# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_6helicene-F4TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1533425'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ([6]helicene)(F4TCNQ)
_chemical_formula_moiety         '(C26 H16), (C12 F4 N4)'
_chemical_formula_sum            'C38 H16 F4 N4'
_chemical_formula_weight         604.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbcn '

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

_cell_length_a                   7.1454(4)
_cell_length_b                   17.2601(9)
_cell_length_c                   22.2970(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2749.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8752
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.27

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            13444
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2811
_reflns_number_gt                2477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+1.0215P] 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         2811
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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 0.50690(19) 1.12839(7) 0.62494(5) 0.0228(3) Uani 1 1 d . . .
H1 H 0.4829 1.1762 0.6072 0.027 Uiso 1 1 calc R . .
C2 C 0.36552(17) 1.08973(7) 0.65650(5) 0.0208(3) Uani 1 1 d . . .
H2 H 0.2465 1.1114 0.6588 0.025 Uiso 1 1 calc R . .
C3 C 0.68095(18) 1.09539(7) 0.62029(6) 0.0229(3) Uani 1 1 d . . .
H3 H 0.7743 1.1210 0.5991 0.027 Uiso 1 1 calc R . .
C4 C 0.40131(16) 1.01993(6) 0.68413(5) 0.0182(2) Uani 1 1 d . . .
H4 H 0.3056 0.9950 0.7048 0.022 Uiso 1 1 calc R . .
C5 C 0.72087(17) 1.02298(7) 0.64720(5) 0.0195(3) Uani 1 1 d . . .
C6 C 0.58078(16) 0.98533(6) 0.68174(5) 0.0169(2) Uani 1 1 d . . .
C7 C 0.89657(17) 0.98521(7) 0.63763(6) 0.0240(3) Uani 1 1 d . . .
H7 H 0.9933 1.0118 0.6188 0.029 Uiso 1 1 calc R . .
C8 C 0.92372(18) 0.91110(7) 0.65567(6) 0.0244(3) Uani 1 1 d . . .
H8 H 1.0353 0.8862 0.6463 0.029 Uiso 1 1 calc R . .
C9 C 0.78353(17) 0.87071(7) 0.68891(5) 0.0204(3) Uani 1 1 d . . .
C10 C 0.62301(16) 0.91059(6) 0.70854(5) 0.0172(2) Uani 1 1 d . . .
C11 C 0.80058(18) 0.78958(7) 0.70025(6) 0.0240(3) Uani 1 1 d . . .
H11 H 0.9109 0.7639 0.6906 0.029 Uiso 1 1 calc R . .
C12 C 0.65641(18) 0.74983(7) 0.72510(6) 0.0245(3) Uani 1 1 d . . .
H12 H 0.6596 0.6960 0.7259 0.029 Uiso 1 1 calc R . .
C13 C 0.5000 0.78977(9) 0.7500 0.0207(3) Uani 1 2 d S . .
C14 C 0.5000 0.87176(9) 0.7500 0.0178(3) Uani 1 2 d S . .
C15 C 0.53725(16) 0.92347(6) 0.52511(5) 0.0166(2) Uani 1 1 d . . .
C16 C 0.35895(16) 0.96186(7) 0.52985(5) 0.0177(2) Uani 1 1 d . . .
C17 C 0.32488(15) 1.03251(7) 0.50736(5) 0.0177(2) Uani 1 1 d . . .
C18 C 0.57132(17) 0.85143(6) 0.54917(5) 0.0190(2) Uani 1 1 d . . .
C19 C 0.43761(18) 0.80881(7) 0.58458(6) 0.0223(3) Uani 1 1 d . . .
C20 C 0.74409(18) 0.81033(7) 0.54053(5) 0.0225(3) Uani 1 1 d . . .
N1 N 0.33933(17) 0.77171(7) 0.61309(5) 0.0319(3) Uani 1 1 d . . .
N2 N 0.87682(17) 0.77402(6) 0.53429(5) 0.0311(3) Uani 1 1 d . . .
F1 F 0.21990(10) 0.92406(4) 0.55689(3) 0.02603(19) Uani 1 1 d . . .
F2 F 0.15421(9) 1.06276(4) 0.51412(3) 0.02516(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.3718(19) . ?
C1 C2 1.4004(17) . ?
C1 H1 0.9300 . ?
C2 C4 1.3771(17) . ?
C2 H2 0.9300 . ?
C3 C5 1.4155(17) . ?
C3 H3 0.9300 . ?
C4 C6 1.4156(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.4203(16) . ?
C5 C7 1.4306(17) . ?
C6 C10 1.4534(16) . ?
C7 C8 1.3550(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.4278(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.4074(16) . ?
C9 C11 1.4282(17) . ?
C10 C14 1.4408(13) . ?
C11 C12 1.3560(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.4257(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.415(2) . ?
C13 C12 1.4256(15) 3_656 ?
C14 C10 1.4409(13) 3_656 ?
C15 C18 1.3759(16) . ?
C15 C17 1.4393(16) 5_676 ?
C15 C16 1.4400(16) . ?
C16 F1 1.3327(13) . ?
C16 C17 1.3409(17) . ?
C17 F2 1.3351(13) . ?
C17 C15 1.4393(16) 5_676 ?
C18 C20 1.4368(17) . ?
C18 C19 1.4413(17) . ?
C19 N1 1.1433(17) . ?
C20 N2 1.1453(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 119.61(11) . . ?
C3 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C4 C2 C1 120.51(11) . . ?
C4 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C3 C5 121.15(11) . . ?
C1 C3 H3 119.4 . . ?
C5 C3 H3 119.4 . . ?
C2 C4 C6 121.36(11) . . ?
C2 C4 H4 119.3 . . ?
C6 C4 H4 119.3 . . ?
C3 C5 C6 119.46(11) . . ?
C3 C5 C7 121.06(11) . . ?
C6 C5 C7 119.40(11) . . ?
C4 C6 C5 117.76(10) . . ?
C4 C6 C10 123.16(10) . . ?
C5 C6 C10 118.86(10) . . ?
C8 C7 C5 120.76(11) . . ?
C8 C7 H7 119.6 . . ?
C5 C7 H7 119.6 . . ?
C7 C8 C9 120.97(11) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.63(11) . . ?
C10 C9 C11 119.60(11) . . ?
C8 C9 C11 120.71(11) . . ?
C9 C10 C14 117.98(11) . . ?
C9 C10 C6 118.38(10) . . ?
C14 C10 C6 123.36(10) . . ?
C12 C11 C9 120.24(11) . . ?
C12 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C11 C12 C13 120.67(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.91(8) . 3_656 ?
C14 C13 C12 118.91(8) . . ?
C12 C13 C12 122.17(15) 3_656 . ?
C13 C14 C10 117.72(7) . . ?
C13 C14 C10 117.72(7) . 3_656 ?
C10 C14 C10 124.57(14) . 3_656 ?
C18 C15 C17 123.51(11) . 5_676 ?
C18 C15 C16 122.93(11) . . ?
C17 C15 C16 113.55(10) 5_676 . ?
F1 C16 C17 118.63(10) . . ?
F1 C16 C15 117.88(10) . . ?
C17 C16 C15 123.48(11) . . ?
F2 C17 C16 118.63(10) . . ?
F2 C17 C15 118.39(10) . 5_676 ?
C16 C17 C15 122.95(11) . 5_676 ?
C15 C18 C20 123.08(11) . . ?
C15 C18 C19 123.89(11) . . ?
C20 C18 C19 113.02(10) . . ?
N1 C19 C18 175.99(13) . . ?
N2 C20 C18 176.38(13) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_6helicene-TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1533427'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ([6]helicene)(TCNQ)
_chemical_formula_moiety         '(C26 H16), (C12 H4 N4)'
_chemical_formula_sum            'C38 H20 N4'
_chemical_formula_weight         532.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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                   8.2077(5)
_cell_length_b                   33.7880(19)
_cell_length_c                   19.3173(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.882(1)
_cell_angle_gamma                90.00
_cell_volume                     5350.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8579
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.97

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            55575
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.21
_diffrn_reflns_theta_max         26.37
_reflns_number_total             10950
_reflns_number_gt                6822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0492P)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         10950
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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 0.9275(2) 0.02551(5) 0.10650(9) 0.0253(4) Uani 1 1 d . . .
