# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

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

data_thdb-157_auto
_database_code_depnum_ccdc_archive 'CCDC 2376544'
loop_
_audit_author_name
_audit_author_address
'Clemens Kaussler'
;Aarhus University
Denmark
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
ck@inano.au.dk
julia.kolodiazhnaia@inano.au.dk
frj@chem.au.dk
ts@inano.au.dk
croque@unicamp.br
_chemical_name_common            ?
_chemical_name_systematic        
(R)-5-methyl-2H,2'H-spiro[benzofuran-3,3'-furan]-5'(4'H)-one
_chemical_formula_moiety         '2(C12 H12 O3)'
_chemical_formula_sum            'C24 H24 O6'
_chemical_formula_weight         408.43
_chemical_absolute_configuration R
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H9O5N
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'
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                   13.3053(4)
_cell_length_b                   5.61720(10)
_cell_length_c                   14.4165(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.784(4)
_cell_angle_gamma                90
_cell_volume                     1000.53(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26600
_cell_measurement_temperature    110(10)
_cell_measurement_theta_max      30.4080
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.591
_diffrn_reflns_theta_min         2.626
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00 -26.00   0.50    6.85    --   -2.08 150.00 -82.00  100
  2  ω    -59.00 -11.00   0.50    6.85    --   -2.08 123.00 115.00   96
  3  ω    -31.00  67.00   0.50    6.85    --   -2.08  77.00 -90.00  196
  4  ω    -60.00 -12.00   0.50    6.85    --   -2.08 124.00 174.97   96
  5  ω    -82.00  18.00   0.50    6.85    --   -2.08 -38.00 -60.00  200
  6  ω    -55.00  -5.00   0.50    6.85    --   -2.08 114.00 -18.14  100
  7  ω    -74.00  24.00   0.50    6.85    --    2.62 -57.00 -90.00  196
  8  ω    -74.00  24.00   0.50    6.85    --    2.62 -57.00 120.00  196
  9  ω    -27.00  84.00   0.50    6.85    --    2.62  19.00 -60.00  222
 10  ω    -59.00 -11.00   0.50    6.85    --   -2.08 123.00  44.91   96
 11  ω    -60.00 -12.00   0.50    6.85    --   -2.08 124.00  85.54   96
 12  ω    -58.00  -9.00   0.50    6.85    --   -2.08 120.00-121.54   98
 13  ω    -63.00 -16.00   0.50    6.85    --   -2.08 130.00 -88.50   94
 14  ω    -58.00  -9.00   0.50    6.85    --   -2.08 120.00-142.80   98
 15  ω    -54.00  -4.00   0.50    6.85    --   -2.08 113.00 102.10  100
 16  ω    -57.00  -8.00   0.50    6.85    --   -2.08 118.00  11.98   98
 17  ω     31.00  61.00   0.50    6.85    --    2.62-122.00 -36.22   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0556557000
_diffrn_orient_matrix_UB_12      0.0281276000
_diffrn_orient_matrix_UB_13      0.0139815000
_diffrn_orient_matrix_UB_21      0.0083411000
_diffrn_orient_matrix_UB_22      -0.0229441000
_diffrn_orient_matrix_UB_23      0.0507026000
_diffrn_orient_matrix_UB_31      0.0113557000
_diffrn_orient_matrix_UB_32      -0.1209669000
_diffrn_orient_matrix_UB_33      -0.0063368000
_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         0.735
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                4790
_reflns_number_total             5352
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1905 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.074
_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)+(0.0708P)²+0.0831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1125
_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:
 C2(H2A,H2B), C2'(H2'A,H2'B), C4'(H4'A,H4'B), C2A(H2AA,H2AB), C2A'(H2AC,H2AD),
 C4A'(H4AA,H4AB)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C4A(H4A), C6A(H6A), C7A(H7A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F)
;
_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
O1 O 0.90687(12) 0.6795(3) 0.82336(11) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.90136(17) 0.5530(4) 0.73364(15) 0.0245(4) Uani 1 1 d . . . . .
