# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_bau32
_database_code_depnum_ccdc_archive 'CCDC 2201533'
loop_
_audit_author_name
_audit_author_address
'Andrew Phillips'
;School of Chemistry, University College Dublin
Ireland
;
_audit_update_record             
;
2022-08-15 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT411_bau32               
;
PROBLEM: Short Inter H...H Contact  H6       ..H18B     .       2.14 Ang.
RESPONSE: Difference map checked and proposed hydrogens were located.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            4B
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F2 O3'
_chemical_formula_sum            'C22 H18 F2 O3'
_chemical_formula_weight         368.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H18 O3 F2'
_chemical_oxdiff_usercomment     'Compund 4B, Bau032'
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'
F F 0.0727 0.0534 '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                   7.80430(10)
_cell_length_b                   7.92550(10)
_cell_length_c                   14.73430(10)
_cell_angle_alpha                74.4540(10)
_cell_angle_beta                 77.6380(10)
_cell_angle_gamma                88.2870(10)
_cell_volume                     857.296(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19253
_cell_measurement_temperature    100.55(10)
_cell_measurement_theta_max      76.0780
_cell_measurement_theta_min      5.7840
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.802
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (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    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.0581
1 0 0 0.0403
-5 1 0 0.0686
-3 4 3 0.0735
0 0 1 0.0450
0 0 -1 0.0518
2 2 -6 0.0596
3 3 -3 0.0679
3 4 3 0.0795
0 0 -9 0.0565
-3 -4 -6 0.0865
-3 -4 -1 0.0992
3 0 8 0.0563
0 -3 5 0.0712
-3 0 -8 0.0746
-2 2 -7 0.0709
0 4 -4 0.0703
2 4 0 0.0776
1 5 3 0.0801
-3 4 0 0.0702
-5 0 -4 0.0729
-4 0 3 0.0741
-3 3 6 0.0718
4 0 -4 0.0470
4 2 0 0.0577

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
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
-0.0006 -0.9989 -1.0017 -0.0555 -0.1255 0.1489
1.0012 -0.0002 -0.0028 -0.0741 -0.1425 -0.1233
-4.9731 0.5642 -0.4894 0.2822 0.7917 0.5418
-3.0557 3.8174 2.8350 0.3285 0.9272 -0.1800
0.0009 -0.0003 1.0008 0.1098 -0.0126 -0.0124
-0.0009 0.0003 -1.0008 -0.1098 0.0126 0.0124
1.5337 1.8901 -6.4312 -0.9216 0.1228 -0.3683
2.5938 3.0750 -3.1741 -0.7069 0.0953 -0.7009
3.3945 3.9139 2.8439 -0.1513 0.0225 -0.9882
-0.4993 -0.4350 -9.3330 -0.9635 0.1268 0.2357
-3.2550 -3.7036 -5.8555 -0.2009 0.0241 0.9793
-3.2414 -3.7715 -0.5464 0.3843 -0.0532 0.9217
3.0473 0.0439 8.3978 0.6943 -0.5319 -0.4848
0.0933 -3.4964 4.9278 0.7241 -0.5576 0.4058
-3.2199 -0.4142 -8.3822 -0.6597 0.5050 0.5565
-1.6359 2.0676 -7.3008 -0.7930 0.6092 0.0088
0.1718 3.6781 -4.4348 -0.6995 0.5389 -0.4694
2.1092 4.4122 -0.0388 -0.3999 0.3101 -0.8625
1.0320 5.0658 2.8590 -0.0382 0.5177 -0.8547
-2.7300 4.1724 -0.4497 -0.0752 0.9707 -0.2283
-4.9474 -0.2333 -3.9701 -0.0582 0.7211 0.6904
-4.1935 0.2042 3.4827 0.6802 0.5817 0.4461
-2.5365 2.6272 6.4798 0.7549 0.6436 -0.1262
4.0640 0.2955 -3.6390 -0.7150 -0.4923 -0.4965
4.3514 2.1553 -0.2058 -0.4607 -0.3188 -0.8283

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33181
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.698
_diffrn_reflns_theta_min         5.797
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.55(10)
_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 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -59.00   0.30    0.30    --  -38.50-152.00 152.00  170
  2  ω    -85.00  -2.80   0.30    0.30    --  -38.50 121.00  35.00  274
  3  ω   -106.00 -20.80   0.30    0.30    --  -38.50 152.00-165.00  284
  4  ω     24.00  96.00   0.30    0.30    --   43.37-121.00 -48.00  240
  5  ω     41.00 116.00   0.30    0.30    --   43.37-152.00 152.00  250
  6  ω     39.00 111.00   0.30    0.40    --  111.00-121.00 -48.00  240
  7  ω     81.00 163.20   0.30    0.40    --  111.00 152.00-165.00  274
  8  ω     41.00 131.00   0.30    0.40    --  111.00-152.00 152.00  300
  9  ω     99.00 177.00   0.30    0.40    --  111.00 121.00  35.00  260
 10  ω     -2.00  23.20   0.30    0.30    --   34.00  91.00-112.92   84
 11  ω   -110.00  -9.80   0.30    0.30    --  -38.50 -68.00  45.81  334
 12  ω   -111.00 -16.80   0.30    0.30    --  -38.50 -37.00-150.00  314
 13  ω     12.00  42.00   0.30    0.30    --   43.37  78.00  23.25  100
 14  ω     14.00  41.00   0.30    0.30    --   46.00  81.00 -56.64   90
 15  ω     13.00  40.90   0.30    0.30    --   46.00  82.00 176.58   93
 16  ω     14.00  41.00   0.30    0.30    --   46.00  80.00-164.03   90
 17  ω     14.00  41.00   0.30    0.30    --   46.00  79.00 -10.55   90
 18  ω     14.00  41.00   0.30    0.30    --   46.00  79.00 134.39   90
 19  ω     14.00  41.00   0.30    0.30    --   46.00  80.00 170.33   90
 20  ω     14.00  41.00   0.30    0.30    --   46.00  80.00  52.25   90
 21  ω     25.00 124.00   0.30    0.30    --   54.00  69.00 -59.78  330
 22  ω     29.00 128.00   0.30    0.30    --   58.00  67.00 159.18  330
 23  ω     30.00 127.20   0.30    0.30    --   58.00  64.00  11.88  324
 24  ω     32.00 134.00   0.30    0.30    --   62.00  70.00-108.45  340
 25  ω     36.00 138.00   0.30    0.30    --   66.00  71.00  56.12  340
 26  ω     36.00 138.00   0.30    0.30    --   66.00  70.00-170.71  340
 27  ω     36.00 138.00   0.30    0.30    --   66.00  71.00  82.12  340
 28  ω     36.00 138.00   0.30    0.30    --   66.00  71.00 -48.67  340
 29  ω     42.00 141.00   0.30    0.30    --   70.00  65.00-111.24  330
 30  ω     41.00 140.00   0.30    0.30    --   70.00  69.00  17.12  330
 31  ω     52.00 148.00   0.30    0.40    --   78.00  55.00  69.33  320
 32  ω     54.00 151.20   0.30    0.40    --   82.00  63.00 -94.52  324
 33  ω     54.00 151.20   0.30    0.40    --   82.00  64.00  99.88  324
 34  ω     53.00 152.00   0.30    0.40    --   82.00  67.00 143.77  330
 35  ω     59.00 155.00   0.30    0.40    --   86.00  59.00 -53.36  320
 36  ω     59.00 155.00   0.30    0.40    --   86.00  57.00  92.63  320
 37  ω     65.00 164.00   0.30    0.40    --   94.00  67.00 143.18  330
 38  ω     64.00 166.00   0.30    0.40    --   94.00  70.00   3.35  340
 39  ω     67.00 163.00   0.30    0.40    --   94.00  58.00   0.36  320
 40  ω     66.00 163.20   0.30    0.40    --   94.00  61.00-159.94  324
 41  ω     64.00 166.00   0.30    0.40    --   94.00  71.00 -43.21  340
 42  ω     69.00 168.00   0.30    0.40    --   98.00  68.00  70.17  330
 43  ω     69.00 168.00   0.30    0.40    --   98.00  67.00-101.72  330
 44  ω     72.00 168.00   0.30    0.40    --   98.00  53.00 128.54  320
 45  ω     76.00 178.00   0.30    0.40    --  106.00  70.00  -7.47  340
 46  ω     34.00 106.90   0.30    0.40    --  111.00-105.00 157.13  243
 47  ω     84.00 177.00   0.30    0.40    --  111.00  59.00 172.11  310
 48  ω     30.00 105.90   0.30    0.40    --  111.00 -94.00-120.00  253
 49  ω     41.00 138.20   0.30    0.40    --  111.00 -61.00  90.00  324
 50  ω     40.00 134.20   0.30    0.40    --  111.00 -45.00-180.00  314
 51  ω     83.00 177.20   0.30    0.40    --  111.00  61.00 -60.00  314
 52  ω     36.00 108.00   0.30    0.40    --  111.00-111.00  30.00  240
 53  ω     83.00 177.20   0.30    0.40    --  111.00  61.00 120.00  314
 54  ω     30.00 105.90   0.30    0.40    --  111.00 -94.00  60.00  253
 55  ω     83.00 177.20   0.30    0.40    --  111.00  61.00  30.00  314
 56  ω     83.00 177.20   0.30    0.40    --  111.00  61.00  90.00  314
 57  ω     83.00 177.20   0.30    0.40    --  111.00  61.00-120.00  314
 58  ω     83.00 177.20   0.30    0.40    --  111.00  61.00-150.00  314
 59  ω     87.00 177.00   0.30    0.40    --  111.00  45.00 -90.00  300
 60  ω     87.00 177.00   0.30    0.40    --  111.00  45.00-150.00  300
 61  ω     83.00 177.20   0.30    0.40    --  111.00  64.00  59.76  314
 62  ω     30.00 105.90   0.30    0.40    --  111.00 -94.00-180.00  253
 63  ω     83.00 177.20   0.30    0.40    --  111.00  61.00 150.00  314
 64  ω     37.00 142.00   0.30    0.40    --  111.00 -77.00 -60.00  350
 65  ω     87.00 177.00   0.30    0.40    --  111.00  45.00  60.00  300
 66  ω     83.00 177.20   0.30    0.40    --  111.00  61.00 -30.00  314
 67  ω      6.00 121.20   0.30    0.30    --   43.37  19.00  90.00  384
 68  ω     13.00  40.90   0.30    0.30    --   46.00  82.00  99.72   93
;
_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      -0.0737223000
_diffrn_orient_matrix_UB_12      -0.0544380000
_diffrn_orient_matrix_UB_13      0.1097176000
_diffrn_orient_matrix_UB_21      -0.1423046000
_diffrn_orient_matrix_UB_22      0.1381935000
_diffrn_orient_matrix_UB_23      -0.0124174000
_diffrn_orient_matrix_UB_31      -0.1232355000
_diffrn_orient_matrix_UB_32      -0.1366794000
_diffrn_orient_matrix_UB_33      -0.0122938000
_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                3216
_reflns_number_total             3560
_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 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0017(4)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.3324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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
F26 F 0.34347(12) 0.59352(12) 0.06622(6) 0.0425(2) Uani 1 1 d . . . . .
