# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Keiichiro Ogawa'
'Jun Harada'
'Mayuko Harakawa'

_publ_contact_author_name        'Keiichiro Ogawa'
_publ_contact_author_email       OGAWA@RAMIE.C.U-TOKYO.AC.JP

_publ_section_title              
;
Conformational change of
all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms
;

# Attachment 'ogawa.cif'

data_monort
_database_code_depnum_ccdc_archive 'CCDC 693552'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenyl-1,3,5-hexatriene
;
_chemical_name_common            ?
_chemical_melting_point          196.2_C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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   P_1_21/c_1

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                   14.566(3)
_cell_length_b                   7.4368(14)
_cell_length_c                   6.2542(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.822(4)
_cell_angle_gamma                90.00
_cell_volume                     672.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    2159
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      25.7

_exptl_crystal_description       plate
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 20s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      300
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8242
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1539
_reflns_number_gt                976
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0353P)²+0.1595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77311(12) 0.4963(2) 0.4749(3) 0.0506(4) Uani 1 1 d . . .
C2 C 0.75200(15) 0.4192(2) 0.2715(3) 0.0627(5) Uani 1 1 d . . .
C3 C 0.66368(17) 0.4231(3) 0.1667(3) 0.0719(6) Uani 1 1 d . . .
C4 C 0.59494(16) 0.5065(3) 0.2594(3) 0.0700(6) Uani 1 1 d . . .
C5 C 0.61482(14) 0.5883(3) 0.4570(3) 0.0649(5) Uani 1 1 d . . .
C6 C 0.70237(13) 0.5841(2) 0.5618(3) 0.0567(5) Uani 1 1 d . . .
C7 C 0.86593(13) 0.4735(2) 0.5876(3) 0.0568(5) Uani 1 1 d . . .
C8 C 0.89581(13) 0.5210(2) 0.7891(3) 0.0556(5) Uani 1 1 d . . .
C9 C 0.98529(13) 0.4796(2) 0.8978(3) 0.0597(5) Uani 1 1 d . . .
H2 H 0.8033(14) 0.364(3) 0.208(3) 0.078(6) Uiso 1 1 d . . .
H3 H 0.6504(14) 0.371(3) 0.025(4) 0.088(7) Uiso 1 1 d . . .
H4 H 0.5305(17) 0.508(3) 0.191(3) 0.083(6) Uiso 1 1 d . . .
H5 H 0.5649(14) 0.646(3) 0.527(3) 0.080(6) Uiso 1 1 d . . .
H6 H 0.7153(12) 0.637(3) 0.706(3) 0.068(5) Uiso 1 1 d . . .
H7 H 0.9127(13) 0.409(3) 0.510(3) 0.073(6) Uiso 1 1 d . . .
H8 H 0.8517(13) 0.580(3) 0.864(3) 0.063(5) Uiso 1 1 d . . .
H9 H 1.0280(14) 0.410(3) 0.820(3) 0.080(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0634(11) 0.0379(8) 0.0504(9) 0.0031(7) 0.0059(7) -0.0058(7)
C2 0.0843(14) 0.0499(10) 0.0545(11) -0.0036(8) 0.0112(10) 0.0044(9)
C3 0.1021(18) 0.0616(12) 0.0488(11) -0.0049(9) -0.0044(11) -0.0061(11)
C4 0.0727(13) 0.0690(13) 0.0642(12) 0.0071(10) -0.0095(10) -0.0077(10)
C5 0.0653(13) 0.0645(12) 0.0648(12) -0.0010(9) 0.0076(10) 0.0004(9)
C6 0.0674(12) 0.0516(10) 0.0509(10) -0.0053(8) 0.0068(8) -0.0058(8)
C7 0.0626(11) 0.0480(10) 0.0606(11) 0.0005(8) 0.0109(9) -0.0025(8)
C8 0.0577(11) 0.0491(10) 0.0603(11) 0.0018(8) 0.0080(8) -0.0068(8)
C9 0.0584(11) 0.0539(10) 0.0669(11) 0.0023(10) 0.0073(9) -0.0048(8)