H2A H 0.825009 0.527568 0.689149 0.029 Uiso 1 1 calc R U . . .
H2B H 0.937232 0.395955 0.751201 0.029 Uiso 1 1 calc R U . . .
C3 C 0.96021(15) 0.7097(3) 0.68102(13) 0.0192(4) Uani 1 1 d . . . . .
C4 C 1.11123(14) 1.0212(3) 0.77556(14) 0.0203(4) Uani 1 1 d . . . . .
H4 H 1.136715 1.037164 0.722430 0.024 Uiso 1 1 calc R U . . .
C5 C 1.15781(15) 1.1552(4) 0.86281(15) 0.0230(4) Uani 1 1 d . . . . .
C6 C 1.11911(16) 1.1232(4) 0.94018(15) 0.0261(4) Uani 1 1 d . . . . .
H6 H 1.151170 1.211692 1.000146 0.031 Uiso 1 1 calc R U . . .
C7 C 1.03546(16) 0.9666(4) 0.93206(14) 0.0255(4) Uani 1 1 d . . . . .
H7 H 1.009921 0.947540 0.985019 0.031 Uiso 1 1 calc R U . . .
C8 C 0.99076(15) 0.8395(4) 0.84423(14) 0.0209(4) Uani 1 1 d . . . . .
C9 C 1.02770(14) 0.8651(3) 0.76704(13) 0.0178(3) Uani 1 1 d . . . . .
C10 C 1.24581(18) 1.3334(4) 0.87270(18) 0.0329(5) Uani 1 1 d . . . . .
H10A H 1.270719 1.313433 0.817169 0.049 Uiso 1 1 calc R U . . .
H10B H 1.306515 1.307720 0.936090 0.049 Uiso 1 1 calc R U . . .
H10C H 1.217429 1.494882 0.871294 0.049 Uiso 1 1 calc R U . . .
O1' O 0.95235(12) 0.5206(3) 0.53033(10) 0.0264(3) Uani 1 1 d . . . . .
C2' C 1.02517(17) 0.5667(4) 0.63199(15) 0.0248(4) Uani 1 1 d . . . . .
H2'A H 1.088796 0.658826 0.632500 0.030 Uiso 1 1 calc R U . . .
H2'B H 1.050724 0.415233 0.668203 0.030 Uiso 1 1 calc R U . . .
C4' C 0.88198(15) 0.8464(4) 0.59036(14) 0.0215(4) Uani 1 1 d . . . . .
H4'A H 0.810591 0.868189 0.595911 0.026 Uiso 1 1 calc R U . . .
H4'B H 0.911710 1.004270 0.583766 0.026 Uiso 1 1 calc R U . . .
C5' C 0.87307(16) 0.6868(4) 0.50266(14) 0.0246(4) Uani 1 1 d . . . . .
O6' O 0.80871(12) 0.6951(3) 0.41822(11) 0.0302(4) Uani 1 1 d . . . . .
O1A O 0.59642(12) 0.2781(3) 0.16296(10) 0.0265(3) Uani 1 1 d . . . . .
C2A C 0.60824(17) 0.4275(4) 0.24838(14) 0.0257(4) Uani 1 1 d . . . . .
H2AA H 0.571299 0.581969 0.226264 0.031 Uiso 1 1 calc R U . . .
H2AB H 0.685719 0.458030 0.287777 0.031 Uiso 1 1 calc R U . . .
C3A C 0.55589(15) 0.2901(4) 0.31176(13) 0.0199(4) Uani 1 1 d . . . . .
C4A C 0.39350(15) -0.0109(3) 0.23300(15) 0.0223(4) Uani 1 1 d . . . . .
H4A H 0.371055 -0.008424 0.288331 0.027 Uiso 1 1 calc R U . . .
C5A C 0.34188(16) -0.1609(4) 0.15123(16) 0.0265(4) Uani 1 1 d . . . . .
C6A C 0.37612(17) -0.1575(4) 0.07100(16) 0.0281(4) Uani 1 1 d . . . . .
