# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008


data_global

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Chin H Chen'
'Kok-Wai Cheah.'
'Wang Lei.'
'Mei-Fang Lin.'
'Hoi-Lam Tam.'
'Wai-Yeung Wong.'
'Wai-Kwok Wong.'

_publ_contact_author_name        'Chin H Chen'
_publ_contact_author_email       FREDCHEN@HKBU.EDU.HK

_publ_section_title              
;
Novel host material for single-component white organic
light-emitting diodes based on 9-naphthylanthracene derivatives
;

# Attachment 'compound_4c.cif'

data_wy1616wm
_database_code_depnum_ccdc_archive 'CCDC 685067'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C78.50 H49 Cl'
_chemical_formula_weight         1027.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   15.3491(10)
_cell_length_b                   15.7065(10)
_cell_length_c                   15.7888(10)
_cell_angle_alpha                66.0330(10)
_cell_angle_beta                 61.6080(10)
_cell_angle_gamma                62.4360(10)
_cell_volume                     2882.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1074
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8964
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13788
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9623
_reflns_number_gt                6089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1723P)^2^+1.8549P] where P=(Fo^2^+2Fc^2^)/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         9623
_refine_ls_number_parameters     725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0932
_refine_ls_wR_factor_ref         0.2973
_refine_ls_wR_factor_gt          0.2521
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.3580(7) 0.3524(9) 0.2214(6) 0.173(4) Uani 1 1 d . . .
H1A H 1.4128 0.2926 0.2257 0.208 Uiso 1 1 calc R . .
C2 C 1.3752(7) 0.4413(13) 0.2015(10) 0.210(5) Uani 1 1 d . . .
H2A H 1.4391 0.4419 0.1933 0.253 Uiso 1 1 calc R . .
C3 C 1.2915(5) 0.5252(8) 0.1954(6) 0.175(4) Uani 1 1 d . . .
H3A H 1.3000 0.5846 0.1829 0.210 Uiso 1 1 calc R . .
C4 C 1.1973(4) 0.5297(5) 0.2061(4) 0.1029(16) Uani 1 1 d . . .
H4A H 1.1441 0.5904 0.2004 0.124 Uiso 1 1 calc R . .
C5 C 1.1795(4) 0.4429(5) 0.2256(4) 0.1104(19) Uani 1 1 d . . .
C6 C 1.2656(6) 0.3521(6) 0.2340(5) 0.128(3) Uani 1 1 d . . .
C7 C 1.2507(8) 0.2625(11) 0.2533(8) 0.190(5) Uani 1 1 d . . .
H7A H 1.3054 0.2030 0.2596 0.228 Uiso 1 1 calc R . .
C8 C 1.1550(11) 0.2618(5) 0.2633(7) 0.201(5) Uani 1 1 d . . .
H8A H 1.1466 0.2028 0.2740 0.242 Uiso 1 1 calc R . .
C9 C 1.0723(5) 0.3523(3) 0.2566(5) 0.1131(19) Uani 1 1 d . . .
H9A H 1.0076 0.3528 0.2660 0.136 Uiso 1 1 calc R . .
C10 C 1.0864(4) 0.4446(4) 0.2355(4) 0.0944(15) Uani 1 1 d . . .
C11 C 0.9954(3) 0.5402(3) 0.2310(3) 0.0666(10) Uani 1 1 d . . .
C12 C 0.9269(3) 0.5737(3) 0.3189(3) 0.0596(9) Uani 1 1 d . . .
C13 C 0.9359(3) 0.5184(3) 0.4123(3) 0.0758(11) Uani 1 1 d . . .
H13A H 0.9890 0.4574 0.4171 0.091 Uiso 1 1 calc R . .
C14 C 0.8689(4) 0.5523(3) 0.4946(3) 0.0829(12) Uani 1 1 d . . .
H14A H 0.8776 0.5146 0.5550 0.099 Uiso 1 1 calc R . .
C15 C 0.7869(3) 0.6426(3) 0.4917(3) 0.0791(11) Uani 1 1 d . . .
H15A H 0.7414 0.6647 0.5493 0.095 Uiso 1 1 calc R . .
C16 C 0.7742(3) 0.6976(3) 0.4038(3) 0.0629(9) Uani 1 1 d . . .
H16A H 0.7202 0.7582 0.4019 0.075 Uiso 1 1 calc R . .
C17 C 0.8410(2) 0.6655(2) 0.3144(2) 0.0516(8) Uani 1 1 d . . .
C18 C 0.8242(2) 0.7195(2) 0.2253(2) 0.0464(7) Uani 1 1 d . . .
C19 C 0.8894(2) 0.6843(2) 0.1386(2) 0.0475(7) Uani 1 1 d . . .
C20 C 0.8714(3) 0.7330(3) 0.0486(3) 0.0600(9) Uani 1 1 d . . .
H20A H 0.8148 0.7914 0.0454 0.072 Uiso 1 1 calc R . .
C21 C 0.9348(3) 0.6970(3) -0.0339(3) 0.0689(10) Uani 1 1 d . . .
H21A H 0.9205 0.7304 -0.0922 0.083 Uiso 1 1 calc R . .
