# Perkin Transactions I © The Royal Society of Chemistry, 1999
# CCDC Number: 207/341

#=======================================================================

data_global
#=======================================================================


# 1. SUBMISSION DETAILS

_publ_contact_author
;
    Shuntaro Mataka
    Institute of Advanced Material Study
    Kyushu University
    6-1, Kasuga-koh-en, Kasuga,
    Fukuoka 816, Japan
;
_publ_contact_author_phone        '+81-92-583-7811'
_publ_contact_author_fax          '+81-92-583-7811'
_publ_contact_author_email        mataka@cm.kyushu-u.ac.jp

_publ_requested_journal        'J. Chem. Soc. Perkin. 1' 
_publ_requested_coeditor_name     ? 

_publ_contact_letter
;
?
;

#=======================================================================


# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic     ? 

_journal_date_to_coeditor         ? 
_journal_date_from_coeditor       ? 
_journal_date_accepted            ? 

_journal_date_printers_first      ? 
_journal_date_printers_final      ? 
_journal_date_proofs_out          ? 
_journal_date_proofs_in           ? 

_journal_coeditor_name            ? 
_journal_coeditor_code            ? 
_journal_coeditor_notes
; ?
;

_journal_techeditor_code          ? 
_journal_techeditor_notes
; ?
;

_journal_coden_ASTM               ? 
_journal_name_full                ? 
_journal_year                     ? 
_journal_volume                   ? 
_journal_issue                    ? 
_journal_page_first               ? 
_journal_page_last                ? 

_journal_suppl_publ_number        ? 
_journal_suppl_publ_pages         ? 

#=======================================================================


# 3. TITLE AND AUTHOR LIST

_publ_section_title
; Novel rearrangement of Confomationally
Restrained [3.3]Orthocyclophanes.  
;

#The loop structure below should contain the names and addresses of all 
#authors, in the required order of publication.  Repeat as necessary.

loop_
      _publ_author_name
      _publ_author_address
'Isobe, Shin-ichiro'
;
      Department of Molecular Science and Technology,
      Graduate School of Engeneering Sciences,
      Kyushu University
      6-1, Kasuga-koh-en, Kasuga,
      Fukuoka  816, Japan
;
'Taniguchi, Masahiko'
;
      Department of Molecular Science and Technology,
      Graduate School of Engeneering Sciences,
      Kyushu University
      6-1, Kasuga-koh-en, Kasuga,
      Fukuoka  816, Japan
;
'Sawada, Tsuyoshi'
;
      Institute of Advanced Material Study
      Kyushu University
      6-1, Kasuga-koh-en, Kasuga,
      Fukuoka  816, Japan
;
'Thiemann, Thies'
;
      Institute of Advanced Material Study
      Kyushu University
      6-1, Kasuga-koh-en, Kasuga,
      Fukuoka  816, Japan
;
'Yonemitsu, Tadashi'
;
      Department of Industrial Chemistry, 
Faculty of Engineering, Kyushu Sangyo University,
Matsukadai, Kashi-i, Higashiku, 
Fukuoka 813-0004, Japan
;
'Mataka, Shuntaro'
;
      Institute of Advanced Material Study
      Kyushu University
      6-1, Kasuga-koh-en, Kasuga,
      Fukuoka  816, Japan
;
     
#=======================================================================


# 4. TEXT

_publ_section_abstract
;
 ? 
;
_publ_section_comment
;
 ? 
;

_publ_section_experimental
;
SIR92 and SHELXL-93 were used for structure solution and refinement, 
respectively.  All H atoms were located at ideal positions (SHELXL-93) and were 
included in refinement, but restrained to ride on the atom to which they are 
bonded.  Isotropic thermal factors of H atoms were held fixed to 1.3 times 
U~eq~ of the riding atoms.  
;

_publ_section_references
;
Altomare, M. C., Burla, M., Camalli, G., Cascarano, C., Giacovazzo, 
A., Guagliardi, G. & Polidori, J. (1994). SIR92. J. Appl. Cryst. 27, 
435.
 
Hall, S. R. & du Boulay, D. (1995). Xtal_GX. University of 
Western Australia, Austaralia. 
 
Sheldrick, G. M. (1993). SHELXL-93. University of G_"ottingen, 
Germany.
;

_publ_section_figure_captions
;
 ? 
;

_publ_section_acknowledgements
;
The authors are grateful to authors of SIR92, SHELXL-93, and Xtal_GX 
for their permission to use their programs.  Acknowledgements are 
also due to Dr. H. Uekusa and Prof. Y. Ohashi, Tokyo Institute of 
Technology, for their kind instructions on using these programs. 
;
#=======================================================================


data_11b

#=======================================================================


# 5. CHEMICAL DATA

_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 1-(1'-Naphthyl)-4,5:9,10-dibenzobicyclo[5,4,0,02,11]undeca-4,9-diene 
; 
_chemical_name_common             11b 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C35 H30' 
_chemical_formula_weight          450.59 
_chemical_melting_point           245c 
_chemical_compound_source         ? 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0181    .0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
#=======================================================================


# 6. CRYSTAL DATA

_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'p 1 21/c 1' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    12.260(4) 
_cell_length_b                    19.770(9) 
_cell_length_c                    10.336(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.688(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2496.9(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     19 
_cell_measurement_theta_min       22 
_cell_measurement_theta_max       42 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.199 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              960 
_exptl_absorpt_coefficient_mu     0.507 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.903
_exptl_absorpt_correction_T_max   0.913
 
#=======================================================================


# 7. EXPERIMENTAL DATA

_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuKa  
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        Enraf_Nonius_CAD4  
_diffrn_measurement_method  \w/2\q
_diffrn_standards_number       3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   120 
_diffrn_standards_decay_%         -1.71 
_diffrn_reflns_number             4817 
_diffrn_reflns_av_R_equivalents   0.0768 
_diffrn_reflns_av_sigmaI/netI     0.0619 
_diffrn_reflns_limit_h_min        -14 
_diffrn_reflns_limit_h_max        14 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        23 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          3.62 
_diffrn_reflns_theta_max          68.00 
_reflns_number_total              4549 
_reflns_number_gt           2481 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'CAD4 Enraf-Nonius software' 
_computing_cell_refinement        'CAD4 Enraf-Nonius software'  
_computing_data_reduction         'MolEN  Enraf-Nonius software'
_computing_structure_solution     
;SIR92 (Altomare, Burla, Camalli, Cascarano, Giacovazzo,
Guagliardi & Polidori, 1994) 
;
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Xtal_GX (Hall & Boulay, 1995)' 
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)' 
 
#=======================================================================


# 8. REFINEMENT DATA

_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 w=1/[s^2^(Fo^2^)+( 0.0732P)^2^+0.7478P] 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     riding 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0015(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' 
_refine_ls_number_reflns          4548 
_refine_ls_number_parameters      317 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1323 
_refine_ls_R_factor_gt           0.0569 
_refine_ls_wR_factor_ref          0.1869 
_refine_ls_wR_factor_gt          0.1317 
_refine_ls_goodness_of_fit_all    1.108 
_refine_ls_goodness_of_fit_ref    1.087 
_refine_ls_restrained_S_all       1.108 
_refine_ls_restrained_S_obs       1.087 
_refine_ls_shift/su_max          0.000 
_refine_ls_shift/esd_mean         0.000 
_refine_diff_density_max     .202 
_refine_diff_density_min    -.211 
_refine_diff_density_rms     .055  

