# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_aghwla
_database_code_depnum_ccdc_archive 'CCDC 1959877'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_nottingham_internal_coll_name   AGHWLA
_nottingham_internal_coll_number 17911
_nottingham_internal_coll_client AG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczlt
_nottingham_internal_coll_date   10/09/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 11/09/2018
_nottingham_internal_process_user pczlt
_nottingham_internal_solution_date 15/07/2019
_nottingham_internal_solution_user pczlt
_nottingham_internal_refinement_date 15/07/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 15/07/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
'Hydroxy hydrogen atom H2 was observed in the electron denisty map and has been refined with the distance O2...H2 restrained to have a value of 0.82 A (DFIX). All other hydrogen atoms were observed in the electron density map before being geometrically placed and refined with riding models.'
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 F O2'
_chemical_formula_sum            'C21 H21 F O2'
_chemical_formula_weight         324.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H21 F O2'
_chemical_oxdiff_usercomment     
'AGHWA #17911 IN A FOMBLIN FILM ON A MICROMOUNT FOR AG/HWL'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.5120(2)
_cell_length_b                   15.3360(3)
_cell_length_c                   8.7541(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.502(3)
_cell_angle_gamma                90
_cell_volume                     813.41(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24403
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2730
_cell_measurement_theta_min      2.8630
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.393
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 2 -2 0.2369
3 -6 0 0.2145
-1 -9 1 0.2412
-4 1 1 0.1927
0 -1 -5 0.1116
1 -1 5 0.1005
-1 3 5 0.1037
1 -2 -6 0.1197
3 -7 -3 0.2258
0 10 1 0.1947
3 5 2 0.2002
4 0 1 0.1995
0 7 -4 0.1899
4 0 -5 0.1950
0 -6 4 0.1738

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/dichloromethane'
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.443
_exptl_crystal_size_min          0.219
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
3.9967 2.0028 -1.9956 -0.2225 -0.7808 0.5248
2.9969 -5.9965 0.0007 0.0390 -0.0621 0.9690
-0.9993 -8.9979 0.9963 0.0701 0.8121 0.4659
-3.9963 0.9971 0.9968 0.0672 0.5792 -0.7734
0.0024 -0.9944 -4.9991 -0.9207 0.1721 -0.1619
0.9966 -1.0044 4.9993 0.9337 -0.1928 0.4849
-1.0014 2.9932 4.9988 0.9076 -0.1514 -0.1611
1.0019 -1.9926 -5.9983 -1.0810 0.0974 0.0476
2.9984 -6.9930 -2.9989 -0.5170 0.0707 0.8989
-0.0006 9.9950 1.0027 0.2725 -0.7571 -0.6295
2.9958 4.9971 2.0034 0.5029 -0.9125 0.3179
3.9953 0.0004 1.0030 0.3065 -0.6923 0.7976
0.0018 7.0014 -3.9970 -0.6662 -0.4375 -0.6564
3.9982 0.0067 -4.9955 -0.7875 -0.5743 0.5222
-0.0018 -6.0018 3.9972 0.6752 0.3637 0.5888

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32574
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.496
_diffrn_reflns_theta_min         5.431
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  34.00   1.00    1.00    --  -38.50  38.00  90.00   84
  2  ω    -93.00  -2.00   1.00    1.00    --  -38.50 125.00 -60.00   91
