) . . ?
N7 C23 H23 118.9 . . ?
N7 C23 C24 122.2(9) . . ?
C24 C23 H23 118.9 . . ?
N8 C24 C23 122.3(8) . . ?
N8 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
N8 C25 C22 123.1(8) . . ?
N8 C25 H25 118.4 . . ?
C22 C25 H25 118.4 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 N5 125.2(8) . . ?
O4 C27 C28 121.3(8) . . ?
N5 C27 C28 113.5(7) . . ?
O3 C28 C27 115.9(7) . . ?
C39 C28 O3 113.1(7) . . ?
C39 C28 C27 131.1(8) . . ?
O3 C29 C30 123.2(7) . . ?
C38 C29 O3 110.9(7) . . ?
C38 C29 C30 125.7(8) . . ?
C29 C30 H30 122.5 . . ?
C31 C30 C29 115.1(7) . . ?
C31 C30 H30 122.5 . . ?
C30 C31 H31 118.8 . . ?
C30 C31 C32 122.4(8) . . ?
C32 C31 H31 118.8 . . ?
C31 C32 C37 121.8(8) . . ?
C33 C32 C31 120.2(7) . . ?
C33 C32 C37 118.1(8) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.8(8) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.4(8) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 119.8 . . ?
C36 C35 C34 120.5(8) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.2(8) . . ?
C37 C36 H36 119.9 . . ?
C32 C37 C38 115.4(7) . . ?
C36 C37 C32 120.1(8) . . ?
C36 C37 C38 124.4(7) . . ?
C29 C38 C37 119.5(7) . . ?
C29 C38 C39 106.5(7) . . ?
C37 C38 C39 133.9(8) . . ?
C28 C39 C38 104.8(7) . . ?
C28 C39 H39 127.6 . . ?
C38 C39 H39 127.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.94(7) 2.22(10) 2.633(9) 106(8) . yes
N5 H5A O3 0.94(7) 2.22(11) 2.637(9) 106(8) . yes

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
O1 C8 C19 C18 0.1(10) . . . . ?
O1 C9 C10 C11 -177.0(8) . . . . ?
O1 C9 C18 C17 176.8(8) . . . . ?
O1 C9 C18 C19 1.1(10) . . . . ?
O2 C7 C8 O1 172.1(8) . . . . ?
O2 C7 C8 C19 -6.3(15) . . . . ?
N1 N2 C1 C2 -176.1(7) . . . . ?
N1 N2 C1 C6 3.0(12) . . . . ?
N1 C7 C8 O1 -7.0(11) . . . . ?
N1 C7 C8 C19 174.6(9) . . . . ?
N2 N1 C7 O2 -1.3(13) . . . . ?
N2 N1 C7 C8 177.8(7) . . . . ?
N2 C1 C2 N3 175.3(8) . . . . ?
N2 C1 C2 C5 -0.1(12) . . . . ?
N3 C2 C5 N4 1.8(14) . . . . ?
N3 C3 C4 N4 1.0(15) . . . . ?
C1 C2 C5 N4 177.0(8) . . . . ?
C2 N3 C3 C4 -1.0(14) . . . . ?
C3 N3 C2 C1 -175.8(8) . . . . ?
C3 N3 C2 C5 -0.3(13) . . . . ?
C4 N4 C5 C2 -1.7(14) . . . . ?
C5 N4 C4 C3 0.4(14) . . . . ?
C6 C1 C2 N3 -3.8(12) . . . . ?
C6 C1 C2 C5 -179.3(8) . . . . ?
C7 N1 N2 C1 -177.6(8) . . . . ?
C7 C8 C19 C18 178.6(9) . . . . ?
C8 O1 C9 C10 176.7(8) . . . . ?
C8 O1 C9 C18 -1.0(10) . . . . ?
C9 O1 C8 C7 -178.2(7) . . . . ?
C9 O1 C8 C19 0.5(10) . . . . ?
C9 C10 C11 C12 -0.6(12) . . . . ?
C9 C18 C19 C8 -0.7(9) . . . . ?
C10 C9 C18 C17 -0.9(13) . . . . ?
C10 C9 C18 C19 -176.6(8) . . . . ?
C10 C11 C12 C13 179.6(8) . . . . ?
C10 C11 C12 C17 1.2(13) . . . . ?
C11 C12 C13 C14 -177.9(8) . . . . ?
C11 C12 C17 C16 179.7(8) . . . . ?
C11 C12 C17 C18 -1.5(13) . . . . ?
C12 C13 C14 C15 -1.1(14) . . . . ?
C12 C17 C18 C9 1.4(13) . . . . ?
C12 C17 C18 C19 175.5(10) . . . . ?
C13 C12 C17 C16 1.2(13) . . . . ?
C13 C12 C17 C18 180.0(8) . . . . ?
C13 C14 C15 C16 -0.3(14) . . . . ?
C14 C15 C16 C17 2.1(14) . . . . ?
C15 C16 C17 C12 -2.5(13) . . . . ?
C15 C16 C17 C18 178.8(9) . . . . ?
C16 C17 C18 C9 -179.9(9) . . . . ?
C16 C17 C18 C19 -5.8(17) . . . . ?
C17 C12 C13 C14 0.6(14) . . . . ?
C17 C18 C19 C8 -175.4(11) . . . . ?
C18 C9 C10 C11 0.5(12) . . . . ?
O3 C28 C39 C38 0.1(9) . . . . ?
O3 C29 C30 C31 178.8(8) . . . . ?
O3 C29 C38 C37 179.8(7) . . . . ?
O3 C29 C38 C39 1.2(9) . . . . ?
O4 C27 C28 O3 -171.1(8) . . . . ?
O4 C27 C28 C39 7.9(14) . . . . ?
N5 N6 C21 C22 175.4(7) . . . . ?
N5 N6 C21 C26 -2.3(13) . . . . ?
N5 C27 C28 O3 9.3(11) . . . . ?
N5 C27 C28 C39 -171.7(9) . . . . ?
N6 N5 C27 O4 3.5(14) . . . . ?
N6 N5 C27 C28 -176.9(7) . . . . ?
N6 C21 C22 N7 177.3(8) . . . . ?
N6 C21 C22 C25 -3.0(13) . . . . ?
N7 C22 C25 N8 0.6(14) . . . . ?
N7 C23 C24 N8 -1.2(14) . . . . ?
C21 C22 C25 N8 -179.1(9) . . . . ?
C22 N7 C23 C24 1.1(13) . . . . ?
C23 N7 C22 C21 178.9(8) . . . . ?
C23 N7 C22 C25 -0.8(12) . . . . ?
C24 N8 C25 C22 -0.5(14) . . . . ?
C25 N8 C24 C23 0.8(13) . . . . ?
C26 C21 C22 N7 -4.8(12) . . . . ?
C26 C21 C22 C25 174.8(8) . . . . ?
C27 N5 N6 C21 175.5(8) . . . . ?
C27 C28 C39 C38 -178.9(9) . . . . ?
C28 O3 C29 C30 -177.3(8) . . . . ?
C28 O3 C29 C38 -1.2(9) . . . . ?
C29 O3 C28 C27 179.8(7) . . . . ?
C29 O3 C28 C39 0.6(10) . . . . ?
C29 C30 C31 C32 -1.0(12) . . . . ?