#=======================================================================


# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
C01 C -0.1019(3) 0.66070(14) 0.3490(3) 0.0497(8) Uani 1 d . . 
C02 C -0.1984(3) 0.6572(2) 0.4088(4) 0.0648(9) Uani 1 d . . 
H02 H -0.1964(3) 0.6459(2) 0.4963(4) 0.084 Uiso 1 calc R . 
C03 C -0.2972(3) 0.6701(2) 0.3416(4) 0.0777(12) Uani 1 d . . 
H03 H -0.3615(3) 0.6677(2) 0.3835(4) 0.101 Uiso 1 calc R . 
C04 C -0.3013(3) 0.6868(2) 0.2109(4) 0.0762(11) Uani 1 d . . 
H04 H -0.3683(3) 0.6951(2) 0.1647(4) 0.099 Uiso 1 calc R . 
C05 C -0.2061(3) 0.6910(2) 0.1501(4) 0.0623(9) Uani 1 d . . 
H05 H -0.2092(3) 0.7033(2) 0.0630(4) 0.081 Uiso 1 calc R . 
C06 C -0.1058(3) 0.67743(14) 0.2158(3) 0.0486(8) Uani 1 d . . 
C07 C -0.0025(3) 0.67593(14) 0.1493(3) 0.0490(8) Uani 1 d . . 
H07A H 0.0533(3) 0.70170(14) 0.1998(3) 0.064 Uiso 1 calc R . 
H07B H -0.0148(3) 0.69721(14) 0.0648(3) 0.064 Uiso 1 calc R . 
C08 C 0.0381(2) 0.60415(14) 0.1323(3) 0.0427(7) Uani 1 d . . 
H08 H 0.0072(2) 0.58244(14) 0.0523(3) 0.056 Uiso 1 calc R . 
C09 C 0.1539(2) 0.58347(14) 0.1713(3) 0.0445(7) Uani 1 d . . 
H09 H 0.1855(2) 0.55150(14) 0.1123(3) 0.058 Uiso 1 calc R . 
C10 C 0.2343(2) 0.62814(14) 0.2450(3) 0.0446(7) Uani 1 d . . 
C11 C 0.2995(3) 0.67307(15) 0.1825(3) 0.0536(8) Uani 1 d . . 
H11 H 0.2910(3) 0.67703(15) 0.0926(3) 0.070 Uiso 1 calc R . 
C12 C 0.3771(3) 0.7119(2) 0.2529(4) 0.0607(9) Uani 1 d . . 
H12 H 0.4211(3) 0.7414(2) 0.2103(4) 0.079 Uiso 1 calc R . 
C13 C 0.3891(3) 0.7070(2) 0.3860(4) 0.0638(9) Uani 1 d . . 
H13 H 0.4411(3) 0.7334(2) 0.4332(4) 0.083 Uiso 1 calc R . 
C14 C 0.3244(3) 0.6631(2) 0.4495(3) 0.0582(9) Uani 1 d . . 
H14 H 0.3325(3) 0.6605(2) 0.5397(3) 0.076 Uiso 1 calc R . 
C15 C 0.2472(2) 0.62272(15) 0.3806(3) 0.0476(8) Uani 1 d . . 
C16 C 0.1763(3) 0.5744(2) 0.4485(3) 0.0523(8) Uani 1 d . . 
H16A H 0.1779(3) 0.5862(2) 0.5397(3) 0.068 Uiso 1 calc R . 
H16B H 0.2046(3) 0.5288(2) 0.4421(3) 0.068 Uiso 1 calc R . 
C17 C 0.0587(3) 0.57695(14) 0.3879(3) 0.0453(7) Uani 1 d . . 
H17 H 0.0183(3) 0.54181(14) 0.4308(3) 0.059 Uiso 1 calc R . 
C18 C 0.0063(3) 0.6451(2) 0.4199(3) 0.0510(8) Uani 1 d . . 
H18A H -0.0026(3) 0.6461(2) 0.5123(3) 0.066 Uiso 1 calc R . 
H18B H 0.0570(3) 0.6809(2) 0.4020(3) 0.066 Uiso 1 calc R . 
C19 C 0.0609(2) 0.55532(13) 0.2441(3) 0.0402(7) Uani 1 d . . 
C20 C 0.0342(2) 0.48128(13) 0.2230(3) 0.0407(7) Uani 1 d . . 
C21 C 0.1186(3) 0.43583(14) 0.2232(3) 0.0479(8) Uani 1 d . . 
H21 H 0.1903(3) 0.45153(14) 0.2317(3) 0.062 Uiso 1 calc R . 
C22 C 0.0990(3) 0.36565(15) 0.2107(3) 0.0526(8) Uani 1 d . . 
H22 H 0.1574(3) 0.33562(15) 0.2111(3) 0.068 Uiso 1 calc R . 
C23 C -0.0047(3) 0.34233(15) 0.1983(3) 0.0496(8) Uani 1 d . . 
H23 H -0.0168(3) 0.29603(15) 0.1900(3) 0.065 Uiso 1 calc R . 
C24 C -0.0947(2) 0.38609(14) 0.1975(3) 0.0434(7) Uani 1 d . . 
C25 C -0.2027(3) 0.3625(2) 0.1851(3) 0.0577(9) Uani 1 d . . 
H25 H -0.2154(3) 0.3163(2) 0.1761(3) 0.075 Uiso 1 calc R . 
C26 C -0.2889(3) 0.4049(2) 0.1860(3) 0.0661(10) Uani 1 d . . 
H26 H -0.3599(3) 0.3880(2) 0.1783(3) 0.086 Uiso 1 calc R . 
C27 C -0.2703(3) 0.4752(2) 0.1988(3) 0.0616(9) Uani 1 d . . 
H27 H -0.3295(3) 0.5045(2) 0.1996(3) 0.080 Uiso 1 calc R . 
C28 C -0.1678(2) 0.5001(2) 0.2097(3) 0.0508(8) Uani 1 d . . 
H28 H -0.1576(2) 0.5466(2) 0.2170(3) 0.066 Uiso 1 calc R . 
C29 C -0.0751(2) 0.45748(14) 0.2102(3) 0.0413(7) Uani 1 d . . 
C30 C 0.4143(3) 0.4848(2) 0.1481(5) 0.0826(12) Uani 1 d . . 
H30 H 0.4148(3) 0.5223(2) 0.0939(5) 0.107 Uiso 1 calc R . 
C31 C 0.4316(3) 0.4928(3) 0.2793(5) 0.0902(14) Uani 1 d . . 
H31 H 0.4445(3) 0.5356(3) 0.3146(5) 0.117 Uiso 1 calc R . 
C32 C 0.3961(4) 0.4219(2) 0.0958(4) 0.0841(12) Uani 1 d . . 
H32 H 0.3846(4) 0.4165(2) 0.0064(4) 0.109 Uiso 1 calc R . 
C33 C 0.4299(4) 0.4371(3) 0.3592(5) 0.0951(14) Uani 1 d . . 
H33 H 0.4411(4) 0.4421(3) 0.4488(5) 0.124 Uiso 1 calc R . 
C34 C 0.3948(3) 0.3669(2) 0.1756(5) 0.0803(12) Uani 1 d . . 
H34 H 0.3823(3) 0.3240(2) 0.1403(5) 0.104 Uiso 1 calc R . 
C35 C 0.4116(4) 0.3745(2) 0.3060(5) 0.0883(13) Uani 1 d . . 
H35 H 0.4107(4) 0.3368(2) 0.3597(5) 0.115 Uiso 1 calc R . 
 
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 
C01 0.062(2) 0.038(2) 0.049(2) -0.0104(14) 0.0057(15) 0.0034(14) 
C02 0.070(2) 0.065(2) 0.062(2) -0.007(2) 0.015(2) 0.011(2) 
C03 0.068(3) 0.079(3) 0.088(3) -0.011(2) 0.018(2) 0.013(2) 
C04 0.069(3) 0.068(2) 0.090(3) -0.008(2) -0.004(2) 0.016(2) 
C05 0.075(2) 0.048(2) 0.063(2) -0.002(2) -0.005(2) 0.013(2) 
C06 0.067(2) 0.0290(14) 0.050(2) -0.0029(13) 0.004(2) 0.0054(14) 
C07 0.071(2) 0.033(2) 0.043(2) 0.0027(13) 0.0027(15) -0.0002(14) 
C08 0.059(2) 0.0335(14) 0.036(2) -0.0037(12) 0.0061(14) -0.0020(13) 
C09 0.055(2) 0.0366(15) 0.042(2) -0.0060(13) 0.0046(14) -0.0041(13) 
C10 0.051(2) 0.038(2) 0.045(2) -0.0010(13) 0.0052(14) -0.0020(13) 
C11 0.060(2) 0.047(2) 0.055(2) 0.004(2) 0.008(2) -0.003(2) 
C12 0.053(2) 0.050(2) 0.079(3) 0.000(2) 0.007(2) -0.012(2) 
C13 0.059(2) 0.057(2) 0.075(3) -0.010(2) -0.003(2) -0.009(2) 
C14 0.059(2) 0.059(2) 0.054(2) -0.006(2) -0.007(2) 0.000(2) 
C15 0.049(2) 0.043(2) 0.050(2) -0.0011(14) 0.0012(14) -0.0003(13) 
C16 0.065(2) 0.047(2) 0.044(2) 0.0055(14) 0.000(2) 0.000(2) 
C17 0.061(2) 0.0360(15) 0.040(2) 0.0041(13) 0.0059(14) -0.0042(13) 
C18 0.065(2) 0.048(2) 0.040(2) -0.0087(14) 0.0041(15) 0.004(2) 
C19 0.051(2) 0.0297(14) 0.040(2) -0.0021(12) 0.0042(13) -0.0011(12) 
C20 0.051(2) 0.0327(15) 0.039(2) 0.0002(12) 0.0027(13) -0.0012(13) 
C21 0.050(2) 0.039(2) 0.053(2) -0.0009(14) 0.0009(14) -0.0008(14) 
C22 0.069(2) 0.035(2) 0.054(2) 0.0006(14) 0.007(2) 0.0065(15) 
C23 0.076(2) 0.0310(15) 0.042(2) 0.0033(13) 0.005(2) -0.001(2) 
C24 0.062(2) 0.0362(15) 0.032(2) 0.0013(12) 0.0018(13) -0.0101(14) 
C25 0.072(2) 0.052(2) 0.049(2) 0.003(2) 0.000(2) -0.021(2) 
C26 0.058(2) 0.078(3) 0.061(2) 0.006(2) -0.003(2) -0.022(2) 
C27 0.054(2) 0.065(2) 0.066(2) 0.006(2) 0.002(2) -0.001(2) 
C28 0.051(2) 0.044(2) 0.056(2) 0.0058(15) 0.0024(15) -0.0005(15) 
C29 0.054(2) 0.0366(15) 0.033(2) 0.0032(12) 0.0039(13) -0.0032(13) 
C30 0.066(3) 0.082(3) 0.101(4) 0.016(3) 0.010(2) 0.004(2) 
C31 0.069(3) 0.087(3) 0.112(4) -0.025(3) -0.007(3) -0.001(2) 
C32 0.087(3) 0.093(3) 0.072(3) -0.002(3) 0.006(2) 0.001(2) 
C33 0.098(3) 0.114(4) 0.071(3) -0.002(3) -0.012(2) 0.012(3) 
C34 0.070(3) 0.075(3) 0.095(3) -0.008(3) 0.005(2) 0.004(2) 
C35 0.089(3) 0.084(3) 0.090(4) 0.017(3) -0.003(3) 0.010(2) 
 
