# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_bm301124_2_1
_database_code_depnum_ccdc_archive 'CCDC 2418538'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-01-21 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
ann-sophie.paschke@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        'tert-butyl benzo[d]isoxazol-5-ylcarbamate'
_chemical_formula_moiety         'C12 H14 N2 O3'
_chemical_formula_sum            'C12 H14 N2 O3'
_chemical_formula_weight         234.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H14N2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.2172(2)
_cell_length_b                   8.9168(3)
_cell_length_c                   13.0925(4)
_cell_angle_alpha                79.389(3)
_cell_angle_beta                 78.628(3)
_cell_angle_gamma                76.805(3)
_cell_volume                     575.14(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7549
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.5990
_cell_measurement_theta_min      3.4520
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 8 0.0157
0 1 -8 0.0028
0 -5 -4 0.0341
3 -1 1 0.0574
1 6 3 0.0446
0 5 3 0.0428
-2 -5 -4 0.0536
-1 -5 1 0.0458
0 -4 6 0.0153
-1 -4 4 0.0380
-1 4 6 0.0395
-2 3 -1 0.0774
3 -1 3 0.0571
2 -2 6 0.0383
1 -1 7 0.0244

_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.021
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
-0.3634 -0.9334 7.7682 -0.0782 0.9970 0.0363
0.2352 0.7670 -7.9036 0.0784 -0.9972 0.0072
-0.1698 -5.4198 -3.7245 0.8390 -0.1122 0.5287
3.1117 -0.9722 0.5821 0.7891 -0.0183 -0.6125
1.1931 5.5920 3.4242 -0.6438 0.0184 -0.7621
-0.1507 5.4370 2.8860 -0.8938 0.0264 -0.4471
-1.6215 -5.4456 -3.5052 0.5333 -0.0167 0.8455
-1.3438 -5.3151 1.1485 0.4880 0.5163 0.7034
0.0127 -3.5095 5.6969 0.4222 0.8864 0.1921
-1.1375 -4.4744 3.6111 0.3616 0.7495 0.5533
-0.9923 3.9798 6.0450 -0.9111 0.5285 -0.1939
-2.0158 2.9880 -0.9784 -0.8516 -0.2002 0.2167
3.0083 -0.9863 3.0172 0.7253 0.2771 -0.6258
2.0031 -1.9950 6.0123 0.6098 0.7406 -0.3702
0.9978 -0.9998 7.0098 0.2319 0.8470 -0.2450

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13801
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.391
_diffrn_reflns_theta_min         3.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00 -26.00   0.50    0.15    --  -14.00 -62.00-101.06   52
  2  ω    -52.00 -26.00   0.50    0.15    --  -14.00 -62.00 -11.51   52
  3  ω    -71.00 -41.00   0.50    0.15    --  -26.00 -55.00  18.74   60
  4  ω    -52.00 -26.00   0.50    0.15    --  -14.00 -62.00  78.29   52
  5  ω    -52.00 -23.00   0.50    0.15    --  -10.00 -61.00 139.47   58
  6  ω    -87.00 -57.00   0.50    0.15    --  -42.00 -55.00 143.19   60
  7  ω    -96.00 -65.00   0.50    0.15    --  -50.00 -52.00 175.60   62
  8  ω    -80.00 -49.00   0.50    0.15    --  -34.00 -52.00  84.51   62
  9  ω    -79.00 -49.00   0.50    0.15    --  -34.00 -55.00  63.35   60
 10  ω    -82.00 -48.00   0.50    0.15    --  -34.00 -44.00 -48.11   68
 11  ω    -85.00 -54.00   0.50    0.15    --  -38.00 -49.00-159.46   62
 12  ω    -94.00 -60.00   0.50    0.15    --  -46.00 -42.00-119.36   68
 13  ω   -113.00 -78.00   0.50    0.15    --  -72.64 -16.00-108.33   70
 14  ω   -124.00 -89.00   0.50    0.60    --  -75.17 -42.00 -80.19   70
 15  ω   -114.00 -83.00   0.50    0.15    --  -70.00 -61.00  48.73   62
 16  ω   -122.00 -91.00   0.50    0.60    --  -75.17 -38.00 -24.92   62
 17  ω   -108.00 -77.00   0.50    0.15    --  -62.00 -54.00 -33.88   62
 18  ω   -109.00 -77.00   0.50    0.15    --  -62.00 -36.00 -83.84   64
 19  ω   -116.00 -85.00   0.50    0.15    --  -70.00 -52.00  51.68   62
 20  ω   -109.00 -78.00   0.50    0.15    --  -62.00 -50.00  83.02   62
 21  ω   -121.00 -90.00   0.50    0.15    --  -74.00 -39.00 129.37   62
 22  ω   -121.00 -93.00   0.50    0.60    --  -75.17 -34.00 159.01   56
 23  ω   -116.00 -90.00   0.50    0.15    --  -72.64 -27.00 127.35   52
 24  ω   -112.00 -83.00   0.50    0.15    --  -66.00 -32.00  -5.85   58
 25  ω   -104.00 -76.00   0.50    0.15    --  -58.00 -33.00-133.81   56
 26  ω   -110.00 -84.00   0.50    0.15    --  -66.00 -27.00-160.35   52
 27  ω   -121.00 -93.00   0.50    0.60    --  -75.17 -33.00-175.86   56
 28  ω   -116.00 -90.00   0.50    0.15    --  -72.64 -26.00-143.05   52
 29  ω   -119.00 -92.00   0.50    0.60    --  -75.17 -26.00 -28.27   54
 30  ω   -115.00 -88.00   0.50    0.15    --  -72.64 -22.00 -64.78   54
 31  ω   -114.00 -87.00   0.50    0.15    --  -72.64 -21.00-174.13   54
 32  ω   -111.00 -84.00   0.50    0.15    --  -70.00 -20.00-138.93   54
 33  ω   -117.00 -90.00   0.50    0.60    --  -75.17 -21.00   6.15   54
 34  ω   -119.00 -92.00   0.50    0.60    --  -75.17 -25.00  35.70   54
 35  ω   -117.00 -89.00   0.50    0.60    --  -75.17 -20.00  55.72   56
 36  ω   -113.00 -86.00   0.50    0.15    --  -70.00 -25.00 150.62   54
 37  ω   -117.00 -89.00   0.50    0.60    --  -75.17 -20.00 133.75   56
 38  ω   -111.00 -81.00   0.50    0.15    --  -70.00 -18.00  76.01   60
 39  ω    -35.00  -8.00   0.50    0.15    --  -54.00  52.00  54.13   54
 40  ω    -38.00 -12.00   0.50    0.15    --  -58.00  54.00 106.27   52
 41  ω    -64.00 -33.00   0.50    0.15    --  -72.64  73.00 135.70   62
 42  ω    -63.00 -33.00   0.50    0.15    --  -72.64  72.00  87.88   60
 43  ω    -35.00  -8.00   0.50    0.15    --  -54.00  52.00 -27.08   54
 44  ω    -35.00  -8.00   0.50    0.15    --  -54.00  52.00 -89.04   54
