# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_q
_database_code_depnum_ccdc_archive 'CCDC 1412198'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22'
_chemical_formula_sum            'C30 H22'
_chemical_formula_weight         382.48

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/N
_symmetry_space_group_name_Hall  '-P 2yn'

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                   5.2605(11)
_cell_length_b                   9.4604(19)
_cell_length_c                   20.691(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.70(3)
_cell_angle_gamma                90.00
_cell_volume                     1029.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2050
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.1240
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.37
_reflns_number_total             1845
_reflns_number_gt                883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1845
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1681
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_ref         0.1940
_refine_ls_wR_factor_gt          0.1640
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1575(8) 0.3981(4) 0.65043(18) 0.0566(11) Uani 1 1 d . . .
H1A H 1.1989 0.3930 0.6069 0.068 Uiso 1 1 calc R . .
C2 C 1.2969(8) 0.4829(5) 0.6899(2) 0.0719(13) Uani 1 1 d . . .
H2A H 1.4275 0.5375 0.6732 0.086 Uiso 1 1 calc R . .
C3 C 1.2441(10) 0.4882(5) 0.7556(2) 0.0740(14) Uani 1 1 d . . .
H3A H 1.3414 0.5447 0.7831 0.089 Uiso 1 1 calc R . .
C4 C 1.0516(10) 0.4111(5) 0.7790(2) 0.0757(14) Uani 1 1 d . . .
H4A H 1.0160 0.4146 0.8229 0.091 Uiso 1 1 calc R . .
C5 C 0.9061(8) 0.3268(4) 0.73869(18) 0.0607(12) Uani 1 1 d . . .
H5A H 0.7731 0.2745 0.7557 0.073 Uiso 1 1 calc R . .
C6 C 0.9557(7) 0.3187(4) 0.67260(17) 0.0498(10) Uani 1 1 d . . .
C7 C 0.7981(8) 0.2252(4) 0.63124(18) 0.0611(12) Uani 1 1 d . . .
H7A H 0.6618 0.1818 0.6515 0.073 Uiso 1 1 calc R . .
C8 C 0.8243(7) 0.1961(4) 0.57133(17) 0.0538(11) Uani 1 1 d . . .
H8A H 0.9542 0.2413 0.5493 0.065 Uiso 1 1 calc R . .
C9 C 0.6627(7) 0.0957(4) 0.53472(16) 0.0475(10) Uani 1 1 d . . .
C10 C 0.4757(7) 0.1470(4) 0.49085(17) 0.0488(10) Uani 1 1 d . . .
C11 C 0.3092(7) 0.0500(4) 0.45667(16) 0.0484(10) Uani 1 1 d . . .
C12 C 0.1188(8) 0.1091(4) 0.41555(17) 0.0573(11) Uani 1 1 d . . .
H12A H 0.0060 0.0484 0.3945 0.069 Uiso 1 1 calc R . .
C13 C 0.0946(9) 0.2507(5) 0.40567(19) 0.0646(12) Uani 1 1 d . . .
H13A H -0.0316 0.2852 0.3780 0.077 Uiso 1 1 calc R . .
C14 C 0.2611(8) 0.3443(5) 0.43741(18) 0.0619(12) Uani 1 1 d . . .
H14A H 0.2458 0.4410 0.4303 0.074 Uiso 1 1 calc R . .
C15 C 0.4439(8) 0.2953(4) 0.47827(19) 0.0586(11) Uani 1 1 d . . .
H15A H 0.5519 0.3595 0.4988 0.070 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
C1 C2 1.354(5) . ?
C1 C6 1.383(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.392(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.343(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.397(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.478(5) . ?
C7 C8 1.279(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.477(5) . ?
C8 H8A 0.9300 . ?
C9 C11 1.398(5) 3_656 ?
C9 C10 1.416(5) . ?
C10 C15 1.436(5) . ?
C10 C11 1.447(5) . ?
C11 C9 1.398(5) 3_656 ?
C11 C12 1.421(5) . ?
C12 C13 1.361(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.404(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.354(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

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 C6 122.2(4) . . ?
C2 C1 H1A 118.9 . . ?
C6 C1 H1A 118.9 . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 116.6(4) . . ?
C1 C6 C7 124.1(3) . . ?
C5 C6 C7 119.3(4) . . ?
C8 C7 C6 128.6(4) . . ?
C8 C7 H7A 115.7 . . ?
C6 C7 H7A 115.7 . . ?
C7 C8 C9 124.5(4) . . ?
C7 C8 H8A 117.7 . . ?
C9 C8 H8A 117.7 . . ?
C11 C9 C10 119.4(3) 3_656 . ?
C11 C9 C8 120.6(3) 3_656 . ?
C10 C9 C8 120.0(4) . . ?
C9 C10 C15 122.0(4) . . ?
C9 C10 C11 120.5(3) . . ?
C15 C10 C11 117.6(3) . . ?
C9 C11 C12 122.5(4) 3_656 . ?
C9 C11 C10 120.1(3) 3_656 . ?
C12 C11 C10 117.5(3) . . ?
C13 C12 C11 122.8(4) . . ?
C13 C12 H12A 118.6 . . ?
C11 C12 H12A 118.6 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C10 121.8(4) . . ?
C14 C15 H15A 119.1 . . ?
C10 C15 H15A 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.3(6) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C2 C1 C6 C5 -1.9(6) . . . . ?
