# Electronic Supplementary Material (ESI) for RSC Chemical Biology.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo114_auto
_database_code_depnum_ccdc_archive 'CCDC 2264764'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H28 N2 O4 S'
_chemical_formula_sum            'C29 H28 N2 O4 S'
_chemical_formula_weight         500.59
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N S O '
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                   6.44134(7)
_cell_length_b                   17.00295(19)
_cell_length_c                   23.3012(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2551.99(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10266
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      71.3350
_cell_measurement_theta_min      4.5840
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    1.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13429
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.413
_diffrn_reflns_theta_min         3.794
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9399
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  14.00   1.00   13.91    --  -36.25  89.00  -8.00   84
  2  ω    -33.00  70.00   1.00   13.91    --   36.25 -89.00-123.00  103
  3  ω     82.00 176.00   1.00   55.66    --  107.00  89.00  -8.00   94
  4  ω    -90.00 -22.00   1.00   13.91    --  -36.25 125.00  30.00   68
  5  ω     20.00 104.00   1.00   13.91    --   36.25  57.00  60.00   84
  6  ω    -31.00  53.00   1.00   13.91    --   36.25 -57.00 120.00   84
  7  ω     90.00 175.00   1.00   55.66    --  107.00  45.00 -60.00   85
  8  ω     37.00  84.00   1.00   55.66    --  107.00-111.00-180.00   47
  9  ω     90.00 175.00   1.00   55.66    --  107.00  45.00  60.00   85
 10  ω     40.00 125.00   1.00   55.66    --  107.00 -61.00   0.00   85
 11  ω     37.00  84.00   1.00   55.66    --  107.00-111.00 -90.00   47
 12  ω     37.00  84.00   1.00   55.66    --  107.00-111.00 150.00   47
 13  ω     37.00  84.00   1.00   55.66    --  107.00-111.00 -60.00   47
 14  ω     20.00 104.00   1.00   13.91    --   36.25  57.00 150.00   84
 15  ω     20.00 104.00   1.00   13.91    --   36.25  57.00 -30.00   84
 16  ω    -31.00  -6.00   1.00   13.91    --   36.25 -57.00 -90.00   25
 17  ω     17.00  67.00   1.00   13.91    --   36.25  38.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133962000
_diffrn_orient_matrix_UB_12      -0.0839135000
_diffrn_orient_matrix_UB_13      0.0246273000
_diffrn_orient_matrix_UB_21      -0.1027438000
_diffrn_orient_matrix_UB_22      -0.0324968000
_diffrn_orient_matrix_UB_23      -0.0547715000
_diffrn_orient_matrix_UB_31      0.2156162000
_diffrn_orient_matrix_UB_32      -0.0102971000
_diffrn_orient_matrix_UB_33      -0.0276767000
_diffrn_oxdiff_digest_frames     
;
0111babeca6015839a49b620eac7b071b600027eff5
;
_diffrn_oxdiff_digest_hkl        
;
016922848f785b1e1713e5ec1bcb458b95ad3c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                4489
_reflns_number_total             4668
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     767
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.047
_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)+(0.0541P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 C23, S1, O3, O4, N2, H2, C10, C24, C28, C9, H10, C17, H24, C25, C27, H28, N1,
 H9, C11, C18, C22, H25, C26, H27, C8, C12, C16, H18, C19, C21, H22, C29, C6,
 H8, H12, C13, C15, H16, H19, C20, H21, H29A, H29B, H29C, C1, C5, H13, C14, H15,
  H20, O1, C2, C4, H5, H14, H1, H2A, C3, O2, H3, C7, H7A, H7B, H7C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
C26 \\sim S1 \\sim O3 \\sim O4 \\sim N2 \\sim C23 \\sim H2 \\sim C10 \\sim C24
\\sim C28 \\sim C9 \\sim H10 \\sim C17 \\sim H24 \\sim C25 \\sim C27 \\sim H28
\\sim N1 \\sim H9 \\sim C11 \\sim C18 \\sim C22 \\sim H25 \\sim H27 \\sim C8
\\sim C12 \\sim C16 \\sim H18 \\sim C19 \\sim C21 \\sim H22 \\sim C29 \\sim C6
\\sim H8 \\sim H12 \\sim C13 \\sim C15 \\sim H16 \\sim H19 \\sim C20 \\sim H21
\\sim H29A \\sim H29B \\sim H29C \\sim C1 \\sim C5 \\sim H13 \\sim C14 \\sim
H15 \\sim H20 \\sim O1 \\sim C2 \\sim C4 \\sim H5 \\sim H14 \\sim H1 \\sim H2A
\\sim C3 \\sim O2 \\sim H3 \\sim C7 \\sim H7A \\sim H7B \\sim H7C: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
3. Rigid body (RIGU) restrains
 C26, S1, O3, O4, N2, C23, H2, C10, C24, C28, C9, H10, C17, H24, C25, C27, H28,
  N1, H9, C11, C18, C22, H25, H27, C8, C12, C16, H18, C19, C21, H22, C29, C6,
 H8, H12, C13, C15, H16, H19, C20, H21, H29A, H29B, H29C, C1, C5, H13, C14, H15,
  H20, O1, C2, C4, H5, H14, H1, H2A, C3, O2, H3, C7, H7A, H7B, H7C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C27(H27), C28(H28)
4.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C29(H29A,H29B,H29C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46620(7) 0.34271(3) 0.26304(2) 0.01078(13) Uani 1 1 d . U . . .
O1 O 0.8763(2) 0.44840(10) 0.47719(7) 0.0163(3) Uani 1 1 d . U . . .
