# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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-366_auto
_database_code_depnum_ccdc_archive 'CCDC 2311799'
_audit_update_record             
;
2023-12-02 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2023-12-02
_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        SMT-366
_chemical_formula_moiety         'C21 H17 N O4'
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     01-12-2023
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/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                   14.2969(17)
_cell_length_b                   6.8015(6)
_cell_length_c                   18.834(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.036(14)
_cell_angle_gamma                90
_cell_volume                     1697.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    224(40)
_cell_measurement_theta_max      27.7640
_cell_measurement_theta_min      3.2550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10835
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.919
_diffrn_reflns_theta_min         3.214
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      224(40)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.721
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  33.00   0.50    1.60    --   -5.21  16.00 104.00  102
  2  ω     -9.00  21.00   0.50    1.60    --    5.37 -77.00  90.00   60
  3  ω    -58.00 -24.00   0.50    1.60    --    5.37 -77.00  90.00   68
  4  ω    -23.00  21.00   0.50    1.60    --   -5.21 -99.00 -30.00   88
  5  ω     -7.00  26.00   0.50    1.60    --   -5.21 -99.00 -60.00   66
;
_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      -0.0520922000
_diffrn_orient_matrix_UB_12      0.0209084000
_diffrn_orient_matrix_UB_13      -0.0104430000
_diffrn_orient_matrix_UB_21      -0.0055450000
_diffrn_orient_matrix_UB_22      0.0077910000
_diffrn_orient_matrix_UB_23      -0.0389298000
_diffrn_orient_matrix_UB_31      -0.0111235000
_diffrn_orient_matrix_UB_32      -0.1018721000
_diffrn_orient_matrix_UB_33      -0.0051310000
_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                2494
_reflns_number_total             3870
_reflns_odcompleteness_completeness 94.43
_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 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.064
_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)+(0.0477P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1469
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00C,H00H,H00L), C00Q(H00N,H00P,H00Q)
;
_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 0.55962(11) 0.7289(2) 0.56277(9) 0.0479(4) Uani 1 1 d . . . . .
O002 O 0.79392(11) 0.2499(2) 0.59738(9) 0.0491(4) Uani 1 1 d . . . . .
O003 O 0.66018(11) 0.9344(2) 0.48753(9) 0.0504(4) Uani 1 1 d . . . . .
N004 N 0.67012(12) 0.4767(2) 0.57806(9) 0.0361(4) Uani 1 1 d . . . . .
O005 O 0.58351(19) 0.1851(3) 0.87028(12) 0.0811(6) Uani 1 1 d . . . . .
C006 C 0.62601(14) 0.6542(3) 0.54680(12) 0.0370(5) Uani 1 1 d . . . . .
C007 C 0.76847(14) 0.7464(3) 0.40743(11) 0.0360(4) Uani 1 1 d . . . . .
C008 C 0.64135(14) 0.3850(3) 0.63627(11) 0.0365(4) Uani 1 1 d . . . . .
C009 C 0.66926(14) 0.7585(3) 0.49324(11) 0.0356(4) Uani 1 1 d . . . . .
C00A C 0.71470(14) 0.6369(3) 0.44952(11) 0.0355(4) Uani 1 1 d . . . . .
C00B C 0.74314(14) 0.3776(3) 0.55688(12) 0.0376(5) Uani 1 1 d . . . . .
C00C C 0.58585(15) 0.2050(3) 0.74615(12) 0.0405(5) Uani 1 1 d . . . . .
C00D C 0.91675(16) 0.9069(3) 0.40460(13) 0.0429(5) Uani 1 1 d . . . . .
H00D H 0.985064 0.941295 0.429170 0.051 Uiso 1 1 calc R U . . .
C00E C 0.56756(15) 0.1135(3) 0.67609(12) 0.0413(5) Uani 1 1 d . . . . .
H00E H 0.536132 -0.010407 0.666176 0.050 Uiso 1 1 calc R U . . .
C00F C 0.86940(15) 0.8002(3) 0.44397(12) 0.0401(5) Uani 1 1 d . . . . .
H00F H 0.905145 0.764044 0.495234 0.048 Uiso 1 1 calc R U . . .
C00G C 0.59509(15) 0.2026(3) 0.62113(12) 0.0399(5) Uani 1 1 d . . . . .
H00G H 0.582589 0.140308 0.573903 0.048 Uiso 1 1 calc R U . . .
C00H C 0.75052(15) 0.4312(3) 0.48248(12) 0.0393(5) Uani 1 1 d . . . . .
C00I C 0.63289(15) 0.3890(3) 0.76048(12) 0.0427(5) Uani 1 1 d . . . . .
H00I H 0.645629 0.451706 0.807682 0.051 Uiso 1 1 calc R U . . .
C00J C 0.66069(15) 0.4791(3) 0.70583(12) 0.0420(5) Uani 1 1 d . . . . .
H00J H 0.692359 0.602775 0.715500 0.050 Uiso 1 1 calc R U . . .
C00K C 0.71706(16) 0.8037(3) 0.33242(13) 0.0454(5) Uani 1 1 d . . . . .
H00K H 0.648900 0.768770 0.307417 0.055 Uiso 1 1 calc R U . . .
C00L C 0.65290(16) 0.4536(3) 0.41482(13) 0.0446(5) Uani 1 1 d . . . . .
H00A H 0.590018 0.433335 0.423302 0.054 Uiso 1 1 calc R U . . .
H00B H 0.651138 0.409366 0.364817 0.054 Uiso 1 1 calc R U . . .
C00M C 0.86510(17) 0.9633(3) 0.32991(13) 0.0475(5) Uani 1 1 d . . . . .
H00M H 0.897868 1.036375 0.303694 0.057 Uiso 1 1 calc R U . . .
C00N C 0.55861(17) 0.1097(3) 0.80756(14) 0.0514(6) Uani 1 1 d . . . . .
C00O C 0.76493(18) 0.9122(3) 0.29364(14) 0.0537(6) Uani 1 1 d . . . . .
H00O H 0.729190 0.950831 0.242675 0.064 Uiso 1 1 calc R U . . .
C00P C 0.83887(18) 0.3382(3) 0.47006(15) 0.0534(6) Uani 1 1 d . . . . .
H00C H 0.838453 0.376955 0.420377 0.080 Uiso 1 1 calc R U . . .
H00H H 0.833826 0.196201 0.471992 0.080 Uiso 1 1 calc R U . . .
H00L H 0.901202 0.381518 0.509811 0.080 Uiso 1 1 calc R U . . .
C00Q C 0.5020(2) -0.0812(4) 0.79069(16) 0.0680(8) Uani 1 1 d . . . . .
H00N H 0.545451 -0.184407 0.784912 0.102 Uiso 1 1 calc R U . . .
H00P H 0.443108 -0.068854 0.743673 0.102 Uiso 1 1 calc R U . . .
H00Q H 0.480909 -0.113760 0.832561 0.102 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 C006 1.210(2) . ?
O002 C00B 1.203(2) . ?
O003 C009 1.204(2) . ?
N004 C006 1.387(2) . ?
N004 C008 1.449(2) . ?