  3  ω      1.00  83.00   1.00    1.00    --   43.32 -99.00 -30.00   82
  4  ω     31.00  91.00   1.00    4.00    --  106.13 -30.00-150.00   60
  5  ω     25.00 109.00   1.00    4.00    --  106.13 -95.00 120.00   84
  6  ω     31.00  91.00   1.00    4.00    --  106.13 -30.00  60.00   60
  7  ω     25.00 109.00   1.00    4.00    --  106.13 -95.00   0.00   84
  8  ω     35.00 117.00   1.00    4.00    --  106.13-125.00 -30.00   82
  9  ω     82.00 177.00   1.00    4.00    --  106.13  45.00 120.00   95
 10  ω     17.00 113.00   1.00    1.00    --   43.32  57.00  60.00   96
 11  ω     17.00 113.00   1.00    1.00    --   43.32  57.00 -60.00   96
 12  ω     79.00 176.00   1.00    4.00    --  106.13  61.00   0.00   97
 13  ω     61.00 178.00   1.00    4.00    --  106.13  15.00 -30.00  117
 14  ω     79.00 176.00   1.00    4.00    --  106.13  61.00  60.00   97
 15  ω     82.00 178.00   1.00    4.00    --  106.13  30.00-150.00   96
 16  ω    -50.00  28.00   1.00    1.00    --  -38.50  38.00-150.00   78
 17  ω     17.00 113.00   1.00    1.00    --   43.32  57.00-180.00   96
 18  ω     61.00  87.00   1.00    1.00    --   43.38  38.00 120.00   26
 19  ω     91.00 116.00   1.00    1.00    --   43.38  38.00 120.00   25
 20  ω    144.00 170.00   1.00    4.00    --  106.13  61.00  90.00   26
 21  ω     79.00 105.00   1.00    4.00    --  106.13  61.00  90.00   26
 22  ω     61.00 106.00   1.00    4.00    --  106.13 -61.00 120.00   45
 23  ω     95.00 132.00   1.00    4.00    --  106.13  30.00 150.00   37
 24  ω    137.00 165.00   1.00    4.00    --  106.13 125.00   0.00   28
 25  ω     97.00 123.00   1.00    4.00    --  106.13 125.00   0.00   26
 26  ω   -112.00  -7.00   1.00    1.00    --  -38.50 -77.00  90.00  105
 27  ω     21.00 116.00   1.00    1.00    --   43.38  38.00 -60.00   95
 28  ω     12.00 117.00   1.00    1.00    --   43.38  77.00-150.00  105
 29  ω     12.00 117.00   1.00    1.00    --   43.38  77.00  90.00  105
 30  ω     23.00  98.00   1.00    1.00    --   43.38-125.00-120.00   75
 31  ω    -29.00  66.00   1.00    1.00    --   43.38 -38.00  30.00   95
 32  ω     12.00 117.00   1.00    1.00    --   43.38  77.00 -30.00  105
 33  ω     79.00 176.00   1.00    4.00    --  106.13  61.00 -90.00   97
 34  ω     25.00 109.00   1.00    4.00    --  106.13 -95.00-150.00   84
 35  ω     79.00 176.00   1.00    4.00    --  106.13  61.00  30.00   97
 36  ω     75.00 178.00   1.00    4.00    --  106.13  77.00 -60.00  103
 37  ω     75.00 178.00   1.00    4.00    --  106.13  77.00 150.00  103
 38  ω     79.00 176.00   1.00    4.00    --  106.13  61.00 150.00   97
 39  ω     75.00 178.00   1.00    4.00    --  106.13  77.00-180.00  103
 40  ω     79.00 176.00   1.00    4.00    --  106.13  61.00-120.00   97
 41  ω     75.00 178.00   1.00    4.00    --  106.13  77.00-150.00  103
 42  ω     79.00 176.00   1.00    4.00    --  106.13  61.00 -60.00   97
 43  ω     75.00 178.00   1.00    4.00    --  106.13  77.00 -30.00  103
 44  ω     79.00 176.00   1.00    4.00    --  106.13  61.00 120.00   97
 45  ω     75.00 178.00   1.00    4.00    --  106.13  77.00  60.00  103
 46  ω     35.00  98.00   1.00    4.00    --  106.13 -45.00 -30.00   63
 47  ω    -75.00  40.00   1.00    1.00    --  -38.50  19.00 -30.00  115
 48  ω    -43.00 130.00   1.00    1.00    --   43.38   0.00-150.00  173
