# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_rjkt1902
_database_code_depnum_ccdc_archive 'CCDC 1945618'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;Department of Chemistry, University of York
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N O S'
_chemical_formula_sum            'C21 H19 N O S'
_chemical_formula_weight         333.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21  H19 N1 O1 S1'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh-APG-84'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2702(8)
_cell_length_b                   8.7819(9)
_cell_length_c                   13.6782(8)
_cell_angle_alpha                98.564(7)
_cell_angle_beta                 100.026(7)
_cell_angle_gamma                104.633(10)
_cell_volume                     814.84(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      69.3250
_cell_measurement_theta_min      5.6720
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0031
0 -1 0 0.0091
-1 1 -5 0.1062
1 0 -5 0.0684
3 0 -5 0.0605
4 -1 -5 0.0553
5 -1 0 0.0821
0 0 1 0.0905
-4 1 -3 0.1219
-3 0 5 0.0605

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'evaporation of dichloromethane/hexane'
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.012
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
0.0011 0.9989 -0.0016 -0.0517 0.1776 -0.0046
-0.0011 -0.9989 0.0016 0.0517 -0.1776 0.0046
-0.9940 0.9993 -5.0057 0.5704 0.1754 0.2452
1.0036 -0.0024 -5.0042 0.2615 0.0334 0.5145
3.0023 -0.0052 -5.0044 -0.0991 0.0690 0.7792
4.0006 -1.0056 -5.0028 -0.2277 -0.0907 0.9161
4.9957 -1.0060 0.0012 -0.8497 -0.0886 0.6663
-0.0009 0.0002 1.0008 -0.0883 -0.0031 -0.0764
-3.9938 1.0040 -3.0038 0.9345 0.1158 -0.3047
-3.0023 0.0052 5.0044 0.0991 -0.0690 -0.7792

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4947
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         5.316
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00 -16.00   1.00    4.50    --    0.00 -37.00 150.00   43
  2  ω     -9.00  25.00   1.00    4.50    --    0.00 -37.00 150.00   34
  3  ω    -14.00  29.00   1.00    4.50    --    0.00  57.00 -30.00   43
  4  ω     37.00  84.00   1.00   18.00    --   54.00  57.00 -60.00   47
  5  ω     25.00  66.00   1.00   18.00    --   54.00-125.00  60.00   41
  6  ω     69.00 107.00   1.00   18.00    --   54.00-125.00  60.00   38
  7  ω     29.00  69.00   1.00   18.00    --   54.00-125.00-120.00   40
  8  ω     40.00  91.00   1.00   18.00    --   54.00  57.00 -30.00   51
  9  ω     35.00  83.00   1.00   18.00    --   54.00  65.00-110.00   48
 10  ω     31.00 122.00   1.00   18.00    --   54.00  37.00-180.00   91
 11  ω    -18.00  79.00   1.00   18.00    --   54.00 -37.00   0.00   97
 12  ω     36.00 110.00   1.00   18.00    --  108.00-111.00-180.00   74
 13  ω     90.00 149.00   1.00   18.00    --  108.00  63.00  90.00   59
 14  ω     57.00 107.00   1.00   18.00    --  108.00-111.00  90.00   50
 15  ω     38.00 142.00   1.00   18.00    --  108.00 -91.00-150.00  104
 16  ω     38.00 132.00   1.00   18.00    --  108.00 -37.00 -60.00   94
 17  ω    114.00 159.00   1.00   18.00    --  108.00  63.00   0.00   45
 18  ω     65.00 126.00   1.00   18.00    --  108.00 -50.00-180.00   61
 19  ω     86.00 158.00   1.00   18.00    --  108.00  50.00 -30.00   72
 20  ω    108.00 135.00   1.00   18.00    --  108.00 111.00 -90.00   27
 21  ω     42.00  77.00   1.00   18.00    --  108.00 -37.00 120.00   35
 22  ω     87.00 122.00   1.00   18.00    --  108.00 -37.00 120.00   35
 23  ω     73.00 108.00   1.00   18.00    --  108.00-111.00   0.00   35
 24  ω     39.00 138.00   1.00   18.00    --  108.00 -77.00   0.00   99
 25  ω    108.00 178.00   1.00   18.00    --  108.00  37.00  60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1804714000
_diffrn_orient_matrix_UB_12      -0.0516730000
_diffrn_orient_matrix_UB_13      -0.0884194000
_diffrn_orient_matrix_UB_21      0.0180494000
_diffrn_orient_matrix_UB_22      0.1777158000
_diffrn_orient_matrix_UB_23      -0.0031478000
_diffrn_orient_matrix_UB_31      0.1324261000
_diffrn_orient_matrix_UB_32      -0.0048301000
_diffrn_orient_matrix_UB_33      -0.0762432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2386
_reflns_number_total             2912
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2912
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.058
_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)+(0.0475P)²+0.4485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          
;
The structure is disordered in two ways.  Firstly, the sulfur was
modelled in two positions with refined occupancies of 0.747:0.253(8).
The each pairs of C-S bonds were restrained to be equal, S1-C5 & 
S1a-C5 and S1-C16 & S1a-C16.  There is evidence from the ADP that
the phenyl (C16-C21) and 5-membered (C1-C5) rings are also 
disordered, but the difference in positions of the atoms in both
form is too little to create discrete models for each form.
The cyclopropyl group was disordered and also modelled
in two positions with refined occupancies of 0.672:0.328(2).
Equivalent pairs of disordered atoms were constrained to 
have the same ADP, namely S1 & S1a, C6 & C6a, C7 & C7a 
and C8 & C8a.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 S1-C16 \\sim S1A-C16
 with sigma of 0.01
 S1-C5 \\sim S1A-C5
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
Uanis(C6A) = Uanis(C6)
Uanis(S1) = Uanis(S1A)
4. Others
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=1-
 FVAR(1)
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=FVAR(1)
 Sof(S1A)=1-FVAR(2)
 Sof(S1)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C6A(H6A)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C7A(H7AA,H7AB), C8(H8A,H8B), C8A(H8AA,H8AB), C9(H9A,
 H9B)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1883(3) 0.4146(2) 0.88603(15) 0.0305(4) Uani 1 1 d . . . . .
C2 C 0.0880(3) 0.5449(3) 0.88577(16) 0.0335(5) Uani 1 1 d . . . . .
H2A H 0.0644 0.5782 0.9538 0.040 Uiso 1 1 calc R . . . .
H2B H -0.0389 0.5062 0.8362 0.040 Uiso 1 1 calc R . . . .
C3 C 0.2242(3) 0.6863(2) 0.85615(15) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.4086(3) 0.6320(3) 0.85225(14) 0.0356(5) Uani 1 1 d . . . . .
C5 C 0.3815(3) 0.4799(3) 0.86621(15) 0.0321(5) Uani 1 1 d D . . . .
C6 C 0.6019(5) 0.7091(4) 0.8336(2) 0.0318(6) Uani 0.672(2) 1 d . . P A 1
H6 H 0.7052 0.6566 0.8551 0.038 Uiso 0.672(2) 1 calc R . P A 1
C6A C 0.5504(10) 0.7810(9) 0.8322(5) 0.0318(6) Uani 0.328(2) 1 d . . P A 2
H6A H 0.4992 0.8734 0.8194 0.038 Uiso 0.328(2) 1 calc R . P A 2
C7 C 0.6767(5) 0.8877(4) 0.8380(2) 0.0360(6) Uani 0.672(2) 1 d . . P A 1
H7A H 0.5917 0.9551 0.8550 0.043 Uiso 0.672(2) 1 calc R . P A 1
H7B H 0.8179 0.9399 0.8649 0.043 Uiso 0.672(2) 1 calc R . P A 1
C7A C 0.7606(10) 0.8184(8) 0.8878(5) 0.0360(6) Uani 0.328(2) 1 d . . P A 2
H7AA H 0.8377 0.9328 0.9096 0.043 Uiso 0.328(2) 1 calc R . P A 2
H7AB H 0.7927 0.7483 0.9346 0.043 Uiso 0.328(2) 1 calc R . P A 2
C8 C 0.6160(5) 0.7777(4) 0.7377(2) 0.0363(7) Uani 0.672(2) 1 d . . P A 1
H8A H 0.7194 0.7611 0.7025 0.044 Uiso 0.672(2) 1 calc R . P A 1
H8B H 0.4930 0.7762 0.6926 0.044 Uiso 0.672(2) 1 calc R . P A 1
C8A C 0.7036(10) 0.7484(9) 0.7773(5) 0.0363(7) Uani 0.328(2) 1 d . . P A 2
H8AA H 0.7006 0.6350 0.7556 0.044 Uiso 0.328(2) 1 calc R . P A 2
H8AB H 0.7456 0.8194 0.7306 0.044 Uiso 0.328(2) 1 calc R . P A 2
C9 C 0.2600(4) 0.8498(3) 0.92911(17) 0.0496(6) Uani 1 1 d . . . . .
H9A H 0.1537 0.8459 0.9660 0.060 Uiso 1 1 calc R . . . .
H9B H 0.3854 0.8770 0.9791 0.060 Uiso 1 1 calc R . . . .
C10 C 0.1688(3) 0.8878(3) 0.76563(17) 0.0386(5) Uani 1 1 d . . . . .
C11 C 0.1081(4) 0.9512(3) 0.68282(18) 0.0428(5) Uani 1 1 d . . . . .
H11 H 0.1295 1.0638 0.6886 0.051 Uiso 1 1 calc R . . . .
C12 C 0.0157(4) 0.8461(3) 0.59175(17) 0.0435(6) Uani 1 1 d . . . . .
H12 H -0.0279 0.8877 0.5346 0.052 Uiso 1 1 calc R . . . .
C13 C -0.0150(3) 0.6819(3) 0.58140(16) 0.0407(5) Uani 1 1 d . . . . .
H13 H -0.0802 0.6123 0.5180 0.049 Uiso 1 1 calc R . . . .
C14 C 0.0495(3) 0.6193(3) 0.66367(15) 0.0353(5) Uani 1 1 d . . . . .
H14 H 0.0307 0.5069 0.6572 0.042 Uiso 1 1 calc R . . . .
C15 C 0.1416(3) 0.7230(2) 0.75519(15) 0.0338(5) Uani 1 1 d . . . . .
C16 C 0.5588(3) 0.3094(2) 0.74034(16) 0.0330(5) Uani 1 1 d D . . . .
C17 C 0.4607(3) 0.3559(3) 0.65959(16) 0.0350(5) Uani 1 1 d . . . . .
H17 H 0.3774 0.4215 0.6704 0.042 Uiso 1 1 calc R . . . .
C18 C 0.4842(3) 0.3066(3) 0.56245(18) 0.0448(6) Uani 1 1 d . . . . .
H18 H 0.4176 0.3394 0.5069 0.054 Uiso 1 1 calc R . . . .
C19 C 0.6040(4) 0.2100(3) 0.5462(2) 0.0546(7) Uani 1 1 d . . . . .
H19 H 0.6192 0.1759 0.4796 0.065 Uiso 1 1 calc R . . . .
C20 C 0.7014(4) 0.1634(3) 0.6270(2) 0.0562(7) Uani 1 1 d . . . . .
H20 H 0.7839 0.0972 0.6159 0.067 Uiso 1 1 calc R . . . .
C21 C 0.6800(3) 0.2119(3) 0.7233(2) 0.0467(6) Uani 1 1 d . . . . .
H21 H 0.7476 0.1793 0.7786 0.056 Uiso 1 1 calc R . . . .
N1 N 0.2639(3) 0.9671(2) 0.86373(15) 0.0489(5) Uani 1 1 d . . . . .
H1 H 0.241(4) 1.057(4) 0.883(2) 0.061(8) Uiso 1 1 d . . . . .
O1 O 0.1201(2) 0.28091(18) 0.90109(13) 0.0453(4) Uani 1 1 d . . . . .
S1 S 0.5401(3) 0.3531(4) 0.86884(9) 0.0353(5) Uani 0.749(8) 1 d D . P . .
S1A S 0.5748(7) 0.4084(8) 0.8689(3) 0.0353(5) Uani 0.251(8) 1 d D . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.505(3) . ?
C1 C5 1.465(3) . ?
C1 O1 1.217(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.535(3) . ?
C3 C4 1.539(3) . ?
C3 C9 1.555(3) . ?
C3 C15 1.521(3) . ?
C4 C5 1.347(3) . ?
C4 C6 1.481(4) . ?
C4 C6A 1.541(7) . ?
C5 S1 1.794(3) . ?
C5 S1A 1.674(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.513(4) . ?
C6 C8 1.531(4) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.513(9) . ?
C6A C8A 1.508(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.479(4) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.487(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N1 1.460(3) . ?
C10 C11 1.388(3) . ?
C10 C15 1.392(3) . ?
C10 N1 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(3) . ?
C16 C17 1.379(3) . ?
C16 C21 1.399(3) . ?
C16 S1 1.779(2) . ?
C16 S1A 1.813(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.370(4) . ?
C21 H21 0.9500 . ?
N1 H1 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 107.29(17) . . ?
O1 C1 C2 125.6(2) . . ?
O1 C1 C5 127.15(19) . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
C1 C2 C3 106.64(17) . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C2 C3 C4 103.21(16) . . ?
C2 C3 C9 113.28(18) . . ?
C4 C3 C9 114.5(2) . . ?
C15 C3 C2 113.81(18) . . ?
C15 C3 C4 111.20(16) . . ?
C15 C3 C9 101.25(17) . . ?
C3 C4 C6A 102.6(3) . . ?
C5 C4 C3 111.16(18) . . ?
C5 C4 C6 115.1(2) . . ?
C5 C4 C6A 146.2(3) . . ?
C6 C4 C3 133.7(2) . . ?
C1 C5 S1 117.09(19) . . ?
C1 C5 S1A 132.3(3) . . ?
C4 C5 C1 111.34(18) . . ?
C4 C5 S1 131.5(2) . . ?
C4 C5 S1A 116.0(3) . . ?
S1A C5 S1 15.68(16) . . ?
C4 C6 H6 114.6 . . ?
C4 C6 C7 123.1(3) . . ?
C4 C6 C8 120.0(3) . . ?
C7 C6 H6 114.6 . . ?
C7 C6 C8 58.1(2) . . ?
C8 C6 H6 114.6 . . ?
C4 C6A H6A 117.8 . . ?
C7A C6A C4 115.6(5) . . ?
C7A C6A H6A 117.8 . . ?
C8A C6A C4 115.7(6) . . ?
C8A C6A H6A 117.8 . . ?
C8A C6A C7A 59.0(5) . . ?
C6 C7 H7A 117.6 . . ?
C6 C7 H7B 117.6 . . ?
H7A C7 H7B 114.7 . . ?
C8 C7 C6 61.6(2) . . ?
C8 C7 H7A 117.6 . . ?
C8 C7 H7B 117.6 . . ?
C6A C7A H7AA 117.7 . . ?
C6A C7A H7AB 117.7 . . ?
H7AA C7A H7AB 114.9 . . ?
C8A C7A C6A 60.3(5) . . ?
C8A C7A H7AA 117.7 . . ?
C8A C7A H7AB 117.7 . . ?
C6 C8 H8A 117.7 . . ?
C6 C8 H8B 117.7 . . ?
C7 C8 C6 60.3(2) . . ?
C7 C8 H8A 117.7 . . ?
C7 C8 H8B 117.7 . . ?
H8A C8 H8B 114.9 . . ?
C6A C8A H8AA 117.7 . . ?
C6A C8A H8AB 117.7 . . ?
C7A C8A C6A 60.7(4) . . ?
C7A C8A H8AA 117.7 . . ?
C7A C8A H8AB 117.7 . . ?
H8AA C8A H8AB 114.8 . . ?
C3 C9 H9A 110.7 . . ?
C3 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
N1 C9 C3 105.04(18) . . ?
N1 C9 H9A 110.7 . . ?
N1 C9 H9B 110.7 . . ?
C11 C10 C15 120.2(2) . . ?
N1 C10 C11 129.0(2) . . ?
N1 C10 C15 110.70(19) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11 120.9 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.9(2) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.9(2) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 C3 109.49(18) . . ?
C14 C15 C3 129.48(19) . . ?
C14 C15 C10 121.03(19) . . ?
C17 C16 C21 119.5(2) . . ?
C17 C16 S1 126.44(17) . . ?
C17 C16 S1A 120.0(2) . . ?
C21 C16 S1 113.96(18) . . ?
C21 C16 S1A 119.1(2) . . ?
S1 C16 S1A 15.57(14) . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C9 N1 H1 121.1(19) . . ?
C10 N1 C9 109.04(19) . . ?
C10 N1 H1 115(2) . . ?
C16 S1 C5 103.28(12) . . ?
C5 S1A C16 106.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86(3) 2.34(3) 3.190(3) 167(3) 1_565

