# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_san649x
_database_code_depnum_ccdc_archive 'CCDC 943496'
_audit_update_record             
;
2013-06-08 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;







# start Validation Reply Form

_vrf_PLAT220_ALERT_2_B           
;
PROBLEM: Large Non-Solvent    C     Ueq(max)/Ueq(min)   4.2 Ratio
RESPONSE: This alert is mainly occasioned because additional to 
the disorder in the phenylene moiety, there are indications of large amplitude 
movements in one of the Isopropyl fragments, initially we try to treat the case
 as a positional disorder, and although efforts to find suitable positions for 
the components of the disorder where made, the improvements in the refinement 
were not satisfactory and more importantly made little chemical sense. 
Instead, we made use of restrains (in the respective Carbon, Oxygen and Silicon atoms)
to made the anisotropic displacement parameters to be equal in the direction of the bond
between atoms, using the DELU instruction in SHELEX. 
To further improve the geometry of the slightly disordered isopropyl we also applied
the similarity restraint in SHELX for averaging the 1,2-and 1,3 distances with the distances 
found in the other two fragments.
;


# end Validation Reply Form
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-06-05
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------ AUTHOR DETAILS -------------------------------------------#

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

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

_chemical_name_systematic        
;
1,4-bis[(3,3,-diphenyl-3-(3?-(tri-isopropylsylanoxy)-phenyl)-prop-1-yn-1-yl)]-2,3-difluorobenzene
;
_chemical_name_common            
;
1,4-bis[(3,3,-diphenyl-3-(3?-(tri-isopropylsylanoxy)-phenyl)-prop-1-yn-1-yl)]-2,3-difluorobenzene'
;
_chemical_formula_moiety         'C66 H72 F2 O2 Si2'
_chemical_formula_sum            'C66 H72 F2 O2 Si2'
_chemical_formula_weight         991.42
_chemical_compound_source        'synthesis as described'

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

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_IT_number           56

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

_cell_length_a                   25.02220(50)
_cell_length_b                   29.77010(50)
_cell_length_c                   7.49480(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     5582.977(163)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    44750
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2120
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.114
_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  0.9024
_exptl_absorpt_correction_T_max  1.0328

#----------------------------------------------------------------------------#
#                   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  graphite
_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      0.74309E-2
_diffrn_orient_matrix_ub_12      0.122964E-1
_diffrn_orient_matrix_ub_13      0.319064E-1
_diffrn_orient_matrix_ub_21      0.672499E-1
_diffrn_orient_matrix_ub_22      0.324735E-1
_diffrn_orient_matrix_ub_23      -0.9834E-2
_diffrn_orient_matrix_ub_31      -0.114999
_diffrn_orient_matrix_ub_32      0.197847E-1
_diffrn_orient_matrix_ub_33      -0.36891E-2
_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  0.1228
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_number            44573
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             6385
_reflns_number_gt                3446
_reflns_threshold_expression     >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    'SIR2004 (Giacovazzo et al, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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 > 2σ(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)+(0.1237P)²+9.3189P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0054(12)
_refine_ls_number_reflns         6385
_refine_ls_number_parameters     343
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1799
_refine_ls_R_factor_gt           0.0952
_refine_ls_wR_factor_ref         0.2778
_refine_ls_wR_factor_gt          0.2273
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   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'
Si Si 0.0817 0.0704 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.61774(4) 0.36587(4) 0.91519(16) 0.0350(4) Uani 1 1 d U . .
O1 O 0.57079(12) 0.37277(10) 0.7623(5) 0.0585(10) Uani 1 1 d . . .
C20 C 0.43386(15) 0.30789(12) 0.5927(5) 0.0294(9) Uani 1 1 d . . .
H20 H 0.4026 0.2932 0.5508 0.035 Uiso 1 1 calc R . .
C19 C 0.44173(15) 0.35296(12) 0.5550(5) 0.0272(8) Uani 1 1 d . . .
C24 C 0.48776(15) 0.37387(12) 0.6170(6) 0.0331(9) Uani 1 1 d . . .
H24 H 0.4934 0.4048 0.593 0.04 Uiso 1 1 calc R . .
C13 C 0.36368(14) 0.40661(12) 0.5840(5) 0.0288(8) Uani 1 1 d . . .
C7 C 0.36741(15) 0.34964(12) 0.3260(5) 0.0269(8) Uani 1 1 d . . .
C1 C 0.39981(14) 0.38076(12) 0.4517(5) 0.0260(8) Uani 1 1 d . . .
C11 C 0.36718(18) 0.29959(13) 0.0730(5) 0.0376(10) Uani 1 1 d . . .
H11 H 0.3857 0.2857 -0.0229 0.045 Uiso 1 1 calc R . .
C2 C 0.42812(15) 0.41327(13) 0.3357(6) 0.0323(9) Uani 1 1 d . . .
C8 C 0.31388(15) 0.33981(13) 0.3526(5) 0.0336(9) Uani 1 1 d . . .
H8 H 0.2953 0.3535 0.4488 0.04 Uiso 1 1 calc R . .
C12 C 0.39335(16) 0.32947(14) 0.1826(5) 0.0360(10) Uani 1 1 d . . .
H12 H 0.4298 0.3365 0.1599 0.043 Uiso 1 1 calc R . .
C10 C 0.31395(19) 0.28969(14) 0.1024(6) 0.0424(11) Uani 1 1 d . . .
H10 H 0.2959 0.2688 0.0277 0.051 Uiso 1 1 calc R . .
C21 C 0.47113(16) 0.28418(13) 0.6909(6) 0.0373(10) Uani 1 1 d . . .
H21 H 0.4651 0.2533 0.7166 0.045 Uiso 1 1 calc R . .
C23 C 0.52555(16) 0.34996(14) 0.7135(6) 0.0399(10) Uani 1 1 d . . .
C18 C 0.34619(17) 0.44960(14) 0.5487(6) 0.0402(10) Uani 1 1 d . . .
H18 H 0.3568 0.464 0.4412 0.048 Uiso 1 1 calc R . .
C14 C 0.34754(16) 0.38634(14) 0.7431(6) 0.0382(10) Uani 1 1 d . . .
H14 H 0.3591 0.3567 0.7701 0.046 Uiso 1 1 calc R . .
C3 C 0.45058(18) 0.43880(14) 0.2397(7) 0.0442(11) Uani 1 1 d . . .
C9 C 0.28713(18) 0.31038(15) 0.2410(6) 0.0419(11) Uani 1 1 d . . .
H9 H 0.2503 0.3044 0.2598 0.05 Uiso 1 1 calc R . .
C5 C 0.4658(2) 0.46829(15) -0.0608(8) 0.0594(15) Uani 1 1 d D . .
C4 C 0.47631(19) 0.46964(14) 0.1205(7) 0.0500(13) Uani 1 1 d . B .
C22 C 0.51712(17) 0.30479(14) 0.7520(6) 0.0410(10) Uani 1 1 d . . .
H22 H 0.5426 0.2883 0.8194 0.049 Uiso 1 1 calc R . .
C16 C 0.29757(19) 0.45201(17) 0.8217(7) 0.0522(13) Uani 1 1 d . . .
H16 H 0.2747 0.4676 0.9017 0.063 Uiso 1 1 calc R . .
C15 C 0.31481(18) 0.40895(16) 0.8619(6) 0.0472(12) Uani 1 1 d . . .
H15 H 0.3042 0.395 0.9703 0.057 Uiso 1 1 calc R . .
C6 C 0.5111(2) 0.50193(16) 0.1755(8) 0.0584(15) Uani 1 1 d D . .
C17 C 0.3136(2) 0.47199(16) 0.6666(7) 0.0538(13) Uani 1 1 d . . .
H17 H 0.3021 0.5017 0.64 0.065 Uiso 1 1 calc R . .
C32 C 0.6602(2) 0.2998(2) 0.6830(10) 0.0918(17) Uani 1 1 d DU . .
H32A H 0.6798 0.2714 0.676 0.138 Uiso 1 1 calc R A .
H32B H 0.6805 0.3234 0.6221 0.138 Uiso 1 1 calc R . .
H32C H 0.6253 0.2964 0.6255 0.138 Uiso 1 1 calc R . .
C33 C 0.7071(2) 0.3116(2) 0.9711(12) 0.0949(17) Uani 1 1 d DU . .
H33A H 0.729 0.3369 0.9302 0.142 Uiso 1 1 calc R A .
H33B H 0.7255 0.2833 0.9445 0.142 Uiso 1 1 calc R . .
H33C H 0.7014 0.314 1.1001 0.142 Uiso 1 1 calc R . .
C31 C 0.6525(2) 0.31241(18) 0.8741(10) 0.0772(14) Uani 1 1 d DU . .
H31 H 0.6301 0.2883 0.9293 0.093 Uiso 1 1 calc R . .
C30 C 0.6303(3) 0.45925(19) 0.8757(11) 0.090(2) Uani 1 1 d DU . .
H30A H 0.6082 0.4597 0.7679 0.136 Uiso 1 1 calc R A .
H30B H 0.6549 0.4849 0.8741 0.136 Uiso 1 1 calc R . .
H30C H 0.6074 0.4611 0.9814 0.136 Uiso 1 1 calc R . .
C29 C 0.6974(3) 0.4157(2) 0.7124(10) 0.096(2) Uani 1 1 d DU . .
H29A H 0.7197 0.4427 0.7089 0.144 Uiso 1 1 calc R A .
H29B H 0.6747 0.4146 0.6059 0.144 Uiso 1 1 calc R . .
H29C H 0.7203 0.389 0.7155 0.144 Uiso 1 1 calc R . .
C28 C 0.66178(18) 0.41665(15) 0.8814(7) 0.0506(12) Uani 1 1 d DU . .
H28 H 0.6862 0.4186 0.9868 0.061 Uiso 1 1 calc R . .
C26 C 0.5614(3) 0.3236(2) 1.2036(8) 0.0928(19) Uani 1 1 d U A 1
H26A H 0.5896 0.3009 1.2085 0.139 Uiso 1 1 calc R A 1
H26B H 0.5334 0.3139 1.1207 0.139 Uiso 1 1 calc R A 1
H26C H 0.546 0.3276 1.3228 0.139 Uiso 1 1 calc R A 1
C27 C 0.6111(3) 0.3939(3) 1.2791(9) 0.110(2) Uani 1 1 d U A 1
H27A H 0.587 0.3965 1.3815 0.165 Uiso 1 1 calc R A 1
H27B H 0.6201 0.424 1.235 0.165 Uiso 1 1 calc R A 1
H27C H 0.6439 0.3784 1.3158 0.165 Uiso 1 1 calc R A 1
C25 C 0.5851(3) 0.3686(3) 1.1387(8) 0.0990(17) Uani 1 1 d U A 1
H25 H 0.5525 0.3869 1.1142 0.119 Uiso 1 1 calc R A 1
F1 F 0.5179(2) 0.50240(18) 0.3277(7) 0.054(2) Uani 0.511(8) 1 d PD B 1
F1A F 0.4367(2) 0.44033(19) -0.1024(7) 0.053(2) Uani 0.489(8) 1 d PD B 2
H5 H 0.44 0.4446 -0.1001 0.064 Uiso 0.511(8) 1 d P B 1
H6 H 0.5194 0.5041 0.312 0.064 Uiso 0.489(8) 1 d P B 2



