# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cmpd2a_sh009
_database_code_depnum_ccdc_archive 'CCDC 997310'
_audit_update_record             
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
5-(cyclohexylidenemethyl)-3,3-diphenyldihydrofuran-2(3H)-one
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_exptl_crystal_recrystallization_method 
'slow diff of pentane into ether/dichloromethane soln'
_chemical_melting_point          367-370

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      125(2)
_chemical_formula_weight         332.42

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.28820(10)
_cell_length_b                   10.08340(10)
_cell_length_c                   17.6278(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.1728(4)
_cell_angle_gamma                90
_cell_volume                     1799.96(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9853
_cell_measurement_theta_min      5.07
_cell_measurement_theta_max      68.75
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.598
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.75
_diffrn_reflns_number            26227
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.366
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_full        66.595
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3169
_reflns_number_gt                3122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL (XP)'
_computing_publication_material  'Bruker SHELXTL (XCIF)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.7764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3169
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96731(8) 0.41437(8) 0.33833(5) 0.0250(2) Uani 1 1 d . . . . .
C2 C 0.87425(11) 0.42403(11) 0.27439(6) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.86556(8) 0.52105(8) 0.23419(5) 0.0271(2) Uani 1 1 d . . . . .
C3 C 0.78677(10) 0.29920(11) 0.26454(6) 0.0185(2) Uani 1 1 d . . . . .
C4 C 0.87716(11) 0.20106(11) 0.31577(6) 0.0209(3) Uani 1 1 d . . . . .
H4A H 0.8247 0.1334 0.3377 0.025 Uiso 1 1 calc R U . . .
H4B H 0.9376 0.1559 0.2862 0.025 Uiso 1 1 calc R U . . .
C5 C 0.95365(11) 0.28798(12) 0.37891(7) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.9013 0.3019 0.4210 0.027 Uiso 1 1 calc R U . . .
C6 C 1.08790(11) 0.23616(12) 0.41152(7) 0.0239(3) Uani 1 1 d . . . . .
H6 H 1.1337 0.1917 0.3767 0.029 Uiso 1 1 calc R U . . .
C7 C 1.15013(11) 0.24578(12) 0.48431(7) 0.0231(3) Uani 1 1 d . . . . .
C8 C 1.09945(13) 0.31396(13) 0.54927(7) 0.0294(3) Uani 1 1 d . . . . .
H8A H 1.0078 0.3444 0.5309 0.035 Uiso 1 1 calc R U . . .
H8B H 1.1545 0.3929 0.5656 0.035 Uiso 1 1 calc R U . . .
C9 C 1.10211(13) 0.22116(14) 0.61848(7) 0.0333(3) Uani 1 1 d . . . . .
H9A H 1.0775 0.2717 0.6620 0.040 Uiso 1 1 calc R U . . .
H9B H 1.0362 0.1497 0.6045 0.040 Uiso 1 1 calc R U . . .
C10 C 1.23837(14) 0.15988(13) 0.64361(7) 0.0312(3) Uani 1 1 d . . . . .
H10A H 1.3023 0.2304 0.6635 0.037 Uiso 1 1 calc R U . . .
H10B H 1.2352 0.0960 0.6859 0.037 Uiso 1 1 calc R U . . .
C11 C 1.28474(13) 0.08895(13) 0.57691(7) 0.0293(3) Uani 1 1 d . . . . .
H11A H 1.2259 0.0128 0.5603 0.035 Uiso 1 1 calc R U . . .
H11B H 1.3752 0.0543 0.5942 0.035 Uiso 1 1 calc R U . . .
C12 C 1.28419(12) 0.18331(13) 0.50884(7) 0.0272(3) Uani 1 1 d . . . . .
H12A H 1.3509 0.2537 0.5237 0.033 Uiso 1 1 calc R U . . .
H12B H 1.3086 0.1337 0.4650 0.033 Uiso 1 1 calc R U . . .
C13 C 0.65988(10) 0.32606(11) 0.29716(6) 0.0181(2) Uani 1 1 d . . . . .
C14 C 0.57368(11) 0.22006(12) 0.30091(6) 0.0217(2) Uani 1 1 d . . . . .
H14 H 0.5958 0.1343 0.2848 0.026 Uiso 1 1 calc R U . . .
C15 C 0.45637(11) 0.23872(12) 0.32782(7) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.3982 0.1660 0.3295 0.030 Uiso 1 1 calc R U . . .
C16 C 0.42346(11) 0.36319(13) 0.35232(7) 0.0251(3) Uani 1 1 d . . . . .
H16 H 0.3433 0.3757 0.3711 0.030 Uiso 1 1 calc R U . . .
C17 C 0.50797(12) 0.46866(12) 0.34919(7) 0.0242(3) Uani 1 1 d . . . . .
H17 H 0.4860 0.5539 0.3661 0.029 Uiso 1 1 calc R U . . .
C18 C 0.62540(11) 0.45053(11) 0.32125(6) 0.0210(2) Uani 1 1 d . . . . .
H18 H 0.6824 0.5239 0.3187 0.025 Uiso 1 1 calc R U . . .
C19 C 0.75049(10) 0.26201(11) 0.17919(6) 0.0188(2) Uani 1 1 d . . . . .
C20 C 0.79419(11) 0.14608(12) 0.14937(7) 0.0223(3) Uani 1 1 d . . . . .
H20 H 0.8479 0.0858 0.1826 0.027 Uiso 1 1 calc R U . . .
C21 C 0.75974(12) 0.11756(13) 0.07100(7) 0.0265(3) Uani 1 1 d . . . . .
H21 H 0.7898 0.0377 0.0513 0.032 Uiso 1 1 calc R U . . .
C22 C 0.68233(12) 0.20432(13) 0.02184(7) 0.0281(3) Uani 1 1 d . . . . .
H22 H 0.6600 0.1850 -0.0316 0.034 Uiso 1 1 calc R U . . .
C23 C 0.63746(12) 0.31971(13) 0.05117(7) 0.0277(3) Uani 1 1 d . . . . .
H23 H 0.5839 0.3797 0.0177 0.033 Uiso 1 1 calc R U . . .
C24 C 0.67037(11) 0.34798(12) 0.12918(7) 0.0243(3) Uani 1 1 d . . . . .
H24 H 0.6381 0.4267 0.1489 0.029 Uiso 1 1 calc R U . . .


_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 1.3474(14) . ?
O1 C5 1.4802(14) . ?
C2 O2 1.2020(14) . ?
C2 C3 1.5393(15) . ?
C3 C19 1.5315(15) . ?
C3 C4 1.5372(15) . ?
C3 C13 1.5406(15) . ?
C4 C5 1.5222(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.4935(16) . ?
C5 H5 1.0000 . ?
C6 C7 1.3325(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.5056(17) . ?
C7 C12 1.5084(16) . ?
C8 C9 1.5338(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5244(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5231(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5307(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.3908(16) . ?
C13 C14 1.3978(16) . ?
C14 C15 1.3854(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3885(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3810(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3950(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3886(16) . ?
C19 C24 1.3969(16) . ?
C20 C21 1.3942(17) . ?
C20 H20 0.9500 . ?
C21 C22 1.3808(19) . ?
C21 H21 0.9500 . ?
C22 C23 1.3851(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.3865(17) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 110.63(8) . . ?
O2 C2 O1 121.32(10) . . ?
O2 C2 C3 128.16(10) . . ?
O1 C2 C3 110.50(9) . . ?
C19 C3 C4 115.89(9) . . ?
C19 C3 C2 110.32(9) . . ?
C4 C3 C2 100.32(8) . . ?
C19 C3 C13 109.53(8) . . ?
C4 C3 C13 111.01(9) . . ?
C2 C3 C13 109.35(9) . . ?
C5 C4 C3 103.88(9) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
O1 C5 C6 109.08(9) . . ?
O1 C5 C4 102.91(8) . . ?
C6 C5 C4 113.80(10) . . ?
O1 C5 H5 110.3 . . ?
C6 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?
C7 C6 C5 126.84(11) . . ?
C7 C6 H6 116.6 . . ?
C5 C6 H6 116.6 . . ?
C6 C7 C8 126.41(11) . . ?
C6 C7 C12 120.34(11) . . ?
C8 C7 C12 113.24(10) . . ?
C7 C8 C9 111.50(10) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 111.40(11) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 111.31(10) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.79(10) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C7 C12 C11 111.16(10) . . ?
C7 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C7 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 118.52(10) . . ?
C18 C13 C3 123.45(10) . . ?
C14 C13 C3 118.01(10) . . ?
C15 C14 C13 120.70(11) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.29(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.59(10) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.25(11) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.63(11) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C24 118.55(10) . . ?
C20 C19 C3 122.61(10) . . ?
C24 C19 C3 118.83(10) . . ?
C19 C20 C21 120.40(11) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.58(11) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.42(11) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.25(12) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.78(11) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?