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -5.9(2) . . . . ?
C1 C2 C3 C9 -130.3(2) . . . . ?
C1 C2 C3 C15 114.75(19) . . . . ?
C1 C5 S1 C16 112.4(2) . . . . ?
C1 C5 S1A C16 95.0(4) . . . . ?
C2 C1 C5 C4 -1.1(2) . . . . ?
C2 C1 C5 S1 176.78(14) . . . . ?
C2 C1 C5 S1A 172.2(3) . . . . ?
C2 C3 C4 C5 5.5(2) . . . . ?
C2 C3 C4 C6 -176.7(2) . . . . ?
C2 C3 C4 C6A -175.0(3) . . . . ?
C2 C3 C9 N1 -141.6(2) . . . . ?
C2 C3 C15 C10 133.74(19) . . . . ?
C2 C3 C15 C14 -45.5(3) . . . . ?
C3 C4 C5 C1 -2.9(2) . . . . ?
C3 C4 C5 S1 179.62(16) . . . . ?
C3 C4 C5 S1A -177.3(2) . . . . ?
C3 C4 C6 C7 15.5(4) . . . . ?
C3 C4 C6 C8 -53.9(4) . . . . ?
C3 C4 C6A C7A 141.2(5) . . . . ?
C3 C4 C6A C8A -152.6(5) . . . . ?
C3 C9 N1 C10 21.2(3) . . . . ?
C4 C3 C9 N1 100.4(2) . . . . ?
C4 C3 C15 C10 -110.2(2) . . . . ?
C4 C3 C15 C14 70.5(3) . . . . ?
C4 C5 S1 C16 -70.2(3) . . . . ?
C4 C5 S1A C16 -92.0(4) . . . . ?
C4 C6 C7 C8 -107.4(3) . . . . ?
C4 C6 C8 C7 112.5(3) . . . . ?
C4 C6A C7A C8A 105.9(6) . . . . ?
C4 C6A C8A C7A -105.6(6) . . . . ?
C5 C1 C2 C3 4.6(2) . . . . ?
C5 C4 C6 C7 -166.8(2) . . . . ?
C5 C4 C6 C8 123.8(3) . . . . ?
C5 C4 C6A C7A -39.6(8) . . . . ?
C5 C4 C6A C8A 26.5(9) . . . . ?
C6 C4 C5 C1 178.90(19) . . . . ?
C6 C4 C5 S1 1.4(3) . . . . ?
C6 C4 C5 S1A 4.4(3) . . . . ?
C6A C4 C5 C1 178.0(5) . . . . ?
C6A C4 C5 S1 0.5(6) . . . . ?
C6A C4 C5 S1A 3.6(6) . . . . ?
C9 C3 C4 C5 129.10(19) . . . . ?
C9 C3 C4 C6 -53.1(3) . . . . ?
C9 C3 C4 C6A -51.4(3) . . . . ?
C9 C3 C15 C10 11.9(2) . . . . ?
C9 C3 C15 C14 -167.4(2) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C10 C15 C3 178.9(2) . . . . ?
C11 C10 C15 C14 -1.8(3) . . . . ?
C11 C10 N1 C9 167.8(3) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C3 179.6(2) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C15 C3 C4 C5 -116.9(2) . . . . ?
C15 C3 C4 C6 60.9(3) . . . . ?
C15 C3 C4 C6A 62.6(3) . . . . ?
C15 C3 C9 N1 -19.4(3) . . . . ?
C15 C10 C11 C12 1.9(3) . . . . ?
C15 C10 N1 C9 -14.2(3) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C16 S1 C5 -3.9(3) . . . . ?
C17 C16 S1A C5 26.0(5) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C21 C16 C17 C18 -0.5(3) . . . . ?
C21 C16 S1 C5 179.13(19) . . . . ?
C21 C16 S1A C5 -167.7(3) . . . . ?
N1 C10 C11 C12 179.8(2) . . . . ?
N1 C10 C15 C3 0.6(3) . . . . ?
N1 C10 C15 C14 180.0(2) . . . . ?
O1 C1 C2 C3 -176.1(2) . . . . ?
O1 C1 C5 C4 179.6(2) . . . . ?
O1 C1 C5 S1 -2.5(3) . . . . ?
O1 C1 C5 S1A -7.1(4) . . . . ?
S1 C5 S1A C16 79.6(7) . . . . ?
S1 C16 C17 C18 -177.2(2) . . . . ?
S1 C16 C21 C20 177.3(2) . . . . ?
S1 C16 S1A C5 -93.0(7) . . . . ?
S1A C5 S1 C16 -80.3(6) . . . . ?
S1A C16 C17 C18 165.8(3) . . . . ?
S1A C16 C21 C20 -166.2(3) . . . . ?
S1A C16 S1 C5 66.5(6) . . . . ?