C29 C38 C39 C28 -0.8(9) . . . . ?
C30 C29 C38 C37 -4.2(13) . . . . ?
C30 C29 C38 C39 177.3(8) . . . . ?
C30 C31 C32 C33 178.9(8) . . . . ?
C30 C31 C32 C37 0.0(13) . . . . ?
C31 C32 C33 C34 179.3(8) . . . . ?
C31 C32 C37 C36 -178.8(8) . . . . ?
C31 C32 C37 C38 -0.8(11) . . . . ?
C32 C33 C34 C35 0.1(13) . . . . ?
C32 C37 C38 C29 2.7(11) . . . . ?
C32 C37 C38 C39 -179.2(8) . . . . ?
C33 C32 C37 C36 2.3(12) . . . . ?
C33 C32 C37 C38 -179.7(7) . . . . ?
C33 C34 C35 C36 1.3(13) . . . . ?
C34 C35 C36 C37 -0.8(13) . . . . ?
C35 C36 C37 C32 -1.0(12) . . . . ?
C35 C36 C37 C38 -178.8(8) . . . . ?
C36 C37 C38 C29 -179.3(8) . . . . ?
C36 C37 C38 C39 -1.3(14) . . . . ?
C37 C32 C33 C34 -1.8(13) . . . . ?
C37 C38 C39 C28 -179.0(9) . . . . ?
C38 C29 C30 C31 3.2(12) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_data_collection 2019-09-27
_olex2_date_sample_submission    2019-08-26
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-53
_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 2.038
_oxdiff_exptl_absorpt_empirical_full_min 0.600
####################################################################### 
# 
# 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_drr19_s1897
_database_code_depnum_ccdc_archive 'CCDC 1982909'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1897
_sydney_internal_submission_date 2019-09-12
_sydney_internal_submission_number s1897
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richardson'
_sydney_internal_collection_date 2019-10-17
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-11-01
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-11-01
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-11-01
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-11-01
_sydney_internal_check_user      wlew0588
_refine_special_details          ?
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O2'
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16N2O2
_chemical_oxdiff_usercomment     SF-91(L5)
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                   14.6062(12)
_cell_length_b                   5.3852(4)
_cell_length_c                   19.6687(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.433(7)
_cell_angle_gamma                90
_cell_volume                     1545.68(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.7680
_cell_measurement_theta_min      5.3320
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0564
0 0 1 0.0424
0 1 0 0.0807
0 -1 1 0.0933
-1 0 0 0.0148
1 0 0 0.0148

_exptl_crystal_recrystallization_method 'crystallised fom DMSO'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.03
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
0.0015 -0.0002 -1.0007 -0.0675 0.0032 -0.0399
-0.0015 0.0002 1.0007 0.0675 -0.0032 0.0399
-0.0060 0.9993 0.0024 0.1451 -0.0156 -0.2457
0.0044 -0.9992 0.9983 -0.0776 0.0124 0.2856
-0.9990 -0.0002 -0.0039 0.0026 0.1054 -0.0052
0.9990 0.0002 0.0039 -0.0026 -0.1054 0.0052

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5396
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.181
_diffrn_reflns_theta_min         4.500
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  45.00   1.00   30.00    --  -38.44  19.00  30.00   44
  2  ω    -68.00 -23.00   1.00   30.00    --  -38.44  77.00-120.00   45
  3  ω    -97.00  48.00   1.00   30.00    --  -38.44   0.00-180.00  145
  4  ω    125.00 151.00   1.00  120.00    --  106.69 111.00-150.00   26
  5  ω     28.00  53.00   1.00  120.00    --  106.69 -30.00-150.00   25
  6  ω     27.00  56.00   1.00  120.00    --  106.69 -30.00 -30.00   29
  7  ω    107.00 178.00   1.00  120.00    --  106.69 111.00 -30.00   71
  8  ω     30.00  67.00   1.00  120.00    --  106.69 -45.00 -90.00   37
  9  ω     27.00  55.00   1.00  120.00    --  106.69 -30.00 -60.00   28
 10  ω     27.00  56.00   1.00  120.00    --  106.69 -30.00-180.00   29
 11  ω     76.00 173.00   1.00  120.00    --  106.69  61.00  60.00   97
 12  ω     38.00  83.00   1.00  120.00    --  106.69 -61.00 120.00   45
 13  ω     40.00  68.00   1.00  120.00    --  106.69 -45.00 120.00   28
 14  ω     30.00 123.00   1.00  120.00    --  106.69 -77.00 -90.00   93
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0028577000
_diffrn_orient_matrix_UB_12      0.1450286000
_diffrn_orient_matrix_UB_13      0.0674075000
_diffrn_orient_matrix_UB_21      -0.1054457000
_diffrn_orient_matrix_UB_22      -0.0162513000
_diffrn_orient_matrix_UB_23      -0.0033341000
_diffrn_orient_matrix_UB_31      0.0051433000
_diffrn_orient_matrix_UB_32      -0.2459000000
_diffrn_orient_matrix_UB_33      0.0399087000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2477
_reflns_number_total             2963
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.096
_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)+(0.0746P)²+0.7412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1459
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.84218(10) -0.3933(3) 0.43740(7) 0.0328(4) Uani 1 1 d . . . . .
O2 O 0.57396(10) -0.1829(3) 0.54922(7) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.73543(12) -0.0657(3) 0.49992(8) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.81358(12) 0.0061(3) 0.46817(8) 0.0278(4) Uani 1 1 d . . . . .
H2 H 0.8262(17) 0.174(5) 0.4633(13) 0.033 Uiso 1 1 d . U . . .
C1 C 0.86128(14) -0.1717(4) 0.43533(10) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.94131(14) -0.0821(4) 0.39730(10) 0.0268(4) Uani 1 1 d . . . . .
C3 C 0.96733(14) -0.2296(4) 0.34272(10) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.932462 -0.372690 0.330304 0.035 Uiso 1 1 calc R U . . .
C4 C 1.04344(15) -0.1681(4) 0.30684(11) 0.0322(5) Uani 1 1 d . . . . .
H4 H 1.059516 -0.265803 0.268937 0.039 Uiso 1 1 calc R U . . .
C5 C 1.09643(15) 0.0362(4) 0.32607(11) 0.0317(5) Uani 1 1 d . . . . .
H5 H 1.149666 0.075952 0.302168 0.038 Uiso 1 1 calc R U . . .
C6 C 1.07131(15) 0.1815(4) 0.38023(11) 0.0335(5) Uani 1 1 d . . . . .
H6 H 1.107780 0.320738 0.393545 0.040 Uiso 1 1 calc R U . . .
C7 C 0.99378(15) 0.1263(4) 0.41512(10) 0.0303(5) Uani 1 1 d . . . . .
H7 H 0.976149 0.230381 0.451303 0.036 Uiso 1 1 calc R U . . .
C8 C 0.70400(14) 0.0931(4) 0.54265(9) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.74739(15) 0.3355(4) 0.56275(10) 0.0298(5) Uani 1 1 d . . . . .
H9A H 0.813644 0.312602 0.570049 0.045 Uiso 1 1 calc R U . . .
H9B H 0.721371 0.394984 0.604882 0.045 Uiso 1 1 calc R U . . .
H9C H 0.735575 0.457620 0.526495 0.045 Uiso 1 1 calc R U . . .