_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 C6 1.385(2) . ?
C1 C2 1.396(2) . ?
C1 C7 1.458(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.98(2) . ?
C3 C4 1.364(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.377(3) . ?
C4 H4 0.98(2) . ?
C5 C6 1.363(3) . ?
C5 H5 0.99(2) . ?
C6 H6 0.984(19) . ?
C7 C8 1.331(2) . ?
C7 H7 1.01(2) . ?
C8 C9 1.430(3) . ?
C8 H8 0.948(19) . ?
C9 C9 1.334(4) 3_767 ?
C9 H9 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.25(17) . . ?
C6 C1 C7 123.75(16) . . ?
C2 C1 C7 118.94(17) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 122.2(11) . . ?
C1 C2 H2 116.6(11) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 119.7(12) . . ?
C2 C3 H3 120.2(12) . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 122.0(12) . . ?
C5 C4 H4 118.3(13) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.4(12) . . ?
C4 C5 H5 120.1(12) . . ?
C5 C6 C1 121.29(17) . . ?
C5 C6 H6 119.9(10) . . ?
C1 C6 H6 118.7(10) . . ?
C8 C7 C1 127.35(18) . . ?
C8 C7 H7 114.9(10) . . ?
C1 C7 H7 117.6(10) . . ?
C7 C8 C9 124.73(19) . . ?
C7 C8 H8 115.3(11) . . ?
C9 C8 H8 119.9(11) . . ?
C9 C9 C8 125.3(2) 3_767 . ?
C9 C9 H9 116.5(12) 3_767 . ?
C8 C9 H9 118.2(12) . . ?

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 -3.0(3) . . . . ?
C7 C1 C2 C3 174.25(17) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
C7 C1 C6 C5 -174.34(17) . . . . ?
C6 C1 C7 C8 4.4(3) . . . . ?
C2 C1 C7 C8 -172.70(17) . . . . ?
C1 C7 C8 C9 173.61(16) . . . . ?
C7 C8 C9 C9 -177.3(2) . . . 3_767 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.033

#===END

data_mono90k
_database_code_depnum_ccdc_archive 'CCDC 693553'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenyl-1,3,5-hexatriene
;
_chemical_name_common            ?
_chemical_melting_point          196.2_C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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   P_1_21/c_1

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                   14.4012(13)
_cell_length_b                   7.2212(6)
_cell_length_c                   6.2416(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.338(2)
_cell_angle_gamma                90.00
_cell_volume                     645.12(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3692
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      30.0

_exptl_crystal_description       plate
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      90
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7571
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1491
_reflns_number_gt                1266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0577P)²+0.2750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1491
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77317(8) 0.49908(15) 0.46948(18) 0.0168(3) Uani 1 1 d . . .
C2 C 0.75314(9) 0.41912(16) 0.26485(19) 0.0199(3) Uani 1 1 d . . .
C3 C 0.66318(9) 0.42065(17) 0.15888(19) 0.0213(3) Uani 1 1 d . . .
C4 C 0.59145(8) 0.50405(17) 0.25454(19) 0.0204(3) Uani 1 1 d . . .
C5 C 0.61098(8) 0.58991(16) 0.45408(19) 0.0199(3) Uani 1 1 d . . .
C6 C 0.70039(8) 0.58785(16) 0.56049(18) 0.0181(3) Uani 1 1 d . . .
C7 C 0.86698(8) 0.47637(16) 0.58331(19) 0.0188(3) Uani 1 1 d . . .
C8 C 0.89528(8) 0.52546(16) 0.78792(19) 0.0187(3) Uani 1 1 d . . .
C9 C 0.98590(8) 0.47948(16) 0.89619(19) 0.0193(3) Uani 1 1 d . . .
H2 H 0.8036(10) 0.360(2) 0.200(2) 0.027(4) Uiso 1 1 d . . .
H3 H 0.6503(10) 0.360(2) 0.016(2) 0.026(4) Uiso 1 1 d . . .
H4 H 0.5274(10) 0.503(2) 0.182(2) 0.018(3) Uiso 1 1 d . . .
H5 H 0.5613(11) 0.649(2) 0.521(2) 0.027(4) Uiso 1 1 d . . .
H6 H 0.7116(9) 0.647(2) 0.703(2) 0.022(4) Uiso 1 1 d . . .
H7 H 0.9112(10) 0.412(2) 0.504(2) 0.026(4) Uiso 1 1 d . . .
H8 H 0.8513(10) 0.588(2) 0.872(2) 0.025(4) Uiso 1 1 d . . .
H9 H 1.0291(11) 0.409(2) 0.810(2) 0.029(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0200(6) 0.0134(5) 0.0170(5) 0.0020(4) 0.0017(4) -0.0021(4)
C2 0.0253(6) 0.0160(5) 0.0188(6) -0.0005(4) 0.0042(4) 0.0014(4)
C3 0.0296(6) 0.0183(6) 0.0153(5) -0.0009(4) -0.0006(4) -0.0027(5)
C4 0.0209(6) 0.0207(6) 0.0187(5) 0.0027(4) -0.0026(4) -0.0030(4)
C5 0.0202(6) 0.0189(6) 0.0208(6) 0.0013(4) 0.0032(5) -0.0009(4)
C6 0.0218(6) 0.0162(5) 0.0164(5) -0.0006(4) 0.0022(4) -0.0020(4)
C7 0.0193(6) 0.0160(5) 0.0213(6) 0.0011(4) 0.0032(5) -0.0003(4)
C8 0.0186(6) 0.0164(5) 0.0210(6) 0.0011(4) 0.0021(4) -0.0012(4)
C9 0.0189(6) 0.0166(5) 0.0222(6) 0.0013(4) 0.0015(4) -0.0014(4)