H6A H 0.340668 -0.257961 0.015428 0.034 Uiso 1 1 calc R U . . .
C7A C 0.46033(17) -0.0126(4) 0.06881(14) 0.0269(4) Uani 1 1 d . . . . .
H7A H 0.482510 -0.012495 0.013312 0.032 Uiso 1 1 calc R U . . .
C8A C 0.51015(15) 0.1310(4) 0.15118(14) 0.0216(4) Uani 1 1 d . . . . .
C9A C 0.47754(15) 0.1335(4) 0.23212(13) 0.0192(4) Uani 1 1 d . . . . .
C10A C 0.25281(19) -0.3267(5) 0.1521(2) 0.0371(5) Uani 1 1 d . . . . .
H10D H 0.251048 -0.331858 0.219395 0.056 Uiso 1 1 calc R U . . .
H10E H 0.266506 -0.486834 0.132490 0.056 Uiso 1 1 calc R U . . .
H10F H 0.183095 -0.268884 0.104858 0.056 Uiso 1 1 calc R U . . .
O1A' O 0.67906(12) 0.2911(3) 0.48163(10) 0.0288(3) Uani 1 1 d . . . . .
C2A' C 0.63804(18) 0.1381(4) 0.39458(14) 0.0272(4) Uani 1 1 d . . . . .
H2AC H 0.602303 -0.003974 0.409050 0.033 Uiso 1 1 calc R U . . .
H2AD H 0.697657 0.085003 0.374045 0.033 Uiso 1 1 calc R U . . .
C4A' C 0.51500(17) 0.4546(4) 0.37360(15) 0.0247(4) Uani 1 1 d . . . . .
H4AA H 0.496542 0.613282 0.341942 0.030 Uiso 1 1 calc R U . . .
H4AB H 0.450403 0.386945 0.382392 0.030 Uiso 1 1 calc R U . . .
C5A' C 0.60925(17) 0.4703(4) 0.47223(15) 0.0264(4) Uani 1 1 d . . . . .
O6A' O 0.62589(14) 0.6161(3) 0.53792(12) 0.0367(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.454(2) . ?
O1 C8 1.377(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.551(3) . ?
C3 C9 1.510(2) . ?
C3 C2' 1.531(3) . ?
C3 C4' 1.540(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.398(3) . ?
C4 C9 1.385(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.506(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(3) . ?
C8 C9 1.381(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1' C2' 1.449(2) . ?
O1' C5' 1.353(3) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4' C5' 1.518(3) . ?
C5' O6' 1.201(3) . ?
O1A C2A 1.450(2) . ?
O1A C8A 1.373(2) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.545(3) . ?
C3A C9A 1.513(3) . ?
C3A C2A' 1.543(3) . ?
C3A C4A' 1.518(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.404(3) . ?
C4A C9A 1.385(3) . ?
C5A C6A 1.392(3) . ?
C5A C10A 1.511(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.395(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.384(3) . ?
C8A C9A 1.388(3) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
O1A' C2A' 1.450(2) . ?
O1A' C5A' 1.342(3) . ?
C2A' H2AC 0.9900 . ?
C2A' H2AD 0.9900 . ?
C4A' H4AA 0.9900 . ?
C4A' H4AB 0.9900 . ?
C4A' C5A' 1.510(3) . ?
C5A' O6A' 1.209(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C2 106.43(14) . . ?
O1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
O1 C2 C3 106.84(15) . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C9 C3 C2 100.42(14) . . ?
C9 C3 C2' 114.64(16) . . ?
C9 C3 C4' 114.69(16) . . ?
C2' C3 C2 113.69(16) . . ?
C2' C3 C4' 100.91(15) . . ?
C4' C3 C2 113.16(16) . . ?
C5 C4 H4 120.2 . . ?
C9 C4 H4 120.2 . . ?
C9 C4 C5 119.60(17) . . ?
C4 C5 C6 118.40(18) . . ?