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Si1 O1 1.654(3) . ?
Si1 C31 1.840(5) . ?
Si1 C25 1.865(6) . ?
Si1 C28 1.888(5) . ?
O1 C23 1.370(5) . ?
C20 C21 1.382(5) . ?
C20 C19 1.385(5) . ?
C20 H20 0.95 . ?
C19 C24 1.389(5) . ?
C19 C1 1.544(5) . ?
C24 C23 1.387(6) . ?
C24 H24 0.95 . ?
C13 C18 1.378(5) . ?
C13 C14 1.396(6) . ?
C13 C1 1.547(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.392(6) . ?
C7 C1 1.550(5) . ?
C1 C2 1.481(5) . ?
C11 C12 1.376(6) . ?
C11 C10 1.382(6) . ?
C11 H11 0.95 . ?
C2 C3 1.188(6) . ?
C8 C9 1.384(6) . ?
C8 H8 0.95 . ?
C12 H12 0.95 . ?
C10 C9 1.382(6) . ?
C10 H10 0.95 . ?
C21 C22 1.382(6) . ?
C21 H21 0.95 . ?
C23 C22 1.391(6) . ?
C18 C17 1.375(6) . ?
C18 H18 0.95 . ?
C14 C15 1.385(6) . ?
C14 H14 0.95 . ?
C3 C4 1.434(6) . ?
C9 H9 0.95 . ?
C5 F1A 1.149(7) . ?
C5 C6 1.363(6) 5_665 ?
C5 C4 1.385(8) . ?
C5 H5 1.000(6) . ?
C4 C6 1.361(8) . ?
C22 H22 0.95 . ?
C16 C17 1.366(7) . ?
C16 C15 1.386(7) . ?
C16 H16 0.95 . ?
C15 H15 0.95 . ?
C6 F1 1.154(7) . ?
C6 C5 1.363(6) 5_665 ?
C6 H6 1.046(6) . ?
C17 H17 0.95 . ?
C32 C31 1.493(9) . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 C31 1.548(8) . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C31 H31 1 . ?
C30 C28 1.493(7) . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C29 C28 1.549(8) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C28 H28 1 . ?
C26 C25 1.543(9) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 C25 1.448(9) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C25 H25 1 . ?
F1 H6 0.133(5) . ?
F1A H5 0.153(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


O1 Si1 C31 109.1(2) . . ?
O1 Si1 C25 107.8(3) . . ?
C31 Si1 C25 113.2(4) . . ?
O1 Si1 C28 102.83(19) . . ?
C31 Si1 C28 113.2(2) . . ?
C25 Si1 C28 109.9(3) . . ?
C23 O1 Si1 135.3(3) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C19 C24 118.9(3) . . ?
C20 C19 C1 121.7(3) . . ?
C24 C19 C1 119.4(3) . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C18 C13 C14 118.3(4) . . ?
C18 C13 C1 121.6(3) . . ?
C14 C13 C1 120.1(3) . . ?
C8 C7 C12 118.1(4) . . ?
C8 C7 C1 123.0(3) . . ?
C12 C7 C1 118.9(3) . . ?
C2 C1 C19 108.6(3) . . ?
C2 C1 C13 109.3(3) . . ?
C19 C1 C13 110.0(3) . . ?
C2 C1 C7 106.5(3) . . ?
C19 C1 C7 109.9(3) . . ?
C13 C1 C7 112.4(3) . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C3 C2 C1 178.7(5) . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C11 C12 C7 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
O1 C23 C24 116.6(4) . . ?
O1 C23 C22 123.3(4) . . ?
C24 C23 C22 120.1(4) . . ?
C17 C18 C13 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C2 C3 C4 178.3(5) . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
F1A C5 C6 124.7(7) . 5_665 ?
F1A C5 C4 114.0(5) . . ?
C6 C5 C4 121.3(6) 5_665 . ?
C6 C5 H5 123.1(6) 5_665 . ?
C4 C5 H5 115.6(4) . . ?
C6 C4 C5 116.0(4) . . ?
C6 C4 C3 123.4(5) . . ?
C5 C4 C3 120.5(5) . . ?
C21 C22 C23 119.1(4) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
F1 C6 C4 113.7(5) . . ?
F1 C6 C5 123.6(7) . 5_665 ?
C4 C6 C5 122.6(6) . 5_665 ?
C4 C6 H6 117.8(4) . . ?
C5 C6 H6 119.5(6) 5_665 . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C31 C33 109.4(5) . . ?
C32 C31 Si1 116.0(5) . . ?
C33 C31 Si1 110.7(4) . . ?
C32 C31 H31 106.7 . . ?
C33 C31 H31 106.7 . . ?
Si1 C31 H31 106.7 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C30 C28 C29 107.2(5) . . ?
C30 C28 Si1 112.1(4) . . ?
C29 C28 Si1 115.5(4) . . ?
C30 C28 H28 107.2 . . ?
C29 C28 H28 107.2 . . ?
Si1 C28 H28 107.2 . . ?
C27 C25 C26 113.3(6) . . ?
C27 C25 Si1 118.6(5) . . ?
C26 C25 Si1 114.5(4) . . ?
C27 C25 H25 102.5 . . ?
C26 C25 H25 102.5 . . ?
Si1 C25 H25 102.5 . . ?



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





C31 Si1 O1 C23 61.7(5) . . . . ?
C25 Si1 O1 C23 -61.7(5) . . . . ?
C28 Si1 O1 C23 -177.9(5) . . . . ?
C21 C20 C19 C24 0.2(6) . . . . ?
C21 C20 C19 C1 -177.7(4) . . . . ?
C20 C19 C24 C23 0.7(6) . . . . ?
C1 C19 C24 C23 178.6(4) . . . . ?
C20 C19 C1 C2 -144.0(4) . . . . ?
C24 C19 C1 C2 38.1(5) . . . . ?
C20 C19 C1 C13 96.3(4) . . . . ?
C24 C19 C1 C13 -81.5(4) . . . . ?
C20 C19 C1 C7 -27.9(5) . . . . ?
C24 C19 C1 C7 154.2(3) . . . . ?
C18 C13 C1 C2 22.7(5) . . . . ?
C14 C13 C1 C2 -157.8(4) . . . . ?
C18 C13 C1 C19 142.0(4) . . . . ?
C14 C13 C1 C19 -38.6(5) . . . . ?
C18 C13 C1 C7 -95.3(4) . . . . ?
C14 C13 C1 C7 84.1(4) . . . . ?
C8 C7 C1 C2 -131.2(4) . . . . ?
C12 C7 C1 C2 50.7(4) . . . . ?
C8 C7 C1 C19 111.3(4) . . . . ?
C12 C7 C1 C19 -66.8(4) . . . . ?
C8 C7 C1 C13 -11.5(5) . . . . ?
C12 C7 C1 C13 170.4(3) . . . . ?
C12 C7 C8 C9 0.8(6) . . . . ?
C1 C7 C8 C9 -177.3(4) . . . . ?
C10 C11 C12 C7 1.2(6) . . . . ?
C8 C7 C12 C11 -1.9(6) . . . . ?
C1 C7 C12 C11 176.3(3) . . . . ?
C12 C11 C10 C9 0.7(6) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
Si1 O1 C23 C24 159.9(4) . . . . ?
Si1 O1 C23 C22 -21.8(8) . . . . ?
C19 C24 C23 O1 177.2(4) . . . . ?
C19 C24 C23 C22 -1.2(7) . . . . ?
C14 C13 C18 C17 -0.1(6) . . . . ?
C1 C13 C18 C17 179.3(4) . . . . ?
C18 C13 C14 C15 0.0(6) . . . . ?
C1 C13 C14 C15 -179.4(4) . . . . ?
C11 C10 C9 C8 -1.8(6) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
F1A C5 C4 C6 179.2(5) . . . . ?
C6 C5 C4 C6 -0.7(8) 5_665 . . . ?
F1A C5 C4 C3 -1.8(7) . . . . ?
C6 C5 C4 C3 178.3(4) 5_665 . . . ?
C20 C21 C22 C23 0.0(7) . . . . ?
O1 C23 C22 C21 -177.4(4) . . . . ?
C24 C23 C22 C21 0.9(7) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C17 C16 C15 C14 -0.9(7) . . . . ?
C5 C4 C6 F1 178.6(5) . . . . ?
C3 C4 C6 F1 -0.3(8) . . . . ?
C5 C4 C6 C5 0.7(8) . . . 5_665 ?
C3 C4 C6 C5 -178.3(4) . . . 5_665 ?
C15 C16 C17 C18 0.8(7) . . . . ?
C13 C18 C17 C16 -0.3(7) . . . . ?
O1 Si1 C31 C32 36.2(5) . . . . ?
C25 Si1 C31 C32 156.3(4) . . . . ?
C28 Si1 C31 C32 -77.7(5) . . . . ?
O1 Si1 C31 C33 161.6(5) . . . . ?
C25 Si1 C31 C33 -78.3(6) . . . . ?
C28 Si1 C31 C33 47.7(6) . . . . ?
O1 Si1 C28 C30 49.8(5) . . . . ?
C31 Si1 C28 C30 167.4(5) . . . . ?
C25 Si1 C28 C30 -64.8(6) . . . . ?
O1 Si1 C28 C29 -73.4(5) . . . . ?
C31 Si1 C28 C29 44.2(5) . . . . ?
C25 Si1 C28 C29 171.9(5) . . . . ?
O1 Si1 C25 C27 -137.0(7) . . . . ?
C31 Si1 C25 C27 102.2(7) . . . . ?
C28 Si1 C25 C27 -25.6(8) . . . . ?
O1 Si1 C25 C26 85.1(7) . . . . ?
C31 Si1 C25 C26 -35.8(7) . . . . ?
C28 Si1 C25 C26 -163.5(6) . . . . ?

