# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_ab-89-2-4f20
_database_code_depnum_ccdc_archive 'CCDC 2378696'
loop_
_audit_author_name
_audit_author_address
'Julia Bruno'
;University College Dublin
Ireland
;
_audit_update_record             
;
2024-08-20 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-10-24
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O2'
_chemical_formula_sum            'C11 H12 O2'
_chemical_formula_weight         176.21
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H14O2
_chemical_oxdiff_usercomment     AB-89-2-4F20_ArleneBooner_Baumann
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.30770(10)
_cell_length_b                   7.30800(10)
_cell_length_c                   10.1790(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     841.16(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7202
_cell_measurement_temperature    104.6(3)
_cell_measurement_theta_max      76.0580
_cell_measurement_theta_min      4.3140
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -2 -4 0.0897
1 0 -7 0.1141
7 2 0 0.0759
-6 -2 -1 0.0703
2 1 6 0.1256
-4 2 -4 0.0648
1 1 -6 0.1077
6 -2 -1 0.0970
4 -2 4 0.1240
-6 2 2 0.0613
0 -5 -2 0.0955
-1 -4 2 0.0865
0 5 0 0.0447
2 4 -4 0.0657
-1 3 5 0.0696

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.4025 -1.9874 -3.5117 -0.2268 -0.9448 0.2365
0.5694 -0.1790 -6.5813 -0.0606 -0.2614 0.9633
6.5353 2.1506 -0.2890 0.2193 0.9073 0.3589
-6.4573 -2.1847 -0.7833 -0.2296 -0.9519 -0.2027
1.9460 0.9926 6.2171 0.1419 0.5975 -0.7892
-4.1831 2.4695 -4.2014 0.6420 -0.6084 0.4666
0.7514 1.0422 -6.4096 0.1829 -0.1705 0.9682
6.3807 -2.2866 -0.7288 -0.6822 0.6493 0.3363
3.9828 -2.4332 4.3956 -0.6277 0.5947 -0.5023
-6.2099 1.8854 2.3488 0.5957 -0.5678 -0.5681
0.3561 -4.5101 -2.0226 -0.9347 -0.2756 0.2246
-1.2647 -4.3322 2.4426 -0.8405 -0.2497 -0.4808
0.3825 4.7376 0.0596 0.9549 0.2825 0.0921
1.7135 3.7145 -3.8113 0.6983 0.2082 0.6849
-1.4719 3.1543 4.7519 0.6973 0.2042 -0.6871

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9796
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.266
_diffrn_reflns_theta_min         6.055
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  75.00   1.00    1.00    --   42.20 -25.00   7.00  111
  2  ω     26.00  95.00   1.00    1.00    --   42.20-123.00 153.00   69
  3  ω     32.00 107.00   1.00    1.50    --  112.00 -99.00-128.00   75
  4  ω     80.00 178.00   1.00    1.50    --  112.00  25.00 170.00   98
  5  ω    104.00 178.00   1.00    1.50    --  112.00  99.00 -22.00   74
  6  ω     40.00 111.00   1.00    1.50    --  112.00-123.00 153.00   71
  7  ω     18.00 117.00   1.00    1.00    --   42.20  37.00  60.00   99
  8  ω      6.00  82.00   1.00    1.00    --   42.20 -99.00   0.00   76
  9  ω     40.00 141.00   1.00    1.50    --  112.00 -61.00-150.00  101
 10  ω     39.00 138.00   1.00    1.50    --  112.00 -45.00  30.00   99
 11  ω     39.00 109.00   1.00    1.50    --  112.00-111.00-150.00   70
 12  ω     39.00 109.00   1.00    1.50    --  112.00-111.00 -60.00   70
 13  ω     36.00 145.00   1.00    1.50    --  112.00 -77.00  30.00  109
 14  ω    -67.00  32.00   1.00    1.00    --  -42.20  37.00 -60.00   99
 15  ω     14.00 114.00   1.00    1.00    --   42.20  57.00-150.00  100
 16  ω     14.00 114.00   1.00    1.00    --   42.20  57.00 150.00  100
 17  ω     14.00 114.00   1.00    1.00    --   42.20  57.00 -60.00  100
