# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_070906a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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   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                   10.3180(11)
_cell_length_b                   12.8037(14)
_cell_length_c                   10.6038(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.7060(10)
_cell_angle_gamma                90.00
_cell_volume                     1292.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2330
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.43

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.815364
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  no
_diffrn_measurement_method       no
_diffrn_detector_area_resol_mean no
_diffrn_standards_number         no
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  no
_diffrn_standards_decay_%        no
_diffrn_reflns_number            10853
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         28.43
_reflns_number_total             3037
_reflns_number_gt                2330
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker apex II'
_computing_cell_refinement       'Bruker apex II'
_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)+(0.0550P)²+0.2196P] 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     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3037
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
C1 C 0.37763(16) 0.15151(14) 0.41147(18) 0.0653(4) Uani 1 1 d . . .
H1A H 0.3046 0.0987 0.3854 0.078 Uiso 1 1 calc R . .
H1B H 0.3390 0.2144 0.3597 0.078 Uiso 1 1 calc R . .
C2 C 0.60897(14) 0.12726(11) 0.50273(14) 0.0472(3) Uani 1 1 d . . .
C3 C 0.56778(14) 0.16081(11) 0.60524(15) 0.0484(3) Uani 1 1 d . . .
C4 C 0.66293(15) 0.17542(11) 0.73616(15) 0.0497(3) Uani 1 1 d . . .
H4 H 0.6344 0.1986 0.8045 0.060 Uiso 1 1 calc R . .
C5 C 0.80529(14) 0.15436(10) 0.76418(13) 0.0405(3) Uani 1 1 d . . .
C6 C 0.84655(13) 0.12162(9) 0.65943(12) 0.0376(3) Uani 1 1 d . . .
C7 C 0.74628(14) 0.10804(11) 0.52580(14) 0.0455(3) Uani 1 1 d . . .
H7 H 0.7727 0.0866 0.4554 0.055 Uiso 1 1 calc R . .
C8 C 0.99888(13) 0.10156(10) 0.68672(12) 0.0380(3) Uani 1 1 d . . .
H8 H 1.0224 0.1379 0.6170 0.046 Uiso 1 1 calc R . .
C9 C 1.09737(13) 0.13911(10) 0.82620(13) 0.0400(3) Uani 1 1 d . . .
H9 H 1.1194 0.2137 0.8280 0.048 Uiso 1 1 calc R . .
C10 C 0.91284(14) 0.16815(11) 0.90859(14) 0.0477(3) Uani 1 1 d . . .
H10A H 0.9353 0.2416 0.9264 0.057 Uiso 1 1 calc R . .
H10B H 0.8743 0.1434 0.9733 0.057 Uiso 1 1 calc R . .
C11 C 1.04027(14) -0.01392(11) 0.68850(13) 0.0431(3) Uani 1 1 d . . .
C12 C 1.18681(14) -0.02720(11) 0.78667(15) 0.0504(4) Uani 1 1 d . . .
H12 H 1.2168 -0.0956 0.8296 0.060 Uiso 1 1 calc R . .
C13 C 1.22686(14) 0.07056(11) 0.87571(14) 0.0465(3) Uani 1 1 d . . .
C14 C 1.29821(15) 0.04952(13) 0.78141(17) 0.0596(4) Uani 1 1 d . . .
H14A H 1.3956 0.0274 0.8210 0.072 Uiso 1 1 calc R . .
H14B H 1.2743 0.0935 0.7011 0.072 Uiso 1 1 calc R . .
C15 C 1.15676(16) 0.11622(13) 1.05885(14) 0.0554(4) Uani 1 1 d . . .
H15A H 1.1385 0.0746 1.1267 0.067 Uiso 1 1 calc R . .
H15B H 1.1743 0.1879 1.0907 0.067 Uiso 1 1 calc R . .
C16 C 1.28196(16) 0.07186(13) 1.03086(15) 0.0568(4) Uani 1 1 d . . .
H16A H 1.3639 0.1165 1.0692 0.068 Uiso 1 1 calc R . .
H16B H 1.3060 0.0021 1.0682 0.068 Uiso 1 1 calc R . .
N1 N 1.03889(11) 0.11034(9) 0.92611(10) 0.0420(3) Uani 1 1 d . . .
