# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mucjhn
_database_code_depnum_ccdc_archive 'CCDC 1571407'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_nottingham_internal_coll_name   MUCJHN
_nottingham_internal_coll_number 11226
_nottingham_internal_coll_client MU/CJH
_nottingham_internal_coll_type   ?
_nottingham_internal_coll_frame_method ?
_nottingham_internal_coll_frame_time ?
_nottingham_internal_coll_frame_width ?
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument SuperNova
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date ?
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user ?
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user ?
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 29/8/2017
_nottingham_internal_validation_user pczwl
_refine_special_details          ?
_audit_creation_date             2017-08-29
_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         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H28 O2'
_chemical_oxdiff_usercomment     
'MUCJHN #11226 IN FOMBLIN FILM ON MICROMOUNT FOR MU/CJH'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3710(2)
_cell_length_b                   11.8296(3)
_cell_length_c                   13.3226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1634.48(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29930
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      76.5227
_cell_measurement_theta_min      3.3146
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  1.443
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.3387
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.1329
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            47596
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.319
_diffrn_reflns_theta_min         5.000
_diffrn_ambient_temperature      90(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127  -38.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127    0.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127    0.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   64.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   64.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   74.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -95.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   84.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   75.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   85.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -61.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega   95.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  120.00  150.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   43.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega   43.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   96.00  151.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
 20 omega  103.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   30.0000  -90.0000 55

#__ type_ start__ end____ width___ exp.time_
 21 omega   43.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 22 omega   36.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 23 omega   48.00   74.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  101.00  139.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   30.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 25 omega   37.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -95.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega -112.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -57.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
 27 omega -112.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -57.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
 28 omega -115.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega    2.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000    0.0000 96

#__ type_ start__ end____ width___ exp.time_
 30 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 31 omega   36.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 32 omega   89.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   30.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 33 omega   36.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 34 omega   87.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 35 omega   89.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   30.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 36 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 37 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 38 omega   30.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -95.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 39 omega   34.00  113.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -104.0000   10.0000 79

#__ type_ start__ end____ width___ exp.time_
 40 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 41 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -90.0000 75

#__ type_ start__ end____ width___ exp.time_
 42 omega   38.00  140.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -77.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
 43 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
 44 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
 45 omega   89.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   30.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
 46 omega -115.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 47 omega  -24.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127  -57.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
 48 omega    2.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
 49 omega   14.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 50 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 51 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 52 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 53 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 54 omega -131.00  -30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -60.0000  -77.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
 55 omega   36.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 56 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 57 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
 58 omega   40.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 59 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 60 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 61 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
 62 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 63 omega   41.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -61.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 64 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 65 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 66 omega -115.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 67 omega -115.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -38.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
 68 omega -115.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127  -77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 69 omega   23.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   38.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
 70 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000   60.0000 75

#__ type_ start__ end____ width___ exp.time_
 71 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
 72 omega   36.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 73 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 74 omega   79.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  150.0000 79

#__ type_ start__ end____ width___ exp.time_
 75 omega   83.00  158.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 76 omega   79.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -60.0000 4
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1063454000
_diffrn_orient_matrix_UB_12      0.0692312000
_diffrn_orient_matrix_UB_13      0.0521703000
_diffrn_orient_matrix_UB_21      -0.0795040000
_diffrn_orient_matrix_UB_22      0.0001555000
_diffrn_orient_matrix_UB_23      0.0977254000
_diffrn_orient_matrix_UB_31      0.0667698000
_diffrn_orient_matrix_UB_32      -0.1102660000
_diffrn_orient_matrix_UB_33      0.0330475000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3355
_reflns_number_total             3410
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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         0.209
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.052
_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)+(0.0476P)²+0.3068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0754
_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:
 C3(H3), C5(H5), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C15(H15A,H15B),
 C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_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
C1 C 0.47120(14) 0.62228(12) 0.26218(11) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.56349(14) 0.72001(13) 0.24304(10) 0.0176(3) Uani 1 1 d . . . . .
H2A H 0.528535 0.768072 0.188639 0.021 Uiso 1 1 calc R . . . .
H2B H 0.647493 0.689587 0.220317 0.021 Uiso 1 1 calc R . . . .
C3 C 0.58438(14) 0.79232(12) 0.33677(11) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.634670 0.863527 0.326605 0.019 Uiso 1 1 calc R . . . .
C4 C 0.45408(14) 0.80533(12) 0.39474(10) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.48714(14) 0.68615(12) 0.44217(11) 0.0148(3) Uani 1 1 d . . . . .
H5 H 0.462824 0.676973 0.514343 0.018 Uiso 1 1 calc R . . . .
C6 C 0.44867(13) 0.58767(12) 0.37342(10) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.31123(14) 0.54426(12) 0.39018(11) 0.0162(3) Uani 1 1 d . . . . .
H7A H 0.290587 0.486668 0.338708 0.019 Uiso 1 1 calc R . . . .
H7B H 0.249669 0.607609 0.382355 0.019 Uiso 1 1 calc R . . . .
C8 C 0.29549(13) 0.49218(12) 0.49501(11) 0.0165(3) Uani 1 1 d . . . . .
H8A H 0.288799 0.553035 0.545753 0.020 Uiso 1 1 calc R . . . .
H8B H 0.215305 0.446865 0.497488 0.020 Uiso 1 1 calc R . . . .
C9 C 0.40913(14) 0.41820(12) 0.51847(10) 0.0154(3) Uani 1 1 d . . . . .
C10 C 0.40687(15) 0.33160(11) 0.60269(11) 0.0158(3) Uani 1 1 d . . . . .
H10 H 0.323923 0.324513 0.640438 0.019 Uiso 1 1 calc R . . . .
C11 C 0.53245(15) 0.34086(11) 0.66793(10) 0.0158(3) Uani 1 1 d . . . . .
