# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Ivan J. B. Lin'
_publ_contact_author_email       d9412003@gmail.com
loop_
_publ_author_name
I.Lin
'Joseph C. Y. Lin'

data_ap56m
_database_code_depnum_ccdc_archive 'CCDC 809541'
#TrackingRef '3936_web_deposit_cif_file_0_JosephC.Y.Lin_1295852605.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H30 N2 O4'
_chemical_formula_weight         302.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   45.265(4)
_cell_length_b                   8.3038(8)
_cell_length_c                   9.1833(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.583(2)
_cell_angle_gamma                90.00
_cell_volume                     3413.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5159
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.04

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.56076
_exptl_absorpt_correction_T_max  0.91932
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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            9472
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         0.91
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3016
_reflns_number_gt                2644
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+1.8004P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3016
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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
O1 O 0.23158(2) 0.66383(13) 0.19828(12) 0.0203(3) Uani 1 1 d . . .
O2 O 0.27930(2) 0.71850(14) 0.18304(12) 0.0214(3) Uani 1 1 d . . .
O3 O 0.32771(3) 1.08037(14) 0.36914(12) 0.0245(3) Uani 1 1 d . . .
H3B H 0.3312 1.0022 0.3002 0.029 Uiso 1 1 d . . .
H3C H 0.3073 1.0812 0.3483 0.029 Uiso 1 1 d . . .
O4 O 0.33571(3) 0.83558(15) 0.16780(12) 0.0252(3) Uani 1 1 d . . .
H4C H 0.3174 0.7908 0.1663 0.030 Uiso 1 1 d . . .
H4D H 0.3363 0.8714 0.0746 0.030 Uiso 1 1 d . . .
N1 N 0.28500(3) 0.44449(15) 0.01730(13) 0.0153(3) Uani 1 1 d . . .
N2 N 0.32656(3) 0.45646(15) -0.07020(13) 0.0149(3) Uani 1 1 d . . .
C1 C 0.30002(3) 0.30301(18) 0.05510(16) 0.0164(3) Uani 1 1 d . . .
H1A H 0.2934 0.2167 0.1098 0.020 Uiso 1 1 calc R . .
C2 C 0.32590(3) 0.30988(18) 0.00011(16) 0.0163(3) Uani 1 1 d . . .
H2A H 0.3409 0.2290 0.0081 0.020 Uiso 1 1 calc R . .
C3 C 0.30143(3) 0.53487(19) -0.05883(16) 0.0155(3) Uani 1 1 d . . .
H3A H 0.2961 0.6383 -0.0985 0.019 Uiso 1 1 calc R . .
C4 C 0.25570(3) 0.48848(19) 0.05505(17) 0.0173(4) Uani 1 1 d . . .
H4A H 0.2477 0.3959 0.1049 0.021 Uiso 1 1 calc R . .
H4B H 0.2419 0.5093 -0.0371 0.021 Uiso 1 1 calc R . .
C5 C 0.25619(3) 0.63712(18) 0.15507(16) 0.0154(3) Uani 1 1 d . . .
C6 C 0.35128(3) 0.5164(2) -0.14207(17) 0.0182(4) Uani 1 1 d . . .
H6A H 0.3452 0.6184 -0.1938 0.022 Uiso 1 1 calc R . .
H6B H 0.3557 0.4371 -0.2163 0.022 Uiso 1 1 calc R . .
C7 C 0.37921(3) 0.54491(19) -0.03100(17) 0.0185(4) Uani 1 1 d . . .
H7A H 0.3846 0.4444 0.0247 0.022 Uiso 1 1 calc R . .
H7B H 0.3751 0.6288 0.0399 0.022 Uiso 1 1 calc R . .
C8 C 0.40543(3) 0.5981(2) -0.10639(17) 0.0196(4) Uani 1 1 d . . .
H8A H 0.4100 0.5122 -0.1745 0.024 Uiso 1 1 calc R . .
H8B H 0.3996 0.6957 -0.1657 0.024 Uiso 1 1 calc R . .
C9 C 0.43342(3) 0.6342(2) 0.00245(18) 0.0210(4) Uani 1 1 d . . .
H9A H 0.4390 0.5369 0.0624 0.025 Uiso 1 1 calc R . .