H1 H 0.9542 0.0015 0.0864 0.030 Uiso 1 1 calc R . .
C2 C 1.0499(2) 0.05290(5) 0.12490(9) 0.0230(4) Uani 1 1 d . . .
H2 H 1.1575 0.0476 0.1151 0.028 Uiso 1 1 calc R . .
C3 C 0.7692(2) 0.03413(5) 0.11812(9) 0.0240(4) Uani 1 1 d . . .
H3 H 0.6883 0.0158 0.1057 0.029 Uiso 1 1 calc R . .
C4 C 1.0117(2) 0.08742(5) 0.15725(8) 0.0196(4) Uani 1 1 d . . .
H4 H 1.0946 0.1051 0.1698 0.024 Uiso 1 1 calc R . .
C5 C 0.72523(19) 0.07028(5) 0.14871(8) 0.0193(4) Uani 1 1 d . . .
C6 C 0.84933(19) 0.09687(5) 0.17209(8) 0.0179(4) Uani 1 1 d . . .
C7 C 0.5581(2) 0.08190(5) 0.15100(8) 0.0233(4) Uani 1 1 d . . .
H7 H 0.4759 0.0636 0.1408 0.028 Uiso 1 1 calc R . .
C8 C 0.5191(2) 0.11938(5) 0.16788(8) 0.0238(4) Uani 1 1 d . . .
H8 H 0.4105 0.1273 0.1643 0.029 Uiso 1 1 calc R . .
C9 C 0.6417(2) 0.14713(5) 0.19117(8) 0.0210(4) Uani 1 1 d . . .
C10 C 0.80379(19) 0.13435(5) 0.20301(8) 0.0184(4) Uani 1 1 d . . .
C11 C 0.6019(2) 0.18762(5) 0.19963(9) 0.0258(4) Uani 1 1 d . . .
H11 H 0.4943 0.1959 0.1929 0.031 Uiso 1 1 calc R . .
C12 C 0.7203(2) 0.21421(5) 0.21746(9) 0.0263(4) Uani 1 1 d . . .
H12 H 0.6957 0.2411 0.2171 0.032 Uiso 1 1 calc R . .
C13 C 0.8813(2) 0.20170(5) 0.23676(8) 0.0230(4) Uani 1 1 d . . .
C14 C 0.9186(2) 0.16084(5) 0.23864(8) 0.0194(4) Uani 1 1 d . . .
C15 C 1.0055(2) 0.22978(6) 0.25313(9) 0.0292(5) Uani 1 1 d . . .
H15 H 0.9820 0.2567 0.2498 0.035 Uiso 1 1 calc R . .
C16 C 1.1581(2) 0.21798(5) 0.27353(9) 0.0285(5) Uani 1 1 d . . .
H16 H 1.2416 0.2365 0.2780 0.034 Uiso 1 1 calc R . .
C17 C 1.1919(2) 0.17751(5) 0.28818(8) 0.0225(4) Uani 1 1 d . . .
C18 C 1.06803(19) 0.14884(5) 0.27595(8) 0.0185(4) Uani 1 1 d . . .
C19 C 1.3487(2) 0.16594(6) 0.31589(9) 0.0265(4) Uani 1 1 d . . .
H19 H 1.4293 0.1850 0.3234 0.032 Uiso 1 1 calc R . .
C20 C 1.3828(2) 0.12793(6) 0.33143(9) 0.0264(4) Uani 1 1 d . . .
H20 H 1.4892 0.1207 0.3445 0.032 Uiso 1 1 calc R . .
C21 C 1.2576(2) 0.09869(5) 0.32803(8) 0.0216(4) Uani 1 1 d . . .
C22 C 1.0964(2) 0.10964(5) 0.30527(8) 0.0193(4) Uani 1 1 d . . .
C23 C 1.2890(2) 0.05975(6) 0.35097(9) 0.0281(4) Uani 1 1 d . . .
H23 H 1.3958 0.0521 0.3624 0.034 Uiso 1 1 calc R . .
C24 C 1.1655(2) 0.03304(6) 0.35667(9) 0.0303(5) Uani 1 1 d . . .
H24 H 1.1883 0.0071 0.3700 0.036 Uiso 1 1 calc R . .
C25 C 1.0045(2) 0.04510(5) 0.34220(9) 0.0254(4) Uani 1 1 d . . .
H25 H 0.9193 0.0277 0.3499 0.030 Uiso 1 1 calc R . .
C26 C 0.9707(2) 0.08233(5) 0.31669(8) 0.0208(4) Uani 1 1 d . . .
H26 H 0.8628 0.0896 0.3068 0.025 Uiso 1 1 calc R . .
C27 C 0.4701(2) 0.77097(5) 0.11816(9) 0.0280(4) Uani 1 1 d . . .
H27 H 0.5038 0.7467 0.1013 0.034 Uiso 1 1 calc R . .
C28 C 0.5844(2) 0.80051(5) 0.13472(9) 0.0248(4) Uani 1 1 d . . .
H28 H 0.6940 0.7962 0.1271 0.030 Uiso 1 1 calc R . .
C29 C 0.3088(2) 0.77798(5) 0.12691(9) 0.0261(4) Uani 1 1 d . . .
H29 H 0.2329 0.7583 0.1156 0.031 Uiso 1 1 calc R . .
C30 C 0.53629(19) 0.83567(5) 0.16212(8) 0.0202(4) Uani 1 1 d . . .
H30 H 0.6144 0.8549 0.1731 0.024 Uiso 1 1 calc R . .
C31 C 0.2549(2) 0.81445(5) 0.15269(8) 0.0206(4) Uani 1 1 d . . .
C32 C 0.37097(19) 0.84357(5) 0.17414(8) 0.0185(4) Uani 1 1 d . . .
C33 C 0.0850(2) 0.82353(6) 0.15252(8) 0.0244(4) Uani 1 1 d . . .
H33 H 0.0081 0.8038 0.1433 0.029 Uiso 1 1 calc R . .
C34 C 0.0361(2) 0.86068(5) 0.16565(8) 0.0236(4) Uani 1 1 d . . .
H34 H -0.0744 0.8668 0.1610 0.028 Uiso 1 1 calc R . .
C35 C 0.1496(2) 0.89091(5) 0.18647(8) 0.0202(4) Uani 1 1 d . . .
C36 C 0.31520(19) 0.88117(5) 0.20073(8) 0.0175(4) Uani 1 1 d . . .
C37 C 0.0979(2) 0.93089(5) 0.19060(9) 0.0251(4) Uani 1 1 d . . .
H37 H -0.0116 0.9372 0.1821 0.030 Uiso 1 1 calc R . .
C38 C 0.2064(2) 0.95983(5) 0.20671(9) 0.0265(4) Uani 1 1 d . . .
H38 H 0.1737 0.9862 0.2035 0.032 Uiso 1 1 calc R . .
C39 C 0.3696(2) 0.95071(5) 0.22850(8) 0.0233(4) Uani 1 1 d . . .
C40 C 0.42077(19) 0.91064(5) 0.23402(8) 0.0193(4) Uani 1 1 d . . .
C41 C 0.4832(2) 0.98174(6) 0.24356(9) 0.0287(5) Uani 1 1 d . . .
H41 H 0.4497 1.0079 0.2390 0.034 Uiso 1 1 calc R . .
C42 C 0.6389(2) 0.97357(6) 0.26433(9) 0.0306(5) Uani 1 1 d . . .
H42 H 0.7153 0.9939 0.2676 0.037 Uiso 1 1 calc R . .
C43 C 0.6872(2) 0.93428(5) 0.28121(8) 0.0231(4) Uani 1 1 d . . .
C44 C 0.5741(2) 0.90285(5) 0.27211(8) 0.0196(4) Uani 1 1 d . . .
C45 C 0.8479(2) 0.92661(6) 0.30909(9) 0.0281(4) Uani 1 1 d . . .
H45 H 0.9213 0.9475 0.3146 0.034 Uiso 1 1 calc R . .
C46 C 0.8964(2) 0.88979(6) 0.32769(9) 0.0270(5) Uani 1 1 d . . .
H46 H 1.0054 0.8850 0.3403 0.032 Uiso 1 1 calc R . .
C47 C 0.7813(2) 0.85824(5) 0.32802(8) 0.0231(4) Uani 1 1 d . . .
