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

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

data_san750
_database_code_depnum_ccdc_archive 'CCDC 1463825'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T15:58:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H27 Br O2'
_chemical_formula_weight         451.38
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.29840(10)
_cell_length_b                   16.7188(3)
_cell_length_c                   20.5514(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2507.69(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20760
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.4711
_exptl_absorpt_correction_T_max  0.6755

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.090099
_diffrn_orient_matrix_ub_12      0.015993
_diffrn_orient_matrix_ub_13      -0.034272
_diffrn_orient_matrix_ub_21      0.051965
_diffrn_orient_matrix_ub_22      0.041289
_diffrn_orient_matrix_ub_23      0.029981
_diffrn_orient_matrix_ub_31      0.089192
_diffrn_orient_matrix_ub_32      -0.040212
_diffrn_orient_matrix_ub_33      0.017153
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.097
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_number            5694
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.706
_diffrn_reflns_theta_max         27.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.763
_reflns_number_total             5694
_reflns_number_gt                4883
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+1.5054P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5694
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_diff_density_max         1.086
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4835(6) 0.6165(3) 0.1985(2) 0.0285(9) Uani 1 1 d . . . . .
H1 H 0.3793 0.5918 0.2176 0.034 Uiso 1 1 calc R U . . .
C1A C 0.5286(7) 0.5214(3) 0.5748(2) 0.0326(10) Uani 1 1 d . . . . .
C2 C 0.4588(6) 0.6637(2) 0.1439(2) 0.0285(9) Uani 1 1 d . . . . .
H2 H 0.3402 0.6709 0.1258 0.034 Uiso 1 1 calc R U . . .
C6A C 0.6167(8) 0.5834(3) 0.6080(3) 0.0447(12) Uani 1 1 d . . . . .
H6A H 0.7448 0.5912 0.6027 0.054 Uiso 1 1 calc R U . . .
C5A C 0.5177(9) 0.6337(3) 0.6488(3) 0.0489(13) Uani 1 1 d . . . . .
H5A H 0.577 0.6768 0.6704 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6095(6) 0.7001(2) 0.11641(18) 0.0234(8) Uani 1 1 d . . . . .
C4 C 0.7809(5) 0.6880(2) 0.14262(19) 0.0245(8) Uani 1 1 d . . . . .
H4 H 0.884 0.7127 0.1228 0.029 Uiso 1 1 calc R U . . .
C4A C 0.3334(8) 0.6208(3) 0.6577(2) 0.0424(12) Uani 1 1 d . . . . .
C5 C 0.8066(5) 0.6403(2) 0.19743(18) 0.0226(7) Uani 1 1 d . . . . .
C3A C 0.2456(8) 0.5581(3) 0.6272(3) 0.0492(13) Uani 1 1 d . . . . .
H3A H 0.1191 0.5485 0.6349 0.059 Uiso 1 1 calc R U . . .
C2A C 0.3434(8) 0.5094(3) 0.5854(3) 0.0460(13) Uani 1 1 d . . . . .
H2A H 0.2825 0.4669 0.5636 0.055 Uiso 1 1 calc R U . . .
C6 C 0.9952(5) 0.6320(3) 0.2252(2) 0.0299(9) Uani 1 1 d . . . . .
H6B H 1.0579 0.6844 0.2228 0.036 Uiso 1 1 calc R U . . .
H6C H 1.0656 0.5937 0.1982 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9973(5) 0.6032(3) 0.2956(2) 0.0292(9) Uani 1 1 d . . . . .
H7A H 0.9533 0.6463 0.3246 0.035 Uiso 1 1 calc R U . . .
H7B H 1.1239 0.5891 0.3085 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8727(5) 0.5299(2) 0.30171(19) 0.0231(8) Uani 1 1 d . . . . .
H8 H 0.9095 0.4901 0.2678 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6729(5) 0.5551(2) 0.2887(2) 0.0257(8) Uani 1 1 d . . . . .
H9 H 0.6368 0.5913 0.3252 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6540(5) 0.6035(2) 0.22652(19) 0.0230(8) Uani 1 1 d . . . . .
C11 C 0.5442(5) 0.4824(3) 0.2920(2) 0.0306(9) Uani 1 1 d . . . . .
H11A H 0.5736 0.4454 0.2559 0.037 Uiso 1 1 calc R U . . .
H11B H 0.4161 0.5006 0.2862 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5607(6) 0.4372(3) 0.3572(2) 0.0295(9) Uani 1 1 d . . . . .
H12A H 0.5156 0.4717 0.3929 0.035 Uiso 1 1 calc R U . . .
H12B H 0.4836 0.3886 0.3558 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7588(5) 0.4138(2) 0.37034(18) 0.0218(7) Uani 1 1 d . . . . .
C14 C 0.8810(5) 0.4891(2) 0.3678(2) 0.0246(8) Uani 1 1 d . . . . .
H14 H 0.8292 0.5278 0.4 0.029 Uiso 1 1 calc R U . . .
C15 C 1.0656(6) 0.4614(3) 0.3951(2) 0.0344(10) Uani 1 1 d . . . . .
H15A H 1.1322 0.5064 0.4155 0.041 Uiso 1 1 calc R U . . .
H15B H 1.1429 0.4381 0.3604 0.041 Uiso 1 1 calc R U . . .
C16 C 1.0142(6) 0.3969(3) 0.4467(2) 0.0290(9) Uani 1 1 d . . . . .
H16A H 1.0799 0.3463 0.4379 0.035 Uiso 1 1 calc R U . . .
H16B H 1.0471 0.4155 0.491 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8039(6) 0.3844(2) 0.44112(18) 0.0249(8) Uani 1 1 d . . . . .
C18 C 0.8219(7) 0.3493(3) 0.3220(2) 0.0315(9) Uani 1 1 d . . . . .
H18A H 0.9495 0.335 0.3312 0.047 Uiso 1 1 calc R U . . .
H18B H 0.7442 0.3018 0.3265 0.047 Uiso 1 1 calc R U . . .
H18C H 0.8123 0.37 0.2775 0.047 Uiso 1 1 calc R U . . .
C20 C 0.7074(6) 0.4327(2) 0.4900(2) 0.0294(9) Uani 1 1 d . . . . .
C21 C 0.6291(7) 0.4725(3) 0.5291(2) 0.0361(10) Uani 1 1 d . . . . .
Br1 Br 0.20404(11) 0.68997(4) 0.71355(3) 0.0681(3) Uani 1 1 d . . . . .
O1 O 0.5961(4) 0.74956(18) 0.06216(14) 0.0265(6) Uani 1 1 d . . . . .
O2 O 0.7529(4) 0.30183(16) 0.44891(14) 0.0269(6) Uani 1 1 d . . . . .
H1A H 0.504(8) 0.765(3) 0.061(3) 0.030(15) Uiso 1 1 d . . . . .
H2AA H 0.819(7) 0.289(3) 0.487(3) 0.026(12) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(6) . ?
C1 C10 1.389(6) . ?
C1 H1 0.95 . ?
C1A C2A 1.384(8) . ?
C1A C6A 1.398(7) . ?
C1A C21 1.444(7) . ?
C2 C3 1.379(6) . ?
C2 H2 0.95 . ?
C6A C5A 1.391(8) . ?
C6A H6A 0.95 . ?
C5A C4A 1.374(9) . ?
C5A H5A 0.95 . ?
C3 C4 1.377(6) . ?
C3 O1 1.391(5) . ?
C4 C5 1.392(5) . ?
C4 H4 0.95 . ?
C4A C3A 1.379(8) . ?
C4A Br1 1.883(5) . ?
C5 C10 1.405(5) . ?
C5 C6 1.497(6) . ?
C3A C2A 1.382(7) . ?
C3A H3A 0.95 . ?
C2A H2A 0.95 . ?
C6 C7 1.523(6) . ?
C6 H6B 0.99 . ?
C6 H6C 0.99 . ?
C7 C8 1.532(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C14 1.521(6) . ?
C8 C9 1.541(5) . ?
C8 H8 1 . ?
C9 C10 1.519(5) . ?
C9 C11 1.537(5) . ?
C9 H9 1 . ?
C11 C12 1.542(6) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.522(6) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C18 1.537(6) . ?
C13 C14 1.544(5) . ?
C13 C17 1.570(5) . ?
C14 C15 1.531(6) . ?
C14 H14 1 . ?
C15 C16 1.558(6) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.554(6) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 O2 1.439(5) . ?
C17 C20 1.468(6) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C20 C21 1.190(6) . ?
O1 H1A 0.72(6) . ?
O2 H2AA 0.94(5) . ?

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 C10 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
C10 C1 H1 118.6 . . ?
C2A C1A C6A 118.7(5) . . ?
C2A C1A C21 121.1(4) . . ?
C6A C1A C21 120.2(5) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C5A C6A C1A 120.3(5) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C4A C5A C6A 119.6(5) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 O1 117.7(3) . . ?
C2 C3 O1 122.4(4) . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C5A C4A C3A 121.0(5) . . ?
C5A C4A Br1 118.3(4) . . ?
C3A C4A Br1 120.7(4) . . ?
C4 C5 C10 119.2(3) . . ?
C4 C5 C6 119.1(3) . . ?
C10 C5 C6 121.7(3) . . ?
C4A C3A C2A 119.3(5) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C3A C2A C1A 121.1(5) . . ?
C3A C2A H2A 119.4 . . ?
C1A C2A H2A 119.4 . . ?
C5 C6 C7 113.6(3) . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6C 108.8 . . ?
C7 C6 H6C 108.8 . . ?
H6B C6 H6C 107.7 . . ?
C6 C7 C8 109.0(3) . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C14 C8 C7 114.1(3) . . ?
C14 C8 C9 108.4(3) . . ?
C7 C8 C9 109.2(3) . . ?
C14 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C10 C9 C11 113.8(3) . . ?
C10 C9 C8 112.2(3) . . ?
C11 C9 C8 110.7(3) . . ?
C10 C9 H9 106.5 . . ?
C11 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C1 C10 C5 117.7(3) . . ?
C1 C10 C9 120.9(3) . . ?
C5 C10 C9 121.3(3) . . ?
C9 C11 C12 112.2(4) . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 110.8(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C18 110.5(4) . . ?
C12 C13 C14 109.5(3) . . ?
C18 C13 C14 112.1(3) . . ?
C12 C13 C17 116.4(3) . . ?
C18 C13 C17 108.4(3) . . ?
C14 C13 C17 99.5(3) . . ?
C8 C14 C15 119.9(4) . . ?
C8 C14 C13 111.9(3) . . ?
C15 C14 C13 104.5(3) . . ?
C8 C14 H14 106.6 . . ?
C15 C14 H14 106.6 . . ?
C13 C14 H14 106.6 . . ?
C14 C15 C16 104.3(3) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 106.3(3) . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
O2 C17 C20 109.1(3) . . ?
O2 C17 C16 112.1(3) . . ?
C20 C17 C16 110.4(3) . . ?
O2 C17 C13 110.4(3) . . ?
C20 C17 C13 111.2(3) . . ?
C16 C17 C13 103.5(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 179.3(5) . . ?
C20 C21 C1A 177.8(5) . . ?
C3 O1 H1A 108(4) . . ?
C17 O2 H2AA 100(3) . . ?

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
C10 C1 C2 C3 -0.5(7) . . . . ?
C2A C1A C6A C5A -2.5(8) . . . . ?
C21 C1A C6A C5A 175.9(5) . . . . ?
C1A C6A C5A C4A 1.8(8) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C2 C3 O1 -179.0(4) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
O1 C3 C4 C5 179.1(3) . . . . ?
C6A C5A C4A C3A 0.6(9) . . . . ?
C6A C5A C4A Br1 179.8(4) . . . . ?
C3 C4 C5 C10 0.2(6) . . . . ?
C3 C4 C5 C6 -177.6(4) . . . . ?
C5A C4A C3A C2A -2.2(9) . . . . ?
Br1 C4A C3A C2A 178.6(5) . . . . ?
C4A C3A C2A C1A 1.4(9) . . . . ?
C6A C1A C2A C3A 0.9(8) . . . . ?
C21 C1A C2A C3A -177.5(5) . . . . ?
C4 C5 C6 C7 160.5(4) . . . . ?
C10 C5 C6 C7 -17.3(6) . . . . ?
C5 C6 C7 C8 48.8(5) . . . . ?
C6 C7 C8 C14 172.8(3) . . . . ?
C6 C7 C8 C9 -65.7(4) . . . . ?
C14 C8 C9 C10 174.5(3) . . . . ?
C7 C8 C9 C10 49.6(4) . . . . ?
C14 C8 C9 C11 -57.2(5) . . . . ?
C7 C8 C9 C11 178.0(4) . . . . ?
C2 C1 C10 C5 -0.3(6) . . . . ?
C2 C1 C10 C9 176.4(4) . . . . ?
C4 C5 C10 C1 0.4(6) . . . . ?
C6 C5 C10 C1 178.1(4) . . . . ?
C4 C5 C10 C9 -176.3(4) . . . . ?
C6 C5 C10 C9 1.5(6) . . . . ?
C11 C9 C10 C1 38.6(5) . . . . ?
C8 C9 C10 C1 165.3(4) . . . . ?
C11 C9 C10 C5 -144.8(4) . . . . ?
C8 C9 C10 C5 -18.1(5) . . . . ?
C10 C9 C11 C12 -177.2(4) . . . . ?
C8 C9 C11 C12 55.3(5) . . . . ?
C9 C11 C12 C13 -54.5(5) . . . . ?
C11 C12 C13 C18 -68.7(4) . . . . ?
C11 C12 C13 C14 55.3(5) . . . . ?
C11 C12 C13 C17 167.1(3) . . . . ?
C7 C8 C14 C15 -55.1(5) . . . . ?
C9 C8 C14 C15 -176.9(4) . . . . ?
C7 C8 C14 C13 -177.8(3) . . . . ?
C9 C8 C14 C13 60.4(4) . . . . ?
C12 C13 C14 C8 -60.1(4) . . . . ?
C18 C13 C14 C8 63.0(4) . . . . ?
C17 C13 C14 C8 177.4(3) . . . . ?
C12 C13 C14 C15 168.8(4) . . . . ?
C18 C13 C14 C15 -68.2(4) . . . . ?
C17 C13 C14 C15 46.3(4) . . . . ?
C8 C14 C15 C16 -159.2(4) . . . . ?
C13 C14 C15 C16 -32.9(5) . . . . ?
C14 C15 C16 C17 5.9(5) . . . . ?
C15 C16 C17 O2 141.5(4) . . . . ?
C15 C16 C17 C20 -96.6(4) . . . . ?
C15 C16 C17 C13 22.5(4) . . . . ?
C12 C13 C17 O2 80.8(4) . . . . ?
C18 C13 C17 O2 -44.5(4) . . . . ?
C14 C13 C17 O2 -161.8(3) . . . . ?
C12 C13 C17 C20 -40.4(5) . . . . ?
C18 C13 C17 C20 -165.8(3) . . . . ?
C14 C13 C17 C20 76.9(4) . . . . ?
C12 C13 C17 C16 -159.0(4) . . . . ?
C18 C13 C17 C16 75.7(4) . . . . ?
C14 C13 C17 C16 -41.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.72(6) 1.99(6) 2.702(4) 176(6) 4_655
O2 H2AA O1 0.94(5) 1.79(5) 2.715(4) 167(4) 2_665
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.058 0.250 1.000 253 17 ' '
2 -0.020 0.750 0.500 253 17 ' '
_platon_squeeze_details          
;
;

# END of CIF
####################################################################### 
# 
# 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_san529
_database_code_depnum_ccdc_archive 'CCDC 1463826'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-25T15:17:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26  H27  O2  I1  Cl0'
_chemical_formula_sum            'C26 H27 I O2'
_chemical_formula_weight         498.37
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.3430(2)
_cell_length_b                   17.0390(4)
_cell_length_c                   20.654(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2584.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    13767
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.772
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.806

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.061039
_diffrn_orient_matrix_ub_12      -0.027495
_diffrn_orient_matrix_ub_13      -0.036862
_diffrn_orient_matrix_ub_21      0.112136
_diffrn_orient_matrix_ub_22      -0.006766
_diffrn_orient_matrix_ub_23      0.026903
_diffrn_orient_matrix_ub_31      -0.047406
_diffrn_orient_matrix_ub_32      -0.051406
_diffrn_orient_matrix_ub_33      0.016175
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_number            5816
_diffrn_reflns_limit_h_min       1000000
_diffrn_reflns_limit_h_max       -1000000
_diffrn_reflns_limit_k_min       1000000
_diffrn_reflns_limit_k_max       -1000000
_diffrn_reflns_limit_l_min       1000000
_diffrn_reflns_limit_l_max       -1000000
_diffrn_reflns_theta_min         2.944
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_coverage         0.756
_reflns_number_total             5816
_reflns_number_gt                4632
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+1.8403P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5816
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1619 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(11)
_refine_diff_density_max         0.906
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.068

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4893(7) 0.1092(3) -0.3023(3) 0.0458(13) Uani 1 1 d . . . . .
H1 H 0.3867 0.0858 -0.2843 0.055 Uiso 1 1 calc R U . . .
C1A C 0.5273(10) 0.0170(4) 0.0685(3) 0.0549(15) Uani 1 1 d . . . . .
C2 C 0.4684(7) 0.1580(3) -0.3559(3) 0.0457(13) Uani 1 1 d . . . . .
H2 H 0.3534 0.1669 -0.3734 0.055 Uiso 1 1 calc R U . . .
C2A C 0.6199(11) 0.0765(5) 0.1015(4) 0.072(2) Uani 1 1 d . . . . .
H2A H 0.7455 0.0813 0.097 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6191(7) 0.1930(3) -0.3828(2) 0.0362(10) Uani 1 1 d . . . . .
C3A C 0.5271(12) 0.1279(5) 0.1405(4) 0.073(2) Uani 1 1 d . . . . .
H3A H 0.5895 0.1678 0.1617 0.087 Uiso 1 1 calc R U . . .
C4 C 0.7888(7) 0.1787(3) -0.3572(2) 0.0383(10) Uani 1 1 d . . . . .
H3 H 0.8903 0.2019 -0.3761 0.046 Uiso 1 1 calc R U . . .
C4A C 0.3422(11) 0.1205(4) 0.1484(3) 0.0614(17) Uani 1 1 d . . . . .
C5 C 0.8117(7) 0.1302(3) -0.3033(2) 0.0367(10) Uani 1 1 d . . . . .
C5A C 0.2516(12) 0.0599(5) 0.1175(4) 0.076(2) Uani 1 1 d . . . . .
H5A H 0.1272 0.0534 0.124 0.091 Uiso 1 1 calc R U . . .
C6 C 1.0005(7) 0.1187(4) -0.2762(3) 0.0470(13) Uani 1 1 d . . . . .
H6C H 1.0658 0.0819 -0.3034 0.056 Uiso 1 1 calc R U . . .
H6B H 1.0649 0.1684 -0.2778 0.056 Uiso 1 1 calc R U . . .
C6A C 0.3432(11) 0.0096(4) 0.0776(4) 0.069(2) Uani 1 1 d . . . . .
H6A H 0.2799 -0.03 0.0564 0.082 Uiso 1 1 calc R U . . .
C7 C 1.0023(7) 0.0890(3) -0.2080(3) 0.0439(12) Uani 1 1 d . . . . .
H7A H 0.9633 0.1304 -0.1788 0.053 Uiso 1 1 calc R U . . .
H7B H 1.1252 0.0738 -0.1961 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8751(6) 0.0185(3) -0.2016(3) 0.0379(10) Uani 1 1 d . . . . .
H8 H 0.9075 -0.02 -0.2349 0.045 Uiso 1 1 calc R U . . .
C9 C 0.6761(7) 0.0455(3) -0.2133(3) 0.0396(10) Uani 1 1 d . . . . .
H9 H 0.6428 0.0797 -0.1771 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6599(6) 0.0942(3) -0.2748(2) 0.0360(10) Uani 1 1 d . . . . .
C11 C 0.5472(7) -0.0251(4) -0.2112(3) 0.0484(13) Uani 1 1 d . . . . .
H11A H 0.577 -0.0605 -0.2464 0.058 Uiso 1 1 calc R U . . .
H11B H 0.4231 -0.0071 -0.2176 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5594(8) -0.0697(4) -0.1467(3) 0.0468(13) Uani 1 1 d . . . . .
H12A H 0.5154 -0.0364 -0.1119 0.056 Uiso 1 1 calc R U . . .
H12B H 0.4822 -0.1158 -0.1485 0.056 Uiso 1 1 calc R U . . .
C13 C 0.7549(6) -0.0946(3) -0.1322(2) 0.0351(10) Uani 1 1 d . . . . .
C14 C 0.8805(7) -0.0221(3) -0.1353(3) 0.0383(11) Uani 1 1 d . . . . .
H14 H 0.8322 0.0157 -0.104 0.046 Uiso 1 1 calc R U . . .
C15 C 1.0613(8) -0.0510(4) -0.1081(3) 0.0528(15) Uani 1 1 d . . . . .
H15A H 1.1354 -0.0743 -0.1419 0.063 Uiso 1 1 calc R U . . .
H15B H 1.1285 -0.0081 -0.0885 0.063 Uiso 1 1 calc R U . . .
C16 C 1.0101(8) -0.1118(4) -0.0576(3) 0.0465(13) Uani 1 1 d . . . . .
H16A H 1.0442 -0.0939 -0.0147 0.056 Uiso 1 1 calc R U . . .
H16B H 1.0716 -0.161 -0.0662 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7961(8) -0.1227(3) -0.0622(2) 0.0398(11) Uani 1 1 d . . . . .
C18 C 0.8141(9) -0.1590(3) -0.1800(3) 0.0491(13) Uani 1 1 d . . . . .
H18A H 0.7946 -0.1412 -0.2235 0.074 Uiso 1 1 calc R U . . .
H18B H 0.7437 -0.2056 -0.1724 0.074 Uiso 1 1 calc R U . . .
H18C H 0.941 -0.1704 -0.1738 0.074 Uiso 1 1 calc R U . . .
C20 C 0.7026(9) -0.0737(3) -0.0143(3) 0.0470(12) Uani 1 1 d . . . . .
C21 C 0.6249(10) -0.0341(4) 0.0245(3) 0.0561(16) Uani 1 1 d . . . . .
O1 O 0.6056(5) 0.2438(2) -0.43468(17) 0.0420(8) Uani 1 1 d . . . . .
H01 H 0.4982 0.2546 -0.441 0.063 Uiso 1 1 calc R U . . .
O2 O 0.7449(5) -0.2031(2) -0.05306(16) 0.0427(8) Uani 1 1 d . . . . .
H02 H 0.7906 -0.2196 -0.0195 0.064 Uiso 1 1 calc R U . . .
I1 I 0.20676(10) 0.20075(3) 0.20700(3) 0.0934(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.394(8) . ?
C1 C10 1.399(7) . ?
C1 H1 0.93 . ?
C1A C6A 1.371(11) . ?
C1A C2A 1.399(10) . ?
C1A C21 1.448(9) . ?
C2 C3 1.373(8) . ?
C2 H2 0.93 . ?
C2A C3A 1.371(11) . ?
C2A H2A 0.93 . ?
C3 C4 1.375(7) . ?
C3 O1 1.382(6) . ?
C3A C4A 1.373(11) . ?
C3A H3A 0.93 . ?
C4 C5 1.397(7) . ?
C4 H3 0.93 . ?
C4A C5A 1.384(10) . ?
C4A I1 2.079(6) . ?
C5 C10 1.402(7) . ?
C5 C6 1.508(7) . ?
C5A C6A 1.365(10) . ?
C5A H5A 0.93 . ?
C6 C7 1.498(8) . ?
C6 H6C 0.97 . ?
C6 H6B 0.97 . ?
C6A H6A 0.93 . ?
C7 C8 1.527(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C14 1.534(7) . ?
C8 C9 1.551(7) . ?
C8 H8 0.98 . ?
C9 C10 1.522(7) . ?
C9 C11 1.531(7) . ?
C9 H9 0.98 . ?
C11 C12 1.538(8) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.526(7) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C18 1.538(7) . ?
C13 C14 1.543(7) . ?
C13 C17 1.553(7) . ?
C14 C15 1.524(8) . ?
C14 H14 0.98 . ?
C15 C16 1.517(8) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.585(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 O2 1.433(6) . ?
C17 C20 1.467(8) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C20 C21 1.192(8) . ?
O1 H01 0.82 . ?
O2 H02 0.82 . ?