H1 H 0.785388 0.463843 0.453930 0.025 Uiso 1 1 calc R U . . .
O2 O 0.5773(2) 0.21766(10) 0.62258(7) 0.0182(3) Uani 1 1 d . U . . .
O3 O 0.6695(2) 0.37397(10) 0.25273(6) 0.0171(3) Uani 1 1 d . U . . .
O4 O 0.4399(2) 0.26054(9) 0.27542(6) 0.0150(3) Uani 1 1 d . U . . .
N1 N 0.5137(3) 0.44982(10) 0.42602(7) 0.0119(3) Uani 1 1 d . U . . .
N2 N 0.3731(3) 0.38819(10) 0.31856(7) 0.0106(3) Uani 1 1 d . U . . .
H2 H 0.308627 0.360623 0.345105 0.013 Uiso 1 1 calc R U . . .
C1 C 0.7947(3) 0.39212(12) 0.51171(9) 0.0130(4) Uani 1 1 d . U . . .
C2 C 0.9168(3) 0.36213(13) 0.55617(9) 0.0149(4) Uani 1 1 d . U . . .
H2A H 1.053902 0.381362 0.561567 0.018 Uiso 1 1 calc R U . . .
C3 C 0.8399(3) 0.30475(14) 0.59237(9) 0.0149(4) Uani 1 1 d . U . . .
H3 H 0.923866 0.285195 0.622694 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6385(3) 0.27521(13) 0.58463(9) 0.0133(4) Uani 1 1 d . U . . .
C5 C 0.5150(3) 0.30500(12) 0.54137(9) 0.0123(4) Uani 1 1 d . U . . .
H5 H 0.378075 0.285430 0.536358 0.015 Uiso 1 1 calc R U . . .
C6 C 0.5905(3) 0.36413(13) 0.50464(9) 0.0119(4) Uani 1 1 d . U . . .
C7 C 0.3607(3) 0.20207(14) 0.62568(10) 0.0169(4) Uani 1 1 d . U . . .
H7A H 0.314498 0.177776 0.589750 0.025 Uiso 1 1 calc R U . . .
H7B H 0.285414 0.251457 0.631722 0.025 Uiso 1 1 calc R U . . .
H7C H 0.333047 0.166228 0.657718 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4505(3) 0.39899(12) 0.46242(9) 0.0118(4) Uani 1 1 d . U . . .
H8 H 0.308839 0.383471 0.462005 0.014 Uiso 1 1 calc R U . . .
C9 C 0.3594(3) 0.49106(12) 0.39109(9) 0.0114(4) Uani 1 1 d . U . . .
H9 H 0.217433 0.473222 0.402572 0.014 Uiso 1 1 calc R U . . .
C10 C 0.3923(3) 0.47370(12) 0.32622(9) 0.0113(4) Uani 1 1 d . U . . .
H10 H 0.537213 0.489279 0.315878 0.014 Uiso 1 1 calc R U . . .
C11 C 0.3813(3) 0.57823(13) 0.40421(9) 0.0135(4) Uani 1 1 d . U . . .
C12 C 0.2166(3) 0.61982(14) 0.42767(9) 0.0188(5) Uani 1 1 d . U . . .
H12 H 0.088309 0.594061 0.434857 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2392(4) 0.69940(15) 0.44070(11) 0.0264(5) Uani 1 1 d . U . . .
H13 H 0.125728 0.727882 0.456419 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4256(4) 0.73690(14) 0.43084(11) 0.0267(5) Uani 1 1 d . U . . .
H14 H 0.440228 0.791141 0.439756 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5922(4) 0.69560(15) 0.40791(10) 0.0234(5) Uani 1 1 d . U . . .
H15 H 0.720671 0.721486 0.401253 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5705(4) 0.61643(14) 0.39477(9) 0.0177(4) Uani 1 1 d . U . . .
H16 H 0.684540 0.588075 0.379292 0.021 Uiso 1 1 calc R U . . .
C17 C 0.2434(3) 0.52248(13) 0.29020(8) 0.0120(4) Uani 1 1 d . U . . .
C18 C 0.3058(3) 0.59561(13) 0.26944(10) 0.0161(4) Uani 1 1 d . U . . .
H18 H 0.443907 0.613148 0.275810 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1675(4) 0.64316(13) 0.23946(10) 0.0207(5) Uani 1 1 d . U . . .
H19 H 0.210490 0.693514 0.226382 0.025 Uiso 1 1 calc R U . . .
C20 C -0.0337(4) 0.61724(14) 0.22854(10) 0.0198(5) Uani 1 1 d . U . . .
H20 H -0.128090 0.649647 0.207977 0.024 Uiso 1 1 calc R U . . .
C21 C -0.0952(3) 0.54381(14) 0.24790(10) 0.0172(4) Uani 1 1 d . U . . .
H21 H -0.231414 0.525355 0.239974 0.021 Uiso 1 1 calc R U . . .
C22 C 0.0422(3) 0.49689(12) 0.27898(9) 0.0138(4) Uani 1 1 d . U . . .
H22 H -0.001976 0.446973 0.292633 0.017 Uiso 1 1 calc R U . . .
C23 C 0.3135(3) 0.36497(12) 0.20234(9) 0.0127(4) Uani 1 1 d . U . . .
C24 C 0.3874(4) 0.41712(14) 0.16113(10) 0.0192(5) Uani 1 1 d . U . . .
H24 H 0.520751 0.440351 0.165067 0.023 Uiso 1 1 calc R U . . .