C10 C 0.61837(14) 0.0277(4) 0.57331(9) 0.0252(4) Uani 1 1 d . . . . .
C11 C 0.49603(14) -0.2030(4) 0.58471(9) 0.0247(4) Uani 1 1 d . . . . .
C12 C 0.43013(15) -0.3903(4) 0.57489(10) 0.0278(4) Uani 1 1 d . . . . .
H12 H 0.437134 -0.518634 0.542373 0.033 Uiso 1 1 calc R U . . .
C13 C 0.35583(14) -0.3799(4) 0.61399(10) 0.0270(4) Uani 1 1 d . . . . .
H13 H 0.309625 -0.503254 0.608381 0.032 Uiso 1 1 calc R U . . .
C14 C 0.34518(14) -0.1880(4) 0.66347(9) 0.0252(4) Uani 1 1 d . . . . .
C15 C 0.26679(14) -0.1809(4) 0.70331(10) 0.0285(4) Uani 1 1 d . . . . .
H15 H 0.220306 -0.302773 0.696465 0.034 Uiso 1 1 calc R U . . .
C16 C 0.25698(15) -0.0005(4) 0.75164(10) 0.0303(5) Uani 1 1 d . . . . .
H16 H 0.203761 0.002516 0.777767 0.036 Uiso 1 1 calc R U . . .
C17 C 0.32561(15) 0.1800(4) 0.76260(10) 0.0294(4) Uani 1 1 d . . . . .
H17 H 0.319033 0.302255 0.796869 0.035 Uiso 1 1 calc R U . . .
C18 C 0.40197(14) 0.1813(4) 0.72431(10) 0.0269(4) Uani 1 1 d . . . . .
H18 H 0.447519 0.305297 0.731929 0.032 Uiso 1 1 calc R U . . .
C19 C 0.41328(13) -0.0009(4) 0.67353(9) 0.0243(4) Uani 1 1 d . . . . .
C20 C 0.49036(14) -0.0108(4) 0.63127(9) 0.0248(4) Uani 1 1 d . . . . .
C21 C 0.57020(14) 0.1375(4) 0.62317(9) 0.0250(4) Uani 1 1 d . . . . .
H21 H 0.586602 0.284029 0.647680 0.030 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
O1 C1 1.227(3) . ?
O2 C10 1.381(2) . ?
O2 C11 1.365(2) . ?
N1 N2 1.380(2) . ?
N1 C8 1.297(3) . ?
N2 H2 0.93(3) . ?
N2 C1 1.363(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.497(3) . ?
C8 C10 1.455(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C21 1.366(3) . ?
C11 C12 1.402(3) . ?
C11 C20 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.358(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.432(3) . ?
C14 C15 1.415(3) . ?
C14 C19 1.424(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.415(3) . ?
C19 C20 1.429(3) . ?
C20 C21 1.428(3) . ?
C21 H21 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
C11 O2 C10 106.23(15) . . ?
C8 N1 N2 115.53(18) . . ?
N1 N2 H2 119.5(16) . . ?
C1 N2 N1 117.83(18) . . ?
C1 N2 H2 121.8(16) . . ?
O1 C1 N2 123.12(19) . . ?
O1 C1 C2 120.97(19) . . ?
N2 C1 C2 115.89(19) . . ?
C3 C2 C1 116.35(19) . . ?
C7 C2 C1 124.54(18) . . ?
C7 C2 C3 118.99(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C9 126.07(19) . . ?
N1 C8 C10 116.32(19) . . ?
C10 C8 C9 117.60(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C8 117.14(17) . . ?
C21 C10 O2 110.69(18) . . ?
C21 C10 C8 132.17(19) . . ?
O2 C11 C12 124.71(18) . . ?
O2 C11 C20 110.67(17) . . ?
C20 C11 C12 124.61(18) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 C11 116.93(18) . . ?
C13 C12 H12 121.5 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.81(19) . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 120.64(19) . . ?
C15 C14 C19 118.72(18) . . ?
C19 C14 C13 120.63(18) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.08(19) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.67(19) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.39(19) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C20 117.14(18) . . ?
C18 C19 C14 119.15(18) . . ?
C18 C19 C20 123.70(19) . . ?
C11 C20 C19 118.84(18) . . ?
C11 C20 C21 105.77(17) . . ?
C21 C20 C19 135.38(18) . . ?
C10 C21 C20 106.63(18) . . ?
C10 C21 H21 126.7 . . ?
C20 C21 H21 126.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.93(3) 2.40(3) 3.320(2) 172(2) 1_565 yes

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
O1 C1 C2 C3 26.9(3) . . . . ?
O1 C1 C2 C7 -149.0(2) . . . . ?
O2 C10 C21 C20 -0.2(2) . . . . ?
O2 C11 C12 C13 -178.98(18) . . . . ?
O2 C11 C20 C19 -179.74(16) . . . . ?
O2 C11 C20 C21 0.4(2) . . . . ?
N1 N2 C1 O1 -6.0(3) . . . . ?
N1 N2 C1 C2 175.54(16) . . . . ?
N1 C8 C10 O2 -6.4(3) . . . . ?
N1 C8 C10 C21 174.0(2) . . . . ?
N2 N1 C8 C9 -3.6(3) . . . . ?
N2 N1 C8 C10 176.14(16) . . . . ?
N2 C1 C2 C3 -154.64(18) . . . . ?
N2 C1 C2 C7 29.4(3) . . . . ?
C1 C2 C3 C4 -176.67(19) . . . . ?
C1 C2 C7 C6 174.3(2) . . . . ?
C2 C3 C4 C5 2.1(3) . . . . ?
C3 C2 C7 C6 -1.5(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C2 2.0(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C8 N1 N2 C1 165.20(18) . . . . ?
C8 C10 C21 C20 179.4(2) . . . . ?
C9 C8 C10 O2 173.37(16) . . . . ?
C9 C8 C10 C21 -6.2(3) . . . . ?
C10 O2 C11 C12 178.72(18) . . . . ?
C10 O2 C11 C20 -0.5(2) . . . . ?
C11 O2 C10 C8 -179.24(16) . . . . ?
C11 O2 C10 C21 0.4(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C11 C20 C21 C10 -0.1(2) . . . . ?
C12 C11 C20 C19 1.0(3) . . . . ?
C12 C11 C20 C21 -178.83(18) . . . . ?
C12 C13 C14 C15 179.67(19) . . . . ?
C12 C13 C14 C19 -0.4(3) . . . . ?
C13 C14 C15 C16 178.76(19) . . . . ?
C13 C14 C19 C18 -178.03(17) . . . . ?
C13 C14 C19 C20 1.5(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C19 C20 C11 -1.8(3) . . . . ?
C14 C19 C20 C21 178.0(2) . . . . ?
C15 C14 C19 C18 1.9(3) . . . . ?
C15 C14 C19 C20 -178.54(17) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 -1.0(3) . . . . ?
C17 C18 C19 C20 179.47(18) . . . . ?
C18 C19 C20 C11 177.72(18) . . . . ?
C18 C19 C20 C21 -2.5(3) . . . . ?
C19 C14 C15 C16 -1.2(3) . . . . ?
C19 C20 C21 C10 -179.9(2) . . . . ?