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 C10 122.0(5) . . ?
C2 C1 H1 119 . . ?
C10 C1 H1 119 . . ?
C6A C1A C2A 118.6(6) . . ?
C6A C1A C21 121.3(6) . . ?
C2A C1A C21 120.1(7) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C3A C2A C1A 120.5(7) . . ?
C3A C2A H2A 119.8 . . ?
C1A C2A H2A 119.8 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 O1 121.8(5) . . ?
C4 C3 O1 118.3(4) . . ?
C2A C3A C4A 120.2(7) . . ?
C2A C3A H3A 119.9 . . ?
C4A C3A H3A 119.9 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 H3 119.3 . . ?
C5 C4 H3 119.3 . . ?
C3A C4A C5A 119.2(7) . . ?
C3A C4A I1 118.8(5) . . ?
C5A C4A I1 121.9(6) . . ?
C4 C5 C10 119.9(5) . . ?
C4 C5 C6 118.9(4) . . ?
C10 C5 C6 121.2(4) . . ?
C6A C5A C4A 120.6(8) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
C7 C6 C5 113.7(4) . . ?
C7 C6 H6C 108.8 . . ?
C5 C6 H6C 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6C C6 H6B 107.7 . . ?
C5A C6A C1A 120.8(7) . . ?
C5A C6A H6A 119.6 . . ?
C1A C6A H6A 119.6 . . ?
C6 C7 C8 110.0(4) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C14 114.6(4) . . ?
C7 C8 C9 109.3(4) . . ?
C14 C8 C9 107.3(4) . . ?
C7 C8 H8 108.5 . . ?
C14 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C10 C9 C11 113.8(4) . . ?
C10 C9 C8 111.4(4) . . ?
C11 C9 C8 110.3(4) . . ?
C10 C9 H9 107 . . ?
C11 C9 H9 107 . . ?
C8 C9 H9 107 . . ?
C1 C10 C5 117.5(4) . . ?
C1 C10 C9 120.6(4) . . ?
C5 C10 C9 121.8(4) . . ?
C9 C11 C12 112.1(5) . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.2(4) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108 . . ?
C12 C13 C18 109.8(5) . . ?
C12 C13 C14 109.3(4) . . ?
C18 C13 C14 112.1(4) . . ?
C12 C13 C17 116.8(4) . . ?
C18 C13 C17 108.8(4) . . ?
C14 C13 C17 99.7(4) . . ?
C15 C14 C8 119.8(4) . . ?
C15 C14 C13 104.3(4) . . ?
C8 C14 C13 112.5(4) . . ?
C15 C14 H14 106.4 . . ?
C8 C14 H14 106.4 . . ?
C13 C14 H14 106.4 . . ?
C16 C15 C14 105.0(5) . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.8 . . ?
C15 C16 C17 106.5(4) . . ?
C15 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
O2 C17 C20 109.4(4) . . ?
O2 C17 C13 111.5(4) . . ?
C20 C17 C13 111.3(4) . . ?
O2 C17 C16 111.4(4) . . ?
C20 C17 C16 110.9(5) . . ?
C13 C17 C16 102.3(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 179.3(7) . . ?
C20 C21 C1A 176.8(7) . . ?
C3 O1 H01 109.5 . . ?
C17 O2 H02 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
C10 C1 C2 C3 -0.2(9) . . . . ?
C6A C1A C2A C3A -2.0(12) . . . . ?
C21 C1A C2A C3A 176.3(7) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
C1 C2 C3 O1 -177.9(5) . . . . ?
C1A C2A C3A C4A 1.1(13) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
O1 C3 C4 C5 177.7(4) . . . . ?
C2A C3A C4A C5A 1.2(13) . . . . ?
C2A C3A C4A I1 -179.1(6) . . . . ?
C3 C4 C5 C10 0.8(8) . . . . ?
C3 C4 C5 C6 -178.2(5) . . . . ?
C3A C4A C5A C6A -2.5(12) . . . . ?
I1 C4A C5A C6A 177.8(6) . . . . ?
C4 C5 C6 C7 160.8(5) . . . . ?
C10 C5 C6 C7 -18.1(8) . . . . ?
C4A C5A C6A C1A 1.5(13) . . . . ?
C2A C1A C6A C5A 0.8(12) . . . . ?
C21 C1A C6A C5A -177.6(7) . . . . ?
C5 C6 C7 C8 48.9(7) . . . . ?
C6 C7 C8 C14 174.1(5) . . . . ?
C6 C7 C8 C9 -65.5(6) . . . . ?
C7 C8 C9 C10 49.2(6) . . . . ?
C14 C8 C9 C10 174.0(4) . . . . ?
C7 C8 C9 C11 176.5(5) . . . . ?
C14 C8 C9 C11 -58.6(6) . . . . ?
C2 C1 C10 C5 -0.2(9) . . . . ?
C2 C1 C10 C9 175.4(5) . . . . ?
C4 C5 C10 C1 -0.1(8) . . . . ?
C6 C5 C10 C1 178.8(5) . . . . ?
C4 C5 C10 C9 -175.7(5) . . . . ?
C6 C5 C10 C9 3.2(8) . . . . ?
C11 C9 C10 C1 39.9(7) . . . . ?
C8 C9 C10 C1 165.3(5) . . . . ?
C11 C9 C10 C5 -144.6(5) . . . . ?
C8 C9 C10 C5 -19.2(7) . . . . ?
C10 C9 C11 C12 -176.5(5) . . . . ?
C8 C9 C11 C12 57.5(7) . . . . ?
C9 C11 C12 C13 -55.1(7) . . . . ?
C11 C12 C13 C18 -69.3(6) . . . . ?
C11 C12 C13 C14 54.0(7) . . . . ?
C11 C12 C13 C17 166.2(5) . . . . ?
C7 C8 C14 C15 -54.8(7) . . . . ?
C9 C8 C14 C15 -176.3(5) . . . . ?
C7 C8 C14 C13 -177.9(4) . . . . ?
C9 C8 C14 C13 60.6(5) . . . . ?
C12 C13 C14 C15 169.7(5) . . . . ?
C18 C13 C14 C15 -68.3(6) . . . . ?
C17 C13 C14 C15 46.7(5) . . . . ?
C12 C13 C14 C8 -58.9(6) . . . . ?
C18 C13 C14 C8 63.2(6) . . . . ?
C17 C13 C14 C8 178.1(4) . . . . ?
C8 C14 C15 C16 -159.8(5) . . . . ?
C13 C14 C15 C16 -32.8(6) . . . . ?
C14 C15 C16 C17 5.7(7) . . . . ?
C12 C13 C17 O2 81.7(6) . . . . ?
C18 C13 C17 O2 -43.3(6) . . . . ?
C14 C13 C17 O2 -160.8(4) . . . . ?
C12 C13 C17 C20 -40.7(6) . . . . ?
C18 C13 C17 C20 -165.7(5) . . . . ?
C14 C13 C17 C20 76.8(5) . . . . ?
C12 C13 C17 C16 -159.2(5) . . . . ?
C18 C13 C17 C16 75.9(5) . . . . ?
C14 C13 C17 C16 -41.6(5) . . . . ?
C15 C16 C17 O2 142.2(5) . . . . ?
C15 C16 C17 C20 -95.8(6) . . . . ?
C15 C16 C17 C13 22.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H01 O2 0.82 1.93 2.740(5) 169.5 4_654
O2 H02 O1 0.82 1.95 2.769(5) 171.8 2_655

# SQUEEZE RESULTS (Version =  30715)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.019 0.250 0.000 261 114 ' '
2 -0.054 0.750 0.500 261 114 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

# END of CIF
####################################################################### 
# 
# 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_san817
_database_code_depnum_ccdc_archive 'CCDC 1463827'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2014-09-26T15:18:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C27 H31 I O2'
_chemical_formula_weight         514.42
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.4755(2)
_cell_length_b                   16.0635(3)
_cell_length_c                   22.8738(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2379.31(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1
_cell_measurement_theta_max      14
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.9171
_exptl_absorpt_correction_T_max  1.0434

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.150077
_diffrn_orient_matrix_ub_12      0.01011
_diffrn_orient_matrix_ub_13      -0.007468
_diffrn_orient_matrix_ub_21      0.01096
_diffrn_orient_matrix_ub_22      -0.030474
_diffrn_orient_matrix_ub_23      -0.037995
_diffrn_orient_matrix_ub_31      -0.03471
_diffrn_orient_matrix_ub_32      -0.053334
_diffrn_orient_matrix_ub_33      0.020294
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_number            19231
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         27.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.974
_reflns_number_total             5340
_reflns_number_gt                4638
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+1.4231P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5340
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C -0.0144(13) 0.6196(4) 0.2459(3) 0.080(2) Uani 1 d . .
H1A H -0.1496 0.6381 0.2586 0.096 Uiso 1 calc . .
H1B H 0.087 0.6441 0.2719 0.096 Uiso 1 calc . .
C1A C 0.4759(8) 0.5924(3) 0.54986(18) 0.0406(10) Uani 1 d . .
C2 C 0.0227(17) 0.6512(6) 0.1859(3) 0.104(3) Uani 1 d . .
H2B H 0.0215 0.7116 0.1863 0.124 Uiso 1 calc . .
H2C H -0.0874 0.6325 0.1603 0.124 Uiso 1 calc . .
C2A C 0.6782(9) 0.5730(3) 0.5663(2) 0.0449(11) Uani 1 d . .
H2A H 0.7238 0.5182 0.5643 0.054 Uiso 1 calc . .
C3 C 0.2256(12) 0.6212(4) 0.1628(2) 0.0673(17) Uani 1 d . .
C3A C 0.8107(9) 0.6343(3) 0.5855(2) 0.0499(11) Uani 1 d . .
H3A H 0.9459 0.6211 0.5955 0.06 Uiso 1 calc . .
C4 C 0.2760(9) 0.5351(3) 0.17580(19) 0.0502(12) Uani 1 d . .
H4 H 0.3858 0.5106 0.1561 0.06 Uiso 1 calc . .
C4A C 0.7428(8) 0.7149(3) 0.5899(2) 0.0494(11) Uani 1 d . .
C5 C 0.1712(9) 0.4889(3) 0.2152(2) 0.0477(11) Uani 1 d . .
C5A C 0.5442(11) 0.7359(3) 0.5731(3) 0.0645(15) Uani 1 d . .
H5A H 0.5001 0.7909 0.5752 0.077 Uiso 1 calc . .
C6 C 0.2303(12) 0.3997(4) 0.2257(2) 0.0617(15) Uani 1 d . .
H6B H 0.3527 0.3866 0.2031 0.074 Uiso 1 calc . .
H6C H 0.1195 0.3637 0.2124 0.074 Uiso 1 calc . .
C6A C 0.4123(9) 0.6749(3) 0.5532(3) 0.0585(13) Uani 1 d . .
H6A H 0.279 0.6891 0.5418 0.07 Uiso 1 calc . .
C7 C 0.2727(10) 0.3828(3) 0.2902(2) 0.0517(12) Uani 1 d . .
H7A H 0.2952 0.3237 0.2958 0.062 Uiso 1 calc . .
H7B H 0.3978 0.4117 0.3017 0.062 Uiso 1 calc . .
C8 C 0.0955(7) 0.4111(3) 0.32892(17) 0.0372(9) Uani 1 d . .
H8 H -0.0263 0.3769 0.3205 0.045 Uiso 1 calc . .
C9 C 0.0424(8) 0.5034(3) 0.31739(17) 0.0378(8) Uani 1 d . .
H9 H 0.1669 0.535 0.3275 0.045 Uiso 1 calc . .
C10 C -0.0038(8) 0.5241(4) 0.2520(2) 0.0511(12) Uani 1 d . .
C11 C -0.1265(8) 0.5347(3) 0.3588(2) 0.0454(11) Uani 1 d . .
H11A H -0.2546 0.5061 0.3499 0.054 Uiso 1 calc . .
H11B H -0.1482 0.5937 0.3521 0.054 Uiso 1 calc . .
C12 C -0.0730(9) 0.5208(3) 0.42377(18) 0.0414(10) Uani 1 d . .
H12A H 0.0454 0.5547 0.4342 0.05 Uiso 1 calc . .
H12B H -0.1886 0.5379 0.4479 0.05 Uiso 1 calc . .
C13 C -0.0244(7) 0.4294(2) 0.43515(17) 0.0345(8) Uani 1 d . .
C14 C 0.1512(7) 0.4022(2) 0.39378(17) 0.0333(8) Uani 1 d . .
H14 H 0.2666 0.4403 0.4009 0.04 Uiso 1 calc . .
C15 C 0.2181(8) 0.3173(3) 0.41738(19) 0.0437(10) Uani 1 d . .
H15A H 0.1296 0.2734 0.4026 0.052 Uiso 1 calc . .
H15B H 0.3599 0.3052 0.4067 0.052 Uiso 1 calc . .
C16 C 0.1957(8) 0.3262(3) 0.48365(19) 0.0408(9) Uani 1 d . .
H16A H 0.3307 0.3277 0.502 0.049 Uiso 1 calc . .
H16B H 0.1193 0.2794 0.4995 0.049 Uiso 1 calc . .
C17 C 0.0772(7) 0.4092(2) 0.49553(17) 0.0356(8) Uani 1 d . .
C18 C -0.2204(8) 0.3765(3) 0.4283(2) 0.0496(11) Uani 1 d . .
H18A H -0.1887 0.3193 0.4364 0.074 Uiso 1 calc . .
H18B H -0.271 0.3814 0.389 0.074 Uiso 1 calc . .
H18C H -0.324 0.3958 0.4551 0.074 Uiso 1 calc . .
C19 C -0.2089(11) 0.4845(7) 0.2321(3) 0.086(2) Uani 1 d . .
H19A H -0.2287 0.4947 0.1911 0.129 Uiso 1 calc . .
H19B H -0.321 0.5085 0.2537 0.129 Uiso 1 calc . .
H19C H -0.2046 0.4255 0.239 0.129 Uiso 1 calc . .
C20 C 0.2224(8) 0.4752(3) 0.51377(19) 0.0404(10) Uani 1 d . .
C21 C 0.3380(9) 0.5285(3) 0.5301(2) 0.0453(11) Uani 1 d . .
O1 O 0.3350(11) 0.6638(3) 0.1309(2) 0.0916(17) Uani 1 d . .
O2 O -0.0782(6) 0.3997(2) 0.53967(13) 0.0456(7) Uani 1 d . .
H2 H -0.0235 0.3868 0.5707 0.068 Uiso 1 calc . .
I1 I 0.94604(7) 0.80771(3) 0.61983(2) 0.0788(2) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.482(9) . ?
C1 C10 1.541(9) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C1A C6A 1.390(7) . ?
C1A C2A 1.398(7) . ?
C1A C21 1.434(7) . ?
C2 C3 1.496(11) . ?
C2 H2B 0.97 . ?
C2 H2C 0.97 . ?
C2A C3A 1.378(7) . ?
C2A H2A 0.93 . ?
C3 O1 1.225(8) . ?
C3 C4 1.452(8) . ?
C3A C4A 1.370(7) . ?
C3A H3A 0.93 . ?
C4 C5 1.350(7) . ?
C4 H4 0.93 . ?
C4A C5A 1.384(9) . ?
C4A I1 2.104(5) . ?
C5 C6 1.502(8) . ?
C5 C10 1.521(7) . ?
C5A C6A 1.378(8) . ?
C5A H5A 0.93 . ?
C6 C7 1.524(8) . ?
C6 H6B 0.97 . ?
C6 H6C 0.97 . ?
C6A H6A 0.93 . ?
C7 C8 1.520(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C14 1.534(6) . ?
C8 C9 1.545(6) . ?
C8 H8 0.98 . ?
C9 C11 1.531(7) . ?
C9 C10 1.561(6) . ?
C9 H9 0.98 . ?
C10 C19 1.542(9) . ?
C11 C12 1.543(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.523(6) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C18 1.535(6) . ?
C13 C14 1.543(6) . ?
C13 C17 1.564(6) . ?
C14 C15 1.529(6) . ?
C14 H14 0.98 . ?
C15 C16 1.529(6) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.563(6) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 O2 1.433(6) . ?
C17 C20 1.478(6) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 C21 1.196(7) . ?
O2 H2 0.82 . ?

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 C10 114.7(6) . . ?
C2 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
C10 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C6A C1A C2A 118.4(4) . . ?
C6A C1A C21 121.0(5) . . ?
C2A C1A C21 120.6(4) . . ?
C1 C2 C3 111.1(6) . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2C 109.4 . . ?
C3 C2 H2C 109.4 . . ?
H2B C2 H2C 108 . . ?
C3A C2A C1A 120.6(4) . . ?
C3A C2A H2A 119.7 . . ?
C1A C2A H2A 119.7 . . ?
O1 C3 C4 121.6(6) . . ?
O1 C3 C2 122.6(6) . . ?
C4 C3 C2 115.5(6) . . ?
C4A C3A C2A 119.9(5) . . ?
C4A C3A H3A 120 . . ?
C2A C3A H3A 120 . . ?
C5 C4 C3 123.2(5) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C3A C4A C5A 120.6(5) . . ?
C3A C4A I1 119.5(4) . . ?
C5A C4A I1 119.9(4) . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 C10 122.6(5) . . ?
C6 C5 C10 117.1(5) . . ?
C6A C5A C4A 119.6(5) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5 C6 C7 111.7(4) . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6C 109.3 . . ?
C7 C6 H6C 109.3 . . ?
H6B C6 H6C 107.9 . . ?
C5A C6A C1A 120.8(5) . . ?
C5A C6A H6A 119.6 . . ?
C1A C6A H6A 119.6 . . ?
C8 C7 C6 112.0(5) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C14 111.0(4) . . ?
C7 C8 C9 110.8(4) . . ?
C14 C8 C9 107.9(3) . . ?
C7 C8 H8 109 . . ?
C14 C8 H8 109 . . ?
C9 C8 H8 109 . . ?
C11 C9 C8 111.6(4) . . ?
C11 C9 C10 112.7(4) . . ?
C8 C9 C10 114.2(4) . . ?
C11 C9 H9 105.8 . . ?
C8 C9 H9 105.8 . . ?
C10 C9 H9 105.8 . . ?
C5 C10 C1 110.7(5) . . ?
C5 C10 C19 108.9(5) . . ?
C1 C10 C19 110.2(6) . . ?
C5 C10 C9 108.0(4) . . ?
C1 C10 C9 107.9(4) . . ?
C19 C10 C9 111.1(4) . . ?
C9 C11 C12 112.8(4) . . ?
C9 C11 H11A 109 . . ?
C12 C11 H11A 109 . . ?
C9 C11 H11B 109 . . ?
C12 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 110.5(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C18 110.2(4) . . ?
C12 C13 C14 108.7(3) . . ?
C18 C13 C14 112.9(4) . . ?
C12 C13 C17 116.0(3) . . ?
C18 C13 C17 108.9(3) . . ?
C14 C13 C17 100.0(3) . . ?
C15 C14 C8 119.4(3) . . ?
C15 C14 C13 104.2(3) . . ?
C8 C14 C13 113.2(3) . . ?
C15 C14 H14 106.4 . . ?
C8 C14 H14 106.4 . . ?
C13 C14 H14 106.4 . . ?
C16 C15 C14 103.9(3) . . ?
C16 C15 H15A 111 . . ?
C14 C15 H15A 111 . . ?
C16 C15 H15B 111 . . ?
C14 C15 H15B 111 . . ?
H15A C15 H15B 109 . . ?
C15 C16 C17 107.4(3) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O2 C17 C20 108.9(3) . . ?
O2 C17 C16 112.1(3) . . ?
C20 C17 C16 110.4(4) . . ?
O2 C17 C13 110.4(4) . . ?
C20 C17 C13 111.6(3) . . ?
C16 C17 C13 103.3(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 178.2(5) . . ?
C20 C21 C1A 179.8(6) . . ?
C17 O2 H2 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
C10 C1 C2 C3 -55.8(11) . . . . ?
C6A C1A C2A C3A 0.2(7) . . . . ?
C21 C1A C2A C3A -179.8(5) . . . . ?
C1 C2 C3 O1 -144.7(8) . . . . ?
C1 C2 C3 C4 41.0(11) . . . . ?
C1A C2A C3A C4A 1.5(7) . . . . ?
O1 C3 C4 C5 173.1(6) . . . . ?
C2 C3 C4 C5 -12.6(10) . . . . ?
C2A C3A C4A C5A -2.4(8) . . . . ?
C2A C3A C4A I1 179.6(4) . . . . ?
C3 C4 C5 C6 179.1(6) . . . . ?
C3 C4 C5 C10 -3.1(9) . . . . ?
C3A C4A C5A C6A 1.6(9) . . . . ?
I1 C4A C5A C6A 179.6(5) . . . . ?
C4 C5 C6 C7 125.5(6) . . . . ?
C10 C5 C6 C7 -52.5(7) . . . . ?
C4A C5A C6A C1A 0.2(10) . . . . ?
C2A C1A C6A C5A -1.0(8) . . . . ?
C21 C1A C6A C5A 178.9(5) . . . . ?
C5 C6 C7 C8 52.6(7) . . . . ?
C6 C7 C8 C14 -173.9(4) . . . . ?
C6 C7 C8 C9 -54.0(6) . . . . ?
C7 C8 C9 C11 -176.3(4) . . . . ?
C14 C8 C9 C11 -54.6(5) . . . . ?
C7 C8 C9 C10 54.4(6) . . . . ?
C14 C8 C9 C10 176.1(4) . . . . ?
C4 C5 C10 C1 -10.2(8) . . . . ?
C6 C5 C10 C1 167.7(5) . . . . ?
C4 C5 C10 C19 111.2(6) . . . . ?
C6 C5 C10 C19 -70.9(7) . . . . ?
C4 C5 C10 C9 -128.0(5) . . . . ?
C6 C5 C10 C9 49.9(6) . . . . ?
C2 C1 C10 C5 39.8(9) . . . . ?
C2 C1 C10 C19 -80.8(8) . . . . ?
C2 C1 C10 C9 157.7(7) . . . . ?
C11 C9 C10 C5 -179.0(4) . . . . ?
C8 C9 C10 C5 -50.2(6) . . . . ?
C11 C9 C10 C1 61.4(6) . . . . ?
C8 C9 C10 C1 -169.9(5) . . . . ?
C11 C9 C10 C19 -59.5(7) . . . . ?
C8 C9 C10 C19 69.2(6) . . . . ?
C8 C9 C11 C12 54.6(6) . . . . ?
C10 C9 C11 C12 -175.3(4) . . . . ?
C9 C11 C12 C13 -55.1(6) . . . . ?
C11 C12 C13 C18 -68.3(5) . . . . ?
C11 C12 C13 C14 55.9(5) . . . . ?
C11 C12 C13 C17 167.5(4) . . . . ?
C7 C8 C14 C15 -56.3(5) . . . . ?
C9 C8 C14 C15 -177.9(4) . . . . ?
C7 C8 C14 C13 -179.5(4) . . . . ?
C9 C8 C14 C13 58.9(5) . . . . ?
C12 C13 C14 C15 168.3(4) . . . . ?
C18 C13 C14 C15 -69.1(4) . . . . ?
C17 C13 C14 C15 46.4(4) . . . . ?
C12 C13 C14 C8 -60.4(4) . . . . ?
C18 C13 C14 C8 62.2(5) . . . . ?
C17 C13 C14 C8 177.7(3) . . . . ?
C8 C14 C15 C16 -163.3(4) . . . . ?
C13 C14 C15 C16 -35.8(4) . . . . ?
C14 C15 C16 C17 10.7(5) . . . . ?
C15 C16 C17 O2 136.6(4) . . . . ?
C15 C16 C17 C20 -101.8(4) . . . . ?
C15 C16 C17 C13 17.7(5) . . . . ?
C12 C13 C17 O2 84.9(5) . . . . ?
C18 C13 C17 O2 -40.0(5) . . . . ?
C14 C13 C17 O2 -158.5(3) . . . . ?
C12 C13 C17 C20 -36.4(5) . . . . ?
C18 C13 C17 C20 -161.3(4) . . . . ?
C14 C13 C17 C20 80.2(4) . . . . ?
C12 C13 C17 C16 -155.0(4) . . . . ?
C18 C13 C17 C16 80.1(4) . . . . ?
C14 C13 C17 C16 -38.5(4) . . . . ?