F27 F -0.01152(10) 0.94890(11) 0.18454(6) 0.0378(2) Uani 1 1 d . . . . .
O2 O 0.65523(13) 0.77620(14) 0.63841(6) 0.0348(2) Uani 1 1 d . . . . .
O5 O 0.84404(12) 0.90741(14) 0.49296(6) 0.0330(2) Uani 1 1 d . . . . .
O16 O 0.02789(12) 0.56390(13) 0.29407(7) 0.0345(2) Uani 1 1 d . . . . .
C1 C 0.82232(18) 0.86423(19) 0.59613(9) 0.0303(3) Uani 1 1 d . . . . .
H1A H 0.917159 0.787293 0.616536 0.036 Uiso 1 1 calc R U . . .
H1B H 0.827545 0.972186 0.617207 0.036 Uiso 1 1 calc R U . . .
C3 C 0.57934(17) 0.77074(17) 0.56346(9) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.69170(16) 0.85074(17) 0.47595(9) 0.0253(3) Uani 1 1 d . . . . .
C6 C 0.41935(17) 0.69632(17) 0.56954(9) 0.0264(3) Uani 1 1 d . . . . .
H6 H 0.343535 0.643019 0.629621 0.032 Uiso 1 1 calc R U . . .
C7 C 0.37552(16) 0.70414(16) 0.48169(8) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.48687(16) 0.78897(16) 0.39282(8) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.65040(16) 0.86478(16) 0.38814(9) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.726515 0.921385 0.328768 0.029 Uiso 1 1 calc R U . . .
C10 C 0.21458(16) 0.62558(17) 0.46549(8) 0.0255(3) Uani 1 1 d . . . . .
H10A H 0.207776 0.496607 0.491858 0.031 Uiso 1 1 calc R U . . .
H10B H 0.105732 0.676228 0.494357 0.031 Uiso 1 1 calc R U . . .
C11 C 0.24711(16) 0.67782(16) 0.35754(9) 0.0244(3) Uani 1 1 d . . . . .
C12 C 0.39851(16) 0.77320(16) 0.31779(8) 0.0230(3) Uani 1 1 d . . . . .
C13 C 0.15755(16) 0.65381(17) 0.28507(9) 0.0263(3) Uani 1 1 d . . . . .
C14 C 0.26166(16) 0.77001(17) 0.18920(9) 0.0257(3) Uani 1 1 d . . . . .
C15 C 0.42974(16) 0.84229(17) 0.20906(8) 0.0236(3) Uani 1 1 d . . . . .
C17 C 0.60378(16) 0.79024(17) 0.15323(8) 0.0251(3) Uani 1 1 d . . . . .
H17A H 0.598684 0.816844 0.084276 0.030 Uiso 1 1 calc R U . . .
H17B H 0.699612 0.864171 0.158135 0.030 Uiso 1 1 calc R U . . .
C18 C 0.64993(17) 0.59910(18) 0.18693(9) 0.0278(3) Uani 1 1 d . . . . .
H18A H 0.543255 0.524238 0.200417 0.033 Uiso 1 1 calc R U . . .
H18B H 0.691742 0.579909 0.247681 0.033 Uiso 1 1 calc R U . . .
C19 C 0.79127(17) 0.54534(19) 0.11189(9) 0.0308(3) Uani 1 1 d . . . . .
H19A H 0.743736 0.551731 0.053954 0.037 Uiso 1 1 calc R U . . .
H19B H 0.891837 0.629953 0.092540 0.037 Uiso 1 1 calc R U . . .
C20 C 0.85644(19) 0.3621(2) 0.14731(11) 0.0372(3) Uani 1 1 d . . . . .
H20A H 0.939841 0.332110 0.094420 0.056 Uiso 1 1 calc R U . . .
H20B H 0.756804 0.278074 0.169861 0.056 Uiso 1 1 calc R U . . .
H20C H 0.914741 0.357856 0.200512 0.056 Uiso 1 1 calc R U . . .
C21 C 0.26656(18) 0.72780(19) 0.09547(9) 0.0314(3) Uani 1 1 d . . . . .
C22 C 0.18490(18) 0.8644(2) 0.05288(10) 0.0347(3) Uani 1 1 d . . . . .
H22 H 0.152342 0.902311 -0.007787 0.042 Uiso 1 1 calc R U . . .
C23 C 0.16406(16) 0.93633(19) 0.14002(9) 0.0298(3) Uani 1 1 d . . . . .
C24 C 0.27148(17) 1.08896(18) 0.13894(9) 0.0298(3) Uani 1 1 d . . . . .
H24 H 0.243848 1.207676 0.114162 0.036 Uiso 1 1 calc R U . . .
C25 C 0.41063(17) 1.03926(17) 0.17677(9) 0.0263(3) Uani 1 1 d . . . . .
H25 H 0.491626 1.120291 0.183116 0.032 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
F26 C21 1.3325(17) . ?
F27 C23 1.3999(15) . ?
O2 C1 1.4315(17) . ?
O2 C3 1.3710(15) . ?
O5 C1 1.4391(15) . ?
O5 C4 1.3776(15) . ?
O16 C13 1.2184(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.3944(18) . ?
C3 C6 1.3721(19) . ?
C4 C9 1.3746(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3933(17) . ?
C7 C8 1.4134(16) . ?
C7 C10 1.5090(17) . ?
C8 C9 1.4073(17) . ?
C8 C12 1.4556(16) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.4988(16) . ?
C11 C12 1.3530(18) . ?
C11 C13 1.4496(17) . ?
C12 C15 1.5154(16) . ?
C13 C14 1.5361(17) . ?
C14 C15 1.5600(17) . ?
C14 C21 1.4984(17) . ?
C14 C23 1.5834(18) . ?
C15 C17 1.5368(17) . ?
C15 C25 1.5178(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5205(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5241(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.318(2) . ?
C21 C23 2.020(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.5159(19) . ?
C23 C24 1.487(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.3271(18) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C1 106.49(10) . . ?
C4 O5 C1 106.08(10) . . ?
O2 C1 O5 107.96(10) . . ?
O2 C1 H1A 110.1 . . ?
O2 C1 H1B 110.1 . . ?
O5 C1 H1A 110.1 . . ?
O5 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
O2 C3 C4 109.82(11) . . ?
O2 C3 C6 127.13(11) . . ?
C6 C3 C4 123.04(11) . . ?
O5 C4 C3 109.62(10) . . ?
C9 C4 O5 127.50(11) . . ?
C9 C4 C3 122.88(12) . . ?