C20 C11 C12 C13 0.2(3) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
_olex2_date_sample_data_collection 2019-10-17
_olex2_date_sample_submission    2019-09-12
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-91(L5)
_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 1.428
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# 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_drr19_s1909
_database_code_depnum_ccdc_archive 'CCDC 1982911'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1909
_sydney_internal_submission_date 2019-09-30
_sydney_internal_submission_number s1909
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richardson'
_sydney_internal_collection_date 2019-10-24
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-10-30
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-11-01
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-11-01
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-11-01
_sydney_internal_check_user      wlew0588
_refine_special_details          
;
The thiophene ring rotationally disordered over two orientations. The occupancies of 
the disordered atoms were refined competitively, converging to a ratio of 0.61:0.39. 
Chemcially equivalent bonds of the disordered atoms were restrained to be 
approximately equal. Enhanced rigid bond restraints were applied to the thermal 
parameters of the thiophene ring non-hydrogen atoms.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N2 O2 S'
_chemical_formula_sum            'C19 H14 N2 O2 S'
_chemical_formula_weight         334.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 N2 O2 S'
_chemical_oxdiff_usercomment     L7(SF-89)
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                   10.6903(5)
_cell_length_b                   18.2865(7)
_cell_length_c                   8.5178(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.100(5)
_cell_angle_gamma                90
_cell_volume                     1582.73(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.3210
_cell_measurement_theta_min      4.8350
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    1.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0305
-3 3 5 0.0509
0 -1 0 0.0464
0 1 0 0.0264
1 0 0 0.0027
-1 0 0 0.0167

_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.019
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
-0.0009 -0.0013 -0.9996 0.1468 0.0420 0.1135
-2.9962 2.9994 5.0011 -0.8893 0.1941 -0.2788
0.0005 -0.9989 -0.0004 0.0482 0.0141 -0.0675
-0.0005 0.9989 0.0004 -0.0482 -0.0141 0.0675
0.9996 0.0012 -0.0006 0.0035 -0.1488 -0.0286
-0.9996 -0.0012 0.0006 -0.0035 0.1488 0.0286

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6006
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.560
_diffrn_reflns_theta_min         4.351
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  23.00   1.00   20.00    --  -39.19  19.00   0.00   27
  2  ω     -5.00  40.00   1.00   20.00    --  -39.19  19.00  30.00   45
  3  ω     11.00  38.00   1.00   20.00    --  -39.19  38.00 -90.00   27
  4  ω     -4.00  40.00   1.00   20.00    --  -39.19  19.00 -30.00   44
  5  ω   -130.00 -39.00   1.00   20.00    --  -39.19-178.00  30.00   91
  6  ω     13.00  41.00   1.00   20.00    --  -39.19  19.00  60.00   28
  7  ω     30.00  57.00   1.00   80.00    --  106.69 -30.00 -60.00   27
  8  ω     79.00 115.00   1.00   80.00    --  106.69  30.00  60.00   36
  9  ω     34.00  66.00   1.00   80.00    --  106.69 -45.00 -90.00   32
 10  ω    105.00 178.00   1.00   80.00    --  106.69 111.00   0.00   73
 11  ω     30.00  55.00   1.00   80.00    --  106.69 -30.00   0.00   25
 12  ω    148.00 175.00   1.00   80.00    --  106.69  30.00  60.00   27
 13  ω     33.00  60.00   1.00   80.00    --  106.69 -45.00  60.00   27
 14  ω     35.00  69.00   1.00   80.00    --  106.69 -45.00 -30.00   34
 15  ω    110.00 165.00   1.00   80.00    --  106.69 111.00 -30.00   55
 16  ω     28.00  55.00   1.00   80.00    --  106.69 -30.00-120.00   27
 17  ω     35.00 106.00   1.00   80.00    --  106.69-111.00 -60.00   71
 18  ω     28.00  54.00   1.00   80.00    --  106.69 -30.00  30.00   26
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0035231000
_diffrn_orient_matrix_UB_12      -0.0482318000
_diffrn_orient_matrix_UB_13      -0.1467767000
_diffrn_orient_matrix_UB_21      -0.1488602000
_diffrn_orient_matrix_UB_22      -0.0141700000
_diffrn_orient_matrix_UB_23      -0.0418661000
_diffrn_orient_matrix_UB_31      -0.0287960000
_diffrn_orient_matrix_UB_32      0.0676171000
_diffrn_orient_matrix_UB_33      -0.1135597000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2418
_reflns_number_total             3053
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'ShelXS n/a (Sheldrick, 2008)'
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.043
_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)+(0.0726P)²+0.5383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1358
_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 C(H,H,H) groups
2. Restrained distances
 C5A-C2 \\sim C5-C2
 with sigma of 0.02
 C5A-C3 \\sim C5-C4
 with sigma of 0.02
 S1A-C4 \\sim S1-C3
 with sigma of 0.02
 S1-C2 \\sim S1A-C2
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 S1, S1A, C2, C3, C4, C5, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(S1A)=Sof(H3B)=Sof(H4B)=Sof(C5A)=Sof(H5A)=1-FVAR(1)
 Sof(S1)=Sof(H3)=Sof(H4)=Sof(C5)=Sof(H5)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3(H3B), C4(H4), C4(H4B), C5(H5), C5A(H5A), C10(H10), C11(H11),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19)
5.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.8081(2) 0.15840(13) 0.5325(3) 0.0286(4) Uani 0.611(4) 1 d D . P A 1
S1A S 0.6344(3) 0.1154(2) 0.7202(5) 0.0305(7) Uani 0.389(4) 1 d D . P A 2
O1 O 0.84682(15) 0.03890(9) 0.93392(19) 0.0294(4) Uani 1 1 d . . . . .
O2 O 1.05423(15) 0.11664(8) 0.38334(18) 0.0276(3) Uani 1 1 d . . . . .
N1 N 1.02259(18) 0.06827(10) 0.6580(2) 0.0260(4) Uani 1 1 d . . . . .
N2 N 0.99251(19) 0.04294(10) 0.7926(2) 0.0256(4) Uani 1 1 d . . . . .
H2 H 1.044(3) 0.0162(16) 0.872(4) 0.031 Uiso 1 1 d . U . . .
C1 C 0.8768(2) 0.06191(11) 0.8141(3) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.7839(2) 0.11079(11) 0.6941(3) 0.0259(4) Uani 1 1 d D . . . .
C3 C 0.6642(3) 0.19761(14) 0.4895(3) 0.0380(6) Uani 1 1 d D . . . .
H3 H 0.636785 0.233334 0.404776 0.046 Uiso 0.611(4) 1 calc R U P A 1
H3B H 0.644653 0.229962 0.397829 0.046 Uiso 0.389(4) 1 calc R U P A 2
C4 C 0.5855(3) 0.17725(14) 0.5794(3) 0.0379(6) Uani 1 1 d D . . . .
H4 H 0.497303 0.192317 0.563134 0.045 Uiso 0.611(4) 1 calc R U P A 1
H4B H 0.501560 0.199359 0.559505 0.045 Uiso 0.389(4) 1 calc R U P A 2
C5 C 0.6651(10) 0.1264(7) 0.7089(17) 0.047(3) Uani 0.611(4) 1 d D . P A 1
H5 H 0.634773 0.106917 0.793938 0.056 Uiso 0.611(4) 1 calc R U P A 1
C5A C 0.7937(16) 0.1556(10) 0.5720(18) 0.040(3) Uani 0.389(4) 1 d D . P A 2
H5A H 0.871132 0.160632 0.540533 0.048 Uiso 0.389(4) 1 calc R U P A 2
C6 C 1.1334(2) 0.04968(11) 0.6395(3) 0.0260(4) Uani 1 1 d . . . . .