H9B H 0.4289 0.7207 0.0699 0.025 Uiso 1 1 calc R . .
C10 C 0.45993(3) 0.6860(2) -0.07128(17) 0.0211(4) Uani 1 1 d . . .
H10A H 0.4645 0.5992 -0.1383 0.025 Uiso 1 1 calc R . .
H10B H 0.4542 0.7829 -0.1319 0.025 Uiso 1 1 calc R . .
C11 C 0.48798(3) 0.7236(2) 0.03686(17) 0.0218(4) Uani 1 1 d . . .
H11A H 0.4833 0.8094 0.1048 0.026 Uiso 1 1 calc R . .
H11B H 0.4939 0.6263 0.0964 0.026 Uiso 1 1 calc R . .
C12 C 0.51415(3) 0.7774(2) -0.03752(17) 0.0217(4) Uani 1 1 d . . .
H12A H 0.5081 0.8740 -0.0978 0.026 Uiso 1 1 calc R . .
H12B H 0.5188 0.6912 -0.1050 0.026 Uiso 1 1 calc R . .
C13 C 0.54233(3) 0.8167(2) 0.06925(18) 0.0226(4) Uani 1 1 d . . .
H13A H 0.5376 0.9013 0.1381 0.027 Uiso 1 1 calc R . .
H13B H 0.5487 0.7194 0.1280 0.027 Uiso 1 1 calc R . .
C14 C 0.56816(4) 0.8739(2) -0.0063(2) 0.0264(4) Uani 1 1 d . . .
H14A H 0.5618 0.9706 -0.0658 0.032 Uiso 1 1 calc R . .
H14B H 0.5730 0.7888 -0.0743 0.032 Uiso 1 1 calc R . .
C15 C 0.59615(4) 0.9146(2) 0.1008(2) 0.0353(5) Uani 1 1 d . . .
H15A H 0.6119 0.9507 0.0457 0.053 Uiso 1 1 calc R . .
H15B H 0.6030 0.8187 0.1584 0.053 Uiso 1 1 calc R . .
H15C H 0.5916 1.0005 0.1673 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0205(6) 0.0230(6) 0.0186(6) -0.0004(5) 0.0068(5) 0.0029(5)
O2 0.0221(6) 0.0226(6) 0.0199(6) -0.0042(5) 0.0041(5) -0.0037(5)
O3 0.0236(6) 0.0272(7) 0.0219(6) -0.0034(5) 0.0005(5) 0.0018(5)
O4 0.0230(6) 0.0330(7) 0.0195(6) -0.0014(5) 0.0027(5) -0.0033(5)
N1 0.0169(6) 0.0178(7) 0.0112(6) -0.0028(5) 0.0021(5) -0.0018(5)
N2 0.0153(7) 0.0180(7) 0.0113(6) -0.0011(5) 0.0018(5) -0.0012(5)
C1 0.0211(8) 0.0150(8) 0.0125(7) -0.0005(6) 0.0005(6) -0.0022(6)
C2 0.0184(8) 0.0166(8) 0.0129(7) 0.0011(6) -0.0004(6) 0.0017(6)
C3 0.0178(8) 0.0170(8) 0.0117(7) -0.0020(6) 0.0022(6) -0.0005(6)
C4 0.0145(8) 0.0221(8) 0.0157(8) -0.0023(6) 0.0029(6) -0.0015(6)
C5 0.0176(8) 0.0188(8) 0.0094(7) 0.0044(6) 0.0007(6) 0.0009(6)
C6 0.0170(8) 0.0249(9) 0.0136(8) 0.0012(6) 0.0055(6) -0.0012(7)
C7 0.0197(8) 0.0209(8) 0.0150(8) -0.0004(6) 0.0027(6) -0.0009(6)
C8 0.0184(8) 0.0234(9) 0.0174(8) -0.0004(7) 0.0042(6) -0.0020(7)
C9 0.0199(8) 0.0255(9) 0.0175(8) -0.0001(7) 0.0027(7) -0.0024(7)
C10 0.0191(8) 0.0260(9) 0.0183(8) -0.0003(7) 0.0030(7) -0.0027(7)
C11 0.0191(8) 0.0258(9) 0.0202(8) 0.0003(7) 0.0024(7) -0.0016(7)
C12 0.0208(8) 0.0251(9) 0.0190(8) 0.0008(7) 0.0028(7) -0.0017(7)
C13 0.0189(8) 0.0258(9) 0.0227(9) -0.0003(7) 0.0016(7) -0.0010(7)
C14 0.0193(9) 0.0285(10) 0.0312(10) 0.0018(8) 0.0031(7) -0.0011(7)
C15 0.0204(9) 0.0365(11) 0.0479(12) -0.0048(9) 0.0012(8) -0.0045(8)

_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
O1 C5 1.2566(18) . ?