C22 C 1.0222(3) 0.6092(3) -0.0316(3) 0.0692(10) Uani 1 1 d . . .
H22A H 1.0651 0.5850 -0.0884 0.083 Uiso 1 1 calc R . .
C23 C 1.0435(3) 0.5605(3) 0.0524(3) 0.0670(10) Uani 1 1 d . . .
H23A H 1.1026 0.5040 0.0521 0.080 Uiso 1 1 calc R . .
C24 C 0.9777(3) 0.5932(2) 0.1419(3) 0.0559(8) Uani 1 1 d . . .
C25 C 0.7341(2) 0.8154(2) 0.2221(2) 0.0463(7) Uani 1 1 d . . .
C26 C 0.6384(2) 0.8185(2) 0.2299(2) 0.0520(8) Uani 1 1 d . . .
H26A H 0.6298 0.7605 0.2381 0.062 Uiso 1 1 calc R . .
C27 C 0.5554(2) 0.9076(2) 0.2257(2) 0.0498(7) Uani 1 1 d . . .
C28 C 0.5694(2) 0.9938(2) 0.2140(2) 0.0503(7) Uani 1 1 d . . .
H28A H 0.5146 1.0537 0.2106 0.060 Uiso 1 1 calc R . .
C29 C 0.6644(2) 0.9921(2) 0.2072(2) 0.0487(7) Uani 1 1 d . . .
C30 C 0.7450(2) 0.9032(2) 0.2113(2) 0.0487(7) Uani 1 1 d . . .
H30A H 0.8084 0.9013 0.2068 0.058 Uiso 1 1 calc R . .
C31 C 0.6756(2) 1.0854(2) 0.1986(3) 0.0490(7) Uani 1 1 d . . .
C32 C 0.6122(2) 1.1349(2) 0.2754(3) 0.0536(8) Uani 1 1 d . . .
C33 C 0.5380(3) 1.0988(3) 0.3646(3) 0.0615(9) Uani 1 1 d . . .
H33A H 0.5312 1.0399 0.3728 0.074 Uiso 1 1 calc R . .
C34 C 0.4771(3) 1.1476(3) 0.4379(3) 0.0723(10) Uani 1 1 d . . .
H34A H 0.4296 1.1217 0.4953 0.087 Uiso 1 1 calc R . .
C35 C 0.4851(3) 1.2364(3) 0.4281(4) 0.0821(12) Uani 1 1 d . . .
H35A H 0.4436 1.2690 0.4793 0.099 Uiso 1 1 calc R . .
C36 C 0.5536(3) 1.2753(3) 0.3439(4) 0.0878(14) Uani 1 1 d . . .
H36A H 0.5567 1.3355 0.3373 0.105 Uiso 1 1 calc R . .
C37 C 0.6203(3) 1.2258(3) 0.2659(3) 0.0695(10) Uani 1 1 d . . .
C38 C 0.6958(3) 1.2639(3) 0.1799(3) 0.0746(12) Uani 1 1 d . . .
C39 C 0.7627(3) 1.2118(2) 0.1059(3) 0.0618(9) Uani 1 1 d . . .
C40 C 0.8439(3) 1.2437(3) 0.0215(3) 0.0748(11) Uani 1 1 d . . .
H40A H 0.8525 1.3010 0.0156 0.090 Uiso 1 1 calc R . .
C41 C 0.9081(3) 1.1937(3) -0.0494(3) 0.0731(10) Uani 1 1 d . . .
H41A H 0.9608 1.2161 -0.1031 0.088 Uiso 1 1 calc R . .
C42 C 0.8965(3) 1.1076(3) -0.0433(3) 0.0677(10) Uani 1 1 d . . .
H42A H 0.9411 1.0735 -0.0932 0.081 Uiso 1 1 calc R . .
C43 C 0.8209(3) 1.0739(3) 0.0345(3) 0.0566(8) Uani 1 1 d . . .
H43A H 0.8132 1.0178 0.0363 0.068 Uiso 1 1 calc R . .
C44 C 0.7523(2) 1.1220(2) 0.1143(3) 0.0512(8) Uani 1 1 d . . .
C45 C 0.6974(4) 1.3647(4) 0.1638(5) 0.116(2) Uani 1 1 d . . .
C46 C 0.6610(4) 1.4459(3) 0.0894(4) 0.1039(18) Uani 1 1 d . . .
H46A H 0.6387 1.4356 0.0501 0.125 Uiso 1 1 calc R . .
C47 C 0.6591(7) 1.5432(5) 0.0757(9) 0.208(6) Uani 1 1 d . . .
H47A H 0.6350 1.5947 0.0274 0.250 Uiso 1 1 calc R . .
C48 C 0.6914(8) 1.5627(10) 0.1313(11) 0.200(6) Uani 1 1 d . . .
H48A H 0.6915 1.6252 0.1217 0.240 Uiso 1 1 calc R . .
C49 C 0.7254(6) 1.4785(6) 0.2062(8) 0.145(4) Uani 1 1 d . . .
C50 C 0.7294(4) 1.3827(5) 0.2195(7) 0.135(3) Uani 1 1 d . . .