# 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 943497'
_audit_update_record             
;
2013-06-08 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;
#TrackingRef '- Rho-1(cif).txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H38 Cl2 N4 O3'
_chemical_formula_weight         633.59

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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)/n

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

_cell_length_a                   14.119(4)
_cell_length_b                   15.494(5)
_cell_length_c                   15.319(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.080(5)
_cell_angle_gamma                90.00
_cell_volume                     3235.8(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3107
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.89

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1336
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9646
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_process_details   SADABS

_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  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15949
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0959
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5705
_reflns_number_gt                3701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0969P)²+0.8345P] 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         5705
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1737
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.76258(15) 0.10859(16) 0.48318(15) 0.0203(6) Uani 1 1 d . . .
O2 O 0.83917(16) 0.48502(16) 0.59266(15) 0.0218(6) Uani 1 1 d . . .
O3 O 0.61961(18) 0.15089(18) 0.92304(16) 0.0285(6) Uani 1 1 d . . .
H3 H 0.6264 0.0977 0.9160 0.043 Uiso 1 1 calc R . .
N1 N 1.09198(19) 0.0377(2) 0.64267(18) 0.0222(7) Uani 1 1 d . . .
H1A H 1.1258 0.0668 0.6937 0.027 Uiso 1 1 calc R . .
H1B H 1.1365 0.0262 0.6097 0.027 Uiso 1 1 calc R . .
N2 N 0.42979(19) 0.1499(2) 0.31137(19) 0.0241(7) Uani 1 1 d . . .
H2A H 0.4129 0.1617 0.2504 0.029 Uiso 1 1 calc R . .
H2B H 0.3897 0.1834 0.3363 0.029 Uiso 1 1 calc R . .
N3 N 0.80060(18) 0.34787(19) 0.53596(17) 0.0159(6) Uani 1 1 d . . .
N4 N 0.77865(18) 0.30764(19) 0.60986(17) 0.0171(7) Uani 1 1 d . . .
C1 C 0.8136(2) 0.2897(2) 0.4604(2) 0.0152(7) Uani 1 1 d . . .
C2 C 0.8882(2) 0.2196(2) 0.4994(2) 0.0160(8) Uani 1 1 d . . .
C3 C 0.9884(2) 0.2392(2) 0.5315(2) 0.0182(8) Uani 1 1 d . . .
H3A H 1.0098 0.2957 0.5217 0.022 Uiso 1 1 calc R . .
C4 C 1.0573(2) 0.1802(2) 0.5765(2) 0.0198(8) Uani 1 1 d . . .
C5 C 1.0255(2) 0.0954(2) 0.5925(2) 0.0181(8) Uani 1 1 d . . .
C6 C 0.9261(2) 0.0748(2) 0.5583(2) 0.0179(8) Uani 1 1 d . . .
H6 H 0.9039 0.0181 0.5660 0.022 Uiso 1 1 calc R . .
C7 C 0.8594(2) 0.1367(2) 0.5130(2) 0.0160(8) Uani 1 1 d . . .
C8 C 0.6943(2) 0.1652(2) 0.4314(2) 0.0168(8) Uani 1 1 d . . .
C9 C 0.6000(2) 0.1301(2) 0.3970(2) 0.0178(8) Uani 1 1 d . . .
H9 H 0.5878 0.0716 0.4089 0.021 Uiso 1 1 calc R . .
C10 C 0.5244(2) 0.1812(2) 0.3454(2) 0.0190(8) Uani 1 1 d . . .
C11 C 0.5435(2) 0.2687(2) 0.3293(2) 0.0177(8) Uani 1 1 d . . .
C12 C 0.6378(2) 0.3001(2) 0.3640(2) 0.0175(8) Uani 1 1 d . . .
H12 H 0.6510 0.3585 0.3524 0.021 Uiso 1 1 calc R . .
C13 C 0.7148(2) 0.2493(2) 0.4156(2) 0.0160(8) Uani 1 1 d . . .
C14 C 1.1645(2) 0.2046(3) 0.6118(3) 0.0282(9) Uani 1 1 d . . .
H14A H 1.1750 0.2627 0.5907 0.042 Uiso 1 1 calc R . .
H14B H 1.2052 0.1632 0.5895 0.042 Uiso 1 1 calc R . .
H14C H 1.1827 0.2037 0.6781 0.042 Uiso 1 1 calc R . .
C15 C 1.0644(2) -0.0447(2) 0.6729(2) 0.0235(8) Uani 1 1 d . . .
H15A H 1.0392 -0.0828 0.6201 0.028 Uiso 1 1 calc R . .
H15B H 1.0112 -0.0362 0.7034 0.028 Uiso 1 1 calc R . .
C16 C 1.1512(3) -0.0872(3) 0.7376(3) 0.0316(9) Uani 1 1 d . . .
H16A H 1.2015 -0.1002 0.7059 0.047 Uiso 1 1 calc R . .
H16B H 1.1300 -0.1408 0.7607 0.047 Uiso 1 1 calc R . .
H16C H 1.1785 -0.0480 0.7882 0.047 Uiso 1 1 calc R . .
C17 C 0.4016(2) 0.0609(2) 0.3205(2) 0.0244(9) Uani 1 1 d . . .
H17A H 0.4559 0.0226 0.3150 0.029 Uiso 1 1 calc R . .
H17B H 0.3438 0.0470 0.2702 0.029 Uiso 1 1 calc R . .
C18 C 0.3775(3) 0.0422(3) 0.4088(3) 0.0349(10) Uani 1 1 d . . .
H18A H 0.4337 0.0572 0.4591 0.052 Uiso 1 1 calc R . .
H18B H 0.3626 -0.0194 0.4120 0.052 Uiso 1 1 calc R . .
H18C H 0.3204 0.0764 0.4128 0.052 Uiso 1 1 calc R . .
C19 C 0.4621(2) 0.3265(3) 0.2772(2) 0.0241(8) Uani 1 1 d . . .
H19A H 0.4879 0.3847 0.2734 0.036 Uiso 1 1 calc R . .
H19B H 0.4096 0.3290 0.3083 0.036 Uiso 1 1 calc R . .
H19C H 0.4359 0.3034 0.2161 0.036 Uiso 1 1 calc R . .
C20 C 0.8489(2) 0.3571(2) 0.4034(2) 0.0165(8) Uani 1 1 d . . .
C21 C 0.8604(2) 0.4373(2) 0.4458(2) 0.0178(8) Uani 1 1 d . . .
C22 C 0.8915(2) 0.5095(2) 0.4071(2) 0.0199(8) Uani 1 1 d . . .
H22 H 0.8994 0.5637 0.4371 0.024 Uiso 1 1 calc R . .
C23 C 0.9109(2) 0.5001(3) 0.3233(2) 0.0237(9) Uani 1 1 d . . .
H23 H 0.9325 0.5483 0.2953 0.028 Uiso 1 1 calc R . .
C24 C 0.8987(2) 0.4202(3) 0.2801(2) 0.0235(9) Uani 1 1 d . . .
H24 H 0.9114 0.4151 0.2223 0.028 Uiso 1 1 calc R . .
C25 C 0.8685(2) 0.3474(2) 0.3194(2) 0.0200(8) Uani 1 1 d . . .
H25 H 0.8614 0.2930 0.2898 0.024 Uiso 1 1 calc R . .
C26 C 0.8334(2) 0.4295(2) 0.5335(2) 0.0179(8) Uani 1 1 d . . .
C27 C 0.7059(2) 0.3385(2) 0.6369(2) 0.0206(8) Uani 1 1 d . . .
C28 C 0.6837(2) 0.2902(3) 0.7129(2) 0.0214(8) Uani 1 1 d . . .
C29 C 0.6435(2) 0.3296(3) 0.7769(2) 0.0261(9) Uani 1 1 d . . .
H29 H 0.6302 0.3898 0.7727 0.031 Uiso 1 1 calc R . .
C30 C 0.6225(2) 0.2821(2) 0.8471(2) 0.0231(9) Uani 1 1 d . . .
H30 H 0.5964 0.3102 0.8908 0.028 Uiso 1 1 calc R . .
C31 C 0.6397(2) 0.1945(3) 0.8531(2) 0.0232(9) Uani 1 1 d . . .
C32 C 0.6788(2) 0.1538(2) 0.7891(2) 0.0217(8) Uani 1 1 d . . .
H32 H 0.6904 0.0933 0.7930 0.026 Uiso 1 1 calc R . .
C33 C 0.7007(2) 0.2001(3) 0.7202(2) 0.0213(8) Uani 1 1 d . . .
H33 H 0.7274 0.1715 0.6772 0.026 Uiso 1 1 calc R . .
C34 C 0.6430(2) 0.4148(3) 0.5979(3) 0.0290(9) Uani 1 1 d . . .
H34A H 0.6708 0.4673 0.6303 0.044 Uiso 1 1 calc R . .
H34B H 0.5764 0.4059 0.6044 0.044 Uiso 1 1 calc R . .
H34C H 0.6407 0.4207 0.5337 0.044 Uiso 1 1 calc R . .
Cl1 Cl 0.44563(9) 0.21936(9) 0.59722(8) 0.0603(4) Uani 1 1 d . . .
Cl2 Cl 0.36968(9) 0.37967(9) 0.50474(9) 0.0585(4) Uani 1 1 d . . .
C35 C 0.3754(4) 0.2672(3) 0.4980(3) 0.0510(13) Uani 1 1 d . . .
H35A H 0.4036 0.2515 0.4473 0.061 Uiso 1 1 calc R . .
H35B H 0.3079 0.2436 0.4843 0.061 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.389(4) . ?
O1 C7 1.393(4) . ?
O2 C26 1.237(4) . ?
O3 C31 1.358(4) . ?
O3 H3 0.8400 . ?
N1 C5 1.376(4) . ?
N1 C15 1.446(5) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
N2 C10 1.388(4) . ?
N2 C17 1.452(5) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N3 C26 1.351(4) . ?
N3 N4 1.396(4) . ?
N3 C1 1.514(4) . ?
N4 C27 1.295(4) . ?
C1 C13 1.521(4) . ?
C1 C2 1.523(5) . ?
C1 C20 1.525(5) . ?
C2 C7 1.378(5) . ?
C2 C3 1.406(4) . ?
C3 C4 1.382(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.429(5) . ?
C4 C14 1.518(5) . ?
C5 C6 1.401(4) . ?
C6 C7 1.396(5) . ?
C6 H6 0.9500 . ?
C8 C13 1.370(5) . ?
C8 C9 1.408(4) . ?
C9 C10 1.397(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.417(5) . ?
C11 C12 1.387(4) . ?
C11 C19 1.512(5) . ?
C12 C13 1.406(5) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.512(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.507(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.392(5) . ?
C20 C25 1.394(4) . ?
C21 C22 1.390(5) . ?
C21 C26 1.494(4) . ?
C22 C23 1.387(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C27 C28 1.485(5) . ?
C27 C34 1.506(5) . ?
C28 C29 1.394(5) . ?
C28 C33 1.416(5) . ?
C29 C30 1.398(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.377(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.395(5) . ?
C32 C33 1.377(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
Cl1 C35 1.749(4) . ?
Cl2 C35 1.749(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