 49  ω     12.00 117.00   1.00    1.00    --   43.38  77.00   0.00  105
 50  ω    -43.00 130.00   1.00    1.00    --   43.38   0.00-180.00  173
 51  ω    -43.00 130.00   1.00    1.00    --   43.38   0.00 -90.00  173
 52  ω    -43.00 130.00   1.00    1.00    --   43.38   0.00-120.00  173
 53  ω     21.00 116.00   1.00    1.00    --   43.38  38.00   0.00   95
 54  ω     82.00 177.00   1.00    4.00    --  106.13  45.00-120.00   95
 55  ω     75.00 178.00   1.00    4.00    --  106.13  77.00  90.00  103
 56  ω     79.00 176.00   1.00    4.00    --  106.13  61.00 -30.00   97
 57  ω     35.00 117.00   1.00    4.00    --  106.13-125.00 120.00   82
 58  ω     82.00 177.00   1.00    4.00    --  106.13  45.00 -30.00   95
 59  ω     75.00 178.00   1.00    4.00    --  106.13  77.00 120.00  103
 60  ω     79.00 176.00   1.00    4.00    --  106.13  61.00-180.00   97
 61  ω     82.00 177.00   1.00    4.00    --  106.13  45.00 150.00   95
 62  ω     75.00 178.00   1.00    4.00    --  106.13  77.00  30.00  103
 63  ω     75.00 178.00   1.00    4.00    --  106.13  77.00-120.00  103
 64  ω     82.00 177.00   1.00    4.00    --  106.13  45.00 -60.00   95
 65  ω     75.00 178.00   1.00    4.00    --  106.13  77.00 -90.00  103
 66  ω     82.00 177.00   1.00    4.00    --  106.13  45.00   0.00   95
 67  ω     75.00 178.00   1.00    4.00    --  106.13  77.00   0.00  103
 68  ω    -43.00  84.00   1.00    1.00    --   43.38   0.00 -60.00  127
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0309232000
_diffrn_orient_matrix_UB_12      0.0089661000
_diffrn_orient_matrix_UB_13      0.1823973000
_diffrn_orient_matrix_UB_21      -0.1682928000
_diffrn_orient_matrix_UB_22      -0.0737634000
_diffrn_orient_matrix_UB_23      -0.0198384000
_diffrn_orient_matrix_UB_31      0.1881130000
_diffrn_orient_matrix_UB_32      -0.0675807000
_diffrn_orient_matrix_UB_33      0.0459263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3269
_reflns_number_total             3270
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.090
_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)+(0.0482P)²+0.1303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0735
_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, All O(H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C24(H24), C16(H16), C13(H13), C15(H15), C23(H23), C22(H22),
 C21(H21), C14(H14)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F20 F 0.70708(16) 0.64506(8) 1.00564(14) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.6011(2) 0.43473(9) 0.19246(16) 0.0242(3) Uani 1 1 d D . . . .
H2 H 0.684(4) 0.4786(16) 0.227(3) 0.036 Uiso 1 1 d DR . . . .
O6 O 0.7285(2) 0.57825(9) 0.37647(18) 0.0284(3) Uani 1 1 d . . . . .
C10 C 0.5098(3) 0.46991(10) 0.6462(2) 0.0144(3) Uani 1 1 d . . . . .
C12 C 0.6821(3) 0.38792(10) 0.4753(2) 0.0156(3) Uani 1 1 d . . . . .
C17 C 0.5392(3) 0.51040(11) 0.7891(2) 0.0166(3) Uani 1 1 d . . . . .
H17 H 0.671933 0.496861 0.878034 0.020 Uiso 1 1 calc R . . . .
C19 C 0.4834(3) 0.64019(12) 0.9355(2) 0.0185(3) Uani 1 1 d . . . . .
C24 C 0.1603(3) 0.56985(12) 0.7582(2) 0.0190(3) Uani 1 1 d . . . . .
H24 H 0.088641 0.524074 0.684936 0.023 Uiso 1 1 calc R . . . .
C16 C 0.8402(3) 0.37215(12) 0.7698(2) 0.0200(3) Uani 1 1 d . . . . .
H16 H 0.838398 0.385113 0.875455 0.024 Uiso 1 1 calc R . . . .