C12 C 0.59842(14) 0.27419(12) 0.58032(11) 0.0166(3) Uani 1 1 d . . . . .
H12 H 0.667767 0.220358 0.601191 0.020 Uiso 1 1 calc R . . . .
C13 C 0.63307(14) 0.35245(12) 0.49208(11) 0.0178(3) Uani 1 1 d . . . . .
H13A H 0.706582 0.401467 0.510871 0.021 Uiso 1 1 calc R . . . .
H13B H 0.658798 0.306660 0.433196 0.021 Uiso 1 1 calc R . . . .
C14 C 0.51798(14) 0.42418(12) 0.46596(10) 0.0157(3) Uani 1 1 d . . . . .
C15 C 0.63137(14) 0.71501(13) 0.42277(11) 0.0176(3) Uani 1 1 d . . . . .
H15A H 0.673742 0.755819 0.478629 0.021 Uiso 1 1 calc R . . . .
H15B H 0.683904 0.649917 0.400200 0.021 Uiso 1 1 calc R . . . .
C16 C 0.33219(15) 0.82491(13) 0.33252(11) 0.0177(3) Uani 1 1 d . . . . .
H16A H 0.339624 0.896711 0.296282 0.027 Uiso 1 1 calc GR . . . .
H16B H 0.257090 0.827567 0.377102 0.027 Uiso 1 1 calc GR . . . .
H16C H 0.321759 0.763017 0.284312 0.027 Uiso 1 1 calc GR . . . .
C17 C 0.46089(15) 0.89869(12) 0.47418(11) 0.0193(3) Uani 1 1 d . . . . .
H17A H 0.460204 0.972692 0.441117 0.029 Uiso 1 1 calc GR . . . .
H17B H 0.540466 0.890437 0.513165 0.029 Uiso 1 1 calc GR . . . .
H17C H 0.386367 0.892690 0.519087 0.029 Uiso 1 1 calc GR . . . .
C18 C 0.46415(15) 0.21956(12) 0.55952(11) 0.0179(3) Uani 1 1 d . . . . .
H18A H 0.445542 0.151568 0.600348 0.021 Uiso 1 1 calc R . . . .
H18B H 0.445257 0.206552 0.487603 0.021 Uiso 1 1 calc R . . . .
C19 C 0.52460(15) 0.26967(13) 0.76389(11) 0.0205(3) Uani 1 1 d . . . . .
H19A H 0.466422 0.306332 0.811850 0.031 Uiso 1 1 calc GR . . . .
H19B H 0.610692 0.262948 0.793625 0.031 Uiso 1 1 calc GR . . . .
H19C H 0.491680 0.194235 0.747543 0.031 Uiso 1 1 calc GR . . . .
C20 C 0.58068(16) 0.45813(13) 0.69589(12) 0.0211(3) Uani 1 1 d . . . . .
H20A H 0.586316 0.504936 0.635356 0.032 Uiso 1 1 calc GR . . . .
H20B H 0.666145 0.452045 0.726799 0.032 Uiso 1 1 calc GR . . . .
H20C H 0.520649 0.492974 0.743538 0.032 Uiso 1 1 calc GR . . . .
O1 O 0.41651(12) 0.57386(9) 0.19467(8) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.53973(10) 0.49496(9) 0.38483(8) 0.0173(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
C1 C2 1.522(2) . ?
C1 C6 1.5553(19) . ?
C1 O1 1.2078(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5290(19) . ?
C3 H3 1.0000 . ?
C3 C4 1.5641(19) . ?
C3 C15 1.5448(19) . ?
C4 C5 1.5826(19) . ?
C4 C16 1.529(2) . ?
C4 C17 1.5312(19) . ?
C5 H5 1.0000 . ?
C5 C6 1.5346(19) . ?
C5 C15 1.556(2) . ?
C6 C7 1.5315(19) . ?
C6 O2 1.4552(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.535(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5008(19) . ?
C9 C10 1.5195(19) . ?
C9 C14 1.330(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.570(2) . ?
C10 C18 1.562(2) . ?
C11 C12 1.5661(19) . ?
C11 C19 1.5331(19) . ?
C11 C20 1.5211(19) . ?
C12 H12 1.0000 . ?
C12 C13 1.539(2) . ?
C12 C18 1.560(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5052(19) . ?
C14 O2 1.3858(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 116.99(12) . . ?
O1 C1 C2 122.06(13) . . ?
O1 C1 C6 120.95(13) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 112.16(11) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C2 C3 H3 115.8 . . ?
C2 C3 C4 109.63(12) . . ?
C2 C3 C15 108.61(12) . . ?
C4 C3 H3 115.8 . . ?
C15 C3 H3 115.8 . . ?
C15 C3 C4 87.97(10) . . ?
C3 C4 C5 85.54(10) . . ?
C16 C4 C3 117.48(11) . . ?
C16 C4 C5 122.03(12) . . ?
C16 C4 C17 107.67(12) . . ?
C17 C4 C3 111.86(12) . . ?
C17 C4 C5 110.89(11) . . ?
C4 C5 H5 115.2 . . ?
C6 C5 C4 112.44(11) . . ?
C6 C5 H5 115.2 . . ?
C6 C5 C15 108.50(12) . . ?
C15 C5 C4 86.93(10) . . ?
C15 C5 H5 115.2 . . ?
C5 C6 C1 109.26(11) . . ?
C7 C6 C1 111.53(11) . . ?
C7 C6 C5 114.17(12) . . ?
O2 C6 C1 101.56(11) . . ?
O2 C6 C5 109.94(11) . . ?
O2 C6 C7 109.64(11) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.47(12) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.88(12) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 C10 122.33(12) . . ?
C14 C9 C8 121.73(13) . . ?
C14 C9 C10 115.94(13) . . ?
C9 C10 H10 116.2 . . ?
C9 C10 C11 110.43(12) . . ?
C9 C10 C18 107.11(11) . . ?