C25 C 0.2633(4) 0.43468(15) 0.11417(10) 0.0232(5) Uani 1 1 d . U . . .
H25 H 0.313550 0.469560 0.085509 0.028 Uiso 1 1 calc R U . . .
C26 C 0.0659(4) 0.40187(13) 0.10841(9) 0.0176(4) Uani 1 1 d . U . . .
C27 C -0.0036(3) 0.34970(13) 0.15039(9) 0.0163(4) Uani 1 1 d . U . . .
H27 H -0.137649 0.326885 0.146900 0.020 Uiso 1 1 calc R U . . .
C28 C 0.1195(3) 0.33055(13) 0.19712(9) 0.0147(4) Uani 1 1 d . U . . .
H28 H 0.071528 0.294331 0.225187 0.018 Uiso 1 1 calc R U . . .
C29 C -0.0695(4) 0.42248(16) 0.05770(11) 0.0264(5) Uani 1 1 d . U . . .
H29A H -0.027245 0.473637 0.042236 0.040 Uiso 1 1 calc R U . . .
H29B H -0.214853 0.425053 0.069994 0.040 Uiso 1 1 calc R U . . .
H29C H -0.054321 0.382147 0.027953 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4338(15) . ?
S1 O4 1.4367(15) . ?
S1 N2 1.6222(17) . ?
S1 C23 1.764(2) . ?
O1 C1 1.356(3) . ?
O2 C4 1.377(3) . ?
O2 C7 1.422(2) . ?
N1 C8 1.277(3) . ?
N1 C9 1.463(3) . ?
N2 C10 1.470(2) . ?
C1 C2 1.397(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.407(3) . ?
C6 C8 1.461(3) . ?
C9 C10 1.555(3) . ?
C9 C11 1.520(3) . ?
C10 C17 1.520(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.379(4) . ?
C14 C15 1.389(4) . ?
C15 C16 1.388(3) . ?
C17 C18 1.393(3) . ?
C17 C22 1.392(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.385(3) . ?
C21 C22 1.394(3) . ?
C23 C24 1.391(3) . ?
C23 C28 1.385(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.395(3) . ?
C26 C27 1.394(3) . ?
C26 C29 1.510(3) . ?
C27 C28 1.386(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
O3 S1 O4 120.11(9) . . ?
O3 S1 N2 107.14(9) . . ?
O3 S1 C23 107.19(9) . . ?
O4 S1 N2 105.06(9) . . ?
O4 S1 C23 107.70(10) . . ?
N2 S1 C23 109.34(9) . . ?
C4 O2 C7 116.52(17) . . ?
C8 N1 C9 118.50(18) . . ?
C10 N2 S1 122.49(14) . . ?
O1 C1 C2 118.65(19) . . ?
O1 C1 C6 122.07(19) . . ?
C2 C1 C6 119.28(19) . . ?
C3 C2 C1 120.57(19) . . ?
C2 C3 C4 120.41(19) . . ?
O2 C4 C3 115.92(19) . . ?
O2 C4 C5 124.37(19) . . ?
C5 C4 C3 119.70(19) . . ?
C4 C5 C6 120.47(19) . . ?
C1 C6 C8 121.22(19) . . ?
C5 C6 C1 119.55(19) . . ?
C5 C6 C8 119.10(18) . . ?
N1 C8 C6 121.68(19) . . ?
N1 C9 C10 110.94(16) . . ?
N1 C9 C11 107.00(17) . . ?
C11 C9 C10 111.59(17) . . ?
N2 C10 C9 107.12(16) . . ?
N2 C10 C17 114.80(17) . . ?
C17 C10 C9 110.33(16) . . ?
C12 C11 C9 120.3(2) . . ?
C12 C11 C16 119.5(2) . . ?
C16 C11 C9 120.16(19) . . ?
C11 C12 C13 120.0(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 120.2(2) . . ?
C16 C15 C14 119.8(2) . . ?
C15 C16 C11 120.3(2) . . ?
C18 C17 C10 119.78(19) . . ?
C22 C17 C10 121.35(19) . . ?
C22 C17 C18 118.8(2) . . ?
C19 C18 C17 120.6(2) . . ?
C18 C19 C20 120.3(2) . . ?
C21 C20 C19 119.5(2) . . ?
C20 C21 C22 120.2(2) . . ?
C17 C22 C21 120.6(2) . . ?
C24 C23 S1 119.98(17) . . ?
C28 C23 S1 118.87(16) . . ?
C28 C23 C24 121.15(19) . . ?
C25 C24 C23 119.0(2) . . ?
C24 C25 C26 121.0(2) . . ?
C25 C26 C29 120.6(2) . . ?
C27 C26 C25 118.6(2) . . ?
C27 C26 C29 120.8(2) . . ?
C28 C27 C26 121.1(2) . . ?
C23 C28 C27 119.08(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.374
_oxdiff_exptl_absorpt_empirical_full_min 0.473
####################################################################### 
# 
# 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_c2_mi
_database_code_depnum_ccdc_archive 'CCDC 2264766'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), C7 H16 N2 O2'
_chemical_formula_sum            'C7 H16 Br2 N2 O2'
_chemical_formula_weight         320.04
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.6763 1.2805 '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                   9.1475(6)
_cell_length_b                   10.8895(8)
_cell_length_c                   12.2544(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1220.68(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6100
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.04
_cell_measurement_theta_min      3.61
_shelx_estimated_absorpt_T_max   0.558
_shelx_estimated_absorpt_T_min   0.264
_exptl_absorpt_coefficient_mu    8.256
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.2713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1524 before and 0.0708 after correction. The Ratio of minimum to maximum transmission is 0.3601. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5642
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.029
_diffrn_reflns_theta_min         5.434
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2211
_reflns_number_total             2220
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.202
_refine_ls_abs_structure_details 
;
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0112(11)
_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   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.140
_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)+(0.0818P)²+0.8076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1)
1.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), N1(H1A,H1B), C3(H3A,H3B), C2(H2D,H2E)
1.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), C7(H7A,H7B,H7C)
;
_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
Br1 Br 0.24607(7) 0.20294(5) 0.90279(5) 0.0185(3) Uani 1 1 d . . . . .
