# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_smt-618m
_database_code_depnum_ccdc_archive 'CCDC 2429043'
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-03-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O '
_chemical_oxdiff_usercomment     24-02-2025
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   21.5147(16)
_cell_length_b                   5.6766(5)
_cell_length_c                   24.744(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3022.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    158(11)
_cell_measurement_theta_max      27.5770
_cell_measurement_theta_min      2.0520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_av_unetI/netI     0.1105
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15576
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.893
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      158(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  79.00   0.50    3.50    --    6.31  57.00  30.00  168
  2  ω     51.00  78.00   0.50    3.50    --    6.31  30.00 140.00   54
  3  ω      8.00  37.00   0.50    3.50    --    6.31  30.00 140.00   58
  4  ω    -23.00  11.00   0.50    3.50    --   -5.22 -99.00 -60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0248035000
_diffrn_orient_matrix_UB_12      0.0300391000
_diffrn_orient_matrix_UB_13      -0.0103580000
_diffrn_orient_matrix_UB_21      0.0420222000
_diffrn_orient_matrix_UB_22      -0.0135088000
_diffrn_orient_matrix_UB_23      -0.0243085000
_diffrn_orient_matrix_UB_31      -0.1150265000
_diffrn_orient_matrix_UB_32      0.0015496000
_diffrn_orient_matrix_UB_33      -0.0111043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.848
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                3552
_reflns_number_total             5574
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5574
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.000
_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)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1573
_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:
 C00L(H00A,H00B), C00R(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018),
 C019(H019), C01A(H01G)
2.c Idealised Me refined as rotating group:
 C010(H01D,H01E,H01F), C013(H01A,H01B,H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.6924(2) 0.5289(8) 0.3659(2) 0.0277(13) Uani 1 1 d . . . . .
O002 O 0.59519(18) 1.6931(7) 0.53260(19) 0.0273(10) Uani 1 1 d . . . . .
O003 O 0.64967(19) 1.1890(8) 0.46594(19) 0.0294(10) Uani 1 1 d . . . . .
O004 O 0.38249(19) 1.1301(8) 0.5743(2) 0.0341(11) Uani 1 1 d . . . . .
O005 O 0.86491(19) 0.6408(8) 0.4194(2) 0.0360(12) Uani 1 1 d . . . . .
O006 O 0.5563(2) 1.0325(8) 0.6331(3) 0.0308(13) Uani 1 1 d . . . . .
N007 N 0.6551(2) 0.8463(8) 0.4155(2) 0.0228(11) Uani 1 1 d . . . . .
N008 N 0.5912(2) 1.3534(9) 0.5836(2) 0.0238(12) Uani 1 1 d . . . . .
C009 C 0.7000(3) 0.6857(10) 0.3982(3) 0.0213(13) Uani 1 1 d . . . . .
C00A C 0.5675(4) 1.5216(10) 0.5480(3) 0.0219(18) Uani 1 1 d . . . . .
C00B C 0.8223(3) 0.8298(11) 0.3427(3) 0.0276(14) Uani 1 1 d . . . . .
C00C C 0.5472(3) 1.1869(10) 0.6001(3) 0.0232(14) Uani 1 1 d . . . . .
C00D C 0.6540(2) 1.3561(11) 0.6031(3) 0.0224(14) Uani 1 1 d . . . . .
C00E C 0.5919(3) 0.8399(11) 0.3964(3) 0.0225(13) Uani 1 1 d . . . . .
C00F C 0.6785(4) 1.0192(10) 0.4500(3) 0.0225(19) Uani 1 1 d . . . . .
C00G C 0.4278(3) 1.2116(10) 0.5977(3) 0.0246(14) Uani 1 1 d . . . . .
C00H C 0.7590(3) 0.7445(10) 0.4273(3) 0.0213(14) Uani 1 1 d . . . . .
C00I C 0.4886(3) 1.2372(10) 0.5702(3) 0.0226(14) Uani 1 1 d . . . . .
C00J C 0.5008(3) 1.4570(11) 0.5353(3) 0.0211(15) Uani 1 1 d . . . . .
C00K C 0.8196(3) 0.7254(10) 0.3979(3) 0.0245(14) Uani 1 1 d . . . . .
C00L C 0.7536(3) 0.7207(10) 0.4882(3) 0.0236(14) Uani 1 1 d . . . . .
H00A H 0.716447 0.639398 0.502736 0.028 Uiso 1 1 calc R U . . .
H00B H 0.792274 0.693970 0.508952 0.028 Uiso 1 1 calc R U . . .
C00M C 0.6750(3) 1.5465(12) 0.6314(4) 0.0301(17) Uani 1 1 d . . . . .
H00M H 0.648612 1.678118 0.637271 0.036 Uiso 1 1 calc R U . . .
C00N C 0.5563(3) 0.6418(11) 0.4064(3) 0.0264(14) Uani 1 1 d . . . . .
H00N H 0.572922 0.512501 0.426064 0.032 Uiso 1 1 calc R U . . .
C00O C 0.3812(3) 1.1872(12) 0.6893(3) 0.0315(15) Uani 1 1 d . . . . .
H00O H 0.358434 1.053169 0.677638 0.038 Uiso 1 1 calc R U . . .
C00P C 0.4228(3) 1.2977(11) 0.6543(3) 0.0271(15) Uani 1 1 d . . . . .
C00Q C 0.7857(4) 1.0197(12) 0.3281(4) 0.035(2) Uani 1 1 d . . . . .
H00Q H 0.755242 1.077940 0.352465 0.042 Uiso 1 1 calc R U . . .
C00R C 0.4948(3) 1.2167(10) 0.5096(3) 0.0261(15) Uani 1 1 d . . . . .
H00C H 0.456732 1.183398 0.488534 0.031 Uiso 1 1 calc R U . . .
H00D H 0.533106 1.142777 0.495229 0.031 Uiso 1 1 calc R U . . .
C00S C 0.7443(3) 0.9596(12) 0.4629(3) 0.0241(16) Uani 1 1 d . . . . .
C00T C 0.4956(3) 0.6363(12) 0.3871(3) 0.0312(15) Uani 1 1 d . . . . .
H00T H 0.470516 0.501224 0.393100 0.037 Uiso 1 1 calc R U . . .
C00U C 0.8653(3) 0.7398(12) 0.3057(3) 0.0323(16) Uani 1 1 d . . . . .
H00U H 0.890095 0.607245 0.314966 0.039 Uiso 1 1 calc R U . . .
C00V C 0.6918(3) 1.1639(11) 0.5933(3) 0.0268(15) Uani 1 1 d . . . . .
H00V H 0.676683 1.031574 0.573821 0.032 Uiso 1 1 calc R U . . .
C00W C 0.5690(3) 1.0284(12) 0.3676(4) 0.0293(18) Uani 1 1 d . . . . .
H00W H 0.594556 1.161053 0.360405 0.035 Uiso 1 1 calc R U . . .
C00X C 0.4563(4) 1.4930(11) 0.6717(4) 0.030(2) Uani 1 1 d . . . . .
H00X H 0.485387 1.565567 0.648115 0.036 Uiso 1 1 calc R U . . .
C00Y C 0.8362(4) 1.0380(16) 0.2422(5) 0.048(2) Uani 1 1 d . . . . .
H00Y H 0.841466 1.111174 0.207968 0.058 Uiso 1 1 calc R U . . .
C00Z C 0.7528(3) 1.1688(12) 0.6126(3) 0.0310(16) Uani 1 1 d . . . . .
H00Z H 0.779762 1.039698 0.605775 0.037 Uiso 1 1 calc R U . . .
C010 C 0.4536(3) 1.6429(11) 0.5252(3) 0.0295(15) Uani 1 1 d . . . . .
H01D H 0.446690 1.733030 0.558413 0.044 Uiso 1 1 calc R U . . .
H01E H 0.414530 1.569631 0.513739 0.044 Uiso 1 1 calc R U . . .
H01F H 0.468527 1.748723 0.496693 0.044 Uiso 1 1 calc R U . . .
C011 C 0.7354(3) 1.5463(13) 0.6514(4) 0.037(2) Uani 1 1 d . . . . .
H011 H 0.749903 1.676077 0.672124 0.044 Uiso 1 1 calc R U . . .
C012 C 0.3734(3) 1.2746(14) 0.7415(3) 0.0432(18) Uani 1 1 d . . . . .
H012 H 0.345604 1.198696 0.765678 0.052 Uiso 1 1 calc R U . . .
C013 C 0.7909(3) 1.1538(11) 0.4718(3) 0.0301(15) Uani 1 1 d . . . . .
H01A H 0.791392 1.258052 0.440184 0.045 Uiso 1 1 calc R U . . .
H01B H 0.832324 1.085324 0.476872 0.045 Uiso 1 1 calc R U . . .
H01C H 0.779388 1.244413 0.503935 0.045 Uiso 1 1 calc R U . . .
C014 C 0.7739(3) 1.3594(12) 0.6414(3) 0.0372(18) Uani 1 1 d . . . . .
H014 H 0.815479 1.361617 0.654398 0.045 Uiso 1 1 calc R U . . .
C015 C 0.8715(3) 0.8448(14) 0.2556(3) 0.0422(19) Uani 1 1 d . . . . .
H015 H 0.900440 0.783091 0.230252 0.051 Uiso 1 1 calc R U . . .
C016 C 0.5085(4) 1.0226(12) 0.3493(4) 0.037(2) Uani 1 1 d . . . . .
H016 H 0.492029 1.152844 0.329872 0.045 Uiso 1 1 calc R U . . .