_olex2_date_sample_data_collection 2019-01-21
_olex2_date_sample_submission    2019-01-21
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id heh-APG-84
_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 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.798
####################################################################### 
# 
# 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_rjkt1907
_database_code_depnum_ccdc_archive 'CCDC 1945620'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;Department of Chemistry, University of York
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_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         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H13 N1 O1'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh260'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.42288(17)
_cell_length_b                   8.41061(12)
_cell_length_c                   28.0872(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.4536(13)
_cell_angle_gamma                90
_cell_volume                     2653.65(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.8250
_cell_measurement_theta_min      4.5920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (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    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0663
0 -1 0 0.0612
1 0 -2 0.0588
-2 0 1 0.0897
0 0 1 0.0426
0 0 -1 0.0361
-1 -2 5 0.0653
-1 1 0 0.0867

_exptl_crystal_recrystallization_method 
'crystallisation from dichloromethane/hexane'
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.079
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
0.0000 1.0000 0.0000 -0.0934 -0.1554 0.0266
-0.0000 -1.0000 -0.0000 0.0934 0.1554 -0.0266
0.9999 0.0001 -1.9997 -0.0566 0.0578 0.1384
-1.9999 -0.0003 0.9995 -0.0290 -0.0283 -0.2668
0.0000 0.0000 1.0000 0.0474 -0.0291 -0.0033
-0.0000 -0.0000 -1.0000 -0.0474 0.0291 0.0033
-0.9999 -2.0002 4.9995 0.3857 0.1656 -0.2016
-1.0000 0.9999 -0.0002 -0.1316 -0.1550 -0.1051

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.048
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         3.935
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  20.00   1.00    1.00    --    0.00  37.00  60.00   45
  2  ω     42.00  68.00   1.00    1.00    --    0.00  37.00  60.00   26
  3  ω    -13.00  26.00   1.00    1.00    --    0.00  57.00-180.00   39
  4  ω     39.00  66.00   1.00    1.00    --    0.00  57.00-180.00   27
  5  ω     49.00  86.00   1.00    2.00    --   54.00  57.00-120.00   37
  6  ω     -9.00  83.00   1.00    2.00    --   54.00 -77.00   0.00   92
  7  ω     28.00 120.00   1.00    2.00    --   54.00  77.00 120.00   92
  8  ω     73.00 126.00   1.00    2.00    --   54.00  37.00-150.00   53
  9  ω     97.00 127.00   1.00    4.00    --  108.00 161.00-106.00   30
 10  ω     82.00 177.00   1.00    4.00    --  108.00  37.00-150.00   95
 11  ω     36.00 146.00   1.00    4.00    --  108.00 -91.00   0.00  110
 12  ω     87.00 168.00   1.00    4.00    --  108.00  63.00 120.00   81
 13  ω     74.00 126.00   1.00    4.00    --  108.00 -63.00 120.00   52
 14  ω    135.00 160.00   1.00    4.00    --  108.00 161.00-106.00   25
 15  ω    141.00 178.00   1.00    4.00    --  108.00 111.00  30.00   37
 16  ω    122.00 176.00   1.00    4.00    --  108.00  63.00 150.00   54
 17  ω     73.00 115.00   1.00    4.00    --  108.00 178.00-180.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382430000
_diffrn_orient_matrix_UB_12      -0.0933793000
_diffrn_orient_matrix_UB_13      0.0474352000
_diffrn_orient_matrix_UB_21      -0.0003485000
_diffrn_orient_matrix_UB_22      -0.1553655000
_diffrn_orient_matrix_UB_23      -0.0291016000
_diffrn_orient_matrix_UB_31      0.1317303000
_diffrn_orient_matrix_UB_32      0.0266480000
_diffrn_orient_matrix_UB_33      -0.0033158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4079
_reflns_number_total             4722
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00071(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.057
_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)+(0.0371P)²+0.7948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0858
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C1(H1A), C26(H26), C18(H18), C8(H8), C25(H25), C23(H23), C14(H14),
 C5(H5), C24(H24), C17(H17), C36(H36), C6(H6), C7(H7), C16(H16), C32(H32),
 C15(H15), C35(H35), C33(H33), C34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.86095(8) 0.94377(11) 0.51749(3) 0.0255(2) Uani 1 1 d . . . . .
O1 O 0.67018(8) 0.43982(11) 0.52501(3) 0.0268(2) Uani 1 1 d . . . . .
N2 N 0.46916(9) 0.76408(13) 0.42387(4) 0.0208(2) Uani 1 1 d . . . . .
N1 N 0.96340(9) 0.26291(13) 0.42578(4) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.80710(10) 0.40141(15) 0.38668(4) 0.0181(3) Uani 1 1 d . . . . .
C20 C 0.61701(10) 0.94334(14) 0.43208(4) 0.0170(2) Uani 1 1 d . . . . .
C21 C 0.58912(10) 0.89560(14) 0.38233(4) 0.0179(2) Uani 1 1 d . . . . .
C2 C 0.82704(10) 0.44430(14) 0.43684(4) 0.0167(2) Uani 1 1 d . . . . .
C19 C 0.54191(10) 0.86013(14) 0.45567(4) 0.0188(3) Uani 1 1 d . . . . .
H19 H 0.540502 0.867752 0.488592 0.023 Uiso 1 1 calc R . . . .
C28 C 0.82593(10) 0.96083(14) 0.47397(4) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.66092(11) 0.46039(14) 0.48139(5) 0.0194(3) Uani 1 1 d . . . . .
C22 C 0.49643(10) 0.78239(15) 0.37851(4) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.89436(10) 0.28728(15) 0.38100(4) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.92181(10) 0.35628(14) 0.45905(4) 0.0186(3) Uani 1 1 d . . . . .
H1A H 0.953504 0.359281 0.491960 0.022 Uiso 1 1 calc R . . . .
C27 C 0.71480(10) 1.05436(14) 0.45463(4) 0.0192(3) Uani 1 1 d . . . . .
H27A H 0.689822 1.113109 0.480773 0.023 Uiso 1 1 calc R . . . .
H27B H 0.731173 1.130087 0.430623 0.023 Uiso 1 1 calc R . . . .
C13 C 0.40020(11) 0.23537(15) 0.38686(5) 0.0210(3) Uani 1 1 d . . . . .
C11 C 0.56569(11) 0.38749(15) 0.44739(5) 0.0207(3) Uani 1 1 d . . . . .
C31 C 0.99024(11) 0.72956(15) 0.37667(5) 0.0223(3) Uani 1 1 d . . . . .
C26 C 0.63324(11) 0.93853(16) 0.34054(4) 0.0224(3) Uani 1 1 d . . . . .
H26 H 0.693072 1.014327 0.342011 0.027 Uiso 1 1 calc R . . . .
C9 C 0.75204(11) 0.55540(14) 0.46066(5) 0.0199(3) Uani 1 1 d . . . . .
H9A H 0.712156 0.631057 0.437098 0.024 Uiso 1 1 calc R . . . .
H9B H 0.802202 0.614138 0.486287 0.024 Uiso 1 1 calc R . . . .
C12 C 0.48953(11) 0.32058(15) 0.41937(5) 0.0209(3) Uani 1 1 d . . . . .
C30 C 0.93345(10) 0.81580(15) 0.41006(5) 0.0210(3) Uani 1 1 d . . . . .
C29 C 0.88626(11) 0.88490(15) 0.43897(5) 0.0206(3) Uani 1 1 d . . . . .
C18 C 0.31445(11) 0.14657(16) 0.40488(5) 0.0242(3) Uani 1 1 d . . . . .
H18 H 0.312563 0.147982 0.437840 0.029 Uiso 1 1 calc R . . . .
C8 C 0.72379(11) 0.44882(16) 0.34619(5) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.665993 0.524252 0.349124 0.028 Uiso 1 1 calc R . . . .
C25 C 0.58596(12) 0.86593(17) 0.29738(5) 0.0278(3) Uani 1 1 d . . . . .
H25 H 0.614479 0.893452 0.269510 0.033 Uiso 1 1 calc R . . . .
C23 C 0.44871(11) 0.70892(16) 0.33461(5) 0.0256(3) Uani 1 1 d . . . . .
H23 H 0.387773 0.634524 0.332577 0.031 Uiso 1 1 calc R . . . .
C14 C 0.39994(12) 0.23571(16) 0.33705(5) 0.0272(3) Uani 1 1 d . . . . .
H14 H 0.455915 0.295440 0.324590 0.033 Uiso 1 1 calc R . . . .
C5 C 0.90018(12) 0.21996(17) 0.33607(5) 0.0271(3) Uani 1 1 d . . . . .
H5 H 0.958258 0.145517 0.332620 0.033 Uiso 1 1 calc R . . . .
C24 C 0.49540(12) 0.75097(17) 0.29453(5) 0.0285(3) Uani 1 1 d . . . . .
H24 H 0.466531 0.702451 0.264973 0.034 Uiso 1 1 calc R . . . .
C17 C 0.23247(12) 0.05668(17) 0.37392(5) 0.0285(3) Uani 1 1 d . . . . .
H17 H 0.176429 -0.003533 0.386181 0.034 Uiso 1 1 calc R . . . .
C36 C 1.09006(12) 0.63636(17) 0.39368(5) 0.0288(3) Uani 1 1 d . . . . .
H36 H 1.122000 0.634492 0.426580 0.035 Uiso 1 1 calc R . . . .
C6 C 0.81647(13) 0.26809(18) 0.29700(5) 0.0319(3) Uani 1 1 d . . . . .
H6 H 0.817780 0.224567 0.266661 0.038 Uiso 1 1 calc R . . . .
C7 C 0.72933(12) 0.38141(18) 0.30205(5) 0.0303(3) Uani 1 1 d . . . . .
H7 H 0.674197 0.411516 0.274983 0.036 Uiso 1 1 calc R . . . .
C16 C 0.23347(12) 0.05594(17) 0.32482(5) 0.0309(3) Uani 1 1 d . . . . .
H16 H 0.178713 -0.005546 0.304114 0.037 Uiso 1 1 calc R . . . .
C32 C 0.94448(12) 0.73390(19) 0.32721(5) 0.0327(3) Uani 1 1 d . . . . .
H32 H 0.878340 0.796378 0.315505 0.039 Uiso 1 1 calc R . . . .
C15 C 0.31637(13) 0.14715(18) 0.30639(5) 0.0326(3) Uani 1 1 d . . . . .
H15 H 0.315599 0.148595 0.273224 0.039 Uiso 1 1 calc R . . . .
C35 C 1.14161(14) 0.54678(18) 0.36176(6) 0.0372(4) Uani 1 1 d . . . . .
H35 H 1.207555 0.483729 0.373278 0.045 Uiso 1 1 calc R . . . .
C33 C 0.99764(14) 0.6451(2) 0.29556(6) 0.0426(4) Uani 1 1 d . . . . .
H33 H 0.967563 0.648706 0.262506 0.051 Uiso 1 1 calc R . . . .
C34 C 1.09546(14) 0.55068(19) 0.31288(6) 0.0412(4) Uani 1 1 d . . . . .
H34 H 1.130093 0.489836 0.291506 0.049 Uiso 1 1 calc R . . . .
H2 H 0.4189(13) 0.6972(19) 0.4332(5) 0.027(4) Uiso 1 1 d . . . . .
H1 H 1.0212(15) 0.192(2) 0.4336(6) 0.036(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C28 1.2237(15) . ?
O1 C10 1.2228(15) . ?
N2 C19 1.3680(16) . ?
N2 C22 1.3742(16) . ?
N1 C4 1.3733(16) . ?
N1 C1 1.3698(16) . ?
C3 C2 1.4319(17) . ?
C3 C4 1.4135(17) . ?
C3 C8 1.4018(17) . ?
C20 C21 1.4328(16) . ?
C20 C19 1.3679(17) . ?
C20 C27 1.5047(16) . ?
C21 C22 1.4135(17) . ?
C21 C26 1.4061(17) . ?
C2 C1 1.3652(17) . ?
C2 C9 1.5043(16) . ?
C28 C27 1.5084(16) . ?
C28 C29 1.4473(17) . ?
C10 C11 1.4472(18) . ?
C10 C9 1.5103(16) . ?
C22 C23 1.3982(18) . ?
C4 C5 1.3956(18) . ?
C13 C12 1.4320(18) . ?
C13 C18 1.3976(18) . ?
C13 C14 1.3983(18) . ?
C11 C12 1.2018(18) . ?
C31 C30 1.4308(18) . ?
C31 C36 1.3947(19) . ?
C31 C32 1.3930(19) . ?
C26 C25 1.3772(19) . ?
C30 C29 1.2028(19) . ?
C18 C17 1.3818(19) . ?
C8 C7 1.375(2) . ?
C25 C24 1.408(2) . ?
C23 C24 1.377(2) . ?
C14 C15 1.382(2) . ?
C5 C6 1.379(2) . ?
C17 C16 1.381(2) . ?
C36 C35 1.382(2) . ?
C6 C7 1.404(2) . ?
C16 C15 1.390(2) . ?
C32 C33 1.383(2) . ?
C35 C34 1.379(2) . ?
C33 C34 1.385(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N2 C22 109.03(10) . . ?
C1 N1 C4 109.05(10) . . ?
C4 C3 C2 107.01(10) . . ?
C8 C3 C2 133.62(12) . . ?
C8 C3 C4 119.37(11) . . ?
C21 C20 C27 126.95(11) . . ?
C19 C20 C21 106.32(11) . . ?
C19 C20 C27 126.62(11) . . ?
C22 C21 C20 107.09(10) . . ?
C26 C21 C20 133.80(12) . . ?
C26 C21 C22 119.11(11) . . ?
C3 C2 C9 126.32(11) . . ?
C1 C2 C3 106.52(11) . . ?
C1 C2 C9 127.01(11) . . ?
C20 C19 N2 110.24(11) . . ?
O2 C28 C27 121.47(11) . . ?
O2 C28 C29 121.14(11) . . ?
C29 C28 C27 117.31(10) . . ?
O1 C10 C11 121.28(11) . . ?
O1 C10 C9 121.39(11) . . ?
C11 C10 C9 117.24(11) . . ?
N2 C22 C21 107.32(11) . . ?
N2 C22 C23 130.57(12) . . ?
C23 C22 C21 122.11(12) . . ?
N1 C4 C3 107.31(11) . . ?
N1 C4 C5 130.84(12) . . ?
C5 C4 C3 121.85(12) . . ?
C2 C1 N1 110.10(11) . . ?
C20 C27 C28 109.87(10) . . ?
C18 C13 C12 120.10(11) . . ?
C18 C13 C14 119.28(12) . . ?
C14 C13 C12 120.59(12) . . ?
C12 C11 C10 177.00(13) . . ?
C36 C31 C30 120.00(12) . . ?
C32 C31 C30 120.50(12) . . ?
C32 C31 C36 119.47(13) . . ?
C25 C26 C21 118.58(12) . . ?
C2 C9 C10 109.31(10) . . ?
C11 C12 C13 177.87(14) . . ?
C29 C30 C31 178.24(14) . . ?
C30 C29 C28 177.08(13) . . ?
C17 C18 C13 120.26(12) . . ?
C7 C8 C3 118.59(13) . . ?
C26 C25 C24 121.43(12) . . ?
C24 C23 C22 117.43(13) . . ?
C15 C14 C13 119.88(13) . . ?
C6 C5 C4 117.42(13) . . ?
C23 C24 C25 121.31(12) . . ?
C16 C17 C18 120.23(13) . . ?
C35 C36 C31 120.15(14) . . ?
C5 C6 C7 121.39(13) . . ?
C8 C7 C6 121.37(13) . . ?
C17 C16 C15 119.94(13) . . ?
C33 C32 C31 119.85(14) . . ?
C14 C15 C16 120.38(13) . . ?
C34 C35 C36 120.14(15) . . ?
C32 C33 C34 120.27(15) . . ?
C35 C34 C33 120.11(14) . . ?