Br2 Br 0.43879(7) 0.38148(6) 0.47312(5) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.5457(5) 0.5859(4) 0.8443(4) 0.0223(10) Uani 1 1 d . . . . .
O1 O 0.5478(5) 0.3883(4) 0.7926(4) 0.0267(11) Uani 1 1 d . . . . .
C4 C 0.1424(7) 0.6366(6) 0.6692(5) 0.0196(13) Uani 1 1 d . . . . .
H4A H 0.129570 0.709194 0.621487 0.024 Uiso 1 1 calc R . . . .
H4B H 0.079433 0.647695 0.734155 0.024 Uiso 1 1 calc R . . . .
N2 N 0.4024(5) 0.6399(5) 0.6076(4) 0.0168(10) Uani 1 1 d . . . . .
H2A H 0.364253 0.695027 0.559662 0.020 Uiso 1 1 calc GR . . . .
H2B H 0.411217 0.565463 0.574508 0.020 Uiso 1 1 calc GR . . . .
H2C H 0.492027 0.666048 0.629980 0.020 Uiso 1 1 calc GR . . . .
N1 N 0.2766(5) 0.3976(5) 0.7087(4) 0.0171(11) Uani 1 1 d . . . . .
H1A H 0.288163 0.330715 0.752395 0.020 Uiso 1 1 calc R . . . .
H1B H 0.332045 0.385946 0.647879 0.020 Uiso 1 1 calc R . . . .
C5 C 0.3023(6) 0.6284(6) 0.7053(5) 0.0152(12) Uani 1 1 d . . . . .
H5 H 0.322656 0.698718 0.755585 0.018 Uiso 1 1 calc R . . . .
C7 C 0.6956(8) 0.5748(7) 0.8861(6) 0.0255(15) Uani 1 1 d . . . . .
H7A H 0.763839 0.568657 0.824698 0.038 Uiso 1 1 calc GR . . . .
H7B H 0.703378 0.500966 0.931465 0.038 Uiso 1 1 calc GR . . . .
H7C H 0.719491 0.647292 0.929939 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.0949(7) 0.5210(6) 0.6076(6) 0.0224(14) Uani 1 1 d . . . . .
H3A H -0.009992 0.527441 0.588513 0.027 Uiso 1 1 calc R . . . .
H3B H 0.151303 0.514135 0.538895 0.027 Uiso 1 1 calc R . . . .
C6 C 0.4892(7) 0.4859(5) 0.8010(5) 0.0158(12) Uani 1 1 d . . . . .
C2 C 0.1195(7) 0.4075(6) 0.6761(6) 0.0222(14) Uani 1 1 d . . . . .
H2D H 0.057500 0.411477 0.742219 0.027 Uiso 1 1 calc R . . . .
H2E H 0.090821 0.333784 0.633947 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3300(6) 0.5090(5) 0.7677(5) 0.0148(12) Uani 1 1 d . . . . .
H1 H 0.272328 0.514491 0.836829 0.018 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.469(7) . ?
O2 C6 1.317(8) . ?
O1 C6 1.195(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(8) . ?
C4 C3 1.532(9) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C5 1.512(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 C2 1.496(8) . ?
N1 C1 1.495(8) . ?
C5 H5 1.0000 . ?
C5 C1 1.529(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.510(9) . ?
C6 C1 1.533(8) . ?
C2 H2D 0.9900 . ?
C2 H2E 0.9900 . ?
C1 H1 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C7 116.0(5) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C5 C4 C3 111.5(5) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 N2 H2A 109.5 . . ?
C5 N2 H2B 109.5 . . ?
C5 N2 H2C 109.5 . . ?
H1A N1 H1B 107.8 . . ?
C2 N1 H1A 109.1 . . ?
C2 N1 H1B 109.1 . . ?
C1 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C1 N1 C2 112.6(5) . . ?
C4 C5 H5 108.2 . . ?
N2 C5 C4 110.2(5) . . ?
N2 C5 H5 108.2 . . ?
N2 C5 C1 111.4(5) . . ?
C1 C5 C4 110.7(5) . . ?
C1 C5 H5 108.2 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C2 C3 C4 110.9(5) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
O2 C6 C1 110.1(5) . . ?
O1 C6 O2 126.5(6) . . ?
O1 C6 C1 123.3(6) . . ?
N1 C2 C3 110.5(5) . . ?
N1 C2 H2D 109.5 . . ?
N1 C2 H2E 109.5 . . ?
C3 C2 H2D 109.5 . . ?
C3 C2 H2E 109.5 . . ?
H2D C2 H2E 108.1 . . ?
N1 C1 C5 113.2(5) . . ?
N1 C1 C6 107.8(5) . . ?
N1 C1 H1 106.6 . . ?
C5 C1 C6 115.5(5) . . ?
C5 C1 H1 106.6 . . ?
