# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Chuluo Yang'
_publ_contact_author_email       CLYANG@WHU.EDU.CN

_publ_section_title              
;
Aryl-bridged 4,4'-(bis(9-carbazolyl))biphenyl:
Morphological Stable Host Material for Highly Efficient Electrophosphorescence
;
loop_
_publ_author_name
'Chuluo Yang.'
'Zucheng Jiang.'
'Zhongyin Liu.'
'Dong-ge Ma.'
'Jingui Qin.'
;
Youtian Tao
;
'Zhiqiang Zhang.'

# Attachment 'CCDC-732327.cif.cif'

data_81021ycl_0m
_database_code_depnum_ccdc_archive 'CCDC 732327'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C51 H36 N2), C H2 Cl2, C2 H5 OH '
_chemical_formula_sum            'C105 H80 Cl2 N4 O'
_chemical_formula_weight         1484.69

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'
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                   10.1508(11)
_cell_length_b                   12.2571(13)
_cell_length_c                   16.6606(18)
_cell_angle_alpha                79.161(2)
_cell_angle_beta                 77.551(2)
_cell_angle_gamma                88.507(2)
_cell_volume                     1987.8(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10775
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6918
_reflns_number_gt                5168
_reflns_threshold_expression     >2sigma(I)

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

_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. During the refinement, the
CH~2~Cl~2~ and C~2~H~5~OH solvent molecules were both disordered and DFIX
and ISOR commands were used to restrain some related bond lengths and thermal
factors.
;

_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^)+(0.2000P)^2^] 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         6918
_refine_ls_number_parameters     525
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.3095
_refine_ls_wR_factor_gt          0.2842
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_restrained_S_all      1.291
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1693(3) 0.8305(3) 0.18290(19) 0.0445(8) Uani 1 1 d . . .
C2 C 1.0900(4) 0.8722(3) 0.2478(2) 0.0602(10) Uani 1 1 d . . .
H2 H 1.0041 0.8432 0.2730 0.072 Uiso 1 1 calc R . .
C3 C 1.1426(5) 0.9587(4) 0.2741(3) 0.0773(13) Uani 1 1 d . . .
H3 H 1.0911 0.9880 0.3182 0.093 Uiso 1 1 calc R . .
C4 C 1.2703(5) 1.0031(4) 0.2365(3) 0.0785(13) Uani 1 1 d . . .
H4 H 1.3030 1.0615 0.2554 0.094 Uiso 1 1 calc R . .
C5 C 1.3473(4) 0.9618(3) 0.1724(2) 0.0655(11) Uani 1 1 d . . .
H5 H 1.4328 0.9917 0.1473 0.079 Uiso 1 1 calc R . .
C6 C 1.2981(3) 0.8739(3) 0.1439(2) 0.0469(8) Uani 1 1 d . . .
C7 C 1.3499(3) 0.8137(3) 0.0779(2) 0.0476(8) Uani 1 1 d . . .
C8 C 1.4721(4) 0.8193(3) 0.0187(2) 0.0632(10) Uani 1 1 d . . .
H8 H 1.5392 0.8702 0.0174 0.076 Uiso 1 1 calc R . .
C9 C 1.4906(5) 0.7482(4) -0.0374(3) 0.0766(13) Uani 1 1 d . . .
H9 H 1.5713 0.7506 -0.0768 0.092 Uiso 1 1 calc R . .
C10 C 1.3884(5) 0.6715(3) -0.0357(2) 0.0685(11) Uani 1 1 d . . .
H10 H 1.4034 0.6237 -0.0739 0.082 Uiso 1 1 calc R . .
C11 C 1.2666(4) 0.6657(3) 0.0212(2) 0.0559(9) Uani 1 1 d . . .
H11 H 1.1988 0.6159 0.0216 0.067 Uiso 1 1 calc R . .
C12 C 1.2496(3) 0.7377(3) 0.07825(19) 0.0433(7) Uani 1 1 d . . .
C13 C 1.0158(3) 0.6866(2) 0.16221(19) 0.0424(7) Uani 1 1 d . . .
C14 C 0.9403(3) 0.6888(3) 0.1010(2) 0.0468(8) Uani 1 1 d . . .
H14 H 0.9719 0.7290 0.0473 0.056 Uiso 1 1 calc R . .
C15 C 0.8187(3) 0.6315(3) 0.12027(18) 0.0450(8) Uani 1 1 d . . .
H15 H 0.7706 0.6315 0.0786 0.054 Uiso 1 1 calc R . .