C7 C 1.2346(2) 0.00093(13) 0.7522(3) 0.0306(5) Uani 1 1 d . . . . .
H7A H 1.262139 0.021494 0.863961 0.046 Uiso 1 1 calc R U . . .
H7B H 1.311036 -0.002816 0.712225 0.046 Uiso 1 1 calc R U . . .
H7C H 1.196993 -0.047804 0.754141 0.046 Uiso 1 1 calc R U . . .
C8 C 1.1577(2) 0.07856(12) 0.4922(3) 0.0269(5) Uani 1 1 d . . . . .
C9 C 1.0977(2) 0.13750(11) 0.2554(3) 0.0274(5) Uani 1 1 d . . . . .
C10 C 1.0237(2) 0.17816(12) 0.1193(3) 0.0295(5) Uani 1 1 d . . . . .
H10 H 0.936147 0.193170 0.107411 0.035 Uiso 1 1 calc R U . . .
C11 C 1.0840(2) 0.19513(12) 0.0042(3) 0.0290(5) Uani 1 1 d . . . . .
H11 H 1.036882 0.223108 -0.089462 0.035 Uiso 1 1 calc R U . . .
C12 C 1.2143(2) 0.17259(12) 0.0192(3) 0.0282(5) Uani 1 1 d . . . . .
C13 C 1.2729(2) 0.18917(12) -0.1043(3) 0.0312(5) Uani 1 1 d . . . . .
H13 H 1.224778 0.216445 -0.198643 0.037 Uiso 1 1 calc R U . . .
C14 C 1.3979(2) 0.16650(13) -0.0898(3) 0.0335(5) Uani 1 1 d . . . . .
H14 H 1.435932 0.178536 -0.173492 0.040 Uiso 1 1 calc R U . . .
C15 C 1.4704(2) 0.12556(14) 0.0479(3) 0.0350(5) Uani 1 1 d . . . . .
H15 H 1.557060 0.110050 0.056464 0.042 Uiso 1 1 calc R U . . .
C16 C 1.4171(2) 0.10777(13) 0.1702(3) 0.0318(5) Uani 1 1 d . . . . .
H16 H 1.467031 0.079956 0.262596 0.038 Uiso 1 1 calc R U . . .
C17 C 1.2883(2) 0.13055(12) 0.1595(3) 0.0273(5) Uani 1 1 d . . . . .
C18 C 1.2255(2) 0.11415(11) 0.2806(3) 0.0255(4) Uani 1 1 d . . . . .
C19 C 1.2619(2) 0.07562(12) 0.4354(3) 0.0274(5) Uani 1 1 d . . . . .
H19 H 1.343900 0.052487 0.487568 0.033 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 C2 1.714(3) . ?
S1 C3 1.632(3) . ?
S1A C2 1.683(4) . ?
S1A C4 1.613(5) . ?
O1 C1 1.235(3) . ?
O2 C8 1.390(3) . ?
O2 C9 1.365(3) . ?
N1 N2 1.364(3) . ?
N1 C6 1.288(3) . ?
N2 H2 0.88(3) . ?
N2 C1 1.351(3) . ?
C1 C2 1.483(3) . ?
C2 C5 1.345(10) . ?
C2 C5A 1.353(12) . ?
C3 H3 0.9500 . ?
C3 H3B 0.9500 . ?
C3 C4 1.354(4) . ?
C3 C5A 1.548(15) . ?
C4 H4 0.9500 . ?
C4 H4B 0.9500 . ?
C4 C5 1.491(12) . ?
C5 H5 0.9500 . ?
C5A H5A 0.9500 . ?
C6 C7 1.498(3) . ?
C6 C8 1.457(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C19 1.347(3) . ?
C9 C10 1.397(3) . ?
C9 C18 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.365(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.420(3) . ?
C12 C13 1.414(3) . ?
C12 C17 1.434(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.404(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.373(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.414(3) . ?
C17 C18 1.427(3) . ?
C18 C19 1.438(3) . ?
C19 H19 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
C3 S1 C2 92.09(15) . . ?
C4 S1A C2 92.2(2) . . ?
C9 O2 C8 105.96(17) . . ?
C6 N1 N2 118.63(19) . . ?
N1 N2 H2 125.5(18) . . ?
C1 N2 N1 119.43(18) . . ?
C1 N2 H2 115.0(17) . . ?
O1 C1 N2 120.5(2) . . ?
O1 C1 C2 119.0(2) . . ?
N2 C1 C2 120.48(19) . . ?
C1 C2 S1 128.54(18) . . ?
C1 C2 S1A 113.6(2) . . ?
C5 C2 S1 110.5(5) . . ?
C5 C2 C1 120.9(5) . . ?
C5A C2 S1A 112.0(6) . . ?
C5A C2 C1 134.3(7) . . ?
S1 C3 H3 121.3 . . ?
C4 C3 S1 117.4(2) . . ?
C4 C3 H3 121.3 . . ?
C4 C3 H3B 128.3 . . ?
C4 C3 C5A 103.5(5) . . ?
C5A C3 H3B 128.3 . . ?
S1A C4 H4B 120.1 . . ?
C3 C4 S1A 119.9(2) . . ?
C3 C4 H4 126.9 . . ?
C3 C4 H4B 120.1 . . ?
C3 C4 C5 106.1(4) . . ?
C5 C4 H4 126.9 . . ?
C2 C5 C4 113.7(7) . . ?
C2 C5 H5 123.2 . . ?
C4 C5 H5 123.2 . . ?
C2 C5A C3 112.1(10) . . ?
C2 C5A H5A 123.9 . . ?
C3 C5A H5A 123.9 . . ?
N1 C6 C7 125.97(19) . . ?
N1 C6 C8 115.3(2) . . ?
C8 C6 C7 118.74(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C6 115.98(19) . . ?
C19 C8 O2 110.86(18) . . ?
C19 C8 C6 133.2(2) . . ?
O2 C9 C10 124.4(2) . . ?
O2 C9 C18 110.76(19) . . ?
C18 C9 C10 124.8(2) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 C9 116.4(2) . . ?
C11 C10 H10 121.8 . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.6(2) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C17 120.1(2) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 C17 118.5(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 119.0(2) . . ?
C16 C17 C18 124.0(2) . . ?
C18 C17 C12 117.0(2) . . ?
C9 C18 C17 119.1(2) . . ?
C9 C18 C19 105.50(19) . . ?
C17 C18 C19 135.4(2) . . ?
C8 C19 C18 106.9(2) . . ?
C8 C19 H19 126.5 . . ?
C18 C19 H19 126.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.88(3) 1.98(3) 2.851(2) 174(3) 3_757 yes

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 C2 C5 C4 2.5(11) . . . . ?
S1 C3 C4 C5 5.2(6) . . . . ?
S1A C2 C5A C3 -0.7(15) . . . . ?
O1 C1 C2 S1 171.8(2) . . . . ?