C11 C10 H10 116.2 . . ?
C18 C10 H10 116.2 . . ?
C18 C10 C11 86.99(11) . . ?
C12 C11 C10 85.11(10) . . ?
C19 C11 C10 112.30(12) . . ?
C19 C11 C12 111.60(12) . . ?
C20 C11 C10 118.17(12) . . ?
C20 C11 C12 119.88(13) . . ?
C20 C11 C19 108.31(12) . . ?
C11 C12 H12 115.3 . . ?
C13 C12 C11 111.61(11) . . ?
C13 C12 H12 115.3 . . ?
C13 C12 C18 108.78(12) . . ?
C18 C12 C11 87.19(11) . . ?
C18 C12 H12 115.3 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 C12 109.31(12) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C9 C14 C13 121.43(13) . . ?
C9 C14 O2 125.50(13) . . ?
O2 C14 C13 113.07(12) . . ?
C3 C15 C5 87.12(11) . . ?
C3 C15 H15A 114.1 . . ?
C3 C15 H15B 114.1 . . ?
C5 C15 H15A 114.1 . . ?
C5 C15 H15B 114.1 . . ?
H15A C15 H15B 111.3 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 H18A 114.4 . . ?
C10 C18 H18B 114.4 . . ?
C12 C18 C10 85.56(10) . . ?
C12 C18 H18A 114.4 . . ?
C12 C18 H18B 114.4 . . ?
H18A C18 H18B 111.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 O2 C6 115.54(11) . . ?

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 -39.01(15) . . . . ?
C1 C2 C3 C15 55.61(15) . . . . ?
C1 C6 C7 C8 170.68(11) . . . . ?
C1 C6 O2 C14 -161.94(11) . . . . ?
C2 C1 C6 C5 20.15(17) . . . . ?
C2 C1 C6 C7 147.32(12) . . . . ?
C2 C1 C6 O2 -95.97(13) . . . . ?
C2 C3 C4 C5 82.93(12) . . . . ?
C2 C3 C4 C16 -41.07(17) . . . . ?
C2 C3 C4 C17 -166.33(12) . . . . ?
C2 C3 C15 C5 -83.49(12) . . . . ?
C3 C4 C5 C6 -82.82(13) . . . . ?
C3 C4 C5 C15 25.94(10) . . . . ?
C4 C3 C15 C5 26.55(10) . . . . ?
C4 C5 C6 C1 35.73(16) . . . . ?
C4 C5 C6 C7 -89.93(14) . . . . ?
C4 C5 C6 O2 146.37(11) . . . . ?
C4 C5 C15 C3 -26.24(10) . . . . ?
C5 C6 C7 C8 -64.87(15) . . . . ?
C5 C6 O2 C14 82.44(14) . . . . ?
C6 C1 C2 C3 -18.87(17) . . . . ?
C6 C5 C15 C3 86.41(12) . . . . ?
C6 C7 C8 C9 -44.01(15) . . . . ?
C7 C6 O2 C14 -43.86(15) . . . . ?
C7 C8 C9 C10 -163.55(12) . . . . ?
C7 C8 C9 C14 15.98(19) . . . . ?
C8 C9 C10 C11 -132.95(13) . . . . ?
C8 C9 C10 C18 133.84(13) . . . . ?
C8 C9 C14 C13 177.94(13) . . . . ?
C8 C9 C14 O2 -1.2(2) . . . . ?
C9 C10 C11 C12 -78.40(12) . . . . ?
C9 C10 C11 C19 170.24(11) . . . . ?
C9 C10 C11 C20 43.03(17) . . . . ?
C9 C10 C18 C12 81.61(12) . . . . ?
C9 C14 O2 C6 16.0(2) . . . . ?
C10 C9 C14 C13 -2.49(19) . . . . ?
C10 C9 C14 O2 178.39(13) . . . . ?
C10 C11 C12 C13 80.31(13) . . . . ?
C10 C11 C12 C18 -28.79(10) . . . . ?
C11 C10 C18 C12 -28.86(10) . . . . ?
C11 C12 C13 C14 -48.64(16) . . . . ?
C11 C12 C18 C10 28.92(10) . . . . ?
C12 C13 C14 C9 2.68(19) . . . . ?
C12 C13 C14 O2 -178.10(12) . . . . ?
C13 C12 C18 C10 -82.97(12) . . . . ?
C13 C14 O2 C6 -163.18(12) . . . . ?
C14 C9 C10 C11 47.49(16) . . . . ?
C14 C9 C10 C18 -45.73(16) . . . . ?
C15 C3 C4 C5 -26.12(10) . . . . ?
C15 C3 C4 C16 -150.12(13) . . . . ?
C15 C3 C4 C17 84.62(13) . . . . ?
C15 C5 C6 C1 -58.70(14) . . . . ?
C15 C5 C6 C7 175.65(11) . . . . ?
C15 C5 C6 O2 51.95(14) . . . . ?
C16 C4 C5 C6 36.99(18) . . . . ?
C16 C4 C5 C15 145.76(13) . . . . ?
C17 C4 C5 C6 165.46(12) . . . . ?
C17 C4 C5 C15 -85.78(13) . . . . ?
C18 C10 C11 C12 28.75(10) . . . . ?
C18 C10 C11 C19 -82.61(12) . . . . ?
C18 C10 C11 C20 150.18(13) . . . . ?
C18 C12 C13 C14 45.89(15) . . . . ?
C19 C11 C12 C13 -167.62(12) . . . . ?
C19 C11 C12 C18 83.28(13) . . . . ?
C20 C11 C12 C13 -39.51(18) . . . . ?
C20 C11 C12 C18 -148.61(13) . . . . ?
O1 C1 C2 C3 160.48(14) . . . . ?
O1 C1 C6 C5 -159.20(13) . . . . ?
O1 C1 C6 C7 -32.04(19) . . . . ?