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
C8 O1 C7 117.7(3) . . ?
C31 O3 H3 109.5 . . ?
C5 N1 C15 123.4(3) . . ?
C5 N1 H1A 106.5 . . ?
C15 N1 H1A 106.5 . . ?
C5 N1 H1B 106.5 . . ?
C15 N1 H1B 106.5 . . ?
H1A N1 H1B 106.5 . . ?
C10 N2 C17 123.8(3) . . ?
C10 N2 H2A 106.4 . . ?
C17 N2 H2A 106.4 . . ?
C10 N2 H2B 106.4 . . ?
C17 N2 H2B 106.4 . . ?
H2A N2 H2B 106.5 . . ?
C26 N3 N4 126.2(3) . . ?
C26 N3 C1 115.1(2) . . ?
N4 N3 C1 116.8(3) . . ?
C27 N4 N3 117.2(3) . . ?
N3 C1 C13 108.1(2) . . ?
N3 C1 C2 109.5(2) . . ?
C13 C1 C2 110.0(3) . . ?
N3 C1 C20 98.8(3) . . ?
C13 C1 C20 114.9(3) . . ?
C2 C1 C20 114.7(2) . . ?
C7 C2 C3 117.3(3) . . ?
C7 C2 C1 121.6(3) . . ?
C3 C2 C1 120.8(3) . . ?
C4 C3 C2 123.0(3) . . ?
C4 C3 H3A 118.5 . . ?
C2 C3 H3A 118.5 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C14 121.3(3) . . ?
C5 C4 C14 119.8(3) . . ?
N1 C5 C6 122.1(3) . . ?
N1 C5 C4 119.6(3) . . ?
C6 C5 C4 118.3(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C7 O1 123.0(3) . . ?
C2 C7 C6 121.8(3) . . ?
O1 C7 C6 115.2(3) . . ?
C13 C8 O1 123.7(3) . . ?
C13 C8 C9 121.6(3) . . ?
O1 C8 C9 114.7(3) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C10 C9 122.3(3) . . ?
N2 C10 C11 118.5(3) . . ?
C9 C10 C11 119.2(3) . . ?
C12 C11 C10 118.5(3) . . ?
C12 C11 C19 121.1(3) . . ?
C10 C11 C19 120.4(3) . . ?
C11 C12 C13 122.9(3) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C8 C13 C12 117.6(3) . . ?
C8 C13 C1 121.5(3) . . ?
C12 C13 C1 120.5(3) . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 110.7(3) . . ?
N1 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 113.7(3) . . ?
N2 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N2 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 120.0(3) . . ?
C21 C20 C1 111.1(3) . . ?
C25 C20 C1 128.9(3) . . ?
C22 C21 C20 122.1(3) . . ?
C22 C21 C26 129.2(3) . . ?
C20 C21 C26 108.7(3) . . ?
C23 C22 C21 118.1(3) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 121.8(3) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C20 C25 C24 117.8(3) . . ?
C20 C25 H25 121.1 . . ?
C24 C25 H25 121.1 . . ?
O2 C26 N3 126.1(3) . . ?
O2 C26 C21 128.2(3) . . ?
N3 C26 C21 105.7(3) . . ?
N4 C27 C28 114.4(3) . . ?
N4 C27 C34 126.8(3) . . ?
C28 C27 C34 118.9(3) . . ?
C29 C28 C33 118.0(3) . . ?
C29 C28 C27 122.6(4) . . ?
C33 C28 C27 119.4(3) . . ?
C28 C29 C30 121.1(4) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
O3 C31 C30 118.3(3) . . ?
O3 C31 C32 122.1(4) . . ?
C30 C31 C32 119.6(3) . . ?
C33 C32 C31 120.8(4) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C28 120.5(3) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
C27 C34 H34A 109.5 . . ?
C27 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C27 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
Cl2 C35 Cl1 113.3(3) . . ?
Cl2 C35 H35A 108.9 . . ?
Cl1 C35 H35A 108.9 . . ?
Cl2 C35 H35B 108.9 . . ?
Cl1 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?

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
C26 N3 N4 C27 65.3(4) . . . . ?
C1 N3 N4 C27 -131.1(3) . . . . ?
C26 N3 C1 C13 -127.4(3) . . . . ?
N4 N3 C1 C13 67.2(3) . . . . ?
C26 N3 C1 C2 112.8(3) . . . . ?
N4 N3 C1 C2 -52.6(3) . . . . ?
C26 N3 C1 C20 -7.5(3) . . . . ?
N4 N3 C1 C20 -172.9(2) . . . . ?
N3 C1 C2 C7 101.9(3) . . . . ?
C13 C1 C2 C7 -16.8(4) . . . . ?
C20 C1 C2 C7 -148.1(3) . . . . ?
N3 C1 C2 C3 -71.6(3) . . . . ?
C13 C1 C2 C3 169.7(3) . . . . ?
C20 C1 C2 C3 38.4(4) . . . . ?
C7 C2 C3 C4 -1.2(5) . . . . ?
C1 C2 C3 C4 172.6(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C2 C3 C4 C14 -178.6(3) . . . . ?
C15 N1 C5 C6 -7.0(5) . . . . ?
C15 N1 C5 C4 171.1(3) . . . . ?
C3 C4 C5 N1 -175.5(3) . . . . ?
C14 C4 C5 N1 2.3(5) . . . . ?
C3 C4 C5 C6 2.7(5) . . . . ?
C14 C4 C5 C6 -179.5(3) . . . . ?
N1 C5 C6 C7 175.6(3) . . . . ?
C4 C5 C6 C7 -2.6(5) . . . . ?
C3 C2 C7 O1 -178.9(3) . . . . ?
C1 C2 C7 O1 7.4(4) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
C1 C2 C7 C6 -172.4(3) . . . . ?
C8 O1 C7 C2 5.3(4) . . . . ?
C8 O1 C7 C6 -175.0(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C6 C7 O1 -179.2(3) . . . . ?
C7 O1 C8 C13 -6.5(4) . . . . ?
C7 O1 C8 C9 174.7(3) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
O1 C8 C9 C10 178.7(3) . . . . ?
C17 N2 C10 C9 -4.2(5) . . . . ?
C17 N2 C10 C11 177.7(3) . . . . ?
C8 C9 C10 N2 -178.9(3) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
N2 C10 C11 C12 179.4(3) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
N2 C10 C11 C19 0.9(4) . . . . ?
C9 C10 C11 C19 -177.3(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C19 C11 C12 C13 177.6(3) . . . . ?
O1 C8 C13 C12 -178.3(3) . . . . ?
C9 C8 C13 C12 0.5(4) . . . . ?
O1 C8 C13 C1 -5.0(5) . . . . ?
C9 C8 C13 C1 173.8(3) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C11 C12 C13 C1 -173.3(3) . . . . ?
N3 C1 C13 C8 -103.9(3) . . . . ?
C2 C1 C13 C8 15.6(4) . . . . ?
C20 C1 C13 C8 146.9(3) . . . . ?
N3 C1 C13 C12 69.2(4) . . . . ?
C2 C1 C13 C12 -171.3(3) . . . . ?
C20 C1 C13 C12 -40.0(4) . . . . ?
C5 N1 C15 C16 -171.6(3) . . . . ?
C10 N2 C17 C18 84.5(4) . . . . ?
N3 C1 C20 C21 4.2(3) . . . . ?
C13 C1 C20 C21 118.9(3) . . . . ?
C2 C1 C20 C21 -112.1(3) . . . . ?
N3 C1 C20 C25 -175.3(3) . . . . ?
C13 C1 C20 C25 -60.6(4) . . . . ?
C2 C1 C20 C25 68.4(4) . . . . ?
C25 C20 C21 C22 -0.2(5) . . . . ?
C1 C20 C21 C22 -179.8(3) . . . . ?
C25 C20 C21 C26 179.3(3) . . . . ?
C1 C20 C21 C26 -0.2(3) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C26 C21 C22 C23 -179.1(3) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C21 C20 C25 C24 -0.5(4) . . . . ?
C1 C20 C25 C24 179.0(3) . . . . ?
C23 C24 C25 C20 1.0(5) . . . . ?
N4 N3 C26 O2 -8.5(5) . . . . ?
C1 N3 C26 O2 -172.4(3) . . . . ?
N4 N3 C26 C21 171.5(3) . . . . ?
C1 N3 C26 C21 7.7(3) . . . . ?
C22 C21 C26 O2 -4.9(5) . . . . ?
C20 C21 C26 O2 175.6(3) . . . . ?
C22 C21 C26 N3 175.0(3) . . . . ?
C20 C21 C26 N3 -4.4(3) . . . . ?
N3 N4 C27 C28 177.3(3) . . . . ?
N3 N4 C27 C34 -1.1(5) . . . . ?
N4 C27 C28 C29 150.2(3) . . . . ?
C34 C27 C28 C29 -31.3(5) . . . . ?
N4 C27 C28 C33 -31.8(4) . . . . ?
C34 C27 C28 C33 146.8(3) . . . . ?
C33 C28 C29 C30 1.3(5) . . . . ?
C27 C28 C29 C30 179.4(3) . . . . ?
C28 C29 C30 C31 -1.2(5) . . . . ?
C29 C30 C31 O3 179.1(3) . . . . ?
C29 C30 C31 C32 0.4(5) . . . . ?
O3 C31 C32 C33 -178.4(3) . . . . ?
C30 C31 C32 C33 0.3(5) . . . . ?
C31 C32 C33 C28 -0.2(5) . . . . ?
C29 C28 C33 C32 -0.6(5) . . . . ?
C27 C28 C33 C32 -178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_san183a
_database_code_depnum_ccdc_archive 'CCDC 943819'
_audit_update_record             
;
2013-06-10 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;
#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#
#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2013-06-10
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------ AUTHOR DETAILS -------------------------------------------#

