# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4_Epi_2_hydroxyacorenone
_audit_creation_date             2014-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            4-epi-2-hydroxyacorenone
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '3(C15 H24 O2)'
_chemical_formula_sum            'C45 H54 O6'
_chemical_formula_weight         690.88
_chemical_absolute_configuration ad
_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 0.0181 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.45530(10)
_cell_length_b                   19.4162(2)
_cell_length_c                   25.3236(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4157.37(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19497
_cell_measurement_temperature    155.5
_cell_measurement_theta_max      62.7015
_cell_measurement_theta_min      3.4878
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32665
_diffrn_reflns_theta_full        62.79
_diffrn_reflns_theta_max         62.79
_diffrn_reflns_theta_min         3.49
_diffrn_ambient_temperature      155.5
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184   48.0000  -57.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega   76.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   22.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   80.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  160.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   81.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega   23.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -80.0000   36.0000 93

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega  -77.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  103.0000   68.0000 77

#__ type_ start__ end____ width___ exp.time_
 14 omega    8.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 15 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 16 omega   67.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000  -60.0000 127

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -80.0000 -159.0000 102

#__ type_ start__ end____ width___ exp.time_
 19 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 20 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 21 omega   67.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
 22 omega  -49.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  -80.0000 -143.0000 47

#__ type_ start__ end____ width___ exp.time_
 23 omega  -37.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -77.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000 -180.0000 100
;
_diffrn_measurement_device_type  'Gemini S ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0704946000
_diffrn_orient_matrix_UB_12      -0.0087713000
_diffrn_orient_matrix_UB_13      -0.0557394000
_diffrn_orient_matrix_UB_21      -0.0806263000
_diffrn_orient_matrix_UB_22      0.0673116000
_diffrn_orient_matrix_UB_23      -0.0176088000
_diffrn_orient_matrix_UB_31      0.1472619000
_diffrn_orient_matrix_UB_32      0.0410772000
_diffrn_orient_matrix_UB_33      0.0169921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6446
_reflns_number_total             6625
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0441P)²+0.5224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0756
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1A(H1AA), C1B(H1BA), C4C(H4C), C4B(H4B), C11A(H11A), C2A(H2A), C2B(H2B),
 C11B(H11B), C4A(H4A), C11C(H11C), C1C(H1CA), C2C(H2C)
2.b Secondary CH2 refined with riding coordinates:
 C6B(H6BA,H6BB), C3A(H3AA,H3AB), C6A(H6AA,H6AB), C10C(H10E,H10F), C6C(H6CA,
 H6CB), C10A(H10A,H10B), C3B(H3BA,H3BB), C3C(H3CA,H3CB), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C9C(H9C), C9B(H9B)
2.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14C(H14G,H14H,H14I), C13C(H13G,H13H,H13I), C12C(H12G,
 H12H,H12I), C12A(H12A,H12B,H12C), C14A(H14A,H14B,H14C), C12B(H12D,H12E,H12F),
 C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F), C15C(H15G,H15H,H15I), C15B(H15D,
 H15E,H15F), C15A(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B), O1C(H1C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1A O -1.50709(12) -0.68441(5) -0.31055(4) 0.0322(2) Uani 1 d . . .
H1A H -1.5220 -0.7215 -0.3252 0.048 Uiso 1 calc . . GR
O1B O -1.50912(12) -0.78786(5) -0.68701(4) 0.0336(2) Uani 1 d . . .
H1B H -1.4927 -0.8284 -0.6799 0.050 Uiso 1 calc . . GR
O2C O -1.14442(12) -0.18153(5) -0.59528(4) 0.0369(2) Uani 1 d . . .
O2A O -0.97886(12) -0.57231(5) -0.34737(5) 0.0428(3) Uani 1 d . . .
O1C O -1.43728(12) -0.35057(7) -0.48755(4) 0.0443(3) Uani 1 d . . .
H1C H -1.5140 -0.3399 -0.4695 0.066 Uiso 1 calc . . GR
O2B O -2.03573(13) -0.69017(6) -0.62797(5) 0.0475(3) Uani 1 d . . .