C3 C6 H6 122.2 . . ?
C3 C6 C7 115.53(11) . . ?
C7 C6 H6 122.2 . . ?
C6 C7 C8 121.68(12) . . ?
C6 C7 C10 127.56(11) . . ?
C8 C7 C10 110.75(10) . . ?
C7 C8 C12 106.36(11) . . ?
C9 C8 C7 121.88(11) . . ?
C9 C8 C12 131.74(11) . . ?
C4 C9 C8 114.95(11) . . ?
C4 C9 H9 122.5 . . ?
C8 C9 H9 122.5 . . ?
C7 C10 H10A 111.5 . . ?
C7 C10 H10B 111.5 . . ?
H10A C10 H10B 109.4 . . ?
C11 C10 C7 101.13(10) . . ?
C11 C10 H10A 111.5 . . ?
C11 C10 H10B 111.5 . . ?
C12 C11 C10 111.51(11) . . ?
C12 C11 C13 112.03(11) . . ?
C13 C11 C10 136.46(11) . . ?
C8 C12 C15 136.22(11) . . ?
C11 C12 C8 110.18(11) . . ?
C11 C12 C15 113.54(11) . . ?
O16 C13 C11 129.80(12) . . ?
O16 C13 C14 125.22(11) . . ?
C11 C13 C14 104.98(10) . . ?
C13 C14 C15 107.98(10) . . ?
C13 C14 C23 115.73(10) . . ?
C15 C14 C23 105.89(10) . . ?
C21 C14 C13 121.45(11) . . ?
C21 C14 C15 120.37(10) . . ?
C21 C14 C23 81.85(10) . . ?
C12 C15 C14 100.91(9) . . ?
C12 C15 C17 115.15(10) . . ?
C12 C15 C25 112.39(10) . . ?
C17 C15 C14 114.84(10) . . ?
C25 C15 C14 102.80(10) . . ?
C25 C15 C17 109.89(10) . . ?
C15 C17 H17A 108.4 . . ?
C15 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
C18 C17 C15 115.33(10) . . ?
C18 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C17 C18 C19 111.87(11) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.49(11) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F26 C21 C14 127.61(12) . . ?
F26 C21 C23 176.63(11) . . ?
C14 C21 C23 50.90(7) . . ?
C22 C21 F26 132.75(13) . . ?
C22 C21 C14 99.53(12) . . ?
C22 C21 C23 48.63(8) . . ?
C21 C22 H22 134.7 . . ?
C21 C22 C23 90.64(11) . . ?
C23 C22 H22 134.7 . . ?
F27 C23 C14 115.71(10) . . ?
F27 C23 C21 125.06(10) . . ?
F27 C23 C22 113.11(11) . . ?
F27 C23 C24 111.15(11) . . ?
C14 C23 C21 47.25(7) . . ?
C22 C23 C14 87.98(10) . . ?
C22 C23 C21 40.73(8) . . ?
C24 C23 C14 104.89(10) . . ?
C24 C23 C21 123.48(10) . . ?
C24 C23 C22 121.75(11) . . ?
C23 C24 H24 124.1 . . ?
C25 C24 C23 111.81(12) . . ?
C25 C24 H24 124.1 . . ?
C15 C25 H25 122.8 . . ?
C24 C25 C15 114.48(12) . . ?
C24 C25 H25 122.8 . . ?

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
F26 C21 C22 C23 -175.85(15) . . . . ?
F27 C23 C24 C25 126.58(12) . . . . ?
O2 C3 C4 O5 0.84(15) . . . . ?
O2 C3 C4 C9 179.99(12) . . . . ?
O2 C3 C6 C7 -178.02(12) . . . . ?
O5 C4 C9 C8 177.77(12) . . . . ?
O16 C13 C14 C15 -172.86(12) . . . . ?
O16 C13 C14 C21 -27.6(2) . . . . ?
O16 C13 C14 C23 68.72(17) . . . . ?
C1 O2 C3 C4 0.27(14) . . . . ?
C1 O2 C3 C6 178.97(12) . . . . ?
C1 O5 C4 C3 -1.57(14) . . . . ?
C1 O5 C4 C9 179.34(13) . . . . ?
C3 O2 C1 O5 -1.22(14) . . . . ?
C3 C4 C9 C8 -1.22(18) . . . . ?
C3 C6 C7 C8 -2.16(18) . . . . ?
C3 C6 C7 C10 176.34(12) . . . . ?
C4 O5 C1 O2 1.71(14) . . . . ?
C4 C3 C6 C7 0.52(19) . . . . ?
C6 C3 C4 O5 -177.93(11) . . . . ?
C6 C3 C4 C9 1.2(2) . . . . ?
C6 C7 C8 C9 2.20(19) . . . . ?
C6 C7 C8 C12 -179.23(11) . . . . ?
C6 C7 C10 C11 -179.30(12) . . . . ?
C7 C8 C9 C4 -0.43(17) . . . . ?
C7 C8 C12 C11 -2.78(14) . . . . ?
C7 C8 C12 C15 173.97(13) . . . . ?
C7 C10 C11 C12 -1.10(14) . . . . ?
C7 C10 C11 C13 179.59(14) . . . . ?
C8 C7 C10 C11 -0.67(13) . . . . ?
C8 C12 C15 C14 -176.12(13) . . . . ?
C8 C12 C15 C17 59.61(19) . . . . ?
C8 C12 C15 C25 -67.25(18) . . . . ?
C9 C8 C12 C11 175.60(13) . . . . ?
C9 C8 C12 C15 -7.6(2) . . . . ?
C10 C7 C8 C9 -176.52(11) . . . . ?
C10 C7 C8 C12 2.05(14) . . . . ?
C10 C11 C12 C8 2.44(15) . . . . ?
C10 C11 C12 C15 -175.11(10) . . . . ?
C10 C11 C13 O16 -7.7(3) . . . . ?
C10 C11 C13 C14 172.02(14) . . . . ?
C11 C12 C15 C14 0.55(14) . . . . ?
C11 C12 C15 C17 -123.72(12) . . . . ?
C11 C12 C15 C25 109.42(12) . . . . ?
C11 C13 C14 C15 7.39(13) . . . . ?
C11 C13 C14 C21 152.63(12) . . . . ?
C11 C13 C14 C23 -111.03(12) . . . . ?
C12 C8 C9 C4 -178.60(12) . . . . ?
C12 C11 C13 O16 172.98(13) . . . . ?
C12 C11 C13 C14 -7.29(14) . . . . ?
C12 C15 C17 C18 44.88(15) . . . . ?
C12 C15 C25 C24 -110.92(12) . . . . ?
C13 C11 C12 C8 -178.07(10) . . . . ?
C13 C11 C12 C15 4.38(15) . . . . ?
C13 C14 C15 C12 -4.89(13) . . . . ?
C13 C14 C15 C17 119.59(11) . . . . ?
C13 C14 C15 C25 -121.09(11) . . . . ?
C13 C14 C21 F26 -68.61(18) . . . . ?
C13 C14 C21 C22 114.94(13) . . . . ?
C13 C14 C21 C23 115.25(13) . . . . ?
C13 C14 C23 F27 -6.03(16) . . . . ?
C13 C14 C23 C21 -121.07(13) . . . . ?
C13 C14 C23 C22 -120.80(11) . . . . ?
C13 C14 C23 C24 116.82(12) . . . . ?
C14 C15 C17 C18 -71.72(13) . . . . ?
C14 C15 C25 C24 -3.25(14) . . . . ?
C14 C21 C22 C23 0.32(11) . . . . ?
C14 C23 C24 C25 0.84(14) . . . . ?
C15 C14 C21 F26 72.45(18) . . . . ?
C15 C14 C21 C22 -104.01(13) . . . . ?
C15 C14 C21 C23 -103.69(13) . . . . ?
C15 C14 C23 F27 -125.60(11) . . . . ?
C15 C14 C23 C21 119.36(11) . . . . ?
C15 C14 C23 C22 119.63(10) . . . . ?
C15 C14 C23 C24 -2.75(12) . . . . ?
C15 C17 C18 C19 163.09(10) . . . . ?
C17 C15 C25 C24 119.45(12) . . . . ?
C17 C18 C19 C20 173.18(11) . . . . ?
C21 C14 C15 C12 -150.57(12) . . . . ?
C21 C14 C15 C17 -26.09(16) . . . . ?
C21 C14 C15 C25 93.22(13) . . . . ?
C21 C14 C23 F27 115.04(12) . . . . ?
C21 C14 C23 C22 0.27(9) . . . . ?
C21 C14 C23 C24 -122.11(11) . . . . ?
C21 C22 C23 F27 -117.49(12) . . . . ?
C21 C22 C23 C14 -0.30(10) . . . . ?
C21 C22 C23 C24 106.00(14) . . . . ?
C21 C23 C24 C25 -47.39(16) . . . . ?
