# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_150416_zyy_26
_database_code_depnum_ccdc_archive 'CCDC 1533084'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;
_audit_creation_date             2015-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H13 Br O'
_chemical_formula_sum            'C23 H13 Br O'
_chemical_formula_weight         385.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.7948(7)
_cell_length_b                   21.5595(13)
_cell_length_c                   7.9044(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.573(7)
_cell_angle_gamma                90.00
_cell_volume                     1615.48(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2184
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.4896
_cell_measurement_theta_min      2.9652
_exptl_absorpt_coefficient_mu    2.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6705
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0118764000
_diffrn_orient_matrix_UB_12      0.0119738000
_diffrn_orient_matrix_UB_13      0.0786649000
_diffrn_orient_matrix_UB_21      -0.0737488000
_diffrn_orient_matrix_UB_22      -0.0004444000
_diffrn_orient_matrix_UB_23      -0.0378720000
_diffrn_orient_matrix_UB_31      -0.0035616000
_diffrn_orient_matrix_UB_32      -0.0306492000
_diffrn_orient_matrix_UB_33      0.0313063000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2440
_reflns_number_total             2945
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.4851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0745
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.44720(3) 0.412499(13) -0.07564(3) 0.04023(12) Uani 1 d . . .
O1 O 0.8396(2) 0.37511(7) 0.0619(2) 0.0346(5) Uani 1 d . . .
C1 C 0.5055(3) 0.33389(11) 0.0255(3) 0.0261(5) Uani 1 d . . .
C2 C 0.4090(3) 0.28536(13) -0.0012(3) 0.0388(7) Uani 1 d . . .
H2 H 0.3143 0.2919 -0.0655 0.047 Uiso 1 calc . . R
C3 C 0.4523(3) 0.22767(13) 0.0665(4) 0.0428(8) Uani 1 d . . .
H3 H 0.3869 0.1943 0.0500 0.051 Uiso 1 calc . . R
C4 C 0.5899(3) 0.21839(11) 0.1581(3) 0.0355(7) Uani 1 d . . .
H4 H 0.6195 0.1786 0.2047 0.043 Uiso 1 calc . . R
C5 C 0.6848(3) 0.26652(10) 0.1825(3) 0.0278(6) Uani 1 d . . .
H5 H 0.7800 0.2594 0.2443 0.033 Uiso 1 calc . . R
C6 C 0.6436(3) 0.32564(10) 0.1179(3) 0.0213(5) Uani 1 d . . .
C7 C 0.7508(3) 0.37696(10) 0.1458(3) 0.0208(5) Uani 1 d . . .
C8 C 0.7456(2) 0.42449(10) 0.2804(3) 0.0194(5) Uani 1 d . . .
C9 C 0.6692(3) 0.40936(10) 0.4025(3) 0.0243(5) Uani 1 d . . .
H9 H 0.6204 0.3709 0.3920 0.029 Uiso 1 calc . . R
C10 C 0.6630(3) 0.44860(10) 0.5368(3) 0.0279(6) Uani 1 d . . .
H10 H 0.6117 0.4365 0.6186 0.033 Uiso 1 calc . . R
C11 C 0.7305(3) 0.50586(10) 0.5553(3) 0.0231(5) Uani 1 d . . .
C12 C 0.8069(2) 0.52332(10) 0.4317(3) 0.0191(5) Uani 1 d . . .
C13 C 0.8149(2) 0.48251(10) 0.2926(3) 0.0180(5) Uani 1 d . . .
C14 C 0.8885(3) 0.50423(10) 0.1689(3) 0.0242(5) Uani 1 d . . .
H14 H 0.8949 0.4780 0.0746 0.029 Uiso 1 calc . . R
C15 C 0.9490(3) 0.56089(11) 0.1825(3) 0.0268(6) Uani 1 d . . .
H15 H 0.9968 0.5735 0.0975 0.032 Uiso 1 calc . . R
C16 C 0.9433(3) 0.60209(10) 0.3201(3) 0.0238(5) Uani 1 d . . .
C17 C 0.8706(2) 0.58302(9) 0.4454(3) 0.0198(5) Uani 1 d . . .
C18 C 0.8618(3) 0.62388(10) 0.5829(3) 0.0248(5) Uani 1 d . . .
C19 C 0.9228(3) 0.68277(10) 0.5893(3) 0.0311(6) Uani 1 d . . .
H19 H 0.9159 0.7106 0.6800 0.037 Uiso 1 calc . . R
C20 C 0.9928(3) 0.70125(11) 0.4665(3) 0.0336(6) Uani 1 d . . .
H20 H 1.0339 0.7414 0.4735 0.040 Uiso 1 calc . . R
C21 C 1.0033(3) 0.66131(10) 0.3330(3) 0.0297(6) Uani 1 d . . .
H21 H 1.0518 0.6743 0.2491 0.036 Uiso 1 calc . . R
C22 C 0.7872(3) 0.60385(11) 0.7071(3) 0.0297(6) Uani 1 d . . .
H22 H 0.7820 0.6305 0.8010 0.036 Uiso 1 calc . . R
C23 C 0.7245(3) 0.54796(11) 0.6934(3) 0.0301(6) Uani 1 d . . .
H23 H 0.6750 0.5361 0.7773 0.036 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.900(2) . ?
O1 C7 1.221(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.377(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C7 1.502(3) . ?
C7 C8 1.487(3) . ?
C8 C9 1.401(3) . ?
C8 C13 1.415(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 C12 1.422(3) . ?
C11 C23 1.432(3) . ?
C12 C13 1.426(3) . ?
C12 C17 1.423(3) . ?
C13 C14 1.432(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.350(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.416(3) . ?
C16 C17 1.418(3) . ?
C16 C21 1.398(3) . ?
C17 C18 1.418(3) . ?
C18 C19 1.399(3) . ?
C18 C22 1.430(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.345(4) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 119.1(2) . . ?
C6 C1 Br1 119.31(17) . . ?
C6 C1 C2 121.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.8(2) . . ?
C1 C6 C7 122.6(2) . . ?
C5 C6 C7 119.5(2) . . ?
O1 C7 C6 117.6(2) . . ?
O1 C7 C8 124.6(2) . . ?
C8 C7 C6 117.67(19) . . ?
C9 C8 C7 116.9(2) . . ?
C9 C8 C13 119.3(2) . . ?
C13 C8 C7 123.80(19) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 118.8(2) . . ?
C10 C11 C23 122.2(2) . . ?
C12 C11 C23 119.0(2) . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 C17 118.9(2) . . ?
C17 C12 C13 120.6(2) . . ?
C8 C13 C12 118.69(19) . . ?
C8 C13 C14 123.9(2) . . ?
C12 C13 C14 117.4(2) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.9(2) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(2) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 118.6(2) . . ?
C21 C16 C15 122.1(2) . . ?
C21 C16 C17 119.3(2) . . ?
C16 C17 C12 119.8(2) . . ?
C16 C17 C18 119.5(2) . . ?
C18 C17 C12 120.7(2) . . ?
C17 C18 C22 118.6(2) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 C22 122.4(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.3(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C18 C22 H22 119.4 . . ?
C23 C22 C18 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C11 C23 H23 119.2 . . ?
C22 C23 C11 121.6(2) . . ?
C22 C23 H23 119.2 . . ?