C51 C 0.7692(4) 1.3039(5) 0.2930(4) 0.0918(14) Uani 1 1 d . . .
H51A H 0.7764 1.2383 0.3050 0.110 Uiso 1 1 calc R . .
C52 C 0.7944(5) 1.3350(8) 0.3417(8) 0.186(5) Uani 1 1 d . . .
H52A H 0.8232 1.2849 0.3879 0.224 Uiso 1 1 calc R . .
C53 C 0.7861(8) 1.4251(11) 0.3368(10) 0.192(5) Uani 1 1 d . . .
H53A H 0.8008 1.4382 0.3802 0.230 Uiso 1 1 calc R . .
C54 C 0.7535(7) 1.4976(8) 0.2606(9) 0.162(4) Uani 1 1 d . . .
H54A H 0.7516 1.5615 0.2481 0.194 Uiso 1 1 calc R . .
C55 C 0.4536(2) 0.9110(3) 0.2337(3) 0.0543(8) Uani 1 1 d . . .
C56 C 0.3646(3) 0.9303(3) 0.3187(3) 0.0668(10) Uani 1 1 d . . .
C57 C 0.3666(3) 0.9451(4) 0.4010(3) 0.0865(13) Uani 1 1 d . . .
H57A H 0.4300 0.9410 0.3989 0.104 Uiso 1 1 calc R . .
C58 C 0.2802(4) 0.9647(5) 0.4815(4) 0.118(2) Uani 1 1 d . . .
H58A H 0.2851 0.9720 0.5345 0.142 Uiso 1 1 calc R . .
C59 C 0.1826(4) 0.9743(7) 0.4861(5) 0.158(3) Uani 1 1 d . . .
H59A H 0.1231 0.9879 0.5420 0.190 Uiso 1 1 calc R . .
C60 C 0.1751(4) 0.9637(7) 0.4094(5) 0.157(3) Uani 1 1 d . . .
H60A H 0.1095 0.9730 0.4122 0.189 Uiso 1 1 calc R . .
C61 C 0.2640(3) 0.9391(5) 0.3254(4) 0.0994(17) Uani 1 1 d . . .
C62 C 0.2578(4) 0.9261(5) 0.2454(4) 0.1109(19) Uani 1 1 d . . .
C63 C 0.3491(3) 0.8921(4) 0.1676(3) 0.0844(13) Uani 1 1 d . . .
C64 C 0.3469(4) 0.8658(5) 0.0927(4) 0.1064(18) Uani 1 1 d . . .
H64A H 0.2833 0.8678 0.0972 0.128 Uiso 1 1 calc R . .
C65 C 0.4338(4) 0.8383(5) 0.0157(4) 0.1023(17) Uani 1 1 d . . .
H65A H 0.4316 0.8158 -0.0291 0.123 Uiso 1 1 calc R . .
C66 C 0.5284(4) 0.8436(4) 0.0032(3) 0.0954(15) Uani 1 1 d . . .
H66A H 0.5874 0.8292 -0.0529 0.115 Uiso 1 1 calc R . .
C67 C 0.5347(3) 0.8692(3) 0.0714(3) 0.0715(10) Uani 1 1 d . . .
H67A H 0.5973 0.8745 0.0604 0.086 Uiso 1 1 calc R . .
C68 C 0.4481(3) 0.8881(3) 0.1591(3) 0.0591(8) Uani 1 1 d . . .
C69 C 0.1464(4) 0.9579(4) 0.2441(4) 0.0877(13) Uani 1 1 d . . .
C70 C 0.0949(4) 1.0373(4) 0.2021(5) 0.1077(18) Uani 1 1 d . . .
H70A H 0.1311 1.0819 0.1623 0.129 Uiso 1 1 calc R . .
C71 C -0.0066(4) 1.0722(3) 0.2031(4) 0.0859(13) Uani 1 1 d . . .
H71A H -0.0359 1.1368 0.1711 0.103 Uiso 1 1 calc R . .
C72 C -0.0635(5) 1.0062(5) 0.2545(4) 0.114(2) Uani 1 1 d . . .
H72A H -0.1318 1.0242 0.2582 0.137 Uiso 1 1 calc R . .
C73 C -0.0037(3) 0.8999(4) 0.3053(3) 0.0823(13) Uani 1 1 d . . .
C74 C 0.0943(3) 0.8913(3) 0.2926(3) 0.0687(10) Uani 1 1 d . . .
C75 C 0.1477(6) 0.7872(6) 0.3495(6) 0.149(3) Uani 1 1 d . . .
H75A H 0.2133 0.7704 0.3516 0.179 Uiso 1 1 calc R . .
C76 C 0.0945(6) 0.7211(5) 0.3963(8) 0.181(4) Uani 1 1 d . . .
H76A H 0.1242 0.6577 0.4302 0.217 Uiso 1 1 calc R . .
C77 C 0.0031(8) 0.7473(7) 0.3929(9) 0.189(5) Uani 1 1 d . . .
H77A H -0.0256 0.6974 0.4186 0.227 Uiso 1 1 calc R . .