C48 C 0.6161(2) 0.86547(5) 0.30538(8) 0.0195(4) Uani 1 1 d . . .
C49 C 0.8261(2) 0.82089(6) 0.35473(9) 0.0291(5) Uani 1 1 d . . .
H49 H 0.9355 0.8155 0.3657 0.035 Uiso 1 1 calc R . .
C50 C 0.7112(2) 0.79235(6) 0.36492(9) 0.0312(5) Uani 1 1 d . . .
H50 H 0.7427 0.7675 0.3812 0.037 Uiso 1 1 calc R . .
C51 C 0.5465(2) 0.80086(5) 0.35066(9) 0.0273(4) Uani 1 1 d . . .
H51 H 0.4675 0.7824 0.3614 0.033 Uiso 1 1 calc R . .
C52 C 0.5004(2) 0.83630(5) 0.32090(8) 0.0217(4) Uani 1 1 d . . .
H52 H 0.3903 0.8412 0.3107 0.026 Uiso 1 1 calc R . .
C53 C 0.3379(2) 0.08599(5) 0.52865(8) 0.0208(4) Uani 1 1 d . . .
C54 C 0.1677(2) 0.07817(5) 0.51168(8) 0.0225(4) Uani 1 1 d . . .
H54 H 0.1266 0.0529 0.5182 0.027 Uiso 1 1 calc R . .
C55 C 0.0676(2) 0.10671(5) 0.48671(8) 0.0228(4) Uani 1 1 d . . .
H55 H -0.0416 0.1010 0.4761 0.027 Uiso 1 1 calc R . .
C56 C 0.1276(2) 0.14607(5) 0.47612(8) 0.0208(4) Uani 1 1 d . . .
C57 C 0.2982(2) 0.15374(5) 0.49207(8) 0.0223(4) Uani 1 1 d . . .
H57 H 0.3396 0.1789 0.4848 0.027 Uiso 1 1 calc R . .
C58 C 0.3981(2) 0.12530(5) 0.51717(8) 0.0221(4) Uani 1 1 d . . .
H58 H 0.5076 0.1310 0.5273 0.026 Uiso 1 1 calc R . .
C59 C 0.4401(2) 0.05686(5) 0.55520(9) 0.0236(4) Uani 1 1 d . . .
C60 C 0.3865(2) 0.01701(6) 0.56254(9) 0.0249(4) Uani 1 1 d . . .
C61 C 0.6076(2) 0.06487(5) 0.57541(9) 0.0272(4) Uani 1 1 d . . .
C62 C 0.0249(2) 0.17591(5) 0.45254(8) 0.0220(4) Uani 1 1 d . . .
C63 C -0.1451(2) 0.16969(5) 0.43514(9) 0.0277(4) Uani 1 1 d . . .
C64 C 0.0818(2) 0.21578(6) 0.44666(9) 0.0221(4) Uani 1 1 d . . .
N1 N 0.34502(19) -0.01536(5) 0.56735(8) 0.0343(4) Uani 1 1 d . . .
N2 N 0.7412(2) 0.07124(5) 0.59147(9) 0.0385(4) Uani 1 1 d . . .
N3 N -0.2812(2) 0.16544(5) 0.42121(9) 0.0445(5) Uani 1 1 d . . .
N4 N 0.12600(18) 0.24779(5) 0.44296(8) 0.0298(4) Uani 1 1 d . . .
C65 C 0.1687(2) 0.83407(5) 0.97253(8) 0.0188(4) Uani 1 1 d . . .
C66 C 0.1007(2) 0.87158(5) 0.99225(8) 0.0200(4) Uani 1 1 d . . .
H66 H -0.0118 0.8751 0.9890 0.024 Uiso 1 1 calc R . .
C67 C 0.19641(19) 0.90131(5) 1.01506(8) 0.0198(4) Uani 1 1 d . . .
H67 H 0.1496 0.9251 1.0280 0.024 Uiso 1 1 calc R . .
C68 C 0.3717(2) 0.89693(5) 1.01990(8) 0.0189(4) Uani 1 1 d . . .
C69 C 0.4394(2) 0.85935(5) 1.00118(8) 0.0199(4) Uani 1 1 d . . .
H69 H 0.5519 0.8558 1.0044 0.024 Uiso 1 1 calc R . .
C70 C 0.34341(19) 0.82939(5) 0.97921(8) 0.0195(4) Uani 1 1 d . . .
H70 H 0.3900 0.8053 0.9681 0.023 Uiso 1 1 calc R . .
C71 C 0.0691(2) 0.80399(5) 0.94810(9) 0.0209(4) Uani 1 1 d . . .
C72 C -0.1035(2) 0.80968(5) 0.93531(9) 0.0256(4) Uani 1 1 d . . .
C73 C 0.1278(2) 0.76508(6) 0.93461(9) 0.0224(4) Uani 1 1 d . . .
C74 C 0.47072(19) 0.92821(5) 1.04028(8) 0.0193(4) Uani 1 1 d . . .
C75 C 0.4058(2) 0.96664(5) 1.05376(8) 0.0198(4) Uani 1 1 d . . .
C76 C 0.6449(2) 0.92480(5) 1.04718(9) 0.0231(4) Uani 1 1 d . . .
N5 N -0.24096(19) 0.81446(5) 0.92430(9) 0.0372(4) Uani 1 1 d . . .
N6 N 0.17231(18) 0.73329(5) 0.92560(8) 0.0314(4) Uani 1 1 d . . .
N7 N 0.35716(17) 0.99795(5) 1.06295(8) 0.0267(4) Uani 1 1 d . . .
N8 N 0.78448(19) 0.92233(5) 1.05314(8) 0.0339(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.362(2) . ?
C1 C2 1.398(2) . ?
C1 H1 0.9300 . ?
C2 C4 1.367(2) . ?
C2 H2 0.9300 . ?
C3 C5 1.412(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.413(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.415(2) . ?
C5 C7 1.429(2) . ?
C6 C10 1.457(2) . ?
C7 C8 1.350(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.431(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.406(2) . ?
C9 C11 1.418(2) . ?
C10 C14 1.448(2) . ?
C11 C12 1.355(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.419(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(2) . ?
C13 C15 1.417(2) . ?
C14 C18 1.449(2) . ?
C15 C16 1.354(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.421(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(2) . ?
C17 C19 1.424(2) . ?
C18 C22 1.455(2) . ?
C19 C20 1.345(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.424(2) . ?
C20 H20 0.9300 . ?
C21 C23 1.408(2) . ?
C21 C22 1.422(2) . ?
C22 C26 1.410(2) . ?
C23 C24 1.366(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.398(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C29 1.364(2) . ?
C27 C28 1.396(2) . ?
C27 H27 0.9300 . ?
C28 C30 1.367(2) . ?
C28 H28 0.9300 . ?
C29 C31 1.409(2) . ?
C29 H29 0.9300 . ?
C30 C32 1.414(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.417(2) . ?
C31 C33 1.427(2) . ?
C32 C36 1.453(2) . ?
C33 C34 1.346(2) . ?
C33 H33 0.9300 . ?
C34 C35 1.427(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.412(2) . ?
C35 C37 1.420(2) . ?
C36 C40 1.449(2) . ?
C37 C38 1.349(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.417(2) . ?
C38 H38 0.9300 . ?
C39 C40 1.420(2) . ?
C39 C41 1.423(2) . ?
C40 C44 1.450(2) . ?
C41 C42 1.348(2) . ?
C41 H41 0.9300 . ?
C42 C43 1.419(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.415(2) . ?
C43 C45 1.423(2) . ?
C44 C48 1.451(2) . ?
C45 C46 1.349(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.425(2) . ?
C46 H46 0.9300 . ?
C47 C49 1.405(3) . ?
C47 C48 1.425(2) . ?
C48 C52 1.411(2) . ?
C49 C50 1.370(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.396(2) . ?
C50 H50 0.9300 . ?
C51 C52 1.373(2) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 C59 1.376(2) . ?
C53 C58 1.438(2) . ?
C53 C54 1.443(2) . ?
C54 C55 1.341(2) . ?
C54 H54 0.9300 . ?
C55 C56 1.436(2) . ?
C55 H55 0.9300 . ?
C56 C62 1.377(2) . ?
C56 C57 1.442(2) . ?
