# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_nhcjhb
_database_code_depnum_ccdc_archive 'CCDC 1030909'
_audit_update_record             
;
2014-10-24 deposited with the CCDC.
2016-01-25 downloaded from the CCDC.
;
_nottingham_internal_coll_name   NHCJHB
_nottingham_internal_coll_number 10024
_nottingham_internal_coll_client NH/CJH
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.6 and 6.4s'
_nottingham_internal_coll_frame_width '1 degree'
_nottingham_internal_coll_user   wl
_nottingham_internal_coll_date   4/1/2011
_nottingham_internal_process_date 05/01/2011
_nottingham_internal_process_user wl
_nottingham_internal_solution_date 5/1/2011
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_date 7/1/2011
_nottingham_internal_refinement_user WL
_nottingham_internal_validation_date 24/10/2014
_nottingham_internal_validation_user WL
_nottingham_internal_archive_date 24/10/2011
_refine_special_details          ?
_audit_creation_date             2014-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H32 O2'
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H32 O2'
_chemical_oxdiff_usercomment     
'NHCJHB #10024 IN FOMBLIN FILM ON MICROMOUNT FOR NH/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                   11.1378(3)
_cell_length_b                   11.3745(2)
_cell_length_c                   13.5667(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1718.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12745
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      77.1368
_cell_measurement_theta_min      3.2548
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2915
_exptl_crystal_size_mid          0.2064
_exptl_crystal_size_min          0.2002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18845
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         5.074
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -65.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127   38.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega   22.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   42.0000  -68.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega   42.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   43.00   71.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   71.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   46.00   73.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   90.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  9 omega   72.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   82.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  117.00  156.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000  -30.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  130.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000    0.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   70.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   93.00  120.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -42.0000 -111.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega  122.00  147.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  104.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 19 omega   41.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 20 omega   51.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -20.0000  168.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   99.00  131.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -20.0000  168.0000 32

#__ type_ start__ end____ width___ exp.time_
 22 omega   66.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -112.0000  111.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   72.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  133.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   15.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   59.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -58.0000  -80.0000 39

#__ type_ start__ end____ width___ exp.time_
 26 omega  100.00  126.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   53.00   79.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000 -120.0000    2.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   93.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -66.0000   28.0000 45

#__ type_ start__ end____ width___ exp.time_
 29 omega   48.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -66.0000   28.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega -113.00  -54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -43.9127 -155.0000  116.0000 59

#__ type_ start__ end____ width___ exp.time_
 31 omega   20.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   54.0000  167.0000 92