C16 C 0.7665(3) 0.5733(2) 0.20136(18) 0.0382(7) Uani 1 1 d . . .
C17 C 0.8426(3) 0.5731(3) 0.26077(19) 0.0485(8) Uani 1 1 d . . .
H17 H 0.8102 0.5353 0.3151 0.058 Uiso 1 1 calc R . .
C18 C 0.9664(4) 0.6280(3) 0.2410(2) 0.0522(9) Uani 1 1 d . . .
H18 H 1.0165 0.6249 0.2820 0.063 Uiso 1 1 calc R . .
C19 C 0.6348(3) 0.5140(2) 0.22056(18) 0.0368(7) Uani 1 1 d . . .
C20 C 0.5352(3) 0.5491(2) 0.17569(18) 0.0410(7) Uani 1 1 d . . .
H20 H 0.5488 0.6141 0.1356 0.049 Uiso 1 1 calc R . .
C21 C 0.4167(3) 0.4886(2) 0.19011(18) 0.0410(7) Uani 1 1 d . . .
H21 H 0.3511 0.5139 0.1600 0.049 Uiso 1 1 calc R . .
C22 C 0.3939(3) 0.3904(2) 0.24905(17) 0.0355(7) Uani 1 1 d . . .
C23 C 0.4874(3) 0.3575(2) 0.30011(17) 0.0346(7) Uani 1 1 d . . .
C24 C 0.6056(3) 0.4196(2) 0.28361(17) 0.0364(7) Uani 1 1 d . . .
H24 H 0.6688 0.3973 0.3162 0.044 Uiso 1 1 calc R . .
C25 C 0.1691(3) 0.3339(3) 0.22094(19) 0.0416(7) Uani 1 1 d . . .
C26 C 0.1629(3) 0.3859(3) 0.1392(2) 0.0493(8) Uani 1 1 d . . .
H26 H 0.2363 0.4253 0.1032 0.059 Uiso 1 1 calc R . .
C27 C 0.0435(4) 0.3759(3) 0.1149(2) 0.0594(10) Uani 1 1 d . . .
H27 H 0.0363 0.4105 0.0614 0.071 Uiso 1 1 calc R . .
C28 C -0.0658(4) 0.3168(4) 0.1664(2) 0.0644(10) Uani 1 1 d . . .
H28 H -0.1448 0.3130 0.1473 0.077 Uiso 1 1 calc R . .
C29 C -0.0597(4) 0.2628(3) 0.2461(2) 0.0594(9) Uani 1 1 d . . .
H29 H -0.1329 0.2211 0.2802 0.071 Uiso 1 1 calc R . .
C30 C 0.0582(3) 0.2723(3) 0.2742(2) 0.0458(8) Uani 1 1 d . . .
C31 C 0.0997(3) 0.2244(3) 0.3516(2) 0.0445(7) Uani 1 1 d . . .
C32 C 0.0386(4) 0.1582(3) 0.4266(2) 0.0560(9) Uani 1 1 d . . .
H32 H -0.0508 0.1346 0.4364 0.067 Uiso 1 1 calc R . .
C33 C 0.1154(4) 0.1282(3) 0.4871(2) 0.0626(10) Uani 1 1 d . . .
H33 H 0.0755 0.0854 0.5385 0.075 Uiso 1 1 calc R . .
C34 C 0.2499(4) 0.1607(3) 0.4726(2) 0.0525(9) Uani 1 1 d . . .
H34 H 0.2977 0.1395 0.5146 0.063 Uiso 1 1 calc R . .
C35 C 0.3145(3) 0.2241(2) 0.39680(18) 0.0404(7) Uani 1 1 d . . .
C36 C 0.2347(3) 0.2565(2) 0.33998(18) 0.0388(7) Uani 1 1 d . . .
C37 C 0.4662(3) 0.2502(2) 0.36767(17) 0.0361(7) Uani 1 1 d . . .
C38 C 0.5265(3) 0.2682(2) 0.44167(17) 0.0382(7) Uani 1 1 d . . .
C39 C 0.6412(3) 0.2174(3) 0.46044(19) 0.0503(8) Uani 1 1 d . . .
H39 H 0.6863 0.1683 0.4280 0.060 Uiso 1 1 calc R . .
C40 C 0.6906(4) 0.2393(3) 0.5281(2) 0.0582(10) Uani 1 1 d . . .
H40 H 0.7684 0.2040 0.5398 0.070 Uiso 1 1 calc R . .
