# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

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

data_2-simonsol-C
_database_code_depnum_ccdc_archive 'CCDC 2327688'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDK
_nottingham_internal_coll_number 17991
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '30.00, 120.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczlt
_nottingham_internal_coll_date   30/11/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 03/12/2018
_nottingham_internal_process_user pczlt
_nottingham_internal_solution_date 03/12/2018
_nottingham_internal_solution_user pczlt
_nottingham_internal_refinement_date 09/08/2022
_nottingham_internal_refinement_user pczlt/pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 09/08/2022
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 09/08/2022
_refine_special_details          
;
All hydrogen atoms were observed in the electron density map before being geometrically placed and refined with a riding model.
Conformational disorder is modelled for propenyl moiety C18-C20 with the occupancies of the two components constrained to sum to unity and refined to values of 0.85(1) and 0.15(1). The atoms of the minor component were refined with isotropic displacement parameters. The displacement parameters of all the disordered atoms were restrained to be similar (SIMU). The equivalent bonds of the two disorder components were restrained to have similar lengths (SADI, esd 0.02 %A). Carbon atom C18B of the minor disorder component was restrained to have a planar geometry with respect to the adjoining phenyl ring (FLAT).
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H26 O3'
_chemical_formula_sum            'C27 H26 O3'
_chemical_formula_weight         398.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H26 O3'
_chemical_oxdiff_usercomment     
'REARDK3 #17991 GVA-1541 IN FOMBLIN FILM ON A MICROMOUNT FOR RA/RD'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.5253(3)
_cell_length_b                   11.2640(3)
_cell_length_c                   33.0222(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.545(2)
_cell_angle_gamma                90
_cell_volume                     4282.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11417
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.4190
_cell_measurement_theta_min      2.6550
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.780
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_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_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -4 -1 0.1748
-7 1 1 0.2071
-1 -7 1 0.0482
1 7 -1 0.0482
0 2 21 0.0197
0 -2 -21 0.0197

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethylacetate, pentane'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.039
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.9922 -3.9979 -1.0166 -0.2626 0.9149 0.5166
-6.9978 0.9993 1.0070 0.1539 -0.5815 -0.7293
-1.0126 -6.9971 0.9781 -0.1986 0.7224 -0.6118
1.0126 6.9971 -0.9781 0.1986 -0.7224 0.6118
0.0135 1.9924 21.0070 1.0107 0.0616 0.1076
-0.0135 -1.9924 -21.0070 -1.0107 -0.0616 -0.1076

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32607
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.971
_diffrn_reflns_theta_min         2.679
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -14.00   1.00   30.00    --  -42.81 -19.00  30.00  105
  2  ω    -50.00  28.00   1.00   30.00    --  -42.81  38.00-150.00   78
  3  ω     23.00  96.00   1.00   30.00    --   42.81-125.00-120.00   73
  4  ω     34.00  98.00   1.00  120.00    --  103.00 -45.00   0.00   64
  5  ω     94.00 175.00   1.00  120.00    --  103.00 125.00-120.00   81
  6  ω     22.00 110.00   1.00  120.00    --  103.00 -94.00 -30.00   88
  7  ω     94.00 175.00   1.00  120.00    --  103.00 125.00-180.00   81
  8  ω     67.00 178.00   1.00  120.00    --  103.00  15.00 -30.00  111
  9  ω     34.00  98.00   1.00  120.00    --  103.00 -45.00  90.00   64
 10  ω     73.00 175.00   1.00  120.00    --  103.00  77.00 150.00  102
 11  ω     34.00  98.00   1.00  120.00    --  103.00 -45.00 -90.00   64
 12  ω    -50.00  28.00   1.00   30.00    --  -42.81  38.00   0.00   78
 13  ω     19.00 112.00   1.00   30.00    --   42.81  57.00 -30.00   93
 14  ω     12.00 115.00   1.00   30.00    --   42.81  77.00-150.00  103
 15  ω     30.00  64.00   1.00  120.00    --  103.00 -30.00-180.00   34
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_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      -0.0103967000
_diffrn_orient_matrix_UB_12      0.0361423000
_diffrn_orient_matrix_UB_13      0.0446910000
_diffrn_orient_matrix_UB_21      0.0691336000
_diffrn_orient_matrix_UB_22      -0.1113632000
_diffrn_orient_matrix_UB_23      0.0134511000
_diffrn_orient_matrix_UB_31      0.1140700000
_diffrn_orient_matrix_UB_32      0.0706979000
_diffrn_orient_matrix_UB_33      -0.0016557000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6588
_reflns_number_total             8478
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         8478
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.091
_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)+(0.0437P)²+6.0770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1651
_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 O(H) groups
2. Restrained distances
 C20B-C19B \\sim C20A-C19A
 with sigma of 0.02
 C18B-C19B \\sim C19A-C18A
 with sigma of 0.02
 C18B-C15A \\sim C18A-C15A
 with sigma of 0.02
3. Restrained planarity
 C16A, C15A, C18B, C14A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C18B \\sim C18A \\sim C19B \\sim C19A \\sim C20B \\sim C20A \\sim C15A: within
0.01A with sigma of 3.5 and sigma for terminal atoms of 0.005 within 0.01A
5. Rigid body (RIGU) restrains
 C20A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20C)=Sof(H20D)=Sof(C18B)=Sof(H18C)=
 Sof(H18D)=1-FVAR(1)
 Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(H20B)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C6A(H6A), C6B(H6B)
7.b Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C18A(H18A,H18B), C28A(H28A,H28B), C7B(H7BA,
 H7BB), C8B(H8BA,H8BB), C3(H3C,H3D), C28B(H28C,H28D), C18B(H18C,H18D)
7.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C9A(H9A), C14A(H14A), C16A(H16A), C19A(H19A), C23A(H23A),
 C24A(H24A), C26A(H26A), C29A(H29A), C3B(H3B), C4B(H4B), C9B(H9B), C14B(H14B),
 C16B(H16B), C1(H1), C23B(H23B), C24B(H24B), C26B(H26B), C29B(H29B), C19B(H19B)
7.d X=CH2 refined with riding coordinates:
 C10A(H10A,H10B), C20A(H20A,H20B), C30A(H30A,H30B), C10B(H10C,H10D), C2(H2A,
 H2B), C30B(H30C,H30D), C20B(H20C,H20D)
7.e Idealised tetrahedral OH refined as rotating group:
 O27A(H27A), O27B(H27B)
;
_atom_sites_solution_hydrogens   geom
_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
O1A O 0.60017(16) 0.17097(19) 0.30613(7) 0.0406(5) Uani 1 1 d . . . . .
C2A C 0.4954(2) 0.1661(2) 0.31196(9) 0.0297(6) Uani 1 1 d . . . . .
C3A C 0.4510(2) 0.1161(2) 0.34885(9) 0.0308(6) Uani 1 1 d . . . . .
H3A H 0.503176 0.076590 0.367424 0.037 Uiso 1 1 calc R U . . .
C4A C 0.3389(2) 0.1241(2) 0.35731(9) 0.0293(6) Uani 1 1 d . . . . .
H4A H 0.314090 0.082819 0.380478 0.035 Uiso 1 1 calc R U . . .
C5A C 0.2486(2) 0.1940(2) 0.33270(9) 0.0276(6) Uani 1 1 d . . . . .
C6A C 0.3041(2) 0.2643(2) 0.29847(8) 0.0264(6) Uani 1 1 d . . . . .
H6A H 0.243684 0.282096 0.276646 0.032 Uiso 1 1 calc R U . . .
C7A C 0.4083(2) 0.2078(2) 0.27997(9) 0.0282(6) Uani 1 1 d . . . . .
H7AA H 0.382395 0.139543 0.262990 0.034 Uiso 1 1 calc R U . . .
H7AB H 0.445375 0.266223 0.262252 0.034 Uiso 1 1 calc R U . . .
C8A C 0.1451(2) 0.1141(3) 0.31893(11) 0.0401(8) Uani 1 1 d . . . . .
H8AA H 0.100467 0.094102 0.342935 0.048 Uiso 1 1 calc R U . . .
H8AB H 0.093143 0.159997 0.300066 0.048 Uiso 1 1 calc R U . . .
C9A C 0.1777(3) 0.0027(3) 0.29877(10) 0.0362(7) Uani 1 1 d . . . . .
H9A H 0.210808 0.008824 0.273014 0.043 Uiso 1 1 calc R U . . .
C10A C 0.1646(3) -0.1032(3) 0.31362(10) 0.0389(7) Uani 1 1 d . . . . .
H10A H 0.131764 -0.112897 0.339298 0.047 Uiso 1 1 calc R U . . .
H10B H 0.187730 -0.170734 0.298779 0.047 Uiso 1 1 calc R U . . .
O11A O 0.34532(15) 0.37596(16) 0.31724(5) 0.0256(4) Uani 1 1 d . . . . .
C12A C 0.2787(2) 0.3944(2) 0.34985(8) 0.0231(5) Uani 1 1 d . . . . .
C13A C 0.2140(2) 0.2956(2) 0.35972(8) 0.0261(6) Uani 1 1 d . . . . .
C14A C 0.1419(2) 0.2996(2) 0.39216(9) 0.0306(6) Uani 1 1 d . . . . .
H14A H 0.096540 0.232517 0.398761 0.037 Uiso 1 1 calc R U . . .
C15A C 0.1369(2) 0.4035(3) 0.41503(9) 0.0308(6) Uani 1 1 d D . . . .
C16A C 0.2060(2) 0.4995(2) 0.40501(8) 0.0272(6) Uani 1 1 d . . . . .
H16A H 0.203551 0.569177 0.421173 0.033 Uiso 1 1 calc R U . . .
C17A C 0.2792(2) 0.4982(2) 0.37216(8) 0.0232(5) Uani 1 1 d . . . . .
C18A C 0.0653(4) 0.4077(4) 0.45277(15) 0.0358(11) Uani 0.849(9) 1 d D . P A 1
H18A H 0.068088 0.489297 0.463957 0.043 Uiso 0.849(9) 1 calc R U P A 1
H18B H -0.016650 0.389492 0.444939 0.043 Uiso 0.849(9) 1 calc R U P A 1
C19A C 0.1068(5) 0.3227(4) 0.48506(14) 0.0386(10) Uani 0.849(9) 1 d D . P A 1
H19A H 0.106914 0.240768 0.478265 0.046 Uiso 0.849(9) 1 calc R U P A 1
C20A C 0.1426(3) 0.3514(4) 0.52161(13) 0.0469(13) Uani 0.849(9) 1 d D . P A 1
H20A H 0.143942 0.432368 0.529685 0.056 Uiso 0.849(9) 1 calc R U P A 1
H20B H 0.167556 0.291441 0.540264 0.056 Uiso 0.849(9) 1 calc R U P A 1
C21A C 0.3564(2) 0.5993(2) 0.36326(8) 0.0232(5) Uani 1 1 d . . . . .
C22A C 0.3558(2) 0.6542(2) 0.32547(8) 0.0246(5) Uani 1 1 d . . . . .
C23A C 0.4305(2) 0.7482(2) 0.31847(8) 0.0276(6) Uani 1 1 d . . . . .
H23A H 0.428882 0.785541 0.292652 0.033 Uiso 1 1 calc R U . . .
C24A C 0.5075(2) 0.7876(2) 0.34905(9) 0.0278(6) Uani 1 1 d . . . . .
H24A H 0.558936 0.851273 0.343984 0.033 Uiso 1 1 calc R U . . .
C25A C 0.5097(2) 0.7342(2) 0.38722(9) 0.0277(6) Uani 1 1 d . . . . .
C26A C 0.4343(2) 0.6415(2) 0.39380(8) 0.0254(5) Uani 1 1 d . . . . .
H26A H 0.435236 0.605180 0.419785 0.030 Uiso 1 1 calc R U . . .
O27A O 0.27995(17) 0.62417(17) 0.29385(6) 0.0295(4) Uani 1 1 d . . . . .
H27A H 0.246999 0.559829 0.299119 0.044 Uiso 1 1 calc R U . . .
C28A C 0.5898(2) 0.7805(3) 0.42124(10) 0.0355(7) Uani 1 1 d . . . . .
H28A H 0.611063 0.714597 0.439982 0.043 Uiso 1 1 calc R U . . .
H28B H 0.661984 0.810962 0.409827 0.043 Uiso 1 1 calc R U . . .
C29A C 0.5329(3) 0.8781(3) 0.44435(9) 0.0386(7) Uani 1 1 d . . . . .
H29A H 0.466809 0.858290 0.459187 0.046 Uiso 1 1 calc R U . . .
C30A C 0.5684(3) 0.9886(3) 0.44536(11) 0.0492(9) Uani 1 1 d . . . . .
H30A H 0.634147 1.011450 0.430859 0.059 Uiso 1 1 calc R U . . .
H30B H 0.528327 1.045872 0.460583 0.059 Uiso 1 1 calc R U . . .
O1B O 0.09597(15) 0.45143(18) 0.27827(6) 0.0333(5) Uani 1 1 d . . . . .
C2B C -0.0010(2) 0.4548(2) 0.29231(8) 0.0262(6) Uani 1 1 d . . . . .
C3B C -0.0273(2) 0.5372(2) 0.32488(9) 0.0305(6) Uani 1 1 d . . . . .
H3B H 0.029867 0.593414 0.333681 0.037 Uiso 1 1 calc R U . . .
C4B C -0.1287(2) 0.5359(2) 0.34257(8) 0.0288(6) Uani 1 1 d . . . . .
H4B H -0.140931 0.594606 0.362579 0.035 Uiso 1 1 calc R U . . .
C5B C -0.2256(2) 0.4493(2) 0.33359(8) 0.0249(5) Uani 1 1 d . . . . .
C6B C -0.1906(2) 0.3494(2) 0.30459(8) 0.0226(5) Uani 1 1 d . . . . .
H6B H -0.261744 0.321085 0.289077 0.027 Uiso 1 1 calc R U . . .
C7B C -0.0992(2) 0.3808(2) 0.27474(8) 0.0250(5) Uani 1 1 d . . . . .
H7BA H -0.066929 0.306379 0.263932 0.030 Uiso 1 1 calc R U . . .
H7BB H -0.137035 0.424370 0.251710 0.030 Uiso 1 1 calc R U . . .
C8B C -0.3381(2) 0.5137(3) 0.31908(9) 0.0306(6) Uani 1 1 d . . . . .
H8BA H -0.403312 0.456455 0.318567 0.037 Uiso 1 1 calc R U . . .
H8BB H -0.355378 0.576939 0.338755 0.037 Uiso 1 1 calc R U . . .
C9B C -0.3304(2) 0.5677(3) 0.27799(9) 0.0333(6) Uani 1 1 d . . . . .
H9B H -0.273807 0.627789 0.274616 0.040 Uiso 1 1 calc R U . . .
C10B C -0.3960(3) 0.5380(3) 0.24639(10) 0.0427(8) Uani 1 1 d . . . . .
H10C H -0.453515 0.478255 0.248665 0.051 Uiso 1 1 calc R U . . .
H10D H -0.386283 0.576180 0.221113 0.051 Uiso 1 1 calc R U . . .
O11B O -0.14533(15) 0.25189(15) 0.33032(5) 0.0238(4) Uani 1 1 d . . . . .
C12B C -0.1912(2) 0.2672(2) 0.36763(8) 0.0225(5) Uani 1 1 d . . . . .
C13B C -0.2405(2) 0.3788(2) 0.37234(8) 0.0237(5) Uani 1 1 d . . . . .
C14B C -0.2883(2) 0.4104(2) 0.40836(8) 0.0279(6) Uani 1 1 d . . . . .
H14B H -0.323027 0.486241 0.411225 0.033 Uiso 1 1 calc R U . . .
C15B C -0.2852(2) 0.3299(3) 0.44062(8) 0.0273(6) Uani 1 1 d . . . . .
C16B C -0.2345(2) 0.2192(2) 0.43517(8) 0.0267(6) Uani 1 1 d . . . . .
H16B H -0.231169 0.165283 0.457321 0.032 Uiso 1 1 calc R U . . .
C17B C -0.1877(2) 0.1832(2) 0.39839(8) 0.0243(5) Uani 1 1 d . . . . .
C3 C -0.3416(2) 0.3601(3) 0.47973(9) 0.0331(6) Uani 1 1 d . . . . .
H3C H -0.312296 0.304779 0.501101 0.040 Uiso 1 1 calc R U . . .
H3D H -0.317883 0.441332 0.488029 0.040 Uiso 1 1 calc R U . . .
C1 C -0.4726(3) 0.3541(3) 0.47714(10) 0.0365(7) Uani 1 1 d . . . . .
H1 H -0.511264 0.375134 0.500925 0.044 Uiso 1 1 calc R U . . .
C2 C -0.5387(3) 0.3230(3) 0.44568(11) 0.0443(8) Uani 1 1 d . . . . .
H2A H -0.504573 0.301033 0.421097 0.053 Uiso 1 1 calc R U . . .
H2B H -0.620729 0.322281 0.447405 0.053 Uiso 1 1 calc R U . . .
C21B C -0.1366(2) 0.0619(2) 0.39466(8) 0.0250(5) Uani 1 1 d . . . . .
C22B C -0.1747(2) -0.0195(2) 0.36493(8) 0.0270(6) Uani 1 1 d . . . . .
C23B C -0.1269(3) -0.1330(3) 0.36419(9) 0.0332(6) Uani 1 1 d . . . . .
H23B H -0.152140 -0.187362 0.343651 0.040 Uiso 1 1 calc R U . . .
C24B C -0.0429(3) -0.1673(3) 0.39318(9) 0.0340(6) Uani 1 1 d . . . . .
H24B H -0.011426 -0.245171 0.392422 0.041 Uiso 1 1 calc R U . . .
C25B C -0.0042(2) -0.0891(3) 0.42324(9) 0.0303(6) Uani 1 1 d . . . . .
C26B C -0.0513(2) 0.0241(2) 0.42311(8) 0.0266(6) Uani 1 1 d . . . . .
H26B H -0.024266 0.078589 0.443356 0.032 Uiso 1 1 calc R U . . .
O27B O -0.26244(17) 0.00031(18) 0.33681(6) 0.0334(5) Uani 1 1 d . . . . .
H27B H -0.277416 0.073260 0.335762 0.050 Uiso 1 1 calc R U . . .
C28B C 0.0891(2) -0.1242(3) 0.45488(10) 0.0374(7) Uani 1 1 d . . . . .
H28C H 0.062655 -0.104129 0.482162 0.045 Uiso 1 1 calc R U . . .
H28D H 0.101138 -0.211168 0.453814 0.045 Uiso 1 1 calc R U . . .
C29B C 0.2011(3) -0.0629(3) 0.44835(11) 0.0433(8) Uani 1 1 d . . . . .
H29B H 0.243845 -0.084942 0.425572 0.052 Uiso 1 1 calc R U . . .
C30B C 0.2437(3) 0.0204(4) 0.47267(14) 0.0615(11) Uani 1 1 d . . . . .
H30C H 0.202509 0.043871 0.495636 0.074 Uiso 1 1 calc R U . . .
H30D H 0.315619 0.057014 0.467265 0.074 Uiso 1 1 calc R U . . .
C19B C 0.056(2) 0.360(2) 0.4812(6) 0.038(6) Uiso 0.151(9) 1 d D . P A 2
H19B H -0.004302 0.363637 0.499655 0.046 Uiso 0.151(9) 1 calc R U P A 2
C20B C 0.149(3) 0.302(4) 0.4930(15) 0.082(15) Uiso 0.151(9) 1 d D . P A 2
H20C H 0.212441 0.296370 0.475654 0.099 Uiso 0.151(9) 1 calc R U P A 2
H20D H 0.153662 0.266207 0.518981 0.099 Uiso 0.151(9) 1 calc R U P A 2
C18B C 0.0357(17) 0.421(2) 0.4423(6) 0.028(7) Uiso 0.151(9) 1 d D . P A 2
H18C H 0.024228 0.506612 0.447168 0.033 Uiso 0.151(9) 1 calc R U P A 2
H18D H -0.036071 0.389180 0.428714 0.033 Uiso 0.151(9) 1 calc R U P A 2


_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
O1A C2A 1.233(3) . ?
C2A C3A 1.456(4) . ?
C2A C7A 1.500(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.337(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.512(4) . ?
C5A C6A 1.542(4) . ?
C5A C8A 1.547(4) . ?
C5A C13A 1.515(4) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.511(4) . ?
C6A O11A 1.472(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.477(4) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.301(4) . ?
C10A H10A 0.9500 . ?
C10A H10B 0.9500 . ?
O11A C12A 1.366(3) . ?
C12A C13A 1.387(4) . ?
C12A C17A 1.382(4) . ?
C13A C14A 1.385(4) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.395(4) . ?
C15A C16A 1.392(4) . ?
C15A C18A 1.526(5) . ?
C15A C18B 1.519(16) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.403(4) . ?
C17A C21A 1.483(4) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C18A C19A 1.496(7) . ?
C19A H19A 0.9500 . ?
C19A C20A 1.299(6) . ?
C20A H20A 0.9500 . ?
C20A H20B 0.9500 . ?
C21A C22A 1.392(4) . ?
C21A C26A 1.403(4) . ?
C22A C23A 1.391(4) . ?
C22A O27A 1.374(3) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.387(4) . ?
C24A H24A 0.9500 . ?
C24A C25A 1.396(4) . ?
C25A C26A 1.382(4) . ?
C25A C28A 1.514(4) . ?
C26A H26A 0.9500 . ?
O27A H27A 0.8400 . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C28A C29A 1.506(4) . ?
C29A H29A 0.9500 . ?
C29A C30A 1.310(5) . ?
C30A H30A 0.9500 . ?
C30A H30B 0.9500 . ?
O1B C2B 1.229(3) . ?
C2B C3B 1.463(4) . ?
C2B C7B 1.502(4) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.330(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.502(4) . ?
C5B C6B 1.542(4) . ?
C5B C8B 1.543(3) . ?
C5B C13B 1.522(4) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.515(4) . ?
C6B O11B 1.470(3) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.493(4) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.305(4) . ?
C10B H10C 0.9500 . ?
C10B H10D 0.9500 . ?
O11B C12B 1.373(3) . ?
C12B C13B 1.391(4) . ?
C12B C17B 1.387(4) . ?
C13B C14B 1.380(4) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.398(4) . ?
C15B C16B 1.392(4) . ?
C15B C3 1.511(4) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.410(4) . ?
C17B C21B 1.495(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C3 C1 1.510(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.308(5) . ?
C2 H2A 0.9500 . ?
C2 H2B 0.9500 . ?
C21B C22B 1.399(4) . ?
C21B C26B 1.396(4) . ?
C22B C23B 1.393(4) . ?
C22B O27B 1.361(3) . ?
C23B H23B 0.9500 . ?
C23B C24B 1.386(4) . ?
C24B H24B 0.9500 . ?
C24B C25B 1.386(4) . ?
C25B C26B 1.386(4) . ?
C25B C28B 1.518(4) . ?
C26B H26B 0.9500 . ?
O27B H27B 0.8400 . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
C28B C29B 1.489(4) . ?
C29B H29B 0.9500 . ?
C29B C30B 1.316(5) . ?
C30B H30C 0.9500 . ?
C30B H30D 0.9500 . ?
C19B H19B 0.9500 . ?
C19B C20B 1.295(19) . ?
C19B C18B 1.462(18) . ?
C20B H20C 0.9500 . ?
C20B H20D 0.9500 . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?