C4 C5 C10 120.83(18) . . ?
C6 C5 C10 120.76(18) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.21(19) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.62(17) . . ?
C8 C7 H7 121.2 . . ?
O1 C8 C7 125.18(17) . . ?
O1 C8 C9 113.21(17) . . ?
C9 C8 C7 121.60(18) . . ?
C4 C9 C3 130.70(17) . . ?
C8 C9 C3 108.70(16) . . ?
C8 C9 C4 120.56(17) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5' O1' C2' 109.30(15) . . ?
C3 C2' H2'A 110.5 . . ?
C3 C2' H2'B 110.5 . . ?
O1' C2' C3 106.29(16) . . ?
O1' C2' H2'A 110.5 . . ?
O1' C2' H2'B 110.5 . . ?
H2'A C2' H2'B 108.7 . . ?
C3 C4' H4'A 111.1 . . ?
C3 C4' H4'B 111.1 . . ?
H4'A C4' H4'B 109.0 . . ?
C5' C4' C3 103.40(16) . . ?
C5' C4' H4'A 111.1 . . ?
C5' C4' H4'B 111.1 . . ?
O1' C5' C4' 110.51(16) . . ?
O6' C5' O1' 120.68(18) . . ?
O6' C5' C4' 128.8(2) . . ?
C8A O1A C2A 106.00(14) . . ?
O1A C2A H2AA 110.4 . . ?
O1A C2A H2AB 110.4 . . ?
O1A C2A C3A 106.42(15) . . ?
H2AA C2A H2AB 108.6 . . ?
C3A C2A H2AA 110.4 . . ?
C3A C2A H2AB 110.4 . . ?
C9A C3A C2A 100.16(14) . . ?
C9A C3A C2A' 110.87(16) . . ?
C9A C3A C4A' 120.21(16) . . ?
C2A' C3A C2A 112.86(16) . . ?
C4A' C3A C2A 112.44(17) . . ?
C4A' C3A C2A' 100.82(15) . . ?
C5A C4A H4A 120.4 . . ?
C9A C4A H4A 120.4 . . ?
C9A C4A C5A 119.27(18) . . ?
C4A C5A C10A 120.3(2) . . ?
C6A C5A C4A 118.73(19) . . ?
C6A C5A C10A 120.98(19) . . ?
C5A C6A H6A 118.6 . . ?
C5A C6A C7A 122.71(18) . . ?
C7A C6A H6A 118.6 . . ?
C6A C7A H7A 121.5 . . ?
C8A C7A C6A 116.98(18) . . ?
C8A C7A H7A 121.5 . . ?
O1A C8A C7A 124.69(18) . . ?
O1A C8A C9A 113.45(17) . . ?
C7A C8A C9A 121.84(18) . . ?
C4A C9A C3A 131.64(17) . . ?
C4A C9A C8A 120.47(17) . . ?
C8A C9A C3A 107.55(16) . . ?
C5A C10A H10D 109.5 . . ?
C5A C10A H10E 109.5 . . ?
C5A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C5A' O1A' C2A' 109.45(15) . . ?
C3A C2A' H2AC 110.6 . . ?
C3A C2A' H2AD 110.6 . . ?
O1A' C2A' C3A 105.82(16) . . ?
O1A' C2A' H2AC 110.6 . . ?
O1A' C2A' H2AD 110.6 . . ?
H2AC C2A' H2AD 108.7 . . ?
C3A C4A' H4AA 111.0 . . ?
C3A C4A' H4AB 111.0 . . ?
H4AA C4A' H4AB 109.0 . . ?
C5A' C4A' C3A 103.61(16) . . ?
C5A' C4A' H4AA 111.0 . . ?
C5A' C4A' H4AB 111.0 . . ?
O1A' C5A' C4A' 110.69(17) . . ?
O6A' C5A' O1A' 120.7(2) . . ?
O6A' C5A' C4A' 128.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C9 20.08(19) . . . . ?
O1 C2 C3 C2' 143.00(16) . . . . ?