O2 C5 1.2398(19) . ?
O3 H3B 0.9365 . ?
O3 H3C 0.9150 . ?
O4 H4C 0.9064 . ?
O4 H4D 0.9103 . ?
N1 C3 1.327(2) . ?
N1 C1 1.376(2) . ?
N1 C4 1.4662(19) . ?
N2 C3 1.328(2) . ?
N2 C2 1.380(2) . ?
N2 C6 1.4683(19) . ?
C1 C2 1.344(2) . ?
C1 H1A 0.9500 . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C4 C5 1.537(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.520(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.526(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.522(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.523(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.522(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
H3B O3 H3C 97.5 . . ?
H4C O4 H4D 106.0 . . ?
C3 N1 C1 108.73(13) . . ?
C3 N1 C4 125.57(13) . . ?
C1 N1 C4 125.70(13) . . ?
C3 N2 C2 108.47(13) . . ?
C3 N2 C6 126.03(13) . . ?
C2 N2 C6 125.48(13) . . ?
C2 C1 N1 107.13(13) . . ?
C2 C1 H1A 126.4 . . ?
N1 C1 H1A 126.4 . . ?
C1 C2 N2 107.11(13) . . ?
C1 C2 H2A 126.4 . . ?
N2 C2 H2A 126.4 . . ?
N1 C3 N2 108.55(14) . . ?
N1 C3 H3A 125.7 . . ?
N2 C3 H3A 125.7 . . ?
N1 C4 C5 114.12(12) . . ?
N1 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
N1 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O2 C5 O1 126.78(14) . . ?
O2 C5 C4 119.87(13) . . ?
O1 C5 C4 113.34(13) . . ?
N2 C6 C7 111.38(12) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.46(12) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 112.75(13) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 113.40(13) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 113.75(13) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 113.39(13) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 114.05(13) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 113.56(14) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.39(15) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.149

# Attachment '3937_web_deposit_cif_file_1_JosephC.Y.Lin_1295852605.cif'

data_jn14_0m
_database_code_depnum_ccdc_archive 'CCDC 809542'
#TrackingRef '3937_web_deposit_cif_file_1_JosephC.Y.Lin_1295852605.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H27 Br N2 O2'
_chemical_formula_weight         347.30

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   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                   7.7796(5)
_cell_length_b                   4.7083(3)
_cell_length_c                   47.139(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.573(3)
_cell_angle_gamma                90.00
_cell_volume                     1726.00(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5081
_cell_measurement_theta_min      3.46
_cell_measurement_theta_max      28.00

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.66352
_exptl_absorpt_correction_T_max  0.91157
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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            19774
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_theta_min         0.86
_diffrn_reflns_theta_max         29.20
_reflns_number_total             4698
_reflns_number_gt                3392
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4698
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.10766(3) 0.60571(7) 0.168850(6) 0.04412(13) Uani 1 1 d . . .
O1 O 0.1355(3) -0.4064(4) -0.27161(4) 0.0517(5) Uani 1 1 d . . .
H1B H 0.1435 -0.3195 -0.2866 0.078 Uiso 1 1 calc R . .
O2 O 0.3047(3) -0.0598(5) -0.25418(4) 0.0617(7) Uani 1 1 d . . .
N1 N 0.3633(3) 0.0035(5) -0.16599(4) 0.0350(5) Uani 1 1 d . . .
N2 N 0.3057(3) -0.2793(5) -0.20078(4) 0.0344(5) Uani 1 1 d . . .
C1 C 0.2374(3) -0.1068(5) -0.18182(5) 0.0331(5) Uani 1 1 d . . .