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene acetone solvate
;
_chemical_name_common            
;
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene acetone solvate
;
_chemical_formula_moiety         'C48 H34 O2, 2(C3 H6 O)'
_chemical_formula_sum            'C54 H46 O4'
_chemical_formula_weight         758.91
_chemical_compound_source        'synthesis as described'

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

_space_group_crystal_system      triclinic

_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'





_cell_length_a                   8.95120(29)
_cell_length_b                   10.13470(40)
_cell_length_c                   13.22790(50)
_cell_angle_alpha                79.9847(17)
_cell_angle_beta                 74.7185(17)
_cell_angle_gamma                64.7483(19)

_cell_volume                     1044.358(69)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4030
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.075
_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  0.97
_exptl_absorpt_correction_T_max  0.996

#----------------------------------------------------------------------------#
#                   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  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.106816
_diffrn_orient_matrix_ub_12      -0.165368E-1
_diffrn_orient_matrix_ub_13      0.217713E-1
_diffrn_orient_matrix_ub_21      0.480902E-1
_diffrn_orient_matrix_ub_22      -0.760013E-1
_diffrn_orient_matrix_ub_23      0.552574E-1
_diffrn_orient_matrix_ub_31      -0.475106E-1
_diffrn_orient_matrix_ub_32      0.768871E-1
_diffrn_orient_matrix_ub_33      0.514289E-1
_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  0.0675
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_number            7523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.818
_diffrn_measured_fraction_theta_max 0.818
_reflns_number_total             4604
_reflns_number_gt                2732
_reflns_threshold_expression     >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 (Nonius BV, 1997-2000)'
_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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 > 2σ(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)+(0.1370P)²+0.1737P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.16(4)
_refine_ls_number_reflns         4604
_refine_ls_number_parameters     299
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.2174
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1229(3) 0.0421(2) 0.77434(17) 0.0417(5) Uani 1 1 d . . .
C2 C 0.0962(3) 0.1616(2) 0.83665(18) 0.0461(6) Uani 1 1 d . . .
C3 C 0.0698(3) 0.2602(3) 0.88610(19) 0.0482(6) Uani 1 1 d . . .
C4 C 0.0358(3) 0.3807(2) 0.94431(17) 0.0429(6) Uani 1 1 d . . .
C5 C -0.1180(3) 0.4413(3) 1.01389(19) 0.0484(6) Uani 1 1 d . . .
C6 C 0.1539(3) 0.4419(3) 0.9309(2) 0.0504(6) Uani 1 1 d . . .
C7 C -0.0510(3) 0.0336(2) 0.79129(17) 0.0442(6) Uani 1 1 d . . .
C8 C -0.0798(4) -0.0897(3) 0.8317(2) 0.0589(7) Uani 1 1 d . . .
H8 H 0.0083 -0.1742 0.8497 0.071 Uiso 1 1 calc R . .
C9 C -0.2387(4) -0.0897(4) 0.8459(3) 0.0749(9) Uani 1 1 d . . .
H9 H -0.2561 -0.174 0.8737 0.09 Uiso 1 1 calc R . .
C10 C -0.3704(4) 0.0330(4) 0.8195(2) 0.0732(9) Uani 1 1 d . B .
H10 H -0.4766 0.0321 0.8289 0.088 Uiso 1 1 calc R . .
C12 C -0.1855(3) 0.1579(3) 0.7654(2) 0.0562(7) Uani 1 1 d . B .
H12 H -0.1689 0.2428 0.7385 0.067 Uiso 1 1 calc R . .
C13 C 0.1861(3) 0.0799(2) 0.65671(17) 0.0434(6) Uani 1 1 d . . .
C14 C 0.2859(3) 0.1596(3) 0.6271(2) 0.0517(6) Uani 1 1 d . C .
H14 H 0.3108 0.1949 0.6781 0.062 Uiso 1 1 calc R . .
C16 C 0.3144(4) 0.1359(3) 0.4444(2) 0.0667(8) Uani 1 1 d . C .
H16 H 0.3565 0.1552 0.3738 0.08 Uiso 1 1 calc R . .
C17 C 0.2167(4) 0.0558(4) 0.4733(2) 0.0690(8) Uani 1 1 d . . .
H17 H 0.1941 0.0195 0.4218 0.083 Uiso 1 1 calc R . .
C18 C 0.1515(3) 0.0285(3) 0.5783(2) 0.0560(7) Uani 1 1 d . . .
H18 H 0.0842 -0.0246 0.5965 0.067 Uiso 1 1 calc R . .
C19 C 0.2581(3) -0.1024(2) 0.81148(18) 0.0437(6) Uani 1 1 d . . .
C20 C 0.3425(4) -0.2182(3) 0.7475(2) 0.0601(7) Uani 1 1 d . A .
H20 H 0.3162 -0.2089 0.6824 0.072 Uiso 1 1 calc R . .
C22 C 0.5074(4) -0.3636(3) 0.8733(3) 0.0676(8) Uani 1 1 d . A .
H22 H 0.5919 -0.4495 0.8935 0.081 Uiso 1 1 calc R . .
C23 C 0.4231(4) -0.2513(3) 0.9380(2) 0.0684(8) Uani 1 1 d . . .
H23 H 0.4498 -0.2617 1.003 0.082 Uiso 1 1 calc R . .
C24 C 0.2983(3) -0.1218(3) 0.9082(2) 0.0555(7) Uani 1 1 d . . .
H24 H 0.2411 -0.0474 0.954 0.067 Uiso 1 1 calc R . .
O1A O 0.5415(9) -0.4602(5) 0.7129(5) 0.109(3) Uani 0.478(8) 1 d P A 1
O1B O -0.4682(8) 0.2688(8) 0.7531(8) 0.096(4) Uani 0.321(8) 1 d P B 2
O1C O 0.4378(14) 0.2721(11) 0.4980(10) 0.083(5) Uani 0.201(9) 1 d P C 3
C11 C 0.4654(4) -0.3476(3) 0.7786(2) 0.0686(8) Uani 1 1 d . . .
C21 C -0.3439(4) 0.1575(4) 0.7788(2) 0.0673(8) Uani 1 1 d . . .
C15 C 0.3487(3) 0.1868(3) 0.5214(2) 0.0641(8) Uani 1 1 d . . .
O2 O 0.3138(10) 0.4929(9) 0.6464(6) 0.236(3) Uani 1 1 d D . .
C27 C 0.0322(14) 0.5664(9) 0.6677(7) 0.214(4) Uani 1 1 d D . .
H27A H 0.0468 0.4702 0.6995 0.321 Uiso 1 1 calc R . .
H27B H -0.0498 0.5982 0.6247 0.321 Uiso 1 1 calc R . .
H27C H -0.0062 0.633 0.7215 0.321 Uiso 1 1 calc R . .
C26 C 0.1933(14) 0.5630(6) 0.6027(8) 0.167(3) Uani 1 1 d D . .
C25 C 0.1986(15) 0.6123(9) 0.4954(8) 0.294(8) Uani 1 1 d D . .
H25A H 0.3124 0.598 0.4605 0.441 Uiso 1 1 calc R . .
H25B H 0.1264 0.7144 0.4898 0.441 Uiso 1 1 calc R . .
H25C H 0.1606 0.558 0.463 0.441 Uiso 1 1 calc R . .
HO1A H 0.4666 -0.4762 0.6918 0.17(6) Uiso 0.478(8) 1 d P A 1
H21 H -0.43 0.2373 0.7565 0.199 Uiso 0.522(8) 1 d P A 1
HO1B H -0.462 0.3617 0.7491 0.08(3) Uiso 0.321(8) 1 d P B 2
H11 H 0.5214 -0.4209 0.733 0.101 Uiso 0.679(8) 1 d P B 2
HO1C H 0.3819 0.3452 0.5311 0.09(6) Uiso 0.201(9) 1 d P C 3
H15 H 0.4195 0.2366 0.5013 0.11 Uiso 0.799(9) 1 d P C 3
H5 H -0.200(4) 0.406(3) 1.020(2) 0.059(7) Uiso 1 1 d . . .
H6 H 0.254(4) 0.406(3) 0.887(2) 0.066(8) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.483(3) . ?
C1 C19 1.549(3) . ?
C1 C13 1.550(3) . ?
C1 C7 1.550(3) . ?
C2 C3 1.195(3) . ?
C3 C4 1.436(3) . ?
C4 C5 1.388(3) . ?
C4 C6 1.398(3) . ?
C5 C6 1.375(3) 2_567 ?
C5 H5 0.93(3) . ?
C6 C5 1.375(3) 2_567 ?
C6 H6 0.89(3) . ?
C7 C8 1.373(3) . ?
C7 C12 1.388(3) . ?
C8 C9 1.384(4) . ?
C8 H8 0.93 . ?
C9 C10 1.368(5) . ?
C9 H9 0.93 . ?
C10 C21 1.376(4) . ?
C10 H10 0.93 . ?
C12 C21 1.383(4) . ?
C12 H12 0.93 . ?
C13 C14 1.387(3) . ?
C13 C18 1.392(3) . ?
C14 C15 1.389(4) . ?
C14 H14 0.93 . ?
C16 C15 1.372(4) . ?
C16 C17 1.375(4) . ?
C16 H16 0.93 . ?
C17 C18 1.387(4) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 C24 1.378(3) . ?
C19 C20 1.384(3) . ?
C20 C11 1.385(4) . ?
C20 H20 0.93 . ?
C22 C23 1.364(5) . ?
C22 C11 1.366(4) . ?
C22 H22 0.93 . ?
C23 C24 1.388(4) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
O1A C11 1.375(6) . ?
O1A HO1A 0.872(9) . ?
O1A H11 0.461(6) . ?
O1B C21 1.273(7) . ?
O1B H21 0.361(7) . ?
O1B HO1B 0.959(7) . ?
O1C C15 1.358(10) . ?
O1C HO1C 0.820(11) . ?
O1C H15 0.446(10) . ?
C11 H11 0.919(3) . ?
C21 H21 0.916(3) . ?
C15 H15 0.930(3) . ?
O2 C26 1.239(8) . ?
C27 C26 1.460(12) . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
C26 C25 1.417(11) . ?
C25 H25A 0.96 . ?
C25 H25B 0.96 . ?
C25 H25C 0.96 . ?