_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 C6 1.4013(16) . ?
C1 C2 1.4023(16) . ?
C1 C7 1.4645(16) . ?
C2 C3 1.3881(17) . ?
C2 H2 0.968(15) . ?
C3 C4 1.3865(18) . ?
C3 H3 0.992(15) . ?
C4 C5 1.3919(16) . ?
C4 H4 0.981(15) . ?
C5 C6 1.3822(16) . ?
C5 H5 0.966(16) . ?
C6 H6 0.981(15) . ?
C7 C8 1.3445(16) . ?
C7 H7 0.967(16) . ?
C8 C9 1.4406(16) . ?
C8 H8 0.979(16) . ?
C9 C9 1.348(2) 3_767 ?
C9 H9 1.003(16) . ?

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 118.01(11) . . ?
C6 C1 C7 123.07(10) . . ?
C2 C1 C7 118.80(11) . . ?
C3 C2 C1 121.20(11) . . ?
C3 C2 H2 120.6(9) . . ?
C1 C2 H2 118.2(9) . . ?
C4 C3 C2 119.92(11) . . ?
C4 C3 H3 120.3(8) . . ?
C2 C3 H3 119.8(8) . . ?
C3 C4 C5 119.49(11) . . ?
C3 C4 H4 120.5(8) . . ?
C5 C4 H4 120.1(8) . . ?
C6 C5 C4 120.71(11) . . ?
C6 C5 H5 119.5(9) . . ?
C4 C5 H5 119.8(9) . . ?
C5 C6 C1 120.59(11) . . ?
C5 C6 H6 118.8(8) . . ?
C1 C6 H6 120.6(8) . . ?
C8 C7 C1 126.73(11) . . ?
C8 C7 H7 117.7(9) . . ?
C1 C7 H7 115.4(9) . . ?
C7 C8 C9 123.28(11) . . ?
C7 C8 H8 119.1(8) . . ?
C9 C8 H8 117.5(8) . . ?
C9 C9 C8 124.17(14) 3_767 . ?
C9 C9 H9 119.2(9) 3_767 . ?
C8 C9 H9 116.7(9) . . ?

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 -2.67(17) . . . . ?
C7 C1 C2 C3 173.62(11) . . . . ?
C1 C2 C3 C4 0.69(18) . . . . ?
C2 C3 C4 C5 1.67(18) . . . . ?
C3 C4 C5 C6 -2.00(18) . . . . ?
C4 C5 C6 C1 -0.04(18) . . . . ?
C2 C1 C6 C5 2.34(16) . . . . ?
C7 C1 C6 C5 -173.79(11) . . . . ?
C6 C1 C7 C8 3.90(19) . . . . ?
C2 C1 C7 C8 -172.20(11) . . . . ?
C1 C7 C8 C9 172.68(11) . . . . ?
C7 C8 C9 C9 -177.06(14) . . . 3_767 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.047
#===END

data_orthort
_database_code_depnum_ccdc_archive 'CCDC 693554'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenyl-1,3,5-hexatriene
;
_chemical_name_common            ?
_chemical_melting_point          200.5_C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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           orthorhombic
_symmetry_space_group_name_H-M   P_b_c_a

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

_cell_length_a                   7.7403(5)
_cell_length_b                   9.8733(7)
_cell_length_c                   18.1285(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1385.42(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4024
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      24.3

