# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_140115_xc_11_33_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H46 N4 O6'
_chemical_formula_sum            'C30 H46 N4 O6'
_chemical_formula_weight         558.71

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   9.4439(4)
_cell_length_b                   11.2685(4)
_cell_length_c                   28.3698(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3019.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5388
_cell_measurement_theta_min      2.8085
_cell_measurement_theta_max      29.5869

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18082
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2764
_reflns_number_gt                2286
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0357P)²+1.3671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.54857(11) 0.36797(10) 0.04103(4) 0.0392(3) Uani 1 1 d . . .
O2 O 0.49551(12) 0.23646(13) 0.09236(6) 0.0642(5) Uani 1 1 d . . .
O3 O 0.15427(10) 0.24682(8) 0.11368(3) 0.0220(2) Uani 1 1 d . . .
N1 N 0.08787(12) 0.13688(10) 0.13077(4) 0.0233(3) Uani 1 1 d . . .
N5 N 0.46170(12) 0.30886(11) 0.06278(5) 0.0290(3) Uani 1 1 d . . .
C1 C -0.11780(15) 0.47695(12) 0.02745(5) 0.0244(3) Uani 1 1 d . . .
H1 H -0.1987 0.4597 0.0461 0.029 Uiso 1 1 calc R . .
C2 C 0.01439(14) 0.44057(12) 0.04243(5) 0.0235(3) Uani 1 1 d . . .
H2 H 0.0240 0.4011 0.0718 0.028 Uiso 1 1 calc R . .
C3 C 0.13384(14) 0.46127(11) 0.01478(5) 0.0217(3) Uani 1 1 d . . .
C4 C 0.27557(14) 0.42192(12) 0.02888(5) 0.0230(3) Uani 1 1 d . . .
H4 H 0.3524 0.4713 0.0198 0.028 Uiso 1 1 calc R . .
C5 C 0.30841(14) 0.32455(12) 0.05307(5) 0.0219(3) Uani 1 1 d . . .
C6 C 0.21608(14) 0.22347(12) 0.06843(5) 0.0222(3) Uani 1 1 d . . .
H6A H 0.1400 0.2111 0.0449 0.027 Uiso 1 1 calc R . .
H6B H 0.2732 0.1499 0.0701 0.027 Uiso 1 1 calc R . .
C7 C -0.06843(15) 0.15687(13) 0.13196(5) 0.0277(3) Uani 1 1 d . . .
C8 C -0.13467(17) 0.04465(14) 0.15353(6) 0.0382(4) Uani 1 1 d . . .
H8A H -0.2376 0.0578 0.1576 0.046 Uiso 1 1 calc R . .
H8B H -0.1223 -0.0221 0.1312 0.046 Uiso 1 1 calc R . .
C9 C -0.07175(19) 0.01007(15) 0.20056(6) 0.0441(4) Uani 1 1 d . . .
H9A H -0.0916 0.0726 0.2242 0.053 Uiso 1 1 calc R . .
H9B H -0.1148 -0.0650 0.2117 0.053 Uiso 1 1 calc R . .
C10 C 0.08633(18) -0.00551(14) 0.19503(6) 0.0386(4) Uani 1 1 d . . .
H10A H 0.1044 -0.0729 0.1735 0.046 Uiso 1 1 calc R . .
H10B H 0.1277 -0.0258 0.2261 0.046 Uiso 1 1 calc R . .
C11 C 0.16105(17) 0.10532(13) 0.17576(5) 0.0295(4) Uani 1 1 d . . .
C12 C -0.11867(17) 0.26914(14) 0.15800(6) 0.0367(4) Uani 1 1 d . . .
H12A H -0.1118 0.2565 0.1921 0.055 Uiso 1 1 calc R . .
H12B H -0.2173 0.2859 0.1495 0.055 Uiso 1 1 calc R . .
H12C H -0.0589 0.3365 0.1490 0.055 Uiso 1 1 calc R . .