C017 C 0.7934(3) 1.1254(15) 0.2781(3) 0.0443(19) Uani 1 1 d . . . . .
H017 H 0.768946 1.258566 0.268568 0.053 Uiso 1 1 calc R U . . .
C018 C 0.4717(3) 0.8277(12) 0.3591(3) 0.0358(17) Uani 1 1 d . . . . .
H018 H 0.429940 0.824722 0.346634 0.043 Uiso 1 1 calc R U . . .
C019 C 0.4473(3) 1.5825(14) 0.7233(3) 0.0416(18) Uani 1 1 d . . . . .
H019 H 0.469336 1.718742 0.734682 0.050 Uiso 1 1 calc R U . . .
C01A C 0.4061(4) 1.4725(15) 0.7581(5) 0.044(2) Uani 1 1 d . . . . .
H01G H 0.400255 1.532756 0.793584 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C009 1.208(8) . ?
O002 C00A 1.204(8) . ?
O003 C00F 1.212(8) . ?
O004 C00G 1.226(7) . ?
O005 C00K 1.209(7) . ?
O006 C00C 1.215(8) . ?
N007 C009 1.395(7) . ?
N007 C00E 1.439(7) . ?
N007 C00F 1.394(9) . ?
N008 C00A 1.396(9) . ?
N008 C00C 1.397(7) . ?
N008 C00D 1.435(7) . ?
C009 C00H 1.497(8) . ?
C00A C00J 1.514(11) . ?
C00B C00K 1.489(9) . ?
C00B C00Q 1.383(10) . ?
C00B C00U 1.398(9) . ?
C00C C00I 1.490(8) . ?
C00D C00M 1.364(10) . ?
C00D C00V 1.383(8) . ?
C00E C00N 1.383(8) . ?
C00E C00W 1.378(9) . ?
C00F C00S 1.491(11) . ?
C00G C00I 1.481(8) . ?
C00G C00P 1.487(9) . ?
C00H C00K 1.498(8) . ?
C00H C00L 1.517(9) . ?
C00H C00S 1.539(9) . ?
C00I C00J 1.540(9) . ?
C00I C00R 1.509(9) . ?
C00J C00R 1.511(9) . ?
C00J C010 1.485(9) . ?
C00L H00A 0.9900 . ?
C00L H00B 0.9900 . ?
C00L C00S 1.507(9) . ?
C00M H00M 0.9500 . ?
C00M C011 1.390(10) . ?
C00N H00N 0.9500 . ?
C00N C00T 1.391(8) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.393(9) . ?
C00O C012 1.393(11) . ?
C00P C00X 1.390(9) . ?
C00Q H00Q 0.9500 . ?
C00Q C017 1.386(13) . ?
C00R H00C 0.9900 . ?
C00R H00D 0.9900 . ?
C00S C013 1.506(9) . ?
C00T H00T 0.9500 . ?
C00T C018 1.388(9) . ?
C00U H00U 0.9500 . ?
C00U C015 1.383(10) . ?
C00V H00V 0.9500 . ?
C00V C00Z 1.396(9) . ?
C00W H00W 0.9500 . ?
C00W C016 1.379(11) . ?
C00X H00X 0.9500 . ?
C00X C019 1.388(12) . ?
C00Y H00Y 0.9500 . ?
C00Y C015 1.375(12) . ?
C00Y C017 1.372(13) . ?
C00Z H00Z 0.9500 . ?
C00Z C014 1.373(10) . ?
C010 H01D 0.9800 . ?
C010 H01E 0.9800 . ?
C010 H01F 0.9800 . ?
C011 H011 0.9500 . ?
C011 C014 1.370(10) . ?
C012 H012 0.9500 . ?
C012 C01A 1.389(11) . ?
C013 H01A 0.9800 . ?
C013 H01B 0.9800 . ?
C013 H01C 0.9800 . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C016 H016 0.9500 . ?
C016 C018 1.381(10) . ?
C017 H017 0.9500 . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C019 C01A 1.385(12) . ?
C01A H01G 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
C009 N007 C00E 122.5(5) . . ?
C00F N007 C009 113.4(5) . . ?
C00F N007 C00E 124.0(5) . . ?
C00A N008 C00C 113.5(5) . . ?
C00A N008 C00D 123.3(5) . . ?
C00C N008 C00D 123.2(5) . . ?
O001 C009 N007 126.2(6) . . ?
O001 C009 C00H 126.7(6) . . ?
N007 C009 C00H 107.1(5) . . ?
O002 C00A N008 124.9(7) . . ?
O002 C00A C00J 126.8(7) . . ?
N008 C00A C00J 108.2(6) . . ?
C00Q C00B C00K 121.8(7) . . ?
C00Q C00B C00U 119.4(7) . . ?
C00U C00B C00K 118.7(6) . . ?
O006 C00C N008 125.1(6) . . ?
O006 C00C C00I 127.5(6) . . ?
N008 C00C C00I 107.4(5) . . ?
C00M C00D N008 119.5(5) . . ?
C00M C00D C00V 121.4(6) . . ?
C00V C00D N008 119.1(5) . . ?
C00N C00E N007 119.0(5) . . ?
C00W C00E N007 119.3(6) . . ?
C00W C00E C00N 121.7(6) . . ?
O003 C00F N007 125.0(7) . . ?
O003 C00F C00S 126.6(7) . . ?
N007 C00F C00S 108.4(6) . . ?
O004 C00G C00I 121.4(6) . . ?
O004 C00G C00P 120.8(6) . . ?
C00I C00G C00P 117.8(5) . . ?
C009 C00H C00K 119.3(5) . . ?
C009 C00H C00L 113.1(5) . . ?
C009 C00H C00S 106.2(5) . . ?
C00K C00H C00L 122.9(5) . . ?
C00K C00H C00S 120.9(5) . . ?
C00L C00H C00S 59.1(4) . . ?
C00C C00I C00J 106.8(5) . . ?
C00C C00I C00R 113.7(5) . . ?
C00G C00I C00C 120.0(5) . . ?
C00G C00I C00J 119.2(5) . . ?
C00G C00I C00R 121.9(6) . . ?
C00R C00I C00J 59.4(4) . . ?
C00A C00J C00I 103.9(6) . . ?
C00R C00J C00A 112.7(5) . . ?
C00R C00J C00I 59.3(4) . . ?
C010 C00J C00A 120.7(5) . . ?
C010 C00J C00I 123.7(6) . . ?
C010 C00J C00R 120.9(6) . . ?
O005 C00K C00B 122.0(5) . . ?
O005 C00K C00H 121.1(6) . . ?
C00B C00K C00H 116.8(5) . . ?
C00H C00L H00A 117.6 . . ?
C00H C00L H00B 117.6 . . ?
H00A C00L H00B 114.8 . . ?
C00S C00L C00H 61.2(5) . . ?
C00S C00L H00A 117.6 . . ?
C00S C00L H00B 117.6 . . ?
C00D C00M H00M 120.3 . . ?
C00D C00M C011 119.5(7) . . ?
C011 C00M H00M 120.3 . . ?
C00E C00N H00N 120.8 . . ?
C00E C00N C00T 118.5(6) . . ?
C00T C00N H00N 120.8 . . ?
C00P C00O H00O 120.2 . . ?
C00P C00O C012 119.5(7) . . ?
C012 C00O H00O 120.2 . . ?
C00O C00P C00G 118.9(6) . . ?
C00X C00P C00G 121.0(7) . . ?
C00X C00P C00O 120.0(7) . . ?
C00B C00Q H00Q 119.9 . . ?
C00B C00Q C017 120.2(9) . . ?
C017 C00Q H00Q 119.9 . . ?
C00I C00R C00J 61.3(5) . . ?
C00I C00R H00C 117.6 . . ?
C00I C00R H00D 117.6 . . ?
C00J C00R H00C 117.6 . . ?
C00J C00R H00D 117.6 . . ?
H00C C00R H00D 114.7 . . ?
C00F C00S C00H 104.5(6) . . ?
C00F C00S C00L 114.7(6) . . ?
C00F C00S C013 119.8(6) . . ?
C00L C00S C00H 59.7(4) . . ?
C013 C00S C00H 121.9(6) . . ?
C013 C00S C00L 120.7(6) . . ?
C00N C00T H00T 119.9 . . ?
C018 C00T C00N 120.2(6) . . ?
C018 C00T H00T 119.9 . . ?
C00B C00U H00U 120.2 . . ?
C015 C00U C00B 119.6(7) . . ?
C015 C00U H00U 120.2 . . ?
C00D C00V H00V 120.8 . . ?
C00D C00V C00Z 118.5(6) . . ?
C00Z C00V H00V 120.8 . . ?
C00E C00W H00W 120.3 . . ?
C00E C00W C016 119.4(6) . . ?
C016 C00W H00W 120.3 . . ?
C00P C00X H00X 119.9 . . ?
C019 C00X C00P 120.3(8) . . ?
C019 C00X H00X 119.9 . . ?
C015 C00Y H00Y 119.9 . . ?
C017 C00Y H00Y 119.9 . . ?
C017 C00Y C015 120.3(9) . . ?
C00V C00Z H00Z 119.8 . . ?
C014 C00Z C00V 120.3(6) . . ?
C014 C00Z H00Z 119.8 . . ?
C00J C010 H01D 109.5 . . ?
C00J C010 H01E 109.5 . . ?
C00J C010 H01F 109.5 . . ?
H01D C010 H01E 109.5 . . ?
H01D C010 H01F 109.5 . . ?
H01E C010 H01F 109.5 . . ?
C00M C011 H011 120.0 . . ?