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      300
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19981
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         30.03
_reflns_number_total             2021
_reflns_number_gt                1192
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0341P)²+0.1813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99504(13) 0.39263(12) 0.61289(6) 0.0622(3) Uani 1 1 d . . .
C2 C 1.06365(17) 0.52223(14) 0.60653(8) 0.0760(4) Uani 1 1 d . . .
C3 C 1.02553(19) 0.62199(15) 0.65774(9) 0.0858(4) Uani 1 1 d . . .
C4 C 0.91940(19) 0.59370(16) 0.71627(8) 0.0834(4) Uani 1 1 d . . .
C5 C 0.85026(19) 0.46725(16) 0.72302(9) 0.0850(4) Uani 1 1 d . . .
C6 C 0.88648(17) 0.36871(14) 0.67254(7) 0.0747(4) Uani 1 1 d . . .
C7 C 1.03833(15) 0.28868(14) 0.55869(6) 0.0699(3) Uani 1 1 d . . .
C8 C 0.98080(15) 0.16210(14) 0.55612(7) 0.0695(3) Uani 1 1 d . . .
C9 C 1.02710(16) 0.06383(14) 0.50118(7) 0.0742(4) Uani 1 1 d . . .
H2 H 1.1359(17) 0.5404(12) 0.5665(7) 0.084(4) Uiso 1 1 d . . .
H3 H 1.0738(19) 0.7090(16) 0.6496(8) 0.103(5) Uiso 1 1 d . . .
H4 H 0.896(2) 0.6656(16) 0.7528(9) 0.111(5) Uiso 1 1 d . . .
H5 H 0.774(2) 0.4474(15) 0.7660(8) 0.115(5) Uiso 1 1 d . . .
H6 H 0.8363(17) 0.2764(14) 0.6764(7) 0.092(4) Uiso 1 1 d . . .
H7 H 1.1180(17) 0.3173(13) 0.5190(7) 0.085(4) Uiso 1 1 d . . .
H8 H 0.9026(17) 0.1317(11) 0.5937(7) 0.076(4) Uiso 1 1 d . . .
H9 H 1.1068(18) 0.0943(13) 0.4628(7) 0.088(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0512(6) 0.0736(7) 0.0616(6) 0.0105(6) -0.0059(5) 0.0055(5)
C2 0.0671(8) 0.0881(9) 0.0729(8) 0.0198(7) -0.0024(6) -0.0037(6)
C3 0.0827(9) 0.0694(9) 0.1053(11) 0.0112(8) -0.0217(8) -0.0010(7)
C4 0.0743(8) 0.0831(9) 0.0929(10) -0.0045(8) -0.0095(7) 0.0208(7)
C5 0.0747(8) 0.0901(10) 0.0902(10) -0.0008(8) 0.0153(7) 0.0116(7)
C6 0.0662(7) 0.0756(8) 0.0824(8) 0.0052(7) 0.0122(6) 0.0019(6)
C7 0.0588(6) 0.0895(9) 0.0613(7) 0.0091(6) 0.0015(5) 0.0039(6)
C8 0.0578(6) 0.0872(9) 0.0634(7) 0.0019(6) -0.0006(5) 0.0055(6)
C9 0.0622(7) 0.0931(9) 0.0673(7) -0.0034(7) -0.0017(6) 0.0069(7)

_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 C6 1.3897(16) . ?
C1 C2 1.3901(17) . ?
C1 C7 1.4599(17) . ?
C2 C3 1.385(2) . ?
C2 H2 0.934(13) . ?
C3 C4 1.371(2) . ?
C3 H3 0.949(16) . ?
C4 C5 1.364(2) . ?
C4 H4 0.987(17) . ?
C5 C6 1.3648(19) . ?
C5 H5 0.996(17) . ?
C6 H6 0.993(14) . ?
C7 C8 1.3275(18) . ?
C7 H7 0.989(13) . ?
C8 C9 1.4359(18) . ?
C8 H8 0.959(13) . ?
C9 C9 1.329(3) 5_756 ?
C9 H9 0.978(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.87(12) . . ?
C6 C1 C7 122.89(11) . . ?
C2 C1 C7 120.24(11) . . ?
C3 C2 C1 121.17(13) . . ?
C3 C2 H2 120.8(8) . . ?
C1 C2 H2 118.1(8) . . ?
C4 C3 C2 120.10(14) . . ?
C4 C3 H3 122.8(9) . . ?
C2 C3 H3 117.1(9) . . ?
C5 C4 C3 119.41(15) . . ?
C5 C4 H4 121.8(9) . . ?
C3 C4 H4 118.8(9) . . ?
C4 C5 C6 120.79(15) . . ?
C4 C5 H5 118.8(9) . . ?
C6 C5 H5 120.4(9) . . ?
C5 C6 C1 121.65(13) . . ?
C5 C6 H6 121.7(8) . . ?
C1 C6 H6 116.6(8) . . ?
C8 C7 C1 127.48(12) . . ?
C8 C7 H7 116.9(7) . . ?
C1 C7 H7 115.6(7) . . ?
C7 C8 C9 125.22(13) . . ?
C7 C8 H8 118.8(7) . . ?
C9 C8 H8 116.0(7) . . ?
C9 C9 C8 125.75(17) 5_756 . ?
C9 C9 H9 117.9(8) 5_756 . ?
C8 C9 H9 116.3(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
C6 C1 C2 C3 0.31(18) . . . . ?
C7 C1 C2 C3 -179.39(11) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 -0.69(18) . . . . ?
C7 C1 C6 C5 179.00(12) . . . . ?
C6 C1 C7 C8 2.00(18) . . . . ?
C2 C1 C7 C8 -178.32(12) . . . . ?
C1 C7 C8 C9 179.70(11) . . . . ?
C7 C8 C9 C9 178.66(15) . . . 5_756 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.032
#===END

data_ortho90
_database_code_depnum_ccdc_archive 'CCDC 693555'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenylhexatriene
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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           orthorhombic
_symmetry_space_group_name_H-M   P_b_c_a