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 C19 109.24(17) . . ?
C2 C1 C13 109.08(17) . . ?
C19 C1 C13 109.23(17) . . ?
C2 C1 C7 106.69(18) . . ?
C19 C1 C7 112.38(17) . . ?
C13 C1 C7 110.15(17) . . ?
C3 C2 C1 177.9(2) . . ?
C2 C3 C4 178.9(3) . . ?
C5 C4 C6 118.4(2) . . ?
C5 C4 C3 120.3(2) . . ?
C6 C4 C3 121.3(2) . . ?
C6 C5 C4 121.2(2) 2_567 . ?
C6 C5 H5 119.6(18) 2_567 . ?
C4 C5 H5 119.1(17) . . ?
C5 C6 C4 120.4(2) 2_567 . ?
C5 C6 H6 118.6(19) 2_567 . ?
C4 C6 H6 121.0(19) . . ?
C8 C7 C12 118.1(2) . . ?
C8 C7 C1 123.6(2) . . ?
C12 C7 C1 118.3(2) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C21 119.3(3) . . ?
C9 C10 H10 120.4 . . ?
C21 C10 H10 120.4 . . ?
C21 C12 C7 121.1(2) . . ?
C21 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C14 C13 C18 118.4(2) . . ?
C14 C13 C1 120.7(2) . . ?
C18 C13 C1 120.8(2) . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C24 C19 C20 117.5(2) . . ?
C24 C19 C1 122.2(2) . . ?
C20 C19 C1 120.3(2) . . ?
C19 C20 C11 121.2(2) . . ?
C19 C20 H20 119.4 . . ?
C11 C20 H20 119.4 . . ?
C23 C22 C11 118.8(3) . . ?
C23 C22 H22 120.6 . . ?
C11 C22 H22 120.6 . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C19 C24 C23 120.7(3) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C11 O1A HO1A 111.2(5) . . ?
C11 O1A H11 7.0(7) . . ?
HO1A O1A H11 116.7(12) . . ?
C21 O1B H21 8.1(12) . . ?
C21 O1B HO1B 116.4(6) . . ?
H21 O1B HO1B 115.2(13) . . ?
C15 O1C HO1C 107.3(9) . . ?
C15 O1C H15 13.5(9) . . ?
HO1C O1C H15 120.7(17) . . ?
C22 C11 O1A 120.9(4) . . ?
C22 C11 C20 120.5(3) . . ?
O1A C11 C20 118.6(4) . . ?
C22 C11 H11 120.6(3) . . ?
O1A C11 H11 3.5(4) . . ?
C20 C11 H11 118.8(3) . . ?
O1B C21 C10 117.7(4) . . ?
O1B C21 C12 122.4(4) . . ?
C10 C21 C12 119.9(3) . . ?
O1B C21 H21 3.2(4) . . ?
C10 C21 H21 119.1(3) . . ?
C12 C21 H21 120.8(3) . . ?
O1C C15 C16 121.7(6) . . ?
O1C C15 C14 117.0(6) . . ?
C16 C15 C14 121.2(3) . . ?
O1C C15 H15 6.4(5) . . ?
C16 C15 H15 118.3(3) . . ?
C14 C15 H15 120.4(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O2 C26 C25 128.0(12) . . ?
O2 C26 C27 113.1(10) . . ?
C25 C26 C27 117.7(8) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

# 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_gg2010s
_database_code_depnum_ccdc_archive 'CCDC 943820'
_audit_update_record             
;
2013-06-10 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene dimethylsulfoxide solvate
;
_chemical_name_common            
;
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene dimethylsulfoxide solvate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H34 O, 2(C2 H6 O S)'
_chemical_formula_sum            'C52 H46 O3 S2'
_chemical_formula_weight         783.01

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'
S S 0.1246 0.1234 '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                   8.7172(7)
_cell_length_b                   9.9498(8)
_cell_length_c                   13.1689(11)
_cell_angle_alpha                86.0670(10)
_cell_angle_beta                 74.4410(10)
_cell_angle_gamma                65.9120(09)
_cell_volume                     1003.44(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7472
_cell_measurement_theta_min      3.84
_cell_measurement_theta_max      30.35

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   'Sadabs (Bruker)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14025
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         30.70
_reflns_number_total             5671
_reflns_number_gt                5112
_reflns_threshold_expression     >2sigma(I)

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

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

_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)+(0.0570P)²+0.8779P] 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         5671
_refine_ls_number_parameters     295
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.009