#=======================================================================

# 10. MOLECULAR GEOMETRY

_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 
C01 C02 1.382(5) . ? 
C01 C06 1.413(4) . ? 
C01 C18 1.495(4) . ? 
C02 C03 1.370(5) . ? 
C03 C04 1.387(6) . ? 
C04 C05 1.373(5) . ? 
C05 C06 1.382(4) . ? 
C06 C07 1.490(4) . ? 
C07 C08 1.519(4) . ? 
C08 C09 1.500(4) . ? 
C08 C19 1.514(4) . ? 
C09 C10 1.486(4) . ? 
C09 C19 1.522(4) . ? 
C10 C11 1.389(4) . ? 
C10 C15 1.402(4) . ? 
C11 C12 1.382(4) . ? 
C12 C13 1.374(5) . ? 
C13 C14 1.378(5) . ? 
C14 C15 1.390(4) . ? 
C15 C16 1.503(4) . ? 
C16 C17 1.525(4) . ? 
C17 C18 1.540(4) . ? 
C17 C19 1.549(4) . ? 
C19 C20 1.512(4) . ? 
C20 C21 1.370(4) . ? 
C20 C29 1.417(4) . ? 
C21 C22 1.412(4) . ? 
C22 C23 1.348(4) . ? 
C23 C24 1.402(4) . ? 
C24 C25 1.401(4) . ? 
C24 C29 1.436(4) . ? 
C25 C26 1.349(5) . ? 
C26 C27 1.413(5) . ? 
C27 C28 1.346(4) . ? 
C28 C29 1.414(4) . ? 
C30 C31 1.365(6) . ? 
C30 C32 1.368(6) . ? 
C31 C33 1.377(7) . ? 
C32 C34 1.365(6) . ? 
C33 C35 1.365(6) . ? 
C34 C35 1.355(6) . ? 
 
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 
C02 C01 C06 119.1(3) . . ? 
C02 C01 C18 121.9(3) . . ? 
C06 C01 C18 119.0(3) . . ? 
C03 C02 C01 121.2(4) . . ? 
C02 C03 C04 119.9(4) . . ? 
C05 C04 C03 119.8(4) . . ? 
C04 C05 C06 121.2(4) . . ? 
C05 C06 C01 118.8(3) . . ? 
C05 C06 C07 122.2(3) . . ? 
C01 C06 C07 118.8(3) . . ? 
C06 C07 C08 111.8(2) . . ? 
C09 C08 C19 60.6(2) . . ? 
C09 C08 C07 122.4(3) . . ? 
C19 C08 C07 123.3(2) . . ? 
C10 C09 C08 123.3(2) . . ? 
C10 C09 C19 117.2(2) . . ? 
C08 C09 C19 60.1(2) . . ? 
C11 C10 C15 119.4(3) . . ? 
C11 C10 C09 121.6(3) . . ? 
C15 C10 C09 118.9(3) . . ? 
C12 C11 C10 120.5(3) . . ? 
C13 C12 C11 120.0(3) . . ? 
C12 C13 C14 120.2(3) . . ? 
C13 C14 C15 120.8(3) . . ? 
C14 C15 C10 119.0(3) . . ? 
C14 C15 C16 121.4(3) . . ? 
C10 C15 C16 119.5(3) . . ? 
C15 C16 C17 110.6(2) . . ? 
C16 C17 C18 109.7(2) . . ? 
C16 C17 C19 107.2(2) . . ? 
C18 C17 C19 119.2(2) . . ? 
C01 C18 C17 116.4(2) . . ? 
C20 C19 C08 118.9(2) . . ? 
C20 C19 C09 116.4(2) . . ? 
C08 C19 C09 59.2(2) . . ? 
C20 C19 C17 112.7(2) . . ? 
C08 C19 C17 122.7(2) . . ? 
C09 C19 C17 116.5(2) . . ? 
C21 C20 C29 119.4(3) . . ? 
C21 C20 C19 118.7(3) . . ? 
C29 C20 C19 121.8(3) . . ? 
C20 C21 C22 121.5(3) . . ? 
C23 C22 C21 119.8(3) . . ? 
C22 C23 C24 121.7(3) . . ? 
C25 C24 C23 122.2(3) . . ? 
C25 C24 C29 119.0(3) . . ? 
C23 C24 C29 118.8(3) . . ? 
C26 C25 C24 121.9(3) . . ? 
C25 C26 C27 119.4(3) . . ? 
C28 C27 C26 120.7(3) . . ? 
C27 C28 C29 121.7(3) . . ? 
C28 C29 C20 123.8(3) . . ? 
C28 C29 C24 117.3(3) . . ? 
C20 C29 C24 119.0(3) . . ? 
C31 C30 C32 120.3(4) . . ? 
C30 C31 C33 119.7(4) . . ? 
C34 C32 C30 119.7(4) . . ? 
C35 C33 C31 119.5(4) . . ? 
C35 C34 C32 120.2(4) . . ? 
C34 C35 C33 120.6(4) . . ? 
 