C6B C -1.77185(16) -0.66736(7) -0.65589(5) 0.0272(3) Uani 1 d . . .
H6BA H -1.7709 -0.6326 -0.6834 0.033 Uiso 1 calc . . R
H6BB H -1.7790 -0.7121 -0.6728 0.033 Uiso 1 calc . . R
C7A C -1.10008(17) -0.53784(7) -0.34859(6) 0.0295(3) Uani 1 d . . .
C3A C -1.57038(17) -0.62805(7) -0.39368(5) 0.0334(3) Uani 1 d . . .
H3AA H -1.6486 -0.5995 -0.4112 0.040 Uiso 1 calc . . R
H3AB H -1.5706 -0.6734 -0.4098 0.040 Uiso 1 calc . . R
C5C C -1.40648(16) -0.32857(6) -0.60553(5) 0.0257(3) Uani 1 d . . .
C1A C -1.55036(15) -0.56240(7) -0.31492(5) 0.0250(3) Uani 1 d . . .
H1AA H -1.6322 -0.5297 -0.3259 0.030 Uiso 1 calc . . R
C5A C -1.39859(16) -0.54415(6) -0.34802(5) 0.0245(3) Uani 1 d . . .
C1B C -1.46695(16) -0.67055(7) -0.66093(5) 0.0287(3) Uani 1 d . . .
H1BA H -1.3846 -0.6420 -0.6448 0.034 Uiso 1 calc . . R
C9A C -1.24613(19) -0.44171(7) -0.38494(6) 0.0344(3) Uani 1 d . . .
H9A H -1.2474 -0.4004 -0.4035 0.041 Uiso 1 calc . . R
C6A C -1.24460(16) -0.55816(7) -0.31776(5) 0.0259(3) Uani 1 d . . .
H6AA H -1.2464 -0.5328 -0.2848 0.031 Uiso 1 calc . . R
H6AB H -1.2386 -0.6068 -0.3093 0.031 Uiso 1 calc . . R
C8A C -1.10679(19) -0.47284(7) -0.37864(6) 0.0335(3) Uani 1 d . . .
C5B C -1.61668(16) -0.66327(6) -0.62480(5) 0.0264(3) Uani 1 d . . .
C10C C -1.42955(17) -0.32811(7) -0.66584(5) 0.0308(3) Uani 1 d . . .
H10E H -1.4282 -0.3752 -0.6786 0.037 Uiso 1 calc . . R
H10F H -1.5327 -0.3089 -0.6739 0.037 Uiso 1 calc . . R
C7B C -1.91441(18) -0.65687(7) -0.62188(6) 0.0325(3) Uani 1 d . . .
C4C C -1.26591(17) -0.37636(7) -0.58712(5) 0.0298(3) Uani 1 d . . .
H4C H -1.1962 -0.3480 -0.5652 0.036 Uiso 1 calc . . R
C9C C -1.30617(18) -0.28775(7) -0.69465(5) 0.0319(3) Uani 1 d . . .
H9C H -1.2938 -0.2966 -0.7305 0.038 Uiso 1 calc . . R
C4B C -1.6078(2) -0.72784(7) -0.58709(6) 0.0359(3) Uani 1 d . . .
H4B H -1.6836 -0.7615 -0.6009 0.043 Uiso 1 calc . . R
C8C C -1.21238(17) -0.24020(7) -0.67322(5) 0.0300(3) Uani 1 d . . .
C11A C -1.54207(17) -0.55793(7) -0.25423(5) 0.0295(3) Uani 1 d . . .
H11A H -1.4521 -0.5856 -0.2422 0.035 Uiso 1 calc . . R
C6C C -1.36987(16) -0.25445(7) -0.58799(5) 0.0284(3) Uani 1 d . . .
H6CA H -1.4629 -0.2262 -0.5936 0.034 Uiso 1 calc . . R
H6CB H -1.3471 -0.2544 -0.5505 0.034 Uiso 1 calc . . R
C2A C -1.60292(17) -0.63267(7) -0.33516(5) 0.0284(3) Uani 1 d . . .