C22 C23 C24 C25 -96.16(15) . . . . ?
C23 C14 C15 C12 119.65(10) . . . . ?
C23 C14 C15 C17 -115.87(11) . . . . ?
C23 C14 C15 C25 3.45(12) . . . . ?
C23 C14 C21 F26 176.14(14) . . . . ?
C23 C14 C21 C22 -0.31(11) . . . . ?
C23 C24 C25 C15 1.58(16) . . . . ?
C25 C15 C17 C18 172.99(10) . . . . ?

_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.854


_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_bau47
_database_code_depnum_ccdc_archive 'CCDC 2201535'
loop_
_audit_author_name
_audit_author_address
'Andrew Phillips'
;School of Chemistry, University College Dublin
Ireland
;
_audit_update_record             
;
2022-08-15 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-06-10

_audit_creation_method           
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            4J
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 F O4'
_chemical_formula_sum            'C23 H21 F O4'
_chemical_formula_weight         380.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' C23 H23 F1 O3'
_chemical_oxdiff_usercomment     'Compound 4J, Bau47'
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'
F F 0.0727 0.0534 '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                   8.6257(3)
_cell_length_b                   10.2667(3)
_cell_length_c                   10.6007(3)
_cell_angle_alpha                86.328(2)
_cell_angle_beta                 76.801(3)
_cell_angle_gamma                87.255(3)
_cell_volume                     911.56(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6698
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.1250
_cell_measurement_theta_min      4.2610
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (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            'metallic dark yellow'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 -1 0.0334
1 6 3 0.0648
5 -1 3 0.0374
-1 -6 -3 0.0643
2 -1 7 0.0368
-3 -6 -3 0.0558
3 6 3 0.0591
-1 0 6 0.0322
1 0 -6 0.0405

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
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
-1.9999 0.9995 -0.9994 -0.1094 -0.3810 -0.0634
1.3519 6.2184 2.7294 -0.0609 -0.2626 0.9630
5.3623 -0.9487 2.8901 0.2168 0.8967 0.3858
-1.0562 -6.3054 -2.5808 0.0735 0.3147 -0.9463
2.4662 -1.0575 6.5097 0.8602 0.3567 0.3645
-2.6155 -5.7332 -2.9098 0.0637 0.0235 -0.9977
2.6212 5.7237 2.9290 -0.0607 -0.0222 0.9979
-0.7351 -0.2373 6.4115 0.9422 -0.2275 0.2461
0.7718 0.3085 -6.3890 -0.9451 0.2281 -0.2341

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14565
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.397
_diffrn_reflns_theta_min         4.290
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(2)
_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 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  18.00   0.50    1.50    --  -41.58  97.00-132.00  196
  2  ω      4.00  81.00   0.50    1.50    --   41.58 -97.00 118.00  154
  3  ω     30.00 107.00   0.50    6.00    --  112.00 -97.00 118.00  154
  4  ω    104.00 178.00   0.50    6.00    --  112.00  97.00-132.00  148
  5  ω   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00  90.00  198
  6  ω   -115.00 -13.00   0.50    1.50    --  -41.58 -57.00   0.00  204
  7  ω    -38.00  83.00   0.50    1.50    --   41.58 -19.00 -60.00  242
  8  ω      8.00  42.00   0.50    1.50    --   41.58  82.00 -34.88   68
  9  ω      8.00  42.00   0.50    1.50    --   41.58  82.00-125.10   68
 10  ω     86.00 178.00   0.50    6.00    --  112.00  45.00   0.00  184
 11  ω     84.00 178.00   0.50    6.00    --  112.00  30.00 -90.00  188
 12  ω     39.00 138.00   0.50    6.00    --  112.00 -45.00 120.00  198
 13  ω     84.00 178.00   0.50    6.00    --  112.00  30.00  60.00  188
 14  ω     36.00 145.00   0.50    6.00    --  112.00 -77.00  30.00  218
 15  ω     36.00 109.00   0.50    6.00    --  112.00-111.00   0.00  146
 16  ω     36.00 109.00   0.50    6.00    --  112.00-111.00-120.00  146
 17  ω    103.00 178.00   0.50    6.00    --  112.00  77.00  90.00  150
 18  ω     36.00 109.00   0.50    6.00    --  112.00-111.00 120.00  146
 19  ω     61.00 146.00   0.50    6.00    --  112.00 178.00  60.00  170
 20  ω     36.00 109.00   0.50    6.00    --  112.00-111.00-150.00  146
 21  ω     29.00 107.00   0.50    6.00    --  112.00 -94.00 -90.00  156
 22  ω     36.00 109.00   0.50    6.00    --  112.00-111.00  60.00  146
 23  ω     36.00 109.00   0.50    6.00    --  112.00-111.00  30.00  146
 24  ω    104.00 178.00   0.50    6.00    --  112.00 111.00-180.00  148
 25  ω    104.00 178.00   0.50    6.00    --  112.00 111.00 150.00  148
 26  ω     39.00 138.00   0.50    6.00    --  112.00 -45.00  90.00  198
 27  ω     29.00 107.00   0.50    6.00    --  112.00 -94.00 -60.00  156
 28  ω     86.00 178.00   0.50    6.00    --  112.00  45.00 150.00  184
 29  ω   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00-120.00  198
 30  ω   -116.00 -17.00   0.50    1.50    --  -41.58 -37.00-180.00  198
 31  ω      8.00  42.00   0.50    1.50    --   41.58  80.00  38.52   68
 32  ω     27.00  98.00   0.50    1.50    --   41.58-125.00   0.00  142
 33  ω    -33.00  66.00   0.50    1.50    --   41.58 -37.00 120.00  198
 34  ω      8.00  42.00   0.50    1.50    --   41.58  82.00 130.33   68
;
_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      -0.0455454000
_diffrn_orient_matrix_UB_12      -0.0611086000
_diffrn_orient_matrix_UB_13      0.1394672000
_diffrn_orient_matrix_UB_21      0.1651975000
_diffrn_orient_matrix_UB_22      -0.0697511000
_diffrn_orient_matrix_UB_23      -0.0191215000
_diffrn_orient_matrix_UB_31      0.0657873000
_diffrn_orient_matrix_UB_32      0.1184736000
_diffrn_orient_matrix_UB_33      0.0503117000
_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                3052
_reflns_number_total             3765
_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 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.035
_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)+(0.0493P)²+0.1895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C10(H10A,H10B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C28(H28A,H28B,H28C)
;
_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
F26 F 0.87532(10) 0.37863(8) -0.13043(8) 0.0308(2) Uani 1 1 d . . . . .
O2 O 0.08661(13) 0.02921(10) 0.65596(11) 0.0351(3) Uani 1 1 d . . . . .
O5 O 0.16477(13) 0.23210(10) 0.69593(10) 0.0327(2) Uani 1 1 d . . . . .
O16 O 0.73459(12) 0.14208(9) -0.04629(10) 0.0298(2) Uani 1 1 d . . . . .
O27 O 0.70761(12) 0.77921(9) 0.03980(10) 0.0295(2) Uani 1 1 d . . . . .
C1 C 0.0855(2) 0.11681(15) 0.75594(15) 0.0361(3) Uani 1 1 d . . . . .
H1A H 0.141566 0.075438 0.820719 0.043 Uiso 1 1 calc R U . . .
H1B H -0.025423 0.139321 0.800694 0.043 Uiso 1 1 calc R U . . .
C3 C 0.20356(17) 0.07253(13) 0.55296(14) 0.0278(3) Uani 1 1 d . . . . .
C4 C 0.24866(17) 0.19591(13) 0.57662(14) 0.0268(3) Uani 1 1 d . . . . .
C6 C 0.26565(17) 0.01166(13) 0.43966(14) 0.0287(3) Uani 1 1 d . . . . .
H6 H 0.234930 -0.072838 0.425462 0.034 Uiso 1 1 calc R U . . .
C7 C 0.37646(16) 0.08166(13) 0.34694(14) 0.0257(3) Uani 1 1 d . . . . .
C8 C 0.41663(16) 0.20939(13) 0.36864(13) 0.0247(3) Uani 1 1 d . . . . .
C9 C 0.35343(17) 0.26890(13) 0.48570(13) 0.0260(3) Uani 1 1 d . . . . .
H9 H 0.381269 0.353956 0.501000 0.031 Uiso 1 1 calc R U . . .
C10 C 0.47008(17) 0.04002(13) 0.21616(14) 0.0269(3) Uani 1 1 d . . . . .
H10A H 0.542784 -0.035856 0.225138 0.032 Uiso 1 1 calc R U . . .
H10B H 0.398840 0.018591 0.159821 0.032 Uiso 1 1 calc R U . . .
C11 C 0.56064(16) 0.16097(12) 0.16527(14) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.52759(16) 0.25529(12) 0.25189(13) 0.0239(3) Uani 1 1 d . . . . .