O1 O 0.42412(11) 0.17266(10) 0.55442(12) 0.0688(3) Uani 1 1 d . . .
O2 O 0.49283(11) 0.11593(10) 0.38237(11) 0.0709(4) Uani 1 1 d . . .
O3 O 0.96187(11) -0.08266(8) 0.62355(11) 0.0609(3) 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
C1 O2 1.4138(19) . ?
C1 O1 1.428(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.3639(19) . ?
C2 C3 1.380(2) . ?
C2 O2 1.3802(16) . ?
C3 C4 1.369(2) . ?
C3 O1 1.3762(17) . ?
C4 C5 1.4076(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3986(17) . ?
C5 C10 1.5151(18) . ?
C6 C7 1.4059(17) . ?
C6 C8 1.5063(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.5136(17) . ?
C8 C11 1.5372(18) . ?
C8 H8 0.9800 . ?
C9 N1 1.4545(16) . ?
C9 C13 1.5131(18) . ?
C9 H9 0.9800 . ?
C10 N1 1.4448(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.2138(16) . ?
C11 C12 1.4777(19) . ?
C12 C13 1.526(2) . ?
C12 C14 1.529(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.477(2) . ?
C13 C16 1.519(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N1 1.4645(16) . ?
C15 C16 1.541(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
O2 C1 O1 109.05(12) . . ?
O2 C1 H1A 109.9 . . ?
O1 C1 H1A 109.9 . . ?
O2 C1 H1B 109.9 . . ?
O1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C7 C2 C3 121.97(13) . . ?
C7 C2 O2 128.16(13) . . ?
C3 C2 O2 109.86(12) . . ?
C4 C3 O1 128.64(13) . . ?
C4 C3 C2 121.54(13) . . ?
O1 C3 C2 109.79(13) . . ?
C3 C4 C5 117.99(12) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 120.16(12) . . ?
C6 C5 C10 120.59(12) . . ?
C4 C5 C10 119.25(12) . . ?
C5 C6 C7 120.42(12) . . ?
C5 C6 C8 120.89(11) . . ?
C7 C6 C8 118.68(11) . . ?
C2 C7 C6 117.89(12) . . ?
C2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C6 C8 C9 113.01(10) . . ?
C6 C8 C11 115.51(10) . . ?
C9 C8 C11 102.41(10) . . ?
C6 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C11 C8 H8 108.5 . . ?
N1 C9 C13 99.17(10) . . ?
N1 C9 C8 108.69(10) . . ?
C13 C9 C8 108.95(11) . . ?
N1 C9 H9 113.0 . . ?
C13 C9 H9 113.0 . . ?
C8 C9 H9 113.0 . . ?
N1 C10 C5 110.00(10) . . ?
N1 C10 H10A 109.7 . . ?
C5 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C5 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O3 C11 C12 126.37(13) . . ?
O3 C11 C8 124.71(12) . . ?
C12 C11 C8 108.85(11) . . ?
C11 C12 C13 107.50(11) . . ?
C11 C12 C14 118.66(12) . . ?
C13 C12 C14 57.84(9) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C12 H12 118.9 . . ?
C14 C13 C9 118.35(12) . . ?
C14 C13 C16 131.22(13) . . ?
C9 C13 C16 106.29(12) . . ?
C14 C13 C12 61.20(10) . . ?
C9 C13 C12 105.62(11) . . ?
C16 C13 C12 125.30(12) . . ?
C13 C14 C12 60.96(9) . . ?
C13 C14 H14A 117.7 . . ?
C12 C14 H14A 117.7 . . ?
C13 C14 H14B 117.7 . . ?
C12 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
N1 C15 C16 104.05(11) . . ?
N1 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
N1 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C13 C16 C15 102.80(11) . . ?
C13 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
C13 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C10 N1 C9 112.49(10) . . ?
C10 N1 C15 118.01(11) . . ?
C9 N1 C15 105.24(10) . . ?
C3 O1 C1 105.33(11) . . ?