N004 C00B 1.420(3) . ?
O005 C00N 1.212(3) . ?
C006 C009 1.540(3) . ?
C007 C00A 1.494(3) . ?
C007 C00F 1.395(3) . ?
C007 C00K 1.382(3) . ?
C008 C00G 1.384(3) . ?
C008 C00J 1.389(3) . ?
C009 C00A 1.478(3) . ?
C00A C00H 1.539(3) . ?
C00A C00L 1.526(3) . ?
C00B C00H 1.489(3) . ?
C00C C00E 1.392(3) . ?
C00C C00I 1.398(3) . ?
C00C C00N 1.499(3) . ?
C00D H00D 0.9400 . ?
C00D C00F 1.382(3) . ?
C00D C00M 1.376(3) . ?
C00E H00E 0.9400 . ?
C00E C00G 1.378(3) . ?
C00F H00F 0.9400 . ?
C00G H00G 0.9400 . ?
C00H C00L 1.503(3) . ?
C00H C00P 1.507(3) . ?
C00I H00I 0.9400 . ?
C00I C00J 1.378(3) . ?
C00J H00J 0.9400 . ?
C00K H00K 0.9400 . ?
C00K C00O 1.386(3) . ?
C00L H00A 0.9800 . ?
C00L H00B 0.9800 . ?
C00M H00M 0.9400 . ?
C00M C00O 1.380(3) . ?
C00N C00Q 1.499(3) . ?
C00O H00O 0.9400 . ?
C00P H00C 0.9700 . ?
C00P H00H 0.9700 . ?
C00P H00L 0.9700 . ?
C00Q H00N 0.9700 . ?
C00Q H00P 0.9700 . ?
C00Q H00Q 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
C006 N004 C008 118.87(16) . . ?
C006 N004 C00B 124.00(17) . . ?
C00B N004 C008 117.13(15) . . ?
O001 C006 N004 122.31(19) . . ?
O001 C006 C009 120.96(18) . . ?
N004 C006 C009 116.67(16) . . ?
C00F C007 C00A 120.81(18) . . ?
C00K C007 C00A 120.07(18) . . ?
C00K C007 C00F 119.05(19) . . ?
C00G C008 N004 118.63(18) . . ?
C00G C008 C00J 121.18(19) . . ?
C00J C008 N004 120.19(17) . . ?
O003 C009 C006 117.39(18) . . ?
O003 C009 C00A 124.16(19) . . ?
C00A C009 C006 118.38(17) . . ?
C007 C00A C00H 120.52(16) . . ?
C007 C00A C00L 120.71(18) . . ?
C009 C00A C007 115.97(16) . . ?
C009 C00A C00H 115.69(17) . . ?
C009 C00A C00L 113.00(17) . . ?
C00L C00A C00H 58.75(13) . . ?
O002 C00B N004 119.79(19) . . ?
O002 C00B C00H 122.29(19) . . ?
N004 C00B C00H 117.86(17) . . ?
C00E C00C C00I 119.28(19) . . ?
C00E C00C C00N 121.8(2) . . ?
C00I C00C C00N 118.9(2) . . ?
C00F C00D H00D 119.6 . . ?
C00M C00D H00D 119.6 . . ?
C00M C00D C00F 120.8(2) . . ?
C00C C00E H00E 119.7 . . ?
C00G C00E C00C 120.65(19) . . ?
C00G C00E H00E 119.7 . . ?
C007 C00F H00F 120.1 . . ?
C00D C00F C007 119.8(2) . . ?
C00D C00F H00F 120.1 . . ?
C008 C00G H00G 120.4 . . ?
C00E C00G C008 119.3(2) . . ?
C00E C00G H00G 120.4 . . ?
C00B C00H C00A 118.14(17) . . ?
C00B C00H C00L 116.83(17) . . ?
C00B C00H C00P 113.75(18) . . ?
C00L C00H C00A 60.21(13) . . ?
C00L C00H C00P 118.46(19) . . ?
C00P C00H C00A 119.37(18) . . ?
C00C C00I H00I 119.8 . . ?
C00J C00I C00C 120.4(2) . . ?
C00J C00I H00I 119.8 . . ?
C008 C00J H00J 120.4 . . ?
C00I C00J C008 119.23(19) . . ?
C00I C00J H00J 120.4 . . ?
C007 C00K H00K 119.6 . . ?
C007 C00K C00O 120.7(2) . . ?
C00O C00K H00K 119.6 . . ?
C00A C00L H00A 117.7 . . ?
C00A C00L H00B 117.7 . . ?
C00H C00L C00A 61.05(13) . . ?
C00H C00L H00A 117.7 . . ?
C00H C00L H00B 117.7 . . ?
H00A C00L H00B 114.8 . . ?
C00D C00M H00M 120.2 . . ?
C00D C00M C00O 119.7(2) . . ?
C00O C00M H00M 120.2 . . ?
O005 C00N C00C 120.1(2) . . ?
O005 C00N C00Q 120.7(2) . . ?
C00C C00N C00Q 119.1(2) . . ?
C00K C00O H00O 120.0 . . ?
C00M C00O C00K 120.0(2) . . ?
C00M C00O H00O 120.0 . . ?
C00H C00P H00C 109.5 . . ?
C00H C00P H00H 109.5 . . ?
C00H C00P H00L 109.5 . . ?
H00C C00P H00H 109.5 . . ?
H00C C00P H00L 109.5 . . ?
H00H C00P H00L 109.5 . . ?
C00N C00Q H00N 109.5 . . ?
C00N C00Q H00P 109.5 . . ?
C00N C00Q H00Q 109.5 . . ?
H00N C00Q H00P 109.5 . . ?
H00N C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 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
O001 C006 C009 O003 23.1(3) . . . . ?
O001 C006 C009 C00A -154.08(18) . . . . ?
O002 C00B C00H C00A -157.90(18) . . . . ?
O002 C00B C00H C00L 133.3(2) . . . . ?
O002 C00B C00H C00P -10.4(3) . . . . ?
O003 C009 C00A C007 11.5(3) . . . . ?
O003 C009 C00A C00H 160.97(18) . . . . ?
O003 C009 C00A C00L -133.9(2) . . . . ?
N004 C006 C009 O003 -154.01(18) . . . . ?
N004 C006 C009 C00A 28.8(2) . . . . ?
N004 C008 C00G C00E 179.82(17) . . . . ?
N004 C008 C00J C00I -179.85(18) . . . . ?
N004 C00B C00H C00A 24.9(3) . . . . ?
N004 C00B C00H C00L -44.0(2) . . . . ?
N004 C00B C00H C00P 172.31(17) . . . . ?
C006 N004 C008 C00G 117.5(2) . . . . ?
C006 N004 C008 C00J -62.8(2) . . . . ?
C006 N004 C00B O002 163.49(18) . . . . ?
C006 N004 C00B C00H -19.2(3) . . . . ?
C006 C009 C00A C007 -171.50(16) . . . . ?
C006 C009 C00A C00H -22.1(2) . . . . ?
C006 C009 C00A C00L 43.0(2) . . . . ?