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 0.877(16) 2.044(16) 2.8922(14) 162.6(14) 3_666 yes
N1 H1 O2 0.889(17) 2.080(17) 2.9028(14) 153.5(15) 3_766 yes

_olex2_date_sample_data_collection 2019-07-09
_olex2_date_sample_submission    2019-07-09
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id heh260
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.854
####################################################################### 
# 
# 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_rjkt1805
_database_code_depnum_ccdc_archive 'CCDC 1945660'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwoord'
;Department of Chemistry, University of York
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-07
_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         'C24 H19 N O S'
_chemical_formula_sum            'C24 H19 N O S'
_chemical_formula_weight         369.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H19 N1 O1 S1'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh-APG-47A'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.81156(11)
_cell_length_b                   17.5470(3)
_cell_length_c                   18.1227(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1848.07(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4053
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.7680
_cell_measurement_theta_min      4.8680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.649
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0176
0 1 0 0.0176
0 0 1 0.0489
0 0 -1 0.0221
1 0 -1 0.0689
-1 0 5 0.0526
3 0 5 0.0806
-4 1 -3 0.0750

_exptl_crystal_recrystallization_method 'From dichloromethane/hexane'
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.035
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
0.0000 -1.0001 -0.0001 0.0250 0.0839 0.0056
-0.0000 1.0001 0.0001 -0.0250 -0.0839 -0.0056
0.0001 -0.0002 0.9999 0.0676 -0.0167 -0.0488
-0.0001 0.0002 -0.9999 -0.0676 0.0167 0.0488
1.0000 -0.0002 -1.0004 0.0747 -0.0397 0.2653
-0.9997 -0.0007 4.9998 0.1955 -0.0271 -0.4606
3.0004 -0.0025 4.9978 0.7647 -0.2525 0.4053
-4.0003 1.0025 -2.9974 -0.7969 0.1915 -0.7251