C41 C 0.6282(4) 0.3111(3) 0.5778(2) 0.0547(9) Uani 1 1 d . . .
C42 C 0.5133(4) 0.3617(3) 0.5583(2) 0.0532(9) Uani 1 1 d . . .
H42 H 0.4683 0.4106 0.5909 0.064 Uiso 1 1 calc R . .
C43 C 0.4636(4) 0.3414(3) 0.4915(2) 0.0478(8) Uani 1 1 d . . .
H43 H 0.3865 0.3776 0.4797 0.057 Uiso 1 1 calc R . .
C44 C 0.5304(3) 0.1509(2) 0.32860(17) 0.0373(7) Uani 1 1 d . . .
C45 C 0.5140(4) 0.0433(3) 0.3761(2) 0.0539(9) Uani 1 1 d . . .
H45 H 0.4664 0.0323 0.4314 0.065 Uiso 1 1 calc R . .
C46 C 0.5676(4) -0.0470(3) 0.3420(2) 0.0609(10) Uani 1 1 d . . .
H46 H 0.5558 -0.1177 0.3749 0.073 Uiso 1 1 calc R . .
C47 C 0.6386(4) -0.0343(3) 0.2597(3) 0.0579(10) Uani 1 1 d . . .
C48 C 0.6548(4) 0.0713(3) 0.2140(2) 0.0576(9) Uani 1 1 d . . .
H48 H 0.7034 0.0823 0.1589 0.069 Uiso 1 1 calc R . .
C49 C 0.6013(3) 0.1625(3) 0.24709(19) 0.0444(7) Uani 1 1 d . . .
H49 H 0.6134 0.2328 0.2136 0.053 Uiso 1 1 calc R . .
C50 C 0.6891(6) -0.1341(4) 0.2224(4) 0.0939(16) Uani 1 1 d . . .
H50A H 0.6152 -0.1703 0.2100 0.141 Uiso 1 1 calc R . .
H50B H 0.7288 -0.1849 0.2615 0.141 Uiso 1 1 calc R . .
H50C H 0.7557 -0.1109 0.1718 0.141 Uiso 1 1 calc R . .
C51 C 0.6792(5) 0.3322(5) 0.6518(3) 0.0869(15) Uani 1 1 d . . .
H51A H 0.6397 0.2787 0.7004 0.130 Uiso 1 1 calc R . .
H51B H 0.6549 0.4057 0.6613 0.130 Uiso 1 1 calc R . .
H51C H 0.7756 0.3259 0.6408 0.130 Uiso 1 1 calc R . .
C52 C 0.9324(9) 1.0003(6) 0.9804(5) 0.152(3) Uani 0.50 1 d PDU . .
C53 C 0.9324(9) 1.0003(6) 0.9804(5) 0.152(3) Uani 0.50 1 d PDU . .
C54 C -0.0118(14) 0.4509(10) 0.4520(8) 0.124(4) Uani 0.50 1 d PDU . .
Cl1 Cl 0.0873(3) 0.4139(3) 0.52699(17) 0.1913(12) Uani 1 1 d D . .
N1 N 1.1404(3) 0.7460(2) 0.14286(16) 0.0451(7) Uani 1 1 d . . .
N2 N 0.2771(2) 0.3249(2) 0.26224(15) 0.0390(6) Uani 1 1 d . . .
O1 O 0.8507(12) 0.9091(7) 0.9635(8) 0.089(4) Uani 0.25 1 d PDU . .
O1' O 0.9810(15) 0.9244(9) 0.9227(5) 0.095(4) Uani 0.25 1 d PDU . .

