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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_e:\140405d\work\t
_database_code_depnum_ccdc_archive 'CCDC 1014213'
_audit_update_record             
;
2014-07-16 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br N O2'
_chemical_formula_weight         360.24

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           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   24.404(4)
_cell_length_b                   4.7162(9)
_cell_length_c                   14.206(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1635.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.71

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.520
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7867
_exptl_absorpt_correction_T_max  0.7867
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16467
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         31.59
_reflns_number_total             5002
_reflns_number_gt                2944
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0506P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.034(9)
_refine_ls_number_reflns         5002
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 0.561688(17) 0.11178(8) -0.06388(4) 0.08470(16) Uani 1 1 d . . .
C1 C 0.71153(11) 0.0157(6) 0.45285(18) 0.0459(6) Uani 1 1 d . . .
C2 C 0.73111(9) -0.1874(5) 0.52486(19) 0.0410(5) Uani 1 1 d . . .
C3 C 0.77946(11) -0.3261(7) 0.5116(2) 0.0579(7) Uani 1 1 d . . .
H3 H 0.8004 -0.2891 0.4583 0.069 Uiso 1 1 calc R . .
C4 C 0.79775(13) -0.5249(8) 0.5781(3) 0.0680(9) Uani 1 1 d . . .
H4 H 0.8308 -0.6184 0.5684 0.082 Uiso 1 1 calc R . .
C5 C 0.76794(13) -0.5825(6) 0.6563(3) 0.0636(8) Uani 1 1 d . . .
H5 H 0.7807 -0.7153 0.6994 0.076 Uiso 1 1 calc R . .
C6 C 0.71774(11) -0.4427(6) 0.6728(2) 0.0467(6) Uani 1 1 d . . .
C7 C 0.68414(13) -0.4974(7) 0.7520(2) 0.0596(8) Uani 1 1 d . . .
H7 H 0.6951 -0.6316 0.7961 0.072 Uiso 1 1 calc R . .
C8 C 0.63631(13) -0.3576(7) 0.7646(2) 0.0593(8) Uani 1 1 d . . .
H8 H 0.6151 -0.3948 0.8176 0.071 Uiso 1 1 calc R . .
C9 C 0.61850(12) -0.1586(6) 0.6989(2) 0.0503(6) Uani 1 1 d . . .
H9 H 0.5854 -0.0648 0.7083 0.060 Uiso 1 1 calc R . .
C10 C 0.64941(9) -0.0991(5) 0.62007(17) 0.0383(5) Uani 1 1 d . . .
C11 C 0.62950(10) 0.1101(5) 0.55087(19) 0.0412(5) Uani 1 1 d . . .
C12 C 0.69948(9) -0.2407(5) 0.60557(18) 0.0377(5) Uani 1 1 d . . .
C13 C 0.64089(11) 0.3503(5) 0.3996(2) 0.0488(6) Uani 1 1 d . . .
H13A H 0.6712 0.4437 0.3683 0.059 Uiso 1 1 calc R . .
H13B H 0.6187 0.4951 0.4297 0.059 Uiso 1 1 calc R . .
C14 C 0.60660(13) 0.1958(6) 0.3274(2) 0.0508(6) Uani 1 1 d . . .
H14A H 0.5776 0.0936 0.3594 0.061 Uiso 1 1 calc R . .
H14B H 0.6294 0.0580 0.2952 0.061 Uiso 1 1 calc R . .
C15 C 0.58137(13) 0.3945(5) 0.2552(2) 0.0505(6) Uani 1 1 d . . .
H15A H 0.6095 0.5219 0.2319 0.061 Uiso 1 1 calc R . .
H15B H 0.5535 0.5087 0.2857 0.061 Uiso 1 1 calc R . .
C16 C 0.55570(10) 0.2389(6) 0.1720(2) 0.0488(6) Uani 1 1 d . . .
H16A H 0.5833 0.1208 0.1424 0.059 Uiso 1 1 calc R . .
H16B H 0.5268 0.1157 0.1949 0.059 Uiso 1 1 calc R . .
C17 C 0.53218(13) 0.4390(6) 0.0995(2) 0.0575(7) Uani 1 1 d . . .
H17A H 0.5043 0.5543 0.1296 0.069 Uiso 1 1 calc R . .
H17B H 0.5611 0.5654 0.0786 0.069 Uiso 1 1 calc R . .
C18 C 0.50747(13) 0.2999(8) 0.0150(2) 0.0652(8) Uani 1 1 d . . .
H18A H 0.4885 0.4420 -0.0221 0.078 Uiso 1 1 calc R . .
H18B H 0.4806 0.1616 0.0356 0.078 Uiso 1 1 calc R . .
N1 N 0.66235(8) 0.1567(4) 0.47163(16) 0.0415(4) Uani 1 1 d . . .
O1 O 0.73549(9) 0.0588(5) 0.37999(16) 0.0686(6) Uani 1 1 d . . .
O2 O 0.58644(8) 0.2358(5) 0.56004(16) 0.0607(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.948(3) . ?
C1 O1 1.206(3) . ?
C1 N1 1.398(4) . ?
C1 C2 1.481(4) . ?
C2 C3 1.362(4) . ?
C2 C12 1.405(4) . ?
C3 C4 1.404(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(4) . ?
C6 C12 1.421(4) . ?
C7 C8 1.353(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C12 1.408(4) . ?
C10 C11 1.475(3) . ?
C11 O2 1.213(3) . ?
C11 N1 1.399(4) . ?
C13 N1 1.468(3) . ?
C13 C14 1.512(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.520(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.525(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.510(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.495(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 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
O1 C1 N1 120.0(3) . . ?
O1 C1 C2 123.1(3) . . ?
N1 C1 C2 116.9(2) . . ?
C3 C2 C12 120.2(3) . . ?
C3 C2 C1 119.7(3) . . ?
C12 C2 C1 120.2(2) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 123.4(3) . . ?
C5 C6 C12 118.2(3) . . ?
C7 C6 C12 118.4(2) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C12 119.8(2) . . ?
C9 C10 C11 119.8(2) . . ?
C12 C10 C11 120.4(2) . . ?
O2 C11 N1 120.4(2) . . ?
O2 C11 C10 122.7(2) . . ?
N1 C11 C10 116.9(2) . . ?
C2 C12 C10 120.8(2) . . ?
C2 C12 C6 119.8(2) . . ?
C10 C12 C6 119.4(2) . . ?
N1 C13 C14 111.7(2) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 112.7(2) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 113.1(2) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 112.5(2) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 115.3(3) . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 Br1 112.8(2) . . ?
C17 C18 H18A 109.0 . . ?
Br1 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
Br1 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C1 N1 C11 124.8(2) . . ?
C1 N1 C13 118.0(2) . . ?
C11 N1 C13 117.0(2) . . ?