C2 O2 C1 105.51(12) . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 989217'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br N O2'
_chemical_formula_sum            'C16 H16 Br N O2'
_chemical_formula_weight         334.21

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  -P1

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

_cell_length_a                   7.7674(11)
_cell_length_b                   9.4798(13)
_cell_length_c                   9.7608(14)
_cell_angle_alpha                103.452(2)
_cell_angle_beta                 95.382(2)
_cell_angle_gamma                93.343(2)
_cell_volume                     693.53(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5439
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    2.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5749
_exptl_absorpt_correction_T_max  0.7559
_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  no
_diffrn_measurement_method       no
_diffrn_detector_area_resol_mean no
_diffrn_standards_number         no
_diffrn_standards_interval_count no
_diffrn_standards_interval_time  no
_diffrn_standards_decay_%        no
_diffrn_reflns_number            6027
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.23
_reflns_number_total             3149
_reflns_number_gt                2131
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker apex II'
_computing_cell_refinement       'Bruker apex II'
_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)+(0.0402P)²+0.0856P] 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         3149
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.47218(4) 0.24340(4) 0.49852(4) 0.06506(16) Uani 1 1 d . . .
O1 O 1.2054(3) 0.7730(3) 0.1265(3) 0.0767(7) Uani 1 1 d . . .
O2 O 0.9187(3) 0.8267(3) 0.0944(3) 0.0713(7) Uani 1 1 d . . .
N1 N 0.9166(3) 0.2382(3) 0.3096(2) 0.0424(6) Uani 1 1 d . . .
C1 C 0.8385(4) 0.4995(3) 0.2343(3) 0.0420(7) Uani 1 1 d . . .
C2 C 0.7954(4) 0.6209(3) 0.1814(3) 0.0503(8) Uani 1 1 d . . .
H2A H 0.6812 0.6447 0.1712 0.060 Uiso 1 1 calc R . .
C3 C 0.9280(4) 0.7025(3) 0.1456(3) 0.0507(8) Uani 1 1 d . . .
C4 C 1.0922(5) 0.8595(4) 0.0660(4) 0.0706(11) Uani 1 1 d . . .
H4A H 1.0976 0.8396 -0.0356 0.085 Uiso 1 1 calc R . .
H4B H 1.1274 0.9619 0.1061 0.085 Uiso 1 1 calc R . .
C5 C 1.0976(4) 0.6698(4) 0.1626(3) 0.0524(8) Uani 1 1 d . . .
C6 C 1.1424(4) 0.5534(4) 0.2127(3) 0.0536(8) Uani 1 1 d . . .
H6A H 1.2576 0.5321 0.2229 0.064 Uiso 1 1 calc R . .
C7 C 1.0098(4) 0.4660(3) 0.2488(3) 0.0428(7) Uani 1 1 d . . .
C8 C 1.0628(4) 0.3413(3) 0.3103(3) 0.0476(8) Uani 1 1 d . . .
H8A H 1.1490 0.2912 0.2560 0.057 Uiso 1 1 calc R . .
H8B H 1.1158 0.3793 0.4070 0.057 Uiso 1 1 calc R . .
C9 C 0.7686(3) 0.3113(3) 0.3671(3) 0.0388(7) Uani 1 1 d . . .
H9A H 0.8054 0.3700 0.4633 0.047 Uiso 1 1 calc R . .
C10 C 0.6936(4) 0.4082(3) 0.2772(3) 0.0422(7) Uani 1 1 d . . .
H10A H 0.6271 0.4767 0.3382 0.051 Uiso 1 1 calc R . .
C11 C 0.5682(4) 0.3259(4) 0.1545(3) 0.0524(8) Uani 1 1 d . . .
H11A H 0.5294 0.3747 0.0867 0.063 Uiso 1 1 calc R . .
C12 C 0.5092(4) 0.1885(4) 0.1365(4) 0.0621(9) Uani 1 1 d . . .
H12A H 0.4261 0.1485 0.0602 0.075 Uiso 1 1 calc R . .
C13 C 0.5677(4) 0.0940(3) 0.2311(4) 0.0593(9) Uani 1 1 d . . .
H13A H 0.6493 0.0301 0.1851 0.071 Uiso 1 1 calc R . .
H13B H 0.4684 0.0334 0.2440 0.071 Uiso 1 1 calc R . .
C14 C 0.6530(4) 0.1778(3) 0.3754(3) 0.0463(7) Uani 1 1 d . . .
C15 C 0.7811(4) 0.0901(4) 0.4432(4) 0.0600(9) Uani 1 1 d . . .
H15A H 0.7835 0.1150 0.5456 0.072 Uiso 1 1 calc R . .