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
Br1 C1 C2 C3 177.66(19) . . . . ?
Br1 C1 C6 C5 -176.65(16) . . . . ?
Br1 C1 C6 C7 1.3(3) . . . . ?
O1 C7 C8 C9 -159.5(2) . . . . ?
O1 C7 C8 C13 19.2(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C7 O1 -106.0(3) . . . . ?
C1 C6 C7 C8 77.2(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 -179.5(2) . . . . ?
C5 C6 C7 O1 71.9(3) . . . . ?
C5 C6 C7 C8 -104.9(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C6 C7 C8 C9 17.1(3) . . . . ?
C6 C7 C8 C13 -164.2(2) . . . . ?
C7 C8 C9 C10 177.0(2) . . . . ?
C7 C8 C13 C12 -177.5(2) . . . . ?
C7 C8 C13 C14 5.2(4) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C8 C13 C14 C15 177.7(2) . . . . ?
C9 C8 C13 C12 1.2(3) . . . . ?
C9 C8 C13 C14 -176.1(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C23 179.4(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C10 C11 C12 C17 177.1(2) . . . . ?
C10 C11 C23 C22 -178.3(2) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C11 C12 C13 C14 177.4(2) . . . . ?
C11 C12 C17 C16 -177.9(2) . . . . ?
C11 C12 C17 C18 1.9(3) . . . . ?
C12 C11 C23 C22 1.1(4) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C17 C18 C19 -178.4(2) . . . . ?
C12 C17 C18 C22 -0.2(3) . . . . ?
C13 C8 C9 C10 -1.9(4) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C13 C12 C17 C18 179.5(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C14 C15 C16 C21 -178.7(2) . . . . ?
C15 C16 C17 C12 0.7(3) . . . . ?
C15 C16 C17 C18 -179.1(2) . . . . ?
C15 C16 C21 C20 178.3(2) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C16 C17 C18 C22 179.6(2) . . . . ?
C17 C12 C13 C8 -177.7(2) . . . . ?
C17 C12 C13 C14 -0.2(3) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C17 C18 C22 C23 -1.0(4) . . . . ?
C18 C19 C20 C21 0.3(4) . . . . ?
C18 C22 C23 C11 0.6(4) . . . . ?
C19 C18 C22 C23 177.1(2) . . . . ?
C19 C20 C21 C16 0.1(4) . . . . ?
C21 C16 C17 C12 178.8(2) . . . . ?
C21 C16 C17 C18 -1.0(3) . . . . ?
C22 C18 C19 C20 -179.2(2) . . . . ?
C23 C11 C12 C13 -180.0(2) . . . . ?
C23 C11 C12 C17 -2.3(3) . . . . ?

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1533086'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 I O'
_chemical_formula_sum            'C23 H13 I O'
_chemical_formula_weight         432.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc  '

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

_cell_length_a                   9.8713(5)
_cell_length_b                   21.9189(11)
_cell_length_c                   8.0295(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.165(2)
_cell_angle_gamma                90.00
_cell_volume                     1676.83(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(2)
_cell_measurement_reflns_used    4283
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.28