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 0.0445(19) 0.0440(17) 0.0464(17) -0.0073(14) -0.0123(14) -0.0113(14)
C2 0.057(2) 0.062(2) 0.062(2) -0.0232(18) -0.0014(18) -0.0156(18)
C3 0.090(3) 0.071(3) 0.074(3) -0.032(2) -0.007(2) -0.018(2)
C4 0.085(3) 0.076(3) 0.083(3) -0.034(2) -0.017(3) -0.027(2)
C5 0.058(2) 0.068(2) 0.074(2) -0.011(2) -0.020(2) -0.0266(19)
C6 0.0437(19) 0.0473(18) 0.0499(18) -0.0029(14) -0.0144(15) -0.0114(14)
C7 0.0410(18) 0.0491(18) 0.0483(18) 0.0033(14) -0.0103(14) -0.0049(14)
C8 0.047(2) 0.073(3) 0.058(2) 0.0063(19) -0.0014(17) -0.0084(18)
C9 0.066(3) 0.088(3) 0.059(2) 0.000(2) 0.011(2) 0.011(2)
C10 0.080(3) 0.063(2) 0.054(2) -0.0121(18) 0.003(2) 0.010(2)
C11 0.070(3) 0.0474(19) 0.0475(18) -0.0063(15) -0.0082(17) 0.0006(17)
C12 0.0435(18) 0.0403(16) 0.0415(16) 0.0008(13) -0.0060(13) -0.0026(13)
C13 0.0430(18) 0.0381(16) 0.0455(17) -0.0079(13) -0.0067(14) -0.0105(13)
C14 0.049(2) 0.0468(18) 0.0403(16) -0.0014(13) -0.0043(14) -0.0140(14)
C15 0.051(2) 0.0456(17) 0.0381(16) -0.0036(13) -0.0107(14) -0.0141(14)
C16 0.0426(18) 0.0292(14) 0.0421(16) -0.0041(12) -0.0090(13) -0.0073(12)
C17 0.053(2) 0.0501(18) 0.0399(16) 0.0037(14) -0.0122(15) -0.0168(15)
C18 0.053(2) 0.059(2) 0.0436(17) -0.0007(15) -0.0145(15) -0.0190(16)
C19 0.0381(17) 0.0323(14) 0.0389(15) -0.0066(12) -0.0055(12) -0.0051(12)
C20 0.0468(19) 0.0338(15) 0.0403(15) 0.0008(12) -0.0113(13) -0.0045(13)
C21 0.0392(17) 0.0408(16) 0.0435(16) -0.0030(13) -0.0134(13) -0.0019(13)
C22 0.0331(16) 0.0346(15) 0.0378(14) -0.0062(12) -0.0056(12) -0.0031(12)
C23 0.0374(16) 0.0320(14) 0.0338(14) -0.0037(11) -0.0077(12) -0.0032(12)
C24 0.0374(17) 0.0324(14) 0.0384(15) -0.0026(12) -0.0087(12) -0.0038(12)
C25 0.0358(17) 0.0422(16) 0.0491(17) -0.0097(13) -0.0128(14) 0.0004(13)
C26 0.046(2) 0.0539(19) 0.0510(18) -0.0102(15) -0.0165(15) -0.0038(15)
C27 0.052(2) 0.069(2) 0.063(2) -0.0112(18) -0.0252(18) 0.0025(18)
C28 0.042(2) 0.085(3) 0.072(2) -0.015(2) -0.0245(18) -0.0037(19)
C29 0.0359(19) 0.071(2) 0.075(2) -0.0179(19) -0.0145(17) -0.0071(16)
C30 0.0366(18) 0.0482(18) 0.0542(18) -0.0126(15) -0.0101(14) -0.0010(14)
C31 0.0362(17) 0.0461(17) 0.0504(18) -0.0109(14) -0.0053(14) -0.0044(13)
C32 0.0416(19) 0.060(2) 0.059(2) -0.0045(17) 0.0018(16) -0.0164(16)
C33 0.057(2) 0.065(2) 0.055(2) 0.0030(18) 0.0006(18) -0.0227(18)
C34 0.049(2) 0.054(2) 0.0475(18) 0.0038(15) -0.0073(15) -0.0134(16)
C35 0.0388(17) 0.0389(16) 0.0403(16) -0.0031(12) -0.0043(13) -0.0080(13)
C36 0.0361(17) 0.0356(15) 0.0425(15) -0.0063(12) -0.0041(13) -0.0029(12)
C37 0.0380(16) 0.0329(14) 0.0358(14) -0.0017(12) -0.0083(12) -0.0041(12)
C38 0.0423(18) 0.0341(15) 0.0362(15) -0.0001(12) -0.0089(13) -0.0065(12)
C39 0.050(2) 0.063(2) 0.0421(17) -0.0192(15) -0.0129(15) 0.0115(16)
C40 0.053(2) 0.078(2) 0.0503(19) -0.0205(18) -0.0210(16) 0.0116(18)
C41 0.066(2) 0.058(2) 0.0439(18) -0.0124(15) -0.0164(16) -0.0053(17)
C42 0.072(3) 0.0424(18) 0.0471(18) -0.0140(14) -0.0117(17) 0.0025(16)
C43 0.056(2) 0.0366(16) 0.0517(18) -0.0059(13) -0.0149(15) 0.0033(14)
C44 0.0402(17) 0.0335(15) 0.0404(15) -0.0044(12) -0.0154(13) -0.0030(12)
C45 0.077(3) 0.0366(17) 0.0464(18) 0.0001(14) -0.0155(17) -0.0023(16)
C46 0.077(3) 0.0350(17) 0.073(2) -0.0047(16) -0.026(2) 0.0009(17)
C47 0.056(2) 0.0452(19) 0.081(3) -0.0251(18) -0.0215(19) 0.0069(16)
C48 0.055(2) 0.057(2) 0.059(2) -0.0209(17) 0.0005(17) -0.0030(17)
