# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H32 Br2 N2 O2'
_chemical_formula_sum            'C18 H32 Br2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         468.28
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.8665(8)
_cell_length_b                   16.429(3)
_cell_length_c                   25.787(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2061.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3775
_cell_measurement_theta_min      2.4794
_cell_measurement_theta_max      25.9990
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale white'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960

_exptl_absorpt_coefficient_mu    3.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scan'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10958
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

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

_reflns_number_total             3640
_reflns_number_gt                3277
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0480
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         3640
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0127P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(9)

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'

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSELL V6. 3. 1'
_computing_publication_material  'Generate Report'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.62404(6) 0.21695(2) 0.451922(14) 0.02658(10) Uani d . 1 . .
Br Br2 -0.21248(6) 0.52332(2) 0.528925(12) 0.02293(9) Uani d . 1 . .
O O1 0.6921(4) 0.09946(14) 0.21215(8) 0.0235(6) Uani d . 1 . .
O O2 -0.1745(4) 0.33158(17) 0.24378(9) 0.0388(7) Uani d . 1 . .
N N1 0.2570(5) 0.14181(15) 0.19746(9) 0.0162(6) Uani d . 1 . .
H H1 0.0832 0.1362 0.2062 0.019 Uiso calc R 1 . .
N N2 0.2570(5) 0.31328(15) 0.21495(8) 0.0157(6) Uani d . 1 . .
H H2 0.4328 0.3189 0.2221 0.019 Uiso calc R 1 . .
C C1 0.9187(7) 0.1660(2) 0.41180(12) 0.0221(8) Uani d . 1 . .
H H1A 0.995 0.2061 0.3871 0.027 Uiso calc R 1 . .
H H1B 1.0682 0.1492 0.4356 0.027 Uiso calc R 1 . .
C C2 0.8171(7) 0.0922(2) 0.38216(11) 0.0186(8) Uani d . 1 . .
H H2A 0.7273 0.0547 0.407 0.022 Uiso calc R 1 . .
H H2B 0.9782 0.0635 0.3675 0.022 Uiso calc R 1 . .
C C3 0.6170(7) 0.10987(19) 0.33842(11) 0.0175(7) Uani d . 1 . .
H H3A 0.7028 0.1483 0.3137 0.021 Uiso calc R 1 . .
H H3B 0.4505 0.1362 0.3528 0.021 Uiso calc R 1 . .
C C4 0.5350(6) 0.0327(2) 0.30988(12) 0.0170(7) Uani d . 1 . .
H H4A 0.4547 -0.0058 0.3352 0.02 Uiso calc R 1 . .
H H4B 0.7029 0.0072 0.2955 0.02 Uiso calc R 1 . .
C C5 0.3304(6) 0.04494(19) 0.26594(11) 0.0160(7) Uani d . 1 . .
H H5A 0.2796 -0.0088 0.2514 0.019 Uiso calc R 1 . .
H H5B 0.1615 0.0703 0.2799 0.019 Uiso calc R 1 . .
C C6 0.4435(7) 0.0979(2) 0.22305(12) 0.0163(8) Uani d . 1 . .
C C7 0.3242(6) 0.19849(18) 0.15601(11) 0.0153(7) Uani d . 1 . .
H H7 0.5272 0.2078 0.1566 0.018 Uiso calc R 1 . .
C C8 0.1833(6) 0.27994(19) 0.16466(10) 0.0149(7) Uani d . 1 . .
H H8 -0.0196 0.2702 0.1646 0.018 Uiso calc R 1 . .
C C9 0.0764(7) 0.3358(2) 0.25076(12) 0.0202(8) Uani d . 1 . .
C C10 0.1975(7) 0.3691(2) 0.30020(11) 0.0275(9) Uani d . 1 . .
H H10A 0.3 0.4195 0.2919 0.033 Uiso calc R 1 . .
H H10B 0.3313 0.3291 0.3139 0.033 Uiso calc R 1 . .