C11 C 0.6790(3) 0.40925(10) 0.6304(2) 0.0153(3) Uani 1 1 d . . . . .
C18 C 0.3917(3) 0.57297(11) 0.82490(19) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.8452(3) 0.33141(11) 0.4641(2) 0.0212(4) Uani 1 1 d . . . . .
H13 H 0.846695 0.316866 0.359078 0.025 Uiso 1 1 calc R . . . .
C1 C 0.5065(3) 0.41918(11) 0.3141(2) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.3892(3) 0.50202(10) 0.3426(2) 0.0153(3) Uani 1 1 d . . . . .
C15 C 1.0013(3) 0.31717(12) 0.7567(2) 0.0238(4) Uani 1 1 d . . . . .
H15 H 1.110205 0.293624 0.852659 0.029 Uiso 1 1 calc R . . . .
C23 C 0.0345(3) 0.63263(13) 0.7977(2) 0.0220(4) Uani 1 1 d . . . . .
H23 H -0.121959 0.629791 0.749956 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3160(3) 0.48658(11) 0.48952(19) 0.0156(3) Uani 1 1 d . . . . .
H9A H 0.234129 0.538328 0.504119 0.019 Uiso 1 1 calc R . . . .
H9B H 0.214771 0.435943 0.465694 0.019 Uiso 1 1 calc R . . . .
C5 C 0.5458(3) 0.58102(11) 0.3843(2) 0.0184(3) Uani 1 1 d . . . . .
C22 C 0.1345(3) 0.69949(12) 0.9062(2) 0.0225(4) Uani 1 1 d . . . . .
H22 H 0.046918 0.742420 0.931794 0.027 Uiso 1 1 calc R . . . .
C21 C 0.3629(3) 0.70344(12) 0.9772(2) 0.0225(4) Uani 1 1 d . . . . .
H21 H 0.434249 0.748471 1.052479 0.027 Uiso 1 1 calc R . . . .
C14 C 1.0036(3) 0.29645(12) 0.6026(3) 0.0251(4) Uani 1 1 d . . . . .
H14 H 1.113392 0.258495 0.592814 0.030 Uiso 1 1 calc R . . . .
C7 C 0.4680(4) 0.66442(12) 0.4357(3) 0.0279(4) Uani 1 1 d . . . . .
H7A H 0.458918 0.656677 0.544162 0.042 Uiso 1 1 calc GR . . . .
H7B H 0.321942 0.679577 0.355744 0.042 Uiso 1 1 calc GR . . . .
H7C H 0.572392 0.711344 0.440642 0.042 Uiso 1 1 calc GR . . . .
C8 C 0.1844(3) 0.52500(13) 0.1906(2) 0.0228(4) Uani 1 1 d . . . . .
H8A H 0.224113 0.525163 0.092843 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.130350 0.582853 0.205096 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.068614 0.481596 0.176982 0.034 Uiso 1 1 calc GR . . . .
C3 C 0.3445(3) 0.34420(12) 0.2418(2) 0.0255(4) Uani 1 1 d . . . . .
H3A H 0.241804 0.360421 0.132111 0.038 Uiso 1 1 calc GR . . . .
H3B H 0.261485 0.332374 0.313032 0.038 Uiso 1 1 calc GR . . . .
H3C H 0.426389 0.291849 0.234088 0.038 Uiso 1 1 calc GR . . . .


_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
F20 C19 1.3597(19) . ?
O2 H2 0.85(2) . ?
O2 C1 1.432(2) . ?
O6 C5 1.217(2) . ?
C10 C17 1.346(2) . ?
C10 C11 1.487(2) . ?
C10 C9 1.507(2) . ?
C12 C11 1.404(2) . ?
C12 C13 1.402(2) . ?
C12 C1 1.531(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.470(2) . ?
C19 C18 1.390(2) . ?
C19 C21 1.379(2) . ?
C24 H24 0.9500 . ?
C24 C18 1.404(2) . ?
C24 C23 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C11 1.406(2) . ?
C16 C15 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C1 C4 1.549(2) . ?
C1 C3 1.532(2) . ?