O1 C1 C2 S1A -11.1(3) . . . . ?
O1 C1 C2 C5 -4.1(7) . . . . ?
O1 C1 C2 C5A 165.2(12) . . . . ?
O2 C8 C19 C18 0.2(2) . . . . ?
O2 C9 C10 C11 178.9(2) . . . . ?
O2 C9 C18 C17 179.79(18) . . . . ?
O2 C9 C18 C19 0.5(2) . . . . ?
N1 N2 C1 O1 179.11(19) . . . . ?
N1 N2 C1 C2 -1.0(3) . . . . ?
N1 C6 C8 O2 -5.7(3) . . . . ?
N1 C6 C8 C19 175.3(2) . . . . ?
N2 N1 C6 C7 0.9(3) . . . . ?
N2 N1 C6 C8 179.61(18) . . . . ?
N2 C1 C2 S1 -8.2(3) . . . . ?
N2 C1 C2 S1A 169.0(2) . . . . ?
N2 C1 C2 C5 175.9(7) . . . . ?
N2 C1 C2 C5A -14.7(13) . . . . ?
C1 C2 C5 C4 179.1(5) . . . . ?
C1 C2 C5A C3 -177.1(4) . . . . ?
C2 S1 C3 C4 -3.5(3) . . . . ?
C2 S1A C4 C3 5.1(3) . . . . ?
C3 S1 C2 C1 -175.9(2) . . . . ?
C3 S1 C2 C5 0.4(7) . . . . ?
C3 C4 C5 C2 -4.8(10) . . . . ?
C4 S1A C2 C1 175.0(2) . . . . ?
C4 S1A C2 C5A -2.1(10) . . . . ?
C4 C3 C5A C2 3.8(14) . . . . ?
C5A C3 C4 S1A -5.8(8) . . . . ?
C6 N1 N2 C1 179.97(19) . . . . ?
C6 C8 C19 C18 179.3(2) . . . . ?
C7 C6 C8 O2 173.11(18) . . . . ?
C7 C6 C8 C19 -6.0(4) . . . . ?
C8 O2 C9 C10 -179.2(2) . . . . ?
C8 O2 C9 C18 -0.3(2) . . . . ?
C9 O2 C8 C6 -179.21(18) . . . . ?
C9 O2 C8 C19 0.1(2) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C9 C18 C19 C8 -0.4(2) . . . . ?
C10 C9 C18 C17 -1.4(3) . . . . ?
C10 C9 C18 C19 179.3(2) . . . . ?
C10 C11 C12 C13 178.1(2) . . . . ?
C10 C11 C12 C17 -0.3(3) . . . . ?
C11 C12 C13 C14 -179.2(2) . . . . ?
C11 C12 C17 C16 179.0(2) . . . . ?
C11 C12 C17 C18 -0.9(3) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C12 C17 C18 C9 1.6(3) . . . . ?
C12 C17 C18 C19 -179.3(2) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C13 C12 C17 C18 -179.30(19) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C15 C16 C17 C18 179.7(2) . . . . ?
C16 C17 C18 C9 -178.2(2) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C17 C18 C19 C8 -179.6(2) . . . . ?
C18 C9 C10 C11 0.3(3) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_data_collection 2019-10-24
_olex2_date_sample_submission    2019-09-30
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.840
####################################################################### 
# 
# 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_drr19_s1875
_database_code_depnum_ccdc_archive 'CCDC 1982907'
loop_
_audit_author_name
_audit_author_address
'William Lewis'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-02-09 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_sydney_internal_submission_code drr19_s1875
_sydney_internal_submission_date 2019-08-26
_sydney_internal_submission_number s1875
_sydney_internal_client_code     rukh
_sydney_internal_client_email    rukhsanaanjum@yahoo.com
_sydney_internal_client_name     'Rukhsana Anjum'
_sydney_internal_supervisor_code drr
_sydney_internal_supervisor_name 'Des Richards'
_sydney_internal_collection_date 2019-09-27
_sydney_internal_collection_user wlew0588
_sydney_internal_process_date    2019-09-30
_sydney_internal_process_user    wlew0588
_sydney_internal_solution_date   2019-09-30
_sydney_internal_solution_user   wlew0588
_sydney_internal_refine_date     2019-09-30
_sydney_internal_refine_user     wlew0588
_sydney_internal_check_and_archive_date 2019-09-30
_sydney_internal_check_user      wlew0588
_refine_special_details          ?
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 N3 O2'
_chemical_formula_sum            'C25 H17 N3 O2'
_chemical_formula_weight         391.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H17 N3 O2'
_chemical_oxdiff_usercomment     SF-77
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                   4.4595(2)
_cell_length_b                   24.1919(8)
_cell_length_c                   17.1497(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.031(4)
_cell_angle_gamma                90
_cell_volume                     1850.17(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6236
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0400
_cell_measurement_theta_min      4.4570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 2 0.0217
0 1 -2 0.0217
-3 -3 -1 0.2829
0 1 0 0.0065
0 -1 0 0.0095
1 1 0 0.3039

_exptl_crystal_recrystallization_method 'crystallised from DMSO'
_exptl_crystal_size_max          0.603
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.016
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
-0.0007 -0.9991 1.9998 0.1532 -0.0461 0.1034
0.0007 0.9991 -1.9998 -0.1532 0.0461 -0.1034
-3.0015 -2.9623 -1.0181 -0.5715 0.1578 0.8766
0.0002 0.9986 -0.0001 0.0057 0.0598 -0.0209
-0.0002 -0.9986 0.0001 -0.0057 -0.0598 0.0209
1.0006 0.9875 0.0061 0.1640 -0.0549 -0.3060

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.711
_diffrn_reflns_theta_min         3.654
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2930
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  44.00   1.00    5.00    --  -39.19  19.00  30.00   49
  2  ω    -21.00  38.00   1.00    5.00    --  -39.19  38.00-120.00   59
  3  ω     -5.00  44.00   1.00    5.00    --  -39.19  19.00   0.00   49
  4  ω     -5.00  44.00   1.00    5.00    --  -39.19  19.00 120.00   49
  5  ω   -122.00  13.00   1.00    5.00    --  -39.19 -19.00-120.00  135
  6  ω     -5.00  44.00   1.00    5.00    --  -39.19  19.00-150.00   49
  7  ω   -130.00 -39.00   1.00    5.00    --  -39.19-178.00-180.00   91
  8  ω     61.00 130.00   1.00    5.00    --   39.19 178.00-120.00   69
  9  ω     27.00  57.00   1.00   20.00    --  106.69 -30.00 -90.00   30
 10  ω     22.00 106.00   1.00   20.00    --  106.69 -95.00  90.00   84