 18  ω     84.00 178.00   1.00    1.50    --  112.00  30.00  60.00   94
 19  ω     86.00 178.00   1.00    1.50    --  112.00  45.00   0.00   92
 20  ω     59.00 178.00   1.00    1.50    --  112.00  15.00 -60.00  119
 21  ω     86.00 178.00   1.00    1.50    --  112.00  45.00-150.00   92
 22  ω     39.00  90.00   1.00    1.50    --  112.00-111.00  30.00   51
 23  ω     83.00 178.00   1.00    1.50    --  112.00  61.00  90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0336297000
_diffrn_orient_matrix_UB_12      0.2042525000
_diffrn_orient_matrix_UB_13      0.0007364000
_diffrn_orient_matrix_UB_21      0.1249024000
_diffrn_orient_matrix_UB_22      0.0489178000
_diffrn_orient_matrix_UB_23      0.0491985000
_diffrn_orient_matrix_UB_31      0.0427342000
_diffrn_orient_matrix_UB_32      0.0177821000
_diffrn_orient_matrix_UB_33      -0.1431595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.838
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                1567
_reflns_number_total             1600
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(10)
_refine_ls_extinction_coef       0.0051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1600
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.062
_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)+(0.0396P)²+0.1149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0655
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11)
;
_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 0.49308(11) 1.00847(15) 0.56573(13) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.66110(10) 0.99756(16) 0.67816(13) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.64600(13) 0.4281(2) 0.50685(18) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.653105 0.347747 0.585971 0.023 Uiso 1 1 calc R U . . .
C2 C 0.65021(14) 0.3356(2) 0.37467(18) 0.0234(4) Uani 1 1 d . . . . .
H2A H 0.688670 0.402108 0.301491 0.028 Uiso 1 1 calc R U . . .
H2B H 0.660701 0.201147 0.372876 0.028 Uiso 1 1 calc R U . . .
C3 C 0.53476(14) 0.4094(2) 0.42587(17) 0.0209(4) Uani 1 1 d . . . . .
H3 H 0.475479 0.317293 0.456603 0.025 Uiso 1 1 calc R U . . .
C4 C 0.67777(12) 0.6311(2) 0.52462(17) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.753618 0.646705 0.573893 0.022 Uiso 1 1 calc R U . . .
C5 C 0.57086(12) 0.71288(19) 0.60163(16) 0.0161(3) Uani 1 1 d . . . . .
H5 H 0.562626 0.650328 0.688524 0.019 Uiso 1 1 calc R U . . .
C6 C 0.45632(13) 0.6896(2) 0.52111(18) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.399384 0.610788 0.570567 0.021 Uiso 1 1 calc R U . . .
C7 C 0.40615(13) 0.8840(2) 0.50872(19) 0.0228(4) Uani 1 1 d . . . . .
H7A H 0.392419 0.914652 0.415222 0.027 Uiso 1 1 calc R U . . .
H7B H 0.330051 0.893560 0.556307 0.027 Uiso 1 1 calc R U . . .
C8 C 0.58318(13) 0.9171(2) 0.62145(16) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.48689(13) 0.5986(2) 0.38793(18) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.415520 0.588332 0.330388 0.023 Uiso 1 1 calc R U . . .
C10 C 0.58248(14) 0.7108(2) 0.32348(18) 0.0227(4) Uani 1 1 d . . . . .
H10 H 0.573013 0.765570 0.239505 0.027 Uiso 1 1 calc R U . . .
C11 C 0.68118(15) 0.7269(2) 0.39365(17) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.748185 0.793315 0.363671 0.027 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
O1 C7 1.4598(19) . ?
O1 C8 1.344(2) . ?
O2 C8 1.206(2) . ?
C1 C2 1.506(2) . ?
C1 C3 1.510(2) . ?
C1 C4 1.537(2) . ?
C2 C3 1.505(2) . ?
C3 C9 1.534(2) . ?