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
C5 O1 C2 O2 177.86(10) . . . . ?
C5 O1 C2 C3 -0.95(12) . . . . ?
O2 C2 C3 C19 38.84(15) . . . . ?
O1 C2 C3 C19 -142.45(9) . . . . ?
O2 C2 C3 C4 161.57(11) . . . . ?
O1 C2 C3 C4 -19.72(11) . . . . ?
O2 C2 C3 C13 -81.68(14) . . . . ?
O1 C2 C3 C13 97.03(10) . . . . ?
C19 C3 C4 C5 150.41(9) . . . . ?
C2 C3 C4 C5 31.68(10) . . . . ?
C13 C3 C4 C5 -83.83(10) . . . . ?
C2 O1 C5 C6 142.78(9) . . . . ?
C2 O1 C5 C4 21.62(11) . . . . ?
C3 C4 C5 O1 -33.12(10) . . . . ?
C3 C4 C5 C6 -151.01(9) . . . . ?
O1 C5 C6 C7 100.37(14) . . . . ?
C4 C5 C6 C7 -145.37(12) . . . . ?
C5 C6 C7 C8 -1.5(2) . . . . ?
C5 C6 C7 C12 177.68(11) . . . . ?
C6 C7 C8 C9 126.18(13) . . . . ?
C12 C7 C8 C9 -53.01(14) . . . . ?
C7 C8 C9 C10 52.95(14) . . . . ?
C8 C9 C10 C11 -55.12(15) . . . . ?
C9 C10 C11 C12 56.18(14) . . . . ?
C6 C7 C12 C11 -125.03(12) . . . . ?
C8 C7 C12 C11 54.22(14) . . . . ?
C10 C11 C12 C7 -55.15(14) . . . . ?
C19 C3 C13 C18 -112.87(11) . . . . ?
C4 C3 C13 C18 117.89(11) . . . . ?
C2 C3 C13 C18 8.13(14) . . . . ?
C19 C3 C13 C14 65.55(12) . . . . ?
C4 C3 C13 C14 -63.68(12) . . . . ?
C2 C3 C13 C14 -173.45(9) . . . . ?
C18 C13 C14 C15 0.18(16) . . . . ?
C3 C13 C14 C15 -178.32(10) . . . . ?
C13 C14 C15 C16 -0.72(17) . . . . ?
C14 C15 C16 C17 0.47(17) . . . . ?
C15 C16 C17 C18 0.31(17) . . . . ?
C14 C13 C18 C17 0.60(16) . . . . ?
C3 C13 C18 C17 179.02(10) . . . . ?
C16 C17 C18 C13 -0.85(17) . . . . ?
C4 C3 C19 C20 0.97(15) . . . . ?
C2 C3 C19 C20 114.05(11) . . . . ?
C13 C3 C19 C20 -125.54(11) . . . . ?
C4 C3 C19 C24 -178.97(10) . . . . ?
C2 C3 C19 C24 -65.89(12) . . . . ?
C13 C3 C19 C24 54.52(13) . . . . ?
C24 C19 C20 C21 0.75(16) . . . . ?
C3 C19 C20 C21 -179.19(10) . . . . ?
C19 C20 C21 C22 0.34(17) . . . . ?
C20 C21 C22 C23 -0.82(17) . . . . ?
C21 C22 C23 C24 0.20(18) . . . . ?
C22 C23 C24 C19 0.91(18) . . . . ?
C20 C19 C24 C23 -1.37(17) . . . . ?
C3 C19 C24 C23 178.57(10) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_standards_number         0
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_decay_%        N/A
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_cmpd4a_sh006_ls1465c_0t
_database_code_depnum_ccdc_archive 'CCDC 997311'
_audit_update_record             
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-cyclohexyl-4-phenyl-1,2,3,4-tetrahydro-1,4-(epoxymethano)naphthalen-9-one
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_exptl_crystal_recrystallization_method 
'slow diff of pentane into ether/dichloromethane soln'
_chemical_melting_point          505-506

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      125(2)
_chemical_formula_weight         332.42

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1469(5)
_cell_length_b                   15.3030(10)
_cell_length_c                   16.4534(10)
_cell_angle_alpha                73.1240(10)
_cell_angle_beta                 89.7970(10)
_cell_angle_gamma                88.8640(10)
_cell_volume                     1721.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    2524
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.40
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   'TWINABS Version 2008/4'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22822
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_sigmaI/netI    0.1177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         30.51
_reflns_number_total             10426
_reflns_number_gt                9443
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 

 EXTI refined to zero and was removed from the refinement.

 Two component non-merohedral twin.  
 Rotated from first domain by 180.0 degrees about
 reciprocal axis  0.031  1.000 -0.005  and real axis  0.003  1.000  0.000

