# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cmpd9_lms226
_database_code_depnum_ccdc_archive 'CCDC 1479924'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
napthto[1,2-s]picene 
;
_chemical_name_common            naphtho[1,2-i]pentahelicene
_chemical_melting_point          503-504
_chemical_formula_moiety         'C30 H18'
_chemical_formula_sum            'C30 H18'
_chemical_formula_weight         378.44

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   Pca2(1)

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

_cell_length_a                   11.2287(3)
_cell_length_b                   21.5577(6)
_cell_length_c                   7.6682(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1856.20(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    9316
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.53

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      115(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 SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 0.75
_diffrn_reflns_number            24906
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.53
_reflns_number_total             4649
_reflns_number_gt                4324
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL (XS)'
_computing_structure_refinement  'Bruker SHELXTL (XL)'
_computing_molecular_graphics    'Bruker SHELXTL (XP)'
_computing_publication_material  'Bruker SHELXTL (XCIF)'

_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)+(0.0457P)²+0.3286P] 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         4649
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.53542(11) 0.30864(6) 0.32324(18) 0.0198(2) Uani 1 1 d . . .
C2 C 0.62270(11) 0.28908(6) 0.20525(18) 0.0210(2) Uani 1 1 d . . .
C3 C 0.69789(12) 0.33463(6) 0.12601(19) 0.0246(3) Uani 1 1 d . . .
H3 H 0.7630 0.3215 0.0560 0.030 Uiso 1 1 calc R . .
C4 C 0.67805(12) 0.39628(6) 0.14898(19) 0.0255(3) Uani 1 1 d . . .
H4 H 0.7340 0.4255 0.1057 0.031 Uiso 1 1 calc R . .
C5 C 0.57465(12) 0.41743(6) 0.23691(18) 0.0240(3) Uani 1 1 d . . .
C6 C 0.53790(13) 0.48052(6) 0.23209(19) 0.0273(3) Uani 1 1 d . . .
H6 H 0.5908 0.5111 0.1877 0.033 Uiso 1 1 calc R . .
C7 C 0.42825(14) 0.49791(6) 0.2899(2) 0.0295(3) Uani 1 1 d . . .
H7 H 0.4051 0.5403 0.2857 0.035 Uiso 1 1 calc R . .
C8 C 0.34885(13) 0.45286(6) 0.3563(2) 0.0272(3) Uani 1 1 d . . .
H8 H 0.2704 0.4645 0.3892 0.033 Uiso 1 1 calc R . .
C9 C 0.38498(12) 0.39243(6) 0.37332(19) 0.0234(3) Uani 1 1 d . . .
H9 H 0.3321 0.3629 0.4228 0.028 Uiso 1 1 calc R . .
C10 C 0.49923(11) 0.37323(6) 0.31880(18) 0.0210(3) Uani 1 1 d . . .
C11 C 0.48197(11) 0.26224(6) 0.43763(17) 0.0196(2) Uani 1 1 d . . .
C12 C 0.48015(11) 0.20038(6) 0.37794(18) 0.0204(2) Uani 1 1 d . . .
C13 C 0.43643(12) 0.15262(6) 0.49107(19) 0.0234(3) Uani 1 1 d . . .
H13 H 0.4388 0.1107 0.4533 0.028 Uiso 1 1 calc R . .
C14 C 0.39185(11) 0.16609(6) 0.65060(19) 0.0239(3) Uani 1 1 d . . .
H14 H 0.3591 0.1337 0.7197 0.029 Uiso 1 1 calc R . .
C15 C 0.39293(11) 0.22745(6) 0.71686(18) 0.0221(3) Uani 1 1 d . . .
C16 C 0.35039(12) 0.24023(6) 0.88662(19) 0.0242(3) Uani 1 1 d . . .
H16 H 0.3105 0.2086 0.9500 0.029 Uiso 1 1 calc R . .
C17 C 0.36552(12) 0.29726(6) 0.96123(19) 0.0253(3) Uani 1 1 d . . .
H17 H 0.3345 0.3056 1.0741 0.030 Uiso 1 1 calc R . .
C18 C 0.42751(12) 0.34339(6) 0.86891(19) 0.0248(3) Uani 1 1 d . . .
H18 H 0.4429 0.3822 0.9229 0.030 Uiso 1 1 calc R . .
C19 C 0.46611(12) 0.33295(6) 0.70163(19) 0.0226(3) Uani 1 1 d . . .
H19 H 0.5080 0.3648 0.6421 0.027 Uiso 1 1 calc R . .
C20 C 0.44507(11) 0.27570(6) 0.61504(18) 0.0206(2) Uani 1 1 d . . .
C21 C 0.53739(11) 0.18428(6) 0.21494(18) 0.0209(2) Uani 1 1 d . . .
C22 C 0.62579(11) 0.22433(6) 0.15168(18) 0.0220(3) Uani 1 1 d . . .
C23 C 0.70814(13) 0.20184(6) 0.0254(2) 0.0269(3) Uani 1 1 d . . .
H23 H 0.7729 0.2274 -0.0091 0.032 Uiso 1 1 calc R . .
C24 C 0.69603(13) 0.14457(7) -0.0470(2) 0.0299(3) Uani 1 1 d . . .
H24 H 0.7562 0.1290 -0.1224 0.036 Uiso 1 1 calc R . .
C25 C 0.59390(13) 0.10785(6) -0.0105(2) 0.0267(3) Uani 1 1 d . . .
C26 C 0.56829(14) 0.05386(6) -0.1092(2) 0.0315(3) Uani 1 1 d . . .
H26 H 0.6256 0.0387 -0.1897 0.038 Uiso 1 1 calc R . .
C27 C 0.46228(15) 0.02323(6) -0.0904(2) 0.0329(3) Uani 1 1 d . . .
H27 H 0.4462 -0.0128 -0.1579 0.039 Uiso 1 1 calc R . .
C28 C 0.37749(14) 0.04512(7) 0.0287(2) 0.0307(3) Uani 1 1 d . . .
H28 H 0.3025 0.0250 0.0381 0.037 Uiso 1 1 calc R . .
C29 C 0.40246(12) 0.09580(6) 0.1324(2) 0.0258(3) Uani 1 1 d . . .
H29 H 0.3449 0.1094 0.2147 0.031 Uiso 1 1 calc R . .
C30 C 0.51202(12) 0.12797(6) 0.11890(19) 0.0233(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3989(19) . ?
C1 C10 1.4510(18) . ?
C1 C11 1.4594(17) . ?
C2 C3 1.4305(17) . ?
C2 C22 1.4554(18) . ?
C3 C4 1.3590(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.4211(18) . ?
C5 C6 1.4217(19) . ?
C6 C7 1.361(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3705(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4113(19) . ?
C9 H9 0.9500 . ?
C11 C12 1.4102(17) . ?
C11 C20 1.4514(18) . ?
C12 C13 1.4330(18) . ?
C12 C21 1.4477(19) . ?
C13 C14 1.353(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.4170(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(2) . ?
C15 C20 1.4263(17) . ?
C16 C17 1.367(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4052(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.4212(18) . ?
C19 H19 0.9500 . ?
C21 C22 1.4022(17) . ?
C21 C30 1.4482(18) . ?
C22 C23 1.4241(19) . ?
C23 C24 1.360(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.421(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.418(2) . ?
C25 C30 1.421(2) . ?
C26 C27 1.369(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.401(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.380(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.4159(19) . ?
C29 H29 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 118.06(12) . . ?
C2 C1 C11 118.05(11) . . ?
C10 C1 C11 123.82(12) . . ?
C1 C2 C3 118.77(12) . . ?
C1 C2 C22 119.23(11) . . ?
C3 C2 C22 121.63(12) . . ?
C4 C3 C2 121.30(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.69(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C10 118.84(12) . . ?
C4 C5 C6 122.20(12) . . ?
C10 C5 C6 118.68(13) . . ?