C C11 -0.0086(6) 0.3880(2) 0.34234(12) 0.0176(8) Uani d . 1 . .
H H11A -0.1052 0.3374 0.3523 0.021 Uiso calc R 1 . .
H H11B -0.1472 0.4266 0.3287 0.021 Uiso calc R 1 . .
C C12 0.1272(7) 0.4250(2) 0.39040(11) 0.0203(8) Uani d . 1 . .
H H12A 0.2645 0.3862 0.4043 0.024 Uiso calc R 1 . .
H H12B 0.2253 0.4754 0.3804 0.024 Uiso calc R 1 . .
C C13 -0.0800(6) 0.4447(2) 0.43241(12) 0.0184(8) Uani d . 1 . .
H H13A -0.2303 0.4779 0.4176 0.022 Uiso calc R 1 . .
H H13B -0.1608 0.3936 0.4459 0.022 Uiso calc R 1 . .
C C14 0.0545(6) 0.49069(19) 0.47634(11) 0.0185(7) Uani d . 1 . .
H H14A 0.1465 0.5397 0.4624 0.022 Uiso calc R 1 . .
H H14B 0.1966 0.4559 0.4926 0.022 Uiso calc R 1 . .
C C15 0.2477(7) 0.33910(19) 0.12096(11) 0.0191(7) Uani d . 1 . .
H H15A 0.4463 0.3521 0.1214 0.023 Uiso calc R 1 . .
H H15B 0.145 0.3904 0.1266 0.023 Uiso calc R 1 . .
C C16 0.1712(7) 0.30407(19) 0.06820(11) 0.0221(8) Uani d . 1 . .
H H16A -0.0306 0.2971 0.0662 0.027 Uiso calc R 1 . .
H H16B 0.2273 0.3426 0.0406 0.027 Uiso calc R 1 . .
C C17 0.3101(6) 0.2226(2) 0.05931(11) 0.0222(8) Uani d . 1 . .
H H17A 0.5112 0.2307 0.0567 0.027 Uiso calc R 1 . .
H H17B 0.2455 0.1992 0.0261 0.027 Uiso calc R 1 . .
C C18 0.2487(7) 0.16318(19) 0.10303(11) 0.0197(7) Uani d . 1 . .
H H18A 0.3534 0.1123 0.0973 0.024 Uiso calc R 1 . .
H H18B 0.0506 0.1495 0.1026 0.024 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.02240(18) 0.02439(19) 0.0329(2) -0.00309(17) -0.00037(15) -0.00980(18)
Br2 0.02325(18) 0.02466(18) 0.02089(16) 0.00164(16) 0.00002(14) -0.00425(16)
O1 0.0055(11) 0.0399(15) 0.0250(13) 0.0005(11) 0.0024(10) 0.0121(11)
O2 0.0097(14) 0.073(2) 0.0338(15) -0.0010(13) -0.0024(11) -0.0288(14)
N1 0.0069(13) 0.0221(15) 0.0196(14) -0.0017(13) 0.0024(12) 0.0096(12)
N2 0.0069(13) 0.0261(16) 0.0141(13) -0.0034(13) -0.0030(12) -0.0055(11)
C1 0.0155(17) 0.028(2) 0.0228(19) 0.0005(17) 0.0021(15) 0.0041(17)
C2 0.0155(17) 0.0209(19) 0.0195(17) 0.0020(16) 0.0010(14) 0.0020(15)
C3 0.0167(17) 0.0178(18) 0.0181(17) -0.0014(16) -0.0009(15) 0.0028(15)
C4 0.0183(17) 0.0161(18) 0.0165(16) 0.0012(16) 0.0019(13) 0.0037(16)
C5 0.0129(16) 0.0186(18) 0.0166(16) -0.0018(14) 0.0031(13) 0.0031(14)
C6 0.0212(19) 0.0144(19) 0.0132(18) -0.0028(16) 0.0021(15) -0.0054(15)
C7 0.0138(16) 0.0166(18) 0.0154(16) -0.0037(14) 0.0018(13) 0.0048(14)
C8 0.0106(15) 0.0168(16) 0.0172(16) -0.0026(16) -0.0035(13) -0.0061(15)
C9 0.0150(19) 0.024(2) 0.0219(19) -0.0019(16) -0.0021(15) -0.0002(16)
C10 0.0173(18) 0.049(2) 0.0163(17) -0.0043(18) -0.0017(15) -0.0133(17)