 BASF 0.477(1)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+2.1711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         17316
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O 0.1857(2) 0.89213(13) 0.35101(12) 0.0176(4) Uani 1 1 d . . .
O12 O -0.1015(2) 0.90176(14) 0.39821(13) 0.0224(4) Uani 1 1 d . . .
O21 O 0.6934(2) 0.61618(13) 0.15651(12) 0.0179(4) Uani 1 1 d . . .
O22 O 0.4077(2) 0.60742(15) 0.10876(13) 0.0235(4) Uani 1 1 d . . .
C11 C 0.3881(3) 0.77254(19) 0.43687(17) 0.0160(5) Uani 1 1 d . . .
C12 C 0.0607(3) 0.88157(18) 0.41466(17) 0.0169(5) Uani 1 1 d . . .
C13 C 0.1471(3) 0.84476(18) 0.50361(16) 0.0154(5) Uani 1 1 d . . .
C14 C 0.2964(3) 0.91675(19) 0.50759(17) 0.0184(5) Uani 1 1 d . . .
H14A H 0.2329 0.9752 0.5065 0.022 Uiso 1 1 calc R . .
H14B H 0.3680 0.8949 0.5613 0.022 Uiso 1 1 calc R . .
C15 C 0.4310(3) 0.93218(19) 0.43172(17) 0.0186(5) Uani 1 1 d . . .
H15A H 0.4212 0.9966 0.3964 0.022 Uiso 1 1 calc R . .
H15B H 0.5614 0.9199 0.4527 0.022 Uiso 1 1 calc R . .
C16 C 0.3836(3) 0.86888(19) 0.37765(17) 0.0159(5) Uani 1 1 d . . .
C17 C 0.4971(3) 0.88379(19) 0.29570(17) 0.0190(5) Uani 1 1 d . . .
H17A H 0.6214 0.8526 0.3123 0.023 Uiso 1 1 calc R . .
C18 C 0.4070(3) 0.8386(2) 0.23400(18) 0.0256(6) Uani 1 1 d . . .
H18A H 0.3928 0.7726 0.2629 0.031 Uiso 1 1 calc R . .
H18B H 0.2805 0.8657 0.2183 0.031 Uiso 1 1 calc R . .
C19 C 0.5226(4) 0.8503(2) 0.15318(19) 0.0289(7) Uani 1 1 d . . .
H19A H 0.6413 0.8147 0.1677 0.035 Uiso 1 1 calc R . .
H19B H 0.4526 0.8256 0.1132 0.035 Uiso 1 1 calc R . .
C21 C 0.8949(3) 0.72899(18) 0.06679(17) 0.0162(5) Uani 1 1 d . . .
C22 C 0.5701(3) 0.62424(19) 0.09251(17) 0.0174(5) Uani 1 1 d . . .
C23 C 0.6589(3) 0.65370(19) 0.00433(17) 0.0170(5) Uani 1 1 d . . .
C24 C 0.8124(3) 0.5789(2) 0.00646(18) 0.0200(6) Uani 1 1 d . . .
H24A H 0.7517 0.5202 0.0105 0.024 Uiso 1 1 calc R . .
H24B H 0.8851 0.5966 -0.0470 0.024 Uiso 1 1 calc R . .
C25 C 0.9456(3) 0.56651(19) 0.08240(18) 0.0195(5) Uani 1 1 d . . .
H25A H 0.9376 0.5035 0.1207 0.023 Uiso 1 1 calc R . .
H25B H 1.0761 0.5765 0.0620 0.023 Uiso 1 1 calc R . .
C26 C 0.8914(3) 0.63505(19) 0.13072(17) 0.0167(5) Uani 1 1 d . . .
C27 C 0.9990(3) 0.62445(19) 0.21366(17) 0.0187(5) Uani 1 1 d . . .
H27A H 1.1280 0.6475 0.1977 0.022 Uiso 1 1 calc R . .
C28 C 0.9105(3) 0.6836(2) 0.26526(18) 0.0226(6) Uani 1 1 d . . .
H28A H 0.9090 0.7483 0.2304 0.027 Uiso 1 1 calc R . .
H28B H 0.7793 0.6652 0.2787 0.027 Uiso 1 1 calc R . .
C29 C 1.0161(4) 0.6748(2) 0.34787(18) 0.0248(6) Uani 1 1 d . . .
H29A H 1.1431 0.6997 0.3346 0.030 Uiso 1 1 calc R . .
H29B H 0.9497 0.7110 0.3805 0.030 Uiso 1 1 calc R . .
C110 C 0.5663(4) 0.9495(2) 0.1102(2) 0.0365(8) Uani 1 1 d . . .
H11A H 0.4491 0.9835 0.0880 0.044 Uiso 1 1 calc R . .
H11B H 0.6511 0.9535 0.0616 0.044 Uiso 1 1 calc R . .
C111 C 0.6579(4) 0.9931(2) 0.1717(2) 0.0369(8) Uani 1 1 d . . .
H11C H 0.6790 1.0585 0.1427 0.044 Uiso 1 1 calc R . .
H11D H 0.7812 0.9631 0.1895 0.044 Uiso 1 1 calc R . .
C112 C 0.5362(4) 0.9843(2) 0.24993(19) 0.0276(6) Uani 1 1 d . . .
H11E H 0.4162 1.0180 0.2326 0.033 Uiso 1 1 calc R . .
H11F H 0.6004 1.0121 0.2893 0.033 Uiso 1 1 calc R . .
C113 C 0.5126(3) 0.70243(19) 0.43443(17) 0.0189(5) Uani 1 1 d . . .
H11G H 0.5998 0.7111 0.3892 0.023 Uiso 1 1 calc R . .
C114 C 0.5098(3) 0.6199(2) 0.49777(18) 0.0215(6) Uani 1 1 d . . .
H11H H 0.5954 0.5723 0.4958 0.026 Uiso 1 1 calc R . .
C115 C 0.3832(3) 0.6063(2) 0.56399(18) 0.0208(6) Uani 1 1 d . . .
H11I H 0.3818 0.5494 0.6070 0.025 Uiso 1 1 calc R . .
C116 C 0.2580(3) 0.67602(19) 0.56758(17) 0.0185(5) Uani 1 1 d . . .
H11J H 0.1712 0.6668 0.6130 0.022 Uiso 1 1 calc R . .
C117 C 0.2607(3) 0.75896(18) 0.50441(17) 0.0159(5) Uani 1 1 d . . .
C118 C -0.0010(3) 0.83084(19) 0.57252(17) 0.0174(5) Uani 1 1 d . . .
C119 C -0.1480(3) 0.7716(2) 0.57355(18) 0.0226(6) Uani 1 1 d . . .
H11K H -0.1547 0.7410 0.5310 0.027 Uiso 1 1 calc R . .
C120 C -0.2844(4) 0.7570(2) 0.63612(19) 0.0258(6) Uani 1 1 d . . .
H12A H -0.3831 0.7163 0.6363 0.031 Uiso 1 1 calc R . .
C121 C -0.2771(4) 0.8019(2) 0.69861(19) 0.0263(6) Uani 1 1 d . . .
H12B H -0.3708 0.7922 0.7412 0.032 Uiso 1 1 calc R . .
C122 C -0.1324(4) 0.8606(2) 0.69796(19) 0.0252(6) Uani 1 1 d . . .
H12C H -0.1261 0.8913 0.7404 0.030 Uiso 1 1 calc R . .
C123 C 0.0049(3) 0.87486(19) 0.63506(17) 0.0193(5) Uani 1 1 d . . .
H12D H 0.1038 0.9154 0.6352 0.023 Uiso 1 1 calc R . .
C210 C 1.0312(4) 0.5762(2) 0.4012(2) 0.0337(7) Uani 1 1 d . . .
H21A H 0.9047 0.5531 0.4192 0.040 Uiso 1 1 calc R . .
H21B H 1.1058 0.5719 0.4528 0.040 Uiso 1 1 calc R . .
C211 C 1.1232(4) 0.5176(2) 0.3516(2) 0.0351(8) Uani 1 1 d . . .
H21C H 1.1262 0.4531 0.3870 0.042 Uiso 1 1 calc R . .
H21D H 1.2540 0.5369 0.3386 0.042 Uiso 1 1 calc R . .
C212 C 1.0197(4) 0.5249(2) 0.2686(2) 0.0275(6) Uani 1 1 d . . .
H21E H 0.8941 0.4983 0.2817 0.033 Uiso 1 1 calc R . .
H21F H 1.0893 0.4892 0.2364 0.033 Uiso 1 1 calc R . .
C213 C 1.0175(3) 0.79838(19) 0.06637(18) 0.0197(5) Uani 1 1 d . . .
H21G H 1.1052 0.7907 0.1113 0.024 Uiso 1 1 calc R . .
C214 C 1.0117(3) 0.8790(2) 0.00013(18) 0.0225(6) Uani 1 1 d . . .
H21H H 1.0960 0.9264 -0.0002 0.027 Uiso 1 1 calc R . .
C215 C 0.8839(3) 0.8906(2) -0.06530(18) 0.0216(6) Uani 1 1 d . . .
H21I H 0.8799 0.9463 -0.1100 0.026 Uiso 1 1 calc R . .
C216 C 0.7609(3) 0.8212(2) -0.06614(18) 0.0196(6) Uani 1 1 d . . .
H21J H 0.6734 0.8293 -0.1112 0.023 Uiso 1 1 calc R . .
C217 C 0.7676(3) 0.74012(19) -0.00042(17) 0.0168(5) Uani 1 1 d . . .
C218 C 0.5136(3) 0.66366(19) -0.06514(17) 0.0182(5) Uani 1 1 d . . .
C219 C 0.3622(3) 0.7245(2) -0.07089(19) 0.0233(6) Uani 1 1 d . . .
H21K H 0.3521 0.7592 -0.0316 0.028 Uiso 1 1 calc R . .
C220 C 0.2264(4) 0.7349(2) -0.1333(2) 0.0276(7) Uani 1 1 d . . .
H22A H 0.1244 0.7765 -0.1364 0.033 Uiso 1 1 calc R . .
C221 C 0.2389(4) 0.6850(2) -0.1911(2) 0.0278(7) Uani 1 1 d . . .
H22B H 0.1459 0.6923 -0.2338 0.033 Uiso 1 1 calc R . .
C222 C 0.3880(4) 0.6245(2) -0.18632(19) 0.0253(6) Uani 1 1 d . . .
H22C H 0.3969 0.5898 -0.2256 0.030 Uiso 1 1 calc R . .
C223 C 0.5250(3) 0.6144(2) -0.12394(18) 0.0214(6) Uani 1 1 d . . .
H22D H 0.6275 0.5732 -0.1216 0.026 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C12 1.350(3) . ?
O11 C16 1.487(3) . ?
O12 C12 1.205(3) . ?
O21 C22 1.352(3) . ?
O21 C26 1.485(3) . ?
O22 C22 1.206(3) . ?
C11 C113 1.390(4) . ?
C11 C117 1.404(3) . ?
C11 C16 1.513(4) . ?
C12 C13 1.535(4) . ?
C13 C118 1.521(3) . ?
C13 C117 1.527(4) . ?
C13 C14 1.564(3) . ?
C14 C15 1.539(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.536(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.533(4) . ?
C17 C18 1.534(4) . ?
C17 C112 1.535(4) . ?
C17 H17A 1.0000 . ?
C18 C19 1.531(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C110 1.516(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C213 1.389(3) . ?