C4 C9 1.545(2) . ?
C4 C5 1.539(2) . ?
C4 C8 1.540(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.387(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C7 1.504(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(3) . ?
C21 H21 0.9500 . ?
C14 H14 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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
C1 O2 H2 105(2) . . ?
C17 C10 C11 121.16(14) . . ?
C17 C10 C9 123.64(15) . . ?
C11 C10 C9 115.06(13) . . ?
C11 C12 C1 123.23(14) . . ?
C13 C12 C11 119.40(15) . . ?
C13 C12 C1 117.28(15) . . ?
C10 C17 H17 115.9 . . ?
C10 C17 C18 128.13(15) . . ?
C18 C17 H17 115.9 . . ?
F20 C19 C18 118.09(14) . . ?
F20 C19 C21 117.47(15) . . ?
C21 C19 C18 124.43(16) . . ?
C18 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C18 120.97(16) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C11 121.47(16) . . ?
C12 C11 C10 120.63(14) . . ?
C12 C11 C16 118.35(15) . . ?
C16 C11 C10 121.02(15) . . ?
C19 C18 C17 119.00(14) . . ?
C19 C18 C24 115.89(15) . . ?
C24 C18 C17 125.10(15) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.38(16) . . ?
C14 C13 H13 119.3 . . ?
O2 C1 C12 110.98(13) . . ?
O2 C1 C4 110.81(13) . . ?
O2 C1 C3 103.72(13) . . ?
C12 C1 C4 110.71(13) . . ?
C12 C1 C3 108.31(14) . . ?
C3 C1 C4 112.10(14) . . ?
C9 C4 C1 109.24(13) . . ?
C5 C4 C1 111.14(13) . . ?
C5 C4 C9 107.65(13) . . ?
C5 C4 C8 108.26(13) . . ?
C8 C4 C1 111.71(13) . . ?
C8 C4 C9 108.72(13) . . ?
C16 C15 H15 120.1 . . ?
C16 C15 C14 119.87(17) . . ?
C14 C15 H15 120.1 . . ?
C24 C23 H23 119.6 . . ?
C22 C23 C24 120.78(16) . . ?
C22 C23 H23 119.6 . . ?
C10 C9 C4 111.87(13) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C4 C9 H9A 109.2 . . ?
C4 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O6 C5 C4 122.38(16) . . ?
O6 C5 C7 119.34(16) . . ?
C7 C5 C4 118.27(15) . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.76(16) . . ?
C21 C22 H22 120.1 . . ?
C19 C21 C22 118.13(16) . . ?
C19 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C13 C14 C15 119.52(16) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O6 0.85(2) 1.96(3) 2.673(2) 141(3) . yes

_olex2_date_sample_submission    2018-09-06
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id AGHWLA
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# 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_aghwlb
_database_code_depnum_ccdc_archive 'CCDC 1959878'
loop_
_audit_author_name
_audit_author_address
'Stephen P. Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_nottingham_internal_coll_name   AGHWLB
_nottingham_internal_coll_number 17920
_nottingham_internal_coll_client AG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczlt
_nottingham_internal_coll_date   11/09/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 12/09/2018
_nottingham_internal_process_user pczlt
_nottingham_internal_solution_date 17/07/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 17/07/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 17/07/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
'Hydroxy hydrogen atom H2 was observed in the electron denisty map and has been refined with the distance O2...H2 restrained to have a value of 0.82 A (DFIX). All other hydrogen atoms were observed in the electron density map before being geometrically placed and refined with riding models.'