 45  ω    -35.00  -8.00   0.50    0.15    --  -54.00  52.00-125.97   54
 46  ω    -68.00 -36.00   0.50    0.15    --  -72.64  79.00 -66.74   64
 47  ω    -66.00 -35.00   0.50    0.15    --  -72.64  76.00 -12.63   62
 48  ω    -35.00  -8.00   0.50    0.15    --  -54.00  52.00 152.73   54
 49  ω    -95.00 -25.00   0.50    0.15    --  -69.39 125.00 120.00  140
 50  ω    -95.00 -25.00   0.50    0.15    --  -69.39 125.00 120.00  140
 51  ω    -91.00 -25.00   0.50    0.15    --  -69.39 119.00 140.00  132
 52  ω    -88.00 -22.00   0.50    0.15    --  -66.25 119.00 140.00  132
 53  ω    -31.00  -5.00   0.50    0.15    --  -10.00 117.00 -61.83   52
 54  ω    -99.00 -30.00   0.50    0.60    --  -75.17 121.00-132.30  138
 55  ω    -98.00 -30.00   0.50    0.60    --  -75.17 120.00-117.82  136
 56  ω    -72.00 -35.00   0.50    0.15    --  -72.64  85.00-111.38   74
 57  ω     61.00 105.00   0.50    0.60    --   75.17  11.00 -28.55   88
 58  ω     33.00 100.00   0.50    0.60    --   77.85-125.00-120.00  134
 59  ω     26.00  97.00   0.50    0.15    --   70.78-125.00-120.00  142
 60  ω     33.00 100.00   0.50    0.60    --   77.85-125.00-180.00  134
 61  ω     33.00 100.00   0.50    0.60    --   77.85-125.00   0.00  134
 62  ω     33.00 100.00   0.50    0.60    --   77.85-125.00  30.00  134
 63  ω     33.00 100.00   0.50    0.60    --   77.85-125.00 120.00  134
 64  ω     34.00  98.00   0.50    0.60    --   77.85-119.00  56.00  128
 65  ω     33.00 100.00   0.50    0.60    --   77.85-125.00  30.00  134
 66  ω     24.00  90.00   0.50    0.15    --   67.93-119.00  56.00  132
 67  ω     27.00  93.00   0.50    0.15    --   70.78-119.00  56.00  132
 68  ω     37.00  85.00   0.50    0.60    --   77.85 -95.00  60.00   96
 69  ω     37.00  85.00   0.50    0.60    --   77.85 -95.00 150.00   96
 70  ω     37.00  85.00   0.50    0.60    --   77.85 -95.00  90.00   96
 71  ω     37.00  85.00   0.50    0.60    --   77.85 -95.00-180.00   96
 72  ω     33.00 100.00   0.50    0.60    --   77.85-125.00-180.00  134
 73  ω     37.00  85.00   0.50    0.60    --   77.85 -95.00-120.00   96
 74  ω     89.00 115.00   0.50    0.15    --   72.89  22.00 147.77   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2104546000
_diffrn_orient_matrix_UB_12      -0.1489454000
_diffrn_orient_matrix_UB_13      -0.0181174000
_diffrn_orient_matrix_UB_21      -0.0467698000
_diffrn_orient_matrix_UB_22      -0.0595958000
_diffrn_orient_matrix_UB_23      0.1189906000
_diffrn_orient_matrix_UB_31      -0.2190635000
_diffrn_orient_matrix_UB_32      -0.0802357000
_diffrn_orient_matrix_UB_33      -0.0152139000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1876
_reflns_number_total             2244
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.038
_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)+(0.0873P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1389
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.93 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C11(H11), C9(H9)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_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
O1 O 0.3125(2) 0.71731(14) 0.21594(8) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.5455(2) 0.74940(15) 0.33828(9) 0.0347(3) Uani 1 1 d . . . . .
O3 O -0.1298(3) 0.78114(15) 0.80082(9) 0.0366(3) Uani 1 1 d . . . . .
N1 N 0.1035(3) 0.73625(18) 0.37702(11) 0.0296(3) Uani 1 1 d D . . . .
N2 N 0.0496(3) 0.87570(19) 0.80968(11) 0.0380(4) Uani 1 1 d . . . . .
C6 C 0.0529(3) 0.7463(2) 0.48633(12) 0.0287(4) Uani 1 1 d . . . . .
C5 C 0.3409(3) 0.73553(19) 0.31195(12) 0.0285(4) Uani 1 1 d . . . . .
C8 C 0.1087(4) 0.8340(2) 0.63982(13) 0.0303(4) Uani 1 1 d . . . . .
C1 C 0.5392(3) 0.7147(2) 0.12640(12) 0.0293(4) Uani 1 1 d . . . . .
C7 C 0.1839(3) 0.8289(2) 0.53096(13) 0.0305(4) Uani 1 1 d . . . . .
H7 H 0.319233 0.880205 0.490057 0.037 Uiso 1 1 calc R U . . .
C10 C -0.0887(4) 0.7592(2) 0.69805(13) 0.0315(4) Uani 1 1 d . . . . .
C12 C -0.1479(3) 0.6707(2) 0.54784(13) 0.0304(4) Uani 1 1 d . . . . .
H12 H -0.234848 0.614846 0.514668 0.036 Uiso 1 1 calc R U . . .
C11 C -0.2221(4) 0.6750(2) 0.65438(13) 0.0329(4) Uani 1 1 d . . . . .
H11 H -0.356824 0.623518 0.695580 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1827(4) 0.9049(2) 0.71645(13) 0.0345(4) Uani 1 1 d . . . . .
H9 H 0.315371 0.966797 0.700451 0.041 Uiso 1 1 calc R U . . .
C2 C 0.6546(4) 0.8601(2) 0.11032(13) 0.0325(4) Uani 1 1 d . . . . .
H2A H 0.509364 0.950663 0.119222 0.049 Uiso 1 1 calc R U . . .
H2B H 0.756975 0.874072 0.039152 0.049 Uiso 1 1 calc R U . . .
H2C H 0.772133 0.849608 0.162174 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7439(4) 0.5659(2) 0.14631(14) 0.0347(4) Uani 1 1 d . . . . .
H3A H 0.820036 0.567469 0.208720 0.052 Uiso 1 1 calc R U . . .
H3B H 0.886166 0.558199 0.085108 0.052 Uiso 1 1 calc R U . . .
H3C H 0.657539 0.476107 0.157954 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4041(4) 0.7121(2) 0.03436(13) 0.0363(4) Uani 1 1 d . . . . .
H4A H 0.323175 0.619956 0.047843 0.054 Uiso 1 1 calc R U . . .
H4B H 0.536556 0.708551 -0.030082 0.054 Uiso 1 1 calc R U . . .
H4C H 0.265290 0.806194 0.025867 0.054 Uiso 1 1 calc R U . . .
H1 H -0.032(4) 0.720(2) 0.3505(16) 0.044 Uiso 1 1 d D 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 C5 1.3373(19) . ?
O1 C1 1.4913(19) . ?
O2 C5 1.223(2) . ?
O3 N2 1.428(2) . ?
O3 C10 1.3634(19) . ?