C007 C00A C00H C00B 143.92(19) . . . . ?
C007 C00A C00H C00L -109.6(2) . . . . ?
C007 C00A C00H C00P -1.7(3) . . . . ?
C007 C00A C00L C00H 109.30(19) . . . . ?
C007 C00K C00O C00M 0.2(3) . . . . ?
C008 N004 C006 O001 -4.9(3) . . . . ?
C008 N004 C006 C009 172.15(16) . . . . ?
C008 N004 C00B O002 -16.1(3) . . . . ?
C008 N004 C00B C00H 161.17(17) . . . . ?
C009 C00A C00H C00B -4.0(2) . . . . ?
C009 C00A C00H C00L 102.44(19) . . . . ?
C009 C00A C00H C00P -149.6(2) . . . . ?
C009 C00A C00L C00H -107.05(19) . . . . ?
C00A C007 C00F C00D -177.96(17) . . . . ?
C00A C007 C00K C00O 177.4(2) . . . . ?
C00B N004 C006 O001 175.47(18) . . . . ?
C00B N004 C006 C009 -7.5(3) . . . . ?
C00B N004 C008 C00G -62.8(2) . . . . ?
C00B N004 C008 C00J 116.8(2) . . . . ?
C00B C00H C00L C00A 108.63(19) . . . . ?
C00C C00E C00G C008 0.0(3) . . . . ?
C00C C00I C00J C008 0.1(3) . . . . ?
C00D C00M C00O C00K -0.3(3) . . . . ?
C00E C00C C00I C00J 0.1(3) . . . . ?
C00E C00C C00N O005 173.5(2) . . . . ?
C00E C00C C00N C00Q -5.5(3) . . . . ?
C00F C007 C00A C009 85.8(2) . . . . ?
C00F C007 C00A C00H -62.0(3) . . . . ?
C00F C007 C00A C00L -131.5(2) . . . . ?
C00F C007 C00K C00O 0.4(3) . . . . ?
C00F C00D C00M C00O -0.3(3) . . . . ?
C00G C008 C00J C00I -0.2(3) . . . . ?
C00I C00C C00E C00G -0.2(3) . . . . ?
C00I C00C C00N O005 -5.1(3) . . . . ?
C00I C00C C00N C00Q 176.0(2) . . . . ?
C00J C008 C00G C00E 0.2(3) . . . . ?
C00K C007 C00A C009 -91.2(2) . . . . ?
C00K C007 C00A C00H 121.0(2) . . . . ?
C00K C007 C00A C00L 51.5(3) . . . . ?
C00K C007 C00F C00D -0.9(3) . . . . ?
C00L C00A C00H C00B -106.5(2) . . . . ?
C00L C00A C00H C00P 107.9(2) . . . . ?
C00M C00D C00F C007 0.9(3) . . . . ?
C00N C00C C00E C00G -178.75(19) . . . . ?
C00N C00C C00I C00J 178.76(19) . . . . ?
C00P C00H C00L C00A -109.4(2) . . . . ?

_olex2_submission_original_sample_id SMT-366
_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.882
####################################################################### 
# 
# 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-238_auto
_database_code_depnum_ccdc_archive 'CCDC 2350836'
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_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        SMT-238
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O I'
_chemical_oxdiff_usercomment     18-04-2023
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2750(5)
_cell_length_b                   6.3644(3)
_cell_length_c                   12.1715(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.449(6)
_cell_angle_gamma                90
_cell_volume                     735.63(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4418
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9740
_cell_measurement_theta_min      3.4490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
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    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_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  0.0310
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7187
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.356
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  76.00   0.50    1.33    --    5.83  23.00 115.00  146
  2  ω      6.00  32.00   0.50    1.33    --    5.83  38.00 -60.00   52
  3  ω     35.00  61.00   0.50    1.33    --    5.83  38.00 -60.00   52
  4  ω      1.00  79.00   0.50    1.33    --    5.83  38.00-180.00  156
  5  ω    -35.00  18.00   0.50    1.33    --    5.83 -23.00 -49.00  106
  6  ω    -67.00 -42.00   0.50    1.33    --    5.83 -23.00 -49.00   50
  7  ω    -17.00   9.00   0.50    1.33    --   -5.68 -99.00  90.00   52
;
_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      -0.0633302000
_diffrn_orient_matrix_UB_12      -0.0284544000
_diffrn_orient_matrix_UB_13      -0.0475052000
_diffrn_orient_matrix_UB_21      -0.0326476000
_diffrn_orient_matrix_UB_22      -0.0178991000
_diffrn_orient_matrix_UB_23      0.0410388000
_diffrn_orient_matrix_UB_31      -0.0224894000
_diffrn_orient_matrix_UB_32      0.1062453000
_diffrn_orient_matrix_UB_33      -0.0058392000
_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         0.755
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                2686
_reflns_number_total             2879
_reflns_odcompleteness_completeness 99.82
_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 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_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   -0.1(7)
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.069
_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)+(0.0323P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0832
_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(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.00144(18) -0.3281(3) -0.45904(14) 0.0286(4) Uani 1 1 d . . . . .
O002 O -0.26080(19) -0.6469(3) -0.27885(15) 0.0314(4) Uani 1 1 d . . . . .
O003 O -0.36884(19) -0.8838(3) -0.48462(15) 0.0298(4) Uani 1 1 d . . . . .
N004 N -0.1367(2) -0.4602(3) -0.36690(17) 0.0244(5) Uani 1 1 d . . . . .
C005 C -0.3246(3) -0.7082(4) -0.4871(2) 0.0232(5) Uani 1 1 d . . . . .
C006 C 0.0803(3) -0.1141(4) -0.0557(2) 0.0272(6) Uani 1 1 d . . . . .
H006 H 0.127597 -0.036318 0.014994 0.033 Uiso 1 1 calc R U . . .
C007 C -0.0596(3) -0.3439(4) -0.2589(2) 0.0240(5) Uani 1 1 d . . . . .
C008 C -0.0367(3) -0.0306(4) -0.1446(2) 0.0279(6) Uani 1 1 d . . . . .
H008 H -0.068727 0.105958 -0.135726 0.034 Uiso 1 1 calc R U . . .
C009 C -0.2280(2) -0.4335(4) -0.5870(2) 0.0233(5) Uani 1 1 d . . . . .
C00A C -0.2394(3) -0.6026(4) -0.3670(2) 0.0253(5) Uani 1 1 d . . . . .
C00B C -0.1100(3) -0.4065(4) -0.4701(2) 0.0236(5) Uani 1 1 d . . . . .
C00C C -0.4218(3) -0.7033(4) -0.7114(2) 0.0227(5) Uani 1 1 d . . . . .
C00D C -0.5593(3) -0.6520(4) -0.7837(2) 0.0270(6) Uani 1 1 d . . . . .
H00D H -0.606466 -0.541433 -0.761611 0.032 Uiso 1 1 calc R U . . .
C00E C -0.3543(3) -0.8645(4) -0.7460(2) 0.0263(5) Uani 1 1 d . . . . .
H00E H -0.260691 -0.902249 -0.696621 0.032 Uiso 1 1 calc R U . . .