C014 C011 C00M 120.1(7) . . ?
C014 C011 H011 120.0 . . ?
C00O C012 H012 119.9 . . ?
C01A C012 C00O 120.1(8) . . ?
C01A C012 H012 119.9 . . ?
C00S C013 H01A 109.5 . . ?
C00S C013 H01B 109.5 . . ?
C00S C013 H01C 109.5 . . ?
H01A C013 H01B 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
C00Z C014 H014 119.9 . . ?
C011 C014 C00Z 120.3(6) . . ?
C011 C014 H014 119.9 . . ?
C00U C015 H015 119.8 . . ?
C00Y C015 C00U 120.4(8) . . ?
C00Y C015 H015 119.8 . . ?
C00W C016 H016 119.9 . . ?
C00W C016 C018 120.1(7) . . ?
C018 C016 H016 119.9 . . ?
C00Q C017 H017 120.0 . . ?
C00Y C017 C00Q 120.1(8) . . ?
C00Y C017 H017 120.0 . . ?
C00T C018 H018 119.9 . . ?
C016 C018 C00T 120.1(7) . . ?
C016 C018 H018 119.9 . . ?
C00X C019 H019 120.1 . . ?
C01A C019 C00X 119.8(8) . . ?
C01A C019 H019 120.1 . . ?
C012 C01A H01G 119.9 . . ?
C019 C01A C012 120.3(10) . . ?
C019 C01A H01G 119.9 . . ?

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
O001 C009 C00H C00K 38.2(9) . . . . ?
O001 C009 C00H C00L -118.1(7) . . . . ?
O001 C009 C00H C00S 179.1(7) . . . . ?
O002 C00A C00J C00I -174.3(7) . . . . ?
O002 C00A C00J C00R 123.5(8) . . . . ?
O002 C00A C00J C010 -30.1(12) . . . . ?
O003 C00F C00S C00H -173.9(7) . . . . ?
O003 C00F C00S C00L 123.1(8) . . . . ?
O003 C00F C00S C013 -32.8(12) . . . . ?
O004 C00G C00I C00C -141.2(6) . . . . ?
O004 C00G C00I C00J 84.0(8) . . . . ?
O004 C00G C00I C00R 13.8(9) . . . . ?
O004 C00G C00P C00O 32.6(9) . . . . ?
O004 C00G C00P C00X -144.1(7) . . . . ?
O006 C00C C00I C00G 37.8(9) . . . . ?
O006 C00C C00I C00J 177.5(7) . . . . ?
O006 C00C C00I C00R -119.1(7) . . . . ?
N007 C009 C00H C00K -141.8(5) . . . . ?
N007 C009 C00H C00L 61.9(6) . . . . ?
N007 C009 C00H C00S -0.9(6) . . . . ?
N007 C00E C00N C00T -179.0(6) . . . . ?
N007 C00E C00W C016 180.0(8) . . . . ?
N007 C00F C00S C00H 5.6(8) . . . . ?
N007 C00F C00S C00L -57.4(9) . . . . ?
N007 C00F C00S C013 146.6(7) . . . . ?
N008 C00A C00J C00I 2.5(8) . . . . ?
N008 C00A C00J C00R -59.7(8) . . . . ?
N008 C00A C00J C010 146.7(7) . . . . ?
N008 C00C C00I C00G -141.6(5) . . . . ?
N008 C00C C00I C00J -1.9(7) . . . . ?
N008 C00C C00I C00R 61.4(6) . . . . ?
N008 C00D C00M C011 178.3(7) . . . . ?
N008 C00D C00V C00Z -179.8(6) . . . . ?
C009 N007 C00E C00N 61.3(8) . . . . ?
C009 N007 C00E C00W -117.1(7) . . . . ?
C009 N007 C00F O003 172.8(7) . . . . ?
C009 N007 C00F C00S -6.7(8) . . . . ?
C009 C00H C00K O005 -137.8(6) . . . . ?
C009 C00H C00K C00B 46.1(7) . . . . ?
C009 C00H C00L C00S -95.6(6) . . . . ?
C009 C00H C00S C00F -2.8(7) . . . . ?
C009 C00H C00S C00L 107.6(5) . . . . ?
C009 C00H C00S C013 -142.9(7) . . . . ?
C00A N008 C00C O006 -175.7(7) . . . . ?
C00A N008 C00C C00I 3.8(7) . . . . ?
C00A N008 C00D C00M 59.6(9) . . . . ?
C00A N008 C00D C00V -121.1(7) . . . . ?
C00A C00J C00R C00I 93.2(7) . . . . ?
C00B C00Q C017 C00Y 1.7(13) . . . . ?
C00B C00U C015 C00Y 0.6(11) . . . . ?
C00C N008 C00A O002 172.9(7) . . . . ?
C00C N008 C00A C00J -4.0(8) . . . . ?
C00C N008 C00D C00M -117.9(8) . . . . ?
C00C N008 C00D C00V 61.4(8) . . . . ?
C00C C00I C00J C00A -0.3(7) . . . . ?
C00C C00I C00J C00R 108.1(5) . . . . ?
C00C C00I C00J C010 -143.2(7) . . . . ?
C00C C00I C00R C00J -96.1(6) . . . . ?
C00D N008 C00A O002 -4.9(11) . . . . ?
C00D N008 C00A C00J 178.2(6) . . . . ?
C00D N008 C00C O006 2.1(10) . . . . ?
C00D N008 C00C C00I -178.4(5) . . . . ?
C00D C00M C011 C014 2.0(13) . . . . ?
C00D C00V C00Z C014 1.0(10) . . . . ?
C00E N007 C009 O001 1.1(10) . . . . ?
C00E N007 C009 C00H -178.9(5) . . . . ?
C00E N007 C00F O003 -3.5(11) . . . . ?
C00E N007 C00F C00S 177.0(6) . . . . ?
C00E C00N C00T C018 -0.8(10) . . . . ?
C00E C00W C016 C018 -1.0(14) . . . . ?
C00F N007 C009 O001 -175.3(7) . . . . ?
C00F N007 C009 C00H 4.7(7) . . . . ?
C00F N007 C00E C00N -122.7(7) . . . . ?
C00F N007 C00E C00W 58.9(9) . . . . ?
C00G C00I C00J C00A 139.7(6) . . . . ?
C00G C00I C00J C00R -111.9(7) . . . . ?
C00G C00I C00J C010 -3.1(10) . . . . ?
C00G C00I C00R C00J 107.4(6) . . . . ?
C00G C00P C00X C019 174.9(7) . . . . ?
C00H C00L C00S C00F 92.9(7) . . . . ?
C00H C00L C00S C013 -111.3(7) . . . . ?
C00I C00G C00P C00O -150.0(6) . . . . ?
C00I C00G C00P C00X 33.4(8) . . . . ?
C00K C00B C00Q C017 174.3(7) . . . . ?
C00K C00B C00U C015 -175.5(6) . . . . ?
C00K C00H C00L C00S 109.0(6) . . . . ?
C00K C00H C00S C00F 137.3(6) . . . . ?
C00K C00H C00S C00L -112.3(6) . . . . ?
C00K C00H C00S C013 -2.8(10) . . . . ?
C00L C00H C00K O005 16.1(9) . . . . ?
C00L C00H C00K C00B -159.9(5) . . . . ?
C00L C00H C00S C00F -110.4(6) . . . . ?
C00L C00H C00S C013 109.5(8) . . . . ?
C00M C00D C00V C00Z -0.5(10) . . . . ?
C00M C011 C014 C00Z -1.6(13) . . . . ?
C00N C00E C00W C016 1.6(12) . . . . ?
C00N C00T C018 C016 1.4(11) . . . . ?
C00O C00P C00X C019 -1.7(11) . . . . ?
C00O C012 C01A C019 -0.8(13) . . . . ?
C00P C00G C00I C00C 41.4(8) . . . . ?
C00P C00G C00I C00J -93.5(7) . . . . ?
C00P C00G C00I C00R -163.6(6) . . . . ?
C00P C00O C012 C01A 0.9(11) . . . . ?
C00P C00X C019 C01A 1.9(12) . . . . ?
C00Q C00B C00K O005 -146.9(7) . . . . ?
C00Q C00B C00K C00H 29.1(9) . . . . ?
C00Q C00B C00U C015 1.4(10) . . . . ?
C00R C00I C00J C00A -108.4(6) . . . . ?
C00R C00I C00J C010 108.8(8) . . . . ?
C00S C00H C00K O005 87.1(8) . . . . ?
C00S C00H C00K C00B -88.9(7) . . . . ?
C00U C00B C00K O005 29.9(9) . . . . ?
C00U C00B C00K C00H -154.1(6) . . . . ?
C00U C00B C00Q C017 -2.5(11) . . . . ?
C00V C00D C00M C011 -1.0(12) . . . . ?
C00V C00Z C014 C011 0.0(11) . . . . ?
C00W C00E C00N C00T -0.7(10) . . . . ?
C00W C016 C018 C00T -0.4(13) . . . . ?
C00X C019 C01A C012 -0.6(13) . . . . ?
C010 C00J C00R C00I -113.3(7) . . . . ?
C012 C00O C00P C00G -176.3(6) . . . . ?
C012 C00O C00P C00X 0.3(10) . . . . ?
C015 C00Y C017 C00Q 0.2(13) . . . . ?