O1 C1 C6 O2 84.68(15) . . . . ?
O2 C6 C7 C8 58.99(15) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_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 -6 6 0.0607 0.0004 -5.9992 6.0003 -0.1023 0.5854 0.8598
0 6 -6 0.0722 -0.0004 5.9992 -6.0003 0.1023 -0.5854 -0.8598
5 -3 -4 0.1609 5.0000 -2.9999 -3.9999 0.1154 -0.7889 0.5325
-5 5 1 0.1493 -5.0002 4.9996 0.9998 -0.1335 0.4960 -0.8521
4 3 6 0.0566 4.0002 3.0008 6.0000 0.9462 0.2688 0.1345
-4 -4 -5 0.1148 -4.0002 -4.0006 -5.0000 -0.9632 -0.1712 0.0088
-5 0 -6 0.1064 -5.0003 -0.0009 -6.0001 -0.8449 -0.1888 -0.5321
6 1 -2 0.1367 6.0000 1.0002 -2.0000 0.6030 -0.6723 0.2242
-3 -6 4 0.1085 -2.9997 -5.9996 4.0002 -0.5257 0.6285 0.5935
-1 -7 4 0.0873 -0.9997 -6.9995 4.0003 -0.3822 0.4693 0.8373
6 -3 0 0.1531 6.0002 -2.9995 0.0002 0.4304 -0.4775 0.7314
5 4 -3 0.1231 4.9999 3.9999 -3.0001 0.6521 -0.6901 -0.2064
-1 4 7 0.0772 -0.9998 4.0005 6.9999 0.5358 0.7642 -0.2765
1 -5 -6 0.1774 0.9999 -5.0003 -5.9999 -0.5529 -0.6666 0.4199
-3 3 -7 0.0904 -3.0004 2.9990 -7.0002 -0.4767 -0.4451 -0.7624

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_spocpr
_database_code_depnum_ccdc_archive 'CCDC 1571409'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_nottingham_internal_coll_name   SPOCPR
_nottingham_internal_coll_number 8600
_nottingham_internal_coll_client MU/CJH
_nottingham_internal_coll_type   ?
_nottingham_internal_coll_frame_method ?
_nottingham_internal_coll_frame_time ?
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   pczajb
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SMART APEX'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date ?
_nottingham_internal_process_user pczajb
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user ?
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user ?
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 29/8/2017
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date ?
_refine_special_details          ?
_vrf_PLAT907_spocpr              
;
PROBLEM: Flack x > 0.5, Structure needs to be Inverted? .       1.70 Check 
RESPONSE: The flack parameter is unreliable for this structure due to 
the very weak anomalous signal for a light atom structure with Mo 
radiation. The chirality was established based on the synthesis.
;
_vrf_STRVA01_spocpr              
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: The flack parameter is unreliable for this structure due to 
the very weak anomalous signal for a light atom structure with Mo 
radiation. The chirality was established based on the synthesis.
;
_audit_creation_date             2017-08-29
_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         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.6086(3)
_cell_length_b                   9.9529(5)
_cell_length_c                   25.6799(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1689.09(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23682
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4; Sheldrick, 1996)'
_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    1.181
_exptl_crystal_density_meas      x
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11395
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.688
_diffrn_reflns_theta_min         3.139
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                3374
_reflns_number_total             3795
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1192 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(7)
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.063
_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)+1.0793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0988
_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:
 C3(H3), C4(H4), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C13(H13A,
 H13B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.0877(3) 0.1025(2) 0.21103(7) 0.0300(5) Uani 1 1 d . . . . .
C1 C 0.9283(4) 0.1502(3) 0.22553(10) 0.0220(6) Uani 1 1 d . . . . .
C2 C 0.9177(4) 0.2590(3) 0.26667(10) 0.0256(6) Uani 1 1 d . . . . .
H2A H 0.916141 0.347296 0.248959 0.031 Uiso 1 1 calc R . . . .
H2B H 1.042699 0.254704 0.287871 0.031 Uiso 1 1 calc R . . . .
C3 C 0.7375(4) 0.2521(3) 0.30304(9) 0.0228(6) Uani 1 1 d . . . . .
H3 H 0.684017 0.341115 0.314709 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5771(4) 0.1441(3) 0.29427(10) 0.0238(6) Uani 1 1 d . . . . .
H4 H 0.434910 0.173416 0.301239 0.029 Uiso 1 1 calc R . . . .
C5 C 0.6007(4) 0.0460(3) 0.24945(10) 0.0240(6) Uani 1 1 d . . . . .
H5A H 0.464778 0.020431 0.236608 0.029 Uiso 1 1 calc R . . . .
H5B H 0.667850 -0.036406 0.262360 0.029 Uiso 1 1 calc R . . . .
C6 C 0.7238(4) 0.1033(3) 0.20415(10) 0.0203(5) Uani 1 1 d . . . . .
O2 O 0.7536(3) -0.00620(18) 0.16911(7) 0.0229(4) Uani 1 1 d . . . . .
C7 C 0.6125(4) 0.2180(3) 0.17687(10) 0.0235(6) Uani 1 1 d . . . . .
H7A H 0.476802 0.187052 0.165828 0.028 Uiso 1 1 calc R . . . .
H7B H 0.594477 0.293751 0.201444 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7314(4) 0.2657(3) 0.12940(10) 0.0248(6) Uani 1 1 d . . . . .
H8A H 0.641011 0.317948 0.106266 0.030 Uiso 1 1 calc R . . . .
H8B H 0.842446 0.325632 0.140837 0.030 Uiso 1 1 calc R . . . .
C9 C 0.8188(4) 0.1486(3) 0.09958(10) 0.0209(5) Uani 1 1 d . . . . .
C10 C 0.9007(4) 0.1801(3) 0.04616(10) 0.0243(6) Uani 1 1 d . . . . .
H10A H 1.003533 0.251794 0.049707 0.029 Uiso 1 1 calc R . . . .