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
O1A C2A C3A 122.1(3) . . ?
O1A C2A C7A 120.4(3) . . ?
C3A C2A C7A 117.5(2) . . ?
C2A C3A H3A 119.1 . . ?
C4A C3A C2A 121.8(3) . . ?
C4A C3A H3A 119.1 . . ?
C3A C4A H4A 117.6 . . ?
C3A C4A C5A 124.8(3) . . ?
C5A C4A H4A 117.6 . . ?
C4A C5A C6A 111.3(2) . . ?
C4A C5A C8A 111.0(2) . . ?
C4A C5A C13A 105.7(2) . . ?
C6A C5A C8A 115.0(2) . . ?
C13A C5A C6A 100.0(2) . . ?
C13A C5A C8A 113.1(2) . . ?
C5A C6A H6A 109.5 . . ?
C7A C6A C5A 116.3(2) . . ?
C7A C6A H6A 109.5 . . ?
O11A C6A C5A 105.5(2) . . ?
O11A C6A H6A 109.5 . . ?
O11A C6A C7A 106.4(2) . . ?
C2A C7A C6A 111.5(2) . . ?
C2A C7A H7AA 109.3 . . ?
C2A C7A H7AB 109.3 . . ?
C6A C7A H7AA 109.3 . . ?
C6A C7A H7AB 109.3 . . ?
H7AA C7A H7AB 108.0 . . ?
C5A C8A H8AA 108.6 . . ?
C5A C8A H8AB 108.6 . . ?
H8AA C8A H8AB 107.6 . . ?
C9A C8A C5A 114.7(2) . . ?
C9A C8A H8AA 108.6 . . ?
C9A C8A H8AB 108.6 . . ?
C8A C9A H9A 117.5 . . ?
C10A C9A C8A 125.0(3) . . ?
C10A C9A H9A 117.5 . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A H10B 120.0 . . ?
H10A C10A H10B 120.0 . . ?
C12A O11A C6A 106.22(19) . . ?
O11A C12A C13A 113.0(2) . . ?
O11A C12A C17A 124.0(2) . . ?
C17A C12A C13A 122.9(2) . . ?
C12A C13A C5A 108.0(2) . . ?
C14A C13A C5A 131.5(2) . . ?
C14A C13A C12A 120.2(3) . . ?
C13A C14A H14A 120.4 . . ?
C13A C14A C15A 119.1(3) . . ?
C15A C14A H14A 120.4 . . ?
C14A C15A C18A 120.4(3) . . ?
C14A C15A C18B 118.7(11) . . ?
C16A C15A C14A 119.0(3) . . ?
C16A C15A C18A 120.4(3) . . ?
C16A C15A C18B 120.3(11) . . ?
C15A C16A H16A 118.5 . . ?
C15A C16A C17A 123.1(3) . . ?
C17A C16A H16A 118.5 . . ?
C12A C17A C16A 115.6(2) . . ?
C12A C17A C21A 122.2(2) . . ?
C16A C17A C21A 122.1(2) . . ?
C15A C18A H18A 108.9 . . ?
C15A C18A H18B 108.9 . . ?
H18A C18A H18B 107.7 . . ?
C19A C18A C15A 113.3(3) . . ?
C19A C18A H18A 108.9 . . ?
C19A C18A H18B 108.9 . . ?
C18A C19A H19A 117.2 . . ?
C20A C19A C18A 125.5(5) . . ?
C20A C19A H19A 117.2 . . ?
C19A C20A H20A 120.0 . . ?
C19A C20A H20B 120.0 . . ?
H20A C20A H20B 120.0 . . ?
C22A C21A C17A 122.6(2) . . ?
C22A C21A C26A 118.2(2) . . ?
C26A C21A C17A 119.2(2) . . ?
C23A C22A C21A 120.5(2) . . ?
O27A C22A C21A 123.4(2) . . ?
O27A C22A C23A 116.0(2) . . ?
C22A C23A H23A 119.9 . . ?
C24A C23A C22A 120.2(3) . . ?
C24A C23A H23A 119.9 . . ?
C23A C24A H24A 119.8 . . ?
C23A C24A C25A 120.3(3) . . ?
C25A C24A H24A 119.8 . . ?
C24A C25A C28A 120.5(3) . . ?
C26A C25A C24A 118.8(2) . . ?
C26A C25A C28A 120.7(3) . . ?
C21A C26A H26A 119.0 . . ?
C25A C26A C21A 121.9(3) . . ?
C25A C26A H26A 119.0 . . ?
C22A O27A H27A 109.5 . . ?
C25A C28A H28A 109.4 . . ?
C25A C28A H28B 109.4 . . ?
H28A C28A H28B 108.0 . . ?
C29A C28A C25A 111.2(2) . . ?
C29A C28A H28A 109.4 . . ?
C29A C28A H28B 109.4 . . ?
C28A C29A H29A 117.8 . . ?
C30A C29A C28A 124.3(3) . . ?
C30A C29A H29A 117.8 . . ?
C29A C30A H30A 120.0 . . ?
C29A C30A H30B 120.0 . . ?
H30A C30A H30B 120.0 . . ?
O1B C2B C3B 121.2(2) . . ?
O1B C2B C7B 121.3(3) . . ?
C3B C2B C7B 117.3(2) . . ?
C2B C3B H3B 119.0 . . ?
C4B C3B C2B 122.1(3) . . ?
C4B C3B H3B 119.0 . . ?
C3B C4B H4B 117.2 . . ?
C3B C4B C5B 125.5(3) . . ?
C5B C4B H4B 117.2 . . ?
C4B C5B C6B 112.5(2) . . ?
C4B C5B C8B 111.3(2) . . ?
C4B C5B C13B 106.5(2) . . ?
C6B C5B C8B 112.9(2) . . ?
C13B C5B C6B 100.6(2) . . ?
C13B C5B C8B 112.4(2) . . ?
C5B C6B H6B 108.6 . . ?
C7B C6B C5B 116.3(2) . . ?
C7B C6B H6B 108.6 . . ?
O11B C6B C5B 106.4(2) . . ?
O11B C6B H6B 108.6 . . ?
O11B C6B C7B 108.14(19) . . ?
C2B C7B C6B 114.3(2) . . ?
C2B C7B H7BA 108.7 . . ?
C2B C7B H7BB 108.7 . . ?
C6B C7B H7BA 108.7 . . ?
C6B C7B H7BB 108.7 . . ?
H7BA C7B H7BB 107.6 . . ?
C5B C8B H8BA 109.0 . . ?
C5B C8B H8BB 109.0 . . ?
H8BA C8B H8BB 107.8 . . ?
C9B C8B C5B 113.0(2) . . ?
C9B C8B H8BA 109.0 . . ?
C9B C8B H8BB 109.0 . . ?
C8B C9B H9B 117.7 . . ?
C10B C9B C8B 124.5(3) . . ?
C10B C9B H9B 117.7 . . ?
C9B C10B H10C 120.0 . . ?
C9B C10B H10D 120.0 . . ?
H10C C10B H10D 120.0 . . ?
C12B O11B C6B 106.51(18) . . ?
O11B C12B C13B 112.9(2) . . ?
O11B C12B C17B 124.9(2) . . ?
C17B C12B C13B 122.2(2) . . ?
C12B C13B C5B 108.4(2) . . ?
C14B C13B C5B 130.9(2) . . ?
C14B C13B C12B 120.7(2) . . ?
C13B C14B H14B 120.3 . . ?
C13B C14B C15B 119.5(3) . . ?
C15B C14B H14B 120.3 . . ?
C14B C15B C3 120.5(3) . . ?
C16B C15B C14B 118.6(3) . . ?
C16B C15B C3 120.8(3) . . ?
C15B C16B H16B 118.4 . . ?
C15B C16B C17B 123.2(3) . . ?
C17B C16B H16B 118.4 . . ?
C12B C17B C16B 115.8(2) . . ?
C12B C17B C21B 124.2(2) . . ?
C16B C17B C21B 120.1(2) . . ?
C15B C3 H3C 108.7 . . ?
C15B C3 H3D 108.7 . . ?
H3C C3 H3D 107.6 . . ?
C1 C3 C15B 114.1(2) . . ?
C1 C3 H3C 108.7 . . ?
C1 C3 H3D 108.7 . . ?
C3 C1 H1 116.5 . . ?
C2 C1 C3 127.0(3) . . ?
C2 C1 H1 116.5 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 H2B 120.0 . . ?
H2A C2 H2B 120.0 . . ?
C22B C21B C17B 123.0(2) . . ?
C26B C21B C17B 119.4(2) . . ?
C26B C21B C22B 117.5(2) . . ?
C23B C22B C21B 120.1(2) . . ?
O27B C22B C21B 124.9(2) . . ?
O27B C22B C23B 114.9(2) . . ?
C22B C23B H23B 119.7 . . ?
C24B C23B C22B 120.6(3) . . ?
C24B C23B H23B 119.7 . . ?
C23B C24B H24B 119.7 . . ?
C25B C24B C23B 120.7(3) . . ?
C25B C24B H24B 119.7 . . ?
C24B C25B C26B 118.0(3) . . ?
C24B C25B C28B 121.5(3) . . ?
C26B C25B C28B 120.5(3) . . ?
C21B C26B H26B 118.4 . . ?
C25B C26B C21B 123.2(3) . . ?
C25B C26B H26B 118.4 . . ?
C22B O27B H27B 109.5 . . ?
C25B C28B H28C 109.2 . . ?
C25B C28B H28D 109.2 . . ?
H28C C28B H28D 107.9 . . ?
C29B C28B C25B 111.8(2) . . ?
C29B C28B H28C 109.2 . . ?
C29B C28B H28D 109.2 . . ?
C28B C29B H29B 118.5 . . ?
C30B C29B C28B 123.0(4) . . ?
C30B C29B H29B 118.5 . . ?
C29B C30B H30C 120.0 . . ?
C29B C30B H30D 120.0 . . ?
H30C C30B H30D 120.0 . . ?
C20B C19B H19B 116.6 . . ?
C20B C19B C18B 127(3) . . ?
C18B C19B H19B 116.6 . . ?
C19B C20B H20C 120.0 . . ?
C19B C20B H20D 120.0 . . ?
H20C C20B H20D 120.0 . . ?
C15A C18B H18C 109.4 . . ?
C15A C18B H18D 109.4 . . ?
C19B C18B C15A 111.2(17) . . ?
C19B C18B H18C 109.4 . . ?
C19B C18B H18D 109.4 . . ?
H18C C18B H18D 108.0 . . ?

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
O27A H27A O1B 0.84 2.21 2.907(3) 140.3 . yes
O27B H27B O1A 0.84 2.01 2.662(3) 134.0 1_455 yes

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
O1A C2A C3A C4A 171.6(3) . . . . ?
O1A C2A C7A C6A -145.4(3) . . . . ?
C2A C3A C4A C5A -6.1(4) . . . . ?
C3A C2A C7A C6A 37.0(3) . . . . ?
C3A C4A C5A C6A -4.9(4) . . . . ?
C3A C4A C5A C8A 124.6(3) . . . . ?
C3A C4A C5A C13A -112.5(3) . . . . ?
C4A C5A C6A C7A 32.7(3) . . . . ?
C4A C5A C6A O11A -84.9(2) . . . . ?
C4A C5A C8A C9A -51.1(4) . . . . ?
C4A C5A C13A C12A 96.1(3) . . . . ?
C4A C5A C13A C14A -77.5(3) . . . . ?
C5A C6A C7A C2A -48.5(3) . . . . ?
C5A C6A O11A C12A -24.7(2) . . . . ?
C5A C8A C9A C10A 112.4(4) . . . . ?
C5A C13A C14A C15A 171.9(3) . . . . ?
C6A C5A C8A C9A 76.4(3) . . . . ?
C6A C5A C13A C12A -19.6(3) . . . . ?
C6A C5A C13A C14A 166.9(3) . . . . ?
C6A O11A C12A C13A 12.4(3) . . . . ?
C6A O11A C12A C17A -170.5(2) . . . . ?
C7A C2A C3A C4A -10.9(4) . . . . ?
C7A C6A O11A C12A -148.8(2) . . . . ?
C8A C5A C6A C7A -94.6(3) . . . . ?
C8A C5A C6A O11A 147.7(2) . . . . ?
C8A C5A C13A C12A -142.4(2) . . . . ?
C8A C5A C13A C14A 44.1(4) . . . . ?
O11A C6A C7A C2A 68.6(3) . . . . ?
O11A C12A C13A C5A 5.4(3) . . . . ?
O11A C12A C13A C14A 179.9(2) . . . . ?
O11A C12A C17A C16A -179.0(2) . . . . ?
O11A C12A C17A C21A -2.0(4) . . . . ?
C12A C13A C14A C15A -1.0(4) . . . . ?
C12A C17A C21A C22A 56.9(4) . . . . ?
C12A C17A C21A C26A -122.5(3) . . . . ?
C13A C5A C6A C7A 144.0(2) . . . . ?
C13A C5A C6A O11A 26.3(2) . . . . ?
C13A C5A C8A C9A -169.6(3) . . . . ?
C13A C12A C17A C16A -2.3(4) . . . . ?
C13A C12A C17A C21A 174.7(2) . . . . ?
C13A C14A C15A C16A -1.1(4) . . . . ?
C13A C14A C15A C18A -175.5(3) . . . . ?
C13A C14A C15A C18B 163.0(9) . . . . ?
C14A C15A C16A C17A 1.6(4) . . . . ?
C14A C15A C18A C19A 62.1(5) . . . . ?
C14A C15A C18B C19B 83(2) . . . . ?
C15A C16A C17A C12A 0.1(4) . . . . ?
C15A C16A C17A C21A -176.9(2) . . . . ?
C15A C18A C19A C20A 120.2(5) . . . . ?
C16A C15A C18A C19A -112.2(4) . . . . ?
C16A C15A C18B C19B -113.0(18) . . . . ?
C16A C17A C21A C22A -126.3(3) . . . . ?
C16A C17A C21A C26A 54.3(3) . . . . ?
C17A C12A C13A C5A -171.6(2) . . . . ?
C17A C12A C13A C14A 2.8(4) . . . . ?
C17A C21A C22A C23A -179.5(2) . . . . ?
C17A C21A C22A O27A 3.5(4) . . . . ?
C17A C21A C26A C25A 179.0(2) . . . . ?
C18A C15A C16A C17A 176.0(3) . . . . ?
C21A C22A C23A C24A 0.6(4) . . . . ?
C22A C21A C26A C25A -0.4(4) . . . . ?
C22A C23A C24A C25A -0.7(4) . . . . ?
C23A C24A C25A C26A 0.3(4) . . . . ?
C23A C24A C25A C28A -177.3(3) . . . . ?
C24A C25A C26A C21A 0.3(4) . . . . ?
C24A C25A C28A C29A 87.7(3) . . . . ?
C25A C28A C29A C30A -114.6(3) . . . . ?
C26A C21A C22A C23A 0.0(4) . . . . ?
C26A C21A C22A O27A -177.0(2) . . . . ?
C26A C25A C28A C29A -89.8(3) . . . . ?
O27A C22A C23A C24A 177.8(2) . . . . ?
C28A C25A C26A C21A 177.9(3) . . . . ?
O1B C2B C3B C4B -174.7(3) . . . . ?
O1B C2B C7B C6B 153.0(2) . . . . ?
C2B C3B C4B C5B 3.0(4) . . . . ?
C3B C2B C7B C6B -31.3(3) . . . . ?
C3B C4B C5B C6B 6.9(4) . . . . ?
C3B C4B C5B C8B -121.0(3) . . . . ?
C3B C4B C5B C13B 116.2(3) . . . . ?
C4B C5B C6B C7B -29.1(3) . . . . ?
C4B C5B C6B O11B 91.4(2) . . . . ?
C4B C5B C8B C9B 69.5(3) . . . . ?
C4B C5B C13B C12B -103.7(2) . . . . ?
C4B C5B C13B C14B 73.9(3) . . . . ?
C5B C6B C7B C2B 41.4(3) . . . . ?
C5B C6B O11B C12B 22.4(2) . . . . ?
C5B C8B C9B C10B 117.9(3) . . . . ?
C5B C13B C14B C15B -176.2(3) . . . . ?
C6B C5B C8B C9B -58.1(3) . . . . ?
C6B C5B C13B C12B 13.8(3) . . . . ?
C6B C5B C13B C14B -168.7(3) . . . . ?
C6B O11B C12B C13B -13.9(3) . . . . ?
C6B O11B C12B C17B 167.6(2) . . . . ?
C7B C2B C3B C4B 9.5(4) . . . . ?
C7B C6B O11B C12B 148.0(2) . . . . ?
C8B C5B C6B C7B 98.0(3) . . . . ?
C8B C5B C6B O11B -141.6(2) . . . . ?
C8B C5B C13B C12B 134.2(2) . . . . ?
C8B C5B C13B C14B -48.2(4) . . . . ?
O11B C6B C7B C2B -78.1(3) . . . . ?
O11B C12B C13B C5B -0.6(3) . . . . ?
O11B C12B C13B C14B -178.5(2) . . . . ?
O11B C12B C17B C16B 176.7(2) . . . . ?
O11B C12B C17B C21B -2.2(4) . . . . ?
C12B C13B C14B C15B 1.1(4) . . . . ?
C12B C17B C21B C22B -57.7(4) . . . . ?
C12B C17B C21B C26B 125.8(3) . . . . ?
C13B C5B C6B C7B -142.0(2) . . . . ?
C13B C5B C6B O11B -21.5(2) . . . . ?
C13B C5B C8B C9B -171.2(2) . . . . ?
C13B C12B C17B C16B -1.7(4) . . . . ?
C13B C12B C17B C21B 179.5(2) . . . . ?
C13B C14B C15B C16B -0.5(4) . . . . ?
C13B C14B C15B C3 -177.2(2) . . . . ?
C14B C15B C16B C17B -1.2(4) . . . . ?
C14B C15B C3 C1 74.3(3) . . . . ?
C15B C16B C17B C12B 2.2(4) . . . . ?
C15B C16B C17B C21B -178.8(2) . . . . ?
C15B C3 C1 C2 2.0(5) . . . . ?
C16B C15B C3 C1 -102.3(3) . . . . ?
C16B C17B C21B C22B 123.5(3) . . . . ?
C16B C17B C21B C26B -53.0(3) . . . . ?
C17B C12B C13B C5B 177.9(2) . . . . ?
C17B C12B C13B C14B 0.1(4) . . . . ?
C17B C21B C22B C23B -177.2(3) . . . . ?
C17B C21B C22B O27B -1.3(4) . . . . ?
C17B C21B C26B C25B 176.2(2) . . . . ?
C3 C15B C16B C17B 175.5(2) . . . . ?
C21B C22B C23B C24B 1.1(4) . . . . ?
C22B C21B C26B C25B -0.5(4) . . . . ?
C22B C23B C24B C25B -0.4(5) . . . . ?
C23B C24B C25B C26B -0.6(4) . . . . ?
C23B C24B C25B C28B -179.0(3) . . . . ?
C24B C25B C26B C21B 1.1(4) . . . . ?
C24B C25B C28B C29B 108.4(3) . . . . ?
C25B C28B C29B C30B 109.9(4) . . . . ?
C26B C21B C22B C23B -0.6(4) . . . . ?
C26B C21B C22B O27B 175.3(2) . . . . ?
C26B C25B C28B C29B -70.0(4) . . . . ?
O27B C22B C23B C24B -175.2(3) . . . . ?
C28B C25B C26B C21B 179.5(3) . . . . ?
C20B C19B C18B C15A 3(4) . . . . ?
C18B C15A C16A C17A -162.3(10) . . . . ?

_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 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.648
####################################################################### 
# 
# 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_44
_database_code_depnum_ccdc_archive 'CCDC 2327695'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDE
_nottingham_internal_coll_number 17310
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 5.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   23/10/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 24/10/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 24/10/2017
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 20/11/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 24/11/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 24/11/2017
_refine_special_details          
;
The two allyl groups of the molecule are each disordered over multiple positions. 
Allyl group C19-C21 has two positions for C20, and the minor component terminal 
atom (C21A and C21B) is additionally disordered over two positions. The 
occupancies of the different components were refined competitviely, and 
converged at ratios of 0.65:0.35 for C20 and 0.65:0.20:0.15 for the C21 
position. 
The second allyl group, C30-C32, is disordered over three positions. Although the 
positions of the alpha carbon atom of this group (C30) were almost coincident, it 
was most straightforward to treat group entirely separately in this case. The 
occupancies of the three components were refined competitively, converging to a 
ratio of 0.47:0.30:0.23.
Equivalent C-C 1,2- and 1,3- distances of the disordered atoms were restrained 
to be approxiamtely equal. Enhanced rigid bond and similarity restraints were 
applied to all allyl group carbon atoms.
;
_audit_creation_date             2017-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H29.99 O4'
_chemical_formula_sum            'C29 H30 O4'
_chemical_formula_weight         442.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H30 O4'
_chemical_oxdiff_usercomment     
'REARDE #17310 GVA-1298 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.1851(6)
_cell_length_b                   7.8229(2)
_cell_length_c                   31.2872(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.510(3)
_cell_angle_gamma                90
_cell_volume                     4695.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4865
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0200
_cell_measurement_theta_min      4.6090
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1888
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0087
0 0 1 0.0357
1 0 0 0.1369
3 4 -5 0.1295
-5 2 -3 0.0873
-1 0 0 0.1607
-4 -4 5 0.1236
5 -2 1 0.1978
5 -2 17 0.1256
7 0 16 0.1002
-6 2 15 0.0856
-7 -1 16 0.1187

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.044
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
0.0004 -0.0002 -0.9992 0.0007 -0.0472 0.0140
-0.0004 0.0002 0.9992 -0.0007 0.0472 -0.0140
0.9996 -0.0001 -0.0002 -0.0773 0.0058 0.0206
2.9958 3.9949 -5.0008 -0.0170 0.0020 0.8572
-4.9991 1.9978 -2.9984 0.4945 -0.0600 0.3016
-0.9996 0.0001 0.0002 0.0773 -0.0058 -0.0206
-3.9953 -3.9948 5.0010 0.0943 -0.0078 -0.8778
4.9999 -1.9983 1.0000 -0.4932 -0.0343 -0.2736
4.9939 -1.9947 16.9870 -0.5036 0.7204 -0.4980
6.9910 0.0031 15.9852 -0.5518 0.7951 -0.0802
-6.0054 2.0020 14.9872 0.5601 0.7833 0.0285
-7.0017 -0.9949 15.9897 0.4779 0.6592 -0.5500