O1 C2 C3 C4' -102.64(18) . . . . ?
O1 C8 C9 C3 1.5(2) . . . . ?
O1 C8 C9 C4 179.37(17) . . . . ?
C2 O1 C8 C7 -168.36(19) . . . . ?
C2 O1 C8 C9 12.1(2) . . . . ?
C2 C3 C9 C4 169.21(19) . . . . ?
C2 C3 C9 C8 -13.3(2) . . . . ?
C2 C3 C2' O1' 90.73(19) . . . . ?
C2 C3 C4' C5' -95.35(18) . . . . ?
C3 C4' C5' O1' -14.3(2) . . . . ?
C3 C4' C5' O6' 166.6(2) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C4 C9 C3 176.78(19) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 O1 -179.22(18) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C3 -178.05(18) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C8 O1 C2 C3 -20.2(2) . . . . ?
C9 C3 C2' O1' -154.53(16) . . . . ?
C9 C3 C4' C5' 150.26(16) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C9 C4 C5 C10 -177.60(18) . . . . ?
C10 C5 C6 C7 177.7(2) . . . . ?
C2' C3 C9 C4 47.0(3) . . . . ?
C2' C3 C9 C8 -135.51(17) . . . . ?
C2' C3 C4' C5' 26.48(18) . . . . ?
C2' O1' C5' C4' -5.6(2) . . . . ?
C2' O1' C5' O6' 173.65(18) . . . . ?
C4' C3 C9 C4 -69.2(3) . . . . ?
C4' C3 C9 C8 108.39(19) . . . . ?
C4' C3 C2' O1' -30.72(19) . . . . ?
C5' O1' C2' C3 23.6(2) . . . . ?
O1A C2A C3A C9A -24.70(19) . . . . ?
O1A C2A C3A C2A' 93.22(19) . . . . ?
O1A C2A C3A C4A' -153.54(16) . . . . ?
O1A C8A C9A C3A -4.0(2) . . . . ?
O1A C8A C9A C4A -178.07(17) . . . . ?
C2A O1A C8A C7A 168.9(2) . . . . ?
C2A O1A C8A C9A -12.6(2) . . . . ?
C2A C3A C9A C4A -169.4(2) . . . . ?
C2A C3A C9A C8A 17.4(2) . . . . ?
C2A C3A C2A' O1A' 90.15(19) . . . . ?
C2A C3A C4A' C5A' -92.48(19) . . . . ?
C3A C4A' C5A' O1A' -17.8(2) . . . . ?
C3A C4A' C5A' O6A' 162.5(2) . . . . ?
C4A C5A C6A C7A 0.6(3) . . . . ?
C5A C4A C9A C3A -172.1(2) . . . . ?
C5A C4A C9A C8A 0.3(3) . . . . ?
C5A C6A C7A C8A 0.1(3) . . . . ?
C6A C7A C8A O1A 177.70(19) . . . . ?
C6A C7A C8A C9A -0.6(3) . . . . ?
C7A C8A C9A C3A 174.49(19) . . . . ?
C7A C8A C9A C4A 0.4(3) . . . . ?
C8A O1A C2A C3A 23.6(2) . . . . ?
C9A C3A C2A' O1A' -158.41(16) . . . . ?
C9A C3A C4A' C5A' 150.05(17) . . . . ?
C9A C4A C5A C6A -0.8(3) . . . . ?
C9A C4A C5A C10A 177.7(2) . . . . ?
C10A C5A C6A C7A -177.9(2) . . . . ?
C2A' C3A C9A C4A 71.2(3) . . . . ?
C2A' C3A C9A C8A -101.98(19) . . . . ?
C2A' C3A C4A' C5A' 28.0(2) . . . . ?
C2A' O1A' C5A' C4A' -1.9(2) . . . . ?
C2A' O1A' C5A' O6A' 177.9(2) . . . . ?
C4A' C3A C9A C4A -45.9(3) . . . . ?
C4A' C3A C9A C8A 140.99(19) . . . . ?