C7 C6 C5 121.16(13) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.91(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.05(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.31(13) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 118.42(12) . . ?
C9 C10 C1 121.95(11) . . ?
C5 C10 C1 119.14(12) . . ?
C12 C11 C20 119.28(11) . . ?
C12 C11 C1 117.32(12) . . ?
C20 C11 C1 122.95(11) . . ?
C11 C12 C13 119.20(12) . . ?
C11 C12 C21 120.04(11) . . ?
C13 C12 C21 120.17(11) . . ?
C14 C13 C12 121.33(12) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.41(12) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 120.62(12) . . ?
C16 C15 C20 120.04(12) . . ?
C14 C15 C20 119.21(12) . . ?
C17 C16 C15 121.26(13) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.16(13) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 120.74(13) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.77(12) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C15 116.47(12) . . ?
C19 C20 C11 124.33(12) . . ?
C15 C20 C11 118.99(11) . . ?
C22 C21 C12 117.73(11) . . ?
C22 C21 C30 118.66(12) . . ?
C12 C21 C30 123.55(12) . . ?
C21 C22 C23 119.02(12) . . ?
C21 C22 C2 118.43(11) . . ?
C23 C22 C2 122.28(12) . . ?
C24 C23 C22 121.44(13) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 120.38(13) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C30 119.48(13) . . ?
C26 C25 C24 121.05(14) . . ?
C30 C25 C24 119.32(12) . . ?
C27 C26 C25 121.07(15) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 119.81(14) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 120.28(14) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 121.46(14) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C29 C30 C25 117.65(12) . . ?
C29 C30 C21 122.97(13) . . ?
C25 C30 C21 118.93(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
C10 C1 C2 C3 19.35(18) . . . . ?
C11 C1 C2 C3 -163.60(12) . . . . ?
C10 C1 C2 C22 -153.76(12) . . . . ?
C11 C1 C2 C22 23.28(18) . . . . ?
C1 C2 C3 C4 -7.0(2) . . . . ?
C22 C2 C3 C4 165.99(13) . . . . ?
C2 C3 C4 C5 -6.8(2) . . . . ?
C3 C4 C5 C10 7.4(2) . . . . ?
C3 C4 C5 C6 -166.55(14) . . . . ?
C4 C5 C6 C7 168.02(14) . . . . ?
C10 C5 C6 C7 -5.9(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 4.4(2) . . . . ?
C7 C8 C9 C10 -2.7(2) . . . . ?
C8 C9 C10 C5 -3.2(2) . . . . ?
C8 C9 C10 C1 -175.08(13) . . . . ?
C4 C5 C10 C9 -166.74(13) . . . . ?
C6 C5 C10 C9 7.4(2) . . . . ?
C4 C5 C10 C1 5.3(2) . . . . ?
C6 C5 C10 C1 179.51(12) . . . . ?
C2 C1 C10 C9 153.12(13) . . . . ?
C11 C1 C10 C9 -23.7(2) . . . . ?
C2 C1 C10 C5 -18.67(19) . . . . ?
C11 C1 C10 C5 164.47(13) . . . . ?
C2 C1 C11 C12 -26.67(18) . . . . ?
C10 C1 C11 C12 150.20(12) . . . . ?
C2 C1 C11 C20 145.55(13) . . . . ?
C10 C1 C11 C20 -37.59(19) . . . . ?
C20 C11 C12 C13 3.00(18) . . . . ?
C1 C11 C12 C13 175.52(11) . . . . ?
C20 C11 C12 C21 -168.18(12) . . . . ?
C1 C11 C12 C21 4.33(18) . . . . ?
C11 C12 C13 C14 3.10(19) . . . . ?
C21 C12 C13 C14 174.27(12) . . . . ?
C12 C13 C14 C15 -3.8(2) . . . . ?
C13 C14 C15 C16 -177.41(12) . . . . ?
C13 C14 C15 C20 -1.73(19) . . . . ?
C14 C15 C16 C17 171.02(13) . . . . ?
C20 C15 C16 C17 -4.62(19) . . . . ?
C15 C16 C17 C18 -1.8(2) . . . . ?
C16 C17 C18 C19 4.1(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C15 -6.35(18) . . . . ?
C18 C19 C20 C11 179.00(12) . . . . ?
C16 C15 C20 C19 8.47(17) . . . . ?
C14 C15 C20 C19 -167.24(12) . . . . ?
C16 C15 C20 C11 -176.58(12) . . . . ?
C14 C15 C20 C11 7.71(18) . . . . ?
C12 C11 C20 C19 166.21(12) . . . . ?
C1 C11 C20 C19 -5.9(2) . . . . ?
C12 C11 C20 C15 -8.32(18) . . . . ?
C1 C11 C20 C15 179.61(11) . . . . ?
C11 C12 C21 C22 21.43(18) . . . . ?
C13 C12 C21 C22 -149.67(13) . . . . ?
C11 C12 C21 C30 -161.47(12) . . . . ?
C13 C12 C21 C30 27.43(19) . . . . ?
C12 C21 C22 C23 160.88(12) . . . . ?
C30 C21 C22 C23 -16.37(19) . . . . ?
C12 C21 C22 C2 -24.96(17) . . . . ?
C30 C21 C22 C2 157.80(12) . . . . ?
C1 C2 C22 C21 2.74(18) . . . . ?
C3 C2 C22 C21 -170.18(13) . . . . ?
C1 C2 C22 C23 176.70(13) . . . . ?
C3 C2 C22 C23 3.8(2) . . . . ?
C21 C22 C23 C24 6.3(2) . . . . ?
C2 C22 C23 C24 -167.61(13) . . . . ?
C22 C23 C24 C25 6.1(2) . . . . ?
C23 C24 C25 C26 167.73(15) . . . . ?
C23 C24 C25 C30 -7.9(2) . . . . ?
C30 C25 C26 C27 4.6(2) . . . . ?
C24 C25 C26 C27 -171.05(14) . . . . ?
C25 C26 C27 C28 -0.3(2) . . . . ?
C26 C27 C28 C29 -2.8(2) . . . . ?
C27 C28 C29 C30 1.7(2) . . . . ?
C28 C29 C30 C25 2.5(2) . . . . ?
C28 C29 C30 C21 174.70(13) . . . . ?
C26 C25 C30 C29 -5.6(2) . . . . ?
C24 C25 C30 C29 170.14(13) . . . . ?
C26 C25 C30 C21 -178.05(13) . . . . ?
C24 C25 C30 C21 -2.35(19) . . . . ?
C22 C21 C30 C29 -157.66(13) . . . . ?
C12 C21 C30 C29 25.3(2) . . . . ?
C22 C21 C30 C25 14.41(18) . . . . ?
C12 C21 C30 C25 -162.66(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.53
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.037
_diffrn_standards_number         0
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_decay_%        N/A


####################################################################### 
# 
# 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_cmplx5_aar079
_database_code_depnum_ccdc_archive 'CCDC 1479925'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            
'(2-aminobiphenyl)(xantphos)palladium(II) mesylate'
_chemical_formula_moiety         'C51 H42 N O P2 Pd, C H3 O3 S, 3(C H2 Cl2)'
_chemical_formula_sum            'C55 H51 Cl6 N O4 P2 Pd S'
_exptl_crystal_recrystallization_method 
'slow diff of pentane into dichloromethane soln'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         1203.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6010(12)
_cell_length_b                   14.5905(18)
_cell_length_c                   20.173(3)
_cell_angle_alpha                82.894(2)
_cell_angle_beta                 81.824(2)
_cell_angle_gamma                77.999(2)
_cell_volume                     2723.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9301
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.65
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1228
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8064
_exptl_absorpt_correction_T_max  0.9607
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27009
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.02
_diffrn_reflns_theta_max         27.10
_reflns_number_total             11840
_reflns_number_gt                9219
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEX2 (Bruker-AXS, 2007)'
_computing_cell_refinement       'APEX2 (Bruker-AXS, 2007)'
_computing_data_reduction        'APEX2 (Bruker-AXS, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1000P)²+16.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11840
_refine_ls_number_parameters     689
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.2373
_refine_ls_wR_factor_gt          0.2234
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_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
Pd1 Pd 0.47856(5) 0.64922(3) 0.72072(2) 0.03124(15) Uani 1 1 d . . .