N1 C6 1.419(2) . ?
N1 C5 1.357(2) . ?
N1 H1 0.898(15) . ?
N2 C9 1.293(2) . ?
C6 C7 1.378(3) . ?
C6 C12 1.411(3) . ?
C8 C7 1.408(2) . ?
C8 C10 1.380(3) . ?
C8 C9 1.433(2) . ?
C1 C2 1.514(3) . ?
C1 C3 1.518(2) . ?
C1 C4 1.517(2) . ?
C7 H7 0.9500 . ?
C10 C11 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.377(2) . ?
C11 H11 0.9500 . ?
C9 H9 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
C5 O1 C1 121.45(13) . . ?
C10 O3 N2 107.26(13) . . ?
C6 N1 H1 115.9(14) . . ?
C5 N1 C6 126.42(15) . . ?
C5 N1 H1 117.5(14) . . ?
C9 N2 O3 106.48(14) . . ?
C7 C6 N1 122.74(16) . . ?
C7 C6 C12 120.93(15) . . ?
C12 C6 N1 116.29(15) . . ?
O1 C5 N1 108.89(14) . . ?
O2 C5 O1 126.35(15) . . ?
O2 C5 N1 124.76(15) . . ?
C7 C8 C9 136.36(17) . . ?
C10 C8 C7 120.71(16) . . ?
C10 C8 C9 102.92(15) . . ?
O1 C1 C2 110.99(13) . . ?
O1 C1 C3 108.64(13) . . ?
O1 C1 C4 101.97(13) . . ?
C2 C1 C3 112.98(15) . . ?
C2 C1 C4 110.72(14) . . ?
C4 C1 C3 110.99(14) . . ?
C6 C7 C8 117.13(16) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
O3 C10 C8 110.51(16) . . ?
O3 C10 C11 126.59(17) . . ?
C8 C10 C11 122.90(16) . . ?
C6 C12 H12 118.9 . . ?
C11 C12 C6 122.22(17) . . ?
C11 C12 H12 118.9 . . ?
C10 C11 H11 121.9 . . ?
C12 C11 C10 116.11(17) . . ?
C12 C11 H11 121.9 . . ?
N2 C9 C8 112.83(18) . . ?
N2 C9 H9 123.6 . . ?
C8 C9 H9 123.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
O3 N2 C9 C8 -0.50(19) . . . . ?
O3 C10 C11 C12 179.25(15) . . . . ?
N1 C6 C7 C8 177.89(14) . . . . ?
N1 C6 C12 C11 -178.11(15) . . . . ?
N2 O3 C10 C8 0.24(18) . . . . ?
N2 O3 C10 C11 -179.49(17) . . . . ?
C6 N1 C5 O1 177.11(15) . . . . ?
C6 N1 C5 O2 -2.9(3) . . . . ?
C6 C12 C11 C10 0.3(3) . . . . ?
C5 O1 C1 C2 -55.37(19) . . . . ?
C5 O1 C1 C3 69.43(18) . . . . ?
C5 O1 C1 C4 -173.32(15) . . . . ?
C5 N1 C6 C7 32.8(3) . . . . ?
C5 N1 C6 C12 -149.26(17) . . . . ?
C8 C10 C11 C12 -0.4(3) . . . . ?
C1 O1 C5 O2 -1.1(3) . . . . ?
C1 O1 C5 N1 178.90(14) . . . . ?
C7 C6 C12 C11 -0.2(3) . . . . ?
C7 C8 C10 O3 -179.37(14) . . . . ?
C7 C8 C10 C11 0.4(3) . . . . ?
C7 C8 C9 N2 179.22(19) . . . . ?
C10 O3 N2 C9 0.16(18) . . . . ?
C10 C8 C7 C6 -0.2(3) . . . . ?
C10 C8 C9 N2 0.6(2) . . . . ?
C12 C6 C7 C8 0.1(2) . . . . ?
C9 C8 C7 C6 -178.57(19) . . . . ?
C9 C8 C10 O3 -0.50(19) . . . . ?
C9 C8 C10 C11 179.24(17) . . . . ?

_olex2_date_sample_submission    2024-11-26
_olex2_submission_original_sample_id bm301124_2_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.372
_oxdiff_exptl_absorpt_empirical_full_min 0.404
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_bm281124_1_1
_database_code_depnum_ccdc_archive 'CCDC 2418539'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-01-21 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
ann-sophie.paschke@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        'tert-butyl benzofuran-5-ylcarbamate'
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H15NO3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.2939(2)
_cell_length_b                   10.5894(3)
_cell_length_c                   11.1328(3)
_cell_angle_alpha                102.318(2)
_cell_angle_beta                 100.925(2)
_cell_angle_gamma                94.671(2)
_cell_volume                     593.83(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8271
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.9040
_cell_measurement_theta_min      4.1310
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             248
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 6 0.0321
0 -1 -6 0.0266
3 3 -2 0.0698
-3 -3 5 0.0776
-1 7 -1 0.0134
1 -7 0 0.0169
-2 -3 7 0.0634
0 6 -4 0.0321
-2 5 3 0.0446
0 4 5 0.0315
-1 -6 -2 0.0423
-1 -6 1 0.0587
1 6 0 0.0425
2 2 2 0.0592
1 -3 6 0.0317
3 -2 1 0.0578
-1 -2 7 0.0580
2 -6 0 0.0160
-1 5 -5 0.0208
-3 2 3 0.0776
-1 6 -2 0.0219

_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.039
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
0.5778 0.9645 6.2498 0.7727 0.1413 0.6233
-0.3734 -0.7254 -6.4696 -0.7241 -0.1325 -0.6761
2.8375 3.4013 -1.7264 0.7991 0.1487 -0.5845
-2.6421 -3.0550 4.5765 -0.4704 -0.0899 0.8784
-0.7721 6.7929 -1.3339 0.1262 0.9700 -0.2019
1.0693 -6.6175 0.2770 -0.1329 -0.9885 0.0451
-1.6362 -2.8346 6.5975 -0.0154 -0.1390 0.9894
0.1827 6.3723 -4.0512 0.1009 0.7868 -0.6089
-1.7650 5.2876 2.5868 0.1234 0.9134 0.3848
-0.3840 3.9426 4.8308 0.5925 0.6200 0.5106
-0.5424 -5.6344 -2.0112 -0.6891 -0.7206 -0.0524
-1.3698 -6.0214 1.4383 -0.6182 -0.6499 0.4396
1.0563 6.0773 0.0447 0.6742 0.7057 -0.2374
2.4496 2.2412 2.4782 1.0003 0.0805 -0.0409
1.3395 -3.2288 5.7706 0.6514 -0.5009 0.5683
3.1135 -2.2726 1.4804 0.7863 -0.6006 -0.1372
-1.3667 -2.3174 6.9424 0.1189 -0.0932 0.9876
1.5196 -6.3221 -0.0362 -0.0256 -0.9980 -0.0471
-1.0947 4.6300 -5.4068 -0.4640 0.6675 -0.5831
-3.1639 1.7816 3.2858 -0.4039 0.5941 0.6928
-1.3645 6.4693 -1.6579 -0.0768 0.9828 -0.1653

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15691
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.576
_diffrn_reflns_theta_min         4.160
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  -3.00   0.50    0.20    --  -50.00  47.00 -64.73   50
  2  ω    -28.00  -3.00   0.50    0.20    --  -50.00  47.00  55.07   50