H10B H 0.788805 0.216650 0.024807 0.029 Uiso 1 1 calc R . . . .
C11 C 0.9951(4) 0.0642(3) 0.01680(10) 0.0234(6) Uani 1 1 d . . . . .
H11 H 0.971206 0.065120 -0.021646 0.028 Uiso 1 1 calc R . . . .
C12 C 0.9996(4) -0.0742(3) 0.04122(10) 0.0234(6) Uani 1 1 d . . . . .
H12 H 0.978450 -0.149861 0.016184 0.028 Uiso 1 1 calc R . . . .
C13 C 0.9088(4) -0.0966(3) 0.09462(10) 0.0236(6) Uani 1 1 d . . . . .
H13A H 0.798597 -0.163493 0.091553 0.028 Uiso 1 1 calc R . . . .
H13B H 1.014005 -0.135400 0.117583 0.028 Uiso 1 1 calc R . . . .
C14 C 0.8262(4) 0.0267(3) 0.11989(10) 0.0210(6) Uani 1 1 d . . . . .
C15 C 0.7125(4) 0.1392(3) 0.34181(10) 0.0239(6) Uani 1 1 d . . . . .
C16 C 0.6150(5) 0.1737(3) 0.39330(11) 0.0330(7) Uani 1 1 d . . . . .
H16A H 0.515734 0.245628 0.388146 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.719102 0.203834 0.417847 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.546978 0.094046 0.407314 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.8735(5) 0.0322(3) 0.34638(11) 0.0327(7) Uani 1 1 d . . . . .
H17A H 0.974453 0.059974 0.372187 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.939383 0.019766 0.312527 0.049 Uiso 1 1 calc GR . . . .
H17C H 0.811266 -0.052514 0.357380 0.049 Uiso 1 1 calc GR . . . .
C18 C 1.1939(4) 0.0026(3) 0.03346(10) 0.0233(6) Uani 1 1 d . . . . .
C19 C 1.3361(5) -0.0482(3) -0.00870(11) 0.0313(7) Uani 1 1 d . . . . .
H19A H 1.418576 0.026420 -0.021669 0.047 Uiso 1 1 calc GR . . . .
H19B H 1.256720 -0.086064 -0.037418 0.047 Uiso 1 1 calc GR . . . .
H19C H 1.424496 -0.117858 0.005797 0.047 Uiso 1 1 calc GR . . . .
C20 C 1.3030(4) 0.0622(3) 0.07987(11) 0.0263(6) Uani 1 1 d . . . . .
H20A H 1.204066 0.087065 0.106627 0.039 Uiso 1 1 calc GR . . . .
H20B H 1.377950 0.142324 0.068910 0.039 Uiso 1 1 calc GR . . . .
H20C H 1.397482 -0.004147 0.094123 0.039 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.214(3) . ?
C1 C2 1.514(4) . ?
C1 C6 1.532(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.515(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.527(4) . ?
C3 C15 1.510(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.517(4) . ?
C4 C15 1.514(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(4) . ?
C6 O2 1.427(3) . ?
C6 C7 1.528(4) . ?
O2 C14 1.391(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.510(4) . ?
C9 C10 1.508(3) . ?
C9 C14 1.322(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.512(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.514(4) . ?
C11 C18 1.512(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.513(4) . ?
C12 C18 1.508(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.491(4) . ?
C15 C16 1.510(4) . ?
C15 C17 1.510(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.520(4) . ?
C18 C20 1.514(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.3(2) . . ?
O1 C1 C6 122.4(2) . . ?
C2 C1 C6 115.3(2) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C1 C2 C3 115.7(2) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C2 C3 H3 115.0 . . ?
C2 C3 C4 119.1(2) . . ?
C4 C3 H3 115.0 . . ?
C15 C3 C2 121.7(2) . . ?
C15 C3 H3 115.0 . . ?
C15 C3 C4 59.82(17) . . ?
C3 C4 H4 114.9 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 114.9 . . ?
C15 C4 C3 59.55(17) . . ?
C15 C4 H4 114.9 . . ?
C15 C4 C5 122.0(2) . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C4 C5 C6 113.1(2) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 C1 108.1(2) . . ?
O2 C6 C1 109.7(2) . . ?
O2 C6 C5 105.5(2) . . ?
O2 C6 C7 110.4(2) . . ?
C7 C6 C1 111.2(2) . . ?
C7 C6 C5 111.8(2) . . ?
C14 O2 C6 116.15(19) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.5(2) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.2(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 C8 116.0(2) . . ?
C14 C9 C8 121.5(2) . . ?
C14 C9 C10 122.4(2) . . ?
C9 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
C9 C10 C11 116.3(2) . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C10 C11 H11 114.9 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 114.9 . . ?
C18 C11 C10 121.8(2) . . ?
C18 C11 H11 114.9 . . ?
C18 C11 C12 59.78(17) . . ?
C11 C12 H12 114.6 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 114.6 . . ?
C18 C12 C11 60.04(18) . . ?
C18 C12 H12 114.6 . . ?
C18 C12 C13 122.2(2) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.7(2) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
O2 C14 C13 109.2(2) . . ?
C9 C14 O2 124.2(2) . . ?
C9 C14 C13 126.7(2) . . ?
C3 C15 C4 60.63(17) . . ?
C3 C15 C16 117.1(2) . . ?
C3 C15 C17 119.9(2) . . ?
C16 C15 C4 116.5(2) . . ?
C17 C15 C4 120.1(2) . . ?
C17 C15 C16 113.1(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 C19 118.1(2) . . ?
C11 C18 C20 118.5(2) . . ?
C12 C18 C11 60.18(18) . . ?
C12 C18 C19 116.8(2) . . ?
C12 C18 C20 120.0(2) . . ?
C20 C18 C19 113.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -144.7(3) . . . . ?
O1 C1 C6 C5 118.4(3) . . . . ?