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9181
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.693
_diffrn_reflns_theta_min         2.825
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        
'flash frozen in gaseous N2' # assumed default, please check
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 142.00   1.00   20.00    --  103.32  45.00 -60.00   58
  2  ω     60.00  90.00   1.00   20.00    --  103.32 -45.00-180.00   30
  3  ω     41.00  96.00   1.00   20.00    --  103.32 -45.00 -90.00   55
  4  ω     66.00  92.00   1.00   20.00    --  103.32 -45.00 -60.00   26
  5  ω     60.00  90.00   1.00   20.00    --  103.32 -30.00   0.00   30
  6  ω     37.00  87.00   1.00   20.00    --  103.32 -30.00  90.00   50
  7  ω     40.00  90.00   1.00   20.00    --  103.32 -45.00 150.00   50
  8  ω     63.00 121.00   1.00   20.00    --  103.32-125.00 120.00   58
  9  ω     37.00  90.00   1.00   20.00    --  103.32 -30.00 -30.00   53
 10  ω      2.00  28.00   1.00    5.00    --   43.06-125.00 -60.00   26
 11  ω     -8.00  28.00   1.00    5.00    --  -43.06  38.00-150.00   36
 12  ω    -47.00   3.00   1.00    5.00    --  -43.06  38.00  30.00   50
 13  ω   -111.00 -25.00   1.00    5.00    --  -43.06 -57.00  60.00   86
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'MiTeGen micromount' # assumed default, please check
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0773638000
_diffrn_orient_matrix_UB_12      0.0528865000
_diffrn_orient_matrix_UB_13      -0.0006953000
_diffrn_orient_matrix_UB_21      0.0057813000
_diffrn_orient_matrix_UB_22      0.0552550000
_diffrn_orient_matrix_UB_23      0.0471981000
_diffrn_orient_matrix_UB_31      0.0206306000
_diffrn_orient_matrix_UB_32      0.1814784000
_diffrn_orient_matrix_UB_33      -0.0140735000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4160
_reflns_number_total             4611
_reflns_odcompleteness_completeness 99.67
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4611
_refine_ls_number_restraints     273
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0657P)²+2.9875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1261
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20A-C19 \\sim C20-C19
 with sigma of 0.02
 C20-C21 \\sim C21A-C20A \\sim C21B-C20A
 with sigma of 0.02
 C30A-C26 \\sim C30-C26 \\sim C19-C9
 with sigma of 0.02
 C30B-C26 \\sim C30-C26 \\sim C26-C30A \\sim C19-C9
 with sigma of 0.02
 C31A-C32A \\sim C32-C31 \\sim C20-C21 \\sim C21A-C20A \\sim C21B-C20A
 with sigma of 0.02
 C21A-C20A \\sim C21B-C20A \\sim C20-C21 \\sim C32B-C31B \\sim C32-C31 \\sim
C31A-C32A
 with sigma of 0.02
 C20A-C19 \\sim C20-C19 \\sim C30A-C31A \\sim C30-C31
 with sigma of 0.02
 C20-C19 \\sim C20A-C19 \\sim C31B-C30B \\sim C30-C31 \\sim C31A-C30A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20 \\sim C20A \\sim C21 \\sim C21A \\sim C21B \\sim C30 \\sim C30A
\\sim C30B \\sim C31 \\sim C31A \\sim C31B \\sim C32 \\sim C32A \\sim C32B:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C19, C20, C20A, C21, C21A, C21B, C30, C30A, C30B, C31, C31A, C31B, C32, C32A,
 C32B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(H19A)+Sof(H19B)+Sof(H19C)+Sof(H19D)+Sof(C20)+Sof(H20)+Sof(C20A)+
 Sof(C21)+Sof(H21A)+Sof(H21B)]+1*[Sof(H20A)+Sof(C21A)+Sof(H21C)+Sof(H21D)]+1*
 [Sof(H20B)+Sof(C21B)+Sof(H21E)+Sof(H21F)]=1 with esd of 0.001
 1*[Sof(C30)+Sof(H30A)+Sof(H30B)+Sof(C31)+Sof(H31)+Sof(C32)+Sof(H32A)+
 Sof(H32B)]+1*[Sof(C30A)+Sof(H30C)+Sof(H30D)+Sof(C31A)+Sof(H31A)+Sof(C32A)+
 Sof(H32C)+Sof(H32D)]+1*[Sof(C30B)+Sof(H30E)+Sof(H30F)+Sof(C31B)+Sof(H31B)+
 Sof(C32B)+Sof(H32E)+Sof(H32F)]=1 with esd of 0.001
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 FVAR(1)
 Sof(H19C)=Sof(H19D)=Sof(C20A)=1-FVAR(2)
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=FVAR(2)
 Sof(H20A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=FVAR(3)
 Sof(H20B)=Sof(C21B)=Sof(H21E)=Sof(H21F)=FVAR(4)
 Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32C)=
 Sof(H32D)=FVAR(5)
 Sof(C30B)=Sof(H30E)=Sof(H30F)=Sof(C31B)=Sof(H31B)=Sof(C32B)=Sof(H32E)=
 Sof(H32F)=FVAR(6)
6.a Ternary CH refined with riding coordinates:
 C6(H6)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C17(H17A,H17B), C19(H19A,H19B), C19(H19C,H19D), C30(H30A,H30B),
 C30A(H30C,H30D), C30B(H30E,H30F)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C20(H20), C20A(H20A),
 C20A(H20B), C24(H24), C25(H25), C27(H27), C31(H31), C31A(H31A), C31B(H31B)
6.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C21A(H21C,H21D), C21B(H21E,H21F), C32(H32A,H32B), C32A(H32C,
 H32D), C32B(H32E,H32F)
6.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.48845(6) 0.59798(13) 0.60220(3) 0.0321(2) Uani 1 1 d . . . . .
C2 C 0.50651(7) 0.43533(18) 0.58960(4) 0.0274(3) Uani 1 1 d . . . . .
C3 C 0.49060(7) 0.28875(18) 0.61294(4) 0.0265(3) Uani 1 1 d . . . . .
C4 C 0.44707(7) 0.29609(18) 0.65397(4) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.42070(7) 0.4827(2) 0.66032(5) 0.0321(3) Uani 1 1 d . . . . .
H5A H 0.377355 0.499446 0.643419 0.039 Uiso 1 1 calc R . . . .
H5B H 0.409427 0.500423 0.690815 0.039 Uiso 1 1 calc R . . . .
C6 C 0.47388(8) 0.61398(19) 0.64686(5) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.454663 0.730694 0.652323 0.037 Uiso 1 1 calc R . . . .
C7 C 0.54141(8) 0.4227(2) 0.55085(4) 0.0326(3) Uani 1 1 d . . . . .
H7 H 0.551475 0.522779 0.534869 0.039 Uiso 1 1 calc R . . . .
C8 C 0.56135(8) 0.2642(2) 0.53570(5) 0.0351(3) Uani 1 1 d . . . . .
H8 H 0.584417 0.256541 0.509031 0.042 Uiso 1 1 calc R . . . .
C9 C 0.54824(8) 0.1153(2) 0.55885(5) 0.0333(3) Uani 1 1 d D . . . .
C10 C 0.51276(7) 0.13158(19) 0.59715(4) 0.0294(3) Uani 1 1 d . . . . .
H10 H 0.503225 0.031399 0.613229 0.035 Uiso 1 1 calc R . . . .
C11 C 0.38479(7) 0.1823(2) 0.64698(4) 0.0291(3) Uani 1 1 d . . . . .
H11 H 0.353790 0.212009 0.624327 0.035 Uiso 1 1 calc R . . . .
C12 C 0.36913(7) 0.04323(19) 0.66980(4) 0.0265(3) Uani 1 1 d . . . . .
C13 C 0.41528(7) -0.00943(18) 0.70591(4) 0.0263(3) Uani 1 1 d . . . . .
C14 C 0.47419(7) 0.10465(19) 0.71584(4) 0.0280(3) Uani 1 1 d . . . . .
H14 H 0.502281 0.080506 0.740258 0.034 Uiso 1 1 calc R . . . .
C15 C 0.48984(7) 0.24025(19) 0.69207(4) 0.0273(3) Uani 1 1 d . . . . .
H15 H 0.530022 0.305072 0.699526 0.033 Uiso 1 1 calc R . . . .
O16 O 0.53408(5) 0.59227(13) 0.67146(3) 0.0313(2) Uani 1 1 d . . . . .
C17 C 0.58550(9) 0.7228(2) 0.66592(6) 0.0416(4) Uani 1 1 d . . . . .
H17A H 0.567433 0.833859 0.676206 0.050 Uiso 1 1 calc R . . . .
H17B H 0.597009 0.734513 0.635274 0.050 Uiso 1 1 calc R . . . .
C18 C 0.64883(10) 0.6738(2) 0.69082(7) 0.0531(5) Uani 1 1 d . . . . .
H18A H 0.663938 0.559300 0.682173 0.080 Uiso 1 1 calc GR . . . .
H18B H 0.638084 0.673589 0.721381 0.080 Uiso 1 1 calc GR . . . .
H18C H 0.686191 0.756089 0.685303 0.080 Uiso 1 1 calc GR . . . .
C19 C 0.57067(10) -0.0590(2) 0.54272(6) 0.0448(4) Uani 1 1 d D U . . .
H19A H 0.572752 -0.138516 0.567307 0.054 Uiso 0.652(5) 1 calc R . P A 1
H19B H 0.534402 -0.102035 0.522745 0.054 Uiso 0.652(5) 1 calc R . P A 1
H19C H 0.561349 -0.068849 0.511640 0.054 Uiso 0.348(5) 1 calc R . P A 2
H19D H 0.544719 -0.150402 0.557597 0.054 Uiso 0.348(5) 1 calc R . P A 2
C20 C 0.63666(15) -0.0635(3) 0.52139(9) 0.0418(7) Uani 0.652(5) 1 d D U P A 1
H20 H 0.676403 -0.023459 0.536704 0.050 Uiso 0.652(5) 1 calc R . P A 1
C20A C 0.6517(4) -0.0758(11) 0.5523(3) 0.077(2) Uani 0.348(5) 1 d D U P A 2
H20A H 0.667163 -0.103469 0.580398 0.093 Uiso 0.199(6) 1 calc R . P B 3
H20B H 0.683444 0.013624 0.545839 0.093 Uiso 0.149(6) 1 calc R . P C 4
C21 C 0.64599(18) -0.1193(4) 0.48203(9) 0.0569(9) Uani 0.652(5) 1 d D U P A 1
H21A H 0.607434 -0.160274 0.465759 0.068 Uiso 0.652(5) 1 calc R . P A 1
H21B H 0.691268 -0.118459 0.469982 0.068 Uiso 0.652(5) 1 calc R . P A 1
C21A C 0.7013(7) -0.0503(16) 0.5199(5) 0.078(4) Uani 0.199(6) 1 d D U P A 3
H21C H 0.686362 -0.022531 0.491683 0.093 Uiso 0.199(6) 1 calc R . P B 3
H21D H 0.749629 -0.060869 0.526220 0.093 Uiso 0.199(6) 1 calc R . P B 3
C21B C 0.6731(10) -0.224(2) 0.5701(4) 0.091(5) Uani 0.149(6) 1 d D U P A 4
H21E H 0.640206 -0.311045 0.576263 0.110 Uiso 0.149(6) 1 calc R . P C 4
H21F H 0.721084 -0.241022 0.576591 0.110 Uiso 0.149(6) 1 calc R . P C 4
C22 C 0.30863(7) -0.06603(19) 0.65768(5) 0.0292(3) Uani 1 1 d . . . . .
C23 C 0.25187(7) -0.08710(18) 0.68527(5) 0.0289(3) Uani 1 1 d . . . . .
C24 C 0.19455(8) -0.1834(2) 0.67208(6) 0.0379(4) Uani 1 1 d . . . . .
H24 H 0.155769 -0.196716 0.690462 0.046 Uiso 1 1 calc R . . . .
C25 C 0.19412(9) -0.2598(2) 0.63220(6) 0.0450(4) Uani 1 1 d . . . . .
H25 H 0.154425 -0.323796 0.623442 0.054 Uiso 1 1 calc R . . . .
C26 C 0.25003(9) -0.2454(2) 0.60466(6) 0.0444(4) Uani 1 1 d D . . . .
C27 C 0.30664(8) -0.1466(2) 0.61813(5) 0.0369(3) Uani 1 1 d . . . . .
H27 H 0.345223 -0.133958 0.599572 0.044 Uiso 1 1 calc R . . . .
O28 O 0.25718(5) -0.00368(14) 0.72339(3) 0.0322(2) Uani 1 1 d . . . . .
C29 C 0.20171(8) -0.0259(2) 0.75305(5) 0.0415(4) Uani 1 1 d . . . . .
H29A H 0.158071 0.015684 0.740274 0.062 Uiso 1 1 calc GR . . . .
H29B H 0.211981 0.038917 0.779167 0.062 Uiso 1 1 calc GR . . . .
H29C H 0.197030 -0.147396 0.760057 0.062 Uiso 1 1 calc GR . . . .
C30 C 0.2462(12) -0.3443(12) 0.5630(3) 0.0486(16) Uani 0.477(6) 1 d D U P D 1
H30A H 0.207328 -0.295495 0.545944 0.058 Uiso 0.477(6) 1 calc R . P D 1
H30B H 0.289607 -0.320340 0.547236 0.058 Uiso 0.477(6) 1 calc R . P D 1
C30A C 0.2621(6) -0.3161(19) 0.5591(4) 0.047(2) Uani 0.296(4) 1 d D U P D 2
H30C H 0.220641 -0.383670 0.550556 0.057 Uiso 0.296(4) 1 calc R . P D 2
H30D H 0.265413 -0.218129 0.539210 0.057 Uiso 0.296(4) 1 calc R . P D 2
C30B C 0.246(3) -0.330(3) 0.5608(6) 0.048(2) Uani 0.226(6) 1 d D U P D 6
H30E H 0.196397 -0.338305 0.551241 0.058 Uiso 0.226(6) 1 calc R . P D 6
H30F H 0.271600 -0.261758 0.539571 0.058 Uiso 0.226(6) 1 calc R . P D 6
C31 C 0.2367(3) -0.5322(6) 0.56363(13) 0.0437(11) Uani 0.477(6) 1 d D U P D 1
H31 H 0.229917 -0.585718 0.536662 0.052 Uiso 0.477(6) 1 calc R . P D 1
C31A C 0.3256(4) -0.4259(9) 0.5536(2) 0.0551(15) Uani 0.296(4) 1 d D U P D 2
H31A H 0.368292 -0.371834 0.561154 0.066 Uiso 0.296(4) 1 calc R . P D 2
C31B C 0.2769(6) -0.5048(11) 0.5650(3) 0.0485(18) Uani 0.226(6) 1 d D U P D 6
H31B H 0.324092 -0.534764 0.559801 0.058 Uiso 0.226(6) 1 calc R . P D 6
C32 C 0.2367(2) -0.6377(5) 0.59855(16) 0.0430(11) Uani 0.477(6) 1 d D U P D 1
H32A H 0.243284 -0.591360 0.626363 0.052 Uiso 0.477(6) 1 calc R . P D 1
H32B H 0.230082 -0.757187 0.594967 0.052 Uiso 0.477(6) 1 calc R . P D 1
C32A C 0.3317(3) -0.5777(8) 0.54069(19) 0.0450(14) Uani 0.296(4) 1 d D U P D 2
H32C H 0.291507 -0.641083 0.532511 0.054 Uiso 0.296(4) 1 calc R . P D 2
H32D H 0.376540 -0.628814 0.539132 0.054 Uiso 0.296(4) 1 calc R . P D 2
C32B C 0.2277(7) -0.6081(15) 0.5771(6) 0.074(4) Uani 0.226(6) 1 d D U P D 6
H32E H 0.181928 -0.565743 0.581501 0.089 Uiso 0.226(6) 1 calc R . P D 6
H32F H 0.237573 -0.725801 0.581521 0.089 Uiso 0.226(6) 1 calc R . P D 6
O33 O 0.40616(5) -0.14351(13) 0.72530(3) 0.0319(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3774(17) . ?
O1 C6 1.4326(17) . ?
C2 C3 1.3947(19) . ?
C2 C7 1.394(2) . ?
C3 C4 1.5387(18) . ?
C3 C10 1.393(2) . ?
C4 C5 1.559(2) . ?
C4 C11 1.5043(19) . ?
C4 C15 1.5060(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.510(2) . ?
C6 H6 1.0000 . ?
C6 O16 1.3927(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(2) . ?
C9 C10 1.389(2) . ?
C9 C19 1.518(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.337(2) . ?
C12 C13 1.4873(19) . ?
C12 C22 1.488(2) . ?
C13 C14 1.471(2) . ?
C13 O33 1.2252(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.331(2) . ?
C15 H15 0.9500 . ?
O16 C17 1.4316(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.488(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 H19C 0.9900 . ?
C19 H19D 0.9900 . ?
C19 C20 1.437(3) . ?
C19 C20A 1.587(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.320(4) . ?
C20A H20A 0.9500 . ?
C20A H20B 0.9500 . ?
C20A C21A 1.411(11) . ?
C20A C21B 1.348(13) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C21A H21C 0.9500 . ?
C21A H21D 0.9500 . ?
C21B H21E 0.9500 . ?
C21B H21F 0.9500 . ?
C22 C23 1.405(2) . ?
C22 C27 1.389(2) . ?
C23 C24 1.393(2) . ?
C23 O28 1.3625(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(3) . ?
C26 C27 1.395(2) . ?
C26 C30 1.516(8) . ?
C26 C30A 1.547(11) . ?
C26 C30B 1.525(14) . ?
C27 H27 0.9500 . ?
O28 C29 1.4287(17) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.481(10) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C30A C31A 1.501(11) . ?
C30B H30E 0.9900 . ?
C30B H30F 0.9900 . ?
C30B C31B 1.500(15) . ?
C31 H31 0.9500 . ?
C31 C32 1.369(6) . ?
C31A H31A 0.9500 . ?
C31A C32A 1.261(8) . ?
C31B H31B 0.9500 . ?
C31B C32B 1.301(12) . ?
C32 H32A 0.9500 . ?
C32 H32B 0.9500 . ?
C32A H32C 0.9500 . ?
C32A H32D 0.9500 . ?
C32B H32E 0.9500 . ?
C32B H32F 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
C2 O1 C6 114.31(11) . . ?
O1 C2 C3 123.56(12) . . ?
O1 C2 C7 116.03(12) . . ?
C7 C2 C3 120.40(13) . . ?
C2 C3 C4 121.94(13) . . ?
C10 C3 C2 118.11(12) . . ?
C10 C3 C4 119.90(12) . . ?
C3 C4 C5 108.70(11) . . ?
C11 C4 C3 107.04(11) . . ?
C11 C4 C5 108.32(11) . . ?
C11 C4 C15 111.71(12) . . ?
C15 C4 C3 110.71(11) . . ?
C15 C4 C5 110.25(12) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 112.36(11) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
O1 C6 C5 110.53(12) . . ?
O1 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
O16 C6 O1 111.12(11) . . ?
O16 C6 C5 108.79(12) . . ?
O16 C6 H6 108.8 . . ?
C2 C7 H7 120.0 . . ?
C8 C7 C2 119.91(13) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.25(13) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C19 121.63(13) . . ?
C10 C9 C8 117.59(14) . . ?
C10 C9 C19 120.77(14) . . ?
C3 C10 H10 118.7 . . ?
C9 C10 C3 122.69(13) . . ?
C9 C10 H10 118.7 . . ?
C4 C11 H11 117.1 . . ?
C12 C11 C4 125.86(13) . . ?
C12 C11 H11 117.1 . . ?
C11 C12 C13 119.73(13) . . ?
C11 C12 C22 120.67(13) . . ?
C13 C12 C22 119.48(12) . . ?
C14 C13 C12 116.33(12) . . ?
O33 C13 C12 121.78(13) . . ?
O33 C13 C14 121.84(13) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 C13 122.83(13) . . ?
C15 C14 H14 118.6 . . ?
C4 C15 H15 118.3 . . ?
C14 C15 C4 123.32(13) . . ?
C14 C15 H15 118.3 . . ?
C6 O16 C17 114.52(12) . . ?
O16 C17 H17A 110.1 . . ?
O16 C17 H17B 110.1 . . ?
O16 C17 C18 108.23(13) . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
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 . . ?
C9 C19 H19A 108.4 . . ?
C9 C19 H19B 108.4 . . ?
C9 C19 H19C 110.3 . . ?
C9 C19 H19D 110.3 . . ?
C9 C19 C20A 107.0(3) . . ?
H19A C19 H19B 107.5 . . ?
H19C C19 H19D 108.6 . . ?
C20 C19 C9 115.47(17) . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
C20A C19 H19C 110.3 . . ?
C20A C19 H19D 110.3 . . ?
C19 C20 H20 117.7 . . ?
C21 C20 C19 124.7(3) . . ?
C21 C20 H20 117.7 . . ?
C19 C20A H20A 119.4 . . ?
C19 C20A H20B 121.8 . . ?
C21A C20A C19 121.2(9) . . ?
C21A C20A H20A 119.4 . . ?
C21B C20A C19 116.3(11) . . ?
C21B C20A H20B 121.8 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C20A C21A H21C 120.0 . . ?
C20A C21A H21D 120.0 . . ?
H21C C21A H21D 120.0 . . ?
C20A C21B H21E 120.0 . . ?
C20A C21B H21F 120.0 . . ?
H21E C21B H21F 120.0 . . ?
C23 C22 C12 121.20(13) . . ?
C27 C22 C12 120.19(13) . . ?
C27 C22 C23 118.60(14) . . ?
C24 C23 C22 119.71(14) . . ?
O28 C23 C22 115.42(12) . . ?
O28 C23 C24 124.83(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.94(15) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.1 . . ?
C24 C25 C26 121.83(15) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C27 117.49(16) . . ?
C25 C26 C30 117.4(9) . . ?
C25 C26 C30A 131.8(5) . . ?
C25 C26 C30B 119(2) . . ?
C27 C26 C30 125.0(9) . . ?
C27 C26 C30A 110.7(5) . . ?
C27 C26 C30B 123(2) . . ?
C22 C27 C26 122.39(15) . . ?
C22 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C23 O28 C29 117.39(12) . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 H30A 107.3 . . ?
C26 C30 H30B 107.3 . . ?
H30A C30 H30B 106.9 . . ?
C31 C30 C26 120.0(8) . . ?
C31 C30 H30A 107.3 . . ?
C31 C30 H30B 107.3 . . ?
C26 C30A H30C 108.3 . . ?
C26 C30A H30D 108.3 . . ?
H30C C30A H30D 107.4 . . ?
C31A C30A C26 116.0(8) . . ?
C31A C30A H30C 108.3 . . ?
C31A C30A H30D 108.3 . . ?
C26 C30B H30E 110.3 . . ?
C26 C30B H30F 110.3 . . ?
H30E C30B H30F 108.5 . . ?
C31B C30B C26 107.3(12) . . ?
C31B C30B H30E 110.3 . . ?
C31B C30B H30F 110.3 . . ?
C30 C31 H31 116.2 . . ?
C32 C31 C30 127.5(5) . . ?
C32 C31 H31 116.2 . . ?
C30A C31A H31A 114.6 . . ?
C32A C31A C30A 130.8(8) . . ?
C32A C31A H31A 114.6 . . ?
C30B C31B H31B 126.3 . . ?
C32B C31B C30B 107(2) . . ?
C32B C31B H31B 126.3 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
C31A C32A H32C 120.0 . . ?
C31A C32A H32D 120.0 . . ?
H32C C32A H32D 120.0 . . ?
C31B C32B H32E 120.0 . . ?
C31B C32B H32F 120.0 . . ?
H32E C32B H32F 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 3.8(2) . . . . ?
O1 C2 C3 C10 -178.95(13) . . . . ?
O1 C2 C7 C8 -179.84(13) . . . . ?
O1 C6 O16 C17 65.95(16) . . . . ?
C2 O1 C6 C5 -52.44(15) . . . . ?
C2 O1 C6 O16 68.45(15) . . . . ?
C2 C3 C4 C5 5.43(17) . . . . ?
C2 C3 C4 C11 122.22(14) . . . . ?
C2 C3 C4 C15 -115.81(14) . . . . ?
C2 C3 C10 C9 -1.7(2) . . . . ?
C2 C7 C8 C9 -1.1(2) . . . . ?
C3 C2 C7 C8 -1.0(2) . . . . ?
C3 C4 C5 C6 -36.71(16) . . . . ?
C3 C4 C11 C12 118.48(15) . . . . ?
C3 C4 C15 C14 -118.15(15) . . . . ?
C4 C3 C10 C9 175.69(13) . . . . ?
C4 C5 C6 O1 62.05(15) . . . . ?
C4 C5 C6 O16 -60.22(15) . . . . ?
C4 C11 C12 C13 0.4(2) . . . . ?
C4 C11 C12 C22 -175.51(13) . . . . ?
C5 C4 C11 C12 -124.48(15) . . . . ?
C5 C4 C15 C14 121.54(14) . . . . ?
C5 C6 O16 C17 -172.14(12) . . . . ?
C6 O1 C2 C3 20.40(18) . . . . ?
C6 O1 C2 C7 -160.78(13) . . . . ?
C6 O16 C17 C18 -174.67(14) . . . . ?
C7 C2 C3 C4 -175.02(13) . . . . ?
C7 C2 C3 C10 2.3(2) . . . . ?
C7 C8 C9 C10 1.7(2) . . . . ?
C7 C8 C9 C19 -179.29(16) . . . . ?
C8 C9 C10 C3 -0.3(2) . . . . ?
C8 C9 C19 C20 37.5(3) . . . . ?
C8 C9 C19 C20A 78.2(4) . . . . ?
C9 C19 C20 C21 -123.0(3) . . . . ?
C9 C19 C20A C21A -101.0(8) . . . . ?
C9 C19 C20A C21B 133.6(7) . . . . ?
C10 C3 C4 C5 -171.81(12) . . . . ?
C10 C3 C4 C11 -55.02(16) . . . . ?
C10 C3 C4 C15 66.95(16) . . . . ?
C10 C9 C19 C20 -143.47(19) . . . . ?
C10 C9 C19 C20A -102.8(4) . . . . ?
C11 C4 C5 C6 -152.68(12) . . . . ?
C11 C4 C15 C14 1.05(19) . . . . ?
C11 C12 C13 C14 3.71(18) . . . . ?
C11 C12 C13 O33 -173.76(13) . . . . ?
C11 C12 C22 C23 -117.36(15) . . . . ?
C11 C12 C22 C27 61.19(19) . . . . ?
C12 C13 C14 C15 -5.54(19) . . . . ?
C12 C22 C23 C24 176.85(13) . . . . ?
C12 C22 C23 O28 -1.05(19) . . . . ?
C12 C22 C27 C26 -177.69(15) . . . . ?
C13 C12 C22 C23 66.69(18) . . . . ?
C13 C12 C22 C27 -114.76(15) . . . . ?
C13 C14 C15 C4 3.1(2) . . . . ?
C15 C4 C5 C6 84.82(14) . . . . ?
C15 C4 C11 C12 -2.9(2) . . . . ?
C19 C9 C10 C3 -179.34(14) . . . . ?
C22 C12 C13 C14 179.70(12) . . . . ?
C22 C12 C13 O33 2.23(19) . . . . ?
C22 C23 C24 C25 0.9(2) . . . . ?
C22 C23 O28 C29 -178.02(13) . . . . ?
C23 C22 C27 C26 0.9(2) . . . . ?
C23 C24 C25 C26 0.9(3) . . . . ?
C24 C23 O28 C29 4.2(2) . . . . ?
C24 C25 C26 C27 -1.7(3) . . . . ?
C24 C25 C26 C30 175.8(5) . . . . ?
C24 C25 C26 C30A -179.5(7) . . . . ?
C24 C25 C26 C30B -178.9(8) . . . . ?
C25 C26 C27 C22 0.8(3) . . . . ?
C25 C26 C30 C31 -57.4(18) . . . . ?
C25 C26 C30A C31A -123.1(8) . . . . ?
C25 C26 C30B C31B -93(3) . . . . ?
C26 C30 C31 C32 -6(2) . . . . ?
C26 C30A C31A C32A 122.0(10) . . . . ?
C26 C30B C31B C32B 87(3) . . . . ?
C27 C22 C23 C24 -1.7(2) . . . . ?
C27 C22 C23 O28 -179.63(13) . . . . ?
C27 C26 C30 C31 119.9(14) . . . . ?
C27 C26 C30A C31A 59.0(12) . . . . ?
C27 C26 C30B C31B 90(3) . . . . ?
O28 C23 C24 C25 178.56(14) . . . . ?
C30 C26 C27 C22 -176.5(6) . . . . ?
C30A C26 C27 C22 179.1(6) . . . . ?
C30B C26 C27 C22 177.8(8) . . . . ?
O33 C13 C14 C15 171.93(13) . . . . ?