#__ type_ start__ end____ width___ exp.time_
 32 omega   14.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 33 omega    2.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127 -125.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 34 omega   14.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       43.9127   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
 36 omega   89.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   45.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
 37 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 38 omega   41.00   77.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000  -45.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 39 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
 40 omega   81.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   77.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 41 omega   80.00   86.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0000   79.0000  111.0000 6
;
_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      -0.0979634000
_diffrn_orient_matrix_UB_12      0.0750827000
_diffrn_orient_matrix_UB_13      -0.0496098000
_diffrn_orient_matrix_UB_21      -0.0962831000
_diffrn_orient_matrix_UB_22      -0.0882174000
_diffrn_orient_matrix_UB_23      0.0342779000
_diffrn_orient_matrix_UB_31      -0.0161048000
_diffrn_orient_matrix_UB_32      0.0701880000
_diffrn_orient_matrix_UB_33      0.0962320000
_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_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3555
_reflns_number_total             3624
_reflns_odcompleteness_completeness 93.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     86.18
_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 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.044
_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)+(0.0734P)²+0.3065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1074
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,
 H13B), C14(H14A,H14B)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.28040(16) 0.77502(16) 0.41111(13) 0.0196(4) Uani 1 1 d . . . . .
H1 H 0.2567 0.7991 0.4793 0.024 Uiso 1 1 calc R . . . .
C2 C 0.18739(16) 0.83197(15) 0.34124(13) 0.0206(4) Uani 1 1 d . . . . .
H2A H 0.1755 0.9146 0.3620 0.025 Uiso 1 1 calc R . . . .
H2B H 0.1098 0.7908 0.3500 0.025 Uiso 1 1 calc R . . . .
C3 C 0.21911(16) 0.83122(15) 0.23011(13) 0.0187(4) Uani 1 1 d . . . . .
H3 H 0.3010 0.7956 0.2256 0.022 Uiso 1 1 calc R . . . .
C4 C 0.22940(17) 0.95172(16) 0.18193(14) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.27964(18) 0.94771(17) 0.07779(14) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.2789 1.0288 0.0492 0.029 Uiso 1 1 calc R . . . .
C6 C 0.20354(19) 0.86709(18) 0.01363(15) 0.0268(4) Uani 1 1 d . . . . .
H6A H 0.2426 0.8579 -0.0515 0.032 Uiso 1 1 calc R . . . .
H6B H 0.1240 0.9037 0.0029 0.032 Uiso 1 1 calc R . . . .
C7 C 0.18653(17) 0.74586(16) 0.06041(13) 0.0223(4) Uani 1 1 d . . . . .
H7A H 0.2649 0.7048 0.0617 0.027 Uiso 1 1 calc R . . . .
H7B H 0.1313 0.6992 0.0187 0.027 Uiso 1 1 calc R . . . .
C8 C 0.13580(16) 0.75078(15) 0.16620(13) 0.0201(4) Uani 1 1 d . . . . .
C9 C 0.12479(16) 0.62519(15) 0.20871(14) 0.0207(4) Uani 1 1 d . . . . .
H9A H 0.0759 0.6312 0.2695 0.025 Uiso 1 1 calc R . . . .