C017 C00Y C015 C00U -1.4(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_dioxo_auto
_database_code_depnum_ccdc_archive 'CCDC 2467033'
_audit_update_record             
;
2025-06-24 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-06-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N O5'
_chemical_formula_sum            'C20 H15 N O5'
_chemical_formula_weight         349.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     24-06-2025
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5100(6)
_cell_length_b                   23.2440(13)
_cell_length_c                   7.6943(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.888(7)
_cell_angle_gamma                90
_cell_volume                     1635.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5220
_cell_measurement_theta_min      2.4440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.227
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 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     12.00  65.00   0.50    5.00    --    6.31  19.00  90.00  106
  2  ω    -59.00  29.00   0.50    5.00    --    6.31 -77.00 -30.00  176
  3  ω    -22.00   3.00   0.50    5.00    --   -5.22 -99.00 -60.00   50
  4  ω    -14.00  16.00   0.50    5.00    --   -5.22 -99.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0407210000
_diffrn_orient_matrix_UB_12      0.0240350000
_diffrn_orient_matrix_UB_13      -0.0159203000
_diffrn_orient_matrix_UB_21      0.0541286000
_diffrn_orient_matrix_UB_22      -0.0187728000
_diffrn_orient_matrix_UB_23      -0.0155674000
_diffrn_orient_matrix_UB_31      -0.0377526000
_diffrn_orient_matrix_UB_32      -0.0009679000
_diffrn_orient_matrix_UB_33      -0.0932064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2427
_reflns_number_total             3333
_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 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.044
_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)+(0.0579P)²+0.1633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1263
_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:
 C00J(H00A,H00C), C00Q(H00G,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.11645(13) 0.54511(5) 0.60932(17) 0.0497(3) Uani 1 1 d . . . . .
O002 O 0.12593(14) 0.37423(5) 0.27044(17) 0.0567(4) Uani 1 1 d . . . . .
O003 O 0.31607(16) 0.46920(5) 0.18517(19) 0.0649(4) Uani 1 1 d . . . . .
O004 O 0.05230(14) 0.68016(5) 0.2529(2) 0.0692(4) Uani 1 1 d . . . . .
N005 N 0.21033(15) 0.49221(5) 0.41239(19) 0.0438(3) Uani 1 1 d . . . . .
O006 O 0.17223(17) 0.29171(5) 0.4438(2) 0.0722(4) Uani 1 1 d . . . . .
C007 C 0.25573(17) 0.66560(6) 0.5045(2) 0.0424(4) Uani 1 1 d . . . . .
C008 C 0.14458(17) 0.54038(6) 0.4666(2) 0.0407(4) Uani 1 1 d . . . . .
C009 C 0.11555(17) 0.58292(7) 0.3160(2) 0.0432(4) Uani 1 1 d . . . . .
C00A C 0.19789(18) 0.38775(7) 0.4444(2) 0.0449(4) Uani 1 1 d . . . . .
C00B C 0.38112(18) 0.63258(7) 0.5699(2) 0.0465(4) Uani 1 1 d . . . . .
H00B H 0.385819 0.595813 0.524175 0.056 Uiso 1 1 calc R U . . .
C00C C 0.13278(17) 0.64604(7) 0.3527(2) 0.0454(4) Uani 1 1 d . . . . .
C00D C 0.17351(19) 0.55605(7) 0.1675(2) 0.0451(4) Uani 1 1 d . . . . .
C00E C 0.24324(18) 0.44082(7) 0.5171(2) 0.0441(4) Uani 1 1 d . . . . .
C00F C 0.24207(19) 0.50077(7) 0.2471(2) 0.0470(4) Uani 1 1 d . . . . .
C00G C 0.22599(19) 0.33889(7) 0.5487(3) 0.0511(4) Uani 1 1 d . . . . .
C00H C 0.4984(2) 0.65385(8) 0.7018(3) 0.0545(5) Uani 1 1 d . . . . .
H00H H 0.581970 0.631559 0.744469 0.065 Uiso 1 1 calc R U . . .
C00I C 0.3188(2) 0.44278(7) 0.7001(2) 0.0531(5) Uani 1 1 d . . . . .
H00I H 0.353041 0.477873 0.753035 0.064 Uiso 1 1 calc R U . . .
C00J C 0.0118(2) 0.55986(8) 0.1472(2) 0.0530(5) Uani 1 1 d . . . . .
H00A H -0.044140 0.587446 0.060972 0.064 Uiso 1 1 calc R U . . .
H00C H -0.039593 0.524460 0.156619 0.064 Uiso 1 1 calc R U . . .
C00K C 0.2517(2) 0.72051(7) 0.5751(3) 0.0549(5) Uani 1 1 d . . . . .
H00K H 0.168759 0.743200 0.533126 0.066 Uiso 1 1 calc R U . . .
C00L C 0.4916(2) 0.70806(9) 0.7702(3) 0.0621(5) Uani 1 1 d . . . . .
H00L H 0.570281 0.722244 0.860349 0.075 Uiso 1 1 calc R U . . .
C00M C 0.3689(2) 0.74141(8) 0.7059(3) 0.0652(6) Uani 1 1 d . . . . .
H00M H 0.365509 0.778307 0.751328 0.078 Uiso 1 1 calc R U . . .
C00N C 0.3433(2) 0.39355(8) 0.8033(3) 0.0605(5) Uani 1 1 d . . . . .
H00N H 0.392157 0.396082 0.925527 0.073 Uiso 1 1 calc R U . . .
C00O C 0.2965(2) 0.34007(8) 0.7285(3) 0.0614(5) Uani 1 1 d . . . . .
H00O H 0.312470 0.306715 0.797900 0.074 Uiso 1 1 calc R U . . .
C00P C 0.2446(2) 0.58950(9) 0.0478(3) 0.0590(5) Uani 1 1 d . . . . .
H00D H 0.195411 0.625678 0.017159 0.089 Uiso 1 1 calc R U . . .
H00E H 0.238591 0.567998 -0.060511 0.089 Uiso 1 1 calc R U . . .
H00F H 0.345420 0.596217 0.110237 0.089 Uiso 1 1 calc R U . . .
C00Q C 0.0914(2) 0.31420(8) 0.2748(3) 0.0649(5) Uani 1 1 d . . . . .
H00G H -0.012499 0.309299 0.259973 0.078 Uiso 1 1 calc R U . . .
H00J H 0.117054 0.294064 0.177339 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.205(2) . ?
O002 C00A 1.363(2) . ?
O002 C00Q 1.436(2) . ?
O003 C00F 1.202(2) . ?
O004 C00C 1.218(2) . ?
N005 C008 1.400(2) . ?
N005 C00E 1.427(2) . ?
N005 C00F 1.399(2) . ?
O006 C00G 1.374(2) . ?
O006 C00Q 1.417(3) . ?
C007 C00B 1.391(2) . ?
C007 C00C 1.480(2) . ?
C007 C00K 1.391(2) . ?
C008 C009 1.490(2) . ?
C009 C00C 1.495(2) . ?
C009 C00D 1.531(2) . ?
C009 C00J 1.499(2) . ?
C00A C00E 1.374(2) . ?
C00A C00G 1.374(2) . ?
C00B H00B 0.9300 . ?
C00B C00H 1.378(3) . ?
C00D C00F 1.494(2) . ?
C00D C00J 1.505(3) . ?
C00D C00P 1.501(3) . ?
C00E C00I 1.395(2) . ?
C00G C00O 1.363(3) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.374(3) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.376(3) . ?
C00J H00A 0.9700 . ?
C00J H00C 0.9700 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.370(3) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.375(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00O 1.391(3) . ?
C00O H00O 0.9300 . ?
C00P H00D 0.9600 . ?
C00P H00E 0.9600 . ?
C00P H00F 0.9600 . ?
C00Q H00G 0.9700 . ?
C00Q H00J 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O002 C00Q 104.94(14) . . ?
C008 N005 C00E 123.24(14) . . ?
C00F N005 C008 112.44(13) . . ?
C00F N005 C00E 124.31(14) . . ?
C00G O006 C00Q 105.39(13) . . ?
C00B C007 C00C 121.97(14) . . ?
C00K C007 C00B 118.52(16) . . ?
C00K C007 C00C 119.31(15) . . ?
O001 C008 N005 124.97(15) . . ?
O001 C008 C009 127.46(15) . . ?
N005 C008 C009 107.57(14) . . ?
C008 C009 C00C 121.13(15) . . ?
C008 C009 C00D 106.35(13) . . ?
C008 C009 C00J 111.99(13) . . ?
C00C C009 C00D 119.89(14) . . ?
C00C C009 C00J 121.80(14) . . ?
C00J C009 C00D 59.56(12) . . ?
O002 C00A C00E 128.61(15) . . ?
O002 C00A C00G 110.36(14) . . ?
C00G C00A C00E 121.02(16) . . ?
C007 C00B H00B 119.7 . . ?
C00H C00B C007 120.61(15) . . ?
C00H C00B H00B 119.7 . . ?
O004 C00C C007 121.47(15) . . ?
O004 C00C C009 120.17(16) . . ?
C007 C00C C009 118.22(13) . . ?
C00F C00D C009 104.54(13) . . ?
C00F C00D C00J 114.34(15) . . ?
C00F C00D C00P 118.53(16) . . ?
C00J C00D C009 59.17(11) . . ?
C00P C00D C009 124.16(15) . . ?
C00P C00D C00J 121.67(15) . . ?
C00A C00E N005 121.73(15) . . ?
C00A C00E C00I 117.23(15) . . ?
C00I C00E N005 121.00(15) . . ?
O003 C00F N005 124.66(16) . . ?
O003 C00F C00D 126.87(17) . . ?
N005 C00F C00D 108.43(14) . . ?
C00A C00G O006 109.60(16) . . ?