_olex2_date_sample_data_collection 2017-10-23
_olex2_date_sample_submission    2017-10-20
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
# This is the default assumed mounting details'
_olex2_submission_original_sample_id RA-235-002
_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 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.868
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
####################################################################### 
# 
# 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_42a
_database_code_depnum_ccdc_archive 'CCDC 2327693'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDC
_nottingham_internal_coll_number 17201
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   23/08/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 17/11/2017
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 17/11/2017
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 17/11/2017
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 10/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 10/2/2018
_refine_special_details          ?
_audit_creation_date             2018-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Br O3'
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 Br O'
_chemical_oxdiff_usercomment     
'REARDC #17201 SN-1190 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0694(3)
_cell_length_b                   10.5320(3)
_cell_length_c                   17.2799(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.156(3)
_cell_angle_gamma                90
_cell_volume                     1624.70(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4257
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2860
_cell_measurement_theta_min      4.1770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.215
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 5 -7 0.1929
-2 -6 1 0.2119
-2 -6 -3 0.2456
2 6 4 0.3657
-2 -6 6 0.2624
5 -3 -4 0.2004
-5 3 1 0.1839
2 -2 -11 0.3654
4 -2 6 0.3092
0 0 11 0.2544
5 2 -6 0.2322
1 1 10 0.2660
-5 -2 -1 0.2427
-3 -2 -8 0.3183
5 2 3 0.3057
-3 5 -4 0.1418
3 -6 0 0.2278
3 -6 -4 0.2530
6 -2 -3 0.1796

_exptl_crystal_size_max          0.719
_exptl_crystal_size_mid          0.486
_exptl_crystal_size_min          0.412
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
1.9946 4.9922 -6.9972 -0.7868 -0.3201 0.5049
-1.9973 -5.9923 0.9995 0.8850 0.3148 0.0490
-1.9990 -5.9933 -2.9990 0.8534 0.3140 0.4097
1.9995 5.9936 3.9986 -0.8456 -0.3138 -0.4998
-1.9952 -5.9910 5.9975 0.9244 0.3158 -0.4019
4.9897 -2.9935 -3.9990 0.3933 -0.8605 0.2424
-4.9910 2.9928 1.0002 -0.4170 0.8599 0.0281
1.9917 -1.9987 -10.9960 0.1996 -0.3493 0.9548
3.9958 -1.9930 5.9972 0.3290 -0.6850 -0.6408
0.0047 0.0029 10.9957 0.0867 0.0022 -0.9920
4.9897 1.9987 -5.9980 -0.3495 -0.8406 0.3590
1.0028 1.0018 9.9961 -0.0689 -0.1635 -0.9458
-4.9927 -2.0005 -0.9993 0.2944 0.8392 0.2722
-2.9989 -2.0011 -7.9967 0.2346 0.4988 0.8409
4.9936 2.0010 2.9985 -0.2786 -0.8388 -0.4526
-2.9961 4.9898 -3.9980 -0.7518 0.5281 0.3909
2.9942 -5.9894 -0.0005 0.8657 -0.5329 -0.0174
2.9925 -5.9905 -3.9990 0.8342 -0.5337 0.3433
5.9887 -1.9941 -2.9994 0.2535 -1.0258 0.1082

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6146
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.449
_diffrn_reflns_theta_min         4.939
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        
'flash frozen in gaseous N2' # assumed default, please check
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  86.00   1.00    1.00    --  106.13 -30.00   0.00   35
  2  ω     54.00  89.00   1.00    1.00    --  106.13 -45.00  90.00   35
  3  ω     38.00 109.00   1.00    1.00    --  106.13 -95.00 120.00   71
  4  ω     50.00  83.00   1.00    1.00    --   43.32 -99.00  30.00   33
  5  ω     55.00  91.00   1.00    1.00    --  106.13 -30.00 -90.00   36
  6  ω     65.00  90.00   1.00    1.00    --  106.13 -30.00-180.00   25
  7  ω     50.00  89.00   1.00    1.00    --  106.13 -45.00-180.00   39
  8  ω     39.00 104.00   1.00    1.00    --  106.13 -95.00-150.00   65
  9  ω     31.00  85.00   1.00    1.00    --  106.13 -30.00-120.00   54
 10  ω     32.00  82.00   1.00    1.00    --  106.13 -30.00 -30.00   50
 11  ω    -49.00  31.00   1.00    1.00    --  -38.50  38.00-150.00   80
 12  ω    -61.00 -12.00   1.00    1.00    --  -38.50 -57.00  30.00   49
 13  ω    -37.00  33.00   1.00    1.00    --  -38.50  38.00 -90.00   70
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'MiTeGen micromount' # assumed default, please check
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0021901000
_diffrn_orient_matrix_UB_12      -0.1456334000
_diffrn_orient_matrix_UB_13      0.0079238000
_diffrn_orient_matrix_UB_21      -0.1697838000
_diffrn_orient_matrix_UB_22      0.0041016000
_diffrn_orient_matrix_UB_23      0.0002696000
_diffrn_orient_matrix_UB_31      -0.0313630000
_diffrn_orient_matrix_UB_32      -0.0127608000
_diffrn_orient_matrix_UB_33      -0.0901961000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3110
_reflns_number_total             3197
_reflns_odcompleteness_completeness 99.81
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.104
_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)+(0.0465P)²+0.7565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0785
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.56198(16) 0.34726(13) 0.54587(8) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.5006(2) 0.22371(19) 0.52656(11) 0.0177(4) Uani 1 1 d . . . . .
H2 H 0.388936 0.231296 0.514801 0.021 Uiso 1 1 calc R . . . .
C3 C 0.5421(2) 0.13298(19) 0.59470(11) 0.0182(4) Uani 1 1 d . . . . .
H3A H 0.497142 0.048954 0.579595 0.022 Uiso 1 1 calc R . . . .
H3B H 0.499120 0.164364 0.639940 0.022 Uiso 1 1 calc R . . . .
C4 C 0.7140(2) 0.11705(17) 0.62044(11) 0.0149(4) Uani 1 1 d . . . . .
C5 C 0.7900(2) 0.24698(17) 0.61642(10) 0.0147(4) Uani 1 1 d . . . . .
C6 C 0.9391(2) 0.26358(18) 0.65036(10) 0.0162(4) Uani 1 1 d . . . . .
H6 H 0.992612 0.193832 0.676568 0.019 Uiso 1 1 calc R . . . .
C7 C 1.0134(2) 0.37875(19) 0.64739(11) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.9331(2) 0.47961(18) 0.60764(11) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.981491 0.558929 0.604302 0.026 Uiso 1 1 calc R . . . .
C9 C 0.7844(2) 0.46573(18) 0.57310(11) 0.0203(4) Uani 1 1 d . . . . .
H9 H 0.731544 0.535127 0.546123 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7121(2) 0.35001(18) 0.57784(11) 0.0161(4) Uani 1 1 d . . . . .
C11 C 0.7774(2) 0.02794(17) 0.56624(10) 0.0142(3) Uani 1 1 d . . . . .
H11 H 0.764291 0.048434 0.511922 0.017 Uiso 1 1 calc R . . . .
C12 C 0.8507(2) -0.07776(17) 0.59095(10) 0.0143(3) Uani 1 1 d . . . . .
C13 C 0.8748(2) -0.12142(18) 0.67368(11) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.8135(2) -0.03744(19) 0.72766(11) 0.0193(4) Uani 1 1 d . . . . .
H14 H 0.825191 -0.060434 0.781562 0.023 Uiso 1 1 calc R . . . .
C15 C 0.7419(2) 0.07015(18) 0.70398(11) 0.0175(4) Uani 1 1 d . . . . .
H15 H 0.706107 0.120446 0.742399 0.021 Uiso 1 1 calc R . . . .
O16 O 0.54848(16) 0.17440(12) 0.46010(9) 0.0176(3) Uani 1 1 d . . . . .
C17 C 0.4950(2) 0.2420(2) 0.38798(11) 0.0210(4) Uani 1 1 d . . . . .
H17A H 0.394204 0.276583 0.389834 0.025 Uiso 1 1 calc R . . . .
H17B H 0.485298 0.181652 0.343429 0.025 Uiso 1 1 calc R . . . .
C18 C 0.5969(3) 0.3493(2) 0.37354(13) 0.0276(5) Uani 1 1 d . . . . .
H18A H 0.588131 0.418974 0.410053 0.041 Uiso 1 1 calc GR . . . .
H18B H 0.567965 0.379551 0.319354 0.041 Uiso 1 1 calc GR . . . .
H18C H 0.700671 0.319119 0.381835 0.041 Uiso 1 1 calc GR . . . .
Br19 Br 0.93171(2) -0.18300(2) 0.51944(2) 0.01712(10) Uani 1 1 d . . . . .
O20 O 0.93961(17) -0.22040(14) 0.69547(9) 0.0240(3) Uani 1 1 d . . . . .
C21 C 1.1750(2) 0.3961(2) 0.68667(13) 0.0241(4) Uani 1 1 d . . . . .
H21A H 1.214548 0.314299 0.709798 0.029 Uiso 1 1 calc R . . . .
H21B H 1.235292 0.421011 0.646617 0.029 Uiso 1 1 calc R . . . .
C22 C 1.1915(2) 0.4959(2) 0.75036(12) 0.0236(4) Uani 1 1 d . . . . .
H22 H 1.148756 0.576992 0.736865 0.028 Uiso 1 1 calc R . . . .
C23 C 1.2610(2) 0.4788(2) 0.82341(13) 0.0287(5) Uani 1 1 d . . . . .
H23A H 1.305134 0.398923 0.839101 0.034 Uiso 1 1 calc R . . . .
H23B H 1.266807 0.546249 0.860299 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
O1 C2 1.431(2) . ?
O1 C10 1.376(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.512(3) . ?
C2 O16 1.398(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.553(3) . ?
C4 C5 1.539(3) . ?
C4 C11 1.510(2) . ?
C4 C15 1.504(2) . ?
C5 C6 1.388(3) . ?
C5 C10 1.398(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(3) . ?
C7 C8 1.398(3) . ?
C7 C21 1.514(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.328(3) . ?
C12 C13 1.481(3) . ?
C12 Br19 1.9014(18) . ?
C13 C14 1.464(3) . ?
C13 O20 1.223(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.334(3) . ?
C15 H15 0.9500 . ?
O16 C17 1.443(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.508(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.510(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.320(3) . ?
C23 H23A 0.9500 . ?
C23 H23B 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
C10 O1 C2 115.43(14) . . ?
O1 C2 H2 108.2 . . ?
O1 C2 C3 111.08(15) . . ?
C3 C2 H2 108.2 . . ?
O16 C2 O1 111.39(15) . . ?
O16 C2 H2 108.2 . . ?
O16 C2 C3 109.52(15) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 113.04(15) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 C4 C3 109.02(15) . . ?
C11 C4 C3 111.26(15) . . ?
C11 C4 C5 107.58(14) . . ?
C15 C4 C3 107.51(15) . . ?
C15 C4 C5 109.53(15) . . ?
C15 C4 C11 111.91(15) . . ?
C6 C5 C4 120.26(17) . . ?
C6 C5 C10 118.47(17) . . ?
C10 C5 C4 121.26(17) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.40(18) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 117.84(18) . . ?
C6 C7 C21 121.65(18) . . ?
C8 C7 C21 120.50(18) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.02(18) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.03(18) . . ?
C10 C9 H9 120.0 . . ?
O1 C10 C5 123.77(17) . . ?
O1 C10 C9 115.94(17) . . ?
C9 C10 C5 120.23(18) . . ?
C4 C11 H11 118.5 . . ?
C12 C11 C4 123.07(16) . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C13 123.45(17) . . ?
C11 C12 Br19 120.57(14) . . ?
C13 C12 Br19 115.98(13) . . ?
C14 C13 C12 114.79(16) . . ?
O20 C13 C12 122.90(18) . . ?
O20 C13 C14 122.31(17) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.46(17) . . ?
C15 C14 H14 118.8 . . ?
C4 C15 H15 117.8 . . ?
C14 C15 C4 124.31(17) . . ?
C14 C15 H15 117.8 . . ?
C2 O16 C17 114.87(15) . . ?
O16 C17 H17A 109.0 . . ?
O16 C17 H17B 109.0 . . ?
O16 C17 C18 112.97(16) . . ?
H17A C17 H17B 107.8 . . ?
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 . . ?
C7 C21 H21A 109.2 . . ?
C7 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C7 111.99(17) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22 117.6 . . ?
C23 C22 C21 124.8(2) . . ?
C23 C22 H22 117.6 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -59.2(2) . . . . ?
O1 C2 O16 C17 -66.1(2) . . . . ?
C2 O1 C10 C5 -23.2(2) . . . . ?
C2 O1 C10 C9 159.65(16) . . . . ?
C2 C3 C4 C5 39.4(2) . . . . ?
C2 C3 C4 C11 -79.11(19) . . . . ?
C2 C3 C4 C15 158.04(16) . . . . ?
C2 O16 C17 C18 88.7(2) . . . . ?
C3 C2 O16 C17 170.65(15) . . . . ?
C3 C4 C5 C6 167.76(16) . . . . ?
C3 C4 C5 C10 -13.2(2) . . . . ?
C3 C4 C11 C12 -121.25(19) . . . . ?
C3 C4 C15 C14 122.2(2) . . . . ?
C4 C5 C6 C7 179.15(16) . . . . ?
C4 C5 C10 O1 4.8(3) . . . . ?
C4 C5 C10 C9 -178.22(16) . . . . ?
C4 C11 C12 C13 1.6(3) . . . . ?
C4 C11 C12 Br19 -178.41(13) . . . . ?
C5 C4 C11 C12 119.41(19) . . . . ?
C5 C4 C15 C14 -119.4(2) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C21 178.32(17) . . . . ?
C6 C5 C10 O1 -176.21(16) . . . . ?
C6 C5 C10 C9 0.8(3) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C21 C22 -117.9(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C7 C21 C22 C23 127.1(2) . . . . ?
C8 C7 C21 C22 61.2(2) . . . . ?
C8 C9 C10 O1 176.26(17) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
C10 O1 C2 C3 49.5(2) . . . . ?
C10 O1 C2 O16 -72.86(19) . . . . ?
C10 C5 C6 C7 0.1(3) . . . . ?
C11 C4 C5 C6 -71.5(2) . . . . ?
C11 C4 C5 C10 107.55(19) . . . . ?
C11 C4 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C11 C12 C13 O20 178.32(19) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C4 0.7(3) . . . . ?
C15 C4 C5 C6 50.4(2) . . . . ?
C15 C4 C5 C10 -130.60(18) . . . . ?
C15 C4 C11 C12 -1.0(3) . . . . ?
O16 C2 C3 C4 64.2(2) . . . . ?
Br19 C12 C13 C14 179.00(13) . . . . ?
Br19 C12 C13 O20 -1.6(3) . . . . ?
O20 C13 C14 C15 -179.52(19) . . . . ?
C21 C7 C8 C9 -178.50(18) . . . . ?

_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
# This is the default assumed mounting details'
_olex2_submission_original_sample_id RA-174-002
_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.817
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
####################################################################### 
# 
# 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_34
_database_code_depnum_ccdc_archive 'CCDC 2327692'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDJ
_nottingham_internal_coll_number 17781
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time 1.00
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   09/07/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017-09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 09/07/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 9/7/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 9/7/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 9/7/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 9/7/2018
_refine_special_details          ?
_audit_creation_date             2018-07-09
_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         'C18 H17 Br O2'
_chemical_formula_sum            'C18 H17 Br O2'
_chemical_formula_weight         345.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 Br O2'
_chemical_oxdiff_usercomment     
'REARDJ #17781 SN-1362 IN FOMBLIN FILM ON MICROOUNT FOR REA/RD'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   17.6068(5)
_cell_length_b                   7.4294(2)
_cell_length_c                   12.3043(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.692(3)
_cell_angle_gamma                90
_cell_volume                     1524.62(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17249
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3420
_cell_measurement_theta_min      3.8030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.683
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.144
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.1189
1 0 0 0.1139
1 0 -2 0.2897
-1 0 2 0.2537
1 2 0 0.2801
-1 -2 0 0.2625
-2 0 -5 0.2508
-5 0 2 0.2016
5 -3 0 0.2820
5 4 -2 0.2949
-5 2 7 0.3221

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.601
_exptl_crystal_size_mid          0.543
_exptl_crystal_size_min          0.233
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
-1.0000 0.0000 -0.0000 -0.0045 -0.0895 0.0222
1.0000 -0.0000 0.0000 0.0045 0.0895 -0.0222
1.0000 0.0000 -2.0000 -0.2379 0.0370 0.0693
-1.0000 -0.0000 2.0000 0.2379 -0.0370 -0.0693
1.0000 2.0000 0.0000 0.1303 0.1783 0.3629
-1.0000 -2.0000 -0.0000 -0.1303 -0.1783 -0.3629
-2.0000 0.0000 -5.0000 -0.6150 -0.3105 0.2730
-5.0000 0.0000 2.0000 0.2199 -0.3952 0.0195
5.0000 -3.0000 -0.0000 -0.1663 0.3146 -0.6885
5.0000 4.0000 -2.0000 0.0317 0.5728 0.7506
-5.0000 2.0000 7.0000 0.9518 -0.1750 0.1759