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 
 C06 C01 C02 C03 -0.4(5) . . . . ? 
 C18 C01 C02 C03 -178.4(3) . . . . ? 
 C01 C02 C03 C04 0.2(6) . . . . ? 
 C02 C03 C04 C05 -0.7(6) . . . . ? 
 C03 C04 C05 C06 1.5(5) . . . . ? 
 C04 C05 C06 C01 -1.7(5) . . . . ? 
 C04 C05 C06 C07 174.7(3) . . . . ? 
 C02 C01 C06 C05 1.2(4) . . . . ? 
 C18 C01 C06 C05 179.2(3) . . . . ? 
 C02 C01 C06 C07 -175.3(3) . . . . ? 
 C18 C01 C06 C07 2.7(4) . . . . ? 
 C05 C06 C07 C08 -105.8(3) . . . . ? 
 C01 C06 C07 C08 70.6(4) . . . . ? 
 C06 C07 C08 C09 -130.0(3) . . . . ? 
 C06 C07 C08 C19 -56.2(4) . . . . ? 
 C19 C08 C09 C10 -104.6(3) . . . . ? 
 C07 C08 C09 C10 8.3(4) . . . . ? 
 C19 C08 C09 C19 0.0 . . . . ? 
 C07 C08 C09 C19 112.9(3) . . . . ? 
 C08 C09 C10 C11 -88.4(4) . . . . ? 
 C19 C09 C10 C11 -159.0(3) . . . . ? 
 C08 C09 C10 C15 94.0(3) . . . . ? 
 C19 C09 C10 C15 23.5(4) . . . . ? 
 C15 C10 C11 C12 0.4(4) . . . . ? 
 C09 C10 C11 C12 -177.1(3) . . . . ? 
 C10 C11 C12 C13 -0.9(5) . . . . ? 
 C11 C12 C13 C14 0.3(5) . . . . ? 
 C12 C13 C14 C15 0.7(5) . . . . ? 
 C13 C14 C15 C10 -1.2(5) . . . . ? 
 C13 C14 C15 C16 179.8(3) . . . . ? 
 C11 C10 C15 C14 0.7(4) . . . . ? 
 C09 C10 C15 C14 178.2(3) . . . . ? 
 C11 C10 C15 C16 179.7(3) . . . . ? 
 C09 C10 C15 C16 -2.7(4) . . . . ? 
 C14 C15 C16 C17 137.6(3) . . . . ? 
 C10 C15 C16 C17 -41.4(4) . . . . ? 
 C15 C16 C17 C18 -69.6(3) . . . . ? 
 C15 C16 C17 C19 61.1(3) . . . . ? 
 C02 C01 C18 C17 105.7(3) . . . . ? 
 C06 C01 C18 C17 -72.3(4) . . . . ? 
 C16 C17 C18 C01 169.7(3) . . . . ? 
 C19 C17 C18 C01 45.7(4) . . . . ? 
 C09 C08 C19 C20 -105.2(3) . . . . ? 
 C07 C08 C19 C20 143.4(3) . . . . ? 
 C09 C08 C19 C09 0.0 . . . . ? 
 C07 C08 C19 C09 -111.4(3) . . . . ? 
 C09 C08 C19 C17 103.6(3) . . . . ? 
 C07 C08 C19 C17 -7.9(4) . . . . ? 
 C10 C09 C19 C20 -135.9(3) . . . . ? 
 C08 C09 C19 C20 109.4(3) . . . . ? 
 C10 C09 C19 C08 114.7(3) . . . . ? 
 C08 C09 C19 C08 0.0 . . . . ? 
 C10 C09 C19 C17 0.7(4) . . . . ? 
 C08 C09 C19 C17 -113.9(3) . . . . ? 
 C16 C17 C19 C20 96.5(3) . . . . ? 
 C18 C17 C19 C20 -138.2(3) . . . . ? 
 C16 C17 C19 C08 -110.7(3) . . . . ? 
 C18 C17 C19 C08 14.6(4) . . . . ? 
 C16 C17 C19 C09 -41.8(3) . . . . ? 
 C18 C17 C19 C09 83.5(3) . . . . ? 
 C08 C19 C20 C21 111.3(3) . . . . ? 
 C09 C19 C20 C21 43.5(4) . . . . ? 
 C17 C19 C20 C21 -94.7(3) . . . . ? 
 C08 C19 C20 C29 -72.2(4) . . . . ? 
 C09 C19 C20 C29 -139.9(3) . . . . ? 
 C17 C19 C20 C29 81.8(3) . . . . ? 
 C29 C20 C21 C22 0.1(5) . . . . ? 
 C19 C20 C21 C22 176.7(3) . . . . ? 
 C20 C21 C22 C23 0.0(5) . . . . ? 
 C21 C22 C23 C24 -0.1(5) . . . . ? 
 C22 C23 C24 C25 -179.7(3) . . . . ? 
 C22 C23 C24 C29 0.0(4) . . . . ? 
 C23 C24 C25 C26 179.2(3) . . . . ? 
 C29 C24 C25 C26 -0.6(5) . . . . ? 
 C24 C25 C26 C27 0.5(5) . . . . ? 
 C25 C26 C27 C28 0.2(5) . . . . ? 
 C26 C27 C28 C29 -0.7(5) . . . . ? 
 C27 C28 C29 C20 -179.2(3) . . . . ? 
 C27 C28 C29 C24 0.6(5) . . . . ? 
 C21 C20 C29 C28 179.6(3) . . . . ? 
 C19 C20 C29 C28 3.1(4) . . . . ? 
 C21 C20 C29 C24 -0.1(4) . . . . ? 
 C19 C20 C29 C24 -176.6(3) . . . . ? 
 C25 C24 C29 C28 0.1(4) . . . . ? 
 C23 C24 C29 C28 -179.7(3) . . . . ? 
 C25 C24 C29 C20 179.8(3) . . . . ? 
 C23 C24 C29 C20 0.1(4) . . . . ? 
 C32 C30 C31 C33 -0.5(7) . . . . ? 
 C31 C30 C32 C34 0.3(7) . . . . ? 
 C30 C31 C33 C35 0.4(7) . . . . ? 
 C30 C32 C34 C35 -0.1(7) . . . . ? 
 C32 C34 C35 C33 0.1(7) . . . . ? 
 C31 C33 C35 C34 -0.2(7) . . . . ? 

#=END

data_6a

#=======================================================================


# 5. CHEMICAL DATA

_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 5-Bromomethyl-5a-phenyl-5,5a,6,11,11a,12-hexahydronaphthacene 
; 
_chemical_name_common             6a 
_chemical_melting_point           141-144 
_chemical_formula_moiety          ? 
_chemical_formula_sum               'C25 H23 Br' 
_chemical_formula_weight          403.34 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0181    .0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'   -.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

#=======================================================================


# 6. CRYSTAL DATA

_symmetry_cell_setting            'monoclinic'
_symmetry_space_group_name_H-M     'p 1 21/a 1'
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z' 
 
_cell_length_a                    18.639(4) 
_cell_length_b                    10.296(2) 
_cell_length_c                    9.869(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.77(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1880.7(7) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     22 
_cell_measurement_theta_min       22 
_cell_measurement_theta_max       40 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.424 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              832 
_exptl_absorpt_coefficient_mu     2.991 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.9327 
_exptl_absorpt_correction_T_max   0.9998 


#=======================================================================



# 7. EXPERIMENTAL DATA

_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   Enraf_Nonius_CAD4 
_diffrn_measurement_method        \w/2\q 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   120 
_diffrn_standards_decay_%         -21.9 
_diffrn_reflns_number             3953 
_diffrn_reflns_av_R_equivalents   0.0424 
_diffrn_reflns_av_sigmaI/netI     0.0254 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        23 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          4.51 
_diffrn_reflns_theta_max          74.27 
_reflns_number_total              3830 
_reflns_number_gt                 3265 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CAD4 Enraf-Nonius software' 
_computing_cell_refinement        'CAD4 Enraf-Nonius software' 
_computing_data_reduction         'MolEN Enraf-Nonius software' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Xtal_GX (Hall & Boulay, 1995)' 
_computing_publication_material   'SHELXL-97 (Sheldrick, 1997)' 
 
#=======================================================================

# 8. REFINEMENT DATA

_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^)+(0.1073P)^2^+1.7062P] 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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0005(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          3830 
_refine_ls_number_parameters      236 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0586 
_refine_ls_R_factor_gt            0.0438 
_refine_ls_wR_factor_ref          0.1830 
_refine_ls_wR_factor_gt           0.1437 
_refine_ls_goodness_of_fit_ref    1.160 
_refine_ls_restrained_S_all       1.160 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
_refine_diff_density_max     .905 
_refine_diff_density_min    -.567 
_refine_diff_density_rms     .148 