C11 0.0159(17) 0.020(2) 0.0168(18) 0.0003(15) -0.0015(14) -0.0006(16)
C12 0.0161(18) 0.026(2) 0.0191(18) -0.0010(16) -0.0015(15) -0.0043(15)
C13 0.0198(17) 0.0176(18) 0.0178(17) -0.0010(15) -0.0024(14) 0.0008(15)
C14 0.0180(16) 0.0215(18) 0.0159(16) -0.0054(14) 0.0019(14) -0.0005(16)
C15 0.0222(18) 0.0153(17) 0.0200(17) -0.0011(16) -0.0031(15) 0.0022(14)
C16 0.0253(19) 0.024(2) 0.0173(16) -0.0074(16) -0.0032(15) 0.0043(15)
C17 0.0244(18) 0.0277(19) 0.0146(16) -0.0086(18) 0.0014(14) -0.0004(16)
C18 0.0262(18) 0.0132(16) 0.0197(17) -0.0001(17) 0.0034(16) -0.0035(14)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.957(3) ?
Br2 C14 . 1.953(3) ?
O1 C6 . 1.242(4) ?
O2 C9 . 1.236(4) ?
N1 C6 . 1.334(4) ?
N1 C7 . 1.455(4) ?
N1 H1 . 0.88 ?
N2 C9 . 1.327(4) ?
N2 C8 . 1.453(3) ?
N2 H2 . 0.88 ?
C1 C2 . 1.515(4) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.518(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.519(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.522(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.511(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C7 C8 . 1.520(4) ?
C7 C18 . 1.529(4) ?
C7 H7 . 1.0 ?
C8 C15 . 1.521(4) ?
C8 H8 . 1.0 ?
C9 C10 . 1.507(4) ?
C10 C11 . 1.511(4) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.530(4) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.515(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.511(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.523(4) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.517(4) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.521(4) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C7 . . 123.8(3) ?
C6 N1 H1 . . 118.1 ?
C7 N1 H1 . . 118.1 ?
C9 N2 C8 . . 124.2(2) ?
C9 N2 H2 . . 117.9 ?
C8 N2 H2 . . 117.9 ?
C2 C1 Br1 . . 111.7(2) ?
C2 C1 H1A . . 109.3 ?
Br1 C1 H1A . . 109.3 ?
C2 C1 H1B . . 109.3 ?
Br1 C1 H1B . . 109.3 ?
H1A C1 H1B . . 107.9 ?
C1 C2 C3 . . 115.6(3) ?
C1 C2 H2A . . 108.4 ?
C3 C2 H2A . . 108.4 ?
C1 C2 H2B . . 108.4 ?
C3 C2 H2B . . 108.4 ?
H2A C2 H2B . . 107.5 ?
C2 C3 C4 . . 111.7(3) ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 107.9 ?
C3 C4 C5 . . 115.0(3) ?
C3 C4 H4A . . 108.5 ?
C5 C4 H4A . . 108.5 ?
C3 C4 H4B . . 108.5 ?
C5 C4 H4B . . 108.5 ?
H4A C4 H4B . . 107.5 ?
C6 C5 C4 . . 112.5(3) ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5B . . 109.1 ?
C4 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.8 ?
O1 C6 N1 . . 122.6(3) ?
O1 C6 C5 . . 122.2(3) ?
N1 C6 C5 . . 115.2(3) ?