O1 O 0.5745(5) 0.4152(3) 0.7629(2) 0.0372(10) Uani 1 1 d . . .
N1 N 0.3696(7) 0.7856(4) 0.7477(3) 0.0418(13) Uani 1 1 d . . .
H1 H 0.280(8) 0.782(5) 0.741(4) 0.038(19) Uiso 1 1 d . . .
H2 H 0.374(8) 0.790(5) 0.795(4) 0.05(2) Uiso 1 1 d . . .
C1 C 0.3814(7) 0.6933(5) 0.6362(3) 0.0403(15) Uani 1 1 d . . .
P1 P 0.50742(17) 0.58176(12) 0.83644(8) 0.0334(3) Uani 1 1 d . . .
C2 C 0.3067(7) 0.6304(6) 0.6155(4) 0.0460(17) Uani 1 1 d . . .
H2A H 0.3191 0.5670 0.6351 0.055 Uiso 1 1 calc R . .
P2 P 0.64195(17) 0.54574(12) 0.65923(8) 0.0342(4) Uani 1 1 d . . .
C3 C 0.2153(9) 0.6608(7) 0.5666(4) 0.063(2) Uani 1 1 d . . .
H3A H 0.1634 0.6186 0.5535 0.075 Uiso 1 1 calc R . .
C4 C 0.1994(10) 0.7510(8) 0.5371(4) 0.066(2) Uani 1 1 d . . .
H4A H 0.1383 0.7707 0.5028 0.079 Uiso 1 1 calc R . .
C5 C 0.2705(9) 0.8135(7) 0.5565(4) 0.060(2) Uani 1 1 d . . .
H5A H 0.2584 0.8760 0.5353 0.072 Uiso 1 1 calc R . .
C6 C 0.3616(8) 0.7863(5) 0.6076(3) 0.0467(17) Uani 1 1 d . . .
C7 C 0.4273(8) 0.8548(5) 0.6324(4) 0.0484(17) Uani 1 1 d . . .
C8 C 0.4881(10) 0.9218(6) 0.5889(5) 0.065(2) Uani 1 1 d . . .
H8A H 0.4814 0.9260 0.5420 0.078 Uiso 1 1 calc R . .
C9 C 0.5571(12) 0.9813(7) 0.6130(7) 0.079(3) Uani 1 1 d . . .
H9A H 0.5984 1.0263 0.5827 0.094 Uiso 1 1 calc R . .
C10 C 0.5676(10) 0.9769(7) 0.6800(7) 0.080(3) Uani 1 1 d . . .
H10A H 0.6169 1.0184 0.6958 0.096 Uiso 1 1 calc R . .
C11 C 0.5072(9) 0.9127(6) 0.7253(5) 0.065(2) Uani 1 1 d . . .
H11A H 0.5148 0.9101 0.7719 0.078 Uiso 1 1 calc R . .
C12 C 0.4359(8) 0.8527(5) 0.7021(4) 0.0463(16) Uani 1 1 d . . .
C13 C 0.4735(7) 0.4014(5) 0.8176(3) 0.0370(13) Uani 1 1 d . . .
C14 C 0.4376(7) 0.4729(5) 0.8602(3) 0.0368(13) Uani 1 1 d . . .
C15 C 0.3443(7) 0.4591(5) 0.9178(3) 0.0432(15) Uani 1 1 d . . .
H15A H 0.3191 0.5051 0.9491 0.052 Uiso 1 1 calc R . .
C16 C 0.2872(9) 0.3770(6) 0.9297(4) 0.0540(19) Uani 1 1 d . . .
H16A H 0.2232 0.3673 0.9692 0.065 Uiso 1 1 calc R . .
C17 C 0.3228(8) 0.3103(6) 0.8846(4) 0.0522(18) Uani 1 1 d . . .
H17A H 0.2806 0.2559 0.8930 0.063 Uiso 1 1 calc R . .
C18 C 0.4186(7) 0.3199(5) 0.8273(4) 0.0441(15) Uani 1 1 d . . .
C19 C 0.4688(8) 0.2494(5) 0.7754(4) 0.0497(18) Uani 1 1 d . . .
C20 C 0.4928(7) 0.3042(5) 0.7073(4) 0.0461(16) Uani 1 1 d . . .
C21 C 0.4657(8) 0.2804(6) 0.6460(4) 0.0535(19) Uani 1 1 d . . .
H21A H 0.4265 0.2261 0.6451 0.064 Uiso 1 1 calc R . .
C22 C 0.4954(9) 0.3350(7) 0.5869(4) 0.060(2) Uani 1 1 d . . .
H22A H 0.4759 0.3174 0.5459 0.072 Uiso 1 1 calc R . .
C23 C 0.5524(7) 0.4139(5) 0.5859(4) 0.0445(16) Uani 1 1 d . . .
H23A H 0.5726 0.4502 0.5445 0.053 Uiso 1 1 calc R . .
C24 C 0.5807(7) 0.4409(5) 0.6461(3) 0.0391(14) Uani 1 1 d . . .
C25 C 0.5476(7) 0.3849(5) 0.7047(3) 0.0382(14) Uani 1 1 d . . .
C26 C 0.6175(9) 0.1900(6) 0.7930(6) 0.067(2) Uani 1 1 d . . .
H26A H 0.6837 0.2323 0.7945 0.100 Uiso 1 1 calc R . .
H26B H 0.6572 0.1466 0.7586 0.100 Uiso 1 1 calc R . .
H26C H 0.6043 0.1539 0.8370 0.100 Uiso 1 1 calc R . .
C27 C 0.3657(9) 0.1832(6) 0.7772(5) 0.064(2) Uani 1 1 d . . .
H27A H 0.2723 0.2194 0.7665 0.096 Uiso 1 1 calc R . .
H27B H 0.3546 0.1496 0.8222 0.096 Uiso 1 1 calc R . .
H27C H 0.4035 0.1377 0.7440 0.096 Uiso 1 1 calc R . .
C28 C 0.6815(7) 0.5572(5) 0.8671(3) 0.0395(14) Uani 1 1 d . . .
C29 C 0.7419(8) 0.4693(6) 0.8955(4) 0.0523(18) Uani 1 1 d . . .
H29A H 0.6931 0.4181 0.8995 0.063 Uiso 1 1 calc R . .
C30 C 0.8756(9) 0.4572(8) 0.9182(5) 0.070(3) Uani 1 1 d . . .
H30A H 0.9187 0.3971 0.9375 0.084 Uiso 1 1 calc R . .
C31 C 0.9464(9) 0.5319(9) 0.9128(5) 0.075(3) Uani 1 1 d . . .
H31A H 1.0370 0.5234 0.9289 0.090 Uiso 1 1 calc R . .
C32 C 0.8842(9) 0.6189(8) 0.8840(4) 0.067(2) Uani 1 1 d . . .
H32A H 0.9316 0.6707 0.8808 0.080 Uiso 1 1 calc R . .
C33 C 0.7561(8) 0.6306(6) 0.8604(4) 0.0516(18) Uani 1 1 d . . .
H33A H 0.7164 0.6900 0.8389 0.062 Uiso 1 1 calc R . .
C34 C 0.3937(7) 0.6582(5) 0.8958(3) 0.0392(14) Uani 1 1 d . . .
C35 C 0.2506(8) 0.6940(5) 0.8839(4) 0.0472(16) Uani 1 1 d . . .
H35A H 0.2168 0.6784 0.8455 0.057 Uiso 1 1 calc R . .
C36 C 0.1592(10) 0.7511(6) 0.9272(4) 0.062(2) Uani 1 1 d . . .