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

_cell_length_a                   7.4842(3)
_cell_length_b                   10.0656(4)
_cell_length_c                   17.6698(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1331.12(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    7802
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      30.0

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      90
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19219
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0107
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         30.03
_reflns_number_total             1949
_reflns_number_gt                1730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0715P)²+0.3144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1949
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99257(10) 0.38811(8) 0.61389(4) 0.01612(18) Uani 1 1 d . . .
C2 C 1.05718(11) 0.51790(9) 0.60431(5) 0.01891(19) Uani 1 1 d . . .
C3 C 1.01818(12) 0.61709(8) 0.65677(5) 0.0208(2) Uani 1 1 d . . .
C4 C 0.91526(12) 0.58798(9) 0.72008(5) 0.0208(2) Uani 1 1 d . . .
C5 C 0.84880(11) 0.45989(9) 0.73009(5) 0.0210(2) Uani 1 1 d . . .
C6 C 0.88639(11) 0.36138(8) 0.67765(5) 0.01888(19) Uani 1 1 d . . .
C7 C 1.03802(11) 0.28584(8) 0.55805(4) 0.01820(19) Uani 1 1 d . . .
C8 C 0.97871(11) 0.15911(9) 0.55748(5) 0.01891(19) Uani 1 1 d . . .
C9 C 1.02825(11) 0.06383(9) 0.50011(5) 0.0200(2) Uani 1 1 d . . .
H2 H 1.1314(16) 0.5381(11) 0.5597(7) 0.025(3) Uiso 1 1 d . . .
H3 H 1.0669(17) 0.7080(13) 0.6480(7) 0.029(3) Uiso 1 1 d . . .
H4 H 0.8923(18) 0.6587(13) 0.7573(8) 0.033(3) Uiso 1 1 d . . .
H5 H 0.7755(18) 0.4396(13) 0.7743(6) 0.028(3) Uiso 1 1 d . . .
H6 H 0.8345(15) 0.2708(11) 0.6860(6) 0.023(3) Uiso 1 1 d . . .
H7 H 1.1193(17) 0.3128(13) 0.5165(7) 0.030(3) Uiso 1 1 d . . .
H8 H 0.8953(17) 0.1266(12) 0.5979(7) 0.026(3) Uiso 1 1 d . . .
H9 H 1.1082(18) 0.0937(13) 0.4585(7) 0.033(3) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0142(3) 0.0183(4) 0.0159(4) 0.0014(3) -0.0011(3) 0.0015(3)
C2 0.0181(4) 0.0203(4) 0.0184(4) 0.0040(3) -0.0007(3) -0.0007(3)
C3 0.0210(4) 0.0166(4) 0.0248(4) 0.0021(3) -0.0042(3) 0.0000(3)
C4 0.0195(4) 0.0203(4) 0.0225(4) -0.0025(3) -0.0027(3) 0.0048(3)
C5 0.0191(4) 0.0223(4) 0.0214(4) -0.0001(3) 0.0034(3) 0.0029(3)
C6 0.0178(4) 0.0187(4) 0.0202(4) 0.0012(3) 0.0027(3) 0.0001(3)
C7 0.0170(4) 0.0215(4) 0.0161(4) 0.0005(3) 0.0001(3) 0.0020(3)
C8 0.0168(4) 0.0220(4) 0.0179(4) -0.0022(3) -0.0003(3) 0.0019(3)
C9 0.0172(4) 0.0234(4) 0.0193(4) -0.0029(3) -0.0008(3) 0.0024(3)