C00O C00G O006 127.78(16) . . ?
C00O C00G C00A 122.63(16) . . ?
C00B C00H H00H 120.1 . . ?
C00L C00H C00B 119.86(17) . . ?
C00L C00H H00H 120.1 . . ?
C00E C00I H00I 119.5 . . ?
C00N C00I C00E 120.95(17) . . ?
C00N C00I H00I 119.5 . . ?
C009 C00J C00D 61.28(11) . . ?
C009 C00J H00A 117.6 . . ?
C009 C00J H00C 117.6 . . ?
C00D C00J H00A 117.6 . . ?
C00D C00J H00C 117.6 . . ?
H00A C00J H00C 114.7 . . ?
C007 C00K H00K 119.7 . . ?
C00M C00K C007 120.52(17) . . ?
C00M C00K H00K 119.7 . . ?
C00H C00L H00L 119.9 . . ?
C00H C00L C00M 120.21(18) . . ?
C00M C00L H00L 119.9 . . ?
C00K C00M C00L 120.27(17) . . ?
C00K C00M H00M 119.9 . . ?
C00L C00M H00M 119.9 . . ?
C00I C00N H00N 119.3 . . ?
C00I C00N C00O 121.34(18) . . ?
C00O C00N H00N 119.3 . . ?
C00G C00O C00N 116.80(17) . . ?
C00G C00O H00O 121.6 . . ?
C00N C00O H00O 121.6 . . ?
C00D C00P H00D 109.5 . . ?
C00D C00P H00E 109.5 . . ?
C00D C00P H00F 109.5 . . ?
H00D C00P H00E 109.5 . . ?
H00D C00P H00F 109.5 . . ?
H00E C00P H00F 109.5 . . ?
O002 C00Q H00G 110.1 . . ?
O002 C00Q H00J 110.1 . . ?
O006 C00Q O002 108.05(15) . . ?
O006 C00Q H00G 110.1 . . ?
O006 C00Q H00J 110.1 . . ?
H00G C00Q H00J 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C008 C009 C00C 37.9(2) . . . . ?
O001 C008 C009 C00D 179.51(15) . . . . ?
O001 C008 C009 C00J -117.30(19) . . . . ?
O002 C00A C00E N005 3.8(3) . . . . ?
O002 C00A C00E C00I -178.38(17) . . . . ?
O002 C00A C00G O006 0.0(2) . . . . ?
O002 C00A C00G C00O -179.75(17) . . . . ?
N005 C008 C009 C00C -142.82(15) . . . . ?
N005 C008 C009 C00D -1.21(17) . . . . ?
N005 C008 C009 C00J 61.98(18) . . . . ?
N005 C00E C00I C00N 176.33(18) . . . . ?
O006 C00G C00O C00N 178.69(19) . . . . ?
C007 C00B C00H C00L 0.3(3) . . . . ?
C007 C00K C00M C00L -0.6(3) . . . . ?
C008 N005 C00E C00A 127.66(18) . . . . ?
C008 N005 C00E C00I -50.1(2) . . . . ?
C008 N005 C00F O003 169.19(16) . . . . ?
C008 N005 C00F C00D -8.73(18) . . . . ?
C008 C009 C00C O004 -145.98(18) . . . . ?
C008 C009 C00C C007 38.3(2) . . . . ?
C008 C009 C00D C00F -3.67(16) . . . . ?
C008 C009 C00D C00J 106.27(14) . . . . ?
C008 C009 C00D C00P -144.23(16) . . . . ?
C008 C009 C00J C00D -96.59(15) . . . . ?
C009 C00D C00F O003 -170.52(17) . . . . ?
C009 C00D C00F N005 7.35(17) . . . . ?
C00A O002 C00Q O006 -12.6(2) . . . . ?
C00A C00E C00I C00N -1.5(3) . . . . ?
C00A C00G C00O C00N -1.7(3) . . . . ?
C00B C007 C00C O004 -152.09(19) . . . . ?
C00B C007 C00C C009 23.6(2) . . . . ?
C00B C007 C00K C00M 0.1(3) . . . . ?
C00B C00H C00L C00M -0.8(3) . . . . ?
C00C C007 C00B C00H 174.89(17) . . . . ?
C00C C007 C00K C00M -174.85(18) . . . . ?
C00C C009 C00D C00F 138.51(14) . . . . ?
C00C C009 C00D C00J -111.54(17) . . . . ?
C00C C009 C00D C00P -2.0(2) . . . . ?
C00C C009 C00J C00D 108.40(18) . . . . ?
C00D C009 C00C O004 77.4(2) . . . . ?
C00D C009 C00C C007 -98.33(18) . . . . ?
C00E N005 C008 O001 4.4(2) . . . . ?
C00E N005 C008 C009 -174.91(14) . . . . ?
C00E N005 C00F O003 -9.7(3) . . . . ?
C00E N005 C00F C00D 172.41(14) . . . . ?
C00E C00A C00G O006 -178.80(17) . . . . ?
C00E C00A C00G C00O 1.5(3) . . . . ?
C00E C00I C00N C00O 1.3(3) . . . . ?
C00F N005 C008 O001 -174.49(15) . . . . ?
C00F N005 C008 C009 6.21(18) . . . . ?
C00F N005 C00E C00A -53.6(2) . . . . ?
C00F N005 C00E C00I 128.69(18) . . . . ?
C00F C00D C00J C009 92.91(15) . . . . ?
C00G O006 C00Q O002 12.6(2) . . . . ?
C00G C00A C00E N005 -177.67(16) . . . . ?
C00G C00A C00E C00I 0.1(3) . . . . ?
C00H C00L C00M C00K 1.0(3) . . . . ?
C00I C00N C00O C00G 0.3(3) . . . . ?
C00J C009 C00C O004 6.8(3) . . . . ?
C00J C009 C00C C007 -168.99(16) . . . . ?
C00J C009 C00D C00F -109.95(15) . . . . ?
C00J C009 C00D C00P 109.50(19) . . . . ?
C00J C00D C00F O003 127.1(2) . . . . ?
C00J C00D C00F N005 -55.01(18) . . . . ?
C00K C007 C00B C00H 0.1(3) . . . . ?
C00K C007 C00C O004 22.6(3) . . . . ?
C00K C007 C00C C009 -161.65(17) . . . . ?
C00P C00D C00F O003 -27.3(3) . . . . ?
C00P C00D C00F N005 150.60(15) . . . . ?
C00P C00D C00J C009 -113.59(18) . . . . ?
C00Q O002 C00A C00E -173.56(19) . . . . ?
C00Q O002 C00A C00G 7.8(2) . . . . ?
C00Q O006 C00G C00A -7.9(2) . . . . ?
C00Q O006 C00G C00O 171.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.608
_oxdiff_exptl_absorpt_empirical_full_min 0.304
####################################################################### 
# 
# 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_smt-me_auto
_database_code_depnum_ccdc_archive 'CCDC 2468455'
_audit_update_record             
;
2025-06-30 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-06-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Br N O3'
_chemical_formula_sum            'C14 H12 Br N O3'
_chemical_formula_weight         322.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C  H N O'
_chemical_oxdiff_usercomment     30-06-2025
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2247(8)
_cell_length_b                   7.7018(6)
_cell_length_c                   15.9626(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.502(7)
_cell_angle_gamma                90
_cell_volume                     1368.16(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2591
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3190
_cell_measurement_theta_min      2.0890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.106a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8499
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.873
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   8.00   0.50    2.68    --   -4.75 -19.00  30.00  174
  2  ω    -23.00   9.00   0.50    2.68    --   -4.75 -99.00 -60.00   64
  3  ω    -12.00  17.00   0.50    2.68    --   -4.75 -99.00-150.00   58
  4  ω    -10.00  49.00   0.50    2.68    --   -4.75  19.00-120.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0502355000
_diffrn_orient_matrix_UB_12      0.0486936000
_diffrn_orient_matrix_UB_13      0.0093936000
_diffrn_orient_matrix_UB_21      -0.0242334000
_diffrn_orient_matrix_UB_22      -0.0756755000
_diffrn_orient_matrix_UB_23      0.0166517000
_diffrn_orient_matrix_UB_31      0.0308383000
_diffrn_orient_matrix_UB_32      0.0197585000
_diffrn_orient_matrix_UB_33      0.0405232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2346
_reflns_number_total             3442
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.106a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.057
_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)+(0.0256P)²+1.3381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0995
_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:
 C00F(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00I(H00C,H00F,H00G), C00J(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.19154(3) 0.67515(5) 0.83759(2) 0.05439(14) Uani 1 1 d . . . . .
O002 O 0.5257(2) 0.3025(3) 0.56443(16) 0.0584(7) Uani 1 1 d . . . . .
N003 N 0.6185(2) 0.5079(3) 0.65560(16) 0.0398(6) Uani 1 1 d . . . . .
O004 O 0.7595(2) 0.6767(3) 0.73569(18) 0.0619(7) Uani 1 1 d . . . . .
C005 C 0.5177(3) 0.5487(4) 0.69817(19) 0.0354(7) Uani 1 1 d . . . . .
C006 C 0.5175(3) 0.4922(4) 0.78079(19) 0.0398(7) Uani 1 1 d . . . . .
H006 H 0.582018 0.428988 0.807758 0.048 Uiso 1 1 calc R U . . .
C007 C 0.4204(3) 0.5310(4) 0.8225(2) 0.0416(7) Uani 1 1 d . . . . .
H007 H 0.419438 0.495360 0.878040 0.050 Uiso 1 1 calc R U . . .