H36A H 0.0622 0.7737 0.9194 0.075 Uiso 1 1 calc R . .
C37 C 0.2096(11) 0.7757(7) 0.9827(4) 0.070(3) Uani 1 1 d . . .
H37A H 0.1475 0.8163 1.0124 0.084 Uiso 1 1 calc R . .
C38 C 0.3488(11) 0.7414(6) 0.9946(4) 0.065(2) Uani 1 1 d . . .
H38A H 0.3820 0.7581 1.0327 0.078 Uiso 1 1 calc R . .
C39 C 0.4420(9) 0.6830(6) 0.9520(3) 0.0498(17) Uani 1 1 d . . .
H39A H 0.5382 0.6597 0.9609 0.060 Uiso 1 1 calc R . .
C40 C 0.8116(7) 0.5031(5) 0.6927(3) 0.0384(14) Uani 1 1 d . . .
C41 C 0.8823(8) 0.5702(5) 0.7104(4) 0.0469(16) Uani 1 1 d . . .
H41A H 0.8371 0.6348 0.7080 0.056 Uiso 1 1 calc R . .
C42 C 1.0161(9) 0.5431(7) 0.7309(4) 0.058(2) Uani 1 1 d . . .
H42A H 1.0611 0.5891 0.7440 0.070 Uiso 1 1 calc R . .
C43 C 1.0871(9) 0.4498(7) 0.7331(4) 0.064(2) Uani 1 1 d . . .
H43A H 1.1806 0.4319 0.7467 0.076 Uiso 1 1 calc R . .
C44 C 1.0201(9) 0.3852(7) 0.7156(4) 0.060(2) Uani 1 1 d . . .
H44A H 1.0682 0.3213 0.7168 0.072 Uiso 1 1 calc R . .
C45 C 0.8828(8) 0.4093(6) 0.6959(4) 0.0495(17) Uani 1 1 d . . .
H45A H 0.8378 0.3620 0.6848 0.059 Uiso 1 1 calc R . .
C46 C 0.7122(7) 0.5983(5) 0.5779(3) 0.0380(14) Uani 1 1 d . . .
C47 C 0.7915(8) 0.5419(5) 0.5286(4) 0.0481(17) Uani 1 1 d . . .
H47A H 0.7989 0.4756 0.5349 0.058 Uiso 1 1 calc R . .
C48 C 0.8590(9) 0.5833(6) 0.4704(4) 0.056(2) Uani 1 1 d . . .
H48A H 0.9108 0.5453 0.4366 0.067 Uiso 1 1 calc R . .
C49 C 0.8508(8) 0.6782(6) 0.4619(4) 0.055(2) Uani 1 1 d . . .
H49A H 0.8966 0.7062 0.4219 0.066 Uiso 1 1 calc R . .
C50 C 0.7767(9) 0.7343(6) 0.5107(4) 0.0556(19) Uani 1 1 d . . .
H50A H 0.7739 0.8003 0.5051 0.067 Uiso 1 1 calc R . .
C51 C 0.7067(7) 0.6937(5) 0.5681(4) 0.0442(16) Uani 1 1 d . . .
H51A H 0.6538 0.7326 0.6012 0.053 Uiso 1 1 calc R . .
S1S S -0.0483(3) 0.8499(2) 0.74601(12) 0.0774(7) Uani 1 1 d . . .
C1S C -0.0821(13) 0.8402(10) 0.6671(6) 0.099(4) Uani 1 1 d . A .
H1SA H 0.0033 0.8043 0.6426 0.148 Uiso 1 1 calc R . .
H1SB H -0.1067 0.9031 0.6434 0.148 Uiso 1 1 calc R . .
H1SC H -0.1624 0.8075 0.6697 0.148 Uiso 1 1 calc R . .
Cl1A Cl -0.4847(8) 0.9514(6) 0.9141(3) 0.218(3) Uani 1 1 d D . .
Cl2A Cl -0.2251(8) 0.8763(7) 0.9794(3) 0.270(5) Uani 1 1 d D . .
C1A C -0.3022(14) 0.9440(18) 0.9131(10) 0.139(10) Uani 0.509(7) 1 d PD A 1
H1AA H -0.2530 0.9184 0.8709 0.167 Uiso 0.509(7) 1 calc PR A 1
H1AB H -0.2840 1.0086 0.9120 0.167 Uiso 0.509(7) 1 calc PR A 1
C1C C -0.384(2) 0.8557(12) 0.9563(14) 0.139(10) Uani 0.491(7) 1 d PD A 2
H1CA H -0.3590 0.8032 0.9273 0.167 Uiso 0.491(7) 1 calc PR A 2
H1CB H -0.4432 0.8351 0.9974 0.167 Uiso 0.491(7) 1 calc PR A 2
Cl1B Cl 1.0205(10) 0.8188(8) 0.1578(6) 0.097(3) Uani 0.509(7) 1 d PD A 1
Cl2B Cl 0.877(3) 0.9881(13) 0.1003(11) 0.283(12) Uani 0.509(7) 1 d PD A 1
C1B C 0.955(5) 0.9367(12) 0.1725(16) 0.183(12) Uani 0.509(7) 1 d PD A 1
H1BA H 0.8823 0.9415 0.2128 0.219 Uiso 0.509(7) 1 calc PR A 1
H1BB H 1.0334 0.9677 0.1793 0.219 Uiso 0.509(7) 1 calc PR A 1
O2 O -0.1301(13) 0.9355(11) 0.7675(7) 0.171(6) Uani 1 1 d . A 1
O3 O 0.0887(16) 0.8887(15) 0.7302(8) 0.135(6) Uani 0.654(13) 1 d P . 1
O4 O -0.1817(16) 0.8036(13) 0.7735(9) 0.098(4) Uani 0.509(7) 1 d P A 1
O4A O 0.0636(16) 0.7733(13) 0.7627(9) 0.098(4) Uani 0.491(7) 1 d P . 2
Cl1D Cl 0.8269(8) 0.9090(6) 0.3525(5) 0.122(3) Uani 0.509(7) 1 d PD A 1
Cl2D Cl 1.1290(10) 0.8436(9) 0.3678(5) 0.127(4) Uani 0.509(7) 1 d PD A 1
C1D C 0.9809(19) 0.9361(17) 0.375(3) 0.183(12) Uani 0.509(7) 1 d PD A 1
H1DA H 0.9619 0.9519 0.4225 0.219 Uiso 0.509(7) 1 calc PR A 1
H1DB H 1.0038 0.9923 0.3465 0.219 Uiso 0.509(7) 1 calc PR A 1
Cl2E Cl 0.7835(14) 1.0174(7) 0.1446(11) 0.218(9) Uani 0.491(7) 1 d PD A 2
Cl1E Cl 1.0153(18) 0.8693(12) 0.1419(8) 0.157(6) Uani 0.491(7) 1 d PD A 2
C1E C 0.966(2) 0.9888(14) 0.115(2) 0.183(12) Uani 0.491(7) 1 d PD A 2
H1EA H 0.9818 0.9997 0.0653 0.219 Uiso 0.491(7) 1 calc PR A 2
H1EB H 1.0219 1.0267 0.1343 0.219 Uiso 0.491(7) 1 calc PR A 2
Cl1F Cl 1.038(3) 0.8583(12) 0.3389(11) 0.276(13) Uani 0.491(7) 1 d PD A 2
Cl2F Cl 0.9483(16) 0.9514(7) 0.4562(7) 0.186(6) Uani 0.491(7) 1 d PD A 2
C1F C 0.891(3) 0.930(3) 0.3814(13) 0.183(12) Uani 0.491(7) 1 d PD A 2
H1FA H 0.8090 0.8972 0.3917 0.219 Uiso 0.491(7) 1 calc PR A 2
H1FB H 0.8621 0.9896 0.3535 0.219 Uiso 0.491(7) 1 calc PR A 2
O3A O -0.065(3) 0.783(3) 0.7979(15) 0.135(6) Uani 0.346(13) 1 d P A 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
Pd1 C1 2.031(7) . ?