C57 C58 1.338(2) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 C60 1.426(3) . ?
C59 C61 1.436(3) . ?
C60 N1 1.151(2) . ?
C61 N2 1.145(2) . ?
C62 C64 1.432(3) . ?
C62 C63 1.434(2) . ?
C63 N3 1.145(2) . ?
C64 N4 1.144(2) . ?
C65 C71 1.373(2) . ?
C65 C70 1.442(2) . ?
C65 C66 1.444(2) . ?
C66 C67 1.336(2) . ?
C66 H66 0.9300 . ?
C67 C68 1.444(2) . ?
C67 H67 0.9300 . ?
C68 C74 1.379(2) . ?
C68 C69 1.440(2) . ?
C69 C70 1.338(2) . ?
C69 H69 0.9300 . ?
C70 H70 0.9300 . ?
C71 C73 1.428(2) . ?
C71 C72 1.439(2) . ?
C72 N5 1.149(2) . ?
C73 N6 1.151(2) . ?
C74 C75 1.432(2) . ?
C74 C76 1.433(2) . ?
C75 N7 1.148(2) . ?
C76 N8 1.149(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
C3 C1 C2 119.71(16) . . ?
C3 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C4 C2 C1 120.17(16) . . ?
C4 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C1 C3 C5 121.35(16) . . ?
C1 C3 H3 119.3 . . ?
C5 C3 H3 119.3 . . ?
C2 C4 C6 121.70(16) . . ?
C2 C4 H4 119.1 . . ?
C6 C4 H4 119.1 . . ?
C3 C5 C6 119.21(15) . . ?
C3 C5 C7 121.08(15) . . ?
C6 C5 C7 119.49(16) . . ?
C4 C6 C5 117.57(15) . . ?
C4 C6 C10 122.91(15) . . ?
C5 C6 C10 119.16(15) . . ?
C8 C7 C5 120.33(16) . . ?
C8 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C7 C8 C9 121.21(16) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C11 119.94(16) . . ?
C10 C9 C8 119.65(16) . . ?
C11 C9 C8 120.36(15) . . ?
C9 C10 C14 118.37(15) . . ?
C9 C10 C6 117.40(15) . . ?
C14 C10 C6 123.90(14) . . ?
C12 C11 C9 120.17(16) . . ?
C12 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C11 C12 C13 121.02(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C15 119.71(16) . . ?
C14 C13 C12 119.68(16) . . ?
C15 C13 C12 120.61(17) . . ?
C13 C14 C10 117.15(15) . . ?
C13 C14 C18 117.56(15) . . ?
C10 C14 C18 125.29(15) . . ?
C16 C15 C13 120.84(18) . . ?
C16 C15 H15 119.6 . . ?
C13 C15 H15 119.6 . . ?
C15 C16 C17 120.64(17) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.62(16) . . ?
C18 C17 C19 120.20(16) . . ?
C16 C17 C19 120.17(16) . . ?
C17 C18 C14 118.31(15) . . ?
C17 C18 C22 117.30(15) . . ?
C14 C18 C22 124.29(14) . . ?
C20 C19 C17 121.31(16) . . ?
C20 C19 H19 119.3 . . ?
C17 C19 H19 119.3 . . ?
C19 C20 C21 120.72(17) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C23 C21 C22 119.53(16) . . ?
C23 C21 C20 120.91(16) . . ?
C22 C21 C20 119.44(17) . . ?
C26 C22 C21 117.28(16) . . ?
C26 C22 C18 123.57(15) . . ?
C21 C22 C18 119.03(15) . . ?
C24 C23 C21 121.18(17) . . ?
C24 C23 H23 119.4 . . ?
C21 C23 H23 119.4 . . ?
C23 C24 C25 119.33(18) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.67(17) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C22 121.29(16) . . ?
C25 C26 H26 119.4 . . ?
C22 C26 H26 119.4 . . ?
C29 C27 C28 119.53(17) . . ?
C29 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C30 C28 C27 120.40(16) . . ?
C30 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C27 C29 C31 121.33(17) . . ?
C27 C29 H29 119.3 . . ?
C31 C29 H29 119.3 . . ?
C28 C30 C32 121.76(16) . . ?
C28 C30 H30 119.1 . . ?
C32 C30 H30 119.1 . . ?
C29 C31 C32 119.49(16) . . ?
C29 C31 C33 120.75(16) . . ?
C32 C31 C33 119.58(16) . . ?
C30 C32 C31 117.24(15) . . ?
C30 C32 C36 123.04(15) . . ?
C31 C32 C36 119.43(15) . . ?
C34 C33 C31 120.06(16) . . ?
C34 C33 H33 120.0 . . ?
C31 C33 H33 120.0 . . ?
C33 C34 C35 121.57(16) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C36 C35 C37 119.92(16) . . ?
C36 C35 C34 119.79(16) . . ?
C37 C35 C34 120.26(15) . . ?
C35 C36 C40 118.33(15) . . ?
C35 C36 C32 116.89(14) . . ?
C40 C36 C32 124.46(14) . . ?
C38 C37 C35 120.46(16) . . ?
C38 C37 H37 119.8 . . ?
C35 C37 H37 119.8 . . ?
C37 C38 C39 120.94(17) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C38 C39 C40 120.08(16) . . ?
C38 C39 C41 120.01(17) . . ?
C40 C39 C41 119.90(16) . . ?
C39 C40 C36 116.99(15) . . ?
C39 C40 C44 117.21(15) . . ?
C36 C40 C44 125.81(15) . . ?
C42 C41 C39 120.76(18) . . ?
C42 C41 H41 119.6 . . ?
C39 C41 H41 119.6 . . ?
C41 C42 C43 120.65(17) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C44 C43 C42 119.94(16) . . ?
C44 C43 C45 120.00(17) . . ?
C42 C43 C45 120.04(16) . . ?
C43 C44 C40 118.31(15) . . ?
C43 C44 C48 117.29(15) . . ?
C40 C44 C48 124.29(15) . . ?
C46 C45 C43 121.60(17) . . ?
C46 C45 H45 119.2 . . ?
C43 C45 H45 119.2 . . ?
C45 C46 C47 120.29(17) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C49 C47 C48 119.63(16) . . ?
C49 C47 C46 120.80(16) . . ?
C48 C47 C46 119.43(16) . . ?
C52 C48 C47 117.06(16) . . ?
C52 C48 C44 123.72(15) . . ?
C47 C48 C44 119.10(15) . . ?
C50 C49 C47 121.02(17) . . ?
C50 C49 H49 119.5 . . ?
C47 C49 H49 119.5 . . ?
C49 C50 C51 119.58(18) . . ?
C49 C50 H50 120.2 . . ?
C51 C50 H50 120.2 . . ?
C52 C51 C50 120.38(17) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C51 C52 C48 121.61(16) . . ?
C51 C52 H52 119.2 . . ?
C48 C52 H52 119.2 . . ?
C59 C53 C58 120.68(16) . . ?
C59 C53 C54 121.26(16) . . ?
C58 C53 C54 118.06(15) . . ?
C55 C54 C53 121.24(17) . . ?
C55 C54 H54 119.4 . . ?
C53 C54 H54 119.4 . . ?
C54 C55 C56 120.61(16) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C62 C56 C55 121.13(16) . . ?
C62 C56 C57 120.69(16) . . ?
C55 C56 C57 118.17(15) . . ?
C58 C57 C56 121.28(16) . . ?
C58 C57 H57 119.4 . . ?
C56 C57 H57 119.4 . . ?
C57 C58 C53 120.64(16) . . ?
C57 C58 H58 119.7 . . ?
C53 C58 H58 119.7 . . ?
C53 C59 C60 121.83(16) . . ?
C53 C59 C61 121.60(17) . . ?
C60 C59 C61 116.55(15) . . ?
N1 C60 C59 178.6(2) . . ?
N2 C61 C59 179.9(3) . . ?
C56 C62 C64 121.26(15) . . ?
C56 C62 C63 122.83(16) . . ?
C64 C62 C63 115.86(15) . . ?
N3 C63 C62 178.8(2) . . ?
N4 C64 C62 178.86(19) . . ?
C71 C65 C70 121.44(16) . . ?
C71 C65 C66 120.60(15) . . ?
C70 C65 C66 117.96(15) . . ?
C67 C66 C65 121.20(16) . . ?