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      172(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8283
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.31
_reflns_number_total             3024
_reflns_number_gt                2421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0406P)²+0.8630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8647(4) 0.58266(16) 0.9334(5) 0.0213(8) Uani 1 1 d . . .
C2 C 0.8088(4) 0.52229(16) 0.9281(5) 0.0203(8) Uani 1 1 d . . .
C3 C 0.8235(3) 0.48061(16) 0.7955(5) 0.0195(8) Uani 1 1 d . . .
C4 C 0.7622(4) 0.42180(16) 0.7905(5) 0.0196(8) Uani 1 1 d . . .
C5 C 0.6885(4) 0.40702(17) 0.9135(5) 0.0263(9) Uani 1 1 d . . .
H5 H 0.6461 0.3679 0.9087 0.032 Uiso 1 1 calc R . .
C6 C 0.6758(4) 0.44687(18) 1.0396(5) 0.0301(9) Uani 1 1 d . . .
H6 H 0.6262 0.4349 1.1209 0.036 Uiso 1 1 calc R . .
C7 C 0.7350(4) 0.50506(17) 1.0499(5) 0.0255(9) Uani 1 1 d . . .
C8 C 0.7231(4) 0.54785(19) 1.1804(5) 0.0336(10) Uani 1 1 d . . .
H8 H 0.6758 0.5361 1.2643 0.040 Uiso 1 1 calc R . .
C9 C 0.7776(4) 0.60427(18) 1.1862(5) 0.0330(10) Uani 1 1 d . . .
H9 H 0.7688 0.6315 1.2749 0.040 Uiso 1 1 calc R . .
C10 C 0.8485(4) 0.62415(17) 1.0618(5) 0.0249(9) Uani 1 1 d . . .
C11 C 0.9015(4) 0.68356(18) 1.0613(5) 0.0318(10) Uani 1 1 d . . .
H11 H 0.8912 0.7117 1.1470 0.038 Uiso 1 1 calc R . .
C12 C 0.9684(4) 0.70184(19) 0.9387(5) 0.0344(10) Uani 1 1 d . . .
H12 H 1.0034 0.7423 0.9408 0.041 Uiso 1 1 calc R . .
C13 C 0.9847(4) 0.66138(17) 0.8125(6) 0.0322(10) Uani 1 1 d . . .
H13 H 1.0310 0.6743 0.7288 0.039 Uiso 1 1 calc R . .
C14 C 0.9335(4) 0.60184(17) 0.8076(5) 0.0253(9) Uani 1 1 d . . .
C15 C 0.9452(4) 0.55940(18) 0.6782(6) 0.0306(9) Uani 1 1 d . . .
H15 H 0.9908 0.5717 0.5933 0.037 Uiso 1 1 calc R . .
C16 C 0.8935(4) 0.50215(17) 0.6718(5) 0.0259(9) Uani 1 1 d . . .
H16 H 0.9040 0.4755 0.5828 0.031 Uiso 1 1 calc R . .
C17 C 0.7729(4) 0.37407(16) 0.6635(5) 0.0217(8) Uani 1 1 d . . .
C18 C 0.5306(4) 0.32842(17) 0.5454(5) 0.0239(8) Uani 1 1 d . . .
C19 C 0.6696(4) 0.32212(16) 0.6374(5) 0.0202(8) Uani 1 1 d . . .
C20 C 0.7155(4) 0.26472(17) 0.7049(5) 0.0251(8) Uani 1 1 d . . .
H20 H 0.8107 0.2594 0.7677 0.030 Uiso 1 1 calc R . .
C21 C 0.6247(5) 0.21559(18) 0.6816(5) 0.0306(9) Uani 1 1 d . . .
H21 H 0.6571 0.1768 0.7285 0.037 Uiso 1 1 calc R . .
C22 C 0.4870(5) 0.22328(19) 0.5900(5) 0.0363(10) Uani 1 1 d . . .
H22 H 0.4241 0.1897 0.5752 0.044 Uiso 1 1 calc R . .
C23 C 0.4393(4) 0.27890(19) 0.5198(5) 0.0319(10) Uani 1 1 d . . .
H23 H 0.3447 0.2835 0.4541 0.038 Uiso 1 1 calc R . .
I1 I 0.45774(3) 0.412520(12) 0.43097(3) 0.03259(11) Uani 1 1 d . . .
O1 O 0.8629(3) 0.37255(12) 0.5844(4) 0.0318(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.415(5) . ?
C1 C14 1.421(6) . ?
C1 C2 1.430(5) . ?
C2 C7 1.415(5) . ?
C2 C3 1.439(5) . ?
C3 C4 1.420(5) . ?
C3 C16 1.430(5) . ?
C4 C5 1.409(5) . ?
C4 C17 1.484(5) . ?
C5 C6 1.368(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.434(5) . ?
C8 C9 1.345(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.429(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(5) . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.422(6) . ?
C15 C16 1.350(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.220(4) . ?
C17 C19 1.507(5) . ?
C18 C19 1.384(5) . ?
C18 C23 1.391(5) . ?
C18 I1 2.101(4) . ?
C19 C20 1.398(5) . ?
C20 C21 1.383(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.374(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C14 119.6(3) . . ?
C10 C1 C2 120.1(4) . . ?
C14 C1 C2 120.3(3) . . ?
C7 C2 C1 119.4(3) . . ?
C7 C2 C3 120.8(3) . . ?
C1 C2 C3 119.8(3) . . ?
C4 C3 C16 124.0(3) . . ?
C4 C3 C2 118.2(3) . . ?
C16 C3 C2 117.7(3) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 C17 117.5(3) . . ?
C3 C4 C17 123.6(3) . . ?
C6 C5 C4 122.4(3) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.1(4) . . ?
C6 C7 C8 121.8(4) . . ?
C2 C7 C8 119.1(4) . . ?
C9 C8 C7 121.2(4) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.4(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C1 118.7(4) . . ?
C11 C10 C9 122.4(4) . . ?
C1 C10 C9 118.9(3) . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C1 119.6(4) . . ?
C13 C14 C15 122.3(4) . . ?
C1 C14 C15 118.1(3) . . ?
C16 C15 C14 122.3(4) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C3 121.8(4) . . ?
C15 C16 H16 119.1 . . ?
C3 C16 H16 119.1 . . ?
O1 C17 C4 124.7(3) . . ?
O1 C17 C19 117.8(3) . . ?
C4 C17 C19 117.5(3) . . ?
C19 C18 C23 120.9(3) . . ?
C19 C18 I1 119.9(3) . . ?
C23 C18 I1 119.0(3) . . ?
C18 C19 C20 118.2(3) . . ?
C18 C19 C17 122.6(3) . . ?
C20 C19 C17 119.2(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C18 119.5(4) . . ?
C22 C23 H23 120.2 . . ?
C18 C23 H23 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.31
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1533087'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 Br O'
_chemical_formula_sum            'C23 H13 Br O'
_chemical_formula_weight         385.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

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

_cell_length_a                   7.9050(5)
_cell_length_b                   9.5802(5)
_cell_length_c                   10.6200(6)
_cell_angle_alpha                94.977(2)
_cell_angle_beta                 101.008(2)
_cell_angle_gamma                93.532(2)
_cell_volume                     783.98(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3975
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.36