C2 C1 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 179.0(4) . . . . ?
C1 C6 C7 C8 3.6(7) . . . . ?
C5 C6 C7 C8 -174.7(4) . . . . ?
C6 C7 C8 C9 177.1(4) . . . . ?
C7 C8 C9 C11 -74.7(5) . . . 3_656 ?
C7 C8 C9 C10 104.8(5) . . . . ?
C11 C9 C10 C15 -177.8(3) 3_656 . . . ?
C8 C9 C10 C15 2.8(5) . . . . ?
C11 C9 C10 C11 2.0(6) 3_656 . . . ?
C8 C9 C10 C11 -177.5(3) . . . . ?
C9 C10 C11 C9 -2.0(6) . . . 3_656 ?
C15 C10 C11 C9 177.8(3) . . . 3_656 ?
C9 C10 C11 C12 177.3(3) . . . . ?
C15 C10 C11 C12 -2.9(5) . . . . ?
C9 C11 C12 C13 -178.3(4) 3_656 . . . ?
C10 C11 C12 C13 2.4(6) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
C9 C10 C15 C14 -178.5(4) . . . . ?
C11 C10 C15 C14 1.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1412199'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 F2'
_chemical_formula_sum            'C30 H20 F2'
_chemical_formula_weight         418.46

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'
F F 0.0171 0.0103 '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                   9.4080(19)
_cell_length_b                   10.249(2)
_cell_length_c                   12.766(3)
_cell_angle_alpha                106.25(3)
_cell_angle_beta                 90.87(3)
_cell_angle_gamma                115.16(3)
_cell_volume                     1056.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4138
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0738
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.36
_reflns_number_total             3883
_reflns_number_gt                2101
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.5500P] 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     SHELXL
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3883
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1926
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
F1 F 0.5308(4) 0.1269(3) -0.24153(18) 0.1021(10) Uani 1 1 d . . .
C1 C 0.8501(4) 0.1820(4) 0.3859(3) 0.0559(10) Uani 1 1 d . . .
H1A H 0.8139 0.1456 0.3104 0.067 Uiso 1 1 calc R . .
C2 C 0.8329(5) 0.0817(5) 0.4404(3) 0.0638(11) Uani 1 1 d . . .
H2A H 0.7862 -0.0220 0.4024 0.077 Uiso 1 1 calc R . .
C3 C 0.8861(5) 0.1348(5) 0.5545(3) 0.0653(12) Uani 1 1 d . . .
H3A H 0.8741 0.0656 0.5918 0.078 Uiso 1 1 calc R . .
C4 C 0.9543(5) 0.2847(5) 0.6110(3) 0.0570(10) Uani 1 1 d . . .
H4A H 0.9879 0.3167 0.6866 0.068 Uiso 1 1 calc R . .
C5 C 0.9761(4) 0.3951(4) 0.5574(3) 0.0433(9) Uani 1 1 d . . .
C6 C 0.9220(4) 0.3421(4) 0.4408(3) 0.0443(9) Uani 1 1 d . . .
C7 C 0.9470(4) 0.4482(4) 0.3844(3) 0.0458(9) Uani 1 1 d . . .
C8 C 0.8987(5) 0.3988(4) 0.2624(3) 0.0600(11) Uani 1 1 d . . .
H8A H 0.9797 0.4295 0.2208 0.072 Uiso 1 1 calc R . .
C9 C 0.7564(5) 0.3179(5) 0.2092(3) 0.0589(11) Uani 1 1 d . . .
H9A H 0.6769 0.2853 0.2516 0.071 Uiso 1 1 calc R . .
C10 C 0.7028(5) 0.2700(4) 0.0887(3) 0.0542(10) Uani 1 1 d . . .
C11 C 0.5431(5) 0.2027(5) 0.0504(3) 0.0639(11) Uani 1 1 d . . .
H11A H 0.4719 0.1887 0.1007 0.077 Uiso 1 1 calc R . .
C12 C 0.4854(5) 0.1554(5) -0.0594(3) 0.0668(12) Uani 1 1 d . . .
H12A H 0.3765 0.1098 -0.0833 0.080 Uiso 1 1 calc R . .
C13 C 0.5875(6) 0.1756(5) -0.1322(3) 0.0629(12) Uani 1 1 d . . .
C14 C 0.7480(6) 0.2424(5) -0.1007(3) 0.0724(13) Uani 1 1 d . . .
H14A H 0.8169 0.2556 -0.1526 0.087 Uiso 1 1 calc R . .
C15 C 0.8062(5) 0.2903(5) 0.0117(3) 0.0667(12) Uani 1 1 d . . .
H15A H 0.9152 0.3363 0.0352 0.080 Uiso 1 1 calc R . .
F2 F 1.5667(3) 0.4220(3) 0.71534(19) 0.1008(10) Uani 1 1 d . . .
C16 C 1.0370(4) 0.0720(4) -0.0824(3) 0.0432(9) Uani 1 1 d . . .
C17 C 1.0869(5) 0.1496(4) -0.1626(3) 0.0548(10) Uani 1 1 d . . .
H17A H 1.0437 0.0975 -0.2366 0.066 Uiso 1 1 calc R . .
C18 C 1.1962(5) 0.2976(5) -0.1325(3) 0.0642(11) Uani 1 1 d . . .
H18A H 1.2259 0.3455 -0.1861 0.077 Uiso 1 1 calc R . .