O1 C1 C6 O2 3.9(3) . . . . ?
O1 C1 C6 C7 -118.5(3) . . . . ?
C1 C2 C3 C4 -3.3(4) . . . . ?
C1 C2 C3 C15 67.4(3) . . . . ?
C1 C6 O2 C14 -76.4(3) . . . . ?
C1 C6 C7 C8 63.5(3) . . . . ?
C2 C1 C6 C5 -60.7(3) . . . . ?
C2 C1 C6 O2 -175.2(2) . . . . ?
C2 C1 C6 C7 62.4(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C4 C15 111.9(3) . . . . ?
C2 C3 C15 C4 -107.6(3) . . . . ?
C2 C3 C15 C16 145.7(3) . . . . ?
C2 C3 C15 C17 2.3(4) . . . . ?
C3 C4 C5 C6 -27.0(3) . . . . ?
C3 C4 C15 C16 107.6(3) . . . . ?
C3 C4 C15 C17 -109.6(3) . . . . ?
C4 C3 C15 C16 -106.7(3) . . . . ?
C4 C3 C15 C17 109.9(3) . . . . ?
C4 C5 C6 C1 55.2(3) . . . . ?
C4 C5 C6 O2 172.5(2) . . . . ?
C4 C5 C6 C7 -67.4(3) . . . . ?
C5 C4 C15 C3 107.9(3) . . . . ?
C5 C4 C15 C16 -144.5(3) . . . . ?
C5 C4 C15 C17 -1.7(4) . . . . ?
C5 C6 O2 C14 167.4(2) . . . . ?
C5 C6 C7 C8 -175.6(2) . . . . ?
C6 C1 C2 C3 34.4(3) . . . . ?
C6 O2 C14 C9 -18.3(4) . . . . ?
C6 O2 C14 C13 162.5(2) . . . . ?
C6 C7 C8 C9 41.3(3) . . . . ?
O2 C6 C7 C8 -58.5(3) . . . . ?
C7 C6 O2 C14 46.5(3) . . . . ?
C7 C8 C9 C10 167.4(2) . . . . ?
C7 C8 C9 C14 -14.0(4) . . . . ?
C8 C9 C10 C11 177.9(2) . . . . ?
C8 C9 C14 O2 1.0(4) . . . . ?
C8 C9 C14 C13 -179.8(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C9 C10 C11 C18 -69.8(3) . . . . ?
C10 C9 C14 O2 179.6(2) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C18 -111.7(3) . . . . ?
C10 C11 C18 C12 108.3(3) . . . . ?
C10 C11 C18 C19 -145.2(3) . . . . ?
C10 C11 C18 C20 -1.9(4) . . . . ?
C11 C12 C13 C14 -2.1(4) . . . . ?
C11 C12 C18 C19 -108.5(3) . . . . ?
C11 C12 C18 C20 107.7(3) . . . . ?
C12 C11 C18 C19 106.5(3) . . . . ?
C12 C11 C18 C20 -110.2(3) . . . . ?
C12 C13 C14 O2 -178.1(2) . . . . ?
C12 C13 C14 C9 2.7(4) . . . . ?
C13 C12 C18 C11 -108.7(3) . . . . ?
C13 C12 C18 C19 142.7(3) . . . . ?
C13 C12 C18 C20 -1.0(4) . . . . ?
C14 C9 C10 C11 -0.7(4) . . . . ?
C15 C3 C4 C5 -112.0(3) . . . . ?
C15 C4 C5 C6 -97.6(3) . . . . ?
C18 C11 C12 C13 112.1(3) . . . . ?
C18 C12 C13 C14 69.4(3) . . . . ?

_olex2_date_sample_data_collection 2009-05-26
_olex2_date_sample_submission    2009-04-25
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cypspo
_database_code_depnum_ccdc_archive 'CCDC 1571408'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_nottingham_internal_coll_name   CYPSPO
_nottingham_internal_coll_number 8601
_nottingham_internal_coll_client MU/CJH
_nottingham_internal_coll_type   ?
_nottingham_internal_coll_frame_method ?
_nottingham_internal_coll_frame_time ?
_nottingham_internal_coll_frame_width 0.3
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SMART APEX'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date ?
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user ?
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user ?
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 29/8/2017
_nottingham_internal_validation_user pczwl
_refine_special_details          ?
_vrf_PLAT907_cypspo              
;
PROBLEM: Flack x > 0.5, Structure needs to be Inverted? .       1.70 Check 
RESPONSE: The flack parameter is unreliable for this structure due to 
the very weak anomalous signal for a light atom structure with Mo 
radiation. The chirality was established based on the synthesis.
;
_vrf_STRVA01_cypspo              
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE: The flack parameter is unreliable for this structure due to 
the very weak anomalous signal for a light atom structure with Mo 
radiation. The chirality was established based on the synthesis.
;
_audit_creation_date             2017-08-29
_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         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2525(6)
_cell_length_b                   10.9938(10)
_cell_length_c                   24.717(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1699.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.543
_cell_measurement_theta_min      2.479
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.8723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2007/2 (Bruker,2007) was used for absorption correction. wR2(int) was 0.0545 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.8898. The λ/2 correction factor is 0.0015.'
_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    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method 
'slow evaporation of a pentane solution of the compound'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15135
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.027
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3681
_reflns_number_total             3900
_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       'SAINT V6.36A (Bruker, 2016)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (Bruker, 2016)'
_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    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.184
_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)+(0.0526P)²+0.3481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1211
_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:
 C3(H3), C4(H4), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C5(H5a,H5b), C7(H7a,H7b), C8(H8a,H8b), C10(H10a,H10b), C13(H13a,
 H13b)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c), C20(H20a,H20b,
 H20c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5805(4) 0.7838(2) 0.80610(9) 0.0226(5) Uani 1 1 d . . . . .