C00F C -0.1078(3) -0.1458(4) -0.2472(2) 0.0256(5) Uani 1 1 d . . . . .
H00F H -0.188415 -0.088994 -0.308582 0.031 Uiso 1 1 calc R U . . .
C00G C 0.0578(3) -0.4294(4) -0.1709(2) 0.0281(6) Uani 1 1 d . . . . .
H00G H 0.089628 -0.566222 -0.179542 0.034 Uiso 1 1 calc R U . . .
C00H C -0.4228(3) -0.9706(4) -0.8519(2) 0.0286(6) Uani 1 1 d . . . . .
H00H H -0.375033 -1.078055 -0.875872 0.034 Uiso 1 1 calc R U . . .
C00I C -0.5606(3) -0.9205(4) -0.9232(2) 0.0277(6) Uani 1 1 d . . . . .
H00I H -0.608228 -0.994601 -0.995172 0.033 Uiso 1 1 calc R U . . .
C00J C 0.1283(3) -0.3110(5) -0.0697(2) 0.0297(6) Uani 1 1 d . . . . .
H00J H 0.210588 -0.366055 -0.009336 0.036 Uiso 1 1 calc R U . . .
C00K C -0.3473(3) -0.5894(4) -0.5966(2) 0.0230(5) Uani 1 1 d . . . . .
C00L C -0.1870(3) -0.4064(4) -0.6925(2) 0.0245(5) Uani 1 1 d . . . . .
H00A H -0.139461 -0.270967 -0.686709 0.037 Uiso 1 1 calc R U . . .
H00B H -0.271683 -0.410358 -0.765841 0.037 Uiso 1 1 calc R U . . .
H00C H -0.123324 -0.520175 -0.693690 0.037 Uiso 1 1 calc R U . . .
C00M C -0.3683(2) -0.3539(4) -0.5907(2) 0.0247(5) Uani 1 1 d . . . . .
H00K H -0.430968 -0.282691 -0.664222 0.030 Uiso 1 1 calc R U . . .
H00L H -0.371773 -0.296169 -0.516351 0.030 Uiso 1 1 calc R U . . .
C00N C -0.6277(3) -0.7621(4) -0.8882(2) 0.0307(6) Uani 1 1 d . . . . .
H00N H -0.722289 -0.727698 -0.936564 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00B 1.208(3) . ?
O002 C00A 1.208(3) . ?
O003 C005 1.211(3) . ?
N004 C007 1.452(3) . ?
N004 C00A 1.390(3) . ?
N004 C00B 1.426(3) . ?
C005 C00A 1.542(3) . ?
C005 C00K 1.471(3) . ?
C006 H006 0.9500 . ?
C006 C008 1.380(4) . ?
C006 C00J 1.381(4) . ?
C007 C00F 1.381(4) . ?
C007 C00G 1.382(3) . ?
C008 H008 0.9500 . ?
C008 C00F 1.391(3) . ?
C009 C00B 1.486(3) . ?
C009 C00K 1.546(3) . ?
C009 C00L 1.507(3) . ?
C009 C00M 1.512(3) . ?
C00C C00D 1.388(3) . ?
C00C C00E 1.391(3) . ?
C00C C00K 1.499(3) . ?
C00D H00D 0.9500 . ?
C00D C00N 1.386(4) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.386(3) . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00J 1.389(4) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.386(4) . ?
C00I H00I 0.9500 . ?
C00I C00N 1.377(4) . ?
C00J H00J 0.9500 . ?
C00K C00M 1.520(3) . ?
C00L H00A 0.9800 . ?
C00L H00B 0.9800 . ?
C00L H00C 0.9800 . ?
C00M H00K 0.9900 . ?
C00M H00L 0.9900 . ?
C00N H00N 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
C00A N004 C007 118.99(19) . . ?
C00A N004 C00B 123.84(19) . . ?
C00B N004 C007 116.93(19) . . ?
O003 C005 C00A 117.5(2) . . ?
O003 C005 C00K 124.4(2) . . ?
C00K C005 C00A 118.1(2) . . ?
C008 C006 H006 120.1 . . ?
C008 C006 C00J 119.9(2) . . ?
C00J C006 H006 120.1 . . ?
C00F C007 N004 117.7(2) . . ?
C00F C007 C00G 121.4(2) . . ?
C00G C007 N004 120.9(2) . . ?
C006 C008 H008 119.9 . . ?
C006 C008 C00F 120.2(2) . . ?
C00F C008 H008 119.9 . . ?
C00B C009 C00K 118.7(2) . . ?
C00B C009 C00L 114.3(2) . . ?
C00B C009 C00M 114.2(2) . . ?
C00L C009 C00K 118.8(2) . . ?
C00L C009 C00M 120.7(2) . . ?
C00M C009 C00K 59.60(15) . . ?
O002 C00A N004 123.1(2) . . ?
O002 C00A C005 120.7(2) . . ?
N004 C00A C005 116.2(2) . . ?
O001 C00B N004 119.6(2) . . ?
O001 C00B C009 123.1(2) . . ?
N004 C00B C009 117.0(2) . . ?
C00D C00C C00E 119.1(2) . . ?
C00D C00C C00K 120.8(2) . . ?
C00E C00C C00K 120.2(2) . . ?
C00C C00D H00D 120.0 . . ?
C00N C00D C00C 120.0(2) . . ?
C00N C00D H00D 120.0 . . ?
C00C C00E H00E 119.8 . . ?
C00H C00E C00C 120.4(2) . . ?
C00H C00E H00E 119.8 . . ?
C007 C00F C008 119.2(2) . . ?
C007 C00F H00F 120.4 . . ?
C008 C00F H00F 120.4 . . ?
C007 C00G H00G 120.7 . . ?
C007 C00G C00J 118.6(2) . . ?
C00J C00G H00G 120.7 . . ?
C00E C00H H00H 119.9 . . ?
C00I C00H C00E 120.3(2) . . ?
C00I C00H H00H 119.9 . . ?
C00H C00I H00I 120.4 . . ?
C00N C00I C00H 119.2(2) . . ?
C00N C00I H00I 120.4 . . ?
C006 C00J C00G 120.8(2) . . ?
C006 C00J H00J 119.6 . . ?
C00G C00J H00J 119.6 . . ?
C005 C00K C009 114.5(2) . . ?
C005 C00K C00C 116.4(2) . . ?
C005 C00K C00M 116.1(2) . . ?
C00C C00K C009 119.2(2) . . ?
C00C C00K C00M 119.3(2) . . ?
C00M C00K C009 59.08(15) . . ?
C009 C00L H00A 109.5 . . ?
C009 C00L H00B 109.5 . . ?
C009 C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
C009 C00M C00K 61.32(16) . . ?
C009 C00M H00K 117.6 . . ?
C009 C00M H00L 117.6 . . ?
C00K C00M H00K 117.6 . . ?
C00K C00M H00L 117.6 . . ?
H00K C00M H00L 114.7 . . ?
C00D C00N H00N 119.5 . . ?
C00I C00N C00D 121.0(2) . . ?