H2A H -1.7155 -0.6405 -0.3282 0.034 Uiso 1 calc . . R
C10A C -1.40000(18) -0.46810(7) -0.36445(6) 0.0324(3) Uani 1 d . . .
H10A H -1.4800 -0.4618 -0.3915 0.039 Uiso 1 calc . . R
H10B H -1.4307 -0.4405 -0.3342 0.039 Uiso 1 calc . . R
C13A C -1.69262(19) -0.58762(8) -0.22972(6) 0.0406(4) Uani 1 d . . .
H13A H -1.7834 -0.5664 -0.2456 0.061 Uiso 1 calc . . GR
H13B H -1.6929 -0.5787 -0.1924 0.061 Uiso 1 calc . . GR
H13C H -1.6960 -0.6364 -0.2357 0.061 Uiso 1 calc . . GR
C2B C -1.41336(17) -0.74511(7) -0.65407(6) 0.0333(3) Uani 1 d . . .
H2B H -1.3009 -0.7504 -0.6625 0.040 Uiso 1 calc . . R
C11B C -1.47817(18) -0.64761(7) -0.71893(6) 0.0349(3) Uani 1 d . . .
H11B H -1.5698 -0.6705 -0.7349 0.042 Uiso 1 calc . . R
C4A C -1.40655(18) -0.59533(7) -0.39674(5) 0.0325(3) Uani 1 d . . .
H4A H -1.3299 -0.6321 -0.3898 0.039 Uiso 1 calc . . R
C11C C -1.69373(16) -0.31068(8) -0.56217(5) 0.0331(3) Uani 1 d . . .
H11C H -1.6540 -0.2754 -0.5379 0.040 Uiso 1 calc . . R
C14C C -1.0860(2) -0.20277(8) -0.70309(6) 0.0411(4) Uani 1 d . . .
H14G H -1.0747 -0.2228 -0.7375 0.062 Uiso 1 calc . . GR
H14H H -0.9877 -0.2063 -0.6843 0.062 Uiso 1 calc . . GR
H14I H -1.1147 -0.1551 -0.7065 0.062 Uiso 1 calc . . GR
C13C C -1.82272(18) -0.35143(9) -0.53338(6) 0.0423(4) Uani 1 d . . .
H13G H -1.9114 -0.3219 -0.5265 0.063 Uiso 1 calc . . GR
H13H H -1.7816 -0.3686 -0.5006 0.063 Uiso 1 calc . . GR
H13I H -1.8560 -0.3894 -0.5550 0.063 Uiso 1 calc . . GR
C3B C -1.44448(19) -0.75802(8) -0.59604(6) 0.0399(4) Uani 1 d . . .
H3BA H -1.3663 -0.7351 -0.5742 0.048 Uiso 1 calc . . R
H3BB H -1.4431 -0.8069 -0.5882 0.048 Uiso 1 calc . . R
C9B C -1.7668(2) -0.57411(8) -0.57069(6) 0.0421(4) Uani 1 d . . .
H9B H -1.7646 -0.5390 -0.5457 0.051 Uiso 1 calc . . R
C8B C -1.9065(2) -0.60218(7) -0.58135(6) 0.0386(3) Uani 1 d . . .
C12C C -1.76949(19) -0.27405(9) -0.60931(6) 0.0428(4) Uani 1 d . . .
H12G H -1.8047 -0.3076 -0.6345 0.064 Uiso 1 calc . . GR
H12H H -1.6931 -0.2442 -0.6256 0.064 Uiso 1 calc . . GR
H12I H -1.8582 -0.2473 -0.5974 0.064 Uiso 1 calc . . GR
C1C C -1.55486(16) -0.35852(7) -0.57634(5) 0.0289(3) Uani 1 d . . .
H1CA H -1.5984 -0.3941 -0.5996 0.035 Uiso 1 calc . . R
C12A C -1.5194(2) -0.48433(8) -0.23437(6) 0.0396(4) Uani 1 d . . .