C13 C 0.67557(16) 0.20436(12) 0.04950(13) 0.0250(3) Uani 1 1 d . . . . .
C14 C 0.70568(16) 0.34280(12) 0.07106(13) 0.0240(3) Uani 1 1 d . . . . .
C15 C 0.61632(16) 0.37951(12) 0.20574(13) 0.0229(3) Uani 1 1 d . . . . .
C17 C 0.72724(16) 0.40696(12) 0.29748(13) 0.0247(3) Uani 1 1 d . . . . .
H17A H 0.799248 0.477686 0.256734 0.030 Uiso 1 1 calc R U . . .
H17B H 0.661213 0.437876 0.379938 0.030 Uiso 1 1 calc R U . . .
C18 C 0.82714(17) 0.28736(13) 0.32712(14) 0.0269(3) Uani 1 1 d . . . . .
H18A H 0.884311 0.251043 0.244266 0.032 Uiso 1 1 calc R U . . .
H18B H 0.755095 0.219976 0.375798 0.032 Uiso 1 1 calc R U . . .
C19 C 0.94864(19) 0.31569(14) 0.40572(15) 0.0326(3) Uani 1 1 d . . . . .
H19A H 1.012323 0.234748 0.416971 0.039 Uiso 1 1 calc R U . . .
H19B H 1.022322 0.381572 0.356227 0.039 Uiso 1 1 calc R U . . .
C20 C 0.8730(2) 0.36548(15) 0.53873(16) 0.0378(4) Uani 1 1 d . . . . .
H20A H 0.825554 0.453075 0.528453 0.057 Uiso 1 1 calc R U . . .
H20B H 0.954605 0.369093 0.589175 0.057 Uiso 1 1 calc R U . . .
H20C H 0.789953 0.306328 0.584229 0.057 Uiso 1 1 calc R U . . .
C21 C 0.79084(16) 0.42645(13) -0.01759(13) 0.0248(3) Uani 1 1 d . . . . .
C22 C 0.80545(17) 0.56470(13) -0.01675(14) 0.0265(3) Uani 1 1 d . . . . .
H22 H 0.899399 0.601680 -0.068635 0.032 Uiso 1 1 calc R U . . .
C23 C 0.69510(17) 0.64685(12) 0.05266(13) 0.0259(3) Uani 1 1 d . . . . .
C24 C 0.54408(17) 0.61261(13) 0.13890(13) 0.0262(3) Uani 1 1 d . . . . .
H24 H 0.464300 0.680488 0.153567 0.031 Uiso 1 1 calc R U . . .
C25 C 0.50417(17) 0.49665(13) 0.20010(13) 0.0251(3) Uani 1 1 d . . . . .
H25 H 0.395865 0.487094 0.243848 0.030 Uiso 1 1 calc R U . . .
C28 C 0.83950(19) 0.83076(13) -0.05542(16) 0.0339(3) Uani 1 1 d . . . . .
H28A H 0.836595 0.801311 -0.140958 0.051 Uiso 1 1 calc R U . . .
H28B H 0.939520 0.799786 -0.032911 0.051 Uiso 1 1 calc R U . . .
H28C H 0.832491 0.926397 -0.057451 0.051 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
F26 C21 1.3586(16) . ?
O2 C1 1.4314(18) . ?
O2 C3 1.3730(18) . ?
O5 C1 1.4336(17) . ?
O5 C4 1.3704(17) . ?
O16 C13 1.2308(17) . ?
O27 C23 1.3640(16) . ?
O27 C28 1.4346(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C3 C4 1.3968(19) . ?
C3 C6 1.375(2) . ?
C4 C9 1.372(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C7 C8 1.4183(18) . ?
C7 C10 1.513(2) . ?
C8 C9 1.4024(19) . ?
C8 C12 1.4483(19) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5026(18) . ?
C11 C12 1.3527(19) . ?
C11 C13 1.451(2) . ?
C12 C15 1.5147(17) . ?
C13 C14 1.4980(17) . ?
C14 C15 1.5209(18) . ?
C14 C21 1.3423(19) . ?
C15 C17 1.5576(17) . ?
C15 C25 1.5138(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5238(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5285(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.4318(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.357(2) . ?
C23 C24 1.454(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.3398(19) . ?
C25 H25 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C3 O2 C1 105.03(11) . . ?
C4 O5 C1 104.89(11) . . ?
C23 O27 C28 117.50(11) . . ?
O2 C1 O5 107.68(12) . . ?
O2 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
O5 C1 H1A 110.2 . . ?
O5 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O2 C3 C4 109.20(12) . . ?
O2 C3 C6 127.69(12) . . ?
C6 C3 C4 123.04(13) . . ?
O5 C4 C3 109.81(12) . . ?
O5 C4 C9 127.57(12) . . ?
C9 C4 C3 122.45(13) . . ?
C3 C6 H6 122.1 . . ?
C3 C6 C7 115.83(12) . . ?
C7 C6 H6 122.1 . . ?
C6 C7 C8 121.06(13) . . ?
C6 C7 C10 128.58(12) . . ?
C8 C7 C10 110.35(12) . . ?
C7 C8 C12 106.63(12) . . ?
C9 C8 C7 122.09(13) . . ?
C9 C8 C12 131.28(12) . . ?
C4 C9 C8 115.43(12) . . ?
C4 C9 H9 122.3 . . ?
C8 C9 H9 122.3 . . ?
C7 C10 H10A 111.6 . . ?
C7 C10 H10B 111.6 . . ?
H10A C10 H10B 109.4 . . ?
C11 C10 C7 101.10(11) . . ?
C11 C10 H10A 111.6 . . ?
C11 C10 H10B 111.6 . . ?
C12 C11 C10 111.41(12) . . ?
C12 C11 C13 110.92(12) . . ?
C13 C11 C10 137.66(12) . . ?
C8 C12 C15 135.91(12) . . ?
C11 C12 C8 110.40(12) . . ?
C11 C12 C15 113.67(12) . . ?
O16 C13 C11 127.84(12) . . ?
O16 C13 C14 127.30(13) . . ?
C11 C13 C14 104.85(11) . . ?
C13 C14 C15 110.39(11) . . ?
C21 C14 C13 125.47(13) . . ?
C21 C14 C15 124.01(12) . . ?
C12 C15 C14 100.01(10) . . ?
C12 C15 C17 110.30(10) . . ?
C14 C15 C17 113.75(11) . . ?
C25 C15 C12 112.10(11) . . ?
C25 C15 C14 111.81(11) . . ?
C25 C15 C17 108.72(10) . . ?
C15 C17 H17A 109.0 . . ?
C15 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C15 113.03(10) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.73(11) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.37(13) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F26 C21 C22 111.44(12) . . ?
C14 C21 F26 118.04(12) . . ?
C14 C21 C22 130.48(13) . . ?
C21 C22 H22 117.6 . . ?
C23 C22 C21 124.86(13) . . ?
C23 C22 H22 117.6 . . ?
O27 C23 C24 110.17(12) . . ?
C22 C23 O27 122.33(13) . . ?
C22 C23 C24 127.26(12) . . ?
C23 C24 H24 116.2 . . ?
C25 C24 C23 127.68(13) . . ?
C25 C24 H24 116.2 . . ?
C15 C25 H25 117.1 . . ?
C24 C25 C15 125.79(13) . . ?
C24 C25 H25 117.1 . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
F26 C21 C22 C23 153.14(13) . . . . ?
O2 C3 C4 O5 1.53(16) . . . . ?
O2 C3 C4 C9 -174.10(13) . . . . ?
O2 C3 C6 C7 175.79(13) . . . . ?
O5 C4 C9 C8 -176.89(13) . . . . ?
O16 C13 C14 C15 -176.61(13) . . . . ?
O16 C13 C14 C21 7.3(2) . . . . ?
O27 C23 C24 C25 -162.29(13) . . . . ?
C1 O2 C3 C4 -12.26(15) . . . . ?
C1 O2 C3 C6 170.65(15) . . . . ?
C1 O5 C4 C3 9.88(15) . . . . ?
C1 O5 C4 C9 -174.78(14) . . . . ?
C3 O2 C1 O5 18.34(16) . . . . ?
C3 C4 C9 C8 -2.1(2) . . . . ?
C3 C6 C7 C8 -2.1(2) . . . . ?
C3 C6 C7 C10 177.35(13) . . . . ?
C4 O5 C1 O2 -17.40(16) . . . . ?
C4 C3 C6 C7 -0.9(2) . . . . ?
C6 C3 C4 O5 178.78(13) . . . . ?
C6 C3 C4 C9 3.2(2) . . . . ?
C6 C7 C8 C9 3.1(2) . . . . ?
C6 C7 C8 C12 -177.27(12) . . . . ?
C6 C7 C10 C11 178.01(14) . . . . ?
C7 C8 C9 C4 -0.9(2) . . . . ?