  3  ω    -24.00   1.00   0.50    0.20    --  -46.00  45.00 108.07   50
  4  ω    -38.00 -13.00   0.50    0.20    --  -58.00  54.00 144.60   50
  5  ω    -57.00 -32.00   0.50    0.20    --  -72.64  68.00 171.82   50
  6  ω    -35.00 -10.00   0.50    0.20    --  -54.00  52.00 152.71   50
  7  ω    -34.00  -9.00   0.50    0.20    --  -54.00  52.00  86.33   50
  8  ω    -35.00 -10.00   0.50    0.20    --  -54.00  52.00  40.22   50
  9  ω    -35.00  -9.00   0.50    0.20    --  -54.00  52.00  12.70   52
 10  ω    -33.00  -7.00   0.50    0.20    --  -54.00  51.00 -86.35   52
 11  ω    -32.00  -7.00   0.50    0.20    --  -54.00  51.00-140.63   50
 12  ω    -72.00 -26.00   0.50    0.20    --  -66.25 125.00-150.00   92
 13  ω    -75.00 -38.00   0.50    0.20    --  -69.39 125.00-180.00   74
 14  ω    -67.00 -27.00   0.50    0.20    --  -69.39 125.00 -90.00   80
 15  ω    -64.00 -39.00   0.50    0.80    --  -75.17 121.00-146.27   50
 16  ω    -57.00 -25.00   0.50    0.20    --  -69.39 125.00   0.00   64
 17  ω    -88.00 -62.00   0.50    0.20    --  -69.39 125.00   0.00   52
 18  ω    -56.00 -27.00   0.50    0.20    --  -69.39 125.00 150.00   58
 19  ω    -23.00   2.00   0.50    0.20    --  -26.00  81.00 110.04   50
 20  ω     61.00  86.00   0.50    0.20    --   46.00  55.00 153.09   50
 21  ω     68.00  97.00   0.50    0.80    --   75.17  11.00 166.00   58
 22  ω     79.00 104.00   0.50    0.20    --   72.89  11.00   4.74   50
 23  ω     61.00  86.00   0.50    0.20    --   46.00  54.00 -38.49   50
 24  ω     61.00  86.00   0.50    0.20    --   46.00  55.00 -61.34   50
 25  ω     73.00 103.00   0.50    0.80    --   75.17  11.00-109.47   60
 26  ω     67.00 112.00   0.50    0.20    --   72.89  14.00 -72.35   90
 27  ω    -28.00  -3.00   0.50    0.20    --    6.00 -73.00 134.27   50
 28  ω     24.00  50.00   0.50    0.20    --   67.93-125.00 150.00   52
 29  ω     63.00  89.00   0.50    0.20    --   67.93-125.00 150.00   52
 30  ω     26.00  61.00   0.50    0.20    --   70.78-125.00  30.00   70
 31  ω     69.00  96.00   0.50    0.20    --   70.78-125.00  30.00   54
 32  ω     74.00 100.00   0.50    0.80    --   77.85-125.00  30.00   52
 33  ω     29.00  55.00   0.50    0.20    --   70.78-125.00 -90.00   52
 34  ω     29.00  59.00   0.50    0.20    --   67.93-125.00-150.00   60
 35  ω     63.00  89.00   0.50    0.20    --   67.93-125.00-150.00   52
 36  ω     72.00  97.00   0.50    0.20    --   70.78-125.00 -90.00   50
 37  ω     42.00  68.00   0.50    0.80    --   77.85-125.00  30.00   52
 38  ω     72.00  99.00   0.50    0.80    --   77.85-125.00  60.00   54
 39  ω     75.00 100.00   0.50    0.80    --   77.85-125.00 150.00   50
 40  ω     41.00  67.00   0.50    0.80    --   77.85-125.00 150.00   52
 41  ω     35.00  99.00   0.50    0.80    --   77.85-125.00 120.00  128
 42  ω     36.00  67.00   0.50    0.80    --   77.85-125.00  60.00   62
 43  ω     34.00  64.00   0.50    0.20    --   67.93 -95.00  60.00   60
 44  ω     34.00  70.00   0.50    0.20    --   70.78 -95.00 -30.00   72
 45  ω     34.00 100.00   0.50    0.80    --   77.85-125.00 -30.00  132
 46  ω     35.00 100.00   0.50    0.80    --   77.85-125.00-120.00  130
 47  ω     42.00  98.00   0.50    0.80    --   77.85-125.00-180.00  112
 48  ω    -42.00 -17.00   0.50    0.20    --   -2.00 -67.00  -3.68   50
 49  ω    -50.00 -25.00   0.50    0.20    --  -10.00 -63.00 -79.64   50
 50  ω    -47.00 -22.00   0.50    0.20    --   -6.00 -65.00 -51.54   50
 51  ω    -52.00 -27.00   0.50    0.20    --  -10.00 -61.00-160.12   50
 52  ω    -52.00 -26.00   0.50    0.20    --  -14.00 -62.00  48.73   52
 53  ω    -52.00 -27.00   0.50    0.20    --  -14.00 -62.00  93.24   50
 54  ω    -50.00 -25.00   0.50    0.20    --  -10.00 -63.00 120.66   50
 55  ω    -51.00 -26.00   0.50    0.20    --  -14.00 -62.00 147.23   50
 56  ω    -95.00 -70.00   0.50    0.20    --  -50.00 -55.00  75.15   50
 57  ω    -53.00 -28.00   0.50    0.20    --  -14.00 -59.00  17.92   50
 58  ω    -67.00 -41.00   0.50    0.20    --  -26.00 -55.00 -27.03   52
 59  ω    -53.00 -28.00   0.50    0.20    --  -14.00 -59.00-123.43   50
 60  ω    -80.00 -54.00   0.50    0.20    --  -38.00 -54.00-170.65   52
 61  ω    -90.00 -64.00   0.50    0.20    --  -46.00 -54.00-136.59   52
 62  ω    -92.00 -66.00   0.50    0.20    --  -50.00 -53.00 -33.18   52
 63  ω    -75.00 -49.00   0.50    0.20    --  -34.00 -53.00 -60.37   52
 64  ω    -90.00 -65.00   0.50    0.20    --  -50.00 -54.00  50.52   50
 65  ω    -80.00 -54.00   0.50    0.20    --  -38.00 -52.00  54.14   52
 66  ω    -63.00 -38.00   0.50    0.20    --  -22.00 -53.00  72.35   50
 67  ω    -64.00 -39.00   0.50    0.20    --  -18.00 -54.00 125.39   50
 68  ω    -78.00 -53.00   0.50    0.20    --  -38.00 -52.00  73.53   50
 69  ω    -90.00 -64.00   0.50    0.20    --  -46.00 -51.00 169.85   52
 70  ω    -82.00 -57.00   0.50    0.20    --  -38.00 -51.00  25.55   50
 71  ω    -74.00 -48.00   0.50    0.20    --  -30.00 -51.00 -12.46   52
 72  ω    -90.00 -65.00   0.50    0.20    --  -50.00 -52.00 -77.65   50
 73  ω    -87.00 -61.00   0.50    0.20    --  -46.00 -52.00 -70.71   52