N1 C7 C8 . . 110.7(2) ?
N1 C7 C18 . . 111.1(2) ?
C8 C7 C18 . . 110.9(2) ?
N1 C7 H7 . . 108.0 ?
C8 C7 H7 . . 108.0 ?
C18 C7 H7 . . 108.0 ?
N2 C8 C15 . . 111.7(2) ?
N2 C8 C7 . . 110.6(2) ?
C15 C8 C7 . . 111.2(2) ?
N2 C8 H8 . . 107.7 ?
C15 C8 H8 . . 107.7 ?
C7 C8 H8 . . 107.7 ?
O2 C9 N2 . . 122.5(3) ?
O2 C9 C10 . . 122.0(3) ?
N2 C9 C10 . . 115.5(3) ?
C9 C10 C11 . . 115.1(3) ?
C9 C10 H10A . . 108.5 ?
C11 C10 H10A . . 108.5 ?
C9 C10 H10B . . 108.5 ?
C11 C10 H10B . . 108.5 ?
H10A C10 H10B . . 107.5 ?
C10 C11 C12 . . 112.2(3) ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.2 ?
C10 C11 H11B . . 109.2 ?
C12 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C13 C12 C11 . . 112.1(3) ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12B . . 109.2 ?
C11 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C14 C13 C12 . . 110.8(3) ?
C14 C13 H13A . . 109.5 ?
C12 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C13 C14 Br2 . . 111.70(19) ?
C13 C14 H14A . . 109.3 ?
Br2 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
Br2 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
C8 C15 C16 . . 111.7(3) ?
C8 C15 H15A . . 109.3 ?
C16 C15 H15A . . 109.3 ?
C8 C15 H15B . . 109.3 ?
C16 C15 H15B . . 109.3 ?
H15A C15 H15B . . 107.9 ?
C17 C16 C15 . . 111.1(3) ?
C17 C16 H16A . . 109.4 ?
C15 C16 H16A . . 109.4 ?
C17 C16 H16B . . 109.4 ?
C15 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C16 C17 C18 . . 111.5(2) ?
C16 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
C16 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 108.0 ?
C17 C18 C7 . . 111.8(3) ?
C17 C18 H18A . . 109.3 ?
C7 C18 H18A . . 109.3 ?
C17 C18 H18B . . 109.3 ?
C7 C18 H18B . . 109.3 ?
H18A C18 H18B . . 107.9 ?

_database_code_depnum_ccdc_archive 'CCDC 946263'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H40 Br2 N2 O2'
_chemical_formula_sum            'C22 H40 Br2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         524.38
_chemical_absolute_configuration rm

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.8466(7)
_cell_length_b                   17.841(3)
_cell_length_c                   28.081(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2428.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4092
_cell_measurement_theta_min      2.2831
_cell_measurement_theta_max      26.9218
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale white'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088

_exptl_absorpt_coefficient_mu    3.358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.73

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15510
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       36

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

_reflns_number_total             5612
_reflns_number_gt                4654
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0826
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_number_reflns         5612
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.9407P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.756
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(10)

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'

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSELL V6.3.1'
_computing_publication_material  'Generate Report'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.12531(9) 0.74021(2) 0.853956(13) 0.02798(10) Uani d . 1 . .
Br Br2 0.34747(10) 0.67097(2) 1.027166(13) 0.03337(12) Uani d . 1 . .
O O1 0.7502(5) 0.15669(15) 0.91886(9) 0.0234(6) Uani d . 1 . .
O O2 -0.0719(5) 0.15627(14) 0.79531(9) 0.0251(6) Uani d . 1 . .
N N1 0.3627(7) 0.12006(14) 0.81260(9) 0.0149(6) Uani d . 1 . .
H H1 0.5351 0.1304 0.8095 0.018 Uiso calc R 1 . .
N N2 0.3204(6) 0.10846(15) 0.91212(9) 0.0149(6) Uani d . 1 . .