C4 C5 1.560(2) . ?
C4 C11 1.506(2) . ?
C5 C6 1.542(2) . ?
C5 C8 1.512(2) . ?
C6 C7 1.534(2) . ?
C6 C9 1.549(2) . ?
C9 C10 1.507(2) . ?
C10 C11 1.330(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 111.63(12) . . ?
C2 C1 C3 59.88(11) . . ?
C2 C1 C4 122.06(15) . . ?
C3 C1 C4 110.27(13) . . ?
C3 C2 C1 60.18(11) . . ?
C1 C3 C9 110.46(13) . . ?
C2 C3 C1 59.94(11) . . ?
C2 C3 C9 122.78(14) . . ?
C1 C4 C5 104.33(12) . . ?
C11 C4 C1 110.51(14) . . ?
C11 C4 C5 106.66(12) . . ?
C6 C5 C4 109.98(12) . . ?
C8 C5 C4 111.93(12) . . ?
C8 C5 C6 104.89(12) . . ?
C5 C6 C9 108.97(12) . . ?
C7 C6 C5 104.61(12) . . ?
C7 C6 C9 114.08(15) . . ?
O1 C7 C6 107.17(12) . . ?
O1 C8 C5 111.36(13) . . ?
O2 C8 O1 120.89(14) . . ?
O2 C8 C5 127.75(14) . . ?
C3 C9 C6 104.21(13) . . ?
C10 C9 C3 110.30(12) . . ?
C10 C9 C6 107.89(13) . . ?
C11 C10 C9 114.60(16) . . ?
C10 C11 C4 114.36(15) . . ?

_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.633
####################################################################### 
# 
# 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_exp_1817_AB-89-2-5F29
_database_code_depnum_ccdc_archive 'CCDC 2378697'
loop_
_audit_author_name
_audit_author_address
'Julia Bruno'
;University College Dublin
Ireland
;
_audit_update_record             
;
2024-08-20 deposited with the CCDC.	2024-09-18 downloaded from the CCDC.
;
_audit_creation_date             2023-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11H12O3 '
_chemical_oxdiff_usercomment     AB-89-2-5F29_ArleneBonner_Baumann
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   6.28270(10)
_cell_length_b                   6.33670(10)
_cell_length_c                   23.1722(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.5670(10)
_cell_angle_gamma                90
_cell_volume                     919.59(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8807
_cell_measurement_temperature    104.70(14)
_cell_measurement_theta_max      76.0860
_cell_measurement_theta_min      3.8100
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.765
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.1190
0 -1 -1 0.1023
0 1 1 0.1153
0 0 -15 0.0577
1 0 15 0.0842
-4 0 3 0.1301
0 0 15 0.0773
2 0 12 0.1213
4 0 2 0.1768

_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.138
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9998 -0.0002 -1.0091 0.0173 0.0130 0.2591
0.0006 -0.9996 -0.9978 0.0682 0.2425 0.0055
-0.0006 0.9996 0.9978 -0.0682 -0.2425 -0.0055
0.0005 -0.3223 -14.9434 0.9609 0.0757 0.2664
0.5028 0.2832 14.6918 -0.9206 -0.0729 -0.3836
-4.0394 0.3320 2.8866 -0.3788 -0.0272 0.9251
-0.3722 0.3479 14.9821 -0.9812 -0.0771 -0.1772
2.3355 0.0942 11.5996 -0.6342 -0.0515 -0.7715
3.9808 -0.2226 2.0030 0.0616 0.0023 -0.9981

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15698
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.259
_diffrn_reflns_theta_min         3.827
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104.70(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -14.00   1.00    1.00    --  -41.95 142.00 -62.00   85
  2  ω   -114.00 -66.00   1.00    1.00    --  -41.95-142.00-119.00   48
  3  ω    -88.00  -7.00   1.00    1.00    --  -41.95 127.00 126.00   81
  4  ω     29.00  98.00   1.00    1.00    --   41.95-127.00  51.00   69
  5  ω     87.00 172.00   1.00    1.00    --  112.00 142.00 -62.00   85
