# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Zhan-Ting Li'
_publ_contact_author_email       ZTLI@MAIL.SIOC.AC.CN

_publ_section_title              
;
Intramolecular six-membered N-H***Br and N-H***I
hydrogen bonding
in aromatic amides in the absence of competing interactions
;
loop_
_publ_author_name
'Zhan-Ting Li.'
'Long Jiang.'
'Tong-Bu Lu.'
'Yuan-Yuan Zhu.'

# Attachment 'ZHU-YY-S-3.cif'

data_080701b_0m
_database_code_depnum_ccdc_archive 'CCDC 699574'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 Br N2 O, C H Cl3'
_chemical_formula_sum            'C27 H22 Br Cl3 N2 O'
_chemical_formula_weight         576.73

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'
Br Br -0.2901 2.4595 '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           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.101(7)
_cell_length_b                   10.531(6)
_cell_length_c                   19.954(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.860(7)
_cell_angle_gamma                90.00
_cell_volume                     2673(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2120
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      20.75

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_T_max  0.7678
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13228
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4723
_reflns_number_gt                2504
_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1031P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4723
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1650
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Br1 Br 0.36713(5) 0.28740(7) 0.15383(4) 0.0657(3) Uani 1 1 d . . .
Cl1 Cl 0.3192(2) -0.2939(2) -0.01439(15) 0.1224(10) Uani 1 1 d . . .
Cl2 Cl 0.17647(18) -0.0912(3) -0.06745(12) 0.1071(8) Uani 1 1 d . . .
Cl3 Cl 0.37868(18) -0.0303(3) 0.02107(13) 0.1128(9) Uani 1 1 d . . .
C1 C 0.2367(4) 0.2852(6) 0.0849(3) 0.0461(15) Uani 1 1 d . . .
C2 C 0.2151(5) 0.3907(6) 0.0430(3) 0.0567(17) Uani 1 1 d . . .
H2 H 0.2601 0.4602 0.0516 0.068 Uiso 1 1 calc R . .
C3 C 0.1285(6) 0.3944(7) -0.0107(3) 0.067(2) Uani 1 1 d . . .
H3 H 0.1158 0.4663 -0.0385 0.080 Uiso 1 1 calc R . .
C4 C 0.0588(5) 0.2927(6) -0.0249(3) 0.0544(17) Uani 1 1 d . . .
C5 C 0.0793(5) 0.1889(6) 0.0194(3) 0.0441(15) Uani 1 1 d . . .
H5 H 0.0326 0.1210 0.0118 0.053 Uiso 1 1 calc R . .
C6 C 0.1672(4) 0.1829(5) 0.0750(3) 0.0377(13) Uani 1 1 d . . .
C7 C 0.1704(4) 0.0683(6) 0.1206(3) 0.0382(13) Uani 1 1 d . . .
C8 C 0.2168(4) -0.0087(5) 0.2459(3) 0.0358(13) Uani 1 1 d . . .
C9 C 0.2811(4) 0.0589(6) 0.3111(3) 0.0420(14) Uani 1 1 d . . .
C10 C 0.2434(5) 0.1741(7) 0.3310(3) 0.0579(17) Uani 1 1 d . . .
H10 H 0.1815 0.2084 0.3042 0.070 Uiso 1 1 calc R . .
C11 C 0.2966(6) 0.2376(7) 0.3897(4) 0.073(2) Uani 1 1 d . . .
H11 H 0.2714 0.3147 0.4020 0.088 Uiso 1 1 calc R . .
C12 C 0.3878(6) 0.1852(9) 0.4301(4) 0.077(2) Uani 1 1 d . . .
H12 H 0.4244 0.2274 0.4695 0.092 Uiso 1 1 calc R . .
C13 C 0.4243(6) 0.0703(9) 0.4119(4) 0.071(2) Uani 1 1 d . . .
H13 H 0.4850 0.0353 0.4396 0.086 Uiso 1 1 calc R . .
C14 C 0.3719(5) 0.0066(7) 0.3531(3) 0.0529(17) Uani 1 1 d . . .
H14 H 0.3972 -0.0709 0.3416 0.063 Uiso 1 1 calc R . .
C15 C 0.2772(4) -0.1227(6) 0.2262(3) 0.0419(14) Uani 1 1 d . . .
C16 C 0.3699(5) -0.1011(7) 0.2044(3) 0.0541(17) Uani 1 1 d . . .
H16 H 0.3920 -0.0183 0.2000 0.065 Uiso 1 1 calc R . .
C17 C 0.4288(5) -0.2015(8) 0.1894(3) 0.0637(19) Uani 1 1 d . . .
H17 H 0.4906 -0.1859 0.1757 0.076 Uiso 1 1 calc R . .
C18 C 0.3959(6) -0.3242(8) 0.1947(4) 0.081(2) Uani 1 1 d . . .
H18 H 0.4355 -0.3916 0.1845 0.097 Uiso 1 1 calc R . .
C19 C 0.3046(6) -0.3475(7) 0.2149(4) 0.082(2) Uani 1 1 d . . .
H19 H 0.2825 -0.4306 0.2184 0.098 Uiso 1 1 calc R . .
C20 C 0.2452(5) -0.2468(6) 0.2302(4) 0.0563(17) Uani 1 1 d . . .
H20 H 0.1830 -0.2634 0.2433 0.068 Uiso 1 1 calc R . .
C21 C 0.1095(4) -0.0418(5) 0.2598(3) 0.0355(13) Uani 1 1 d . . .
C22 C 0.1075(5) -0.1075(6) 0.3198(3) 0.0491(16) Uani 1 1 d . . .
H22 H 0.1705 -0.1355 0.3481 0.059 Uiso 1 1 calc R . .
C23 C 0.0132(5) -0.1330(6) 0.3388(3) 0.0546(17) Uani 1 1 d . . .
H23 H 0.0137 -0.1770 0.3793 0.065 Uiso 1 1 calc R . .
C24 C -0.0797(5) -0.0919(6) 0.2968(4) 0.0559(17) Uani 1 1 d . . .
H24 H -0.1429 -0.1075 0.3087 0.067 Uiso 1 1 calc R . .
C25 C -0.0790(5) -0.0284(7) 0.2378(4) 0.068(2) Uani 1 1 d . . .
H25 H -0.1422 -0.0011 0.2094 0.081 Uiso 1 1 calc R . .
C26 C 0.0150(4) -0.0033(6) 0.2190(3) 0.0505(16) Uani 1 1 d . . .
H26 H 0.0135 0.0401 0.1782 0.061 Uiso 1 1 calc R . .
N1 N 0.2035(3) 0.0888(4) 0.1896(2) 0.0381(11) Uani 1 1 d . . .
H1 H 0.2184 0.1659 0.2024 0.046 Uiso 1 1 calc R . .
N2 N -0.0295(5) 0.2951(6) -0.0803(3) 0.092(2) Uani 1 1 d . . .
H2A H -0.0722 0.2318 -0.0874 0.111 Uiso 1 1 calc R . .
H2B H -0.0412 0.3599 -0.1073 0.111 Uiso 1 1 calc R . .
O1 O 0.1389(3) -0.0358(4) 0.09640(19) 0.0480(10) Uani 1 1 d . . .
C27 C 0.2779(5) -0.1415(8) -0.0004(4) 0.074(2) Uani 1 1 d . . .
H27 H 0.2479 -0.1477 0.0401 0.088 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.921(6) . ?
Cl1 C27 1.737(9) . ?
Cl2 C27 1.728(7) . ?
Cl3 C27 1.740(8) . ?
C1 C2 1.377(8) . ?
C1 C6 1.394(8) . ?
C2 C3 1.362(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(8) . ?
C4 N2 1.396(8) . ?
C5 C6 1.396(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(8) . ?
C7 O1 1.229(6) . ?
C7 N1 1.357(6) . ?
C8 N1 1.501(7) . ?
C8 C21 1.537(7) . ?
C8 C15 1.539(8) . ?
C8 C9 1.544(7) . ?
C9 C14 1.394(8) . ?
C9 C10 1.403(9) . ?
C10 C11 1.384(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.381(8) . ?
C15 C16 1.403(8) . ?
C16 C17 1.383(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.370(7) . ?
C21 C22 1.388(7) . ?
C22 C23 1.402(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C27 H27 0.9800 . ?

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 120.4(6) . . ?
C2 C1 Br1 116.3(5) . . ?
C6 C1 Br1 123.3(4) . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.3(6) . . ?
C5 C4 N2 121.0(6) . . ?
C3 C4 N2 121.7(6) . . ?
C4 C5 C6 122.5(6) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 117.6(5) . . ?
C1 C6 C7 127.7(5) . . ?
C5 C6 C7 114.5(5) . . ?
O1 C7 N1 122.4(5) . . ?
O1 C7 C6 121.3(5) . . ?
N1 C7 C6 116.2(5) . . ?
N1 C8 C21 110.1(4) . . ?
N1 C8 C15 108.4(4) . . ?
C21 C8 C15 114.7(5) . . ?
N1 C8 C9 104.9(4) . . ?
C21 C8 C9 106.9(4) . . ?
C15 C8 C9 111.4(4) . . ?
C14 C9 C10 118.7(6) . . ?
C14 C9 C8 122.6(6) . . ?
C10 C9 C8 118.6(5) . . ?
C11 C10 C9 121.1(7) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.3(7) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.1(7) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.1(7) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C9 119.8(7) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C20 C15 C16 117.9(6) . . ?
C20 C15 C8 122.8(5) . . ?
C16 C15 C8 119.3(5) . . ?
C17 C16 C15 120.8(7) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.1(6) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.1(7) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.1(7) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.0(6) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C26 C21 C22 117.4(5) . . ?
C26 C21 C8 124.1(5) . . ?
C22 C21 C8 118.4(5) . . ?
C21 C22 C23 121.9(6) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
C24 C23 C22 118.9(6) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 119.8(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 121.1(6) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 120.9(6) . . ?
C21 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C7 N1 C8 127.1(5) . . ?
C7 N1 H1 116.5 . . ?
C8 N1 H1 116.5 . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
Cl2 C27 Cl1 111.7(4) . . ?
Cl2 C27 Cl3 112.4(5) . . ?
Cl1 C27 Cl3 114.5(4) . . ?
Cl2 C27 H27 105.8 . . ?
Cl1 C27 H27 105.8 . . ?
Cl3 C27 H27 105.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.23 3.065(8) 163.1 3
C27 H27 O1 0.98 2.34 3.158(8) 140.7 .
N1 H1 Br1 0.86 2.70 3.196(4) 118.3 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.083

data_080703c_0m
_database_code_depnum_ccdc_archive 'CCDC 699575'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 I N2 O, C H Cl3'
_chemical_formula_sum            'C27 H22 Cl3 I N2 O'
_chemical_formula_weight         623.72