H9B H 0.0772 0.5788 0.1609 0.025 Uiso 1 1 calc R . . . .
C10 C 0.23654(16) 0.55112(15) 0.23471(13) 0.0201(4) Uani 1 1 d . . . . .
H10A H 0.2079 0.4745 0.2601 0.024 Uiso 1 1 calc R . . . .
H10B H 0.2800 0.5351 0.1725 0.024 Uiso 1 1 calc R . . . .
C11 C 0.32738(16) 0.59890(15) 0.30832(12) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.44217(16) 0.65115(16) 0.27307(13) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.49797(16) 0.74904(17) 0.33502(13) 0.0224(4) Uani 1 1 d . . . . .
H13A H 0.5445 0.8011 0.2907 0.027 Uiso 1 1 calc R . . . .
H13B H 0.5553 0.7131 0.3820 0.027 Uiso 1 1 calc R . . . .
C14 C 0.40790(17) 0.82607(16) 0.39438(14) 0.0234(4) Uani 1 1 d . . . . .
H14A H 0.4438 0.8425 0.4597 0.028 Uiso 1 1 calc R . . . .
H14B H 0.3994 0.9023 0.3598 0.028 Uiso 1 1 calc R . . . .
C15 C 0.28509(16) 0.63897(16) 0.41205(13) 0.0194(4) Uani 1 1 d . . . . .
C16 C 0.37330(18) 0.60033(17) 0.49390(13) 0.0239(4) Uani 1 1 d . . . . .
H16A H 0.3746 0.5143 0.4979 0.036 Uiso 1 1 calc GR . . . .
H16B H 0.3472 0.6329 0.5572 0.036 Uiso 1 1 calc GR . . . .
H16C H 0.4540 0.6293 0.4784 0.036 Uiso 1 1 calc GR . . . .
C17 C 0.16500(18) 0.58428(17) 0.44418(14) 0.0247(4) Uani 1 1 d . . . . .
H17A H 0.1004 0.6139 0.4019 0.037 Uiso 1 1 calc GR . . . .
H17B H 0.1484 0.6056 0.5128 0.037 Uiso 1 1 calc GR . . . .
H17C H 0.1697 0.4985 0.4383 0.037 Uiso 1 1 calc GR . . . .
C18 C 0.48412(17) 0.65069(17) 0.16750(14) 0.0236(4) Uani 1 1 d . . . . .
H18A H 0.5717 0.6430 0.1657 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.4604 0.7244 0.1356 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.4475 0.5843 0.1326 0.035 Uiso 1 1 calc GR . . . .
C19 C 0.00706(17) 0.80074(18) 0.16322(15) 0.0272(4) Uani 1 1 d . . . . .
H19A H 0.0093 0.8821 0.1396 0.041 Uiso 1 1 calc GR . . . .
H19B H -0.0276 0.7986 0.2296 0.041 Uiso 1 1 calc GR . . . .
H19C H -0.0422 0.7532 0.1186 0.041 Uiso 1 1 calc GR . . . .
C20 C 0.19624(19) 1.05452(18) 0.22009(16) 0.0284(4) Uani 1 1 d . . . . .
H20A H 0.2041 1.1244 0.1823 0.034 Uiso 1 1 calc R . . . .
H20B H 0.1647 1.0580 0.2851 0.034 Uiso 1 1 calc R . . . .
O1 O 0.39923(13) 0.90231(12) 0.07469(10) 0.0246(3) Uani 1 1 d . . . . .
H1A H 0.444(3) 0.947(3) 0.108(2) 0.037 Uiso 1 1 d R . . . .
O2 O 0.43900(12) 0.53152(11) 0.31259(10) 0.0212(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
C1 H1 1.0000 . ?
C1 C2 1.546(2) . ?
C1 C14 1.551(3) . ?
C1 C15 1.548(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.548(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.523(2) . ?
C3 C8 1.565(2) . ?
C4 C5 1.520(3) . ?
C4 C20 1.331(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(3) . ?
C5 O1 1.429(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.530(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.543(2) . ?
C8 C9 1.545(2) . ?
C8 C19 1.543(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.544(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.522(2) . ?
C11 C12 1.489(2) . ?
C11 C15 1.552(2) . ?
C11 O2 1.462(2) . ?
C12 C13 1.527(3) . ?
C12 C18 1.506(2) . ?
C12 O2 1.463(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.556(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.546(3) . ?
C15 C17 1.538(2) . ?
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 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?
O1 H1A 0.84(3) . ?