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    2.629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8086
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2852
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0314P)²+0.4307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33994(4) 1.31412(4) 0.51075(3) 0.02848(12) Uani 1 1 d . . .
C1 C 0.8228(4) 0.4549(3) 0.0635(3) 0.0174(7) Uani 1 1 d . . .
C2 C 0.7666(4) 0.5939(3) 0.0630(3) 0.0171(7) Uani 1 1 d . . .
C3 C 0.8241(4) 0.6930(3) 0.1724(3) 0.0159(6) Uani 1 1 d . . .
C4 C 0.7673(4) 0.8297(3) 0.1687(3) 0.0176(7) Uani 1 1 d . . .
C5 C 0.6555(4) 0.8637(3) 0.0596(3) 0.0214(7) Uani 1 1 d . . .
H5 H 0.6161 0.9554 0.0586 0.026 Uiso 1 1 calc R . .
C6 C 0.6007(4) 0.7675(3) -0.0471(3) 0.0224(7) Uani 1 1 d . . .
H6 H 0.5254 0.7939 -0.1205 0.027 Uiso 1 1 calc R . .
C7 C 0.6550(4) 0.6319(3) -0.0479(3) 0.0178(7) Uani 1 1 d . . .
C8 C 0.6046(4) 0.5297(3) -0.1582(3) 0.0236(7) Uani 1 1 d . . .
H8 H 0.5294 0.5539 -0.2327 0.028 Uiso 1 1 calc R . .
C9 C 0.6618(4) 0.4004(3) -0.1582(3) 0.0238(7) Uani 1 1 d . . .
H9 H 0.6275 0.3361 -0.2334 0.029 Uiso 1 1 calc R . .
C10 C 0.7723(4) 0.3570(3) -0.0485(3) 0.0199(7) Uani 1 1 d . . .
C11 C 0.8323(4) 0.2231(3) -0.0456(3) 0.0240(7) Uani 1 1 d . . .
H11 H 0.8005 0.1572 -0.1199 0.029 Uiso 1 1 calc R . .
C12 C 0.9371(4) 0.1850(3) 0.0633(3) 0.0258(8) Uani 1 1 d . . .
H12 H 0.9754 0.0929 0.0633 0.031 Uiso 1 1 calc R . .
C13 C 0.9870(4) 0.2789(3) 0.1724(3) 0.0234(7) Uani 1 1 d . . .
H13 H 1.0596 0.2511 0.2466 0.028 Uiso 1 1 calc R . .
C14 C 0.9312(4) 0.4145(3) 0.1744(3) 0.0196(7) Uani 1 1 d . . .
C15 C 0.9830(4) 0.5166(3) 0.2844(3) 0.0220(7) Uani 1 1 d . . .
H15 H 1.0533 0.4902 0.3602 0.026 Uiso 1 1 calc R . .
C16 C 0.9343(4) 0.6491(3) 0.2830(3) 0.0200(7) Uani 1 1 d . . .
H16 H 0.9739 0.7146 0.3567 0.024 Uiso 1 1 calc R . .
C17 C 0.8343(4) 0.9432(3) 0.2763(3) 0.0199(7) Uani 1 1 d . . .
C18 C 0.4885(4) 1.2011(3) 0.4328(3) 0.0206(7) Uani 1 1 d . . .
C19 C 0.4206(4) 1.0767(3) 0.3603(3) 0.0201(7) Uani 1 1 d . . .
H19 H 0.3007 1.0485 0.3471 0.024 Uiso 1 1 calc R . .
C20 C 0.5327(4) 0.9938(3) 0.3069(3) 0.0187(7) Uani 1 1 d . . .
H20 H 0.4882 0.9085 0.2556 0.022 Uiso 1 1 calc R . .
C21 C 0.7092(4) 1.0337(3) 0.3274(3) 0.0190(7) Uani 1 1 d . . .
C22 C 0.7728(4) 1.1593(3) 0.4021(3) 0.0214(7) Uani 1 1 d . . .
H22 H 0.8930 1.1872 0.4175 0.026 Uiso 1 1 calc R . .
C23 C 0.6624(4) 1.2436(3) 0.4539(3) 0.0251(7) Uani 1 1 d . . .
H23 H 0.7059 1.3301 0.5035 0.030 Uiso 1 1 calc R . .
O1 O 0.9890(3) 0.9638(2) 0.3220(2) 0.0283(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.900(3) . ?
C1 C14 1.417(4) . ?
C1 C10 1.425(4) . ?
C1 C2 1.430(4) . ?
C2 C3 1.419(4) . ?
C2 C7 1.419(4) . ?
C3 C4 1.411(4) . ?
C3 C16 1.433(4) . ?
C4 C5 1.392(4) . ?
C4 C17 1.500(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.437(4) . ?
C8 C9 1.344(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.426(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(4) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.435(4) . ?
C15 C16 1.349(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.223(4) . ?
C17 C21 1.502(4) . ?
C18 C19 1.381(4) . ?
C18 C23 1.380(4) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(4) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C10 119.7(3) . . ?
C14 C1 C2 120.2(3) . . ?
C10 C1 C2 120.1(3) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 119.5(3) . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 C16 122.9(3) . . ?
C2 C3 C16 118.6(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 C17 118.7(3) . . ?
C3 C4 C17 121.4(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.0(3) . . ?
C6 C7 C8 122.3(3) . . ?
C2 C7 C8 118.7(3) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 123.0(3) . . ?
C11 C10 C1 118.6(3) . . ?
C9 C10 C1 118.3(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C1 119.4(3) . . ?
C13 C14 C15 122.3(3) . . ?
C1 C14 C15 118.2(3) . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C3 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C3 C16 H16 119.3 . . ?
O1 C17 C4 121.1(3) . . ?
O1 C17 C21 119.6(3) . . ?
C4 C17 C21 119.3(3) . . ?
C19 C18 C23 121.9(3) . . ?
C19 C18 Br1 119.2(2) . . ?
C23 C18 Br1 118.9(2) . . ?
C18 C19 C20 118.1(3) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C21 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 C17 118.7(3) . . ?
C20 C21 C17 122.3(3) . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C18 119.4(3) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1533090'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H9 F5 O'
_chemical_formula_sum            'C23 H9 F5 O'
_chemical_formula_weight         396.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.9511(5)
_cell_length_b                   8.4125(7)
_cell_length_c                   24.0545(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1609.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2880
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.31