H15B H 0.7510 -0.0136 0.4079 0.072 Uiso 1 1 calc R . .
C16 C 0.9558(4) 0.1350(4) 0.3983(4) 0.0558(8) Uani 1 1 d . . .
H16A H 1.0366 0.1813 0.4806 0.067 Uiso 1 1 calc R . .
H16B H 1.0059 0.0510 0.3447 0.067 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 C14 1.968(3) . ?
O1 C5 1.379(4) . ?
O1 C4 1.417(4) . ?
O2 C3 1.384(4) . ?
O2 C4 1.432(4) . ?
N1 C8 1.453(4) . ?
N1 C9 1.467(3) . ?
N1 C16 1.476(4) . ?
C1 C7 1.388(4) . ?
C1 C2 1.412(4) . ?
C1 C10 1.528(4) . ?
C2 C3 1.372(4) . ?
C2 H2A 0.9300 . ?
C3 C5 1.374(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.358(4) . ?
C6 C7 1.406(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.506(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.515(4) . ?
C9 C14 1.531(4) . ?
C9 H9A 0.9800 . ?
C10 C11 1.500(4) . ?
C10 H10A 0.9800 . ?
C11 C12 1.321(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.489(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.515(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.532(4) . ?
C15 C16 1.531(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 C4 104.9(3) . . ?
C3 O2 C4 104.3(3) . . ?
C8 N1 C9 111.8(2) . . ?
C8 N1 C16 113.2(2) . . ?
C9 N1 C16 104.8(2) . . ?
C7 C1 C2 120.3(3) . . ?
C7 C1 C10 121.1(3) . . ?
C2 C1 C10 118.7(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C5 121.7(3) . . ?
C2 C3 O2 128.2(3) . . ?
C5 C3 O2 110.1(3) . . ?
O1 C4 O2 109.2(3) . . ?
O1 C4 H4A 109.8 . . ?
O2 C4 H4A 109.8 . . ?
O1 C4 H4B 109.8 . . ?
O2 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
C6 C5 C3 121.9(3) . . ?
C6 C5 O1 128.1(3) . . ?
C3 C5 O1 110.0(3) . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 H6A 120.9 . . ?
C7 C6 H6A 121.0 . . ?
C1 C7 C6 120.5(3) . . ?
C1 C7 C8 122.1(3) . . ?
C6 C7 C8 117.3(3) . . ?
N1 C8 C7 112.2(2) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 112.7(2) . . ?
N1 C9 C14 99.2(2) . . ?
C10 C9 C14 116.9(2) . . ?
N1 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C14 C9 H9A 109.2 . . ?
C11 C10 C9 112.7(2) . . ?
C11 C10 C1 113.6(2) . . ?
C9 C10 C1 110.6(2) . . ?
C11 C10 H10A 106.5 . . ?
C9 C10 H10A 106.5 . . ?
C1 C10 H10A 106.5 . . ?
C12 C11 C10 124.3(3) . . ?
C12 C11 H11A 117.9 . . ?
C10 C11 H11A 117.9 . . ?
C11 C12 C13 123.9(3) . . ?
C11 C12 H12A 118.1 . . ?
C13 C12 H12A 118.1 . . ?
C12 C13 C14 113.8(3) . . ?
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 . . ?
C13 C14 C9 112.4(3) . . ?
C13 C14 C15 112.7(3) . . ?
C9 C14 C15 102.3(2) . . ?
C13 C14 Br1 109.2(2) . . ?
C9 C14 Br1 108.44(19) . . ?
C15 C14 Br1 111.6(2) . . ?
C16 C15 C14 103.7(2) . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C14 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
N1 C16 C15 105.3(2) . . ?
N1 C16 H16A 110.7 . . ?
C15 C16 H16A 110.7 . . ?
N1 C16 H16B 110.7 . . ?
C15 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 989218'
#######################################################################
#
#                 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_120925c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N O4'
_chemical_formula_weight         301.33
_chemical_absolute_configuration unk

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   P2(1)2(1)2(1)

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'

_cell_length_a                   9.1314(13)
_cell_length_b                   12.4725(18)
_cell_length_c                   12.8711(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1465.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1467
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7651
_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 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            10110
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.28
_reflns_number_total             3441
_reflns_number_gt                2052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker apex II'
_computing_cell_refinement       'Bruker apex II'
_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)+(0.0372P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0144(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(14)
_refine_ls_number_reflns         3441
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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
N1 N 0.26084(19) 0.86274(13) 0.82217(14) 0.0462(5) Uani 1 1 d . . .