C67 C66 H66 119.4 . . ?
C65 C66 H66 119.4 . . ?
C66 C67 C68 120.76(16) . . ?
C66 C67 H67 119.6 . . ?
C68 C67 H67 119.6 . . ?
C74 C68 C69 121.22(15) . . ?
C74 C68 C67 120.74(15) . . ?
C69 C68 C67 118.02(15) . . ?
C70 C69 C68 121.22(16) . . ?
C70 C69 H69 119.4 . . ?
C68 C69 H69 119.4 . . ?
C69 C70 C65 120.80(16) . . ?
C69 C70 H70 119.6 . . ?
C65 C70 H70 119.6 . . ?
C65 C71 C73 122.95(15) . . ?
C65 C71 C72 121.61(16) . . ?
C73 C71 C72 115.44(15) . . ?
N5 C72 C71 179.1(2) . . ?
N6 C73 C71 177.73(19) . . ?
C68 C74 C75 121.83(15) . . ?
C68 C74 C76 122.40(16) . . ?
C75 C74 C76 115.74(15) . . ?
N7 C75 C74 177.71(19) . . ?
N8 C76 C74 179.4(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_6helicene-Me22TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1533428'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ([6]helicene)(Me2TCNQ)
_chemical_formula_moiety         '(C26 H16), (C14 H8 N4)'
_chemical_formula_sum            'C40 H24 N4'
_chemical_formula_weight         560.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   14.4593(7)
_cell_length_b                   11.4032(6)
_cell_length_c                   17.8273(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.652(1)
_cell_angle_gamma                90.00
_cell_volume                     2868.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6251
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.15

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7341
_diffrn_reflns_av_R_equivalents  0.0095
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2929
_reflns_number_gt                2687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0549P)²+1.3694P] 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         2929
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.46194(8) 0.86568(9) 0.87868(6) 0.0292(2) Uani 1 1 d . . .
H1 H 0.4668 0.9435 0.8946 0.035 Uiso 1 1 calc R . .
C2 C 0.54176(8) 0.80624(9) 0.86532(6) 0.0255(2) Uani 1 1 d . . .
H2 H 0.6005 0.8433 0.8758 0.031 Uiso 1 1 calc R . .
C3 C 0.37704(8) 0.80838(9) 0.86818(6) 0.0271(2) Uani 1 1 d . . .
H3 H 0.3248 0.8469 0.8790 0.032 Uiso 1 1 calc R . .
C4 C 0.53394(7) 0.69387(9) 0.83692(5) 0.0209(2) Uani 1 1 d . . .
H4 H 0.5877 0.6557 0.8287 0.025 Uiso 1 1 calc R . .
C5 C 0.36746(7) 0.69159(9) 0.84123(5) 0.0218(2) Uani 1 1 d . . .
C6 C 0.44549(7) 0.63511(8) 0.81994(5) 0.0192(2) Uani 1 1 d . . .
C7 C 0.28133(7) 0.62859(10) 0.83786(6) 0.0251(2) Uani 1 1 d . . .
H7 H 0.2294 0.6667 0.8496 0.030 Uiso 1 1 calc R . .
C8 C 0.27461(7) 0.51438(10) 0.81787(6) 0.0255(2) Uani 1 1 d . . .
H8 H 0.2198 0.4730 0.8200 0.031 Uiso 1 1 calc R . .
C9 C 0.35022(7) 0.45573(9) 0.79339(5) 0.0226(2) Uani 1 1 d . . .
C10 C 0.43213(6) 0.51884(8) 0.78635(5) 0.0194(2) Uani 1 1 d . . .
C11 C 0.34474(7) 0.33286(9) 0.77926(6) 0.0261(2) Uani 1 1 d . . .
H11 H 0.2891 0.2926 0.7803 0.031 Uiso 1 1 calc R . .
C12 C 0.42013(7) 0.27409(9) 0.76426(5) 0.0265(2) Uani 1 1 d . . .
H12 H 0.4197 0.1926 0.7633 0.032 Uiso 1 1 calc R . .
C13 C 0.5000 0.33604(12) 0.7500 0.0230(3) Uani 1 2 d S . .
C14 C 0.5000 0.46069(12) 0.7500 0.0200(3) Uani 1 2 d S . .
C15 C 0.49103(7) 0.61901(8) 0.47498(5) 0.0184(2) Uani 1 1 d . . .
C16 C 0.57985(6) 0.55638(8) 0.47868(5) 0.0186(2) Uani 1 1 d . . .
C17 C 0.58556(6) 0.44392(8) 0.50316(5) 0.0191(2) Uani 1 1 d . . .
H17 H 0.6426 0.4045 0.5061 0.023 Uiso 1 1 calc R . .
C18 C 0.47546(7) 0.73470(8) 0.45270(5) 0.0206(2) Uani 1 1 d . . .
C19 C 0.54318(7) 0.81401(8) 0.43302(6) 0.0237(2) Uani 1 1 d . . .
C20 C 0.38458(7) 0.78961(9) 0.44787(6) 0.0239(2) Uani 1 1 d . . .
C21 C 0.66373(7) 0.61018(9) 0.45476(6) 0.0242(2) Uani 1 1 d . . .
H21A H 0.7137 0.5533 0.4600 0.036 Uiso 1 1 calc R . .
H21B H 0.6855 0.6766 0.4868 0.036 Uiso 1 1 calc R . .
H21C H 0.6456 0.6350 0.4021 0.036 Uiso 1 1 calc R . .
N1 N 0.59203(7) 0.88468(8) 0.41677(6) 0.0319(2) Uani 1 1 d . . .
N2 N 0.31305(7) 0.83614(9) 0.44241(6) 0.0338(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.3670(16) . ?
C1 C2 1.4030(15) . ?
C1 H1 0.9300 . ?
C2 C4 1.3733(14) . ?
C2 H2 0.9300 . ?
C3 C5 1.4123(15) . ?
C3 H3 0.9300 . ?
C4 C6 1.4165(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.4211(13) . ?
C5 C7 1.4275(14) . ?
C6 C10 1.4502(13) . ?
C7 C8 1.3481(16) . ?
C7 H7 0.9300 . ?
C8 C9 1.4291(15) . ?
C8 H8 0.9300 . ?
C9 C10 1.4147(13) . ?
C9 C11 1.4227(15) . ?
C10 C14 1.4496(11) . ?
C11 C12 1.3553(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.4233(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.4213(19) . ?
C13 C12 1.4234(12) 2_656 ?
C14 C10 1.4496(11) 2_656 ?
C15 C18 1.3819(13) . ?
C15 C17 1.4430(13) 5_666 ?
C15 C16 1.4584(13) . ?
C16 C17 1.3513(14) . ?
C16 C21 1.5018(13) . ?
C17 C15 1.4430(13) 5_666 ?
C17 H17 0.9300 . ?
C18 C19 1.4319(14) . ?
C18 C20 1.4410(13) . ?
C19 N1 1.1497(14) . ?
C20 N2 1.1474(14) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 119.56(10) . . ?
C3 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C4 C2 C1 120.60(10) . . ?
C4 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C3 C5 121.04(10) . . ?
C1 C3 H3 119.5 . . ?
C5 C3 H3 119.5 . . ?
C2 C4 C6 121.18(9) . . ?
C2 C4 H4 119.4 . . ?
C6 C4 H4 119.4 . . ?
C3 C5 C6 119.59(9) . . ?
C3 C5 C7 120.56(9) . . ?
C6 C5 C7 119.81(9) . . ?
C4 C6 C5 117.46(9) . . ?
C4 C6 C10 123.58(9) . . ?
C5 C6 C10 118.87(9) . . ?
C8 C7 C5 120.60(9) . . ?
C8 C7 H7 119.7 . . ?
C5 C7 H7 119.7 . . ?
C7 C8 C9 121.14(9) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C11 120.04(9) . . ?
C10 C9 C8 120.03(9) . . ?
C11 C9 C8 119.88(9) . . ?
C9 C10 C14 117.96(9) . . ?
C9 C10 C6 117.83(9) . . ?
C14 C10 C6 124.11(9) . . ?
C12 C11 C9 120.39(9) . . ?
C12 C11 H11 119.8 . . ?
C9 C11 H11 119.8 . . ?
C11 C12 C13 120.60(10) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.76(7) . . ?