C49 0.0447(19) 0.0376(16) 0.0487(17) -0.0058(13) -0.0063(14) -0.0042(13)
C50 0.098(4) 0.059(3) 0.133(4) -0.043(3) -0.024(3) 0.022(2)
C51 0.105(4) 0.111(4) 0.064(3) -0.043(3) -0.037(3) 0.016(3)
C52 0.190(6) 0.112(4) 0.165(5) 0.035(4) -0.115(4) 0.003(4)
C53 0.190(6) 0.112(4) 0.165(5) 0.035(4) -0.115(4) 0.003(4)
C54 0.159(9) 0.096(7) 0.132(8) -0.036(6) -0.045(7) -0.025(6)
Cl1 0.191(3) 0.210(3) 0.176(2) -0.0478(19) -0.0466(18) 0.087(2)
N1 0.0448(16) 0.0445(15) 0.0443(14) -0.0091(11) -0.0036(12) -0.0135(12)
N2 0.0332(14) 0.0403(14) 0.0431(13) -0.0041(11) -0.0097(11) -0.0055(10)
O1 0.071(6) 0.068(6) 0.113(7) 0.057(5) -0.057(6) 0.009(5)
O1' 0.115(8) 0.089(7) 0.042(5) 0.043(5) 0.012(5) 0.051(6)

_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 1.374(5) . ?
C1 C6 1.398(4) . ?
C1 N1 1.400(4) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.353(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(5) . ?
C7 C12 1.396(4) . ?
C7 C8 1.402(5) . ?
C8 C9 1.375(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.411(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(5) . ?
C11 H11 0.9300 . ?
C12 N1 1.385(4) . ?
C13 C18 1.368(4) . ?
C13 C14 1.397(4) . ?
C13 N1 1.422(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.401(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 C19 1.482(4) . ?
C17 C18 1.387(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.396(4) . ?
C19 C24 1.399(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(4) . ?
C21 H21 0.9300 . ?
C22 N2 1.404(4) . ?
C22 C23 1.409(4) . ?
C23 C24 1.386(4) . ?
C23 C37 1.548(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.405(4) . ?
C25 N2 1.407(4) . ?
C25 C30 1.409(4) . ?
C26 C27 1.373(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.374(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.381(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.392(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.456(5) . ?
C31 C32 1.384(5) . ?
C31 C36 1.398(4) . ?
C32 C33 1.393(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.390(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.389(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.372(4) . ?
C35 C37 1.534(4) . ?
C36 N2 1.391(4) . ?
C37 C38 1.542(4) . ?
C37 C44 1.550(4) . ?
C38 C39 1.374(4) . ?
C38 C43 1.387(4) . ?
C39 C40 1.399(4) . ?
C39 H39 0.9300 . ?
C40 C41 1.371(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.378(5) . ?
C41 C51 1.502(5) . ?
C42 C43 1.382(5) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 C49 1.376(4) . ?
C44 C45 1.398(4) . ?
C45 C46 1.385(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.386(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.367(5) . ?
C47 C50 1.505(5) . ?
C48 C49 1.385(5) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 O1' 1.464(7) . ?
C52 O1 1.512(7) . ?
C52 C53 1.641(14) 2_777 ?
C52 C52 1.641(14) 2_777 ?
C54 Cl1 1.756(9) . ?
C54 Cl1 1.869(13) 2_566 ?
Cl1 C54 1.869(13) 2_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.8(3) . . ?
C2 C1 N1 129.5(3) . . ?
C6 C1 N1 108.7(3) . . ?
C1 C2 C3 117.5(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 C7 107.0(3) . . ?
C5 C6 C7 134.2(3) . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 C6 106.9(3) . . ?
C8 C7 C6 133.2(3) . . ?
C9 C8 C7 118.7(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 117.2(4) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C11 128.7(3) . . ?
N1 C12 C7 109.3(3) . . ?