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
O2 H2 O1 0.82 2.01 2.807(6) 163.2 2_565

# END of CIF
####################################################################### 
# 
# 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_san465
_database_code_depnum_ccdc_archive 'CCDC 1463828'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-19T10:36:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C27 H30 Br1 F1 O2'
_chemical_formula_sum            'C27 H30 Br Ca0 F O2'
_chemical_formula_weight         485.42
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.396
_cell_length_b                   16.289
_cell_length_c                   22.678
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2362.7
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12980
_cell_measurement_theta_min      0.78
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.225
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_T_max  0.587
_shelx_estimated_absorpt_T_min   0.503
_shelx_estimated_absorpt_T_max   0.692

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.043513
_diffrn_orient_matrix_ub_12      -0.014418
_diffrn_orient_matrix_ub_13      0.041069
_diffrn_orient_matrix_ub_21      -0.047699
_diffrn_orient_matrix_ub_22      0.057772
_diffrn_orient_matrix_ub_23      0.006444
_diffrn_orient_matrix_ub_31      -0.142399
_diffrn_orient_matrix_ub_32      -0.014946
_diffrn_orient_matrix_ub_33      -0.014708
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_number            20922
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.677
_diffrn_reflns_theta_max         27.754
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.939
_reflns_Friedel_fraction_full    0.99
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_coverage         0.716
_reflns_number_total             5234
_reflns_number_gt                3844
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+1.8408P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5234
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.096
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1263 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(5)
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O2 O -0.5902(8) 0.5968(3) 0.94982(17) 0.0491(9) Uani 1 1 d . . . . .
H2 H -0.5301 0.6106 0.9195 0.074 Uiso 1 1 calc R U . . .
O1 O -0.1797(12) 0.3332(3) 1.3640(3) 0.088(2) Uani 1 1 d . . . . .
C14 C -0.3806(8) 0.5928(3) 1.1001(2) 0.0360(11) Uani 1 1 d . . . . .
H3 H -0.2611 0.5565 1.093 0.043 Uiso 1 1 calc R U . . .
C13 C -0.5515(9) 0.5662(3) 1.0562(2) 0.0384(12) Uani 1 1 d . . . . .
C12 C -0.5964(11) 0.4755(3) 1.0664(2) 0.0455(13) Uani 1 1 d . . . . .
H5C H -0.4738 0.4435 1.0562 0.055 Uiso 1 1 calc R U . . .
H5B H -0.7104 0.4582 1.041 0.055 Uiso 1 1 calc R U . . .
C8 C -0.4395(9) 0.5817(3) 1.1650(2) 0.0409(12) Uani 1 1 d . . . . .
H7 H -0.5666 0.6133 1.1732 0.049 Uiso 1 1 calc R U . . .
C9 C -0.4860(9) 0.4899(3) 1.1741(2) 0.0388(11) Uani 1 1 d . . . . .
H8 H -0.3574 0.4609 1.1632 0.047 Uiso 1 1 calc R U . . .
C1A C -0.0343(10) 0.4078(4) 0.9440(3) 0.0459(14) Uani 1 1 d . . . . .
C3A C 0.2885(11) 0.3613(4) 0.9035(3) 0.0558(16) Uani 1 1 d . . . . .
C15 C -0.3140(11) 0.6785(3) 1.0781(3) 0.0457(13) Uani 1 1 d . . . . .
H11A H -0.4073 0.7207 1.0929 0.055 Uiso 1 1 calc R U . . .
H11B H -0.1723 0.6912 1.0903 0.055 Uiso 1 1 calc R U . . .
C18 C -0.7516(10) 0.6172(4) 1.0614(3) 0.0523(15) Uani 1 1 d . . . . .
H12A H -0.8477 0.6013 1.031 0.078 Uiso 1 1 calc R U . . .
H12B H -0.7183 0.6744 1.0573 0.078 Uiso 1 1 calc R U . . .
H12C H -0.8143 0.6078 1.0993 0.078 Uiso 1 1 calc R U . . .
C4 C -0.2554(11) 0.4587(4) 1.3186(3) 0.0516(15) Uani 1 1 d . . . . .
H13 H -0.149 0.4852 1.3391 0.062 Uiso 1 1 calc R U . . .
C17 C -0.4391(9) 0.5880(3) 0.9969(2) 0.0378(11) Uani 1 1 d . . . . .
C7 C -0.2666(12) 0.6110(4) 1.2054(3) 0.0519(15) Uani 1 1 d . . . . .
H15A H -0.2467 0.6696 1.2004 0.062 Uiso 1 1 calc R U . . .
H15B H -0.1368 0.5837 1.1952 0.062 Uiso 1 1 calc R U . . .
C11 C -0.6549(9) 0.4594(4) 1.1310(3) 0.0449(13) Uani 1 1 d . . . . .
H16A H -0.6754 0.4009 1.1367 0.054 Uiso 1 1 calc R U . . .
H16B H -0.786 0.4867 1.1398 0.054 Uiso 1 1 calc R U . . .
C3 C -0.2935(15) 0.3735(5) 1.3314(3) 0.069(2) Uani 1 1 d . . . . .
C6 C -0.3217(14) 0.5926(4) 1.2699(3) 0.0618(18) Uani 1 1 d . . . . .
H18A H -0.2067 0.6092 1.2951 0.074 Uiso 1 1 calc R U . . .
H18B H -0.444 0.6241 1.2812 0.074 Uiso 1 1 calc R U . . .
C2 C -0.4876(18) 0.3366(7) 1.3059(4) 0.091(3) Uani 1 1 d . . . . .
H2B H -0.6062 0.3497 1.3308 0.11 Uiso 1 1 calc R U . . .
H2C H -0.4734 0.2774 1.3044 0.11 Uiso 1 1 calc R U . . .
C21 C -0.1698(10) 0.4717(4) 0.9636(3) 0.0470(14) Uani 1 1 d . . . . .
C20 C -0.2880(10) 0.5247(3) 0.9797(2) 0.0432(13) Uani 1 1 d . . . . .
C6A C -0.0954(12) 0.3256(4) 0.9477(4) 0.0654(18) Uani 1 1 d . . . . .
H6A H -0.2259 0.3128 0.9634 0.078 Uiso 1 1 calc R U . . .
C16 C -0.3291(10) 0.6716(3) 1.0108(3) 0.0441(13) Uani 1 1 d . . . . .
H23A H -0.1906 0.6729 0.9933 0.053 Uiso 1 1 calc R U . . .
H23B H -0.4099 0.7169 0.9949 0.053 Uiso 1 1 calc R U . . .
C5 C -0.3649(10) 0.5025(4) 1.2787(3) 0.0478(14) Uani 1 1 d . . . . .
C4A C 0.2267(12) 0.2815(4) 0.9069(4) 0.065(2) Uani 1 1 d . . . . .
C2A C 0.1626(11) 0.4249(4) 0.9213(3) 0.0493(14) Uani 1 1 d . . . . .
H2A H 0.2088 0.4789 0.9182 0.059 Uiso 1 1 calc R U . . .
C19 C -0.7471(14) 0.4972(8) 1.2604(3) 0.088(3) Uani 1 1 d . . . . .
H27A H -0.757 0.493 1.3025 0.133 Uiso 1 1 calc R U . . .
H27B H -0.8562 0.4653 1.2425 0.133 Uiso 1 1 calc R U . . .
H27C H -0.7614 0.5536 1.2489 0.133 Uiso 1 1 calc R U . . .
C10 C -0.5328(10) 0.4646(4) 1.2400(3) 0.0531(15) Uani 1 1 d . . . . .
C1 C -0.5252(15) 0.3699(5) 1.2440(3) 0.076(3) Uani 1 1 d . . . . .
H1B H -0.6565 0.348 1.2294 0.091 Uiso 1 1 calc R U . . .
H1A H -0.415 0.35 1.2183 0.091 Uiso 1 1 calc R U . . .
C5A C 0.0313(13) 0.2637(4) 0.9290(4) 0.073(2) Uani 1 1 d D . . . .
H5A H -0.0138 0.2095 0.9312 0.087 Uiso 1 1 calc R U . . .
Br1 Br 0.41048(16) 0.19617(6) 0.88425(6) 0.1015(5) Uani 1 1 d . . . . .
F1 F 0.4701(10) 0.3770(4) 0.8809(3) 0.112(2) Uani 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O2 C17 1.447(7) . ?
O2 H2 0.82 . ?
O1 C3 1.227(10) . ?
C14 C8 1.531(8) . ?
C14 C13 1.541(8) . ?
C14 C15 1.542(7) . ?
C14 H3 0.98 . ?
C13 C12 1.523(7) . ?
C13 C18 1.530(8) . ?
C13 C17 1.565(8) . ?
C12 C11 1.535(8) . ?
C12 H5C 0.97 . ?
C12 H5B 0.97 . ?
C8 C7 1.514(8) . ?
C8 C9 1.538(8) . ?
C8 H7 0.98 . ?
C9 C11 1.540(8) . ?
C9 C10 1.578(8) . ?
C9 H8 0.98 . ?
C1A C2A 1.388(9) . ?
C1A C6A 1.398(9) . ?
C1A C21 1.427(8) . ?
C3A F1 1.296(9) . ?
C3A C4A 1.360(11) . ?
C3A C2A 1.372(9) . ?
C15 C16 1.533(9) . ?
C15 H11A 0.97 . ?
C15 H11B 0.97 . ?
C18 H12A 0.96 . ?
C18 H12B 0.96 . ?
C18 H12C 0.96 . ?
C4 C5 1.348(9) . ?
C4 C3 1.439(10) . ?
C4 H13 0.93 . ?
C17 C20 1.466(8) . ?
C17 C16 1.565(8) . ?
C7 C6 1.534(10) . ?
C7 H15A 0.97 . ?
C7 H15B 0.97 . ?
C11 H16A 0.97 . ?
C11 H16B 0.97 . ?
C3 C2 1.495(13) . ?
C6 C5 1.507(9) . ?
C6 H18A 0.97 . ?
C6 H18B 0.97 . ?
C2 C1 1.524(10) . ?
C2 H2B 0.97 . ?
C2 H2C 0.97 . ?
C21 C20 1.203(8) . ?
C6A C5A 1.361(10) . ?
C6A H6A 0.93 . ?
C16 H23A 0.97 . ?
C16 H23B 0.97 . ?
C5 C10 1.519(9) . ?
C4A C5A 1.377(12) . ?
C4A Br1 1.891(6) . ?
C2A H2A 0.93 . ?
C19 C10 1.541(12) . ?
C19 H27A 0.96 . ?
C19 H27B 0.96 . ?
C19 H27C 0.96 . ?
C10 C1 1.545(11) . ?
C1 H1B 0.97 . ?
C1 H1A 0.97 . ?
C5A H5A 0.93 . ?

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
C17 O2 H2 109.5 . . ?
C8 C14 C13 114.4(5) . . ?
C8 C14 C15 119.1(4) . . ?
C13 C14 C15 104.0(4) . . ?
C8 C14 H3 106.1 . . ?
C13 C14 H3 106.1 . . ?
C15 C14 H3 106.1 . . ?
C12 C13 C18 110.9(5) . . ?
C12 C13 C14 108.0(4) . . ?
C18 C13 C14 113.0(5) . . ?
C12 C13 C17 115.9(4) . . ?
C18 C13 C17 109.2(5) . . ?
C14 C13 C17 99.5(4) . . ?
C13 C12 C11 110.9(5) . . ?
C13 C12 H5C 109.5 . . ?
C11 C12 H5C 109.5 . . ?
C13 C12 H5B 109.5 . . ?
C11 C12 H5B 109.5 . . ?
H5C C12 H5B 108 . . ?
C7 C8 C14 111.4(5) . . ?
C7 C8 C9 111.5(5) . . ?
C14 C8 C9 107.0(4) . . ?
C7 C8 H7 108.9 . . ?
C14 C8 H7 108.9 . . ?
C9 C8 H7 108.9 . . ?
C8 C9 C11 111.4(4) . . ?
C8 C9 C10 114.7(5) . . ?
C11 C9 C10 112.5(5) . . ?
C8 C9 H8 105.8 . . ?
C11 C9 H8 105.8 . . ?
C10 C9 H8 105.8 . . ?
C2A C1A C6A 117.9(6) . . ?
C2A C1A C21 121.4(6) . . ?
C6A C1A C21 120.7(6) . . ?
F1 C3A C4A 118.1(7) . . ?
F1 C3A C2A 119.5(7) . . ?
C4A C3A C2A 122.3(7) . . ?
C16 C15 C14 103.8(4) . . ?
C16 C15 H11A 111 . . ?
C14 C15 H11A 111 . . ?
C16 C15 H11B 111 . . ?
C14 C15 H11B 111 . . ?
H11A C15 H11B 109 . . ?
C13 C18 H12A 109.5 . . ?
C13 C18 H12B 109.5 . . ?
H12A C18 H12B 109.5 . . ?
C13 C18 H12C 109.5 . . ?
H12A C18 H12C 109.5 . . ?
H12B C18 H12C 109.5 . . ?
C5 C4 C3 123.9(7) . . ?
C5 C4 H13 118.1 . . ?
C3 C4 H13 118.1 . . ?
O2 C17 C20 108.3(4) . . ?
O2 C17 C16 111.3(4) . . ?
C20 C17 C16 111.7(5) . . ?
O2 C17 C13 110.4(5) . . ?
C20 C17 C13 111.9(4) . . ?
C16 C17 C13 103.3(4) . . ?
C8 C7 C6 110.3(6) . . ?
C8 C7 H15A 109.6 . . ?
C6 C7 H15A 109.6 . . ?
C8 C7 H15B 109.6 . . ?
C6 C7 H15B 109.6 . . ?
H15A C7 H15B 108.1 . . ?
C12 C11 C9 112.3(5) . . ?
C12 C11 H16A 109.1 . . ?
C9 C11 H16A 109.1 . . ?
C12 C11 H16B 109.1 . . ?
C9 C11 H16B 109.1 . . ?
H16A C11 H16B 107.9 . . ?
O1 C3 C4 122.5(8) . . ?
O1 C3 C2 120.7(8) . . ?
C4 C3 C2 116.7(7) . . ?
C5 C6 C7 111.1(5) . . ?
C5 C6 H18A 109.4 . . ?
C7 C6 H18A 109.4 . . ?
C5 C6 H18B 109.4 . . ?
C7 C6 H18B 109.4 . . ?
H18A C6 H18B 108 . . ?
C3 C2 C1 110.2(7) . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2C 109.6 . . ?
C1 C2 H2C 109.6 . . ?
H2B C2 H2C 108.1 . . ?
C20 C21 C1A 178.5(7) . . ?
C21 C20 C17 177.2(6) . . ?
C5A C6A C1A 121.6(7) . . ?
C5A C6A H6A 119.2 . . ?
C1A C6A H6A 119.2 . . ?
C15 C16 C17 107.0(4) . . ?
C15 C16 H23A 110.3 . . ?
C17 C16 H23A 110.3 . . ?
C15 C16 H23B 110.3 . . ?
C17 C16 H23B 110.3 . . ?
H23A C16 H23B 108.6 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 C10 122.7(6) . . ?
C6 C5 C10 116.7(5) . . ?
C3A C4A C5A 119.0(6) . . ?
C3A C4A Br1 120.4(6) . . ?
C5A C4A Br1 120.5(6) . . ?
C3A C2A C1A 119.3(6) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
C10 C19 H27A 109.5 . . ?
C10 C19 H27B 109.5 . . ?
H27A C19 H27B 109.5 . . ?
C10 C19 H27C 109.5 . . ?
H27A C19 H27C 109.5 . . ?
H27B C19 H27C 109.5 . . ?
C5 C10 C19 108.4(6) . . ?
C5 C10 C1 110.5(5) . . ?
C19 C10 C1 110.7(7) . . ?
C5 C10 C9 107.8(5) . . ?
C19 C10 C9 111.3(6) . . ?
C1 C10 C9 108.1(6) . . ?
C2 C1 C10 114.4(7) . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
H1B C1 H1A 107.6 . . ?
C6A C5A C4A 119.9(7) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?

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
C8 C14 C13 C12 -59.8(6) . . . . ?
C15 C14 C13 C12 168.6(5) . . . . ?
C8 C14 C13 C18 63.2(6) . . . . ?
C15 C14 C13 C18 -68.4(6) . . . . ?
C8 C14 C13 C17 178.9(4) . . . . ?
C15 C14 C13 C17 47.3(5) . . . . ?
C18 C13 C12 C11 -69.0(6) . . . . ?
C14 C13 C12 C11 55.3(6) . . . . ?
C17 C13 C12 C11 165.8(5) . . . . ?
C13 C14 C8 C7 -178.6(5) . . . . ?
C15 C14 C8 C7 -54.7(7) . . . . ?
C13 C14 C8 C9 59.3(6) . . . . ?
C15 C14 C8 C9 -176.9(5) . . . . ?
C7 C8 C9 C11 -177.4(5) . . . . ?
C14 C8 C9 C11 -55.3(6) . . . . ?
C7 C8 C9 C10 53.3(7) . . . . ?
C14 C8 C9 C10 175.4(5) . . . . ?
C8 C14 C15 C16 -164.4(5) . . . . ?
C13 C14 C15 C16 -35.7(6) . . . . ?
C12 C13 C17 O2 85.3(6) . . . . ?
C18 C13 C17 O2 -40.8(6) . . . . ?
C14 C13 C17 O2 -159.3(4) . . . . ?
C12 C13 C17 C20 -35.4(7) . . . . ?
C18 C13 C17 C20 -161.5(5) . . . . ?
C14 C13 C17 C20 80.0(5) . . . . ?
C12 C13 C17 C16 -155.7(5) . . . . ?
C18 C13 C17 C16 78.2(6) . . . . ?
C14 C13 C17 C16 -40.3(5) . . . . ?
C14 C8 C7 C6 -175.3(5) . . . . ?
C9 C8 C7 C6 -55.8(7) . . . . ?
C13 C12 C11 C9 -55.9(7) . . . . ?
C8 C9 C11 C12 56.1(7) . . . . ?
C10 C9 C11 C12 -173.4(5) . . . . ?
C5 C4 C3 O1 173.2(8) . . . . ?
C5 C4 C3 C2 -10.3(11) . . . . ?
C8 C7 C6 C5 56.3(8) . . . . ?
O1 C3 C2 C1 -145.1(9) . . . . ?
C4 C3 C2 C1 38.4(12) . . . . ?
C2A C1A C6A C5A -1.0(11) . . . . ?
C21 C1A C6A C5A 179.8(8) . . . . ?
C14 C15 C16 C17 9.4(6) . . . . ?
O2 C17 C16 C15 138.0(5) . . . . ?
C20 C17 C16 C15 -100.8(6) . . . . ?
C13 C17 C16 C15 19.5(6) . . . . ?
C3 C4 C5 C6 177.2(7) . . . . ?
C3 C4 C5 C10 -3.9(10) . . . . ?
C7 C6 C5 C4 123.3(7) . . . . ?
C7 C6 C5 C10 -55.7(8) . . . . ?
F1 C3A C4A C5A -177.9(8) . . . . ?
C2A C3A C4A C5A -0.2(12) . . . . ?
F1 C3A C4A Br1 4.5(11) . . . . ?
C2A C3A C4A Br1 -177.8(6) . . . . ?
F1 C3A C2A C1A 178.2(7) . . . . ?
C4A C3A C2A C1A 0.5(10) . . . . ?
C6A C1A C2A C3A 0.1(9) . . . . ?
C21 C1A C2A C3A 179.3(6) . . . . ?
C4 C5 C10 C19 109.9(8) . . . . ?
C6 C5 C10 C19 -71.1(8) . . . . ?
C4 C5 C10 C1 -11.6(9) . . . . ?
C6 C5 C10 C1 167.4(6) . . . . ?
C4 C5 C10 C9 -129.5(6) . . . . ?
C6 C5 C10 C9 49.5(8) . . . . ?
C8 C9 C10 C5 -47.7(7) . . . . ?
C11 C9 C10 C5 -176.4(5) . . . . ?
C8 C9 C10 C19 71.0(8) . . . . ?
C11 C9 C10 C19 -57.6(8) . . . . ?
C8 C9 C10 C1 -167.1(6) . . . . ?
C11 C9 C10 C1 64.2(7) . . . . ?
C3 C2 C1 C10 -54.6(12) . . . . ?
C5 C10 C1 C2 40.9(10) . . . . ?
C19 C10 C1 C2 -79.1(9) . . . . ?
C9 C10 C1 C2 158.7(7) . . . . ?
C1A C6A C5A C4A 1.3(13) . . . . ?
C3A C4A C5A C6A -0.7(13) . . . . ?
Br1 C4A C5A C6A 176.9(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 2.05 2.841(7) 160.5 2_464
C2A H2A O2 0.93 2.42 3.280(8) 153.7 1_655
O2 H2 O1 0.82 2.05 2.841(7) 160.5 2_464
C2A H2A O2 0.93 2.42 3.280(8) 153.7 1_655

# END of CIF
####################################################################### 
# 
# 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_san749
_database_code_depnum_ccdc_archive 'CCDC 1463829'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T16:42:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H25 Br F2 O2'
_chemical_formula_weight         487.37
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.36240(10)
_cell_length_b                   16.7118(3)
_cell_length_c                   20.7142(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.65(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    45395
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.27
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.5847
_exptl_absorpt_correction_T_max  0.6852

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.090987
_diffrn_orient_matrix_ub_12      -0.026028
_diffrn_orient_matrix_ub_13      -0.029048
_diffrn_orient_matrix_ub_21      0.016331
_diffrn_orient_matrix_ub_22      0.044051
_diffrn_orient_matrix_ub_23      -0.032153
_diffrn_orient_matrix_ub_31      0.099515
_diffrn_orient_matrix_ub_32      -0.031027
_diffrn_orient_matrix_ub_33      -0.021283
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_number            5796
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.99
_reflns_Friedel_coverage         0.758
_reflns_number_total             5796
_reflns_number_gt                5087
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.0937P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5796
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_diff_density_max         0.762
_refine_diff_density_min         -0.816
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C13 C 0.7514(5) 0.58999(18) 0.62901(15) 0.0268(6) Uani 1 1 d . . . . .
C7 C 0.9989(4) 0.4045(2) 0.70412(17) 0.0326(7) Uani 1 1 d . . . . .
H7A H 1.1231 0.4203 0.691 0.039 Uiso 1 1 calc R U . . .
H7B H 0.9578 0.3608 0.6753 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7897(5) 0.31667(19) 0.85625(15) 0.0286(6) Uani 1 1 d . . . . .
H4 H 0.8937 0.2932 0.8757 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6221(4) 0.3026(2) 0.88240(15) 0.0279(6) Uani 1 1 d . . . . .
C2 C 0.4697(5) 0.3382(2) 0.85519(19) 0.0343(8) Uani 1 1 d . . . . .
H2 H 0.3528 0.33 0.8735 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8106(6) 0.6560(2) 0.67623(17) 0.0369(8) Uani 1 1 d . . . . .
H18A H 0.9362 0.6716 0.6669 0.055 Uiso 1 1 calc R U . . .
H18B H 0.7308 0.7025 0.6713 0.055 Uiso 1 1 calc R U . . .
H18C H 0.8026 0.6358 0.7206 0.055 Uiso 1 1 calc R U . . .
C1 C 0.4909(5) 0.3856(2) 0.80107(19) 0.0366(8) Uani 1 1 d . . . . .
H1 H 0.3863 0.4092 0.7821 0.044 Uiso 1 1 calc R U . . .
C14 C 0.8763(4) 0.5162(2) 0.63203(17) 0.0290(7) Uani 1 1 d . . . . .
H14 H 0.8275 0.4766 0.6003 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7929(5) 0.61883(19) 0.55910(15) 0.0291(7) Uani 1 1 d . . . . .
C12 C 0.5559(5) 0.5648(2) 0.64287(18) 0.0349(8) Uani 1 1 d . . . . .
H12A H 0.5119 0.5297 0.6077 0.042 Uiso 1 1 calc R U . . .
H12B H 0.4772 0.6129 0.6442 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8714(4) 0.4758(2) 0.69811(16) 0.0270(7) Uani 1 1 d . . . . .
H8 H 0.906 0.5162 0.7315 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0582(5) 0.5459(2) 0.6050(2) 0.0384(8) Uani 1 1 d . . . . .
H15A H 1.1271 0.5015 0.585 0.046 Uiso 1 1 calc R U . . .
H15B H 1.1332 0.5703 0.6394 0.046 Uiso 1 1 calc R U . . .
C20 C 0.7022(5) 0.5679(2) 0.51083(17) 0.0355(8) Uani 1 1 d . . . . .
C10 C 0.6594(4) 0.4002(2) 0.77330(16) 0.0282(7) Uani 1 1 d . . . . .
C6 C 1.0001(5) 0.3754(2) 0.77395(18) 0.0344(8) Uani 1 1 d . . . . .
H6B H 1.0655 0.3237 0.7762 0.041 Uiso 1 1 calc R U . . .
H6C H 1.0675 0.4144 0.8008 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8118(4) 0.36462(19) 0.80172(15) 0.0272(7) Uani 1 1 d . . . . .
C9 C 0.6741(4) 0.4487(2) 0.71122(18) 0.0294(7) Uani 1 1 d . . . . .
H9 H 0.6398 0.4119 0.6751 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5432(5) 0.5199(2) 0.70799(19) 0.0378(8) Uani 1 1 d . . . . .
H11A H 0.5714 0.5575 0.7435 0.045 Uiso 1 1 calc R U . . .
H11B H 0.4174 0.5006 0.7142 0.045 Uiso 1 1 calc R U . . .
C21 C 0.6298(6) 0.5272(2) 0.47167(18) 0.0407(9) Uani 1 1 d . . . . .
C16 C 1.0032(5) 0.6092(2) 0.55376(18) 0.0345(8) Uani 1 1 d . . . . .
H16A H 1.0375 0.5909 0.51 0.041 Uiso 1 1 calc R U . . .
H16B H 1.0645 0.6608 0.5625 0.041 Uiso 1 1 calc R U . . .
F1 F 0.6111(8) 0.2967(3) 0.3279(2) 0.0615(16) Uani 0.545(6) 1 d . . P A 1
F2 F 0.2799(8) 0.5490(3) 0.4401(3) 0.0736(19) Uani 0.545(6) 1 d . . P A 1
F1B F 0.0687(9) 0.4308(5) 0.3767(4) 0.077(2) Uani 0.455(6) 1 d . . P A 2
F2B F 0.8010(8) 0.4242(5) 0.3935(4) 0.072(2) Uani 0.455(6) 1 d . . P A 2
C1A C 0.5345(6) 0.4770(2) 0.42674(18) 0.0384(8) Uani 1 1 d . . . . .
C6A C 0.3503(7) 0.4841(3) 0.4165(2) 0.0532(11) Uani 1 1 d . . . . .
C5A C 0.2570(6) 0.4343(3) 0.3747(2) 0.0542(11) Uani 1 1 d . . . . .
C4A C 0.3470(6) 0.3749(2) 0.34246(19) 0.0420(9) Uani 1 1 d . . . . .
C3A C 0.5298(7) 0.3659(3) 0.3519(2) 0.0492(10) Uani 1 1 d . . . . .
C2A C 0.6226(6) 0.4161(3) 0.3921(2) 0.0515(11) Uani 1 1 d . . . . .
O3 O 0.6098(3) 0.25271(15) 0.93565(11) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.5007 0.2489 0.9471 0.047 Uiso 1 1 calc R U . . .
O17 O 0.7367(3) 0.70042(13) 0.54983(11) 0.0315(5) Uani 1 1 d . . . . .
H17 H 0.7653 0.7154 0.5125 0.047 Uiso 1 1 calc R U . . .
Br1 Br 0.22433(8) 0.30580(3) 0.28624(2) 0.0666(2) Uani 1 1 d . . . . .
H2A H 0.7525 0.4127 0.3962 0.08 Uiso 0.545(6) 1 d . U P A 1
H5A H 0.1284 0.4401 0.3712 0.08 Uiso 0.545(6) 1 d . U P A 1
H3A H 0.5949 0.3203 0.3324 0.08 Uiso 0.455(6) 1 d . U P A 2
H6A H 0.2859 0.5264 0.44 0.08 Uiso 0.455(6) 1 d . U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C13 C12 1.527(5) . ?
C13 C18 1.537(5) . ?
C13 C14 1.540(5) . ?
C13 C17 1.557(4) . ?
C7 C8 1.522(5) . ?
C7 C6 1.526(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C4 C3 1.368(5) . ?
C4 C5 1.394(4) . ?
C4 H4 0.95 . ?
C3 O3 1.385(4) . ?
C3 C2 1.390(5) . ?
C2 C1 1.382(5) . ?
C2 H2 0.95 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C1 C10 1.389(5) . ?
C1 H1 0.95 . ?
C14 C8 1.527(5) . ?
C14 C15 1.534(5) . ?
C14 H14 1 . ?
C17 O17 1.438(4) . ?
C17 C20 1.473(5) . ?
C17 C16 1.560(5) . ?
C12 C11 1.546(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C8 C9 1.546(4) . ?
C8 H8 1 . ?
C15 C16 1.552(5) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C20 C21 1.185(5) . ?
C10 C5 1.400(5) . ?
C10 C9 1.524(5) . ?
C6 C5 1.511(5) . ?
C6 H6B 0.99 . ?
C6 H6C 0.99 . ?
C9 C11 1.533(5) . ?
C9 H9 1 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C21 C1A 1.436(6) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
F1 C3A 1.394(6) . ?
F2 C6A 1.298(6) . ?
F1B C5A 1.388(8) . ?
F2B C2A 1.320(8) . ?
C1A C6A 1.378(7) . ?
C1A C2A 1.404(6) . ?
C6A C5A 1.382(6) . ?
C6A H6A 0.982(5) . ?
C5A C4A 1.368(6) . ?
C5A H5A 0.955(5) . ?
C4A C3A 1.368(7) . ?
C4A Br1 1.872(4) . ?
C3A C2A 1.366(6) . ?
C3A H3A 0.986(4) . ?
C2A H2A 0.962(4) . ?
O3 H3 0.84 . ?
O17 H17 0.84 . ?