Pd1 N1 2.142(6) . ?
Pd1 P2 2.2812(16) . ?
Pd1 P1 2.4489(16) . ?
O1 C25 1.379(8) . ?
O1 C13 1.387(8) . ?
N1 C12 1.442(10) . ?
N1 H1 0.90(8) . ?
N1 H2 0.96(8) . ?
C1 C6 1.394(10) . ?
C1 C2 1.408(10) . ?
P1 C28 1.815(7) . ?
P1 C34 1.822(7) . ?
P1 C14 1.834(7) . ?
C2 C3 1.384(11) . ?
C2 H2A 0.9500 . ?
P2 C24 1.810(7) . ?
P2 C40 1.812(7) . ?
P2 C46 1.822(7) . ?
C3 C4 1.362(14) . ?
C3 H3A 0.9500 . ?
C4 C5 1.369(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.411(11) . ?
C5 H5A 0.9500 . ?
C6 C7 1.458(11) . ?
C7 C8 1.395(11) . ?
C7 C12 1.416(11) . ?
C8 C9 1.366(15) . ?
C8 H8A 0.9500 . ?
C9 C10 1.362(16) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(15) . ?
C10 H10A 0.9500 . ?
C11 C12 1.376(12) . ?
C11 H11A 0.9500 . ?
C13 C18 1.380(10) . ?
C13 C14 1.391(9) . ?
C14 C15 1.384(9) . ?
C15 C16 1.400(11) . ?
C15 H15A 0.9500 . ?
C16 C17 1.371(12) . ?
C16 H16A 0.9500 . ?
C17 C18 1.383(10) . ?
C17 H17A 0.9500 . ?
C18 C19 1.518(10) . ?
C19 C27 1.514(10) . ?
C19 C20 1.514(11) . ?
C19 C26 1.572(11) . ?
C20 C25 1.378(10) . ?
C20 C21 1.397(11) . ?
C21 C22 1.378(13) . ?
C21 H21A 0.9500 . ?
C22 C23 1.370(11) . ?
C22 H22A 0.9500 . ?
C23 C24 1.401(9) . ?
C23 H23A 0.9500 . ?
C24 C25 1.388(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.384(11) . ?
C28 C33 1.390(10) . ?
C29 C30 1.393(11) . ?
C29 H29A 0.9500 . ?
C30 C31 1.386(15) . ?
C30 H30A 0.9500 . ?
C31 C32 1.381(15) . ?
C31 H31A 0.9500 . ?
C32 C33 1.352(11) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 C39 1.397(10) . ?
C34 C35 1.408(10) . ?
C35 C36 1.373(11) . ?
C35 H35A 0.9500 . ?
C36 C37 1.394(14) . ?
C36 H36A 0.9500 . ?
C37 C38 1.370(14) . ?
C37 H37A 0.9500 . ?
C38 C39 1.383(11) . ?
C38 H38A 0.9500 . ?
C39 H39A 0.9500 . ?
C40 C45 1.396(10) . ?
C40 C41 1.406(10) . ?
C41 C42 1.370(11) . ?
C41 H41A 0.9500 . ?
C42 C43 1.388(13) . ?
C42 H42A 0.9500 . ?
C43 C44 1.352(13) . ?
C43 H43A 0.9500 . ?
C44 C45 1.393(11) . ?
C44 H44A 0.9500 . ?
C45 H45A 0.9500 . ?
C46 C51 1.374(10) . ?
C46 C47 1.405(9) . ?
C47 C48 1.390(11) . ?
C47 H47A 0.9500 . ?
C48 C49 1.362(12) . ?
C48 H48A 0.9500 . ?
C49 C50 1.380(12) . ?
C49 H49A 0.9500 . ?
C50 C51 1.384(10) . ?
C50 H50A 0.9500 . ?
C51 H51A 0.9500 . ?
S1S O3A 1.35(4) . ?
S1S O2 1.411(12) . ?
S1S O4A 1.424(17) 1 ?
S1S O4A 1.424(17) . ?
S1S O3 1.516(16) . ?
S1S O3 1.516(16) 1 ?
S1S O4 1.572(16) . ?
S1S C1S 1.698(11) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
Cl1A C1C 1.731(10) . ?
Cl1A C1A 1.731(10) . ?
Cl2A C1A 1.721(10) . ?
Cl2A C1C 1.747(10) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?
Cl1B C1B 1.752(10) . ?
Cl2B C1B 1.745(10) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
O3 O3 0.00(4) 1 ?
O4A O4A 0.00(6) 1 ?
Cl1D C1D 1.742(10) . ?
Cl2D C1D 1.748(10) . ?
C1D H1DA 0.9900 . ?
C1D H1DB 0.9900 . ?
Cl2E C1E 1.751(10) . ?
Cl1E C1E 1.748(10) . ?
C1E H1EA 0.9900 . ?
C1E H1EB 0.9900 . ?
Cl1F C1F 1.755(10) . ?
Cl2F C1F 1.761(10) . ?
C1F H1FA 0.9900 . ?
C1F H1FB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Pd1 N1 82.0(3) . . ?
C1 Pd1 P2 87.66(19) . . ?
N1 Pd1 P2 155.40(18) . . ?
C1 Pd1 P1 158.5(2) . . ?
N1 Pd1 P1 95.11(16) . . ?
P2 Pd1 P1 102.36(6) . . ?
C25 O1 C13 113.6(5) . . ?
C12 N1 Pd1 106.1(4) . . ?
C12 N1 H1 116(5) . . ?
Pd1 N1 H1 99(5) . . ?
C12 N1 H2 114(5) . . ?
Pd1 N1 H2 110(5) . . ?
H1 N1 H2 110(6) . . ?
C6 C1 C2 119.6(7) . . ?
C6 C1 Pd1 122.8(5) . . ?
C2 C1 Pd1 116.2(5) . . ?
C28 P1 C34 103.9(3) . . ?
C28 P1 C14 104.7(3) . . ?
C34 P1 C14 100.7(3) . . ?
C28 P1 Pd1 121.1(2) . . ?
C34 P1 Pd1 110.2(2) . . ?
C14 P1 Pd1 113.9(2) . . ?
C3 C2 C1 120.0(8) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C24 P2 C40 105.1(3) . . ?
C24 P2 C46 108.5(3) . . ?
C40 P2 C46 97.6(3) . . ?
C24 P2 Pd1 114.8(2) . . ?
C40 P2 Pd1 115.4(2) . . ?
C46 P2 Pd1 113.8(2) . . ?
C4 C3 C2 120.4(8) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C5 120.6(8) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.9(8) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 118.4(8) . . ?
C1 C6 C7 120.6(6) . . ?
C5 C6 C7 121.0(7) . . ?
C8 C7 C12 117.9(8) . . ?
C8 C7 C6 121.7(8) . . ?
C12 C7 C6 120.4(7) . . ?
C9 C8 C7 120.6(10) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 120.9(10) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 120.7(10) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 119.4(10) . . ?
C12 C11 H11A 120.3 . . ?
C10 C11 H11A 120.3 . . ?
C11 C12 C7 120.5(8) . . ?
C11 C12 N1 121.2(8) . . ?
C7 C12 N1 118.3(7) . . ?
C18 C13 O1 119.8(6) . . ?
C18 C13 C14 124.8(6) . . ?
O1 C13 C14 115.3(6) . . ?
C15 C14 C13 117.2(6) . . ?
C15 C14 P1 123.2(5) . . ?
C13 C14 P1 119.6(5) . . ?
C14 C15 C16 119.6(7) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C17 C16 C15 120.5(7) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C16 C17 C18 121.8(7) . . ?
C16 C17 H17A 119.1 . . ?
C18 C17 H17A 119.1 . . ?
C13 C18 C17 116.0(7) . . ?
C13 C18 C19 117.9(6) . . ?