 74  ω    -67.00 -41.00   0.50    0.20    --  -26.00 -52.00-168.27   52
 75  ω    -85.00 -59.00   0.50    0.20    --  -42.00 -49.00-118.05   52
 76  ω    -90.00 -65.00   0.50    0.20    --  -50.00 -47.00 -25.92   50
 77  ω    -83.00 -57.00   0.50    0.20    --  -38.00 -48.00 106.61   52
 78  ω   -114.00 -86.00   0.50    0.20    --  -72.64 -67.00  69.15   56
 79  ω   -114.00 -89.00   0.50    0.20    --  -72.64 -67.00  32.57   50
 80  ω   -115.00 -85.00   0.50    0.20    --  -72.64 -66.00  84.14   60
 81  ω   -109.00 -84.00   0.50    0.20    --  -72.64 -65.00 139.33   50
 82  ω   -109.00 -84.00   0.50    0.20    --  -72.64 -65.00 155.76   50
 83  ω   -110.00 -85.00   0.50    0.20    --  -72.64 -64.00 -84.53   50
 84  ω   -117.00 -86.00   0.50    0.80    --  -75.17 -67.00 -72.22   62
 85  ω   -113.00 -87.00   0.50    0.20    --  -72.64 -65.00-110.33   52
 86  ω   -114.00 -88.00   0.50    0.20    --  -72.64 -67.00-117.85   52
 87  ω   -111.00 -85.00   0.50    0.20    --  -72.64 -64.00 -96.25   52
 88  ω   -110.00 -85.00   0.50    0.20    --  -72.64 -64.00 -57.64   50
 89  ω   -115.00 -90.00   0.50    0.80    --  -75.17 -63.00-133.16   50
 90  ω   -108.00 -83.00   0.50    0.20    --  -70.00 -63.00-153.83   50
 91  ω   -114.00 -88.00   0.50    0.20    --  -72.64 -64.00 -43.87   52
 92  ω   -115.00 -90.00   0.50    0.20    --  -72.64 -61.00  -4.51   50
 93  ω   -112.00 -87.00   0.50    0.20    --  -74.00 -61.00   8.77   50
 94  ω   -110.00 -80.00   0.50    0.20    --  -66.00 -59.00  32.98   60
 95  ω   -115.00 -87.00   0.50    0.20    --  -72.64 -61.00  52.66   56
 96  ω   -114.00 -86.00   0.50    0.20    --  -74.00 -64.00 100.50   56
 97  ω   -110.00 -85.00   0.50    0.20    --  -72.64 -64.00 119.83   50
 98  ω    -94.00 -69.00   0.50    0.20    --  -54.00 -54.00 149.54   50
 99  ω   -103.00 -78.00   0.50    0.20    --  -62.00 -50.00 162.11   50
100  ω    -94.00 -69.00   0.50    0.20    --  -54.00 -54.00  29.46   50
101  ω   -104.00 -78.00   0.50    0.20    --  -62.00 -46.00 127.80   52
102  ω    -98.00 -72.00   0.50    0.20    --  -54.00 -55.00   9.63   52
103  ω   -106.00 -81.00   0.50    0.20    --  -62.00 -50.00 -44.42   50
104  ω    -96.00 -71.00   0.50    0.20    --  -54.00 -54.00-155.03   50
105  ω   -115.00 -90.00   0.50    0.80    --  -75.17 -21.00-132.58   50
106  ω   -117.00 -92.00   0.50    0.80    --  -75.17 -21.00 -39.15   50
107  ω   -102.00 -76.00   0.50    0.20    --  -72.64 -14.00-115.30   52
108  ω   -107.00 -81.00   0.50    0.20    --  -70.00 -18.00 -27.29   52
109  ω   -102.00 -75.00   0.50    0.20    --  -72.64 -11.00 -83.35   54
110  ω   -109.00 -70.00   0.50    0.80    --  -75.17 -11.00   0.76   78
111  ω   -110.00 -84.00   0.50    0.20    --  -70.00 -20.00  72.04   52
112  ω   -104.00 -72.00   0.50    0.20    --  -66.00 -15.00  88.83   64
113  ω   -111.00 -84.00   0.50    0.20    --  -70.00 -17.00 129.06   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2576964000
_diffrn_orient_matrix_UB_12      0.0654787000
_diffrn_orient_matrix_UB_13      0.0897081000
_diffrn_orient_matrix_UB_21      -0.1008022000
_diffrn_orient_matrix_UB_22      0.1335605000
_diffrn_orient_matrix_UB_23      0.0113222000
_diffrn_orient_matrix_UB_31      -0.1127504000
_diffrn_orient_matrix_UB_32      -0.0202932000
_diffrn_orient_matrix_UB_33      0.1132914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1941
_reflns_number_total             2304
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2304
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.029
_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)+(0.0729P)²+0.1025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1197
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.93 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C2(H2), C6(H6), C3(H3), C5(H5)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
O3 O 0.31846(18) 0.71764(9) 0.15967(10) 0.0331(3) Uani 1 1 d . . . . .
O2 O 0.02114(19) 0.59287(10) 0.22377(10) 0.0356(3) Uani 1 1 d . . . . .
O1 O 0.4819(2) 0.12222(10) 0.44120(10) 0.0366(3) Uani 1 1 d . . . . .
N1 N 0.4406(2) 0.54992(12) 0.23175(12) 0.0327(3) Uani 1 1 d D . . . .
C4 C 0.4838(3) 0.22314(14) 0.38097(14) 0.0327(3) Uani 1 1 d . . . . .
C8 C 0.2859(3) 0.41867(14) 0.36770(14) 0.0328(4) Uani 1 1 d . . . . .
H8 H 0.168442 0.477947 0.390864 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4406(3) 0.43906(13) 0.28458(14) 0.0316(3) Uani 1 1 d . . . . .
C9 C 0.2391(3) 0.61774(13) 0.20709(14) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.6148(3) 0.35170(14) 0.25101(15) 0.0336(4) Uani 1 1 d . . . . .
H2 H 0.718504 0.368503 0.193868 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3086(3) 0.30748(14) 0.41653(14) 0.0321(3) Uani 1 1 d . . . . .
C6 C 0.1929(3) 0.25319(15) 0.50496(15) 0.0365(4) Uani 1 1 d . . . . .
H6 H 0.065206 0.287501 0.547610 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6401(3) 0.24213(14) 0.29843(16) 0.0357(4) Uani 1 1 d . . . . .
H3 H 0.758211 0.183093 0.275651 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1344(3) 0.80457(14) 0.11684(15) 0.0324(4) Uani 1 1 d . . . . .
C5 C 0.3012(3) 0.14508(15) 0.51486(15) 0.0364(4) Uani 1 1 d . . . . .