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 C13 C18 110.2(3) . . ?
C12 C13 C14 109.6(3) . . ?
C18 C13 C14 112.3(3) . . ?
C12 C13 C17 116.4(3) . . ?
C18 C13 C17 108.3(3) . . ?
C14 C13 C17 99.7(3) . . ?
C8 C7 C6 109.3(3) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C3 O3 118.6(3) . . ?
C4 C3 C2 119.6(3) . . ?
O3 C3 C2 121.8(3) . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 C10 122.5(3) . . ?
C2 C1 H1 118.7 . . ?
C10 C1 H1 118.7 . . ?
C8 C14 C15 119.4(3) . . ?
C8 C14 C13 112.1(3) . . ?
C15 C14 C13 104.3(3) . . ?
C8 C14 H14 106.8 . . ?
C15 C14 H14 106.8 . . ?
C13 C14 H14 106.8 . . ?
O17 C17 C20 109.1(3) . . ?
O17 C17 C13 111.2(3) . . ?
C20 C17 C13 111.3(3) . . ?
O17 C17 C16 112.0(3) . . ?
C20 C17 C16 110.0(3) . . ?
C13 C17 C16 103.2(3) . . ?
C13 C12 C11 110.8(3) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C7 C8 C14 113.9(3) . . ?
C7 C8 C9 109.6(3) . . ?
C14 C8 C9 108.0(3) . . ?
C7 C8 H8 108.4 . . ?
C14 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C14 C15 C16 104.0(3) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 109 . . ?
C21 C20 C17 179.6(4) . . ?
C1 C10 C5 117.9(3) . . ?
C1 C10 C9 120.4(3) . . ?
C5 C10 C9 121.6(3) . . ?
C5 C6 C7 113.2(3) . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6C 108.9 . . ?
C7 C6 H6C 108.9 . . ?
H6B C6 H6C 107.8 . . ?
C4 C5 C10 119.4(3) . . ?
C4 C5 C6 118.9(3) . . ?
C10 C5 C6 121.6(3) . . ?
C10 C9 C11 113.9(3) . . ?
C10 C9 C8 111.8(3) . . ?
C11 C9 C8 110.8(3) . . ?
C10 C9 H9 106.6 . . ?
C11 C9 H9 106.6 . . ?
C8 C9 H9 106.6 . . ?
C9 C11 C12 112.2(3) . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C20 C21 C1A 176.9(4) . . ?
C15 C16 C17 106.3(3) . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C6A C1A C2A 116.0(4) . . ?
C6A C1A C21 122.1(4) . . ?
C2A C1A C21 121.9(4) . . ?
F2 C6A C1A 114.0(5) . . ?
F2 C6A C5A 122.7(5) . . ?
C1A C6A C5A 122.3(4) . . ?
C1A C6A H6A 117.4(4) . . ?
C5A C6A H6A 120.3(5) . . ?
C4A C5A C6A 120.1(4) . . ?
C4A C5A F1B 117.9(5) . . ?
C6A C5A F1B 120.2(5) . . ?
C4A C5A H5A 121.2(4) . . ?
C6A C5A H5A 118.6(4) . . ?
C3A C4A C5A 119.1(4) . . ?
C3A C4A Br1 119.7(3) . . ?
C5A C4A Br1 121.2(3) . . ?
C2A C3A C4A 120.8(4) . . ?
C2A C3A F1 120.8(5) . . ?
C4A C3A F1 117.6(4) . . ?
C2A C3A H3A 118.7(5) . . ?
C4A C3A H3A 120.4(4) . . ?
F2B C2A C3A 125.1(5) . . ?
F2B C2A C1A 111.9(5) . . ?
C3A C2A C1A 121.7(4) . . ?
C3A C2A H2A 121.1(5) . . ?
C1A C2A H2A 117.2(4) . . ?
C3 O3 H3 109.5 . . ?
C17 O17 H17 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 C4 C3 O3 178.4(3) . . . . ?
C5 C4 C3 C2 -1.5(5) . . . . ?
C4 C3 C2 C1 1.6(5) . . . . ?
O3 C3 C2 C1 -178.3(3) . . . . ?
C3 C2 C1 C10 -1.0(6) . . . . ?
C12 C13 C14 C8 -59.8(4) . . . . ?
C18 C13 C14 C8 63.0(4) . . . . ?
C17 C13 C14 C8 177.5(3) . . . . ?
C12 C13 C14 C15 169.6(3) . . . . ?
C18 C13 C14 C15 -67.6(4) . . . . ?
C17 C13 C14 C15 46.9(3) . . . . ?
C12 C13 C17 O17 79.9(4) . . . . ?
C18 C13 C17 O17 -44.9(4) . . . . ?
C14 C13 C17 O17 -162.4(3) . . . . ?
C12 C13 C17 C20 -41.9(4) . . . . ?
C18 C13 C17 C20 -166.7(3) . . . . ?
C14 C13 C17 C20 75.8(3) . . . . ?
C12 C13 C17 C16 -159.9(3) . . . . ?
C18 C13 C17 C16 75.3(3) . . . . ?
C14 C13 C17 C16 -42.2(3) . . . . ?
C18 C13 C12 C11 -69.1(4) . . . . ?
C14 C13 C12 C11 54.9(4) . . . . ?
C17 C13 C12 C11 167.0(3) . . . . ?
C6 C7 C8 C14 173.1(3) . . . . ?
C6 C7 C8 C9 -65.7(4) . . . . ?
C15 C14 C8 C7 -55.3(4) . . . . ?
C13 C14 C8 C7 -177.6(3) . . . . ?
C15 C14 C8 C9 -177.3(3) . . . . ?
C13 C14 C8 C9 60.3(4) . . . . ?
C8 C14 C15 C16 -159.0(3) . . . . ?
C13 C14 C15 C16 -32.9(4) . . . . ?
C2 C1 C10 C5 0.3(6) . . . . ?
C2 C1 C10 C9 176.2(3) . . . . ?
C8 C7 C6 C5 48.8(4) . . . . ?
C3 C4 C5 C10 0.8(5) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C1 C10 C5 C4 -0.1(5) . . . . ?
C9 C10 C5 C4 -176.0(3) . . . . ?
C1 C10 C5 C6 178.5(3) . . . . ?
C9 C10 C5 C6 2.7(5) . . . . ?
C7 C6 C5 C4 160.8(3) . . . . ?
C7 C6 C5 C10 -17.9(5) . . . . ?
C1 C10 C9 C11 39.0(5) . . . . ?
C5 C10 C9 C11 -145.2(3) . . . . ?
C1 C10 C9 C8 165.6(3) . . . . ?
C5 C10 C9 C8 -18.6(5) . . . . ?
C7 C8 C9 C10 49.7(4) . . . . ?
C14 C8 C9 C10 174.3(3) . . . . ?
C7 C8 C9 C11 177.9(3) . . . . ?
C14 C8 C9 C11 -57.5(4) . . . . ?
C10 C9 C11 C12 -177.1(3) . . . . ?
C8 C9 C11 C12 55.8(4) . . . . ?
C13 C12 C11 C9 -54.4(4) . . . . ?
C14 C15 C16 C17 5.7(4) . . . . ?
O17 C17 C16 C15 142.7(3) . . . . ?
C20 C17 C16 C15 -95.9(3) . . . . ?
C13 C17 C16 C15 23.0(4) . . . . ?
C2A C1A C6A F2 -168.6(5) . . . . ?
C21 C1A C6A F2 13.3(7) . . . . ?
C2A C1A C6A C5A 0.1(7) . . . . ?
C21 C1A C6A C5A -178.0(4) . . . . ?
F2 C6A C5A C4A 168.5(6) . . . . ?
C1A C6A C5A C4A 0.8(8) . . . . ?
C1A C6A C5A F1B 165.1(6) . . . . ?
C6A C5A C4A C3A -0.4(7) . . . . ?
F1B C5A C4A C3A -165.0(6) . . . . ?
C6A C5A C4A Br1 179.3(4) . . . . ?
F1B C5A C4A Br1 14.7(8) . . . . ?
C5A C4A C3A C2A -0.9(7) . . . . ?
Br1 C4A C3A C2A 179.3(4) . . . . ?
C5A C4A C3A F1 168.6(5) . . . . ?
Br1 C4A C3A F1 -11.1(6) . . . . ?
C4A C3A C2A F2B -164.0(6) . . . . ?
C4A C3A C2A C1A 1.9(8) . . . . ?
F1 C3A C2A C1A -167.3(5) . . . . ?
C6A C1A C2A F2B 166.2(6) . . . . ?
C21 C1A C2A F2B -15.7(7) . . . . ?
C6A C1A C2A C3A -1.4(7) . . . . ?
C21 C1A C2A C3A 176.7(4) . . . . ?

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
C2 H2 F2 0.95 2.64 3.167(7) 115.8 2_565
C16 H16A F2 0.99 2.4 3.272(7) 146.2 1_655
O3 H3 O17 0.84 1.93 2.714(3) 155.2 4_646
O17 H17 O3 0.84 1.91 2.736(3) 165.7 2_664
C2 H2 F2 0.95 2.64 3.167(7) 115.8 2_565
C16 H16A F2 0.99 2.4 3.272(7) 146.2 1_655
O3 H3 O17 0.84 1.93 2.714(3) 155.2 4_646
O17 H17 O3 0.84 1.91 2.736(3) 165.7 2_664
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.033 0.250 0.500 231 21 ' '
2 -0.048 0.750 0.000 231 21 ' '
_platon_squeeze_details          
;
;

# END of CIF
####################################################################### 
# 
# 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_san804
_database_code_depnum_ccdc_archive 'CCDC 1463830'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T15:14:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H29 Br F O2'
_chemical_formula_weight         472.4
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.2612(3)
_cell_length_b                   15.8845(6)
_cell_length_c                   19.4007(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2237.69(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9480
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_T_max  0.9144

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      -0.093992
_diffrn_orient_matrix_ub_12      -0.036662
_diffrn_orient_matrix_ub_13      -0.022765
_diffrn_orient_matrix_ub_21      0.058131
_diffrn_orient_matrix_ub_22      -0.050827
_diffrn_orient_matrix_ub_23      0.021252
_diffrn_orient_matrix_ub_31      -0.082174
_diffrn_orient_matrix_ub_32      0.005979
_diffrn_orient_matrix_ub_33      0.041073
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.069
_diffrn_reflns_number            14795
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.945
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.764
_reflns_number_total             4996
_reflns_number_gt                3296
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.9397P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4996
_refine_ls_number_parameters     324
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.025(17)
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C3 C 0.4044(9) 0.3502(5) 0.4505(3) 0.0634(17) Uani 1 1 d . . . . .
C4 C 0.5758(8) 0.3910(4) 0.4699(3) 0.0586(14) Uani 1 1 d . . . . .
H4A H 0.6742 0.3535 0.4556 0.07 Uiso 1 1 calc R U . . .
H4B H 0.586 0.441 0.4416 0.07 Uiso 1 1 calc R U . . .
C5 C 0.6145(6) 0.4144(4) 0.5337(3) 0.0492(12) Uani 1 1 d . . . . .
C6 C 0.8027(8) 0.4475(4) 0.5521(3) 0.0623(16) Uani 1 1 d . . . . .
H6B H 0.8735 0.4553 0.5102 0.075 Uiso 1 1 calc R U . . .
H6A H 0.8661 0.406 0.5802 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7948(8) 0.5302(5) 0.5910(4) 0.0574(16) Uani 1 1 d . . . . .
C8 C 0.6668(7) 0.5240(4) 0.6533(3) 0.0460(12) Uani 1 1 d . . . . .
C9 C 0.4730(7) 0.4941(3) 0.6312(3) 0.0394(11) Uani 1 1 d . . . . .
C10 C 0.4789(7) 0.4092(4) 0.5918(3) 0.0415(11) Uani 1 1 d . . . . .
C1 C 0.2867(7) 0.3844(4) 0.5671(3) 0.0476(13) Uani 1 1 d . . . . .
H1A H 0.2187 0.3608 0.6056 0.057 Uiso 1 1 calc R U . . .
H1B H 0.2222 0.4346 0.552 0.057 Uiso 1 1 calc R U . . .
C2 C 0.2886(10) 0.3212(5) 0.5089(3) 0.0589(16) Uani 1 1 d . . . . .
C11 C 0.3423(8) 0.4900(3) 0.6934(3) 0.0459(12) Uani 1 1 d . . . . .
H11A H 0.22 0.4751 0.6773 0.055 Uiso 1 1 calc R U . . .
H11B H 0.3836 0.4457 0.7242 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3309(8) 0.5721(3) 0.7335(3) 0.0457(12) Uani 1 1 d . . . . .
H12A H 0.2547 0.5641 0.774 0.055 Uiso 1 1 calc R U . . .
H12B H 0.2737 0.6149 0.705 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5226(7) 0.6016(3) 0.7555(2) 0.0409(11) Uani 1 1 d . . . . .
C17 C 0.5392(8) 0.6944(4) 0.7835(3) 0.0462(13) Uani 1 1 d . . . . .
C16 C 0.7447(9) 0.7142(5) 0.7724(4) 0.0556(15) Uani 1 1 d . . . . .
C15 C 0.8182(9) 0.6548(5) 0.7173(4) 0.0608(15) Uani 1 1 d . . . . .
C14 C 0.6455(7) 0.6077(3) 0.6916(3) 0.0426(11) Uani 1 1 d . . . . .
C18 C 0.6010(9) 0.5419(4) 0.8100(3) 0.0577(15) Uani 1 1 d . . . . .
H18A H 0.7212 0.5608 0.8235 0.086 Uiso 1 1 calc R U . . .
H18B H 0.5213 0.5412 0.8494 0.086 Uiso 1 1 calc R U . . .
H18C H 0.6097 0.4862 0.7911 0.086 Uiso 1 1 calc R U . . .
C20 C 0.4182(8) 0.7505(3) 0.7419(3) 0.0494(13) Uani 1 1 d . . . . .
C21 C 0.3131(9) 0.7887(4) 0.7082(3) 0.0530(13) Uani 1 1 d . . . . .
C1A C 0.1709(8) 0.8244(3) 0.6648(3) 0.0475(12) Uani 1 1 d . . . . .
C2A C 0.1621(9) 0.8024(4) 0.5951(3) 0.0608(15) Uani 1 1 d . . . . .
H2 H 0.2555 0.7706 0.5752 0.073 Uiso 1 1 calc R U . . .
C3A C 0.0147(10) 0.8280(4) 0.5567(3) 0.0589(15) Uani 1 1 d . . . . .
C4A C -0.1240(8) 0.8757(4) 0.5840(3) 0.0541(14) Uani 1 1 d . . . . .
C5A C -0.1128(8) 0.8999(4) 0.6519(3) 0.0619(15) Uani 1 1 d . . . . .
H5 H -0.2047 0.9332 0.6711 0.074 Uiso 1 1 calc R U . . .
C6A C 0.0353(9) 0.8747(4) 0.6916(3) 0.0565(15) Uani 1 1 d D . . . .
H6 H 0.0431 0.8921 0.7372 0.068 Uiso 1 1 calc DR U . . .
Br1 Br -0.33323(10) 0.90329(5) 0.53073(4) 0.0829(3) Uani 1 1 d . . . . .
O1 O 0.4978(8) 0.7038(3) 0.8550(2) 0.0575(11) Uani 1 1 d . . . . .
O2 O 0.3679(7) 0.3363(5) 0.3897(2) 0.103(2) Uani 1 1 d . . . . .
F1 F 0.0076(8) 0.8074(4) 0.4898(2) 0.1148(18) Uani 1 1 d . . . . .
H01 H 0.406(8) 0.696(4) 0.860(3) 0.032(18) Uiso 1 1 d . . . . .
H5A H 0.914(8) 0.543(3) 0.605(3) 0.039(14) Uiso 1 1 d . . . . .
H7A H 0.752(8) 0.571(4) 0.565(3) 0.051(18) Uiso 1 1 d . . . . .
H9 H 0.397(8) 0.536(4) 0.601(3) 0.048(15) Uiso 1 1 d . . . . .
H10 H 0.524(8) 0.371(4) 0.621(3) 0.047(16) Uiso 1 1 d . . . . .
H2B H 0.347(8) 0.267(4) 0.521(3) 0.054(16) Uiso 1 1 d . . . . .
H2A H 0.189(10) 0.308(4) 0.495(3) 0.051(16) Uiso 1 1 d . . . . .
H15A H 0.888(10) 0.678(4) 0.687(4) 0.06(2) Uiso 1 1 d . . . . .
H15B H 0.920(10) 0.616(4) 0.738(3) 0.067(19) Uiso 1 1 d . . . . .
H16B H 0.812(9) 0.705(3) 0.809(3) 0.043(14) Uiso 1 1 d . . . . .
H14 H 0.565(9) 0.648(4) 0.666(3) 0.054(16) Uiso 1 1 d . . . . .
H8 H 0.736(9) 0.481(4) 0.691(3) 0.069(19) Uiso 1 1 d . . . . .
H16A H 0.758(9) 0.763(5) 0.763(3) 0.06(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C3 O2 1.229(7) . ?
C3 C4 1.453(9) . ?
C3 C2 1.483(9) . ?
C4 C5 1.323(8) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 C10 1.498(7) . ?
C5 C6 1.507(8) . ?
C6 C7 1.517(9) . ?
C6 H6B 0.97 . ?
C6 H6A 0.97 . ?
C7 C8 1.527(8) . ?
C7 H5A 0.93(6) . ?
C7 H7A 0.88(6) . ?
C8 C14 1.531(8) . ?
C8 C9 1.545(7) . ?
C8 H8 1.11(7) . ?
C9 C11 1.536(7) . ?
C9 C10 1.552(8) . ?
C9 H9 1.05(6) . ?
C10 C1 1.527(7) . ?
C10 H10 0.90(6) . ?
C1 C2 1.511(8) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 H2B 0.99(6) . ?
C2 H2A 0.80(7) . ?
C11 C12 1.521(7) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.530(7) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C18 1.530(8) . ?
C13 C14 1.531(7) . ?
C13 C17 1.575(8) . ?
C17 O1 1.429(7) . ?
C17 C20 1.488(8) . ?
C17 C16 1.540(9) . ?
C16 C15 1.522(10) . ?
C16 H16B 0.88(6) . ?
C16 H16A 0.81(7) . ?
C15 C14 1.544(8) . ?
C15 H15A 0.86(7) . ?
C15 H15B 1.05(7) . ?
C14 H14 1.00(6) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C20 C21 1.174(8) . ?
C21 C1A 1.449(9) . ?
C1A C6A 1.370(8) . ?
C1A C2A 1.397(8) . ?
C2A C3A 1.367(9) . ?
C2A H2 0.93 . ?
C3A F1 1.339(7) . ?
C3A C4A 1.367(9) . ?
C4A C5A 1.375(9) . ?
C4A Br1 1.888(6) . ?
C5A C6A 1.382(9) . ?
C5A H5 0.93 . ?
C6A H6 0.93 . ?
O1 H01 0.68(6) . ?

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
O2 C3 C4 120.9(6) . . ?
O2 C3 C2 123.7(6) . . ?
C4 C3 C2 115.2(5) . . ?
C5 C4 C3 123.4(6) . . ?
C5 C4 H4A 106.5 . . ?
C3 C4 H4A 106.5 . . ?
C5 C4 H4B 106.5 . . ?
C3 C4 H4B 106.5 . . ?
H4A C4 H4B 106.5 . . ?
C4 C5 C10 123.2(5) . . ?
C4 C5 C6 120.8(5) . . ?
C10 C5 C6 115.9(5) . . ?
C5 C6 C7 112.7(5) . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
H6B C6 H6A 107.8 . . ?
C6 C7 C8 111.1(5) . . ?
C6 C7 H5A 107(3) . . ?
C8 C7 H5A 111(3) . . ?
C6 C7 H7A 112(4) . . ?
C8 C7 H7A 107(4) . . ?
H5A C7 H7A 109(5) . . ?
C7 C8 C14 112.9(5) . . ?
C7 C8 C9 110.8(4) . . ?
C14 C8 C9 108.0(4) . . ?
C7 C8 H8 106(4) . . ?
C14 C8 H8 105(3) . . ?
C9 C8 H8 114(3) . . ?
C11 C9 C8 111.0(4) . . ?
C11 C9 C10 111.5(4) . . ?
C8 C9 C10 112.2(4) . . ?
C11 C9 H9 99(3) . . ?
C8 C9 H9 116(3) . . ?
C10 C9 H9 106(3) . . ?
C5 C10 C1 112.3(4) . . ?
C5 C10 C9 110.0(4) . . ?
C1 C10 C9 110.7(4) . . ?
C5 C10 H10 106(4) . . ?
C1 C10 H10 111(4) . . ?
C9 C10 H10 106(4) . . ?
C2 C1 C10 113.4(5) . . ?
C2 C1 H1A 108.9 . . ?
C10 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
C10 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 111.7(6) . . ?
C3 C2 H2B 102(3) . . ?
C1 C2 H2B 114(3) . . ?
C3 C2 H2A 109(4) . . ?
C1 C2 H2A 115(4) . . ?
H2B C2 H2A 104(6) . . ?
C12 C11 C9 113.5(4) . . ?
C12 C11 H11A 108.9 . . ?
C9 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C9 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.9(4) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C18 110.0(5) . . ?
C12 C13 C14 108.9(4) . . ?
C18 C13 C14 112.4(5) . . ?
C12 C13 C17 116.9(4) . . ?
C18 C13 C17 108.3(4) . . ?
C14 C13 C17 100.1(4) . . ?
O1 C17 C20 109.9(5) . . ?
O1 C17 C16 108.5(5) . . ?
C20 C17 C16 112.0(5) . . ?
O1 C17 C13 114.6(4) . . ?
C20 C17 C13 109.1(4) . . ?
C16 C17 C13 102.5(5) . . ?
C15 C16 C17 108.1(5) . . ?
C15 C16 H16B 106(4) . . ?
C17 C16 H16B 113(4) . . ?
C15 C16 H16A 113(5) . . ?
C17 C16 H16A 110(5) . . ?
H16B C16 H16A 107(6) . . ?
C16 C15 C14 104.0(5) . . ?
C16 C15 H15A 115(5) . . ?
C14 C15 H15A 118(5) . . ?
C16 C15 H15B 110(4) . . ?
C14 C15 H15B 114(4) . . ?
H15A C15 H15B 96(6) . . ?
C13 C14 C8 113.5(4) . . ?
C13 C14 C15 104.0(4) . . ?
C8 C14 C15 119.8(5) . . ?
C13 C14 H14 96(3) . . ?
C8 C14 H14 112(3) . . ?
C15 C14 H14 109(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 174.2(6) . . ?
C20 C21 C1A 171.9(6) . . ?
C6A C1A C2A 118.7(5) . . ?
C6A C1A C21 121.3(5) . . ?
C2A C1A C21 119.8(5) . . ?
C3A C2A C1A 119.3(6) . . ?
C3A C2A H2 120.4 . . ?
C1A C2A H2 120.4 . . ?
F1 C3A C2A 119.1(6) . . ?
F1 C3A C4A 118.9(6) . . ?
C2A C3A C4A 122.0(5) . . ?
C3A C4A C5A 118.8(5) . . ?
C3A C4A Br1 120.6(5) . . ?
C5A C4A Br1 120.5(4) . . ?
C4A C5A C6A 119.9(6) . . ?
C4A C5A H5 120 . . ?
C6A C5A H5 120 . . ?
C1A C6A C5A 121.1(6) . . ?
C1A C6A H6 119.4 . . ?
C5A C6A H6 119.4 . . ?
C17 O1 H01 108(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
O2 C3 C4 C5 173.6(8) . . . . ?
C2 C3 C4 C5 -11.3(10) . . . . ?
C3 C4 C5 C10 -6.2(10) . . . . ?
C3 C4 C5 C6 173.1(6) . . . . ?
C4 C5 C6 C7 129.5(7) . . . . ?
C10 C5 C6 C7 -51.2(8) . . . . ?
C5 C6 C7 C8 52.3(8) . . . . ?
C6 C7 C8 C14 -176.6(5) . . . . ?
C6 C7 C8 C9 -55.2(7) . . . . ?
C7 C8 C9 C11 -178.5(5) . . . . ?
C14 C8 C9 C11 -54.4(5) . . . . ?
C7 C8 C9 C10 55.9(6) . . . . ?
C14 C8 C9 C10 -179.9(4) . . . . ?
C4 C5 C10 C1 -7.0(8) . . . . ?
C6 C5 C10 C1 173.7(5) . . . . ?
C4 C5 C10 C9 -130.8(6) . . . . ?
C6 C5 C10 C9 49.9(6) . . . . ?
C11 C9 C10 C5 -177.2(4) . . . . ?
C8 C9 C10 C5 -51.9(6) . . . . ?
C11 C9 C10 C1 58.1(6) . . . . ?
C8 C9 C10 C1 -176.6(4) . . . . ?
C5 C10 C1 C2 36.5(7) . . . . ?
C9 C10 C1 C2 159.9(5) . . . . ?
O2 C3 C2 C1 -144.6(8) . . . . ?
C4 C3 C2 C1 40.4(9) . . . . ?
C10 C1 C2 C3 -53.6(8) . . . . ?
C8 C9 C11 C12 54.4(6) . . . . ?
C10 C9 C11 C12 -179.6(5) . . . . ?
C9 C11 C12 C13 -54.4(6) . . . . ?
C11 C12 C13 C18 -68.6(6) . . . . ?
C11 C12 C13 C14 54.9(6) . . . . ?
C11 C12 C13 C17 167.4(4) . . . . ?
C12 C13 C17 O1 84.6(6) . . . . ?
C18 C13 C17 O1 -40.3(6) . . . . ?
C14 C13 C17 O1 -158.1(5) . . . . ?
C12 C13 C17 C20 -39.1(6) . . . . ?
C18 C13 C17 C20 -164.0(5) . . . . ?
C14 C13 C17 C20 78.2(5) . . . . ?
C12 C13 C17 C16 -158.0(5) . . . . ?
C18 C13 C17 C16 77.1(6) . . . . ?
C14 C13 C17 C16 -40.7(5) . . . . ?
O1 C17 C16 C15 143.3(6) . . . . ?
C20 C17 C16 C15 -95.2(7) . . . . ?
C13 C17 C16 C15 21.7(7) . . . . ?
C17 C16 C15 C14 6.0(8) . . . . ?
C12 C13 C14 C8 -59.6(6) . . . . ?
C18 C13 C14 C8 62.5(6) . . . . ?
C17 C13 C14 C8 177.2(4) . . . . ?
C12 C13 C14 C15 168.6(5) . . . . ?
C18 C13 C14 C15 -69.3(6) . . . . ?
C17 C13 C14 C15 45.4(5) . . . . ?
C7 C8 C14 C13 -178.1(5) . . . . ?
C9 C8 C14 C13 59.0(6) . . . . ?
C7 C8 C14 C15 -54.5(7) . . . . ?
C9 C8 C14 C15 -177.4(5) . . . . ?
C16 C15 C14 C13 -32.5(7) . . . . ?
C16 C15 C14 C8 -160.5(5) . . . . ?
C6A C1A C2A C3A -3.1(9) . . . . ?
C21 C1A C2A C3A 171.9(6) . . . . ?
C1A C2A C3A F1 179.4(6) . . . . ?
C1A C2A C3A C4A 0.9(10) . . . . ?
F1 C3A C4A C5A -177.2(6) . . . . ?
C2A C3A C4A C5A 1.3(10) . . . . ?
F1 C3A C4A Br1 5.8(9) . . . . ?
C2A C3A C4A Br1 -175.6(5) . . . . ?
C3A C4A C5A C6A -1.2(9) . . . . ?
Br1 C4A C5A C6A 175.8(5) . . . . ?
C2A C1A C6A C5A 3.3(9) . . . . ?
C21 C1A C6A C5A -171.7(6) . . . . ?
C4A C5A C6A C1A -1.2(10) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_san650x
_database_code_depnum_ccdc_archive 'CCDC 1463831'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T15:34:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C35 H47 I1 O3'
_chemical_formula_sum            'C35 H47 I O3'
_chemical_formula_weight         642.62
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   20.978
_cell_length_b                   6.314
_cell_length_c                   23.951
_cell_angle_alpha                90
_cell_angle_beta                 106.06
_cell_angle_gamma                90
_cell_volume                     3048.7
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    17433
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.4
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.913
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.948