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'
I I -0.4742 1.8119 '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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.107(5)
_cell_length_b                   10.608(4)
_cell_length_c                   19.586(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.603(5)
_cell_angle_gamma                90.00
_cell_volume                     2657.4(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4402
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    1.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7496
_exptl_absorpt_correction_T_max  0.8031
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13422
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4697
_reflns_number_gt                3699
_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+5.2020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4697
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
I1 I 0.37834(3) 0.28805(3) 0.152148(19) 0.05892(15) Uani 1 1 d . . .
C1 C 0.2325(3) 0.2842(4) 0.0810(2) 0.0386(10) Uani 1 1 d . . .
C2 C 0.2083(4) 0.3885(5) 0.0387(3) 0.0510(12) Uani 1 1 d . . .
H2 H 0.2531 0.4576 0.0455 0.061 Uiso 1 1 calc R . .
C3 C 0.1192(4) 0.3922(5) -0.0136(3) 0.0575(14) Uani 1 1 d . . .
H3 H 0.1035 0.4646 -0.0406 0.069 Uiso 1 1 calc R . .
C4 C 0.0523(4) 0.2894(5) -0.0265(2) 0.0497(12) Uani 1 1 d . . .
C5 C 0.0760(3) 0.1864(4) 0.0168(2) 0.0384(10) Uani 1 1 d . . .
H5 H 0.0317 0.1170 0.0092 0.046 Uiso 1 1 calc R . .
C6 C 0.1639(3) 0.1818(4) 0.0717(2) 0.0329(9) Uani 1 1 d . . .
C7 C 0.1696(3) 0.0679(4) 0.1178(2) 0.0327(9) Uani 1 1 d . . .
C8 C 0.2124(3) -0.0045(4) 0.2442(2) 0.0343(9) Uani 1 1 d . . .
C9 C 0.2752(3) 0.0640(4) 0.3094(2) 0.0366(10) Uani 1 1 d . . .
C10 C 0.2374(4) 0.1775(5) 0.3296(2) 0.0518(12) Uani 1 1 d . . .
H10 H 0.1755 0.2104 0.3032 0.062 Uiso 1 1 calc R . .
C11 C 0.2893(5) 0.2424(5) 0.3878(3) 0.0650(15) Uani 1 1 d . . .
H11 H 0.2632 0.3188 0.3999 0.078 Uiso 1 1 calc R . .
C12 C 0.3805(5) 0.1933(6) 0.4280(3) 0.0680(17) Uani 1 1 d . . .
H12 H 0.4165 0.2366 0.4672 0.082 Uiso 1 1 calc R . .
C13 C 0.4169(4) 0.0810(6) 0.4097(3) 0.0634(16) Uani 1 1 d . . .
H13 H 0.4779 0.0474 0.4370 0.076 Uiso 1 1 calc R . .
C14 C 0.3649(3) 0.0155(5) 0.3509(2) 0.0475(12) Uani 1 1 d . . .
H14 H 0.3909 -0.0614 0.3396 0.057 Uiso 1 1 calc R . .
C15 C 0.2726(3) -0.1178(4) 0.2250(2) 0.0360(10) Uani 1 1 d . . .
C16 C 0.3647(4) -0.0963(5) 0.2022(2) 0.0471(11) Uani 1 1 d . . .
H16 H 0.3869 -0.0141 0.1975 0.056 Uiso 1 1 calc R . .
C17 C 0.4233(4) -0.1962(5) 0.1865(3) 0.0556(13) Uani 1 1 d . . .
H17 H 0.4844 -0.1806 0.1711 0.067 Uiso 1 1 calc R . .
C18 C 0.3930(5) -0.3163(5) 0.1932(3) 0.0669(16) Uani 1 1 d . . .
H18 H 0.4334 -0.3830 0.1833 0.080 Uiso 1 1 calc R . .
C19 C 0.3025(5) -0.3390(5) 0.2147(3) 0.0714(17) Uani 1 1 d . . .
H19 H 0.2811 -0.4216 0.2191 0.086 Uiso 1 1 calc R . .
C20 C 0.2418(4) -0.2400(4) 0.2302(3) 0.0537(13) Uani 1 1 d . . .
H20 H 0.1798 -0.2570 0.2442 0.064 Uiso 1 1 calc R . .
C21 C 0.1057(3) -0.0381(4) 0.2596(2) 0.0328(9) Uani 1 1 d . . .
C22 C 0.1027(4) -0.1013(5) 0.3209(2) 0.0447(11) Uani 1 1 d . . .
H22 H 0.1650 -0.1265 0.3504 0.054 Uiso 1 1 calc R . .
C23 C 0.0092(4) -0.1276(5) 0.3393(3) 0.0526(13) Uani 1 1 d . . .
H23 H 0.0089 -0.1711 0.3805 0.063 Uiso 1 1 calc R . .
C24 C -0.0831(4) -0.0897(5) 0.2971(3) 0.0521(13) Uani 1 1 d . . .
H24 H -0.1462 -0.1068 0.3095 0.063 Uiso 1 1 calc R . .
C25 C -0.0816(4) -0.0266(6) 0.2364(3) 0.0609(15) Uani 1 1 d . . .
H25 H -0.1440 0.0001 0.2077 0.073 Uiso 1 1 calc R . .
C26 C 0.0120(4) -0.0021(5) 0.2175(3) 0.0507(12) Uani 1 1 d . . .
H26 H 0.0116 0.0393 0.1756 0.061 Uiso 1 1 calc R . .
N1 N 0.1993(3) 0.0896(3) 0.18685(17) 0.0339(8) Uani 1 1 d . . .
H1 H 0.2121 0.1668 0.1992 0.041 Uiso 1 1 calc R . .
N2 N -0.0356(4) 0.2915(5) -0.0792(2) 0.0810(17) Uani 1 1 d . . .
H2A H -0.0771 0.2277 -0.0857 0.097 Uiso 1 1 calc R . .
H2B H -0.0492 0.3566 -0.1058 0.097 Uiso 1 1 calc R . .
O1 O 0.1415(2) -0.0361(3) 0.09365(15) 0.0437(7) Uani 1 1 d . . .
C27 C 0.2810(4) -0.1494(6) -0.0020(3) 0.0630(14) Uani 1 1 d . . .
H27 H 0.2529 -0.1551 0.0404 0.076 Uiso 1 1 calc R . .
Cl1 Cl 0.32603(17) -0.29778(18) -0.01595(12) 0.1099(7) Uani 1 1 d . . .
Cl2 Cl 0.17751(14) -0.1061(2) -0.06923(9) 0.0990(6) Uani 1 1 d . . .
Cl3 Cl 0.37735(16) -0.0362(2) 0.01411(12) 0.1131(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.106(4) . ?
C1 C2 1.378(6) . ?
C1 C6 1.396(6) . ?
C2 C3 1.375(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(7) . ?
C3 H3 0.9300 . ?
C4 N2 1.369(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.394(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(6) . ?
C7 O1 1.225(5) . ?
C7 N1 1.343(5) . ?
C8 N1 1.484(5) . ?
C8 C15 1.530(6) . ?
C8 C21 1.535(6) . ?
C8 C9 1.543(6) . ?
C9 C14 1.375(6) . ?
C9 C10 1.392(7) . ?
C10 C11 1.377(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.361(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.368(6) . ?
C15 C16 1.395(6) . ?
C16 C17 1.383(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.349(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.376(6) . ?
C21 C22 1.384(6) . ?
C22 C23 1.379(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C27 Cl3 1.722(6) . ?
C27 Cl1 1.723(6) . ?
C27 Cl2 1.734(6) . ?
C27 H27 0.9800 . ?

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 119.3(4) . . ?
C2 C1 I1 116.1(3) . . ?
C6 C1 I1 124.6(3) . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N2 C4 C5 121.2(5) . . ?
N2 C4 C3 121.2(4) . . ?
C5 C4 C3 117.6(4) . . ?
C4 C5 C6 122.7(4) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 118.3(4) . . ?
C5 C6 C7 114.6(4) . . ?
C1 C6 C7 127.0(4) . . ?
O1 C7 N1 122.6(4) . . ?
O1 C7 C6 121.5(4) . . ?
N1 C7 C6 115.7(4) . . ?
N1 C8 C15 108.9(3) . . ?
N1 C8 C21 110.2(3) . . ?
C15 C8 C21 114.0(3) . . ?
N1 C8 C9 105.2(3) . . ?
C15 C8 C9 111.3(3) . . ?
C21 C8 C9 106.9(3) . . ?
C14 C9 C10 117.9(4) . . ?
C14 C9 C8 123.1(4) . . ?
C10 C9 C8 119.0(4) . . ?
C11 C10 C9 121.7(5) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.5(5) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.3(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C9 C14 C13 120.3(5) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C20 C15 C16 118.0(4) . . ?
C20 C15 C8 123.4(4) . . ?
C16 C15 C8 118.6(4) . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.5(5) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.8(5) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.4(5) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C26 C21 C22 117.6(4) . . ?
C26 C21 C8 123.4(4) . . ?
C22 C21 C8 118.8(4) . . ?
C23 C22 C21 121.3(4) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 120.1(5) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.4(5) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C24 C25 C26 120.4(5) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C21 C26 C25 121.1(4) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C7 N1 C8 127.4(3) . . ?
C7 N1 H1 116.3 . . ?
C8 N1 H1 116.3 . . ?
C4 N2 H2A 120.0 . . ?
C4 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
Cl3 C27 Cl1 113.8(3) . . ?
Cl3 C27 Cl2 112.0(3) . . ?
Cl1 C27 Cl2 111.1(3) . . ?
Cl3 C27 H27 106.5 . . ?
Cl1 C27 H27 106.5 . . ?
Cl2 C27 H27 106.5 . . ?

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 -1.5(7) . . . . ?
I1 C1 C2 C3 174.7(4) . . . . ?
C1 C2 C3 C4 -1.9(8) . . . . ?
C2 C3 C4 N2 -178.8(5) . . . . ?
C2 C3 C4 C5 2.9(8) . . . . ?
N2 C4 C5 C6 -178.9(5) . . . . ?
C3 C4 C5 C6 -0.6(7) . . . . ?
C4 C5 C6 C1 -2.7(6) . . . . ?
C4 C5 C6 C7 173.4(4) . . . . ?
C2 C1 C6 C5 3.7(6) . . . . ?
I1 C1 C6 C5 -172.2(3) . . . . ?
C2 C1 C6 C7 -171.8(4) . . . . ?
I1 C1 C6 C7 12.3(6) . . . . ?
C5 C6 C7 O1 37.9(5) . . . . ?
C1 C6 C7 O1 -146.4(4) . . . . ?
C5 C6 C7 N1 -137.0(4) . . . . ?
C1 C6 C7 N1 38.7(6) . . . . ?
N1 C8 C9 C14 -128.1(4) . . . . ?
C15 C8 C9 C14 -10.3(5) . . . . ?
C21 C8 C9 C14 114.8(4) . . . . ?
N1 C8 C9 C10 55.1(5) . . . . ?
C15 C8 C9 C10 172.8(4) . . . . ?
C21 C8 C9 C10 -62.1(5) . . . . ?
C14 C9 C10 C11 2.3(7) . . . . ?
C8 C9 C10 C11 179.3(5) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C10 C11 C12 C13 -0.5(9) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C10 C9 C14 C13 -2.0(7) . . . . ?
C8 C9 C14 C13 -178.9(4) . . . . ?
C12 C13 C14 C9 0.6(8) . . . . ?
N1 C8 C15 C20 -131.9(4) . . . . ?
C21 C8 C15 C20 -8.5(6) . . . . ?
C9 C8 C15 C20 112.6(5) . . . . ?
N1 C8 C15 C16 49.2(5) . . . . ?
C21 C8 C15 C16 172.6(4) . . . . ?
C9 C8 C15 C16 -66.4(5) . . . . ?
C20 C15 C16 C17 -1.0(7) . . . . ?
C8 C15 C16 C17 177.9(4) . . . . ?
C15 C16 C17 C18 -0.3(8) . . . . ?
C16 C17 C18 C19 1.1(9) . . . . ?
C17 C18 C19 C20 -0.5(10) . . . . ?
C16 C15 C20 C19 1.6(8) . . . . ?
C8 C15 C20 C19 -177.3(5) . . . . ?
C18 C19 C20 C15 -0.9(9) . . . . ?
N1 C8 C21 C26 10.5(6) . . . . ?
C15 C8 C21 C26 -112.2(5) . . . . ?
C9 C8 C21 C26 124.3(4) . . . . ?
N1 C8 C21 C22 -165.4(4) . . . . ?
C15 C8 C21 C22 71.8(5) . . . . ?
C9 C8 C21 C22 -51.6(5) . . . . ?
C26 C21 C22 C23 0.1(7) . . . . ?
C8 C21 C22 C23 176.3(4) . . . . ?
C21 C22 C23 C24 -0.9(7) . . . . ?
C22 C23 C24 C25 0.5(8) . . . . ?
C23 C24 C25 C26 0.6(8) . . . . ?
C22 C21 C26 C25 1.0(7) . . . . ?
C8 C21 C26 C25 -175.0(5) . . . . ?
C24 C25 C26 C21 -1.3(8) . . . . ?
O1 C7 N1 C8 5.7(6) . . . . ?
C6 C7 N1 C8 -179.5(3) . . . . ?
C15 C8 N1 C7 45.5(5) . . . . ?
C21 C8 N1 C7 -80.2(5) . . . . ?
C9 C8 N1 C7 164.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.19 3.029(6) 163.9 3
C27 H27 O1 0.98 2.34 3.129(6) 136.9 .
N1 H1 I1 0.86 2.85 3.331(3) 117.0 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.077

data_cd27557
_database_code_depnum_ccdc_archive 'CCDC 699576'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H35 Br N2 O2, C4 H8 O2'
_chemical_formula_sum            'C50 H43 Br N2 O4'
_chemical_formula_weight         815.77

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-p 1'

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

_cell_length_a                   10.0756(13)
_cell_length_b                   13.5573(17)
_cell_length_c                   16.036(2)
_cell_angle_alpha                99.681(3)
_cell_angle_beta                 95.973(2)
_cell_angle_gamma                99.563(2)
_cell_volume                     2109.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1849
_cell_measurement_theta_min      4.579
_cell_measurement_theta_max      43.376

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6855
_exptl_absorpt_correction_T_max  0.7493
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11628
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_sigmaI/netI    0.1400
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             8165
_reflns_number_gt                4062
_reflns_threshold_expression     >2sigma(I)