C4A' C3A C2A' O1A' -30.0(2) . . . . ?
C5A' O1A' C2A' C3A 20.6(2) . . . . ?

_olex2_date_sample_data_collection 2023-09-06
_olex2_exptl_crystal_mounting_method 
'immersed in Paratone N, mounted on loop, transferred to diffractometer'
_olex2_submission_original_sample_id THDB-157
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.422
####################################################################### 
# 
# 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_thdb-127-100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2376545'
loop_
_audit_author_name
_audit_author_address
'Clemens Kaussler'
;Aarhus University
Denmark
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-12-17 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
ck@inano.au.dk
julia.kolodiazhnaia@inano.au.dk
frj@chem.au.dk
ts@inano.au.dk
croque@unicamp.br
_chemical_name_common            ?
_chemical_name_systematic        
(R)-5'-oxo-4',5'-dihydro-2H,2'H-spiro[benzofuran-3,3'-furan]-6-carbonitrile
_chemical_formula_moiety         'C12 H9 N O3'
_chemical_formula_sum            'C12 H9 N O3'
_chemical_formula_weight         215.20
_chemical_absolute_configuration R
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H9NO3
_chemical_oxdiff_usercomment     'removed edge (possible defects) and 100 K'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.8376(6)
_cell_length_b                   8.7353(3)
_cell_length_c                   6.9909(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     967.16(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20131
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3420
_cell_measurement_theta_min      3.4840
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            42883
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.596
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  69.00   1.00    7.96    --   10.10-131.00  53.00   60
  2  ω     13.00  74.00   1.00    7.96    --   10.10-138.00-121.00   61
  3  ω    -75.00 -13.00   1.00    7.96    --  -10.88 138.00 -60.00   62
  4  ω    -70.00  -9.00   1.00    7.96    --  -10.88 131.00 124.00   61
  5  ω    -18.00  83.00   1.00    7.96    --   10.10  57.00-150.00  101
  6  ω    -63.00  38.00   1.00    7.96    --   10.10 -57.00-120.00  101
  7  ω    -18.00  83.00   1.00    7.96    --   10.10  57.00  30.00  101
  8  ω    -22.00  42.00   1.00    7.96    --   10.10  77.00 -30.00   64
  9  ω    -22.00  42.00   1.00    7.96    --   10.10  77.00 150.00   64
 10  ω    -15.00  50.00   1.00    7.96    --   10.10 -99.00 -30.00   65
 11  ω    -63.00  38.00   1.00    7.96    --   10.10 -57.00  60.00  101
 12  ω    -47.00  31.00   1.00    7.96    --  -10.88  87.00 121.17   78
 13  ω    -78.00  42.00   1.00    7.96    --   10.10   0.00-180.00  120
 14  ω    -86.00 -20.00   1.00    7.96    --  -10.88 153.00 -81.94   66
 15  ω    -86.00 -20.00   1.00    7.96    --  -10.88 153.00 161.40   66
 16  ω    -42.00  22.00   1.00    7.96    --  -10.88 -77.00  30.00   64
 17  ω    -88.00 -22.00   1.00    7.96    --  -10.88 156.00  82.57   66
 18  ω    -86.00 -20.00   1.00    7.96    --  -10.88 153.00-111.59   66
 19  ω    -87.00 -21.00   1.00    7.96    --  -10.88 154.00-161.45   66
 20  ω    -86.00 -20.00   1.00    7.96    --  -10.88 153.00   4.37   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0006628000
_diffrn_orient_matrix_UB_12      0.0019141000
_diffrn_orient_matrix_UB_13      0.1014053000
_diffrn_orient_matrix_UB_21      -0.0447585000
_diffrn_orient_matrix_UB_22      -0.0023684000
_diffrn_orient_matrix_UB_23      -0.0015740000
_diffrn_orient_matrix_UB_31      0.0012924000
_diffrn_orient_matrix_UB_32      -0.0811595000
_diffrn_orient_matrix_UB_33      0.0024354000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2378
_reflns_number_total             2603
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.054
_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)+(0.0670P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2A',H2B'), C4'(H4A',H4B')
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
;
_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
O1 O 0.78438(9) 0.49546(16) 0.7931(3) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.70148(11) 0.5655(2) 0.7839(3) 0.0196(4) Uani 1 1 d . . . . .
