# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_venty15_p21
_database_code_depnum_ccdc_archive 'CCDC 887275'
#TrackingRef 'Venty15_6b_18Oct11_Deposition.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N2 O5'
_chemical_formula_weight         348.39

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)

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

_cell_length_a                   5.0331(3)
_cell_length_b                   33.007(2)
_cell_length_c                   5.5043(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.240(4)
_cell_angle_gamma                90.00
_cell_volume                     902.55(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    155(2)
_cell_measurement_reflns_used    4293
_cell_measurement_theta_min      3.704
_cell_measurement_theta_max      30.070

_exptl_crystal_description       Plates
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      155(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 kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6437
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3076
_reflns_number_gt                2899
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       '<i>APEX2 </i>(Bruker, 2007)'
_computing_cell_refinement       '<i>APEX2 </i>(Bruker, 2007)'
_computing_data_reduction        '<i>APEX2 </i>(Bruker, 2007)'
_computing_structure_solution    '<i>SHELXS-97</i> (Sheldrick, 2008)'
_computing_structure_refinement  '<i>SHELXL-97</i> (Sheldrick, 2008)'
_computing_molecular_graphics    '<i>SHELXTL-Plus</i> (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_number_reflns         3076
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.352
_refine_ls_restrained_S_all      1.352
_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
O2 O 0.4675(2) 0.26481(3) 0.2724(2) 0.0282(3) Uani 1 1 d . . .
O3 O 0.8768(2) 0.34520(3) 0.25080(19) 0.0262(3) Uani 1 1 d . . .
C10 C 0.6553(3) 0.32865(5) 0.2145(3) 0.0208(3) Uani 1 1 d . . .
O2G O 0.7406(2) 0.43437(3) 0.5253(2) 0.0313(3) Uani 1 1 d . . .
C9 C 0.6263(3) 0.28302(5) 0.1660(3) 0.0211(3) Uani 1 1 d . . .
N2G N 0.4284(2) 0.34829(4) 0.2285(2) 0.0206(3) Uani 1 1 d . . .
H2N H 0.2738 0.3353 0.2087 0.025 Uiso 1 1 calc R . .
O1G O 0.5821(2) 0.38112(3) 0.7101(2) 0.0380(3) Uani 1 1 d . . .
C1G C 0.4385(3) 0.39119(4) 0.2767(3) 0.0233(3) Uani 1 1 d . . .
H2G H 0.2530 0.4018 0.2653 0.028 Uiso 1 1 calc R . .
H1G H 0.5248 0.4050 0.1501 0.028 Uiso 1 1 calc R . .
C5 C 1.1388(3) 0.23143(5) -0.2914(3) 0.0316(4) Uani 1 1 d . . .
H5 H 1.2568 0.2203 -0.3925 0.038 Uiso 1 1 calc R . .
C3 C 0.9149(3) 0.28846(5) -0.1572(3) 0.0254(4) Uani 1 1 d . . .
H3 H 0.8752 0.3166 -0.1666 0.030 Uiso 1 1 calc R . .
C2 C 0.8007(3) 0.26403(5) 0.0071(3) 0.0214(3) Uani 1 1 d . . .
C1 C 0.8525(3) 0.22200(5) 0.0141(3) 0.0243(3) Uani 1 1 d . . .
N1 N 0.7271(3) 0.19749(4) 0.1702(2) 0.0285(3) Uani 1 1 d . . .
H1N H 0.5948 0.2090 0.2314 0.034 Uiso 1 1 calc R . .
O1 O 0.9535(3) 0.13789(4) 0.1714(3) 0.0564(4) Uani 1 1 d . . .
C6 C 1.0274(3) 0.20610(5) -0.1351(3) 0.0292(4) Uani 1 1 d . . .
H6 H 1.0694 0.1780 -0.1289 0.035 Uiso 1 1 calc R . .
C4 C 1.0835(3) 0.27222(5) -0.3048(3) 0.0290(4) Uani 1 1 d . . .