C78 C -0.0543(7) 0.8350(9) 0.3582(6) 0.163(3) Uani 1 1 d . . .
H78A H -0.1246 0.8508 0.3694 0.196 Uiso 1 1 calc R . .
C79 C 0.544(2) 0.433(2) 0.587(2) 0.234(10) Uiso 0.50 1 d P . .
H79A H 0.4766 0.4608 0.6349 0.280 Uiso 0.50 1 calc PR . .
H79B H 0.5361 0.4632 0.5232 0.280 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.6223(6) 0.4810(6) 0.5834(9) 0.296(5) Uani 0.50 1 d P . .
Cl2 Cl 0.5544(6) 0.3348(5) 0.6070(7) 0.277(4) Uani 0.50 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.094(6) 0.234(11) 0.124(6) -0.046(7) -0.053(5) 0.014(6)
C2 0.086(5) 0.315(16) 0.222(11) -0.075(11) -0.054(6) -0.052(8)
C3 0.079(4) 0.275(11) 0.156(6) -0.047(6) -0.049(4) -0.042(5)
C4 0.068(3) 0.132(5) 0.103(4) -0.022(3) -0.034(3) -0.030(3)
C5 0.076(3) 0.137(5) 0.091(3) -0.040(3) -0.038(3) 0.006(3)
C6 0.085(4) 0.145(6) 0.096(4) -0.046(4) -0.043(3) 0.032(4)
C7 0.114(6) 0.260(14) 0.153(7) -0.104(9) -0.070(6) 0.041(8)
C8 0.293(14) 0.066(4) 0.186(8) -0.046(4) -0.124(9) 0.039(6)
C9 0.128(4) 0.050(3) 0.134(4) -0.032(3) -0.054(4) 0.008(3)
C10 0.081(3) 0.082(3) 0.086(3) -0.024(2) -0.036(2) 0.011(2)
C11 0.052(2) 0.054(2) 0.082(3) -0.0217(18) -0.0257(19) -0.0021(16)
C12 0.0498(18) 0.055(2) 0.073(2) -0.0106(17) -0.0272(17) -0.0148(15)
C13 0.070(2) 0.068(2) 0.078(3) -0.008(2) -0.037(2) -0.0108(19)
C14 0.080(3) 0.089(3) 0.073(3) -0.003(2) -0.041(2) -0.022(2)
C15 0.066(2) 0.099(3) 0.067(2) -0.025(2) -0.0200(19) -0.023(2)
C16 0.0501(19) 0.069(2) 0.066(2) -0.0207(18) -0.0189(17) -0.0144(16)
C17 0.0413(16) 0.0533(18) 0.0628(19) -0.0153(15) -0.0175(14) -0.0176(14)
C18 0.0408(15) 0.0420(16) 0.0630(19) -0.0148(14) -0.0208(14) -0.0147(13)
C19 0.0423(16) 0.0410(16) 0.0630(19) -0.0125(14) -0.0184(14) -0.0172(13)
C20 0.061(2) 0.0494(19) 0.071(2) -0.0128(16) -0.0273(18) -0.0167(16)
C21 0.080(3) 0.067(2) 0.061(2) -0.0150(18) -0.0225(19) -0.029(2)
C22 0.070(2) 0.066(2) 0.070(2) -0.0287(19) -0.0109(19) -0.0256(19)
C23 0.051(2) 0.058(2) 0.082(3) -0.0295(19) -0.0157(18) -0.0081(16)
C24 0.0473(18) 0.0469(18) 0.069(2) -0.0193(16) -0.0154(16) -0.0133(14)
C25 0.0397(15) 0.0450(17) 0.0591(18) -0.0153(14) -0.0196(13) -0.0135(13)
C26 0.0459(17) 0.0482(18) 0.070(2) -0.0185(15) -0.0221(15) -0.0165(14)
C27 0.0413(16) 0.0534(18) 0.0620(19) -0.0166(15) -0.0211(14) -0.0163(14)
C28 0.0396(16) 0.0439(17) 0.069(2) -0.0177(15) -0.0230(14) -0.0075(13)
C29 0.0445(16) 0.0422(16) 0.0634(19) -0.0162(14) -0.0198(14) -0.0141(13)
C30 0.0380(15) 0.0515(18) 0.0634(19) -0.0183(15) -0.0207(14) -0.0134(13)
C31 0.0393(15) 0.0409(16) 0.071(2) -0.0164(15) -0.0247(15) -0.0089(13)
C32 0.0392(16) 0.0458(17) 0.077(2) -0.0215(16) -0.0202(15) -0.0096(13)
C33 0.056(2) 0.056(2) 0.072(2) -0.0178(17) -0.0182(17) -0.0207(16)
C34 0.062(2) 0.074(3) 0.076(2) -0.026(2) -0.0110(19) -0.0265(19)
C35 0.058(2) 0.089(3) 0.097(3) -0.056(3) -0.001(2) -0.022(2)
C36 0.058(2) 0.079(3) 0.128(4) -0.064(3) 0.003(2) -0.028(2)