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8165
_refine_ls_number_parameters     516
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.906
_refine_ls_shift/su_max          0.003
_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
Br1 Br -0.11149(5) 0.52046(4) 0.67128(3) 0.0559(2) Uani 1 1 d . . .
O1 O -0.1906(4) 0.1541(3) 0.3078(3) 0.0904(14) Uani 1 1 d . . .
O2 O 0.2888(3) 0.4729(3) 0.6407(2) 0.0570(9) Uani 1 1 d . . .
O3 O 0.3105(4) 0.2150(4) 0.4296(3) 0.1083(15) Uani 1 1 d U . .
O4 O 0.5297(5) 0.2388(4) 0.4353(4) 0.1349(15) Uani 1 1 d U . .
N1 N 0.0179(4) 0.2231(3) 0.3771(2) 0.0431(10) Uani 1 1 d . . .
H1A H 0.1029 0.2231 0.3755 0.052 Uiso 1 1 calc R . .
N2 N 0.1460(3) 0.4225(3) 0.7319(2) 0.0389(9) Uani 1 1 d . . .
H2A H 0.0613 0.4057 0.7365 0.047 Uiso 1 1 calc R . .
C1 C -0.0156(4) 0.2912(3) 0.4447(3) 0.0356(11) Uani 1 1 d . . .
C2 C 0.0830(4) 0.3317(3) 0.5138(3) 0.0366(11) Uani 1 1 d . . .
H2 H 0.1678 0.3132 0.5136 0.044 Uiso 1 1 calc R . .
C3 C 0.0602(4) 0.3986(3) 0.5831(3) 0.0346(10) Uani 1 1 d . . .
C4 C -0.0671(4) 0.4258(3) 0.5813(3) 0.0373(11) Uani 1 1 d . . .
C5 C -0.1650(5) 0.3865(4) 0.5112(3) 0.0457(12) Uani 1 1 d . . .
H5 H -0.2495 0.4057 0.5106 0.055 Uiso 1 1 calc R . .
C6 C -0.1409(5) 0.3203(3) 0.4430(3) 0.0415(11) Uani 1 1 d . . .
H6 H -0.2075 0.2951 0.3961 0.050 Uiso 1 1 calc R . .
C7 C -0.0693(5) 0.1576(4) 0.3144(3) 0.0486(13) Uani 1 1 d . . .
C8 C -0.0047(4) 0.0859(3) 0.2495(3) 0.0411(12) Uani 1 1 d . . .
C9 C 0.0335(4) -0.0049(4) 0.2889(3) 0.0441(12) Uani 1 1 d . . .
C10 C 0.0490(7) -0.0068(4) 0.3743(4) 0.0782(19) Uani 1 1 d . . .
H10 H 0.0299 0.0476 0.4117 0.094 Uiso 1 1 calc R . .
C11 C 0.0896(8) -0.0817(5) 0.4060(4) 0.098(2) Uani 1 1 d . . .
H11 H 0.1030 -0.0781 0.4648 0.118 Uiso 1 1 calc R . .
C12 C 0.1121(6) -0.1652(5) 0.3521(5) 0.0803(19) Uani 1 1 d . . .
H12 H 0.1368 -0.2203 0.3733 0.096 Uiso 1 1 calc R . .
C13 C 0.0972(5) -0.1652(4) 0.2659(4) 0.0688(16) Uani 1 1 d . . .
H13 H 0.1148 -0.2203 0.2284 0.083 Uiso 1 1 calc R . .
C14 C 0.0578(5) -0.0876(4) 0.2350(4) 0.0581(14) Uani 1 1 d . . .
H14 H 0.0467 -0.0897 0.1764 0.070 Uiso 1 1 calc R . .
C15 C 0.1204(5) 0.1527(4) 0.2249(3) 0.0446(12) Uani 1 1 d . . .
C16 C 0.2446(5) 0.1234(4) 0.2239(3) 0.0588(14) Uani 1 1 d . . .
H16 H 0.2554 0.0619 0.2396 0.071 Uiso 1 1 calc R . .
C17 C 0.3546(5) 0.1838(5) 0.2001(4) 0.0726(17) Uani 1 1 d . . .
H17 H 0.4377 0.1625 0.2003 0.087 Uiso 1 1 calc R . .
C18 C 0.3416(7) 0.2707(5) 0.1772(4) 0.0788(19) Uani 1 1 d . . .
H18 H 0.4152 0.3113 0.1616 0.095 Uiso 1 1 calc R . .
C19 C 0.2180(7) 0.3009(4) 0.1765(3) 0.0678(16) Uani 1 1 d . . .
H19 H 0.2087 0.3620 0.1597 0.081 Uiso 1 1 calc R . .
C20 C 0.1073(5) 0.2426(4) 0.2001(3) 0.0511(13) Uani 1 1 d . . .
H20 H 0.0245 0.2644 0.1991 0.061 Uiso 1 1 calc R . .
C21 C -0.1127(5) 0.0407(3) 0.1706(3) 0.0455(12) Uani 1 1 d . . .
C22 C -0.0949(5) 0.0580(4) 0.0886(3) 0.0543(13) Uani 1 1 d . . .
H22 H -0.0149 0.0977 0.0796 0.065 Uiso 1 1 calc R . .
C23 C -0.1963(6) 0.0162(4) 0.0205(3) 0.0674(16) Uani 1 1 d . . .
H23 H -0.1843 0.0285 -0.0338 0.081 Uiso 1 1 calc R . .
C24 C -0.3165(6) -0.0442(5) 0.0330(4) 0.0742(17) Uani 1 1 d . . .
H24 H -0.3843 -0.0723 -0.0128 0.089 Uiso 1 1 calc R . .
C25 C -0.3334(6) -0.0615(4) 0.1121(4) 0.0704(17) Uani 1 1 d . . .
H25 H -0.4136 -0.1013 0.1205 0.085 Uiso 1 1 calc R . .
C26 C -0.2345(5) -0.0214(4) 0.1801(3) 0.0560(14) Uani 1 1 d . . .
H26 H -0.2481 -0.0356 0.2337 0.067 Uiso 1 1 calc R . .
C27 C 0.1756(5) 0.4353(3) 0.6538(3) 0.0402(11) Uani 1 1 d . . .
C28 C 0.2419(4) 0.4341(3) 0.8099(3) 0.0394(11) Uani 1 1 d . . .
C29 C 0.3590(5) 0.3810(4) 0.7862(3) 0.0475(12) Uani 1 1 d . . .
C30 C 0.4918(5) 0.4252(5) 0.8068(4) 0.0666(16) Uani 1 1 d . . .
H30 H 0.5142 0.4913 0.8382 0.080 Uiso 1 1 calc R . .
C31 C 0.5941(8) 0.3767(7) 0.7834(5) 0.103(3) Uani 1 1 d . . .
H31 H 0.6843 0.4093 0.7980 0.124 Uiso 1 1 calc R . .
C32 C 0.5620(8) 0.2802(9) 0.7384(6) 0.116(3) Uani 1 1 d . . .
H32 H 0.6315 0.2468 0.7225 0.140 Uiso 1 1 calc R . .
C33 C 0.4274(8) 0.2292(6) 0.7150(5) 0.100(2) Uani 1 1 d . . .
H33 H 0.4053 0.1625 0.6847 0.120 Uiso 1 1 calc R . .
C34 C 0.3284(6) 0.2839(5) 0.7399(4) 0.0716(17) Uani 1 1 d . . .
H34 H 0.2375 0.2532 0.7243 0.086 Uiso 1 1 calc R . .
C35 C 0.2891(4) 0.5450(4) 0.8537(3) 0.0431(12) Uani 1 1 d . . .
C36 C 0.3544(5) 0.5671(4) 0.9366(3) 0.0569(14) Uani 1 1 d . . .
H36 H 0.3740 0.5150 0.9641 0.068 Uiso 1 1 calc R . .
C37 C 0.3915(5) 0.6705(5) 0.9796(4) 0.0715(18) Uani 1 1 d . . .
H37 H 0.4359 0.6848 1.0353 0.086 Uiso 1 1 calc R . .
C38 C 0.3639(5) 0.7504(5) 0.9415(4) 0.0661(16) Uani 1 1 d . . .
H38 H 0.3891 0.8174 0.9708 0.079 Uiso 1 1 calc R . .
C39 C 0.2984(5) 0.7281(4) 0.8595(4) 0.0601(15) Uani 1 1 d . . .
H39 H 0.2776 0.7804 0.8326 0.072 Uiso 1 1 calc R . .
C40 C 0.2628(4) 0.6274(4) 0.8162(3) 0.0514(13) Uani 1 1 d . . .
H40 H 0.2199 0.6142 0.7602 0.062 Uiso 1 1 calc R . .
C41 C 0.1559(5) 0.3834(4) 0.8709(3) 0.0424(12) Uani 1 1 d . . .
C42 C 0.0393(5) 0.4172(4) 0.8890(3) 0.0480(12) Uani 1 1 d . . .
H42 H 0.0157 0.4713 0.8657 0.058 Uiso 1 1 calc R . .
C43 C -0.0434(5) 0.3728(4) 0.9409(3) 0.0604(15) Uani 1 1 d . . .
H43 H -0.1224 0.3966 0.9522 0.073 Uiso 1 1 calc R . .
C44 C -0.0076(6) 0.2909(5) 0.9769(3) 0.0681(16) Uani 1 1 d . . .
H44 H -0.0635 0.2598 1.0114 0.082 Uiso 1 1 calc R . .
C45 C 0.1097(6) 0.2578(4) 0.9607(3) 0.0654(16) Uani 1 1 d . . .
H45 H 0.1346 0.2046 0.9848 0.079 Uiso 1 1 calc R . .
C46 C 0.1919(5) 0.3037(4) 0.9081(3) 0.0536(13) Uani 1 1 d . . .
H46 H 0.2719 0.2812 0.8976 0.064 Uiso 1 1 calc R . .
C47 C 0.4335(8) 0.3698(6) 0.4136(6) 0.132(2) Uani 1 1 d U . .
H47A H 0.3531 0.3807 0.3815 0.198 Uiso 1 1 calc R . .
H47B H 0.5093 0.3827 0.3827 0.198 Uiso 1 1 calc R . .
H47C H 0.4510 0.4152 0.4680 0.198 Uiso 1 1 calc R . .
C48 C 0.4149(9) 0.2696(7) 0.4260(6) 0.1178(18) Uani 1 1 d U . .
C49 C 0.5343(10) 0.1355(8) 0.4582(7) 0.154(2) Uani 1 1 d U . .
H49A H 0.6218 0.1390 0.4912 0.185 Uiso 1 1 calc R . .
H49B H 0.4654 0.1217 0.4948 0.185 Uiso 1 1 calc R . .
C50 C 0.5142(11) 0.0520(8) 0.3884(7) 0.190(3) Uani 1 1 d U . .
H50A H 0.5278 0.0770 0.3368 0.285 Uiso 1 1 calc R . .
H50B H 0.4234 0.0140 0.3829 0.285 Uiso 1 1 calc R . .
H50C H 0.5780 0.0086 0.3985 0.285 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.905(4) . ?
O1 C7 1.207(5) . ?
O2 C27 1.224(5) . ?
O3 C48 1.194(8) . ?
O4 C48 1.296(9) . ?
O4 C49 1.513(9) . ?
N1 C7 1.351(5) . ?
N1 C1 1.409(5) . ?
N1 H1A 0.8600 . ?
N2 C27 1.349(5) . ?
N2 C28 1.468(5) . ?
N2 H2A 0.8600 . ?
C1 C2 1.379(6) . ?
C1 C6 1.382(6) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(6) . ?
C3 C27 1.493(6) . ?
C4 C5 1.383(6) . ?
C5 C6 1.364(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.570(6) . ?
C8 C21 1.547(6) . ?
C8 C15 1.552(6) . ?
C8 C9 1.559(6) . ?
C9 C10 1.367(7) . ?
C9 C14 1.367(7) . ?
C10 C11 1.314(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.336(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.366(6) . ?
C15 C16 1.375(6) . ?
C16 C17 1.391(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.314(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.398(6) . ?
C21 C26 1.407(6) . ?
C22 C23 1.388(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.398(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.352(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C28 C35 1.522(6) . ?
C28 C29 1.530(6) . ?
C28 C41 1.544(6) . ?
C29 C30 1.354(7) . ?
C29 C34 1.367(7) . ?
C30 C31 1.363(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.353(10) . ?
C31 H31 0.9300 . ?
C32 C33 1.398(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.391(8) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.381(6) . ?
C35 C40 1.404(6) . ?
C36 C37 1.423(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.382(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.370(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.393(7) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C42 1.370(6) . ?
C41 C46 1.399(6) . ?
C42 C43 1.377(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.416(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.367(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.391(6) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 C48 1.391(10) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C49 C50 1.423(12) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C48 O4 C49 120.0(7) . . ?
C7 N1 C1 127.0(4) . . ?
C7 N1 H1A 116.5 . . ?
C1 N1 H1A 116.5 . . ?
C27 N2 C28 127.4(4) . . ?
C27 N2 H2A 116.3 . . ?
C28 N2 H2A 116.3 . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 N1 117.8(4) . . ?
C6 C1 N1 122.6(4) . . ?
C3 C2 C1 122.3(4) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 117.6(4) . . ?
C2 C3 C27 116.4(4) . . ?
C4 C3 C27 125.9(4) . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 Br1 117.8(3) . . ?
C3 C4 Br1 122.2(3) . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O1 C7 N1 122.4(5) . . ?
O1 C7 C8 121.2(4) . . ?
N1 C7 C8 116.4(4) . . ?
C21 C8 C15 111.0(4) . . ?
C21 C8 C9 107.4(4) . . ?
C15 C8 C9 112.5(4) . . ?
C21 C8 C7 107.9(4) . . ?
C15 C8 C7 107.0(4) . . ?
C9 C8 C7 110.9(4) . . ?
C10 C9 C14 117.1(5) . . ?
C10 C9 C8 124.6(5) . . ?
C14 C9 C8 118.2(4) . . ?
C11 C10 C9 123.2(6) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C12 119.7(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.1(6) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C20 C15 C16 117.8(4) . . ?
C20 C15 C8 119.6(4) . . ?
C16 C15 C8 122.5(5) . . ?
C15 C16 C17 121.4(5) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 120.4(6) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.2(5) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 119.5(5) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C26 117.5(5) . . ?
C22 C21 C8 122.9(4) . . ?
C26 C21 C8 119.6(4) . . ?
C23 C22 C21 120.2(5) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.4(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.4(5) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.1(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C21 121.3(5) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
O2 C27 N2 123.1(4) . . ?
O2 C27 C3 121.7(4) . . ?
N2 C27 C3 115.2(4) . . ?
N2 C28 C35 112.4(4) . . ?
N2 C28 C29 107.7(4) . . ?
C35 C28 C29 113.1(4) . . ?
N2 C28 C41 103.9(3) . . ?
C35 C28 C41 105.8(4) . . ?
C29 C28 C41 113.7(4) . . ?
C30 C29 C34 117.8(5) . . ?
C30 C29 C28 123.9(5) . . ?
C34 C29 C28 118.3(5) . . ?
C29 C30 C31 122.6(7) . . ?
C29 C30 H30 118.7 . . ?
C31 C30 H30 118.7 . . ?
C32 C31 C30 118.9(8) . . ?
C32 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
C31 C32 C33 121.9(8) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C34 C33 C32 116.1(7) . . ?
C34 C33 H33 122.0 . . ?
C32 C33 H33 122.0 . . ?
C29 C34 C33 122.7(6) . . ?
C29 C34 H34 118.6 . . ?
C33 C34 H34 118.6 . . ?
C36 C35 C40 117.3(5) . . ?
C36 C35 C28 119.2(4) . . ?
C40 C35 C28 123.5(4) . . ?
C35 C36 C37 119.3(5) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C38 C37 C36 122.4(5) . . ?
C38 C37 H37 118.8 . . ?
C36 C37 H37 118.8 . . ?
C39 C38 C37 118.1(5) . . ?
C39 C38 H38 120.9 . . ?
C37 C38 H38 120.9 . . ?
C38 C39 C40 120.2(5) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 C35 122.7(5) . . ?
C39 C40 H40 118.6 . . ?
C35 C40 H40 118.6 . . ?
C42 C41 C46 118.6(4) . . ?
C42 C41 C28 118.9(4) . . ?
C46 C41 C28 122.5(4) . . ?
C41 C42 C43 121.4(5) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C42 C43 C44 119.6(5) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 119.6(5) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 119.8(5) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C41 121.0(5) . . ?
C45 C46 H46 119.5 . . ?
C41 C46 H46 119.5 . . ?
C48 C47 H47A 109.5 . . ?
C48 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C48 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O3 C48 O4 121.0(9) . . ?
O3 C48 C47 127.6(9) . . ?
O4 C48 C47 111.3(8) . . ?
C50 C49 O4 116.1(9) . . ?
C50 C49 H49A 108.3 . . ?
O4 C49 H49A 108.3 . . ?
C50 C49 H49B 108.3 . . ?
O4 C49 H49B 108.3 . . ?
H49A C49 H49B 107.4 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