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6997
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2903
_reflns_number_gt                2157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.7981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(11)
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6111(4) 0.7737(4) 0.91931(14) 0.0239(8) Uani 1 1 d . . .
C2 C 0.6945(5) 0.6347(5) 0.90265(16) 0.0290(9) Uani 1 1 d . . .
H2 H 0.6976 0.5460 0.9271 0.035 Uiso 1 1 calc R . .
C3 C 0.7718(5) 0.6243(4) 0.85157(16) 0.0286(9) Uani 1 1 d . . .
H3 H 0.8286 0.5292 0.8415 0.034 Uiso 1 1 calc R . .
C4 C 0.7680(4) 0.7513(5) 0.81434(15) 0.0257(8) Uani 1 1 d . . .
C5 C 0.8408(5) 0.7418(5) 0.75957(15) 0.0302(9) Uani 1 1 d . . .
H5 H 0.8916 0.6450 0.7481 0.036 Uiso 1 1 calc R . .
C6 C 0.8390(5) 0.8645(5) 0.72462(16) 0.0324(10) Uani 1 1 d . . .
H6 H 0.8881 0.8532 0.6888 0.039 Uiso 1 1 calc R . .
C7 C 0.7641(5) 1.0134(5) 0.73997(16) 0.0291(9) Uani 1 1 d . . .
C8 C 0.7625(5) 1.1433(5) 0.70382(17) 0.0354(10) Uani 1 1 d . . .
H8 H 0.8120 1.1339 0.6680 0.042 Uiso 1 1 calc R . .
C9 C 0.6899(5) 1.2848(5) 0.71964(17) 0.0377(11) Uani 1 1 d . . .
H9 H 0.6915 1.3727 0.6949 0.045 Uiso 1 1 calc R . .
C10 C 0.6144(5) 1.3006(5) 0.77130(17) 0.0347(10) Uani 1 1 d . . .
H10 H 0.5649 1.3992 0.7815 0.042 Uiso 1 1 calc R . .
C11 C 0.6102(5) 1.1730(4) 0.80855(16) 0.0268(9) Uani 1 1 d . . .
C12 C 0.5275(5) 1.1800(4) 0.86107(16) 0.0307(9) Uani 1 1 d . . .
H12 H 0.4718 1.2757 0.8712 0.037 Uiso 1 1 calc R . .
C13 C 0.5246(5) 1.0568(4) 0.89707(16) 0.0263(9) Uani 1 1 d . . .
H13 H 0.4669 1.0674 0.9315 0.032 Uiso 1 1 calc R . .
C14 C 0.6090(5) 0.9077(4) 0.88369(14) 0.0229(8) Uani 1 1 d . . .
C15 C 0.6887(4) 0.8963(4) 0.83055(14) 0.0215(8) Uani 1 1 d . . .
C16 C 0.6894(4) 1.0276(4) 0.79314(15) 0.0243(9) Uani 1 1 d . . .
C17 C 0.5331(5) 0.7757(4) 0.97530(15) 0.0284(9) Uani 1 1 d . . .
C18 C 0.5009(5) 0.6170(4) 1.00437(14) 0.0231(8) Uani 1 1 d . . .
C19 C 0.4006(5) 0.4968(4) 0.98262(15) 0.0268(8) Uani 1 1 d . . .
C20 C 0.3628(4) 0.3617(4) 1.01191(16) 0.0269(9) Uani 1 1 d . . .
C21 C 0.4266(4) 0.3414(4) 1.06460(16) 0.0289(9) Uani 1 1 d . . .
C22 C 0.5262(5) 0.4576(5) 1.08756(16) 0.0286(9) Uani 1 1 d . . .
C23 C 0.5613(4) 0.5925(4) 1.05782(15) 0.0271(9) Uani 1 1 d . . .
F1 F 0.3367(3) 0.5109(3) 0.93097(9) 0.0368(6) Uani 1 1 d . . .
F2 F 0.2640(3) 0.2482(3) 0.98983(10) 0.0427(6) Uani 1 1 d . . .
F3 F 0.3950(3) 0.2078(3) 1.09322(10) 0.0448(6) Uani 1 1 d . . .
F4 F 0.5909(3) 0.4376(3) 1.13873(9) 0.0441(7) Uani 1 1 d . . .
F5 F 0.6631(3) 0.7013(3) 1.08099(9) 0.0386(6) Uani 1 1 d . . .
O1 O 0.4951(4) 0.8950(3) 1.00087(11) 0.0484(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.403(5) . ?
C1 C14 1.416(5) . ?
C1 C17 1.483(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C4 C15 1.428(5) . ?
C4 C5 1.441(5) . ?
C5 C6 1.331(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.436(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(5) . ?
C7 C16 1.415(5) . ?
C8 C9 1.377(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(5) . ?
C10 H10 0.9500 . ?
C11 C16 1.425(5) . ?
C11 C12 1.426(5) . ?
C12 C13 1.351(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.459(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.430(5) . ?
C15 C16 1.424(5) . ?
C17 O1 1.215(4) . ?
C17 C18 1.529(5) . ?
C18 C23 1.388(5) . ?
C18 C19 1.390(5) . ?
C19 F1 1.348(4) . ?
C19 C20 1.370(5) . ?
C20 F2 1.346(4) . ?
C20 C21 1.376(5) . ?
C21 F3 1.342(4) . ?
C21 C22 1.374(5) . ?
C22 F4 1.344(4) . ?
C22 C23 1.370(5) . ?
C23 F5 1.344(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
C2 C1 C14 119.8(3) . . ?
C2 C1 C17 117.8(3) . . ?
C14 C1 C17 122.4(3) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C15 119.3(3) . . ?
C3 C4 C5 122.4(4) . . ?
C15 C4 C5 118.3(3) . . ?
C6 C5 C4 122.0(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C16 119.6(4) . . ?
C8 C7 C6 121.8(4) . . ?
C16 C7 C6 118.7(3) . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C16 118.8(4) . . ?
C10 C11 C12 123.2(4) . . ?
C16 C11 C12 118.0(3) . . ?
C13 C12 C11 123.0(3) . . ?
C13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C1 C14 C15 118.9(3) . . ?
C1 C14 C13 123.8(3) . . ?
C15 C14 C13 117.3(3) . . ?
C16 C15 C4 119.2(3) . . ?
C16 C15 C14 121.0(3) . . ?
C4 C15 C14 119.8(3) . . ?
C7 C16 C15 120.5(3) . . ?
C7 C16 C11 119.5(3) . . ?
C15 C16 C11 120.0(3) . . ?
O1 C17 C1 125.0(3) . . ?
O1 C17 C18 116.6(3) . . ?
C1 C17 C18 118.4(3) . . ?
C23 C18 C19 116.0(3) . . ?
C23 C18 C17 119.7(3) . . ?
C19 C18 C17 124.0(3) . . ?
F1 C19 C20 117.7(3) . . ?
F1 C19 C18 119.9(3) . . ?
C20 C19 C18 122.4(3) . . ?
F2 C20 C19 120.9(3) . . ?
F2 C20 C21 119.4(3) . . ?
C19 C20 C21 119.7(3) . . ?
F3 C21 C22 119.8(3) . . ?
F3 C21 C20 120.5(3) . . ?
C22 C21 C20 119.7(3) . . ?
F4 C22 C23 120.2(3) . . ?
F4 C22 C21 120.0(3) . . ?
C23 C22 C21 119.8(3) . . ?
F5 C23 C22 118.1(3) . . ?
F5 C23 C18 119.4(3) . . ?
C22 C23 C18 122.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1533088'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H18 O'
_chemical_formula_sum            'C29 H18 O'
_chemical_formula_weight         382.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab '

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

_cell_length_a                   5.2858(7)
_cell_length_b                   8.2060(11)
_cell_length_c                   42.862(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1859.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5233
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.33

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8476
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         0.95
_diffrn_reflns_theta_max         24.50
_reflns_number_total             1847
_reflns_number_gt                1559
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0869P)²+4.3272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         1847
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1953
_refine_ls_wR_factor_gt          0.1803
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4194(13) 0.9280(7) 0.94039(13) 0.0256(14) Uani 1 1 d . . .
C2 C 0.6163(12) 0.9187(7) 0.91793(12) 0.0216(13) Uani 1 1 d . . .
C3 C 0.6653(11) 0.7678(7) 0.90228(12) 0.0223(13) Uani 1 1 d . . .
C4 C 0.8609(12) 0.7637(7) 0.88001(12) 0.0240(14) Uani 1 1 d . . .
C5 C 1.0069(14) 0.9030(7) 0.87408(13) 0.0267(14) Uani 1 1 d . . .
H5 H 1.1409 0.8982 0.8593 0.032 Uiso 1 1 calc R . .
C6 C 0.9568(12) 1.0478(7) 0.88962(13) 0.0263(14) Uani 1 1 d . . .
H6 H 1.0567 1.1413 0.8853 0.032 Uiso 1 1 calc R . .
C7 C 0.7641(12) 1.0581(7) 0.91127(12) 0.0238(14) Uani 1 1 d . . .
C8 C 0.7052(14) 1.2075(7) 0.92682(13) 0.0299(15) Uani 1 1 d . . .
H8 H 0.8013 1.3024 0.9223 0.036 Uiso 1 1 calc R . .
C9 C 0.5167(14) 1.2160(7) 0.94772(14) 0.0336(16) Uani 1 1 d . . .
H9 H 0.4805 1.3175 0.9574 0.040 Uiso 1 1 calc R . .
C10 C 0.3695(14) 1.0769(8) 0.95569(13) 0.0312(16) Uani 1 1 d . . .
C11 C 0.1768(14) 1.0839(8) 0.97766(13) 0.0351(17) Uani 1 1 d . . .
H11 H 0.1421 1.1838 0.9880 0.042 Uiso 1 1 calc R . .
C12 C 0.0350(13) 0.9473(9) 0.98464(14) 0.0364(17) Uani 1 1 d . . .
H12 H -0.0923 0.9535 1.0002 0.044 Uiso 1 1 calc R . .
C13 C 0.0758(14) 0.8017(9) 0.96920(13) 0.0351(16) Uani 1 1 d . . .
H13 H -0.0287 0.7101 0.9734 0.042 Uiso 1 1 calc R . .
C14 C 0.2705(12) 0.7899(7) 0.94750(13) 0.0262(14) Uani 1 1 d . . .
C15 C 0.3200(13) 0.6433(8) 0.93080(14) 0.0300(15) Uani 1 1 d . . .
H15 H 0.2175 0.5503 0.9347 0.036 Uiso 1 1 calc R . .
C16 C 0.5092(13) 0.6325(7) 0.90952(14) 0.0282(14) Uani 1 1 d . . .
H16 H 0.5378 0.5317 0.8992 0.034 Uiso 1 1 calc R . .
C17 C 0.9418(13) 0.6107(7) 0.86437(12) 0.0255(14) Uani 1 1 d . . .
C18 C 1.0377(12) 0.6226(6) 0.83139(13) 0.0233(13) Uani 1 1 d . . .
C19 C 0.9192(12) 0.7193(7) 0.80963(13) 0.0262(14) Uani 1 1 d . . .
H19 H 0.7812 0.7864 0.8157 0.031 Uiso 1 1 calc R . .
C20 C 1.0009(12) 0.7190(7) 0.77895(13) 0.0263(14) Uani 1 1 d . . .
H20 H 0.9145 0.7841 0.7640 0.032 Uiso 1 1 calc R . .
C21 C 1.2061(12) 0.6258(7) 0.76947(13) 0.0233(13) Uani 1 1 d . . .
C22 C 1.3231(12) 0.5301(8) 0.79171(13) 0.0282(14) Uani 1 1 d . . .
H22 H 1.4640 0.4651 0.7859 0.034 Uiso 1 1 calc R . .
C23 C 1.2393(13) 0.5265(7) 0.82258(13) 0.0290(14) Uani 1 1 d . . .
H23 H 1.3206 0.4583 0.8374 0.035 Uiso 1 1 calc R . .
C24 C 1.2935(12) 0.6275(7) 0.73657(12) 0.0214(13) Uani 1 1 d . . .
C25 C 1.1640(13) 0.7102(8) 0.71340(13) 0.0313(15) Uani 1 1 d . . .
H25 H 1.0164 0.7698 0.7189 0.038 Uiso 1 1 calc R . .
C26 C 1.2409(14) 0.7095(8) 0.68281(14) 0.0333(16) Uani 1 1 d . . .
H26 H 1.1461 0.7666 0.6675 0.040 Uiso 1 1 calc R . .
C27 C 1.4569(13) 0.6253(8) 0.67438(14) 0.0308(15) Uani 1 1 d . . .
H27 H 1.5119 0.6247 0.6533 0.037 Uiso 1 1 calc R . .