H H2 0.1502 0.1128 0.9203 0.018 Uiso calc R 1 . .
C C1 0.1204(8) 0.66517(19) 0.82559(13) 0.0239(8) Uani d . 1 . .
H H1A 0.1455 0.6759 0.792 0.029 Uiso calc R 1 . .
H H1B 0.2996 0.6673 0.8409 0.029 Uiso calc R 1 . .
C C2 -0.0014(8) 0.5878(2) 0.83156(14) 0.0231(8) Uani d . 1 . .
H H2A -0.1822 0.5864 0.8168 0.028 Uiso calc R 1 . .
H H2B -0.0248 0.5774 0.8652 0.028 Uiso calc R 1 . .
C C3 0.1796(8) 0.52716(19) 0.80948(13) 0.0220(8) Uani d . 1 . .
H H3A 0.1952 0.536 0.7755 0.026 Uiso calc R 1 . .
H H3B 0.3632 0.53 0.8231 0.026 Uiso calc R 1 . .
C C4 0.0614(7) 0.44886(19) 0.81796(13) 0.0208(8) Uani d . 1 . .
H H4A 0.0493 0.4402 0.852 0.025 Uiso calc R 1 . .
H H4B -0.1244 0.447 0.8052 0.025 Uiso calc R 1 . .
C C5 0.2295(8) 0.3866(2) 0.79574(13) 0.0204(8) Uani d . 1 . .
H H5A 0.4162 0.3888 0.8081 0.025 Uiso calc R 1 . .
H H5B 0.2388 0.3946 0.7616 0.025 Uiso calc R 1 . .
C C6 0.1126(8) 0.30892(17) 0.80514(12) 0.0188(7) Uani d . 1 . .
H H6A -0.0717 0.306 0.7918 0.023 Uiso calc R 1 . .
H H6B 0.0975 0.3015 0.8393 0.023 Uiso calc R 1 . .
C C7 0.2878(7) 0.2462(2) 0.78411(13) 0.0205(8) Uani d . 1 . .
H H7A 0.2895 0.2507 0.7497 0.025 Uiso calc R 1 . .
H H7B 0.4762 0.2513 0.7953 0.025 Uiso calc R 1 . .
C C8 0.1785(7) 0.1696(2) 0.79780(11) 0.0152(7) Uani d . 1 . .
C C9 0.2852(7) 0.04858(19) 0.83393(12) 0.0149(7) Uani d . 1 . .
H H9 0.0835 0.0465 0.8359 0.018 Uiso calc R 1 . .
C C10 0.4024(7) 0.04312(17) 0.88482(11) 0.0130(7) Uani d . 1 . .
H H10 0.6042 0.0429 0.8826 0.016 Uiso calc R 1 . .
C C11 0.4977(7) 0.1624(2) 0.92518(12) 0.0166(8) Uani d . 1 . .
C C12 0.3758(8) 0.23138(17) 0.94750(11) 0.0162(7) Uani d . 1 . .
H H12A 0.3952 0.2279 0.9818 0.019 Uiso calc R 1 . .
H H12B 0.1802 0.2332 0.9403 0.019 Uiso calc R 1 . .
C C13 0.5101(7) 0.30397(18) 0.93051(12) 0.0150(7) Uani d . 1 . .
H H13A 0.4963 0.307 0.8961 0.018 Uiso calc R 1 . .
H H13B 0.7043 0.3034 0.9388 0.018 Uiso calc R 1 . .
C C14 0.3745(8) 0.37274(18) 0.95250(12) 0.0190(7) Uani d . 1 . .
H H14A 0.1827 0.3744 0.9427 0.023 Uiso calc R 1 . .
H H14B 0.3784 0.3678 0.9869 0.023 Uiso calc R 1 . .
C C15 0.5124(8) 0.4463(2) 0.93870(14) 0.0221(8) Uani d . 1 . .
H H15A 0.5187 0.4498 0.9042 0.027 Uiso calc R 1 . .