C13 C -0.11937(15) 0.16344(14) 0.08109(6) 0.0323(4) Uani 1 1 d . . .
H13A H -0.0854 0.2371 0.0667 0.048 Uiso 1 1 calc R . .
H13B H -0.2231 0.1620 0.0804 0.048 Uiso 1 1 calc R . .
H13C H -0.0824 0.0954 0.0634 0.048 Uiso 1 1 calc R . .
C14 C 0.1653(2) 0.20514(15) 0.21274(6) 0.0410(4) Uani 1 1 d . . .
H14A H 0.1911 0.2800 0.1974 0.062 Uiso 1 1 calc R . .
H14B H 0.2356 0.1858 0.2370 0.062 Uiso 1 1 calc R . .
H14C H 0.0718 0.2131 0.2274 0.062 Uiso 1 1 calc R . .
C15 C 0.31257(18) 0.07048(16) 0.16323(6) 0.0395(4) Uani 1 1 d . . .
H15A H 0.3113 0.0122 0.1376 0.059 Uiso 1 1 calc R . .
H15B H 0.3587 0.0358 0.1909 0.059 Uiso 1 1 calc R . .
H15C H 0.3650 0.1411 0.1531 0.059 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
O1 N5 1.2238(16) . ?
O2 N5 1.2132(17) . ?
O3 C6 1.4344(16) . ?
O3 N1 1.4708(14) . ?
N1 C7 1.4935(18) . ?
N1 C11 1.4944(19) . ?
N5 C5 1.4842(18) . ?
C1 C2 1.381(2) . ?
C1 C3 1.394(2) 5_565 ?
C1 H1 0.9500 . ?
C2 C3 1.3935(19) . ?
C2 H2 0.9500 . ?
C3 C1 1.394(2) 5_565 ?
C3 C4 1.4657(19) . ?
C4 C5 1.3308(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4991(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C13 1.523(2) . ?
C7 C8 1.538(2) . ?
C7 C12 1.540(2) . ?
C8 C9 1.512(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.511(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.535(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.526(2) . ?
C11 C14 1.539(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
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
C6 O3 N1 108.31(9) . . ?
O3 N1 C7 107.57(10) . . ?
O3 N1 C11 106.55(10) . . ?
C7 N1 C11 118.27(11) . . ?
O2 N5 O1 122.58(12) . . ?
O2 N5 C5 117.73(12) . . ?
O1 N5 C5 119.69(12) . . ?
C2 C1 C3 120.72(13) . 5_565 ?
C2 C1 H1 119.6 . . ?
C3 C1 H1 119.6 5_565 . ?
C1 C2 C3 120.60(13) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C1 118.65(13) . 5_565 ?
C2 C3 C4 122.35(13) . . ?
C1 C3 C4 119.00(12) 5_565 . ?
C5 C4 C3 127.08(13) . . ?
C5 C4 H4 116.5 . . ?
C3 C4 H4 116.5 . . ?
C4 C5 N5 114.91(12) . . ?
C4 C5 C6 129.85(12) . . ?
N5 C5 C6 115.01(11) . . ?
O3 C6 C5 110.95(11) . . ?
O3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C13 107.34(12) . . ?
N1 C7 C8 106.68(12) . . ?
C13 C7 C8 106.77(13) . . ?
N1 C7 C12 116.06(12) . . ?
C13 C7 C12 108.50(13) . . ?
C8 C7 C12 111.06(12) . . ?
C9 C8 C7 113.78(14) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 109.06(13) . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 C11 113.36(13) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 C15 107.22(12) . . ?
N1 C11 C10 106.57(12) . . ?
C15 C11 C10 107.74(13) . . ?
N1 C11 C14 114.85(12) . . ?
C15 C11 C14 108.83(14) . . ?