C14 C13 C12 119.75(7) . 2_656 ?
C12 C13 C12 120.49(13) . 2_656 ?
C13 C14 C10 117.22(6) . 2_656 ?
C13 C14 C10 117.22(6) . . ?
C10 C14 C10 125.55(12) 2_656 . ?
C18 C15 C17 117.77(9) . 5_666 ?
C18 C15 C16 124.54(9) . . ?
C17 C15 C16 117.68(9) 5_666 . ?
C17 C16 C15 118.05(9) . . ?
C17 C16 C21 118.90(9) . . ?
C15 C16 C21 123.02(9) . . ?
C16 C17 C15 124.26(9) . 5_666 ?
C16 C17 H17 117.9 . . ?
C15 C17 H17 117.9 5_666 . ?
C15 C18 C19 126.61(9) . . ?
C15 C18 C20 121.40(9) . . ?
C19 C18 C20 111.99(8) . . ?
N1 C19 C18 174.42(10) . . ?
N2 C20 C18 177.69(11) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_6helicene-F2TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1533426'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ([6]helicene)(F2TCNQ)
_chemical_formula_moiety         '(C26 H16), (C12 H2 F2 N4)'
_chemical_formula_sum            'C38 H18 F2 N4'
_chemical_formula_weight         568.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   8.3747(4)
_cell_length_b                   16.7659(8)
_cell_length_c                   19.2823(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.488(1)
_cell_angle_gamma                90.00
_cell_volume                     2707.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7073
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.07

_exptl_crystal_description       'hexagonal bifrustum'
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14102
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5528
_reflns_number_gt                4532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.9402P] 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         5528
_refine_ls_number_parameters     404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.0559(2) 0.03524(9) 0.87662(8) 0.0382(4) Uani 1 1 d . . .
H1 H 0.0294 -0.0147 0.8941 0.046 Uiso 1 1 calc R . .
C2 C -0.06394(19) 0.09027(9) 0.86010(7) 0.0327(3) Uani 1 1 d . . .
H2 H -0.1701 0.0777 0.8688 0.039 Uiso 1 1 calc R . .
C3 C 0.2119(2) 0.05528(9) 0.86695(8) 0.0349(4) Uani 1 1 d . . .
H3 H 0.2915 0.0187 0.8782 0.042 Uiso 1 1 calc R . .
C4 C -0.02656(17) 0.16261(8) 0.83115(7) 0.0254(3) Uani 1 1 d . . .
H4 H -0.1081 0.1980 0.8198 0.030 Uiso 1 1 calc R . .
C5 C 0.25497(18) 0.13049(8) 0.84024(7) 0.0274(3) Uani 1 1 d . . .
C6 C 0.13352(16) 0.18432(8) 0.81830(7) 0.0225(3) Uani 1 1 d . . .
C7 C 0.41779(18) 0.15586(9) 0.84087(7) 0.0322(3) Uani 1 1 d . . .
H7 H 0.4986 0.1193 0.8504 0.039 Uiso 1 1 calc R . .
C8 C 0.45489(17) 0.23269(10) 0.82773(7) 0.0320(3) Uani 1 1 d . . .
H8 H 0.5599 0.2497 0.8333 0.038 Uiso 1 1 calc R . .
C9 C 0.33614(17) 0.28829(8) 0.80543(7) 0.0269(3) Uani 1 1 d . . .
C10 C 0.17862(16) 0.26205(8) 0.79153(7) 0.0226(3) Uani 1 1 d . . .
C11 C 0.37477(19) 0.37058(9) 0.79954(7) 0.0341(4) Uani 1 1 d . . .
H11 H 0.4794 0.3874 0.8068 0.041 Uiso 1 1 calc R . .
C12 C 0.2606(2) 0.42431(9) 0.78346(8) 0.0353(4) Uani 1 1 d . . .
H12 H 0.2844 0.4785 0.7855 0.042 Uiso 1 1 calc R . .
C13 C 0.1048(2) 0.39966(8) 0.76344(7) 0.0305(3) Uani 1 1 d . . .
C14 C 0.06865(17) 0.31702(8) 0.75811(7) 0.0233(3) Uani 1 1 d . . .
C15 C -0.0163(2) 0.45711(9) 0.75010(7) 0.0389(4) Uani 1 1 d . . .
H15 H 0.0068 0.5111 0.7549 0.047 Uiso 1 1 calc R . .
C16 C -0.1646(2) 0.43412(9) 0.73043(8) 0.0400(4) Uani 1 1 d . . .
H16 H -0.2466 0.4715 0.7285 0.048 Uiso 1 1 calc R . .
C17 C -0.19640(19) 0.35325(9) 0.71270(7) 0.0316(3) Uani 1 1 d . . .
C18 C -0.07545(16) 0.29500(8) 0.72081(7) 0.0243(3) Uani 1 1 d . . .
C19 C -0.34857(19) 0.33113(11) 0.68515(8) 0.0397(4) Uani 1 1 d . . .
H19 H -0.4274 0.3698 0.6801 0.048 Uiso 1 1 calc R . .
C20 C -0.38054(18) 0.25540(11) 0.66630(8) 0.0383(4) Uani 1 1 d . . .
H20 H -0.4842 0.2411 0.6538 0.046 Uiso 1 1 calc R . .
C21 C -0.25713(17) 0.19689(9) 0.66526(7) 0.0299(3) Uani 1 1 d . . .
C22 C -0.10038(16) 0.21819(8) 0.68749(7) 0.0237(3) Uani 1 1 d . . .
C23 C -0.2849(2) 0.11983(10) 0.63847(8) 0.0379(4) Uani 1 1 d . . .
H23 H -0.3888 0.1044 0.6276 0.046 Uiso 1 1 calc R . .
C24 C -0.1628(2) 0.06743(9) 0.62810(8) 0.0378(4) Uani 1 1 d . . .
H24 H -0.1836 0.0162 0.6119 0.045 Uiso 1 1 calc R . .
C25 C -0.0059(2) 0.09155(8) 0.64206(7) 0.0313(3) Uani 1 1 d . . .
H25 H 0.0786 0.0578 0.6313 0.038 Uiso 1 1 calc R . .
C26 C 0.02450(17) 0.16480(8) 0.67159(7) 0.0236(3) Uani 1 1 d . . .
H26 H 0.1295 0.1794 0.6813 0.028 Uiso 1 1 calc R . .
C27 C 0.36973(16) 0.20451(8) 1.01868(7) 0.0239(3) Uani 1 1 d . A .
C28 C 0.20134(16) 0.19268(8) 1.00605(7) 0.0241(3) Uani 1 1 d . . .
H28 H 0.1579 0.1430 1.0160 0.029 Uiso 0.0661(13) 1 calc PR A 1
F1 F 0.14118(10) 0.12132(5) 1.02186(5) 0.0293(2) Uani 0.9339(13) 1 d P A 2
C29 C 0.10442(16) 0.24910(8) 0.98094(7) 0.0240(3) Uani 1 1 d . A .
H29 H -0.0028 0.2376 0.9730 0.029 Uiso 0.9339(13) 1 calc PR A 1
F1B F 0.5776(14) 0.2956(7) 1.0094(6) 0.0293(2) Uani 0.0661(13) 1 d P A 2
C30 C 0.16463(16) 0.32751(8) 0.96607(6) 0.0227(3) Uani 1 1 d . . .
C31 C 0.33279(17) 0.33967(8) 0.97909(7) 0.0242(3) Uani 1 1 d . A .
H31 H 0.3756 0.3898 0.9704 0.029 Uiso 0.0661(13) 1 calc PR A 1
F2 F 0.39220(10) 0.41224(5) 0.96511(5) 0.0292(2) Uani 0.9339(13) 1 d P A 2
C32 C 0.43037(16) 0.28265(8) 1.00303(7) 0.0247(3) Uani 1 1 d . . .
H32 H 0.5383 0.2936 1.0096 0.030 Uiso 0.9339(13) 1 calc PR A 1
F2B F -0.0510(14) 0.2310(7) 0.9768(6) 0.0292(2) Uani 0.0661(13) 1 d P A 2
C33 C 0.46738(17) 0.14546(8) 1.04414(7) 0.0271(3) Uani 1 1 d . . .
C34 C 0.41714(17) 0.06510(9) 1.05745(7) 0.0281(3) Uani 1 1 d . A .