C6 C1 H1 106.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo260_auto
_database_code_depnum_ccdc_archive 'CCDC 2264765'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H28 N2 O4 S'
_chemical_formula_sum            'C29 H28 N2 O4 S'
_chemical_formula_weight         500.59
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
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                   6.43966(10)
_cell_length_b                   16.9994(3)
_cell_length_c                   23.3008(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2550.74(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13728
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      66.9720
_cell_measurement_theta_min      5.1920
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    1.436
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14476
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.085
_diffrn_reflns_theta_max         67.085
_diffrn_reflns_theta_min         5.204
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9737
_diffrn_measured_fraction_theta_max 0.9741
_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  93.00   1.00    1.00    --    5.00  33.00 109.00   85
  2  ω    -69.00 -42.00   1.00    1.00    --  -87.00  33.00 109.00   27
  3  ω    -86.00 -43.00   1.00    1.00    --  -87.00  40.00-180.00   43
  4  ω    -26.00   0.00   1.00    1.00    --  -87.00  40.00-180.00   26
  5  ω   -173.00 -14.00   1.00    1.00    --  -87.00  40.00  30.00  159
  6  ω   -176.00   1.00   1.00    1.00    --  -87.00  30.00-120.00  177
  7  ω   -176.00-143.00   1.00    1.00    --  -87.00  40.00 -90.00   33
  8  ω   -136.00 -22.00   1.00    1.00    --  -87.00  40.00 -90.00  114
  9  ω   -173.00-120.00   1.00    1.00    --  -87.00  50.00 -60.00   53
 10  ω   -153.00-128.00   1.00    1.00    --  -87.00  40.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1783352000
_diffrn_orient_matrix_UB_12      -0.0389589000
_diffrn_orient_matrix_UB_13      -0.0336767000
_diffrn_orient_matrix_UB_21      0.0945780000
_diffrn_orient_matrix_UB_22      0.0816054000
_diffrn_orient_matrix_UB_23      -0.0119326000
_diffrn_orient_matrix_UB_31      0.1282782000
_diffrn_orient_matrix_UB_32      -0.0061011000
_diffrn_orient_matrix_UB_33      0.0556437000
_diffrn_oxdiff_digest_frames     
;
01cfe702da1de2288813d2a33a58d18c62000252fdd
;
_diffrn_oxdiff_digest_hkl        
;
011c876fd3c69f4dfbbb2d23cd5539d1ceb14a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4441
_reflns_number_total             4451
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.055
_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)+(0.0430P)²+0.6617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
1.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C8(H8), C19(H19), C20(H20), C22(H22),
 C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
  C34(H34), C35(H35), C36(H36)
1.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C24(H24A,H24B,H24C)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46625(7) 0.34269(3) 0.73697(2) 0.01403(13) Uani 1 1 d . . . . .
O1 O 0.8763(2) 0.44852(8) 0.52278(6) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.785513 0.463687 0.546197 0.029 Uiso 1 1 calc R U . . .
O2 O 0.5775(2) 0.21767(8) 0.37746(6) 0.0211(3) Uani 1 1 d . . . . .
O3 O 0.6696(2) 0.37404(8) 0.74722(6) 0.0195(3) Uani 1 1 d . . . . .
O4 O 0.4398(2) 0.26084(8) 0.72459(6) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.5136(2) 0.44969(9) 0.57386(6) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.3732(2) 0.38819(9) 0.68136(7) 0.0145(3) Uani 1 1 d . . . . .
H2 H 0.308680 0.360609 0.654838 0.017 Uiso 1 1 calc R U . . .
C1 C 0.7948(3) 0.39215(11) 0.48820(8) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.9162(3) 0.36217(11) 0.44381(9) 0.0183(4) Uani 1 1 d . . . . .
H2A H 1.053244 0.381518 0.438363 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8400(3) 0.30475(12) 0.40767(8) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.924349 0.285043 0.377462 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6387(3) 0.27539(11) 0.41535(8) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.5148(3) 0.30508(11) 0.45857(8) 0.0155(4) Uani 1 1 d . . . . .
H5 H 0.377761 0.285570 0.463521 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5907(3) 0.36408(11) 0.49529(8) 0.0150(4) Uani 1 1 d . . . . .
C7 C 0.3605(3) 0.20201(12) 0.37425(9) 0.0200(4) Uani 1 1 d . . . . .
H7A H 0.333428 0.165096 0.342814 0.030 Uiso 1 1 calc R U . . .
H7B H 0.285387 0.251206 0.367190 0.030 Uiso 1 1 calc R U . . .
H7C H 0.313342 0.178939 0.410522 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4504(3) 0.39894(10) 0.53765(8) 0.0148(4) Uani 1 1 d . . . . .
H8 H 0.308800 0.383328 0.538146 0.018 Uiso 1 1 calc R U . . .
C9 C 0.3594(3) 0.49114(11) 0.60896(8) 0.0146(4) Uani 1 1 d . . . . .
H9 H 0.217249 0.473347 0.597583 0.017 Uiso 1 1 calc R U . . .
C10 C 0.3927(3) 0.47373(10) 0.67361(8) 0.0146(4) Uani 1 1 d . . . . .
H10 H 0.537684 0.489346 0.683943 0.017 Uiso 1 1 calc R U . . .
C18 C 0.3137(3) 0.36496(11) 0.79770(8) 0.0156(4) Uani 1 1 d . . . . .
C19 C 0.3875(3) 0.41709(12) 0.83888(9) 0.0221(4) Uani 1 1 d . . . . .