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6650
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.002
_diffrn_reflns_theta_max         67.002
_diffrn_reflns_theta_min         3.506
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  41.00   1.00    2.00    --    0.00  57.00  30.00   49
  2  ω      9.00  58.00   1.00    2.00    --    0.00  74.00  50.00   49
  3  ω     -7.00  83.00   1.00    8.00    --   54.00 -77.00  90.00   90
  4  ω     23.00  65.00   1.00    8.00    --   54.00-125.00  90.00   42
  5  ω     28.00 124.00   1.00    8.00    --   54.00  77.00-150.00   96
  6  ω     55.00 109.00   1.00    8.00    --   54.00-125.00 -90.00   54
  7  ω     38.00 109.00   1.00   16.00    --  108.00 -77.00  30.00   71
  8  ω     82.00 136.00   1.00   16.00    --  108.00  37.00 -90.00   54
  9  ω     46.00 129.00   1.00   16.00    --  108.00 -37.00  30.00   83
 10  ω     54.00 115.00   1.00   16.00    --  108.00 -50.00 120.00   61
 11  ω     38.00  88.00   1.00   16.00    --  108.00-111.00 -90.00   50
 12  ω     57.00 110.00   1.00   16.00    --  108.00-111.00 -30.00   53
 13  ω     87.00 149.00   1.00   16.00    --  108.00  63.00 -30.00   62
 14  ω    127.00 153.00   1.00   16.00    --  108.00 111.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1423156000
_diffrn_orient_matrix_UB_12      -0.0250005000
_diffrn_orient_matrix_UB_13      0.0675627000
_diffrn_orient_matrix_UB_21      -0.0563949000
_diffrn_orient_matrix_UB_22      -0.0839347000
_diffrn_orient_matrix_UB_23      -0.0167141000
_diffrn_orient_matrix_UB_31      0.2164658000
_diffrn_orient_matrix_UB_32      -0.0056049000
_diffrn_orient_matrix_UB_33      -0.0488501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3120
_reflns_number_total             3220
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1220 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(10)
_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     248
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.046
_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)+(0.0327P)²+0.3713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6749(4) 0.31202(12) 0.23041(12) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.8196(4) 0.25345(12) 0.26631(12) 0.0176(5) Uani 1 1 d . . . . .
C3 C 0.7415(4) 0.24786(12) 0.34570(12) 0.0178(5) Uani 1 1 d . . . . .
H3A H 0.872417 0.248804 0.378871 0.021 Uiso 1 1 calc R . . . .
H3B H 0.656012 0.201118 0.353828 0.021 Uiso 1 1 calc R . . . .
C4 C 0.5855(4) 0.31841(12) 0.35838(12) 0.0155(4) Uani 1 1 d . . . . .
C5 C 0.5502(4) 0.35073(12) 0.28063(12) 0.0152(5) Uani 1 1 d . . . . .
C6 C 0.3557(4) 0.29793(14) 0.39647(12) 0.0197(5) Uani 1 1 d . . . . .
H6A H 0.235279 0.333396 0.382545 0.024 Uiso 1 1 calc R . . . .
H6B H 0.307657 0.246658 0.383713 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6934(4) 0.37096(12) 0.41589(11) 0.0165(4) Uani 1 1 d . . . . .
C8 C 0.8796(4) 0.41864(13) 0.41103(13) 0.0200(5) Uani 1 1 d . . . . .
H8 H 0.950145 0.427593 0.365782 0.024 Uiso 1 1 calc R . . . .
C9 C 0.9620(5) 0.45362(14) 0.47517(16) 0.0277(6) Uani 1 1 d . . . . .
H9 H 1.090003 0.485355 0.472917 0.033 Uiso 1 1 calc R . . . .
C10 C 0.8529(5) 0.44099(14) 0.54213(14) 0.0302(6) Uani 1 1 d . . . . .
H10 H 0.909488 0.464254 0.584517 0.036 Uiso 1 1 calc R . . . .
C11 C 0.6597(5) 0.39402(14) 0.54708(13) 0.0275(6) Uani 1 1 d . . . . .
H11 H 0.584625 0.386859 0.591862 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5825(4) 0.35823(13) 0.48332(13) 0.0214(5) Uani 1 1 d . . . . .
C13 C 0.3925(4) 0.41519(13) 0.26563(12) 0.0165(4) Uani 1 1 d . . . . .
C14 C 0.2251(4) 0.40888(13) 0.21061(13) 0.0213(5) Uani 1 1 d . . . . .
H14 H 0.214386 0.364325 0.183044 0.026 Uiso 1 1 calc R . . . .
C15 C 0.0748(5) 0.46869(14) 0.19684(14) 0.0260(6) Uani 1 1 d . . . . .
H15 H -0.035487 0.463928 0.159946 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0876(5) 0.53552(14) 0.23760(14) 0.0249(5) Uani 1 1 d . . . . .
H16 H -0.013916 0.575379 0.228348 0.030 Uiso 1 1 calc R . . . .
C17 C 0.2529(5) 0.54218(13) 0.29214(13) 0.0244(5) Uani 1 1 d . . . . .
H17 H 0.263416 0.587025 0.319288 0.029 Uiso 1 1 calc R . . . .
C18 C 0.4030(4) 0.48275(13) 0.30672(13) 0.0202(5) Uani 1 1 d . . . . .
H18 H 0.511635 0.487718 0.344095 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6217(4) 0.23841(12) 0.09966(12) 0.0165(5) Uani 1 1 d . . . . .
C20 C 0.4153(4) 0.20382(13) 0.11927(12) 0.0196(5) Uani 1 1 d . . . . .
H20 H 0.320816 0.225842 0.154781 0.024 Uiso 1 1 calc R . . . .
C21 C 0.3517(4) 0.13620(13) 0.08539(13) 0.0216(5) Uani 1 1 d . . . . .
H21 H 0.215188 0.112331 0.098879 0.026 Uiso 1 1 calc R . . . .
C22 C 0.4906(5) 0.10385(14) 0.03142(13) 0.0231(5) Uani 1 1 d . . . . .
H22 H 0.446027 0.058896 0.008293 0.028 Uiso 1 1 calc R . . . .
C23 C 0.6961(5) 0.13892(13) 0.01217(12) 0.0211(5) Uani 1 1 d . . . . .
H23 H 0.789077 0.117537 -0.024120 0.025 Uiso 1 1 calc R . . . .
C24 C 0.7633(4) 0.20578(13) 0.04692(12) 0.0180(5) Uani 1 1 d . . . . .
H24 H 0.902762 0.228586 0.034848 0.022 Uiso 1 1 calc R . . . .
N1 N 0.4080(4) 0.30385(12) 0.47546(11) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.289(6) 0.3105(19) 0.5029(19) 0.044(9) Uiso 1 1 d . . . . .
O1 O 0.9762(3) 0.21771(10) 0.23862(9) 0.0246(4) Uani 1 1 d . . . . .
S1 S 0.70125(10) 0.32960(3) 0.13533(3) 0.01984(14) 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
C1 C2 1.479(3) . ?
C1 C5 1.347(3) . ?
C1 S1 1.757(2) . ?
C2 C3 1.512(3) . ?
C2 O1 1.214(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.552(3) . ?
C4 C5 1.533(3) . ?
C4 C6 1.545(3) . ?
C4 C7 1.527(3) . ?
C5 C13 1.481(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.467(3) . ?
C7 C8 1.371(3) . ?
C7 C12 1.400(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(3) . ?
C12 N1 1.399(3) . ?
C13 C14 1.397(3) . ?
C13 C18 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(3) . ?
C19 C24 1.385(3) . ?
C19 S1 1.787(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(3) . ?
C24 H24 0.9300 . ?
N1 H1 0.86(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
C2 C1 S1 120.27(17) . . ?
C5 C1 C2 111.04(19) . . ?
C5 C1 S1 128.37(17) . . ?
C1 C2 C3 107.05(19) . . ?
O1 C2 C1 127.1(2) . . ?
O1 C2 C3 125.8(2) . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C2 C3 C4 105.34(18) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C5 C4 C3 103.73(17) . . ?
C5 C4 C6 112.40(18) . . ?
C6 C4 C3 112.67(18) . . ?
C7 C4 C3 110.05(18) . . ?
C7 C4 C5 117.34(18) . . ?
C7 C4 C6 100.99(18) . . ?
C1 C5 C4 111.25(19) . . ?
C1 C5 C13 126.4(2) . . ?
C13 C5 C4 122.29(19) . . ?
C4 C6 H6A 111.0 . . ?
C4 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
N1 C6 C4 103.91(18) . . ?
N1 C6 H6A 111.0 . . ?
N1 C6 H6B 111.0 . . ?
C8 C7 C4 130.5(2) . . ?
C8 C7 C12 121.1(2) . . ?
C12 C7 C4 108.1(2) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 N1 128.8(2) . . ?
N1 C12 C7 110.7(2) . . ?
C14 C13 C5 120.1(2) . . ?
C14 C13 C18 118.5(2) . . ?
C18 C13 C5 121.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(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 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.7 . . ?
C20 C19 S1 121.43(18) . . ?
C24 C19 C20 120.6(2) . . ?
C24 C19 S1 117.80(17) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 119.7(2) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C6 N1 H1 114(2) . . ?
C12 N1 C6 107.32(19) . . ?
C12 N1 H1 116(2) . . ?
C1 S1 C19 100.08(10) . . ?

_olex2_date_sample_data_collection 2018-12-05
_olex2_date_sample_submission    2018-11-28
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id heh-AIG47
_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 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.893
####################################################################### 
# 
# 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_rjkt1905
_database_code_depnum_ccdc_archive 'CCDC 1945621'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;Department of Chemistry, University of York
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-17
_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         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H15 N1 O1'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh-JPA-569P'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.42250(12)
_cell_length_b                   9.90594(16)
_cell_length_c                   19.5109(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1434.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6762
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      70.9330
_cell_measurement_theta_min      4.5240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0520
0 0 1 0.0390
4 3 -4 0.1020
4 -3 4 0.0831
0 -5 4 0.0624
-1 -5 4 0.0640
-5 0 2 0.1029
-2 5 -4 0.0814
3 1 5 0.0778
-2 2 5 0.0791
-1 -5 1 0.0672
2 -5 -4 0.1003
-1 -2 -5 0.0717
-3 0 -5 0.0866
-1 5 3 0.1010
-1 0 5 0.0602

_exptl_crystal_recrystallization_method 
'crystallisation from dichloromethane/hexane'
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.091
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
0.0001 0.0002 -0.9996 -0.0741 0.0089 0.0256
-0.0001 -0.0002 0.9996 0.0741 -0.0089 -0.0256
4.0020 3.0007 -3.9910 0.0162 0.0481 1.0018
4.0014 -3.0004 4.0037 0.5423 0.7793 0.3249
-0.0001 -5.0003 3.9967 0.2407 0.6330 -0.4957
-1.0006 -5.0004 3.9951 0.1709 0.5296 -0.6616
-5.0024 -0.0006 1.9912 -0.2008 -0.5349 -0.8805
-2.0007 5.0003 -3.9999 -0.3803 -0.8399 0.1640
3.0006 0.9989 5.0029 0.5913 0.1321 0.4479
-2.0016 1.9987 4.9952 0.2534 -0.5187 -0.3027
-1.0002 -4.9997 0.9964 -0.0515 0.5563 -0.5846
2.0017 -4.9986 -3.9966 -0.2128 0.9110 0.0412
-0.9997 -1.9988 -5.0000 -0.4629 0.2085 -0.1949
-3.0006 0.0010 -5.0026 -0.5801 -0.2658 -0.3693
-1.0012 4.9988 2.9986 0.2085 -0.7987 0.1503
-1.0010 -0.0011 4.9962 0.3009 -0.1479 -0.2941