O1 O 0.4581(3) 0.71474(17) 0.82844(8) 0.0330(5) Uani 1 1 d . . . . .
C2 C 0.5074(4) 0.8967(2) 0.77659(11) 0.0262(5) Uani 1 1 d . . . . .
H2A H 0.523470 0.967387 0.801070 0.031 Uiso 1 1 calc R . . . .
H2B H 0.353441 0.888242 0.768075 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6285(4) 0.9229(2) 0.72421(10) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.654681 1.011117 0.716810 0.031 Uiso 1 1 calc R . . . .
C4 C 0.8087(4) 0.8386(2) 0.70703(10) 0.0262(6) Uani 1 1 d . . . . .
H4 H 0.934003 0.880317 0.690064 0.031 Uiso 1 1 calc R . . . .
C5 C 0.8659(4) 0.7316(2) 0.74332(10) 0.0270(6) Uani 1 1 d . . . . .
H5A H 1.019413 0.712033 0.738724 0.032 Uiso 1 1 calc R . . . .
H5B H 0.782064 0.659560 0.732081 0.032 Uiso 1 1 calc R . . . .
C6 C 0.8216(4) 0.7583(2) 0.80296(10) 0.0231(5) Uani 1 1 d . . . . .
O2 O 0.9346(3) 0.86976(16) 0.81420(7) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.8952(5) 0.6570(2) 0.83995(11) 0.0287(6) Uani 1 1 d . . . . .
H7A H 1.047252 0.638393 0.832422 0.034 Uiso 1 1 calc R . . . .
H7B H 0.810506 0.582810 0.832439 0.034 Uiso 1 1 calc R . . . .
C8 C 0.8703(5) 0.6914(2) 0.89936(11) 0.0306(6) Uani 1 1 d . . . . .
H8A H 0.719378 0.680263 0.910424 0.037 Uiso 1 1 calc R . . . .
H8B H 0.959920 0.637078 0.921839 0.037 Uiso 1 1 calc R . . . .
C9 C 0.9356(4) 0.8218(2) 0.90889(10) 0.0236(5) Uani 1 1 d . . . . .
C10 C 0.9735(4) 0.8580(2) 0.96666(10) 0.0260(5) Uani 1 1 d . . . . .
H10A H 1.085065 0.803879 0.981802 0.031 Uiso 1 1 calc R . . . .
H10B H 0.840336 0.842958 0.987254 0.031 Uiso 1 1 calc R . . . .
C11 C 1.0412(4) 0.9883(2) 0.97639(10) 0.0270(6) Uani 1 1 d . . . . .
H11 H 0.978688 1.026622 1.009487 0.032 Uiso 1 1 calc R . . . .
C12 C 1.0721(4) 1.0740(2) 0.92896(10) 0.0265(6) Uani 1 1 d . . . . .
H12 H 1.026693 1.159830 0.935753 0.032 Uiso 1 1 calc R . . . .
C13 C 1.0326(4) 1.0287(2) 0.87215(10) 0.0236(5) Uani 1 1 d . . . . .
H13A H 0.921716 1.080541 0.855221 0.028 Uiso 1 1 calc R . . . .
H13B H 1.165757 1.038724 0.850949 0.028 Uiso 1 1 calc R . . . .
C14 C 0.9627(4) 0.8988(2) 0.86831(10) 0.0208(5) Uani 1 1 d . . . . .
C15 C 0.6039(4) 0.8447(2) 0.67432(10) 0.0270(6) Uani 1 1 d . . . . .
C16 C 0.6157(6) 0.9093(3) 0.62036(11) 0.0380(7) Uani 1 1 d . . . . .
H16A H 0.473892 0.940594 0.610815 0.057 Uiso 1 1 calc GR . . . .
H16B H 0.663678 0.852040 0.592490 0.057 Uiso 1 1 calc GR . . . .
H16C H 0.717119 0.976991 0.622830 0.057 Uiso 1 1 calc GR . . . .
C17 C 0.4475(5) 0.7396(2) 0.67450(11) 0.0311(6) Uani 1 1 d . . . . .
H17A H 0.304955 0.769170 0.664601 0.047 Uiso 1 1 calc GR . . . .
H17B H 0.442454 0.703389 0.710712 0.047 Uiso 1 1 calc GR . . . .
H17C H 0.493909 0.678081 0.648295 0.047 Uiso 1 1 calc GR . . . .
C18 C 1.2625(4) 1.0321(2) 0.96174(11) 0.0261(6) Uani 1 1 d . . . . .
C19 C 1.3642(6) 1.1239(3) 0.99917(13) 0.0415(8) Uani 1 1 d . . . . .
H19A H 1.433668 1.081465 1.029270 0.062 Uiso 1 1 calc GR . . . .
H19B H 1.253892 1.178690 1.013337 0.062 Uiso 1 1 calc GR . . . .
H19C H 1.470989 1.171284 0.979201 0.062 Uiso 1 1 calc GR . . . .
C20 C 1.4199(4) 0.9444(3) 0.93720(12) 0.0304(6) Uani 1 1 d . . . . .
H20A H 1.490279 0.898136 0.966030 0.046 Uiso 1 1 calc GR . . . .
H20B H 1.527493 0.989652 0.916568 0.046 Uiso 1 1 calc GR . . . .
H20C H 1.344248 0.888333 0.913036 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.211(3) . ?
C1 C2 1.511(4) . ?
C1 C6 1.535(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.527(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.520(4) . ?
C3 C15 1.512(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(4) . ?
C4 C15 1.516(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.528(4) . ?
C6 O2 1.441(3) . ?
C6 C7 1.513(4) . ?
O2 C14 1.386(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(4) . ?
C9 C10 1.501(4) . ?
C9 C14 1.323(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.516(4) . ?
C11 C18 1.509(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.510(3) . ?
C12 C18 1.512(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.496(3) . ?
C15 C16 1.513(4) . ?
C15 C17 1.514(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.510(4) . ?