H4 H 1.1610 0.2890 -0.4149 0.035 Uiso 1 1 calc R . .
C13 C 1.2151(4) 0.49648(5) 0.9731(3) 0.0335(4) Uani 1 1 d . . .
H13A H 1.3303 0.4740 1.0478 0.040 Uiso 1 1 calc R . .
H13B H 1.0833 0.5025 1.0837 0.040 Uiso 1 1 calc R . .
C14 C 1.3907(3) 0.53360(5) 0.9608(3) 0.0317(4) Uani 1 1 d . . .
H14A H 1.5209 0.5280 0.8479 0.038 Uiso 1 1 calc R . .
H14B H 1.2761 0.5566 0.8922 0.038 Uiso 1 1 calc R . .
C7 C 0.7804(3) 0.15851(5) 0.2406(3) 0.0331(4) Uani 1 1 d . . .
C2G C 0.5935(3) 0.40049(5) 0.5276(3) 0.0248(4) Uani 1 1 d . . .
C8 C 0.6069(4) 0.14238(5) 0.4167(3) 0.0400(4) Uani 1 1 d . . .
H82 H 0.4253 0.1372 0.3281 0.060 Uiso 1 1 calc R . .
H81 H 0.5979 0.1624 0.5469 0.060 Uiso 1 1 calc R . .
H83 H 0.6845 0.1171 0.4901 0.060 Uiso 1 1 calc R . .
C12 C 1.0627(4) 0.48230(6) 0.7276(3) 0.0334(4) Uani 1 1 d . . .
H12B H 0.9454 0.5044 0.6509 0.040 Uiso 1 1 calc R . .
H12A H 1.1921 0.4755 0.6161 0.040 Uiso 1 1 calc R . .
C15 C 1.5432(4) 0.54549(6) 1.2101(3) 0.0393(5) Uani 1 1 d . . .
H15A H 1.6525 0.5221 1.2805 0.047 Uiso 1 1 calc R . .
H15B H 1.4120 0.5517 1.3210 0.047 Uiso 1 1 calc R . .
C11 C 0.8941(4) 0.44582(6) 0.7610(3) 0.0370(5) Uani 1 1 d . . .
H11A H 1.0115 0.4231 0.8287 0.044 Uiso 1 1 calc R . .
H11B H 0.7704 0.4521 0.8787 0.044 Uiso 1 1 calc R . .
C16 C 1.7273(4) 0.58181(6) 1.2032(4) 0.0485(5) Uani 1 1 d . . .
H16A H 1.8581 0.5760 1.0938 0.073 Uiso 1 1 calc R . .
H16C H 1.8227 0.5873 1.3694 0.073 Uiso 1 1 calc R . .
H16B H 1.6197 0.6055 1.1419 0.073 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0262(6) 0.0290(6) 0.0321(6) -0.0014(5) 0.0128(5) -0.0022(5)
O3 0.0180(6) 0.0310(6) 0.0297(6) -0.0023(5) 0.0043(5) -0.0016(5)
C10 0.0178(8) 0.0280(9) 0.0169(8) 0.0027(7) 0.0037(6) -0.0001(7)
O2G 0.0378(7) 0.0289(6) 0.0249(6) 0.0006(5) -0.0014(5) -0.0074(5)
C9 0.0160(8) 0.0291(9) 0.0177(7) 0.0010(7) 0.0012(6) 0.0004(6)
N2G 0.0147(6) 0.0213(7) 0.0262(7) -0.0009(5) 0.0042(5) -0.0012(5)
O1G 0.0547(8) 0.0360(8) 0.0233(6) 0.0036(5) 0.0066(6) -0.0091(6)
C1G 0.0223(8) 0.0222(8) 0.0258(8) 0.0016(7) 0.0050(6) 0.0009(6)
C5 0.0271(9) 0.0450(11) 0.0244(9) -0.0033(8) 0.0098(7) 0.0062(8)
C3 0.0233(8) 0.0327(9) 0.0199(8) 0.0010(7) 0.0029(6) 0.0018(7)
C2 0.0170(8) 0.0261(9) 0.0204(8) -0.0008(6) 0.0009(6) 0.0012(6)
C1 0.0203(8) 0.0301(9) 0.0214(8) -0.0031(7) 0.0005(6) 0.0001(7)
N1 0.0264(7) 0.0236(7) 0.0374(8) -0.0011(6) 0.0108(6) 0.0018(6)
O1 0.0529(9) 0.0363(8) 0.0874(10) 0.0144(8) 0.0342(8) 0.0159(7)
C6 0.0261(9) 0.0309(9) 0.0305(9) -0.0069(7) 0.0043(7) 0.0047(7)
C4 0.0264(9) 0.0410(10) 0.0204(8) 0.0024(7) 0.0062(7) 0.0035(7)
C13 0.0382(10) 0.0283(9) 0.0319(10) 0.0007(8) -0.0007(8) -0.0005(8)
C14 0.0326(9) 0.0288(9) 0.0327(10) -0.0023(8) 0.0025(7) -0.0008(7)
C7 0.0285(10) 0.0290(10) 0.0416(11) -0.0030(8) 0.0050(8) -0.0015(8)
C2G 0.0286(9) 0.0214(9) 0.0259(9) -0.0013(7) 0.0088(7) 0.0021(6)
C8 0.0402(11) 0.0293(10) 0.0522(11) 0.0040(9) 0.0127(9) -0.0010(8)
C12 0.0369(10) 0.0323(10) 0.0294(10) 0.0001(8) 0.0002(8) -0.0033(8)
C15 0.0397(11) 0.0394(11) 0.0364(11) -0.0040(8) -0.0010(9) -0.0051(9)
C11 0.0475(12) 0.0367(11) 0.0236(10) -0.0030(7) -0.0040(8) -0.0081(8)
C16 0.0420(12) 0.0499(13) 0.0540(13) -0.0138(10) 0.0089(10) -0.0120(10)