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.013376
_diffrn_orient_matrix_ub_12      -0.114332
_diffrn_orient_matrix_ub_13      -0.023371
_diffrn_orient_matrix_ub_21      0.015738
_diffrn_orient_matrix_ub_22      -0.088431
_diffrn_orient_matrix_ub_23      0.035817
_diffrn_orient_matrix_ub_31      -0.0451
_diffrn_orient_matrix_ub_32      -0.064769
_diffrn_orient_matrix_ub_33      -0.007648
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_number            20437
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.032
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.836
_reflns_number_total             6932
_reflns_number_gt                5469
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+4.7667P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6932
_refine_ls_number_parameters     361
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.075
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.05(2)
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.06755(16) 0.1950(10) 0.02924(14) 0.0326(7) Uani 1 1 d D . . . .
C7 C 0.1718(2) 0.6990(14) 0.20866(17) 0.0265(9) Uani 1 1 d . . . . .
H7A H 0.1377 0.588 0.2061 0.032 Uiso 1 1 calc R U . . .
H7B H 0.1693 0.7987 0.2399 0.032 Uiso 1 1 calc R U . . .
C5 C 0.1660(2) 0.6783(12) 0.10153(19) 0.0228(10) Uani 1 1 d . . . . .
H5 H 0.1607 0.771 0.0667 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3309(2) 0.2190(12) 0.24973(18) 0.0260(12) Uani 1 1 d . . . . .
H12B H 0.2992 0.1001 0.2454 0.031 Uiso 1 1 calc R U . . .
H12A H 0.3763 0.1592 0.2599 0.031 Uiso 1 1 calc R U . . .
C1 C 0.2381(2) 0.4355(8) 0.0639(2) 0.0236(11) Uani 1 1 d . . . . .
H1B H 0.2341 0.5263 0.0294 0.028 Uiso 1 1 calc R U . . .
H1A H 0.2819 0.3645 0.0727 0.028 Uiso 1 1 calc R U . . .
C4 C 0.1107(2) 0.5105(9) 0.0859(2) 0.0246(11) Uani 1 1 d . . . . .
H4A H 0.1131 0.4227 0.1206 0.029 Uiso 1 1 calc R U . . .
H4B H 0.0672 0.5833 0.0752 0.029 Uiso 1 1 calc R U . . .
C20 C 0.3832(2) 0.2335(9) 0.4079(2) 0.0260(14) Uani 1 1 d . . . . .
H21 H 0.4184 0.3246 0.3994 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2503(2) 0.4544(8) 0.1739(2) 0.0202(10) Uani 1 1 d . . . . .
H9 H 0.2157 0.3414 0.1678 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3238(2) 0.3656(8) 0.2986(2) 0.0221(10) Uani 1 1 d . . . . .
C10 C 0.2365(2) 0.5775(8) 0.1155(2) 0.0218(11) Uani 1 1 d . . . . .
O2 O 0.31399(17) 0.4900(6) 0.43176(14) 0.0269(8) Uani 1 1 d . . . . .
C17 C 0.3202(2) 0.2531(7) 0.35569(19) 0.0226(12) Uani 1 1 d . . . . .
H17 H 0.2998 0.1099 0.346 0.027 Uiso 1 1 calc R U . . .
C29 C 0.0797(2) 0.5964(9) -0.0613(2) 0.0264(12) Uani 1 1 d . . . . .
C16 C 0.2727(3) 0.3953(9) 0.3796(2) 0.0272(12) Uani 1 1 d . . . . .
H16 H 0.2368 0.3083 0.3883 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3785(3) 0.5371(9) 0.3109(2) 0.0296(12) Uani 1 1 d . . . . .
H18B H 0.422 0.469 0.3183 0.044 Uiso 1 1 calc R U . . .
H18C H 0.3765 0.6201 0.3449 0.044 Uiso 1 1 calc R U . . .
H18A H 0.3715 0.6307 0.2771 0.044 Uiso 1 1 calc R U . . .
C14 C 0.2535(2) 0.4649(8) 0.2785(2) 0.0236(11) Uani 1 1 d . . . . .
H14 H 0.2219 0.343 0.2688 0.028 Uiso 1 1 calc R U . . .
C6A C 0.0353(2) 0.6621(10) -0.1674(2) 0.0287(14) Uani 1 1 d . . . . .
H6A H 0.0452 0.5202 -0.1752 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1146(2) 0.3655(8) 0.0359(2) 0.0235(11) Uani 1 1 d . . . . .
C11 C 0.3176(2) 0.3397(8) 0.1915(2) 0.0262(11) Uani 1 1 d . . . . .
H11B H 0.3534 0.4451 0.1944 0.031 Uiso 1 1 calc R U . . .
H11A H 0.3195 0.2381 0.1605 0.031 Uiso 1 1 calc R U . . .
C1A C 0.0527(2) 0.7322(10) -0.1101(2) 0.0267(14) Uani 1 1 d . . . . .
C15 C 0.2435(3) 0.5630(9) 0.3340(2) 0.0307(13) Uani 1 1 d . . . . .
H15A H 0.2675 0.6991 0.3433 0.037 Uiso 1 1 calc R U . . .
H15B H 0.1959 0.5865 0.3304 0.037 Uiso 1 1 calc R U . . .
C28 C 0.0972(2) 0.4875(8) -0.0190(2) 0.0264(12) Uani 1 1 d . . . . .
C2A C 0.0397(3) 0.9468(9) -0.0999(2) 0.0308(12) Uani 1 1 d . . . . .
H2A H 0.0521 1.0007 -0.0614 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2406(2) 0.5962(8) 0.2240(2) 0.0237(11) Uani 1 1 d . . . . .
H8 H 0.2745 0.7119 0.2309 0.028 Uiso 1 1 calc R U . . .
C2 C 0.1841(2) 0.2667(8) 0.0487(2) 0.0249(12) Uani 1 1 d . . . . .
H2C H 0.1904 0.1661 0.0815 0.03 Uiso 1 1 calc R U . . .
H2B H 0.1878 0.1865 0.0142 0.03 Uiso 1 1 calc R U . . .
C6 C 0.1571(3) 0.8182(9) 0.1508(2) 0.0300(12) Uani 1 1 d . . . . .
H6C H 0.111 0.8719 0.1407 0.036 Uiso 1 1 calc R U . . .
H6B H 0.1872 0.9417 0.1552 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3623(3) 0.3359(9) 0.4582(2) 0.0274(12) Uani 1 1 d . . . . .
C19 C 0.2887(3) 0.7512(8) 0.1184(2) 0.0289(14) Uani 1 1 d . . . . .
H19B H 0.3317 0.6855 0.1209 0.043 Uiso 1 1 calc R U . . .
H19C H 0.2923 0.8396 0.1528 0.043 Uiso 1 1 calc R U . . .
H19A H 0.2753 0.839 0.0834 0.043 Uiso 1 1 calc R U . . .
C3A C 0.0091(3) 1.0775(9) -0.1454(2) 0.0323(13) Uani 1 1 d . . . . .
H3A H 0.0003 1.2211 -0.1382 0.039 Uiso 1 1 calc R U . . .
O3 O 0.33323(16) 0.1747(9) 0.48471(13) 0.0324(9) Uani 1 1 d . . . . .
C27 C 0.4148(3) 0.1794(18) 0.6097(2) 0.0488(16) Uani 1 1 d . . . . .
H27C H 0.3947 0.0789 0.631 0.073 Uiso 1 1 calc R U . . .
H27B H 0.4525 0.2498 0.6368 0.073 Uiso 1 1 calc R U . . .
H27A H 0.4303 0.1032 0.5802 0.073 Uiso 1 1 calc R U . . .
C4A C -0.0090(3) 0.9993(9) -0.2017(2) 0.0283(12) Uani 1 1 d . . . . .
C26 C 0.3090(3) 0.2492(10) 0.5321(2) 0.0391(18) Uani 1 1 d . . . . .
H26A H 0.2886 0.1295 0.5477 0.047 Uiso 1 1 calc R U . . .
H26B H 0.2742 0.3573 0.5174 0.047 Uiso 1 1 calc R U . . .
C5A C 0.0043(3) 0.7917(9) -0.2131(2) 0.0289(12) Uani 1 1 d . . . . .
H5A H -0.0078 0.7393 -0.2518 0.035 Uiso 1 1 calc R U . . .
C23 C 0.4174(3) 0.4497(9) 0.5028(2) 0.0289(12) Uani 1 1 d . . . . .
H23B H 0.4325 0.5727 0.4842 0.035 Uiso 1 1 calc R U . . .
H23A H 0.4556 0.3525 0.5166 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3950(3) 0.5262(10) 0.5549(2) 0.0372(14) Uani 1 1 d . . . . .
H24B H 0.3623 0.6418 0.5426 0.045 Uiso 1 1 calc R U . . .
H24A H 0.4336 0.5829 0.585 0.045 Uiso 1 1 calc R U . . .
C25 C 0.3638(3) 0.3437(11) 0.5804(2) 0.0384(14) Uani 1 1 d . . . . .
H25 H 0.3436 0.4035 0.6102 0.046 Uiso 1 1 calc R U . . .
I1 I -0.05845(2) 1.19626(7) -0.27090(2) 0.04342(12) Uani 1 1 d . . . . .
C21 C 0.4107(3) 0.0102(10) 0.4191(3) 0.0384(14) Uani 1 1 d . . . . .
H21A H 0.4463 0.0072 0.4555 0.058 Uiso 1 1 calc R U . . .
H21C H 0.4283 -0.034 0.387 0.058 Uiso 1 1 calc R U . . .
H21B H 0.3752 -0.0867 0.4218 0.058 Uiso 1 1 calc R U . . .
H1 H 0.069(6) 0.128(17) 0.059(3) 0.16(5) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C3 1.439(7) . ?
O1 H1 0.82(3) . ?
C7 C6 1.531(7) . ?
C7 C8 1.533(7) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C5 C6 1.526(7) . ?
C5 C4 1.538(8) . ?
C5 C10 1.561(7) . ?
C5 H5 1 . ?
C12 C13 1.532(7) . ?
C12 C11 1.546(7) . ?
C12 H12B 0.99 . ?
C12 H12A 0.99 . ?
C1 C2 1.526(7) . ?
C1 C10 1.535(7) . ?
C1 H1B 0.99 . ?
C1 H1A 0.99 . ?
C4 C3 1.527(7) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C20 C21 1.519(8) . ?
C20 C22 1.535(7) . ?
C20 C17 1.553(6) . ?
C20 H21 1 . ?
C9 C11 1.539(7) . ?
C9 C8 1.555(7) . ?
C9 C10 1.556(6) . ?
C9 H9 1 . ?
C13 C18 1.545(7) . ?
C13 C14 1.551(7) . ?
C13 C17 1.560(6) . ?
C10 C19 1.536(7) . ?
O2 C22 1.422(6) . ?
O2 C16 1.438(6) . ?
C17 C16 1.562(7) . ?
C17 H17 1 . ?
C29 C28 1.194(7) . ?
C29 C1A 1.435(8) . ?
C16 C15 1.523(8) . ?
C16 H16 1 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C18 H18A 0.98 . ?
C14 C8 1.508(7) . ?
C14 C15 1.531(7) . ?
C14 H14 1 . ?
C6A C5A 1.378(7) . ?
C6A C1A 1.390(7) . ?
C6A H6A 0.95 . ?
C3 C28 1.481(7) . ?
C3 C2 1.536(7) . ?
C11 H11B 0.99 . ?
C11 H11A 0.99 . ?
C1A C2A 1.417(9) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C2A C3A 1.376(7) . ?
C2A H2A 0.95 . ?
C8 H8 1 . ?
C2 H2C 0.99 . ?
C2 H2B 0.99 . ?
C6 H6C 0.99 . ?
C6 H6B 0.99 . ?
C22 O3 1.423(7) . ?
C22 C23 1.521(7) . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C19 H19A 0.98 . ?
C3A C4A 1.387(8) . ?
C3A H3A 0.95 . ?
O3 C26 1.445(7) . ?
C27 C25 1.517(10) . ?
C27 H27C 0.98 . ?
C27 H27B 0.98 . ?
C27 H27A 0.98 . ?
C4A C5A 1.382(8) . ?
C4A I1 2.102(5) . ?
C26 C25 1.510(8) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C5A H5A 0.95 . ?
C23 C24 1.527(7) . ?
C23 H23B 0.99 . ?
C23 H23A 0.99 . ?
C24 C25 1.533(9) . ?
C24 H24B 0.99 . ?
C24 H24A 0.99 . ?
C25 H25 1 . ?
C21 H21A 0.98 . ?
C21 H21C 0.98 . ?
C21 H21B 0.98 . ?

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
C3 O1 H1 116(8) . . ?
C6 C7 C8 111.4(4) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
C6 C5 C4 110.1(4) . . ?
C6 C5 C10 112.4(4) . . ?
C4 C5 C10 112.2(5) . . ?
C6 C5 H5 107.3 . . ?
C4 C5 H5 107.3 . . ?
C10 C5 H5 107.3 . . ?
C13 C12 C11 111.1(5) . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
H12B C12 H12A 108 . . ?
C2 C1 C10 114.8(4) . . ?
C2 C1 H1B 108.6 . . ?
C10 C1 H1B 108.6 . . ?
C2 C1 H1A 108.6 . . ?
C10 C1 H1A 108.6 . . ?
H1B C1 H1A 107.5 . . ?
C3 C4 C5 113.9(4) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C21 C20 C22 115.4(5) . . ?
C21 C20 C17 114.4(4) . . ?
C22 C20 C17 103.5(4) . . ?
C21 C20 H21 107.7 . . ?
C22 C20 H21 107.7 . . ?
C17 C20 H21 107.7 . . ?
C11 C9 C8 111.4(4) . . ?
C11 C9 C10 114.1(4) . . ?
C8 C9 C10 112.0(4) . . ?
C11 C9 H9 106.2 . . ?
C8 C9 H9 106.2 . . ?
C10 C9 H9 106.2 . . ?
C12 C13 C18 110.1(4) . . ?
C12 C13 C14 107.0(4) . . ?
C18 C13 C14 111.6(4) . . ?
C12 C13 C17 115.7(4) . . ?
C18 C13 C17 111.5(4) . . ?
C14 C13 C17 100.6(4) . . ?
C1 C10 C19 106.2(4) . . ?
C1 C10 C9 113.1(4) . . ?
C19 C10 C9 111.3(4) . . ?
C1 C10 C5 107.2(4) . . ?
C19 C10 C5 109.9(5) . . ?
C9 C10 C5 109.0(4) . . ?
C22 O2 C16 106.6(4) . . ?
C20 C17 C13 120.3(4) . . ?
C20 C17 C16 103.8(4) . . ?
C13 C17 C16 104.4(4) . . ?
C20 C17 H17 109.2 . . ?
C13 C17 H17 109.2 . . ?
C16 C17 H17 109.2 . . ?
C28 C29 C1A 174.0(6) . . ?
O2 C16 C15 111.1(5) . . ?
O2 C16 C17 105.4(4) . . ?
C15 C16 C17 107.9(4) . . ?
O2 C16 H16 110.7 . . ?
C15 C16 H16 110.7 . . ?
C17 C16 H16 110.7 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
C8 C14 C15 119.6(4) . . ?
C8 C14 C13 114.7(4) . . ?
C15 C14 C13 103.9(4) . . ?
C8 C14 H14 105.8 . . ?
C15 C14 H14 105.8 . . ?
C13 C14 H14 105.8 . . ?
C5A C6A C1A 122.2(6) . . ?
C5A C6A H6A 118.9 . . ?
C1A C6A H6A 118.9 . . ?
O1 C3 C28 107.3(4) . . ?
O1 C3 C4 110.6(4) . . ?
C28 C3 C4 109.3(4) . . ?
O1 C3 C2 107.6(4) . . ?
C28 C3 C2 112.1(4) . . ?
C4 C3 C2 109.9(4) . . ?
C9 C11 C12 113.7(4) . . ?
C9 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
H11B C11 H11A 107.7 . . ?
C6A C1A C2A 117.7(5) . . ?
C6A C1A C29 123.4(6) . . ?
C2A C1A C29 118.8(5) . . ?
C16 C15 C14 102.5(4) . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15B 111.3 . . ?
C14 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C29 C28 C3 174.4(5) . . ?
C3A C2A C1A 120.4(5) . . ?
C3A C2A H2A 119.8 . . ?
C1A C2A H2A 119.8 . . ?
C14 C8 C7 111.8(4) . . ?
C14 C8 C9 108.8(4) . . ?
C7 C8 C9 112.0(4) . . ?
C14 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C1 C2 C3 111.5(4) . . ?
C1 C2 H2C 109.3 . . ?
C3 C2 H2C 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2C C2 H2B 108 . . ?
C5 C6 C7 112.2(5) . . ?
C5 C6 H6C 109.2 . . ?
C7 C6 H6C 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6C C6 H6B 107.9 . . ?
O2 C22 O3 110.3(4) . . ?
O2 C22 C23 107.4(4) . . ?
O3 C22 C23 111.1(4) . . ?
O2 C22 C20 105.2(4) . . ?
O3 C22 C20 107.5(5) . . ?
C23 C22 C20 115.1(4) . . ?
C10 C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
C2A C3A C4A 119.9(5) . . ?
C2A C3A H3A 120 . . ?
C4A C3A H3A 120 . . ?
C22 O3 C26 113.9(5) . . ?
C25 C27 H27C 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27C C27 H27B 109.5 . . ?
C25 C27 H27A 109.5 . . ?
H27C C27 H27A 109.5 . . ?
H27B C27 H27A 109.5 . . ?
C5A C4A C3A 120.9(5) . . ?
C5A C4A I1 119.2(4) . . ?
C3A C4A I1 119.9(4) . . ?
O3 C26 C25 111.7(4) . . ?
O3 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
O3 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
C6A C5A C4A 118.9(5) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C22 C23 C24 112.2(4) . . ?
C22 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
H23B C23 H23A 107.9 . . ?
C23 C24 C25 110.4(5) . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
H24B C24 H24A 108.1 . . ?
C26 C25 C27 112.0(6) . . ?
C26 C25 C24 108.1(5) . . ?
C27 C25 C24 111.9(5) . . ?
C26 C25 H25 108.2 . . ?
C27 C25 H25 108.2 . . ?
C24 C25 H25 108.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21C C21 H21B 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
C6 C5 C4 C3 178.8(4) . . . . ?
C10 C5 C4 C3 -55.3(5) . . . . ?
C11 C12 C13 C18 -65.8(5) . . . . ?
C11 C12 C13 C14 55.6(5) . . . . ?
C11 C12 C13 C17 166.8(4) . . . . ?
C2 C1 C10 C19 -173.1(4) . . . . ?
C2 C1 C10 C9 64.6(6) . . . . ?
C2 C1 C10 C5 -55.6(6) . . . . ?
C11 C9 C10 C1 58.6(6) . . . . ?
C8 C9 C10 C1 -173.6(4) . . . . ?
C11 C9 C10 C19 -60.9(5) . . . . ?
C8 C9 C10 C19 66.9(5) . . . . ?
C11 C9 C10 C5 177.7(4) . . . . ?
C8 C9 C10 C5 -54.5(5) . . . . ?
C6 C5 C10 C1 178.0(5) . . . . ?
C4 C5 C10 C1 53.3(5) . . . . ?
C6 C5 C10 C19 -66.9(6) . . . . ?
C4 C5 C10 C19 168.4(4) . . . . ?
C6 C5 C10 C9 55.3(6) . . . . ?
C4 C5 C10 C9 -69.4(5) . . . . ?
C21 C20 C17 C13 -109.4(5) . . . . ?
C22 C20 C17 C13 124.2(5) . . . . ?
C21 C20 C17 C16 134.5(5) . . . . ?
C22 C20 C17 C16 8.1(5) . . . . ?
C12 C13 C17 C20 97.9(5) . . . . ?
C18 C13 C17 C20 -28.9(6) . . . . ?
C14 C13 C17 C20 -147.3(4) . . . . ?
C12 C13 C17 C16 -146.3(4) . . . . ?
C18 C13 C17 C16 86.9(5) . . . . ?
C14 C13 C17 C16 -31.5(5) . . . . ?
C22 O2 C16 C15 -151.9(4) . . . . ?
C22 O2 C16 C17 -35.2(5) . . . . ?
C20 C17 C16 O2 15.3(5) . . . . ?
C13 C17 C16 O2 -111.5(4) . . . . ?
C20 C17 C16 C15 134.2(4) . . . . ?
C13 C17 C16 C15 7.3(5) . . . . ?
C12 C13 C14 C8 -61.0(6) . . . . ?
C18 C13 C14 C8 59.4(6) . . . . ?
C17 C13 C14 C8 177.8(4) . . . . ?
C12 C13 C14 C15 166.5(4) . . . . ?
C18 C13 C14 C15 -73.0(5) . . . . ?
C17 C13 C14 C15 45.3(5) . . . . ?
C5 C4 C3 O1 171.8(4) . . . . ?
C5 C4 C3 C28 -70.3(6) . . . . ?
C5 C4 C3 C2 53.1(6) . . . . ?
C8 C9 C11 C12 51.6(6) . . . . ?
C10 C9 C11 C12 179.7(5) . . . . ?
C13 C12 C11 C9 -54.5(6) . . . . ?
C5A C6A C1A C2A -2.3(7) . . . . ?
C5A C6A C1A C29 174.3(5) . . . . ?
O2 C16 C15 C14 135.5(4) . . . . ?
C17 C16 C15 C14 20.4(5) . . . . ?
C8 C14 C15 C16 -170.5(4) . . . . ?
C13 C14 C15 C16 -41.0(5) . . . . ?
C6A C1A C2A C3A 1.8(7) . . . . ?
C29 C1A C2A C3A -174.9(5) . . . . ?
C15 C14 C8 C7 -52.3(7) . . . . ?
C13 C14 C8 C7 -176.9(5) . . . . ?
C15 C14 C8 C9 -176.5(4) . . . . ?
C13 C14 C8 C9 59.0(5) . . . . ?
C6 C7 C8 C14 -175.7(5) . . . . ?
C6 C7 C8 C9 -53.4(7) . . . . ?
C11 C9 C8 C14 -51.9(5) . . . . ?
C10 C9 C8 C14 178.9(4) . . . . ?
C11 C9 C8 C7 -175.9(5) . . . . ?
C10 C9 C8 C7 54.9(6) . . . . ?
C10 C1 C2 C3 56.9(6) . . . . ?
O1 C3 C2 C1 -172.9(4) . . . . ?
C28 C3 C2 C1 69.3(5) . . . . ?
C4 C3 C2 C1 -52.4(5) . . . . ?
C4 C5 C6 C7 69.9(6) . . . . ?
C10 C5 C6 C7 -55.9(6) . . . . ?
C8 C7 C6 C5 54.1(7) . . . . ?
C16 O2 C22 O3 -74.6(5) . . . . ?
C16 O2 C22 C23 164.1(4) . . . . ?
C16 O2 C22 C20 41.0(5) . . . . ?
C21 C20 C22 O2 -155.1(4) . . . . ?
C17 C20 C22 O2 -29.3(5) . . . . ?
C21 C20 C22 O3 -37.6(6) . . . . ?
C17 C20 C22 O3 88.2(5) . . . . ?
C21 C20 C22 C23 86.8(6) . . . . ?
C17 C20 C22 C23 -147.4(4) . . . . ?
C1A C2A C3A C4A -0.2(8) . . . . ?
O2 C22 O3 C26 -63.9(5) . . . . ?
C23 C22 O3 C26 55.1(6) . . . . ?
C20 C22 O3 C26 -178.1(4) . . . . ?
C2A C3A C4A C5A -1.0(8) . . . . ?
C2A C3A C4A I1 178.1(4) . . . . ?
C22 O3 C26 C25 -60.3(6) . . . . ?
C1A C6A C5A C4A 1.1(8) . . . . ?
C3A C4A C5A C6A 0.6(8) . . . . ?
I1 C4A C5A C6A -178.5(4) . . . . ?
O2 C22 C23 C24 69.6(6) . . . . ?
O3 C22 C23 C24 -51.2(6) . . . . ?
C20 C22 C23 C24 -173.7(5) . . . . ?
C22 C23 C24 C25 52.1(6) . . . . ?
O3 C26 C25 C27 -65.7(6) . . . . ?
O3 C26 C25 C24 58.2(7) . . . . ?
C23 C24 C25 C26 -54.5(6) . . . . ?
C23 C24 C25 C27 69.4(6) . . . . ?