C18 C20 1.505(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 123.0(2) . . ?
O1 C1 C6 122.0(2) . . ?
C2 C1 C6 115.0(2) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 C3 114.5(2) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C2 C3 H3 114.8 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 114.8 . . ?
C15 C3 C2 122.2(2) . . ?
C15 C3 H3 114.8 . . ?
C15 C3 C4 60.01(17) . . ?
C3 C4 H4 114.7 . . ?
C3 C4 C5 118.8(2) . . ?
C5 C4 H4 114.7 . . ?
C15 C4 C3 59.73(17) . . ?
C15 C4 H4 114.7 . . ?
C15 C4 C5 123.2(2) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 112.2(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 C1 105.2(2) . . ?
O2 C6 C1 108.5(2) . . ?
O2 C6 C5 105.1(2) . . ?
O2 C6 C7 111.1(2) . . ?
C7 C6 C1 113.7(2) . . ?
C7 C6 C5 112.7(2) . . ?
C14 O2 C6 116.35(18) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.6(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.0(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 C8 116.3(2) . . ?
C14 C9 C8 121.6(2) . . ?
C14 C9 C10 122.1(2) . . ?
C9 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
C9 C10 C11 116.5(2) . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C10 C11 H11 114.8 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 114.8 . . ?
C18 C11 C10 121.4(2) . . ?
C18 C11 H11 114.8 . . ?
C18 C11 C12 59.95(17) . . ?
C11 C12 H12 114.9 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 114.9 . . ?
C13 C12 C18 121.8(2) . . ?
C18 C12 C11 59.79(17) . . ?
C18 C12 H12 114.9 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 114.9(2) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
O2 C14 C13 108.5(2) . . ?
C9 C14 O2 124.6(2) . . ?
C9 C14 C13 126.9(2) . . ?
C3 C15 C4 60.27(17) . . ?
C3 C15 C16 116.6(2) . . ?
C3 C15 C17 119.9(2) . . ?
C16 C15 C4 116.7(2) . . ?
C16 C15 C17 113.1(2) . . ?
C17 C15 C4 120.7(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 C12 60.26(18) . . ?
C11 C18 C19 116.9(3) . . ?
C19 C18 C12 117.2(2) . . ?
C20 C18 C11 119.4(2) . . ?
C20 C18 C12 119.6(2) . . ?
C20 C18 C19 113.6(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C15 69.9(3) . . . . ?
C1 C6 O2 C14 82.8(2) . . . . ?
C1 C6 C7 C8 -66.3(3) . . . . ?
O1 C1 C2 C3 -140.9(3) . . . . ?
O1 C1 C6 C5 111.1(3) . . . . ?
O1 C1 C6 O2 -136.8(2) . . . . ?
O1 C1 C6 C7 -12.7(3) . . . . ?
C2 C1 C6 C5 -65.4(3) . . . . ?
C2 C1 C6 O2 46.6(3) . . . . ?
C2 C1 C6 C7 170.7(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C2 C3 C4 C15 112.5(3) . . . . ?
C2 C3 C15 C4 -107.7(3) . . . . ?
C2 C3 C15 C16 145.3(3) . . . . ?
C2 C3 C15 C17 2.8(4) . . . . ?
C3 C4 C5 C6 -30.0(3) . . . . ?
C3 C4 C15 C16 106.8(3) . . . . ?
C3 C4 C15 C17 -109.1(3) . . . . ?
C4 C3 C15 C16 -107.1(3) . . . . ?
C4 C3 C15 C17 110.5(3) . . . . ?
C4 C5 C6 C1 60.5(3) . . . . ?
C4 C5 C6 O2 -54.0(3) . . . . ?
C4 C5 C6 C7 -175.1(2) . . . . ?
C5 C4 C15 C3 106.5(3) . . . . ?
C5 C4 C15 C16 -146.7(2) . . . . ?
C5 C4 C15 C17 -2.6(4) . . . . ?
C5 C6 O2 C14 -165.2(2) . . . . ?
C5 C6 C7 C8 174.1(2) . . . . ?
C6 C1 C2 C3 35.7(3) . . . . ?
C6 O2 C14 C9 15.1(3) . . . . ?
C6 O2 C14 C13 -166.3(2) . . . . ?
C6 C7 C8 C9 -41.0(3) . . . . ?
O2 C6 C7 C8 56.5(3) . . . . ?
C7 C6 O2 C14 -42.9(3) . . . . ?
C7 C8 C9 C10 -164.6(2) . . . . ?
C7 C8 C9 C14 13.8(4) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C14 O2 0.2(4) . . . . ?
C8 C9 C14 C13 -178.2(2) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C9 C10 C11 C18 -72.4(3) . . . . ?
C10 C9 C14 O2 178.5(2) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C10 C11 C12 C18 -111.1(3) . . . . ?
C10 C11 C18 C12 109.0(3) . . . . ?
C10 C11 C18 C19 -143.6(3) . . . . ?
C10 C11 C18 C20 -0.4(4) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C18 C19 -107.0(3) . . . . ?
C11 C12 C18 C20 109.0(3) . . . . ?
C12 C11 C18 C19 107.5(3) . . . . ?
C12 C11 C18 C20 -109.3(3) . . . . ?
C12 C13 C14 O2 -179.4(2) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C13 C12 C18 C11 -108.1(3) . . . . ?
C13 C12 C18 C19 144.9(3) . . . . ?
C13 C12 C18 C20 0.9(4) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C15 C3 C4 C5 -113.7(3) . . . . ?
C15 C4 C5 C6 -100.9(3) . . . . ?
C18 C11 C12 C13 111.8(3) . . . . ?
C18 C12 C13 C14 71.2(3) . . . . ?

_olex2_date_sample_data_collection 2009-06-11
_olex2_date_sample_submission    2009-06-08
_olex2_submission_special_instructions 'No special instructions were received'