H H15B 0.701 0.446 0.9503 0.027 Uiso calc R 1 . .
C C16 0.3653(8) 0.51523(18) 0.95838(12) 0.0203(7) Uani d . 1 . .
H H16A 0.1759 0.5153 0.9472 0.024 Uiso calc R 1 . .
H H16B 0.3617 0.5122 0.9929 0.024 Uiso calc R 1 . .
C C17 0.5026(8) 0.5883(2) 0.94369(14) 0.0242(8) Uani d . 1 . .
H H17A 0.6863 0.5897 0.9574 0.029 Uiso calc R 1 . .
H H17B 0.5229 0.5885 0.9093 0.029 Uiso calc R 1 . .
C C18 0.3491(9) 0.65907(19) 0.95851(11) 0.0218(8) Uani d . 1 . .
H H18A 0.1605 0.6566 0.947 0.026 Uiso calc R 1 . .
H H18B 0.4365 0.7023 0.944 0.026 Uiso calc R 1 . .
C C19 0.3124(8) -0.03034(18) 0.90762(12) 0.0186(8) Uani d . 1 . .
H H19A 0.1133 -0.0305 0.9111 0.022 Uiso calc R 1 . .
H H19B 0.3931 -0.0343 0.9391 0.022 Uiso calc R 1 . .
C C20 0.4006(8) -0.09790(18) 0.87769(12) 0.0198(8) Uani d . 1 . .
H H20A 0.6003 -0.1012 0.8773 0.024 Uiso calc R 1 . .
H H20B 0.3294 -0.1434 0.892 0.024 Uiso calc R 1 . .
C C21 0.2941(8) -0.09153(19) 0.82659(12) 0.0227(9) Uani d . 1 . .
H H21A 0.3651 -0.1329 0.8078 0.027 Uiso calc R 1 . .
H H21B 0.0943 -0.0946 0.8266 0.027 Uiso calc R 1 . .
C C22 0.3836(9) -0.01762(18) 0.80423(11) 0.0202(7) Uani d . 1 . .
H H22A 0.5832 -0.0164 0.8018 0.024 Uiso calc R 1 . .
H H22B 0.308 -0.0138 0.7723 0.024 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0288(2) 0.01995(18) 0.0351(2) -0.00233(18) 0.00275(19) -0.00675(15)
Br2 0.0495(3) 0.0250(2) 0.02556(19) 0.0080(2) 0.0027(2) -0.00076(15)
O1 0.0067(13) 0.0251(16) 0.0383(16) 0.0004(11) 0.0001(11) -0.0127(12)
O2 0.0059(14) 0.0232(14) 0.0460(16) -0.0027(11) 0.0011(11) 0.0096(12)
N1 0.0037(13) 0.0164(14) 0.0245(14) -0.0015(13) 0.0010(14) 0.0042(11)
N2 0.0037(15) 0.0167(15) 0.0242(15) 0.0017(12) 0.0030(12) -0.0056(11)
C1 0.0152(19) 0.0225(18) 0.0339(19) -0.0025(19) -0.0005(17) -0.0030(15)
C2 0.018(2) 0.0172(19) 0.034(2) 0.0016(16) 0.0008(17) -0.0014(16)
C3 0.015(2) 0.0210(19) 0.0295(19) -0.0041(16) 0.0054(16) -0.0020(15)
C4 0.014(2) 0.0226(19) 0.0258(19) -0.0024(15) 0.0013(14) 0.0003(15)
C5 0.0153(19) 0.0171(19) 0.029(2) -0.0036(15) 0.0052(15) 0.0025(15)
C6 0.0118(18) 0.0157(17) 0.0290(18) 0.0003(16) 0.0002(17) 0.0037(13)
C7 0.0129(18) 0.020(2) 0.0283(19) -0.0014(15) 0.0047(13) 0.0060(15)
C8 0.0105(19) 0.0158(16) 0.0195(16) -0.0034(15) 0.0027(14) 0.0006(13)
C9 0.0058(16) 0.0149(17) 0.0240(17) -0.0044(13) 0.0001(13) -0.0004(13)
C10 0.0063(17) 0.0132(16) 0.0194(16) 0.0029(14) 0.0003(14) -0.0034(12)
C11 0.0108(19) 0.020(2) 0.0188(18) -0.0002(16) 0.0007(14) -0.0016(15)
C12 0.0099(16) 0.0190(17) 0.0197(16) 0.0016(17) 0.0019(15) -0.0057(13)
C13 0.0087(17) 0.0155(18) 0.0208(18) 0.0007(14) -0.0018(14) -0.0029(13)
C14 0.0103(17) 0.0180(17) 0.0286(18) 0.0045(17) 0.0027(17) -0.0035(13)