H5 H 0.258102 0.090007 0.567035 0.044 Uiso 1 1 calc R U . . .
C11 C -0.0766(3) 0.72731(15) 0.00762(15) 0.0369(4) Uani 1 1 d . . . . .
H11A H 0.002530 0.672155 -0.053681 0.055 Uiso 1 1 calc R U . . .
H11B H -0.173555 0.787491 -0.032809 0.055 Uiso 1 1 calc R U . . .
H11C H -0.194824 0.672433 0.038893 0.055 Uiso 1 1 calc R U . . .
C12 C 0.0262(3) 0.87533(15) 0.22591(16) 0.0383(4) Uani 1 1 d . . . . .
H12A H -0.100111 0.814693 0.246254 0.057 Uiso 1 1 calc R U . . .
H12B H -0.058951 0.947888 0.202304 0.057 Uiso 1 1 calc R U . . .
H12C H 0.167967 0.909037 0.299507 0.057 Uiso 1 1 calc R U . . .
C13 C 0.3076(3) 0.89918(15) 0.07343(18) 0.0402(4) Uani 1 1 d . . . . .
H13A H 0.446123 0.945481 0.144522 0.060 Uiso 1 1 calc R U . . .
H13B H 0.204504 0.962144 0.040960 0.060 Uiso 1 1 calc R U . . .
H13C H 0.384035 0.851017 0.006779 0.060 Uiso 1 1 calc R U . . .
H1 H 0.595(3) 0.5782(17) 0.2149(17) 0.048 Uiso 1 1 d D 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
O3 C9 1.3506(17) . ?
O3 C10 1.4771(17) . ?
O2 C9 1.2198(17) . ?
O1 C4 1.3778(17) . ?
O1 C5 1.3773(19) . ?
N1 C1 1.4208(19) . ?
N1 C9 1.3515(18) . ?
N1 H1 0.915(14) . ?
C4 C7 1.392(2) . ?
C4 C3 1.382(2) . ?
C8 H8 0.9500 . ?
C8 C1 1.385(2) . ?
C8 C7 1.403(2) . ?
C1 C2 1.403(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(2) . ?
C7 C6 1.445(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.337(2) . ?
C3 H3 0.9500 . ?
C10 C11 1.519(2) . ?
C10 C12 1.519(2) . ?
C10 C13 1.518(2) . ?
C5 H5 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C9 O3 C10 120.77(11) . . ?
C4 O1 C5 105.06(11) . . ?
C1 N1 H1 115.4(11) . . ?
C9 N1 C1 126.68(13) . . ?
C9 N1 H1 117.9(11) . . ?
O1 C4 C7 110.73(14) . . ?
O1 C4 C3 125.74(13) . . ?
C3 C4 C7 123.51(14) . . ?
C1 C8 H8 121.1 . . ?
C1 C8 C7 117.70(13) . . ?
C7 C8 H8 121.1 . . ?
C8 C1 N1 122.92(13) . . ?
C8 C1 C2 121.03(14) . . ?
C2 C1 N1 116.03(14) . . ?
O3 C9 N1 108.59(12) . . ?
O2 C9 O3 125.41(13) . . ?
O2 C9 N1 125.99(14) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.01(15) . . ?
C3 C2 H2 119.0 . . ?
C4 C7 C8 119.56(14) . . ?
C4 C7 C6 105.15(13) . . ?
C8 C7 C6 135.27(14) . . ?
C7 C6 H6 126.8 . . ?
C5 C6 C7 106.39(14) . . ?
C5 C6 H6 126.8 . . ?
C4 C3 H3 121.9 . . ?
C2 C3 C4 116.19(14) . . ?
C2 C3 H3 121.9 . . ?
O3 C10 C11 109.90(12) . . ?
O3 C10 C12 110.37(13) . . ?
O3 C10 C13 101.85(11) . . ?
C11 C10 C12 112.64(12) . . ?
C13 C10 C11 110.82(14) . . ?
C13 C10 C12 110.73(13) . . ?
O1 C5 H5 123.7 . . ?
C6 C5 O1 112.68(14) . . ?
C6 C5 H5 123.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C4 C7 C8 178.47(12) . . . . ?
O1 C4 C7 C6 0.06(16) . . . . ?
O1 C4 C3 C2 -178.45(13) . . . . ?
N1 C1 C2 C3 178.09(13) . . . . ?
C4 O1 C5 C6 -0.41(16) . . . . ?
C4 C7 C6 C5 -0.30(16) . . . . ?
C8 C1 C2 C3 0.1(2) . . . . ?
C8 C7 C6 C5 -178.34(16) . . . . ?
C1 N1 C9 O3 178.76(12) . . . . ?
C1 N1 C9 O2 -1.7(2) . . . . ?
C1 C8 C7 C4 0.3(2) . . . . ?
C1 C8 C7 C6 178.14(15) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C9 O3 C10 C11 -62.76(17) . . . . ?
C9 O3 C10 C12 62.07(16) . . . . ?
C9 O3 C10 C13 179.70(12) . . . . ?
C9 N1 C1 C8 -30.0(2) . . . . ?
C9 N1 C1 C2 152.06(14) . . . . ?
C7 C4 C3 C2 0.0(2) . . . . ?
C7 C8 C1 N1 -178.13(12) . . . . ?
C7 C8 C1 C2 -0.3(2) . . . . ?
C7 C6 C5 O1 0.45(17) . . . . ?
C3 C4 C7 C8 -0.2(2) . . . . ?
C3 C4 C7 C6 -178.58(14) . . . . ?
C10 O3 C9 O2 -3.1(2) . . . . ?
C10 O3 C9 N1 176.43(12) . . . . ?
C5 O1 C4 C7 0.20(15) . . . . ?
C5 O1 C4 C3 178.80(15) . . . . ?