C11 C12 C7 122.0(3) . . ?
C18 C13 C14 118.9(3) . . ?
C18 C13 N1 120.9(3) . . ?
C14 C13 N1 120.2(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.6(3) . . ?
C17 C16 C19 122.4(3) . . ?
C15 C16 C19 120.0(3) . . ?
C16 C17 C18 121.3(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 121.0(3) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C24 117.1(3) . . ?
C20 C19 C16 121.4(3) . . ?
C24 C19 C16 121.5(3) . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 N2 122.1(3) . . ?
C21 C22 C23 119.5(3) . . ?
N2 C22 C23 118.4(3) . . ?
C24 C23 C22 117.8(3) . . ?
C24 C23 C37 120.3(2) . . ?
C22 C23 C37 121.8(3) . . ?
C23 C24 C19 123.4(3) . . ?
C23 C24 H24 118.3 . . ?
C19 C24 H24 118.3 . . ?
C26 C25 N2 130.3(3) . . ?
C26 C25 C30 121.0(3) . . ?
N2 C25 C30 108.6(3) . . ?
C27 C26 C25 116.9(3) . . ?
C27 C26 H26 121.5 . . ?
C25 C26 H26 121.5 . . ?
C26 C27 C28 122.7(4) . . ?
C26 C27 H27 118.6 . . ?
C28 C27 H27 118.6 . . ?
C27 C28 C29 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C30 118.5(4) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C29 C30 C25 119.9(3) . . ?
C29 C30 C31 132.7(3) . . ?
C25 C30 C31 107.3(3) . . ?
C32 C31 C36 118.7(3) . . ?
C32 C31 C30 135.3(3) . . ?
C36 C31 C30 105.9(3) . . ?
C31 C32 C33 117.7(3) . . ?
C31 C32 H32 121.1 . . ?
C33 C32 H32 121.1 . . ?
C34 C33 C32 121.8(3) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C35 C34 C33 121.5(3) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C36 C35 C34 115.4(3) . . ?
C36 C35 C37 117.6(3) . . ?
C34 C35 C37 126.7(3) . . ?
C35 C36 N2 124.8(3) . . ?
C35 C36 C31 124.8(3) . . ?
N2 C36 C31 110.4(3) . . ?
C35 C37 C38 110.5(2) . . ?
C35 C37 C23 108.9(2) . . ?
C38 C37 C23 109.0(2) . . ?
C35 C37 C44 106.5(2) . . ?
C38 C37 C44 112.3(2) . . ?
C23 C37 C44 109.6(2) . . ?
C39 C38 C43 117.6(3) . . ?
C39 C38 C37 123.8(3) . . ?
C43 C38 C37 118.6(3) . . ?
C38 C39 C40 120.3(3) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 122.2(3) . . ?
C41 C40 H40 118.9 . . ?
C39 C40 H40 118.9 . . ?
C40 C41 C42 117.0(3) . . ?
C40 C41 C51 122.1(4) . . ?
C42 C41 C51 120.8(3) . . ?
C41 C42 C43 121.5(3) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C38 121.4(3) . . ?
C42 C43 H43 119.3 . . ?
C38 C43 H43 119.3 . . ?
C49 C44 C45 117.1(3) . . ?
C49 C44 C37 123.0(3) . . ?
C45 C44 C37 119.8(3) . . ?
C46 C45 C44 120.9(3) . . ?
C46 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?
C45 C46 C47 121.4(3) . . ?
C45 C46 H46 119.3 . . ?
C47 C46 H46 119.3 . . ?
C48 C47 C46 117.2(3) . . ?
C48 C47 C50 122.2(4) . . ?
C46 C47 C50 120.5(4) . . ?
C47 C48 C49 122.1(3) . . ?
C47 C48 H48 118.9 . . ?
C49 C48 H48 118.9 . . ?
C44 C49 C48 121.2(3) . . ?
C44 C49 H49 119.4 . . ?
C48 C49 H49 119.4 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C41 C51 H51A 109.5 . . ?
C41 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C41 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O1' C52 O1 54.0(7) . . ?
O1' C52 C53 97.2(11) . 2_777 ?
O1 C52 C53 132.9(7) . 2_777 ?
O1' C52 C52 97.2(11) . 2_777 ?
O1 C52 C52 132.9(7) . 2_777 ?
C53 C52 C52 0.0(5) 2_777 2_777 ?
Cl1 C54 Cl1 104.2(5) . 2_566 ?
C54 Cl1 C54 75.8(5) . 2_566 ?