H19 H 0.520754 0.440453 0.834941 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2636(4) 0.43435(13) 0.88570(9) 0.0259(5) Uani 1 1 d . . . . .
H20 H 0.314113 0.469102 0.914410 0.031 Uiso 1 1 calc R U . . .
C21 C 0.0658(4) 0.40181(11) 0.89164(9) 0.0207(4) Uani 1 1 d . . . . .
C22 C -0.0034(3) 0.34972(11) 0.84967(8) 0.0190(4) Uani 1 1 d . . . . .
H22 H -0.137408 0.326851 0.853210 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1191(3) 0.33063(11) 0.80292(8) 0.0177(4) Uani 1 1 d . . . . .
H23 H 0.070671 0.294550 0.774810 0.021 Uiso 1 1 calc R U . . .
C24 C -0.0695(4) 0.42247(14) 0.94223(10) 0.0295(5) Uani 1 1 d . . . . .
H24A H -0.215484 0.422169 0.930398 0.044 Uiso 1 1 calc R U . . .
H24B H -0.032306 0.474920 0.956343 0.044 Uiso 1 1 calc R U . . .
H24C H -0.048521 0.383745 0.972849 0.044 Uiso 1 1 calc R U . . .
C25 C 0.3816(3) 0.57830(11) 0.59566(8) 0.0169(4) Uani 1 1 d . . . . .
C26 C 0.2165(3) 0.61987(12) 0.57224(8) 0.0216(4) Uani 1 1 d . . . . .
H26 H 0.088111 0.594173 0.565081 0.026 Uiso 1 1 calc R U . . .
C27 C 0.2397(4) 0.69922(13) 0.55930(10) 0.0293(5) Uani 1 1 d . . . . .
H27 H 0.126242 0.727719 0.543563 0.035 Uiso 1 1 calc R U . . .
C28 C 0.4255(4) 0.73682(12) 0.56910(10) 0.0295(5) Uani 1 1 d . . . . .
H28 H 0.439858 0.791074 0.560164 0.035 Uiso 1 1 calc R U . . .
C29 C 0.5925(4) 0.69557(13) 0.59206(9) 0.0262(5) Uani 1 1 d . . . . .
H29 H 0.721036 0.721455 0.598680 0.031 Uiso 1 1 calc R U . . .
C30 C 0.5704(3) 0.61648(12) 0.60524(8) 0.0205(4) Uani 1 1 d . . . . .
H30 H 0.684325 0.588127 0.620859 0.025 Uiso 1 1 calc R U . . .
C31 C 0.2431(3) 0.52245(11) 0.70977(8) 0.0152(4) Uani 1 1 d . . . . .
C32 C 0.3057(3) 0.59577(11) 0.73061(9) 0.0194(4) Uani 1 1 d . . . . .
H32 H 0.443716 0.613409 0.724211 0.023 Uiso 1 1 calc R U . . .
C33 C 0.1674(3) 0.64300(12) 0.76061(9) 0.0236(4) Uani 1 1 d . . . . .
H33 H 0.210540 0.693241 0.773904 0.028 Uiso 1 1 calc R U . . .
C34 C -0.0339(3) 0.61730(12) 0.77135(9) 0.0229(4) Uani 1 1 d . . . . .
H34 H -0.128504 0.649891 0.791688 0.027 Uiso 1 1 calc R U . . .
C35 C -0.0953(3) 0.54384(12) 0.75215(9) 0.0196(4) Uani 1 1 d . . . . .
H35 H -0.231439 0.525315 0.760201 0.024 Uiso 1 1 calc R U . . .
C36 C 0.0421(3) 0.49700(11) 0.72105(8) 0.0174(4) Uani 1 1 d . . . . .
H36 H -0.002208 0.447079 0.707401 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4336(15) . ?
S1 O4 1.4311(14) . ?
S1 N2 1.6237(16) . ?
S1 C18 1.7638(19) . ?
O1 C1 1.358(2) . ?
O2 C4 1.377(2) . ?
O2 C7 1.425(2) . ?
N1 C8 1.273(2) . ?
N1 C9 1.467(2) . ?
N2 C10 1.471(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.406(3) . ?
C6 C8 1.463(3) . ?
C9 C10 1.550(3) . ?
C9 C25 1.520(3) . ?
C10 C31 1.524(3) . ?
C18 C19 1.390(3) . ?
C18 C23 1.388(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.392(3) . ?
C21 C24 1.507(3) . ?
C22 C23 1.383(3) . ?
C25 C26 1.388(3) . ?
C25 C30 1.397(3) . ?
C26 C27 1.390(3) . ?
C27 C28 1.376(4) . ?
C28 C29 1.391(4) . ?
C29 C30 1.386(3) . ?
C31 C32 1.397(3) . ?
C31 C36 1.390(3) . ?
C32 C33 1.388(3) . ?
C33 C34 1.391(3) . ?
C34 C35 1.384(3) . ?
C35 C36 1.394(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
O3 S1 N2 107.03(8) . . ?
O3 S1 C18 107.17(9) . . ?
O4 S1 O3 120.23(8) . . ?
O4 S1 N2 104.98(8) . . ?
O4 S1 C18 107.71(9) . . ?
N2 S1 C18 109.42(9) . . ?
C4 O2 C7 116.57(16) . . ?
C8 N1 C9 118.61(17) . . ?
C10 N2 S1 122.52(13) . . ?
O1 C1 C2 118.80(18) . . ?
O1 C1 C6 122.03(17) . . ?
C2 C1 C6 119.16(18) . . ?