C00I C00N H00N 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O003 C005 C00A O002 -28.5(4) . . . . ?
O003 C005 C00A N004 150.0(2) . . . . ?
O003 C005 C00K C009 -150.0(2) . . . . ?
O003 C005 C00K C00C -4.5(4) . . . . ?
O003 C005 C00K C00M 143.9(2) . . . . ?
N004 C007 C00F C008 179.7(2) . . . . ?
N004 C007 C00G C00J 179.6(2) . . . . ?
C005 C00K C00M C009 104.1(2) . . . . ?
C006 C008 C00F C007 -0.1(4) . . . . ?
C007 N004 C00A O002 -5.8(4) . . . . ?
C007 N004 C00A C005 175.6(2) . . . . ?
C007 N004 C00B O001 25.2(3) . . . . ?
C007 N004 C00B C009 -149.5(2) . . . . ?
C007 C00G C00J C006 1.6(4) . . . . ?
C008 C006 C00J C00G -2.0(4) . . . . ?
C00A N004 C007 C00F -95.0(3) . . . . ?
C00A N004 C007 C00G 84.9(3) . . . . ?
C00A N004 C00B O001 -160.4(2) . . . . ?
C00A N004 C00B C009 24.9(3) . . . . ?
C00A C005 C00K C009 30.3(3) . . . . ?
C00A C005 C00K C00C 175.9(2) . . . . ?
C00A C005 C00K C00M -35.8(3) . . . . ?
C00B N004 C007 C00F 79.6(3) . . . . ?
C00B N004 C007 C00G -100.5(3) . . . . ?
C00B N004 C00A O002 179.9(2) . . . . ?
C00B N004 C00A C005 1.3(3) . . . . ?
C00B C009 C00K C005 -4.2(3) . . . . ?
C00B C009 C00K C00C -148.7(2) . . . . ?
C00B C009 C00K C00M 102.7(2) . . . . ?
C00B C009 C00M C00K -110.3(2) . . . . ?
C00C C00D C00N C00I -1.1(4) . . . . ?
C00C C00E C00H C00I -1.6(4) . . . . ?
C00C C00K C00M C009 -108.4(2) . . . . ?
C00D C00C C00E C00H 0.8(4) . . . . ?
C00D C00C C00K C005 108.1(3) . . . . ?
C00D C00C C00K C009 -108.0(3) . . . . ?
C00D C00C C00K C00M -39.2(3) . . . . ?
C00E C00C C00D C00N 0.5(4) . . . . ?
C00E C00C C00K C005 -70.9(3) . . . . ?
C00E C00C C00K C009 72.9(3) . . . . ?
C00E C00C C00K C00M 141.7(2) . . . . ?
C00E C00H C00I C00N 1.0(4) . . . . ?
C00F C007 C00G C00J -0.5(4) . . . . ?
C00G C007 C00F C008 -0.2(4) . . . . ?
C00H C00I C00N C00D 0.3(4) . . . . ?
C00J C006 C008 C00F 1.2(4) . . . . ?
C00K C005 C00A O002 151.1(2) . . . . ?
C00K C005 C00A N004 -30.3(3) . . . . ?
C00K C009 C00B O001 162.6(2) . . . . ?
C00K C009 C00B N004 -23.0(3) . . . . ?
C00K C00C C00D C00N -178.5(2) . . . . ?
C00K C00C C00E C00H 179.9(2) . . . . ?
C00L C009 C00B O001 14.5(4) . . . . ?
C00L C009 C00B N004 -171.0(2) . . . . ?
C00L C009 C00K C005 142.4(2) . . . . ?
C00L C009 C00K C00C -2.0(3) . . . . ?
C00L C009 C00K C00M -110.6(2) . . . . ?
C00L C009 C00M C00K 107.5(2) . . . . ?
C00M C009 C00B O001 -130.2(2) . . . . ?
C00M C009 C00B N004 44.3(3) . . . . ?
C00M C009 C00K C005 -106.9(2) . . . . ?
C00M C009 C00K C00C 108.6(3) . . . . ?

_olex2_submission_original_sample_id SMT-238
_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 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.776
####################################################################### 
# 
# 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-317_auto
_database_code_depnum_ccdc_archive 'CCDC 2330995'
_audit_update_record             
;
2024-02-04 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_audit_creation_date             2024-02-04
_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         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     14-09-2023
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6199(4)
_cell_length_b                   10.8504(5)
_cell_length_c                   15.1555(6)
_cell_angle_alpha                103.773(4)
_cell_angle_beta                 97.032(3)
_cell_angle_gamma                114.529(4)
_cell_volume                     1493.92(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8660
_cell_measurement_theta_min      3.5090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88031
_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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_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  0.0447
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21311
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.130
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  69.00   0.50    5.00    --    5.23  73.00  85.00  132
  2  ω    -64.00  25.00   0.50    5.00    --    5.23 -73.00 -43.00  178
  3  ω    -16.00  10.00   0.50    5.00    --   -4.91 -99.00 -60.00   52
  4  ω    -22.00  27.00   0.50    5.00    --   -4.91 -99.00 150.00   98
  5  ω    -23.00  28.00   0.50    5.00    --   -4.91 -99.00  30.00  102
  6  ω    -48.00  10.00   0.50    5.00    --    5.23 -57.00  30.00  116
  7  ω     12.00  38.00   0.50    5.00    --    5.23 -99.00-120.00   52
  8  ω     -1.00  47.00   0.50    5.00    --    5.23  38.00-120.00   96
  9  ω    -22.00   3.00   0.50    5.00    --    5.23 -99.00-120.00   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      -0.0322609000
_diffrn_orient_matrix_UB_12      -0.0131420000
_diffrn_orient_matrix_UB_13      0.0373303000
_diffrn_orient_matrix_UB_21      0.0094341000
_diffrn_orient_matrix_UB_22      0.0711006000
_diffrn_orient_matrix_UB_23      0.0143476000
_diffrn_orient_matrix_UB_31      -0.0679747000
_diffrn_orient_matrix_UB_32      -0.0228916000
_diffrn_orient_matrix_UB_33      -0.0296296000
_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                3685
_reflns_number_total             6120
_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 1.3 (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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6120
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1019P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.2094
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C9-C10 \\sim C8-C7 \\sim C6-C5
 with sigma of 0.02
2. Restrained planarity
 C10, C9, C8, C7, C6, C5
 with sigma of 0.1
3. Rigid bond restraints
 C9, C10, C5, C4, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C3 \\sim C4 \\sim C5 \\sim C10 \\sim C9: within 1.4A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.4A
Uanis(C21) = Uanis(C22) = Uanis(C23)
Uanis(C9) = Uanis(C10)
5. Rigid body (RIGU) restrains
 C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C31(H31A,H31B)
6.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C9(H9), C25(H25), C22(H22), C2(H2), C26(H26), C28(H28),
 C27(H27), C6(H6), C4(H4), C8(H8), C3(H3), C7(H7)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C36(H36A,H36B,H36C), C35(H35A,H35B,
 H35C)
;
_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
O5 O -0.0622(2) 0.3848(2) 0.54590(14) 0.0668(5) Uani 1 1 d . . . . .