O008 O 0.8769(3) 0.2191(5) 0.4991(2) 0.0921(11) Uani 1 1 d . . . . .
C009 C 0.3253(3) 0.6225(4) 0.7813(2) 0.0392(7) Uani 1 1 d . . . . .
C00A C 0.7336(3) 0.5770(4) 0.6782(2) 0.0418(8) Uani 1 1 d . . . . .
C00B C 0.6144(3) 0.3832(4) 0.5917(2) 0.0427(8) Uani 1 1 d . . . . .
C00C C 0.7358(3) 0.3773(5) 0.5633(2) 0.0443(8) Uani 1 1 d . . . . .
C00D C 0.4226(3) 0.6423(4) 0.6576(2) 0.0467(8) Uani 1 1 d . . . . .
H00D H 0.424178 0.680886 0.602511 0.056 Uiso 1 1 calc R U . . .
C00E C 0.3251(3) 0.6783(5) 0.6990(2) 0.0468(8) Uani 1 1 d . . . . .
H00E H 0.259898 0.739639 0.671833 0.056 Uiso 1 1 calc R U . . .
C00F C 0.7715(4) 0.5485(5) 0.5286(2) 0.0612(11) Uani 1 1 d . . . . .
H00A H 0.830438 0.546796 0.489217 0.073 Uiso 1 1 calc R U . . .
H00B H 0.709762 0.636563 0.517111 0.073 Uiso 1 1 calc R U . . .
C00G C 0.8141(3) 0.5069(4) 0.6189(2) 0.0451(8) Uani 1 1 d . . . . .
C00H C 0.7868(4) 0.2119(5) 0.5348(2) 0.0599(11) Uani 1 1 d . . . . .
C00I C 0.9454(3) 0.4817(6) 0.6529(3) 0.0681(11) Uani 1 1 d . . . . .
H00C H 0.981479 0.592425 0.667575 0.102 Uiso 1 1 calc R U . . .
H00F H 0.986122 0.427587 0.610476 0.102 Uiso 1 1 calc R U . . .
H00G H 0.951793 0.409086 0.702153 0.102 Uiso 1 1 calc R U . . .
C00J C 0.7306(5) 0.0495(6) 0.5527(3) 0.0804(14) Uani 1 1 d . . . . .
H00H H 0.653359 0.041126 0.519185 0.121 Uiso 1 1 calc R U . . .
H00I H 0.720936 0.044914 0.611541 0.121 Uiso 1 1 calc R U . . .
H00J H 0.780296 -0.045370 0.539306 0.121 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
Br01 C009 1.892(3) . ?
O002 C00B 1.206(4) . ?
N003 C005 1.429(4) . ?
N003 C00A 1.400(4) . ?
N003 C00B 1.398(4) . ?
O004 C00A 1.203(4) . ?
C005 C006 1.389(4) . ?
C005 C00D 1.378(4) . ?
C006 H006 0.9300 . ?
C006 C007 1.382(4) . ?
C007 H007 0.9300 . ?
C007 C009 1.373(4) . ?
O008 C00H 1.225(5) . ?
C009 C00E 1.381(5) . ?
C00A C00G 1.493(5) . ?
C00B C00C 1.491(5) . ?
C00C C00F 1.505(5) . ?
C00C C00G 1.534(5) . ?
C00C C00H 1.492(5) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.379(4) . ?
C00E H00E 0.9300 . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00F C00G 1.493(5) . ?
C00G C00I 1.515(5) . ?
C00H C00J 1.446(6) . ?
C00I H00C 0.9600 . ?
C00I H00F 0.9600 . ?
C00I H00G 0.9600 . ?
C00J H00H 0.9600 . ?
C00J H00I 0.9600 . ?
C00J H00J 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A N003 C005 123.7(3) . . ?
C00B N003 C005 123.1(3) . . ?
C00B N003 C00A 113.0(3) . . ?
C006 C005 N003 118.8(3) . . ?
C00D C005 N003 120.3(3) . . ?
C00D C005 C006 120.9(3) . . ?
C005 C006 H006 120.4 . . ?
C007 C006 C005 119.2(3) . . ?
C007 C006 H006 120.4 . . ?
C006 C007 H007 120.2 . . ?
C009 C007 C006 119.6(3) . . ?
C009 C007 H007 120.2 . . ?
C007 C009 Br01 119.9(2) . . ?
C007 C009 C00E 121.3(3) . . ?
C00E C009 Br01 118.9(2) . . ?
N003 C00A C00G 108.2(3) . . ?
O004 C00A N003 124.2(3) . . ?
O004 C00A C00G 127.5(3) . . ?
O002 C00B N003 124.3(3) . . ?
O002 C00B C00C 128.3(3) . . ?
N003 C00B C00C 107.3(3) . . ?
C00B C00C C00F 112.5(3) . . ?
C00B C00C C00G 106.4(3) . . ?
C00B C00C C00H 121.4(3) . . ?
C00F C00C C00G 58.8(2) . . ?
C00H C00C C00F 120.3(3) . . ?
C00H C00C C00G 121.2(3) . . ?
C005 C00D H00D 120.2 . . ?
C005 C00D C00E 119.6(3) . . ?
C00E C00D H00D 120.2 . . ?
C009 C00E H00E 120.3 . . ?
C00D C00E C009 119.4(3) . . ?
C00D C00E H00E 120.3 . . ?
C00C C00F H00A 117.6 . . ?
C00C C00F H00B 117.6 . . ?
H00A C00F H00B 114.7 . . ?
C00G C00F C00C 61.5(2) . . ?
C00G C00F H00A 117.6 . . ?
C00G C00F H00B 117.6 . . ?
C00A C00G C00C 104.7(3) . . ?
C00A C00G C00I 117.4(3) . . ?
C00F C00G C00A 113.0(3) . . ?
C00F C00G C00C 59.6(2) . . ?
C00F C00G C00I 123.2(3) . . ?
C00I C00G C00C 125.5(3) . . ?
O008 C00H C00C 118.4(4) . . ?
O008 C00H C00J 122.6(4) . . ?
C00J C00H C00C 118.9(4) . . ?
C00G C00I H00C 109.5 . . ?
C00G C00I H00F 109.5 . . ?
C00G C00I H00G 109.5 . . ?
H00C C00I H00F 109.5 . . ?
H00C C00I H00G 109.5 . . ?
H00F C00I H00G 109.5 . . ?
C00H C00J H00H 109.5 . . ?
C00H C00J H00I 109.5 . . ?
C00H C00J H00J 109.5 . . ?
H00H C00J H00I 109.5 . . ?
H00H C00J H00J 109.5 . . ?
H00I C00J H00J 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br01 C009 C00E C00D 179.3(3) . . . . ?
O002 C00B C00C C00F 117.0(4) . . . . ?
O002 C00B C00C C00G 179.4(4) . . . . ?
O002 C00B C00C C00H -36.3(5) . . . . ?
N003 C005 C006 C007 -180.0(3) . . . . ?
N003 C005 C00D C00E 179.0(3) . . . . ?
N003 C00A C00G C00C -4.4(3) . . . . ?
N003 C00A C00G C00F 58.4(4) . . . . ?
N003 C00A C00G C00I -148.8(3) . . . . ?
N003 C00B C00C C00F -60.6(4) . . . . ?
N003 C00B C00C C00G 1.8(3) . . . . ?
N003 C00B C00C C00H 146.1(3) . . . . ?
O004 C00A C00G C00C 176.1(3) . . . . ?
O004 C00A C00G C00F -121.0(4) . . . . ?
O004 C00A C00G C00I 31.8(5) . . . . ?
C005 N003 C00A O004 0.4(5) . . . . ?
C005 N003 C00A C00G -179.1(3) . . . . ?
C005 N003 C00B O002 2.5(5) . . . . ?
C005 N003 C00B C00C -179.8(3) . . . . ?
C005 C006 C007 C009 0.9(5) . . . . ?
C005 C00D C00E C009 1.1(5) . . . . ?
C006 C005 C00D C00E -0.9(5) . . . . ?
C006 C007 C009 Br01 179.7(2) . . . . ?
C006 C007 C009 C00E -0.7(5) . . . . ?
C007 C009 C00E C00D -0.3(5) . . . . ?
C00A N003 C005 C006 -67.6(4) . . . . ?
C00A N003 C005 C00D 112.4(4) . . . . ?
C00A N003 C00B O002 177.4(3) . . . . ?
C00A N003 C00B C00C -4.9(4) . . . . ?
C00B N003 C005 C006 106.7(4) . . . . ?
C00B N003 C005 C00D -73.2(4) . . . . ?
C00B N003 C00A O004 -174.5(3) . . . . ?
C00B N003 C00A C00G 6.0(4) . . . . ?
C00B C00C C00F C00G 96.1(3) . . . . ?
C00B C00C C00G C00A 1.6(3) . . . . ?
C00B C00C C00G C00F -106.8(3) . . . . ?
C00B C00C C00G C00I 142.1(3) . . . . ?
C00B C00C C00H O008 167.9(3) . . . . ?
C00B C00C C00H C00J -14.1(5) . . . . ?
C00C C00F C00G C00A -94.1(3) . . . . ?
C00C C00F C00G C00I 114.9(4) . . . . ?
C00D C005 C006 C007 -0.1(5) . . . . ?
C00F C00C C00G C00A 108.3(3) . . . . ?
C00F C00C C00G C00I -111.2(4) . . . . ?
C00F C00C C00H O008 16.8(5) . . . . ?
C00F C00C C00H C00J -165.3(4) . . . . ?
C00G C00C C00H O008 -52.9(5) . . . . ?