H12A H -1.4191 -0.4671 -0.2462 0.059 Uiso 1 calc . . GR
H12B H -1.5225 -0.4839 -0.1965 0.059 Uiso 1 calc . . GR
H12C H -1.6025 -0.4556 -0.2479 0.059 Uiso 1 calc . . GR
C14A C -0.9539(2) -0.44713(9) -0.40175(8) 0.0538(5) Uani 1 d . . .
H14A H -0.8813 -0.4365 -0.3738 0.081 Uiso 1 calc . . GR
H14B H -0.9738 -0.4064 -0.4222 0.081 Uiso 1 calc . . GR
H14C H -0.9092 -0.4820 -0.4240 0.081 Uiso 1 calc . . GR
C3C C -1.3398(2) -0.43023(9) -0.55079(6) 0.0421(4) Uani 1 d . . .
H3CA H -1.3673 -0.4714 -0.5705 0.051 Uiso 1 calc . . R
H3CB H -1.2672 -0.4427 -0.5227 0.051 Uiso 1 calc . . R
C12B C -1.5001(2) -0.56976(8) -0.72487(7) 0.0456(4) Uani 1 d . . .
H12D H -1.5954 -0.5559 -0.7072 0.068 Uiso 1 calc . . GR
H12E H -1.5072 -0.5582 -0.7617 0.068 Uiso 1 calc . . GR
H12F H -1.4114 -0.5463 -0.7094 0.068 Uiso 1 calc . . GR
C10B C -1.61323(19) -0.59402(7) -0.59526(6) 0.0350(3) Uani 1 d . . .
H10C H -1.5333 -0.5964 -0.5678 0.042 Uiso 1 calc . . R
H10D H -1.5818 -0.5582 -0.6198 0.042 Uiso 1 calc . . R
C2C C -1.48625(19) -0.39652(8) -0.52847(6) 0.0371(3) Uani 1 d . . .
H2C H -1.5607 -0.4310 -0.5150 0.045 Uiso 1 calc . . R
C13B C -1.3303(2) -0.66903(9) -0.74984(7) 0.0514(4) Uani 1 d . . .
H13D H -1.2380 -0.6511 -0.7326 0.077 Uiso 1 calc . . GR
H13E H -1.3363 -0.6511 -0.7851 0.077 Uiso 1 calc . . GR
H13F H -1.3241 -0.7184 -0.7512 0.077 Uiso 1 calc . . GR
C14B C -2.0582(2) -0.58379(9) -0.55379(8) 0.0606(5) Uani 1 d . . .
H14D H -2.1364 -0.5712 -0.5795 0.091 Uiso 1 calc . . GR
H14E H -2.0400 -0.5458 -0.5303 0.091 Uiso 1 calc . . GR
H14F H -2.0950 -0.6227 -0.5339 0.091 Uiso 1 calc . . GR
C15C C -1.1623(2) -0.41059(9) -0.62841(6) 0.0434(4) Uani 1 d . . .
H15G H -1.2266 -0.4388 -0.6510 0.065 Uiso 1 calc . . GR
H15H H -1.0844 -0.4387 -0.6112 0.065 Uiso 1 calc . . GR
H15I H -1.1105 -0.3759 -0.6491 0.065 Uiso 1 calc . . GR
C15B C -1.6464(3) -0.71864(10) -0.52866(7) 0.0607(5) Uani 1 d . . .
H15D H -1.5833 -0.6820 -0.5144 0.091 Uiso 1 calc . . GR
H15E H -1.6237 -0.7606 -0.5101 0.091 Uiso 1 calc . . GR
H15F H -1.7564 -0.7075 -0.5247 0.091 Uiso 1 calc . . GR
C15A C -1.3700(3) -0.56760(11) -0.45163(6) 0.0625(6) Uani 1 d . . .