C37 0.0473(19) 0.057(2) 0.102(3) -0.039(2) -0.0105(19) -0.0151(16)
C38 0.053(2) 0.057(2) 0.109(3) -0.043(2) -0.003(2) -0.0219(17)
C39 0.0453(18) 0.0499(19) 0.087(2) -0.0239(18) -0.0151(17) -0.0162(15)
C40 0.061(2) 0.065(2) 0.097(3) -0.028(2) -0.009(2) -0.0327(19)
C41 0.058(2) 0.074(3) 0.083(3) -0.023(2) -0.0097(19) -0.0319(19)
C42 0.063(2) 0.077(3) 0.067(2) -0.0280(19) -0.0170(18) -0.0235(19)
C43 0.0548(19) 0.0556(19) 0.068(2) -0.0198(16) -0.0246(17) -0.0183(16)
C44 0.0417(16) 0.0442(17) 0.072(2) -0.0176(15) -0.0232(15) -0.0115(13)
C45 0.082(3) 0.099(4) 0.149(5) -0.076(4) 0.031(3) -0.050(3)
C46 0.094(3) 0.039(2) 0.119(4) -0.011(2) -0.007(3) -0.015(2)
C47 0.140(6) 0.057(4) 0.247(11) -0.026(5) 0.059(7) -0.035(4)
C48 0.139(7) 0.173(10) 0.275(14) -0.162(11) 0.056(7) -0.084(7)
C49 0.092(4) 0.118(5) 0.216(8) -0.122(6) 0.048(5) -0.066(4)
C50 0.077(3) 0.132(5) 0.196(7) -0.123(6) 0.048(4) -0.064(4)
C51 0.081(3) 0.101(4) 0.114(4) -0.045(3) -0.019(3) -0.045(3)
C52 0.107(5) 0.278(11) 0.267(10) -0.202(9) -0.001(5) -0.087(6)
C53 0.144(7) 0.270(13) 0.241(12) -0.182(11) 0.025(7) -0.125(9)
C54 0.120(6) 0.154(8) 0.202(10) -0.078(7) 0.015(6) -0.083(6)
C55 0.0426(17) 0.061(2) 0.067(2) -0.0182(16) -0.0218(15) -0.0179(14)
C56 0.0462(19) 0.094(3) 0.070(2) -0.028(2) -0.0191(17) -0.0255(18)
C57 0.061(2) 0.140(4) 0.085(3) -0.049(3) -0.020(2) -0.040(2)
C58 0.078(3) 0.220(7) 0.090(3) -0.079(4) -0.010(3) -0.060(4)
C59 0.077(3) 0.338(11) 0.109(4) -0.125(6) 0.012(3) -0.093(5)
C60 0.064(3) 0.341(11) 0.115(4) -0.123(6) 0.009(3) -0.090(5)
C61 0.055(2) 0.185(5) 0.088(3) -0.066(3) -0.009(2) -0.053(3)
C62 0.072(3) 0.206(6) 0.095(3) -0.064(4) -0.013(3) -0.071(4)
C63 0.057(2) 0.144(4) 0.075(3) -0.044(3) -0.017(2) -0.043(2)
C64 0.076(3) 0.190(6) 0.090(3) -0.056(4) -0.028(3) -0.056(3)
C65 0.086(3) 0.170(5) 0.084(3) -0.053(3) -0.031(3) -0.048(3)
C66 0.069(3) 0.149(5) 0.078(3) -0.052(3) -0.018(2) -0.031(3)
C67 0.052(2) 0.096(3) 0.070(2) -0.025(2) -0.0199(18) -0.0250(19)
C68 0.0469(18) 0.070(2) 0.066(2) -0.0177(17) -0.0235(16) -0.0199(16)
C69 0.080(3) 0.097(3) 0.095(3) -0.025(3) -0.039(3) -0.027(3)
C70 0.075(3) 0.116(4) 0.146(5) -0.066(4) -0.070(3) 0.020(3)
C71 0.069(3) 0.071(3) 0.119(4) -0.015(2) -0.049(3) -0.014(2)
C72 0.104(4) 0.161(5) 0.095(4) -0.069(4) -0.042(3) -0.018(4)
C73 0.054(2) 0.136(4) 0.078(3) -0.035(3) -0.021(2) -0.042(2)
C74 0.050(2) 0.083(3) 0.089(3) -0.031(2) -0.0256(19) -0.0245(19)
C75 0.150(6) 0.156(6) 0.190(7) -0.005(5) -0.112(6) -0.067(5)
C76 0.141(6) 0.114(5) 0.290(11) 0.070(6) -0.128(7) -0.091(5)
C77 0.197(9) 0.122(6) 0.326(14) -0.020(7) -0.191(11) -0.040(6)
C78 0.135(6) 0.251(11) 0.172(7) -0.050(7) -0.050(5) -0.124(7)
Cl1 0.192(5) 0.227(7) 0.519(15) -0.230(9) -0.095(7) -0.020(5)
Cl2 0.230(7) 0.148(5) 0.375(11) -0.013(5) -0.058(7) -0.097(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.337(13) . ?
C1 C2 1.423(15) . ?
C1 H1A 0.9300 . ?
C2 C3 1.358(15) . ?