H1A H 0.1208 -0.0700 -0.1800 0.040 Uiso 1 1 calc R . .
C2 C 0.5166(4) -0.1049(7) -0.17481(6) 0.0488(8) Uani 1 1 d . . .
H2A H 0.6249 -0.0661 -0.1669 0.059 Uiso 1 1 calc R . .
C3 C 0.4820(4) -0.2750(8) -0.19664(6) 0.0499(7) Uani 1 1 d . . .
H3A H 0.5618 -0.3733 -0.2072 0.060 Uiso 1 1 calc R . .
C4 C 0.2104(4) -0.4266(6) -0.22340(5) 0.0450(7) Uani 1 1 d . . .
H4A H 0.0904 -0.4408 -0.2185 0.054 Uiso 1 1 calc R . .
H4B H 0.2553 -0.6176 -0.2253 0.054 Uiso 1 1 calc R . .
C5 C 0.2238(4) -0.2722(6) -0.25137(5) 0.0379(6) Uani 1 1 d . . .
C6 C 0.3413(4) 0.1877(6) -0.14134(6) 0.0428(6) Uani 1 1 d . . .
H6A H 0.2435 0.3118 -0.1448 0.051 Uiso 1 1 calc R . .
H6B H 0.4427 0.3056 -0.1386 0.051 Uiso 1 1 calc R . .
C7 C 0.3133(4) 0.0166(6) -0.11462(5) 0.0411(6) Uani 1 1 d . . .
H7A H 0.2084 -0.0933 -0.1169 0.049 Uiso 1 1 calc R . .
H7B H 0.4080 -0.1153 -0.1118 0.049 Uiso 1 1 calc R . .
C8 C 0.3005(4) 0.2052(6) -0.08872(6) 0.0442(6) Uani 1 1 d . . .
H8A H 0.2030 0.3319 -0.0913 0.053 Uiso 1 1 calc R . .
H8B H 0.4034 0.3208 -0.0869 0.053 Uiso 1 1 calc R . .
C9 C 0.2796(4) 0.0354(6) -0.06164(6) 0.0426(7) Uani 1 1 d . . .
H9A H 0.3754 -0.0953 -0.0595 0.051 Uiso 1 1 calc R . .
H9B H 0.1752 -0.0765 -0.0634 0.051 Uiso 1 1 calc R . .
C10 C 0.2710(4) 0.2183(7) -0.03502(6) 0.0472(7) Uani 1 1 d . . .
H10A H 0.1742 0.3471 -0.0371 0.057 Uiso 1 1 calc R . .
H10B H 0.3747 0.3324 -0.0334 0.057 Uiso 1 1 calc R . .
C11 C 0.2526(4) 0.0488(6) -0.00751(6) 0.0453(7) Uani 1 1 d . . .
H11A H 0.1493 -0.0661 -0.0091 0.054 Uiso 1 1 calc R . .
H11B H 0.3497 -0.0793 -0.0053 0.054 Uiso 1 1 calc R . .
C12 C 0.2432(4) 0.2307(7) 0.01874(6) 0.0457(7) Uani 1 1 d . . .
H12A H 0.1463 0.3593 0.0165 0.055 Uiso 1 1 calc R . .
H12B H 0.3467 0.3451 0.0204 0.055 Uiso 1 1 calc R . .
C13 C 0.2241(4) 0.0619(6) 0.04631(6) 0.0455(7) Uani 1 1 d . . .
H13A H 0.1208 -0.0529 0.0447 0.055 Uiso 1 1 calc R . .
H13B H 0.3211 -0.0664 0.0485 0.055 Uiso 1 1 calc R . .
C14 C 0.2143(4) 0.2436(8) 0.07269(6) 0.0561(8) Uani 1 1 d . . .
H14A H 0.1178 0.3729 0.0705 0.067 Uiso 1 1 calc R . .
H14B H 0.3181 0.3572 0.0745 0.067 Uiso 1 1 calc R . .
C15 C 0.1939(5) 0.0733(10) 0.09994(7) 0.0717(11) Uani 1 1 d . . .
H15A H 0.1885 0.2010 0.1158 0.108 Uiso 1 1 calc R . .