C15 0.017(2) 0.020(2) 0.029(2) -0.0035(16) 0.0010(16) -0.0031(15)
C16 0.0112(17) 0.0201(17) 0.0295(18) -0.0042(18) 0.0009(17) -0.0027(13)
C17 0.021(2) 0.021(2) 0.030(2) -0.0022(16) 0.0057(16) -0.0008(16)
C18 0.025(2) 0.0179(17) 0.0229(17) -0.0004(19) -0.0030(17) 0.0003(13)
C19 0.015(2) 0.0175(18) 0.0228(17) 0.0016(15) 0.0030(14) 0.0018(14)
C20 0.019(2) 0.0140(17) 0.0267(18) 0.0017(16) 0.0011(16) 0.0009(13)
C21 0.027(2) 0.0137(18) 0.027(2) -0.0001(16) 0.0023(16) -0.0038(14)
C22 0.021(2) 0.0206(17) 0.0186(16) -0.0031(18) 0.0007(17) -0.0003(13)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.961(4) ?
Br2 C18 . 1.940(3) ?
O1 C11 . 1.241(4) ?
O2 C8 . 1.239(4) ?
N1 C8 . 1.323(4) ?
N1 C9 . 1.458(4) ?
N1 H1 . 0.86 ?
N2 C11 . 1.341(4) ?
N2 C10 . 1.451(4) ?
N2 H2 . 0.86 ?
C1 C2 . 1.511(5) ?
C1 H1A . 0.97 ?
C1 H1B . 0.97 ?
C2 C3 . 1.524(5) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.528(5) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.513(5) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 C6 . 1.520(5) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C7 . 1.523(5) ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.516(5) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C9 C22 . 1.522(5) ?
C9 C10 . 1.541(5) ?
C9 H9 . 0.98 ?
C10 C19 . 1.522(4) ?
C10 H10 . 0.98 ?
C11 C12 . 1.502(5) ?
C12 C13 . 1.526(5) ?
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
C13 C14 . 1.523(4) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.522(5) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.525(5) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C17 . 1.520(5) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C18 . 1.524(5) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.530(5) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.529(5) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 C22 . 1.524(5) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C22 H22A . 0.97 ?
C22 H22B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C9 . . 122.6(3) ?
C8 N1 H1 . . 118.7 ?
C9 N1 H1 . . 118.7 ?
C11 N2 C10 . . 123.1(3) ?
C11 N2 H2 . . 118.5 ?
C10 N2 H2 . . 118.5 ?
C2 C1 Br1 . . 110.0(3) ?
C2 C1 H1A . . 109.7 ?
Br1 C1 H1A . . 109.7 ?
C2 C1 H1B . . 109.7 ?
Br1 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
C1 C2 C3 . . 112.2(3) ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 111.7(3) ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
C5 C4 C3 . . 113.9(3) ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C4 C5 C6 . . 113.4(3) ?
C4 C5 H5A . . 108.9 ?
C6 C5 H5A . . 108.9 ?
C4 C5 H5B . . 108.9 ?
C6 C5 H5B . . 108.9 ?