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 H1 106.0 . . ?
C2 C1 C14 111.52(14) . . ?
C2 C1 C15 116.51(15) . . ?
C14 C1 H1 106.0 . . ?
C15 C1 H1 106.0 . . ?
C15 C1 C14 110.15(14) . . ?
C1 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
C1 C2 C3 116.21(14) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C2 C3 H3 105.7 . . ?
C2 C3 C8 114.04(14) . . ?
C4 C3 C2 115.47(15) . . ?
C4 C3 H3 105.7 . . ?
C4 C3 C8 109.45(14) . . ?
C8 C3 H3 105.7 . . ?
C5 C4 C3 113.55(16) . . ?
C20 C4 C3 127.08(18) . . ?
C20 C4 C5 119.33(18) . . ?
C4 C5 H5 109.2 . . ?
C4 C5 C6 110.15(16) . . ?
C6 C5 H5 109.2 . . ?
O1 C5 C4 112.41(15) . . ?
O1 C5 H5 109.2 . . ?
O1 C5 C6 106.52(16) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 112.01(15) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.48(15) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 C3 108.62(14) . . ?
C7 C8 C9 110.03(14) . . ?
C9 C8 C3 112.37(14) . . ?
C19 C8 C3 110.49(14) . . ?
C19 C8 C7 109.22(15) . . ?
C19 C8 C9 106.05(15) . . ?
C8 C9 H9A 106.9 . . ?
C8 C9 H9B 106.9 . . ?
H9A C9 H9B 106.7 . . ?
C10 C9 C8 121.72(15) . . ?
C10 C9 H9A 106.9 . . ?
C10 C9 H9B 106.9 . . ?
C9 C10 H10A 107.5 . . ?
C9 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C11 C10 C9 119.41(14) . . ?
C11 C10 H10A 107.5 . . ?
C11 C10 H10B 107.5 . . ?
C10 C11 C15 119.86(15) . . ?
C12 C11 C10 120.18(15) . . ?
C12 C11 C15 115.76(14) . . ?
O2 C11 C10 113.84(14) . . ?
O2 C11 C12 59.45(11) . . ?
O2 C11 C15 112.09(14) . . ?
C11 C12 C13 117.62(15) . . ?
C11 C12 C18 124.77(15) . . ?
C18 C12 C13 113.55(16) . . ?
O2 C12 C11 59.35(11) . . ?
O2 C12 C13 119.09(14) . . ?
O2 C12 C18 110.65(14) . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
C12 C13 C14 115.65(15) . . ?
H13A C13 H13B 107.4 . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C1 C14 C13 117.07(14) . . ?
C1 C14 H14A 108.0 . . ?
C1 C14 H14B 108.0 . . ?
C13 C14 H14A 108.0 . . ?
C13 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
C1 C15 C11 107.23(14) . . ?
C16 C15 C1 108.15(15) . . ?
C16 C15 C11 112.01(14) . . ?
C17 C15 C1 112.16(15) . . ?
C17 C15 C11 113.70(15) . . ?
C17 C15 C16 103.53(14) . . ?
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 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C20 H20A 120.0 . . ?
C4 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
C5 O1 H1A 109(2) . . ?
C11 O2 C12 61.20(11) . . ?