H15A H -1.3799 -0.6040 -0.4770 0.094 Uiso 1 calc . . GR
H15B H -1.2641 -0.5499 -0.4523 0.094 Uiso 1 calc . . GR
H15C H -1.4430 -0.5314 -0.4601 0.094 Uiso 1 calc . . GR
C7C C -1.23260(17) -0.22287(6) -0.61694(5) 0.0273(3) Uani 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
O1A C2A 1.4332(16) . ?
O1B C2B 1.4285(17) . ?
O2C C7C 1.2251(17) . ?
O2A C7A 1.2244(18) . ?
O1C C2C 1.4288(19) . ?
O2B C7B 1.2223(18) . ?
C6B C5B 1.5322(19) . ?
C6B C7B 1.495(2) . ?
C7A C6A 1.5027(19) . ?
C7A C8A 1.4749(19) . ?
C3A C2A 1.5099(19) . ?
C3A C4A 1.526(2) . ?
C5C C10C 1.5399(17) . ?
C5C C4C 1.5782(19) . ?
C5C C6C 1.5375(18) . ?
C5C C1C 1.5678(19) . ?
C1A C5A 1.5732(18) . ?
C1A C11A 1.5408(18) . ?
C1A C2A 1.5237(18) . ?
C5A C6A 1.5351(18) . ?
C5A C10A 1.5341(18) . ?
C5A C4A 1.5857(17) . ?
C1B C5B 1.5683(19) . ?
C1B C2B 1.5270(19) . ?
C1B C11B 1.538(2) . ?
C9A C8A 1.334(2) . ?
C9A C10A 1.491(2) . ?
C8A C14A 1.504(2) . ?
C5B C4B 1.5778(18) . ?
C5B C10B 1.5389(18) . ?
C10C C9C 1.495(2) . ?
C7B C8B 1.478(2) . ?
C4C C3C 1.527(2) . ?
C4C C15C 1.517(2) . ?
C9C C8C 1.333(2) . ?
C4B C3B 1.517(2) . ?
C4B C15B 1.526(2) . ?
C8C C14C 1.497(2) . ?
C8C C7C 1.4744(18) . ?
C11A C13A 1.529(2) . ?
C11A C12A 1.527(2) . ?
C6C C7C 1.503(2) . ?
C2B C3B 1.514(2) . ?
C11B C12B 1.530(2) . ?
C11B C13B 1.532(2) . ?
C4A C15A 1.522(2) . ?
C11C C13C 1.532(2) . ?
C11C C12C 1.530(2) . ?
C11C C1C 1.5395(19) . ?
C9B C8B 1.329(2) . ?
C9B C10B 1.491(2) . ?
C8B C14B 1.503(2) . ?
C1C C2C 1.533(2) . ?
C3C C2C 1.510(2) . ?

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
C7B C6B C5B 112.78(11) . . ?
O2A C7A C6A 121.61(12) . . ?
O2A C7A C8A 120.86(13) . . ?
C8A C7A C6A 117.48(12) . . ?
C2A C3A C4A 103.89(11) . . ?
C10C C5C C4C 113.06(11) . . ?
C10C C5C C1C 111.61(11) . . ?
C6C C5C C10C 107.85(10) . . ?
C6C C5C C4C 108.26(11) . . ?
C6C C5C C1C 111.84(11) . . ?
C1C C5C C4C 104.21(10) . . ?
C11A C1A C5A 118.79(11) . . ?
C2A C1A C5A 105.10(10) . . ?
C2A C1A C11A 113.53(11) . . ?
C1A C5A C4A 103.81(10) . . ?
C6A C5A C1A 112.70(10) . . ?
C6A C5A C4A 108.26(11) . . ?
C10A C5A C1A 110.79(11) . . ?
C10A C5A C6A 108.21(11) . . ?
C10A C5A C4A 113.07(11) . . ?
C2B C1B C5B 104.99(11) . . ?
C2B C1B C11B 113.68(12) . . ?
C11B C1B C5B 118.77(11) . . ?
C8A C9A C10A 124.98(12) . . ?
C7A C6A C5A 112.57(10) . . ?