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
O1 C1 C2 C3 2.8(4) . . . . ?
N1 C1 C2 C3 -178.4(2) . . . . ?
O1 C1 C2 C12 -176.0(3) . . . . ?
N1 C1 C2 C12 2.8(3) . . . . ?
C12 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C4 C5 C6 C12 -0.1(4) . . . . ?
C5 C6 C7 C8 -179.9(3) . . . . ?
C12 C6 C7 C8 -1.2(4) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C12 0.0(4) . . . . ?
C8 C9 C10 C11 179.3(3) . . . . ?
C9 C10 C11 O2 0.2(4) . . . . ?
C12 C10 C11 O2 179.5(3) . . . . ?
C9 C10 C11 N1 -178.9(2) . . . . ?
C12 C10 C11 N1 0.4(3) . . . . ?
C3 C2 C12 C10 -179.9(2) . . . . ?
C1 C2 C12 C10 -1.1(3) . . . . ?
C3 C2 C12 C6 -0.8(4) . . . . ?
C1 C2 C12 C6 178.0(2) . . . . ?
C9 C10 C12 C2 178.8(2) . . . . ?
C11 C10 C12 C2 -0.5(3) . . . . ?
C9 C10 C12 C6 -0.3(3) . . . . ?
C11 C10 C12 C6 -179.6(2) . . . . ?
C5 C6 C12 C2 0.6(3) . . . . ?
C7 C6 C12 C2 -178.2(2) . . . . ?
C5 C6 C12 C10 179.7(2) . . . . ?
C7 C6 C12 C10 0.9(3) . . . . ?
N1 C13 C14 C15 176.9(2) . . . . ?
C13 C14 C15 C16 169.3(3) . . . . ?
C14 C15 C16 C17 -178.4(3) . . . . ?
C15 C16 C17 C18 178.7(3) . . . . ?
C16 C17 C18 Br1 -67.7(3) . . . . ?
O1 C1 N1 C11 175.8(3) . . . . ?
C2 C1 N1 C11 -3.0(4) . . . . ?
O1 C1 N1 C13 1.3(4) . . . . ?
C2 C1 N1 C13 -177.5(2) . . . . ?
O2 C11 N1 C1 -177.6(3) . . . . ?
C10 C11 N1 C1 1.4(3) . . . . ?
O2 C11 N1 C13 -3.0(3) . . . . ?
C10 C11 N1 C13 176.0(2) . . . . ?
C14 C13 N1 C1 86.0(3) . . . . ?
C14 C13 N1 C11 -89.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        31.59
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_d:\data\guest\140701a\work\mo_140701a_0m
_database_code_depnum_ccdc_archive 'CCDC 1014214'
_audit_update_record             
;
2014-07-16 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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)/n