C17 C18 C19 126.2(7) . . ?
C27 C19 C20 113.1(7) . . ?
C27 C19 C18 112.1(7) . . ?
C20 C19 C18 107.7(6) . . ?
C27 C19 C26 108.6(7) . . ?
C20 C19 C26 108.2(7) . . ?
C18 C19 C26 106.9(7) . . ?
C25 C20 C21 116.1(7) . . ?
C25 C20 C19 117.7(7) . . ?
C21 C20 C19 126.1(7) . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C23 C22 C21 121.7(7) . . ?
C23 C22 H22A 119.2 . . ?
C21 C22 H22A 119.2 . . ?
C22 C23 C24 119.7(7) . . ?
C22 C23 H23A 120.1 . . ?
C24 C23 H23A 120.1 . . ?
C25 C24 C23 116.9(6) . . ?
C25 C24 P2 114.5(5) . . ?
C23 C24 P2 128.3(6) . . ?
C20 C25 O1 120.3(6) . . ?
C20 C25 C24 124.8(6) . . ?
O1 C25 C24 114.9(6) . . ?
C19 C26 H26A 109.5 . . ?
C19 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C19 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C27 H27A 109.5 . . ?
C19 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C19 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C33 119.7(7) . . ?
C29 C28 P1 122.7(6) . . ?
C33 C28 P1 117.6(6) . . ?
C28 C29 C30 118.7(8) . . ?
C28 C29 H29A 120.6 . . ?
C30 C29 H29A 120.6 . . ?
C31 C30 C29 120.7(9) . . ?
C31 C30 H30A 119.7 . . ?
C29 C30 H30A 119.7 . . ?
C32 C31 C30 119.5(8) . . ?
C32 C31 H31A 120.2 . . ?
C30 C31 H31A 120.2 . . ?
C33 C32 C31 120.1(9) . . ?
C33 C32 H32A 119.9 . . ?
C31 C32 H32A 119.9 . . ?
C32 C33 C28 121.2(8) . . ?
C32 C33 H33A 119.4 . . ?
C28 C33 H33A 119.4 . . ?
C39 C34 C35 118.8(6) . . ?
C39 C34 P1 123.1(6) . . ?
C35 C34 P1 118.1(5) . . ?
C36 C35 C34 120.7(7) . . ?
C36 C35 H35A 119.6 . . ?
C34 C35 H35A 119.6 . . ?
C35 C36 C37 119.7(8) . . ?
C35 C36 H36A 120.2 . . ?
C37 C36 H36A 120.2 . . ?
C38 C37 C36 120.0(8) . . ?
C38 C37 H37A 120.0 . . ?
C36 C37 H37A 120.0 . . ?
C37 C38 C39 121.2(8) . . ?
C37 C38 H38A 119.4 . . ?
C39 C38 H38A 119.4 . . ?
C38 C39 C34 119.6(8) . . ?
C38 C39 H39A 120.2 . . ?
C34 C39 H39A 120.2 . . ?
C45 C40 C41 117.9(7) . . ?
C45 C40 P2 124.1(6) . . ?
C41 C40 P2 117.7(5) . . ?
C42 C41 C40 120.4(7) . . ?
C42 C41 H41A 119.8 . . ?
C40 C41 H41A 119.8 . . ?
C41 C42 C43 121.4(8) . . ?
C41 C42 H42A 119.3 . . ?
C43 C42 H42A 119.3 . . ?
C44 C43 C42 118.4(8) . . ?
C44 C43 H43A 120.8 . . ?
C42 C43 H43A 120.8 . . ?
C43 C44 C45 122.2(8) . . ?
C43 C44 H44A 118.9 . . ?
C45 C44 H44A 118.9 . . ?
C44 C45 C40 119.7(8) . . ?
C44 C45 H45A 120.2 . . ?
C40 C45 H45A 120.2 . . ?
C51 C46 C47 118.6(6) . . ?
C51 C46 P2 119.6(5) . . ?
C47 C46 P2 121.1(5) . . ?
C48 C47 C46 120.0(7) . . ?
C48 C47 H47A 120.0 . . ?
C46 C47 H47A 120.0 . . ?
C49 C48 C47 120.0(7) . . ?
C49 C48 H48A 120.0 . . ?
C47 C48 H48A 120.0 . . ?
C48 C49 C50 120.7(7) . . ?
C48 C49 H49A 119.7 . . ?
C50 C49 H49A 119.7 . . ?
C49 C50 C51 119.5(8) . . ?
C49 C50 H50A 120.3 . . ?
C51 C50 H50A 120.3 . . ?
C46 C51 C50 121.2(7) . . ?
C46 C51 H51A 119.4 . . ?
C50 C51 H51A 119.4 . . ?
O3A S1S O2 106.2(16) . . ?
O3A S1S O4A 56.9(15) . 1 ?
O2 S1S O4A 143.3(10) . 1 ?
O3A S1S O4A 56.9(15) . . ?
O2 S1S O4A 143.3(10) . . ?
O4A S1S O4A 0.0(18) 1 . ?
O3A S1S O3 121.3(14) . . ?
O2 S1S O3 93.2(10) . . ?
O4A S1S O3 74.5(10) 1 . ?
O4A S1S O3 74.5(10) . . ?
O3A S1S O3 121.3(14) . 1 ?
O2 S1S O3 93.2(10) . 1 ?
O4A S1S O3 74.5(10) 1 1 ?
O4A S1S O3 74.5(10) . 1 ?
O3 S1S O3 0.0(19) . 1 ?
O3A S1S O4 49.9(12) . . ?
O2 S1S O4 87.7(9) . . ?
O4A S1S O4 99.5(9) 1 . ?
O4A S1S O4 99.5(9) . . ?
O3 S1S O4 170.8(9) . . ?
O3 S1S O4 170.8(9) 1 . ?
O3A S1S C1S 122.8(14) . . ?
O2 S1S C1S 108.7(7) . . ?
O4A S1S C1S 107.5(9) 1 . ?
O4A S1S C1S 107.5(9) . . ?
O3 S1S C1S 100.4(8) . . ?
O3 S1S C1S 100.4(8) 1 . ?
O4 S1S C1S 87.9(8) . . ?
S1S C1S H1SA 109.5 . . ?
S1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
S1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1C Cl1A C1A 59.8(9) . . ?
C1A Cl2A C1C 59.7(9) . . ?
Cl2A C1A Cl1A 116.2(9) . . ?
Cl2A C1A H1AA 108.2 . . ?
Cl1A C1A H1AA 108.2 . . ?
Cl2A C1A H1AB 108.2 . . ?
Cl1A C1A H1AB 108.2 . . ?
H1AA C1A H1AB 107.4 . . ?
Cl1A C1C Cl2A 114.9(9) . . ?
Cl1A C1C H1CA 108.5 . . ?
Cl2A C1C H1CA 108.5 . . ?
Cl1A C1C H1CB 108.5 . . ?
Cl2A C1C H1CB 108.5 . . ?
H1CA C1C H1CB 107.5 . . ?
Cl2B C1B Cl1B 104.7(12) . . ?
Cl2B C1B H1BA 110.8 . . ?
Cl1B C1B H1BA 110.8 . . ?
Cl2B C1B H1BB 110.8 . . ?
Cl1B C1B H1BB 110.8 . . ?
H1BA C1B H1BB 108.9 . . ?
O3 O3 S1S 0(10) 1 . ?
O4A O4A S1S 0(10) 1 . ?
Cl1D C1D Cl2D 112.8(9) . . ?
Cl1D C1D H1DA 109.0 . . ?
Cl2D C1D H1DA 109.0 . . ?
Cl1D C1D H1DB 109.0 . . ?
Cl2D C1D H1DB 109.0 . . ?
H1DA C1D H1DB 107.8 . . ?
Cl1E C1E Cl2E 104.1(12) . . ?
Cl1E C1E H1EA 110.9 . . ?
Cl2E C1E H1EA 110.9 . . ?