C28 C 1.5901(13) 0.5432(9) 0.69660(14) 0.0354(16) Uani 1 1 d . . .
H28 H 1.7380 0.4844 0.6909 0.042 Uiso 1 1 calc R . .
C29 C 1.5112(13) 0.5450(8) 0.72748(14) 0.0302(14) Uani 1 1 d . . .
H29 H 1.6078 0.4886 0.7427 0.036 Uiso 1 1 calc R . .
O1 O 0.9417(9) 0.4798(5) 0.87744(9) 0.0327(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.412(8) . ?
C1 C14 1.413(9) . ?
C1 C2 1.420(8) . ?
C2 C7 1.414(8) . ?
C2 C3 1.432(8) . ?
C3 C4 1.407(8) . ?
C3 C16 1.418(8) . ?
C4 C5 1.402(9) . ?
C4 C17 1.487(8) . ?
C5 C6 1.388(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.430(8) . ?
C8 C9 1.342(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(9) . ?
C11 C12 1.382(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.425(8) . ?
C15 C16 1.356(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O1 1.212(7) . ?
C17 C18 1.505(8) . ?
C18 C19 1.376(8) . ?
C18 C23 1.378(9) . ?
C19 C20 1.384(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(8) . ?
C21 C24 1.484(8) . ?
C22 C23 1.395(8) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.384(8) . ?
C24 C29 1.391(9) . ?
C25 C26 1.373(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.363(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.388(8) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C14 119.3(6) . . ?
C10 C1 C2 119.9(6) . . ?
C14 C1 C2 120.8(5) . . ?
C7 C2 C1 119.9(5) . . ?
C7 C2 C3 120.3(5) . . ?
C1 C2 C3 119.8(5) . . ?
C4 C3 C16 123.9(5) . . ?
C4 C3 C2 118.1(5) . . ?
C16 C3 C2 118.0(5) . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 C17 116.7(5) . . ?
C3 C4 C17 122.5(5) . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 119.6(5) . . ?
C6 C7 C8 121.7(6) . . ?
C2 C7 C8 118.7(5) . . ?
C9 C8 C7 121.2(6) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.6(6) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C1 119.2(6) . . ?
C11 C10 C9 122.1(6) . . ?
C1 C10 C9 118.7(6) . . ?
C12 C11 C10 120.8(6) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.9(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.7(7) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C1 120.1(6) . . ?
C13 C14 C15 122.0(6) . . ?
C1 C14 C15 117.8(5) . . ?
C16 C15 C14 121.9(6) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C3 121.7(6) . . ?
C15 C16 H16 119.1 . . ?
C3 C16 H16 119.1 . . ?
O1 C17 C4 122.7(5) . . ?
O1 C17 C18 119.5(5) . . ?
C4 C17 C18 117.8(5) . . ?
C19 C18 C23 119.8(5) . . ?
C19 C18 C17 121.4(6) . . ?
C23 C18 C17 118.7(5) . . ?
C18 C19 C20 120.1(6) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 121.5(6) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 117.4(5) . . ?
C22 C21 C24 121.5(6) . . ?
C20 C21 C24 121.1(5) . . ?
C21 C22 C23 121.6(6) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C22 119.6(6) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C29 116.5(5) . . ?
C25 C24 C21 122.2(5) . . ?
C29 C24 C21 121.3(5) . . ?
C26 C25 C24 122.4(6) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C27 119.8(6) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C26 119.4(6) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C27 C28 C29 120.4(6) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 121.4(6) . . ?
C28 C29 H29 119.3 . . ?
C24 C29 H29 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        24.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1533089'
_audit_update_record             
;
2017-02-16 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O'
_chemical_formula_sum            'C23 H14 O'
_chemical_formula_weight         306.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