C10 C11 C14 111.33(13) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 993058'
#######################################################################
#
#                 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_140120_xc_10_005_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 Br N2 O3'
_chemical_formula_sum            'C18 H25 Br N2 O3'
_chemical_formula_weight         397.31

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   18.9268(13)
_cell_length_b                   8.3654(5)
_cell_length_c                   23.4009(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3705.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4398
_cell_measurement_theta_min      2.9875
_cell_measurement_theta_max      29.3479

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    2.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4758
_exptl_absorpt_correction_T_max  0.6272
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011) 
;

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23814
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3383
_reflns_number_gt                2519
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0330P)²+3.0411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.11314(2) -0.04504(4) 0.230494(15) 0.06668(15) Uani 1 1 d . . .
O1 O 0.20126(15) 0.7647(3) 0.45859(13) 0.0987(10) Uani 1 1 d . . .
O2 O 0.13297(15) 0.9252(3) 0.41556(13) 0.0883(9) Uani 1 1 d . . .
O3 O 0.00601(8) 0.62293(19) 0.40125(7) 0.0334(4) Uani 1 1 d . . .
N1 N 0.15557(13) 0.7924(3) 0.42434(12) 0.0537(7) Uani 1 1 d . . .
N2 N -0.06501(10) 0.6775(2) 0.38624(8) 0.0315(5) Uani 1 1 d . . .
C1 C 0.21072(14) 0.3300(3) 0.31375(13) 0.0464(7) Uani 1 1 d . . .
H1 H 0.2555 0.3757 0.3144 0.056 Uiso 1 1 calc R . .
C2 C 0.19802(15) 0.2001(3) 0.27892(13) 0.0494(7) Uani 1 1 d . . .
H2 H 0.2335 0.1601 0.2554 0.059 Uiso 1 1 calc R . .
C3 C 0.13219(15) 0.1304(3) 0.27951(12) 0.0429(7) Uani 1 1 d . . .
C4 C 0.07956(14) 0.1856(3) 0.31494(12) 0.0438(7) Uani 1 1 d . . .
H4 H 0.0358 0.1350 0.3162 0.053 Uiso 1 1 calc R . .
C5 C 0.09291(14) 0.3174(3) 0.34853(12) 0.0418(6) Uani 1 1 d . . .
H5 H 0.0574 0.3561 0.3723 0.050 Uiso 1 1 calc R . .
C6 C 0.15769(13) 0.3934(3) 0.34783(11) 0.0395(6) Uani 1 1 d . . .
C7 C 0.17192(14) 0.5368(3) 0.38175(12) 0.0435(7) Uani 1 1 d . . .
H7 H 0.2155 0.5426 0.4000 0.052 Uiso 1 1 calc R . .
C8 C 0.12830(13) 0.6591(3) 0.38887(11) 0.0385(6) Uani 1 1 d . . .
C9 C 0.05738(13) 0.6861(3) 0.36257(11) 0.0366(6) Uani 1 1 d . . .
H9A H 0.0494 0.7995 0.3566 0.044 Uiso 1 1 calc R . .
H9B H 0.0543 0.6322 0.3260 0.044 Uiso 1 1 calc R . .
C10 C -0.10556(13) 0.5342(3) 0.36709(12) 0.0394(6) Uani 1 1 d . . .
C11 C -0.18267(14) 0.5860(3) 0.35991(14) 0.0523(8) Uani 1 1 d . . .
H11A H -0.1858 0.6601 0.3281 0.063 Uiso 1 1 calc R . .
H11B H -0.2109 0.4929 0.3505 0.063 Uiso 1 1 calc R . .
C12 C -0.21323(15) 0.6644(4) 0.41237(16) 0.0645(9) Uani 1 1 d . . .
H12A H -0.2616 0.6966 0.4052 0.077 Uiso 1 1 calc R . .
H12B H -0.2130 0.5898 0.4441 0.077 Uiso 1 1 calc R . .
C13 C -0.16898(15) 0.8082(4) 0.42668(14) 0.0544(8) Uani 1 1 d . . .
H13A H -0.1880 0.8585 0.4607 0.065 Uiso 1 1 calc R . .