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
C7 N1 C1 C2 163.3(4) . . . . ?
C7 N1 C1 C6 -18.4(7) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
N1 C1 C2 C3 -179.7(4) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C1 C2 C3 C27 179.3(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C27 C3 C4 C5 179.6(4) . . . . ?
C2 C3 C4 Br1 -178.2(3) . . . . ?
C27 C3 C4 Br1 1.8(6) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
Br1 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
N1 C1 C6 C5 179.9(4) . . . . ?
C1 N1 C7 O1 3.3(8) . . . . ?
C1 N1 C7 C8 -176.9(4) . . . . ?
O1 C7 C8 C21 15.6(6) . . . . ?
N1 C7 C8 C21 -164.2(4) . . . . ?
O1 C7 C8 C15 135.2(5) . . . . ?
N1 C7 C8 C15 -44.6(5) . . . . ?
O1 C7 C8 C9 -101.8(5) . . . . ?
N1 C7 C8 C9 78.4(5) . . . . ?
C21 C8 C9 C10 -136.5(5) . . . . ?
C15 C8 C9 C10 101.0(5) . . . . ?
C7 C8 C9 C10 -18.8(6) . . . . ?
C21 C8 C9 C14 45.7(5) . . . . ?
C15 C8 C9 C14 -76.8(5) . . . . ?
C7 C8 C9 C14 163.4(4) . . . . ?
C14 C9 C10 C11 2.2(9) . . . . ?
C8 C9 C10 C11 -175.6(6) . . . . ?
C9 C10 C11 C12 -3.2(11) . . . . ?
C10 C11 C12 C13 3.0(10) . . . . ?
C11 C12 C13 C14 -2.0(9) . . . . ?
C12 C13 C14 C9 1.2(8) . . . . ?
C10 C9 C14 C13 -1.2(8) . . . . ?
C8 C9 C14 C13 176.8(4) . . . . ?
C21 C8 C15 C20 68.2(5) . . . . ?
C9 C8 C15 C20 -171.5(4) . . . . ?
C7 C8 C15 C20 -49.4(5) . . . . ?
C21 C8 C15 C16 -109.4(5) . . . . ?
C9 C8 C15 C16 11.0(6) . . . . ?
C7 C8 C15 C16 133.0(5) . . . . ?
C20 C15 C16 C17 1.2(8) . . . . ?
C8 C15 C16 C17 178.8(5) . . . . ?
C15 C16 C17 C18 -0.5(9) . . . . ?
C16 C17 C18 C19 -0.4(10) . . . . ?
C17 C18 C19 C20 0.6(9) . . . . ?
C16 C15 C20 C19 -1.0(7) . . . . ?
C8 C15 C20 C19 -178.7(4) . . . . ?
C18 C19 C20 C15 0.1(8) . . . . ?
C15 C8 C21 C22 1.1(6) . . . . ?
C9 C8 C21 C22 -122.2(5) . . . . ?
C7 C8 C21 C22 118.2(5) . . . . ?
C15 C8 C21 C26 -179.4(4) . . . . ?
C9 C8 C21 C26 57.3(5) . . . . ?
C7 C8 C21 C26 -62.4(5) . . . . ?
C26 C21 C22 C23 1.2(7) . . . . ?
C8 C21 C22 C23 -179.3(5) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C22 C23 C24 C25 0.2(9) . . . . ?
C23 C24 C25 C26 -0.4(9) . . . . ?
C24 C25 C26 C21 1.2(9) . . . . ?
C22 C21 C26 C25 -1.5(8) . . . . ?
C8 C21 C26 C25 179.0(5) . . . . ?
C28 N2 C27 O2 -10.7(7) . . . . ?
C28 N2 C27 C3 168.4(4) . . . . ?
C2 C3 C27 O2 52.6(6) . . . . ?
C4 C3 C27 O2 -127.4(5) . . . . ?
C2 C3 C27 N2 -126.6(4) . . . . ?
C4 C3 C27 N2 53.4(6) . . . . ?
C27 N2 C28 C35 80.6(5) . . . . ?
C27 N2 C28 C29 -44.6(6) . . . . ?
C27 N2 C28 C41 -165.5(4) . . . . ?
N2 C28 C29 C30 129.0(5) . . . . ?
C35 C28 C29 C30 4.2(6) . . . . ?
C41 C28 C29 C30 -116.5(5) . . . . ?
N2 C28 C29 C34 -49.5(5) . . . . ?
C35 C28 C29 C34 -174.3(4) . . . . ?
C41 C28 C29 C34 65.0(6) . . . . ?
C34 C29 C30 C31 -0.2(9) . . . . ?
C28 C29 C30 C31 -178.7(6) . . . . ?
C29 C30 C31 C32 -0.6(11) . . . . ?
C30 C31 C32 C33 0.2(12) . . . . ?
C31 C32 C33 C34 0.8(11) . . . . ?
C30 C29 C34 C33 1.3(9) . . . . ?
C28 C29 C34 C33 179.9(5) . . . . ?
C32 C33 C34 C29 -1.6(10) . . . . ?
N2 C28 C35 C36 165.6(4) . . . . ?
C29 C28 C35 C36 -72.1(5) . . . . ?
C41 C28 C35 C36 52.9(5) . . . . ?
N2 C28 C35 C40 -10.4(6) . . . . ?
C29 C28 C35 C40 111.9(5) . . . . ?
C41 C28 C35 C40 -123.1(4) . . . . ?
C40 C35 C36 C37 0.0(7) . . . . ?
C28 C35 C36 C37 -176.3(4) . . . . ?
C35 C36 C37 C38 0.3(8) . . . . ?
C36 C37 C38 C39 0.1(8) . . . . ?
C37 C38 C39 C40 -0.8(8) . . . . ?
C38 C39 C40 C35 1.2(8) . . . . ?
C36 C35 C40 C39 -0.8(7) . . . . ?
C28 C35 C40 C39 175.3(4) . . . . ?
N2 C28 C41 C42 -56.0(5) . . . . ?
C35 C28 C41 C42 62.6(5) . . . . ?
C29 C28 C41 C42 -172.8(4) . . . . ?
N2 C28 C41 C46 123.6(5) . . . . ?
C35 C28 C41 C46 -117.8(5) . . . . ?
C29 C28 C41 C46 6.9(6) . . . . ?
C46 C41 C42 C43 -1.6(7) . . . . ?
C28 C41 C42 C43 178.0(4) . . . . ?
C41 C42 C43 C44 0.3(8) . . . . ?
C42 C43 C44 C45 0.9(8) . . . . ?
C43 C44 C45 C46 -0.9(8) . . . . ?
C44 C45 C46 C41 -0.3(8) . . . . ?
C42 C41 C46 C45 1.6(7) . . . . ?
C28 C41 C46 C45 -178.0(4) . . . . ?
C49 O4 C48 O3 -5.0(13) . . . . ?
C49 O4 C48 C47 174.0(8) . . . . ?
C48 O4 C49 C50 88.3(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.21 3.006(6) 154.6 .
N2 H2A Br1 0.86 2.76 3.239(4) 116.8 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.066

data_cd2875
_database_code_depnum_ccdc_archive 'CCDC 699577'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H36 Br Cl3 N2 O2'
_chemical_formula_weight         738.95

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.3955(11)
_cell_length_b                   11.1852(11)
_cell_length_c                   27.326(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.064(2)
_cell_angle_gamma                90.00
_cell_volume                     3478.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3507
_cell_measurement_theta_min      4.709
_cell_measurement_theta_max      43.396

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    1.449
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5246
_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  'CCD area detecter'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20059
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_sigmaI/netI    0.1016
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7549
_reflns_number_gt                3948
_reflns_threshold_expression     >2sigma(I)