#=======================================================================


# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

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 
Br1 Br 0.44354(2) 0.11932(4) 0.09742(4) 0.0527(2) Uani 1 1 d . . . 
C01 C 0.46937(18) 0.4913(4) 0.2766(4) 0.0387(8) Uani 1 1 d . . . 
C02 C 0.5016(2) 0.5863(5) 0.2024(4) 0.0506(10) Uani 1 1 d . . . 
H02 H 0.5299 0.5612 0.1354 0.066 Uiso 1 1 calc R . . 
C03 C 0.4920(3) 0.7172(5) 0.2272(6) 0.0647(13) Uani 1 1 d . . . 
H03 H 0.5145 0.7794 0.1784 0.084 Uiso 1 1 calc R . . 
C04 C 0.4496(3) 0.7543(4) 0.3233(5) 0.0609(13) Uani 1 1 d . . . 
H04 H 0.4431 0.8422 0.3398 0.079 Uiso 1 1 calc R . . 
C05 C 0.4158(2) 0.6624(4) 0.3973(4) 0.0482(9) Uani 1 1 d . . . 
H05 H 0.3862 0.6894 0.4613 0.063 Uiso 1 1 calc R . . 
C06 C 0.42608(18) 0.5300(3) 0.3764(4) 0.0378(8) Uani 1 1 d . . . 
C07 C 0.39045(19) 0.4309(3) 0.4575(3) 0.0367(7) Uani 1 1 d . . . 
H07A H 0.3693 0.4746 0.5303 0.048 Uiso 1 1 calc R . . 
H07B H 0.4270 0.3714 0.4992 0.048 Uiso 1 1 calc R . . 
C08 C 0.33107(18) 0.3521(3) 0.3717(3) 0.0316(7) Uani 1 1 d . . . 
H08 H 0.3057 0.4114 0.3047 0.041 Uiso 1 1 calc R . . 
C09 C 0.27576(17) 0.3021(3) 0.4625(3) 0.0351(7) Uani 1 1 d . . . 
H09A H 0.2593 0.3742 0.5142 0.046 Uiso 1 1 calc R . . 
H09B H 0.2342 0.2678 0.4052 0.046 Uiso 1 1 calc R . . 
C10 C 0.30610(17) 0.1978(3) 0.5602(3) 0.0337(7) Uani 1 1 d . . . 
C11 C 0.2804(2) 0.1802(4) 0.6866(4) 0.0432(8) Uani 1 1 d . . . 
H11 H 0.2438 0.2337 0.7108 0.056 Uiso 1 1 calc R . . 
C12 C 0.3083(2) 0.0856(4) 0.7754(4) 0.0485(9) Uani 1 1 d . . . 
H12 H 0.2907 0.0757 0.8592 0.063 Uiso 1 1 calc R . . 
C13 C 0.3624(2) 0.0049(4) 0.7407(4) 0.0485(9) Uani 1 1 d . . . 
H13 H 0.3812 -0.0597 0.8005 0.063 Uiso 1 1 calc R . . 
C14 C 0.3882(2) 0.0206(4) 0.6174(4) 0.0408(8) Uani 1 1 d . . . 
H14 H 0.4247 -0.0340 0.5943 0.053 Uiso 1 1 calc R . . 
C15 C 0.36091(18) 0.1173(3) 0.5249(3) 0.0323(7) Uani 1 1 d . . . 
C16 C 0.39473(18) 0.1366(3) 0.3945(4) 0.0344(7) Uani 1 1 d . . . 
H16A H 0.3960 0.0531 0.3494 0.045 Uiso 1 1 calc R . . 
H16B H 0.4444 0.1641 0.4187 0.045 Uiso 1 1 calc R . . 
C17 C 0.35816(16) 0.2341(3) 0.2915(3) 0.0304(6) Uani 1 1 d . . . 
C18 C 0.41262(18) 0.2771(3) 0.1931(3) 0.0351(7) Uani 1 1 d . . . 
H18 H 0.3863 0.3329 0.1237 0.046 Uiso 1 1 calc R . . 
C19 C 0.48109(19) 0.3490(4) 0.2486(4) 0.0395(8) Uani 1 1 d . . . 
H19A H 0.5016 0.3075 0.3326 0.051 Uiso 1 1 calc R . . 
H19B H 0.5160 0.3414 0.1835 0.051 Uiso 1 1 calc R . . 
C20 C 0.29104(17) 0.1784(3) 0.2053(3) 0.0337(7) Uani 1 1 d . . . 
C21 C 0.2643(2) 0.0552(4) 0.2231(4) 0.0437(8) Uani 1 1 d . . . 
H21 H 0.2890 0.0003 0.2873 0.057 Uiso 1 1 calc R . . 
C22 C 0.2013(2) 0.0113(4) 0.1473(5) 0.0555(11) Uani 1 1 d . . . 
H22 H 0.1840 -0.0715 0.1624 0.072 Uiso 1 1 calc R . . 
C23 C 0.1644(2) 0.0901(5) 0.0502(5) 0.0557(11) Uani 1 1 d . . . 
H23 H 0.1225 0.0604 -0.0010 0.072 Uiso 1 1 calc R . . 
C24 C 0.1898(2) 0.2131(4) 0.0292(4) 0.0494(9) Uani 1 1 d . . . 
H24 H 0.1650 0.2669 -0.0361 0.064 Uiso 1 1 calc R . . 
C25 C 0.25262(19) 0.2569(4) 0.1055(4) 0.0392(8) Uani 1 1 d . . . 
H25 H 0.2695 0.3400 0.0902 0.051 Uiso 1 1 calc R . . 
 
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 
Br1 0.0564(3) 0.0586(3) 0.0451(3) -0.01553(17) 0.0136(2) 0.00241(19) 
C01 0.0320(16) 0.0441(19) 0.0370(17) 0.0035(14) -0.0086(13) -0.0067(14) 
C02 0.047(2) 0.062(2) 0.040(2) 0.0065(18) -0.0051(16) -0.0146(19) 
C03 0.066(3) 0.053(3) 0.071(3) 0.020(2) -0.009(2) -0.020(2) 
C04 0.064(3) 0.036(2) 0.077(3) 0.009(2) -0.020(2) -0.0040(19) 
C05 0.044(2) 0.0396(19) 0.056(2) 0.0006(17) -0.0126(17) 0.0018(16) 
C06 0.0337(16) 0.0370(17) 0.0390(18) -0.0006(14) -0.0111(13) -0.0043(14) 
C07 0.0381(17) 0.0377(17) 0.0329(16) -0.0040(14) -0.0016(13) 0.0006(14) 
C08 0.0303(15) 0.0297(15) 0.0333(16) -0.0010(12) -0.0022(12) 0.0055(12) 
C09 0.0304(15) 0.0382(17) 0.0360(16) -0.0043(13) 0.0010(13) 0.0035(13) 
C10 0.0298(15) 0.0366(17) 0.0336(16) -0.0017(13) -0.0004(12) -0.0062(13) 
C11 0.0409(18) 0.050(2) 0.0400(19) -0.0063(16) 0.0081(15) -0.0101(16) 
C12 0.053(2) 0.059(2) 0.0335(18) 0.0011(17) 0.0045(16) -0.0169(19) 
C13 0.056(2) 0.046(2) 0.0401(19) 0.0109(16) -0.0083(17) -0.0120(18) 
C14 0.0399(18) 0.0389(18) 0.0414(19) 0.0027(15) -0.0045(14) -0.0034(15) 
C15 0.0327(16) 0.0332(16) 0.0291(16) -0.0002(12) -0.0042(12) -0.0023(12) 
C16 0.0324(16) 0.0344(17) 0.0355(17) 0.0029(13) 0.0007(13) 0.0076(13) 
C17 0.0282(14) 0.0306(15) 0.0317(15) -0.0004(12) 0.0011(12) 0.0040(12) 
C18 0.0342(16) 0.0378(17) 0.0327(16) -0.0031(13) 0.0021(13) 0.0003(13) 
C19 0.0309(16) 0.050(2) 0.0373(18) -0.0020(15) 0.0006(13) -0.0031(15) 
C20 0.0321(16) 0.0365(17) 0.0314(15) -0.0055(13) -0.0006(12) 0.0002(13) 
C21 0.048(2) 0.0374(19) 0.044(2) -0.0003(15) -0.0020(16) -0.0022(15) 
C22 0.055(2) 0.049(2) 0.060(3) -0.011(2) -0.005(2) -0.0173(19) 
C23 0.042(2) 0.063(3) 0.059(3) -0.019(2) -0.0089(18) -0.0072(19) 
C24 0.041(2) 0.060(2) 0.043(2) -0.0044(18) -0.0098(16) 0.0077(18) 
C25 0.0388(17) 0.0382(17) 0.0383(18) -0.0004(14) -0.0045(14) 0.0024(14) 

#=======================================================================


# 10. MOLECULAR GEOMETRY

_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 
Br1 C18 1.998(3) . ? 
C01 C02 1.399(6) . ? 
C01 C06 1.403(5) . ? 
C01 C19 1.511(5) . ? 
C02 C03 1.385(7) . ? 
C03 C04 1.359(8) . ? 
C04 C05 1.390(7) . ? 
C05 C06 1.395(6) . ? 
C06 C07 1.500(5) . ? 
C07 C08 1.542(4) . ? 
C08 C09 1.532(5) . ? 
C08 C17 1.566(4) . ? 
C09 C10 1.508(5) . ? 
C10 C15 1.392(5) . ? 
C10 C11 1.399(5) . ? 
C11 C12 1.371(6) . ? 
C12 C13 1.382(6) . ? 
C13 C14 1.370(6) . ? 
C14 C15 1.405(5) . ? 
C15 C16 1.511(5) . ? 
C16 C17 1.530(4) . ? 
C17 C20 1.539(4) . ? 
C17 C18 1.550(5) . ? 
C18 C19 1.521(5) . ? 
C20 C21 1.382(5) . ? 
C20 C25 1.403(5) . ? 
C21 C22 1.391(6) . ? 
C22 C23 1.377(7) . ? 
C23 C24 1.376(6) . ? 
C24 C25 1.390(5) . ? 
 