 11  ω     22.00 106.00   1.00   20.00    --  106.69 -95.00-150.00   84
 12  ω     77.00 178.00   1.00   20.00    --  106.69  45.00  30.00  101
 13  ω     73.00 178.00   1.00   20.00    --  106.69  30.00-120.00  105
 14  ω     30.00  93.00   1.00   20.00    --  106.69 -61.00 -30.00   63
 15  ω     27.00  57.00   1.00   20.00    --  106.69 -30.00-150.00   30
 16  ω     22.00 106.00   1.00   20.00    --  106.69 -95.00   0.00   84
 17  ω     77.00 178.00   1.00   20.00    --  106.69  45.00   0.00  101
 18  ω     27.00  57.00   1.00   20.00    --  106.69 -30.00   0.00   30
 19  ω     30.00  93.00   1.00   20.00    --  106.69 -61.00-150.00   63
 20  ω     73.00 178.00   1.00   20.00    --  106.69  30.00 -30.00  105
 21  ω     30.00  72.00   1.00   20.00    --  106.69 -45.00 120.00   42
 22  ω     27.00 109.00   1.00   20.00    --  106.69-111.00 150.00   82
 23  ω    104.00 178.00   1.00   20.00    --  106.69 111.00-120.00   74
 24  ω    104.00 178.00   1.00   20.00    --  106.69 111.00 -90.00   74
 25  ω   -115.00  -8.00   1.00    5.00    --  -39.19 -57.00 150.00  107
 26  ω   -115.00  -8.00   1.00    5.00    --  -39.19 -57.00 -60.00  107
 27  ω   -115.00  -8.00   1.00    5.00    --  -39.19 -57.00  90.00  107
 28  ω   -115.00  -8.00   1.00    5.00    --  -39.19 -57.00  30.00  107
 29  ω   -115.00  -8.00   1.00    5.00    --  -39.19 -57.00-120.00  107
 30  ω      8.00 115.00   1.00    5.00    --   39.19  57.00  60.00  107
 31  ω     61.00 130.00   1.00    5.00    --   39.19 178.00-180.00   69
 32  ω     77.00 147.00   1.00   20.00    --  106.69  45.00 -90.00   70
 33  ω     77.00 178.00   1.00   20.00    --  106.69  45.00-180.00  101
 34  ω     77.00 178.00   1.00   20.00    --  106.69  45.00  90.00  101
 35  ω     27.00  57.00   1.00   20.00    --  106.69 -30.00-120.00   30
 36  ω     73.00 178.00   1.00   20.00    --  106.69  30.00 150.00  105
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1578610000
_diffrn_orient_matrix_UB_12      0.0056447000
_diffrn_orient_matrix_UB_13      0.0794969000
_diffrn_orient_matrix_UB_21      -0.1140098000
_diffrn_orient_matrix_UB_22      0.0599149000
_diffrn_orient_matrix_UB_23      0.0068204000
_diffrn_orient_matrix_UB_31      -0.2854606000
_diffrn_orient_matrix_UB_32      -0.0208405000
_diffrn_orient_matrix_UB_33      0.0412000000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3659
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.031
_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)+(0.0644P)²+0.5173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1295
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.2217(3) 0.85465(5) 0.31790(7) 0.0258(3) Uani 1 1 d . . . . .
O2 O -0.0223(3) 0.82594(6) 0.51132(7) 0.0318(3) Uani 1 1 d . . . . .
N1 N -0.1591(4) 0.78929(6) 0.39303(9) 0.0253(3) Uani 1 1 d . . . . .
H1 H -0.139(5) 0.7882(9) 0.3383(13) 0.030 Uiso 1 1 d . U . . .
N2 N -0.3217(3) 0.74732(6) 0.42600(9) 0.0252(3) Uani 1 1 d . . . . .
N3 N -0.2972(4) 0.75111(7) 0.25585(9) 0.0294(4) Uani 1 1 d . . . . .
C1 C -0.4540(4) 0.71227(7) 0.38010(10) 0.0236(4) Uani 1 1 d . . . . .
C2 C -0.4707(4) 0.71382(7) 0.29322(10) 0.0250(4) Uani 1 1 d . . . . .
C3 C -0.3094(5) 0.75306(9) 0.17819(11) 0.0334(4) Uani 1 1 d . . . . .
H3 H -0.185186 0.779049 0.152096 0.040 Uiso 1 1 calc R U . . .
C4 C -0.4922(5) 0.71947(8) 0.13335(11) 0.0322(4) Uani 1 1 d . . . . .
H4 H -0.492754 0.722083 0.078073 0.039 Uiso 1 1 calc R U . . .
C5 C -0.6736(5) 0.68208(8) 0.17159(12) 0.0329(4) Uani 1 1 d . . . . .
H5 H -0.803828 0.658600 0.142866 0.039 Uiso 1 1 calc R U . . .
C6 C -0.6642(5) 0.67904(8) 0.25243(11) 0.0304(4) Uani 1 1 d . . . . .
H6 H -0.788109 0.653563 0.279578 0.037 Uiso 1 1 calc R U . . .
C7 C -0.5908(4) 0.66454(8) 0.42274(10) 0.0252(4) Uani 1 1 d . . . . .
C8 C -0.5144(5) 0.61048(8) 0.40192(11) 0.0295(4) Uani 1 1 d . . . . .
H8 H -0.388845 0.604106 0.358100 0.035 Uiso 1 1 calc R U . . .
C9 C -0.6212(5) 0.56603(8) 0.44503(12) 0.0324(4) Uani 1 1 d . . . . .
H9 H -0.565814 0.529431 0.431055 0.039 Uiso 1 1 calc R U . . .
C10 C -0.8082(5) 0.57487(8) 0.50832(11) 0.0324(4) Uani 1 1 d . . . . .
H10 H -0.881857 0.544425 0.537576 0.039 Uiso 1 1 calc R U . . .
C11 C -0.8871(5) 0.62840(8) 0.52873(11) 0.0311(4) Uani 1 1 d . . . . .
H11 H -1.017680 0.634477 0.571635 0.037 Uiso 1 1 calc R U . . .
C12 C -0.7771(4) 0.67317(8) 0.48700(11) 0.0271(4) Uani 1 1 d . . . . .
H12 H -0.828542 0.709721 0.502186 0.033 Uiso 1 1 calc R U . . .
C13 C -0.0054(4) 0.82429(8) 0.44032(11) 0.0256(4) Uani 1 1 d . . . . .
C14 C 0.1967(4) 0.86204(8) 0.39763(10) 0.0249(4) Uani 1 1 d . . . . .
C15 C 0.4224(4) 0.89378(8) 0.29339(11) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.5137(4) 0.90098(8) 0.21595(11) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.441574 0.877987 0.175139 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7117(4) 0.94281(8) 0.20234(11) 0.0289(4) Uani 1 1 d . . . . .
H17 H 0.779717 0.948780 0.150537 0.035 Uiso 1 1 calc R U . . .
C18 C 0.8211(4) 0.97802(8) 0.26289(11) 0.0265(4) Uani 1 1 d . . . . .
C19 C 1.0229(4) 1.02163(8) 0.24721(11) 0.0299(4) Uani 1 1 d . . . . .
H19 H 1.089444 1.027515 0.195258 0.036 Uiso 1 1 calc R U . . .
C20 C 1.1245(5) 1.05556(8) 0.30533(12) 0.0324(4) Uani 1 1 d . . . . .
H20 H 1.260188 1.084648 0.293523 0.039 Uiso 1 1 calc R U . . .
C21 C 1.0278(4) 1.04734(8) 0.38287(12) 0.0312(4) Uani 1 1 d . . . . .
H21 H 1.097111 1.071146 0.423071 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8341(4) 1.00513(8) 0.40028(11) 0.0277(4) Uani 1 1 d . . . . .