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11327
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.058
_diffrn_reflns_theta_max         67.058
_diffrn_reflns_theta_min         4.532
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  69.00   1.00    1.00    --    0.00  57.00  60.00   52
  2  ω    -61.00 -20.00   1.00    1.00    --    0.00 -57.00 -60.00   41
  3  ω     53.00  94.00   1.00    1.50    --   54.00  57.00 -90.00   41
  4  ω    -15.00  73.00   1.00    1.50    --   54.00 -57.00  60.00   88
  5  ω     28.00 112.00   1.00    1.50    --   54.00  37.00-120.00   84
  6  ω     45.00 121.00   1.00    1.50    --   54.00  57.00 -30.00   76
  7  ω     86.00 177.00   1.00    2.00    --  108.00  50.00 -60.00   91
  8  ω     68.00 135.00   1.00    2.00    --  108.00 178.00-150.00   67
  9  ω     41.00 130.00   1.00    2.00    --  108.00 -63.00 150.00   89
 10  ω     58.00 110.00   1.00    2.00    --  108.00 178.00-180.00   52
 11  ω    117.00 149.00   1.00    2.00    --  108.00 178.00-180.00   32
 12  ω     36.00 113.00   1.00    2.00    --  108.00-111.00-180.00   77
 13  ω    112.00 160.00   1.00    2.00    --  108.00  12.00  90.00   48
 14  ω    -35.00  11.00   1.00    1.00    --    0.00  99.00  46.00   46
 15  ω     23.00  68.00   1.00    1.50    --   54.40-125.00   0.00   45
 16  ω     24.00  84.00   1.00    1.50    --   54.40  77.00  30.00   60
 17  ω     14.00  40.00   1.00    1.50    --   54.40  19.00-180.00   26
 18  ω     85.00 114.00   1.00    1.50    --   54.40  19.00-180.00   29
 19  ω    -19.00  58.00   1.00    1.50    --   54.40   0.00 150.00   77
 20  ω    129.00 173.00   1.00    2.00    --  108.00 -12.00 -90.00   44
 21  ω     80.00 161.00   1.00    2.00    --  108.00  77.00 -30.00   81
 22  ω     78.00 104.00   1.00    2.00    --  108.00  77.00  60.00   26
 23  ω     86.00 112.00   1.00    2.00    --  108.00  63.00  90.00   26
 24  ω    129.00 155.00   1.00    2.00    --  108.00  63.00  90.00   26
 25  ω     79.00 105.00   1.00    2.00    --  108.00  77.00  30.00   26
 26  ω    142.00 168.00   1.00    2.00    --  108.00  77.00  30.00   26
 27  ω     78.00 104.00   1.00    2.00    --  108.00  77.00   0.00   26
 28  ω    120.00 170.00   1.00    2.00    --  108.00  77.00   0.00   50
 29  ω     84.00 110.00   1.00    2.00    --  108.00  37.00  30.00   26
 30  ω    146.00 171.00   1.00    2.00    --  108.00  37.00  30.00   25
 31  ω     86.00 112.00   1.00    2.00    --  108.00  63.00  30.00   26
 32  ω     84.00 110.00   1.00    2.00    --  108.00  37.00  90.00   26
 33  ω     86.00 120.00   1.00    2.00    --  108.00  63.00  60.00   34
 34  ω     95.00 121.00   1.00    2.00    --  108.00  50.00  90.00   26
 35  ω     86.00 118.00   1.00    2.00    --  108.00  50.00 120.00   32
 36  ω     94.00 120.00   1.00    2.00    --  108.00  50.00  30.00   26
 37  ω     95.00 121.00   1.00    2.00    --  108.00  50.00  60.00   26
 38  ω     82.00 108.00   1.00    2.00    --  108.00  37.00  60.00   26
 39  ω     85.00 111.00   1.00    2.00    --  108.00  43.00  29.76   26
 40  ω     78.00 103.00   1.00    2.00    --  108.00  77.00  56.79   25
 41  ω     79.00 104.00   1.00    2.00    --  108.00  76.00  79.73   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0696679000
_diffrn_orient_matrix_UB_12      0.0111551000
_diffrn_orient_matrix_UB_13      0.0741822000
_diffrn_orient_matrix_UB_21      0.1033955000
_diffrn_orient_matrix_UB_22      -0.1337223000
_diffrn_orient_matrix_UB_23      -0.0089103000
_diffrn_orient_matrix_UB_31      0.1658117000
_diffrn_orient_matrix_UB_32      0.0786523000
_diffrn_orient_matrix_UB_33      -0.0256210000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2471
_reflns_number_total             2565
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(11)
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.099
_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)+(0.0299P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0605
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2388(2) 0.63869(16) 0.69574(8) 0.0236(3) Uani 1 1 d . . . . .
H1 H 0.124893 0.644045 0.715377 0.028 Uiso 1 1 calc R . . . .
C2 C 0.3620(2) 0.54007(15) 0.70922(8) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.5181(2) 0.57083(16) 0.66916(8) 0.0218(3) Uani 1 1 d . . . . .
C4 C 0.6889(2) 0.51173(18) 0.66188(9) 0.0304(4) Uani 1 1 d . . . . .
H4 H 0.719127 0.434573 0.686486 0.036 Uiso 1 1 calc R . . . .
C5 C 0.8107(2) 0.5697(2) 0.61786(10) 0.0431(5) Uani 1 1 d . . . . .
H5 H 0.923723 0.530483 0.612522 0.052 Uiso 1 1 calc R . . . .
C6 C 0.7686(3) 0.6865(2) 0.58083(10) 0.0472(6) Uani 1 1 d . . . . .
H6 H 0.854045 0.723218 0.551368 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6027(3) 0.7485(2) 0.58714(9) 0.0398(5) Uani 1 1 d . . . . .
H7 H 0.574775 0.826335 0.562727 0.048 Uiso 1 1 calc R . . . .
C8 C 0.4787(2) 0.68913(16) 0.63175(8) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.3359(2) 0.42029(16) 0.75536(8) 0.0261(4) Uani 1 1 d . . . . .
H9A H 0.254445 0.443847 0.792343 0.031 Uiso 1 1 calc R . . . .
H9B H 0.450546 0.394466 0.775328 0.031 Uiso 1 1 calc R . . . .
C10 C 0.2594(2) 0.30327(15) 0.71517(8) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.3819(2) 0.23959(16) 0.66727(8) 0.0240(3) Uani 1 1 d . . . . .
C12 C 0.4943(2) 0.19659(15) 0.62854(8) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.6363(2) 0.14928(15) 0.58460(8) 0.0218(3) Uani 1 1 d . . . . .
C14 C 0.6004(2) 0.09524(16) 0.51994(8) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.482337 0.088510 0.504353 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7416(2) 0.05170(16) 0.47912(8) 0.0280(4) Uani 1 1 d . . . . .
H15 H 0.717651 0.015230 0.436146 0.034 Uiso 1 1 calc R . . . .
C16 C 0.9180(2) 0.06194(17) 0.50166(8) 0.0266(4) Uani 1 1 d . . . . .
H16 H 1.011972 0.032540 0.473912 0.032 Uiso 1 1 calc R . . . .
C17 C 0.9540(2) 0.11622(17) 0.56579(9) 0.0261(4) Uani 1 1 d . . . . .
H17 H 1.072389 0.123280 0.580955 0.031 Uiso 1 1 calc R . . . .
C18 C 0.8145(2) 0.15983(15) 0.60723(8) 0.0243(3) Uani 1 1 d . . . . .
H18 H 0.839244 0.196187 0.650160 0.029 Uiso 1 1 calc R . . . .
C19 C 0.2157(3) 0.84964(17) 0.62488(10) 0.0422(5) Uani 1 1 d . . . . .
H19A H 0.284670 0.927873 0.637280 0.063 Uiso 1 1 calc GR . . . .
H19B H 0.098394 0.855045 0.645457 0.063 Uiso 1 1 calc GR . . . .
H19C H 0.203526 0.845731 0.575931 0.063 Uiso 1 1 calc GR . . . .
N1 N 0.3070(2) 0.72899(14) 0.64903(7) 0.0278(3) Uani 1 1 d . . . . .
O1 O 0.10255(17) 0.26819(14) 0.72032(7) 0.0373(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
C1 H1 0.9300 . ?
C1 C2 1.363(2) . ?
C1 N1 1.374(2) . ?
C2 C3 1.430(2) . ?
C2 C9 1.502(2) . ?
C3 C4 1.404(2) . ?
C3 C8 1.411(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(2) . ?
C8 N1 1.376(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(2) . ?
C10 C11 1.449(2) . ?
C10 O1 1.219(2) . ?
C11 C12 1.203(2) . ?
C12 C13 1.437(2) . ?
C13 C14 1.396(2) . ?
C13 C18 1.399(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 N1 1.453(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 124.8 . . ?
C2 C1 N1 110.34(14) . . ?
N1 C1 H1 124.8 . . ?
C1 C2 C3 106.56(14) . . ?
C1 C2 C9 126.53(15) . . ?
C3 C2 C9 126.88(14) . . ?
C4 C3 C2 134.27(16) . . ?
C4 C3 C8 118.76(15) . . ?
C8 C3 C2 106.95(14) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.93(18) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.43(18) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.37(18) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.15(19) . . ?
C8 C7 H7 121.4 . . ?
C7 C8 C3 122.35(17) . . ?
N1 C8 C3 107.67(14) . . ?
N1 C8 C7 129.97(17) . . ?
C2 C9 H9A 109.6 . . ?
C2 C9 H9B 109.6 . . ?
C2 C9 C10 110.09(13) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C11 C10 C9 115.64(14) . . ?
O1 C10 C9 122.37(15) . . ?
O1 C10 C11 121.92(15) . . ?
C12 C11 C10 173.95(17) . . ?
C11 C12 C13 176.67(17) . . ?
C14 C13 C12 121.63(15) . . ?
C14 C13 C18 119.62(15) . . ?
C18 C13 C12 118.74(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.66(16) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.65(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.79(15) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.27(16) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.01(15) . . ?
C17 C18 H18 120.0 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
C1 N1 C8 108.47(14) . . ?
C1 N1 C19 125.39(15) . . ?
C8 N1 C19 126.07(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 177.87(16) . . . . ?
C1 C2 C3 C8 -0.80(17) . . . . ?
C1 C2 C9 C10 89.47(19) . . . . ?
C2 C1 N1 C8 -0.27(17) . . . . ?
C2 C1 N1 C19 -177.46(15) . . . . ?
C2 C3 C4 C5 -179.57(16) . . . . ?
C2 C3 C8 C7 179.73(14) . . . . ?
C2 C3 C8 N1 0.65(17) . . . . ?
C2 C9 C10 C11 71.25(17) . . . . ?
C2 C9 C10 O1 -105.63(18) . . . . ?
C3 C2 C9 C10 -88.36(19) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C8 N1 C1 -0.25(17) . . . . ?
C3 C8 N1 C19 176.92(15) . . . . ?
C4 C3 C8 C7 0.8(2) . . . . ?
C4 C3 C8 N1 -178.26(13) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C6 C7 C8 N1 178.72(16) . . . . ?
C7 C8 N1 C1 -179.25(16) . . . . ?
C7 C8 N1 C19 -2.1(3) . . . . ?
C8 C3 C4 C5 -1.0(2) . . . . ?
C9 C2 C3 C4 -4.0(3) . . . . ?
C9 C2 C3 C8 177.38(14) . . . . ?
C12 C13 C14 C15 179.57(15) . . . . ?
C12 C13 C18 C17 -179.44(15) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
N1 C1 C2 C3 0.66(17) . . . . ?
N1 C1 C2 C9 -177.52(14) . . . . ?