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
C26 H26A O2 0.99 2.5 3.363(7) 146 4_546

# END of CIF
####################################################################### 
# 
# 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_san681
_database_code_depnum_ccdc_archive 'CCDC 1463832'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T14:51:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C26 H29 I1 O2'
_chemical_formula_sum            'C26 H29 I O2'
_chemical_formula_weight         500.39
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.30450(10)
_cell_length_b                   16.0693(4)
_cell_length_c                   22.1170(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2240.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14436
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.809
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.857

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.026394
_diffrn_orient_matrix_ub_12      -0.020295
_diffrn_orient_matrix_ub_13      -0.042075
_diffrn_orient_matrix_ub_21      0.044268
_diffrn_orient_matrix_ub_22      0.057296
_diffrn_orient_matrix_ub_23      -0.012333
_diffrn_orient_matrix_ub_31      0.15001
_diffrn_orient_matrix_ub_32      -0.013338
_diffrn_orient_matrix_ub_33      0.011042
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_number            16477
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_coverage         0.744
_reflns_number_total             5110
_reflns_number_gt                4388
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0277P)²+1.5393P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5110
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1626 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.043(13)
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C9 C 0.0268(7) 0.4940(3) 0.3052(2) 0.0363(10) Uani 1 1 d . . . . .
H9 H 0.1539 0.527 0.3139 0.044 Uiso 1 1 calc R U . . .
C10 C -0.0205(9) 0.5027(4) 0.2360(2) 0.0509(13) Uani 1 1 d . . . . .
H10 H -0.136 0.464 0.2265 0.061 Uiso 1 1 calc R U . . .
C5 C 0.1732(10) 0.4723(4) 0.2032(2) 0.0511(14) Uani 1 1 d . . . . .
C6 C 0.2237(13) 0.3822(4) 0.2135(2) 0.0642(17) Uani 1 1 d . . . . .
H6C H 0.3489 0.3665 0.1907 0.077 Uiso 1 1 calc R U . . .
H6B H 0.1062 0.3477 0.2003 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2632(9) 0.3699(3) 0.2818(2) 0.0456(12) Uani 1 1 d . . . . .
H7B H 0.2829 0.3111 0.29 0.055 Uiso 1 1 calc R U . . .
H7A H 0.3926 0.3986 0.2932 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0790(8) 0.4028(3) 0.32036(18) 0.0344(9) Uani 1 1 d . . . . .
H8 H -0.0468 0.3688 0.3122 0.041 Uiso 1 1 calc R U . . .
C14 C 0.1301(6) 0.3970(2) 0.38769(18) 0.0276(8) Uani 1 1 d . . . . .
H14 H 0.2489 0.435 0.395 0.033 Uiso 1 1 calc R U . . .
C13 C -0.0553(6) 0.4272(3) 0.42814(19) 0.0304(9) Uani 1 1 d . . . . .
C12 C -0.1058(9) 0.5172(3) 0.4130(2) 0.0378(10) Uani 1 1 d . . . . .
H12A H 0.0133 0.5522 0.4243 0.045 Uiso 1 1 calc R U . . .
H12B H -0.2284 0.5351 0.4361 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1514(8) 0.5275(3) 0.3450(2) 0.0427(12) Uani 1 1 d . . . . .
H11B H -0.2819 0.4985 0.3352 0.051 Uiso 1 1 calc R U . . .
H11A H -0.1723 0.586 0.3362 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1934(7) 0.3131(3) 0.41478(19) 0.0360(9) Uani 1 1 d . . . . .
H15A H 0.3389 0.2992 0.4047 0.043 Uiso 1 1 calc R U . . .
H15B H 0.1009 0.269 0.4005 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1676(7) 0.3266(3) 0.4832(2) 0.0351(10) Uani 1 1 d . . . . .
H16B H 0.3055 0.3293 0.5026 0.042 Uiso 1 1 calc R U . . .
H16A H 0.0882 0.281 0.501 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0457(6) 0.4104(3) 0.4921(2) 0.0315(9) Uani 1 1 d . . . . .
C20 C 0.1906(8) 0.4779(3) 0.5097(2) 0.0364(10) Uani 1 1 d . . . . .
C21 C 0.3057(8) 0.5325(3) 0.5260(2) 0.0400(11) Uani 1 1 d . . . . .
C18 C -0.2532(8) 0.3723(3) 0.4213(2) 0.0439(12) Uani 1 1 d . . . . .
H18B H -0.3622 0.3918 0.448 0.066 Uiso 1 1 calc R U . . .
H18C H -0.2181 0.3158 0.4312 0.066 Uiso 1 1 calc R U . . .
H18A H -0.3029 0.375 0.3803 0.066 Uiso 1 1 calc R U . . .
C1A C 0.4435(8) 0.5979(3) 0.54780(19) 0.0353(10) Uani 1 1 d . . . . .
C2A C 0.3753(7) 0.6793(3) 0.5512(2) 0.0421(11) Uani 1 1 d . . . . .
H2A H 0.239 0.6927 0.5384 0.05 Uiso 1 1 calc R U . . .
C6A C 0.6509(8) 0.5791(3) 0.5654(2) 0.0424(11) Uani 1 1 d . . . . .
H6A H 0.7007 0.5247 0.5624 0.051 Uiso 1 1 calc R U . . .
C5A C 0.7817(8) 0.6405(3) 0.5873(2) 0.0453(12) Uani 1 1 d . . . . .
H5A H 0.9193 0.6277 0.5992 0.054 Uiso 1 1 calc R U . . .
C4A C 0.7085(7) 0.7211(3) 0.5915(2) 0.0375(11) Uani 1 1 d . . . . .
C3A C 0.5055(8) 0.7409(3) 0.5731(3) 0.0453(12) Uani 1 1 d . . . . .
H3A H 0.4572 0.7955 0.5755 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3021(10) 0.5231(4) 0.1718(2) 0.0529(14) Uani 1 1 d . . . . .
H4 H 0.4167 0.5001 0.1513 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2701(11) 0.6124(4) 0.1685(2) 0.0564(15) Uani 1 1 d . . . . .
C2 C 0.0939(13) 0.6472(4) 0.2073(3) 0.0710(18) Uani 1 1 d . . . . .
H2C H 0.1494 0.6596 0.2472 0.085 Uiso 1 1 calc R U . . .
H2B H 0.0443 0.699 0.1896 0.085 Uiso 1 1 calc R U . . .
C1 C -0.0884(12) 0.5889(5) 0.2133(3) 0.0701(18) Uani 1 1 d . . . . .
H1A H -0.1572 0.583 0.1743 0.084 Uiso 1 1 calc R U . . .
H1B H -0.1909 0.6123 0.2412 0.084 Uiso 1 1 calc R U . . .
O2 O -0.1176(6) 0.4030(2) 0.53684(15) 0.0417(8) Uani 1 1 d D . . . .
O1 O 0.3877(9) 0.6571(3) 0.13937(19) 0.0762(13) Uani 1 1 d . . . . .
I1 I 0.91095(6) 0.81398(2) 0.62534(2) 0.05872(14) Uani 1 1 d . . . . .
H2 H -0.075(7) 0.387(3) 0.5688(14) 0.027(12) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C9 C11 1.525(7) . ?
C9 C8 1.540(6) . ?
C9 C10 1.567(7) . ?
C9 H9 0.98 . ?
C10 C5 1.502(8) . ?
C10 C1 1.535(9) . ?
C10 H10 0.98 . ?
C5 C4 1.345(8) . ?
C5 C6 1.499(8) . ?
C6 C7 1.544(8) . ?
C6 H6C 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.535(7) . ?
C7 H7B 0.97 . ?
C7 H7A 0.97 . ?
C8 C14 1.526(6) . ?
C8 H8 0.98 . ?
C14 C15 1.529(6) . ?
C14 C13 1.550(6) . ?
C14 H14 0.98 . ?
C13 C12 1.519(6) . ?
C13 C18 1.535(6) . ?
C13 C17 1.574(6) . ?
C12 C11 1.540(7) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C11 H11B 0.97 . ?
C11 H11A 0.97 . ?
C15 C16 1.538(6) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.563(6) . ?
C16 H16B 0.97 . ?
C16 H16A 0.97 . ?
C17 O2 1.433(5) . ?
C17 C20 1.472(6) . ?
C20 C21 1.193(7) . ?
C21 C1A 1.447(7) . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C18 H18A 0.96 . ?
C1A C2A 1.379(7) . ?
C1A C6A 1.398(7) . ?
C2A C3A 1.374(7) . ?
C2A H2A 0.93 . ?
C6A C5A 1.374(7) . ?
C6A H6A 0.93 . ?
C5A C4A 1.378(7) . ?
C5A H5A 0.93 . ?
C4A C3A 1.380(7) . ?
C4A I1 2.102(5) . ?
C3A H3A 0.93 . ?
C4 C3 1.451(8) . ?
C4 H4 0.93 . ?
C3 O1 1.217(7) . ?
C3 C2 1.510(9) . ?
C2 C1 1.489(10) . ?
C2 H2C 0.97 . ?
C2 H2B 0.97 . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
O2 H2 0.80(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
C11 C9 C8 111.6(4) . . ?
C11 C9 C10 113.1(4) . . ?
C8 C9 C10 109.8(4) . . ?
C11 C9 H9 107.4 . . ?
C8 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C5 C10 C1 111.3(5) . . ?
C5 C10 C9 106.8(4) . . ?
C1 C10 C9 116.9(5) . . ?
C5 C10 H10 107.1 . . ?
C1 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
C4 C5 C6 122.5(6) . . ?
C4 C5 C10 122.8(6) . . ?
C6 C5 C10 114.4(5) . . ?
C5 C6 C7 107.9(4) . . ?
C5 C6 H6C 110.1 . . ?
C7 C6 H6C 110.1 . . ?
C5 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6C C6 H6B 108.4 . . ?
C8 C7 C6 112.2(5) . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
H7B C7 H7A 107.9 . . ?
C14 C8 C7 111.2(4) . . ?
C14 C8 C9 108.4(3) . . ?
C7 C8 C9 111.6(4) . . ?
C14 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C8 C14 C15 119.4(3) . . ?
C8 C14 C13 112.6(3) . . ?
C15 C14 C13 104.3(3) . . ?
C8 C14 H14 106.6 . . ?
C15 C14 H14 106.6 . . ?
C13 C14 H14 106.6 . . ?
C12 C13 C18 110.8(4) . . ?
C12 C13 C14 109.2(3) . . ?
C18 C13 C14 112.1(4) . . ?
C12 C13 C17 116.5(4) . . ?
C18 C13 C17 108.6(3) . . ?
C14 C13 C17 99.2(3) . . ?
C13 C12 C11 110.9(4) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108 . . ?
C9 C11 C12 112.8(4) . . ?
C9 C11 H11B 109 . . ?
C12 C11 H11B 109 . . ?
C9 C11 H11A 109 . . ?
C12 C11 H11A 109 . . ?
H11B C11 H11A 107.8 . . ?
C14 C15 C16 103.5(3) . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109 . . ?
C15 C16 C17 107.2(3) . . ?
C15 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
C15 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
H16B C16 H16A 108.5 . . ?
O2 C17 C20 108.9(4) . . ?
O2 C17 C16 111.6(3) . . ?
C20 C17 C16 111.3(4) . . ?
O2 C17 C13 110.1(3) . . ?
C20 C17 C13 111.3(3) . . ?
C16 C17 C13 103.5(3) . . ?
C21 C20 C17 177.8(5) . . ?
C20 C21 C1A 178.0(5) . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
C2A C1A C6A 118.8(4) . . ?
C2A C1A C21 121.3(4) . . ?
C6A C1A C21 119.9(4) . . ?
C3A C2A C1A 121.1(5) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C5A C6A C1A 120.3(5) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C6A C5A C4A 119.9(4) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
C5A C4A C3A 120.5(4) . . ?
C5A C4A I1 119.2(3) . . ?
C3A C4A I1 120.3(4) . . ?
C2A C3A C4A 119.4(5) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5 C4 C3 122.9(6) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
O1 C3 C4 121.6(6) . . ?
O1 C3 C2 122.1(6) . . ?
C4 C3 C2 116.1(5) . . ?
C1 C2 C3 112.6(6) . . ?
C1 C2 H2C 109.1 . . ?
C3 C2 H2C 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2C C2 H2B 107.8 . . ?
C2 C1 C10 112.5(5) . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C17 O2 H2 113(4) . . ?

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
C11 C9 C10 C5 176.6(5) . . . . ?
C8 C9 C10 C5 -58.1(6) . . . . ?
C11 C9 C10 C1 51.3(7) . . . . ?
C8 C9 C10 C1 176.6(5) . . . . ?
C1 C10 C5 C4 17.8(7) . . . . ?
C9 C10 C5 C4 -110.9(6) . . . . ?
C1 C10 C5 C6 -168.2(5) . . . . ?
C9 C10 C5 C6 63.1(6) . . . . ?
C4 C5 C6 C7 113.5(6) . . . . ?
C10 C5 C6 C7 -60.5(7) . . . . ?
C5 C6 C7 C8 53.5(7) . . . . ?
C6 C7 C8 C14 -174.9(4) . . . . ?
C6 C7 C8 C9 -53.8(6) . . . . ?
C11 C9 C8 C14 -55.3(5) . . . . ?
C10 C9 C8 C14 178.4(4) . . . . ?
C11 C9 C8 C7 -178.1(4) . . . . ?
C10 C9 C8 C7 55.7(5) . . . . ?
C7 C8 C14 C15 -55.4(5) . . . . ?
C9 C8 C14 C15 -178.5(4) . . . . ?
C7 C8 C14 C13 -178.2(4) . . . . ?
C9 C8 C14 C13 58.7(5) . . . . ?
C8 C14 C13 C12 -59.4(5) . . . . ?
C15 C14 C13 C12 169.7(4) . . . . ?
C8 C14 C13 C18 63.7(5) . . . . ?
C15 C14 C13 C18 -67.2(4) . . . . ?
C8 C14 C13 C17 178.3(3) . . . . ?
C15 C14 C13 C17 47.4(4) . . . . ?
C18 C13 C12 C11 -69.0(5) . . . . ?
C14 C13 C12 C11 55.0(5) . . . . ?
C17 C13 C12 C11 166.2(4) . . . . ?
C8 C9 C11 C12 54.5(6) . . . . ?
C10 C9 C11 C12 178.9(4) . . . . ?
C13 C12 C11 C9 -54.4(6) . . . . ?
C8 C14 C15 C16 -164.1(4) . . . . ?
C13 C14 C15 C16 -37.3(4) . . . . ?
C14 C15 C16 C17 11.8(4) . . . . ?
C15 C16 C17 O2 135.7(4) . . . . ?
C15 C16 C17 C20 -102.4(4) . . . . ?
C15 C16 C17 C13 17.2(4) . . . . ?
C12 C13 C17 O2 85.1(5) . . . . ?
C18 C13 C17 O2 -40.8(5) . . . . ?
C14 C13 C17 O2 -158.0(3) . . . . ?
C12 C13 C17 C20 -35.8(5) . . . . ?
C18 C13 C17 C20 -161.7(4) . . . . ?
C14 C13 C17 C20 81.1(4) . . . . ?
C12 C13 C17 C16 -155.5(4) . . . . ?
C18 C13 C17 C16 78.6(4) . . . . ?
C14 C13 C17 C16 -38.6(4) . . . . ?
C6A C1A C2A C3A -1.9(7) . . . . ?
C21 C1A C2A C3A 178.7(5) . . . . ?
C2A C1A C6A C5A 1.8(7) . . . . ?
C21 C1A C6A C5A -178.8(5) . . . . ?
C1A C6A C5A C4A -0.4(8) . . . . ?
C6A C5A C4A C3A -0.9(8) . . . . ?
C6A C5A C4A I1 179.8(4) . . . . ?
C1A C2A C3A C4A 0.7(8) . . . . ?
C5A C4A C3A C2A 0.8(8) . . . . ?
I1 C4A C3A C2A -179.9(4) . . . . ?
C6 C5 C4 C3 -171.3(6) . . . . ?
C10 C5 C4 C3 2.2(8) . . . . ?
C5 C4 C3 O1 -179.2(6) . . . . ?
C5 C4 C3 C2 5.5(9) . . . . ?
O1 C3 C2 C1 151.0(6) . . . . ?
C4 C3 C2 C1 -33.7(8) . . . . ?
C3 C2 C1 C10 54.0(7) . . . . ?
C5 C10 C1 C2 -45.4(7) . . . . ?
C9 C10 C1 C2 77.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2C I1 0.97 3.29 4.253(7) 170.3 3_466
O2 H2 O1 0.80(2) 2.08(3) 2.859(6) 165(5) 2_565
C2 H2C I1 0.97 3.29 4.253(7) 170.3 3_466
O2 H2 O1 0.80(2) 2.08(3) 2.859(6) 165(5) 2_565

# END of CIF
####################################################################### 
# 
# 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_rsyl03
_database_code_depnum_ccdc_archive 'CCDC 1463833'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-17T16:19:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C28  H35  O2  Br1'
_chemical_formula_sum            'C28 H28 Br O2'
_chemical_formula_weight         476.41
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.7512(16)
_cell_length_b                   14.839(3)
_cell_length_c                   20.627(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2372.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      1
_cell_measurement_theta_max      14
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_T_max  0.664
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.743

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_diffrn_measurement_method       CCD

# Orientation matrix from 'scale_all.out'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0807462
_diffrn_orient_matrix_UB_21      0.0051075
_diffrn_orient_matrix_UB_31      0.1004895
_diffrn_orient_matrix_UB_12      0.0492961
_diffrn_orient_matrix_UB_22      0.0213355
_diffrn_orient_matrix_UB_32      -0.0406952
_diffrn_orient_matrix_UB_13      -0.0131144
_diffrn_orient_matrix_UB_23      0.0459465
_diffrn_orient_matrix_UB_33      0.0082025
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.1344
_diffrn_reflns_number            16831
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.041
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.949
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_coverage         0.715
_reflns_number_total             5160
_reflns_number_gt                2730
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1864P)²+4.4160P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.060(12)
_refine_ls_number_reflns         5160
_refine_ls_number_parameters     326
_refine_ls_number_restraints     127
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2076
_refine_ls_R_factor_gt           0.124
_refine_ls_wR_factor_ref         0.3645
_refine_ls_wR_factor_gt          0.3187
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.064(15)
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.109

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C20A C -0.085(6) 0.474(2) 0.579(2) 0.055(3) Uani 0.5 1 d D U P A 1
C21A C -0.065(5) 0.525(2) 0.5354(17) 0.055(3) Uani 0.5 1 d D U P A 1
C1A C -0.064(3) 0.5933(13) 0.4834(9) 0.069(5) Uani 0.5 1 d G U P A 1
C2A C -0.211(2) 0.6374(15) 0.4621(10) 0.079(6) Uani 0.5 1 d G U P A 1
H2A H -0.3186 0.6272 0.4833 0.095 Uiso 0.5 1 calc R U P A 1
C3A C -0.202(3) 0.6964(14) 0.4099(10) 0.086(6) Uani 0.5 1 d G U P A 1
H3A H -0.3034 0.7265 0.3953 0.104 Uiso 0.5 1 calc R U P A 1
C4A C -0.046(3) 0.7113(15) 0.3789(9) 0.085(6) Uani 0.5 1 d G U P A 1
C5A C 0.102(3) 0.6672(16) 0.4002(11) 0.089(6) Uani 0.5 1 d G U P A 1
H5A H 0.2091 0.6774 0.3791 0.107 Uiso 0.5 1 calc R U P A 1
C6A C 0.093(2) 0.6082(15) 0.4525(11) 0.080(6) Uani 0.5 1 d G U P A 1
H6A H 0.194 0.5781 0.467 0.096 Uiso 0.5 1 calc R U P A 1
Br1A Br 0.0449(11) 0.7918(9) 0.3098(5) 0.150(5) Uani 0.5 1 d . . P A 1
C20B C -0.059(6) 0.492(2) 0.580(2) 0.055(3) Uani 0.5 1 d D U P A 2
C21B C -0.039(5) 0.549(2) 0.5400(17) 0.055(3) Uani 0.5 1 d D U P A 2
C1B C -0.016(2) 0.6140(7) 0.4884(5) 0.056(4) Uani 0.5 1 d G U P A 2
C2B C -0.006(2) 0.5805(7) 0.4256(6) 0.063(5) Uani 0.5 1 d G U P A 2
H2B H -0.0014 0.5174 0.4184 0.076 Uiso 0.5 1 calc R U P A 2
C3B C -0.004(3) 0.6396(9) 0.3733(5) 0.063(5) Uani 0.5 1 d G U P A 2
H3B H 0.0021 0.6167 0.3303 0.075 Uiso 0.5 1 calc R U P A 2
C4B C -0.011(3) 0.7320(8) 0.3838(4) 0.065(5) Uani 0.5 1 d G U P A 2
C5B C -0.0208(19) 0.7654(7) 0.4466(5) 0.077(5) Uani 0.5 1 d G U P A 2
C6B C -0.0229(18) 0.7064(7) 0.4990(4) 0.070(4) Uani 0.5 1 d G U P A 2
C7B C -0.032(3) 0.7398(10) 0.5618(4) 0.079(5) Uani 0.5 1 d G U P A 2
H7B H -0.0336 0.6995 0.5976 0.095 Uiso 0.5 1 calc R U P A 2
C8B C -0.039(3) 0.8323(10) 0.5723(6) 0.088(6) Uani 0.5 1 d G U P A 2
H8B H -0.0457 0.8551 0.6153 0.105 Uiso 0.5 1 calc R U P A 2
C9B C -0.037(3) 0.8913(8) 0.5200(7) 0.091(6) Uani 0.5 1 d G U P A 2
H9B H -0.0422 0.9545 0.5272 0.11 Uiso 0.5 1 calc R U P A 2
C10B C -0.028(3) 0.8579(7) 0.4572(7) 0.087(6) Uani 0.5 1 d G U P A 2
H10B H -0.0265 0.8982 0.4214 0.105 Uiso 0.5 1 calc R U P A 2
Br1B Br -0.0387(10) 0.8027(4) 0.3101(3) 0.094(2) Uani 0.5 1 d . . P A 2
C5 C -0.0429(13) 0.6164(7) 0.9070(5) 0.041(3) Uani 1 1 d . . . . .
C14 C -0.1552(13) 0.4930(9) 0.7196(5) 0.046(3) Uani 1 1 d . . . . .
H14 H -0.1512 0.5485 0.6921 0.055 Uiso 1 1 calc R U . . .
C16 C -0.2924(16) 0.3942(11) 0.6400(7) 0.069(4) Uani 1 1 d . . . . .
H16A H -0.3631 0.4196 0.6045 0.082 Uiso 1 1 calc R U . . .
H16B H -0.3201 0.3294 0.6448 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2933(18) 0.6436(8) 0.9472(6) 0.056(3) Uani 1 1 d . . . . .
H2 H 0.4093 0.6551 0.9596 0.067 Uiso 1 1 calc R U . . .
C6 C -0.2338(15) 0.6039(11) 0.8864(7) 0.062(4) Uani 1 1 d . . . . .
H6C H -0.2835 0.5532 0.9114 0.075 Uiso 1 1 calc R U . . .
HCD H -0.2987 0.659 0.8982 0.075 Uiso 1 1 calc R U . . .
C4 C -0.0071(14) 0.6414(7) 0.9689(5) 0.044(2) Uani 1 1 d . . . . .
H4 H -0.1005 0.652 0.9978 0.052 Uiso 1 1 calc R U . . .
C11 C 0.2001(16) 0.5102(10) 0.7647(6) 0.053(3) Uani 1 1 d . . . . .
H11A H 0.2207 0.4577 0.7932 0.064 Uiso 1 1 calc R U . . .
H11B H 0.3077 0.546 0.7628 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0176(13) 0.4289(8) 0.6930(5) 0.045(3) Uani 1 1 d . . . . .
C10 C 0.0921(14) 0.6005(8) 0.8617(5) 0.044(3) Uani 1 1 d . . . . .
C9 C 0.0540(13) 0.5684(8) 0.7931(5) 0.042(3) Uani 1 1 d . . . . .
H9 H 0.0464 0.6236 0.7654 0.051 Uiso 1 1 calc R U . . .
C1 C 0.2557(15) 0.6185(9) 0.8849(6) 0.052(3) Uani 1 1 d . . . . .
H1 H 0.3492 0.613 0.8554 0.062 Uiso 1 1 calc R U . . .
C7 C -0.2596(14) 0.5856(10) 0.8155(7) 0.058(4) Uani 1 1 d . . . . .
H7A H -0.2573 0.6432 0.7913 0.07 Uiso 1 1 calc R U . . .
H7C H -0.374 0.5575 0.8087 0.07 Uiso 1 1 calc R U . . .
C15 C -0.3258(17) 0.4449(10) 0.7037(6) 0.060(3) Uani 1 1 d . . . . .
H15A H -0.3574 0.4024 0.7387 0.072 Uiso 1 1 calc R U . . .
H15B H -0.4204 0.4891 0.6983 0.072 Uiso 1 1 calc R U . . .
C8 C -0.1186(11) 0.5231(7) 0.7895(5) 0.033(2) Uani 1 1 d . . . . .
H8 H -0.115 0.4682 0.8176 0.04 Uiso 1 1 calc R U . . .
C17 C -0.0961(13) 0.4077(8) 0.6260(6) 0.046(3) Uani 1 1 d . . . . .
C18 C -0.0031(19) 0.3392(9) 0.7296(5) 0.058(3) Uani 1 1 d . . . . .
H18B H -0.1144 0.3079 0.7283 0.087 Uiso 1 1 calc R U . . .
H18C H 0.0854 0.3016 0.7092 0.087 Uiso 1 1 calc R U . . .
H18A H 0.0288 0.3509 0.7748 0.087 Uiso 1 1 calc R U . . .
C12 C 0.1524(15) 0.4767(10) 0.6952(6) 0.056(3) Uani 1 1 d . . . . .
H12B H 0.1485 0.529 0.6654 0.068 Uiso 1 1 calc R U . . .
H12A H 0.2436 0.4353 0.6796 0.068 Uiso 1 1 calc R U . . .
C3 C 0.1615(16) 0.6524(8) 0.9920(5) 0.046(3) Uani 1 1 d . . . . .
O2 O -0.0176(13) 0.3304(6) 0.5950(4) 0.064(2) Uani 1 1 d . . . . .
H002 H 0.0871 0.341 0.5879 0.096 Uiso 1 1 calc R U . . .
O1 O 0.1876(11) 0.6774(7) 1.0542(4) 0.063(3) Uani 1 1 d . . . . .
H1A H 0.1067 0.6578 1.0774 0.094 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C20A C21A 1.18(2) . ?
C20A C17 1.39(4) . ?
C21A C1A 1.48(4) . ?
C1A C2A 1.39 . ?
C1A C6A 1.39 . ?
C2A C3A 1.39 . ?
C3A C4A 1.39 . ?
C4A C5A 1.39 . ?
C4A Br1A 1.989(18) . ?
C5A C6A 1.39 . ?
C20B C21B 1.18(2) . ?
C20B C17 1.60(4) . ?
C21B C1B 1.45(4) . ?
C1B C2B 1.39 . ?
C1B C6B 1.39 . ?
C2B C3B 1.39 . ?
C3B C4B 1.39 . ?
C4B C5B 1.39 . ?
C4B Br1B 1.859(12) . ?
C5B C6B 1.39 . ?
C5B C10B 1.39 . ?
C6B C7B 1.39 . ?
C7B C8B 1.39 . ?
C8B C9B 1.39 . ?
C9B C10B 1.39 . ?
C5 C4 1.360(15) . ?
C5 C10 1.422(15) . ?
C5 C6 1.550(17) . ?
C14 C13 1.530(16) . ?
C14 C8 1.536(14) . ?
C14 C15 1.538(16) . ?
C16 C15 1.536(17) . ?
C16 C17 1.562(16) . ?
C2 C1 1.368(18) . ?
C2 C3 1.383(17) . ?
C6 C7 1.502(19) . ?
C4 C3 1.400(17) . ?
C11 C9 1.540(16) . ?
C11 C12 1.562(16) . ?
C13 C12 1.497(17) . ?
C13 C18 1.534(17) . ?
C13 C17 1.542(16) . ?
C10 C1 1.382(17) . ?
C10 C9 1.523(15) . ?
C9 C8 1.499(14) . ?
C7 C8 1.531(15) . ?
C17 O2 1.448(14) . ?
C3 O1 1.352(13) . ?