C21 C217 1.404(4) . ?
C21 C26 1.516(4) . ?
C22 C23 1.528(4) . ?
C23 C218 1.519(4) . ?
C23 C217 1.529(4) . ?
C23 C24 1.563(3) . ?
C24 C25 1.539(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.532(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.534(4) . ?
C27 C212 1.534(4) . ?
C27 C28 1.536(4) . ?
C27 H27A 1.0000 . ?
C28 C29 1.527(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C210 1.511(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C110 C111 1.519(5) . ?
C110 H11A 0.9900 . ?
C110 H11B 0.9900 . ?
C111 C112 1.526(4) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C112 H11E 0.9900 . ?
C112 H11F 0.9900 . ?
C113 C114 1.385(4) . ?
C113 H11G 0.9500 . ?
C114 C115 1.385(4) . ?
C114 H11H 0.9500 . ?
C115 C116 1.394(4) . ?
C115 H11I 0.9500 . ?
C116 C117 1.388(4) . ?
C116 H11J 0.9500 . ?
C118 C123 1.385(4) . ?
C118 C119 1.398(3) . ?
C119 C120 1.388(4) . ?
C119 H11K 0.9500 . ?
C120 C121 1.394(4) . ?
C120 H12A 0.9500 . ?
C121 C122 1.382(4) . ?
C121 H12B 0.9500 . ?
C122 C123 1.397(4) . ?
C122 H12C 0.9500 . ?
C123 H12D 0.9500 . ?
C210 C211 1.515(5) . ?
C210 H21A 0.9900 . ?
C210 H21B 0.9900 . ?
C211 C212 1.530(4) . ?
C211 H21C 0.9900 . ?
C211 H21D 0.9900 . ?
C212 H21E 0.9900 . ?
C212 H21F 0.9900 . ?
C213 C214 1.389(4) . ?
C213 H21G 0.9500 . ?
C214 C215 1.384(4) . ?
C214 H21H 0.9500 . ?
C215 C216 1.396(4) . ?
C215 H21I 0.9500 . ?
C216 C217 1.389(4) . ?
C216 H21J 0.9500 . ?
C218 C223 1.390(4) . ?
C218 C219 1.399(4) . ?
C219 C220 1.389(4) . ?
C219 H21K 0.9500 . ?
C220 C221 1.383(4) . ?
C220 H22A 0.9500 . ?
C221 C222 1.385(4) . ?
C221 H22B 0.9500 . ?
C222 C223 1.395(4) . ?
C222 H22C 0.9500 . ?
C223 H22D 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O11 C16 115.7(2) . . ?
C22 O21 C26 115.78(19) . . ?
C113 C11 C117 119.3(3) . . ?
C113 C11 C16 126.9(2) . . ?
C117 C11 C16 113.5(2) . . ?
O12 C12 O11 119.6(2) . . ?
O12 C12 C13 126.5(2) . . ?
O11 C12 C13 113.8(2) . . ?
C118 C13 C117 114.7(2) . . ?
C118 C13 C12 111.51(19) . . ?
C117 C13 C12 106.9(2) . . ?
C118 C13 C14 113.7(2) . . ?
C117 C13 C14 104.80(19) . . ?
C12 C13 C14 104.5(2) . . ?
C15 C14 C13 110.2(2) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.4(2) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
O11 C16 C11 107.38(18) . . ?
O11 C16 C17 106.3(2) . . ?
C11 C16 C17 115.6(2) . . ?
O11 C16 C15 104.86(19) . . ?
C11 C16 C15 106.6(2) . . ?
C17 C16 C15 115.3(2) . . ?
C16 C17 C18 111.9(2) . . ?
C16 C17 C112 114.2(2) . . ?
C18 C17 C112 110.0(2) . . ?
C16 C17 H17A 106.8 . . ?
C18 C17 H17A 106.8 . . ?
C112 C17 H17A 106.8 . . ?
C19 C18 C17 112.4(2) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C110 C19 C18 112.0(3) . . ?
C110 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
C110 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C213 C21 C217 119.8(3) . . ?
C213 C21 C26 126.5(2) . . ?
C217 C21 C26 113.5(2) . . ?
O22 C22 O21 119.5(2) . . ?
O22 C22 C23 126.8(2) . . ?
O21 C22 C23 113.70(19) . . ?
C218 C23 C22 111.47(19) . . ?
C218 C23 C217 115.1(2) . . ?
C22 C23 C217 106.3(2) . . ?
C218 C23 C24 113.6(2) . . ?
C22 C23 C24 104.7(2) . . ?
C217 C23 C24 104.88(19) . . ?
C25 C24 C23 111.1(2) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 109.4(2) . . ?
C26 C25 H25A 109.8 . . ?
C24 C25 H25A 109.8 . . ?
C26 C25 H25B 109.8 . . ?
C24 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
O21 C26 C21 107.24(19) . . ?
O21 C26 C25 105.6(2) . . ?
C21 C26 C25 106.6(2) . . ?
O21 C26 C27 105.32(19) . . ?
C21 C26 C27 115.8(2) . . ?
C25 C26 C27 115.5(2) . . ?
C212 C27 C26 113.2(2) . . ?
C212 C27 C28 110.5(2) . . ?
C26 C27 C28 111.4(2) . . ?
C212 C27 H27A 107.2 . . ?
C26 C27 H27A 107.2 . . ?
C28 C27 H27A 107.2 . . ?
C29 C28 C27 112.4(2) . . ?
C29 C28 H28A 109.1 . . ?
C27 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.9 . . ?
C210 C29 C28 111.0(2) . . ?
C210 C29 H29A 109.4 . . ?
C28 C29 H29A 109.4 . . ?
C210 C29 H29B 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C19 C110 C111 111.3(3) . . ?
C19 C110 H11A 109.4 . . ?
C111 C110 H11A 109.4 . . ?
C19 C110 H11B 109.4 . . ?
C111 C110 H11B 109.4 . . ?
H11A C110 H11B 108.0 . . ?
C110 C111 C112 111.2(3) . . ?
C110 C111 H11C 109.4 . . ?
C112 C111 H11C 109.4 . . ?
C110 C111 H11D 109.4 . . ?
C112 C111 H11D 109.4 . . ?
H11C C111 H11D 108.0 . . ?
C111 C112 C17 110.9(3) . . ?
C111 C112 H11E 109.5 . . ?
C17 C112 H11E 109.5 . . ?
C111 C112 H11F 109.5 . . ?
C17 C112 H11F 109.5 . . ?
H11E C112 H11F 108.0 . . ?
C114 C113 C11 120.2(2) . . ?
C114 C113 H11G 119.9 . . ?
C11 C113 H11G 119.9 . . ?
C115 C114 C113 120.5(3) . . ?
C115 C114 H11H 119.8 . . ?
C113 C114 H11H 119.8 . . ?
C114 C115 C116 120.1(3) . . ?
C114 C115 H11I 120.0 . . ?
C116 C115 H11I 120.0 . . ?
C117 C116 C115 119.6(2) . . ?
C117 C116 H11J 120.2 . . ?
C115 C116 H11J 120.2 . . ?
C116 C117 C11 120.3(2) . . ?
C116 C117 C13 126.0(2) . . ?
C11 C117 C13 113.4(2) . . ?
C123 C118 C119 118.5(2) . . ?
C123 C118 C13 122.1(2) . . ?
C119 C118 C13 119.4(2) . . ?
C120 C119 C118 120.7(3) . . ?
C120 C119 H11K 119.7 . . ?
C118 C119 H11K 119.7 . . ?
C119 C120 C121 120.3(3) . . ?
C119 C120 H12A 119.8 . . ?
C121 C120 H12A 119.8 . . ?
C122 C121 C120 119.4(3) . . ?
C122 C121 H12B 120.3 . . ?
C120 C121 H12B 120.3 . . ?
C121 C122 C123 120.2(3) . . ?
C121 C122 H12C 119.9 . . ?
C123 C122 H12C 119.9 . . ?
C118 C123 C122 121.0(2) . . ?
C118 C123 H12D 119.5 . . ?
C122 C123 H12D 119.5 . . ?
C29 C210 C211 110.9(3) . . ?
C29 C210 H21A 109.5 . . ?
C211 C210 H21A 109.5 . . ?
C29 C210 H21B 109.5 . . ?
C211 C210 H21B 109.5 . . ?
H21A C210 H21B 108.0 . . ?
C210 C211 C212 112.1(3) . . ?
C210 C211 H21C 109.2 . . ?
C212 C211 H21C 109.2 . . ?
C210 C211 H21D 109.2 . . ?
C212 C211 H21D 109.2 . . ?
H21C C211 H21D 107.9 . . ?
C211 C212 C27 111.5(2) . . ?
C211 C212 H21E 109.3 . . ?
C27 C212 H21E 109.3 . . ?
C211 C212 H21F 109.3 . . ?
C27 C212 H21F 109.3 . . ?
H21E C212 H21F 108.0 . . ?
C21 C213 C214 119.8(2) . . ?
C21 C213 H21G 120.1 . . ?
C214 C213 H21G 120.1 . . ?
C215 C214 C213 120.3(3) . . ?
C215 C214 H21H 119.8 . . ?
C213 C214 H21H 119.8 . . ?
C214 C215 C216 120.5(3) . . ?
C214 C215 H21I 119.8 . . ?
C216 C215 H21I 119.8 . . ?
C217 C216 C215 119.3(2) . . ?
C217 C216 H21J 120.3 . . ?
C215 C216 H21J 120.3 . . ?
C216 C217 C21 120.2(2) . . ?
C216 C217 C23 126.4(2) . . ?
C21 C217 C23 113.3(2) . . ?
C223 C218 C219 118.2(2) . . ?
C223 C218 C23 122.5(2) . . ?
C219 C218 C23 119.4(2) . . ?
C220 C219 C218 120.8(3) . . ?
C220 C219 H21K 119.6 . . ?
C218 C219 H21K 119.6 . . ?
C221 C220 C219 120.4(3) . . ?
C221 C220 H22A 119.8 . . ?
C219 C220 H22A 119.8 . . ?
C220 C221 C222 119.5(3) . . ?
C220 C221 H22B 120.2 . . ?
C222 C221 H22B 120.2 . . ?
C221 C222 C223 120.2(3) . . ?
C221 C222 H22C 119.9 . . ?
C223 C222 H22C 119.9 . . ?
C218 C223 C222 120.9(3) . . ?
C218 C223 H22D 119.5 . . ?
C222 C223 H22D 119.5 . . ?