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 
C02 C01 C06 119.1(4) . . ? 
C02 C01 C19 120.1(4) . . ? 
C06 C01 C19 120.8(3) . . ? 
C03 C02 C01 121.0(5) . . ? 
C04 C03 C02 119.6(4) . . ? 
C03 C04 C05 120.8(4) . . ? 
C04 C05 C06 120.6(4) . . ? 
C05 C06 C01 118.8(4) . . ? 
C05 C06 C07 120.6(4) . . ? 
C01 C06 C07 120.6(3) . . ? 
C06 C07 C08 113.5(3) . . ? 
C09 C08 C07 110.1(3) . . ? 
C09 C08 C17 108.3(3) . . ? 
C07 C08 C17 115.6(3) . . ? 
C10 C09 C08 112.7(3) . . ? 
C15 C10 C11 119.0(3) . . ? 
C15 C10 C09 119.7(3) . . ? 
C11 C10 C09 121.3(3) . . ? 
C12 C11 C10 121.2(4) . . ? 
C11 C12 C13 120.1(4) . . ? 
C14 C13 C12 119.5(4) . . ? 
C13 C14 C15 121.5(4) . . ? 
C10 C15 C14 118.7(3) . . ? 
C10 C15 C16 121.8(3) . . ? 
C14 C15 C16 119.4(3) . . ? 
C15 C16 C17 117.0(3) . . ? 
C16 C17 C20 113.1(3) . . ? 
C16 C17 C18 109.3(3) . . ? 
C20 C17 C18 108.0(3) . . ? 
C16 C17 C08 108.6(3) . . ? 
C20 C17 C08 106.2(2) . . ? 
C18 C17 C08 111.7(3) . . ? 
C19 C18 C17 119.8(3) . . ? 
C19 C18 Br1 106.8(2) . . ? 
C17 C18 Br1 108.1(2) . . ? 
C01 C19 C18 113.9(3) . . ? 
C21 C20 C25 117.1(3) . . ? 
C21 C20 C17 123.6(3) . . ? 
C25 C20 C17 119.2(3) . . ? 
C20 C21 C22 121.6(4) . . ? 
C23 C22 C21 120.3(4) . . ? 
C24 C23 C22 119.6(4) . . ? 
C23 C24 C25 120.0(4) . . ? 
C24 C25 C20 121.4(4) . . ? 
 
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 
C06 C01 C02 C03 0.8(6) . . . . ? 
C19 C01 C02 C03 -179.5(4) . . . . ? 
C01 C02 C03 C04 -1.2(7) . . . . ? 
C02 C03 C04 C05 0.1(7) . . . . ? 
C03 C04 C05 C06 1.4(6) . . . . ? 
C04 C05 C06 C01 -1.8(5) . . . . ? 
C04 C05 C06 C07 179.2(3) . . . . ? 
C02 C01 C06 C05 0.7(5) . . . . ? 
C19 C01 C06 C05 -179.0(3) . . . . ? 
C02 C01 C06 C07 179.8(3) . . . . ? 
C19 C01 C06 C07 0.0(5) . . . . ? 
C05 C06 C07 C08 111.6(4) . . . . ? 
C01 C06 C07 C08 -67.4(4) . . . . ? 
C06 C07 C08 C09 -154.0(3) . . . . ? 
C06 C07 C08 C17 82.8(4) . . . . ? 
C07 C08 C09 C10 -69.8(3) . . . . ? 
C17 C08 C09 C10 57.6(3) . . . . ? 
C08 C09 C10 C15 -28.9(4) . . . . ? 
C08 C09 C10 C11 150.9(3) . . . . ? 
C15 C10 C11 C12 0.0(5) . . . . ? 
C09 C10 C11 C12 -179.8(3) . . . . ? 
C10 C11 C12 C13 -0.3(6) . . . . ? 
C11 C12 C13 C14 0.3(6) . . . . ? 
C12 C13 C14 C15 0.0(6) . . . . ? 
C11 C10 C15 C14 0.4(5) . . . . ? 
C09 C10 C15 C14 -179.9(3) . . . . ? 
C11 C10 C15 C16 -175.8(3) . . . . ? 
C09 C10 C15 C16 4.0(5) . . . . ? 
C13 C14 C15 C10 -0.4(5) . . . . ? 
C13 C14 C15 C16 175.8(3) . . . . ? 
C10 C15 C16 C17 -9.7(5) . . . . ? 
C14 C15 C16 C17 174.2(3) . . . . ? 
C15 C16 C17 C20 -79.5(4) . . . . ? 
C15 C16 C17 C18 160.1(3) . . . . ? 
C15 C16 C17 C08 38.1(4) . . . . ? 
C09 C08 C17 C16 -61.4(3) . . . . ? 
C07 C08 C17 C16 62.7(4) . . . . ? 
C09 C08 C17 C20 60.5(3) . . . . ? 
C07 C08 C17 C20 -175.4(3) . . . . ? 
C09 C08 C17 C18 178.1(3) . . . . ? 
C07 C08 C17 C18 -57.8(4) . . . . ? 
C16 C17 C18 C19 -62.9(4) . . . . ? 
C20 C17 C18 C19 173.7(3) . . . . ? 
C08 C17 C18 C19 57.2(4) . . . . ? 
C16 C17 C18 Br1 59.7(3) . . . . ? 
C20 C17 C18 Br1 -63.8(3) . . . . ? 
C08 C17 C18 Br1 179.8(2) . . . . ? 
C02 C01 C19 C18 -115.7(4) . . . . ? 
C06 C01 C19 C18 64.1(4) . . . . ? 
C17 C18 C19 C01 -78.5(4) . . . . ? 
Br1 C18 C19 C01 158.3(3) . . . . ? 
C16 C17 C20 C21 3.0(5) . . . . ? 
C18 C17 C20 C21 124.1(4) . . . . ? 
C08 C17 C20 C21 -116.0(4) . . . . ? 
C16 C17 C20 C25 -179.3(3) . . . . ? 
C18 C17 C20 C25 -58.2(4) . . . . ? 
C08 C17 C20 C25 61.7(4) . . . . ? 
C25 C20 C21 C22 -1.1(6) . . . . ? 
C17 C20 C21 C22 176.7(4) . . . . ? 
C20 C21 C22 C23 1.0(7) . . . . ? 
C21 C22 C23 C24 -0.5(7) . . . . ? 
C22 C23 C24 C25 0.2(7) . . . . ? 
C23 C24 C25 C20 -0.4(6) . . . . ? 
C21 C20 C25 C24 0.8(5) . . . . ? 
C17 C20 C25 C24 -177.1(3) . . . . ? 

#===END

data_5

#=======================================================================


# 5. CHEMICAL DATA

_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 12-Bromo-11a-phenyl-5a,6,11,11a,12,13-hexahydro-5H-benzo[4,5]cyclohepta[1,2
b]naphthalene 
; 
_chemical_name_common             5 
_chemical_melting_point           180(decompose) 
_chemical_formula_moiety          ? 
_chemical_formula_sum             'C25 H23 Br' 
_chemical_formula_weight          403.34 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'    .0181    .0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'    .0000    .0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Br'  'Br'   -.6763   1.2805 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
#=======================================================================


# 6. CRYSTAL DATA

_symmetry_cell_setting            'monoclinic' 
_symmetry_space_group_name_H-M    'p 1 21/a 1' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z' 
 
_cell_length_a                    9.376(2) 
_cell_length_b                    23.622(3) 
_cell_length_c                    9.288(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  112.03(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1906.9(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       23 
_cell_measurement_theta_max       43 
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.30 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.405 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              832 
_exptl_absorpt_coefficient_mu     2.950 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.9017 
_exptl_absorpt_correction_T_max   0.9988 
 
#=======================================================================


# 7. EXPERIMENTAL DATA

_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuKa  
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        Enraf_Nonius_CAD4  
_diffrn_measurement_method        \w/2\q 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   120 
_diffrn_standards_decay_%         -1.2 
_diffrn_reflns_number             4128 
_diffrn_reflns_av_R_equivalents   0.0411 
_diffrn_reflns_av_sigmaI/netI     0.0189 
_diffrn_reflns_limit_h_min        0 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        29 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          3.74 
_diffrn_reflns_theta_max          74.42 
_reflns_number_total              3889 
_reflns_number_gt           3467 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        'CAD4 Enraf-Nonius software' 
_computing_cell_refinement        'CAD4 Enraf-Nonius software' 
_computing_data_reduction         'MolEN Enraf-Nonius software'  
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 
_computing_molecular_graphics     'Xtal_GX (Hall & Boulay, 1995)' 
_computing_publication_material   'SHELXL-93 (Sheldrick, 1993)' 
 
#=======================================================================


# 8. REFINEMENT DATA

_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 w=1/[s^2^(Fo^2^)+( 0.0704P)^2^+2.1349P] 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     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0025(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' 
_refine_ls_number_reflns          3889 
_refine_ls_number_parameters      236 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0542 
_refine_ls_R_factor_gt           0.0476 
_refine_ls_wR_factor_ref          0.1475 
_refine_ls_wR_factor_gt          0.1328 
_refine_ls_goodness_of_fit_ref    1.099 
_refine_ls_restrained_S_all       1.099 
_refine_ls_shift/su_max          0.000 
_refine_ls_shift/su_mean         0.000 
_refine_diff_density_max     .745 
_refine_diff_density_min    -.776 
_refine_diff_density_rms     .078 