_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 1.4032(11) . ?
C1 C6 1.4047(11) . ?
C1 C7 1.4659(11) . ?
C2 C3 1.3932(12) . ?
C2 H2 0.985(12) . ?
C3 C4 1.3896(13) . ?
C3 H3 0.997(13) . ?
C4 C5 1.3932(12) . ?
C4 H4 0.984(14) . ?
C5 C6 1.3859(12) . ?
C5 H5 0.976(12) . ?
C6 H6 1.002(11) . ?
C7 C8 1.3506(12) . ?
C7 H7 0.992(13) . ?
C8 C9 1.4439(12) . ?
C8 H8 1.004(13) . ?
C9 C9 1.3527(18) 5_756 ?
C9 H9 0.994(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.03(7) . . ?
C2 C1 C7 119.52(7) . . ?
C6 C1 C7 122.45(7) . . ?
C3 C2 C1 120.98(8) . . ?
C3 C2 H2 120.1(7) . . ?
C1 C2 H2 118.9(7) . . ?
C4 C3 C2 120.04(8) . . ?
C4 C3 H3 121.4(7) . . ?
C2 C3 H3 118.5(7) . . ?
C3 C4 C5 119.68(8) . . ?
C3 C4 H4 118.9(8) . . ?
C5 C4 H4 121.5(8) . . ?
C6 C5 C4 120.32(8) . . ?
C6 C5 H5 120.0(7) . . ?
C4 C5 H5 119.7(7) . . ?
C5 C6 C1 120.93(8) . . ?
C5 C6 H6 118.3(7) . . ?
C1 C6 H6 120.8(7) . . ?
C8 C7 C1 126.30(8) . . ?
C8 C7 H7 117.0(8) . . ?
C1 C7 H7 116.7(8) . . ?
C7 C8 C9 123.24(8) . . ?
C7 C8 H8 120.5(7) . . ?
C9 C8 H8 116.3(7) . . ?
C9 C9 C8 123.55(10) 5_756 . ?
C9 C9 H9 118.3(8) 5_756 . ?
C8 C9 H9 118.2(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
C6 C1 C2 C3 0.43(12) . . . . ?
C7 C1 C2 C3 -179.27(7) . . . . ?
C1 C2 C3 C4 0.59(13) . . . . ?
C2 C3 C4 C5 -1.14(13) . . . . ?
C3 C4 C5 C6 0.65(13) . . . . ?
C4 C5 C6 C1 0.39(13) . . . . ?
C2 C1 C6 C5 -0.92(12) . . . . ?
C7 C1 C6 C5 178.77(8) . . . . ?
C2 C1 C7 C8 -176.35(8) . . . . ?
C6 C1 C7 C8 3.97(13) . . . . ?
C1 C7 C8 C9 179.50(8) . . . . ?
C7 C8 C9 C9 178.85(10) . . . 5_756 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.055
#===END

data_ortho370
_database_code_depnum_ccdc_archive 'CCDC 693556'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenyl-1,3,5-hexatriene
;
_chemical_name_common            ?
_chemical_melting_point          200.5_C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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           orthorhombic
_symmetry_space_group_name_H-M   P_b_c_a

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

_cell_length_a                   7.883(2)
_cell_length_b                   9.670(3)
_cell_length_c                   18.529(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1412.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    370
_cell_measurement_reflns_used    3248
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      21.5

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 20s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      370
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20490
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         30.08
_reflns_number_total             2071
_reflns_number_gt                874
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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+0.1205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2071
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.2354
_refine_ls_wR_factor_gt          0.1712
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9957(2) 0.3979(2) 0.61244(9) 0.0926(6) Uani 1 1 d . . .
C2 C 1.0685(3) 0.5285(3) 0.60810(14) 0.1159(8) Uani 1 1 d . . .
C3 C 1.0311(4) 0.6298(3) 0.65909(18) 0.1300(9) Uani 1 1 d . . .
C4 C 0.9226(4) 0.6003(3) 0.71418(16) 0.1245(8) Uani 1 1 d . . .
C5 C 0.8514(3) 0.4747(3) 0.71820(16) 0.1279(9) Uani 1 1 d . . .
C6 C 0.8854(3) 0.3760(3) 0.66906(12) 0.1120(7) Uani 1 1 d . . .
C7 C 1.0384(3) 0.2930(3) 0.55896(11) 0.1060(7) Uani 1 1 d . . .
C8 C 0.9812(2) 0.1648(3) 0.55533(11) 0.1008(6) Uani 1 1 d . . .
C9 C 1.0264(3) 0.0645(2) 0.50167(12) 0.1107(7) Uani 1 1 d . . .
H2 H 1.137(3) 0.546(2) 0.5727(12) 0.124(8) Uiso 1 1 d . . .
H3 H 1.073(4) 0.716(3) 0.6507(13) 0.154(10) Uiso 1 1 d . . .
H4 H 0.902(4) 0.670(3) 0.7473(18) 0.163(10) Uiso 1 1 d . . .
H5 H 0.769(4) 0.453(3) 0.7590(15) 0.177(10) Uiso 1 1 d . . .
H6 H 0.833(3) 0.280(2) 0.6691(12) 0.136(7) Uiso 1 1 d . . .
H7 H 1.121(3) 0.323(2) 0.5203(11) 0.125(6) Uiso 1 1 d . . .
H8 H 0.902(3) 0.1426(19) 0.5943(11) 0.116(6) Uiso 1 1 d . . .
H9 H 1.112(3) 0.097(2) 0.4626(12) 0.143(8) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0762(10) 0.1098(14) 0.0918(12) 0.0154(10) -0.0095(8) 0.0095(9)
C2 0.0959(14) 0.143(2) 0.1093(16) 0.0299(15) -0.0017(12) -0.0068(13)
C3 0.1199(19) 0.1089(18) 0.161(2) 0.0177(19) -0.0328(18) -0.0056(15)
C4 0.1098(17) 0.128(2) 0.136(2) -0.0045(18) -0.0123(15) 0.0297(15)
C5 0.1097(16) 0.132(2) 0.142(2) 0.0027(17) 0.0189(15) 0.0163(14)
C6 0.0973(13) 0.1140(16) 0.1248(16) 0.0075(13) 0.0184(12) 0.0046(12)
C7 0.0857(12) 0.1383(19) 0.0941(13) 0.0160(12) 0.0028(10) 0.0056(11)
C8 0.0826(11) 0.1283(17) 0.0915(13) 0.0056(12) -0.0006(10) 0.0060(11)
C9 0.0911(13) 0.1409(18) 0.0999(13) 0.0015(16) -0.0048(10) 0.0090(13)