C19 C 1.2653(5) 0.3796(4) -0.0215(3) 0.0601(11) Uani 1 1 d . . .
H19A H 1.3381 0.4817 -0.0018 0.072 Uiso 1 1 calc R . .
C20 C 1.2256(4) 0.3097(4) 0.0565(3) 0.0518(10) Uani 1 1 d . . .
H20A H 1.2736 0.3646 0.1294 0.062 Uiso 1 1 calc R . .
C21 C 1.1122(4) 0.1542(4) 0.0302(3) 0.0431(8) Uani 1 1 d . . .
C22 C 1.0763(4) 0.0819(4) 0.1114(3) 0.0424(8) Uani 1 1 d . . .
C23 C 1.1590(4) 0.1680(4) 0.2268(3) 0.0505(9) Uani 1 1 d . . .
H23A H 1.1388 0.2485 0.2649 0.061 Uiso 1 1 calc R . .
C24 C 1.2583(4) 0.1400(4) 0.2793(3) 0.0460(9) Uani 1 1 d . . .
H24A H 1.2791 0.0609 0.2391 0.055 Uiso 1 1 calc R . .
C25 C 1.3405(4) 0.2180(4) 0.3936(3) 0.0425(9) Uani 1 1 d . . .
C26 C 1.4602(4) 0.1894(4) 0.4300(3) 0.0521(9) Uani 1 1 d . . .
H26A H 1.4891 0.1225 0.3806 0.062 Uiso 1 1 calc R . .
C27 C 1.5378(5) 0.2568(5) 0.5372(3) 0.0627(11) Uani 1 1 d . . .
H27A H 1.6183 0.2366 0.5604 0.075 Uiso 1 1 calc R . .
C28 C 1.4929(5) 0.3541(4) 0.6082(3) 0.0619(12) Uani 1 1 d . . .
C29 C 1.3752(5) 0.3862(4) 0.5777(3) 0.0603(11) Uani 1 1 d . . .
H29A H 1.3468 0.4525 0.6283 0.072 Uiso 1 1 calc R . .
C30 C 1.2995(4) 0.3180(4) 0.4701(3) 0.0513(9) Uani 1 1 d . . .
H30A H 1.2193 0.3392 0.4479 0.062 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
F1 C13 1.357(4) . ?
C1 C2 1.353(5) . ?
C1 C6 1.428(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.404(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.349(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.425(5) . ?
C4 H4A 0.9300 . ?
C5 C7 1.407(5) 2_766 ?
C5 C6 1.436(4) . ?
C6 C7 1.408(5) . ?
C7 C5 1.407(5) 2_766 ?
C7 C8 1.493(5) . ?
C8 C9 1.287(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.485(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.371(5) . ?
C10 C15 1.387(5) . ?
C11 C12 1.367(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.340(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.364(6) . ?
C14 C15 1.398(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
F2 C28 1.365(4) . ?
C16 C22 1.412(5) 2_755 ?
C16 C17 1.433(5) . ?
C16 C21 1.436(4) . ?
C17 C18 1.357(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.407(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.351(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.427(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.401(4) . ?
C22 C16 1.412(5) 2_755 ?
C22 C23 1.486(4) . ?
C23 C24 1.312(5) . ?
C23 H23A 0.9300 . ?
C24 C25 1.468(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.382(5) . ?
C25 C30 1.392(5) . ?
C26 C27 1.376(5) . ?
C26 H26A 0.9300 . ?
C27 C28 1.363(6) . ?
C27 H27A 0.9300 . ?
C28 C29 1.361(6) . ?
C29 C30 1.377(5) . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?

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 C6 122.0(4) . . ?
C2 C1 H1A 119.0 . . ?
C6 C1 H1A 119.0 . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C7 C5 C4 121.4(3) 2_766 . ?
C7 C5 C6 120.6(3) 2_766 . ?
C4 C5 C6 117.9(3) . . ?
C7 C6 C1 122.7(3) . . ?
C7 C6 C5 119.5(3) . . ?
C1 C6 C5 117.8(3) . . ?
C5 C7 C6 120.0(3) 2_766 . ?
C5 C7 C8 118.6(3) 2_766 . ?
C6 C7 C8 121.4(3) . . ?
C9 C8 C7 126.5(4) . . ?
C9 C8 H8A 116.7 . . ?
C7 C8 H8A 116.7 . . ?
C8 C9 C10 128.3(4) . . ?
C8 C9 H9A 115.9 . . ?
C10 C9 H9A 115.9 . . ?
C11 C10 C15 117.6(4) . . ?
C11 C10 C9 118.9(4) . . ?
C15 C10 C9 123.5(4) . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C12 C13 F1 119.5(4) . . ?
C12 C13 C14 122.3(4) . . ?
F1 C13 C14 118.2(4) . . ?
C13 C14 C15 118.1(4) . . ?
C13 C14 H14A 120.9 . . ?
C15 C14 H14A 120.9 . . ?
C10 C15 C14 120.7(4) . . ?
C10 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C22 C16 C17 122.4(3) 2_755 . ?
C22 C16 C21 119.9(3) 2_755 . ?
C17 C16 C21 117.7(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17A 119.4 . . ?
C16 C17 H17A 119.4 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 H20A 119.0 . . ?
C21 C20 H20A 119.0 . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 C16 120.5(3) . . ?
C20 C21 C16 118.3(3) . . ?
C21 C22 C16 119.6(3) . 2_755 ?