#=======================================================================


# 9. ATOMIC COORDINATES AND THERMAL PARAMETERS

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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Br01 Br 0.16740(5) 0.57868(2) -0.26333(4) 0.0671(2) Uani 1 d . . 
C01 C 0.3061(3) 0.57860(10) 0.1622(3) 0.0344(6) Uani 1 d . . 
C02 C 0.1487(4) 0.56571(13) 0.1051(4) 0.0437(7) Uani 1 d . . 
H02 H 0.0900(4) 0.57120(13) 0.0003(4) 0.057 Uiso 1 calc R . 
C03 C 0.0792(4) 0.54499(14) 0.2018(4) 0.0499(8) Uani 1 d . . 
H03 H -0.0258(4) 0.53744(14) 0.1622(4) 0.065 Uiso 1 calc R . 
C04 C 0.1646(4) 0.53550(13) 0.3564(4) 0.0480(7) Uani 1 d . . 
H04 H 0.1190(4) 0.51993(13) 0.4206(4) 0.062 Uiso 1 calc R . 
C05 C 0.3196(4) 0.54938(11) 0.4156(4) 0.0416(6) Uani 1 d . . 
H05 H 0.3770(4) 0.54401(11) 0.5207(4) 0.054 Uiso 1 calc R . 
C06 C 0.3910(3) 0.57126(10) 0.3201(3) 0.0343(6) Uani 1 d . . 
C07 C 0.5558(3) 0.59005(11) 0.3938(3) 0.0376(6) Uani 1 d . . 
H07A H 0.6123(3) 0.56201(11) 0.4703(3) 0.049 Uiso 1 calc R . 
H07B H 0.5591(3) 0.62529(11) 0.4486(3) 0.049 Uiso 1 calc R . 
C08 C 0.6375(3) 0.59881(10) 0.2813(3) 0.0337(5) Uani 1 d . . 
H08 H 0.6608(3) 0.56151(10) 0.2493(3) 0.044 Uiso 1 calc R . 
C09 C 0.7892(3) 0.62999(12) 0.3624(4) 0.0411(6) Uani 1 d . . 
H09A H 0.8461(3) 0.61138(12) 0.4603(4) 0.053 Uiso 1 calc R . 
H09B H 0.8504(3) 0.62772(12) 0.2984(4) 0.053 Uiso 1 calc R . 
C10 C 0.7662(3) 0.69141(12) 0.3929(3) 0.0371(6) Uani 1 d . . 
C11 C 0.8813(4) 0.7208(2) 0.5098(4) 0.0514(8) Uani 1 d . . 
H11 H 0.9700(4) 0.7019(2) 0.5725(4) 0.067 Uiso 1 calc R . 
C12 C 0.8638(5) 0.7781(2) 0.5327(5) 0.0660(12) Uani 1 d . . 
H12 H 0.9406(5) 0.7973(2) 0.6114(5) 0.086 Uiso 1 calc R . 
C13 C 0.7351(5) 0.8063(2) 0.4407(5) 0.0647(11) Uani 1 d . . 
H13 H 0.7253(5) 0.8448(2) 0.4557(5) 0.084 Uiso 1 calc R . 
C14 C 0.6194(4) 0.77785(12) 0.3255(5) 0.0496(8) Uani 1 d . . 
H14 H 0.5320(4) 0.79743(12) 0.2633(5) 0.065 Uiso 1 calc R . 
C15 C 0.6320(3) 0.71985(10) 0.3012(3) 0.0359(6) Uani 1 d . . 
C16 C 0.4970(3) 0.68946(10) 0.1854(3) 0.0339(6) Uani 1 d . . 
H16A H 0.4527(3) 0.71323(10) 0.0942(3) 0.044 Uiso 1 calc R . 
H16B H 0.4196(3) 0.68431(10) 0.2301(3) 0.044 Uiso 1 calc R . 
C17 C 0.5350(3) 0.63128(10) 0.1339(3) 0.0303(5) Uani 1 d . . 
C18 C 0.3841(3) 0.59725(11) 0.0525(3) 0.0333(5) Uani 1 d . . 
H18 H 0.4143(3) 0.56241(11) 0.0141(3) 0.043 Uiso 1 calc R . 
C19 C 0.6203(3) 0.63672(11) 0.0214(3) 0.0345(6) Uani 1 d . . 
C20 C 0.6649(4) 0.68829(13) -0.0202(4) 0.0450(7) Uani 1 d . . 
H20 H 0.6437(4) 0.72147(13) 0.0219(4) 0.058 Uiso 1 calc R . 
C21 C 0.7401(4) 0.6914(2) -0.1226(4) 0.0560(8) Uani 1 d . . 
H21 H 0.7681(4) 0.7265(2) -0.1490(4) 0.073 Uiso 1 calc R . 
C22 C 0.7739(4) 0.6429(2) -0.1858(4) 0.0575(9) Uani 1 d . . 
H22 H 0.8248(4) 0.6451(2) -0.2544(4) 0.075 Uiso 1 calc R . 
C23 C 0.7316(4) 0.5912(2) -0.1466(5) 0.0574(9) Uani 1 d . . 
H23 H 0.7532(4) 0.5582(2) -0.1893(5) 0.075 Uiso 1 calc R . 
C24 C 0.6567(4) 0.58825(13) -0.0431(4) 0.0468(7) Uani 1 d . . 
H24 H 0.6302(4) 0.55300(13) -0.0161(4) 0.061 Uiso 1 calc R . 
C25 C 0.2780(4) 0.62913(13) -0.0913(3) 0.0442(7) Uani 1 d . . 
H25A H 0.3389(4) 0.65546(13) -0.1247(3) 0.057 Uiso 1 calc R . 
H25B H 0.2042(4) 0.65095(13) -0.0640(3) 0.057 Uiso 1 calc R . 
 
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 
Br01 0.0646(3) 0.0879(4) 0.0383(2) -0.0070(2) 0.0073(2) -0.0226(2) 
C01 0.0388(14) 0.0219(11) 0.0425(15) -0.0023(10) 0.0152(12) -0.0028(9) 
C02 0.0405(15) 0.0412(15) 0.048(2) -0.0038(13) 0.0146(13) -0.0060(12) 
C03 0.044(2) 0.046(2) 0.065(2) -0.0100(15) 0.026(2) -0.0107(13) 
C04 0.061(2) 0.0381(15) 0.057(2) -0.0074(13) 0.035(2) -0.0112(13) 
C05 0.056(2) 0.0284(13) 0.043(2) -0.0011(11) 0.0219(13) -0.0049(12) 
C06 0.0439(15) 0.0199(11) 0.0392(14) -0.0009(9) 0.0157(12) -0.0006(10) 
C07 0.0444(15) 0.0284(12) 0.0355(14) 0.0040(10) 0.0097(12) -0.0018(11) 
C08 0.0368(13) 0.0227(11) 0.0377(14) -0.0003(10) 0.0095(11) 0.0037(10) 
C09 0.0332(13) 0.0374(14) 0.048(2) -0.0008(12) 0.0103(12) 0.0044(11) 
C10 0.0407(14) 0.0349(13) 0.0392(14) -0.0046(11) 0.0192(12) -0.0100(11) 
C11 0.049(2) 0.062(2) 0.047(2) -0.0101(15) 0.0227(14) -0.021(2) 
C12 0.080(3) 0.064(2) 0.066(2) -0.035(2) 0.042(2) -0.048(2) 
C13 0.089(3) 0.040(2) 0.087(3) -0.026(2) 0.059(3) -0.028(2) 
C14 0.063(2) 0.0255(13) 0.077(2) -0.0102(13) 0.045(2) -0.0083(12) 
C15 0.0449(15) 0.0240(12) 0.048(2) -0.0042(10) 0.0277(13) -0.0049(10) 
C16 0.0368(13) 0.0221(11) 0.0447(15) 0.0035(10) 0.0172(11) 0.0039(9) 
C17 0.0318(12) 0.0211(11) 0.0364(13) -0.0014(9) 0.0110(10) 0.0010(9) 
C18 0.0348(13) 0.0260(11) 0.0359(13) -0.0011(10) 0.0095(11) -0.0009(10) 
C19 0.0312(12) 0.0328(13) 0.0374(14) -0.0003(10) 0.0105(11) 0.0013(10) 
C20 0.054(2) 0.0398(15) 0.044(2) -0.0039(12) 0.0222(14) -0.0088(13) 
C21 0.064(2) 0.062(2) 0.048(2) -0.004(2) 0.027(2) -0.017(2) 
C22 0.052(2) 0.083(3) 0.043(2) -0.005(2) 0.0246(15) -0.002(2) 
C23 0.058(2) 0.062(2) 0.060(2) -0.008(2) 0.031(2) 0.012(2) 
C24 0.051(2) 0.039(2) 0.056(2) -0.0044(13) 0.0257(15) 0.0046(13) 
C25 0.0415(15) 0.045(2) 0.0380(15) 0.0038(12) 0.0051(12) -0.0079(12) 
 