H5A C5 H5B . . 107.7 ?
C5 C6 C7 . . 113.2(3) ?
C5 C6 H6A . . 108.9 ?
C7 C6 H6A . . 108.9 ?
C5 C6 H6B . . 108.9 ?
C7 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.8 ?
C8 C7 C6 . . 111.7(3) ?
C8 C7 H7A . . 109.3 ?
C6 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
C6 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
O2 C8 N1 . . 123.4(3) ?
O2 C8 C7 . . 120.1(3) ?
N1 C8 C7 . . 116.5(3) ?
N1 C9 C22 . . 111.9(3) ?
N1 C9 C10 . . 109.9(3) ?
C22 C9 C10 . . 110.1(3) ?
N1 C9 H9 . . 108.3 ?
C22 C9 H9 . . 108.3 ?
C10 C9 H9 . . 108.3 ?
N2 C10 C19 . . 113.0(3) ?
N2 C10 C9 . . 109.8(3) ?
C19 C10 C9 . . 109.8(3) ?
N2 C10 H10 . . 108.0 ?
C19 C10 H10 . . 108.0 ?
C9 C10 H10 . . 108.0 ?
O1 C11 N2 . . 122.3(4) ?
O1 C11 C12 . . 121.0(3) ?
N2 C11 C12 . . 116.7(3) ?
C11 C12 C13 . . 113.4(3) ?
C11 C12 H12A . . 108.9 ?
C13 C12 H12A . . 108.9 ?
C11 C12 H12B . . 108.9 ?
C13 C12 H12B . . 108.9 ?
H12A C12 H12B . . 107.7 ?
C12 C13 C14 . . 111.9(3) ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C15 C14 C13 . . 113.7(3) ?
C15 C14 H14A . . 108.8 ?
C13 C14 H14A . . 108.8 ?
C15 C14 H14B . . 108.8 ?
C13 C14 H14B . . 108.8 ?
H14A C14 H14B . . 107.7 ?
C14 C15 C16 . . 113.4(3) ?
C14 C15 H15A . . 108.9 ?
C16 C15 H15A . . 108.9 ?
C14 C15 H15B . . 108.9 ?
C16 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
C17 C16 C15 . . 112.8(3) ?
C17 C16 H16A . . 109.0 ?
C15 C16 H16A . . 109.0 ?
C17 C16 H16B . . 109.0 ?
C15 C16 H16B . . 109.0 ?
H16A C16 H16B . . 107.8 ?
C18 C17 C16 . . 115.0(3) ?
C18 C17 H17A . . 108.5 ?
C16 C17 H17A . . 108.5 ?
C18 C17 H17B . . 108.5 ?
C16 C17 H17B . . 108.5 ?
H17A C17 H17B . . 107.5 ?
C17 C18 Br2 . . 111.3(2) ?
C17 C18 H18A . . 109.4 ?
Br2 C18 H18A . . 109.4 ?
C17 C18 H18B . . 109.4 ?
Br2 C18 H18B . . 109.4 ?
H18A C18 H18B . . 108.0 ?
C10 C19 C20 . . 111.5(3) ?
C10 C19 H19A . . 109.3 ?
C20 C19 H19A . . 109.3 ?
C10 C19 H19B . . 109.3 ?
C20 C19 H19B . . 109.3 ?
H19A C19 H19B . . 108.0 ?
C21 C20 C19 . . 111.3(3) ?
C21 C20 H20A . . 109.4 ?
C19 C20 H20A . . 109.4 ?
C21 C20 H20B . . 109.4 ?
C19 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108.0 ?
C22 C21 C20 . . 110.8(3) ?
C22 C21 H21A . . 109.5 ?
C20 C21 H21A . . 109.5 ?
C22 C21 H21B . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 108.1 ?
C9 C22 C21 . . 110.9(3) ?
C9 C22 H22A . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C9 C22 H22B . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?

_database_code_depnum_ccdc_archive 'CCDC 946264'