C21 C22 C23 119.5(3) . . ?
C16 C22 C23 120.9(3) 2_755 . ?
C24 C23 C22 125.4(3) . . ?
C24 C23 H23A 117.3 . . ?
C22 C23 H23A 117.3 . . ?
C23 C24 C25 128.1(3) . . ?
C23 C24 H24A 116.0 . . ?
C25 C24 H24A 116.0 . . ?
C26 C25 C30 117.4(3) . . ?
C26 C25 C24 120.0(3) . . ?
C30 C25 C24 122.5(3) . . ?
C27 C26 C25 122.1(4) . . ?
C27 C26 H26A 119.0 . . ?
C25 C26 H26A 119.0 . . ?
C28 C27 C26 117.9(4) . . ?
C28 C27 H27A 121.1 . . ?
C26 C27 H27A 121.1 . . ?
C29 C28 C27 122.9(3) . . ?
C29 C28 F2 117.7(4) . . ?
C27 C28 F2 119.3(4) . . ?
C28 C29 C30 118.3(4) . . ?
C28 C29 H29A 120.9 . . ?
C30 C29 H29A 120.9 . . ?
C29 C30 C25 121.4(4) . . ?
C29 C30 H30A 119.3 . . ?
C25 C30 H30A 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C7 -177.4(4) . . . 2_766 ?
C3 C4 C5 C6 0.4(5) . . . . ?
C2 C1 C6 C7 177.2(4) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C7 C5 C6 C7 0.2(5) 2_766 . . . ?
C4 C5 C6 C7 -177.6(3) . . . . ?
C7 C5 C6 C1 177.7(3) 2_766 . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C1 C6 C7 C5 -177.6(3) . . . 2_766 ?
C5 C6 C7 C5 -0.2(5) . . . 2_766 ?
C1 C6 C7 C8 0.1(5) . . . . ?
C5 C6 C7 C8 177.5(3) . . . . ?
C5 C7 C8 C9 -119.0(5) 2_766 . . . ?
C6 C7 C8 C9 63.3(6) . . . . ?
C7 C8 C9 C10 178.1(4) . . . . ?
C8 C9 C10 C11 -170.5(4) . . . . ?
C8 C9 C10 C15 9.2(7) . . . . ?
C15 C10 C11 C12 0.5(6) . . . . ?
C9 C10 C11 C12 -179.8(4) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 F1 179.0(4) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
F1 C13 C14 C15 -179.0(4) . . . . ?
C11 C10 C15 C14 -0.4(6) . . . . ?
C9 C10 C15 C14 179.9(4) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
C22 C16 C17 C18 -179.9(4) 2_755 . . . ?
C21 C16 C17 C18 -2.9(5) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C17 C18 C19 C20 1.6(6) . . . . ?
C18 C19 C20 C21 -1.3(6) . . . . ?
C19 C20 C21 C22 177.8(4) . . . . ?
C19 C20 C21 C16 -1.2(5) . . . . ?
C22 C16 C21 C22 1.2(5) 2_755 . . . ?
C17 C16 C21 C22 -175.8(3) . . . . ?
C22 C16 C21 C20 -179.8(3) 2_755 . . . ?
C17 C16 C21 C20 3.2(5) . . . . ?
C20 C21 C22 C16 179.8(3) . . . 2_755 ?
C16 C21 C22 C16 -1.2(5) . . . 2_755 ?
C20 C21 C22 C23 -0.7(5) . . . . ?
C16 C21 C22 C23 178.2(3) . . . . ?
C21 C22 C23 C24 -114.1(4) . . . . ?
C16 C22 C23 C24 65.4(5) 2_755 . . . ?
C22 C23 C24 C25 -178.3(3) . . . . ?
C23 C24 C25 C26 -169.7(4) . . . . ?
C23 C24 C25 C30 12.5(6) . . . . ?
C30 C25 C26 C27 -0.3(5) . . . . ?
C24 C25 C26 C27 -178.3(3) . . . . ?
C25 C26 C27 C28 0.2(6) . . . . ?
C26 C27 C28 C29 0.3(6) . . . . ?
C26 C27 C28 F2 179.5(3) . . . . ?
C27 C28 C29 C30 -0.5(6) . . . . ?
F2 C28 C29 C30 -179.8(3) . . . . ?
C28 C29 C30 C25 0.3(6) . . . . ?
C26 C25 C30 C29 0.1(5) . . . . ?
C24 C25 C30 C29 178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1412200'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 Cl2'
_chemical_formula_sum            'C30 H20 Cl2'
_chemical_formula_weight         451.36

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'
Cl Cl 0.1484 0.1585 '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                   6.9264(14)
_cell_length_b                   9.7188(19)
_cell_length_c                   9.951(2)
_cell_angle_alpha                64.11(3)
_cell_angle_beta                 71.29(3)
_cell_angle_gamma                76.17(3)
_cell_volume                     567.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             234
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2191
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_sigmaI/netI    0.1430
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2016
_reflns_number_gt                931
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2016
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Cl Cl -1.41453(19) 0.92035(18) 0.32653(18) 0.0782(6) Uani 1 1 d . . .
C1 C -0.8922(6) 0.6532(5) 0.2558(5) 0.0516(14) Uani 1 1 d . . .
H1A H -0.8518 0.5488 0.2777 0.062 Uiso 1 1 calc R . .
C2 C -1.0981(7) 0.7022(6) 0.3021(6) 0.0556(15) Uani 1 1 d . . .