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
O1 H1A O2 0.84(3) 1.95(3) 2.7830(19) 172(3) 4_655

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 -119.58(17) . . . . ?
C1 C2 C3 C8 112.37(17) . . . . ?
C2 C1 C14 C13 -102.79(17) . . . . ?
C2 C1 C15 C11 64.97(19) . . . . ?
C2 C1 C15 C16 -174.07(14) . . . . ?
C2 C1 C15 C17 -60.5(2) . . . . ?
C2 C3 C4 C5 170.86(15) . . . . ?
C2 C3 C4 C20 -11.4(3) . . . . ?
C2 C3 C8 C7 -172.98(14) . . . . ?
C2 C3 C8 C9 -51.01(19) . . . . ?
C2 C3 C8 C19 67.22(19) . . . . ?
C3 C4 C5 C6 56.4(2) . . . . ?
C3 C4 C5 O1 -62.23(19) . . . . ?
C3 C8 C9 C10 -51.9(2) . . . . ?
C4 C3 C8 C7 55.95(18) . . . . ?
C4 C3 C8 C9 177.92(15) . . . . ?
C4 C3 C8 C19 -63.84(19) . . . . ?
C4 C5 C6 C7 -52.2(2) . . . . ?
C5 C6 C7 C8 54.1(2) . . . . ?
C6 C7 C8 C3 -55.07(19) . . . . ?
C6 C7 C8 C9 -178.46(15) . . . . ?
C6 C7 C8 C19 65.5(2) . . . . ?
C7 C8 C9 C10 69.3(2) . . . . ?
C8 C3 C4 C5 -58.85(19) . . . . ?
C8 C3 C4 C20 118.9(2) . . . . ?
C8 C9 C10 C11 57.7(2) . . . . ?
C9 C10 C11 C12 -101.8(2) . . . . ?
C9 C10 C11 C15 54.2(2) . . . . ?
C9 C10 C11 O2 -169.12(15) . . . . ?
C10 C11 C12 C13 149.35(16) . . . . ?
C10 C11 C12 C18 -6.5(3) . . . . ?
C10 C11 C12 O2 -101.52(16) . . . . ?
C10 C11 C15 C1 -102.66(18) . . . . ?
C10 C11 C15 C16 138.85(16) . . . . ?
C10 C11 C15 C17 21.9(2) . . . . ?
C10 C11 O2 C12 112.17(16) . . . . ?
C11 C12 C13 C14 -29.4(2) . . . . ?
C12 C11 C15 C1 54.35(19) . . . . ?
C12 C11 C15 C16 -64.14(19) . . . . ?
C12 C11 C15 C17 178.92(15) . . . . ?
C12 C13 C14 C1 18.3(2) . . . . ?
C13 C12 O2 C11 106.68(18) . . . . ?
C14 C1 C2 C3 52.22(19) . . . . ?
C14 C1 C15 C11 -63.33(18) . . . . ?
C14 C1 C15 C16 57.64(19) . . . . ?
C14 C1 C15 C17 171.17(14) . . . . ?
C15 C1 C2 C3 -75.4(2) . . . . ?
C15 C1 C14 C13 28.2(2) . . . . ?
C15 C11 C12 C13 -7.6(2) . . . . ?
C15 C11 C12 C18 -163.43(16) . . . . ?
C15 C11 C12 O2 101.54(15) . . . . ?
C15 C11 O2 C12 -107.76(16) . . . . ?
C18 C12 C13 C14 129.07(16) . . . . ?
C18 C12 O2 C11 -119.02(16) . . . . ?
C19 C8 C9 C10 -172.70(16) . . . . ?
C20 C4 C5 C6 -121.6(2) . . . . ?
C20 C4 C5 O1 119.82(19) . . . . ?
O1 C5 C6 C7 70.0(2) . . . . ?
O2 C11 C12 C13 -109.13(16) . . . . ?
O2 C11 C12 C18 95.03(18) . . . . ?
O2 C11 C15 C1 119.94(15) . . . . ?
O2 C11 C15 C16 1.4(2) . . . . ?
O2 C11 C15 C17 -115.49(16) . . . . ?
O2 C12 C13 C14 -97.87(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
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
-7 2 2 0.0953 -7.0000 2.0000 2.0000 0.7463 0.5655 0.4488
-3 4 7 0.1063 -3.0000 4.0000 7.0000 0.2581 0.1737 1.0042
4 3 6 0.1324 4.0000 3.0000 6.0000 -0.4612 -0.4460 0.7215
7 1 2 0.1059 7.0000 1.0000 2.0000 -0.7141 -0.6943 0.1461
-4 -3 -7 0.0715 -4.0000 -3.0000 -7.0000 0.5101 0.4121 -0.8182
4 4 -6 0.0798 4.0000 4.0000 -6.0000 0.2014 -0.9421 -0.3692
-4 -5 4 0.1110 -4.0000 -5.0000 4.0000 -0.1795 0.9624 0.1065
-3 0 8 0.1080 -3.0000 0.0000 8.0000 -0.0944 0.5607 0.8234
-2 -7 -3 0.1113 -2.0000 -7.0000 -3.0000 -0.1869 0.7085 -0.7424
3 7 0 0.1027 3.0000 7.0000 0.0000 0.2347 -0.9067 0.4357
1 -4 -7 0.1230 1.0000 -4.0000 -7.0000 -0.0603 0.0189 -0.9709
1 -6 5 0.1088 1.0000 -6.0000 5.0000 -0.7988 0.6032 0.0504
0 0 9 0.1196 0.0000 0.0000 9.0000 -0.4400 0.3059 0.8701
1 -7 1 0.1217 1.0000 -7.0000 1.0000 -0.6791 0.5555 -0.4057
-1 6 -5 0.1000 -1.0000 6.0000 -5.0000 0.7988 -0.6032 -0.0504
-1 7 -1 0.1144 -1.0000 7.0000 -1.0000 0.6791 -0.5555 0.4057
5 -3 4 0.1118 5.0000 -3.0000 4.0000 -0.9177 -0.0807 0.0952
-5 3 -5 0.1016 -5.0000 3.0000 -5.0000 0.9666 0.0467 -0.1919
-7 -3 0 0.0858 -7.0000 -3.0000 -0.0000 0.4645 0.9388 -0.0915
-7 0 4 0.0880 -7.0000 0.0000 4.0000 0.4967 0.8100 0.5034

_olex2_submission_special_instructions 'No special instructions were received'