_audit_creation_date             2019-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 O2'
_chemical_oxdiff_usercomment     
'AGHWLB #17920 Crystal mounted on Micromount in fomblin for AG/HWL'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5439(2)
_cell_length_b                   10.5734(2)
_cell_length_c                   17.3218(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.97(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14650
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.2300
_cell_measurement_theta_min      4.6370
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -11 0.0684
3 -6 0 0.1440
1 -1 11 0.1157
-6 2 1 0.0815
6 0 -1 0.0469
2 6 -1 0.0655
-5 -4 1 0.0994
-3 -6 1 0.1179
4 -1 8 0.0806
4 3 7 0.0724
0 7 3 0.0785
-4 -4 6 0.0985
-3 1 9 0.1147
-2 5 6 0.0796
-5 -4 4 0.0849
-6 1 4 0.0749
6 0 2 0.0460
2 6 2 0.0594

_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.143
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
0.0031 -0.0270 -11.0046 0.8634 -0.4590 0.0270
3.0085 -5.9970 0.0091 0.0431 0.0164 -0.9990
0.9984 -0.9722 11.0053 -0.8876 0.4000 -0.2349
-6.0043 1.9976 1.0058 0.2207 0.6533 0.7448
6.0017 0.0021 -1.0105 -0.2978 -0.7821 -0.4947
1.9930 5.9983 -1.0179 -0.2781 -0.6751 0.5872
-4.9962 -4.0008 1.0182 0.3892 0.9165 -0.0885
-2.9932 -5.9991 1.0196 0.3409 0.7985 -0.5043
4.0000 -0.9772 7.9990 -0.8403 -0.0954 -0.4761
3.9951 3.0198 6.9892 -0.9159 -0.3948 0.0266
-0.0099 7.0065 2.9848 -0.5052 -0.3258 0.8682
-3.9974 -3.9878 6.0187 -0.0660 1.0017 -0.1836
-3.0045 1.0197 9.0065 -0.5568 0.6813 0.3516
-2.0123 5.1424 6.4863 -0.5816 0.1877 0.7915
-5.0054 -3.9901 4.0031 0.1554 1.0417 -0.0947
-5.9986 1.0133 4.0035 0.0236 0.8415 0.6130
6.0022 -0.0101 1.9932 -0.5328 -0.6558 -0.5046
2.0097 5.9991 1.9964 -0.5155 -0.5511 0.5775

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.788
_diffrn_reflns_theta_min         4.900
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00 120.00  132
  2  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00  60.00  132
  3  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00   0.00  132
  4  ω     13.00 129.00   0.50    4.00    --  102.40 -61.00-180.00  232
  5  ω     13.00  69.00   0.50    4.00    --  102.40 -30.00  30.00  112
  6  ω     13.00  69.00   0.50    4.00    --  102.40 -30.00   0.00  112
  7  ω     13.00  69.00   0.50    4.00    --  102.40 -30.00  60.00  112
  8  ω     13.00  77.00   0.50    4.00    --  102.40 -45.00 -60.00  128
  9  ω     13.00 136.00   0.50    4.00    --  102.40 -82.00-150.00  246
 10  ω     80.00 192.00   0.50    4.00    --  102.40  77.00  30.00  224
 11  ω     13.00  77.00   0.50    4.00    --  102.40 -45.00 150.00  128
 12  ω     65.00 192.00   0.50    4.00    --  102.40  15.00 -90.00  254
 13  ω     13.00 192.00   0.50    4.00    --  102.40   0.00-120.00  358
 14  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00-120.00  132
 15  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00 -60.00  132
 16  ω     78.00 192.00   0.50    4.00    --  102.40  30.00   0.00  228
 17  ω     13.00  81.00   0.50    4.00    --  102.40 -82.00  30.00  136
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628039000
_diffrn_orient_matrix_UB_12      -0.0388046000
_diffrn_orient_matrix_UB_13      -0.0783831000
_diffrn_orient_matrix_UB_21      -0.1232541000
_diffrn_orient_matrix_UB_22      -0.0645001000
_diffrn_orient_matrix_UB_23      0.0418290000
_diffrn_orient_matrix_UB_31      -0.0829352000
_diffrn_orient_matrix_UB_32      0.1249774000
_diffrn_orient_matrix_UB_33      -0.0027808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3520
_reflns_number_total             3631
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.132
_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)+(0.0780P)²+0.4869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1384
_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, All O(H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4979(3) 0.7085(2) 0.63191(13) 0.0272(5) Uani 1 1 d . . . . .