C00G C00C C00H C00J 125.0(4) . . . . ?
C00H C00C C00F C00G -110.4(4) . . . . ?
C00H C00C C00G C00A -142.8(3) . . . . ?
C00H C00C C00G C00F 108.8(4) . . . . ?
C00H C00C C00G C00I -2.3(5) . . . . ?

_olex2_submission_original_sample_id SMT-Me
_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 1.768
_oxdiff_exptl_absorpt_empirical_full_min 0.587
####################################################################### 
# 
# 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_smt-788p-r_auto
_database_code_depnum_ccdc_archive 'CCDC 2463231'
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2025-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 N O3 S'
_chemical_formula_sum            'C25 H19 N O3 S'
_chemical_formula_weight         413.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     09-06-2025
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   29.481(5)
_cell_length_b                   6.8544(3)
_cell_length_c                   15.489(3)
_cell_angle_alpha                90
_cell_angle_beta                 138.05(4)
_cell_angle_gamma                90
_cell_volume                     2092.4(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      2.0460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17563
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.067
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00   5.00   0.50    3.00    --   -5.22 -43.00  29.00  164
  2  ω    -23.00  11.00   0.50    3.00    --   -5.22 -99.00 -30.00   68
  3  ω    -23.00   2.00   0.50    3.00    --   -5.22 -99.00 -60.00   50
  4  ω    -19.00  67.00   0.50    3.00    --   -5.22  43.00-178.00  172
  5  ω     43.00  69.00   0.50    3.00    --    6.31  43.00-178.00   52
  6  ω     14.00  39.00   0.50    3.00    --    6.31  43.00-178.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0331938000
_diffrn_orient_matrix_UB_12      -0.0137061000
_diffrn_orient_matrix_UB_13      0.0337990000
_diffrn_orient_matrix_UB_21      -0.0488276000
_diffrn_orient_matrix_UB_22      0.0530831000
_diffrn_orient_matrix_UB_23      -0.0075835000
_diffrn_orient_matrix_UB_31      -0.0346865000
_diffrn_orient_matrix_UB_32      -0.0877900000
_diffrn_orient_matrix_UB_33      -0.0098407000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             4266
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.738
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.1225
_refine_ls_restrained_S_all      1.297
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3044
_refine_ls_wR_factor_ref         0.3454
_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:
 C00M(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00N(H00D,H00E,H00G)
;
_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
S01 S 0.37488(6) 0.76808(18) 0.82177(11) 0.0675(5) Uani 1 1 d . . . . .
O002 O 0.17113(15) 0.8031(5) 0.5397(3) 0.0593(8) Uani 1 1 d . . . . .
O003 O 0.30168(16) 0.5098(4) 0.5203(3) 0.0624(9) Uani 1 1 d . . . . .
N004 N 0.24809(14) 0.6415(4) 0.5628(3) 0.0431(8) Uani 1 1 d . . . . .
C005 C 0.19994(18) 0.7825(5) 0.5128(4) 0.0416(9) Uani 1 1 d . . . . .
O006 O 0.12527(19) 1.1798(5) 0.2934(4) 0.0936(14) Uani 1 1 d . . . . .
C007 C 0.5080(2) 0.7550(6) 1.0557(5) 0.0538(11) Uani 1 1 d . . . . .
H007 H 0.515860 0.725893 1.009106 0.065 Uiso 1 1 calc R U . . .
C008 C 0.26635(18) 0.6350(6) 0.5020(4) 0.0455(9) Uani 1 1 d . . . . .
C009 C 0.27251(18) 0.5087(5) 0.6619(4) 0.0412(9) Uani 1 1 d . . . . .
C00A C 0.3163(2) 0.2602(5) 0.8519(5) 0.0502(10) Uani 1 1 d . . . . .
H00A H 0.330915 0.175386 0.915635 0.060 Uiso 1 1 calc R U . . .
C00B C 0.0637(2) 0.8847(7) 0.2199(4) 0.0539(10) Uani 1 1 d . . . . .
C00C C 0.4430(2) 0.7812(6) 0.9924(4) 0.0521(11) Uani 1 1 d . . . . .
C00D C 0.2350(2) 0.8057(7) 0.4132(4) 0.0505(10) Uani 1 1 d . . . . .
C00E C 0.19270(19) 0.9075(5) 0.4228(4) 0.0463(9) Uani 1 1 d . . . . .
C00F C 0.2583(2) 0.2218(6) 0.7257(5) 0.0583(12) Uani 1 1 d . . . . .
H00F H 0.233002 0.111921 0.704047 0.070 Uiso 1 1 calc R U . . .
C00G C 0.33236(18) 0.5525(5) 0.7913(4) 0.0447(9) Uani 1 1 d . . . . .
C00H C 0.3534(2) 0.4256(6) 0.8856(4) 0.0531(10) Uani 1 1 d . . . . .
H00H H 0.392937 0.452044 0.972172 0.064 Uiso 1 1 calc R U . . .
C00I C 0.2361(2) 0.3428(5) 0.6284(4) 0.0522(10) Uani 1 1 d . . . . .
H00I H 0.197330 0.312300 0.542081 0.063 Uiso 1 1 calc R U . . .
C00J C 0.5620(2) 0.7717(7) 1.1886(5) 0.0693(14) Uani 1 1 d . . . . .
H00J H 0.605892 0.747053 1.231386 0.083 Uiso 1 1 calc R U . . .
C00K C 0.1259(2) 1.0071(6) 0.3097(4) 0.0553(11) Uani 1 1 d . . . . .
C00L C 0.0646(2) 0.6823(7) 0.2177(5) 0.0735(15) Uani 1 1 d . . . . .
H00L H 0.105484 0.614522 0.274546 0.088 Uiso 1 1 calc R U . . .
C00M C 0.2578(2) 1.0001(6) 0.4853(5) 0.0604(12) Uani 1 1 d . . . . .
H00B H 0.296092 0.997588 0.578879 0.073 Uiso 1 1 calc R U . . .
H00C H 0.254632 1.116286 0.445378 0.073 Uiso 1 1 calc R U . . .
C00N C 0.2149(3) 0.7847(8) 0.2923(5) 0.0632(12) Uani 1 1 d . . . . .
H00D H 0.254199 0.754834 0.313891 0.095 Uiso 1 1 calc R U . . .
H00E H 0.195092 0.904486 0.244430 0.095 Uiso 1 1 calc R U . . .
H00G H 0.182355 0.681111 0.240882 0.095 Uiso 1 1 calc R U . . .
C00O C 0.4320(2) 0.8363(7) 1.0634(5) 0.0658(13) Uani 1 1 d . . . . .
H00O H 0.388292 0.861906 1.021025 0.079 Uiso 1 1 calc R U . . .
C00P C 0.4868(3) 0.8521(7) 1.1968(6) 0.0732(14) Uani 1 1 d . . . . .
H00P H 0.480021 0.881456 1.245232 0.088 Uiso 1 1 calc R U . . .
C00Q C 0.5513(3) 0.8236(9) 1.2562(5) 0.0769(15) Uani 1 1 d . . . . .
H00Q H 0.588298 0.840526 1.345086 0.092 Uiso 1 1 calc R U . . .
C00R C 0.0017(3) 0.9773(8) 0.1326(6) 0.090(2) Uani 1 1 d . . . . .
H00R H 0.000238 1.112846 0.133048 0.108 Uiso 1 1 calc R U . . .
C00S C -0.0579(3) 0.8749(11) 0.0454(7) 0.105(2) Uani 1 1 d . . . . .
H00S H -0.099130 0.940526 -0.014579 0.126 Uiso 1 1 calc R U . . .
C00T C 0.0035(3) 0.5837(9) 0.1294(7) 0.105(3) Uani 1 1 d . . . . .
H00T H 0.003669 0.448193 0.127108 0.127 Uiso 1 1 calc R U . . .
C00U C -0.0564(3) 0.6784(10) 0.0467(7) 0.110(3) Uani 1 1 d . . . . .
H00U H -0.096718 0.608042 -0.009610 0.131 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
S01 C00C 1.769(5) . ?
S01 C00G 1.760(4) . ?
O002 C005 1.200(5) . ?
O003 C008 1.209(5) . ?
N004 C005 1.383(5) . ?
N004 C008 1.390(5) . ?
N004 C009 1.436(5) . ?
C005 C00E 1.510(6) . ?
O006 C00K 1.208(5) . ?
C007 H007 0.9300 . ?
C007 C00C 1.367(6) . ?
C007 C00J 1.381(7) . ?
C008 C00D 1.492(6) . ?
C009 C00G 1.400(6) . ?
C009 C00I 1.372(5) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.357(7) . ?
C00A C00H 1.381(6) . ?
C00B C00K 1.485(6) . ?
C00B C00L 1.389(7) . ?
C00B C00R 1.378(6) . ?
C00C C00O 1.409(7) . ?
C00D C00E 1.531(6) . ?
C00D C00M 1.536(6) . ?
C00D C00N 1.491(7) . ?
C00E C00K 1.510(6) . ?
C00E C00M 1.503(6) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.386(6) . ?
C00G C00H 1.387(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00Q 1.349(9) . ?
C00L H00L 0.9300 . ?
C00L C00T 1.382(7) . ?
C00M H00B 0.9700 . ?
C00M H00C 0.9700 . ?
C00N H00D 0.9600 . ?
C00N H00E 0.9600 . ?
C00N H00G 0.9600 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.388(8) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.378(8) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00S 1.368(8) . ?
C00S H00S 0.9300 . ?
C00S C00U 1.347(10) . ?