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
C16 O11 C12 O12 177.7(2) . . . . ?
C16 O11 C12 C13 -1.5(3) . . . . ?
O12 C12 C13 C118 3.1(4) . . . . ?
O11 C12 C13 C118 -177.8(2) . . . . ?
O12 C12 C13 C117 129.2(3) . . . . ?
O11 C12 C13 C117 -51.7(3) . . . . ?
O12 C12 C13 C14 -120.1(3) . . . . ?
O11 C12 C13 C14 59.0(3) . . . . ?
C118 C13 C14 C15 -175.5(2) . . . . ?
C117 C13 C14 C15 58.5(3) . . . . ?
C12 C13 C14 C15 -53.7(3) . . . . ?
C13 C14 C15 C16 -2.7(3) . . . . ?
C12 O11 C16 C11 54.4(3) . . . . ?
C12 O11 C16 C17 178.7(2) . . . . ?
C12 O11 C16 C15 -58.8(3) . . . . ?
C113 C11 C16 O11 133.4(2) . . . . ?
C117 C11 C16 O11 -52.5(3) . . . . ?
C113 C11 C16 C17 15.0(4) . . . . ?
C117 C11 C16 C17 -170.9(2) . . . . ?
C113 C11 C16 C15 -114.6(3) . . . . ?
C117 C11 C16 C15 59.4(2) . . . . ?
C14 C15 C16 O11 58.4(3) . . . . ?
C14 C15 C16 C11 -55.3(3) . . . . ?
C14 C15 C16 C17 174.8(2) . . . . ?
O11 C16 C17 C18 -48.3(3) . . . . ?
C11 C16 C17 C18 70.7(3) . . . . ?
C15 C16 C17 C18 -164.0(2) . . . . ?
O11 C16 C17 C112 77.5(3) . . . . ?
C11 C16 C17 C112 -163.5(2) . . . . ?
C15 C16 C17 C112 -38.2(3) . . . . ?
C16 C17 C18 C19 -178.1(2) . . . . ?
C112 C17 C18 C19 53.9(3) . . . . ?
C17 C18 C19 C110 -53.2(3) . . . . ?
C26 O21 C22 O22 177.9(2) . . . . ?
C26 O21 C22 C23 -1.3(3) . . . . ?
O22 C22 C23 C218 2.2(4) . . . . ?
O21 C22 C23 C218 -178.8(2) . . . . ?
O22 C22 C23 C217 128.3(3) . . . . ?
O21 C22 C23 C217 -52.6(3) . . . . ?
O22 C22 C23 C24 -121.0(3) . . . . ?
O21 C22 C23 C24 58.0(3) . . . . ?
C218 C23 C24 C25 -175.3(2) . . . . ?
C22 C23 C24 C25 -53.5(3) . . . . ?
C217 C23 C24 C25 58.2(3) . . . . ?
C23 C24 C25 C26 -2.6(3) . . . . ?
C22 O21 C26 C21 54.3(3) . . . . ?
C22 O21 C26 C25 -59.1(3) . . . . ?
C22 O21 C26 C27 178.2(2) . . . . ?
C213 C21 C26 O21 133.4(2) . . . . ?
C217 C21 C26 O21 -51.6(3) . . . . ?
C213 C21 C26 C25 -113.8(3) . . . . ?
C217 C21 C26 C25 61.1(2) . . . . ?
C213 C21 C26 C27 16.2(4) . . . . ?
C217 C21 C26 C27 -168.8(2) . . . . ?
C24 C25 C26 O21 58.0(3) . . . . ?
C24 C25 C26 C21 -55.9(3) . . . . ?
C24 C25 C26 C27 173.9(2) . . . . ?
O21 C26 C27 C212 72.0(3) . . . . ?
C21 C26 C27 C212 -169.8(2) . . . . ?
C25 C26 C27 C212 -44.2(3) . . . . ?
O21 C26 C27 C28 -53.2(3) . . . . ?
C21 C26 C27 C28 65.0(3) . . . . ?
C25 C26 C27 C28 -169.3(2) . . . . ?
C212 C27 C28 C29 53.7(3) . . . . ?
C26 C27 C28 C29 -179.5(2) . . . . ?
C27 C28 C29 C210 -55.7(3) . . . . ?
C18 C19 C110 C111 53.6(3) . . . . ?
C19 C110 C111 C112 -56.3(3) . . . . ?
C110 C111 C112 C17 57.9(3) . . . . ?
C16 C17 C112 C111 177.1(2) . . . . ?
C18 C17 C112 C111 -56.1(3) . . . . ?
C117 C11 C113 C114 0.4(4) . . . . ?
C16 C11 C113 C114 174.2(2) . . . . ?
C11 C113 C114 C115 0.1(4) . . . . ?
C113 C114 C115 C116 -0.4(4) . . . . ?
C114 C115 C116 C117 0.1(4) . . . . ?
C115 C116 C117 C11 0.4(4) . . . . ?
C115 C116 C117 C13 -173.6(2) . . . . ?
C113 C11 C117 C116 -0.7(4) . . . . ?
C16 C11 C117 C116 -175.2(2) . . . . ?
C113 C11 C117 C13 174.0(2) . . . . ?
C16 C11 C117 C13 -0.6(3) . . . . ?
C118 C13 C117 C116 -9.5(3) . . . . ?
C12 C13 C117 C116 -133.7(2) . . . . ?
C14 C13 C117 C116 115.9(3) . . . . ?
C118 C13 C117 C11 176.2(2) . . . . ?
C12 C13 C117 C11 52.0(3) . . . . ?
C14 C13 C117 C11 -58.5(3) . . . . ?
C117 C13 C118 C123 117.2(3) . . . . ?
C12 C13 C118 C123 -121.2(3) . . . . ?
C14 C13 C118 C123 -3.4(4) . . . . ?
C117 C13 C118 C119 -62.5(3) . . . . ?
C12 C13 C118 C119 59.1(3) . . . . ?
C14 C13 C118 C119 176.9(2) . . . . ?
C123 C118 C119 C120 -0.3(4) . . . . ?
C13 C118 C119 C120 179.5(3) . . . . ?
C118 C119 C120 C121 0.4(5) . . . . ?
C119 C120 C121 C122 -0.3(5) . . . . ?
C120 C121 C122 C123 0.2(5) . . . . ?
C119 C118 C123 C122 0.1(4) . . . . ?
C13 C118 C123 C122 -179.7(3) . . . . ?
C121 C122 C123 C118 0.0(5) . . . . ?
C28 C29 C210 C211 56.1(3) . . . . ?
C29 C210 C211 C212 -56.4(3) . . . . ?
C210 C211 C212 C27 55.0(3) . . . . ?
C26 C27 C212 C211 -178.5(2) . . . . ?
C28 C27 C212 C211 -52.8(3) . . . . ?
C217 C21 C213 C214 1.0(4) . . . . ?
C26 C21 C213 C214 175.7(2) . . . . ?
C21 C213 C214 C215 0.2(4) . . . . ?
C213 C214 C215 C216 -0.8(4) . . . . ?
C214 C215 C216 C217 0.1(4) . . . . ?
C215 C216 C217 C21 1.1(4) . . . . ?
C215 C216 C217 C23 -173.1(2) . . . . ?
C213 C21 C217 C216 -1.6(4) . . . . ?
C26 C21 C217 C216 -177.0(2) . . . . ?
C213 C21 C217 C23 173.3(2) . . . . ?
C26 C21 C217 C23 -2.1(3) . . . . ?
C218 C23 C217 C216 -7.9(3) . . . . ?
C22 C23 C217 C216 -131.8(3) . . . . ?
C24 C23 C217 C216 117.6(3) . . . . ?
C218 C23 C217 C21 177.6(2) . . . . ?
C22 C23 C217 C21 53.7(3) . . . . ?
C24 C23 C217 C21 -56.9(3) . . . . ?
C22 C23 C218 C223 -121.7(3) . . . . ?
C217 C23 C218 C223 117.2(3) . . . . ?
C24 C23 C218 C223 -3.8(4) . . . . ?
C22 C23 C218 C219 58.3(3) . . . . ?
C217 C23 C218 C219 -62.8(3) . . . . ?
C24 C23 C218 C219 176.3(2) . . . . ?
C223 C218 C219 C220 0.4(4) . . . . ?
C23 C218 C219 C220 -179.6(3) . . . . ?
C218 C219 C220 C221 0.0(5) . . . . ?
C219 C220 C221 C222 0.0(5) . . . . ?
C220 C221 C222 C223 -0.4(5) . . . . ?
C219 C218 C223 C222 -0.8(4) . . . . ?
C23 C218 C223 C222 179.3(3) . . . . ?
C221 C222 C223 C218 0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.070