  6  ω     40.00 114.00   1.00    1.00    --  112.00-127.00  51.00   74
  7  ω     96.00 178.00   1.00    1.00    --  112.00 127.00 126.00   82
  8  ω     40.00 126.00   1.00    1.00    --  112.00-142.00-119.00   86
  9  ω    -66.00  33.00   1.00    1.00    --  -41.95  37.00  30.00   99
 10  ω   -116.00 -18.00   1.00    1.00    --  -41.95 -37.00-150.00   98
 11  ω    103.00 178.00   1.00    1.00    --  112.00  77.00   0.00   75
 12  ω    104.00 178.00   1.00    1.00    --  112.00 111.00  90.00   74
 13  ω     39.00 109.00   1.00    1.00    --  112.00-111.00-120.00   70
 14  ω     29.00 107.00   1.00    1.00    --  112.00 -94.00 -90.00   78
 15  ω     84.00 178.00   1.00    1.00    --  112.00  30.00 -60.00   94
 16  ω     39.00 109.00   1.00    1.00    --  112.00-111.00  90.00   70
 17  ω     39.00 109.00   1.00    1.00    --  112.00-111.00  60.00   70
 18  ω    104.00 178.00   1.00    1.00    --  112.00 111.00 120.00   74
 19  ω     39.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   70
 20  ω     39.00 109.00   1.00    1.00    --  112.00-111.00  30.00   70
 21  ω    103.00 178.00   1.00    1.00    --  112.00  77.00-150.00   75
 22  ω    -66.00  33.00   1.00    1.00    --  -41.95  37.00 -90.00   99
 23  ω   -115.00 -14.00   1.00    1.00    --  -41.95 -57.00 -30.00  101
 24  ω   -115.00 -14.00   1.00    1.00    --  -41.95 -57.00  90.00  101
 25  ω     10.00  36.00   1.00    1.00    --   41.95  75.00 119.79   26
 26  ω      8.00  42.00   1.00    1.00    --   41.95  81.00  61.31   34
 27  ω      8.00  34.00   1.00    1.00    --   41.95  83.00-145.32   26
 28  ω     84.00 178.00   1.00    1.00    --  112.00  30.00  90.00   94
 29  ω     83.00 178.00   1.00    1.00    --  112.00  59.00 -47.55   95
 30  ω     83.00 178.00   1.00    1.00    --  112.00  61.00 120.00   95
 31  ω     83.00 178.00   1.00    1.00    --  112.00  61.00-150.00   95
 32  ω    104.00 178.00   1.00    1.00    --  112.00 111.00-120.00   74
 33  ω     86.00 178.00   1.00    1.00    --  112.00  45.00   0.00   92
 34  ω     83.00 178.00   1.00    1.00    --  112.00  61.00  30.00   95
 35  ω     83.00 178.00   1.00    1.00    --  112.00  61.00-120.00   95
 36  ω     83.00 118.00   1.00    1.00    --  112.00  61.00-180.00   35
 37  ω     84.00 178.00   1.00    1.00    --  112.00  56.00  79.50   94
 38  ω     84.00 178.00   1.00    1.00    --  112.00  30.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0475517000
_diffrn_orient_matrix_UB_12      -0.0041438000
_diffrn_orient_matrix_UB_13      -0.0642107000
_diffrn_orient_matrix_UB_21      -0.0130916000
_diffrn_orient_matrix_UB_22      -0.2427589000
_diffrn_orient_matrix_UB_23      0.0001677000
_diffrn_orient_matrix_UB_31      -0.2409287000
_diffrn_orient_matrix_UB_32      0.0123843000
_diffrn_orient_matrix_UB_33      -0.0181013000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1730
_reflns_number_total             1910
_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 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.036
_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)+(0.0338P)²+0.5281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0850
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1753(2) 0.4161(2) 0.42614(5) 0.0221(3) Uani 1 1 d . . . . .
H1 H 0.048953 0.511995 0.420288 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1549(2) 0.2276(2) 0.46518(6) 0.0256(3) Uani 1 1 d . . . . .