C7 C8 C12 C11 -2.67(16) . . . . ?
C7 C8 C12 C15 179.02(14) . . . . ?
C7 C10 C11 C12 0.87(14) . . . . ?
C7 C10 C11 C13 179.84(15) . . . . ?
C8 C7 C10 C11 -2.53(14) . . . . ?
C8 C12 C15 C14 -179.80(15) . . . . ?
C8 C12 C15 C17 60.11(19) . . . . ?
C8 C12 C15 C25 -61.19(19) . . . . ?
C9 C8 C12 C11 176.94(14) . . . . ?
C9 C8 C12 C15 -1.4(3) . . . . ?
C10 C7 C8 C9 -176.42(12) . . . . ?
C10 C7 C8 C12 3.23(15) . . . . ?
C10 C11 C12 C8 1.05(16) . . . . ?
C10 C11 C12 C15 179.77(11) . . . . ?
C10 C11 C13 O16 -1.1(3) . . . . ?
C10 C11 C13 C14 178.24(15) . . . . ?
C11 C12 C15 C14 1.93(14) . . . . ?
C11 C12 C15 C17 -118.16(13) . . . . ?
C11 C12 C15 C25 120.54(13) . . . . ?
C11 C13 C14 C15 4.05(14) . . . . ?
C11 C13 C14 C21 -172.03(13) . . . . ?
C12 C8 C9 C4 179.52(14) . . . . ?
C12 C11 C13 O16 177.88(13) . . . . ?
C12 C11 C13 C14 -2.79(15) . . . . ?
C12 C15 C17 C18 47.62(16) . . . . ?
C12 C15 C25 C24 -165.29(12) . . . . ?
C13 C11 C12 C8 -178.20(11) . . . . ?
C13 C11 C12 C15 0.52(16) . . . . ?
C13 C14 C15 C12 -3.60(13) . . . . ?
C13 C14 C15 C17 113.95(12) . . . . ?
C13 C14 C15 C25 -122.42(12) . . . . ?
C13 C14 C21 F26 -9.6(2) . . . . ?
C13 C14 C21 C22 167.92(13) . . . . ?
C14 C15 C17 C18 -63.81(14) . . . . ?
C14 C15 C25 C24 -53.91(17) . . . . ?
C14 C21 C22 C23 -24.5(2) . . . . ?
C15 C14 C21 F26 174.84(11) . . . . ?
C15 C14 C21 C22 -7.7(2) . . . . ?
C15 C17 C18 C19 174.18(12) . . . . ?
C17 C15 C25 C24 72.50(17) . . . . ?
C17 C18 C19 C20 61.56(17) . . . . ?
C21 C14 C15 C12 172.56(13) . . . . ?
C21 C14 C15 C17 -69.89(16) . . . . ?
C21 C14 C15 C25 53.74(17) . . . . ?
C21 C22 C23 O27 -173.19(12) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
C22 C23 C24 C25 23.4(2) . . . . ?
C23 C24 C25 C15 8.2(2) . . . . ?
C25 C15 C17 C18 170.90(11) . . . . ?
C28 O27 C23 C22 2.87(19) . . . . ?
C28 O27 C23 C24 -171.80(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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.882

_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_bau45
_database_code_depnum_ccdc_archive 'CCDC 2201534'
loop_
_audit_author_name
_audit_author_address
'Andrew Phillips'
;School of Chemistry, University College Dublin
Ireland
;
_audit_update_record             
;
2022-08-15 deposited with the CCDC.	2023-02-01 downloaded from the CCDC.
;
_audit_creation_date             2022-06-11
_audit_creation_method           
;
Olex2 1.5-ac5-021
(compiled 2022.02.15 svn.rf212a0ae for Rigaku Oxford Diffraction, GUI svn.r6439)
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            4K
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 O5'
_chemical_formula_sum            'C23 H24 O5'
_chemical_formula_weight         380.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H24O5
_chemical_oxdiff_usercomment     'Compound 4K, Bau45'
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      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                   9.14550(10)
_cell_length_b                   9.46920(10)
_cell_length_c                   11.22560(10)
_cell_angle_alpha                102.2020(10)
_cell_angle_beta                 91.5720(10)
_cell_angle_gamma                100.0760(10)
_cell_volume                     933.428(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19427
_cell_measurement_temperature    103.8(3)
_cell_measurement_theta_max      76.3590
_cell_measurement_theta_min      4.0130
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (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            'clear pale colourless'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 6 0.0459
-6 2 -1 0.0708
1 -2 -6 0.0513
6 -2 1 0.0597
3 1 -6 0.0396
-1 -2 7 0.0478
4 -4 5 0.0597
0 -6 0 0.0338
1 5 0 0.0344

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
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
1.0317 1.3606 6.3141 -0.2340 -0.9722 0.0088
-5.8332 1.9829 -0.7956 0.0500 0.2174 -0.9748
0.6643 -1.9820 -6.2448 0.2254 0.9335 0.2789
5.8128 -1.8976 1.0754 -0.0601 -0.2594 0.9639
2.7825 1.1771 -6.4968 -0.4149 0.7677 0.4883
-0.5074 -2.4309 7.1146 0.4743 -0.8753 -0.0940
3.5483 -3.5438 5.2138 0.3784 -0.6949 0.6115
0.1026 -5.8773 -0.2310 0.9280 0.2749 0.2514
1.3376 5.4874 0.0739 -0.9590 -0.2834 -0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28164
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.358
_diffrn_reflns_theta_min         4.038
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103.8(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 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -59.00   0.50    1.00    --  -41.70-152.00  72.00  112
  2  ω    -85.00  -2.00   0.50    1.00    --  -41.70 121.00 -44.00  166
  3  ω   -105.00 -20.00   0.50    1.00    --  -41.70 152.00 115.00  170
  4  ω     24.00  95.00   0.50    1.00    --   41.70-121.00-127.00  142
  5  ω     41.00 115.00   0.50    1.00    --   41.70-152.00  72.00  148
  6  ω     41.00 131.00   0.50    4.00    --  112.00-152.00  72.00  180
  7  ω     38.00 111.00   0.50    4.00    --  112.00-121.00-127.00  146
  8  ω     99.00 178.00   0.50    4.00    --  112.00 121.00 -44.00  158
  9  ω     81.00 164.00   0.50    4.00    --  112.00 152.00 115.00  166
 10  ω      2.00  30.00   0.50    1.00    --   38.00  88.00 127.64   56
 11  ω   -115.00 -14.00   0.50    1.00    --  -41.70 -57.00-150.00  202
 12  ω   -116.00 -17.00   0.50    1.00    --  -41.70 -37.00 -30.00  198
 13  ω     27.00  98.00   0.50    1.00    --   41.70-125.00-180.00  142
 14  ω     13.00  42.00   0.50    1.00    --   46.00  80.00-131.90   58
 15  ω     13.00  42.00   0.50    1.00    --   46.00  80.00 -54.49   58
 16  ω     16.00  42.00   0.50    1.00    --   50.00  82.00  88.04   52
 17  ω     16.00  42.00   0.50    1.00    --   50.00  81.00 -45.13   52
 18  ω     16.00  42.00   0.50    1.00    --   50.00  82.00  23.38   52
 19  ω     16.00  42.00   0.50    1.00    --   50.00  82.00 158.60   52
 20  ω     30.00 130.00   0.50    1.00    --   58.00  55.00-105.43  200
 21  ω     31.00 136.00   0.50    1.00    --   62.00  71.00 165.32  210
 22  ω     32.00 135.00   0.50    1.00    --   62.00  64.00 105.71  206
 23  ω     35.00 139.00   0.50    1.00    --   66.00  69.00 -15.23  208
 24  ω     35.00 140.00   0.50    1.00    --   66.00  70.00  60.32  210
 25  ω     36.00 139.00   0.50    1.00    --   66.00  64.00-162.54  206
 26  ω     39.00 143.00   0.50    1.00    --   70.00  69.00 126.64  208
 27  ω     40.00 143.00   0.50    1.00    --   70.00  65.00 -99.37  206
 28  ω     39.00 143.00   0.50    1.00    --   70.00  69.00 115.11  208
 29  ω     43.00 148.00   0.50    1.00    --   74.00  71.00 -62.08  210
 30  ω     43.00 147.00   0.50    1.00    --   74.00  69.00  15.56  208