C00T H00T 0.9300 . ?
C00T C00U 1.346(9) . ?
C00U H00U 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00G S01 C00C 103.5(2) . . ?
C005 N004 C008 113.4(3) . . ?
C005 N004 C009 122.1(3) . . ?
C008 N004 C009 124.4(3) . . ?
O002 C005 N004 125.8(4) . . ?
O002 C005 C00E 127.1(3) . . ?
N004 C005 C00E 107.1(3) . . ?
C00C C007 H007 119.8 . . ?
C00C C007 C00J 120.4(5) . . ?
C00J C007 H007 119.8 . . ?
O003 C008 N004 124.3(4) . . ?
O003 C008 C00D 127.4(4) . . ?
N004 C008 C00D 108.3(3) . . ?
C00G C009 N004 119.4(3) . . ?
C00I C009 N004 119.4(4) . . ?
C00I C009 C00G 121.2(4) . . ?
C00F C00A H00A 120.1 . . ?
C00F C00A C00H 119.9(4) . . ?
C00H C00A H00A 120.1 . . ?
C00L C00B C00K 123.7(4) . . ?
C00R C00B C00K 118.2(4) . . ?
C00R C00B C00L 118.1(4) . . ?
C007 C00C S01 119.6(4) . . ?
C007 C00C C00O 119.2(4) . . ?
C00O C00C S01 121.0(3) . . ?
C008 C00D C00E 104.9(3) . . ?
C008 C00D C00M 111.9(4) . . ?
C00E C00D C00M 58.7(3) . . ?
C00N C00D C008 118.5(4) . . ?
C00N C00D C00E 125.0(4) . . ?
C00N C00D C00M 123.2(4) . . ?
C005 C00E C00D 105.4(3) . . ?
C005 C00E C00K 119.6(3) . . ?
C00K C00E C00D 123.1(4) . . ?
C00M C00E C005 114.1(4) . . ?
C00M C00E C00D 60.8(3) . . ?
C00M C00E C00K 119.6(4) . . ?
C00A C00F H00F 119.3 . . ?
C00A C00F C00I 121.4(4) . . ?
C00I C00F H00F 119.3 . . ?
C009 C00G S01 116.9(3) . . ?
C00H C00G S01 124.9(3) . . ?
C00H C00G C009 118.2(3) . . ?
C00A C00H C00G 120.6(4) . . ?
C00A C00H H00H 119.7 . . ?
C00G C00H H00H 119.7 . . ?
C009 C00I C00F 118.7(4) . . ?
C009 C00I H00I 120.7 . . ?
C00F C00I H00I 120.7 . . ?
C007 C00J H00J 119.9 . . ?
C00Q C00J C007 120.1(5) . . ?
C00Q C00J H00J 119.9 . . ?
O006 C00K C00B 122.7(4) . . ?
O006 C00K C00E 119.3(4) . . ?
C00B C00K C00E 117.9(3) . . ?
C00B C00L H00L 120.7 . . ?
C00T C00L C00B 118.6(5) . . ?
C00T C00L H00L 120.7 . . ?
C00D C00M H00B 117.7 . . ?
C00D C00M H00C 117.7 . . ?
C00E C00M C00D 60.5(3) . . ?
C00E C00M H00B 117.7 . . ?
C00E C00M H00C 117.7 . . ?
H00B C00M H00C 114.8 . . ?
C00D C00N H00D 109.5 . . ?
C00D C00N H00E 109.5 . . ?
C00D C00N H00G 109.5 . . ?
H00D C00N H00E 109.5 . . ?
H00D C00N H00G 109.5 . . ?
H00E C00N H00G 109.5 . . ?
C00C C00O H00O 120.2 . . ?
C00P C00O C00C 119.7(4) . . ?
C00P C00O H00O 120.2 . . ?
C00O C00P H00P 120.6 . . ?
C00Q C00P C00O 118.8(5) . . ?
C00Q C00P H00P 120.6 . . ?
C00J C00Q C00P 121.6(5) . . ?
C00J C00Q H00Q 119.2 . . ?
C00P C00Q H00Q 119.2 . . ?
C00B C00R H00R 119.2 . . ?
C00S C00R C00B 121.6(6) . . ?
C00S C00R H00R 119.2 . . ?
C00R C00S H00S 120.2 . . ?
C00U C00S C00R 119.7(5) . . ?
C00U C00S H00S 120.2 . . ?
C00L C00T H00T 119.1 . . ?
C00U C00T C00L 121.9(6) . . ?
C00U C00T H00T 119.1 . . ?
C00S C00U H00U 120.0 . . ?
C00T C00U C00S 120.1(5) . . ?
C00T C00U H00U 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S01 C00C C00O C00P -177.7(4) . . . . ?
S01 C00G C00H C00A 179.6(3) . . . . ?
O002 C005 C00E C00D -174.6(4) . . . . ?
O002 C005 C00E C00K -30.5(6) . . . . ?
O002 C005 C00E C00M 120.9(5) . . . . ?
O003 C008 C00D C00E 176.8(4) . . . . ?
O003 C008 C00D C00M -121.4(5) . . . . ?
O003 C008 C00D C00N 31.6(6) . . . . ?
N004 C005 C00E C00D 7.3(4) . . . . ?
N004 C005 C00E C00K 151.4(3) . . . . ?
N004 C005 C00E C00M -57.1(4) . . . . ?
N004 C008 C00D C00E -3.2(4) . . . . ?
N004 C008 C00D C00M 58.6(4) . . . . ?
N004 C008 C00D C00N -148.3(4) . . . . ?
N004 C009 C00G S01 -1.9(5) . . . . ?
N004 C009 C00G C00H 177.5(3) . . . . ?
N004 C009 C00I C00F -176.4(4) . . . . ?
C005 N004 C008 O003 -171.5(4) . . . . ?
C005 N004 C008 C00D 8.5(4) . . . . ?
C005 N004 C009 C00G -95.2(4) . . . . ?
C005 N004 C009 C00I 83.6(4) . . . . ?
C005 C00E C00K O006 129.0(5) . . . . ?
C005 C00E C00K C00B -53.4(5) . . . . ?
C005 C00E C00M C00D 94.8(4) . . . . ?
C007 C00C C00O C00P -3.7(7) . . . . ?
C007 C00J C00Q C00P 3.2(9) . . . . ?
C008 N004 C005 O002 171.8(4) . . . . ?
C008 N004 C005 C00E -10.0(4) . . . . ?
C008 N004 C009 C00G 89.1(4) . . . . ?
C008 N004 C009 C00I -92.1(4) . . . . ?
C008 C00D C00E C005 -2.5(4) . . . . ?
C008 C00D C00E C00K -145.0(4) . . . . ?
C008 C00D C00E C00M 106.9(4) . . . . ?
C008 C00D C00M C00E -94.6(4) . . . . ?
C009 N004 C005 O002 -4.3(6) . . . . ?
C009 N004 C005 C00E 173.8(3) . . . . ?
C009 N004 C008 O003 4.6(6) . . . . ?
C009 N004 C008 C00D -175.5(3) . . . . ?
C009 C00G C00H C00A 0.2(6) . . . . ?
C00A C00F C00I C009 -2.6(7) . . . . ?
C00B C00L C00T C00U -0.4(12) . . . . ?
C00B C00R C00S C00U 2.2(12) . . . . ?
C00C S01 C00G C009 176.1(3) . . . . ?
C00C S01 C00G C00H -3.3(4) . . . . ?
C00C C007 C00J C00Q -3.4(8) . . . . ?
C00C C00O C00P C00Q 3.5(7) . . . . ?
C00D C00E C00K O006 -93.6(6) . . . . ?
C00D C00E C00K C00B 84.1(5) . . . . ?
C00F C00A C00H C00G -0.5(7) . . . . ?
C00G S01 C00C C007 111.2(3) . . . . ?
C00G S01 C00C C00O -74.9(4) . . . . ?
C00G C009 C00I C00F 2.4(6) . . . . ?
C00H C00A C00F C00I 1.7(7) . . . . ?
C00I C009 C00G S01 179.3(3) . . . . ?
C00I C009 C00G C00H -1.2(6) . . . . ?
C00J C007 C00C S01 177.7(4) . . . . ?
C00J C007 C00C C00O 3.6(6) . . . . ?
C00K C00B C00L C00T -179.8(6) . . . . ?
C00K C00B C00R C00S 178.9(6) . . . . ?
C00K C00E C00M C00D -113.7(4) . . . . ?
C00L C00B C00K O006 163.8(6) . . . . ?
C00L C00B C00K C00E -13.7(7) . . . . ?
C00L C00B C00R C00S -0.3(10) . . . . ?
C00L C00T C00U C00S 2.3(14) . . . . ?
C00M C00D C00E C005 -109.4(4) . . . . ?
C00M C00D C00E C00K 108.2(4) . . . . ?
C00M C00E C00K O006 -20.9(7) . . . . ?
C00M C00E C00K C00B 156.7(4) . . . . ?
C00N C00D C00E C005 139.7(4) . . . . ?
C00N C00D C00E C00K -2.8(6) . . . . ?
C00N C00D C00E C00M -110.9(5) . . . . ?
C00N C00D C00M C00E 113.9(5) . . . . ?
C00O C00P C00Q C00J -3.2(8) . . . . ?
C00R C00B C00K O006 -15.3(8) . . . . ?
C00R C00B C00K C00E 167.1(5) . . . . ?
C00R C00B C00L C00T -0.6(9) . . . . ?
C00R C00S C00U C00T -3.1(13) . . . . ?

_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.693