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.554
_diffrn_reflns_theta_min         5.304
_diffrn_ambient_environment      'N2 gas'
_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 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -20.00   1.00    1.00    --  -38.50 -38.00-180.00   87
  2  ω    -48.00  28.00   1.00    1.00    --  -38.50  38.00   0.00   76
  3  ω     21.00  54.00   1.00    1.00    --   43.13  57.00-180.00   33
  4  ω     22.00 100.00   1.00    1.00    --   43.13  57.00  30.00   78
  5  ω     26.00 112.00   1.00    1.00    --   43.13  57.00  90.00   86
  6  ω     43.00  96.00   1.00    1.00    --   43.13-125.00 -30.00   53
  7  ω     76.00 102.00   1.00    1.00    --  106.13  77.00 -30.00   26
  8  ω     36.00  63.00   1.00    1.00    --  106.13 -30.00 -60.00   27
  9  ω     49.00  91.00   1.00    1.00    --  106.13 -30.00-120.00   42
 10  ω     75.00 100.00   1.00    1.00    --  106.13  77.00   0.00   25
 11  ω     36.00  92.00   1.00    1.00    --  106.13 -45.00-180.00   56
 12  ω     75.00 101.00   1.00    1.00    --  106.13  77.00  60.00   26
 13  ω    116.00 172.00   1.00    1.00    --  106.13  77.00  60.00   56
 14  ω     66.00 117.00   1.00    1.00    --  106.13-125.00   0.00   51
 15  ω     79.00 105.00   1.00    1.00    --  106.13  61.00   0.00   26
 16  ω     80.00 111.00   1.00    1.00    --  106.13  61.00  90.00   31
 17  ω     79.00 119.00   1.00    1.00    --  106.13  61.00  60.00   40
 18  ω     80.00 106.00   1.00    1.00    --  106.13  61.00  30.00   26
 19  ω     41.00  85.00   1.00    1.00    --  106.13 -30.00 -30.00   44
 20  ω     79.00 105.00   1.00    1.00    --  106.13  61.00 -30.00   26
 21  ω     75.00 120.00   1.00    1.00    --  106.13  77.00  90.00   45
 22  ω    108.00 177.00   1.00    1.00    --  106.13 107.00 135.00   69
 23  ω    114.00 177.00   1.00    1.00    --  106.13  77.00 -30.00   63
 24  ω     83.00 116.00   1.00    1.00    --  106.13  45.00  60.00   33
 25  ω     89.00 121.00   1.00    1.00    --  106.13  45.00 -30.00   32
 26  ω     82.00 112.00   1.00    1.00    --  106.13  45.00  90.00   30
 27  ω     75.00 100.00   1.00    1.00    --  106.13  77.00  30.00   25
 28  ω     83.00 108.00   1.00    1.00    --  106.13  45.00   0.00   25
 29  ω     83.00 109.00   1.00    1.00    --  106.13  45.00  30.00   26
 30  ω    116.00 175.00   1.00    1.00    --  106.13  45.00  30.00   59
 31  ω     27.00  82.00   1.00    1.00    --  106.13 -95.00  90.00   55
 32  ω    128.00 177.00   1.00    1.00    --  106.13  45.00 -60.00   49
 33  ω    -29.00  19.00   1.00    1.00    --  -38.50  38.00 -90.00   48
 34  ω    -61.00  28.00   1.00    1.00    --  -38.50  57.00-180.00   89
 35  ω     13.00  84.00   1.00    1.00    --   43.13  77.00 -60.00   71
 36  ω     12.00  67.00   1.00    1.00    --   43.13  77.00  90.00   55
 37  ω     14.00  40.00   1.00    1.00    --   43.13  77.00  30.00   26
 38  ω     20.00  47.00   1.00    1.00    --   43.13  77.00-120.00   27
 39  ω     57.00 110.00   1.00    1.00    --   43.13  77.00-120.00   53
 40  ω      9.00  55.00   1.00    1.00    --   43.13 -99.00  60.00   46
 41  ω     68.00 102.00   1.00    1.00    --   43.13  77.00-180.00   34
 42  ω     13.00  54.00   1.00    1.00    --   43.13  77.00-180.00   41
 43  ω     79.00 105.00   1.00    1.00    --  106.13  61.00 120.00   26
 44  ω     79.00 111.00   1.00    1.00    --  106.13  61.00 -90.00   32
 45  ω     75.00 178.00   1.00    1.00    --  106.13  77.00-120.00  103
 46  ω     55.00  81.00   1.00    1.00    --  106.13 -95.00  60.00   26
 47  ω     75.00 101.00   1.00    1.00    --  106.13  77.00-180.00   26
 48  ω     66.00 136.00   1.00    1.00    --  106.13 -77.00-180.00   70
 49  ω     79.00 147.00   1.00    1.00    --  106.13  61.00-150.00   68
 50  ω     34.00  62.00   1.00    1.00    --  106.13 -77.00-180.00   28
 51  ω     79.00 133.00   1.00    1.00    --  106.13  61.00 150.00   54
 52  ω     82.00 127.00   1.00    1.00    --  106.13  61.00-180.00   45
 53  ω     81.00 124.00   1.00    1.00    --  106.13  61.00-120.00   43
 54  ω     75.00 101.00   1.00    1.00    --  106.13  77.00 150.00   26
 55  ω    148.00 174.00   1.00    1.00    --  106.13  61.00 -60.00   26
 56  ω     80.00 106.00   1.00    1.00    --  106.13  61.00 -60.00   26
 57  ω     82.00 108.00   1.00    1.00    --  106.13 -95.00  60.00   26
 58  ω     75.00 101.00   1.00    1.00    --  106.13  77.00-150.00   26
 59  ω     76.00 102.00   1.00    1.00    --  106.13  77.00 120.00   26
 60  ω    150.00 176.00   1.00    1.00    --  106.13  77.00 120.00   26
 61  ω    111.00 137.00   1.00    1.00    --  106.13  61.00 120.00   26
 62  ω     75.00 130.00   1.00    1.00    --  106.13  77.00 -90.00   55
 63  ω     36.00 106.00   1.00    1.00    --  106.13 -95.00 150.00   70
;
_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      0.0044965000
_diffrn_orient_matrix_UB_12      0.0629202000
_diffrn_orient_matrix_UB_13      0.1212106000
_diffrn_orient_matrix_UB_21      0.0895497000
_diffrn_orient_matrix_UB_22      0.0443941000
_diffrn_orient_matrix_UB_23      0.0262782000
_diffrn_orient_matrix_UB_31      -0.0221851000
_diffrn_orient_matrix_UB_32      0.1925200000
_diffrn_orient_matrix_UB_33      -0.0457253000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3072
_reflns_number_total             3083
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.188
_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)+(0.0343P)²+1.4451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0751
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C16(H16), C19(H19)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.25240(8) 0.58920(18) 0.27528(11) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.21327(10) 0.6819(3) 0.17765(15) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.24203(10) 0.8537(3) 0.17382(16) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.31135(11) 0.8848(2) 0.28403(16) 0.0154(4) Uani 1 1 d . . . . .
C5 C 0.29973(10) 0.7228(3) 0.35686(15) 0.0147(3) Uani 1 1 d . . . . .
H5 H 0.268687 0.763361 0.407708 0.018 Uiso 1 1 calc R . . . .
C6 C 0.15073(11) 0.6150(2) 0.08733(17) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.11689(11) 0.7234(3) -0.00750(16) 0.0182(4) Uani 1 1 d . . . . .
H7 H 0.073493 0.678838 -0.069554 0.022 Uiso 1 1 calc R . . . .
C8 C 0.14552(11) 0.8966(3) -0.01323(16) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.20933(10) 0.9617(3) 0.07804(16) 0.0162(4) Uani 1 1 d . . . . .
H9 H 0.230197 1.078726 0.074687 0.019 Uiso 1 1 calc R . . . .
C10 C 0.38786(11) 0.8697(3) 0.25387(16) 0.0183(4) Uani 1 1 d . . . . .
H10 H 0.400161 0.964508 0.210433 0.022 Uiso 1 1 calc R . . . .
C11 C 0.43916(11) 0.7331(3) 0.28385(16) 0.0209(4) Uani 1 1 d . . . . .
H11 H 0.483491 0.729867 0.255734 0.025 Uiso 1 1 calc R . . . .
C12 C 0.42967(11) 0.5867(3) 0.35908(16) 0.0182(4) Uani 1 1 d . . . . .
C13 C 0.37508(11) 0.6274(3) 0.42881(16) 0.0170(4) Uani 1 1 d . . . . .
H13A H 0.403813 0.704096 0.495024 0.020 Uiso 1 1 calc R . . . .
H13B H 0.360332 0.513685 0.458900 0.020 Uiso 1 1 calc R . . . .
Br14 Br 0.11248(2) 0.37919(3) 0.09427(2) 0.02313(9) Uani 1 1 d . . . . .
C15 C 0.10613(11) 1.0086(3) -0.11954(16) 0.0211(4) Uani 1 1 d . . . . .
H15A H 0.135298 1.123994 -0.113473 0.025 Uiso 1 1 calc R . . . .
H15B H 0.110324 0.943920 -0.187742 0.025 Uiso 1 1 calc R . . . .
C16 C 0.01957(11) 1.0466(3) -0.13580(16) 0.0193(4) Uani 1 1 d . . . . .
H16 H 0.007752 1.120693 -0.080346 0.023 Uiso 1 1 calc R . . . .
C17 C -0.04131(12) 0.9856(3) -0.22082(18) 0.0251(4) Uani 1 1 d . . . . .
H17A H -0.032005 0.911135 -0.278032 0.030 Uiso 1 1 calc R . . . .
H17B H -0.094586 1.015997 -0.225006 0.030 Uiso 1 1 calc R . . . .
C18 C 0.30448(12) 1.0675(3) 0.34009(17) 0.0206(4) Uani 1 1 d . . . . .
H18A H 0.311319 1.165559 0.289518 0.025 Uiso 1 1 calc R . . . .
H18B H 0.249969 1.078478 0.346257 0.025 Uiso 1 1 calc R . . . .
C19 C 0.36496(13) 1.0918(3) 0.45721(18) 0.0236(4) Uani 1 1 d . . . . .
H19 H 0.419705 1.103916 0.462299 0.028 Uiso 1 1 calc R . . . .
C20 C 0.34711(16) 1.0972(3) 0.5533(2) 0.0313(5) Uani 1 1 d . . . . .
H20A H 0.292946 1.085498 0.551286 0.038 Uiso 1 1 calc R . . . .
H20B H 0.388395 1.112929 0.624560 0.038 Uiso 1 1 calc R . . . .
O21 O 0.46509(9) 0.4447(2) 0.36607(12) 0.0269(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.364(2) . ?
O1 C5 1.467(2) . ?
C2 C3 1.379(3) . ?
C2 C6 1.382(3) . ?
C3 C4 1.524(2) . ?
C3 C9 1.389(3) . ?
C4 C5 1.553(2) . ?
C4 C10 1.512(3) . ?
C4 C18 1.545(3) . ?
C5 H5 1.0000 . ?
C5 C13 1.514(2) . ?
C6 C7 1.385(3) . ?
C6 Br14 1.8885(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(3) . ?
C8 C9 1.396(3) . ?
C8 C15 1.517(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.330(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.472(3) . ?
C12 C13 1.510(3) . ?
C12 O21 1.214(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.499(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.315(3) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.503(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.318(3) . ?
C20 H20A 0.9500 . ?
C20 H20B 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
C2 O1 C5 106.05(14) . . ?
O1 C2 C3 114.20(16) . . ?
O1 C2 C6 125.00(17) . . ?
C3 C2 C6 120.80(17) . . ?
C2 C3 C4 107.97(16) . . ?
C2 C3 C9 120.44(17) . . ?
C9 C3 C4 131.55(17) . . ?
C3 C4 C5 100.35(14) . . ?
C3 C4 C18 112.08(15) . . ?
C10 C4 C3 107.03(15) . . ?
C10 C4 C5 112.13(15) . . ?
C10 C4 C18 112.23(15) . . ?
C18 C4 C5 112.32(15) . . ?
O1 C5 C4 106.31(14) . . ?
O1 C5 H5 109.1 . . ?
O1 C5 C13 106.39(15) . . ?
C4 C5 H5 109.1 . . ?
C13 C5 C4 116.58(15) . . ?
C13 C5 H5 109.1 . . ?
C2 C6 C7 118.99(17) . . ?
C2 C6 Br14 120.08(15) . . ?
C7 C6 Br14 120.93(14) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.00(17) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 119.38(17) . . ?
C7 C8 C15 118.52(17) . . ?
C9 C8 C15 122.09(18) . . ?
C3 C9 C8 119.36(18) . . ?
C3 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C4 C10 H10 117.7 . . ?
C11 C10 C4 124.61(17) . . ?
C11 C10 H10 117.7 . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.31(17) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 115.50(17) . . ?
O21 C12 C11 121.81(18) . . ?
O21 C12 C13 122.67(18) . . ?
C5 C13 H13A 109.4 . . ?
C5 C13 H13B 109.4 . . ?
C12 C13 C5 111.07(15) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C8 C15 H15A 109.1 . . ?
C8 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C8 112.51(15) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16 117.4 . . ?
C17 C16 C15 125.14(19) . . ?
C17 C16 H16 117.4 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C4 C18 H18A 108.8 . . ?
C4 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C4 113.60(17) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19 117.8 . . ?
C20 C19 C18 124.4(2) . . ?
C20 C19 H19 117.8 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 0.4(2) . . . . ?
O1 C2 C3 C9 178.18(16) . . . . ?
O1 C2 C6 C7 -179.30(16) . . . . ?
O1 C2 C6 Br14 0.8(3) . . . . ?
O1 C5 C13 C12 70.39(19) . . . . ?
C2 O1 C5 C4 -22.14(17) . . . . ?
C2 O1 C5 C13 -147.03(14) . . . . ?
C2 C3 C4 C5 -13.47(18) . . . . ?
C2 C3 C4 C10 103.69(17) . . . . ?
C2 C3 C4 C18 -132.86(16) . . . . ?
C2 C3 C9 C8 1.7(3) . . . . ?
C2 C6 C7 C8 0.7(3) . . . . ?
C3 C2 C6 C7 -0.2(3) . . . . ?
C3 C2 C6 Br14 179.84(13) . . . . ?
C3 C4 C5 O1 21.28(17) . . . . ?
C3 C4 C5 C13 139.65(16) . . . . ?
C3 C4 C10 C11 -108.0(2) . . . . ?
C3 C4 C18 C19 171.72(17) . . . . ?
C4 C3 C9 C8 178.92(18) . . . . ?
C4 C5 C13 C12 -47.9(2) . . . . ?
C4 C10 C11 C12 -5.2(3) . . . . ?
C4 C18 C19 C20 -111.5(2) . . . . ?
C5 O1 C2 C3 14.01(19) . . . . ?
C5 O1 C2 C6 -166.86(17) . . . . ?
C5 C4 C10 C11 1.1(3) . . . . ?
C5 C4 C18 C19 59.6(2) . . . . ?
C6 C2 C3 C4 -178.79(16) . . . . ?
C6 C2 C3 C9 -1.0(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C15 179.81(17) . . . . ?
C7 C8 C9 C3 -1.2(3) . . . . ?
C7 C8 C15 C16 62.8(2) . . . . ?
C8 C15 C16 C17 -114.0(2) . . . . ?
C9 C3 C4 C5 169.07(19) . . . . ?
C9 C3 C4 C10 -73.8(2) . . . . ?
C9 C3 C4 C18 49.7(3) . . . . ?
C9 C8 C15 C16 -117.4(2) . . . . ?
C10 C4 C5 O1 -92.03(17) . . . . ?
C10 C4 C5 C13 26.3(2) . . . . ?
C10 C4 C18 C19 -67.8(2) . . . . ?
C10 C11 C12 C13 -18.2(3) . . . . ?
C10 C11 C12 O21 163.50(19) . . . . ?
C11 C12 C13 C5 43.2(2) . . . . ?
Br14 C6 C7 C8 -179.37(14) . . . . ?
C15 C8 C9 C3 178.99(17) . . . . ?
C18 C4 C5 O1 140.49(15) . . . . ?
C18 C4 C5 C13 -101.13(19) . . . . ?
C18 C4 C10 C11 128.6(2) . . . . ?
O21 C12 C13 C5 -138.44(19) . . . . ?

loop_
_audit_author_email
pcxra5@nottingham.ac.uk
william.lewis@nottingham.ac.uk
''
_olex2_exptl_crystal_mounting_method 'in fomblin film on a Mitegen micromount'
_olex2_submission_original_sample_id RA-425-001
_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 4.380
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 2327690'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDH
_nottingham_internal_coll_number 17457
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 80.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/01/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 23/01/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 23/1/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 23/1/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 13/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/2/2018
_refine_special_details          ?
_audit_creation_date             2018-02-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 B2 O4'
_chemical_formula_sum            'C18 H18 B2 O4'
_chemical_formula_weight         319.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H18 B2 O4'
_chemical_oxdiff_usercomment     
'REARDH #17457 GVB-1442 IN FOMBLIN FILM ON MICROMOUNT FOR REA/RD'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.4184(9)
_cell_length_b                   4.96092(16)
_cell_length_c                   21.7474(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.804(3)
_cell_angle_gamma                90
_cell_volume                     3317.97(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1530
_cell_measurement_theta_min      4.5360
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.792
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0148
-1 0 1 0.0308
-1 -2 5 0.1554
-2 3 -1 0.1651
-1 0 0 0.0010
1 0 0 0.0177
1 -3 -1 0.1738

_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.019
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
0.9988 -0.0003 -0.9973 -0.0275 -0.0240 -0.0701
-0.9988 0.0003 0.9973 0.0275 0.0240 0.0701
-0.9951 -1.9985 5.0124 -0.4656 -0.0402 0.5411
-2.0069 2.9993 -1.0218 0.8608 0.0681 -0.3736
-0.9975 0.0002 -0.0048 0.0054 0.0494 0.0058
0.9975 -0.0002 0.0048 -0.0054 -0.0494 -0.0058
1.0119 -2.9993 -0.9872 -0.8995 0.0321 0.2509

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.746
_diffrn_reflns_theta_min         4.154
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        
'flash frozen in gaseous N2' # assumed default, please check
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.984
_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   20.00    --  -38.50  38.00 120.00   84
  2  ω    -90.00   2.00   1.00   20.00    --  -38.50 120.00 -54.00   92
  3  ω    -36.00  80.00   1.00   20.00    --   42.83 -19.00 -90.00  116
  4  ω     33.00 122.00   1.00   80.00    --  104.50-125.00 -90.00   89
  5  ω     33.00  98.00   1.00   80.00    --  104.50 -45.00  90.00   65
  6  ω     31.00 136.00   1.00   80.00    --  104.50 -77.00 -60.00  105
  7  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00 -60.00   61
  8  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00  30.00   61
  9  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00-180.00   61
 10  ω     73.00 178.00   1.00   80.00    --  104.50  77.00  60.00  105
 11  ω     30.00  91.00   1.00   80.00    --  104.50 -30.00 -30.00   61
 12  ω     16.00 113.00   1.00   20.00    --   42.83  57.00 120.00   97
 13  ω     16.00 113.00   1.00   20.00    --   42.83  57.00-120.00   97
 14  ω     11.00 117.00   1.00   20.00    --   42.83  77.00   0.00  106
 15  ω     81.00 178.00   1.00   80.00    --  104.50  30.00-120.00   97
 16  ω     81.00 178.00   1.00   80.00    --  104.50  30.00 150.00   97
 17  ω     77.00 175.00   1.00   80.00    --  104.50  61.00  30.00   98
 18  ω     80.00 176.00   1.00   80.00    --  104.50  45.00 -90.00   96
 19  ω     23.00 109.00   1.00   80.00    --  104.50 -94.00  90.00   86
 20  ω     59.00 178.00   1.00   80.00    --  104.50  15.00   0.00  119
 21  ω   -110.00 -55.00   1.00   20.00    --  -38.50-154.00  64.00   55
 22  ω    -94.00  -2.00   1.00   20.00    --  -38.50 125.00-180.00   92
 23  ω     11.00 117.00   1.00   20.00    --   42.83  77.00 -90.00  106
 24  ω     80.00 105.00   1.00   80.00    --  104.50  45.00-180.00   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'MiTeGen micromount' # assumed default, please check
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0054633000
_diffrn_orient_matrix_UB_12      0.2908389000
_diffrn_orient_matrix_UB_13      0.0219773000
_diffrn_orient_matrix_UB_21      -0.0494110000
_diffrn_orient_matrix_UB_22      -0.0190106000
_diffrn_orient_matrix_UB_23      -0.0254186000
_diffrn_orient_matrix_UB_31      -0.0061681000
_diffrn_orient_matrix_UB_32      -0.1068536000
_diffrn_orient_matrix_UB_33      0.0641253000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3014
_reflns_number_total             3296
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.151
_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)+(0.0859P)²+24.1703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2607
_refine_ls_wR_factor_ref         0.2630
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H14C)=Sof(H14D)=Sof(H16C)=Sof(H16D)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15)=Sof(H16A)=Sof(H16B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C14(H14C,H14D), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C15(H15), C18(H18), C20(H20), C21(H21), C23(H23),
 C15A(H15A)
3.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16(H16C,H16D), C24(H24A,H24B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.63036(8) 0.6427(5) 0.57819(11) 0.0274(6) Uani 1 1 d . . . . .
B2 B 0.66719(13) 0.4983(9) 0.57576(19) 0.0259(8) Uani 1 1 d . . . . .
O3 O 0.69031(8) 0.5427(5) 0.52931(11) 0.0261(6) Uani 1 1 d . . . . .
B4 B 0.67754(14) 0.7353(9) 0.48244(19) 0.0275(9) Uani 1 1 d . . . . .
C5 C 0.63644(11) 0.9018(7) 0.48614(17) 0.0260(8) Uani 1 1 d . . . . .
C6 C 0.61476(11) 0.8404(7) 0.53416(17) 0.0258(8) Uani 1 1 d . . . . .
C7 C 0.68250(11) 0.2766(7) 0.62623(16) 0.0256(8) Uani 1 1 d . . . . .
C8 C 0.71732(11) 0.1047(7) 0.62326(16) 0.0254(7) Uani 1 1 d . . . . .
C9 C 0.73037(12) -0.0943(8) 0.66808(18) 0.0299(8) Uani 1 1 d . . . . .
H9 H 0.753973 -0.209829 0.665086 0.036 Uiso 1 1 calc R . . . .
C10 C 0.70881(12) -0.1232(8) 0.71703(18) 0.0322(9) Uani 1 1 d . . . . .
H10 H 0.717760 -0.259176 0.747717 0.039 Uiso 1 1 calc R . . . .
C11 C 0.67391(13) 0.0455(9) 0.72201(18) 0.0352(9) Uani 1 1 d . . . . .
C12 C 0.66121(12) 0.2392(8) 0.67576(17) 0.0307(8) Uani 1 1 d . . . . .
H12 H 0.637005 0.350732 0.678042 0.037 Uiso 1 1 calc R . . . .
O13 O 0.74021(9) 0.1224(6) 0.57568(14) 0.0360(7) Uani 1 1 d . . . . .
H13 H 0.7271(17) 0.261(12) 0.548(2) 0.054 Uiso 1 1 d R . . . .
C14 C 0.64987(16) 0.0071(13) 0.7750(2) 0.0543(14) Uani 1 1 d . . . . .
H14A H 0.666130 -0.123656 0.805362 0.065 Uiso 0.870(14) 1 calc R . P A 1
H14B H 0.649437 0.181044 0.797186 0.065 Uiso 0.870(14) 1 calc R . P A 1
H14C H 0.645012 -0.189060 0.778241 0.065 Uiso 0.130(14) 1 calc R . P A 2
H14D H 0.670188 0.060866 0.814115 0.065 Uiso 0.130(14) 1 calc R . P A 2
C15 C 0.6059(2) -0.0868(13) 0.7552(3) 0.0516(19) Uani 0.870(14) 1 d . . P A 1
H15 H 0.602096 -0.257477 0.734944 0.062 Uiso 0.870(14) 1 calc R . P A 1
C16 C 0.57002(17) 0.0411(16) 0.7623(2) 0.0675(17) Uani 1 1 d . . . . .
H16A H 0.572065 0.212354 0.782181 0.081 Uiso 0.870(14) 1 calc R . P A 1
H16B H 0.542347 -0.038831 0.747413 0.081 Uiso 0.870(14) 1 calc R . P A 1
H16C H 0.563860 -0.139550 0.748831 0.081 Uiso 0.130(14) 1 calc R . P A 2
H16D H 0.546959 0.159802 0.765980 0.081 Uiso 0.130(14) 1 calc R . P A 2
O17 O 0.69953(10) 0.7679(6) 0.43614(13) 0.0382(7) Uani 1 1 d . . . . .
H17 H 0.7186(18) 0.648(12) 0.435(3) 0.057 Uiso 1 1 d R . . . .
C18 C 0.61811(12) 1.0994(8) 0.44245(17) 0.0279(8) Uani 1 1 d . . . . .
H18 H 0.632465 1.145079 0.409444 0.033 Uiso 1 1 calc R . . . .
C19 C 0.57968(12) 1.2298(8) 0.44607(17) 0.0292(8) Uani 1 1 d . . . . .
C20 C 0.55926(12) 1.1602(8) 0.49495(19) 0.0330(9) Uani 1 1 d . . . . .
H20 H 0.532908 1.248121 0.497998 0.040 Uiso 1 1 calc R . . . .
C21 C 0.57616(12) 0.9667(8) 0.53936(18) 0.0313(8) Uani 1 1 d . . . . .
H21 H 0.561763 0.921869 0.572370 0.038 Uiso 1 1 calc R . . . .
C22 C 0.56024(13) 1.4410(8) 0.3979(2) 0.0356(9) Uani 1 1 d . . . . .
H22A H 0.562605 1.619905 0.418426 0.043 Uiso 1 1 calc R . . . .
H22B H 0.577373 1.446604 0.364408 0.043 Uiso 1 1 calc R . . . .
C23 C 0.51414(15) 1.3894(10) 0.3689(2) 0.0445(11) Uani 1 1 d . . . . .
H23 H 0.507225 1.220975 0.348497 0.053 Uiso 1 1 calc R . . . .
C24 C 0.48227(16) 1.5572(13) 0.3691(3) 0.0606(15) Uani 1 1 d . . . . .
H24A H 0.487866 1.727716 0.389047 0.073 Uiso 1 1 calc R . . . .
H24B H 0.453437 1.509086 0.349429 0.073 Uiso 1 1 calc R . . . .
C15A C 0.6115(11) 0.129(8) 0.7760(15) 0.041(11) Uani 0.130(14) 1 d . . P A 2
H15A H 0.614267 0.311931 0.788990 0.049 Uiso 0.130(14) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B2 1.371(5) . ?
O1 C6 1.388(4) . ?
B2 O3 1.377(5) . ?
B2 C7 1.559(5) . ?
O3 B4 1.395(5) . ?
B4 C5 1.549(5) . ?
B4 O17 1.342(5) . ?
C5 C6 1.392(5) . ?
C5 C18 1.404(5) . ?
C6 C21 1.390(5) . ?
C7 C8 1.399(5) . ?
C7 C12 1.392(5) . ?
C8 C9 1.389(5) . ?
C8 O13 1.378(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(6) . ?
C11 C12 1.389(6) . ?
C11 C14 1.513(6) . ?
C12 H12 0.9500 . ?
O13 H13 0.95(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C15 1.438(8) . ?
C14 C15A 1.35(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.330(8) . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C16 H16C 0.9500 . ?
C16 H16D 0.9500 . ?
C16 C15A 1.35(3) . ?
O17 H17 0.85(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(5) . ?
C19 C20 1.393(5) . ?
C19 C22 1.519(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.479(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.303(7) . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C15A H15A 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
B2 O1 C6 121.6(3) . . ?
O1 B2 O3 121.4(3) . . ?
O1 B2 C7 118.9(3) . . ?
O3 B2 C7 119.8(3) . . ?
B2 O3 B4 122.0(3) . . ?
O3 B4 C5 116.5(3) . . ?
O17 B4 O3 121.0(3) . . ?
O17 B4 C5 122.5(3) . . ?
C6 C5 B4 117.6(3) . . ?
C6 C5 C18 117.7(3) . . ?
C18 C5 B4 124.6(3) . . ?
O1 C6 C5 120.9(3) . . ?
O1 C6 C21 116.9(3) . . ?
C21 C6 C5 122.1(3) . . ?
C8 C7 B2 121.9(3) . . ?
C12 C7 B2 120.7(3) . . ?
C12 C7 C8 117.3(3) . . ?
C9 C8 C7 121.5(3) . . ?
O13 C8 C7 121.9(3) . . ?
O13 C8 C9 116.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.3(4) . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 C14 121.6(4) . . ?
C7 C12 H12 118.6 . . ?
C11 C12 C7 122.7(4) . . ?
C11 C12 H12 118.6 . . ?
C8 O13 H13 107(3) . . ?
C11 C14 H14A 108.7 . . ?
C11 C14 H14B 108.7 . . ?
C11 C14 H14C 106.6 . . ?
C11 C14 H14D 106.6 . . ?
H14A C14 H14B 107.6 . . ?
H14C C14 H14D 106.6 . . ?
C15 C14 C11 114.2(4) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C15A C14 C11 122.8(14) . . ?
C15A C14 H14C 106.6 . . ?
C15A C14 H14D 106.6 . . ?
C14 C15 H15 116.7 . . ?
C16 C15 C14 126.5(6) . . ?
C16 C15 H15 116.7 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
H16C C16 H16D 120.0 . . ?
C15A C16 H16C 120.0 . . ?
C15A C16 H16D 120.0 . . ?
B4 O17 H17 114(4) . . ?
C5 C18 H18 119.0 . . ?
C19 C18 C5 121.9(3) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 C22 121.0(3) . . ?
C20 C19 C22 121.0(3) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 C19 122.1(4) . . ?
C21 C20 H20 118.9 . . ?
C6 C21 H21 120.9 . . ?
C20 C21 C6 118.1(3) . . ?
C20 C21 H21 120.9 . . ?
C19 C22 H22A 108.9 . . ?
C19 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 C19 113.3(4) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23 117.5 . . ?
C24 C23 C22 125.0(5) . . ?
C24 C23 H23 117.5 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C14 C15A H15A 113.7 . . ?
C16 C15A C14 133(3) . . ?
C16 C15A H15A 113.7 . . ?

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
O13 H13 O3 0.95(6) 1.81(6) 2.679(4) 152(5) . yes
O17 H17 O13 0.85(6) 1.91(6) 2.756(4) 174(5) 7_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 B2 O3 B4 -0.2(6) . . . . ?
O1 B2 C7 C8 173.9(3) . . . . ?
O1 B2 C7 C12 -4.9(5) . . . . ?
O1 C6 C21 C20 -178.4(3) . . . . ?
B2 O1 C6 C5 -0.8(5) . . . . ?
B2 O1 C6 C21 177.3(3) . . . . ?
B2 O3 B4 C5 1.3(5) . . . . ?
B2 O3 B4 O17 -177.3(4) . . . . ?
B2 C7 C8 C9 -179.2(3) . . . . ?
B2 C7 C8 O13 0.3(5) . . . . ?
B2 C7 C12 C11 -179.6(4) . . . . ?
O3 B2 C7 C8 -5.1(5) . . . . ?
O3 B2 C7 C12 176.1(3) . . . . ?
O3 B4 C5 C6 -2.2(5) . . . . ?
O3 B4 C5 C18 -178.4(3) . . . . ?
B4 C5 C6 O1 2.0(5) . . . . ?
B4 C5 C6 C21 -176.1(4) . . . . ?
B4 C5 C18 C19 175.8(4) . . . . ?
C5 C6 C21 C20 -0.2(6) . . . . ?
C5 C18 C19 C20 0.2(6) . . . . ?
C5 C18 C19 C22 -179.4(4) . . . . ?
C6 O1 B2 O3 -0.2(5) . . . . ?
C6 O1 B2 C7 -179.2(3) . . . . ?
C6 C5 C18 C19 -0.4(6) . . . . ?
C7 B2 O3 B4 178.9(3) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C8 C7 C12 C11 1.6(6) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C9 C10 C11 C14 178.5(4) . . . . ?
C10 C11 C12 C7 -1.9(6) . . . . ?
C10 C11 C14 C15 -112.0(5) . . . . ?
C10 C11 C14 C15A -168(2) . . . . ?
C11 C14 C15 C16 -118.6(6) . . . . ?
C11 C14 C15A C16 101(3) . . . . ?
C12 C7 C8 C9 -0.4(5) . . . . ?
C12 C7 C8 O13 179.1(3) . . . . ?
C12 C11 C14 C15 65.3(7) . . . . ?
C12 C11 C14 C15A 10(2) . . . . ?
O13 C8 C9 C10 -180.0(3) . . . . ?
C14 C11 C12 C7 -179.3(4) . . . . ?
O17 B4 C5 C6 176.4(4) . . . . ?
O17 B4 C5 C18 0.2(6) . . . . ?
C18 C5 C6 O1 178.4(3) . . . . ?
C18 C5 C6 C21 0.4(6) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C18 C19 C22 C23 127.6(4) . . . . ?
C19 C20 C21 C6 0.0(6) . . . . ?
C19 C22 C23 C24 123.2(5) . . . . ?
C20 C19 C22 C23 -52.0(5) . . . . ?
C22 C19 C20 C21 179.5(4) . . . . ?