H22 H 0.771572 0.999768 0.452684 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7268(4) 0.96964(7) 0.34163(10) 0.0252(4) Uani 1 1 d . . . . .
C24 C 0.5218(4) 0.92545(7) 0.35535(10) 0.0242(4) Uani 1 1 d . . . . .
C25 C 0.3746(4) 0.90350(8) 0.42312(11) 0.0256(4) Uani 1 1 d . . . . .
H25 H 0.397752 0.915704 0.475425 0.031 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
O1 C14 1.384(2) . ?
O1 C15 1.369(2) . ?
O2 C13 1.221(2) . ?
N1 H1 0.94(2) . ?
N1 N2 1.370(2) . ?
N1 C13 1.358(2) . ?
N2 C1 1.299(2) . ?
N3 C2 1.350(2) . ?
N3 C3 1.334(3) . ?
C1 C2 1.492(2) . ?
C1 C7 1.497(3) . ?
C2 C6 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(3) . ?
C7 C12 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.477(3) . ?
C14 C25 1.351(3) . ?
C15 C16 1.400(3) . ?
C15 C24 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.429(3) . ?
C18 C19 1.413(3) . ?
C18 C23 1.429(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.368(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.412(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.406(3) . ?
C23 C24 1.426(3) . ?
C24 C25 1.437(3) . ?
C25 H25 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
C15 O1 C14 105.49(14) . . ?
N2 N1 H1 116.1(14) . . ?
C13 N1 H1 124.4(14) . . ?
C13 N1 N2 118.86(15) . . ?
C1 N2 N1 118.30(15) . . ?
C3 N3 C2 118.32(17) . . ?
N2 C1 C2 127.68(17) . . ?
N2 C1 C7 113.13(15) . . ?
C2 C1 C7 119.14(16) . . ?
N3 C2 C1 117.54(16) . . ?
N3 C2 C6 121.33(17) . . ?
C6 C2 C1 121.10(17) . . ?
N3 C3 H3 118.0 . . ?
N3 C3 C4 123.90(19) . . ?
C4 C3 H3 118.0 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.78(18) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.46(19) . . ?
C6 C5 H5 120.3 . . ?
C2 C6 H6 120.4 . . ?
C5 C6 C2 119.18(19) . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C1 119.83(17) . . ?
C12 C7 C1 120.87(17) . . ?
C12 C7 C8 119.13(17) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.30(18) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.27(19) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.65(19) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.57(18) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.07(18) . . ?
C11 C12 H12 120.0 . . ?
O2 C13 N1 125.78(18) . . ?
O2 C13 C14 120.81(17) . . ?
N1 C13 C14 113.41(16) . . ?
O1 C14 C13 117.34(16) . . ?
C25 C14 O1 111.59(16) . . ?
C25 C14 C13 131.05(17) . . ?
O1 C15 C16 124.59(17) . . ?
O1 C15 C24 110.90(16) . . ?
C24 C15 C16 124.51(18) . . ?
C15 C16 H16 121.8 . . ?
C17 C16 C15 116.33(18) . . ?
C17 C16 H16 121.8 . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.62(18) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 C23 120.12(17) . . ?
C19 C18 C17 121.62(18) . . ?
C19 C18 C23 118.26(17) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.35(18) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.01(19) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.20(18) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.88(18) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 119.30(17) . . ?
C22 C23 C24 123.88(17) . . ?
C24 C23 C18 116.81(16) . . ?
C15 C24 C23 119.60(17) . . ?
C15 C24 C25 105.68(16) . . ?
C23 C24 C25 134.72(17) . . ?
C14 C25 C24 106.33(16) . . ?
C14 C25 H25 126.8 . . ?
C24 C25 H25 126.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N3 0.94(2) 1.82(2) 2.601(2) 138.9(19) . yes

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
O1 C14 C25 C24 1.1(2) . . . . ?
O1 C15 C16 C17 178.89(17) . . . . ?
O1 C15 C24 C23 -178.31(15) . . . . ?
O1 C15 C24 C25 1.0(2) . . . . ?
O2 C13 C14 O1 174.88(16) . . . . ?
O2 C13 C14 C25 -3.4(3) . . . . ?
N1 N2 C1 C2 -4.7(3) . . . . ?
N1 N2 C1 C7 172.67(15) . . . . ?
N1 C13 C14 O1 -4.7(2) . . . . ?
N1 C13 C14 C25 177.03(19) . . . . ?
N2 N1 C13 O2 -8.5(3) . . . . ?
N2 N1 C13 C14 171.06(15) . . . . ?
N2 C1 C2 N3 9.9(3) . . . . ?
N2 C1 C2 C6 -168.49(19) . . . . ?
N2 C1 C7 C8 -125.16(19) . . . . ?
N2 C1 C7 C12 50.0(2) . . . . ?
N3 C2 C6 C5 1.4(3) . . . . ?
N3 C3 C4 C5 0.4(3) . . . . ?
C1 C2 C6 C5 179.67(18) . . . . ?
C1 C7 C8 C9 174.85(18) . . . . ?
C1 C7 C12 C11 -176.05(17) . . . . ?
C2 N3 C3 C4 0.7(3) . . . . ?
C2 C1 C7 C8 52.5(2) . . . . ?
C2 C1 C7 C12 -132.37(19) . . . . ?
C3 N3 C2 C1 180.00(17) . . . . ?
C3 N3 C2 C6 -1.7(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C2 -0.2(3) . . . . ?
C7 C1 C2 N3 -167.38(16) . . . . ?
C7 C1 C2 C6 14.3(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C7 C12 C11 -0.8(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C7 1.5(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C13 N1 N2 C1 -176.20(16) . . . . ?
C13 C14 C25 C24 179.50(18) . . . . ?
C14 O1 C15 C16 180.00(18) . . . . ?
C14 O1 C15 C24 -0.29(19) . . . . ?
C15 O1 C14 C13 -179.17(16) . . . . ?
C15 O1 C14 C25 -0.6(2) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C15 C24 C25 C14 -1.2(2) . . . . ?
C16 C15 C24 C23 1.4(3) . . . . ?
C16 C15 C24 C25 -179.33(18) . . . . ?
C16 C17 C18 C19 -179.06(18) . . . . ?
C16 C17 C18 C23 0.9(3) . . . . ?
C17 C18 C19 C20 179.34(18) . . . . ?
C17 C18 C23 C22 -179.26(17) . . . . ?
C17 C18 C23 C24 -0.3(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C18 C23 C24 C15 -0.8(3) . . . . ?
C18 C23 C24 C25 -179.79(19) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
C19 C18 C23 C24 179.69(16) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
C21 C22 C23 C24 -179.05(18) . . . . ?
C22 C23 C24 C15 178.11(18) . . . . ?
C22 C23 C24 C25 -0.9(3) . . . . ?
C23 C18 C19 C20 -0.7(3) . . . . ?
C23 C24 C25 C14 177.9(2) . . . . ?
C24 C15 C16 C17 -0.8(3) . . . . ?

loop_
_audit_author_email
rukhsana.anjum@sydney.edu.au
?
d.richardson@sydney.edu.au
_olex2_date_sample_data_collection 2019-09-27
_olex2_date_sample_submission    2019-08-26
_olex2_exptl_crystal_mounting_method 'in paratone on a micromount'
_olex2_submission_original_sample_id SF-77
_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 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.676