C35 C 0.63357(19) 0.16084(9) 1.05821(8) 0.0350(4) Uani 1 1 d . A .
C36 C 0.06434(16) 0.38629(8) 0.94152(7) 0.0247(3) Uani 1 1 d . A .
C37 C -0.09958(18) 0.36808(8) 0.92475(8) 0.0285(3) Uani 1 1 d . . .
C38 C 0.10733(16) 0.46851(8) 0.93342(7) 0.0260(3) Uani 1 1 d . . .
N1 N 0.38663(16) -0.00042(8) 1.06771(7) 0.0369(3) Uani 1 1 d . . .
N2 N 0.76506(17) 0.17360(10) 1.06993(9) 0.0532(4) Uani 1 1 d . . .
N3 N -0.22943(16) 0.35302(8) 0.91078(8) 0.0397(3) Uani 1 1 d . A .
N4 N 0.13147(15) 0.53560(7) 0.92824(7) 0.0339(3) Uani 1 1 d . A .


_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 C3 1.363(2) . ?
C1 C2 1.398(2) . ?
C1 H1 0.9300 . ?
C2 C4 1.3725(19) . ?
C2 H2 0.9300 . ?
C3 C5 1.410(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.4131(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4215(19) . ?
C5 C7 1.428(2) . ?
C6 C10 1.4530(18) . ?
C7 C8 1.350(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.414(2) . ?
C9 C11 1.422(2) . ?
C10 C14 1.4501(19) . ?
C11 C12 1.348(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.420(2) . ?
C12 H12 0.9300 . ?
C13 C15 1.420(2) . ?
C13 C14 1.4216(19) . ?
C14 C18 1.447(2) . ?
C15 C16 1.352(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.423(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.4148(19) . ?
C17 C19 1.426(2) . ?
C18 C22 1.4534(19) . ?
C19 C20 1.347(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.425(2) . ?
C20 H20 0.9300 . ?
C21 C23 1.410(2) . ?
C21 C22 1.423(2) . ?
C22 C26 1.4123(19) . ?
C23 C24 1.364(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.399(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.3765(19) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C33 1.3722(19) . ?
C27 C32 1.4381(19) . ?
C27 C28 1.4427(19) . ?
C28 F1 1.3346(15) . ?
C28 C29 1.335(2) . ?
C28 H28 0.9300 . ?
C29 F2B 1.339(12) . ?
C29 C30 1.4378(19) . ?
C29 H29 0.9300 . ?
F1B C32 1.257(12) . ?
C30 C36 1.3763(19) . ?
C30 C31 1.4429(19) . ?
C31 C32 1.337(2) . ?
C31 F2 1.3428(15) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.435(2) . ?
C33 C35 1.439(2) . ?
C34 N1 1.1454(19) . ?
C35 N2 1.142(2) . ?
C36 C38 1.4336(19) . ?
C36 C37 1.440(2) . ?
C37 N3 1.146(2) . ?
C38 N4 1.1474(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 119.55(14) . . ?
C3 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C4 C2 C1 120.67(14) . . ?
C4 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C3 C5 121.23(14) . . ?
C1 C3 H3 119.4 . . ?
C5 C3 H3 119.4 . . ?
C2 C4 C6 121.26(14) . . ?
C2 C4 H4 119.4 . . ?
C6 C4 H4 119.4 . . ?
C3 C5 C6 119.47(14) . . ?
C3 C5 C7 120.68(14) . . ?
C6 C5 C7 119.61(13) . . ?
C4 C6 C5 117.50(12) . . ?
C4 C6 C10 122.90(12) . . ?
C5 C6 C10 119.19(12) . . ?
C8 C7 C5 120.26(14) . . ?
C8 C7 H7 119.9 . . ?
C5 C7 H7 119.9 . . ?
C7 C8 C9 121.28(14) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C11 119.95(14) . . ?
C10 C9 C8 120.04(13) . . ?
C11 C9 C8 119.97(14) . . ?
C9 C10 C14 118.33(12) . . ?
C9 C10 C6 117.17(12) . . ?
C14 C10 C6 124.19(12) . . ?
C12 C11 C9 120.36(14) . . ?
C12 C11 H11 119.8 . . ?
C9 C11 H11 119.8 . . ?
C11 C12 C13 121.11(13) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C15 120.32(14) . . ?
C12 C13 C14 119.87(14) . . ?
C15 C13 C14 119.80(15) . . ?
C13 C14 C18 117.42(13) . . ?
C13 C14 C10 116.96(13) . . ?
C18 C14 C10 125.62(12) . . ?
C16 C15 C13 120.67(14) . . ?
C16 C15 H15 119.7 . . ?
C13 C15 H15 119.7 . . ?
C15 C16 C17 120.58(14) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.93(15) . . ?
C18 C17 C19 119.90(14) . . ?
C16 C17 C19 120.15(14) . . ?
C17 C18 C14 118.16(13) . . ?
C17 C18 C22 117.57(13) . . ?
C14 C18 C22 124.17(12) . . ?
C20 C19 C17 121.39(14) . . ?
C20 C19 H19 119.3 . . ?
C17 C19 H19 119.3 . . ?
C19 C20 C21 120.67(15) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C23 C21 C22 119.30(14) . . ?
C23 C21 C20 121.21(15) . . ?
C22 C21 C20 119.36(14) . . ?
C26 C22 C21 117.29(13) . . ?
C26 C22 C18 123.62(12) . . ?
C21 C22 C18 118.96(12) . . ?
C24 C23 C21 121.47(15) . . ?
C24 C23 H23 119.3 . . ?
C21 C23 H23 119.3 . . ?
C23 C24 C25 119.33(14) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.50(15) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C22 121.39(14) . . ?
C25 C26 H26 119.3 . . ?
C22 C26 H26 119.3 . . ?
C33 C27 C32 121.46(13) . . ?
C33 C27 C28 122.68(13) . . ?
C32 C27 C28 115.86(12) . . ?
F1 C28 C29 119.25(12) . . ?
F1 C28 C27 117.07(12) . . ?
C29 C28 C27 123.67(13) . . ?
F1 C28 H28 1.5 . . ?
C29 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
C28 C29 F2B 116.7(5) . . ?
C28 C29 C30 120.47(13) . . ?
F2B C29 C30 122.6(5) . . ?
C28 C29 H29 119.8 . . ?
F2B C29 H29 6.1 . . ?
C30 C29 H29 119.8 . . ?
C36 C30 C29 120.62(13) . . ?
C36 C30 C31 123.40(13) . . ?
C29 C30 C31 115.97(12) . . ?
C32 C31 F2 119.39(13) . . ?
C32 C31 C30 123.48(13) . . ?
F2 C31 C30 117.12(12) . . ?
C32 C31 H31 118.3 . . ?
F2 C31 H31 1.4 . . ?
C30 C31 H31 118.3 . . ?
F1B C32 C31 120.4(5) . . ?
F1B C32 C27 119.0(5) . . ?
C31 C32 C27 120.52(13) . . ?
F1B C32 H32 2.7 . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C27 C33 C34 124.51(13) . . ?
C27 C33 C35 120.71(13) . . ?
C34 C33 C35 114.77(13) . . ?
N1 C34 C33 175.80(15) . . ?
N2 C35 C33 179.3(2) . . ?
C30 C36 C38 124.96(13) . . ?
C30 C36 C37 120.20(13) . . ?
C38 C36 C37 114.78(12) . . ?
N3 C37 C36 179.19(17) . . ?
N4 C38 C36 175.39(15) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_M-6helicene
_database_code_depnum_ccdc_archive 'CCDC 1535631'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            (M)-[6]helicene
_chemical_formula_moiety         'C26 H16'
_chemical_formula_sum            'C26 H16'
_chemical_formula_weight         328.41

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   'P2(1)2(1)2(1) '

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

_cell_length_a                   7.3079(3)
_cell_length_b                   12.9491(6)
_cell_length_c                   17.4393(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1650.3(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9466
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.23

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            17487
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3371
_reflns_number_gt                3136
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.1878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(9)
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.0672(2) 0.79947(10) 0.07419(8) 0.0313(3) Uani 1 1 d . . .
H1 H 0.0858 0.8682 0.0610 0.038 Uiso 1 1 calc R . .