O1 O 0.20526(15) 0.89179(12) 1.03957(13) 0.0528(4) Uani 1 1 d . . .
H1 H 0.1719 0.8799 0.9816 0.079 Uiso 1 1 calc R . .
O2 O 0.32184(19) 0.70137(11) 1.15994(12) 0.0568(5) Uani 1 1 d . . .
O3 O 0.5692(2) 1.25836(13) 1.04740(15) 0.0753(5) Uani 1 1 d . . .
O4 O 0.4325(2) 1.32939(12) 0.91192(14) 0.0708(6) Uani 1 1 d . . .
C1 C 0.3497(2) 0.84824(16) 1.04682(17) 0.0423(5) Uani 1 1 d . . .
H1A H 0.3945 0.8770 1.1102 0.051 Uiso 1 1 calc R . .
C2 C 0.3443(2) 0.72876(16) 1.05760(18) 0.0430(5) Uani 1 1 d . . .
C3 C 0.3565(2) 0.66250(17) 0.97793(17) 0.0472(6) Uani 1 1 d . . .
H3 H 0.3508 0.5892 0.9906 0.057 Uiso 1 1 calc R . .
C4 C 0.2469(3) 0.67736(19) 0.7958(2) 0.0675(8) Uani 1 1 d . . .
H4A H 0.2722 0.6247 0.7434 0.081 Uiso 1 1 calc R . .
H4B H 0.1645 0.6506 0.8357 0.081 Uiso 1 1 calc R . .
C5 C 0.2093(3) 0.78404(17) 0.74568(19) 0.0586(7) Uani 1 1 d . . .
H5A H 0.2597 0.7926 0.6799 0.070 Uiso 1 1 calc R . .
H5B H 0.1047 0.7906 0.7343 0.070 Uiso 1 1 calc R . .
C7 C 0.2790(3) 0.97103(17) 0.7808(2) 0.0566(7) Uani 1 1 d . . .
H7A H 0.1834 1.0017 0.7667 0.068 Uiso 1 1 calc R . .
H7B H 0.3324 0.9676 0.7158 0.068 Uiso 1 1 calc R . .
C8 C 0.3512(2) 1.15514(18) 0.84154(18) 0.0510(6) Uani 1 1 d . . .
H8 H 0.2971 1.1845 0.7873 0.061 Uiso 1 1 calc R . .
C9 C 0.4249(3) 1.21836(17) 0.91064(19) 0.0508(6) Uani 1 1 d . . .
C10 C 0.5061(2) 1.17659(18) 0.99002(18) 0.0508(6) Uani 1 1 d . . .
C11 C 0.5181(2) 1.06880(17) 1.00585(18) 0.0490(6) Uani 1 1 d . . .
H11 H 0.5737 1.0414 1.0603 0.059 Uiso 1 1 calc R . .
C12 C 0.5114(4) 1.3541(2) 1.0041(2) 0.0835(9) Uani 1 1 d . . .
H12A H 0.5905 1.4033 0.9883 0.100 Uiso 1 1 calc R . .
H12B H 0.4468 1.3884 1.0539 0.100 Uiso 1 1 calc R . .
C13 C 0.3160(3) 0.59024(16) 1.1853(2) 0.0644(7) Uani 1 1 d . . .
H13A H 0.2379 0.5568 1.1474 0.097 Uiso 1 1 calc R . .
H13B H 0.2991 0.5821 1.2585 0.097 Uiso 1 1 calc R . .
H13C H 0.4073 0.5569 1.1672 0.097 Uiso 1 1 calc R . .
C3A C 0.3790(3) 0.69960(17) 0.86757(19) 0.0510(6) Uani 1 1 d . . .
H3A H 0.4647 0.6625 0.8391 0.061 Uiso 1 1 calc R . .
C7A C 0.3609(2) 1.04304(16) 0.85623(17) 0.0422(6) Uani 1 1 d . . .
C11A C 0.4429(2) 1.00044(15) 0.93642(18) 0.0416(5) Uani 1 1 d . . .
C11B C 0.4476(2) 0.88051(15) 0.95522(16) 0.0398(5) Uani 1 1 d . . .