C12 N1 C1 108.1(3) . . ?
C12 N1 C13 126.8(3) . . ?
C1 N1 C13 124.9(3) . . ?
C36 N2 C22 118.1(2) . . ?
C36 N2 C25 107.7(2) . . ?
C22 N2 C25 131.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(6) . . . . ?
N1 C1 C2 C3 -178.2(4) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
N1 C1 C6 C5 178.5(3) . . . . ?
C2 C1 C6 C7 -178.2(3) . . . . ?
N1 C1 C6 C7 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C5 C6 C7 178.1(4) . . . . ?
C1 C6 C7 C12 1.2(4) . . . . ?
C5 C6 C7 C12 -177.1(4) . . . . ?
C1 C6 C7 C8 -179.5(4) . . . . ?
C5 C6 C7 C8 2.2(7) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
C6 C7 C8 C9 -180.0(4) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C10 C11 C12 N1 -177.6(3) . . . . ?
C10 C11 C12 C7 0.7(5) . . . . ?
C8 C7 C12 N1 178.8(3) . . . . ?
C6 C7 C12 N1 -1.8(4) . . . . ?
C8 C7 C12 C11 0.2(5) . . . . ?
C6 C7 C12 C11 179.6(3) . . . . ?
C18 C13 C14 C15 -0.8(5) . . . . ?
N1 C13 C14 C15 -179.6(3) . . . . ?
C13 C14 C15 C16 2.1(5) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C14 C15 C16 C19 179.0(3) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C19 C16 C17 C18 179.2(3) . . . . ?
C14 C13 C18 C17 -1.0(5) . . . . ?
N1 C13 C18 C17 177.8(3) . . . . ?
C16 C17 C18 C13 1.6(5) . . . . ?
C17 C16 C19 C20 152.8(3) . . . . ?
C15 C16 C19 C20 -27.8(4) . . . . ?
C17 C16 C19 C24 -28.1(4) . . . . ?
C15 C16 C19 C24 151.3(3) . . . . ?
C24 C19 C20 C21 -3.8(4) . . . . ?
C16 C19 C20 C21 175.3(3) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C20 C21 C22 N2 -177.1(3) . . . . ?
C20 C21 C22 C23 5.9(4) . . . . ?
C21 C22 C23 C24 -6.2(4) . . . . ?
N2 C22 C23 C24 176.7(2) . . . . ?
C21 C22 C23 C37 179.0(3) . . . . ?
N2 C22 C23 C37 1.9(4) . . . . ?
C22 C23 C24 C19 1.6(4) . . . . ?
C37 C23 C24 C19 176.5(3) . . . . ?
C20 C19 C24 C23 3.4(4) . . . . ?
C16 C19 C24 C23 -175.7(3) . . . . ?
N2 C25 C26 C27 176.7(3) . . . . ?
C30 C25 C26 C27 1.4(5) . . . . ?
C25 C26 C27 C28 -1.0(5) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C28 C29 C30 1.9(6) . . . . ?
C28 C29 C30 C25 -1.4(5) . . . . ?
C28 C29 C30 C31 -177.5(3) . . . . ?
C26 C25 C30 C29 -0.3(5) . . . . ?
N2 C25 C30 C29 -176.5(3) . . . . ?
C26 C25 C30 C31 176.7(3) . . . . ?
N2 C25 C30 C31 0.5(3) . . . . ?
C29 C30 C31 C32 -4.3(7) . . . . ?
C25 C30 C31 C32 179.3(4) . . . . ?
C29 C30 C31 C36 174.5(4) . . . . ?
C25 C30 C31 C36 -1.9(3) . . . . ?
C36 C31 C32 C33 0.7(5) . . . . ?
C30 C31 C32 C33 179.4(4) . . . . ?
C31 C32 C33 C34 -1.6(6) . . . . ?
C32 C33 C34 C35 -0.4(6) . . . . ?
C33 C34 C35 C36 3.3(5) . . . . ?
C33 C34 C35 C37 -169.8(3) . . . . ?
C34 C35 C36 N2 176.5(3) . . . . ?
C37 C35 C36 N2 -9.7(4) . . . . ?
C34 C35 C36 C31 -4.3(5) . . . . ?
C37 C35 C36 C31 169.4(3) . . . . ?
C32 C31 C36 C35 2.4(5) . . . . ?
C30 C31 C36 C35 -176.6(3) . . . . ?
C32 C31 C36 N2 -178.3(3) . . . . ?