_olex2_date_sample_data_collection 2019-05-15
_olex2_date_sample_submission    2019-05-13
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id heh-jpa-569p
_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 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.864
####################################################################### 
# 
# 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_rjkt1804
_database_code_depnum_ccdc_archive 'CCDC 1945619'
loop_
_audit_author_name
_audit_author_address
'Adrian C. Whitwood'
;Department of Chemistry, University of York
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H21 N O S'
_chemical_formula_sum            'C25 H21 N O S'
_chemical_formula_weight         383.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H21 N O S'
_chemical_oxdiff_usercomment     'Hon Eong Ho heh-APG-37 (A)'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7543(5)
_cell_length_b                   9.9710(6)
_cell_length_c                   11.6327(6)
_cell_angle_alpha                81.846(4)
_cell_angle_beta                 74.281(5)
_cell_angle_gamma                81.076(5)
_cell_volume                     960.27(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7579
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      70.7950
_cell_measurement_theta_min      3.9550
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    1.605
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 5 0 0.1818
-5 1 3 0.1344
0 5 -2 0.2454
-1 -5 2 0.2386
4 1 -3 0.1396
3 -4 0 0.1654
3 2 5 0.0554
-2 -1 -5 0.1077
-4 -1 -5 0.0574
-5 -2 -5 0.0554
-5 -2 -2 0.0736
-5 1 -4 0.1094
-5 -1 -3 0.0795
5 2 2 0.0827
5 -2 4 0.1276
5 1 3 0.0726
1 -2 -5 0.1400
1 -5 -4 0.1516
1 4 -5 0.2251
-1 -3 5 0.2295
-1 2 5 0.1400
2 3 5 0.0660
-5 -4 -4 0.0935
1 0 0 0.0772
-3 -4 -6 0.1028
-3 -3 -7 0.0987
-5 -3 -5 0.0529

_exptl_crystal_recrystallization_method DCM/Et2O/hexane
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.124
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0000 5.0000 -0.0000 0.3804 -0.6570 0.6736
-5.0000 1.0000 2.9999 0.5641 -0.9619 -0.1344
0.0000 5.0000 -2.0000 0.0532 -0.0913 0.8540
-1.0000 -5.0000 2.0000 -0.0245 -0.0900 -0.8696
4.0000 1.0000 -3.0000 -0.4177 0.7354 0.4070
3.0000 -4.0000 0.0000 -0.3216 0.6344 -0.5295
3.0000 2.0000 5.0000 0.6348 0.4438 0.0005
-2.0000 -1.0000 -5.0000 -0.6046 -0.2852 0.1591
-4.0000 -1.0000 -5.0000 -0.5472 -0.6477 0.1280
-5.0000 -2.0000 -5.0000 -0.5774 -0.8064 -0.0317
-5.0000 -2.0000 -2.0000 -0.2156 -0.8393 -0.2323
-5.0000 1.0000 -4.0000 -0.2802 -0.8852 0.3337
-5.0000 -1.0000 -3.0000 -0.2773 -0.8509 -0.0213
5.0000 2.0000 2.0000 0.2156 0.8393 0.2323
5.0000 -2.0000 4.0000 0.2213 0.9079 -0.4777
5.0000 1.0000 3.0000 0.2773 0.8509 0.0213
1.0000 -2.0000 -5.0000 -0.7495 0.2813 0.0618
1.0000 -5.0000 -4.0000 -0.8055 0.3383 -0.4373
1.0000 4.0000 -5.0000 -0.3962 0.1455 0.9262
-1.0000 -3.0000 5.0000 0.4551 -0.1682 -0.7821
-1.0000 2.0000 5.0000 0.7495 -0.2813 -0.0618
2.0000 3.0000 5.0000 0.7223 0.2399 0.1290
-5.0000 -4.0000 -4.0000 -0.5746 -0.7721 -0.3867
1.0000 -0.0000 0.0000 -0.0287 0.1813 0.0156
-3.0000 -4.0000 -6.0000 -0.8732 -0.3876 -0.2218
-3.0000 -3.0000 -7.0000 -0.9349 -0.3993 -0.0108
-5.0000 -3.0000 -5.0000 -0.6363 -0.7838 -0.1757