O4 O 0.17114(19) 0.5948(2) 0.67957(14) 0.0664(5) Uani 1 1 d . . . . .
O3 O 0.4022(2) 0.4379(2) 0.66718(14) 0.0713(6) Uani 1 1 d . . . . .
O6 O -0.0332(2) 0.8861(2) 0.68591(18) 0.0837(7) Uani 1 1 d . . . . .
O1 O 0.3211(2) 0.6637(2) 0.92874(15) 0.0820(7) Uani 1 1 d . . . . .
N1 N 0.3719(2) 0.5458(2) 0.80417(15) 0.0572(6) Uani 1 1 d . . . . .
N2 N 0.0671(2) 0.7406(2) 0.69346(15) 0.0547(6) Uani 1 1 d . . . . .
O2 O 0.0382(2) 0.4886(2) 0.84860(19) 0.0931(8) Uani 1 1 d . . . . .
C13 C -0.2079(2) 0.4916(3) 0.59220(17) 0.0480(6) Uani 1 1 d . . . . .
C12 C -0.0721(3) 0.4849(3) 0.59339(17) 0.0484(6) Uani 1 1 d . . . . .
C14 C -0.1954(2) 0.6403(3) 0.63350(17) 0.0495(6) Uani 1 1 d . . . . .
C23 C 0.7689(3) 0.7908(3) 0.8871(2) 0.0656(5) Uani 1 1 d . . . . .
C11 C 0.0666(3) 0.6108(3) 0.66007(18) 0.0505(6) Uani 1 1 d . . . . .
C15 C -0.0518(3) 0.7651(3) 0.67007(19) 0.0553(6) Uani 1 1 d . . . . .
C16 C -0.2295(3) 0.5384(3) 0.68920(18) 0.0564(7) Uani 1 1 d . . . . .
H16A H -0.325981 0.495928 0.697045 0.068 Uiso 1 1 calc R U . . .
H16B H -0.155347 0.558451 0.742650 0.068 Uiso 1 1 calc R U . . .
C33 C 0.3273(3) 0.4302(3) 0.72171(19) 0.0544(6) Uani 1 1 d . . . . .
C24 C 0.6340(3) 0.6710(3) 0.86925(18) 0.0580(7) Uani 1 1 d . . . . .
C32 C 0.1932(3) 0.2974(3) 0.70784(19) 0.0560(6) Uani 1 1 d . . . . .
C30 C 0.1240(3) 0.4504(3) 0.8249(2) 0.0604(7) Uani 1 1 d . . . . .
C10 C 0.2971(3) 0.9543(3) 0.7182(2) 0.0640(5) Uani 1 1 d D U . . .
C34 C 0.0863(3) 0.3060(3) 0.7657(2) 0.0584(7) Uani 1 1 d . . . . .
C18 C -0.3112(3) 0.6724(3) 0.5926(2) 0.0665(8) Uani 1 1 d . . . . .
H18A H -0.299051 0.686812 0.533500 0.100 Uiso 1 1 calc R U . . .
H18B H -0.304953 0.757174 0.635008 0.100 Uiso 1 1 calc R U . . .
H18C H -0.403183 0.593406 0.583295 0.100 Uiso 1 1 calc R U . . .
C1 C 0.1997(3) 0.8625(3) 0.7564(2) 0.0609(7) Uani 1 1 d . . . . .
C19 C 0.5125(3) 0.6713(3) 0.82281(19) 0.0584(7) Uani 1 1 d . . . . .
C20 C 0.5213(3) 0.7822(3) 0.7949(2) 0.0649(7) Uani 1 1 d . . . . .
H20 H 0.438038 0.778743 0.764169 0.078 Uiso 1 1 calc R U . . .
C29 C 0.2815(3) 0.5628(3) 0.85895(19) 0.0592(7) Uani 1 1 d . . . . .
C17 C -0.3326(3) 0.3815(3) 0.5109(2) 0.0674(8) Uani 1 1 d . . . . .
H17A H -0.325512 0.411668 0.456286 0.101 Uiso 1 1 calc R U . . .
H17B H -0.420481 0.371708 0.526517 0.101 Uiso 1 1 calc R U . . .
H17C H -0.331106 0.291188 0.498251 0.101 Uiso 1 1 calc R U . . .
C21 C 0.6521(3) 0.9033(3) 0.8106(2) 0.0656(5) Uani 1 1 d . . . . .
H21 H 0.655606 0.979009 0.790525 0.079 Uiso 1 1 calc R U . . .
C9 C 0.2784(3) 0.9337(3) 0.6205(2) 0.0640(5) Uani 1 1 d D U . . .
H9 H 0.196384 0.858371 0.577695 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6300(3) 0.5527(3) 0.89911(19) 0.0668(8) Uani 1 1 d . . . . .
H25 H 0.543487 0.472643 0.889702 0.080 Uiso 1 1 calc R U . . .
C22 C 0.7749(3) 0.9081(3) 0.8562(2) 0.0656(5) Uani 1 1 d . . . . .
H22 H 0.862389 0.987718 0.867100 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4212(3) 1.0724(3) 0.7815(2) 0.0738(9) Uani 1 1 d D U . . .
C36 C 0.1370(3) 0.1956(3) 0.6093(2) 0.0742(9) Uani 1 1 d . . . . .
H36A H 0.105469 0.237627 0.568041 0.111 Uiso 1 1 calc R U . . .
H36B H 0.058143 0.108022 0.606919 0.111 Uiso 1 1 calc R U . . .
H36C H 0.211451 0.176208 0.589931 0.111 Uiso 1 1 calc R U . . .
C31 C 0.1835(3) 0.2439(3) 0.7908(2) 0.0668(8) Uani 1 1 d . . . . .
H31A H 0.261525 0.299784 0.846882 0.080 Uiso 1 1 calc R U . . .
H31B H 0.140886 0.141316 0.778507 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2221(3) 0.8817(4) 0.8490(2) 0.0732(9) Uani 1 1 d . . . . .
H2 H 0.156089 0.816733 0.871347 0.088 Uiso 1 1 calc R U . . .
C26 C 0.7544(4) 0.5606(4) 0.9410(2) 0.0748(9) Uani 1 1 d . . . . .
H26 H 0.752281 0.484192 0.959650 0.090 Uiso 1 1 calc R U . . .
C28 C 0.8930(3) 0.7932(4) 0.9321(2) 0.0753(9) Uani 1 1 d . . . . .
H28 H 0.980645 0.873350 0.944777 0.090 Uiso 1 1 calc R U . . .
C35 C -0.0719(3) 0.2092(3) 0.7251(3) 0.0827(10) Uani 1 1 d . . . . .
H35A H -0.108361 0.243772 0.680620 0.124 Uiso 1 1 calc R U . . .
H35B H -0.120297 0.208192 0.774566 0.124 Uiso 1 1 calc R U . . .
H35C H -0.087526 0.114021 0.694121 0.124 Uiso 1 1 calc R U . . .
C27 C 0.8869(4) 0.6807(4) 0.9572(2) 0.0843(10) Uani 1 1 d . . . . .