####################################################################### 
# 
# 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_cmpd9_sh012_12115
_database_code_depnum_ccdc_archive 'CCDC 997312'
_audit_update_record             
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;        
2-methoxy-4-phenyl-4,5,5a,6,6a,7,8,9,10,10a-decahydroacephenanthrylene-
4-carboxylic acid
;
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H26 O3'
_chemical_formula_sum            'C24 H26 O3'
_exptl_crystal_recrystallization_method 
'slow diff of pentane into ether/dichloromethane soln'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         362.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7954(4)
_cell_length_b                   9.8427(4)
_cell_length_c                   11.0909(5)
_cell_angle_alpha                78.548(2)
_cell_angle_beta                 77.234(2)
_cell_angle_gamma                64.389(3)
_cell_volume                     933.94(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8356
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.27
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   'SADABS (Sheldirck, 2001)'

_exptl_special_details           
; 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17614
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.30
_reflns_number_total             4626
_reflns_number_gt                4139
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4626
_refine_ls_number_parameters     303
_refine_ls_number_restraints     322
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20040(12) 0.45337(12) 0.75786(10) 0.0189(2) Uani 1 1 d . A .
H1 H 0.2077 0.4733 0.6652 0.023 Uiso 1 1 calc R . .
C2 C 0.08156(12) 0.38528(12) 0.80955(10) 0.0202(2) Uani 1 1 d . A .
H2A H -0.0062 0.4338 0.7628 0.024 Uiso 1 1 calc R . .
H2B H 0.0431 0.3988 0.8986 0.024 Uiso 1 1 calc R . .
C3 C 0.16964(11) 0.21328(11) 0.79213(9) 0.0173(2) Uani 1 1 d D . .
C4 C 0.33314(11) 0.18380(12) 0.80550(9) 0.0167(2) Uani 1 1 d . A .
C5 C 0.34518(12) 0.32218(12) 0.79035(9) 0.0174(2) Uani 1 1 d . . .
C6 C 0.45751(11) 0.04798(12) 0.83221(9) 0.0173(2) Uani 1 1 d . . .
H6 H 0.4513 -0.0472 0.8408 0.021 Uiso 1 1 calc R A .
C7 C 0.59189(12) 0.05773(12) 0.84587(9) 0.0178(2) Uani 1 1 d . A .
C8 C 0.59877(12) 0.19830(12) 0.84055(10) 0.0195(2) Uani 1 1 d . . .
H8 H 0.6894 0.2015 0.8549 0.023 Uiso 1 1 calc R A .
C9 C 0.47397(12) 0.33332(12) 0.81451(9) 0.0182(2) Uani 1 1 d . A .
C10 C 0.46141(12) 0.48846(12) 0.83278(10) 0.0205(2) Uani 1 1 d . . .
H10 H 0.4331 0.4947 0.9245 0.025 Uiso 1 1 calc R A .
C11 C 0.32962(13) 0.62101(12) 0.77289(11) 0.0225(2) Uani 1 1 d . A .
H11 H 0.3106 0.7144 0.8085 0.027 Uiso 1 1 calc R . .
C12 C 0.17996(13) 0.59643(12) 0.80752(11) 0.0232(2) Uani 1 1 d . . .
H12A H 0.1511 0.5864 0.8992 0.028 Uiso 1 1 calc R A .
H12B H 0.0964 0.6854 0.7718 0.028 Uiso 1 1 calc R . .
C13 C 0.61101(13) 0.51216(13) 0.79418(11) 0.0248(2) Uani 1 1 d . A .
H13A H 0.6000 0.6006 0.8312 0.030 Uiso 1 1 calc R . .
H13B H 0.6953 0.4218 0.8277 0.030 Uiso 1 1 calc R . .
C14 C 0.65296(14) 0.53847(14) 0.65278(11) 0.0271(2) Uani 1 1 d . . .
H14A H 0.7471 0.5578 0.6325 0.033 Uiso 1 1 calc R A .
H14B H 0.6739 0.4464 0.6158 0.033 Uiso 1 1 calc R . .
C15 C 0.52257(14) 0.67356(14) 0.59731(12) 0.0287(3) Uani 1 1 d . A .
H15A H 0.5075 0.7671 0.6289 0.034 Uiso 1 1 calc R . .
H15B H 0.5496 0.6865 0.5056 0.034 Uiso 1 1 calc R . .
C16 C 0.37428(14) 0.64945(13) 0.63182(11) 0.0261(2) Uani 1 1 d . . .
H16A H 0.3868 0.5617 0.5930 0.031 Uiso 1 1 calc R A .
H16B H 0.2906 0.7401 0.5980 0.031 Uiso 1 1 calc R . .
C17 C 0.1623(7) 0.1760(7) 0.6648(3) 0.0169(9) Uani 0.60(2) 1 d PDU A 1
C18 C 0.0156(6) 0.2110(9) 0.6429(6) 0.0291(9) Uani 0.60(2) 1 d PDU A 1
H18 H -0.0703 0.2580 0.7029 0.035 Uiso 0.60(2) 1 calc PR A 1
C19 C -0.0070(6) 0.1782(10) 0.5349(7) 0.0374(11) Uani 0.60(2) 1 d PDU A 1
H19 H -0.1079 0.2025 0.5217 0.045 Uiso 0.60(2) 1 calc PR A 1
C20 C 0.1167(8) 0.1103(9) 0.4462(5) 0.0317(10) Uani 0.60(2) 1 d PDU A 1
H20 H 0.1012 0.0888 0.3717 0.038 Uiso 0.60(2) 1 calc PR A 1
C21 C 0.2628(7) 0.0741(10) 0.4675(6) 0.0286(12) Uani 0.60(2) 1 d PDU A 1
H21 H 0.3485 0.0266 0.4076 0.034 Uiso 0.60(2) 1 calc PR A 1
C22 C 0.2855(6) 0.1066(9) 0.5760(6) 0.0233(11) Uani 0.60(2) 1 d PDU A 1
H22 H 0.3867 0.0809 0.5894 0.028 Uiso 0.60(2) 1 calc PR A 1
C17' C 0.1478(11) 0.1848(11) 0.6664(5) 0.0216(16) Uani 0.40(2) 1 d PDU A 2
C18' C 0.0089(9) 0.2412(13) 0.6230(8) 0.0350(16) Uani 0.40(2) 1 d PDU A 2
H18' H -0.0814 0.3042 0.6713 0.042 Uiso 0.40(2) 1 calc PR A 2
C19' C -0.0006(9) 0.2074(13) 0.5105(9) 0.0353(16) Uani 0.40(2) 1 d PDU A 2
H19' H -0.0968 0.2468 0.4823 0.042 Uiso 0.40(2) 1 calc PR A 2
C20' C 0.1307(12) 0.1160(12) 0.4389(7) 0.0304(16) Uani 0.40(2) 1 d PDU A 2
H20' H 0.1252 0.0938 0.3610 0.036 Uiso 0.40(2) 1 calc PR A 2
C21' C 0.2695(9) 0.0576(13) 0.4822(8) 0.0244(14) Uani 0.40(2) 1 d PDU A 2
H21' H 0.3593 -0.0075 0.4348 0.029 Uiso 0.40(2) 1 calc PR A 2
C22' C 0.2786(9) 0.0934(12) 0.5943(9) 0.0174(12) Uani 0.40(2) 1 d PDU A 2
H22' H 0.3750 0.0550 0.6218 0.021 Uiso 0.40(2) 1 calc PR A 2
C23 C 0.09807(11) 0.11928(12) 0.88948(10) 0.0181(2) Uani 1 1 d . A .
O24 O -0.02926(9) 0.17747(9) 0.94999(8) 0.02413(18) Uani 1 1 d . . .
O25 O 0.18071(9) -0.02789(9) 0.89635(8) 0.02241(18) Uani 1 1 d . . .
H25 H 0.1263(17) -0.0746(17) 0.9485(15) 0.027 Uiso 1 1 d . . .
O26 O 0.72424(8) -0.06568(9) 0.86954(7) 0.02111(18) Uani 1 1 d . . .
C27 C 0.72495(12) -0.21195(12) 0.87505(10) 0.0222(2) Uani 1 1 d . A .
H27A H 0.6452 -0.2235 0.9420 0.033 Uiso 1 1 calc R . .
H27B H 0.8252 -0.2902 0.8915 0.033 Uiso 1 1 calc R . .
H27C H 0.7049 -0.2227 0.7955 0.033 Uiso 1 1 calc R . .


_geom_special_details            
; 
;