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1191P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7549
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.2144
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.27064(4) 1.03217(5) 0.342750(18) 0.0596(2) Uani 1 1 d . . .
O1 O -0.1488(3) 0.7480(3) 0.32991(11) 0.0457(8) Uani 1 1 d . . .
O2 O 0.2758(3) 0.8631(4) 0.26585(19) 0.1004(17) Uani 1 1 d . . .
N1 N -0.0299(3) 0.8180(3) 0.39220(12) 0.0382(8) Uani 1 1 d . . .
H1A H 0.0096 0.8801 0.4016 0.046 Uiso 1 1 calc R . .
N2 N 0.1883(3) 1.0328(3) 0.23992(14) 0.0447(9) Uani 1 1 d . . .
H2A H 0.1959 1.0945 0.2216 0.054 Uiso 1 1 calc R . .
C1 C -0.0822(3) 0.8231(4) 0.34718(15) 0.0360(10) Uani 1 1 d . . .
C2 C -0.0508(3) 0.9315(4) 0.31843(14) 0.0352(9) Uani 1 1 d . . .
C3 C -0.1249(4) 1.0298(4) 0.31221(15) 0.0388(10) Uani 1 1 d . . .
C4 C -0.0945(4) 1.1259(4) 0.28402(16) 0.0493(12) Uani 1 1 d . . .
H4 H -0.1449 1.1911 0.2801 0.059 Uiso 1 1 calc R . .
C5 C 0.0101(4) 1.1251(4) 0.26183(16) 0.0459(11) Uani 1 1 d . . .
H5 H 0.0316 1.1913 0.2438 0.055 Uiso 1 1 calc R . .
C6 C 0.0849(4) 1.0273(4) 0.26569(15) 0.0383(10) Uani 1 1 d . . .
C7 C 0.0539(4) 0.9315(4) 0.29432(15) 0.0394(10) Uani 1 1 d . . .
H7 H 0.1038 0.8659 0.2975 0.047 Uiso 1 1 calc R . .
C8 C 0.2777(4) 0.9521(4) 0.2406(2) 0.0528(13) Uani 1 1 d . . .
C9 C -0.0318(4) 0.7180(4) 0.42787(15) 0.0390(10) Uani 1 1 d . . .
C10 C -0.1453(4) 0.7187(4) 0.45562(15) 0.0421(10) Uani 1 1 d . . .
C11 C -0.2482(4) 0.7716(5) 0.43729(18) 0.0560(13) Uani 1 1 d . . .
H11 H -0.2495 0.8106 0.4072 0.067 Uiso 1 1 calc R . .
C12 C -0.3492(5) 0.7673(6) 0.4632(2) 0.0734(17) Uani 1 1 d . . .
H12 H -0.4182 0.8021 0.4503 0.088 Uiso 1 1 calc R . .
C13 C -0.3476(6) 0.7120(6) 0.5078(2) 0.0786(18) Uani 1 1 d . . .
H13 H -0.4152 0.7097 0.5254 0.094 Uiso 1 1 calc R . .
C14 C -0.2473(5) 0.6605(5) 0.5262(2) 0.0728(17) Uani 1 1 d . . .
H14 H -0.2465 0.6219 0.5563 0.087 Uiso 1 1 calc R . .
C15 C -0.1483(5) 0.6646(5) 0.50118(18) 0.0573(13) Uani 1 1 d . . .
H15 H -0.0801 0.6300 0.5150 0.069 Uiso 1 1 calc R . .
C16 C 0.0727(4) 0.7421(4) 0.46467(16) 0.0447(11) Uani 1 1 d . . .
C17 C 0.0732(5) 0.8469(5) 0.49125(19) 0.0674(16) Uani 1 1 d . . .
H17 H 0.0108 0.8999 0.4867 0.081 Uiso 1 1 calc R . .
C18 C 0.1654(6) 0.8747(6) 0.5247(2) 0.090(2) Uani 1 1 d . . .
H18 H 0.1650 0.9460 0.5422 0.108 Uiso 1 1 calc R . .
C19 C 0.2566(6) 0.7963(7) 0.5316(2) 0.087(2) Uani 1 1 d . . .
H19 H 0.3190 0.8146 0.5536 0.104 Uiso 1 1 calc R . .
C20 C 0.2563(5) 0.6903(6) 0.5061(2) 0.0701(16) Uani 1 1 d . . .
H20 H 0.3180 0.6364 0.5110 0.084 Uiso 1 1 calc R . .
C21 C 0.1640(4) 0.6646(5) 0.47309(18) 0.0547(13) Uani 1 1 d . . .
H21 H 0.1640 0.5925 0.4561 0.066 Uiso 1 1 calc R . .
C22 C -0.0155(4) 0.5992(4) 0.40047(15) 0.0381(10) Uani 1 1 d . . .
C23 C -0.0782(4) 0.4983(4) 0.41130(19) 0.0472(12) Uani 1 1 d . . .
H23 H -0.1358 0.5013 0.4341 0.057 Uiso 1 1 calc R . .
C24 C -0.0540(5) 0.3910(5) 0.38743(19) 0.0575(13) Uani 1 1 d . . .
H24 H -0.0962 0.3227 0.3948 0.069 Uiso 1 1 calc R . .
C25 C 0.0299(4) 0.3839(5) 0.35358(19) 0.0571(13) Uani 1 1 d . . .
H25 H 0.0462 0.3114 0.3387 0.068 Uiso 1 1 calc R . .
C26 C 0.0892(4) 0.4846(5) 0.34200(19) 0.0568(14) Uani 1 1 d . . .
H26 H 0.1445 0.4818 0.3182 0.068 Uiso 1 1 calc R . .
C27 C 0.0673(4) 0.5917(4) 0.36558(17) 0.0477(11) Uani 1 1 d . . .
H27 H 0.1093 0.6597 0.3577 0.057 Uiso 1 1 calc R . .
C28 C 0.3781(4) 0.9757(4) 0.20860(18) 0.0485(12) Uani 1 1 d . . .
C29 C 0.3799(5) 1.0946(6) 0.1842(3) 0.103(3) Uani 1 1 d . . .
H29A H 0.3851 1.1566 0.2091 0.124 Uiso 1 1 calc R . .
H29B H 0.3068 1.1058 0.1649 0.124 Uiso 1 1 calc R . .
C30 C 0.4853(5) 1.1082(7) 0.1501(3) 0.100(3) Uani 1 1 d . . .
H30 H 0.4847 1.1856 0.1333 0.120 Uiso 1 1 calc R . .
C31 C 0.4788(7) 1.0055(8) 0.1148(3) 0.104(2) Uani 1 1 d . . .
H31A H 0.4050 1.0103 0.0955 0.125 Uiso 1 1 calc R . .
H31B H 0.5418 1.0135 0.0925 0.125 Uiso 1 1 calc R . .
C32 C 0.4870(6) 0.8895(7) 0.1375(3) 0.088(2) Uani 1 1 d . . .
H32 H 0.4850 0.8274 0.1122 0.106 Uiso 1 1 calc R . .
C33 C 0.5951(5) 0.8738(6) 0.1712(3) 0.0826(19) Uani 1 1 d . . .
H33A H 0.5929 0.7963 0.1872 0.099 Uiso 1 1 calc R . .
H33B H 0.6649 0.8770 0.1525 0.099 Uiso 1 1 calc R . .
C34 C 0.5997(5) 0.9681(6) 0.2081(3) 0.0767(18) Uani 1 1 d . . .
H34 H 0.6714 0.9583 0.2291 0.092 Uiso 1 1 calc R . .
C35 C 0.4943(5) 0.9547(6) 0.2389(2) 0.0806(19) Uani 1 1 d . . .
H35A H 0.5003 1.0115 0.2657 0.097 Uiso 1 1 calc R . .
H35B H 0.4940 0.8749 0.2528 0.097 Uiso 1 1 calc R . .
C36 C 0.3776(5) 0.8779(7) 0.1684(2) 0.092(2) Uani 1 1 d . . .
H36A H 0.3769 0.7996 0.1836 0.111 Uiso 1 1 calc R . .
H36B H 0.3070 0.8855 0.1472 0.111 Uiso 1 1 calc R . .
C37 C 0.5994(6) 1.0913(6) 0.1859(3) 0.098(2) Uani 1 1 d . . .
H37A H 0.6695 1.1022 0.1677 0.118 Uiso 1 1 calc R . .
H37B H 0.5999 1.1510 0.2116 0.118 Uiso 1 1 calc R . .
Cl1 Cl 0.2094(3) 1.0864(3) 0.39452(14) 0.1957(17) Uani 1 1 d . . .
Cl2 Cl 0.3084(2) 0.8590(2) 0.40060(14) 0.1707(12) Uani 1 1 d . . .
Cl3 Cl 0.4590(3) 1.0532(3) 0.3971(2) 0.237(2) Uani 1 1 d . . .
C38 C 0.3248(8) 0.9943(8) 0.3832(6) 0.168(5) Uani 1 1 d . . .
H38 H 0.3217 0.9884 0.3474 0.202 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.898(4) . ?
O1 C1 1.211(5) . ?
O2 C8 1.212(6) . ?
N1 C1 1.339(5) . ?
N1 C9 1.485(5) . ?
N1 H1A 0.8600 . ?
N2 C8 1.361(6) . ?
N2 C6 1.406(5) . ?
N2 H2A 0.8600 . ?
C1 C2 1.499(6) . ?
C2 C3 1.392(6) . ?
C2 C7 1.393(6) . ?
C3 C4 1.378(6) . ?
C4 C5 1.366(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.384(6) . ?
C7 H7 0.9300 . ?
C8 C28 1.500(6) . ?
C9 C10 1.534(6) . ?
C9 C16 1.541(6) . ?
C9 C22 1.542(6) . ?
C10 C11 1.383(6) . ?
C10 C15 1.386(6) . ?
C11 C12 1.384(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.352(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.351(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.364(6) . ?
C16 C17 1.378(7) . ?
C17 C18 1.390(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.376(6) . ?
C22 C27 1.379(6) . ?
C23 C24 1.400(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.489(8) . ?
C28 C35 1.542(7) . ?
C28 C36 1.549(8) . ?
C29 C30 1.568(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.498(10) . ?
C30 C37 1.596(10) . ?
C30 H30 0.9800 . ?
C31 C32 1.439(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.508(9) . ?
C32 C36 1.548(8) . ?
C32 H32 0.9800 . ?
C33 C34 1.457(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C37 1.505(9) . ?
C34 C35 1.511(8) . ?
C34 H34 0.9800 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
Cl1 C38 1.712(11) . ?
Cl2 C38 1.600(9) . ?
Cl3 C38 1.689(9) . ?
C38 H38 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 127.9(3) . . ?
C1 N1 H1A 116.1 . . ?
C9 N1 H1A 116.1 . . ?
C8 N2 C6 127.7(4) . . ?
C8 N2 H2A 116.1 . . ?
C6 N2 H2A 116.1 . . ?
O1 C1 N1 124.6(4) . . ?
O1 C1 C2 121.3(4) . . ?
N1 C1 C2 114.2(4) . . ?
C3 C2 C7 118.1(4) . . ?
C3 C2 C1 122.9(4) . . ?
C7 C2 C1 118.8(4) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 Br1 119.2(3) . . ?
C2 C3 Br1 119.8(3) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.6(4) . . ?
C7 C6 N2 124.3(4) . . ?
C5 C6 N2 117.1(4) . . ?
C6 C7 C2 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O2 C8 N2 121.0(4) . . ?
O2 C8 C28 120.9(4) . . ?
N2 C8 C28 118.0(4) . . ?
N1 C9 C10 111.3(3) . . ?
N1 C9 C16 105.0(3) . . ?
C10 C9 C16 108.6(3) . . ?
N1 C9 C22 108.9(3) . . ?
C10 C9 C22 111.8(3) . . ?
C16 C9 C22 111.0(3) . . ?
C11 C10 C15 116.8(4) . . ?
C11 C10 C9 123.0(4) . . ?
C15 C10 C9 120.2(4) . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 122.0(5) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
C21 C16 C17 118.0(4) . . ?
C21 C16 C9 123.7(4) . . ?
C17 C16 C9 118.3(4) . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.4(6) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.1(6) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.5(5) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 121.8(5) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C27 118.8(4) . . ?
C23 C22 C9 121.6(4) . . ?
C27 C22 C9 119.5(4) . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 121.8(5) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C26 C25 C24 118.9(5) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C27 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 121.3(5) . . ?
C22 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C8 116.5(4) . . ?
C29 C28 C35 110.2(5) . . ?
C8 C28 C35 108.7(4) . . ?
C29 C28 C36 108.3(5) . . ?
C8 C28 C36 108.3(4) . . ?
C35 C28 C36 104.1(5) . . ?
C28 C29 C30 112.4(5) . . ?
C28 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C31 C30 C29 107.2(6) . . ?
C31 C30 C37 108.3(6) . . ?
C29 C30 C37 104.4(6) . . ?
C31 C30 H30 112.2 . . ?
C29 C30 H30 112.2 . . ?
C37 C30 H30 112.2 . . ?
C32 C31 C30 114.4(6) . . ?
C32 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C31 C32 C33 113.7(6) . . ?
C31 C32 C36 105.9(6) . . ?
C33 C32 C36 108.2(6) . . ?
C31 C32 H32 109.6 . . ?
C33 C32 H32 109.6 . . ?
C36 C32 H32 109.6 . . ?
C34 C33 C32 109.6(5) . . ?
C34 C33 H33A 109.8 . . ?
C32 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 C37 112.7(6) . . ?
C33 C34 C35 108.2(5) . . ?
C37 C34 C35 109.3(5) . . ?
C33 C34 H34 108.9 . . ?
C37 C34 H34 108.9 . . ?
C35 C34 H34 108.9 . . ?
C34 C35 C28 111.7(5) . . ?
C34 C35 H35A 109.3 . . ?
C28 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
C28 C35 H35B 109.3 . . ?
H35A C35 H35B 107.9 . . ?
C32 C36 C28 110.7(5) . . ?
C32 C36 H36A 109.5 . . ?
C28 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C28 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C34 C37 C30 109.8(5) . . ?
C34 C37 H37A 109.7 . . ?
C30 C37 H37A 109.7 . . ?
C34 C37 H37B 109.7 . . ?
C30 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
Cl2 C38 Cl3 114.9(7) . . ?
Cl2 C38 Cl1 114.4(6) . . ?
Cl3 C38 Cl1 114.8(6) . . ?
Cl2 C38 H38 103.5 . . ?
Cl3 C38 H38 103.5 . . ?
Cl1 C38 H38 103.5 . . ?

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
C9 N1 C1 O1 6.4(6) . . . . ?
C9 N1 C1 C2 -173.1(4) . . . . ?
O1 C1 C2 C3 78.4(5) . . . . ?
N1 C1 C2 C3 -102.1(5) . . . . ?
O1 C1 C2 C7 -97.7(5) . . . . ?
N1 C1 C2 C7 81.8(5) . . . . ?
C7 C2 C3 C4 -1.6(6) . . . . ?
C1 C2 C3 C4 -177.7(4) . . . . ?
C7 C2 C3 Br1 178.2(3) . . . . ?
C1 C2 C3 Br1 2.2(6) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
Br1 C3 C4 C5 -179.9(3) . . . . ?
C3 C4 C5 C6 2.3(7) . . . . ?
C4 C5 C6 C7 -2.6(7) . . . . ?
C4 C5 C6 N2 177.5(4) . . . . ?
C8 N2 C6 C7 -4.4(7) . . . . ?
C8 N2 C6 C5 175.5(5) . . . . ?
C5 C6 C7 C2 0.8(6) . . . . ?
N2 C6 C7 C2 -179.2(4) . . . . ?
C3 C2 C7 C6 1.2(6) . . . . ?
C1 C2 C7 C6 177.4(4) . . . . ?
C6 N2 C8 O2 -1.1(8) . . . . ?
C6 N2 C8 C28 178.2(4) . . . . ?
C1 N1 C9 C10 -81.0(5) . . . . ?
C1 N1 C9 C16 161.7(4) . . . . ?
C1 N1 C9 C22 42.7(5) . . . . ?
N1 C9 C10 C11 23.7(6) . . . . ?
C16 C9 C10 C11 138.8(5) . . . . ?
C22 C9 C10 C11 -98.3(5) . . . . ?
N1 C9 C10 C15 -156.4(4) . . . . ?
C16 C9 C10 C15 -41.3(6) . . . . ?
C22 C9 C10 C15 81.5(5) . . . . ?
C15 C10 C11 C12 -1.5(8) . . . . ?
C9 C10 C11 C12 178.4(5) . . . . ?
C10 C11 C12 C13 1.0(9) . . . . ?
C11 C12 C13 C14 -0.7(10) . . . . ?
C12 C13 C14 C15 0.9(10) . . . . ?
C13 C14 C15 C10 -1.4(9) . . . . ?
C11 C10 C15 C14 1.7(8) . . . . ?
C9 C10 C15 C14 -178.2(5) . . . . ?
N1 C9 C16 C21 -120.5(5) . . . . ?
C10 C9 C16 C21 120.4(5) . . . . ?
C22 C9 C16 C21 -3.0(6) . . . . ?
N1 C9 C16 C17 60.6(5) . . . . ?
C10 C9 C16 C17 -58.5(5) . . . . ?
C22 C9 C16 C17 178.2(4) . . . . ?
C21 C16 C17 C18 1.7(8) . . . . ?
C9 C16 C17 C18 -179.3(5) . . . . ?
C16 C17 C18 C19 -0.5(10) . . . . ?
C17 C18 C19 C20 -0.7(11) . . . . ?
C18 C19 C20 C21 0.7(10) . . . . ?
C17 C16 C21 C20 -1.7(8) . . . . ?
C9 C16 C21 C20 179.4(5) . . . . ?
C19 C20 C21 C16 0.5(9) . . . . ?
N1 C9 C22 C23 -139.8(4) . . . . ?
C10 C9 C22 C23 -16.4(6) . . . . ?
C16 C9 C22 C23 105.1(5) . . . . ?
N1 C9 C22 C27 42.9(5) . . . . ?
C10 C9 C22 C27 166.3(4) . . . . ?
C16 C9 C22 C27 -72.2(5) . . . . ?
C27 C22 C23 C24 1.5(7) . . . . ?
C9 C22 C23 C24 -175.9(4) . . . . ?
C22 C23 C24 C25 -0.2(8) . . . . ?
C23 C24 C25 C26 -1.7(8) . . . . ?
C24 C25 C26 C27 2.3(8) . . . . ?
C23 C22 C27 C26 -0.9(7) . . . . ?
C9 C22 C27 C26 176.5(4) . . . . ?
C25 C26 C27 C22 -1.0(7) . . . . ?
O2 C8 C28 C29 -172.1(6) . . . . ?
N2 C8 C28 C29 8.6(8) . . . . ?
O2 C8 C28 C35 -46.9(7) . . . . ?
N2 C8 C28 C35 133.7(5) . . . . ?
O2 C8 C28 C36 65.7(7) . . . . ?
N2 C8 C28 C36 -113.7(6) . . . . ?
C8 C28 C29 C30 -177.7(6) . . . . ?
C35 C28 C29 C30 57.9(8) . . . . ?
C36 C28 C29 C30 -55.4(8) . . . . ?
C28 C29 C30 C31 54.6(9) . . . . ?
C28 C29 C30 C37 -60.2(8) . . . . ?
C29 C30 C31 C32 -60.3(9) . . . . ?
C37 C30 C31 C32 51.9(8) . . . . ?
C30 C31 C32 C33 -54.8(8) . . . . ?
C30 C31 C32 C36 63.9(8) . . . . ?
C31 C32 C33 C34 55.4(8) . . . . ?
C36 C32 C33 C34 -62.0(7) . . . . ?
C32 C33 C34 C37 -57.6(7) . . . . ?
C32 C33 C34 C35 63.5(7) . . . . ?
C33 C34 C35 C28 -64.9(7) . . . . ?
C37 C34 C35 C28 58.2(7) . . . . ?
C29 C28 C35 C34 -55.3(7) . . . . ?
C8 C28 C35 C34 175.9(5) . . . . ?
C36 C28 C35 C34 60.6(6) . . . . ?
C31 C32 C36 C28 -61.4(7) . . . . ?
C33 C32 C36 C28 60.8(8) . . . . ?
C29 C28 C36 C32 58.8(7) . . . . ?
C8 C28 C36 C32 -174.0(5) . . . . ?
C35 C28 C36 C32 -58.4(7) . . . . ?
C33 C34 C37 C30 57.5(7) . . . . ?
C35 C34 C37 C30 -62.9(7) . . . . ?
C31 C30 C37 C34 -52.0(7) . . . . ?
C29 C30 C37 C34 62.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C38 H38 O2 0.98 2.66 3.545(15) 150.1 .
N2 H2A O1 0.86 2.27 3.089(5) 160.3 2