H2A H -1.1947 0.6323 0.3538 0.067 Uiso 1 1 calc R . .
C3 C -1.1564(6) 0.8572(6) 0.2696(5) 0.0478(13) Uani 1 1 d . . .
C4 C -1.0154(7) 0.9611(5) 0.1940(5) 0.0471(13) Uani 1 1 d . . .
H4A H -1.0566 1.0653 0.1728 0.056 Uiso 1 1 calc R . .
C5 C -0.8100(7) 0.9086(5) 0.1494(5) 0.0492(13) Uani 1 1 d . . .
H5A H -0.7137 0.9787 0.0990 0.059 Uiso 1 1 calc R . .
C6 C -0.7448(6) 0.7537(5) 0.1783(5) 0.0392(12) Uani 1 1 d . . .
C7 C -0.5256(6) 0.7076(5) 0.1221(5) 0.0432(12) Uani 1 1 d . . .
H7A H -0.4393 0.7836 0.0827 0.052 Uiso 1 1 calc R . .
C8 C -0.4363(6) 0.5729(5) 0.1205(5) 0.0394(12) Uani 1 1 d . . .
H8A H -0.5183 0.4938 0.1620 0.047 Uiso 1 1 calc R . .
C9 C -0.2130(6) 0.5377(5) 0.0568(5) 0.0334(11) Uani 1 1 d . . .
C10 C -0.0999(6) 0.4184(5) 0.1537(5) 0.0342(11) Uani 1 1 d . . .
C11 C -0.1933(7) 0.3356(5) 0.3135(5) 0.0462(13) Uani 1 1 d . . .
H11A H -0.3335 0.3568 0.3513 0.055 Uiso 1 1 calc R . .
C12 C -0.0820(7) 0.2274(5) 0.4103(5) 0.0509(13) Uani 1 1 d . . .
H12A H -0.1460 0.1742 0.5129 0.061 Uiso 1 1 calc R . .
C13 C 0.1310(6) 0.1955(5) 0.3553(5) 0.0443(12) Uani 1 1 d . . .
H13A H 0.2076 0.1238 0.4232 0.053 Uiso 1 1 calc R . .
C14 C 0.2262(6) 0.2678(5) 0.2049(5) 0.0413(12) Uani 1 1 d . . .
H14A H 0.3664 0.2426 0.1710 0.050 Uiso 1 1 calc R . .
C15 C -0.1158(6) 0.6183(5) -0.0975(5) 0.0338(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C3 1.739(4) . ?
C1 C6 1.380(5) . ?
C1 C2 1.385(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.380(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(6) . ?
C4 C5 1.388(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.472(5) . ?
C7 C8 1.312(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.489(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.401(5) . ?
C9 C15 1.402(5) . ?
C10 C15 1.434(5) 2_565 ?
C10 C11 1.438(5) . ?
C11 C12 1.353(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.408(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.356(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.428(5) 2_565 ?
C14 H14A 0.9300 . ?
C15 C14 1.428(5) 2_565 ?
C15 C10 1.434(5) 2_565 ?

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
C6 C1 C2 122.4(4) . . ?
C6 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 Cl 119.8(4) . . ?
C2 C3 Cl 118.9(4) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C1 C6 C5 117.3(4) . . ?
C1 C6 C7 124.2(4) . . ?
C5 C6 C7 118.5(4) . . ?
C8 C7 C6 128.3(4) . . ?
C8 C7 H7A 115.9 . . ?
C6 C7 H7A 115.9 . . ?
C7 C8 C9 124.6(4) . . ?
C7 C8 H8A 117.7 . . ?
C9 C8 H8A 117.7 . . ?
C10 C9 C15 119.7(4) . . ?
C10 C9 C8 118.7(4) . . ?
C15 C9 C8 121.6(4) . . ?
C9 C10 C15 120.5(4) . 2_565 ?
C9 C10 C11 121.2(4) . . ?
C15 C10 C11 118.2(4) 2_565 . ?
C12 C11 C10 121.6(4) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 121.4(4) . 2_565 ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 2_565 . ?
C9 C15 C14 122.2(4) . 2_565 ?
C9 C15 C10 119.8(4) . 2_565 ?
C14 C15 C10 117.9(4) 2_565 2_565 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(8) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C1 C2 C3 Cl 179.8(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
Cl C3 C4 C5 -180.0(4) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
C2 C1 C6 C7 -177.7(4) . . . . ?
C4 C5 C6 C1 -1.1(7) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C1 C6 C7 C8 7.5(8) . . . . ?
C5 C6 C7 C8 -171.2(5) . . . . ?
C6 C7 C8 C9 178.1(4) . . . . ?
C7 C8 C9 C10 122.5(5) . . . . ?
C7 C8 C9 C15 -59.0(6) . . . . ?
C15 C9 C10 C15 2.1(7) . . . 2_565 ?
C8 C9 C10 C15 -179.4(4) . . . 2_565 ?
C15 C9 C10 C11 178.6(4) . . . . ?
C8 C9 C10 C11 -2.9(6) . . . . ?
C9 C10 C11 C12 -175.5(4) . . . . ?
C15 C10 C11 C12 1.1(7) 2_565 . . . ?
C10 C11 C12 C13 0.9(7) . . . . ?
C11 C12 C13 C14 -2.4(7) . . . . ?
C12 C13 C14 C15 1.7(7) . . . 2_565 ?