C3 C2 C1 120.80(18) . . ?
C2 C3 C4 120.24(18) . . ?
O2 C4 C3 115.89(17) . . ?
O2 C4 C5 124.25(18) . . ?
C5 C4 C3 119.85(18) . . ?
C4 C5 C6 120.26(18) . . ?
C1 C6 C8 121.22(17) . . ?
C5 C6 C1 119.65(17) . . ?
C5 C6 C8 118.99(17) . . ?
N1 C8 C6 121.60(18) . . ?
N1 C9 C10 110.89(15) . . ?
N1 C9 C25 106.93(15) . . ?
C25 C9 C10 111.79(15) . . ?
N2 C10 C9 107.24(14) . . ?
N2 C10 C31 114.54(15) . . ?
C31 C10 C9 110.24(15) . . ?
C19 C18 S1 120.01(16) . . ?
C23 C18 S1 118.89(14) . . ?
C23 C18 C19 121.09(18) . . ?
C20 C19 C18 118.8(2) . . ?
C19 C20 C21 121.4(2) . . ?
C20 C21 C24 120.84(19) . . ?
C22 C21 C20 118.34(19) . . ?
C22 C21 C24 120.8(2) . . ?
C23 C22 C21 121.30(19) . . ?
C22 C23 C18 119.03(18) . . ?
C26 C25 C9 120.30(18) . . ?
C26 C25 C30 119.54(18) . . ?
C30 C25 C9 120.13(17) . . ?
C25 C26 C27 119.8(2) . . ?
C28 C27 C26 120.5(2) . . ?
C27 C28 C29 120.15(19) . . ?
C30 C29 C28 119.7(2) . . ?
C29 C30 C25 120.3(2) . . ?
C32 C31 C10 119.65(18) . . ?
C36 C31 C10 121.60(17) . . ?
C36 C31 C32 118.71(18) . . ?
C33 C32 C31 120.42(19) . . ?
C32 C33 C34 120.46(18) . . ?
C35 C34 C33 119.45(19) . . ?
C34 C35 C36 120.14(19) . . ?
C31 C36 C35 120.78(18) . . ?

_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 1.611
_oxdiff_exptl_absorpt_empirical_full_min 0.511
####################################################################### 
# 
# 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_2015ncs0302y
_database_code_depnum_ccdc_archive 'CCDC 2264767'
loop_
_audit_author_name
_audit_author_address
'George Kostakis'
;University of Sussex
United Kingdom
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-05-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
loop_
_audit_author_email
j.spencer@sussex.ac.uk
Graham.Tizzard@soton.ac.uk
_chemical_formula_moiety         'C10 H11 N3'
_chemical_formula_sum            'C10 H11 N3'
_chemical_formula_weight         173.219
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C10 H11 N3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.9358(2)
_cell_length_b                   8.3325(3)
_cell_length_c                   17.6337(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     872.16(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8849
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5610
_cell_measurement_theta_min      2.3000
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       chip
_exptl_crystal_F_000             368.216
_exptl_crystal_recrystallization_method 
'The material was recrystallised from acetone by slow evaporation'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11078
_diffrn_reflns_point_group_measured_fraction_full 0.9994
_diffrn_reflns_point_group_measured_fraction_max 0.9961
_diffrn_reflns_theta_full        25.2425
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  74.00   1.00   60.00    --  -16.00   0.00   0.00  180
  2  ω    -67.00  23.00   1.00   60.00    --  -16.00 -72.00 -60.00   90
  3  ω    -59.00  22.00   1.00   60.00    --  -16.00 -72.00 120.00   81
  4  ω    -23.00  74.00   1.00   60.00    --  -16.00  72.00  60.00   97
  5  ω    -18.00  -3.00   1.00   60.00    --  -16.00  72.00-150.00   15
  6  ω    -30.00  53.00   1.00   60.00    --  -16.00  72.00 150.00   83
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ diffractometer equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0035973000
_diffrn_orient_matrix_UB_12      -0.0260972000
_diffrn_orient_matrix_UB_13      0.0382551000
_diffrn_orient_matrix_UB_21      0.1102467000
_diffrn_orient_matrix_UB_22      0.0319521000
_diffrn_orient_matrix_UB_23      0.0037185000
_diffrn_orient_matrix_UB_31      -0.0460731000
_diffrn_orient_matrix_UB_32      0.0744578000
_diffrn_orient_matrix_UB_33      0.0118114000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.994
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                1914
_reflns_number_total             2018
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1760
_refine_diff_density_min         -0.1777
_refine_diff_density_rms         0.0375
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_d_res_high            0.7670
_refine_ls_d_res_low             7.5337
_refine_ls_goodness_of_fit_ref   1.0645
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.0645
_refine_ls_shift/su_max          -0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.1883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0810
_olex2_refinement_description    
;
1.a Rotating group:
 N3(H3a,H3b)
1.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
1.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
N1 N 0.27143(18) 0.58984(13) 0.42836(6) 0.0206(2) Uani 1.000000 .
N2 N 0.38133(19) 0.46604(13) 0.46332(6) 0.0214(2) Uani 1.000000 .
N3 N 0.7081(2) 0.31473(14) 0.43749(6) 0.0235(3) Uani 1.000000 .
H3a H 0.6496(7) 0.2521(9) 0.4709(5) 0.0282(3) Uiso 1.000000 GR
H3b H 0.7470(15) 0.2596(9) 0.39840(13) 0.0282(3) Uiso 1.000000 GR
C10 C 0.0732(2) 0.65736(17) 0.46433(8) 0.0262(3) Uani 1.000000 .