_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 C6 1.379(3) . ?
C1 C2 1.390(3) . ?
C1 C7 1.457(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.86(2) . ?
C3 C4 1.362(4) . ?
C3 H3 0.91(3) . ?
C4 C5 1.340(4) . ?
C4 H4 0.93(3) . ?
C5 C6 1.346(3) . ?
C5 H5 1.02(3) . ?
C6 H6 1.02(2) . ?
C7 C8 1.320(3) . ?
C7 H7 1.01(2) . ?
C8 C9 1.434(3) . ?
C8 H8 0.98(2) . ?
C9 C9 1.317(5) 5_756 ?
C9 H9 1.04(3) . ?

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 116.3(2) . . ?
C6 C1 C7 123.8(2) . . ?
C2 C1 C7 119.9(2) . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 118.5(15) . . ?
C3 C2 H2 120.6(15) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 123.2(17) . . ?
C2 C3 H3 116.9(17) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 123.5(18) . . ?
C3 C4 H4 116.9(18) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.8(17) . . ?
C6 C5 H5 118.8(17) . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 H6 124.5(13) . . ?
C1 C6 H6 113.4(13) . . ?
C8 C7 C1 127.5(2) . . ?
C8 C7 H7 117.1(12) . . ?
C1 C7 H7 115.4(12) . . ?
C7 C8 C9 125.8(2) . . ?
C7 C8 H8 112.7(11) . . ?
C9 C8 H8 121.4(11) . . ?
C9 C9 C8 126.5(3) 5_756 . ?
C9 C9 H9 117.2(13) 5_756 . ?
C8 C9 H9 116.3(13) . . ?

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(3) . . . . ?
C7 C1 C2 C3 -179.25(18) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C7 C1 C6 C5 178.8(2) . . . . ?
C6 C1 C7 C8 0.2(3) . . . . ?
C2 C1 C7 C8 179.91(19) . . . . ?
C1 C7 C8 C9 179.98(17) . . . . ?
C7 C8 C9 C9 178.3(2) . . . 5_756 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.020
#===END

data_orthort2
_database_code_depnum_ccdc_archive 'CCDC 693557'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
E,E,E-1,6-diphenyl-1,3,5-hexatriene
;
_chemical_name_common            ?
_chemical_melting_point          200.5_C
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16'
_chemical_formula_weight         232.31

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           orthorhombic
_symmetry_space_group_name_H-M   P_b_c_a

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

_cell_length_a                   7.7439(5)
_cell_length_b                   9.8691(7)
_cell_length_c                   18.1365(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1386.09(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    300
_cell_measurement_reflns_used    3568
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      24.3

_exptl_crystal_description       block
_exptl_crystal_colour            pale_yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.9815
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
The data collection covered over a full sphere of reciprocal space by a
combination of four sets of exposures; each set had a different φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. The crystal-to-detector distance was 4 cm and the detector swing angle
was -32°. Crystal decay was monitored by repeating the measurement of the
initial 50 frames at the end of data collection and analyzing the duplicate
reflections.
;