H2A H 0.283707 0.182006 0.489358 0.031 Uiso 1 1 calc R U . . .
H2B H 0.018634 0.208923 0.483271 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1529(2) 0.1970(2) 0.40075(5) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.012300 0.161241 0.379768 0.027 Uiso 1 1 calc R U . . .
C4 C 0.39475(19) 0.5093(2) 0.41574(5) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.416689 0.650702 0.434418 0.024 Uiso 1 1 calc R U . . .
C5 C 0.39751(19) 0.52270(19) 0.34847(5) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.288547 0.626007 0.332085 0.023 Uiso 1 1 calc R U . . .
C6 C 0.35771(19) 0.30292(19) 0.32130(5) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.216849 0.302525 0.297938 0.023 Uiso 1 1 calc R U . . .
C7 C 0.53688(19) 0.2758(2) 0.28093(5) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.597704 0.130048 0.283848 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6167(2) 0.58229(19) 0.33214(5) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.35380(19) 0.13718(19) 0.37060(5) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.344152 -0.009827 0.354913 0.025 Uiso 1 1 calc R U . . .
C10 C 0.55057(19) 0.1666(2) 0.41144(5) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.652567 0.057747 0.419495 0.026 Uiso 1 1 calc R U . . .
C11 C 0.56998(19) 0.3572(2) 0.43530(5) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.685056 0.394402 0.462488 0.025 Uiso 1 1 calc R U . . .
O1 O 0.69937(13) 0.43405(14) 0.29911(4) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.45997(15) 0.32137(15) 0.22451(4) 0.0248(2) Uani 1 1 d . . . . .
O3 O 0.71789(15) 0.74025(14) 0.34620(4) 0.0260(2) Uani 1 1 d . . . . .
H2 H 0.570(3) 0.290(3) 0.2001(9) 0.054(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 1.0000 . ?
C1 C2 1.5099(18) . ?
C1 C3 1.5102(18) . ?
C1 C4 1.5366(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5046(17) . ?
C3 H3 1.0000 . ?
C3 C9 1.5377(17) . ?
C4 H4 1.0000 . ?
C4 C5 1.5626(16) . ?
C4 C11 1.5055(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5406(16) . ?
C5 C8 1.5048(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5295(16) . ?
C6 C9 1.5534(16) . ?
C7 H7 1.0000 . ?
C7 O1 1.4684(14) . ?
C7 O2 1.3876(14) . ?
C8 O1 1.3422(14) . ?
C8 O3 1.2164(15) . ?
C9 H9 1.0000 . ?
C9 C10 1.5075(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3298(18) . ?
C11 H11 0.9500 . ?
O2 H2 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 117.2 . . ?
C2 C1 C3 59.76(8) . . ?
C2 C1 C4 121.18(11) . . ?
C3 C1 H1 117.2 . . ?
C3 C1 C4 110.41(10) . . ?
C4 C1 H1 117.2 . . ?
C1 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
C3 C2 C1 60.13(8) . . ?
C3 C2 H2A 117.8 . . ?
C3 C2 H2B 117.8 . . ?
C1 C3 H3 116.7 . . ?
C1 C3 C9 110.46(10) . . ?
C2 C3 C1 60.11(8) . . ?
C2 C3 H3 116.7 . . ?
C2 C3 C9 122.71(11) . . ?
C9 C3 H3 116.7 . . ?
C1 C4 H4 111.8 . . ?
C1 C4 C5 105.00(10) . . ?
C5 C4 H4 111.8 . . ?
C11 C4 C1 110.54(10) . . ?
C11 C4 H4 111.8 . . ?
C11 C4 C5 105.62(9) . . ?
C4 C5 H5 110.7 . . ?
C6 C5 C4 110.13(10) . . ?
C6 C5 H5 110.7 . . ?
C8 C5 C4 110.34(10) . . ?
C8 C5 H5 110.7 . . ?
C8 C5 C6 104.25(9) . . ?
C5 C6 H6 109.4 . . ?