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

_cell_length_a                   8.2418(14)
_cell_length_b                   16.336(3)
_cell_length_c                   11.3610(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.266(3)
_cell_angle_gamma                90.00
_cell_volume                     1488.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5056
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      31.54

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11160
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2930
_reflns_number_gt                2338
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0873P)²+0.5474P] 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       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.0515(2) 0.15499(10) 0.29738(16) 0.0466(4) Uani 1 1 d . . .
C2 C -0.1272(2) 0.07353(10) 0.29884(15) 0.0435(4) Uani 1 1 d . . .
C3 C -0.2973(2) 0.06475(13) 0.26492(19) 0.0577(5) Uani 1 1 d . . .
H3 H -0.3643 0.1104 0.2416 0.069 Uiso 1 1 calc R . .
C4 C -0.3706(3) -0.01301(15) 0.2653(2) 0.0676(6) Uani 1 1 d . . .
H4 H -0.4858 -0.0184 0.2417 0.081 Uiso 1 1 calc R . .
C5 C -0.2749(3) -0.08013(13) 0.29964(19) 0.0621(6) Uani 1 1 d . . .
H5 H -0.3252 -0.1312 0.2986 0.075 Uiso 1 1 calc R . .
C6 C -0.0999(3) -0.07354(11) 0.33695(16) 0.0504(5) Uani 1 1 d . . .
C7 C -0.0251(2) 0.00447(10) 0.33621(14) 0.0405(4) Uani 1 1 d . . .
C8 C 0.1489(2) 0.01281(10) 0.37437(15) 0.0439(4) Uani 1 1 d . . .
C9 C 0.2470(3) -0.05443(12) 0.41451(18) 0.0569(5) Uani 1 1 d . . .
H9 H 0.3618 -0.0486 0.4413 0.068 Uiso 1 1 calc R . .
C10 C 0.1727(3) -0.13167(12) 0.4148(2) 0.0663(6) Uani 1 1 d . . .
H10 H 0.2391 -0.1770 0.4416 0.080 Uiso 1 1 calc R . .
C11 C 0.0053(3) -0.14116(11) 0.37640(19) 0.0622(6) Uani 1 1 d . . .
H11 H -0.0409 -0.1931 0.3761 0.075 Uiso 1 1 calc R . .
C12 C 0.2277(2) 0.09372(11) 0.37292(17) 0.0479(4) Uani 1 1 d . . .
C13 C 0.2016(3) 0.24006(11) 0.32695(18) 0.0545(5) Uani 1 1 d . . .
H13A H 0.1352 0.2722 0.2615 0.065 Uiso 1 1 calc R . .
H13B H 0.3108 0.2322 0.3103 0.065 Uiso 1 1 calc R . .
C14 C 0.2199(3) 0.28624(12) 0.4436(2) 0.0582(5) Uani 1 1 d . . .
H14A H 0.2653 0.2499 0.5106 0.070 Uiso 1 1 calc R . .
H14B H 0.1107 0.3039 0.4519 0.070 Uiso 1 1 calc R . .
C15 C 0.3329(3) 0.36069(12) 0.4504(2) 0.0608(6) Uani 1 1 d . . .
H15A H 0.3145 0.3971 0.5135 0.073 Uiso 1 1 calc R . .
H15B H 0.3042 0.3901 0.3742 0.073 Uiso 1 1 calc R . .
C16 C 0.5186(3) 0.33645(13) 0.4770(2) 0.0650(6) Uani 1 1 d . . .
H16A H 0.5418 0.3001 0.5463 0.078 Uiso 1 1 calc R . .
H16B H 0.5386 0.3060 0.4083 0.078 Uiso 1 1 calc R . .
C17 C 0.6381(3) 0.40648(14) 0.5017(2) 0.0677(6) Uani 1 1 d . . .
H17A H 0.6169 0.4427 0.4322 0.081 Uiso 1 1 calc R . .
H17B H 0.6189 0.4372 0.5703 0.081 Uiso 1 1 calc R . .
C18 C 0.8158(3) 0.37955(19) 0.5277(3) 0.0885(8) Uani 1 1 d . . .
H18A H 0.8409 0.3487 0.6016 0.133 Uiso 1 1 calc R . .
H18B H 0.8870 0.4267 0.5358 0.133 Uiso 1 1 calc R . .
H18C H 0.8337 0.3460 0.4626 0.133 Uiso 1 1 calc R . .
N1 N 0.12175(19) 0.15952(9) 0.33084(14) 0.0467(4) Uani 1 1 d . . .
O1 O -0.13357(18) 0.21649(8) 0.26760(15) 0.0694(5) Uani 1 1 d . . .
O2 O 0.37689(17) 0.10468(10) 0.40545(16) 0.0729(5) 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 O1 1.215(2) . ?
C1 N1 1.393(2) . ?
C1 C2 1.472(2) . ?
C2 C3 1.373(3) . ?
C2 C7 1.413(2) . ?
C3 C4 1.407(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 C11 1.413(3) . ?
C6 C7 1.417(2) . ?
C7 C8 1.406(2) . ?
C8 C9 1.378(2) . ?
C8 C12 1.474(3) . ?
C9 C10 1.403(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 O2 1.214(2) . ?
C12 N1 1.398(2) . ?
C13 N1 1.476(2) . ?
C13 C14 1.502(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.542(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.493(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.493(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
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
O1 C1 N1 120.17(16) . . ?
O1 C1 C2 122.70(17) . . ?
N1 C1 C2 117.12(15) . . ?
C3 C2 C7 120.02(16) . . ?
C3 C2 C1 119.96(16) . . ?
C7 C2 C1 120.02(16) . . ?
C2 C3 C4 120.31(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.64(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.81(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C11 123.14(18) . . ?
C5 C6 C7 118.90(18) . . ?
C11 C6 C7 117.96(19) . . ?
C8 C7 C2 120.68(15) . . ?
C8 C7 C6 119.99(16) . . ?
C2 C7 C6 119.32(17) . . ?
C9 C8 C7 120.28(17) . . ?
C9 C8 C12 119.46(17) . . ?
C7 C8 C12 120.26(15) . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.96(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 121.17(19) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
O2 C12 N1 120.01(17) . . ?
O2 C12 C8 123.17(17) . . ?
N1 C12 C8 116.81(15) . . ?
N1 C13 C14 112.10(16) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 112.45(17) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 111.89(17) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 114.96(18) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 112.7(2) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C12 124.96(14) . . ?
C1 N1 C13 118.38(15) . . ?
C12 N1 C13 116.61(15) . . ?