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.089

data_cd27640
_database_code_depnum_ccdc_archive 'CCDC 699578'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H35 Br N2 O2, C4 H8 O2'
_chemical_formula_sum            'C41 H43 Br N2 O4'
_chemical_formula_weight         707.68

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.8909(11)
_cell_length_b                   10.2401(9)
_cell_length_c                   28.515(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.568(2)
_cell_angle_gamma                90.00
_cell_volume                     3468.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3686
_cell_measurement_theta_min      4.562
_cell_measurement_theta_max      47.454

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6261
_exptl_absorpt_correction_T_max  0.6589
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19939
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_sigmaI/netI    0.1025
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7539
_reflns_number_gt                4374
_reflns_threshold_expression     >2sigma(I)

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7539
_refine_ls_number_parameters     436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1295
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44563(3) 0.87033(4) 0.607832(12) 0.05064(16) Uani 1 1 d . . .
O1 O 0.62320(17) 1.1413(2) 0.65555(7) 0.0338(5) Uani 1 1 d . . .
O2 O 0.6974(2) 1.0014(3) 0.82742(8) 0.0636(8) Uani 1 1 d . . .
O3 O 0.7826(3) 0.7218(4) 0.69922(15) 0.1212(14) Uani 1 1 d . . .
O4 O 0.6769(4) 0.5472(4) 0.69473(15) 0.144(2) Uani 1 1 d . . .
N1 N 0.7336(2) 0.9634(2) 0.64499(8) 0.0285(6) Uani 1 1 d . . .
H1A H 0.7325 0.8795 0.6454 0.034 Uiso 1 1 calc R . .
N2 N 0.5646(2) 0.8458(3) 0.81663(9) 0.0363(7) Uani 1 1 d . . .
H2A H 0.5265 0.7881 0.8311 0.044 Uiso 1 1 calc R . .
C1 C 0.6440(2) 1.0260(3) 0.66154(10) 0.0279(7) Uani 1 1 d . . .
C2 C 0.5723(2) 0.9411(3) 0.69123(10) 0.0285(7) Uani 1 1 d . . .
C3 C 0.4833(3) 0.8685(3) 0.67348(10) 0.0322(7) Uani 1 1 d . . .
C4 C 0.4201(3) 0.7923(3) 0.70241(11) 0.0394(8) Uani 1 1 d . . .
H4 H 0.3600 0.7433 0.6900 0.047 Uiso 1 1 calc R . .
C5 C 0.4471(3) 0.7898(3) 0.74933(11) 0.0390(8) Uani 1 1 d . . .
H5 H 0.4041 0.7396 0.7690 0.047 Uiso 1 1 calc R . .
C6 C 0.5371(3) 0.8605(3) 0.76839(11) 0.0323(7) Uani 1 1 d . . .
C7 C 0.5995(3) 0.9380(3) 0.73890(10) 0.0311(7) Uani 1 1 d . . .
H7 H 0.6593 0.9876 0.7512 0.037 Uiso 1 1 calc R . .
C8 C 0.6437(3) 0.9114(3) 0.84329(11) 0.0363(8) Uani 1 1 d . . .
C9 C 0.8343(2) 1.0270(3) 0.62613(10) 0.0274(7) Uani 1 1 d . . .
C10 C 0.8116(2) 1.0772(3) 0.57589(10) 0.0278(7) Uani 1 1 d . . .
C11 C 0.7049(3) 1.0999(3) 0.55663(11) 0.0387(8) Uani 1 1 d . . .
H11 H 0.6427 1.0818 0.5742 0.046 Uiso 1 1 calc R . .
C12 C 0.6892(3) 1.1488(4) 0.51211(12) 0.0489(10) Uani 1 1 d . . .
H12 H 0.6165 1.1636 0.4999 0.059 Uiso 1 1 calc R . .
C13 C 0.7798(3) 1.1762(4) 0.48512(11) 0.0461(9) Uani 1 1 d . . .
H13 H 0.7689 1.2114 0.4552 0.055 Uiso 1 1 calc R . .
C14 C 0.8863(3) 1.1506(4) 0.50326(12) 0.0496(10) Uani 1 1 d . . .
H14 H 0.9481 1.1669 0.4853 0.060 Uiso 1 1 calc R . .
C15 C 0.9024(3) 1.1008(3) 0.54796(12) 0.0414(9) Uani 1 1 d . . .
H15 H 0.9750 1.0827 0.5596 0.050 Uiso 1 1 calc R . .
C16 C 0.9249(3) 0.9193(3) 0.62488(10) 0.0314(7) Uani 1 1 d . . .
C17 C 0.8993(3) 0.8014(3) 0.60373(12) 0.0410(8) Uani 1 1 d . . .
H17 H 0.8280 0.7879 0.5898 0.049 Uiso 1 1 calc R . .
C18 C 0.9792(3) 0.7027(4) 0.60305(13) 0.0528(10) Uani 1 1 d . . .
H18 H 0.9602 0.6226 0.5896 0.063 Uiso 1 1 calc R . .
C19 C 1.0845(4) 0.7220(4) 0.62181(14) 0.0606(12) Uani 1 1 d . . .
H19 H 1.1372 0.6549 0.6217 0.073 Uiso 1 1 calc R . .
C20 C 1.1131(3) 0.8409(5) 0.64096(14) 0.0599(11) Uani 1 1 d . . .
H20 H 1.1859 0.8554 0.6530 0.072 Uiso 1 1 calc R . .
C21 C 1.0337(3) 0.9390(4) 0.64237(12) 0.0447(9) Uani 1 1 d . . .
H21 H 1.0538 1.0196 0.6553 0.054 Uiso 1 1 calc R . .
C22 C 0.8733(2) 1.1348(3) 0.66096(11) 0.0339(7) Uani 1 1 d . . .
C23 C 0.9129(3) 1.2540(4) 0.64715(13) 0.0488(9) Uani 1 1 d . . .
H23 H 0.9124 1.2749 0.6154 0.059 Uiso 1 1 calc R . .
C24 C 0.9538(4) 1.3437(4) 0.68028(17) 0.0656(12) Uani 1 1 d . . .
H24 H 0.9802 1.4242 0.6704 0.079 Uiso 1 1 calc R . .
C25 C 0.9558(4) 1.3156(5) 0.72669(17) 0.0727(13) Uani 1 1 d . . .
H25 H 0.9836 1.3761 0.7486 0.087 Uiso 1 1 calc R . .
C26 C 0.9160(4) 1.1959(5) 0.74139(14) 0.0676(12) Uani 1 1 d . . .
H26 H 0.9165 1.1758 0.7732 0.081 Uiso 1 1 calc R . .
C27 C 0.8751(3) 1.1059(4) 0.70817(12) 0.0467(9) Uani 1 1 d . . .
H27 H 0.8487 1.0254 0.7180 0.056 Uiso 1 1 calc R . .
C28 C 0.6675(3) 0.8679(3) 0.89361(11) 0.0336(7) Uani 1 1 d . . .
C29 C 0.6016(3) 0.7490(4) 0.90946(12) 0.0499(9) Uani 1 1 d . . .
H29A H 0.6163 0.6755 0.8892 0.060 Uiso 1 1 calc R . .
H29B H 0.5216 0.7677 0.9068 0.060 Uiso 1 1 calc R . .
C30 C 0.6353(3) 0.7134(4) 0.96059(12) 0.0537(10) Uani 1 1 d . . .
H30 H 0.5926 0.6370 0.9704 0.064 Uiso 1 1 calc R . .
C31 C 0.6103(4) 0.8300(4) 0.99145(13) 0.0617(11) Uani 1 1 d . . .
H31A H 0.5304 0.8495 0.9889 0.074 Uiso 1 1 calc R . .
H31B H 0.6300 0.8090 1.0240 0.074 Uiso 1 1 calc R . .
C32 C 0.6763(3) 0.9475(4) 0.97685(12) 0.0528(10) Uani 1 1 d . . .
H32 H 0.6599 1.0214 0.9973 0.063 Uiso 1 1 calc R . .
C33 C 0.8012(3) 0.9180(4) 0.98049(14) 0.0621(11) Uani 1 1 d . . .
H33A H 0.8433 0.9936 0.9707 0.075 Uiso 1 1 calc R . .
H33B H 0.8240 0.8983 1.0128 0.075 Uiso 1 1 calc R . .
C34 C 0.8261(3) 0.8029(4) 0.94960(14) 0.0601(11) Uani 1 1 d . . .
H34 H 0.9068 0.7832 0.9525 0.072 Uiso 1 1 calc R . .
C35 C 0.7943(3) 0.8360(4) 0.89905(13) 0.0515(10) Uani 1 1 d . . .
H35A H 0.8115 0.7626 0.8791 0.062 Uiso 1 1 calc R . .
H35B H 0.8378 0.9105 0.8893 0.062 Uiso 1 1 calc R . .
C36 C 0.6435(3) 0.9828(3) 0.92597(12) 0.0453(9) Uani 1 1 d . . .
H36A H 0.6860 1.0586 0.9166 0.054 Uiso 1 1 calc R . .
H36B H 0.5640 1.0046 0.9233 0.054 Uiso 1 1 calc R . .
C37 C 0.7602(4) 0.6843(4) 0.96381(15) 0.0685(13) Uani 1 1 d . . .
H37A H 0.7827 0.6597 0.9957 0.082 Uiso 1 1 calc R . .
H37B H 0.7765 0.6116 0.9434 0.082 Uiso 1 1 calc R . .
C38 C 0.7352(5) 0.6306(5) 0.71975(19) 0.0830(16) Uani 1 1 d . . .
C39 C 0.7572(5) 0.5982(5) 0.76715(19) 0.1057(19) Uani 1 1 d . . .
H39A H 0.7962 0.6691 0.7828 0.159 Uiso 1 1 calc R . .
H39B H 0.8031 0.5210 0.7692 0.159 Uiso 1 1 calc R . .
H39C H 0.6875 0.5823 0.7819 0.159 Uiso 1 1 calc R . .
C40 C 0.6524(7) 0.5966(9) 0.6464(2) 0.161(3) Uani 1 1 d . . .
H40A H 0.6961 0.6739 0.6397 0.193 Uiso 1 1 calc R . .
H40B H 0.5729 0.6146 0.6405 0.193 Uiso 1 1 calc R . .
C41 C 0.6904(4) 0.4793(6) 0.6193(2) 0.108(2) Uani 1 1 d . . .
H41A H 0.7711 0.4781 0.6192 0.161 Uiso 1 1 calc R . .
H41B H 0.6600 0.4839 0.5876 0.161 Uiso 1 1 calc R . .
H41C H 0.6643 0.4010 0.6339 0.161 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.905(3) . ?
O1 C1 1.217(3) . ?
O2 C8 1.219(4) . ?
O3 C38 1.250(5) . ?
O4 C38 1.294(6) . ?
O4 C40 1.485(7) . ?
N1 C1 1.347(4) . ?
N1 C9 1.484(4) . ?
N1 H1A 0.8600 . ?
N2 C8 1.361(4) . ?
N2 C6 1.408(4) . ?
N2 H2A 0.8600 . ?
C1 C2 1.504(4) . ?
C2 C3 1.372(4) . ?
C2 C7 1.383(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(4) . ?
C7 H7 0.9300 . ?
C8 C28 1.517(4) . ?
C9 C10 1.534(4) . ?
C9 C22 1.542(4) . ?
C9 C16 1.544(4) . ?
C10 C11 1.380(4) . ?
C10 C15 1.391(4) . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.377(5) . ?
C16 C21 1.381(4) . ?
C17 C18 1.388(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.354(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.372(5) . ?
C22 C27 1.378(5) . ?
C23 C24 1.389(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.353(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.393(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.527(4) . ?
C28 C36 1.530(4) . ?
C28 C35 1.544(5) . ?
C29 C30 1.538(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C37 1.514(6) . ?
C30 C31 1.520(5) . ?
C30 H30 0.9800 . ?
C31 C32 1.506(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.515(5) . ?
C32 C36 1.529(5) . ?
C32 H32 0.9800 . ?
C33 C34 1.509(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C37 1.511(6) . ?
C34 C35 1.512(5) . ?
C34 H34 0.9800 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.405(7) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.508(8) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C38 O4 C40 111.5(5) . . ?
C1 N1 C9 125.6(2) . . ?
C1 N1 H1A 117.2 . . ?
C9 N1 H1A 117.2 . . ?
C8 N2 C6 128.1(3) . . ?
C8 N2 H2A 115.9 . . ?
C6 N2 H2A 115.9 . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C2 121.6(3) . . ?
N1 C1 C2 113.5(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 123.5(3) . . ?
C7 C2 C1 116.9(3) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 Br1 120.0(2) . . ?
C4 C3 Br1 118.8(2) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 N2 118.0(3) . . ?
C7 C6 N2 123.0(3) . . ?
C2 C7 C6 119.9(3) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 N2 121.7(3) . . ?
O2 C8 C28 119.7(3) . . ?
N2 C8 C28 118.6(3) . . ?
N1 C9 C10 112.0(2) . . ?
N1 C9 C22 107.7(2) . . ?
C10 C9 C22 113.4(2) . . ?
N1 C9 C16 105.6(2) . . ?
C10 C9 C16 108.1(2) . . ?
C22 C9 C16 109.7(2) . . ?
C11 C10 C15 117.8(3) . . ?
C11 C10 C9 123.2(3) . . ?
C15 C10 C9 119.0(3) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C9 119.7(3) . . ?
C21 C16 C9 122.0(3) . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.9(4) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C27 118.7(3) . . ?
C23 C22 C9 123.3(3) . . ?
C27 C22 C9 117.8(3) . . ?
C22 C23 C24 120.5(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.9(4) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 119.5(4) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 119.5(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 120.8(4) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C8 C28 C29 116.0(3) . . ?
C8 C28 C36 108.2(3) . . ?
C29 C28 C36 108.8(3) . . ?
C8 C28 C35 107.3(3) . . ?
C29 C28 C35 108.3(3) . . ?
C36 C28 C35 108.1(3) . . ?
C28 C29 C30 110.7(3) . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C37 C30 C31 109.6(3) . . ?
C37 C30 C29 108.5(3) . . ?
C31 C30 C29 108.3(3) . . ?
C37 C30 H30 110.1 . . ?
C31 C30 H30 110.1 . . ?
C29 C30 H30 110.1 . . ?
C32 C31 C30 110.5(3) . . ?
C32 C31 H31A 109.6 . . ?
C30 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C30 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
C31 C32 C33 110.0(3) . . ?
C31 C32 C36 109.7(3) . . ?
C33 C32 C36 108.7(3) . . ?
C31 C32 H32 109.5 . . ?
C33 C32 H32 109.5 . . ?
C36 C32 H32 109.5 . . ?
C34 C33 C32 109.5(3) . . ?
C34 C33 H33A 109.8 . . ?
C32 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 C37 110.7(4) . . ?
C33 C34 C35 109.5(3) . . ?
C37 C34 C35 109.0(4) . . ?
C33 C34 H34 109.2 . . ?
C37 C34 H34 109.2 . . ?
C35 C34 H34 109.2 . . ?
C34 C35 C28 110.2(3) . . ?
C34 C35 H35A 109.6 . . ?
C28 C35 H35A 109.6 . . ?
C34 C35 H35B 109.6 . . ?
C28 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C32 C36 C28 110.1(3) . . ?
C32 C36 H36A 109.6 . . ?
C28 C36 H36A 109.6 . . ?
C32 C36 H36B 109.6 . . ?
C28 C36 H36B 109.6 . . ?
H36A C36 H36B 108.2 . . ?
C34 C37 C30 110.2(3) . . ?
C34 C37 H37A 109.6 . . ?
C30 C37 H37A 109.6 . . ?
C34 C37 H37B 109.6 . . ?
C30 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
O3 C38 O4 118.5(5) . . ?
O3 C38 C39 123.9(6) . . ?
O4 C38 C39 116.6(5) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O4 C40 C41 98.8(6) . . ?
O4 C40 H40A 112.0 . . ?
C41 C40 H40A 112.0 . . ?
O4 C40 H40B 112.0 . . ?
C41 C40 H40B 112.0 . . ?
H40A C40 H40B 109.7 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