C2 H2A 0.9300 . ?
C3 C4 1.344(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(8) . ?
C4 H4A 0.9300 . ?
C5 C10 1.350(8) . ?
C5 C6 1.438(8) . ?
C6 C7 1.416(14) . ?
C7 C8 1.407(16) . ?
C7 H7A 0.9300 . ?
C8 C9 1.407(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.446(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.509(5) . ?
C11 C24 1.396(5) . ?
C11 C12 1.416(5) . ?
C12 C13 1.410(5) . ?
C12 C17 1.438(5) . ?
C13 C14 1.347(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.396(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.355(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.422(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.392(4) . ?
C18 C19 1.407(4) . ?
C18 C25 1.503(4) . ?
C19 C20 1.405(5) . ?
C19 C24 1.449(4) . ?
C20 C21 1.359(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.413(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.345(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.427(5) . ?
C23 H23A 0.9300 . ?
C25 C26 1.394(4) . ?
C25 C30 1.397(4) . ?
C26 C27 1.393(4) . ?
C26 H26A 0.9300 . ?
C27 C28 1.395(4) . ?
C27 C55 1.484(4) . ?
C28 C29 1.398(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.374(4) . ?
C29 C31 1.498(4) . ?
C30 H30A 0.9300 . ?
C31 C32 1.401(5) . ?
C31 C44 1.415(5) . ?
C32 C33 1.424(5) . ?
C32 C37 1.432(5) . ?
C33 C34 1.352(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.397(6) . ?
C34 H34A 0.9300 . ?
C35 C36 1.361(6) . ?
C35 H35A 0.9300 . ?
C36 C37 1.418(6) . ?
C36 H36A 0.9300 . ?
C37 C38 1.424(5) . ?
C38 C39 1.395(5) . ?
C38 C45 1.509(6) . ?
C39 C40 1.428(5) . ?
C39 C44 1.438(4) . ?
C40 C41 1.339(6) . ?
C40 H40A 0.9300 . ?
C41 C42 1.405(5) . ?
C41 H41A 0.9300 . ?
C42 C43 1.349(5) . ?
C42 H42A 0.9300 . ?
C43 C44 1.429(5) . ?
C43 H43A 0.9300 . ?
C45 C50 1.354(10) . ?
C45 C46 1.438(9) . ?
C46 C47 1.442(10) . ?
C46 H46A 0.9300 . ?
C47 C48 1.374(18) . ?
C47 H47A 0.9300 . ?
C48 C49 1.448(16) . ?
C48 H48A 0.9300 . ?
C49 C54 1.301(14) . ?
C49 C50 1.408(8) . ?
C50 C51 1.435(10) . ?
C51 C52 1.319(8) . ?
C51 H51A 0.9300 . ?
C52 C53 1.334(13) . ?
C52 H52A 0.9300 . ?
C53 C54 1.389(14) . ?
C53 H53A 0.9300 . ?
C54 H54A 0.9300 . ?
C55 C56 1.401(5) . ?
C55 C68 1.411(5) . ?
C56 C57 1.426(5) . ?
C56 C61 1.440(5) . ?
C57 C58 1.344(6) . ?
C57 H57A 0.9300 . ?
C58 C59 1.403(7) . ?
C58 H58A 0.9300 . ?
C59 C60 1.348(8) . ?
C59 H59A 0.9300 . ?
C60 C61 1.407(7) . ?
C60 H60A 0.9300 . ?
C61 C62 1.410(6) . ?
C62 C63 1.400(6) . ?
C62 C69 1.552(6) . ?
C63 C64 1.421(6) . ?
C63 C68 1.434(5) . ?
C64 C65 1.340(7) . ?
C64 H64A 0.9300 . ?
C65 C66 1.408(6) . ?
C65 H65A 0.9300 . ?
C66 C67 1.348(6) . ?
C66 H66A 0.9300 . ?
C67 C68 1.411(5) . ?
C67 H67A 0.9300 . ?
C69 C70 1.239(7) . ?
C69 C74 1.365(6) . ?
C70 C71 1.385(6) . ?
C70 H70A 0.9300 . ?
C71 C72 1.406(8) . ?
C71 H71A 0.9300 . ?
C72 C73 1.570(8) . ?
C72 H72A 0.9300 . ?
C73 C78 1.329(9) . ?
C73 C74 1.366(5) . ?
C74 C75 1.554(8) . ?
C75 C76 1.371(9) . ?
C75 H75A 0.9300 . ?
C76 C77 1.288(10) . ?
C76 H76A 0.9300 . ?
C77 C78 1.302(11) . ?
C77 H77A 0.9300 . ?
C78 H78A 0.9300 . ?
C79 Cl2 1.39(3) . ?
C79 Cl1 1.65(3) . ?
C79 H79A 0.9700 . ?
C79 H79B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.1(9) . . ?
C6 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C3 C2 C1 115.0(9) . . ?
C3 C2 H2A 122.5 . . ?
C1 C2 H2A 122.5 . . ?
C4 C3 C2 125.5(11) . . ?
C4 C3 H3A 117.2 . . ?
C2 C3 H3A 117.2 . . ?