H2A H 0.696468 0.628661 0.666894 0.024 Uiso 1 1 calc R U . . .
H2B H 0.692415 0.632247 0.896467 0.024 Uiso 1 1 calc R U . . .
C3 C 0.63508(11) 0.4352(2) 0.7811(3) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.67085(13) 0.1418(2) 0.7573(4) 0.0292(5) Uani 1 1 d . . . . .
H4 H 0.613570 0.110062 0.749502 0.035 Uiso 1 1 calc R U . . .
C5 C 0.73566(14) 0.0341(2) 0.7545(4) 0.0294(5) Uani 1 1 d . . . . .
H5 H 0.722873 -0.071967 0.745671 0.035 Uiso 1 1 calc R U . . .
C6 C 0.81951(13) 0.0827(2) 0.7647(3) 0.0220(4) Uani 1 1 d . . . . .
C7 C 0.84098(12) 0.2376(2) 0.7786(3) 0.0219(4) Uani 1 1 d . . . . .
H7 H 0.898087 0.270325 0.786104 0.026 Uiso 1 1 calc R U . . .
C8 C 0.77462(12) 0.3406(2) 0.7807(3) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.69088(12) 0.2954(2) 0.7716(3) 0.0192(4) Uani 1 1 d . . . . .
C10 C 0.88590(13) -0.0298(2) 0.7591(3) 0.0260(4) Uani 1 1 d . . . . .
N11 N 0.93788(13) -0.1213(2) 0.7550(3) 0.0352(5) Uani 1 1 d . . . . .
O1' O 0.50078(10) 0.35679(18) 0.8990(3) 0.0295(4) Uani 1 1 d . . . . .
C2' C 0.57739(13) 0.4340(3) 0.9590(3) 0.0246(4) Uani 1 1 d . . . . .
H2A' H 0.604598 0.378202 1.065754 0.030 Uiso 1 1 calc R U . . .
H2B' H 0.564870 0.539789 1.001301 0.030 Uiso 1 1 calc R U . . .
C4' C 0.56959(13) 0.4425(2) 0.6208(3) 0.0243(4) Uani 1 1 d . . . . .
H4A' H 0.556259 0.549792 0.586789 0.029 Uiso 1 1 calc R U . . .
H4B' H 0.589658 0.388052 0.505242 0.029 Uiso 1 1 calc R U . . .
C5' C 0.49386(13) 0.3633(2) 0.7070(4) 0.0264(5) Uani 1 1 d . . . . .
O6' O 0.43314(10) 0.3093(2) 0.6283(3) 0.0355(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.450(2) . ?
O1 C8 1.365(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.550(2) . ?
C3 C9 1.509(2) . ?
C3 C2' 1.544(3) . ?
C3 C4' 1.528(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C4 C9 1.383(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C6 C7 1.399(3) . ?
C6 C10 1.440(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 C9 1.385(3) . ?
C10 N11 1.148(3) . ?
O1' C2' 1.450(3) . ?
O1' C5' 1.348(3) . ?
C2' H2A' 0.9900 . ?
C2' H2B' 0.9900 . ?
C4' H4A' 0.9900 . ?
C4' H4B' 0.9900 . ?
C4' C5' 1.510(3) . ?
C5' O6' 1.204(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C2 108.22(14) . . ?
O1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
O1 C2 C3 107.78(15) . . ?
H2A C2 H2B 108.5 . . ?
C3 C2 H2A 110.2 . . ?
C3 C2 H2B 110.2 . . ?
C9 C3 C2 101.39(14) . . ?
C9 C3 C2' 112.13(16) . . ?
C9 C3 C4' 113.53(17) . . ?