O2 O 0.5947(2) 0.73352(19) 0.69288(10) 0.0346(4) Uani 1 1 d D . . . .
H2 H 0.563(4) 0.785(3) 0.726(2) 0.052 Uiso 1 1 d DR . . . .
C3 C 0.5295(3) 0.5732(2) 0.60520(13) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.6841(3) 0.5445(2) 0.59341(15) 0.0306(5) Uani 1 1 d . . . . .
H4A H 0.694813 0.457566 0.574686 0.046 Uiso 1 1 calc GR . . . .
H4B H 0.733852 0.554039 0.642547 0.046 Uiso 1 1 calc GR . . . .
H4C H 0.723197 0.603351 0.555398 0.046 Uiso 1 1 calc GR . . . .
C5 C 0.4642(3) 0.4968(3) 0.66964(13) 0.0302(5) Uani 1 1 d . . . . .
O6 O 0.5064(2) 0.39366(18) 0.69143(10) 0.0395(5) Uani 1 1 d . . . . .
C7 C 0.3424(3) 0.5687(3) 0.70411(16) 0.0385(6) Uani 1 1 d . . . . .
H7A H 0.352769 0.576052 0.760800 0.046 Uiso 1 1 calc R . . . .
H7B H 0.252682 0.525707 0.692548 0.046 Uiso 1 1 calc R . . . .
C8 C 0.3478(3) 0.6992(3) 0.66587(15) 0.0326(6) Uani 1 1 d . . . . .
H8A H 0.331269 0.766881 0.704279 0.039 Uiso 1 1 calc R . . . .
H8B H 0.276490 0.706005 0.624555 0.039 Uiso 1 1 calc R . . . .
C9 C 0.4460(2) 0.5464(2) 0.53013(13) 0.0257(5) Uani 1 1 d . . . . .
H9A H 0.459864 0.457317 0.514184 0.031 Uiso 1 1 calc R . . . .
H9B H 0.344746 0.559908 0.539392 0.031 Uiso 1 1 calc R . . . .
C10 C 0.4965(2) 0.6342(2) 0.46695(13) 0.0234(5) Uani 1 1 d . . . . .
C11 C 0.5106(2) 0.7683(2) 0.48941(13) 0.0250(5) Uani 1 1 d . . . . .
C12 C 0.5089(3) 0.8054(2) 0.56747(14) 0.0261(5) Uani 1 1 d . . . . .
C13 C 0.5133(3) 0.9336(2) 0.58677(16) 0.0349(6) Uani 1 1 d . . . . .
H13 H 0.510242 0.956844 0.639718 0.042 Uiso 1 1 calc R . . . .
C14 C 0.5219(3) 1.0281(2) 0.53149(18) 0.0388(6) Uani 1 1 d . . . . .
C15 C 0.5197(5) 1.1657(3) 0.5529(2) 0.0581(10) Uani 1 1 d . . . . .
H15A H 0.592722 1.210559 0.524051 0.087 Uiso 1 1 calc GR . . . .
H15B H 0.536913 1.174657 0.608371 0.087 Uiso 1 1 calc GR . . . .
H15C H 0.427896 1.201659 0.540136 0.087 Uiso 1 1 calc GR . . . .
C16 C 0.5292(3) 0.9903(2) 0.45413(17) 0.0351(6) Uani 1 1 d . . . . .
H16 H 0.539575 1.052539 0.414996 0.042 Uiso 1 1 calc R . . . .
C17 C 0.5217(3) 0.8648(2) 0.43368(15) 0.0298(5) Uani 1 1 d . . . . .
H17 H 0.524022 0.842624 0.380547 0.036 Uiso 1 1 calc R . . . .
C18 C 0.5323(2) 0.5917(2) 0.39664(14) 0.0270(5) Uani 1 1 d . . . . .
H18 H 0.574932 0.651855 0.363363 0.032 Uiso 1 1 calc R . . . .
C19 C 0.5140(3) 0.4642(2) 0.36455(12) 0.0268(5) Uani 1 1 d . . . . .