C3 C4 C5 119.9(7) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C10 C5 C4 121.6(5) . . ?
C10 C5 C6 121.9(8) . . ?
C4 C5 C6 116.5(7) . . ?
C1 C6 C7 120.9(8) . . ?
C1 C6 C5 120.9(10) . . ?
C7 C6 C5 118.2(9) . . ?
C6 C7 C8 121.3(9) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C9 C8 C7 118.4(10) . . ?
C9 C8 H8A 120.8 . . ?
C7 C8 H8A 120.8 . . ?
C8 C9 C10 121.1(8) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C5 C10 C9 119.0(5) . . ?
C5 C10 C11 121.2(5) . . ?
C9 C10 C11 119.7(5) . . ?
C24 C11 C12 120.6(3) . . ?
C24 C11 C10 120.4(3) . . ?
C12 C11 C10 119.0(3) . . ?
C13 C12 C11 122.8(3) . . ?
C13 C12 C17 118.2(3) . . ?
C11 C12 C17 119.0(3) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 121.6(4) . . ?
C13 C14 H14A 119.2 . . ?
C15 C14 H14A 119.2 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C15 C16 C17 122.0(4) . . ?
C15 C16 H16A 119.0 . . ?
C17 C16 H16A 119.0 . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 C12 120.5(3) . . ?
C16 C17 C12 117.6(3) . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 C25 119.7(3) . . ?
C19 C18 C25 119.6(3) . . ?
C20 C19 C18 122.7(3) . . ?
C20 C19 C24 118.2(3) . . ?
C18 C19 C24 119.1(3) . . ?
C21 C20 C19 121.6(3) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C23 C22 C21 120.2(4) . . ?
C23 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C24 121.7(3) . . ?
C22 C23 H23A 119.2 . . ?
C24 C23 H23A 119.2 . . ?
C11 C24 C23 122.2(3) . . ?
C11 C24 C19 120.0(3) . . ?
C23 C24 C19 117.8(3) . . ?
C26 C25 C30 118.8(3) . . ?
C26 C25 C18 120.8(3) . . ?
C30 C25 C18 120.5(2) . . ?
C25 C26 C27 120.8(3) . . ?
C25 C26 H26A 119.6 . . ?
C27 C26 H26A 119.6 . . ?
C26 C27 C28 118.8(3) . . ?
C26 C27 C55 120.8(3) . . ?
C28 C27 C55 120.4(3) . . ?
C27 C28 C29 121.3(3) . . ?
C27 C28 H28A 119.4 . . ?
C29 C28 H28A 119.4 . . ?
C30 C29 C28 118.5(3) . . ?
C30 C29 C31 121.5(3) . . ?
C28 C29 C31 119.9(3) . . ?
C29 C30 C25 121.8(3) . . ?
C29 C30 H30A 119.1 . . ?
C25 C30 H30A 119.1 . . ?
C32 C31 C44 120.0(3) . . ?
C32 C31 C29 120.0(3) . . ?
C44 C31 C29 120.0(3) . . ?
C31 C32 C33 122.8(3) . . ?
C31 C32 C37 120.1(3) . . ?
C33 C32 C37 117.1(3) . . ?
C34 C33 C32 122.1(3) . . ?
C34 C33 H33A 118.9 . . ?
C32 C33 H33A 118.9 . . ?
C33 C34 C35 120.5(4) . . ?
C33 C34 H34A 119.8 . . ?
C35 C34 H34A 119.8 . . ?
C36 C35 C34 120.1(4) . . ?
C36 C35 H35A 120.0 . . ?
C34 C35 H35A 120.0 . . ?
C35 C36 C37 121.3(4) . . ?
C35 C36 H36A 119.4 . . ?
C37 C36 H36A 119.4 . . ?
C36 C37 C38 121.3(3) . . ?
C36 C37 C32 118.8(3) . . ?
C38 C37 C32 119.8(3) . . ?
C39 C38 C37 120.0(3) . . ?
C39 C38 C45 119.5(4) . . ?
C37 C38 C45 120.4(3) . . ?
C38 C39 C40 122.0(3) . . ?
C38 C39 C44 120.0(3) . . ?
C40 C39 C44 118.0(3) . . ?
C41 C40 C39 121.9(3) . . ?
C41 C40 H40A 119.0 . . ?
C39 C40 H40A 119.0 . . ?
C40 C41 C42 120.4(4) . . ?
C40 C41 H41A 119.8 . . ?
C42 C41 H41A 119.8 . . ?
C43 C42 C41 120.3(3) . . ?
C43 C42 H42A 119.8 . . ?
C41 C42 H42A 119.8 . . ?
C42 C43 C44 121.9(3) . . ?
C42 C43 H43A 119.0 . . ?
C44 C43 H43A 119.0 . . ?
C31 C44 C43 122.8(3) . . ?
C31 C44 C39 120.0(3) . . ?
C43 C44 C39 117.3(3) . . ?
C50 C45 C46 118.2(6) . . ?
C50 C45 C38 122.2(7) . . ?
C46 C45 C38 119.6(6) . . ?
C45 C46 C47 120.1(8) . . ?