H13B H -0.1725 0.8846 0.3956 0.065 Uiso 1 1 calc R . .
C14 C -0.09102(15) 0.7694(3) 0.43689(12) 0.0444(7) Uani 1 1 d . . .
C15 C -0.07740(16) 0.4909(4) 0.30800(13) 0.0540(8) Uani 1 1 d . . .
H15A H -0.0759 0.5850 0.2846 0.081 Uiso 1 1 calc R . .
H15B H -0.1079 0.4130 0.2907 0.081 Uiso 1 1 calc R . .
H15C H -0.0307 0.4473 0.3116 0.081 Uiso 1 1 calc R . .
C16 C -0.10031(16) 0.3875(4) 0.40598(16) 0.0597(9) Uani 1 1 d . . .
H16A H -0.0524 0.3746 0.4185 0.090 Uiso 1 1 calc R . .
H16B H -0.1148 0.2941 0.3852 0.090 Uiso 1 1 calc R . .
H16C H -0.1305 0.4019 0.4386 0.090 Uiso 1 1 calc R . .
C17 C -0.05013(18) 0.9261(4) 0.43784(15) 0.0655(9) Uani 1 1 d . . .
H17A H -0.0018 0.9055 0.4480 0.098 Uiso 1 1 calc R . .
H17B H -0.0708 0.9968 0.4655 0.098 Uiso 1 1 calc R . .
H17C H -0.0519 0.9747 0.4007 0.098 Uiso 1 1 calc R . .
C18 C -0.0820(2) 0.6857(5) 0.49457(13) 0.0742(11) Uani 1 1 d . . .
H18A H -0.1155 0.5998 0.4976 0.111 Uiso 1 1 calc R . .
H18B H -0.0900 0.7610 0.5248 0.111 Uiso 1 1 calc R . .
H18C H -0.0350 0.6437 0.4975 0.111 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 1.897(3) . ?
O1 N1 1.201(3) . ?
O2 N1 1.209(3) . ?
O3 C9 1.430(3) . ?
O3 N2 1.462(2) . ?
N1 C8 1.482(3) . ?
N2 C10 1.492(3) . ?
N2 C14 1.496(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(4) . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.463(4) . ?
C7 C8 1.325(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.494(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.526(4) . ?
C10 C16 1.531(4) . ?
C10 C11 1.532(4) . ?
C11 C12 1.507(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.530(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C17 1.522(4) . ?
C14 C18 1.530(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C9 O3 N2 110.95(17) . . ?
O1 N1 O2 123.0(3) . . ?
O1 N1 C8 118.7(3) . . ?
O2 N1 C8 118.2(3) . . ?
O3 N2 C10 107.10(17) . . ?
O3 N2 C14 105.82(17) . . ?
C10 N2 C14 118.8(2) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 Br1 119.6(2) . . ?
C4 C3 Br1 119.1(2) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 119.5(2) . . ?
C8 C7 C6 125.9(2) . . ?
C8 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
C7 C8 N1 115.7(2) . . ?
C7 C8 C9 128.7(2) . . ?
N1 C8 C9 115.5(2) . . ?
O3 C9 C8 107.1(2) . . ?
O3 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C15 106.5(2) . . ?
N2 C10 C16 115.6(2) . . ?
C15 C10 C16 109.0(2) . . ?
N2 C10 C11 107.2(2) . . ?
C15 C10 C11 107.5(2) . . ?
C16 C10 C11 110.7(2) . . ?
C12 C11 C10 113.5(3) . . ?
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 . . ?
C13 C12 C11 108.4(3) . . ?
C13 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 C14 113.7(2) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 C17 106.6(2) . . ?
N2 C14 C13 107.6(2) . . ?
C17 C14 C13 108.0(2) . . ?
N2 C14 C18 115.3(2) . . ?
C17 C14 C18 108.9(3) . . ?
C13 C14 C18 110.0(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 993059'