C2 C 0.21502(18) 0.73101(9) 0.07783(7) 0.0265(3) Uani 1 1 d . . .
H2 H 0.3330 0.7552 0.0692 0.032 Uiso 1 1 calc R . .
C3 C -0.10470(19) 0.76440(10) 0.09025(8) 0.0326(3) Uani 1 1 d . . .
H3 H -0.2028 0.8101 0.0881 0.039 Uiso 1 1 calc R . .
C4 C 0.18771(16) 0.62847(9) 0.09406(7) 0.0230(3) Uani 1 1 d . . .
H4 H 0.2876 0.5840 0.0949 0.028 Uiso 1 1 calc R . .
C5 C -0.13647(17) 0.66056(10) 0.10998(7) 0.0280(3) Uani 1 1 d . . .
C6 C 0.01137(16) 0.58901(10) 0.10945(7) 0.0232(3) Uani 1 1 d . . .
C7 C -0.31231(19) 0.62747(12) 0.13591(9) 0.0357(3) Uani 1 1 d . . .
H7 H -0.4127 0.6710 0.1307 0.043 Uiso 1 1 calc R . .
C8 C -0.33364(18) 0.53394(14) 0.16780(8) 0.0380(4) Uani 1 1 d . . .
H8 H -0.4464 0.5163 0.1887 0.046 Uiso 1 1 calc R . .
C9 C -0.18704(18) 0.46075(12) 0.17039(7) 0.0310(3) Uani 1 1 d . . .
C10 C -0.02246(17) 0.48264(10) 0.13140(7) 0.0242(3) Uani 1 1 d . . .
C11 C -0.2028(2) 0.36844(12) 0.21371(8) 0.0382(4) Uani 1 1 d . . .
H11 H -0.3132 0.3523 0.2374 0.046 Uiso 1 1 calc R . .
C12 C -0.0589(2) 0.30406(12) 0.22078(8) 0.0389(4) Uani 1 1 d . . .
H12 H -0.0650 0.2493 0.2552 0.047 Uiso 1 1 calc R . .
C13 C 0.1021(2) 0.31867(10) 0.17629(8) 0.0322(3) Uani 1 1 d . . .
C14 C 0.10998(17) 0.40055(9) 0.12251(7) 0.0242(3) Uani 1 1 d . . .
C15 C 0.2554(2) 0.25211(11) 0.18471(9) 0.0385(4) Uani 1 1 d . . .
H15 H 0.2522 0.1996 0.2210 0.046 Uiso 1 1 calc R . .
C16 C 0.4058(2) 0.26427(10) 0.14054(9) 0.0387(4) Uani 1 1 d . . .
H16 H 0.5117 0.2275 0.1519 0.046 Uiso 1 1 calc R . .
C17 C 0.40404(18) 0.33250(10) 0.07704(8) 0.0306(3) Uani 1 1 d . . .
C18 C 0.24775(17) 0.39463(9) 0.06295(7) 0.0237(3) Uani 1 1 d . . .
C19 C 0.5538(2) 0.33491(11) 0.02494(9) 0.0372(3) Uani 1 1 d . . .
H19 H 0.6612 0.3002 0.0374 0.045 Uiso 1 1 calc R . .
C20 C 0.54367(19) 0.38632(11) -0.04206(9) 0.0373(3) Uani 1 1 d . . .
H20 H 0.6465 0.3912 -0.0733 0.045 Uiso 1 1 calc R . .
C21 C 0.37534(18) 0.43352(10) -0.06551(8) 0.0289(3) Uani 1 1 d . . .
C22 C 0.22570(17) 0.43774(9) -0.01360(7) 0.0231(3) Uani 1 1 d . . .
C23 C 0.35386(19) 0.47116(11) -0.14101(8) 0.0347(3) Uani 1 1 d . . .
H23 H 0.4533 0.4702 -0.1743 0.042 Uiso 1 1 calc R . .
C24 C 0.1908(2) 0.50875(11) -0.16605(8) 0.0351(3) Uani 1 1 d . . .
H24 H 0.1798 0.5343 -0.2157 0.042 Uiso 1 1 calc R . .
C25 C 0.03908(19) 0.50886(10) -0.11658(7) 0.0287(3) Uani 1 1 d . . .
H25 H -0.0737 0.5323 -0.1341 0.034 Uiso 1 1 calc R . .
C26 C 0.05656(17) 0.47448(9) -0.04242(7) 0.0237(3) Uani 1 1 d . . .
H26 H -0.0451 0.4753 -0.0104 0.028 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 C3 1.365(2) . ?
C1 C2 1.3991(18) . ?
C1 H1 0.9300 . ?
C2 C4 1.3723(18) . ?
C2 H2 0.9300 . ?
C3 C5 1.407(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.4120(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.4233(17) . ?
C5 C7 1.428(2) . ?
C6 C10 1.4509(18) . ?
C7 C8 1.342(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.431(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.4104(17) . ?
C9 C11 1.419(2) . ?
C10 C14 1.4460(18) . ?
C11 C12 1.347(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.423(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.4167(18) . ?
C13 C15 1.421(2) . ?
C14 C18 1.4485(18) . ?
C15 C16 1.352(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.417(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.4186(17) . ?
C17 C19 1.423(2) . ?
C18 C22 1.4560(18) . ?
C19 C20 1.347(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.433(2) . ?
C20 H20 0.9300 . ?
C21 C23 1.413(2) . ?
C21 C22 1.4208(17) . ?
C22 C26 1.4166(18) . ?
C23 C24 1.359(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.405(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.3737(18) . ?
C25 H25 0.9300 . ?
C26 H26 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
C3 C1 C2 119.38(12) . . ?
C3 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C4 C2 C1 120.67(12) . . ?
C4 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C1 C3 C5 121.33(12) . . ?
C1 C3 H3 119.3 . . ?
C5 C3 H3 119.3 . . ?
C2 C4 C6 121.47(11) . . ?
C2 C4 H4 119.3 . . ?
C6 C4 H4 119.3 . . ?
C3 C5 C6 119.68(12) . . ?
C3 C5 C7 120.84(12) . . ?
C6 C5 C7 119.33(12) . . ?
C4 C6 C5 117.29(11) . . ?
C4 C6 C10 123.32(11) . . ?
C5 C6 C10 119.13(11) . . ?
C8 C7 C5 120.44(13) . . ?
C8 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C7 C8 C9 121.59(12) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C11 119.70(14) . . ?
C10 C9 C8 119.34(13) . . ?
C11 C9 C8 120.93(13) . . ?
C9 C10 C14 118.34(12) . . ?
C9 C10 C6 117.61(12) . . ?
C14 C10 C6 123.75(11) . . ?
C12 C11 C9 120.43(14) . . ?
C12 C11 H11 119.8 . . ?
C9 C11 H11 119.8 . . ?
C11 C12 C13 120.90(13) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C15 119.37(14) . . ?
C14 C13 C12 119.61(13) . . ?
C15 C13 C12 121.02(13) . . ?
C13 C14 C10 116.88(12) . . ?
C13 C14 C18 117.60(12) . . ?
C10 C14 C18 125.52(11) . . ?
C16 C15 C13 120.77(13) . . ?
C16 C15 H15 119.6 . . ?
C13 C15 H15 119.6 . . ?
C15 C16 C17 120.70(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 119.78(13) . . ?
C16 C17 C19 120.37(13) . . ?
C18 C17 C19 119.76(13) . . ?
C17 C18 C14 117.74(12) . . ?
C17 C18 C22 117.73(12) . . ?
C14 C18 C22 124.08(11) . . ?
C20 C19 C17 121.49(13) . . ?
C20 C19 H19 119.3 . . ?
C17 C19 H19 119.3 . . ?
C19 C20 C21 120.38(13) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C23 C21 C22 119.67(12) . . ?
C23 C21 C20 120.57(12) . . ?
C22 C21 C20 119.68(13) . . ?
C26 C22 C21 117.29(11) . . ?
C26 C22 C18 123.41(11) . . ?
C21 C22 C18 118.97(11) . . ?
C24 C23 C21 121.37(12) . . ?
C24 C23 H23 119.3 . . ?
C21 C23 H23 119.3 . . ?
C23 C24 C25 119.67(13) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.29(13) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C22 121.60(12) . . ?
C25 C26 H26 119.2 . . ?
C22 C26 H26 119.2 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