C10 C9 C15 C14 174.8(4) . . . 2_565 ?
C8 C9 C15 C14 -3.7(6) . . . 2_565 ?
C10 C9 C15 C10 -2.1(7) . . . 2_565 ?
C8 C9 C15 C10 179.4(4) . . . 2_565 ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1412201'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 Br2'
_chemical_formula_sum            'C30 H20 Br2'
_chemical_formula_weight         540.28

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   4.6220(9)
_cell_length_b                   27.568(6)
_cell_length_c                   9.2820(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.74(3)
_cell_angle_gamma                90.00
_cell_volume                     1148.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       Prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    3.544
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.5375
_exptl_absorpt_correction_T_max  0.7182
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4688
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.1701
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2119
_reflns_number_gt                885
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2021
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Br Br 0.8675(3) 0.14732(3) 0.95825(10) 0.1009(5) Uani 1 1 d . . .
C1 C 0.1649(18) 0.4440(3) 0.7579(7) 0.058(2) Uani 1 1 d . . .
H1A H 0.2047 0.4115 0.7443 0.069 Uiso 1 1 calc R . .
C2 C -0.055(2) 0.4666(3) 0.6630(10) 0.080(3) Uani 1 1 d . . .
H2A H -0.1567 0.4502 0.5787 0.096 Uiso 1 1 calc R . .
C3 C -0.138(2) 0.5141(3) 0.6856(10) 0.089(3) Uani 1 1 d . . .
H3A H -0.3027 0.5274 0.6195 0.107 Uiso 1 1 calc R . .
C4 C 0.003(2) 0.5403(3) 0.7945(8) 0.062(2) Uani 1 1 d . . .
H4A H -0.0565 0.5721 0.8053 0.075 Uiso 1 1 calc R . .
C5 C 0.2597(19) 0.5197(2) 0.9013(7) 0.0531(19) Uani 1 1 d . . .
C6 C 0.344(2) 0.4711(3) 0.8846(9) 0.065(2) Uani 1 1 d . . .
C7 C 0.578(2) 0.4513(2) 0.9848(8) 0.055(2) Uani 1 1 d . . .
C8 C 0.6574(19) 0.4010(3) 0.9664(9) 0.070(2) Uani 1 1 d . . .
H8A H 0.7517 0.3960 0.8896 0.083 Uiso 1 1 calc R . .
C9 C 0.622(2) 0.3620(3) 1.0365(8) 0.086(3) Uani 1 1 d . . .
H9A H 0.5382 0.3679 1.1167 0.103 Uiso 1 1 calc R . .
C10 C 0.6810(13) 0.3119(2) 1.0187(6) 0.0353(15) Uani 1 1 d . . .
C11 C 0.887(2) 0.2973(3) 0.9346(9) 0.082 Uani 1 1 d . . .
H11A H 0.9811 0.3205 0.8889 0.099 Uiso 1 1 calc R . .
C12 C 0.946(2) 0.2489(3) 0.9212(9) 0.080(3) Uani 1 1 d . . .
H12A H 1.0881 0.2400 0.8701 0.096 Uiso 1 1 calc R . .
C13 C 0.8033(18) 0.2134(2) 0.9803(6) 0.0481(19) Uani 1 1 d . . .
C14 C 0.585(3) 0.2288(3) 1.0624(10) 0.092(3) Uani 1 1 d . . .
H14A H 0.4803 0.2063 1.1046 0.110 Uiso 1 1 calc R . .
C15 C 0.545(2) 0.2746(3) 1.0740(10) 0.084(3) Uani 1 1 d . . .
H15A H 0.4051 0.2836 1.1266 0.101 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
Br C13 1.864(7) . ?
C1 C2 1.332(11) . ?
C1 C6 1.471(10) . ?
C1 H1A 0.9300 . ?
C2 C3 1.394(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.287(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.468(10) . ?
C4 H4A 0.9300 . ?
C5 C7 1.394(10) 3_667 ?
C5 C6 1.413(10) . ?
C6 C7 1.363(11) . ?
C7 C5 1.394(10) 3_667 ?
C7 C8 1.455(10) . ?
C8 C9 1.286(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.427(9) . ?
C9 H9A 0.9300 . ?
C10 C15 1.366(10) . ?
C10 C11 1.425(10) . ?
C11 C12 1.373(11) . ?
C11 H11A 0.9300 . ?
C12 C13 1.366(11) . ?
C12 H12A 0.9300 . ?
C13 C14 1.463(13) . ?
C14 C15 1.287(11) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

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 C6 119.1(8) . . ?
C2 C1 H1A 120.4 . . ?
C6 C1 H1A 120.4 . . ?
C1 C2 C3 122.4(8) . . ?
C1 C2 H2A 118.8 . . ?
C3 C2 H2A 118.8 . . ?
C4 C3 C2 122.5(9) . . ?
C4 C3 H3A 118.7 . . ?
C2 C3 H3A 118.7 . . ?
C3 C4 C5 119.4(8) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C7 C5 C6 121.0(8) 3_667 . ?
C7 C5 C4 119.4(7) 3_667 . ?
C6 C5 C4 119.6(7) . . ?
C7 C6 C5 120.0(8) . . ?
C7 C6 C1 123.2(7) . . ?
C5 C6 C1 116.8(8) . . ?
C6 C7 C5 119.0(7) . 3_667 ?
C6 C7 C8 118.9(7) . . ?