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 C5 1.5055(14) . ?
C1 C12 1.5302(14) . ?
C1 C2 1.5362(14) . ?
C1 H1 1.0000 . ?
C2 C3 1.5625(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C23 1.5306(14) . ?
C3 C4 1.5354(13) . ?
C3 C17 1.551(2) . ?
C3 C17' 1.552(3) . ?
C4 C5 1.3915(14) . ?
C4 C6 1.3976(14) . ?
C5 C9 1.3986(14) . ?
C6 C7 1.4028(14) . ?
C6 H6 0.9500 . ?
C7 O26 1.3739(12) . ?
C7 C8 1.4031(14) . ?
C8 C9 1.3940(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.5288(14) . ?
C10 C13 1.5374(15) . ?
C10 C11 1.5455(15) . ?
C10 H10 1.0000 . ?
C11 C16 1.5321(16) . ?
C11 C12 1.5414(15) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5301(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5271(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5260(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.386(2) . ?
C17 C18 1.392(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C17' C18' 1.386(3) . ?
C17' C22' 1.388(3) . ?
C18' C19' 1.386(3) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.387(3) . ?
C19' H19' 0.9500 . ?
C20' C21' 1.383(3) . ?
C20' H20' 0.9500 . ?
C21' C22' 1.389(3) . ?
C21' H21' 0.9500 . ?
C22' H22' 0.9500 . ?
C23 O24 1.2244(13) . ?
C23 O25 1.3149(13) . ?
O25 H25 0.894(16) . ?
O26 C27 1.4259(13) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C5 C1 C12 110.66(9) . . ?
C5 C1 C2 101.17(8) . . ?
C12 C1 C2 118.61(9) . . ?
C5 C1 H1 108.6 . . ?
C12 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C1 C2 C3 104.81(8) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C23 C3 C4 114.57(8) . . ?
C23 C3 C17 105.0(2) . . ?
C4 C3 C17 112.0(2) . . ?
C23 C3 C17' 103.8(4) . . ?
C4 C3 C17' 116.5(4) . . ?
C23 C3 C2 110.29(8) . . ?
C4 C3 C2 101.67(8) . . ?
C17 C3 C2 113.6(2) . . ?
C17' C3 C2 110.1(4) . . ?
C5 C4 C6 120.62(9) . . ?
C5 C4 C3 108.87(9) . . ?
C6 C4 C3 130.48(9) . . ?
C4 C5 C9 121.97(9) . . ?
C4 C5 C1 112.03(9) . . ?
C9 C5 C1 125.76(9) . . ?
C4 C6 C7 117.41(9) . . ?
C4 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
O26 C7 C6 124.10(9) . . ?
O26 C7 C8 114.37(9) . . ?
C6 C7 C8 121.49(10) . . ?
C9 C8 C7 120.67(9) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C5 117.34(9) . . ?
C8 C9 C10 123.07(9) . . ?
C5 C9 C10 118.75(9) . . ?
C9 C10 C13 115.20(9) . . ?
C9 C10 C11 112.56(9) . . ?
C13 C10 C11 110.74(9) . . ?
C9 C10 H10 105.8 . . ?
C13 C10 H10 105.8 . . ?
C11 C10 H10 105.8 . . ?
C16 C11 C12 112.21(9) . . ?
C16 C11 C10 111.56(9) . . ?
C12 C11 C10 111.34(9) . . ?
C16 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
C10 C11 H11 107.1 . . ?
C1 C12 C11 110.38(8) . . ?
C1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C10 112.44(9) . . ?
C14 C13 H13A 109.1 . . ?
C10 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C10 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C13 110.51(10) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.60(9) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 C11 112.30(10) . . ?
C15 C16 H16A 109.1 . . ?
C11 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C11 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C22 C17 C18 118.2(3) . . ?
C22 C17 C3 126.8(4) . . ?
C18 C17 C3 114.9(4) . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.1(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.5(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.9(3) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C18' C17' C22' 118.5(4) . . ?
C18' C17' C3 125.0(6) . . ?
C22' C17' C3 116.4(6) . . ?
C19' C18' C17' 121.2(4) . . ?
C19' C18' H18' 119.4 . . ?
C17' C18' H18' 119.4 . . ?
C18' C19' C20' 119.9(3) . . ?
C18' C19' H19' 120.0 . . ?
C20' C19' H19' 120.0 . . ?
C21' C20' C19' 119.3(3) . . ?
C21' C20' H20' 120.3 . . ?
C19' C20' H20' 120.3 . . ?
C20' C21' C22' 120.5(3) . . ?
C20' C21' H21' 119.8 . . ?
C22' C21' H21' 119.8 . . ?
C17' C22' C21' 120.5(3) . . ?
C17' C22' H22' 119.7 . . ?
C21' C22' H22' 119.7 . . ?
O24 C23 O25 123.64(10) . . ?
O24 C23 C3 121.97(9) . . ?
O25 C23 C3 114.26(8) . . ?
C23 O25 H25 108.5(9) . . ?
C7 O26 C27 117.07(8) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C5 C1 C2 C3 -32.88(10) . . . . ?
C12 C1 C2 C3 -154.02(9) . . . . ?
C1 C2 C3 C23 153.00(8) . . . . ?
C1 C2 C3 C4 31.07(10) . . . . ?
C1 C2 C3 C17 -89.5(3) . . . . ?
C1 C2 C3 C17' -93.1(4) . . . . ?
C23 C3 C4 C5 -136.09(9) . . . . ?
C17 C3 C4 C5 104.5(3) . . . . ?
C17' C3 C4 C5 102.6(4) . . . . ?
C2 C3 C4 C5 -17.17(10) . . . . ?
C23 C3 C4 C6 41.89(14) . . . . ?
C17 C3 C4 C6 -77.5(3) . . . . ?
C17' C3 C4 C6 -79.5(4) . . . . ?
C2 C3 C4 C6 160.82(10) . . . . ?
C6 C4 C5 C9 -7.26(15) . . . . ?
C3 C4 C5 C9 170.95(9) . . . . ?
C6 C4 C5 C1 178.04(9) . . . . ?
C3 C4 C5 C1 -3.74(11) . . . . ?
C12 C1 C5 C4 149.87(9) . . . . ?
C2 C1 C5 C4 23.29(11) . . . . ?
C12 C1 C5 C9 -24.58(14) . . . . ?
C2 C1 C5 C9 -151.16(10) . . . . ?
C5 C4 C6 C7 1.51(14) . . . . ?
C3 C4 C6 C7 -176.28(9) . . . . ?
C4 C6 C7 O26 -178.58(9) . . . . ?
C4 C6 C7 C8 3.80(15) . . . . ?
O26 C7 C8 C9 178.57(9) . . . . ?
C6 C7 C8 C9 -3.60(16) . . . . ?
C7 C8 C9 C5 -1.96(15) . . . . ?
C7 C8 C9 C10 167.36(9) . . . . ?
C4 C5 C9 C8 7.36(15) . . . . ?
C1 C5 C9 C8 -178.71(9) . . . . ?
C4 C5 C9 C10 -162.43(9) . . . . ?
C1 C5 C9 C10 11.50(15) . . . . ?
C8 C9 C10 C13 40.20(14) . . . . ?
C5 C9 C10 C13 -150.63(10) . . . . ?
C8 C9 C10 C11 168.46(9) . . . . ?
C5 C9 C10 C11 -22.36(13) . . . . ?
C9 C10 C11 C16 -78.51(11) . . . . ?
C13 C10 C11 C16 52.05(11) . . . . ?
C9 C10 C11 C12 47.70(12) . . . . ?
C13 C10 C11 C12 178.26(8) . . . . ?
C5 C1 C12 C11 48.25(12) . . . . ?
C2 C1 C12 C11 164.44(9) . . . . ?
C16 C11 C12 C1 63.55(12) . . . . ?
C10 C11 C12 C1 -62.30(12) . . . . ?
C9 C10 C13 C14 75.20(12) . . . . ?
C11 C10 C13 C14 -53.96(12) . . . . ?
C10 C13 C14 C15 56.60(12) . . . . ?
C13 C14 C15 C16 -56.85(13) . . . . ?
C14 C15 C16 C11 56.44(13) . . . . ?
C12 C11 C16 C15 -179.90(9) . . . . ?
C10 C11 C16 C15 -54.17(12) . . . . ?
C23 C3 C17 C22 -117.2(5) . . . . ?
C4 C3 C17 C22 7.8(5) . . . . ?
C2 C3 C17 C22 122.3(5) . . . . ?
C23 C3 C17 C18 59.7(4) . . . . ?
C4 C3 C17 C18 -175.4(4) . . . . ?
C2 C3 C17 C18 -60.9(5) . . . . ?
C22 C17 C18 C19 -0.4(2) . . . . ?
C3 C17 C18 C19 -177.5(5) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C19 C20 C21 C22 -0.6(6) . . . . ?
C18 C17 C22 C21 0.6(4) . . . . ?
C3 C17 C22 C21 177.3(5) . . . . ?
C20 C21 C22 C17 -0.1(6) . . . . ?
C23 C3 C17' C18' 71.2(7) . . . . ?
C4 C3 C17' C18' -161.9(6) . . . . ?
C2 C3 C17' C18' -46.8(8) . . . . ?
C23 C3 C17' C22' -107.7(6) . . . . ?
C4 C3 C17' C22' 19.2(8) . . . . ?
C2 C3 C17' C22' 134.3(6) . . . . ?
C22' C17' C18' C19' 0.2(3) . . . . ?
C3 C17' C18' C19' -178.6(8) . . . . ?
C17' C18' C19' C20' -0.3(3) . . . . ?
C18' C19' C20' C21' 1.1(6) . . . . ?
C19' C20' C21' C22' -1.9(7) . . . . ?
C18' C17' C22' C21' -1.0(6) . . . . ?
C3 C17' C22' C21' 177.9(8) . . . . ?
C20' C21' C22' C17' 1.9(7) . . . . ?
C4 C3 C23 O24 129.50(10) . . . . ?
C17 C3 C23 O24 -107.2(2) . . . . ?
C17' C3 C23 O24 -102.4(4) . . . . ?
C2 C3 C23 O24 15.54(14) . . . . ?
C4 C3 C23 O25 -54.38(12) . . . . ?
C17 C3 C23 O25 68.9(2) . . . . ?
C17' C3 C23 O25 73.7(4) . . . . ?
C2 C3 C23 O25 -168.34(9) . . . . ?
C6 C7 O26 C27 2.74(14) . . . . ?
C8 C7 O26 C27 -179.49(9) . . . . ?

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
O25 H25 O24 0.894(16) 1.762(16) 2.6547(11) 176.4(14) 2_557

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.049

_iucr_refine_instruction_details 
; 
TITL 12115 in P-1
CELL 0.71073   9.7954   9.8427  11.0909  78.548  77.234  64.389
ZERR    2.00   0.0004   0.0004   0.0005   0.002   0.002   0.003
LATT  1
SFAC C  H  O
UNIT 48 52 6
TEMP -173
SIZE 0.02 0.40 0.52
acta 50.5
conf
wpdb -1
eqiv $1 -x, -y, -z+2
htab o25 O24_$1
htab
 
sadi 0.004 c3 c17 c3 c17'
sadi 0.004 c17 c18 c18 c19 c19 c20 c20 c21 c21 c22 c22 c17
sadi 0.004 c17' c18' c18' c19' c19' c20' c20' c21' c21' c22' c22' c17'
sadi 0.004 c17 c18 c18 c19 c19 c20 c20 c21 c21 c22 c22 c17 c17' c18'
sadi 0.008 c17' c19' c19' c21' c21' c17' c18' c20' c20' c22' c22' c20'
sadi 0.008 c17 c19 c19 c21 c21 c17 c18 c20 c20 c22 c22 c20 c17' c19'
flat 0.010 c17 c18 c19 c20 c21 c22
flat 0.010 c17' c18' c19' c20' c21' c22'
delu 0.010 c17 > c22
delu 0.010 c17' > c22'
simu 0.010 c17 > c22'
 