H11B H 0.5486 0.8607 0.9722 0.048 Uiso 1 1 calc R . .
C11C C 0.4036(2) 0.82061(17) 0.85713(17) 0.0438(5) Uani 1 1 d . . .
H11C H 0.4769 0.8338 0.8030 0.053 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
N1 C7 1.461(3) . ?
N1 C5 1.468(3) . ?
N1 C11C 1.475(3) . ?
O1 C1 1.430(2) . ?
O1 H1 0.8200 . ?
O2 C2 1.376(2) . ?
O2 C13 1.425(2) . ?
O3 C10 1.385(3) . ?
O3 C12 1.419(3) . ?
O4 C9 1.387(2) . ?
O4 C12 1.422(3) . ?
C1 C2 1.498(3) . ?
C1 C11B 1.533(3) . ?
C1 H1A 0.9800 . ?
C2 C3 1.322(3) . ?
C3 C3A 1.508(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.518(3) . ?
C4 C3A 1.544(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C7A 1.519(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.366(3) . ?
C8 C7A 1.414(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(3) . ?
C10 C11 1.364(3) . ?
C11 C11A 1.413(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3A C11C 1.532(3) . ?
C3A H3A 0.9800 . ?
C7A C11A 1.381(3) . ?
C11A C11B 1.516(3) . ?
C11B C11C 1.521(3) . ?
C11B H11B 0.9800 . ?
C11C H11C 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
C7 N1 C5 114.22(18) . . ?
C7 N1 C11C 109.88(16) . . ?
C5 N1 C11C 104.45(17) . . ?
C1 O1 H1 109.5 . . ?
C2 O2 C13 117.81(17) . . ?
C10 O3 C12 104.8(2) . . ?
C9 O4 C12 104.58(19) . . ?
O1 C1 C2 110.73(17) . . ?
O1 C1 C11B 112.82(17) . . ?
C2 C1 C11B 110.58(17) . . ?
O1 C1 H1A 107.5 . . ?
C2 C1 H1A 107.5 . . ?
C11B C1 H1A 107.5 . . ?
C3 C2 O2 126.86(19) . . ?
C3 C2 C1 123.2(2) . . ?
O2 C2 C1 109.91(17) . . ?
C2 C3 C3A 123.4(2) . . ?
C2 C3 H3 118.3 . . ?
C3A C3 H3 118.3 . . ?
C5 C4 C3A 105.86(18) . . ?
C5 C4 H4A 110.6 . . ?
C3A C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C3A C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C4 103.22(18) . . ?
N1 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
N1 C7 C7A 111.7(2) . . ?
N1 C7 H7A 109.3 . . ?
C7A C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C7A C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7A 116.9(2) . . ?
C9 C8 H8 121.5 . . ?
C7A C8 H8 121.5 . . ?
C8 C9 C10 122.3(2) . . ?
C8 C9 O4 127.5(2) . . ?
C10 C9 O4 110.2(2) . . ?
C11 C10 C9 122.1(2) . . ?
C11 C10 O3 127.8(2) . . ?
C9 C10 O3 110.1(2) . . ?
C10 C11 C11A 117.4(2) . . ?
C10 C11 H11 121.3 . . ?
C11A C11 H11 121.3 . . ?
O3 C12 O4 109.5(2) . . ?
O3 C12 H12A 109.8 . . ?
O4 C12 H12A 109.8 . . ?
O3 C12 H12B 109.8 . . ?
O4 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C3A C11C 113.89(19) . . ?
C3 C3A C4 113.67(19) . . ?
C11C C3A C4 103.82(19) . . ?
C3 C3A H3A 108.4 . . ?
C11C C3A H3A 108.4 . . ?
C4 C3A H3A 108.4 . . ?
C11A C7A C8 121.0(2) . . ?
C11A C7A C7 121.12(19) . . ?
C8 C7A C7 117.9(2) . . ?
C7A C11A C11 120.3(2) . . ?
C7A C11A C11B 120.93(19) . . ?
C11 C11A C11B 118.7(2) . . ?
C11A C11B C11C 110.17(18) . . ?
C11A C11B C1 111.44(16) . . ?
C11C C11B C1 110.82(16) . . ?
C11A C11B H11B 108.1 . . ?
C11C C11B H11B 108.1 . . ?