_olex2_date_sample_data_collection 2024-11-26
_olex2_date_sample_submission    2024-11-26
_olex2_submission_original_sample_id bm281124_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.733
_oxdiff_exptl_absorpt_empirical_full_min 0.422
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_bm291124_1_1
_database_code_depnum_ccdc_archive 'CCDC 2418540'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2025-01-21 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
ann-sophie.paschke@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        'methyl benzo[d]isoxazole-5-carboxylate'
_chemical_formula_moiety         'C9 H7 N O3'
_chemical_formula_sum            'C9 H7 N O3'
_chemical_formula_weight         177.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H7NO3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.4696(3)
_cell_length_b                   11.1571(3)
_cell_length_c                   7.1041(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.043(3)
_cell_angle_gamma                90
_cell_volume                     789.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8797
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.4290
_cell_measurement_theta_min      3.9520
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0188
0 1 0 0.0197
2 0 -2 0.0925
-1 0 1 0.0968
1 0 0 0.0731
-7 0 0 0.0772
-7 0 1 0.0757
-6 3 1 0.0608
6 -3 0 0.0624
4 -3 -4 0.0844
-2 2 4 0.0978
3 -6 -2 0.0502
4 -6 0 0.0344
1 -7 0 0.0150
-1 0 -4 0.1332
2 7 -2 0.0490
2 7 -1 0.0361
2 -7 0 0.0122
1 4 4 0.0984

_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.039
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
0.0011 -0.9983 0.0084 -0.0147 0.1371 0.0040
0.0009 0.9966 -0.0098 0.0150 -0.1368 -0.0038
1.5015 -0.0278 -1.9872 0.2653 0.0169 0.3515
-1.0003 0.0140 0.9929 -0.1673 -0.0129 -0.1593
0.5011 0.0018 -0.0006 0.0697 0.0087 -0.0326
-6.6029 -0.2957 0.3236 -0.9320 -0.0746 0.3602
-6.8025 -0.2563 1.3375 -0.9882 -0.0767 0.1437
-6.0162 3.3262 0.9533 -0.8152 -0.5568 0.1579
5.8462 -3.0665 0.0013 0.7681 0.5247 -0.3643
3.9258 -2.7735 -3.9986 0.6197 0.4230 0.6642
-2.2379 1.9675 4.4431 -0.4095 -0.2794 -0.8703
3.0604 -5.8583 -2.3055 0.4056 0.8425 0.3562
3.6703 -5.9517 -0.0658 0.4250 0.8814 -0.1897
0.9564 -7.1404 0.1090 0.0251 0.9975 -0.0448
-0.8426 -0.2875 -4.1569 -0.0025 -0.0039 0.9969
1.5604 6.5782 -1.8214 0.3657 -0.8873 0.2709
1.7318 6.8153 -1.2960 0.3780 -0.9132 0.1394
1.6417 -7.0069 -0.1107 0.1287 0.9898 -0.0407
0.9531 3.8093 3.5073 0.0881 -0.4818 -0.8782

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14398
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.445
_diffrn_reflns_theta_min         4.442
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00 100.00   0.50    0.10    --   67.93-140.00  66.00  144
  2  ω     31.00 103.00   0.50    0.10    --   70.78-140.00  66.00  144
  3  ω     38.00 109.00   0.50    0.40    --   77.85-140.00  66.00  142
  4  ω     38.00 109.00   0.50    0.40    --   77.85-140.00  66.00  142
  5  ω     75.00 100.00   0.50    0.40    --   77.85-125.00 -30.00   50
  6  ω     33.00  59.00   0.50    0.40    --   77.85-125.00 -30.00   52
  7  ω     25.00  96.00   0.50    0.10    --   67.93-130.00-119.00  142
  8  ω     28.00  99.00   0.50    0.10    --   70.78-130.00-119.00  142
  9  ω     46.00  98.00   0.50    0.40    --   77.85-125.00-150.00  104
 10  ω     69.00 100.00   0.50    0.40    --   77.85-125.00-120.00   62
 11  ω     35.00 102.00   0.50    0.40    --   77.85-130.00-119.00  134
 12  ω     37.00  94.00   0.50    0.40    --   77.85-125.00 -90.00  114
 13  ω     37.00  84.00   0.50    0.40    --   77.85 -95.00 -90.00   94
 14  ω     44.00  83.00   0.50    0.40    --   77.85 -95.00-120.00   78
 15  ω     27.00  76.00   0.50    0.10    --   67.93 -95.00 -60.00   98
 16  ω     48.00  83.00   0.50    0.40    --   77.85 -95.00 -30.00   70
 17  ω     74.00 100.00   0.50    0.40    --   77.85-125.00   0.00   52
 18  ω     41.00  84.00   0.50    0.40    --   77.85 -95.00  90.00   86
 19  ω     81.00 113.00   0.50    0.10    --   72.89  16.00  24.62   64
 20  ω     92.00 118.00   0.50    0.40    --   75.17  23.00 -84.51   52
 21  ω     91.00 116.00   0.50    0.10    --   72.89  27.00-173.13   50
 22  ω     82.00 112.00   0.50    0.10    --   72.89  17.00  -6.31   60
 23  ω     61.00  92.00   0.50    0.10    --   46.00  53.00  66.92   62
 24  ω     91.00 116.00   0.50    0.40    --   75.17  22.00  94.16   50
 25  ω     91.00 116.00   0.50    0.40    --   75.17  20.00 161.44   50
 26  ω    -92.00 -61.00   0.50    0.10    --  -46.00 -53.00 119.50   62
 27  ω   -112.00 -81.00   0.50    0.10    --  -66.00 -53.00 152.25   62
 28  ω   -106.00 -72.00   0.50    0.10    --  -58.00 -45.00  90.97   68
 29  ω   -117.00 -85.00   0.50    0.10    --  -70.00 -38.00 175.70   64
 30  ω   -118.00 -84.00   0.50    0.10    --  -70.00 -45.00  67.50   68
 31  ω   -120.00 -91.00   0.50    0.10    --  -74.00 -31.00  85.84   58
 32  ω   -108.00 -80.00   0.50    0.10    --  -62.00 -33.00  17.87   56
 33  ω   -119.00 -94.00   0.50    0.40    --  -75.17 -27.00   2.57   50
 34  ω   -110.00 -76.00   0.50    0.10    --  -62.00 -45.00 -60.34   68
 35  ω   -105.00 -74.00   0.50    0.10    --  -58.00 -39.00-103.69   62
 36  ω   -112.00 -87.00   0.50    0.10    --  -70.00 -25.00-170.39   50
 37  ω   -101.00 -69.00   0.50    0.10    --  -54.00 -48.00-140.62   64
 38  ω   -114.00 -88.00   0.50    0.10    --  -72.64 -20.00-117.19   52
 39  ω   -114.00 -88.00   0.50    0.40    --  -75.17 -15.00-118.38   52
 40  ω   -110.00 -84.00   0.50    0.10    --  -70.00 -20.00-143.05   52
 41  ω   -118.00 -91.00   0.50    0.40    --  -75.17 -23.00  51.35   54
 42  ω   -117.00 -92.00   0.50    0.40    --  -75.17 -22.00 174.26   50
 43  ω   -111.00 -86.00   0.50    0.10    --  -70.00 -20.00 110.27   50
 44  ω    -63.00 -36.00   0.50    0.10    --  -72.64  75.00 107.86   54
 45  ω    -57.00 -32.00   0.50    0.10    --  -72.64  70.00 153.47   50
 46  ω    -35.00  -8.00   0.50    0.10    --  -54.00  52.00  67.08   54
 47  ω    -63.00 -38.00   0.50    0.10    --  -72.64  72.00  57.28   50
 48  ω    -98.00 -26.00   0.50    0.10    --  -66.25 140.00 125.00  144
 49  ω   -102.00 -29.00   0.50    0.10    --  -69.39 140.00 125.00  146
 50  ω    -95.00 -25.00   0.50    0.10    --  -69.39 125.00  30.00  140
 51  ω    -63.00 -31.00   0.50    0.40    --  -75.17 125.00   4.14   64
 52  ω    -99.00 -61.00   0.50    0.40    --  -75.17 121.00  -5.02   76
 53  ω    -95.00 -69.00   0.50    0.40    --  -75.17 125.00   4.14   52
 54  ω    -94.00 -23.00   0.50    0.10    --  -66.25 130.00 -47.00  142
 55  ω    -97.00 -26.00   0.50    0.10    --  -69.39 130.00 -47.00  142
 56  ω    -96.00 -68.00   0.50    0.40    --  -75.17 117.00-127.02   56
 57  ω    -62.00 -35.00   0.50    0.40    --  -75.17 115.00 -52.10   54
 58  ω    -99.00 -72.00   0.50    0.40    --  -75.17 121.00 -29.51   54
 59  ω    -95.00 -69.00   0.50    0.40    --  -75.17 115.00 -52.10   52
 60  ω    -68.00 -35.00   0.50    0.10    --  -72.64  99.00 -54.02   66
 61  ω    -64.00 -38.00   0.50    0.10    --  -72.64  84.00-120.13   52
 62  ω    -98.00 -72.00   0.50    0.40    --  -75.17 121.00  58.90   52
 63  ω    -57.00 -30.00   0.50    0.40    --  -75.17 121.00  58.90   54
 64  ω    -92.00 -51.00   0.50    0.10    --  -72.64 116.00 109.30   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1390867000
_diffrn_orient_matrix_UB_12      0.0146745000
_diffrn_orient_matrix_UB_13      -0.0286075000
_diffrn_orient_matrix_UB_21      0.0177816000
_diffrn_orient_matrix_UB_22      -0.1372090000
_diffrn_orient_matrix_UB_23      0.0068293000
_diffrn_orient_matrix_UB_31      -0.0653697000
_diffrn_orient_matrix_UB_32      -0.0059381000
_diffrn_orient_matrix_UB_33      -0.2261690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1380
_reflns_number_total             1556
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.067
_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)+(0.0637P)²+0.2086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O3 O 0.40238(9) 0.26494(8) 0.07092(13) 0.0211(2) Uani 1 1 d . . . . .