C20 C 0.6180(3) 0.4109(3) 0.31797(15) 0.0345(6) Uani 1 1 d . . . . .
H20 H 0.701533 0.457109 0.308324 0.041 Uiso 1 1 calc R . . . .
C21 C 0.6015(3) 0.2915(3) 0.28546(16) 0.0397(6) Uani 1 1 d . . . . .
H21 H 0.673693 0.256499 0.254343 0.048 Uiso 1 1 calc R . . . .
C22 C 0.4800(3) 0.2239(2) 0.29848(14) 0.0354(6) Uani 1 1 d . . . . .
H22 H 0.469291 0.141846 0.276994 0.043 Uiso 1 1 calc R . . . .
C23 C 0.3738(3) 0.2757(3) 0.34283(14) 0.0329(5) Uani 1 1 d . . . . .
H23 H 0.289910 0.229413 0.351296 0.040 Uiso 1 1 calc R . . . .
C24 C 0.3897(3) 0.3959(2) 0.37515(13) 0.0284(5) Uani 1 1 d . . . . .
H24 H 0.315626 0.431595 0.404568 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.428(3) . ?
C1 C3 1.534(3) . ?
C1 C8 1.552(4) . ?
C1 C12 1.519(3) . ?
O2 H2 0.84(2) . ?
C3 C4 1.520(3) . ?
C3 C5 1.512(3) . ?
C3 C9 1.551(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 O6 1.222(3) . ?
C5 C7 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.531(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(3) . ?
C10 C11 1.477(3) . ?
C10 C18 1.342(3) . ?
C11 C12 1.408(3) . ?
C11 C17 1.409(3) . ?
C12 C13 1.396(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(4) . ?
C14 C15 1.501(4) . ?
C14 C16 1.400(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.375(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.469(3) . ?
C19 C20 1.397(4) . ?
C19 C24 1.401(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.396(4) . ?
C24 H24 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
O2 C1 C3 105.57(19) . . ?
O2 C1 C8 109.21(19) . . ?
O2 C1 C12 111.9(2) . . ?
C3 C1 C8 103.7(2) . . ?
C12 C1 C3 113.20(18) . . ?
C12 C1 C8 112.7(2) . . ?
C1 O2 H2 113(3) . . ?
C1 C3 C9 108.80(19) . . ?
C4 C3 C1 114.7(2) . . ?
C4 C3 C9 110.45(19) . . ?
C5 C3 C1 101.22(19) . . ?
C5 C3 C4 113.1(2) . . ?
C5 C3 C9 108.03(19) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O6 C5 C3 124.7(2) . . ?
O6 C5 C7 125.4(2) . . ?
C7 C5 C3 109.9(2) . . ?
C5 C7 H7A 110.8 . . ?
C5 C7 H7B 110.8 . . ?
C5 C7 C8 104.9(2) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C1 C8 H8A 110.8 . . ?
C1 C8 H8B 110.8 . . ?
C7 C8 C1 104.6(2) . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C3 C9 H9A 109.8 . . ?
C3 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 C3 109.29(19) . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C11 C10 C9 115.3(2) . . ?
C18 C10 C9 122.1(2) . . ?
C18 C10 C11 122.5(2) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 C17 117.2(2) . . ?
C17 C11 C10 121.5(2) . . ?
C11 C12 C1 121.23(19) . . ?
C13 C12 C1 118.7(2) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.4(3) . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 C16 117.3(2) . . ?
C16 C14 C15 120.9(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16 119.4 . . ?
C17 C16 C14 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C11 C17 H17 119.1 . . ?
C16 C17 C11 121.8(3) . . ?
C16 C17 H17 119.1 . . ?
C10 C18 H18 115.8 . . ?
C10 C18 C19 128.3(2) . . ?
C19 C18 H18 115.8 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 C24 118.0(2) . . ?
C24 C19 C18 121.6(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O6 0.84(2) 1.95(2) 2.795(3) 175(4) 3_656 yes

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 3.477
_oxdiff_exptl_absorpt_empirical_full_min 0.563
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane/dichloromethane'