C7A C8A C14A 116.86(14) . . ?
C9A C8A C7A 118.92(13) . . ?
C9A C8A C14A 124.20(13) . . ?
C6B C5B C1B 112.76(10) . . ?
C6B C5B C4B 108.09(11) . . ?
C6B C5B C10B 108.13(11) . . ?
C1B C5B C4B 104.08(11) . . ?
C10B C5B C1B 110.30(11) . . ?
C10B C5B C4B 113.52(11) . . ?
C9C C10C C5C 113.50(11) . . ?
O2B C7B C6B 122.13(13) . . ?
O2B C7B C8B 120.35(14) . . ?
C8B C7B C6B 117.48(12) . . ?
C3C C4C C5C 105.81(11) . . ?
C15C C4C C5C 119.26(11) . . ?
C15C C4C C3C 110.58(12) . . ?
C8C C9C C10C 125.43(12) . . ?
C3B C4B C5B 105.04(12) . . ?
C3B C4B C15B 112.62(14) . . ?
C15B C4B C5B 118.94(13) . . ?
C9C C8C C14C 123.72(13) . . ?
C9C C8C C7C 118.87(13) . . ?
C7C C8C C14C 117.41(12) . . ?
C13A C11A C1A 110.23(12) . . ?
C12A C11A C1A 112.77(11) . . ?
C12A C11A C13A 108.86(12) . . ?
C7C C6C C5C 113.35(11) . . ?
O1A C2A C3A 111.43(11) . . ?
O1A C2A C1A 108.45(10) . . ?
C3A C2A C1A 102.93(11) . . ?
C9A C10A C5A 114.72(12) . . ?
O1B C2B C1B 108.43(11) . . ?
O1B C2B C3B 111.86(12) . . ?
C3B C2B C1B 102.47(12) . . ?
C12B C11B C1B 112.80(12) . . ?
C12B C11B C13B 108.46(13) . . ?
C13B C11B C1B 111.04(13) . . ?
C3A C4A C5A 105.07(11) . . ?
C15A C4A C3A 112.20(13) . . ?
C15A C4A C5A 118.70(13) . . ?
C13C C11C C1C 110.03(12) . . ?
C12C C11C C13C 108.26(12) . . ?
C12C C11C C1C 114.69(12) . . ?
C2B C3B C4B 103.85(11) . . ?
C8B C9B C10B 125.68(13) . . ?
C7B C8B C14B 117.04(15) . . ?
C9B C8B C7B 118.40(14) . . ?
C9B C8B C14B 124.53(14) . . ?
C11C C1C C5C 119.77(11) . . ?
C2C C1C C5C 104.38(11) . . ?
C2C C1C C11C 113.24(11) . . ?
C2C C3C C4C 105.32(12) . . ?
C9B C10B C5B 114.39(12) . . ?
O1C C2C C1C 112.51(12) . . ?
O1C C2C C3C 107.72(13) . . ?
C3C C2C C1C 102.88(11) . . ?
O2C C7C C8C 120.77(13) . . ?
O2C C7C C6C 121.25(12) . . ?