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
S1 S 0.71532(8) 0.59274(5) 0.37027(4) 0.03562(15) Uani 0.9420(14) 1 d PD A 1
O26 O 0.6943(2) 0.45341(17) 0.35602(12) 0.0379(3) Uani 0.9420(14) 1 d PD A 1
C28 C 0.6697(5) 0.6233(4) 0.5086(2) 0.0599(8) Uani 0.9420(14) 1 d PD A 1
H28A H 0.7776 0.5750 0.5307 0.072 Uiso 0.9420(14) 1 calc PR A 1
H28B H 0.5859 0.5824 0.5456 0.072 Uiso 0.9420(14) 1 calc PR A 1
H28C H 0.6203 0.7294 0.5257 0.072 Uiso 0.9420(14) 1 calc PR A 1
C27 C 0.9418(3) 0.5481(2) 0.33665(18) 0.0393(5) Uani 0.9420(14) 1 d PD A 1
H27A H 0.9986 0.4634 0.3760 0.047 Uiso 0.9420(14) 1 calc PR A 1
H27B H 0.9614 0.6327 0.3546 0.047 Uiso 0.9420(14) 1 calc PR A 1
H27C H 0.9909 0.5234 0.2608 0.047 Uiso 0.9420(14) 1 calc PR A 1
S1A S 0.6306(13) 0.5899(9) 0.4084(7) 0.03562(15) Uani 0.0580(14) 1 d PD A 2
O26A O 0.618(3) 0.448(2) 0.4016(19) 0.0379(3) Uani 0.0580(14) 1 d PD A 2
C27A C 0.845(3) 0.570(4) 0.335(2) 0.0393(5) Uani 0.0580(14) 1 d PD A 2
H27D H 0.9148 0.5630 0.3838 0.047 Uiso 0.0580(14) 1 calc PR A 2
H27E H 0.8366 0.6556 0.2917 0.047 Uiso 0.0580(14) 1 calc PR A 2
H27F H 0.9005 0.4803 0.2890 0.047 Uiso 0.0580(14) 1 calc PR A 2
C28A C 0.647(7) 0.616(6) 0.5359(16) 0.0599(8) Uani 0.0580(14) 1 d PD A 2
H28D H 0.7639 0.6084 0.5314 0.072 Uiso 0.0580(14) 1 calc PR A 2
H28E H 0.6243 0.5400 0.5813 0.072 Uiso 0.0580(14) 1 calc PR A 2
H28F H 0.5606 0.7135 0.5657 0.072 Uiso 0.0580(14) 1 calc PR A 2
O1 O -0.1922(5) 1.2840(4) 0.5095(3) 0.0295(8) Uani 0.29 1 d PD B 1
H1O H -0.2244 1.3116 0.4541 0.044 Uiso 0.29 1 calc PR B 1
C1 C 0.18144(17) 1.43640(15) -0.02536(11) 0.0179(3) Uani 1 1 d . . .
H1 H 0.3051 1.3930 -0.0428 0.022 Uiso 1 1 calc R . .
C2 C 0.08615(18) 1.38035(14) 0.05596(10) 0.0164(2) Uani 1 1 d . . .
C3 C -0.09650(18) 1.44538(15) 0.08049(11) 0.0184(3) Uani 1 1 d . . .
H3 H -0.1623 1.4081 0.1353 0.022 Uiso 1 1 calc R . .
C4 C 0.17482(18) 1.25875(15) 0.11409(11) 0.0188(3) Uani 1 1 d . . .
C5 C 0.24720(18) 1.15906(15) 0.16385(11) 0.0176(2) Uani 1 1 d . . .
C6 C 0.33899(17) 1.03712(14) 0.22560(10) 0.0150(2) Uani 1 1 d . . .
C7 C 0.52418(17) 1.03246(15) 0.20781(10) 0.0163(2) Uani 1 1 d . . .
C8 C 0.67479(19) 0.90833(17) 0.16767(12) 0.0222(3) Uani 1 1 d . . .
H8 H 0.6670 0.8209 0.1498 0.027 Uiso 1 1 calc R . .
C9 C 0.8384(2) 0.9114(2) 0.15334(13) 0.0289(3) Uani 1 1 d . . .
H9 H 0.9410 0.8264 0.1248 0.035 Uiso 1 1 calc R . .
C10 C 0.8515(2) 1.0374(2) 0.18053(13) 0.0287(3) Uani 1 1 d . D .
H10 H 0.9628 1.0389 0.1708 0.034 Uiso 1 1 calc R . .
C11 C 0.7015(2) 1.16161(19) 0.22215(12) 0.0257(3) Uani 1 1 d D . .
H11 H 0.7098 1.2479 0.2421 0.031 Uiso 0.92 1 calc PR C 1
O1B O 0.756(2) 1.2532(19) 0.2415(14) 0.039(4) Uani 0.08 1 d PD D 2
H1B H 0.6708 1.3320 0.2671 0.058 Uiso 0.08 1 calc PR D 2
C12 C 0.53899(19) 1.15944(16) 0.23461(11) 0.0205(3) Uani 1 1 d . D .
H12 H 0.4367 1.2454 0.2617 0.025 Uiso 1 1 calc R . .
C13 C 0.34315(16) 0.89101(14) 0.18813(10) 0.0154(2) Uani 1 1 d . . .
C14 C 0.33065(19) 0.87301(16) 0.08703(11) 0.0214(3) Uani 1 1 d . . .
H14 H 0.3208 0.9509 0.0398 0.026 Uiso 1 1 calc R . .
C15 C 0.3325(2) 0.74183(17) 0.05444(12) 0.0250(3) Uani 1 1 d . . .
H15 H 0.3222 0.7318 -0.0144 0.030 Uiso 1 1 calc R . .
C16 C 0.34925(19) 0.62591(17) 0.12135(12) 0.0234(3) Uani 1 1 d . F .
H16 H 0.3491 0.5371 0.0991 0.028 Uiso 1 1 calc R . .
C17 C 0.3662(2) 0.64108(16) 0.22110(12) 0.0243(3) Uani 1 1 d D . .
H17 H 0.3810 0.5614 0.2669 0.029 Uiso 0.87 1 calc PR E 1
O1A O 0.4139(14) 0.5211(9) 0.2754(7) 0.0298(19) Uani 0.13 1 d PD F 2
H1A H 0.4202 0.5431 0.3342 0.045 Uiso 0.13 1 calc PR F 2
C18 C 0.3615(2) 0.77323(16) 0.25438(11) 0.0212(3) Uani 1 1 d . F .
H18 H 0.3710 0.7830 0.3234 0.025 Uiso 1 1 calc R . .
C19 C 0.24252(17) 1.07053(14) 0.34425(10) 0.0154(2) Uani 1 1 d . . .
C20 C 0.33176(18) 1.00826(15) 0.42125(11) 0.0185(3) Uani 1 1 d . . .
H20 H 0.4534 0.9492 0.4005 0.022 Uiso 1 1 calc R . .
C21 C 0.2438(2) 1.03212(17) 0.52786(11) 0.0219(3) Uani 1 1 d . . .
H21 H 0.3052 0.9874 0.5793 0.026 Uiso 1 1 calc R . .
C22 C 0.0664(2) 1.12116(16) 0.55962(11) 0.0223(3) Uani 1 1 d . B .
H22 H 0.0065 1.1377 0.6325 0.027 Uiso 1 1 calc R . .
C23 C -0.02217(19) 1.18553(16) 0.48381(12) 0.0218(3) Uani 1 1 d D . .
H23 H -0.1428 1.2478 0.5050 0.026 Uiso 0.71 1 calc PR B 2
C24 C 0.06476(18) 1.15940(15) 0.37658(11) 0.0184(3) Uani 1 1 d . B .
H24 H 0.0023 1.2025 0.3253 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O26 1.5006(16) . ?
S1 C27 1.770(2) . ?
S1 C28 1.777(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S1A O26A 1.465(15) . ?
S1A C28A 1.767(16) . ?
S1A C27A 1.794(15) . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
O1 C23 1.364(4) . ?
O1 H1O 0.8400 . ?
C1 C3 1.3854(18) 2_585 ?
C1 C2 1.4024(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.4035(19) . ?
C2 C4 1.4402(18) . ?
C3 C1 1.3854(18) 2_585 ?
C3 H3 0.9500 . ?
C4 C5 1.197(2) . ?
C5 C6 1.4815(18) . ?
C6 C19 1.5483(18) . ?
C6 C7 1.5494(18) . ?
C6 C13 1.5504(18) . ?
C7 C8 1.3864(19) . ?
C7 C12 1.3987(19) . ?
C8 C9 1.400(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 O1B 1.253(14) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
O1B H1B 0.8400 . ?
C12 H12 0.9500 . ?
C13 C18 1.3934(19) . ?
C13 C14 1.3940(19) . ?
C14 C15 1.394(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 O1A 1.321(8) . ?
C17 C18 1.396(2) . ?
C17 H17 0.9500 . ?
O1A H1A 0.8400 . ?
C18 H18 0.9500 . ?
C19 C24 1.3941(18) . ?
C19 C20 1.4003(18) . ?
C20 C21 1.3911(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O26 S1 C27 106.99(9) . . ?
O26 S1 C28 106.00(12) . . ?
C27 S1 C28 98.46(14) . . ?
S1 C28 H28A 109.5 . . ?
S1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
S1 C28 H28C 109.4 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
S1 C27 H27A 109.5 . . ?
S1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
S1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O26A S1A C28A 108.8(13) . . ?
O26A S1A C27A 108.2(11) . . ?
C28A S1A C27A 98.4(12) . . ?
S1A C27A H27D 109.6 . . ?
S1A C27A H27E 109.4 . . ?
H27D C27A H27E 109.5 . . ?
S1A C27A H27F 109.4 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
S1A C28A H28D 109.1 . . ?
S1A C28A H28E 109.2 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C23 O1 H1O 109.5 . . ?
C3 C1 C2 120.48(12) 2_585 . ?
C3 C1 H1 119.8 2_585 . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.08(12) . . ?
C1 C2 C4 120.33(12) . . ?
C3 C2 C4 120.59(12) . . ?
C1 C3 C2 120.45(12) 2_585 . ?
C1 C3 H3 119.8 2_585 . ?
C2 C3 H3 119.8 . . ?
C5 C4 C2 178.96(15) . . ?
C4 C5 C6 178.88(15) . . ?
C5 C6 C19 109.34(10) . . ?
C5 C6 C7 106.75(11) . . ?
C19 C6 C7 109.10(10) . . ?
C5 C6 C13 109.35(11) . . ?
C19 C6 C13 110.00(10) . . ?
C7 C6 C13 112.21(10) . . ?
C8 C7 C12 118.83(13) . . ?
C8 C7 C6 123.07(12) . . ?
C12 C7 C6 118.09(12) . . ?
C7 C8 C9 120.25(14) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.43(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.74(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
O1B C11 C10 104.5(9) . . ?
O1B C11 C12 135.7(9) . . ?
C10 C11 C12 119.82(15) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 O1B H1B 109.5 . . ?
C11 C12 C7 120.89(14) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 118.10(13) . . ?
C18 C13 C6 120.82(12) . . ?
C14 C13 C6 121.08(12) . . ?
C13 C14 C15 120.67(13) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.71(14) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.17(14) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O1A C17 C16 117.6(4) . . ?
O1A C17 C18 121.4(4) . . ?
C16 C17 C18 120.14(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 O1A H1A 109.5 . . ?
C13 C18 C17 121.18(13) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C24 C19 C20 118.73(12) . . ?
C24 C19 C6 120.87(12) . . ?
C20 C19 C6 120.38(11) . . ?
C21 C20 C19 120.56(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.41(13) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.32(13) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O1 C23 C22 122.3(2) . . ?
O1 C23 C24 117.0(2) . . ?
C22 C23 C24 120.50(13) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 120.46(13) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?

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
C3 C1 C2 C3 0.2(2) 2_585 . . . ?
C3 C1 C2 C4 -179.14(13) 2_585 . . . ?
C1 C2 C3 C1 -0.2(2) . . . 2_585 ?
C4 C2 C3 C1 179.13(13) . . . 2_585 ?
C5 C6 C7 C8 -122.71(14) . . . . ?
C19 C6 C7 C8 119.24(14) . . . . ?
C13 C6 C7 C8 -2.93(18) . . . . ?
C5 C6 C7 C12 57.90(15) . . . . ?
C19 C6 C7 C12 -60.15(15) . . . . ?
C13 C6 C7 C12 177.68(11) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C6 C7 C8 C9 179.91(13) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 O1B 177.8(8) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
O1B C11 C12 C7 -177.1(12) . . . . ?
C10 C11 C12 C7 1.4(2) . . . . ?
C8 C7 C12 C11 -0.5(2) . . . . ?
C6 C7 C12 C11 178.96(12) . . . . ?
C5 C6 C13 C18 -156.25(13) . . . . ?
C19 C6 C13 C18 -36.16(16) . . . . ?
C7 C6 C13 C18 85.49(15) . . . . ?
C5 C6 C13 C14 24.47(17) . . . . ?
C19 C6 C13 C14 144.57(13) . . . . ?
C7 C6 C13 C14 -93.78(14) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
C6 C13 C14 C15 -179.27(13) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 O1A -167.7(5) . . . . ?
C15 C16 C17 C18 1.8(2) . . . . ?
C14 C13 C18 C17 -0.4(2) . . . . ?
C6 C13 C18 C17 -179.69(13) . . . . ?
O1A C17 C18 C13 167.9(6) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C5 C6 C19 C24 26.71(17) . . . . ?
C7 C6 C19 C24 143.12(12) . . . . ?
C13 C6 C19 C24 -93.39(14) . . . . ?
C5 C6 C19 C20 -155.13(12) . . . . ?
C7 C6 C19 C20 -38.71(16) . . . . ?
C13 C6 C19 C20 84.78(15) . . . . ?
C24 C19 C20 C21 1.4(2) . . . . ?
C6 C19 C20 C21 -176.83(12) . . . . ?
C19 C20 C21 C22 -1.5(2) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C21 C22 C23 O1 -174.1(3) . . . . ?
C21 C22 C23 C24 1.1(2) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C6 C19 C24 C23 178.18(12) . . . . ?
O1 C23 C24 C19 174.3(2) . . . . ?
C22 C23 C24 C19 -1.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.908
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_gg3604sm
_database_code_depnum_ccdc_archive 'CCDC 943821'
_audit_update_record             
;
2013-06-10 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene methanol solvate
;
_chemical_name_common            
;
1,4-bis-(([3-hydroxy-diphenyl]-phenylmethyl)-ethynyl)-phenylene methanol solvate
;
_chemical_melting_point          
;
523-525 
;
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H25 O6'
_chemical_formula_weight         697.68

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

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

_cell_length_a                   8.5248(10)
_cell_length_b                   8.5869(10)
_cell_length_c                   14.1894(17)
_cell_angle_alpha                75.054(2)
_cell_angle_beta                 80.680(2)
_cell_angle_gamma                70.627(2)
_cell_volume                     943.39(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    393(2)
_cell_measurement_reflns_used    4674
_cell_measurement_theta_min      2.542
_cell_measurement_theta_max      28.276