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
C9 N1 C1 O1 14.2(5) . . . . ?
C9 N1 C1 C2 -162.5(3) . . . . ?
O1 C1 C2 C3 93.0(4) . . . . ?
N1 C1 C2 C3 -90.2(4) . . . . ?
O1 C1 C2 C7 -87.0(4) . . . . ?
N1 C1 C2 C7 89.9(3) . . . . ?
C7 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C7 C2 C3 Br1 -179.4(2) . . . . ?
C1 C2 C3 Br1 0.7(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
Br1 C3 C4 C5 179.6(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C7 1.5(5) . . . . ?
C4 C5 C6 N2 -175.6(3) . . . . ?
C8 N2 C6 C5 -175.1(3) . . . . ?
C8 N2 C6 C7 8.0(5) . . . . ?
C3 C2 C7 C6 0.6(4) . . . . ?
C1 C2 C7 C6 -179.5(3) . . . . ?
C5 C6 C7 C2 -1.3(4) . . . . ?
N2 C6 C7 C2 175.6(3) . . . . ?
C6 N2 C8 O2 5.1(5) . . . . ?
C6 N2 C8 C28 -173.1(3) . . . . ?
C1 N1 C9 C10 -77.8(3) . . . . ?
C1 N1 C9 C22 47.5(4) . . . . ?
C1 N1 C9 C16 164.7(3) . . . . ?
N1 C9 C10 C11 19.9(4) . . . . ?
C22 C9 C10 C11 -102.2(3) . . . . ?
C16 C9 C10 C11 135.9(3) . . . . ?
N1 C9 C10 C15 -159.8(3) . . . . ?
C22 C9 C10 C15 78.0(3) . . . . ?
C16 C9 C10 C15 -43.8(4) . . . . ?
C15 C10 C11 C12 -2.4(5) . . . . ?
C9 C10 C11 C12 177.9(3) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C12 C13 C14 1.7(6) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
C11 C10 C15 C14 2.8(5) . . . . ?
C9 C10 C15 C14 -177.5(3) . . . . ?
N1 C9 C16 C17 51.1(3) . . . . ?
C10 C9 C16 C17 -69.0(3) . . . . ?
C22 C9 C16 C17 166.9(3) . . . . ?
N1 C9 C16 C21 -132.2(3) . . . . ?
C10 C9 C16 C21 107.8(3) . . . . ?
C22 C9 C16 C21 -16.3(4) . . . . ?
C21 C16 C17 C18 4.3(5) . . . . ?
C9 C16 C17 C18 -178.9(3) . . . . ?
C16 C17 C18 C19 -2.1(5) . . . . ?
C17 C18 C19 C20 -1.1(6) . . . . ?
C18 C19 C20 C21 2.0(6) . . . . ?
C17 C16 C21 C20 -3.4(5) . . . . ?
C9 C16 C21 C20 179.8(3) . . . . ?
C19 C20 C21 C16 0.3(6) . . . . ?
N1 C9 C22 C23 -141.1(3) . . . . ?
C10 C9 C22 C23 -16.6(4) . . . . ?
C16 C9 C22 C23 104.4(3) . . . . ?
N1 C9 C22 C27 43.3(4) . . . . ?
C10 C9 C22 C27 167.8(3) . . . . ?
C16 C9 C22 C27 -71.2(3) . . . . ?
C27 C22 C23 C24 -0.1(5) . . . . ?
C9 C22 C23 C24 -175.7(3) . . . . ?
C22 C23 C24 C25 0.2(6) . . . . ?
C23 C24 C25 C26 -0.3(7) . . . . ?
C24 C25 C26 C27 0.4(7) . . . . ?
C23 C22 C27 C26 0.2(5) . . . . ?
C9 C22 C27 C26 176.0(3) . . . . ?
C25 C26 C27 C22 -0.3(6) . . . . ?
O2 C8 C28 C29 -176.2(3) . . . . ?
N2 C8 C28 C29 2.0(4) . . . . ?
O2 C8 C28 C36 61.2(4) . . . . ?
N2 C8 C28 C36 -120.5(3) . . . . ?
O2 C8 C28 C35 -55.1(4) . . . . ?
N2 C8 C28 C35 123.1(3) . . . . ?
C8 C28 C29 C30 178.7(3) . . . . ?
C36 C28 C29 C30 -59.0(4) . . . . ?
C35 C28 C29 C30 58.2(4) . . . . ?
C28 C29 C30 C37 -59.3(4) . . . . ?
C28 C29 C30 C31 59.6(4) . . . . ?
C37 C30 C31 C32 58.2(4) . . . . ?
C29 C30 C31 C32 -60.0(4) . . . . ?
C30 C31 C32 C33 -59.0(4) . . . . ?
C30 C31 C32 C36 60.5(4) . . . . ?
C31 C32 C33 C34 58.8(4) . . . . ?
C36 C32 C33 C34 -61.4(4) . . . . ?
C32 C33 C34 C37 -58.7(4) . . . . ?
C32 C33 C34 C35 61.4(4) . . . . ?
C33 C34 C35 C28 -60.3(4) . . . . ?
C37 C34 C35 C28 60.9(4) . . . . ?
C8 C28 C35 C34 175.1(3) . . . . ?
C29 C28 C35 C34 -59.0(4) . . . . ?
C36 C28 C35 C34 58.7(4) . . . . ?
C31 C32 C36 C28 -59.3(4) . . . . ?
C33 C32 C36 C28 61.0(4) . . . . ?
C8 C28 C36 C32 -174.9(3) . . . . ?
C29 C28 C36 C32 58.3(4) . . . . ?
C35 C28 C36 C32 -59.1(4) . . . . ?
C33 C34 C37 C30 58.5(4) . . . . ?
C35 C34 C37 C30 -62.0(4) . . . . ?
C31 C30 C37 C34 -57.5(4) . . . . ?
C29 C30 C37 C34 60.5(4) . . . . ?
C40 O4 C38 O3 -15.2(8) . . . . ?
C40 O4 C38 C39 176.0(5) . . . . ?
C38 O4 C40 C41 129.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.29 2.962(5) 135.3 .
N2 H2A O1 0.86 2.37 3.187(3) 157.8 2_646

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.081

data_080625_0m
_database_code_depnum_ccdc_archive 'CCDC 699579'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C26 H19 Br N2 O3'

_chemical_formula_weight         487.34

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'
Br Br -0.2901 2.4595 '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'

_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                   8.292(2)

_cell_length_b                   9.416(3)

_cell_length_c                   15.730(4)

_cell_angle_alpha                77.792(3)

_cell_angle_beta                 85.614(3)

_cell_angle_gamma                65.372(3)

_cell_volume                     1091.1(5)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2648

_cell_measurement_theta_min      2.43

_cell_measurement_theta_max      27.05

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.20

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.483

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             496

_exptl_absorpt_coefficient_mu    1.915

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6460

_exptl_absorpt_correction_T_max  0.7006

_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      296(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  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            5700

_diffrn_reflns_av_R_equivalents  0.0167

_diffrn_reflns_av_sigmaI/netI    0.0327

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       18

_diffrn_reflns_theta_min         2.43

_diffrn_reflns_theta_max         25.05

_reflns_number_total             3799

_reflns_number_gt                3230

_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 F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.4166P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3799