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

_cell_length_a                   8.6959(10)
_cell_length_b                   8.9304(10)
_cell_length_c                   11.2041(13)
_cell_angle_alpha                69.755(4)
_cell_angle_beta                 80.944(4)
_cell_angle_gamma                69.789(4)
_cell_volume                     765.36(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2029
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.43

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6709
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7692
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.55
_reflns_number_total             2815
_reflns_number_gt                1823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2815
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0261(2) 0.34040(19) 0.70653(15) 0.0280(4) Uani 1 1 d . . .
C2 C -0.0859(2) 0.5126(2) 0.64348(15) 0.0328(4) Uani 1 1 d . . .
H2 H -0.1569 0.5519 0.5752 0.039 Uiso 1 1 calc R . .
C3 C -0.0440(2) 0.6273(2) 0.67813(15) 0.0338(4) Uani 1 1 d . . .
H3 H -0.0849 0.7437 0.6325 0.041 Uiso 1 1 calc R . .
C4 C 0.1081(2) 0.6892(2) 0.81525(17) 0.0369(4) Uani 1 1 d . . .
H4 H 0.0721 0.8056 0.7687 0.044 Uiso 1 1 calc R . .
C5 C 0.2051(2) 0.6356(2) 0.91326(17) 0.0382(5) Uani 1 1 d . . .
H5 H 0.2363 0.7150 0.9345 0.046 Uiso 1 1 calc R . .
C6 C 0.3645(2) 0.4015(3) 1.08963(17) 0.0423(5) Uani 1 1 d . . .
H6 H 0.3975 0.4786 1.1125 0.051 Uiso 1 1 calc R . .
C7 C 0.4178(2) 0.2332(3) 1.15828(17) 0.0439(5) Uani 1 1 d . . .
H7 H 0.4857 0.1960 1.2282 0.053 Uiso 1 1 calc R . .
C8 C 0.3734(2) 0.1183(2) 1.12640(16) 0.0395(5) Uani 1 1 d . . .
H8 H 0.4116 0.0025 1.1743 0.047 Uiso 1 1 calc R . .
C9 C 0.2255(2) 0.0552(2) 0.98717(16) 0.0341(4) Uani 1 1 d . . .
H9 H 0.2607 -0.0608 1.0349 0.041 Uiso 1 1 calc R . .
C10 C 0.1322(2) 0.10676(19) 0.88607(15) 0.0307(4) Uani 1 1 d . . .
H10 H 0.1048 0.0260 0.8637 0.037 Uiso 1 1 calc R . .
C11 C 0.11410(19) 0.39983(19) 0.84835(14) 0.0263(4) Uani 1 1 d . . .
C12 C 0.21669(19) 0.3435(2) 0.95337(15) 0.0284(4) Uani 1 1 d . . .
C13 C 0.0573(2) 0.57443(19) 0.77900(15) 0.0293(4) Uani 1 1 d . . .
C14 C 0.2629(2) 0.4614(2) 0.98691(15) 0.0325(4) Uani 1 1 d . . .
C15 C 0.2727(2) 0.1705(2) 1.02430(15) 0.0304(4) Uani 1 1 d . . .
C16 C 0.07362(19) 0.28079(19) 0.81173(14) 0.0252(4) Uani 1 1 d . . .
C17 C -0.0536(2) 0.2205(2) 0.65238(14) 0.0293(4) Uani 1 1 d . . .
C18 C -0.2228(2) 0.2409(2) 0.62301(14) 0.0304(4) Uani 1 1 d . . .
C19 C -0.2414(2) 0.1531(2) 0.54748(16) 0.0370(5) Uani 1 1 d . . .
H19 H -0.1473 0.0897 0.5100 0.044 Uiso 1 1 calc R . .
C20 C -0.3957(3) 0.1580(2) 0.52692(18) 0.0483(5) Uani 1 1 d . . .
H20 H -0.4074 0.0980 0.4753 0.058 Uiso 1 1 calc R . .
C21 C -0.5330(3) 0.2495(3) 0.5810(2) 0.0530(6) Uani 1 1 d . . .
H21 H -0.6386 0.2497 0.5684 0.064 Uiso 1 1 calc R . .
C22 C -0.5179(2) 0.3411(2) 0.65356(18) 0.0509(6) Uani 1 1 d . . .
H22 H -0.6128 0.4064 0.6889 0.061 Uiso 1 1 calc R . .
C23 C -0.3624(2) 0.3367(2) 0.67439(17) 0.0394(5) Uani 1 1 d . . .
H23 H -0.3515 0.3995 0.7240 0.047 Uiso 1 1 calc R . .
O1 O 0.06315(15) 0.10601(14) 0.63162(11) 0.0389(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.395(2) . ?
C1 C16 1.412(2) . ?
C1 C17 1.498(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C13 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.340(2) . ?
C4 C13 1.438(2) . ?
C4 H4 0.9500 . ?
C5 C14 1.434(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(2) . ?
C6 C14 1.400(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C15 1.399(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.350(2) . ?
C9 C15 1.430(2) . ?
C9 H9 0.9500 . ?
C10 C16 1.435(2) . ?
C10 H10 0.9500 . ?
C11 C16 1.424(2) . ?
C11 C13 1.424(2) . ?
C11 C12 1.430(2) . ?
C12 C15 1.417(2) . ?
C12 C14 1.423(2) . ?
C17 O1 1.2265(19) . ?
C17 C18 1.494(2) . ?
C18 C23 1.393(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.393(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C16 119.87(14) . . ?
C2 C1 C17 119.02(14) . . ?
C16 C1 C17 120.76(14) . . ?
C3 C2 C1 121.44(15) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C13 120.81(15) . . ?
C2 C3 H3 119.6 . . ?
C13 C3 H3 119.6 . . ?
C5 C4 C13 121.48(16) . . ?
C5 C4 H4 119.3 . . ?
C13 C4 H4 119.3 . . ?
C4 C5 C14 121.60(15) . . ?
C4 C5 H5 119.2 . . ?
C14 C5 H5 119.2 . . ?
C7 C6 C14 121.39(16) . . ?
C7 C6 H6 119.3 . . ?
C14 C6 H6 119.3 . . ?
C6 C7 C8 120.54(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C15 120.70(17) . . ?
C7 C8 H8 119.7 . . ?
C15 C8 H8 119.7 . . ?
C10 C9 C15 121.80(15) . . ?
C10 C9 H9 119.1 . . ?
C15 C9 H9 119.1 . . ?
C9 C10 C16 121.46(14) . . ?
C9 C10 H10 119.3 . . ?
C16 C10 H10 119.3 . . ?
C16 C11 C13 120.64(14) . . ?
C16 C11 C12 119.83(14) . . ?
C13 C11 C12 119.51(14) . . ?
C15 C12 C14 119.79(15) . . ?
C15 C12 C11 120.24(14) . . ?
C14 C12 C11 119.97(15) . . ?
C3 C13 C11 118.77(14) . . ?
C3 C13 C4 122.47(15) . . ?
C11 C13 C4 118.76(15) . . ?
C6 C14 C12 118.38(16) . . ?
C6 C14 C5 122.95(15) . . ?
C12 C14 C5 118.66(15) . . ?
C8 C15 C12 119.19(15) . . ?
C8 C15 C9 122.46(16) . . ?
C12 C15 C9 118.35(14) . . ?
C1 C16 C11 118.39(14) . . ?
C1 C16 C10 123.31(14) . . ?
C11 C16 C10 118.26(14) . . ?
O1 C17 C18 120.02(15) . . ?
O1 C17 C1 119.87(15) . . ?
C18 C17 C1 120.11(15) . . ?
C23 C18 C19 118.95(16) . . ?
C23 C18 C17 122.21(15) . . ?
C19 C18 C17 118.73(16) . . ?
C20 C19 C18 120.33(19) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.32(18) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.35(18) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 119.5(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 120.52(18) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.55
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039