Cl1E C1E H1EB 110.9 . . ?
Cl2E C1E H1EB 110.9 . . ?
H1EA C1E H1EB 108.9 . . ?
Cl1F C1F Cl2F 106.4(13) . . ?
Cl1F C1F H1FA 110.5 . . ?
Cl2F C1F H1FA 110.5 . . ?
Cl1F C1F H1FB 110.5 . . ?
Cl2F C1F H1FB 110.5 . . ?
H1FA C1F H1FB 108.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.90(8) 2.16(8) 2.848(18) 133(6) 1
N1 H1 O4A 0.90(8) 2.09(8) 2.951(17) 159(7) 1

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         2.168
_refine_diff_density_min         -0.974
_refine_diff_density_rms         0.127


####################################################################### 
# 
# 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_cmpd4a_lms210
_database_code_depnum_ccdc_archive 'CCDC 1479926'
_audit_update_record             
;
2016-05-13 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
1,3-bis(trifluoromethyl)naphtho[1,2-g]chrysene
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H14 F6'
_chemical_formula_sum            'C28 H14 F6'
_exptl_crystal_recrystallization_method 'slow diff of n-hexane into THF soln'
_chemical_melting_point          450-451

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      115(2)
_chemical_formula_weight         464.39

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.81380(10)
_cell_length_b                   22.8364(3)
_cell_length_c                   9.09370(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.9067(7)
_cell_angle_gamma                90
_cell_volume                     2007.62(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.33
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 0.75
_diffrn_reflns_number            38424
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.783
_diffrn_reflns_theta_max         26.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4088
_reflns_number_gt                3187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.9508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4088
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58612(16) 0.36564(6) 0.42661(16) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.45875(16) 0.35191(7) 0.46860(16) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.40673(16) 0.38967(7) 0.57139(17) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.3190 0.3816 0.5976 0.028 Uiso 1 1 calc R U . . .
C4 C 0.47944(17) 0.43680(7) 0.63245(17) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.4379 0.4632 0.6923 0.030 Uiso 1 1 calc R U . . .
C5 C 0.61617(17) 0.44730(7) 0.60855(16) 0.0224(3) Uani 1 1 d . . . . .
C6 C 0.69991(18) 0.49086(7) 0.68995(18) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.6597 0.5175 0.7503 0.033 Uiso 1 1 calc R U . . .
C7 C 0.83714(18) 0.49518(7) 0.68318(18) 0.0284(4) Uani 1 1 d . . . . .
H7 H 0.8920 0.5249 0.7375 0.034 Uiso 1 1 calc R U . . .
C8 C 0.89692(17) 0.45534(7) 0.59533(17) 0.0260(4) Uani 1 1 d . . . . .
H8 H 0.9937 0.4567 0.5953 0.031 Uiso 1 1 calc R U . . .
C9 C 0.81714(16) 0.41451(7) 0.50949(17) 0.0229(3) Uani 1 1 d . . . . .
H9 H 0.8593 0.3886 0.4491 0.027 Uiso 1 1 calc R U . . .
C10 C 0.67291(16) 0.41026(6) 0.50917(16) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.63555(15) 0.32922(6) 0.31509(16) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.59973(16) 0.26992(7) 0.31148(16) 0.0199(3) Uani 1 1 d . . . . .
C13 C 0.67082(16) 0.23006(7) 0.23074(16) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.6529 0.1893 0.2353 0.025 Uiso 1 1 calc R U . . .
C14 C 0.76380(16) 0.24947(7) 0.14741(16) 0.0217(3) Uani 1 1 d . . . . .
H14 H 0.8160 0.2220 0.1018 0.026 Uiso 1 1 calc R U . . .
C15 C 0.78422(15) 0.31044(7) 0.12739(16) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.86325(16) 0.33148(7) 0.02220(17) 0.0252(4) Uani 1 1 d . . . . .
H16 H 0.9101 0.3043 -0.0307 0.030 Uiso 1 1 calc R U . . .
C17 C 0.87355(17) 0.39001(7) -0.00472(18) 0.0281(4) Uani 1 1 d . . . . .
H17 H 0.9277 0.4034 -0.0751 0.034 Uiso 1 1 calc R U . . .
C18 C 0.80339(17) 0.43040(7) 0.07242(18) 0.0283(4) Uani 1 1 d . . . . .
H18 H 0.8081 0.4710 0.0517 0.034 Uiso 1 1 calc R U . . .
C19 C 0.72847(16) 0.41147(7) 0.17719(17) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.6824 0.4393 0.2288 0.029 Uiso 1 1 calc R U . . .
C20 C 0.71825(15) 0.35121(7) 0.21009(16) 0.0207(3) Uani 1 1 d . . . . .
C21 C 0.48477(15) 0.25093(7) 0.38294(16) 0.0202(3) Uani 1 1 d . . . . .
C22 C 0.39712(16) 0.29429(7) 0.43011(16) 0.0202(3) Uani 1 1 d . . . . .
C23 C 0.26472(16) 0.27502(7) 0.45523(17) 0.0226(3) Uani 1 1 d . . . . .
C24 C 0.23739(17) 0.21609(7) 0.46723(17) 0.0241(3) Uani 1 1 d . . . . .
H24 H 0.1504 0.2039 0.4887 0.029 Uiso 1 1 calc R U . . .
C25 C 0.33637(16) 0.17429(7) 0.44807(17) 0.0229(3) Uani 1 1 d . . . . .
C26 C 0.45544(16) 0.19123(7) 0.39900(16) 0.0213(3) Uani 1 1 d . . . . .
H26 H 0.5182 0.1624 0.3758 0.026 Uiso 1 1 calc R U . . .
C27 C 0.14275(16) 0.31473(7) 0.45909(18) 0.0266(4) Uani 1 1 d . . . . .
F1 F 0.12338(10) 0.32868(4) 0.59860(11) 0.0339(2) Uani 1 1 d . . . . .
F2 F 0.14828(10) 0.36495(4) 0.38529(11) 0.0317(2) Uani 1 1 d . . . . .
F3 F 0.02426(9) 0.28837(4) 0.39543(11) 0.0347(3) Uani 1 1 d . . . . .
C28 C 0.30461(17) 0.11125(7) 0.47054(18) 0.0270(4) Uani 1 1 d . . . . .
F4 F 0.24053(12) 0.10354(4) 0.58745(12) 0.0433(3) Uani 1 1 d . . . . .
F5 F 0.21975(11) 0.08810(4) 0.35292(12) 0.0432(3) Uani 1 1 d . . . . .
F6 F 0.41707(10) 0.07730(4) 0.49228(13) 0.0400(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.404(2) . ?
C1 C10 1.452(2) . ?
C1 C11 1.458(2) . ?
C2 C3 1.429(2) . ?
C2 C22 1.465(2) . ?
C3 C4 1.356(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(2) . ?
C5 C10 1.420(2) . ?
C6 C7 1.362(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.398(2) . ?
C11 C20 1.445(2) . ?
C12 C13 1.425(2) . ?
C12 C21 1.461(2) . ?
C13 C14 1.357(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.423(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(2) . ?
C15 C20 1.421(2) . ?
C16 C17 1.366(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.408(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.370(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.415(2) . ?
C19 H19 0.9500 . ?
C21 C26 1.406(2) . ?
C21 C22 1.425(2) . ?
C22 C23 1.427(2) . ?
C23 C24 1.380(2) . ?
C23 C27 1.507(2) . ?
C24 C25 1.394(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.376(2) . ?
C25 C28 1.495(2) . ?
C26 H26 0.9500 . ?
C27 F2 1.3345(18) . ?
C27 F3 1.3483(18) . ?
C27 F1 1.3528(19) . ?
C28 F6 1.3353(19) . ?
C28 F4 1.3367(19) . ?
C28 F5 1.3455(19) . ?

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 C10 119.13(13) . . ?
C2 C1 C11 118.70(13) . . ?