C8C C7C C6C 117.89(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1010744'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_acoronene
_audit_creation_date             2014-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            acoronene
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.33
_chemical_absolute_configuration ad
_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 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.5501(2)
_cell_length_b                   6.48130(10)
_cell_length_c                   12.5837(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.159(2)
_cell_angle_gamma                90.00
_cell_volume                     662.60(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    173.01(18)
_cell_measurement_theta_max      62.5766
_cell_measurement_theta_min      3.6936
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        62.66
_diffrn_reflns_theta_max         62.66
_diffrn_reflns_theta_min         3.70
_diffrn_ambient_temperature      173.01(18)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -101.00  -60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684 -178.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   55.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684   57.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684   57.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684    0.0000 -180.0000 115

#__ type_ start__ end____ width___ exp.time_
  5 omega  -37.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684  -38.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  7 omega   87.00  159.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega   21.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   83.0000 -102.0000 79

#__ type_ start__ end____ width___ exp.time_
 12 omega   18.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega  106.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   18.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega   71.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 17 omega   75.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  128.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 20 omega   26.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
 21 omega   60.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
 22 omega   54.00  148.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 23 omega -109.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684  178.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 24 omega -109.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684  178.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 25 omega  -46.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684  -83.0000  102.0000 46

#__ type_ start__ end____ width___ exp.time_
 26 omega   35.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684  178.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
 27 omega   10.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684   46.0000  -49.0000 94

#__ type_ start__ end____ width___ exp.time_
 28 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega -134.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 30 omega -134.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
 31 omega -134.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 32 omega -134.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 33 omega   61.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
 34 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 35 omega   18.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 36 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 37 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 38 omega   61.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 39 omega   19.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 40 omega   18.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 41 omega -109.00  -57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684 -178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
 42 omega -102.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -32.8684  -57.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
 43 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       32.8684   77.0000  -90.0000 100
;
_diffrn_measurement_device_type  'Gemini S ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0984334000
_diffrn_orient_matrix_UB_12      -0.1991129000
_diffrn_orient_matrix_UB_13      -0.0416509000
_diffrn_orient_matrix_UB_21      0.1242104000
_diffrn_orient_matrix_UB_22      -0.0622737000
_diffrn_orient_matrix_UB_23      -0.0605328000
_diffrn_orient_matrix_UB_31      0.1042260000
_diffrn_orient_matrix_UB_32      -0.1138156000
_diffrn_orient_matrix_UB_33      0.1057984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2064
_reflns_number_total             2074
_reflns_odcompleteness_completeness 98.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2074
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0313P)²+0.1213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0630
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C1(H1), C4(H4), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C12(H12A,H12B,
 H12C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.96305(11) 0.48730(16) 0.00126(7) 0.0316(2) Uani 1 d . . .
O2 O 1.24013(13) 0.78987(16) -0.45150(8) 0.0345(2) Uani 1 d . . .
C1 C 0.95716(15) 0.57203(18) -0.18843(10) 0.0218(3) Uani 1 d . . .
H1 H 0.9520 0.7227 -0.1841 0.026 Uiso 1 calc . . R
C7 C 1.19249(15) 0.6453(2) -0.40706(10) 0.0236(3) Uani 1 d . . .
C6 C 1.07027(16) 0.6775(2) -0.34394(11) 0.0239(3) Uani 1 d . . .
H6A H 0.9599 0.6630 -0.3958 0.029 Uiso 1 calc . . R
H6B H 1.0814 0.8176 -0.3154 0.029 Uiso 1 calc . . R
C5 C 1.09014(14) 0.52826(19) -0.24610(10) 0.0205(3) Uani 1 d . . .
C2 C 1.03314(15) 0.5008(2) -0.06842(10) 0.0236(3) Uani 1 d . . .
C10 C 1.08118(16) 0.3089(2) -0.29426(11) 0.0243(3) Uani 1 d . . .
H10A H 1.1121 0.2106 -0.2331 0.029 Uiso 1 calc . . R
H10B H 0.9685 0.2796 -0.3387 0.029 Uiso 1 calc . . R
C9 C 1.19130(16) 0.2803(2) -0.36551(10) 0.0266(3) Uani 1 d . . .
H9 H 1.2249 0.1466 -0.3742 0.032 Uiso 1 calc . . R
C8 C 1.24501(16) 0.4315(2) -0.41749(10) 0.0247(3) Uani 1 d . . .
C4 C 1.25510(15) 0.5521(2) -0.14801(10) 0.0240(3) Uani 1 d . . .
H4 H 1.3415 0.4711 -0.1645 0.029 Uiso 1 calc . . R
C11 C 0.77831(14) 0.5031(2) -0.24845(10) 0.0248(3) Uani 1 d . . .
H11 H 0.7621 0.5064 -0.3290 0.030 Uiso 1 calc . . R
C14 C 1.35224(19) 0.3957(2) -0.49008(12) 0.0340(3) Uani 1 d . . .