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
C21A C20A C17 174(4) . . ?
C20A C21A C1A 172(4) . . ?
C2A C1A C6A 120 . . ?
C2A C1A C21A 123(2) . . ?
C6A C1A C21A 117(2) . . ?
C3A C2A C1A 120 . . ?
C2A C3A C4A 120 . . ?
C5A C4A C3A 120 . . ?
C5A C4A Br1A 102.6(13) . . ?
C3A C4A Br1A 137.2(13) . . ?
C4A C5A C6A 120 . . ?
C5A C6A C1A 120 . . ?
C21B C20B C17 173(3) . . ?
C20B C21B C1B 176(2) . . ?
C2B C1B C6B 120 . . ?
C2B C1B C21B 117.1(13) . . ?
C6B C1B C21B 122.4(13) . . ?
C3B C2B C1B 120 . . ?
C2B C3B C4B 120 . . ?
C3B C4B C5B 120 . . ?
C3B C4B Br1B 115.7(6) . . ?
C5B C4B Br1B 123.8(6) . . ?
C4B C5B C6B 120 . . ?
C4B C5B C10B 120 . . ?
C6B C5B C10B 120 . . ?
C7B C6B C5B 120 . . ?
C7B C6B C1B 120 . . ?
C5B C6B C1B 120 . . ?
C6B C7B C8B 120 . . ?
C9B C8B C7B 120 . . ?
C8B C9B C10B 120 . . ?
C9B C10B C5B 120 . . ?
C4 C5 C10 120.8(10) . . ?
C4 C5 C6 119.0(10) . . ?
C10 C5 C6 120.2(10) . . ?
C13 C14 C8 112.8(8) . . ?
C13 C14 C15 103.6(10) . . ?
C8 C14 C15 119.5(9) . . ?
C15 C16 C17 105.1(10) . . ?
C1 C2 C3 119.7(12) . . ?
C7 C6 C5 114.5(10) . . ?
C5 C4 C3 122.8(10) . . ?
C9 C11 C12 110.7(9) . . ?
C12 C13 C14 108.0(10) . . ?
C12 C13 C18 109.4(10) . . ?
C14 C13 C18 114.5(9) . . ?
C12 C13 C17 118.0(9) . . ?
C14 C13 C17 100.0(8) . . ?
C18 C13 C17 107.0(10) . . ?
C1 C10 C5 114.6(10) . . ?
C1 C10 C9 124.1(10) . . ?
C5 C10 C9 121.3(9) . . ?
C8 C9 C10 111.0(8) . . ?
C8 C9 C11 112.7(9) . . ?
C10 C9 C11 112.7(10) . . ?
C2 C1 C10 125.0(11) . . ?
C6 C7 C8 110.8(10) . . ?
C16 C15 C14 105.3(10) . . ?
C9 C8 C7 110.4(9) . . ?
C9 C8 C14 109.9(8) . . ?
C7 C8 C14 111.9(9) . . ?
C20A C17 O2 103(2) . . ?
C20A C17 C13 117.4(19) . . ?
O2 C17 C13 113.1(9) . . ?
C20A C17 C16 106(2) . . ?
O2 C17 C16 112.9(10) . . ?
C13 C17 C16 104.2(9) . . ?
O2 C17 C20B 106.3(18) . . ?
C13 C17 C20B 107.8(17) . . ?
C16 C17 C20B 113(2) . . ?
C13 C12 C11 112.7(9) . . ?
O1 C3 C2 123.4(11) . . ?
O1 C3 C4 119.6(9) . . ?
C2 C3 C4 116.8(10) . . ?

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
C6A C1A C2A C3A 0 . . . . ?
C21A C1A C2A C3A -175(2) . . . . ?
C1A C2A C3A C4A 0 . . . . ?
C2A C3A C4A C5A 0 . . . . ?
C2A C3A C4A Br1A -174(2) . . . . ?
C3A C4A C5A C6A 0 . . . . ?
Br1A C4A C5A C6A 175.7(15) . . . . ?
C4A C5A C6A C1A 0 . . . . ?
C2A C1A C6A C5A 0 . . . . ?
C21A C1A C6A C5A 176(2) . . . . ?
C6B C1B C2B C3B 0 . . . . ?
C21B C1B C2B C3B 172(2) . . . . ?
C1B C2B C3B C4B 0 . . . . ?
C2B C3B C4B C5B 0 . . . . ?
C2B C3B C4B Br1B -171.8(13) . . . . ?
C3B C4B C5B C6B 0 . . . . ?
Br1B C4B C5B C6B 171.1(14) . . . . ?
C3B C4B C5B C10B 180 . . . . ?
Br1B C4B C5B C10B -8.9(14) . . . . ?
C4B C5B C6B C7B 180 . . . . ?
C10B C5B C6B C7B 0 . . . . ?
C4B C5B C6B C1B 0 . . . . ?
C10B C5B C6B C1B 180 . . . . ?
C2B C1B C6B C7B 180 . . . . ?
C21B C1B C6B C7B 8(2) . . . . ?
C2B C1B C6B C5B 0 . . . . ?
C21B C1B C6B C5B -172(2) . . . . ?
C5B C6B C7B C8B 0 . . . . ?
C1B C6B C7B C8B 180 . . . . ?
C6B C7B C8B C9B 0 . . . . ?
C7B C8B C9B C10B 0 . . . . ?
C8B C9B C10B C5B 0 . . . . ?
C4B C5B C10B C9B 180 . . . . ?
C6B C5B C10B C9B 0 . . . . ?
C4 C5 C6 C7 173.9(12) . . . . ?
C10 C5 C6 C7 -7.0(18) . . . . ?
C10 C5 C4 C3 -0.5(17) . . . . ?
C6 C5 C4 C3 178.6(12) . . . . ?
C8 C14 C13 C12 -59.3(12) . . . . ?
C15 C14 C13 C12 170.0(10) . . . . ?
C8 C14 C13 C18 62.7(13) . . . . ?
C15 C14 C13 C18 -68.0(12) . . . . ?
C8 C14 C13 C17 176.7(10) . . . . ?
C15 C14 C13 C17 46.0(12) . . . . ?
C4 C5 C10 C1 -4.1(16) . . . . ?
C6 C5 C10 C1 176.8(12) . . . . ?
C4 C5 C10 C9 177.3(11) . . . . ?
C6 C5 C10 C9 -1.8(17) . . . . ?
C1 C10 C9 C8 159.1(11) . . . . ?
C5 C10 C9 C8 -22.5(15) . . . . ?
C1 C10 C9 C11 31.5(16) . . . . ?
C5 C10 C9 C11 -150.1(11) . . . . ?
C12 C11 C9 C8 51.6(14) . . . . ?
C12 C11 C9 C10 178.3(10) . . . . ?
C3 C2 C1 C10 0(2) . . . . ?
C5 C10 C1 C2 4.4(19) . . . . ?
C9 C10 C1 C2 -177.1(12) . . . . ?
C5 C6 C7 C8 39.0(18) . . . . ?
C17 C16 C15 C14 5.8(15) . . . . ?
C13 C14 C15 C16 -32.6(14) . . . . ?
C8 C14 C15 C16 -159.1(11) . . . . ?
C10 C9 C8 C7 55.0(12) . . . . ?
C11 C9 C8 C7 -177.4(10) . . . . ?
C10 C9 C8 C14 179.0(10) . . . . ?
C11 C9 C8 C14 -53.5(13) . . . . ?
C6 C7 C8 C9 -64.9(14) . . . . ?
C6 C7 C8 C14 172.3(11) . . . . ?
C13 C14 C8 C9 58.1(13) . . . . ?
C15 C14 C8 C9 -179.8(11) . . . . ?
C13 C14 C8 C7 -178.9(10) . . . . ?
C15 C14 C8 C7 -56.8(16) . . . . ?
C12 C13 C17 C20A -41(3) . . . . ?
C14 C13 C17 C20A 75(3) . . . . ?
C18 C13 C17 C20A -165(2) . . . . ?
C12 C13 C17 O2 78.2(14) . . . . ?
C14 C13 C17 O2 -165.2(9) . . . . ?
C18 C13 C17 O2 -45.6(12) . . . . ?
C12 C13 C17 C16 -158.8(11) . . . . ?
C14 C13 C17 C16 -42.2(12) . . . . ?
C18 C13 C17 C16 77.4(12) . . . . ?
C12 C13 C17 C20B -39(2) . . . . ?
C14 C13 C17 C20B 78(2) . . . . ?
C18 C13 C17 C20B -163(2) . . . . ?
C15 C16 C17 C20A -102(2) . . . . ?
C15 C16 C17 O2 145.9(11) . . . . ?
C15 C16 C17 C13 22.7(15) . . . . ?
C15 C16 C17 C20B -94(2) . . . . ?
C14 C13 C12 C11 56.8(13) . . . . ?
C18 C13 C12 C11 -68.4(13) . . . . ?
C17 C13 C12 C11 169.0(10) . . . . ?
C9 C11 C12 C13 -54.0(15) . . . . ?
C1 C2 C3 O1 -179.6(12) . . . . ?
C1 C2 C3 C4 -4.9(17) . . . . ?
C5 C4 C3 O1 -180.0(11) . . . . ?
C5 C4 C3 C2 5.2(17) . . . . ?

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
O2 H002 O1 0.84 1.9 2.696(13) 157.7 2_564

# END of CIF
####################################################################### 
# 
# 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_san784
_database_code_depnum_ccdc_archive 'CCDC 1463834'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-23T11:15:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C34 H36 Br O3'
_chemical_formula_weight         572.54
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.59250(10)
_cell_length_b                   22.2328(6)
_cell_length_c                   10.2751(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.2320(10)
_cell_angle_gamma                90
_cell_volume                     1482.07(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10372
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.888
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.871

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.014191
_diffrn_orient_matrix_ub_12      0.019807
_diffrn_orient_matrix_ub_13      -0.0853
_diffrn_orient_matrix_ub_21      -0.048646
_diffrn_orient_matrix_ub_22      0.038842
_diffrn_orient_matrix_ub_23      0.03273
_diffrn_orient_matrix_ub_31      0.145571
_diffrn_orient_matrix_ub_32      0.011049
_diffrn_orient_matrix_ub_33      0.037854
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_number            15438
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.878
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.876
_reflns_Friedel_fraction_full    0.875
_reflns_Friedel_fraction_max     0.754
_reflns_Friedel_coverage         0.722
_reflns_number_total             5978
_reflns_number_gt                4873
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.3494P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5978
_refine_ls_number_parameters     352
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(4)
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9081(5) 0.79638(17) 0.6425(4) 0.0508(8) Uani 1 1 d . . . . .
H1 H 0.7964 0.7784 0.5884 0.061 Uiso 1 1 calc R U . . .
C1A C 0.8849(5) 0.42330(15) 0.6477(4) 0.0480(8) Uani 1 1 d . . . . .
C1AA C 0.4382(5) 0.31564(18) 0.7989(3) 0.0480(8) Uani 1 1 d . . . . .
C2 C 0.8932(6) 0.85683(18) 0.6773(4) 0.0554(9) Uani 1 1 d . . . . .
H2 H 0.773 0.8784 0.648 0.067 Uiso 1 1 calc R U . . .
C2A C 0.7866(6) 0.37557(19) 0.5743(4) 0.0599(10) Uani 1 1 d . . . . .
H2A H 0.8171 0.3668 0.4914 0.072 Uiso 1 1 calc R U . . .
C2AA C 0.4394(6) 0.25334(18) 0.7833(4) 0.0586(10) Uani 1 1 d . . . . .
H2AA H 0.5373 0.2357 0.7405 0.07 Uiso 1 1 calc R U . . .
C3 C 1.0602(6) 0.88395(17) 0.7562(4) 0.0512(9) Uani 1 1 d . . . . .
C3A C 0.6441(6) 0.3414(2) 0.6247(4) 0.0605(10) Uani 1 1 d . . . . .
H3A H 0.5802 0.3095 0.5749 0.073 Uiso 1 1 calc R U . . .
C3AA C 0.2973(7) 0.2175(2) 0.8305(4) 0.0639(11) Uani 1 1 d . . . . .
H3AA H 0.2986 0.176 0.8187 0.077 Uiso 1 1 calc R U . . .
C4 C 1.2332(6) 0.85024(19) 0.8021(3) 0.0530(9) Uani 1 1 d . . . . .
H4 H 1.3439 0.8684 0.8567 0.064 Uiso 1 1 calc R U . . .
C4A C 0.5936(5) 0.35317(16) 0.7475(3) 0.0463(8) Uani 1 1 d . . . . .
C4AA C 0.1550(5) 0.2434(2) 0.8945(4) 0.0584(10) Uani 1 1 d . . . . .
C5 C 1.2475(5) 0.78981(17) 0.7694(3) 0.0465(8) Uani 1 1 d . . . . .
C5A C 0.6938(6) 0.40038(17) 0.8204(4) 0.0516(9) Uani 1 1 d . . . . .
H5A H 0.6636 0.409 0.9034 0.062 Uiso 1 1 calc R U . . .
C5AA C 0.1484(6) 0.3044(2) 0.9112(4) 0.0686(12) Uani 1 1 d . . . . .
H5AA H 0.0506 0.3217 0.9546 0.082 Uiso 1 1 calc R U . . .
C6 C 1.4426(6) 0.75650(19) 0.8274(4) 0.0582(10) Uani 1 1 d . . . . .
H6C H 1.5554 0.7722 0.7884 0.07 Uiso 1 1 calc R U . . .
H6D H 1.4742 0.7644 0.9217 0.07 Uiso 1 1 calc R U . . .
C6A C 0.8378(6) 0.43489(18) 0.7715(4) 0.0521(9) Uani 1 1 d . . . . .
H6A H 0.9037 0.4662 0.8223 0.063 Uiso 1 1 calc R U . . .
C6AA C 0.2904(6) 0.3400(2) 0.8622(4) 0.0592(10) Uani 1 1 d . . . . .
H6AA H 0.2856 0.3815 0.8724 0.071 Uiso 1 1 calc R U . . .
C7 C 1.4295(5) 0.68931(19) 0.8058(3) 0.0531(8) Uani 1 1 d . . . . .
H7A H 1.3521 0.6713 0.8676 0.064 Uiso 1 1 calc R U . . .
H7B H 1.5671 0.6722 0.8218 0.064 Uiso 1 1 calc R U . . .
C8 C 1.3244(5) 0.67536(15) 0.6648(3) 0.0426(8) Uani 1 1 d . . . . .
H8 H 1.3945 0.6982 0.6042 0.051 Uiso 1 1 calc R U . . .
C9 C 1.0978(4) 0.69622(17) 0.6446(3) 0.0434(7) Uani 1 1 d . . . . .
H9 H 1.0303 0.6723 0.7047 0.052 Uiso 1 1 calc R U . . .
C10 C 1.0839(5) 0.76210(16) 0.6857(3) 0.0432(7) Uani 1 1 d . . . . .
C11 C 0.9846(5) 0.68287(18) 0.5042(4) 0.0520(8) Uani 1 1 d . . . . .
H11A H 1.0391 0.7087 0.4426 0.062 Uiso 1 1 calc R U . . .
H11B H 0.8397 0.6924 0.4984 0.062 Uiso 1 1 calc R U . . .
C12 C 1.0049(5) 0.61701(17) 0.4631(4) 0.0501(8) Uani 1 1 d . . . . .
H12A H 0.9303 0.5914 0.5147 0.06 Uiso 1 1 calc R U . . .
H12B H 0.9437 0.6123 0.3706 0.06 Uiso 1 1 calc R U . . .
C13 C 1.2307(5) 0.59741(15) 0.4839(3) 0.0401(7) Uani 1 1 d . . . . .
C14 C 1.3281(5) 0.60943(16) 0.6282(3) 0.0410(7) Uani 1 1 d . . . . .
H14 H 1.2434 0.5882 0.6829 0.049 Uiso 1 1 calc R U . . .
C15 C 1.5367(5) 0.57603(17) 0.6459(4) 0.0534(9) Uani 1 1 d . . . . .
H15A H 1.6437 0.602 0.6236 0.064 Uiso 1 1 calc R U . . .
H15B H 1.5777 0.5623 0.7364 0.064 Uiso 1 1 calc R U . . .
C16 C 1.4976(5) 0.52253(18) 0.5502(4) 0.0547(9) Uani 1 1 d . . . . .
H16A H 1.5141 0.4849 0.5988 0.066 Uiso 1 1 calc R U . . .
H16B H 1.5941 0.5232 0.4892 0.066 Uiso 1 1 calc R U . . .
C17 C 1.2732(5) 0.52883(16) 0.4739(4) 0.0459(8) Uani 1 1 d . . . . .
C18 C 1.3437(6) 0.63034(18) 0.3863(4) 0.0551(9) Uani 1 1 d . . . . .
H18A H 1.3231 0.6729 0.3928 0.083 Uiso 1 1 calc R U . . .
H18B H 1.2902 0.6172 0.2979 0.083 Uiso 1 1 calc R U . . .
H18C H 1.4884 0.6215 0.4073 0.083 Uiso 1 1 calc R U . . .
C20 C 1.1332(5) 0.49230(16) 0.5389(4) 0.0501(8) Uani 1 1 d . . . . .
C21 C 1.0256(6) 0.46083(16) 0.5912(4) 0.0518(9) Uani 1 1 d . . . . .
C35 C 0.5305(15) 0.5335(4) 0.0728(8) 0.136(3) Uani 1 1 d . . . . .
H35A H 0.5663 0.5756 0.0672 0.163 Uiso 1 1 calc R U . . .
H35B H 0.6171 0.5107 0.0235 0.163 Uiso 1 1 calc R U . . .
C36 C 0.3254(17) 0.5260(5) 0.0113(9) 0.172(4) Uani 1 1 d . . . . .
H36A H 0.3091 0.5393 -0.0789 0.258 Uiso 1 1 calc R U . . .
H36B H 0.2885 0.4843 0.0133 0.258 Uiso 1 1 calc R U . . .
H36C H 0.2376 0.5493 0.0571 0.258 Uiso 1 1 calc R U . . .
O10 O 0.5778(6) 0.5157(2) 0.2067(4) 0.1026(13) Uani 1 1 d . . . . .
O1 O 1.0628(5) 0.94336(13) 0.7905(3) 0.0658(7) Uani 1 1 d . . . . .
O2 O 1.2494(5) 0.50693(13) 0.3412(3) 0.0562(7) Uani 1 1 d . . . . .
Br1 Br -0.03039(8) 0.19310(3) 0.96595(5) 0.0978(2) Uani 1 1 d . . . . .
H01 H 0.931(8) 0.957(2) 0.742(5) 0.073(14) Uiso 1 1 d . . . . .
H02 H 1.332(6) 0.512(2) 0.316(4) 0.044(13) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.392(5) . ?
C1 C2 1.399(5) . ?
C1 H1 0.93 . ?
C1A C6A 1.387(5) . ?
C1A C2A 1.393(6) . ?
C1A C21 1.444(5) . ?
C1AA C6AA 1.375(5) . ?
C1AA C2AA 1.394(6) . ?
C1AA C4A 1.489(5) . ?
C2 C3 1.384(6) . ?
C2 H2 0.93 . ?
C2A C3A 1.379(5) . ?
C2A H2A 0.93 . ?
C2AA C3AA 1.382(5) . ?
C2AA H2AA 0.93 . ?
C3 O1 1.366(5) . ?
C3 C4 1.376(5) . ?
C3A C4A 1.386(5) . ?
C3A H3A 0.93 . ?
C3AA C4AA 1.365(6) . ?
C3AA H3AA 0.93 . ?
C4 C5 1.392(6) . ?
C4 H4 0.93 . ?
C4A C5A 1.387(5) . ?
C4AA C5AA 1.370(6) . ?
C4AA Br1 1.898(4) . ?
C5 C10 1.398(5) . ?
C5 C6 1.512(5) . ?
C5A C6A 1.382(5) . ?
C5A H5A 0.93 . ?
C5AA C6AA 1.387(6) . ?
C5AA H5AA 0.93 . ?
C6 C7 1.510(6) . ?
C6 H6C 0.97 . ?
C6 H6D 0.97 . ?
C6A H6A 0.93 . ?
C6AA H6AA 0.93 . ?
C7 C8 1.522(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C14 1.514(5) . ?
C8 C9 1.543(4) . ?
C8 H8 0.98 . ?
C9 C11 1.531(5) . ?
C9 C10 1.532(5) . ?
C9 H9 0.98 . ?
C11 C12 1.536(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.529(5) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.531(5) . ?
C13 C18 1.537(5) . ?
C13 C17 1.557(5) . ?
C14 C15 1.545(4) . ?
C14 H14 0.98 . ?
C15 C16 1.536(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.553(5) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 O2 1.429(5) . ?
C17 C20 1.475(5) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C20 C21 1.191(5) . ?
C35 C36 1.397(11) . ?
C35 O10 1.412(8) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C36 H36A 0.96 . ?
C36 H36B 0.96 . ?
C36 H36C 0.96 . ?
O1 H01 0.97(5) . ?
O2 H02 0.65(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 122.5(3) . . ?
C10 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C6A C1A C2A 118.7(3) . . ?
C6A C1A C21 121.7(3) . . ?
C2A C1A C21 119.5(3) . . ?
C6AA C1AA C2AA 117.7(3) . . ?
C6AA C1AA C4A 122.5(4) . . ?
C2AA C1AA C4A 119.9(3) . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C3A C2A C1A 120.0(4) . . ?
C3A C2A H2A 120 . . ?
C1A C2A H2A 120 . . ?
C3AA C2AA C1AA 121.0(4) . . ?
C3AA C2AA H2AA 119.5 . . ?
C1AA C2AA H2AA 119.5 . . ?
O1 C3 C4 117.8(4) . . ?
O1 C3 C2 123.0(3) . . ?
C4 C3 C2 119.2(3) . . ?
C2A C3A C4A 121.8(4) . . ?
C2A C3A H3A 119.1 . . ?
C4A C3A H3A 119.1 . . ?
C4AA C3AA C2AA 119.5(4) . . ?
C4AA C3AA H3AA 120.2 . . ?
C2AA C3AA H3AA 120.2 . . ?
C3 C4 C5 122.0(4) . . ?
C3 C4 H4 119 . . ?
C5 C4 H4 119 . . ?
C3A C4A C5A 117.8(3) . . ?
C3A C4A C1AA 120.5(3) . . ?
C5A C4A C1AA 121.6(3) . . ?
C3AA C4AA C5AA 121.2(4) . . ?
C3AA C4AA Br1 118.9(4) . . ?
C5AA C4AA Br1 119.9(3) . . ?
C4 C5 C10 119.7(3) . . ?
C4 C5 C6 117.8(3) . . ?
C10 C5 C6 122.4(3) . . ?
C6A C5A C4A 121.1(3) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C4AA C5AA C6AA 118.8(4) . . ?
C4AA C5AA H5AA 120.6 . . ?
C6AA C5AA H5AA 120.6 . . ?
C7 C6 C5 113.8(3) . . ?
C7 C6 H6C 108.8 . . ?
C5 C6 H6C 108.8 . . ?
C7 C6 H6D 108.8 . . ?
C5 C6 H6D 108.8 . . ?
H6C C6 H6D 107.7 . . ?
C5A C6A C1A 120.7(4) . . ?
C5A C6A H6A 119.7 . . ?
C1A C6A H6A 119.7 . . ?
C1AA C6AA C5AA 121.9(4) . . ?
C1AA C6AA H6AA 119.1 . . ?
C5AA C6AA H6AA 119.1 . . ?
C6 C7 C8 110.3(3) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C14 C8 C7 114.1(3) . . ?
C14 C8 C9 108.4(3) . . ?
C7 C8 C9 109.4(3) . . ?
C14 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C11 C9 C10 113.7(3) . . ?
C11 C9 C8 111.5(3) . . ?
C10 C9 C8 110.8(3) . . ?
C11 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C8 C9 H9 106.8 . . ?
C1 C10 C5 117.5(3) . . ?
C1 C10 C9 121.5(3) . . ?
C5 C10 C9 120.9(3) . . ?
C9 C11 C12 113.1(3) . . ?
C9 C11 H11A 109 . . ?
C12 C11 H11A 109 . . ?
C9 C11 H11B 109 . . ?
C12 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 111.3(3) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108 . . ?
C12 C13 C14 108.4(3) . . ?
C12 C13 C18 110.2(3) . . ?
C14 C13 C18 112.4(3) . . ?
C12 C13 C17 116.9(3) . . ?
C14 C13 C17 100.7(3) . . ?
C18 C13 C17 108.0(3) . . ?
C8 C14 C13 112.8(3) . . ?
C8 C14 C15 119.3(3) . . ?
C13 C14 C15 104.0(3) . . ?
C8 C14 H14 106.7 . . ?
C13 C14 H14 106.7 . . ?
C15 C14 H14 106.7 . . ?
C16 C15 C14 104.6(3) . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 C17 106.9(3) . . ?
C15 C16 H16A 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C15 C16 H16B 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.6 . . ?
O2 C17 C20 105.8(3) . . ?
O2 C17 C16 112.6(3) . . ?
C20 C17 C16 109.7(3) . . ?
O2 C17 C13 114.0(3) . . ?
C20 C17 C13 112.0(3) . . ?
C16 C17 C13 102.8(3) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 177.3(4) . . ?
C20 C21 C1A 176.4(4) . . ?
C36 C35 O10 115.9(7) . . ?
C36 C35 H35A 108.3 . . ?
O10 C35 H35A 108.3 . . ?
C36 C35 H35B 108.3 . . ?
O10 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C3 O1 H01 102(3) . . ?
C17 O2 H02 110(4) . . ?