C1 C11B H11B 108.1 . . ?
N1 C11C C11B 108.16(17) . . ?
N1 C11C C3A 104.38(18) . . ?
C11B C11C C3A 116.73(19) . . ?
N1 C11C H11C 109.1 . . ?
C11B C11C H11C 109.1 . . ?
C3A C11C H11C 109.1 . . ?

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
C13 O2 C2 C3 2.6(3) . . . . ?
C13 O2 C2 C1 -178.98(19) . . . . ?
O1 C1 C2 C3 95.1(2) . . . . ?
C11B C1 C2 C3 -30.7(3) . . . . ?
O1 C1 C2 O2 -83.4(2) . . . . ?
C11B C1 C2 O2 150.83(17) . . . . ?
O2 C2 C3 C3A 179.1(2) . . . . ?
C1 C2 C3 C3A 0.8(3) . . . . ?
C7 N1 C5 C4 162.3(2) . . . . ?
C11C N1 C5 C4 42.2(2) . . . . ?
C3A C4 C5 N1 -27.1(2) . . . . ?
C5 N1 C7 C7A -168.39(19) . . . . ?
C11C N1 C7 C7A -51.4(2) . . . . ?
C7A C8 C9 C10 0.7(3) . . . . ?
C7A C8 C9 O4 179.6(2) . . . . ?
C12 O4 C9 C8 175.0(2) . . . . ?
C12 O4 C9 C10 -6.0(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
O4 C9 C10 C11 -179.5(2) . . . . ?
C8 C9 C10 O3 179.7(2) . . . . ?
O4 C9 C10 O3 0.6(3) . . . . ?
C12 O3 C10 C11 -174.9(2) . . . . ?
C12 O3 C10 C9 5.0(2) . . . . ?
C9 C10 C11 C11A 0.0(3) . . . . ?
O3 C10 C11 C11A 180.0(2) . . . . ?
C10 O3 C12 O4 -8.8(3) . . . . ?
C9 O4 C12 O3 9.1(3) . . . . ?
C2 C3 C3A C11C 6.4(3) . . . . ?
C2 C3 C3A C4 -112.3(2) . . . . ?
C5 C4 C3A C3 126.9(2) . . . . ?
C5 C4 C3A C11C 2.6(3) . . . . ?
C9 C8 C7A C11A -0.7(3) . . . . ?
C9 C8 C7A C7 179.6(2) . . . . ?
N1 C7 C7A C11A 17.8(3) . . . . ?
N1 C7 C7A C8 -162.44(19) . . . . ?
C8 C7A C11A C11 0.4(3) . . . . ?
C7 C7A C11A C11 -179.9(2) . . . . ?
C8 C7A C11A C11B 177.10(19) . . . . ?
C7 C7A C11A C11B -3.2(3) . . . . ?
C10 C11 C11A C7A -0.1(3) . . . . ?
C10 C11 C11A C11B -176.83(19) . . . . ?
C7A C11A C11B C11C 21.0(3) . . . . ?
C11 C11A C11B C11C -162.24(19) . . . . ?
C7A C11A C11B C1 -102.4(2) . . . . ?
C11 C11A C11B C1 74.3(2) . . . . ?
O1 C1 C11B C11A 49.9(2) . . . . ?
C2 C1 C11B C11A 174.50(17) . . . . ?
O1 C1 C11B C11C -73.2(2) . . . . ?
C2 C1 C11B C11C 51.4(2) . . . . ?
C7 N1 C11C C11B 71.2(2) . . . . ?
C5 N1 C11C C11B -165.84(17) . . . . ?
C7 N1 C11C C3A -163.83(17) . . . . ?
C5 N1 C11C C3A -40.9(2) . . . . ?
C11A C11B C11C N1 -53.4(2) . . . . ?
C1 C11B C11C N1 70.4(2) . . . . ?
C11A C11B C11C C3A -170.61(18) . . . . ?
C1 C11B C11C C3A -46.8(3) . . . . ?
C3 C3A C11C N1 -101.4(2) . . . . ?
C4 C3A C11C N1 22.7(2) . . . . ?
C3 C3A C11C C11B 17.9(3) . . . . ?
C4 C3A C11C C11B 142.0(2) . . . . ?

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
O1 H1 N1 0.82 2.22 2.867(3) 136.4 .

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 989219'