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14054
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.048
_diffrn_reflns_theta_min         3.970
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  26.00   1.00    1.00    --    0.00 -37.00-120.00   98
  2  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00  30.00   90
  3  ω     23.00 111.00   1.00    1.00    --   54.00-125.00-180.00   88
  4  ω     28.00 126.00   1.00    1.00    --   54.00  37.00 -30.00   98
  5  ω     10.00 127.00   1.00    1.00    --   54.00  19.00 -90.00  117
  6  ω    -18.00  80.00   1.00    1.00    --   54.00 -37.00  90.00   98
  7  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00   0.00   90
  8  ω     33.00 123.00   1.00    1.00    --   54.00  57.00-120.00   90
  9  ω      1.00  96.00   1.00    1.00    --   54.00 -99.00 -30.00   95
 10  ω     36.00 113.00   1.00    1.00    --  108.00-111.00-150.00   77
 11  ω     86.00 176.00   1.00    1.00    --  108.00  63.00-150.00   90
 12  ω     86.00 176.00   1.00    1.00    --  108.00  63.00  90.00   90
 13  ω     40.00 130.00   1.00    1.00    --  108.00 -63.00 -60.00   90
 14  ω     40.00 130.00   1.00    1.00    --  108.00 -63.00-180.00   90
 15  ω     36.00 134.00   1.00    1.00    --  108.00 -37.00  90.00   98
 16  ω     36.00 113.00   1.00    1.00    --  108.00-111.00 -30.00   77
 17  ω     36.00 113.00   1.00    1.00    --  108.00-111.00  60.00   77
 18  ω     82.00 178.00   1.00    1.00    --  108.00  37.00 -90.00   96
 19  ω     38.00 130.00   1.00    1.00    --  108.00 -50.00  60.00   92
 20  ω     35.00 178.00   1.00    1.00    --  108.00 -12.00-120.00  143
 21  ω     36.00 113.00   1.00    1.00    --  108.00-111.00-180.00   77
 22  ω     36.00 113.00   1.00    1.00    --  108.00-111.00 120.00   77
 23  ω    -21.00  69.00   1.00    1.00    --    0.00  57.00-150.00   90
 24  ω    -69.00  21.00   1.00    1.00    --    0.00 -57.00 -30.00   90
 25  ω    -15.00  75.00   1.00    1.00    --   54.00 -57.00-150.00   90
 26  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 -30.00  100
 27  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-180.00  100
 28  ω     24.00 124.00   1.00    1.00    --   54.00  77.00  60.00  100
 29  ω     24.00 124.00   1.00    1.00    --   54.00  77.00-120.00  100
 30  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 -60.00  100
 31  ω     24.00 124.00   1.00    1.00    --   54.00  77.00 120.00  100
 32  ω     24.00 124.00   1.00    1.00    --   54.00  77.00   0.00  100
 33  ω     74.00 136.00   1.00    1.00    --  108.00  25.00-180.00   62
 34  ω     86.00 178.00   1.00    1.00    --  108.00  50.00  60.00   92
 35  ω     78.00 178.00   1.00    1.00    --  108.00  77.00 -60.00  100
 36  ω     74.00 178.00   1.00    1.00    --  108.00  25.00  30.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0286799000
_diffrn_orient_matrix_UB_12      0.0588785000
_diffrn_orient_matrix_UB_13      0.1206137000
_diffrn_orient_matrix_UB_21      0.1812858000
_diffrn_orient_matrix_UB_22      -0.0226316000
_diffrn_orient_matrix_UB_23      -0.0109531000
_diffrn_orient_matrix_UB_31      0.0155755000
_diffrn_orient_matrix_UB_32      0.1440618000
_diffrn_orient_matrix_UB_33      -0.0668677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3469
_reflns_number_total             3652
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.052
_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)+(0.0376P)²+0.4785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25449(15) 0.31659(13) 0.75800(11) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.15540(15) 0.36862(13) 0.87135(11) 0.0165(3) Uani 1 1 d . . . . .
C3 C 0.26236(15) 0.43460(14) 0.92298(11) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.2575 0.3960 1.0051 0.022 Uiso 1 1 calc R . . . .
H3B H 0.2296 0.5321 0.9223 0.022 Uiso 1 1 calc R . . . .
C4 C 0.43260(14) 0.40578(12) 0.84290(11) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.40904(15) 0.33474(12) 0.74028(11) 0.0142(2) Uani 1 1 d . . . . .
C6 C 0.54040(14) 0.28989(13) 0.63702(11) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.56224(15) 0.15315(13) 0.61364(12) 0.0185(3) Uani 1 1 d . . . . .
H7 H 0.4942 0.0931 0.6623 0.022 Uiso 1 1 calc R . . . .
C8 C 0.68408(16) 0.10619(14) 0.51892(12) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.6973 0.0152 0.5045 0.026 Uiso 1 1 calc R . . . .
C9 C 0.78611(16) 0.19471(15) 0.44590(12) 0.0232(3) Uani 1 1 d . . . . .
H9 H 0.8689 0.1631 0.3832 0.028 Uiso 1 1 calc R . . . .
C10 C 0.76405(16) 0.33067(15) 0.46683(12) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.8319 0.3903 0.4173 0.026 Uiso 1 1 calc R . . . .
C11 C 0.64159(15) 0.37888(14) 0.56108(11) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.6271 0.4706 0.5735 0.021 Uiso 1 1 calc R . . . .
C12 C 0.52445(15) 0.52702(13) 0.79144(11) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.47548(17) 0.65473(13) 0.74126(12) 0.0203(3) Uani 1 1 d . . . . .
H13 H 0.3680 0.6823 0.7449 0.024 Uiso 1 1 calc R . . . .
C14 C 0.59039(18) 0.74179(14) 0.68499(13) 0.0254(3) Uani 1 1 d . . . . .
H14 H 0.5598 0.8286 0.6510 0.030 Uiso 1 1 calc R . . . .
C15 C 0.75070(18) 0.69863(15) 0.67974(12) 0.0255(3) Uani 1 1 d . . . . .
H15 H 0.8264 0.7567 0.6401 0.031 Uiso 1 1 calc R . . . .
C16 C 0.80092(16) 0.57132(14) 0.73196(12) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.9083 0.5445 0.7295 0.025 Uiso 1 1 calc R . . . .
C17 C 0.68579(15) 0.48502(13) 0.78802(11) 0.0164(3) Uani 1 1 d . . . . .
C18 C 0.54910(15) 0.31874(13) 0.91265(11) 0.0161(3) Uani 1 1 d . . . . .
H18 H 0.5305 0.3555 0.9897 0.019 Uiso 1 1 calc R . . . .
C19 C 0.53482(16) 0.16744(14) 0.93832(12) 0.0217(3) Uani 1 1 d . . . . .
H19A H 0.5550 0.1285 0.8640 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.4289 0.1540 0.9857 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.6114 0.1239 0.9815 0.033 Uiso 1 1 calc GR . . . .
C20 C 0.08425(15) 0.11290(13) 0.74328(11) 0.0174(3) Uani 1 1 d . . . . .
C21 C -0.05775(15) 0.08459(14) 0.72465(13) 0.0212(3) Uani 1 1 d . . . . .
H21 H -0.1092 0.1444 0.6741 0.025 Uiso 1 1 calc R . . . .
C22 C -0.12163(16) -0.03314(15) 0.78193(13) 0.0253(3) Uani 1 1 d . . . . .
H22 H -0.2156 -0.0527 0.7688 0.030 Uiso 1 1 calc R . . . .
C23 C -0.04743(17) -0.12203(15) 0.85843(13) 0.0258(3) Uani 1 1 d . . . . .
H23 H -0.0909 -0.2012 0.8961 0.031 Uiso 1 1 calc R . . . .
C24 C 0.09245(18) -0.09241(16) 0.87865(12) 0.0263(3) Uani 1 1 d . . . . .
H24 H 0.1415 -0.1510 0.9313 0.032 Uiso 1 1 calc R . . . .
C25 C 0.15899(16) 0.02393(15) 0.82068(12) 0.0220(3) Uani 1 1 d . . . . .
H25 H 0.2536 0.0427 0.8334 0.026 Uiso 1 1 calc R . . . .
N1 N 0.70654(13) 0.35099(11) 0.83857(10) 0.0172(2) Uani 1 1 d . . . . .
H1 H 0.789(2) 0.3274(18) 0.8691(16) 0.029(4) Uiso 1 1 d . . . . .
O1 O 0.01370(10) 0.36076(10) 0.91448(8) 0.0222(2) Uani 1 1 d . . . . .
S1 S 0.16759(4) 0.25833(3) 0.65750(3) 0.01847(10) 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
C1 C2 1.4814(17) . ?
C1 C5 1.3491(17) . ?
C1 S1 1.7592(13) . ?
C2 C3 1.5094(17) . ?
C2 O1 1.2159(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5369(16) . ?
C4 C5 1.5453(16) . ?
C4 C12 1.5171(17) . ?
C4 C18 1.5575(17) . ?
C5 C6 1.4865(16) . ?
C6 C7 1.4020(18) . ?
C6 C11 1.3963(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3877(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3912(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.3790(19) . ?
C12 C17 1.4010(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.3912(18) . ?
C17 N1 1.3872(17) . ?
C18 H18 0.9800 . ?
C18 C19 1.5137(18) . ?
C18 N1 1.4700(16) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.3944(18) . ?
C20 C25 1.3922(19) . ?
C20 S1 1.7759(13) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(2) . ?
C25 H25 0.9300 . ?
N1 H1 0.873(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
C2 C1 S1 121.40(9) . . ?
C5 C1 C2 111.01(11) . . ?
C5 C1 S1 127.22(10) . . ?
C1 C2 C3 107.39(10) . . ?
O1 C2 C1 126.40(12) . . ?
O1 C2 C3 126.21(11) . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C2 C3 C4 106.33(10) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C3 C4 C5 103.78(10) . . ?
C3 C4 C18 112.58(10) . . ?
C5 C4 C18 113.46(10) . . ?
C12 C4 C3 117.38(10) . . ?
C12 C4 C5 110.10(10) . . ?
C12 C4 C18 99.93(10) . . ?
C1 C5 C4 111.13(10) . . ?
C1 C5 C6 124.60(11) . . ?
C6 C5 C4 124.26(10) . . ?
C7 C6 C5 118.75(11) . . ?
C11 C6 C5 122.69(11) . . ?
C11 C6 C7 118.55(11) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.86(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.06(13) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.63(12) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.72(13) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 H11 119.9 . . ?
C10 C11 C6 120.15(12) . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C4 130.43(12) . . ?
C13 C12 C17 121.17(12) . . ?
C17 C12 C4 108.00(11) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.70(13) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.91(13) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.85(13) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 117.96(13) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C12 120.38(12) . . ?
N1 C17 C12 110.60(11) . . ?
N1 C17 C16 128.88(12) . . ?
C4 C18 H18 107.8 . . ?
C19 C18 C4 116.36(11) . . ?
C19 C18 H18 107.8 . . ?
N1 C18 C4 102.63(10) . . ?
N1 C18 H18 107.8 . . ?
N1 C18 C19 114.00(10) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 S1 116.97(10) . . ?
C25 C20 C21 119.85(13) . . ?
C25 C20 S1 123.06(10) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.52(13) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.80(13) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.61(13) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.25(14) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 119.96(13) . . ?
C24 C25 H25 120.0 . . ?
C17 N1 C18 106.98(10) . . ?
C17 N1 H1 116.6(11) . . ?
C18 N1 H1 118.2(11) . . ?
C1 S1 C20 102.03(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -6.01(14) . . . . ?
C1 C5 C6 C7 -53.76(18) . . . . ?
C1 C5 C6 C11 125.22(14) . . . . ?
C2 C1 C5 C4 -0.81(15) . . . . ?
C2 C1 C5 C6 178.02(11) . . . . ?
C2 C1 S1 C20 -65.08(11) . . . . ?
C2 C3 C4 C5 5.37(13) . . . . ?
C2 C3 C4 C12 127.07(11) . . . . ?
C2 C3 C4 C18 -117.73(11) . . . . ?
C3 C4 C5 C1 -2.95(14) . . . . ?
C3 C4 C5 C6 178.22(11) . . . . ?
C3 C4 C12 C13 -42.77(18) . . . . ?
C3 C4 C12 C17 144.53(11) . . . . ?
C3 C4 C18 C19 77.04(14) . . . . ?
C3 C4 C18 N1 -157.78(10) . . . . ?
C4 C5 C6 C7 124.91(13) . . . . ?
C4 C5 C6 C11 -56.10(17) . . . . ?
C4 C12 C13 C14 -171.00(12) . . . . ?
C4 C12 C17 C16 172.57(11) . . . . ?
C4 C12 C17 N1 -3.49(14) . . . . ?
C4 C18 N1 C17 32.50(12) . . . . ?
C5 C1 C2 C3 4.37(15) . . . . ?
C5 C1 C2 O1 -176.19(13) . . . . ?
C5 C1 S1 C20 122.53(12) . . . . ?
C5 C4 C12 C13 75.60(16) . . . . ?
C5 C4 C12 C17 -97.09(12) . . . . ?
C5 C4 C18 C19 -40.47(15) . . . . ?
C5 C4 C18 N1 84.72(12) . . . . ?
C5 C6 C7 C8 -179.44(12) . . . . ?
C5 C6 C11 C10 179.07(12) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C6 C11 C10 -1.95(18) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C11 C6 C7 C8 1.54(19) . . . . ?
C12 C4 C5 C1 -129.39(11) . . . . ?
C12 C4 C5 C6 51.78(15) . . . . ?
C12 C4 C18 C19 -157.62(10) . . . . ?
C12 C4 C18 N1 -32.43(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C12 C17 N1 C18 -18.96(13) . . . . ?
C13 C12 C17 C16 -0.94(18) . . . . ?
C13 C12 C17 N1 -177.00(11) . . . . ?
C13 C14 C15 C16 -1.7(2) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C15 C16 C17 C12 -0.30(19) . . . . ?
C15 C16 C17 N1 174.96(12) . . . . ?
C16 C17 N1 C18 165.40(13) . . . . ?
C17 C12 C13 C14 0.87(19) . . . . ?
C18 C4 C5 C1 119.56(12) . . . . ?
C18 C4 C5 C6 -59.27(15) . . . . ?
C18 C4 C12 C13 -164.76(13) . . . . ?
C18 C4 C12 C17 22.54(12) . . . . ?
C19 C18 N1 C17 159.22(11) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C21 C20 C25 C24 0.15(19) . . . . ?
C21 C20 S1 C1 146.33(10) . . . . ?
C21 C22 C23 C24 0.4(2) . . . . ?
C22 C23 C24 C25 -1.3(2) . . . . ?
C23 C24 C25 C20 1.1(2) . . . . ?
C25 C20 C21 C22 -1.07(19) . . . . ?
C25 C20 S1 C1 -37.73(12) . . . . ?
O1 C2 C3 C4 174.55(12) . . . . ?
S1 C1 C2 C3 -169.15(9) . . . . ?
S1 C1 C2 O1 10.29(19) . . . . ?
S1 C1 C5 C4 172.24(9) . . . . ?
S1 C1 C5 C6 -8.94(19) . . . . ?
S1 C20 C21 C22 175.00(10) . . . . ?
S1 C20 C25 C24 -175.67(10) . . . . ?

_olex2_date_sample_data_collection 2018-12-04
_olex2_date_sample_submission    2018-11-28
_olex2_exptl_crystal_mounting_method 'oil on micromount'
_olex2_submission_original_sample_id heh-APG-37
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.675