_diffrn_ambient_temperature      300
_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 SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19949
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         30.03
_reflns_number_total             2022
_reflns_number_gt                1135
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0358P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0056(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2022
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.99511(13) 0.39273(12) 0.61288(6) 0.0629(3) Uani 1 1 d . . .
C2 C 1.06391(17) 0.52238(15) 0.60651(8) 0.0767(4) Uani 1 1 d . . .
C3 C 1.0257(2) 0.62194(15) 0.65774(9) 0.0867(4) Uani 1 1 d . . .
C4 C 0.91963(19) 0.59389(16) 0.71614(9) 0.0846(4) Uani 1 1 d . . .
C5 C 0.85043(19) 0.46744(16) 0.72286(9) 0.0859(4) Uani 1 1 d . . .
C6 C 0.88665(17) 0.36893(15) 0.67245(7) 0.0757(4) Uani 1 1 d . . .
C7 C 1.03844(15) 0.28866(14) 0.55868(7) 0.0710(3) Uani 1 1 d . . .
C8 C 0.98069(15) 0.16206(14) 0.55604(7) 0.0703(3) Uani 1 1 d . . .
C9 C 1.02708(17) 0.06386(14) 0.50117(7) 0.0751(4) Uani 1 1 d . . .
H2 H 1.1375(17) 0.5399(12) 0.5663(7) 0.086(4) Uiso 1 1 d . . .
H3 H 1.0726(18) 0.7079(15) 0.6504(7) 0.101(5) Uiso 1 1 d . . .
H4 H 0.895(2) 0.6654(16) 0.7527(10) 0.116(5) Uiso 1 1 d . . .
H5 H 0.773(2) 0.4477(15) 0.7650(8) 0.114(5) Uiso 1 1 d . . .
H6 H 0.8367(17) 0.2776(14) 0.6764(7) 0.093(4) Uiso 1 1 d . . .
H7 H 1.1171(17) 0.3170(13) 0.5189(7) 0.088(4) Uiso 1 1 d . . .
H8 H 0.9019(17) 0.1316(11) 0.5934(6) 0.077(4) Uiso 1 1 d . . .
H9 H 1.1061(18) 0.0947(13) 0.4627(7) 0.091(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0509(6) 0.0745(7) 0.0633(6) 0.0110(6) -0.0062(5) 0.0059(5)
C2 0.0670(8) 0.0888(10) 0.0744(8) 0.0193(7) -0.0023(6) -0.0034(7)
C3 0.0839(9) 0.0694(9) 0.1067(11) 0.0112(8) -0.0210(9) -0.0015(7)
C4 0.0759(9) 0.0841(10) 0.0938(10) -0.0042(8) -0.0103(8) 0.0204(7)
C5 0.0745(8) 0.0916(10) 0.0918(10) -0.0006(8) 0.0150(8) 0.0118(7)
C6 0.0673(7) 0.0759(8) 0.0840(8) 0.0051(7) 0.0128(6) 0.0019(6)
C7 0.0595(6) 0.0906(9) 0.0627(7) 0.0093(6) 0.0018(5) 0.0044(6)
C8 0.0584(7) 0.0880(9) 0.0645(7) 0.0023(6) -0.0005(6) 0.0051(6)
C9 0.0627(7) 0.0946(9) 0.0679(7) -0.0034(8) -0.0022(6) 0.0072(7)

_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 C6 1.3885(16) . ?
C1 C2 1.3908(17) . ?
C1 C7 1.4608(17) . ?
C2 C3 1.384(2) . ?
C2 H2 0.941(13) . ?
C3 C4 1.369(2) . ?
C3 H3 0.932(15) . ?
C4 C5 1.364(2) . ?
C4 H4 0.987(17) . ?
C5 C6 1.3637(19) . ?
C5 H5 0.992(16) . ?
C6 H6 0.984(14) . ?
C7 C8 1.3278(18) . ?
C7 H7 0.985(13) . ?
C8 C9 1.4349(18) . ?
C8 H8 0.960(12) . ?
C9 C9 1.329(3) 5_756 ?
C9 H9 0.977(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.87(12) . . ?
C6 C1 C7 122.93(12) . . ?
C2 C1 C7 120.19(11) . . ?
C3 C2 C1 121.02(13) . . ?
C3 C2 H2 121.2(8) . . ?
C1 C2 H2 117.7(8) . . ?
C4 C3 C2 120.27(14) . . ?
C4 C3 H3 121.9(9) . . ?
C2 C3 H3 117.8(9) . . ?
C5 C4 C3 119.35(15) . . ?
C5 C4 H4 121.4(9) . . ?
C3 C4 H4 119.3(9) . . ?
C4 C5 C6 120.78(15) . . ?
C4 C5 H5 119.2(9) . . ?
C6 C5 H5 120.1(9) . . ?
C5 C6 C1 121.70(14) . . ?
C5 C6 H6 121.6(8) . . ?
C1 C6 H6 116.7(8) . . ?
C8 C7 C1 127.48(12) . . ?
C8 C7 H7 116.7(7) . . ?
C1 C7 H7 115.8(7) . . ?
C7 C8 C9 125.18(13) . . ?
C7 C8 H8 118.9(7) . . ?
C9 C8 H8 115.9(7) . . ?
C9 C9 C8 125.72(17) 5_756 . ?
C9 C9 H9 118.1(8) 5_756 . ?
C8 C9 H9 116.2(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
C6 C1 C2 C3 0.31(18) . . . . ?
C7 C1 C2 C3 -179.35(11) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 -0.65(18) . . . . ?
C7 C1 C6 C5 179.00(12) . . . . ?
C6 C1 C7 C8 2.11(19) . . . . ?
C2 C1 C7 C8 -178.25(12) . . . . ?
C1 C7 C8 C9 179.71(11) . . . . ?
C7 C8 C9 C9 178.53(15) . . . 5_756 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.100
_refine_diff_density_rms         0.022