_olex2_date_sample_data_collection 2018-01-19
_olex2_date_sample_submission    2018-01-18
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
# This is the default assumed mounting details'
_olex2_submission_original_sample_id RA-195-001
_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 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.523
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, pentane'
####################################################################### 
# 
# 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_42b
_database_code_depnum_ccdc_archive 'CCDC 2327694'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDF
_nottingham_internal_coll_number 17454
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 3.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   18/01/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 23/01/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 23/1/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 12/2/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 12/2/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 12/2/2018
_refine_special_details          
;
The alyll group C49-C51 is disordered over two orientations. The occupancies 
of the two components were refined competitively, converging to a ratio of 
0.51:0.49.
;
_audit_creation_date             2018-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Br O3'
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 Br O3'
_chemical_oxdiff_usercomment     
'REARDF #17454 GVA-1359 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
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'
Br Br -0.6763 1.2805 '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                   11.1367(5)
_cell_length_b                   12.0896(6)
_cell_length_c                   14.1443(7)
_cell_angle_alpha                66.361(5)
_cell_angle_beta                 82.591(4)
_cell_angle_gamma                75.387(4)
_cell_volume                     1687.30(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9461
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0210
_cell_measurement_theta_min      3.4000
_shelx_estimated_absorpt_T_max   0.715
_shelx_estimated_absorpt_T_min   0.385
_exptl_absorpt_coefficient_mu    3.421
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.437
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0692
-3 5 0 0.0770
4 -4 2 0.0987
-5 4 -2 0.0949
-6 -3 -6 0.1530
0 -7 -3 0.0956
2 5 -4 0.0969
-7 1 -2 0.1228
-7 -3 0 0.1239
-7 -3 -4 0.1437
1 0 -5 0.1558
5 -2 1 0.1193
2 -1 3 0.0804
-2 1 5 0.1545
0 0 -1 0.1534
-2 1 -3 0.1376
-5 2 3 0.1254
-1 -5 4 0.1042
1 0 1 0.0999
0 0 -1 0.1459
0 1 0 0.0362
7 -1 2 0.1182
5 6 7 0.1178

_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.105
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
-0.0004 -0.5001 -0.0019 0.0509 -0.0182 -0.0463
-2.9950 5.4999 0.0185 -0.3352 0.3260 0.8528
3.9911 -4.0017 1.9857 0.1957 -0.1255 -0.9446
-4.9912 3.5011 -1.9884 -0.0698 0.1491 1.0126
-5.9866 -3.4956 -6.0112 0.5417 -0.4396 0.7111
0.0015 -7.4977 -3.0250 0.6315 -0.5549 -0.5204
2.0128 5.0072 -3.9744 -0.8355 -0.2764 0.4678
-6.9925 0.9997 -1.9996 0.3348 0.1415 1.0095
-6.9999 -2.5037 -0.0154 0.7794 0.2014 0.5686
-6.9907 -2.9985 -4.0125 0.6539 -0.1920 0.7553
1.0113 -0.4931 -4.9951 -0.2445 -0.5290 0.1306
4.9947 -1.9995 0.9953 -0.1271 -0.1882 -0.8153
1.9915 -1.0033 2.9942 0.0842 0.1613 -0.4961
-2.0106 0.9928 4.9961 0.2686 0.5890 0.0301
0.0024 0.0013 -0.9988 -0.0441 -0.0938 0.0583
-1.9915 1.0033 -2.9942 -0.0842 -0.1613 0.4961
-5.0042 1.9943 2.9998 0.3035 0.5633 0.5823
-1.0130 -5.0068 3.9752 0.7606 0.2346 -0.5821
0.9977 0.4992 1.0015 -0.0818 0.0702 -0.1262
0.0020 -0.4988 -1.0007 0.0068 -0.1120 0.0119
0.0004 0.5001 0.0019 -0.0509 0.0182 0.0463
6.9925 -0.9997 1.9996 -0.3348 -0.1415 -1.0095
4.9867 6.4945 7.0206 -0.7281 0.6846 -0.3769

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12597
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.677
_diffrn_reflns_theta_min         3.413
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        
'flash frozen in gaseous N2' # assumed default, please check
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  67.00   1.00    1.00    --   42.81 -57.00  90.00   94
  2  ω     38.00  65.00   1.00    3.00    --  103.32-125.00 150.00   27
  3  ω     38.00  64.00   1.00    3.00    --  103.32-125.00 120.00   26
  4  ω     96.00 121.00   1.00    3.00    --  103.32-125.00 120.00   25
  5  ω     61.00 124.00   1.00    3.00    --  103.32 -77.00   0.00   63
  6  ω     92.00 120.00   1.00    3.00    --  103.32-125.00 -90.00   28
  7  ω     70.00 108.00   1.00    3.00    --  103.32 -94.00 -60.00   38
  8  ω     47.00  87.00   1.00    3.00    --  103.32 -94.00 -90.00   40
  9  ω     39.00  98.00   1.00    3.00    --  103.32 -45.00-120.00   59
 10  ω     34.00  77.00   1.00    3.00    --  103.32 -30.00 -60.00   43
 11  ω     34.00  83.00   1.00    3.00    --  103.32 -30.00-180.00   49
 12  ω     20.00 112.00   1.00    1.00    --   42.81  57.00-120.00   92
 13  ω     76.00 168.00   1.00    3.00    --  103.32  77.00-180.00   92
 14  ω     78.00 124.00   1.00    3.00    --  103.32 125.00 -90.00   46
 15  ω     91.00 171.00   1.00    3.00    --  103.32  30.00  90.00   80
 16  ω    135.00 160.00   1.00    3.00    --  103.32 125.00 120.00   25
 17  ω     84.00 117.00   1.00    3.00    --  103.32 125.00 120.00   33
 18  ω     38.00  74.00   1.00    3.00    --  103.32 -30.00  90.00   36
 19  ω     32.00 133.00   1.00    3.00    --  103.32 -77.00 120.00  101
 20  ω    -17.00  70.00   1.00    1.00    --   42.81 -77.00 -30.00   87
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 
'MiTeGen micromount' # assumed default, please check
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0749829000
_diffrn_orient_matrix_UB_12      -0.1019315000
_diffrn_orient_matrix_UB_13      0.0438369000
_diffrn_orient_matrix_UB_21      -0.0419095000
_diffrn_orient_matrix_UB_22      0.0361342000
_diffrn_orient_matrix_UB_23      0.0938547000
_diffrn_orient_matrix_UB_31      -0.1143579000
_diffrn_orient_matrix_UB_32      0.0929788000
_diffrn_orient_matrix_UB_33      -0.0584743000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6212
_reflns_number_total             6604
_reflns_odcompleteness_completeness 99.88
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6604
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.075
_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)+(0.0406P)²+3.5368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1022
_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. Others
 Sof(C49)=Sof(H49C)=Sof(H49D)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51C)=Sof(H51D)=1-
 FVAR(1)
 Sof(C49A)=Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=
 Sof(H51B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C6(H6), C36(H36)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C17(H17A,H17B), C19(H19A,H19B), C35(H35A,H35B), C47(H47A,H47B),
 C49(H49C,H49D), C49A(H49A,H49B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C20(H20), C37(H37),
 C38(H38), C40(H40), C41(H41), C44(H44), C45(H45), C50(H50), C50A(H50A)
3.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C51(H51C,H51D), C51A(H51A,H51B)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C48(H48A,H48B,H48C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.4875(2) 0.8666(3) 0.2594(2) 0.0558(8) Uani 1 1 d . . . . .
C2 C 0.5993(3) 0.8859(4) 0.2746(3) 0.0419(9) Uani 1 1 d . . . . .
C3 C 0.6947(3) 0.7918(3) 0.3322(2) 0.0303(7) Uani 1 1 d . . . . .
C4 C 0.6797(3) 0.6580(3) 0.3857(2) 0.0280(6) Uani 1 1 d . . . . .
C5 C 0.5716(3) 0.6443(4) 0.3338(3) 0.0401(8) Uani 1 1 d . . . . .
H5A H 0.601194 0.641391 0.265628 0.048 Uiso 1 1 calc R . . . .
H5B H 0.547646 0.564988 0.377045 0.048 Uiso 1 1 calc R . . . .
C6 C 0.4586(3) 0.7493(4) 0.3197(3) 0.0429(9) Uani 1 1 d . . . . .
H6 H 0.395278 0.737113 0.282876 0.051 Uiso 1 1 calc R . . . .
C7 C 0.6159(3) 1.0063(4) 0.2268(3) 0.0509(11) Uani 1 1 d . . . . .
H7 H 0.551756 1.069635 0.186316 0.061 Uiso 1 1 calc R . . . .
C8 C 0.7241(3) 1.0355(3) 0.2370(3) 0.0430(9) Uani 1 1 d . . . . .
H8 H 0.732983 1.118757 0.204610 0.052 Uiso 1 1 calc R . . . .
C9 C 0.8212(3) 0.9437(3) 0.2948(2) 0.0316(7) Uani 1 1 d . . . . .
C10 C 0.8045(3) 0.8235(3) 0.3400(2) 0.0278(6) Uani 1 1 d . . . . .
H10 H 0.870271 0.759806 0.377880 0.033 Uiso 1 1 calc R . . . .
C11 C 0.7949(3) 0.5721(3) 0.3674(2) 0.0278(6) Uani 1 1 d . . . . .
H11 H 0.823008 0.585657 0.298106 0.033 Uiso 1 1 calc R . . . .
C12 C 0.8596(3) 0.4783(3) 0.4427(2) 0.0237(6) Uani 1 1 d . . . . .
C13 C 0.8248(3) 0.4482(3) 0.5532(2) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.7170(3) 0.5347(3) 0.5740(2) 0.0251(6) Uani 1 1 d . . . . .
H14 H 0.692527 0.522504 0.643699 0.030 Uiso 1 1 calc R . . . .
C15 C 0.6518(3) 0.6298(3) 0.4991(2) 0.0251(6) Uani 1 1 d . . . . .
H15 H 0.583782 0.682995 0.518206 0.030 Uiso 1 1 calc R . . . .
O16 O 0.4092(2) 0.7435(2) 0.41638(18) 0.0341(5) Uani 1 1 d . . . . .
C17 C 0.2877(3) 0.8224(3) 0.4146(3) 0.0343(7) Uani 1 1 d . . . . .
H17A H 0.228107 0.800009 0.382861 0.041 Uiso 1 1 calc R . . . .
H17B H 0.290667 0.910097 0.374055 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2489(4) 0.8032(4) 0.5245(3) 0.0437(8) Uani 1 1 d . . . . .
H18A H 0.253681 0.714906 0.565119 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.163468 0.849576 0.527307 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.304318 0.832713 0.553050 0.066 Uiso 1 1 calc GR . . . .
C19 C 0.9405(3) 0.9758(3) 0.3045(3) 0.0351(7) Uani 1 1 d . . . . .
H19A H 0.919191 1.051754 0.319696 0.042 Uiso 1 1 calc R . . . .
H19B H 0.985034 0.908157 0.364324 0.042 Uiso 1 1 calc R . . . .
C20 C 1.0269(3) 0.9965(3) 0.2118(3) 0.0397(8) Uani 1 1 d . . . . .
H20 H 1.097618 1.026350 0.212883 0.048 Uiso 1 1 calc R . . . .
C21 C 1.0140(4) 0.9772(4) 0.1298(3) 0.0498(10) Uani 1 1 d . . . . .
H21A H 0.944644 0.947281 0.125271 0.060 Uiso 1 1 calc R . . . .
H21B H 1.073851 0.992971 0.074537 0.060 Uiso 1 1 calc R . . . .
Br22 Br 1.00325(3) 0.37313(3) 0.41303(2) 0.02923(10) Uani 1 1 d . . . . .
O23 O 0.8819(2) 0.3580(2) 0.62169(17) 0.0343(5) Uani 1 1 d . . . . .
O31 O 0.50246(17) 0.60289(18) 0.12937(16) 0.0244(4) Uani 1 1 d . . . . .
C32 C 0.4472(2) 0.5039(2) 0.1651(2) 0.0182(5) Uani 1 1 d . . . . .
C33 C 0.3272(2) 0.5107(2) 0.1411(2) 0.0171(5) Uani 1 1 d . . . . .
C34 C 0.2460(2) 0.6341(2) 0.0727(2) 0.0174(5) Uani 1 1 d . . . . .
C35 C 0.3094(2) 0.7413(2) 0.0566(2) 0.0204(5) Uani 1 1 d . . . . .
H35A H 0.273816 0.815016 -0.003839 0.025 Uiso 1 1 calc R . . . .
H35B H 0.291774 0.763492 0.118015 0.025 Uiso 1 1 calc R . . . .
C36 C 0.4484(2) 0.7062(3) 0.0397(2) 0.0218(5) Uani 1 1 d . . . . .
H36 H 0.467761 0.684958 -0.022886 0.026 Uiso 1 1 calc R . . . .
C37 C 0.5173(2) 0.3927(3) 0.2315(2) 0.0218(5) Uani 1 1 d . . . . .
H37 H 0.598435 0.388744 0.248686 0.026 Uiso 1 1 calc R . . . .
C38 C 0.4684(3) 0.2889(3) 0.2719(2) 0.0288(6) Uani 1 1 d . . . . .
H38 H 0.516048 0.213577 0.317671 0.035 Uiso 1 1 calc R . . . .
C39 C 0.3494(3) 0.2922(3) 0.2468(3) 0.0315(7) Uani 1 1 d . . . . .
C40 C 0.2808(3) 0.4032(3) 0.1816(2) 0.0237(6) Uani 1 1 d . . . . .
H40 H 0.200111 0.406469 0.163962 0.028 Uiso 1 1 calc R . . . .
C41 C 0.2334(2) 0.6272(3) -0.0295(2) 0.0194(5) Uani 1 1 d . . . . .
H41 H 0.306643 0.613450 -0.069524 0.023 Uiso 1 1 calc R . . . .
C42 C 0.1248(3) 0.6395(3) -0.0663(2) 0.0215(5) Uani 1 1 d . . . . .
C43 C 0.0045(3) 0.6589(3) -0.0098(2) 0.0232(6) Uani 1 1 d . . . . .
C44 C 0.0140(3) 0.6690(3) 0.0888(2) 0.0235(6) Uani 1 1 d . . . . .
H44 H -0.060162 0.684629 0.127301 0.028 Uiso 1 1 calc R . . . .
C45 C 0.1221(3) 0.6571(3) 0.1265(2) 0.0208(5) Uani 1 1 d . . . . .
H45 H 0.120980 0.663490 0.191400 0.025 Uiso 1 1 calc R . . . .
O46 O 0.49852(18) 0.80411(19) 0.02774(18) 0.0281(5) Uani 1 1 d . . . . .
C47 C 0.6300(3) 0.7854(3) 0.0023(3) 0.0319(7) Uani 1 1 d . . . . .
H47A H 0.647065 0.766345 -0.060657 0.038 Uiso 1 1 calc R . . . .
H47B H 0.676441 0.715192 0.059593 0.038 Uiso 1 1 calc R . . . .
C48 C 0.6699(3) 0.9026(3) -0.0157(3) 0.0423(9) Uani 1 1 d . . . . .
H48A H 0.623171 0.971517 -0.072360 0.063 Uiso 1 1 calc GR . . . .
H48B H 0.758860 0.892421 -0.033750 0.063 Uiso 1 1 calc GR . . . .
H48C H 0.653594 0.920041 0.047242 0.063 Uiso 1 1 calc GR . . . .
C49 C 0.2969(10) 0.1797(10) 0.3103(8) 0.025(2) Uani 0.510(8) 1 d . . P A 2
H49C H 0.208226 0.199147 0.294218 0.030 Uiso 0.510(8) 1 calc R . P A 2
H49D H 0.340147 0.111390 0.288146 0.030 Uiso 0.510(8) 1 calc R . P A 2
C49A C 0.2984(11) 0.1721(11) 0.2744(9) 0.030(2) Uani 0.490(8) 1 d . . P A 1
H49A H 0.231801 0.188762 0.227170 0.036 Uiso 0.490(8) 1 calc R . P A 1
H49B H 0.365818 0.104090 0.267807 0.036 Uiso 0.490(8) 1 calc R . P A 1
C50 C 0.3061(6) 0.1342(5) 0.4248(5) 0.0255(14) Uani 0.510(8) 1 d . . P A 2
H50 H 0.245226 0.175260 0.460393 0.031 Uiso 0.510(8) 1 calc R . P A 2
C50A C 0.2489(7) 0.1374(6) 0.3827(6) 0.0289(17) Uani 0.490(8) 1 d . . P A 1
H50A H 0.301172 0.129249 0.434148 0.035 Uiso 0.490(8) 1 calc R . P A 1
C51 C 0.3920(6) 0.0416(6) 0.4801(5) 0.0322(16) Uani 0.510(8) 1 d . . P A 2
H51C H 0.454557 -0.001797 0.447309 0.039 Uiso 0.510(8) 1 calc R . P A 2
H51D H 0.391584 0.018223 0.552721 0.039 Uiso 0.510(8) 1 calc R . P A 2
C51A C 0.1362(7) 0.1172(6) 0.4112(6) 0.0354(18) Uani 0.490(8) 1 d . . P A 1
H51A H 0.081893 0.124704 0.361281 0.042 Uiso 0.490(8) 1 calc R . P A 1
H51B H 0.109306 0.095268 0.481554 0.042 Uiso 0.490(8) 1 calc R . P A 1
Br52 Br 0.11252(3) 0.63156(3) -0.19561(2) 0.02832(10) Uani 1 1 d . . . . .
O53 O -0.09377(19) 0.6656(2) -0.04287(19) 0.0354(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.380(5) . ?
O1 C6 1.425(5) . ?
C2 C3 1.399(4) . ?
C2 C7 1.388(6) . ?
C3 C4 1.529(5) . ?
C3 C10 1.399(5) . ?
C4 C5 1.562(4) . ?
C4 C11 1.500(4) . ?
C4 C15 1.507(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.513(5) . ?
C6 H6 1.0000 . ?
C6 O16 1.388(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(5) . ?
C9 C10 1.384(5) . ?
C9 C19 1.512(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.326(4) . ?
C12 C13 1.477(4) . ?
C12 Br22 1.892(3) . ?
C13 C14 1.465(4) . ?
C13 O23 1.223(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.330(4) . ?
C15 H15 0.9500 . ?
O16 C17 1.442(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.499(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.497(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.303(6) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
O31 C32 1.369(3) . ?
O31 C36 1.442(3) . ?
C32 C33 1.395(4) . ?
C32 C37 1.395(4) . ?
C33 C34 1.538(4) . ?
C33 C40 1.397(4) . ?
C34 C35 1.554(4) . ?
C34 C41 1.506(4) . ?
C34 C45 1.505(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.513(4) . ?
C36 H36 1.0000 . ?
C36 O46 1.375(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.373(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.402(4) . ?
C39 C40 1.381(4) . ?
C39 C49 1.512(12) . ?
C39 C49A 1.578(12) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.329(4) . ?
C42 C43 1.484(4) . ?
C42 Br52 1.893(3) . ?
C43 C44 1.466(4) . ?
C43 O53 1.217(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.331(4) . ?
C45 H45 0.9500 . ?
O46 C47 1.445(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.506(4) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49C 0.9900 . ?
C49 H49D 0.9900 . ?
C49 C50 1.495(11) . ?
C49A H49A 0.9900 . ?
C49A H49B 0.9900 . ?
C49A C50A 1.486(11) . ?
C50 H50 0.9500 . ?
C50 C51 1.315(9) . ?
C50A H50A 0.9500 . ?
C50A C51A 1.320(11) . ?
C51 H51C 0.9500 . ?
C51 H51D 0.9500 . ?
C51A H51A 0.9500 . ?
C51A H51B 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
C2 O1 C6 118.1(3) . . ?
O1 C2 C3 123.9(3) . . ?
O1 C2 C7 116.4(3) . . ?
C7 C2 C3 119.7(3) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 C10 118.2(3) . . ?
C10 C3 C4 120.7(3) . . ?
C3 C4 C5 108.0(3) . . ?
C11 C4 C3 109.7(3) . . ?
C11 C4 C5 106.9(3) . . ?
C11 C4 C15 111.9(2) . . ?
C15 C4 C3 109.0(3) . . ?
C15 C4 C5 111.3(3) . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C4 112.5(3) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
O1 C6 C5 111.8(3) . . ?
O1 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
O16 C6 O1 111.5(3) . . ?
O16 C6 C5 108.6(3) . . ?
O16 C6 H6 108.3 . . ?
C2 C7 H7 119.5 . . ?
C8 C7 C2 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C19 120.5(3) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C19 121.8(3) . . ?
C3 C10 H10 118.6 . . ?
C9 C10 C3 122.7(3) . . ?
C9 C10 H10 118.6 . . ?
C4 C11 H11 118.3 . . ?
C12 C11 C4 123.5(3) . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C13 123.1(3) . . ?
C11 C12 Br22 120.8(2) . . ?
C13 C12 Br22 116.1(2) . . ?
C14 C13 C12 114.8(2) . . ?
O23 C13 C12 122.4(3) . . ?
O23 C13 C14 122.8(3) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.6(3) . . ?
C15 C14 H14 118.7 . . ?
C4 C15 H15 118.1 . . ?
C14 C15 C4 123.9(3) . . ?
C14 C15 H15 118.1 . . ?
C6 O16 C17 114.2(3) . . ?
O16 C17 H17A 110.3 . . ?
O16 C17 H17B 110.3 . . ?
O16 C17 C18 106.9(3) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
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 . . ?
C9 C19 H19A 108.4 . . ?
C9 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 C9 115.5(3) . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
C19 C20 H20 117.0 . . ?
C21 C20 C19 126.0(3) . . ?
C21 C20 H20 117.0 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C32 O31 C36 115.6(2) . . ?
O31 C32 C33 123.8(2) . . ?
O31 C32 C37 115.7(2) . . ?
C33 C32 C37 120.5(2) . . ?
C32 C33 C34 121.2(2) . . ?
C32 C33 C40 118.7(2) . . ?
C40 C33 C34 120.1(2) . . ?
C33 C34 C35 109.2(2) . . ?
C41 C34 C33 108.2(2) . . ?
C41 C34 C35 110.2(2) . . ?
C45 C34 C33 109.5(2) . . ?
C45 C34 C35 107.6(2) . . ?
C45 C34 C41 112.1(2) . . ?
C34 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 107.9 . . ?
C36 C35 C34 111.8(2) . . ?
C36 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
O31 C36 C35 110.0(2) . . ?
O31 C36 H36 110.3 . . ?
C35 C36 H36 110.3 . . ?
O46 C36 O31 107.2(2) . . ?
O46 C36 C35 108.7(2) . . ?
O46 C36 H36 110.3 . . ?
C32 C37 H37 120.2 . . ?
C38 C37 C32 119.6(3) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 H38 119.4 . . ?
C37 C38 C39 121.2(3) . . ?
C39 C38 H38 119.4 . . ?
C38 C39 C49 116.1(5) . . ?
C38 C39 C49A 123.1(5) . . ?
C40 C39 C38 118.5(3) . . ?
C40 C39 C49 124.2(5) . . ?
C40 C39 C49A 117.6(5) . . ?
C33 C40 H40 119.3 . . ?
C39 C40 C33 121.5(3) . . ?
C39 C40 H40 119.3 . . ?
C34 C41 H41 118.4 . . ?
C42 C41 C34 123.2(2) . . ?
C42 C41 H41 118.4 . . ?
C41 C42 C43 123.2(3) . . ?
C41 C42 Br52 122.0(2) . . ?
C43 C42 Br52 114.77(19) . . ?
C44 C43 C42 114.6(2) . . ?
O53 C43 C42 122.5(3) . . ?
O53 C43 C44 122.9(3) . . ?
C43 C44 H44 118.6 . . ?
C45 C44 C43 122.8(3) . . ?
C45 C44 H44 118.6 . . ?
C34 C45 H45 118.0 . . ?
C44 C45 C34 124.0(3) . . ?
C44 C45 H45 118.0 . . ?
C36 O46 C47 113.8(2) . . ?
O46 C47 H47A 110.1 . . ?
O46 C47 H47B 110.1 . . ?
O46 C47 C48 107.9(3) . . ?
H47A C47 H47B 108.4 . . ?
C48 C47 H47A 110.1 . . ?
C48 C47 H47B 110.1 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C39 C49 H49C 108.2 . . ?
C39 C49 H49D 108.2 . . ?
H49C C49 H49D 107.4 . . ?
C50 C49 C39 116.2(7) . . ?
C50 C49 H49C 108.2 . . ?
C50 C49 H49D 108.2 . . ?
C39 C49A H49A 110.3 . . ?
C39 C49A H49B 110.3 . . ?
H49A C49A H49B 108.6 . . ?
C50A C49A C39 107.0(7) . . ?
C50A C49A H49A 110.3 . . ?
C50A C49A H49B 110.3 . . ?
C49 C50 H50 117.5 . . ?
C51 C50 C49 125.0(7) . . ?
C51 C50 H50 117.5 . . ?
C49A C50A H50A 118.2 . . ?
C51A C50A C49A 123.5(9) . . ?
C51A C50A H50A 118.2 . . ?
C50 C51 H51C 120.0 . . ?
C50 C51 H51D 120.0 . . ?
H51C C51 H51D 120.0 . . ?
C50A C51A H51A 120.0 . . ?
C50A C51A H51B 120.0 . . ?
H51A C51A H51B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -1.4(6) . . . . ?
O1 C2 C3 C10 178.8(3) . . . . ?
O1 C2 C7 C8 180.0(4) . . . . ?
O1 C6 O16 C17 68.2(3) . . . . ?
C2 O1 C6 C5 -39.0(5) . . . . ?
C2 O1 C6 O16 82.9(4) . . . . ?
C2 C3 C4 C5 19.1(4) . . . . ?
C2 C3 C4 C11 135.2(3) . . . . ?
C2 C3 C4 C15 -102.0(3) . . . . ?
C2 C3 C10 C9 1.2(5) . . . . ?
C2 C7 C8 C9 1.1(6) . . . . ?
C3 C2 C7 C8 -1.5(6) . . . . ?
C3 C4 C5 C6 -46.0(4) . . . . ?
C3 C4 C11 C12 124.8(3) . . . . ?
C3 C4 C15 C14 -125.8(3) . . . . ?
C4 C3 C10 C9 -178.6(3) . . . . ?
C4 C5 C6 O1 57.8(4) . . . . ?
C4 C5 C6 O16 -65.7(4) . . . . ?
C4 C11 C12 C13 0.1(5) . . . . ?
C4 C11 C12 Br22 179.4(2) . . . . ?
C5 C4 C11 C12 -118.4(3) . . . . ?
C5 C4 C15 C14 115.2(3) . . . . ?
C5 C6 O16 C17 -168.1(3) . . . . ?
C6 O1 C2 C3 11.2(6) . . . . ?
C6 O1 C2 C7 -170.3(4) . . . . ?
C6 O16 C17 C18 179.4(3) . . . . ?
C7 C2 C3 C4 -179.8(3) . . . . ?
C7 C2 C3 C10 0.4(5) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C7 C8 C9 C19 179.1(3) . . . . ?
C8 C9 C10 C3 -1.6(5) . . . . ?
C8 C9 C19 C20 -76.4(4) . . . . ?
C9 C19 C20 C21 -7.3(6) . . . . ?
C10 C3 C4 C5 -161.2(3) . . . . ?
C10 C3 C4 C11 -45.1(4) . . . . ?
C10 C3 C4 C15 77.8(4) . . . . ?
C10 C9 C19 C20 102.2(4) . . . . ?
C11 C4 C5 C6 -163.9(3) . . . . ?
C11 C4 C15 C14 -4.3(4) . . . . ?
C11 C12 C13 C14 -3.5(4) . . . . ?
C11 C12 C13 O23 176.4(3) . . . . ?
C12 C13 C14 C15 3.0(4) . . . . ?
C13 C14 C15 C4 1.0(5) . . . . ?
C15 C4 C5 C6 73.6(4) . . . . ?
C15 C4 C11 C12 3.7(4) . . . . ?
C19 C9 C10 C3 179.8(3) . . . . ?
Br22 C12 C13 C14 177.11(19) . . . . ?
Br22 C12 C13 O23 -3.0(4) . . . . ?
O23 C13 C14 C15 -177.0(3) . . . . ?
O31 C32 C33 C34 -1.3(4) . . . . ?
O31 C32 C33 C40 179.6(2) . . . . ?
O31 C32 C37 C38 179.3(3) . . . . ?
O31 C36 O46 C47 66.1(3) . . . . ?
C32 O31 C36 C35 50.2(3) . . . . ?
C32 O31 C36 O46 168.2(2) . . . . ?
C32 C33 C34 C35 -10.2(3) . . . . ?
C32 C33 C34 C41 109.7(3) . . . . ?
C32 C33 C34 C45 -127.8(3) . . . . ?
C32 C33 C40 C39 1.9(4) . . . . ?
C32 C37 C38 C39 0.7(5) . . . . ?
C33 C32 C37 C38 1.2(4) . . . . ?
C33 C34 C35 C36 40.6(3) . . . . ?
C33 C34 C41 C42 120.5(3) . . . . ?
C33 C34 C45 C44 -119.5(3) . . . . ?
C34 C33 C40 C39 -177.2(3) . . . . ?
C34 C35 C36 O31 -61.9(3) . . . . ?
C34 C35 C36 O46 -179.0(2) . . . . ?
C34 C41 C42 C43 -1.2(4) . . . . ?
C34 C41 C42 Br52 179.5(2) . . . . ?
C35 C34 C41 C42 -120.2(3) . . . . ?
C35 C34 C45 C44 121.9(3) . . . . ?
C35 C36 O46 C47 -175.0(2) . . . . ?
C36 O31 C32 C33 -19.3(4) . . . . ?
C36 O31 C32 C37 162.6(2) . . . . ?
C36 O46 C47 C48 176.1(3) . . . . ?
C37 C32 C33 C34 176.7(2) . . . . ?
C37 C32 C33 C40 -2.4(4) . . . . ?
C37 C38 C39 C40 -1.2(5) . . . . ?
C37 C38 C39 C49 -169.3(5) . . . . ?
C37 C38 C39 C49A 168.7(5) . . . . ?
C38 C39 C40 C33 -0.1(5) . . . . ?
C38 C39 C49 C50 47.9(9) . . . . ?
C38 C39 C49A C50A 83.8(8) . . . . ?
C39 C49 C50 C51 -98.6(9) . . . . ?
C39 C49A C50A C51A 127.8(7) . . . . ?
C40 C33 C34 C35 168.9(2) . . . . ?
C40 C33 C34 C41 -71.2(3) . . . . ?
C40 C33 C34 C45 51.3(3) . . . . ?
C40 C39 C49 C50 -119.5(7) . . . . ?
C40 C39 C49A C50A -106.3(7) . . . . ?
C41 C34 C35 C36 -78.1(3) . . . . ?
C41 C34 C45 C44 0.5(4) . . . . ?
C41 C42 C43 C44 2.6(4) . . . . ?
C41 C42 C43 O53 -177.3(3) . . . . ?
C42 C43 C44 C45 -2.4(4) . . . . ?
C43 C44 C45 C34 1.0(5) . . . . ?
C45 C34 C35 C36 159.4(2) . . . . ?
C45 C34 C41 C42 -0.4(4) . . . . ?
C49 C39 C40 C33 167.0(5) . . . . ?
C49A C39 C40 C33 -170.6(5) . . . . ?
Br52 C42 C43 C44 -178.1(2) . . . . ?
Br52 C42 C43 O53 1.9(4) . . . . ?
O53 C43 C44 C45 177.5(3) . . . . ?