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
C10 C1 C2 C3 0.9(6) . . . . ?
C6A C1A C2A C3A 0.6(6) . . . . ?
C21 C1A C2A C3A -176.7(4) . . . . ?
C6AA C1AA C2AA C3AA -0.3(6) . . . . ?
C4A C1AA C2AA C3AA 179.8(4) . . . . ?
C1 C2 C3 O1 177.2(4) . . . . ?
C1 C2 C3 C4 -2.4(6) . . . . ?
C1A C2A C3A C4A 0.4(7) . . . . ?
C1AA C2AA C3AA C4AA -0.7(6) . . . . ?
O1 C3 C4 C5 -178.1(3) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C2A C3A C4A C5A -1.0(6) . . . . ?
C2A C3A C4A C1AA 179.6(4) . . . . ?
C6AA C1AA C4A C3A -137.7(4) . . . . ?
C2AA C1AA C4A C3A 42.3(5) . . . . ?
C6AA C1AA C4A C5A 42.9(5) . . . . ?
C2AA C1AA C4A C5A -137.1(4) . . . . ?
C2AA C3AA C4AA C5AA 0.9(6) . . . . ?
C2AA C3AA C4AA Br1 -177.0(3) . . . . ?
C3 C4 C5 C10 1.1(5) . . . . ?
C3 C4 C5 C6 -178.8(4) . . . . ?
C3A C4A C5A C6A 0.6(6) . . . . ?
C1AA C4A C5A C6A -180.0(3) . . . . ?
C3AA C4AA C5AA C6AA -0.3(6) . . . . ?
Br1 C4AA C5AA C6AA 177.7(3) . . . . ?
C4 C5 C6 C7 170.1(3) . . . . ?
C10 C5 C6 C7 -9.8(5) . . . . ?
C4A C5A C6A C1A 0.4(6) . . . . ?
C2A C1A C6A C5A -1.0(5) . . . . ?
C21 C1A C6A C5A 176.3(4) . . . . ?
C2AA C1AA C6AA C5AA 1.0(6) . . . . ?
C4A C1AA C6AA C5AA -179.1(4) . . . . ?
C4AA C5AA C6AA C1AA -0.7(6) . . . . ?
C5 C6 C7 C8 43.1(4) . . . . ?
C6 C7 C8 C14 172.7(3) . . . . ?
C6 C7 C8 C9 -65.7(4) . . . . ?
C14 C8 C9 C11 -54.7(4) . . . . ?
C7 C8 C9 C11 -179.7(3) . . . . ?
C14 C8 C9 C10 177.6(2) . . . . ?
C7 C8 C9 C10 52.6(4) . . . . ?
C2 C1 C10 C5 1.6(6) . . . . ?
C2 C1 C10 C9 -179.1(3) . . . . ?
C4 C5 C10 C1 -2.5(5) . . . . ?
C6 C5 C10 C1 177.3(4) . . . . ?
C4 C5 C10 C9 178.1(3) . . . . ?
C6 C5 C10 C9 -2.0(5) . . . . ?
C11 C9 C10 C1 34.5(4) . . . . ?
C8 C9 C10 C1 161.0(3) . . . . ?
C11 C9 C10 C5 -146.2(3) . . . . ?
C8 C9 C10 C5 -19.7(4) . . . . ?
C10 C9 C11 C12 178.4(3) . . . . ?
C8 C9 C11 C12 52.3(4) . . . . ?
C9 C11 C12 C13 -52.8(4) . . . . ?
C11 C12 C13 C14 55.1(4) . . . . ?
C11 C12 C13 C18 -68.2(4) . . . . ?
C11 C12 C13 C17 168.0(3) . . . . ?
C7 C8 C14 C13 -177.2(3) . . . . ?
C9 C8 C14 C13 60.6(3) . . . . ?
C7 C8 C14 C15 -54.8(4) . . . . ?
C9 C8 C14 C15 -177.0(3) . . . . ?
C12 C13 C14 C8 -61.2(3) . . . . ?
C18 C13 C14 C8 60.9(4) . . . . ?
C17 C13 C14 C8 175.6(2) . . . . ?
C12 C13 C14 C15 168.2(3) . . . . ?
C18 C13 C14 C15 -69.8(4) . . . . ?
C17 C13 C14 C15 45.0(3) . . . . ?
C8 C14 C15 C16 -157.0(3) . . . . ?
C13 C14 C15 C16 -30.4(4) . . . . ?
C14 C15 C16 C17 3.6(4) . . . . ?
C15 C16 C17 O2 146.9(3) . . . . ?
C15 C16 C17 C20 -95.5(4) . . . . ?
C15 C16 C17 C13 23.9(4) . . . . ?
C12 C13 C17 O2 78.7(4) . . . . ?
C14 C13 C17 O2 -164.1(3) . . . . ?
C18 C13 C17 O2 -46.2(4) . . . . ?
C12 C13 C17 C20 -41.4(4) . . . . ?
C14 C13 C17 C20 75.8(3) . . . . ?
C18 C13 C17 C20 -166.3(3) . . . . ?
C12 C13 C17 C16 -159.1(3) . . . . ?
C14 C13 C17 C16 -42.0(3) . . . . ?
C18 C13 C17 C16 76.0(3) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1463835'
_audit_update_record             
;
2016-03-10 deposited with the CCDC.
2016-07-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-19T10:47:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C27 H29 I O2'
_chemical_formula_weight         512.4
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.63350(10)
_cell_length_b                   16.6143(4)
_cell_length_c                   21.5766(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2377.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24432
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      30.03
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.6520
_exptl_absorpt_correction_T_max  0.7128

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_ub_11      0.139712
_diffrn_orient_matrix_ub_12      0.021704
_diffrn_orient_matrix_ub_13      0.004871
_diffrn_orient_matrix_ub_21      0.028404
_diffrn_orient_matrix_ub_22      -0.041436
_diffrn_orient_matrix_ub_23      0.032461
_diffrn_orient_matrix_ub_31      0.048982
_diffrn_orient_matrix_ub_32      -0.037878
_diffrn_orient_matrix_ub_33      -0.032719
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_number            29917
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.972
_diffrn_reflns_theta_max         29.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.954
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_coverage         0.764
_reflns_number_total             6210
_reflns_number_gt                3967
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+1.7704P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6210
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.093
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C19 C 0.7669(15) 0.7009(5) 0.2379(3) 0.097(2) Uani 1 1 d . . . . .
H19A H 0.8928 0.6726 0.2358 0.146 Uiso 1 1 calc R U . . .
H19B H 0.7892 0.754 0.2542 0.146 Uiso 1 1 calc R U . . .
H19C H 0.7099 0.705 0.1971 0.146 Uiso 1 1 calc R U . . .
C1 C 0.6252(8) 0.5743(3) 0.4319(2) 0.0551(13) Uani 1 1 d . . . . .
H1 H 0.5407 0.5416 0.4553 0.066 Uiso 1 1 calc R U . . .
C1A C 0.7246(9) 0.6042(3) 0.8118(2) 0.0570(13) Uani 1 1 d G . . . .
C2 C 0.5686(9) 0.5940(4) 0.3725(3) 0.0607(15) Uani 1 1 d . . . . .
H2 H 0.4472 0.5755 0.3563 0.073 Uiso 1 1 calc R U . . .
C2A C 0.5757(7) 0.5561(2) 0.8377(2) 0.0663(16) Uani 1 1 d G . . . .
H2A H 0.5717 0.5015 0.8286 0.08 Uiso 1 1 calc R U . . .
C3 C 0.6951(9) 0.6417(3) 0.3370(2) 0.0588(14) Uani 1 1 d . . . . .
C3A C 0.4323(6) 0.5890(2) 0.87733(18) 0.0706(17) Uani 1 1 d G . . . .
H3A H 0.3331 0.5563 0.8945 0.085 Uiso 1 1 calc R U . . .
C4 C 0.8716(9) 0.6692(3) 0.3613(2) 0.0543(13) Uani 1 1 d . . . . .
H4 H 0.957 0.7003 0.3369 0.065 Uiso 1 1 calc R U . . .
C4A C 0.4371(6) 0.6707(3) 0.89123(18) 0.0655(16) Uani 1 1 d G . . . .
C5 C 0.9269(8) 0.6516(3) 0.4227(2) 0.0463(11) Uani 1 1 d . . . . .
C5A C 0.5854(7) 0.7195(2) 0.8656(2) 0.086(2) Uani 1 1 d G . . . .
H5A H 0.5887 0.7741 0.8749 0.103 Uiso 1 1 calc R U . . .
C6 C 1.1174(7) 0.6888(3) 0.4475(3) 0.0544(12) Uani 1 1 d . . . . .
H6C H 1.1206 0.7452 0.436 0.065 Uiso 1 1 calc R U . . .
H6B H 1.2322 0.6627 0.4282 0.065 Uiso 1 1 calc R U . . .
C6A C 0.7288(7) 0.6866(3) 0.8260(3) 0.088(2) Uani 1 1 d G . . . .
H6A H 0.8279 0.7194 0.8088 0.105 Uiso 1 1 calc R U . . .
C7 C 1.1377(8) 0.6822(3) 0.5173(2) 0.0526(12) Uani 1 1 d . . . . .
H7A H 1.0487 0.7207 0.5371 0.063 Uiso 1 1 calc R U . . .
H7B H 1.275 0.6946 0.5295 0.063 Uiso 1 1 calc R U . . .
C8 C 1.0842(7) 0.5978(3) 0.5382(2) 0.0431(11) Uani 1 1 d . . . . .
C9 C 0.8596(7) 0.5806(3) 0.5252(2) 0.0420(10) Uani 1 1 d . . . . .
C10 C 0.8044(7) 0.6015(3) 0.4582(2) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.8038(8) 0.4948(3) 0.5450(2) 0.0542(12) Uani 1 1 d . . . . .
H11A H 0.8748 0.4566 0.519 0.065 Uiso 1 1 calc R U . . .
H11B H 0.6603 0.4867 0.539 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8569(8) 0.4787(3) 0.6133(2) 0.0530(13) Uani 1 1 d . . . . .
H12A H 0.7726 0.5119 0.6396 0.064 Uiso 1 1 calc R U . . .
H12B H 0.8287 0.4228 0.623 0.064 Uiso 1 1 calc R U . . .
C13 C 1.0778(8) 0.4965(3) 0.6270(2) 0.0497(12) Uani 1 1 d . . . . .
C14 C 1.1249(7) 0.5826(3) 0.6067(2) 0.0460(11) Uani 1 1 d . . . . .
C15 C 1.3369(9) 0.5986(4) 0.6323(3) 0.0609(15) Uani 1 1 d . . . . .
H15A H 1.358 0.6556 0.6396 0.073 Uiso 1 1 calc R U . . .
H15B H 1.4395 0.5792 0.6039 0.073 Uiso 1 1 calc R U . . .
C16 C 1.3407(9) 0.5508(4) 0.6937(3) 0.0671(16) Uani 1 1 d . . . . .
H16A H 1.3477 0.5874 0.7286 0.081 Uiso 1 1 calc R U . . .
H16B H 1.4574 0.5157 0.6949 0.081 Uiso 1 1 calc R U . . .
C17 C 1.1446(8) 0.5007(4) 0.6966(3) 0.0590(15) Uani 1 1 d . . . . .
C18 C 1.2107(10) 0.4334(3) 0.5947(3) 0.0662(15) Uani 1 1 d . . . . .
H18A H 1.1916 0.4368 0.5507 0.099 Uiso 1 1 calc R U . . .
H18B H 1.1738 0.3806 0.6088 0.099 Uiso 1 1 calc R U . . .
H18C H 1.3497 0.4434 0.6044 0.099 Uiso 1 1 calc R U . . .
C20 C 0.9919(9) 0.5399(4) 0.7357(3) 0.0628(15) Uani 1 1 d . . . . .
C21 C 0.8701(9) 0.5703(4) 0.7700(3) 0.0615(15) Uani 1 1 d . . . . .
I1 I 0.21641(8) 0.72079(3) 0.94818(2) 0.0975(2) Uani 1 1 d . . . . .
O1 O 0.6319(7) 0.6585(3) 0.27717(19) 0.0791(13) Uani 1 1 d . . . . .
O2 O 1.1936(7) 0.4240(3) 0.7228(2) 0.0781(13) Uani 1 1 d . . . . .
H2AA H 1.103 0.4019 0.7351 0.094 Uiso 1 1 d R U . . .
H8 H 1.1577 0.5663 0.5153 0.094 Uiso 1 1 d R U . . .
H9 H 0.7773 0.6162 0.5556 0.094 Uiso 1 1 d R U . . .
H14 H 1.0402 0.6167 0.6313 0.094 Uiso 1 1 d R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C19 O1 1.420(8) . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C1 C2 1.375(8) . ?
C1 C10 1.392(7) . ?
C1 H1 0.93 . ?
C1A C2A 1.388(7) . ?
C1A C6A 1.404(7) . ?
C1A C21 1.435(8) . ?
C2 C3 1.385(8) . ?
C2 H2 0.93 . ?
C2A C3A 1.39 . ?
C2A H2A 0.93 . ?
C3 C4 1.362(8) . ?
C3 O1 1.386(6) . ?
C3A C4A 1.39 . ?
C3A H3A 0.93 . ?
C4 C5 1.406(7) . ?
C4 H4 0.93 . ?
C4A C5A 1.39 . ?
C4A I1 2.085(3) . ?
C5 C10 1.393(7) . ?
C5 C6 1.505(7) . ?
C5A C6A 1.39 . ?
C5A H5A 0.93 . ?
C6 C7 1.516(7) . ?
C6 H6C 0.97 . ?
C6 H6B 0.97 . ?
C6A H6A 0.93 . ?
C7 C8 1.515(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C14 1.524(7) . ?
C8 C9 1.543(7) . ?
C8 H8 0.8686 . ?
C9 C10 1.531(7) . ?
C9 C11 1.533(7) . ?
C9 H9 1.0385 . ?
C11 C12 1.538(8) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 C13 1.524(8) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.528(7) . ?
C13 C18 1.537(7) . ?
C13 C17 1.567(8) . ?
C14 C15 1.534(7) . ?
C14 H14 0.9583 . ?
C15 C16 1.544(8) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.546(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 O2 1.432(7) . ?
C17 C20 1.470(8) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C20 C21 1.206(8) . ?
O2 H2AA 0.7531 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 C10 122.4(5) . . ?
C2 C1 H1 118.8 . . ?
C10 C1 H1 118.8 . . ?
C2A C1A C6A 119.1(4) . . ?
C2A C1A C21 120.5(5) . . ?
C6A C1A C21 120.4(5) . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C1A C2A C3A 120.6(3) . . ?
C1A C2A H2A 119.7 . . ?
C3A C2A H2A 119.7 . . ?
C4 C3 O1 123.4(6) . . ?
C4 C3 C2 120.0(5) . . ?
O1 C3 C2 116.6(5) . . ?
C4A C3A C2A 120 . . ?
C4A C3A H3A 120 . . ?
C2A C3A H3A 120 . . ?
C3 C4 C5 121.1(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C5A C4A C3A 120 . . ?
C5A C4A I1 119.9(2) . . ?
C3A C4A I1 120.0(2) . . ?
C10 C5 C4 119.4(5) . . ?
C10 C5 C6 122.7(5) . . ?
C4 C5 C6 117.9(5) . . ?
C4A C5A C6A 120 . . ?
C4A C5A H5A 120 . . ?
C6A C5A H5A 120 . . ?
C5 C6 C7 113.4(4) . . ?
C5 C6 H6C 108.9 . . ?
C7 C6 H6C 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6C C6 H6B 107.7 . . ?
C5A C6A C1A 120.2(3) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C6 C7 C8 110.0(4) . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C14 113.6(4) . . ?
C7 C8 C9 110.1(4) . . ?
C14 C8 C9 108.5(4) . . ?
C7 C8 H8 104.9 . . ?
C14 C8 H8 110.6 . . ?
C9 C8 H8 109 . . ?
C10 C9 C11 114.6(4) . . ?
C10 C9 C8 111.2(4) . . ?
C11 C9 C8 110.7(4) . . ?
C10 C9 H9 110 . . ?
C11 C9 H9 103.1 . . ?
C8 C9 H9 106.6 . . ?
C5 C10 C1 117.9(5) . . ?
C5 C10 C9 121.0(4) . . ?
C1 C10 C9 121.0(4) . . ?
C9 C11 C12 112.0(4) . . ?
C9 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C9 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.9(4) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 108.8(4) . . ?
C12 C13 C18 109.3(5) . . ?
C14 C13 C18 113.0(4) . . ?
C12 C13 C17 117.8(4) . . ?
C14 C13 C17 100.1(4) . . ?
C18 C13 C17 107.7(4) . . ?
C8 C14 C13 113.4(4) . . ?
C8 C14 C15 118.8(4) . . ?
C13 C14 C15 104.3(4) . . ?
C8 C14 H14 109.6 . . ?
C13 C14 H14 106 . . ?
C15 C14 H14 103.7 . . ?
C14 C15 C16 103.5(5) . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109 . . ?
C15 C16 C17 107.3(5) . . ?
C15 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
C15 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
O2 C17 C20 108.9(5) . . ?
O2 C17 C16 107.7(5) . . ?
C20 C17 C16 111.4(6) . . ?
O2 C17 C13 113.7(5) . . ?
C20 C17 C13 112.0(4) . . ?
C16 C17 C13 102.9(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C20 C17 177.2(6) . . ?
C20 C21 C1A 178.2(7) . . ?
C3 O1 C19 117.7(5) . . ?
C17 O2 H2AA 113.1 . . ?

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
C10 C1 C2 C3 0.9(8) . . . . ?
C6A C1A C2A C3A -0.1(8) . . . . ?
C21 C1A C2A C3A -178.8(4) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C1 C2 C3 O1 179.0(5) . . . . ?
C1A C2A C3A C4A 0.0(4) . . . . ?
O1 C3 C4 C5 178.8(5) . . . . ?
C2 C3 C4 C5 -1.4(8) . . . . ?
C2A C3A C4A C5A 0 . . . . ?
C2A C3A C4A I1 177.9(3) . . . . ?
C3 C4 C5 C10 3.5(7) . . . . ?
C3 C4 C5 C6 -176.0(5) . . . . ?
C3A C4A C5A C6A 0 . . . . ?
I1 C4A C5A C6A -177.9(3) . . . . ?
C10 C5 C6 C7 -13.0(7) . . . . ?
C4 C5 C6 C7 166.5(4) . . . . ?
C4A C5A C6A C1A 0.0(4) . . . . ?
C2A C1A C6A C5A 0.1(8) . . . . ?
C21 C1A C6A C5A 178.8(4) . . . . ?
C5 C6 C7 C8 45.3(6) . . . . ?
C6 C7 C8 C14 173.0(4) . . . . ?
C6 C7 C8 C9 -65.1(5) . . . . ?
C7 C8 C9 C10 50.3(5) . . . . ?
C14 C8 C9 C10 175.2(4) . . . . ?
C7 C8 C9 C11 179.0(4) . . . . ?
C14 C8 C9 C11 -56.1(5) . . . . ?
C4 C5 C10 C1 -3.4(7) . . . . ?
C6 C5 C10 C1 176.1(4) . . . . ?
C4 C5 C10 C9 179.8(4) . . . . ?
C6 C5 C10 C9 -0.7(7) . . . . ?
C2 C1 C10 C5 1.2(7) . . . . ?
C2 C1 C10 C9 178.1(5) . . . . ?
C11 C9 C10 C5 -144.7(4) . . . . ?
C8 C9 C10 C5 -18.1(6) . . . . ?
C11 C9 C10 C1 38.6(6) . . . . ?
C8 C9 C10 C1 165.2(4) . . . . ?
C10 C9 C11 C12 -178.1(4) . . . . ?
C8 C9 C11 C12 55.1(5) . . . . ?
C9 C11 C12 C13 -54.6(6) . . . . ?
C11 C12 C13 C14 54.4(6) . . . . ?
C11 C12 C13 C18 -69.4(6) . . . . ?
C11 C12 C13 C17 167.3(4) . . . . ?
C7 C8 C14 C13 -177.9(4) . . . . ?
C9 C8 C14 C13 59.3(5) . . . . ?
C7 C8 C14 C15 -55.0(6) . . . . ?
C9 C8 C14 C15 -177.7(4) . . . . ?
C12 C13 C14 C8 -58.4(5) . . . . ?
C18 C13 C14 C8 63.2(6) . . . . ?
C17 C13 C14 C8 177.4(4) . . . . ?
C12 C13 C14 C15 170.9(4) . . . . ?
C18 C13 C14 C15 -67.5(6) . . . . ?
C17 C13 C14 C15 46.7(5) . . . . ?
C8 C14 C15 C16 -161.4(5) . . . . ?
C13 C14 C15 C16 -34.0(6) . . . . ?
C14 C15 C16 C17 7.5(7) . . . . ?
C15 C16 C17 O2 141.2(5) . . . . ?
C15 C16 C17 C20 -99.4(6) . . . . ?
C15 C16 C17 C13 20.8(6) . . . . ?
C12 C13 C17 O2 85.3(6) . . . . ?
C14 C13 C17 O2 -157.0(4) . . . . ?
C18 C13 C17 O2 -38.7(6) . . . . ?
C12 C13 C17 C20 -38.7(7) . . . . ?
C14 C13 C17 C20 79.0(5) . . . . ?
C18 C13 C17 C20 -162.8(5) . . . . ?
C12 C13 C17 C16 -158.5(5) . . . . ?
C14 C13 C17 C16 -40.8(5) . . . . ?
C18 C13 C17 C16 77.5(5) . . . . ?
C4 C3 O1 C19 5.6(8) . . . . ?
C2 C3 O1 C19 -174.3(6) . . . . ?

# END of CIF