O1 O 0.98514(9) 0.28326(8) 0.64016(14) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.39885(10) 0.45795(9) 0.15525(16) 0.0337(3) Uani 1 1 d . . . . .
N1 N 0.99187(11) 0.15530(10) 0.63099(16) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.65199(12) 0.22915(11) 0.32434(18) 0.0184(3) Uani 1 1 d . . . . .
H4 H 0.600064 0.161586 0.264198 0.022 Uiso 1 1 calc R U . . .
C3 C 0.59924(12) 0.34361(11) 0.29539(18) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.85955(12) 0.31672(12) 0.52831(18) 0.0199(3) Uani 1 1 d . . . . .
C5 C 0.78449(13) 0.21674(11) 0.44536(18) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.80887(13) 0.43303(12) 0.50155(19) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.861897 0.500460 0.559642 0.028 Uiso 1 1 calc R U . . .
C2 C 0.45813(12) 0.36399(11) 0.16930(18) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.87538(12) 0.11908(12) 0.51820(19) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.853004 0.037337 0.487523 0.026 Uiso 1 1 calc R U . . .
C8 C 0.67639(13) 0.44412(12) 0.38497(19) 0.0219(3) Uani 1 1 d . . . . .
H8 H 0.636216 0.521340 0.364593 0.026 Uiso 1 1 calc R U . . .
C1 C 0.26684(13) 0.27892(12) -0.0591(2) 0.0229(3) Uani 1 1 d . . . . .
H1A H 0.264094 0.343394 -0.153960 0.034 Uiso 1 1 calc R U . . .
H1B H 0.207403 0.299029 0.019111 0.034 Uiso 1 1 calc R U . . .
H1C H 0.236904 0.203850 -0.130801 0.034 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
O3 C2 1.3408(15) . ?
O3 C1 1.4420(15) . ?
O1 N1 1.4318(15) . ?
O1 C6 1.3611(15) . ?
O2 C2 1.2066(16) . ?
N1 C9 1.2990(17) . ?
C4 H4 0.9500 . ?
C4 C3 1.3812(18) . ?
C4 C5 1.3942(17) . ?
C3 C2 1.4889(16) . ?
C3 C8 1.4129(17) . ?
C6 C5 1.3864(18) . ?
C6 C7 1.3926(19) . ?
C5 C9 1.4337(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3833(17) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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 O3 C1 115.33(10) . . ?
C6 O1 N1 107.41(9) . . ?
C9 N1 O1 106.75(10) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.34(11) . . ?
C5 C4 H4 121.3 . . ?
C4 C3 C2 120.48(11) . . ?
C4 C3 C8 121.35(11) . . ?
C8 C3 C2 118.17(11) . . ?
O1 C6 C5 110.20(11) . . ?
O1 C6 C7 126.41(11) . . ?
C5 C6 C7 123.36(12) . . ?
C4 C5 C9 136.09(12) . . ?
C6 C5 C4 120.45(12) . . ?
C6 C5 C9 103.45(12) . . ?
C6 C7 H7 122.1 . . ?
C8 C7 C6 115.72(12) . . ?
C8 C7 H7 122.1 . . ?
O3 C2 C3 112.23(10) . . ?
O2 C2 O3 122.91(11) . . ?
O2 C2 C3 124.86(11) . . ?
N1 C9 C5 112.19(12) . . ?
N1 C9 H9 123.9 . . ?
C5 C9 H9 123.9 . . ?
C3 C8 H8 119.1 . . ?
C7 C8 C3 121.74(12) . . ?
C7 C8 H8 119.1 . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O1 N1 C9 C5 0.01(14) . . . . ?
O1 C6 C5 C4 179.98(10) . . . . ?
O1 C6 C5 C9 0.48(14) . . . . ?
O1 C6 C7 C8 -178.24(11) . . . . ?
N1 O1 C6 C5 -0.50(13) . . . . ?
N1 O1 C6 C7 177.93(12) . . . . ?
C4 C3 C2 O3 -9.44(16) . . . . ?
C4 C3 C2 O2 170.49(13) . . . . ?
C4 C3 C8 C7 1.6(2) . . . . ?
C4 C5 C9 N1 -179.67(13) . . . . ?
C3 C4 C5 C6 -1.41(18) . . . . ?
C3 C4 C5 C9 177.89(13) . . . . ?
C6 O1 N1 C9 0.30(13) . . . . ?
C6 C5 C9 N1 -0.30(14) . . . . ?
C6 C7 C8 C3 -1.50(19) . . . . ?
C5 C4 C3 C2 -179.54(10) . . . . ?
C5 C4 C3 C8 -0.06(18) . . . . ?
C5 C6 C7 C8 0.00(19) . . . . ?
C7 C6 C5 C4 1.5(2) . . . . ?
C7 C6 C5 C9 -178.01(12) . . . . ?
C2 C3 C8 C7 -178.92(11) . . . . ?
C8 C3 C2 O3 171.06(11) . . . . ?
C8 C3 C2 O2 -9.01(19) . . . . ?
C1 O3 C2 O2 1.88(18) . . . . ?
C1 O3 C2 C3 -178.20(10) . . . . ?

_olex2_date_sample_data_collection 2024-11-26
_olex2_date_sample_submission    2024-11-26
_olex2_submission_original_sample_id bm291124_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.219
_oxdiff_exptl_absorpt_empirical_full_min 0.355
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