C10 C1 C11 121.63(13) . . ?
C1 C2 C3 118.56(14) . . ?
C1 C2 C22 119.07(14) . . ?
C3 C2 C22 121.26(14) . . ?
C4 C3 C2 121.64(15) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.15(15) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.26(14) . . ?
C6 C5 C10 119.71(15) . . ?
C4 C5 C10 118.85(14) . . ?
C7 C6 C5 121.12(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.47(15) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.72(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.30(15) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 117.29(14) . . ?
C9 C10 C1 123.07(14) . . ?
C5 C10 C1 119.21(14) . . ?
C12 C11 C20 119.24(13) . . ?
C12 C11 C1 117.16(13) . . ?
C20 C11 C1 123.59(13) . . ?
C11 C12 C13 119.17(14) . . ?
C11 C12 C21 119.17(14) . . ?
C13 C12 C21 121.55(14) . . ?
C14 C13 C12 120.99(14) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.94(14) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C20 119.21(14) . . ?
C16 C15 C14 121.62(14) . . ?
C20 C15 C14 119.11(14) . . ?
C17 C16 C15 121.29(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.61(15) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.44(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.32(15) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 118.02(14) . . ?
C19 C20 C11 123.07(14) . . ?
C15 C20 C11 118.74(14) . . ?
C26 C21 C22 119.83(14) . . ?
C26 C21 C12 121.43(14) . . ?
C22 C21 C12 118.66(13) . . ?
C21 C22 C23 116.56(14) . . ?
C21 C22 C2 116.75(13) . . ?
C23 C22 C2 126.05(14) . . ?
C24 C23 C22 120.54(14) . . ?
C24 C23 C27 114.77(14) . . ?
C22 C23 C27 124.54(14) . . ?
C23 C24 C25 120.57(15) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 119.80(14) . . ?
C26 C25 C28 121.59(14) . . ?
C24 C25 C28 118.45(14) . . ?
C25 C26 C21 120.44(14) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
F2 C27 F3 105.93(12) . . ?
F2 C27 F1 107.09(13) . . ?
F3 C27 F1 104.94(12) . . ?
F2 C27 C23 113.84(13) . . ?
F3 C27 C23 110.56(13) . . ?
F1 C27 C23 113.82(13) . . ?
F6 C28 F4 107.20(13) . . ?
F6 C28 F5 105.81(13) . . ?
F4 C28 F5 105.60(13) . . ?
F6 C28 C25 113.14(13) . . ?
F4 C28 C25 111.91(14) . . ?
F5 C28 C25 112.63(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
C10 C1 C2 C3 11.9(2) . . . . ?
C11 C1 C2 C3 -176.39(13) . . . . ?
C10 C1 C2 C22 -156.23(13) . . . . ?
C11 C1 C2 C22 15.5(2) . . . . ?
C1 C2 C3 C4 -2.3(2) . . . . ?
C22 C2 C3 C4 165.54(14) . . . . ?
C2 C3 C4 C5 -6.4(2) . . . . ?
C3 C4 C5 C6 -170.06(15) . . . . ?
C3 C4 C5 C10 5.1(2) . . . . ?
C4 C5 C6 C7 170.22(15) . . . . ?
C10 C5 C6 C7 -4.9(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 4.0(2) . . . . ?
C7 C8 C9 C10 -1.5(2) . . . . ?
C8 C9 C10 C5 -4.1(2) . . . . ?
C8 C9 C10 C1 -176.44(14) . . . . ?
C6 C5 C10 C9 7.1(2) . . . . ?
C4 C5 C10 C9 -168.10(14) . . . . ?
C6 C5 C10 C1 179.83(14) . . . . ?
C4 C5 C10 C1 4.6(2) . . . . ?
C2 C1 C10 C9 159.16(14) . . . . ?
C11 C1 C10 C9 -12.3(2) . . . . ?
C2 C1 C10 C5 -13.1(2) . . . . ?
C11 C1 C10 C5 175.45(13) . . . . ?
C2 C1 C11 C12 -32.1(2) . . . . ?
C10 C1 C11 C12 139.42(14) . . . . ?
C2 C1 C11 C20 147.91(14) . . . . ?
C10 C1 C11 C20 -40.6(2) . . . . ?
C20 C11 C12 C13 14.7(2) . . . . ?
C1 C11 C12 C13 -165.30(13) . . . . ?
C20 C11 C12 C21 -161.61(13) . . . . ?
C1 C11 C12 C21 18.4(2) . . . . ?
C11 C12 C13 C14 -5.7(2) . . . . ?
C21 C12 C13 C14 170.57(14) . . . . ?
C12 C13 C14 C15 -5.6(2) . . . . ?
C13 C14 C15 C16 -169.54(14) . . . . ?
C13 C14 C15 C20 7.5(2) . . . . ?
C20 C15 C16 C17 -2.2(2) . . . . ?
C14 C15 C16 C17 174.84(15) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 1.9(2) . . . . ?
C17 C18 C19 C20 -0.5(2) . . . . ?
C18 C19 C20 C15 -2.2(2) . . . . ?
C18 C19 C20 C11 -177.27(15) . . . . ?
C16 C15 C20 C19 3.5(2) . . . . ?
C14 C15 C20 C19 -173.62(14) . . . . ?
C16 C15 C20 C11 178.79(13) . . . . ?
C14 C15 C20 C11 1.7(2) . . . . ?
C12 C11 C20 C19 162.36(14) . . . . ?
C1 C11 C20 C19 -17.6(2) . . . . ?
C12 C11 C20 C15 -12.7(2) . . . . ?
C1 C11 C20 C15 167.30(14) . . . . ?
C11 C12 C21 C26 -171.92(13) . . . . ?
C13 C12 C21 C26 11.8(2) . . . . ?
C11 C12 C21 C22 11.3(2) . . . . ?
C13 C12 C21 C22 -164.98(13) . . . . ?
C26 C21 C22 C23 -15.9(2) . . . . ?
C12 C21 C22 C23 161.01(13) . . . . ?
C26 C21 C22 C2 155.59(13) . . . . ?
C12 C21 C22 C2 -27.54(19) . . . . ?
C1 C2 C22 C21 14.1(2) . . . . ?
C3 C2 C22 C21 -153.73(14) . . . . ?
C1 C2 C22 C23 -175.40(14) . . . . ?
C3 C2 C22 C23 16.8(2) . . . . ?
C21 C22 C23 C24 14.7(2) . . . . ?
C2 C22 C23 C24 -155.88(15) . . . . ?
C21 C22 C23 C27 -160.49(14) . . . . ?
C2 C22 C23 C27 29.0(2) . . . . ?
C22 C23 C24 C25 -3.0(2) . . . . ?
C27 C23 C24 C25 172.59(14) . . . . ?
C23 C24 C25 C26 -8.0(2) . . . . ?
C23 C24 C25 C28 176.67(14) . . . . ?
C24 C25 C26 C21 6.7(2) . . . . ?
C28 C25 C26 C21 -178.14(14) . . . . ?
C22 C21 C26 C25 5.6(2) . . . . ?
C12 C21 C26 C25 -171.23(13) . . . . ?
C24 C23 C27 F2 -152.03(14) . . . . ?
C22 C23 C27 F2 23.4(2) . . . . ?
C24 C23 C27 F3 -32.95(19) . . . . ?
C22 C23 C27 F3 142.46(14) . . . . ?
C24 C23 C27 F1 84.86(17) . . . . ?
C22 C23 C27 F1 -99.73(17) . . . . ?
C26 C25 C28 F6 23.0(2) . . . . ?
C24 C25 C28 F6 -161.73(14) . . . . ?
C26 C25 C28 F4 144.25(15) . . . . ?
C24 C25 C28 F4 -40.5(2) . . . . ?
C26 C25 C28 F5 -96.95(17) . . . . ?
C24 C25 C28 F5 78.32(18) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         0
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_decay_%        N/A
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