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             361
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   'Sadabs (Bruker)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      393(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8564
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4437
_reflns_number_gt                3695
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_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)+(0.0614P)²+0.3652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4437
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
O1S O 0.61755(15) 0.31786(14) 0.08834(8) 0.0359(3) Uani 1 1 d . . .
H1S H 0.5275 0.3294 0.0696 0.054 Uiso 1 1 calc R . .
O1 O 0.69544(14) 0.58877(13) -0.01940(7) 0.0303(2) Uani 1 1 d . . .
H1 H 0.6886 0.5002 0.0178 0.045 Uiso 1 1 calc R . .
C1 C 0.35042(16) 1.10628(16) 0.46239(9) 0.0206(3) Uani 1 1 d . . .
H1A H 0.2509 1.1774 0.4369 0.025 Uiso 1 1 calc R . .
C2 C 0.46522(16) 1.00005(16) 0.40788(9) 0.0207(3) Uani 1 1 d . . .
H2 H 0.4416 0.9998 0.3462 0.025 Uiso 1 1 calc R . .
C3 C 0.61662(15) 0.89286(15) 0.44432(9) 0.0178(2) Uani 1 1 d . . .
C4 C 0.73729(15) 0.78729(15) 0.38543(9) 0.0185(2) Uani 1 1 d . . .
C5 C 0.83686(15) 0.70355(15) 0.33414(8) 0.0168(2) Uani 1 1 d . . .
C6 C 0.95528(14) 0.60601(14) 0.26579(8) 0.0149(2) Uani 1 1 d . . .
C7 C 0.88419(14) 0.68528(15) 0.16461(8) 0.0167(2) Uani 1 1 d . . .
C8 C 0.82980(15) 0.59470(15) 0.11567(9) 0.0183(2) Uani 1 1 d . . .
H8 H 0.8426 0.4805 0.1415 0.022 Uiso 1 1 calc R . .
C9 C 0.75588(16) 0.67441(17) 0.02775(9) 0.0218(3) Uani 1 1 d . . .
C10 C 0.73814(17) 0.84323(18) -0.01253(9) 0.0260(3) Uani 1 1 d . . .
H10 H 0.6889 0.8959 -0.0711 0.031 Uiso 1 1 calc R . .
C11 C 0.79479(19) 0.93317(17) 0.03566(10) 0.0280(3) Uani 1 1 d . . .
H11 H 0.7852 1.0464 0.0085 0.034 Uiso 1 1 calc R . .
C12 C 0.86561(17) 0.85614(16) 0.12387(10) 0.0235(3) Uani 1 1 d . . .
H12 H 0.9009 0.9186 0.1561 0.028 Uiso 1 1 calc R . .
C13 C 0.96842(15) 0.41673(15) 0.29943(8) 0.0162(2) Uani 1 1 d . . .
C14 C 0.86345(17) 0.35915(16) 0.37602(9) 0.0220(3) Uani 1 1 d . . .
H14 H 0.7847 0.4356 0.4090 0.026 Uiso 1 1 calc R . .
C15 C 0.87471(19) 0.18795(17) 0.40403(10) 0.0276(3) Uani 1 1 d . . .
H15 H 0.8045 0.1508 0.4559 0.033 Uiso 1 1 calc R . .
C16 C 0.98997(18) 0.07340(17) 0.35489(10) 0.0269(3) Uani 1 1 d . . .
H16 H 0.9969 -0.0406 0.3733 0.032 Uiso 1 1 calc R . .
C17 C 1.09527(17) 0.12930(16) 0.27802(10) 0.0245(3) Uani 1 1 d . . .
H17 H 1.1724 0.0526 0.2445 0.029 Uiso 1 1 calc R . .
C18 C 1.08600(16) 0.29970(16) 0.25086(9) 0.0202(3) Uani 1 1 d . . .
H18 H 1.1585 0.3359 0.2001 0.024 Uiso 1 1 calc R . .
C19 C 1.12907(15) 0.62655(15) 0.26640(9) 0.0167(2) Uani 1 1 d . . .
C20 C 1.22600(16) 0.66723(16) 0.18089(9) 0.0214(3) Uani 1 1 d . . .
H20 H 1.1880 0.6806 0.1206 0.026 Uiso 1 1 calc R . .
C21 C 1.37992(17) 0.68820(18) 0.18470(11) 0.0274(3) Uani 1 1 d . . .
H21 H 1.4432 0.7170 0.1269 0.033 Uiso 1 1 calc R . .
C22 C 1.43909(17) 0.66650(19) 0.27365(11) 0.0298(3) Uani 1 1 d . . .
H22 H 1.5415 0.6814 0.2760 0.036 Uiso 1 1 calc R . .
C23 C 1.34480(18) 0.6223(2) 0.35947(11) 0.0316(3) Uani 1 1 d . . .
H23 H 1.3848 0.6060 0.4196 0.038 Uiso 1 1 calc R . .
C24 C 1.19081(16) 0.60231(18) 0.35605(10) 0.0245(3) Uani 1 1 d . . .
H24 H 1.1284 0.5725 0.4140 0.029 Uiso 1 1 calc R . .
C1S C 0.6172(2) 0.2457(2) 0.19085(12) 0.0417(4) Uani 1 1 d . . .
H1S1 H 0.7213 0.2356 0.2132 0.063 Uiso 1 1 calc R . .
H1S2 H 0.6030 0.1357 0.2033 0.063 Uiso 1 1 calc R . .
H1S3 H 0.5272 0.3172 0.2250 0.063 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1S C1S 1.4263(19) . ?
O1S H1S 0.8200 . ?
O1 C9 1.3677(16) . ?
O1 H1 0.8200 . ?
C1 C2 1.3836(17) . ?
C1 C3 1.3993(17) 2_676 ?
C1 H1A 0.9300 . ?
C2 C3 1.4010(18) . ?
C2 H2 0.9300 . ?
C3 C1 1.3993(17) 2_676 ?
C3 C4 1.4394(16) . ?
C4 C5 1.1967(17) . ?
C5 C6 1.4840(16) . ?
C6 C13 1.5422(16) . ?
C6 C7 1.5479(16) . ?
C6 C19 1.5506(16) . ?
C7 C8 1.3872(16) . ?
C7 C12 1.3964(17) . ?
C8 C9 1.3963(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.3806(19) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.3862(18) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.3884(17) . ?
C13 C18 1.3981(17) . ?
C14 C15 1.3948(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3921(18) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.3874(17) . ?
C19 C24 1.3951(17) . ?
C20 C21 1.3935(18) . ?
C20 H20 0.9300 . ?
C21 C22 1.380(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.3890(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?

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
C1S O1S H1S 109.5 . . ?
C9 O1 H1 109.5 . . ?
C2 C1 C3 120.29(11) . 2_676 ?
C2 C1 H1A 119.9 . . ?
C3 C1 H1A 119.9 2_676 . ?
C1 C2 C3 120.91(11) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C1 C3 C2 118.80(11) 2_676 . ?
C1 C3 C4 120.90(11) 2_676 . ?
C2 C3 C4 120.28(11) . . ?
C5 C4 C3 178.04(13) . . ?
C4 C5 C6 176.81(13) . . ?
C5 C6 C13 110.46(9) . . ?
C5 C6 C7 105.32(9) . . ?
C13 C6 C7 112.01(9) . . ?
C5 C6 C19 107.96(9) . . ?
C13 C6 C19 108.94(9) . . ?
C7 C6 C19 112.03(9) . . ?
C8 C7 C12 118.92(11) . . ?
C8 C7 C6 122.14(11) . . ?
C12 C7 C6 118.84(10) . . ?
C7 C8 C9 120.24(12) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
O1 C9 C10 118.26(11) . . ?
O1 C9 C8 121.00(12) . . ?
C10 C9 C8 120.72(12) . . ?
C9 C10 C11 119.04(12) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 120.74(13) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 120.33(12) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 118.71(11) . . ?
C14 C13 C6 121.55(11) . . ?
C18 C13 C6 119.73(10) . . ?
C13 C14 C15 120.75(12) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.16(13) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.68(12) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.27(12) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.41(12) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 C24 118.74(11) . . ?
C20 C19 C6 122.34(11) . . ?
C24 C19 C6 118.92(11) . . ?
C19 C20 C21 120.49(12) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 120.43(13) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.49(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.29(13) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.53(13) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 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
C3 C1 C2 C3 -0.6(2) 2_676 . . . ?
C1 C2 C3 C1 0.6(2) . . . 2_676 ?
C1 C2 C3 C4 -177.87(12) . . . . ?
C1 C3 C4 C5 -134(4) 2_676 . . . ?
C2 C3 C4 C5 45(4) . . . . ?
C3 C4 C5 C6 -27(5) . . . . ?
C4 C5 C6 C13 -126(2) . . . . ?
C4 C5 C6 C7 -5(2) . . . . ?
C4 C5 C6 C19 115(2) . . . . ?
C5 C6 C7 C8 -116.11(12) . . . . ?
C13 C6 C7 C8 4.01(16) . . . . ?
C19 C6 C7 C8 126.77(12) . . . . ?
C5 C6 C7 C12 60.25(13) . . . . ?
C13 C6 C7 C12 -179.64(11) . . . . ?
C19 C6 C7 C12 -56.87(14) . . . . ?
C12 C7 C8 C9 -0.80(18) . . . . ?
C6 C7 C8 C9 175.55(11) . . . . ?
C7 C8 C9 O1 -177.31(12) . . . . ?
C7 C8 C9 C10 1.02(19) . . . . ?
O1 C9 C10 C11 178.33(13) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C10 C11 C12 C7 1.4(2) . . . . ?
C8 C7 C12 C11 -0.37(19) . . . . ?
C6 C7 C12 C11 -176.84(12) . . . . ?
C5 C6 C13 C14 7.80(15) . . . . ?
C7 C6 C13 C14 -109.27(12) . . . . ?
C19 C6 C13 C14 126.22(12) . . . . ?
C5 C6 C13 C18 -173.56(10) . . . . ?
C7 C6 C13 C18 69.37(13) . . . . ?
C19 C6 C13 C18 -55.14(13) . . . . ?
C18 C13 C14 C15 -0.07(18) . . . . ?
C6 C13 C14 C15 178.58(11) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C17 C18 C13 -1.26(19) . . . . ?
C14 C13 C18 C17 1.04(18) . . . . ?
C6 C13 C18 C17 -177.64(11) . . . . ?
C5 C6 C19 C20 -132.25(12) . . . . ?
C13 C6 C19 C20 107.77(12) . . . . ?
C7 C6 C19 C20 -16.72(15) . . . . ?
C5 C6 C19 C24 48.15(14) . . . . ?
C13 C6 C19 C24 -71.84(13) . . . . ?
C7 C6 C19 C24 163.67(11) . . . . ?
C24 C19 C20 C21 -1.83(19) . . . . ?
C6 C19 C20 C21 178.56(11) . . . . ?
C19 C20 C21 C22 0.9(2) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
C21 C22 C23 C24 -0.9(2) . . . . ?
C22 C23 C24 C19 -0.1(2) . . . . ?
C20 C19 C24 C23 1.4(2) . . . . ?
C6 C19 C24 C23 -178.96(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