H27 H 0.970528 0.682201 0.985493 0.101 Uiso 1 1 calc R U . . .
C6 C 0.5230(4) 1.1635(4) 0.7426(4) 0.0986(13) Uani 1 1 d D . . . .
H6 H 0.604621 1.242593 0.783062 0.118 Uiso 1 1 calc R U . . .
C4 C 0.4441(4) 1.0952(4) 0.8779(3) 0.0963(12) Uani 1 1 d . U . . .
H4 H 0.525264 1.174045 0.918877 0.116 Uiso 1 1 calc R U . . .
C8 C 0.3825(4) 1.0261(4) 0.5904(3) 0.0966(11) Uani 1 1 d D . . . .
H8 H 0.370382 1.012230 0.526385 0.116 Uiso 1 1 calc R U . . .
C3 C 0.3458(4) 1.0003(5) 0.9127(2) 0.1008(13) Uani 1 1 d . U . . .
H3 H 0.360908 1.014373 0.976842 0.121 Uiso 1 1 calc R U . . .
C7 C 0.5056(5) 1.1396(4) 0.6516(4) 0.1135(15) Uani 1 1 d D . . . .
H7 H 0.575811 1.198939 0.628595 0.136 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
O5 C12 1.203(3) . ?
O4 C11 1.206(3) . ?
O3 C33 1.209(3) . ?
O6 C15 1.201(3) . ?
O1 C29 1.205(3) . ?
N1 C33 1.405(3) . ?
N1 C19 1.479(3) . ?
N1 C29 1.384(3) . ?
N2 C11 1.376(3) . ?
N2 C15 1.416(3) . ?
N2 C1 1.472(3) . ?
O2 C30 1.206(3) . ?
C13 C12 1.472(3) . ?
C13 C14 1.528(3) . ?
C13 C16 1.515(3) . ?
C13 C17 1.512(3) . ?
C12 C11 1.538(3) . ?
C14 C15 1.479(3) . ?
C14 C16 1.501(4) . ?
C14 C18 1.513(4) . ?
C23 C24 1.417(4) . ?
C23 C22 1.438(4) . ?
C23 C28 1.394(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C33 C32 1.492(4) . ?
C24 C19 1.394(4) . ?
C24 C25 1.446(4) . ?
C32 C34 1.536(4) . ?
C32 C36 1.502(4) . ?
C32 C31 1.503(4) . ?
C30 C34 1.463(4) . ?
C30 C29 1.531(4) . ?
C10 C1 1.401(4) . ?
C10 C9 1.420(4) . ?
C10 C5 1.415(4) . ?
C34 C31 1.507(4) . ?
C34 C35 1.509(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 C2 1.343(4) . ?
C19 C20 1.339(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.403(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.363(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.353(4) . ?
C22 H22 0.9300 . ?
C5 C6 1.429(5) . ?
C5 C4 1.395(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.417(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.407(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.341(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C27 H27 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.315(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.389(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(6) . ?
C3 H3 0.9300 . ?
C7 H7 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
C33 N1 C19 118.4(2) . . ?
C29 N1 C33 123.5(2) . . ?
C29 N1 C19 116.7(2) . . ?
C11 N2 C15 124.0(2) . . ?
C11 N2 C1 118.3(2) . . ?
C15 N2 C1 117.6(2) . . ?
C12 C13 C14 115.9(2) . . ?
C12 C13 C16 113.5(2) . . ?
C12 C13 C17 115.7(2) . . ?
C16 C13 C14 59.12(17) . . ?
C17 C13 C14 119.8(2) . . ?
C17 C13 C16 120.9(2) . . ?
O5 C12 C13 124.0(2) . . ?
O5 C12 C11 117.0(2) . . ?
C13 C12 C11 119.0(2) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 C16 115.0(2) . . ?
C15 C14 C18 114.4(2) . . ?
C16 C14 C13 60.02(16) . . ?
C16 C14 C18 119.2(2) . . ?
C18 C14 C13 118.6(2) . . ?
C24 C23 C22 118.4(3) . . ?
C28 C23 C24 120.5(3) . . ?
C28 C23 C22 121.0(3) . . ?
O4 C11 N2 122.2(2) . . ?
O4 C11 C12 120.0(2) . . ?
N2 C11 C12 117.7(2) . . ?
O6 C15 N2 118.9(2) . . ?
O6 C15 C14 122.7(2) . . ?
N2 C15 C14 118.2(2) . . ?
C13 C16 H16A 117.7 . . ?
C13 C16 H16B 117.7 . . ?
C14 C16 C13 60.86(16) . . ?
C14 C16 H16A 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
O3 C33 N1 119.4(2) . . ?
O3 C33 C32 122.0(2) . . ?
N1 C33 C32 118.4(2) . . ?
C23 C24 C25 117.8(3) . . ?
C19 C24 C23 119.0(3) . . ?
C19 C24 C25 123.2(3) . . ?
C33 C32 C34 118.8(2) . . ?
C33 C32 C36 113.7(2) . . ?
C33 C32 C31 114.6(2) . . ?
C36 C32 C34 118.8(2) . . ?
C36 C32 C31 121.2(2) . . ?
C31 C32 C34 59.43(18) . . ?
O2 C30 C34 124.1(3) . . ?
O2 C30 C29 116.7(2) . . ?
C34 C30 C29 119.2(2) . . ?
C1 C10 C9 123.6(3) . . ?
C1 C10 C5 117.3(3) . . ?
C5 C10 C9 119.0(3) . . ?
C30 C34 C32 114.6(2) . . ?
C30 C34 C31 116.6(3) . . ?
C30 C34 C35 115.1(2) . . ?
C31 C34 C32 59.20(18) . . ?
C31 C34 C35 119.7(2) . . ?
C35 C34 C32 120.2(3) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C1 N2 119.2(3) . . ?
C2 C1 N2 118.3(3) . . ?
C2 C1 C10 122.5(3) . . ?
C24 C19 N1 118.8(2) . . ?
C20 C19 N1 120.0(3) . . ?
C20 C19 C24 121.2(3) . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.2(3) . . ?
C21 C20 H20 118.9 . . ?
O1 C29 N1 122.6(3) . . ?
O1 C29 C30 120.2(2) . . ?
N1 C29 C30 117.2(2) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.6 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(3) . . ?
C26 C25 H25 120.6 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C10 C5 C6 117.5(3) . . ?
C4 C5 C10 120.7(3) . . ?
C4 C5 C6 121.8(3) . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C32 C31 C34 61.37(18) . . ?
C32 C31 H31A 117.6 . . ?
C32 C31 H31B 117.6 . . ?
C34 C31 H31A 117.6 . . ?
C34 C31 H31B 117.6 . . ?
H31A C31 H31B 114.7 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C25 C26 H26 119.0 . . ?
C25 C26 C27 122.1(3) . . ?
C27 C26 H26 119.0 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.5(3) . . ?
C27 C28 H28 119.7 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(4) . . ?
C7 C6 H6 118.8 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C9 C8 H8 118.8 . . ?
C9 C8 C7 122.4(4) . . ?