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
O1 C1 C2 C3 0.4(3) . . . . ?
N1 C1 C2 C3 -178.95(16) . . . . ?
O1 C1 C2 C7 -179.01(18) . . . . ?
N1 C1 C2 C7 1.6(3) . . . . ?
C7 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 179.57(18) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C11 178.4(2) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C3 C2 C7 C8 -178.23(16) . . . . ?
C1 C2 C7 C8 1.2(2) . . . . ?
C3 C2 C7 C6 0.7(3) . . . . ?
C1 C2 C7 C6 -179.92(16) . . . . ?
C5 C6 C7 C8 179.22(15) . . . . ?
C11 C6 C7 C8 -0.2(3) . . . . ?
C5 C6 C7 C2 0.3(3) . . . . ?
C11 C6 C7 C2 -179.12(16) . . . . ?
C2 C7 C8 C9 177.81(16) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C2 C7 C8 C12 -1.6(3) . . . . ?
C6 C7 C8 C12 179.52(15) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C12 C8 C9 C10 -179.29(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 -1.1(3) . . . . ?
C5 C6 C11 C10 -178.10(19) . . . . ?
C7 C6 C11 C10 1.3(3) . . . . ?
C9 C8 C12 O2 0.2(3) . . . . ?
C7 C8 C12 O2 179.55(17) . . . . ?
C9 C8 C12 N1 179.77(16) . . . . ?
C7 C8 C12 N1 -0.8(3) . . . . ?
N1 C13 C14 C15 168.16(17) . . . . ?
C13 C14 C15 C16 -76.2(2) . . . . ?
C14 C15 C16 C17 -172.0(2) . . . . ?
C15 C16 C17 C18 179.6(2) . . . . ?
O1 C1 N1 C12 176.28(18) . . . . ?
C2 C1 N1 C12 -4.4(3) . . . . ?
O1 C1 N1 C13 -1.1(3) . . . . ?
C2 C1 N1 C13 178.29(15) . . . . ?
O2 C12 N1 C1 -176.41(18) . . . . ?
C8 C12 N1 C1 4.0(3) . . . . ?
O2 C12 N1 C13 1.0(3) . . . . ?
C8 C12 N1 C13 -178.65(16) . . . . ?
C14 C13 N1 C1 88.4(2) . . . . ?
C14 C13 N1 C12 -89.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.043