#=======================================================================


# 10. MOLECULAR GEOMETRY

_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 
Br01 C25 1.951(3) . ? 
C01 C06 1.393(4) . ? 
C01 C02 1.402(4) . ? 
C01 C18 1.524(4) . ? 
C02 C03 1.382(5) . ? 
C03 C04 1.375(5) . ? 
C04 C05 1.386(5) . ? 
C05 C06 1.395(4) . ? 
C06 C07 1.503(4) . ? 
C07 C08 1.524(4) . ? 
C08 C09 1.526(4) . ? 
C08 C17 1.549(4) . ? 
C09 C10 1.509(4) . ? 
C10 C11 1.395(4) . ? 
C10 C15 1.398(4) . ? 
C11 C12 1.390(5) . ? 
C12 C13 1.362(6) . ? 
C13 C14 1.379(5) . ? 
C14 C15 1.401(4) . ? 
C15 C16 1.501(4) . ? 
C16 C17 1.540(3) . ? 
C17 C19 1.541(4) . ? 
C17 C18 1.555(3) . ? 
C18 C25 1.531(4) . ? 
C19 C20 1.389(4) . ? 
C19 C24 1.393(4) . ? 
C20 C21 1.382(4) . ? 
C21 C22 1.378(5) . ? 
C22 C23 1.375(6) . ? 
C23 C24 1.389(5) . ? 
 
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 
C06 C01 C02 118.4(3) . . ? 
C06 C01 C18 120.8(2) . . ? 
C02 C01 C18 120.7(3) . . ? 
C03 C02 C01 121.2(3) . . ? 
C04 C03 C02 120.3(3) . . ? 
C03 C04 C05 119.3(3) . . ? 
C04 C05 C06 121.2(3) . . ? 
C01 C06 C05 119.6(3) . . ? 
C01 C06 C07 121.8(2) . . ? 
C05 C06 C07 118.4(3) . . ? 
C06 C07 C08 115.0(2) . . ? 
C07 C08 C09 110.0(2) . . ? 
C07 C08 C17 111.6(2) . . ? 
C09 C08 C17 110.6(2) . . ? 
C10 C09 C08 112.6(2) . . ? 
C11 C10 C15 119.5(3) . . ? 
C11 C10 C09 120.0(3) . . ? 
C15 C10 C09 120.5(2) . . ? 
C12 C11 C10 120.1(4) . . ? 
C13 C12 C11 120.5(3) . . ? 
C12 C13 C14 120.2(3) . . ? 
C13 C14 C15 120.8(4) . . ? 
C10 C15 C14 118.9(3) . . ? 
C10 C15 C16 122.1(2) . . ? 
C14 C15 C16 118.9(3) . . ? 
C15 C16 C17 114.7(2) . . ? 
C16 C17 C19 112.1(2) . . ? 
C16 C17 C08 107.8(2) . . ? 
C19 C17 C08 109.5(2) . . ? 
C16 C17 C18 109.7(2) . . ? 
C19 C17 C18 108.8(2) . . ? 
C08 C17 C18 108.9(2) . . ? 
C01 C18 C25 114.1(2) . . ? 
C01 C18 C17 113.7(2) . . ? 
C25 C18 C17 110.2(2) . . ? 
C20 C19 C24 117.0(3) . . ? 
C20 C19 C17 123.3(2) . . ? 
C24 C19 C17 119.8(2) . . ? 
C21 C20 C19 121.5(3) . . ? 
C22 C21 C20 120.4(3) . . ? 
C23 C22 C21 119.5(3) . . ? 
C22 C23 C24 119.8(3) . . ? 
C23 C24 C19 121.8(3) . . ? 
C18 C25 Br01 112.7(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 
 C06 C01 C02 C03 -1.4(4) . . . . ? 
 C18 C01 C02 C03 175.4(3) . . . . ? 
 C01 C02 C03 C04 -1.3(5) . . . . ? 
 C02 C03 C04 C05 3.0(5) . . . . ? 
 C03 C04 C05 C06 -1.8(4) . . . . ? 
 C02 C01 C06 C05 2.5(4) . . . . ? 
 C18 C01 C06 C05 -174.3(2) . . . . ? 
 C02 C01 C06 C07 -173.1(2) . . . . ? 
 C18 C01 C06 C07 10.0(4) . . . . ? 
 C04 C05 C06 C01 -0.9(4) . . . . ? 
 C04 C05 C06 C07 174.9(3) . . . . ? 
 C01 C06 C07 C08 -19.5(3) . . . . ? 
 C05 C06 C07 C08 164.8(2) . . . . ? 
 C06 C07 C08 C09 167.4(2) . . . . ? 
 C06 C07 C08 C17 44.3(3) . . . . ? 
 C07 C08 C09 C10 -71.6(3) . . . . ? 
 C17 C08 C09 C10 52.1(3) . . . . ? 
 C08 C09 C10 C11 157.4(3) . . . . ? 
 C08 C09 C10 C15 -24.8(4) . . . . ? 
 C15 C10 C11 C12 -1.3(4) . . . . ? 
 C09 C10 C11 C12 176.6(3) . . . . ? 
 C10 C11 C12 C13 -0.6(5) . . . . ? 
 C11 C12 C13 C14 1.2(5) . . . . ? 
 C12 C13 C14 C15 0.0(5) . . . . ? 
 C11 C10 C15 C14 2.4(4) . . . . ? 
 C09 C10 C15 C14 -175.5(3) . . . . ? 
 C11 C10 C15 C16 -173.3(3) . . . . ? 
 C09 C10 C15 C16 8.8(4) . . . . ? 
 C13 C14 C15 C10 -1.8(4) . . . . ? 
 C13 C14 C15 C16 174.0(3) . . . . ? 
 C10 C15 C16 C17 -20.4(4) . . . . ? 
 C14 C15 C16 C17 163.9(2) . . . . ? 
 C15 C16 C17 C19 -74.6(3) . . . . ? 
 C15 C16 C17 C08 45.9(3) . . . . ? 
 C15 C16 C17 C18 164.4(2) . . . . ? 
 C07 C08 C17 C16 60.2(3) . . . . ? 
 C09 C08 C17 C16 -62.6(3) . . . . ? 
 C07 C08 C17 C19 -177.6(2) . . . . ? 
 C09 C08 C17 C19 59.6(3) . . . . ? 
 C07 C08 C17 C18 -58.8(3) . . . . ? 
 C09 C08 C17 C18 178.4(2) . . . . ? 
 C06 C01 C18 C25 -153.0(2) . . . . ? 
 C02 C01 C18 C25 30.2(3) . . . . ? 
 C06 C01 C18 C17 -25.6(3) . . . . ? 
 C02 C01 C18 C17 157.6(2) . . . . ? 
 C16 C17 C18 C01 -68.9(3) . . . . ? 
 C19 C17 C18 C01 168.2(2) . . . . ? 
 C08 C17 C18 C01 48.9(3) . . . . ? 
 C16 C17 C18 C25 60.6(3) . . . . ? 
 C19 C17 C18 C25 -62.4(3) . . . . ? 
 C08 C17 C18 C25 178.4(2) . . . . ? 
 C16 C17 C19 C20 3.6(4) . . . . ? 
 C08 C17 C19 C20 -116.0(3) . . . . ? 
 C18 C17 C19 C20 125.1(3) . . . . ? 
 C16 C17 C19 C24 -176.8(3) . . . . ? 
 C08 C17 C19 C24 63.6(3) . . . . ? 
 C18 C17 C19 C24 -55.2(3) . . . . ? 
 C24 C19 C20 C21 0.9(5) . . . . ? 
 C17 C19 C20 C21 -179.5(3) . . . . ? 
 C19 C20 C21 C22 -0.4(5) . . . . ? 
 C20 C21 C22 C23 0.2(6) . . . . ? 
 C21 C22 C23 C24 -0.5(6) . . . . ? 
 C22 C23 C24 C19 1.0(6) . . . . ? 
 C20 C19 C24 C23 -1.2(5) . . . . ? 
 C17 C19 C24 C23 179.1(3) . . . . ? 
 C01 C18 C25 Br01 -88.1(3) . . . . ? 
 C17 C18 C25 Br01 142.6(2) . . . . ?