_refine_ls_number_parameters     289

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0448

_refine_ls_R_factor_gt           0.0349

_refine_ls_wR_factor_ref         0.0856

_refine_ls_wR_factor_gt          0.0806

_refine_ls_goodness_of_fit_ref   1.046

_refine_ls_restrained_S_all      1.046

_refine_ls_shift/su_max          0.001

_refine_ls_shift/su_mean         0.000

loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

Br1 Br 0.07996(4) 0.67073(3) 0.510180(19) 0.04673(12) Uani 1 1 d . . .
C1 C 0.2794(3) 0.4777(3) 0.50577(16) 0.0325(6) Uani 1 1 d . . .
C2 C 0.3658(4) 0.4558(3) 0.42808(16) 0.0402(6) Uani 1 1 d . . .
H2 H 0.3281 0.5368 0.3790 0.048 Uiso 1 1 calc R . .
C3 C 0.5072(4) 0.3147(3) 0.42320(17) 0.0430(7) Uani 1 1 d . . .
H3 H 0.5681 0.2991 0.3715 0.052 Uiso 1 1 calc R . .
C4 C 0.5567(3) 0.1967(3) 0.49674(18) 0.0403(6) Uani 1 1 d . . .
C5 C 0.4737(4) 0.2162(3) 0.57525(17) 0.0384(6) Uani 1 1 d . . .
H5 H 0.5118 0.1340 0.6238 0.046 Uiso 1 1 calc R . .
C6 C 0.3332(3) 0.3592(3) 0.58117(15) 0.0305(5) Uani 1 1 d . . .
C7 C 0.2511(3) 0.3865(3) 0.66840(15) 0.0322(6) Uani 1 1 d . . .
C8 C 0.0843(3) 0.2777(3) 0.78876(15) 0.0312(5) Uani 1 1 d . . .
C9 C -0.1006(3) 0.4162(3) 0.79001(15) 0.0318(6) Uani 1 1 d . . .
C10 C -0.1276(4) 0.5727(3) 0.75407(18) 0.0424(7) Uani 1 1 d . . .
H10 H -0.0337 0.5943 0.7280 0.051 Uiso 1 1 calc R . .
C11 C -0.2919(4) 0.6961(3) 0.7565(2) 0.0493(7) Uani 1 1 d . . .
H11 H -0.3068 0.7999 0.7322 0.059 Uiso 1 1 calc R . .
C12 C -0.4338(4) 0.6690(4) 0.79423(18) 0.0468(7) Uani 1 1 d . . .
H12 H -0.5440 0.7532 0.7959 0.056 Uiso 1 1 calc R . .
C13 C -0.4102(4) 0.5161(4) 0.8292(2) 0.0559(8) Uani 1 1 d . . .
H13 H -0.5056 0.4954 0.8541 0.067 Uiso 1 1 calc R . .
C14 C -0.2446(4) 0.3909(4) 0.82792(19) 0.0481(7) Uani 1 1 d . . .
H14 H -0.2304 0.2877 0.8532 0.058 Uiso 1 1 calc R . .
C15 C 0.0674(3) 0.1161(3) 0.80600(16) 0.0342(6) Uani 1 1 d . . .
C16 C 0.0042(4) 0.0715(4) 0.74151(18) 0.0512(8) Uani 1 1 d . . .
H16 H -0.0300 0.1399 0.6877 0.061 Uiso 1 1 calc R . .
C17 C -0.0084(6) -0.0738(4) 0.7564(2) 0.0690(11) Uani 1 1 d . . .
H17 H -0.0470 -0.1038 0.7119 0.083 Uiso 1 1 calc R . .
C18 C 0.0353(5) -0.1736(4) 0.8359(2) 0.0669(10) Uani 1 1 d . . .
H18 H 0.0260 -0.2708 0.8457 0.080 Uiso 1 1 calc R . .
C19 C 0.0929(4) -0.1296(4) 0.9010(2) 0.0556(8) Uani 1 1 d . . .
H19 H 0.1207 -0.1962 0.9556 0.067 Uiso 1 1 calc R . .
C20 C 0.1098(4) 0.0137(3) 0.88621(17) 0.0426(7) Uani 1 1 d . . .
H20 H 0.1504 0.0416 0.9309 0.051 Uiso 1 1 calc R . .
C21 C 0.2146(3) 0.2706(3) 0.85587(15) 0.0309(5) Uani 1 1 d . . .
C22 C 0.1597(4) 0.3528(3) 0.92282(17) 0.0421(7) Uani 1 1 d . . .
H22 H 0.0410 0.4211 0.9262 0.051 Uiso 1 1 calc R . .
C23 C 0.2799(4) 0.3348(4) 0.98543(19) 0.0528(8) Uani 1 1 d . . .
H23 H 0.2410 0.3915 1.0302 0.063 Uiso 1 1 calc R . .
C24 C 0.4557(4) 0.2340(4) 0.98174(19) 0.0512(8) Uani 1 1 d . . .
H24 H 0.5359 0.2226 1.0236 0.061 Uiso 1 1 calc R . .
C25 C 0.5119(4) 0.1503(3) 0.91584(19) 0.0463(7) Uani 1 1 d . . .
H25 H 0.6306 0.0813 0.9132 0.056 Uiso 1 1 calc R . .
C26 C 0.3930(4) 0.1680(3) 0.85327(18) 0.0394(6) Uani 1 1 d . . .
H26 H 0.4326 0.1106 0.8088 0.047 Uiso 1 1 calc R . .
N1 N 0.1631(3) 0.2939(2) 0.70074(13) 0.0326(5) Uani 1 1 d . . .
H1 H 0.1514 0.2384 0.6667 0.039 Uiso 1 1 calc R . .
N2 N 0.7031(4) 0.0426(3) 0.4920(2) 0.0628(8) Uani 1 1 d . . .
O1 O 0.2714(3) 0.4799(2) 0.70459(12) 0.0424(5) Uani 1 1 d . . .
O2 O 0.7610(4) -0.0525(3) 0.55890(19) 0.1047(11) Uani 1 1 d . . .
O3 O 0.7560(4) 0.0140(3) 0.42080(18) 0.0991(10) Uani 1 1 d . . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;

loop_

_geom_bond_atom_site_label_1

_geom_bond_atom_site_label_2

_geom_bond_distance

_geom_bond_site_symmetry_2

_geom_bond_publ_flag

Br1 C1 1.890(2) . ?
C1 C2 1.378(4) . ?
C1 C6 1.399(3) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 N2 1.466(3) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.508(3) . ?
C7 O1 1.215(3) . ?
C7 N1 1.355(3) . ?
C8 N1 1.491(3) . ?
C8 C21 1.540(3) . ?
C8 C9 1.547(3) . ?
C8 C15 1.551(3) . ?
C9 C14 1.380(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.384(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.376(4) . ?
C21 C26 1.392(4) . ?
C22 C23 1.389(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N2 O2 1.208(4) . ?
N2 O3 1.214(4) . ?

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 121.6(2) . . ?
C2 C1 Br1 119.27(19) . . ?
C6 C1 Br1 119.08(19) . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 122.8(2) . . ?
C3 C4 N2 119.1(2) . . ?
C5 C4 N2 118.0(3) . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C7 119.6(2) . . ?
C1 C6 C7 122.3(2) . . ?
O1 C7 N1 125.9(2) . . ?
O1 C7 C6 120.7(2) . . ?
N1 C7 C6 113.4(2) . . ?
N1 C8 C21 108.34(19) . . ?
N1 C8 C9 110.03(19) . . ?
C21 C8 C9 112.83(19) . . ?
N1 C8 C15 106.09(19) . . ?
C21 C8 C15 109.0(2) . . ?
C9 C8 C15 110.3(2) . . ?
C14 C9 C10 117.1(2) . . ?
C14 C9 C8 121.8(2) . . ?
C10 C9 C8 121.0(2) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 121.6(3) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C20 C15 C16 117.7(2) . . ?
C20 C15 C8 121.6(2) . . ?
C16 C15 C8 120.6(2) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C22 C21 C26 118.2(2) . . ?
C22 C21 C8 122.5(2) . . ?
C26 C21 C8 119.1(2) . . ?
C21 C22 C23 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.4(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.9(3) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C7 N1 C8 127.3(2) . . ?
C7 N1 H1 116.4 . . ?
C8 N1 H1 116.4 . . ?
O2 N2 O3 123.0(3) . . ?
O2 N2 C4 118.6(3) . . ?
O3 N2 C4 118.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.983

_diffrn_reflns_theta_full        25.05

_diffrn_measured_fraction_theta_full 0.983

_refine_diff_density_max         0.274

_refine_diff_density_min         -0.533

_refine_diff_density_rms         0.074

data_080701a_0m
_database_code_depnum_ccdc_archive 'CCDC 699580'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 I N2 O3'
_chemical_formula_sum            'C26 H19 I N2 O3'
_chemical_formula_weight         534.33

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.4506(9)
_cell_length_b                   9.3577(10)
_cell_length_c                   15.3062(16)
_cell_angle_alpha                92.2320(10)
_cell_angle_beta                 95.9420(10)
_cell_angle_gamma                111.2940(10)
_cell_volume                     1117.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3546
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    1.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_T_max  0.7585
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5826
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3876
_reflns_number_gt                3508
_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0201P)²+1.3100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
I1 I -0.25052(3) 0.53049(3) 0.470878(15) 0.05078(9) Uani 1 1 d . . .
C1 C -0.0384(4) 0.7320(3) 0.4624(2) 0.0339(7) Uani 1 1 d . . .
C2 C 0.0083(4) 0.7683(4) 0.3794(2) 0.0440(8) Uani 1 1 d . . .
H2 H -0.0595 0.7083 0.3297 0.053 Uiso 1 1 calc R . .
C3 C 0.1536(4) 0.8918(4) 0.3700(2) 0.0443(8) Uani 1 1 d . . .
H3 H 0.1853 0.9159 0.3145 0.053 Uiso 1 1 calc R . .
C4 C 0.2511(4) 0.9790(4) 0.4442(2) 0.0382(7) Uani 1 1 d . . .
C5 C 0.2065(4) 0.9483(3) 0.5278(2) 0.0358(7) Uani 1 1 d . . .
H5 H 0.2735 1.0109 0.5769 0.043 Uiso 1 1 calc R . .
C6 C 0.0606(4) 0.8229(3) 0.53733(19) 0.0300(6) Uani 1 1 d . . .
C7 C 0.0081(4) 0.7933(3) 0.62848(18) 0.0294(6) Uani 1 1 d . . .
C8 C 0.1131(3) 0.7681(3) 0.78246(18) 0.0285(6) Uani 1 1 d . . .
C9 C -0.0350(4) 0.6224(3) 0.80206(19) 0.0305(6) Uani 1 1 d . . .
C10 C -0.1315(4) 0.5081(3) 0.7373(2) 0.0401(7) Uani 1 1 d . . .
H10 H -0.1123 0.5209 0.6788 0.048 Uiso 1 1 calc R . .
C11 C -0.2569(4) 0.3743(4) 0.7583(2) 0.0483(8) Uani 1 1 d . . .
H11 H -0.3224 0.2993 0.7138 0.058 Uiso 1 1 calc R . .
C12 C -0.2845(4) 0.3523(4) 0.8446(3) 0.0471(9) Uani 1 1 d . . .
H12 H -0.3673 0.2621 0.8586 0.056 Uiso 1 1 calc R . .
C13 C -0.1890(4) 0.4646(4) 0.9099(2) 0.0447(8) Uani 1 1 d . . .
H13 H -0.2080 0.4505 0.9683 0.054 Uiso 1 1 calc R . .
C14 C -0.0644(4) 0.5988(4) 0.8891(2) 0.0379(7) Uani 1 1 d . . .
H14 H 0.0000 0.6737 0.9338 0.045 Uiso 1 1 calc R . .
C15 C 0.0979(4) 0.9208(3) 0.81362(18) 0.0310(6) Uani 1 1 d . . .
C16 C -0.0443(4) 0.9298(4) 0.8464(2) 0.0430(8) Uani 1 1 d . . .
H16 H -0.1370 0.8401 0.8515 0.052 Uiso 1 1 calc R . .
C17 C -0.0506(5) 1.0717(5) 0.8718(2) 0.0575(10) Uani 1 1 d . . .
H17 H -0.1472 1.0760 0.8942 0.069 Uiso 1 1 calc R . .
C18 C 0.0847(6) 1.2058(4) 0.8643(2) 0.0572(10) Uani 1 1 d . . .
H18 H 0.0804 1.3005 0.8818 0.069 Uiso 1 1 calc R . .
C19 C 0.2254(5) 1.1983(4) 0.8307(3) 0.0534(9) Uani 1 1 d . . .
H19 H 0.3172 1.2884 0.8250 0.064 Uiso 1 1 calc R . .
C20 C 0.2322(4) 1.0576(4) 0.8052(2) 0.0428(8) Uani 1 1 d . . .
H20 H 0.3284 1.0544 0.7819 0.051 Uiso 1 1 calc R . .
C21 C 0.2772(3) 0.7535(3) 0.82867(18) 0.0291(6) Uani 1 1 d . . .
C22 C 0.3459(4) 0.8217(4) 0.9131(2) 0.0360(7) Uani 1 1 d . . .
H22 H 0.2990 0.8852 0.9400 0.043 Uiso 1 1 calc R . .
C23 C 0.4833(4) 0.7966(4) 0.9578(2) 0.0419(8) Uani 1 1 d . . .
H23 H 0.5281 0.8434 1.0143 0.050 Uiso 1 1 calc R . .
C24 C 0.5535(4) 0.7030(4) 0.9192(2) 0.0468(8) Uani 1 1 d . . .
H24 H 0.6448 0.6851 0.9496 0.056 Uiso 1 1 calc R . .
C25 C 0.4885(4) 0.6356(4) 0.8352(2) 0.0471(8) Uani 1 1 d . . .
H25 H 0.5379 0.5743 0.8083 0.057 Uiso 1 1 calc R . .
C26 C 0.3495(4) 0.6587(4) 0.7905(2) 0.0388(7) Uani 1 1 d . . .
H26 H 0.3042 0.6102 0.7344 0.047 Uiso 1 1 calc R . .
N1 N 0.1275(3) 0.7724(3) 0.68692(15) 0.0295(5) Uani 1 1 d . . .
H1 H 0.2150 0.7611 0.6679 0.035 Uiso 1 1 calc R . .
N2 N 0.4107(4) 1.1081(4) 0.4359(2) 0.0520(8) Uani 1 1 d . . .
O1 O -0.1295(3) 0.7911(2) 0.64593(13) 0.0375(5) Uani 1 1 d . . .
O2 O 0.4812(4) 1.1971(3) 0.5002(2) 0.0694(8) Uani 1 1 d . . .
O3 O 0.4671(3) 1.1172(4) 0.3647(2) 0.0745(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.097(3) . ?
C1 C2 1.388(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.372(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 N2 1.470(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(4) . ?
C7 O1 1.212(3) . ?
C7 N1 1.352(4) . ?
C8 N1 1.481(3) . ?
C8 C15 1.542(4) . ?
C8 C21 1.544(4) . ?
C8 C9 1.545(4) . ?
C9 C10 1.381(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.391(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.378(4) . ?
C15 C20 1.390(4) . ?
C16 C17 1.391(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.388(4) . ?
C21 C26 1.389(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N2 O2 1.213(4) . ?
N2 O3 1.228(4) . ?

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 120.2(3) . . ?
C2 C1 I1 117.8(2) . . ?
C6 C1 I1 121.9(2) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 N2 119.6(3) . . ?
C5 C4 N2 118.1(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 118.9(3) . . ?
C1 C6 C7 121.8(3) . . ?
O1 C7 N1 124.3(3) . . ?
O1 C7 C6 121.5(3) . . ?
N1 C7 C6 114.2(2) . . ?
N1 C8 C15 106.8(2) . . ?
N1 C8 C21 107.6(2) . . ?
C15 C8 C21 111.1(2) . . ?
N1 C8 C9 111.5(2) . . ?
C15 C8 C9 114.4(2) . . ?
C21 C8 C9 105.2(2) . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C8 122.5(3) . . ?
C14 C9 C8 119.0(3) . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C20 117.9(3) . . ?
C16 C15 C8 123.7(3) . . ?
C20 C15 C8 118.4(3) . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C22 C21 C26 118.2(3) . . ?
C22 C21 C8 120.9(3) . . ?
C26 C21 C8 120.6(3) . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C7 N1 C8 122.3(2) . . ?
C7 N1 H1 118.9 . . ?
C8 N1 H1 118.9 . . ?
O2 N2 O3 123.9(3) . . ?
O2 N2 C4 118.2(3) . . ?
O3 N2 C4 117.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.86 2.62 3.388(3) 149.3 2_676

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.066