H10a H -0.0301(8) 0.57066(19) 0.4786(5) 0.0393(5) Uiso 1.000000 GR
H10b H 0.1181(3) 0.7169(10) 0.5098(3) 0.0393(5) Uiso 1.000000 GR
H10c H -0.0025(10) 0.7302(10) 0.4289(2) 0.0393(5) Uiso 1.000000 GR
C1 C 0.5511(2) 0.43102(14) 0.41668(7) 0.0190(3) Uani 1.000000 .
C2 C 0.5509(2) 0.52956(15) 0.35076(7) 0.0187(3) Uani 1.000000 .
C3 C 0.3665(2) 0.62906(15) 0.36212(7) 0.0202(3) Uani 1.000000 .
H3 H 0.3165(2) 0.71093(15) 0.32863(7) 0.0243(3) Uiso 1.000000 R
C4 C 0.6970(2) 0.52430(15) 0.28338(7) 0.0189(3) Uani 1.000000 .
C5 C 0.6241(2) 0.59191(16) 0.21474(7) 0.0223(3) Uani 1.000000 .
H5 H 0.4805(2) 0.64206(16) 0.21229(7) 0.0268(3) Uiso 1.000000 R
C6 C 0.7584(2) 0.58666(16) 0.15047(8) 0.0252(3) Uani 1.000000 .
H6 H 0.7064(2) 0.63380(16) 0.10464(8) 0.0302(4) Uiso 1.000000 R
C7 C 0.9689(2) 0.51281(16) 0.15253(8) 0.0244(3) Uani 1.000000 .
H7 H 1.0603(2) 0.50881(16) 0.10834(8) 0.0292(3) Uiso 1.000000 R
C8 C 1.0432(2) 0.44535(16) 0.21976(8) 0.0238(3) Uani 1.000000 .
H8 H 1.1861(2) 0.39412(16) 0.22156(8) 0.0285(3) Uiso 1.000000 R
C9 C 0.9104(2) 0.45190(15) 0.28477(7) 0.0212(3) Uani 1.000000 .
H9 H 0.9650(2) 0.40675(15) 0.33069(7) 0.0255(3) Uiso 1.000000 R


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
N1 N2 1.3674(15) . ?
N1 C10 1.4505(17) . ?
N1 C3 1.3379(16) . ?
N2 C1 1.3331(17) . ?
N3 H3a 0.8600 . ?
N3 H3b 0.8600 . ?
N3 C1 1.3935(16) . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C1 C2 1.4232(17) . ?
C2 C3 1.3874(18) . ?
C2 C4 1.4714(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4034(18) . ?
C4 C9 1.4035(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3862(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.3923(18) . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 N2 118.86(10) . . ?
C3 N1 N2 112.12(10) . . ?
C3 N1 C10 129.01(12) . . ?
C1 N2 N1 104.34(10) . . ?
H3b N3 H3a 109.5 . . ?
C1 N3 H3a 109.4 . . ?
C1 N3 H3b 109.9 . . ?
H10a C10 N1 109.5 . . ?
H10b C10 N1 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 N1 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
N3 C1 N2 119.69(11) . . ?
C2 C1 N2 112.15(11) . . ?
C2 C1 N3 128.08(12) . . ?
C3 C2 C1 103.15(11) . . ?
C4 C2 C1 129.93(11) . . ?
C4 C2 C3 126.80(11) . . ?
C2 C3 N1 108.24(11) . . ?
H3 C3 N1 125.88(7) . . ?
H3 C3 C2 125.88(7) . . ?
C5 C4 C2 120.19(12) . . ?
C9 C4 C2 122.05(11) . . ?
C9 C4 C5 117.76(12) . . ?
H5 C5 C4 119.49(8) . . ?
C6 C5 C4 121.02(13) . . ?
C6 C5 H5 119.49(8) . . ?
H6 C6 C5 119.73(8) . . ?
C7 C6 C5 120.55(13) . . ?
C7 C6 H6 119.73(8) . . ?
H7 C7 C6 120.42(8) . . ?
C8 C7 C6 119.17(12) . . ?
C8 C7 H7 120.42(8) . . ?
H8 C8 C7 119.71(8) . . ?
C9 C8 C7 120.59(13) . . ?
C9 C8 H8 119.71(8) . . ?
C8 C9 C4 120.91(12) . . ?
H9 C9 C4 119.55(7) . . ?
H9 C9 C8 119.55(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 N3 176.03(9) . . . . ?
N1 N2 C1 C2 -0.93(11) . . . . ?
N1 C3 C2 C1 -0.10(11) . . . . ?
N1 C3 C2 C4 176.25(9) . . . . ?
N2 C1 C2 C3 0.66(11) . . . . ?
N2 C1 C2 C4 -175.52(10) . . . . ?
N3 C1 C2 C3 -175.98(14) . . . . ?
N3 C1 C2 C4 7.83(16) . . . . ?
C1 C2 C4 C5 157.77(14) . . . . ?
C1 C2 C4 C9 -21.80(16) . . . . ?
C2 C4 C5 C6 -179.34(12) . . . . ?
C2 C4 C9 C8 178.54(12) . . . . ?
C4 C5 C6 C7 0.44(16) . . . . ?
C4 C9 C8 C7 1.15(14) . . . . ?
C5 C6 C7 C8 -0.35(15) . . . . ?
C6 C7 C8 C9 -0.43(15) . . . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id JS2023-1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.283
_oxdiff_exptl_absorpt_empirical_full_min 0.378