C5 C7 C8 122.1(8) 3_667 . ?
C9 C8 C7 132.1(8) . . ?
C9 C8 H8A 114.0 . . ?
C7 C8 H8A 114.0 . . ?
C8 C9 C10 134.3(8) . . ?
C8 C9 H9A 112.8 . . ?
C10 C9 H9A 112.8 . . ?
C15 C10 C11 115.0(7) . . ?
C15 C10 C9 124.5(7) . . ?
C11 C10 C9 120.6(7) . . ?
C12 C11 C10 119.7(8) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C13 C12 C11 122.4(9) . . ?
C13 C12 H12A 118.8 . . ?
C11 C12 H12A 118.8 . . ?
C12 C13 C14 117.3(7) . . ?
C12 C13 Br 123.5(6) . . ?
C14 C13 Br 119.2(6) . . ?
C15 C14 C13 117.5(9) . . ?
C15 C14 H14A 121.2 . . ?
C13 C14 H14A 121.2 . . ?
C14 C15 C10 128.1(10) . . ?
C14 C15 H15A 116.0 . . ?
C10 C15 H15A 116.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -5.4(14) . . . . ?
C1 C2 C3 C4 4.5(15) . . . . ?
C2 C3 C4 C5 -1.1(14) . . . . ?
C3 C4 C5 C7 177.0(8) . . . 3_667 ?
C3 C4 C5 C6 -1.1(12) . . . . ?
C7 C5 C6 C7 3.1(12) 3_667 . . . ?
C4 C5 C6 C7 -178.8(7) . . . . ?
C7 C5 C6 C1 -177.9(7) 3_667 . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C2 C1 C6 C7 -178.1(9) . . . . ?
C2 C1 C6 C5 3.0(11) . . . . ?
C5 C6 C7 C5 -3.0(12) . . . 3_667 ?
C1 C6 C7 C5 178.1(7) . . . 3_667 ?
C5 C6 C7 C8 179.0(7) . . . . ?
C1 C6 C7 C8 0.1(11) . . . . ?
C6 C7 C8 C9 -105.9(12) . . . . ?
C5 C7 C8 C9 76.2(13) 3_667 . . . ?
C7 C8 C9 C10 176.3(9) . . . . ?
C8 C9 C10 C15 -158.3(11) . . . . ?
C8 C9 C10 C11 19.5(14) . . . . ?
C15 C10 C11 C12 -3.3(10) . . . . ?
C9 C10 C11 C12 178.7(8) . . . . ?
C10 C11 C12 C13 3.1(12) . . . . ?
C11 C12 C13 C14 -1.2(12) . . . . ?
C11 C12 C13 Br 177.6(6) . . . . ?
C12 C13 C14 C15 -0.4(12) . . . . ?
Br C13 C14 C15 -179.3(7) . . . . ?
C13 C14 C15 C10 0.0(15) . . . . ?
C11 C10 C15 C14 1.9(13) . . . . ?
C9 C10 C15 C14 179.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1412202'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2015-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H20 I2'
_chemical_formula_sum            'C30 H20 I2'
_chemical_formula_weight         634.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   4.6500(9)
_cell_length_b                   28.225(6)
_cell_length_c                   9.3260(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.36(3)
_cell_angle_gamma                90.00
_cell_volume                     1185.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    2.668
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_T_max  0.7763
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2452
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.1449
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2181
_reflns_number_gt                904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0190P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2181
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2034
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
I I 1.3997(3) -0.35175(3) 0.54029(11) 0.0949(4) Uani 1 1 d . . .
C1 C 1.434(4) -0.2002(6) 0.5738(15) 0.121(6) Uani 1 1 d . . .
H1A H 1.5707 -0.1784 0.6261 0.145 Uiso 1 1 calc R . .
C2 C 1.506(4) -0.2512(6) 0.5820(15) 0.108(5) Uani 1 1 d . . .
H2A H 1.6924 -0.2616 0.6340 0.129 Uiso 1 1 calc R . .
C3 C 1.303(3) -0.2820(5) 0.5149(14) 0.077(3) Uani 1 1 d . . .
C4 C 1.043(4) -0.2692(4) 0.4325(17) 0.108(5) Uani 1 1 d . . .
H4A H 0.9137 -0.2928 0.3858 0.130 Uiso 1 1 calc R . .
C5 C 0.945(3) -0.2200(6) 0.4100(19) 0.135(7) Uani 1 1 d . . .
H5A H 0.7590 -0.2122 0.3508 0.162 Uiso 1 1 calc R . .
C6 C 1.148(3) -0.1841(4) 0.4829(12) 0.061(3) Uani 1 1 d . . .
C7 C 1.077(3) -0.1350(4) 0.4619(11) 0.068(3) Uani 1 1 d . . .
H7A H 0.9256 -0.1286 0.3780 0.082 Uiso 1 1 calc R . .
C8 C 1.184(2) -0.0969(3) 0.5389(12) 0.064(3) Uani 1 1 d . . .
H8A H 1.3400 -0.1015 0.6221 0.077 Uiso 1 1 calc R . .
C9 C 1.088(2) -0.0507(3) 0.5084(11) 0.051(2) Uani 1 1 d . . .
C10 C 1.140(2) -0.0221(3) 0.3896(11) 0.052(2) Uani 1 1 d . . .
C11 C 0.945(2) -0.0273(4) 0.6123(12) 0.063(3) Uani 1 1 d . . .