C45 C46 H46A 120.0 . . ?
C47 C46 H46A 120.0 . . ?
C48 C47 C46 122.6(12) . . ?
C48 C47 H47A 118.7 . . ?
C46 C47 H47A 118.7 . . ?
C47 C48 C49 114.7(9) . . ?
C47 C48 H48A 122.6 . . ?
C49 C48 H48A 122.6 . . ?
C54 C49 C50 121.8(12) . . ?
C54 C49 C48 114.8(8) . . ?
C50 C49 C48 123.4(10) . . ?
C45 C50 C49 121.0(10) . . ?
C45 C50 C51 120.5(5) . . ?
C49 C50 C51 118.5(9) . . ?
C52 C51 C50 112.4(8) . . ?
C52 C51 H51A 123.8 . . ?
C50 C51 H51A 123.8 . . ?
C51 C52 C53 131.8(12) . . ?
C51 C52 H52A 114.1 . . ?
C53 C52 H52A 114.1 . . ?
C52 C53 C54 113.4(10) . . ?
C52 C53 H53A 123.3 . . ?
C54 C53 H53A 123.3 . . ?
C49 C54 C53 121.8(11) . . ?
C49 C54 H54A 119.1 . . ?
C53 C54 H54A 119.1 . . ?
C56 C55 C68 120.1(3) . . ?
C56 C55 C27 119.8(3) . . ?
C68 C55 C27 120.0(3) . . ?
C55 C56 C57 123.2(3) . . ?
C55 C56 C61 120.4(3) . . ?
C57 C56 C61 116.4(3) . . ?
C58 C57 C56 122.4(4) . . ?
C58 C57 H57A 118.8 . . ?
C56 C57 H57A 118.8 . . ?
C57 C58 C59 120.4(4) . . ?
C57 C58 H58A 119.8 . . ?
C59 C58 H58A 119.8 . . ?
C60 C59 C58 120.0(5) . . ?
C60 C59 H59A 120.0 . . ?
C58 C59 H59A 120.0 . . ?
C59 C60 C61 121.7(5) . . ?
C59 C60 H60A 119.2 . . ?
C61 C60 H60A 119.2 . . ?
C60 C61 C62 122.4(4) . . ?
C60 C61 C56 119.0(4) . . ?
C62 C61 C56 118.5(4) . . ?
C63 C62 C61 120.6(4) . . ?
C63 C62 C69 122.0(4) . . ?
C61 C62 C69 117.2(4) . . ?
C62 C63 C64 122.2(4) . . ?
C62 C63 C68 119.8(4) . . ?
C64 C63 C68 118.0(4) . . ?
C65 C64 C63 121.8(4) . . ?
C65 C64 H64A 119.1 . . ?
C63 C64 H64A 119.1 . . ?
C64 C65 C66 119.6(4) . . ?
C64 C65 H65A 120.2 . . ?
C66 C65 H65A 120.2 . . ?
C67 C66 C65 120.8(4) . . ?
C67 C66 H66A 119.6 . . ?
C65 C66 H66A 119.6 . . ?
C66 C67 C68 121.3(4) . . ?
C66 C67 H67A 119.3 . . ?
C68 C67 H67A 119.3 . . ?
C55 C68 C67 122.6(3) . . ?
C55 C68 C63 119.4(3) . . ?
C67 C68 C63 117.8(3) . . ?
C70 C69 C74 111.8(5) . . ?
C70 C69 C62 129.5(5) . . ?
C74 C69 C62 118.8(5) . . ?
C69 C70 C71 132.1(7) . . ?
C69 C70 H70A 114.0 . . ?
C71 C70 H70A 114.0 . . ?
C70 C71 C72 117.4(5) . . ?
C70 C71 H71A 121.3 . . ?
C72 C71 H71A 121.3 . . ?
C71 C72 C73 115.4(5) . . ?
C71 C72 H72A 122.3 . . ?
C73 C72 H72A 122.3 . . ?
C78 C73 C74 129.3(6) . . ?
C78 C73 C72 118.5(6) . . ?
C74 C73 C72 112.1(4) . . ?
C69 C74 C73 131.0(4) . . ?
C69 C74 C75 118.7(4) . . ?
C73 C74 C75 110.2(4) . . ?
C76 C75 C74 117.5(6) . . ?
C76 C75 H75A 121.2 . . ?
C74 C75 H75A 121.2 . . ?
C77 C76 C75 119.6(7) . . ?
C77 C76 H76A 120.2 . . ?
C75 C76 H76A 120.2 . . ?
C76 C77 C78 128.2(9) . . ?
C76 C77 H77A 115.9 . . ?
C78 C77 H77A 115.9 . . ?
C77 C78 C73 114.3(8) . . ?
C77 C78 H78A 122.9 . . ?
C73 C78 H78A 122.9 . . ?
Cl2 C79 Cl1 130.5(19) . . ?
Cl2 C79 H79A 104.7 . . ?
Cl1 C79 H79A 104.7 . . ?
Cl2 C79 H79B 104.6 . . ?
Cl1 C79 H79B 104.7 . . ?
H79A C79 H79B 105.7 . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.057