H14A H 1.2973 0.4453 -0.5642 0.051 Uiso 1 calc . . GR
H14B H 1.3736 0.2507 -0.4929 0.051 Uiso 1 calc . . GR
H14C H 1.4544 0.4681 -0.4596 0.051 Uiso 1 calc . . GR
C13 C 0.73823(18) 0.2846(3) -0.21938(12) 0.0367(3) Uani 1 d . . .
H13A H 0.8217 0.1913 -0.2263 0.055 Uiso 1 calc . . GR
H13B H 0.6334 0.2434 -0.2696 0.055 Uiso 1 calc . . GR
H13C H 0.7344 0.2818 -0.1440 0.055 Uiso 1 calc . . GR
C15 C 1.31330(17) 0.7749(2) -0.12228(12) 0.0328(3) Uani 1 d . . .
H15A H 1.3376 0.8327 -0.1856 0.049 Uiso 1 calc . . GR
H15B H 1.4106 0.7774 -0.0584 0.049 Uiso 1 calc . . GR
H15C H 1.2283 0.8544 -0.1067 0.049 Uiso 1 calc . . GR
C3 C 1.21358(16) 0.4552(2) -0.04902(11) 0.0282(3) Uani 1 d . . .
H3A H 1.2328 0.3075 -0.0465 0.034 Uiso 1 calc . . R
H3B H 1.2806 0.5155 0.0209 0.034 Uiso 1 calc . . R
C12 C 0.65597(16) 0.6546(3) -0.22539(12) 0.0335(3) Uani 1 d . . .
H12A H 0.6686 0.6550 -0.1469 0.050 Uiso 1 calc . . GR
H12B H 0.5459 0.6135 -0.2666 0.050 Uiso 1 calc . . GR
H12C H 0.6765 0.7906 -0.2482 0.050 Uiso 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 C2 1.2095(15) . ?
O2 C7 1.2243(16) . ?
C1 C5 1.5538(16) . ?
C1 C2 1.5180(17) . ?
C1 C11 1.5455(17) . ?
C7 C6 1.5112(17) . ?
C7 C8 1.4748(18) . ?
C6 C5 1.5331(17) . ?
C5 C10 1.5382(17) . ?
C5 C4 1.5657(16) . ?
C2 C3 1.5140(18) . ?
C10 C9 1.5002(17) . ?
C9 C8 1.336(2) . ?
C8 C14 1.5003(19) . ?
C4 C15 1.5286(19) . ?
C4 C3 1.5321(18) . ?
C11 C13 1.528(2) . ?
C11 C12 1.5271(19) . ?

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 C5 105.10(10) . . ?
C2 C1 C11 116.72(10) . . ?
C11 C1 C5 118.40(10) . . ?
O2 C7 C6 121.14(12) . . ?
O2 C7 C8 121.64(11) . . ?
C8 C7 C6 117.15(11) . . ?
C7 C6 C5 114.40(10) . . ?
C1 C5 C4 102.96(9) . . ?
C6 C5 C1 110.23(10) . . ?
C6 C5 C10 106.71(10) . . ?
C6 C5 C4 114.71(10) . . ?
C10 C5 C1 113.51(10) . . ?
C10 C5 C4 108.89(10) . . ?
O1 C2 C1 126.02(11) . . ?
O1 C2 C3 125.40(11) . . ?
C3 C2 C1 108.56(10) . . ?
C9 C10 C5 112.70(11) . . ?
C8 C9 C10 125.27(13) . . ?
C7 C8 C14 117.41(11) . . ?
C9 C8 C7 118.99(11) . . ?
C9 C8 C14 123.56(12) . . ?
C15 C4 C5 114.45(11) . . ?
C15 C4 C3 110.94(11) . . ?
C3 C4 C5 102.74(10) . . ?
C13 C11 C1 114.37(11) . . ?
C12 C11 C1 110.68(11) . . ?
C12 C11 C13 109.42(11) . . ?
C2 C3 C4 105.76(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1010745'