C5 C6 C9 108.80(9) . . ?
C7 C6 C5 104.35(9) . . ?
C7 C6 H6 109.4 . . ?
C7 C6 C9 115.43(10) . . ?
C9 C6 H6 109.4 . . ?
C6 C7 H7 111.0 . . ?
O1 C7 C6 106.06(9) . . ?
O1 C7 H7 111.0 . . ?
O2 C7 C6 109.56(10) . . ?
O2 C7 H7 111.0 . . ?
O2 C7 O1 108.08(10) . . ?
O1 C8 C5 111.80(10) . . ?
O3 C8 C5 127.48(11) . . ?
O3 C8 O1 120.71(11) . . ?
C3 C9 C6 103.24(10) . . ?
C3 C9 H9 111.5 . . ?
C6 C9 H9 111.5 . . ?
C10 C9 C3 110.24(10) . . ?
C10 C9 C6 108.53(10) . . ?
C10 C9 H9 111.5 . . ?
C9 C10 H10 122.7 . . ?
C11 C10 C9 114.64(11) . . ?
C11 C10 H10 122.7 . . ?
C4 C11 H11 122.7 . . ?
C10 C11 C4 114.54(11) . . ?
C10 C11 H11 122.7 . . ?
C8 O1 C7 110.46(9) . . ?
C7 O2 H2 107.6(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C9 96.32(13) . . . . ?
C1 C3 C9 C6 -62.47(12) . . . . ?
C1 C3 C9 C10 53.30(13) . . . . ?
C1 C4 C5 C6 -57.24(12) . . . . ?
C1 C4 C5 C8 -171.79(10) . . . . ?
C1 C4 C11 C10 55.45(14) . . . . ?
C2 C1 C3 C9 -116.79(12) . . . . ?
C2 C1 C4 C5 128.54(12) . . . . ?
C2 C1 C4 C11 15.09(15) . . . . ?
C2 C3 C9 C6 -129.35(12) . . . . ?
C2 C3 C9 C10 -13.59(16) . . . . ?
C3 C1 C4 C5 62.30(12) . . . . ?
C3 C1 C4 C11 -51.16(13) . . . . ?
C3 C9 C10 C11 -53.64(14) . . . . ?
C4 C1 C2 C3 -96.84(12) . . . . ?
C4 C1 C3 C2 114.99(12) . . . . ?
C4 C1 C3 C9 -1.80(14) . . . . ?
C4 C5 C6 C7 -130.10(10) . . . . ?
C4 C5 C6 C9 -6.37(13) . . . . ?
C4 C5 C8 O1 120.15(11) . . . . ?
C4 C5 C8 O3 -58.68(16) . . . . ?
C5 C4 C11 C10 -57.61(13) . . . . ?
C5 C6 C7 O1 17.15(12) . . . . ?
C5 C6 C7 O2 -99.27(11) . . . . ?
C5 C6 C9 C3 66.34(12) . . . . ?
C5 C6 C9 C10 -50.64(12) . . . . ?
C5 C8 O1 C7 9.47(13) . . . . ?
C6 C5 C8 O1 1.94(13) . . . . ?
C6 C5 C8 O3 -176.89(12) . . . . ?
C6 C7 O1 C8 -16.96(12) . . . . ?
C6 C9 C10 C11 58.75(13) . . . . ?
C7 C6 C9 C3 -176.81(10) . . . . ?
C7 C6 C9 C10 66.22(13) . . . . ?
C8 C5 C6 C7 -11.74(12) . . . . ?
C8 C5 C6 C9 111.99(10) . . . . ?
C9 C6 C7 O1 -102.18(11) . . . . ?
C9 C6 C7 O2 141.39(10) . . . . ?
C9 C10 C11 C4 -1.59(15) . . . . ?
C11 C4 C5 C6 59.63(12) . . . . ?
C11 C4 C5 C8 -54.91(13) . . . . ?
O2 C7 O1 C8 100.46(11) . . . . ?
O3 C8 O1 C7 -171.61(11) . . . . ?

_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 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.645