C12 C 0.902(3) -0.0521(4) 0.7446(15) 0.085(4) Uani 1 1 d . . .
H12A H 0.9886 -0.0817 0.7683 0.101 Uiso 1 1 calc R . .
C13 C 0.738(3) -0.0325(4) 0.8342(16) 0.093(4) Uani 1 1 d . . .
H13A H 0.6788 -0.0512 0.9039 0.112 Uiso 1 1 calc R . .
C14 C 0.665(2) 0.0122(3) 0.8214(11) 0.061(3) Uani 1 1 d . . .
H14A H 0.5818 0.0260 0.8924 0.073 Uiso 1 1 calc R . .
C15 C 0.703(2) 0.0377(4) 0.7148(11) 0.056(3) Uani 1 1 d . . .
H15A H 0.6253 0.0682 0.7049 0.067 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
I C3 2.020(13) . ?
C1 C6 1.463(17) . ?
C1 C2 1.475(19) . ?
C1 H1A 0.9300 . ?
C2 C3 1.320(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.312(17) . ?
C4 C5 1.462(17) . ?
C4 H4A 0.9300 . ?
C5 C6 1.435(17) . ?
C5 H5A 0.9300 . ?
C6 C7 1.427(14) . ?
C7 C8 1.322(13) . ?
C7 H7A 0.9300 . ?
C8 C9 1.384(13) . ?
C8 H8A 0.9300 . ?
C9 C10 1.439(12) . ?
C9 C11 1.462(14) . ?
C10 C15 1.422(12) 3_756 ?
C10 C11 1.447(14) 3_756 ?
C11 C10 1.447(14) 3_756 ?
C11 C12 1.474(15) . ?
C12 C13 1.381(16) . ?
C12 H12A 0.9300 . ?
C13 C14 1.305(15) . ?
C13 H13A 0.9300 . ?
C14 C15 1.276(13) . ?
C14 H14A 0.9300 . ?
C15 C10 1.422(12) 3_756 ?
C15 H15A 0.9300 . ?

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
C6 C1 C2 119.7(15) . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 C2 C1 119.5(15) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C4 C3 C2 122.9(15) . . ?
C4 C3 I 118.8(11) . . ?
C2 C3 I 118.3(12) . . ?
C3 C4 C5 123.6(15) . . ?
C3 C4 H4A 118.2 . . ?
C5 C4 H4A 118.2 . . ?
C6 C5 C4 117.3(13) . . ?
C6 C5 H5A 121.3 . . ?
C4 C5 H5A 121.3 . . ?
C7 C6 C5 121.2(12) . . ?
C7 C6 C1 121.9(13) . . ?
C5 C6 C1 116.8(12) . . ?
C8 C7 C6 132.3(11) . . ?
C8 C7 H7A 113.9 . . ?
C6 C7 H7A 113.9 . . ?
C7 C8 C9 126.6(10) . . ?
C7 C8 H8A 116.7 . . ?
C9 C8 H8A 116.7 . . ?
C8 C9 C10 125.4(10) . . ?
C8 C9 C11 117.7(10) . . ?
C10 C9 C11 116.6(9) . . ?
C15 C10 C9 124.4(9) 3_756 . ?
C15 C10 C11 118.4(9) 3_756 3_756 ?
C9 C10 C11 116.9(8) . 3_756 ?
C10 C11 C9 126.5(9) 3_756 . ?
C10 C11 C12 112.0(11) 3_756 . ?
C9 C11 C12 121.2(11) . . ?
C13 C12 C11 121.8(13) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C14 C13 C12 120.1(13) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 122.3(11) . . ?
C15 C14 H14A 118.9 . . ?
C13 C14 H14A 118.9 . . ?
C14 C15 C10 123.5(11) . 3_756 ?
C14 C15 H15A 118.2 . . ?
C10 C15 H15A 118.2 3_756 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -4(2) . . . . ?
C1 C2 C3 C4 4(2) . . . . ?
C1 C2 C3 I -175.9(11) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
I C3 C4 C5 178.0(13) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
C4 C5 C6 C7 177.1(13) . . . . ?
C4 C5 C6 C1 0(2) . . . . ?
C2 C1 C6 C7 -175.0(13) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
C5 C6 C7 C8 161.4(15) . . . . ?
C1 C6 C7 C8 -21(2) . . . . ?
C6 C7 C8 C9 -178.0(13) . . . . ?
C7 C8 C9 C10 -72.8(16) . . . . ?
C7 C8 C9 C11 113.0(13) . . . . ?
C8 C9 C10 C15 0.7(16) . . . 3_756 ?
C11 C9 C10 C15 175.1(10) . . . 3_756 ?
C8 C9 C10 C11 -172.3(10) . . . 3_756 ?
C11 C9 C10 C11 2.0(15) . . . 3_756 ?
C8 C9 C11 C10 172.5(10) . . . 3_756 ?
C10 C9 C11 C10 -2.2(17) . . . 3_756 ?
C8 C9 C11 C12 -0.3(16) . . . . ?
C10 C9 C11 C12 -175.1(9) . . . . ?
C10 C11 C12 C13 13.7(17) 3_756 . . . ?
C9 C11 C12 C13 -172.4(12) . . . . ?
C11 C12 C13 C14 -14(2) . . . . ?
C12 C13 C14 C15 10(2) . . . . ?
C13 C14 C15 C10 -8(2) . . . 3_756 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.119