C30 C31 C36 N2 2.6(3) . . . . ?
C36 C35 C37 C38 149.8(3) . . . . ?
C34 C35 C37 C38 -37.3(4) . . . . ?
C36 C35 C37 C23 30.1(3) . . . . ?
C34 C35 C37 C23 -156.9(3) . . . . ?
C36 C35 C37 C44 -88.0(3) . . . . ?
C34 C35 C37 C44 85.0(4) . . . . ?
C24 C23 C37 C35 158.3(3) . . . . ?
C22 C23 C37 C35 -26.9(4) . . . . ?
C24 C23 C37 C38 37.7(3) . . . . ?
C22 C23 C37 C38 -147.5(3) . . . . ?
C24 C23 C37 C44 -85.6(3) . . . . ?
C22 C23 C37 C44 89.2(3) . . . . ?
C35 C37 C38 C39 130.9(3) . . . . ?
C23 C37 C38 C39 -109.5(3) . . . . ?
C44 C37 C38 C39 12.2(4) . . . . ?
C35 C37 C38 C43 -50.5(3) . . . . ?
C23 C37 C38 C43 69.1(3) . . . . ?
C44 C37 C38 C43 -169.2(3) . . . . ?
C43 C38 C39 C40 0.5(5) . . . . ?
C37 C38 C39 C40 179.1(3) . . . . ?
C38 C39 C40 C41 -0.1(6) . . . . ?
C39 C40 C41 C42 0.0(6) . . . . ?
C39 C40 C41 C51 178.4(4) . . . . ?
C40 C41 C42 C43 -0.3(5) . . . . ?
C51 C41 C42 C43 -178.7(4) . . . . ?
C41 C42 C43 C38 0.7(5) . . . . ?
C39 C38 C43 C42 -0.8(5) . . . . ?
C37 C38 C43 C42 -179.5(3) . . . . ?
C35 C37 C44 C49 121.1(3) . . . . ?
C38 C37 C44 C49 -117.8(3) . . . . ?
C23 C37 C44 C49 3.4(4) . . . . ?
C35 C37 C44 C45 -57.0(3) . . . . ?
C38 C37 C44 C45 64.1(4) . . . . ?
C23 C37 C44 C45 -174.6(3) . . . . ?
C49 C44 C45 C46 0.2(5) . . . . ?
C37 C44 C45 C46 178.4(3) . . . . ?
C44 C45 C46 C47 -0.3(6) . . . . ?
C45 C46 C47 C48 0.7(6) . . . . ?
C45 C46 C47 C50 -176.4(4) . . . . ?
C46 C47 C48 C49 -1.1(6) . . . . ?
C50 C47 C48 C49 176.1(4) . . . . ?
C45 C44 C49 C48 -0.6(5) . . . . ?
C37 C44 C49 C48 -178.7(3) . . . . ?
C47 C48 C49 C44 1.0(6) . . . . ?
Cl1 C54 Cl1 C54 0.000(2) 2_566 . . 2_566 ?
C11 C12 N1 C1 -179.8(3) . . . . ?
C7 C12 N1 C1 1.7(3) . . . . ?
C11 C12 N1 C13 -4.5(5) . . . . ?
C7 C12 N1 C13 177.1(3) . . . . ?
C2 C1 N1 C12 176.9(4) . . . . ?
C6 C1 N1 C12 -1.0(4) . . . . ?
C2 C1 N1 C13 1.4(5) . . . . ?
C6 C1 N1 C13 -176.5(3) . . . . ?
C18 C13 N1 C12 126.9(4) . . . . ?
C14 C13 N1 C12 -54.3(4) . . . . ?
C18 C13 N1 C1 -58.4(4) . . . . ?
C14 C13 N1 C1 120.4(3) . . . . ?
C35 C36 N2 C22 -18.8(4) . . . . ?
C31 C36 N2 C22 161.9(3) . . . . ?
C35 C36 N2 C25 176.9(3) . . . . ?
C31 C36 N2 C25 -2.4(3) . . . . ?
C21 C22 N2 C36 -154.8(3) . . . . ?
C23 C22 N2 C36 22.2(4) . . . . ?
C21 C22 N2 C25 5.0(5) . . . . ?
C23 C22 N2 C25 -178.0(3) . . . . ?
C26 C25 N2 C36 -174.6(3) . . . . ?
C30 C25 N2 C36 1.1(3) . . . . ?
C26 C25 N2 C22 24.0(5) . . . . ?
C30 C25 N2 C22 -160.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.366
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.096