C2' C3 C2 113.34(17) . . ?
C4' C3 C2 116.07(16) . . ?
C4' C3 C2' 100.91(15) . . ?
C5 C4 H4 120.4 . . ?
C9 C4 H4 120.4 . . ?
C9 C4 C5 119.19(19) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.67(18) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 121.94(18) . . ?
C5 C6 C10 119.07(18) . . ?
C7 C6 C10 118.99(18) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 C6 116.43(18) . . ?
C8 C7 H7 121.8 . . ?
O1 C8 C7 124.01(17) . . ?
O1 C8 C9 113.20(16) . . ?
C7 C8 C9 122.79(18) . . ?
C4 C9 C3 130.87(18) . . ?
C4 C9 C8 119.97(18) . . ?
C8 C9 C3 109.16(16) . . ?
N11 C10 C6 178.9(2) . . ?
C5' O1' C2' 109.67(17) . . ?
C3 C2' H2A' 110.7 . . ?
C3 C2' H2B' 110.7 . . ?
O1' C2' C3 105.38(17) . . ?
O1' C2' H2A' 110.7 . . ?
O1' C2' H2B' 110.7 . . ?
H2A' C2' H2B' 108.8 . . ?
C3 C4' H4A' 111.1 . . ?
C3 C4' H4B' 111.1 . . ?
H4A' C4' H4B' 109.1 . . ?
C5' C4' C3 103.17(18) . . ?
C5' C4' H4A' 111.1 . . ?
C5' C4' H4B' 111.1 . . ?
O1' C5' C4' 110.59(18) . . ?
O6' C5' O1' 120.2(2) . . ?
O6' C5' C4' 129.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C9 -4.9(2) . . . . ?
O1 C2 C3 C2' 115.51(19) . . . . ?
O1 C2 C3 C4' -128.35(19) . . . . ?
O1 C8 C9 C3 -0.7(3) . . . . ?
O1 C8 C9 C4 179.6(2) . . . . ?
C2 O1 C8 C7 177.8(2) . . . . ?
C2 O1 C8 C9 -2.6(3) . . . . ?
C2 C3 C9 C4 -176.9(2) . . . . ?
C2 C3 C9 C8 3.4(2) . . . . ?
C2 C3 C2' O1' 155.88(16) . . . . ?
C2 C3 C4' C5' -151.74(16) . . . . ?
C3 C4' C5' O1' 18.0(2) . . . . ?
C3 C4' C5' O6' -161.8(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C4 C5 C6 C10 -179.2(2) . . . . ?
C5 C4 C9 C3 -178.9(2) . . . . ?
C5 C4 C9 C8 0.8(4) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 O1 -179.9(2) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C3 178.85(19) . . . . ?
C7 C8 C9 C4 -0.9(3) . . . . ?
C8 O1 C2 C3 4.7(2) . . . . ?
C9 C3 C2' O1' -90.06(19) . . . . ?
C9 C3 C4' C5' 91.34(19) . . . . ?
C9 C4 C5 C6 -0.5(4) . . . . ?
C10 C6 C7 C8 179.1(2) . . . . ?
C2' C3 C9 C4 61.9(3) . . . . ?
C2' C3 C9 C8 -117.80(19) . . . . ?
C2' C3 C4' C5' -28.82(19) . . . . ?
C2' O1' C5' C4' 2.3(2) . . . . ?
C2' O1' C5' O6' -177.93(18) . . . . ?
C4' C3 C9 C4 -51.7(3) . . . . ?
C4' C3 C9 C8 128.63(19) . . . . ?
C4' C3 C2' O1' 31.09(19) . . . . ?
C5' O1' C2' C3 -21.6(2) . . . . ?

_olex2_date_sample_data_collection 2023-06-01
_olex2_exptl_crystal_mounting_method 
'immersed in Paratone N, mounted on loop, transferred to diffractometer'
_olex2_submission_original_sample_id THDB-127
_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 1.822
_oxdiff_exptl_absorpt_empirical_full_min 0.456
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