_olex2_date_sample_data_collection 2018-01-19
_olex2_date_sample_submission    2018-01-16
_olex2_exptl_crystal_mounting_method "'in fomblin film on a micromount"
# This is the default assumed mounting details'
_olex2_submission_original_sample_id RA-203-006
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.715
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
####################################################################### 
# 
# 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_30
_database_code_depnum_ccdc_archive 'CCDC 2327691'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_refine_special_details          ?
_audit_creation_date             2018-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Br O3'
_chemical_formula_sum            'C19 H19 Br O3'
_chemical_formula_weight         375.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 Br O3'
_chemical_oxdiff_usercomment     
'REARDG #17455 SN-1272 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
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'
Br Br -0.6763 1.2805 '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                   8.0674(3)
_cell_length_b                   10.0413(5)
_cell_length_c                   11.4509(5)
_cell_angle_alpha                90.265(4)
_cell_angle_beta                 105.787(4)
_cell_angle_gamma                106.880(4)
_cell_volume                     850.63(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10446
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4480
_cell_measurement_theta_min      4.0290
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.350
_exptl_absorpt_coefficient_mu    3.393
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_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 0 0.0010
0 -1 0 0.0270
0 -1 1 0.0151
0 1 -1 0.0140
4 -2 -5 0.1443
-5 1 1 0.1969
0 -2 -6 0.0396

_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.028
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
-0.0004 1.0000 0.0007 0.1015 -0.1029 -0.0708
0.0004 -1.0000 -0.0007 -0.1015 0.1029 0.0708
0.0000 -0.9999 0.9969 -0.1519 0.1222 -0.0584
-0.0000 0.9999 -0.9969 0.1519 -0.1222 0.0584
3.9997 -1.9949 -4.9956 0.6173 0.5575 0.3767
-4.9973 0.9931 1.0062 -0.6594 -0.6437 0.3139
0.0028 -2.0007 -5.9868 0.0992 0.0902 0.9170

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16326
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_min         4.029
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_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    2.50    --  -38.50  38.00 -60.00   84
  2  ω   -109.00 -12.00   1.00    2.50    --  -38.50 -57.00   0.00   97
  3  ω    -65.00  32.00   1.00    2.50    --  -38.50  57.00 150.00   97
  4  ω      1.00  83.00   1.00    2.50    --   43.32 -99.00-150.00   82
  5  ω      1.00  83.00   1.00    2.50    --   43.32 -99.00-120.00   82
  6  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00 -60.00   63
  7  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00-120.00   60
  8  ω     32.00 138.00   1.00   10.00    --  106.13 -77.00 120.00  106
  9  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00  90.00   60
 10  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00  60.00   84
 11  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00-120.00   84
 12  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00-150.00   63
 13  ω     35.00 121.00   1.00   10.00    --  106.13-125.00 -60.00   86
 14  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00 120.00   60
 15  ω     35.00  98.00   1.00   10.00    --  106.13 -45.00  30.00   63
 16  ω     31.00  91.00   1.00   10.00    --  106.13 -30.00  60.00   60
 17  ω     25.00 109.00   1.00   10.00    --  106.13 -95.00 -30.00   84
 18  ω     19.00 178.00   1.00   10.00    --  106.13   0.00 -90.00  159
 19  ω    -50.00  34.00   1.00    2.50    --  -38.50  38.00  60.00   84
 20  ω     17.00 113.00   1.00    2.50    --   43.32  57.00 -90.00   96
 21  ω     12.00 117.00   1.00    2.50    --   43.32  77.00 150.00  105
 22  ω     17.00 113.00   1.00    2.50    --   43.32  57.00  60.00   96
 23  ω     12.00 117.00   1.00    2.50    --   43.32  77.00 -60.00  105
 24  ω     82.00 178.00   1.00   10.00    --  106.13  30.00 -30.00   96
 25  ω     75.00 178.00   1.00   10.00    --  106.13  77.00 150.00  103
 26  ω     61.00 178.00   1.00   10.00    --  106.13  15.00  90.00  117
 27  ω     82.00 177.00   1.00   10.00    --  106.13  45.00 -90.00   95
 28  ω     79.00 176.00   1.00   10.00    --  106.13  61.00-150.00   97
 29  ω     79.00 176.00   1.00   10.00    --  106.13  61.00   0.00   97
 30  ω     75.00 178.00   1.00   10.00    --  106.13  77.00  60.00  103
 31  ω     79.00 176.00   1.00   10.00    --  106.13  61.00 -30.00   97
 32  ω     75.00 178.00   1.00   10.00    --  106.13  77.00-180.00  103
 33  ω     79.00 176.00   1.00   10.00    --  106.13  61.00 120.00   97
 34  ω     12.00  67.00   1.00    2.50    --   43.32  77.00  90.00   55
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1419749000
_diffrn_orient_matrix_UB_12      0.1015917000
_diffrn_orient_matrix_UB_13      -0.0504568000
_diffrn_orient_matrix_UB_21      0.1122728000
_diffrn_orient_matrix_UB_22      -0.1028947000
_diffrn_orient_matrix_UB_23      0.0193747000
_diffrn_orient_matrix_UB_31      -0.1029666000
_diffrn_orient_matrix_UB_32      -0.0707896000
_diffrn_orient_matrix_UB_33      -0.1295689000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3321
_reflns_number_total             3423
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.060
_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)+(0.0326P)²+0.5214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0617
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64606(14) 0.71997(12) 0.32510(11) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.7119(2) 0.61153(16) 0.38244(15) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.622112 0.555360 0.422530 0.024 Uiso 1 1 calc R . . . .
C3 C 0.8897(2) 0.67307(16) 0.47845(15) 0.0189(3) Uani 1 1 d . . . . .
H3A H 0.931040 0.596371 0.518083 0.023 Uiso 1 1 calc R . . . .
H3B H 0.872002 0.730773 0.541622 0.023 Uiso 1 1 calc R . . . .
C4 C 1.0385(2) 0.76477(16) 0.42527(14) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.9543(2) 0.85029(16) 0.32955(14) 0.0168(3) Uani 1 1 d . . . . .
C6 C 1.0657(2) 0.95881(17) 0.28476(15) 0.0197(3) Uani 1 1 d . . . . .
H6 H 1.192995 0.978380 0.315012 0.024 Uiso 1 1 calc R . . . .
C7 C 0.9964(2) 1.03933(17) 0.19724(15) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.8092(2) 1.01193(17) 0.15601(15) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.758331 1.066725 0.097681 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6978(2) 0.90465(17) 0.20041(14) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.7670(2) 0.82186(16) 0.28591(14) 0.0168(3) Uani 1 1 d . . . . .
O11 O 0.73141(15) 0.52315(12) 0.29600(11) 0.0221(2) Uani 1 1 d . . . . .
C12 C 0.5641(2) 0.45698(19) 0.20373(17) 0.0276(4) Uani 1 1 d . . . . .
H12A H 0.525105 0.527406 0.152114 0.033 Uiso 1 1 calc R . . . .
H12B H 0.468336 0.411958 0.242267 0.033 Uiso 1 1 calc R . . . .
C13 C 0.5946(3) 0.3497(2) 0.1277(2) 0.0391(5) Uani 1 1 d . . . . .
H13A H 0.482816 0.304494 0.063292 0.059 Uiso 1 1 calc GR . . . .
H13B H 0.630358 0.279257 0.179192 0.059 Uiso 1 1 calc GR . . . .
H13C H 0.690641 0.394994 0.090840 0.059 Uiso 1 1 calc GR . . . .
C14 C 1.1785(2) 0.86060(17) 0.52979(15) 0.0202(3) Uani 1 1 d . . . . .
H14 H 1.145207 0.930105 0.566371 0.024 Uiso 1 1 calc R . . . .
C15 C 1.3464(2) 0.85430(18) 0.57440(15) 0.0228(3) Uani 1 1 d . . . . .
H15 H 1.427142 0.918324 0.641106 0.027 Uiso 1 1 calc R . . . .
C16 C 1.4099(2) 0.75070(18) 0.52293(15) 0.0221(3) Uani 1 1 d . . . . .
C17 C 1.2860(2) 0.66766(17) 0.41058(15) 0.0208(3) Uani 1 1 d . . . . .
H17 H 1.326847 0.607698 0.368502 0.025 Uiso 1 1 calc R . . . .
C18 C 1.1181(2) 0.67385(16) 0.36589(14) 0.0177(3) Uani 1 1 d . . . . .
H18 H 1.044315 0.618023 0.292629 0.021 Uiso 1 1 calc R . . . .
O19 O 1.55674(17) 0.73393(16) 0.57195(12) 0.0319(3) Uani 1 1 d . . . . .
C20 C 1.1241(2) 1.15015(19) 0.14643(17) 0.0271(4) Uani 1 1 d . . . . .
H20A H 1.239208 1.189244 0.211469 0.033 Uiso 1 1 calc R . . . .
H20B H 1.151055 1.104854 0.079828 0.033 Uiso 1 1 calc R . . . .
C21 C 1.0547(3) 1.26745(19) 0.09871(18) 0.0305(4) Uani 1 1 d . . . . .
H21 H 1.020261 1.318853 0.152868 0.037 Uiso 1 1 calc R . . . .
C22 C 1.0376(3) 1.3051(2) -0.0126(2) 0.0384(5) Uani 1 1 d . . . . .
H22A H 1.070700 1.256232 -0.069412 0.046 Uiso 1 1 calc R . . . .
H22B H 0.992216 1.381228 -0.036317 0.046 Uiso 1 1 calc R . . . .
Br23 Br 0.44335(2) 0.86941(2) 0.14596(2) 0.02289(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4324(19) . ?
O1 C10 1.3649(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.506(2) . ?
C2 O11 1.396(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.555(2) . ?
C4 C5 1.531(2) . ?
C4 C14 1.502(2) . ?
C4 C18 1.510(2) . ?
C5 C6 1.395(2) . ?
C5 C10 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 C8 1.396(2) . ?
C7 C20 1.518(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 C10 1.393(2) . ?
C9 Br23 1.8997(15) . ?
O11 C12 1.441(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.497(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.332(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.469(2) . ?
C16 C17 1.468(2) . ?
C16 O19 1.226(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.331(2) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.491(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.314(3) . ?
C22 H22A 0.9500 . ?
C22 H22B 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
C10 O1 C2 115.91(11) . . ?
O1 C2 H2 108.5 . . ?
O1 C2 C3 110.57(13) . . ?
C3 C2 H2 108.5 . . ?
O11 C2 O1 110.47(13) . . ?
O11 C2 H2 108.5 . . ?
O11 C2 C3 110.11(13) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.53(13) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C5 C4 C3 109.07(12) . . ?
C14 C4 C3 106.66(13) . . ?
C14 C4 C5 110.01(12) . . ?
C14 C4 C18 111.68(13) . . ?
C18 C4 C3 110.41(12) . . ?
C18 C4 C5 108.97(12) . . ?
C6 C5 C4 119.74(13) . . ?
C6 C5 C10 119.08(14) . . ?
C10 C5 C4 121.18(13) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.16(15) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 118.32(14) . . ?
C6 C7 C20 119.67(15) . . ?
C8 C7 C20 121.98(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.79(15) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 121.88(14) . . ?
C8 C9 Br23 119.70(12) . . ?
C10 C9 Br23 118.42(12) . . ?
O1 C10 C5 123.86(14) . . ?
O1 C10 C9 117.35(13) . . ?
C9 C10 C5 118.74(14) . . ?
C2 O11 C12 112.81(12) . . ?
O11 C12 H12A 110.1 . . ?
O11 C12 H12B 110.1 . . ?
O11 C12 C13 108.13(15) . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 H14 117.9 . . ?
C15 C14 C4 124.16(15) . . ?
C15 C14 H14 117.9 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.59(16) . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 116.02(14) . . ?
O19 C16 C15 121.75(16) . . ?
O19 C16 C17 122.22(16) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.99(15) . . ?
C18 C17 H17 119.0 . . ?
C4 C18 H18 118.2 . . ?
C17 C18 C4 123.60(15) . . ?
C17 C18 H18 118.2 . . ?
C7 C20 H20A 108.6 . . ?
C7 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 C7 114.84(15) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21 117.5 . . ?
C22 C21 C20 124.9(2) . . ?
C22 C21 H21 117.5 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -60.13(16) . . . . ?
O1 C2 O11 C12 -59.64(16) . . . . ?
C2 O1 C10 C5 -20.4(2) . . . . ?
C2 O1 C10 C9 161.84(14) . . . . ?
C2 C3 C4 C5 39.92(17) . . . . ?
C2 C3 C4 C14 158.70(13) . . . . ?
C2 C3 C4 C18 -79.78(16) . . . . ?
C2 O11 C12 C13 -171.69(15) . . . . ?
C3 C2 O11 C12 177.96(13) . . . . ?
C3 C4 C5 C6 168.40(14) . . . . ?
C3 C4 C5 C10 -11.53(19) . . . . ?
C3 C4 C14 C15 112.85(17) . . . . ?
C3 C4 C18 C17 -110.69(17) . . . . ?
C4 C5 C6 C7 179.62(14) . . . . ?
C4 C5 C10 O1 1.2(2) . . . . ?
C4 C5 C10 C9 178.86(14) . . . . ?
C4 C14 C15 C16 0.4(3) . . . . ?
C5 C4 C14 C15 -128.99(16) . . . . ?
C5 C4 C18 C17 129.54(16) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
C5 C6 C7 C20 -176.27(15) . . . . ?
C6 C5 C10 O1 -178.76(14) . . . . ?
C6 C5 C10 C9 -1.1(2) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
C6 C7 C20 C21 -154.50(16) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 Br23 179.07(12) . . . . ?
C7 C20 C21 C22 -123.3(2) . . . . ?
C8 C7 C20 C21 27.6(2) . . . . ?
C8 C9 C10 O1 179.17(14) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C10 O1 C2 C3 49.16(17) . . . . ?
C10 O1 C2 O11 -72.98(16) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
O11 C2 C3 C4 62.22(16) . . . . ?
C14 C4 C5 C6 51.74(18) . . . . ?
C14 C4 C5 C10 -128.19(15) . . . . ?
C14 C4 C18 C17 7.8(2) . . . . ?
C14 C15 C16 C17 7.6(2) . . . . ?
C14 C15 C16 O19 -171.58(17) . . . . ?
C15 C16 C17 C18 -7.7(2) . . . . ?
C16 C17 C18 C4 -0.3(2) . . . . ?
C18 C4 C5 C6 -71.01(18) . . . . ?
C18 C4 C5 C10 109.06(16) . . . . ?
C18 C4 C14 C15 -7.9(2) . . . . ?
O19 C16 C17 C18 171.54(16) . . . . ?
C20 C7 C8 C9 176.48(16) . . . . ?
Br23 C9 C10 O1 0.04(19) . . . . ?
Br23 C9 C10 C5 -177.80(11) . . . . ?