C7 C8 H8 118.8 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?

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
O5 C12 C11 O4 -17.1(4) . . . . ?
O5 C12 C11 N2 161.1(2) . . . . ?
O3 C33 C32 C34 -165.7(3) . . . . ?
O3 C33 C32 C36 -18.3(4) . . . . ?
O3 C33 C32 C31 127.1(3) . . . . ?
N1 C33 C32 C34 18.8(4) . . . . ?
N1 C33 C32 C36 166.2(2) . . . . ?
N1 C33 C32 C31 -48.4(3) . . . . ?
N1 C19 C20 C21 -179.7(2) . . . . ?
N2 C1 C2 C3 -177.9(3) . . . . ?
O2 C30 C34 C32 152.7(3) . . . . ?
O2 C30 C34 C31 -140.9(3) . . . . ?
O2 C30 C34 C35 7.1(5) . . . . ?
O2 C30 C29 O1 24.5(4) . . . . ?
O2 C30 C29 N1 -152.8(3) . . . . ?
C13 C12 C11 O4 161.8(2) . . . . ?
C13 C12 C11 N2 -20.0(3) . . . . ?
C13 C14 C15 O6 164.7(3) . . . . ?
C13 C14 C15 N2 -20.0(4) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C16 -103.0(2) . . . . ?
C12 C13 C14 C18 147.9(2) . . . . ?
C12 C13 C16 C14 107.2(2) . . . . ?
C14 C13 C12 O5 -162.4(3) . . . . ?
C14 C13 C12 C11 18.7(3) . . . . ?
C23 C24 C19 N1 179.8(2) . . . . ?
C23 C24 C19 C20 0.0(4) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C23 C28 C27 C26 -1.9(5) . . . . ?
C11 N2 C15 O6 -164.4(3) . . . . ?
C11 N2 C15 C14 20.1(4) . . . . ?
C11 N2 C1 C10 92.8(3) . . . . ?
C11 N2 C1 C2 -87.5(3) . . . . ?
C15 N2 C11 O4 178.0(2) . . . . ?
C15 N2 C11 C12 -0.1(4) . . . . ?
C15 N2 C1 C10 -86.4(3) . . . . ?
C15 N2 C1 C2 93.3(3) . . . . ?
C15 C14 C16 C13 -110.5(2) . . . . ?
C16 C13 C12 O5 131.8(3) . . . . ?
C16 C13 C12 C11 -47.0(3) . . . . ?
C16 C13 C14 C15 103.7(3) . . . . ?
C16 C13 C14 C18 -109.1(3) . . . . ?
C16 C14 C15 O6 -127.2(3) . . . . ?
C16 C14 C15 N2 48.2(3) . . . . ?
C33 N1 C19 C24 -87.0(3) . . . . ?
C33 N1 C19 C20 92.8(3) . . . . ?
C33 N1 C29 O1 -178.9(3) . . . . ?
C33 N1 C29 C30 -1.7(4) . . . . ?
C33 C32 C34 C30 4.4(4) . . . . ?
C33 C32 C34 C31 -103.1(3) . . . . ?
C33 C32 C34 C35 148.2(3) . . . . ?
C33 C32 C31 C34 110.1(2) . . . . ?
C24 C23 C22 C21 0.1(4) . . . . ?
C24 C23 C28 C27 1.6(5) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C30 C34 C31 C32 -104.1(3) . . . . ?
C10 C1 C2 C3 1.9(5) . . . . ?
C10 C9 C8 C7 -0.3(5) . . . . ?
C10 C5 C6 C7 -1.0(6) . . . . ?
C10 C5 C4 C3 1.0(5) . . . . ?
C34 C30 C29 O1 -156.4(3) . . . . ?
C34 C30 C29 N1 26.4(4) . . . . ?
C18 C14 C15 O6 16.2(4) . . . . ?
C18 C14 C15 N2 -168.5(2) . . . . ?
C18 C14 C16 C13 108.0(3) . . . . ?
C1 N2 C11 O4 -1.1(4) . . . . ?
C1 N2 C11 C12 -179.3(2) . . . . ?
C1 N2 C15 O6 14.8(4) . . . . ?
C1 N2 C15 C14 -160.8(2) . . . . ?
C1 C10 C9 C8 -177.3(3) . . . . ?
C1 C10 C5 C6 178.0(3) . . . . ?
C1 C10 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C19 N1 C33 O3 -2.2(4) . . . . ?
C19 N1 C33 C32 173.5(2) . . . . ?
C19 N1 C29 O1 -12.6(4) . . . . ?
C19 N1 C29 C30 164.5(2) . . . . ?
C19 C24 C25 C26 177.8(3) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C29 N1 C33 O3 163.9(3) . . . . ?
C29 N1 C33 C32 -20.5(4) . . . . ?
C29 N1 C19 C24 106.0(3) . . . . ?
C29 N1 C19 C20 -74.2(3) . . . . ?
C29 C30 C34 C32 -26.4(4) . . . . ?
C29 C30 C34 C31 40.0(4) . . . . ?
C29 C30 C34 C35 -172.0(3) . . . . ?
C17 C13 C12 O5 -14.4(4) . . . . ?
C17 C13 C12 C11 166.8(2) . . . . ?
C17 C13 C14 C15 -145.9(3) . . . . ?
C17 C13 C14 C16 110.4(3) . . . . ?
C17 C13 C14 C18 1.2(4) . . . . ?
C17 C13 C16 C14 -108.5(3) . . . . ?
C9 C10 C1 N2 -2.5(4) . . . . ?
C9 C10 C1 C2 177.7(3) . . . . ?
C9 C10 C5 C6 -1.2(4) . . . . ?
C9 C10 C5 C4 -179.2(3) . . . . ?
C9 C8 C7 C6 -1.9(7) . . . . ?
C25 C24 C19 N1 1.0(4) . . . . ?
C25 C24 C19 C20 -178.8(3) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C22 C23 C24 C19 -0.1(4) . . . . ?
C22 C23 C24 C25 178.8(3) . . . . ?
C22 C23 C28 C27 -177.3(3) . . . . ?
C5 C10 C1 N2 178.3(2) . . . . ?
C5 C10 C1 C2 -1.4(4) . . . . ?
C5 C10 C9 C8 1.8(4) . . . . ?
C5 C6 C7 C8 2.6(7) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C36 C32 C34 C30 -141.3(3) . . . . ?
C36 C32 C34 C31 111.2(3) . . . . ?
C36 C32 C34 C35 2.5(4) . . . . ?
C36 C32 C31 C34 -107.3(3) . . . . ?
C31 C32 C34 C30 107.5(3) . . . . ?
C31 C32 C34 C35 -108.7(3) . . . . ?
C28 C23 C24 C19 -179.0(3) . . . . ?
C28 C23 C24 C25 -0.1(4) . . . . ?
C28 C23 C22 C21 179.0(3) . . . . ?
C35 C34 C31 C32 109.5(3) . . . . ?
C6 C5 C4 C3 -176.9(3) . . . . ?
C4 C5 C6 C7 177.0(4) . . . . ?

_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.818