H15B H 0.2904 -0.0518 0.1026 0.108 Uiso 1 1 calc R . .
H15C H 0.0900 -0.0363 0.0986 0.108 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04266(19) 0.0523(2) 0.03765(18) -0.00441(12) 0.00539(12) 0.00067(12)
O1 0.0709(15) 0.0526(13) 0.0315(10) 0.0002(9) 0.0000(10) -0.0123(10)
O2 0.0891(18) 0.0564(15) 0.0397(12) 0.0106(10) 0.0032(11) -0.0284(12)
N1 0.0358(12) 0.0411(12) 0.0284(11) -0.0023(9) 0.0072(9) -0.0011(10)
N2 0.0424(12) 0.0355(12) 0.0258(10) -0.0006(9) 0.0077(9) 0.0006(9)
C1 0.0339(13) 0.0370(13) 0.0287(12) 0.0005(10) 0.0060(10) 0.0019(10)
C2 0.0313(14) 0.076(2) 0.0390(15) -0.0021(15) 0.0056(12) 0.0012(14)
C3 0.0400(16) 0.067(2) 0.0432(16) -0.0026(15) 0.0121(13) 0.0133(14)
C4 0.066(2) 0.0405(15) 0.0293(13) -0.0018(11) 0.0093(13) -0.0156(13)
C5 0.0468(15) 0.0398(15) 0.0274(13) -0.0011(11) 0.0083(11) -0.0009(12)
C6 0.0591(18) 0.0395(14) 0.0298(13) -0.0058(11) 0.0007(12) -0.0014(13)
C7 0.0479(16) 0.0448(15) 0.0308(13) -0.0044(12) 0.0058(12) -0.0039(13)
C8 0.0563(18) 0.0443(15) 0.0324(14) -0.0064(12) 0.0049(12) -0.0041(13)
C9 0.0474(17) 0.0458(17) 0.0350(14) -0.0027(12) 0.0073(12) -0.0055(12)
C10 0.0562(18) 0.0523(18) 0.0332(14) -0.0042(13) 0.0062(13) -0.0096(14)
C11 0.0488(17) 0.0473(18) 0.0400(16) -0.0030(12) 0.0057(13) -0.0019(13)
C12 0.0510(17) 0.0507(18) 0.0355(15) -0.0013(13) 0.0038(13) -0.0063(14)
C13 0.0469(17) 0.0544(19) 0.0354(15) -0.0039(13) 0.0059(12) -0.0018(13)
C14 0.0575(19) 0.072(2) 0.0391(16) -0.0087(16) 0.0030(14) -0.0037(17)
C15 0.073(2) 0.109(3) 0.0337(16) -0.0064(18) 0.0078(16) 0.001(2)

_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
O1 C5 1.322(3) . ?
O1 H1B 0.8200 . ?
O2 C5 1.191(3) . ?
N1 C1 1.321(3) . ?
N1 C2 1.372(4) . ?
N1 C6 1.464(3) . ?
N2 C1 1.329(3) . ?
N2 C3 1.381(3) . ?
N2 C4 1.457(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.326(4) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 C5 1.512(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.516(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.515(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.533(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.534(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.526(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C5 O1 H1B 109.5 . . ?
C1 N1 C2 108.6(2) . . ?
C1 N1 C6 125.5(2) . . ?
C2 N1 C6 125.6(2) . . ?
C1 N2 C3 108.1(2) . . ?
C1 N2 C4 125.3(2) . . ?
C3 N2 C4 126.4(2) . . ?
N1 C1 N2 108.4(2) . . ?
N1 C1 H1A 125.8 . . ?
N2 C1 H1A 125.8 . . ?
C3 C2 N1 107.5(3) . . ?
C3 C2 H2A 126.3 . . ?
N1 C2 H2A 126.3 . . ?
C2 C3 N2 107.3(3) . . ?
C2 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
N2 C4 C5 111.3(2) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O2 C5 O1 125.9(2) . . ?
O2 C5 C4 123.4(2) . . ?
O1 C5 C4 110.6(2) . . ?
N1 C6 C7 111.6(2) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.8(2) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.3(2) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 113.7(2) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 114.2(3) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 114.0(2) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 114.1(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 114.3(3) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 113.8(3) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.435
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.207