_olex2_date_sample_data_collection 2018-02-20
_olex2_date_sample_submission    2018-01-16
_olex2_submission_original_sample_id RA-320-001
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.710
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, petroleum ether'
####################################################################### 
# 
# 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_3-simonsol-F
_database_code_depnum_ccdc_archive 'CCDC 2327689'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2024-01-23 deposited with the CCDC.	2024-06-13 downloaded from the CCDC.
;
_nottingham_internal_coll_name   REARDI
_nottingham_internal_coll_number 17626
_nottingham_internal_coll_client REA/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '20.00, 80.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   10/04/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVA, PL13110002'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 12/04/2018
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 25/4/2018
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 25/4/2018
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 7/6/2018
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 7/6/2018
_refine_special_details          
;
The -CH=CH2 termainl part of the allyl groups are each disordered over two 
orientations. The occupancies of each disorder pair was refined competitively, 
converging to ratios of 0.72:0.28, 0.57:0.43 and 0.81:0.19. Equivalent bond 
lengths of the disordered atoms were restrained to be approximately equal. 
Enhanced rigid bond restraints were applied to the thernal parameters of 
all three allyl groups, and in addition similarity restraints were applied to 
the second and third allyl groups.
;
_audit_creation_date             2018-09-05
_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         'C27 H26 O3'
_chemical_formula_sum            'C27 H26 O3'
_chemical_formula_weight         398.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H26 O3'
_chemical_oxdiff_usercomment     
'REARDI #17626 GVA-1420 IN FOMBLIN FILM ON A MICROMOUNT FOR REA/RD'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.6576(9)
_cell_length_b                   11.7041(5)
_cell_length_c                   10.0865(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.695(4)
_cell_angle_gamma                90
_cell_volume                     2148.74(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.7140
_cell_measurement_theta_min      4.4780
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.787
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 0 0.0211
-1 2 0 0.0221
1 0 -2 0.2001
-1 0 2 0.2001
1 0 0 0.0162
-1 0 0 0.0100
5 2 0 0.0174

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether, pentane'
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.026
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
0.9983 -1.9999 -0.0023 0.2695 -0.0615 -0.0043
-0.9983 1.9999 0.0023 -0.2695 0.0615 0.0043
0.9949 -0.0002 -1.9990 0.0112 0.0051 0.3054
-0.9949 0.0002 1.9990 -0.0112 -0.0051 -0.3054
0.9994 -0.0001 -0.0009 0.0074 -0.0841 0.0055
-0.9994 0.0001 0.0009 -0.0074 0.0841 -0.0055
4.9978 1.9994 -0.0029 -0.2249 -0.4429 0.0375

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8284
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 4.2207
_diffrn_detector_type            'Agilent Diffraction Titan S2 detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -25.00   1.00   20.00    --  -42.81 -38.00  30.00   88
  2  ω    -49.00 -22.00   1.00   20.00    --  -42.81  38.00-180.00   27
  3  ω    -92.00  -2.00   1.00   20.00    --  -42.81 125.00-180.00   90
  4  ω     94.00 170.00   1.00   80.00    --  103.32 125.00-150.00   76
  5  ω    143.00 175.00   1.00   80.00    --  103.32  77.00 -90.00   32
  6  ω     40.00 110.00   1.00   80.00    --  103.32 -94.00-150.00   70
  7  ω     88.00 117.00   1.00   80.00    --  103.32-125.00  60.00   29
  8  ω     32.00  63.00   1.00   80.00    --  103.32-125.00  60.00   31
  9  ω     43.00  87.00   1.00   80.00    --  103.32 -45.00-180.00   44
 10  ω     74.00 127.00   1.00   80.00    --  103.32  77.00 -90.00   53
 11  ω     54.00  84.00   1.00   80.00    --  103.32 -94.00 150.00   30
 12  ω     31.00  97.00   1.00   80.00    --  103.32   0.00  60.00   66
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Titan S2'
_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      0.0074255000
_diffrn_orient_matrix_UB_12      -0.1310418000
_diffrn_orient_matrix_UB_13      -0.0019116000
_diffrn_orient_matrix_UB_21      -0.0841561000
_diffrn_orient_matrix_UB_22      -0.0111960000
_diffrn_orient_matrix_UB_23      -0.0444180000
_diffrn_orient_matrix_UB_31      0.0053994000
_diffrn_orient_matrix_UB_32      0.0050157000
_diffrn_orient_matrix_UB_33      -0.1501017000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2758
_reflns_number_total             4132
_reflns_odcompleteness_completeness 97.88
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4132
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.155
_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)+(0.0828P)²+1.5833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.2029
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C22-C21 \\sim C22A-C21 \\sim C26-C25 \\sim C29-C28 \\sim C28-C29A \\sim
C25-C26A
 with sigma of 0.02
 C27-C26 \\sim C30A-C29A \\sim C30-C29 \\sim C23A-C22A \\sim C23-C22 \\sim
C26A-C27A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C26A \\sim C27 \\sim C27A \\sim C28 \\sim C29 \\sim C29A
\\sim C30 \\sim C30A: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
4. Rigid body (RIGU) restrains
 C21, C22, C22A, C23, C23A, C25, C26, C26A, C27, C27A, C28, C29, C29A, C30, C30A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H28D)=Sof(H28C)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=1-FVAR(1)
 Sof(H28a)=Sof(H28b)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30a)=Sof(H30b)=FVAR(1)
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=1-FVAR(2)
 Sof(H21a)=Sof(H21b)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23a)=Sof(H23b)=FVAR(2)
 Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27C)=Sof(H27D)=1-FVAR(3)
 Sof(H25a)=Sof(H25b)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27a)=Sof(H27b)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C21(H21a,H21b), C21(H21C,H21D), C25(H25a,H25b), C25(H25C,H25D),
 C28(H28a,H28b), C28(H28D,H28C)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C10(H10), C16(H16), C18(H18), C19(H19), C22(H22),
 C22A(H22A), C26(H26), C26A(H26A), C29(H29), C29A(H29A)
6.d X=CH2 refined with riding coordinates:
 C23(H23a,H23b), C23A(H23C,H23D), C27(H27a,H27b), C27A(H27C,H27D), C30(H30a,
 H30b), C30A(H30C,H30D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.63704(16) 0.4605(3) 0.5418(3) 0.0349(6) Uani 1 1 d . . . . .
H1A H 0.612506 0.525683 0.575875 0.042 Uiso 1 1 calc R . . . .
H1B H 0.626167 0.465383 0.441338 0.042 Uiso 1 1 calc R . . . .
C2 C 0.60565(16) 0.3518(3) 0.5820(3) 0.0333(6) Uani 1 1 d . . . . .
C3 C 0.65020(15) 0.2460(2) 0.5891(2) 0.0297(6) Uani 1 1 d . . . . .
C4 C 0.72207(15) 0.2553(2) 0.5850(2) 0.0281(6) Uani 1 1 d . . . . .
H4 H 0.749181 0.186222 0.589189 0.034 Uiso 1 1 calc R . . . .
C5 C 0.76314(17) 0.3643(2) 0.5744(3) 0.0322(6) Uani 1 1 d . . . . .
C6 C 0.82471(17) 0.3726(2) 0.7008(3) 0.0312(6) Uani 1 1 d . . . . .
C7 C 0.89351(17) 0.3207(3) 0.7369(3) 0.0356(7) Uani 1 1 d . . . . .
H7 H 0.910197 0.272323 0.674368 0.043 Uiso 1 1 calc R . . . .
C8 C 0.93774(18) 0.3405(3) 0.8658(3) 0.0413(7) Uani 1 1 d . . . . .
C9 C 0.91096(18) 0.4099(3) 0.9564(3) 0.0400(7) Uani 1 1 d . . . . .
H9 H 0.940686 0.421844 1.044600 0.048 Uiso 1 1 calc R . . . .
C10 C 0.84208(17) 0.4626(3) 0.9225(3) 0.0361(7) Uani 1 1 d . . . . .
H10 H 0.824257 0.509284 0.985250 0.043 Uiso 1 1 calc R . . . .
C11 C 0.80153(17) 0.4431(2) 0.7928(3) 0.0328(6) Uani 1 1 d . . . . .
O12 O 0.73300(12) 0.48891(17) 0.74223(18) 0.0364(5) Uani 1 1 d . . . . .
C13 C 0.71852(17) 0.4708(2) 0.5948(3) 0.0335(6) Uani 1 1 d . . . . .
H13 H 0.737100 0.538007 0.551076 0.040 Uiso 1 1 calc R . . . .
O14 O 0.54341(13) 0.3512(2) 0.6062(2) 0.0450(6) Uani 1 1 d . . . . .
C15 C 0.61816(16) 0.1301(3) 0.5957(3) 0.0321(6) Uani 1 1 d . . . . .
C16 C 0.63368(16) 0.0444(3) 0.5106(3) 0.0341(6) Uani 1 1 d . . . . .
H16 H 0.661671 0.063302 0.445549 0.041 Uiso 1 1 calc R . . . .
C17 C 0.60988(18) -0.0680(3) 0.5167(3) 0.0410(7) Uani 1 1 d . . . . .
C18 C 0.56846(19) -0.0941(3) 0.6113(3) 0.0446(8) Uani 1 1 d . . . . .
H18 H 0.552360 -0.170419 0.618601 0.053 Uiso 1 1 calc R . . . .
C19 C 0.55035(18) -0.0107(3) 0.6949(3) 0.0447(8) Uani 1 1 d . . . . .
H19 H 0.521369 -0.030119 0.758184 0.054 Uiso 1 1 calc R . . . .
C20 C 0.57383(17) 0.1011(3) 0.6880(3) 0.0388(7) Uani 1 1 d . . . . .
C21 C 0.6293(2) -0.1593(3) 0.4251(4) 0.0537(9) Uani 1 1 d D U . . .
H21A H 0.637457 -0.124720 0.340114 0.064 Uiso 0.723(10) 1 calc R . P A 1
H21B H 0.588691 -0.215328 0.401318 0.064 Uiso 0.723(10) 1 calc R . P A 1
H21C H 0.590117 -0.217234 0.420640 0.064 Uiso 0.277(10) 1 calc R . P A 2
H21D H 0.619233 -0.122869 0.334337 0.064 Uiso 0.277(10) 1 calc R . P A 2
C22 C 0.6992(3) -0.2186(4) 0.5013(7) 0.0413(13) Uani 0.723(10) 1 d D U P A 1
H22 H 0.699843 -0.248696 0.589069 0.050 Uiso 0.723(10) 1 calc R . P A 1
C22A C 0.6950(8) -0.2269(12) 0.4279(19) 0.059(4) Uani 0.277(10) 1 d D U P A 2
H22A H 0.703642 -0.270151 0.353175 0.070 Uiso 0.277(10) 1 calc R . P A 2
C23 C 0.7592(3) -0.2306(4) 0.4519(6) 0.0536(16) Uani 0.723(10) 1 d D U P A 1
H23A H 0.760176 -0.201397 0.364409 0.064 Uiso 0.723(10) 1 calc R . P A 1
H23B H 0.801128 -0.268325 0.504020 0.064 Uiso 0.723(10) 1 calc R . P A 1
C23A C 0.7413(11) -0.2205(13) 0.5476(17) 0.062(5) Uani 0.277(10) 1 d D U P A 2
H23C H 0.729206 -0.175645 0.618058 0.075 Uiso 0.277(10) 1 calc R . P A 2
H23D H 0.786539 -0.260857 0.563056 0.075 Uiso 0.277(10) 1 calc R . P A 2
O24 O 0.55530(14) 0.1779(2) 0.7778(2) 0.0473(6) Uani 1 1 d . . . . .
H24 H 0.552(3) 0.245(4) 0.732(5) 0.071 Uiso 1 1 d R . . . .
C25 C 0.78615(18) 0.3624(2) 0.4362(3) 0.0352(6) Uani 1 1 d D U . . .
H25A H 0.818897 0.296114 0.434260 0.042 Uiso 0.43(4) 1 calc R . P B 1
H25B H 0.741783 0.351704 0.362753 0.042 Uiso 0.43(4) 1 calc R . P B 1
H25C H 0.810090 0.288125 0.427308 0.042 Uiso 0.57(4) 1 calc R . P B 2
H25D H 0.741186 0.366416 0.362898 0.042 Uiso 0.57(4) 1 calc R . P B 2
C26 C 0.8243(12) 0.4674(18) 0.409(2) 0.042(3) Uani 0.43(4) 1 d D U P B 1
H26 H 0.868999 0.489485 0.468549 0.051 Uiso 0.43(4) 1 calc R . P B 1
C26A C 0.8375(9) 0.4567(13) 0.4139(18) 0.042(2) Uani 0.57(4) 1 d D U P B 2
H26A H 0.881475 0.466486 0.481204 0.050 Uiso 0.57(4) 1 calc R . P B 2
C27 C 0.7958(14) 0.5314(12) 0.3007(13) 0.041(3) Uani 0.43(4) 1 d D U P B 1
H27A H 0.751077 0.509195 0.241343 0.049 Uiso 0.43(4) 1 calc R . P B 1
H27B H 0.820215 0.599015 0.283033 0.049 Uiso 0.43(4) 1 calc R . P B 1
C27A C 0.8263(12) 0.5273(10) 0.3080(11) 0.047(2) Uani 0.57(4) 1 d D U P B 2
H27C H 0.783037 0.520557 0.238291 0.056 Uiso 0.57(4) 1 calc R . P B 2
H27D H 0.861599 0.584509 0.301965 0.056 Uiso 0.57(4) 1 calc R . P B 2
C28 C 1.0133(2) 0.2903(4) 0.9058(4) 0.0637(11) Uani 1 1 d D U . . .
H28A H 1.047138 0.338385 0.866617 0.076 Uiso 0.806(8) 1 calc R . P C 1
H28B H 1.029600 0.294604 1.005949 0.076 Uiso 0.806(8) 1 calc R . P C 1
H28D H 1.041578 0.343609 0.973969 0.076 Uiso 0.194(8) 1 calc R . P C 2
H28C H 1.007638 0.219266 0.955743 0.076 Uiso 0.194(8) 1 calc R . P C 2
C29 C 1.0206(3) 0.1747(4) 0.8651(5) 0.0565(13) Uani 0.806(8) 1 d D U P C 1
H29 H 0.990576 0.117849 0.892639 0.068 Uiso 0.806(8) 1 calc R . P C 1
C29A C 1.0604(10) 0.2620(18) 0.8206(17) 0.060(3) Uani 0.194(8) 1 d D U P C 2
H29A H 1.094217 0.311818 0.791932 0.072 Uiso 0.194(8) 1 calc R . P C 2
C30 C 1.0701(4) 0.1421(8) 0.7862(9) 0.085(2) Uani 0.806(8) 1 d D U P C 1
H30A H 1.100544 0.197672 0.757597 0.101 Uiso 0.806(8) 1 calc R . P C 1
H30B H 1.073198 0.064276 0.761242 0.101 Uiso 0.806(8) 1 calc R . P C 1
C30A C 1.049(2) 0.150(2) 0.786(5) 0.078(6) Uani 0.194(8) 1 d D U P C 2
H30C H 1.013518 0.106724 0.820227 0.093 Uiso 0.194(8) 1 calc R . P C 2
H30D H 1.076000 0.114288 0.728055 0.093 Uiso 0.194(8) 1 calc R . P C 2


_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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.493(4) . ?
C1 C13 1.501(4) . ?
C2 C3 1.484(4) . ?
C2 O14 1.238(4) . ?
C3 C4 1.355(4) . ?
C3 C15 1.490(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.504(4) . ?
C5 C6 1.520(4) . ?
C5 C13 1.537(4) . ?
C5 C25 1.547(4) . ?
C6 C7 1.394(4) . ?
C6 C11 1.380(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(4) . ?
C8 C9 1.395(4) . ?
C8 C28 1.499(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(4) . ?
C11 O12 1.377(4) . ?
O12 C13 1.468(3) . ?
C13 H13 1.0000 . ?
C15 C16 1.391(4) . ?
C15 C20 1.416(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(4) . ?
C17 C18 1.387(5) . ?
C17 C21 1.507(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(5) . ?
C20 O24 1.374(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C21 C22 1.528(7) . ?
C21 C22A 1.455(12) . ?
C22 H22 0.9500 . ?
C22 C23 1.329(8) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.323(14) . ?
C23 H23A 0.9500 . ?
C23 H23B 0.9500 . ?
C23A H23C 0.9500 . ?
C23A H23D 0.9500 . ?
O24 H24 0.90(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 H25C 0.9900 . ?
C25 H25D 0.9900 . ?
C25 C26 1.476(12) . ?
C25 C26A 1.511(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.334(12) . ?
C26A H26A 0.9500 . ?
C26A C27A 1.330(10) . ?
C27 H27A 0.9500 . ?
C27 H27B 0.9500 . ?
C27A H27C 0.9500 . ?
C27A H27D 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 H28D 0.9900 . ?
C28 H28C 0.9900 . ?
C28 C29 1.429(6) . ?
C28 C29A 1.396(13) . ?
C29 H29 0.9500 . ?
C29 C30 1.398(9) . ?
C29A H29A 0.9500 . ?
C29A C30A 1.366(16) . ?
C30 H30A 0.9500 . ?
C30 H30B 0.9500 . ?
C30A H30C 0.9500 . ?
C30A H30D 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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C2 C1 C13 113.5(2) . . ?
C13 C1 H1A 108.9 . . ?
C13 C1 H1B 108.9 . . ?
C3 C2 C1 118.3(2) . . ?
O14 C2 C1 119.9(3) . . ?
O14 C2 C3 121.7(3) . . ?
C2 C3 C15 122.4(2) . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 C15 119.0(3) . . ?
C3 C4 H4 116.8 . . ?
C3 C4 C5 126.4(3) . . ?
C5 C4 H4 116.8 . . ?
C4 C5 C6 107.3(2) . . ?
C4 C5 C13 112.3(2) . . ?
C4 C5 C25 107.3(2) . . ?
C6 C5 C13 99.7(2) . . ?
C6 C5 C25 116.6(3) . . ?
C13 C5 C25 113.5(2) . . ?
C7 C6 C5 132.4(2) . . ?
C11 C6 C5 108.1(3) . . ?
C11 C6 C7 119.4(3) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.5(3) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C28 121.0(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 C28 120.2(3) . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.6(3) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 121.9 . . ?
C11 C10 C9 116.2(3) . . ?
C11 C10 H10 121.9 . . ?
C10 C11 C6 123.3(3) . . ?
O12 C11 C6 112.7(2) . . ?
O12 C11 C10 124.0(3) . . ?
C11 O12 C13 105.6(2) . . ?
C1 C13 C5 115.0(2) . . ?
C1 C13 H13 109.2 . . ?
C5 C13 H13 109.2 . . ?
O12 C13 C1 108.6(2) . . ?
O12 C13 C5 105.5(2) . . ?
O12 C13 H13 109.2 . . ?
C16 C15 C3 119.3(2) . . ?
C16 C15 C20 117.6(3) . . ?
C20 C15 C3 123.1(3) . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C17 122.8(3) . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C21 121.3(3) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C21 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.7(3) . . ?
O24 C20 C15 123.0(3) . . ?
O24 C20 C19 117.2(3) . . ?
C17 C21 H21A 110.1 . . ?
C17 C21 H21B 110.1 . . ?
C17 C21 H21C 103.8 . . ?
C17 C21 H21D 103.8 . . ?
C17 C21 C22 107.9(3) . . ?
H21A C21 H21B 108.4 . . ?
H21C C21 H21D 105.4 . . ?
C22 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
C22A C21 C17 133.5(7) . . ?
C22A C21 H21C 103.8 . . ?
C22A C21 H21D 103.8 . . ?
C21 C22 H22 118.1 . . ?
C23 C22 C21 123.8(6) . . ?
C23 C22 H22 118.1 . . ?
C21 C22A H22A 124.3 . . ?
C23A C22A C21 111.4(16) . . ?
C23A C22A H22A 124.3 . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C22A C23A H23C 120.0 . . ?
C22A C23A H23D 120.0 . . ?
H23C C23A H23D 120.0 . . ?
C20 O24 H24 103(3) . . ?
C5 C25 H25A 108.9 . . ?
C5 C25 H25B 108.9 . . ?
C5 C25 H25C 108.4 . . ?
C5 C25 H25D 108.4 . . ?
H25A C25 H25B 107.7 . . ?
H25C C25 H25D 107.4 . . ?
C26 C25 C5 113.3(12) . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C26A C25 C5 115.7(8) . . ?
C26A C25 H25C 108.4 . . ?
C26A C25 H25D 108.4 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.8(14) . . ?
C27 C26 H26 120.1 . . ?
C25 C26A H26A 117.2 . . ?
C27A C26A C25 125.5(11) . . ?
C27A C26A H26A 117.2 . . ?
C26 C27 H27A 120.0 . . ?
C26 C27 H27B 120.0 . . ?
H27A C27 H27B 120.0 . . ?
C26A C27A H27C 120.0 . . ?
C26A C27A H27D 120.0 . . ?
H27C C27A H27D 120.0 . . ?
C8 C28 H28A 108.3 . . ?
C8 C28 H28B 108.3 . . ?
C8 C28 H28D 105.4 . . ?
C8 C28 H28C 105.4 . . ?
H28A C28 H28B 107.4 . . ?
H28D C28 H28C 106.0 . . ?
C29 C28 C8 115.9(4) . . ?
C29 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C29A C28 C8 127.5(8) . . ?
C29A C28 H28D 105.4 . . ?
C29A C28 H28C 105.4 . . ?
C28 C29 H29 118.7 . . ?
C30 C29 C28 122.6(6) . . ?
C30 C29 H29 118.7 . . ?
C28 C29A H29A 126.3 . . ?
C30A C29A C28 107(3) . . ?
C30A C29A H29A 126.3 . . ?
C29 C30 H30A 120.0 . . ?
C29 C30 H30B 120.0 . . ?
H30A C30 H30B 120.0 . . ?
C29A C30A H30C 120.0 . . ?
C29A C30A H30D 120.0 . . ?
H30C C30A H30D 120.0 . . ?

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
O24 H24 O14 0.90(5) 1.76(5) 2.644(3) 165(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 12.6(3) . . . . ?
C1 C2 C3 C15 -165.2(2) . . . . ?
C2 C1 C13 C5 47.0(3) . . . . ?
C2 C1 C13 O12 -70.9(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C15 C16 132.7(3) . . . . ?
C2 C3 C15 C20 -49.2(4) . . . . ?
C3 C4 C5 C6 119.1(3) . . . . ?
C3 C4 C5 C13 10.5(4) . . . . ?
C3 C4 C5 C25 -114.8(3) . . . . ?
C3 C15 C16 C17 175.7(3) . . . . ?
C3 C15 C20 C19 -175.3(3) . . . . ?
C3 C15 C20 O24 1.3(4) . . . . ?
C4 C3 C15 C16 -45.1(4) . . . . ?
C4 C3 C15 C20 133.0(3) . . . . ?
C4 C5 C6 C7 79.0(4) . . . . ?
C4 C5 C6 C11 -98.0(3) . . . . ?
C4 C5 C13 C1 -34.0(3) . . . . ?
C4 C5 C13 O12 85.7(3) . . . . ?
C4 C5 C25 C26 177.3(10) . . . . ?
C4 C5 C25 C26A -171.7(8) . . . . ?
C5 C6 C7 C8 -176.5(3) . . . . ?
C5 C6 C11 C10 175.2(3) . . . . ?
C5 C6 C11 O12 -3.1(3) . . . . ?
C5 C25 C26 C27 -120(2) . . . . ?
C5 C25 C26A C27A -126.6(16) . . . . ?
C6 C5 C13 C1 -147.4(2) . . . . ?
C6 C5 C13 O12 -27.7(3) . . . . ?
C6 C5 C25 C26 -62.3(10) . . . . ?
C6 C5 C25 C26A -51.3(9) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C6 C7 C8 C28 -177.2(3) . . . . ?
C6 C11 O12 C13 -15.5(3) . . . . ?
C7 C6 C11 C10 -2.3(4) . . . . ?
C7 C6 C11 O12 179.4(2) . . . . ?
C7 C8 C9 C10 -1.4(5) . . . . ?
C7 C8 C28 C29 -41.9(6) . . . . ?
C7 C8 C28 C29A 27.8(13) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C8 C28 C29 C30 123.6(5) . . . . ?
C8 C28 C29A C30A -93(2) . . . . ?
C9 C8 C28 C29 139.4(4) . . . . ?
C9 C8 C28 C29A -150.9(12) . . . . ?
C9 C10 C11 C6 2.4(4) . . . . ?
C9 C10 C11 O12 -179.5(3) . . . . ?
C10 C11 O12 C13 166.2(3) . . . . ?
C11 C6 C7 C8 0.3(4) . . . . ?
C11 O12 C13 C1 151.2(2) . . . . ?
C11 O12 C13 C5 27.4(3) . . . . ?
C13 C1 C2 C3 -36.2(3) . . . . ?
C13 C1 C2 O14 145.1(3) . . . . ?
C13 C5 C6 C7 -163.9(3) . . . . ?
C13 C5 C6 C11 19.1(3) . . . . ?
C13 C5 C25 C26 52.7(10) . . . . ?
C13 C5 C25 C26A 63.7(9) . . . . ?
O14 C2 C3 C4 -168.6(3) . . . . ?
O14 C2 C3 C15 13.6(4) . . . . ?
C15 C3 C4 C5 178.2(2) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C15 C16 C17 C21 -178.5(3) . . . . ?
C16 C15 C20 C19 2.8(4) . . . . ?
C16 C15 C20 O24 179.4(3) . . . . ?
C16 C17 C18 C19 1.2(5) . . . . ?
C16 C17 C21 C22 93.3(4) . . . . ?
C16 C17 C21 C22A 78.9(11) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C17 C21 C22 C23 -126.4(5) . . . . ?
C17 C21 C22A C23A 14(2) . . . . ?
C18 C17 C21 C22 -85.8(4) . . . . ?
C18 C17 C21 C22A -100.2(11) . . . . ?
C18 C19 C20 C15 -1.2(5) . . . . ?
C18 C19 C20 O24 -178.0(3) . . . . ?
C20 C15 C16 C17 -2.5(4) . . . . ?
C21 C17 C18 C19 -179.7(3) . . . . ?
C25 C5 C6 C7 -41.4(4) . . . . ?
C25 C5 C6 C11 141.6(2) . . . . ?
C25 C5 C13 C1 87.9(3) . . . . ?
C25 C5 C13 O12 -152.4(2) . . . . ?
C28 C8 C9 C10 177.3(3) . . . . ?

loop_
_audit_author_email
pcxra5@nottingham.ac.uk
?
''
_olex2_date_sample_data_collection 2018-04-12
_olex2_date_sample_submission    2018-04-09
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id RA-308-004
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.703