 31  ω     57.00 156.00   0.50    4.00    --   82.00  42.00  10.83  198
 32  ω     52.00 155.00   0.50    4.00    --   82.00  64.00 -69.18  206
 33  ω     54.00 154.00   0.50    4.00    --   82.00  54.00  76.19  200
 34  ω     51.00 156.00   0.50    4.00    --   82.00  71.00 132.47  210
 35  ω     65.00 167.00   0.50    4.00    --   94.00  60.00-153.45  204
 36  ω     83.00 178.00   0.50    4.00    --  112.00  61.00-120.00  190
 37  ω     36.00 145.00   0.50    4.00    --  112.00 -77.00-150.00  218
 38  ω     83.00 178.00   0.50    4.00    --  112.00  61.00   0.00  190
 39  ω     83.00 178.00   0.50    4.00    --  112.00  61.00-150.00  190
 40  ω     36.00 109.00   0.50    4.00    --  112.00-111.00  60.00  146
 41  ω     36.00 140.00   0.50    4.00    --  112.00 -30.00-180.00  208
 42  ω     29.00 107.00   0.50    4.00    --  112.00 -94.00-120.00  156
 43  ω     83.00 178.00   0.50    4.00    --  112.00  61.00 -60.00  190
 44  ω    104.00 178.00   0.50    4.00    --  112.00 111.00  60.00  148
 45  ω     83.00 178.00   0.50    4.00    --  112.00  61.00 -90.00  190
 46  ω     83.00 178.00   0.50    4.00    --  112.00  61.00 120.00  190
 47  ω     83.00 178.00   0.50    4.00    --  112.00  61.00-180.00  190
 48  ω     86.00 178.00   0.50    4.00    --  112.00  45.00 150.00  184
 49  ω     39.00 109.00   0.50    4.00    --  112.00-111.00-150.00  140
 50  ω    144.00 170.00   0.50    4.00    --  112.00  61.00 150.00   52
 51  ω     42.00  86.00   0.50    4.00    --  112.00-111.00-180.00   88
 52  ω     84.00 136.00   0.50    4.00    --  112.00  61.00 150.00  104
 53  ω     79.00 119.00   0.50    4.00    --  112.00 -61.00  30.00   80
 54  ω     83.00 178.00   0.50    4.00    --  112.00  61.00  90.00  190
 55  ω     83.00 177.00   0.50    4.00    --  112.00  61.00  30.00  188
 56  ω     30.00 106.00   0.50    4.00    --  112.00 -94.00 120.00  152
 57  ω     83.00 140.00   0.50    4.00    --  112.00  64.00-143.07  114
 58  ω    129.00 163.00   0.50    4.00    --  112.00  61.00 -30.00   68
 59  ω     37.00 108.00   0.50    4.00    --  112.00-111.00  90.00  142
 60  ω     83.00 118.00   0.50    4.00    --  112.00  61.00 -30.00   70
 61  ω     83.00 161.00   0.50    4.00    --  112.00  61.00  60.00  156
;
_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      -0.0637725000
_diffrn_orient_matrix_UB_12      -0.1593142000
_diffrn_orient_matrix_UB_13      0.0076845000
_diffrn_orient_matrix_UB_21      -0.0324451000
_diffrn_orient_matrix_UB_22      -0.0418585000
_diffrn_orient_matrix_UB_23      -0.1396502000
_diffrn_orient_matrix_UB_31      0.1558319000
_diffrn_orient_matrix_UB_32      -0.0394333000
_diffrn_orient_matrix_UB_33      -0.0155656000
_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                3555
_reflns_number_total             3882
_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 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-021 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.2750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C23(H23), C6(H6), C3(H3), C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C18(H18A,H18B,H18C)
;
_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
O19 O 0.84776(8) 0.72101(8) 0.18906(7) 0.02291(18) Uani 1 1 d . . . . .
O27 O 0.77949(9) 0.96633(8) 0.35192(8) 0.02708(19) Uani 1 1 d . . . . .
O14 O 0.27161(8) 0.49084(8) 0.12080(7) 0.02477(18) Uani 1 1 d . . . . .
O25 O 0.28345(9) 1.03172(9) 0.28660(8) 0.02859(19) Uani 1 1 d . . . . .
O20 O 0.79677(9) 0.74852(9) 0.07405(7) 0.02694(19) Uani 1 1 d . . . . .
C11 C 0.45211(11) 0.70046(11) 0.21394(9) 0.0195(2) Uani 1 1 d . . . . .
C5 C 0.74779(12) 0.38868(11) 0.15715(9) 0.0203(2) Uani 1 1 d . . . . .
C10 C 0.40243(11) 0.54053(11) 0.15870(9) 0.0197(2) Uani 1 1 d . . . . .
C12 C 0.60067(11) 0.75887(11) 0.25575(9) 0.0198(2) Uani 1 1 d . . . . .
C21 C 0.34162(12) 0.78701(12) 0.22178(10) 0.0212(2) Uani 1 1 d . . . . .
H21 H 0.242049 0.744320 0.191840 0.025 Uiso 1 1 calc R U . . .
C13 C 0.71954(11) 0.66370(11) 0.24856(10) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.66060(11) 0.50653(11) 0.18477(9) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.51514(11) 0.44931(11) 0.15117(9) 0.0198(2) Uani 1 1 d . . . . .
C4 C 0.64713(12) 0.25590(12) 0.11202(9) 0.0211(2) Uani 1 1 d . . . . .
C22 C 0.37992(12) 0.93529(12) 0.27372(10) 0.0226(2) Uani 1 1 d . . . . .
C7 C 0.49110(12) 0.28552(11) 0.10341(10) 0.0213(2) Uani 1 1 d . . . . .
H7A H 0.448099 0.257192 0.017974 0.026 Uiso 1 1 calc R U . . .
H7B H 0.425316 0.232704 0.154771 0.026 Uiso 1 1 calc R U . . .
C24 C 0.63512(12) 0.91106(12) 0.30937(10) 0.0219(2) Uani 1 1 d . . . . .
C23 C 0.52646(12) 0.99752(12) 0.31821(10) 0.0241(2) Uani 1 1 d . . . . .
H23 H 0.551698 1.099466 0.354646 0.029 Uiso 1 1 calc R U . . .
C6 C 0.90088(12) 0.38995(12) 0.16682(10) 0.0233(2) Uani 1 1 d . . . . .
H6 H 0.969599 0.479646 0.193937 0.028 Uiso 1 1 calc R U . . .
C3 C 0.69779(12) 0.12388(12) 0.08204(10) 0.0240(2) Uani 1 1 d . . . . .
H3 H 0.629804 0.034096 0.052974 0.029 Uiso 1 1 calc R U . . .
C15 C 0.78854(12) 0.66533(12) 0.37688(10) 0.0228(2) Uani 1 1 d . . . . .
H15A H 0.850644 0.588469 0.368766 0.027 Uiso 1 1 calc R U . . .
H15B H 0.854598 0.761550 0.408503 0.027 Uiso 1 1 calc R U . . .
C2 C 0.84977(13) 0.12503(12) 0.09520(10) 0.0256(2) Uani 1 1 d . . . . .
H2 H 0.885579 0.035098 0.076333 0.031 Uiso 1 1 calc R U . . .
C1 C 0.95004(12) 0.25704(13) 0.13584(10) 0.0253(2) Uani 1 1 d . . . . .
H1 H 1.053611 0.255996 0.142436 0.030 Uiso 1 1 calc R U . . .
C26 C 0.13012(12) 0.96990(13) 0.25192(12) 0.0289(3) Uani 1 1 d . . . . .
H26A H 0.119363 0.920950 0.165192 0.043 Uiso 1 1 calc R U . . .
H26B H 0.071239 1.048264 0.265856 0.043 Uiso 1 1 calc R U . . .
H26C H 0.094728 0.898145 0.300958 0.043 Uiso 1 1 calc R U . . .
C16 C 0.67336(13) 0.63930(13) 0.46930(10) 0.0274(2) Uani 1 1 d . . . . .
H16A H 0.595042 0.554136 0.431467 0.033 Uiso 1 1 calc R U . . .
H16B H 0.625692 0.726601 0.491269 0.033 Uiso 1 1 calc R U . . .
C28 C 0.81306(13) 1.11553(13) 0.41748(11) 0.0294(3) Uani 1 1 d . . . . .
H28A H 0.794889 1.179931 0.363045 0.044 Uiso 1 1 calc R U . . .
H28B H 0.917805 1.140058 0.448154 0.044 Uiso 1 1 calc R U . . .
H28C H 0.749584 1.129260 0.486367 0.044 Uiso 1 1 calc R U . . .
C17 C 0.74243(14) 0.61004(13) 0.58529(10) 0.0288(3) Uani 1 1 d . . . . .
H17A H 0.832769 0.685640 0.614073 0.035 Uiso 1 1 calc R U . . .
H17B H 0.670921 0.619598 0.649848 0.035 Uiso 1 1 calc R U . . .
C18 C 0.78391(15) 0.45922(14) 0.56663(12) 0.0328(3) Uani 1 1 d . . . . .
H18A H 0.857215 0.450037 0.504719 0.049 Uiso 1 1 calc R U . . .
H18B H 0.694752 0.383653 0.539272 0.049 Uiso 1 1 calc R U . . .
H18C H 0.826593 0.446404 0.643816 0.049 Uiso 1 1 calc R U . . .