L.S. 8 4
BOND $h
FMAP 2
PLAN 20
 
WGHT    0.080000    0.280000
FVAR       1.00637   0.60115
C1    1    0.200401    0.453374    0.757865    11.00000    0.01746    0.01734 =
         0.02205   -0.00313   -0.00134   -0.00758
AFIX  13
H1    2    0.207683    0.473342    0.665175    11.00000   -1.20000
AFIX   0
C2    1    0.081561    0.385282    0.809552    11.00000    0.01668    0.01856 =
         0.02551   -0.00429   -0.00082   -0.00764
AFIX  23
H2A   2   -0.006196    0.433813    0.762765    11.00000   -1.20000
H2B   2    0.043082    0.398824    0.898626    11.00000   -1.20000
AFIX   0
C3    1    0.169638    0.213276    0.792129    11.00000    0.01450    0.01897 =
         0.01946   -0.00416   -0.00057   -0.00799
C4    1    0.333143    0.183798    0.805499    11.00000    0.01566    0.02006 =
         0.01616   -0.00429   -0.00025   -0.00903
C5    1    0.345181    0.322176    0.790348    11.00000    0.01744    0.01869 =
         0.01671   -0.00297   -0.00087   -0.00845
C6    1    0.457508    0.047979    0.832209    11.00000    0.01754    0.01916 =
         0.01709   -0.00388   -0.00084   -0.00945
AFIX  43
H6    2    0.451283   -0.047236    0.840784    11.00000   -1.20000
AFIX   0
C7    1    0.591892    0.057727    0.845866    11.00000    0.01648    0.02044 =
         0.01656   -0.00312   -0.00146   -0.00765
C8    1    0.598767    0.198297    0.840555    11.00000    0.01877    0.02340 =
         0.02007   -0.00371   -0.00251   -0.01175
AFIX  43
H8    2    0.689395    0.201483    0.854857    11.00000   -1.20000
AFIX   0
C9    1    0.473970    0.333324    0.814507    11.00000    0.02024    0.02003 =
         0.01736   -0.00321   -0.00090   -0.01153
C10   1    0.461405    0.488460    0.832779    11.00000    0.02366    0.02148 =
         0.02094   -0.00522   -0.00205   -0.01288
AFIX  13
H10   2    0.433062    0.494653    0.924462    11.00000   -1.20000
AFIX   0
C11   1    0.329620    0.621010    0.772891    11.00000    0.02301    0.01846 =
         0.02852   -0.00646   -0.00102   -0.01058
AFIX  13
H11   2    0.310638    0.714445    0.808479    11.00000   -1.20000
AFIX   0
C12   1    0.179962    0.596425    0.807524    11.00000    0.02086    0.01919 =
         0.02930   -0.00621   -0.00012   -0.00830
AFIX  23
H12A  2    0.151110    0.586371    0.899170    11.00000   -1.20000
H12B  2    0.096385    0.685408    0.771784    11.00000   -1.20000
AFIX   0
C13   1    0.611009    0.512158    0.794185    11.00000    0.02643    0.02606 =
         0.02905   -0.00552   -0.00412   -0.01644
AFIX  23
H13A  2    0.600012    0.600622    0.831238    11.00000   -1.20000
H13B  2    0.695286    0.421822    0.827705    11.00000   -1.20000
AFIX   0
C14   1    0.652961    0.538473    0.652785    11.00000    0.02555    0.02913 =
         0.03048   -0.00435   -0.00024   -0.01624
AFIX  23
H14A  2    0.747082    0.557831    0.632527    11.00000   -1.20000
H14B  2    0.673877    0.446446    0.615847    11.00000   -1.20000
AFIX   0
C15   1    0.522566    0.673559    0.597310    11.00000    0.03184    0.02739 =
         0.03008    0.00086   -0.00156   -0.01841
AFIX  23
H15A  2    0.507528    0.767121    0.628859    11.00000   -1.20000
H15B  2    0.549638    0.686452    0.505578    11.00000   -1.20000
AFIX   0
C16   1    0.374278    0.649454    0.631816    11.00000    0.02819    0.02415 =
         0.02868    0.00172   -0.00563   -0.01452
AFIX  23
H16A  2    0.386786    0.561660    0.592988    11.00000   -1.20000
H16B  2    0.290596    0.740147    0.597957    11.00000   -1.20000
AFIX   0
PART   1
C17   1    0.162339    0.176031    0.664833    21.00000    0.01167    0.02091 =
         0.02223   -0.00046   -0.00870   -0.00839
C18   1    0.015608    0.211013    0.642934    21.00000    0.01852    0.04281 =
         0.02392   -0.01172   -0.00557   -0.00613
AFIX  43
H18   2   -0.070297    0.258049    0.702870    21.00000   -1.20000
AFIX   0
C19   1   -0.006968    0.178205    0.534926    21.00000    0.02424    0.06152 =
         0.02954   -0.00977   -0.00664   -0.01708
AFIX  43
H19   2   -0.107918    0.202489    0.521672    21.00000   -1.20000
AFIX   0
C20   1    0.116664    0.110273    0.446247    21.00000    0.02849    0.04693 =
         0.02694   -0.00633   -0.01012   -0.01838
AFIX  43
H20   2    0.101189    0.088836    0.371744    21.00000   -1.20000
AFIX   0
C21   1    0.262845    0.074067    0.467530    21.00000    0.02828    0.04260 =
         0.01272   -0.00455   -0.00259   -0.01204
AFIX  43
H21   2    0.348527    0.026583    0.407588    21.00000   -1.20000
AFIX   0
C22   1    0.285474    0.106602    0.575987    21.00000    0.01772    0.03258 =
         0.01557    0.00130    0.00435   -0.01161
AFIX  43
H22   2    0.386667    0.080931    0.589442    21.00000   -1.20000
AFIX   0
PART   2
C17'  1    0.147821    0.184757    0.666390   -21.00000    0.02119    0.02124 =
         0.01636   -0.00853    0.00837   -0.00578
C18'  1    0.008901    0.241236    0.623009   -21.00000    0.02070    0.04345 =
         0.02972   -0.00898   -0.01217    0.00328
AFIX  43
H18'  2   -0.081430    0.304242    0.671307   -21.00000   -1.20000
AFIX   0
C19'  1   -0.000587    0.207450    0.510469   -21.00000    0.02860    0.05257 =
         0.02301   -0.00887   -0.01178   -0.00942
AFIX  43
H19'  2   -0.096840    0.246821    0.482347   -21.00000   -1.20000
AFIX   0
C20'  1    0.130668    0.116045    0.438910   -21.00000    0.03220    0.04388 =
         0.01546   -0.01023    0.00116   -0.01533
AFIX  43
H20'  2    0.125236    0.093834    0.361009   -21.00000   -1.20000
AFIX   0
C21'  1    0.269474    0.057609    0.482151   -21.00000    0.01959    0.03410 =
         0.01945   -0.00367    0.00015   -0.01217
AFIX  43
H21'  2    0.359287   -0.007503    0.434803   -21.00000   -1.20000
AFIX   0
C22'  1    0.278558    0.093400    0.594287   -21.00000    0.02034    0.03007 =
         0.00649    0.00019   -0.00335   -0.01496
AFIX  43
H22'  2    0.375040    0.055035    0.621846   -21.00000   -1.20000
AFIX   0
PART   0
C23   1    0.098074    0.119283    0.889481    11.00000    0.01662    0.01981 =
         0.02059   -0.00543   -0.00169   -0.00922
O24   3   -0.029260    0.177468    0.949994    11.00000    0.01947    0.02090 =
         0.03039   -0.00612    0.00519   -0.00964
O25   3    0.180710   -0.027886    0.896349    11.00000    0.01871    0.01860 =
         0.02883   -0.00512    0.00385   -0.00911
H25   2    0.126301   -0.074558    0.948543    11.00000   -1.20000
O26   3    0.724243   -0.065682    0.869540    11.00000    0.01648    0.01939 =
         0.02824   -0.00366   -0.00489   -0.00694
C27   1    0.724952   -0.211952    0.875050    11.00000    0.02056    0.02032 =
         0.02541   -0.00375   -0.00288   -0.00781
AFIX 137
H27A  2    0.645231   -0.223465    0.941964    11.00000   -1.50000
H27B  2    0.825194   -0.290226    0.891510    11.00000   -1.50000
H27C  2    0.704918   -0.222697    0.795463    11.00000   -1.50000
 
HKLF 4
 
REM  12115 in P-1
REM R1 =  0.0431 for   4139 Fo > 4sig(Fo)  and  0.0472 for all   4626 data
REM    303 parameters refined using    322 restraints
 
END  
     
WGHT      0.0718      0.2827 
REM Highest difference peak  0.422,  deepest hole -0.182,  1-sigma level  0.049
Q1    1   0.2804  0.3846  0.7771  11.00000  0.05    0.42
Q2    1   0.4049  0.5471  0.7973  11.00000  0.05    0.39
Q3    1   0.1393  0.1629  0.8407  11.00000  0.05    0.39
Q4    1   0.2614  0.1863  0.8006  11.00000  0.05    0.35
Q5    1   0.3859  0.1181  0.8271  11.00000  0.05    0.34
Q6    1   0.5362  0.2582  0.8270  11.00000  0.05    0.34
Q7    1   0.4763  0.4048  0.8159  11.00000  0.05    0.34
Q8    1   0.1632  0.1945  0.7260  11.00000  0.05    0.34
Q9    1   0.5944  0.1214  0.8535  11.00000  0.05    0.33
Q10   1   0.5201  0.0536  0.8393  11.00000  0.05    0.33
Q11   1   0.5857  0.5976  0.6254  11.00000  0.05    0.33
Q12   1   0.3378  0.2501  0.7868  11.00000  0.05    0.32
Q13   1   0.1352  0.4166  0.7859  11.00000  0.05    0.32
Q14   1   0.1199  0.3000  0.7966  11.00000  0.05    0.32
Q15   1   0.4070  0.3286  0.8074  11.00000  0.05    0.31
Q16   1   0.1809  0.5327  0.7774  11.00000  0.05    0.31
Q17   1   0.4452  0.6642  0.6167  11.00000  0.05    0.30
Q18   1   0.5355  0.4958  0.8077  11.00000  0.05    0.29
Q19   1   0.6257  0.5231  0.7215  11.00000  0.05    0.28
Q20   1   0.3606  0.6085  0.7028  11.00000  0.05    0.28
;

#===END 