H20 H 0.793(2) 0.653(2) 0.0194(18) 0.064(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
O19 O20 1.4505(10) . ?
O19 C13 1.4454(12) . ?
O27 C24 1.3650(13) . ?
O27 C28 1.4242(13) . ?
O14 C10 1.2346(13) . ?
O25 C22 1.3661(13) . ?
O25 C26 1.4308(13) . ?
O20 H20 0.98(2) . ?
C11 C10 1.4937(14) . ?
C11 C12 1.4016(14) . ?
C11 C21 1.4016(15) . ?
C5 C9 1.4683(15) . ?
C5 C4 1.4090(14) . ?
C5 C6 1.3990(15) . ?
C10 C8 1.4497(15) . ?
C12 C13 1.5223(14) . ?
C12 C24 1.4151(15) . ?
C21 H21 0.9500 . ?
C21 C22 1.3802(15) . ?
C13 C9 1.5053(14) . ?
C13 C15 1.5526(14) . ?
C9 C8 1.3563(14) . ?
C8 C7 1.5047(14) . ?
C4 C7 1.5061(14) . ?
C4 C3 1.3871(15) . ?
C22 C23 1.3983(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C24 C23 1.3868(16) . ?
C23 H23 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.3887(16) . ?
C3 H3 0.9500 . ?
C3 C2 1.3917(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5245(15) . ?
C2 H2 0.9500 . ?
C2 C1 1.3952(16) . ?
C1 H1 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5297(15) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5148(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C13 O19 O20 108.50(7) . . ?
C24 O27 C28 117.15(9) . . ?
C22 O25 C26 116.41(9) . . ?
O19 O20 H20 101.3(12) . . ?
C12 C11 C10 121.38(10) . . ?
C12 C11 C21 122.56(10) . . ?
C21 C11 C10 116.06(9) . . ?
C4 C5 C9 107.53(9) . . ?
C6 C5 C9 132.09(10) . . ?
C6 C5 C4 120.37(10) . . ?
O14 C10 C11 120.72(10) . . ?
O14 C10 C8 122.58(9) . . ?
C8 C10 C11 116.70(9) . . ?
C11 C12 C13 122.22(9) . . ?
C11 C12 C24 116.82(10) . . ?
C24 C12 C13 120.93(9) . . ?
C11 C21 H21 120.6 . . ?
C22 C21 C11 118.88(10) . . ?
C22 C21 H21 120.6 . . ?
O19 C13 C12 112.05(8) . . ?
O19 C13 C9 109.32(8) . . ?
O19 C13 C15 102.21(8) . . ?
C12 C13 C15 112.00(9) . . ?
C9 C13 C12 112.30(8) . . ?
C9 C13 C15 108.45(8) . . ?
C5 C9 C13 126.03(9) . . ?
C8 C9 C5 109.07(9) . . ?
C8 C9 C13 124.75(10) . . ?
C10 C8 C7 126.39(9) . . ?
C9 C8 C10 122.13(10) . . ?
C9 C8 C7 111.46(9) . . ?
C5 C4 C7 109.93(9) . . ?
C3 C4 C5 120.47(10) . . ?
C3 C4 C7 129.60(10) . . ?
O25 C22 C21 124.78(10) . . ?
O25 C22 C23 114.86(10) . . ?
C21 C22 C23 120.37(10) . . ?
C8 C7 C4 101.90(8) . . ?
C8 C7 H7A 111.4 . . ?
C8 C7 H7B 111.4 . . ?
C4 C7 H7A 111.4 . . ?
C4 C7 H7B 111.4 . . ?
H7A C7 H7B 109.3 . . ?
O27 C24 C12 116.37(10) . . ?
O27 C24 C23 122.55(10) . . ?
C23 C24 C12 121.07(10) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.29(10) . . ?
C24 C23 H23 119.9 . . ?
C5 C6 H6 120.8 . . ?
C1 C6 C5 118.46(10) . . ?
C1 C6 H6 120.8 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 118.95(10) . . ?
C2 C3 H3 120.5 . . ?
C13 C15 H15A 108.8 . . ?
C13 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C13 113.70(9) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.61(10) . . ?
C1 C2 H2 119.7 . . ?
C6 C1 C2 121.06(10) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C15 C16 C17 112.12(9) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
O27 C28 H28A 109.5 . . ?
O27 C28 H28B 109.5 . . ?
O27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 113.11(10) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O19 C13 C9 C5 51.63(13) . . . . ?
O19 C13 C9 C8 -133.20(10) . . . . ?
O19 C13 C15 C16 168.23(9) . . . . ?
O27 C24 C23 C22 -179.67(10) . . . . ?
O14 C10 C8 C9 175.05(10) . . . . ?
O14 C10 C8 C7 -2.87(17) . . . . ?
O25 C22 C23 C24 -179.41(10) . . . . ?
O20 O19 C13 C12 -50.76(10) . . . . ?
O20 O19 C13 C9 74.40(9) . . . . ?
O20 O19 C13 C15 -170.83(7) . . . . ?
C11 C10 C8 C9 -4.27(15) . . . . ?
C11 C10 C8 C7 177.81(9) . . . . ?
C11 C12 C13 O19 127.45(10) . . . . ?
C11 C12 C13 C9 3.96(14) . . . . ?
C11 C12 C13 C15 -118.36(11) . . . . ?
C11 C12 C24 O27 178.79(9) . . . . ?
C11 C12 C24 C23 -0.79(16) . . . . ?
C11 C21 C22 O25 179.80(10) . . . . ?
C11 C21 C22 C23 -0.31(16) . . . . ?
C5 C9 C8 C10 -175.39(9) . . . . ?
C5 C9 C8 C7 2.80(12) . . . . ?
C5 C4 C7 C8 -1.11(11) . . . . ?
C5 C4 C3 C2 -1.12(16) . . . . ?
C5 C6 C1 C2 0.42(16) . . . . ?
C10 C11 C12 C13 -0.51(15) . . . . ?
C10 C11 C12 C24 -178.42(9) . . . . ?
C10 C11 C21 C22 178.98(9) . . . . ?
C10 C8 C7 C4 177.01(10) . . . . ?
C12 C11 C10 O14 -179.06(9) . . . . ?
C12 C11 C10 C8 0.27(14) . . . . ?
C12 C11 C21 C22 -0.65(16) . . . . ?
C12 C13 C9 C5 176.64(9) . . . . ?
C12 C13 C9 C8 -8.19(14) . . . . ?
C12 C13 C15 C16 48.12(12) . . . . ?
C12 C24 C23 C22 -0.11(17) . . . . ?
C21 C11 C10 O14 1.31(15) . . . . ?
C21 C11 C10 C8 -179.36(9) . . . . ?
C21 C11 C12 C13 179.10(9) . . . . ?
C21 C11 C12 C24 1.19(15) . . . . ?
C21 C22 C23 C24 0.69(17) . . . . ?
C13 C12 C24 O27 0.84(15) . . . . ?
C13 C12 C24 C23 -178.74(9) . . . . ?
C13 C9 C8 C10 8.74(16) . . . . ?
C13 C9 C8 C7 -173.07(9) . . . . ?
C13 C15 C16 C17 168.19(9) . . . . ?
C9 C5 C4 C7 2.74(11) . . . . ?
C9 C5 C4 C3 -177.73(9) . . . . ?
C9 C5 C6 C1 178.35(11) . . . . ?
C9 C13 C15 C16 -76.37(11) . . . . ?
C9 C8 C7 C4 -1.09(11) . . . . ?
C4 C5 C9 C13 172.35(9) . . . . ?
C4 C5 C9 C8 -3.45(12) . . . . ?
C4 C5 C6 C1 -2.65(15) . . . . ?
C4 C3 C2 C1 -1.12(16) . . . . ?
C7 C4 C3 C2 178.30(10) . . . . ?
C24 C12 C13 O19 -54.72(13) . . . . ?
C24 C12 C13 C9 -178.21(9) . . . . ?
C24 C12 C13 C15 59.47(13) . . . . ?
C6 C5 C9 C13 -8.56(18) . . . . ?
C6 C5 C9 C8 175.64(11) . . . . ?
C6 C5 C4 C7 -176.48(9) . . . . ?
C6 C5 C4 C3 3.05(16) . . . . ?
C3 C4 C7 C8 179.42(11) . . . . ?
C3 C2 C1 C6 1.49(17) . . . . ?
C15 C13 C9 C5 -59.05(13) . . . . ?
C15 C13 C9 C8 116.12(11) . . . . ?
C15 C16 C17 C18 -73.23(13) . . . . ?
C26 O25 C22 C21 5.16(16) . . . . ?
C26 O25 C22 C23 -174.73(10) . . . . ?
C28 O27 C24 C12 -173.61(9) . . . . ?
C28 O27 C24 C23 5.96(16) . . . . ?

_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 1.484
_oxdiff_exptl_absorpt_empirical_full_min 0.910

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