_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
O2 C9 1.2220(17) . ?
O3 C10 1.2288(17) . ?
C10 N2G 1.3262(19) . ?
C10 C9 1.532(2) . ?
O2G C2G 1.3420(19) . ?
O2G C11 1.450(2) . ?
C9 C2 1.475(2) . ?
N2G C1G 1.4401(19) . ?
N2G H2N 0.8800 . ?
O1G C2G 1.1999(18) . ?
C1G C2G 1.505(2) . ?
C1G H2G 0.9900 . ?
C1G H1G 0.9900 . ?
C5 C4 1.374(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C3 C4 1.374(2) . ?
C3 C2 1.402(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.411(2) . ?
C1 C6 1.399(2) . ?
C1 N1 1.4019(19) . ?
N1 C7 1.358(2) . ?
N1 H1N 0.8800 . ?
O1 C7 1.214(2) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C13 C12 1.517(2) . ?
C13 C14 1.519(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.512(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C7 C8 1.503(2) . ?
C8 H82 0.9800 . ?
C8 H81 0.9800 . ?
C8 H83 0.9800 . ?
C12 C11 1.501(2) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 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
O3 C10 N2G 122.71(14) . . ?
O3 C10 C9 121.59(13) . . ?
N2G C10 C9 115.59(13) . . ?
C2G O2G C11 115.12(12) . . ?
O2 C9 C2 124.91(14) . . ?
O2 C9 C10 116.84(13) . . ?
C2 C9 C10 118.16(13) . . ?
C10 N2G C1G 119.07(12) . . ?
C10 N2G H2N 120.5 . . ?
C1G N2G H2N 120.5 . . ?
N2G C1G C2G 111.57(12) . . ?
N2G C1G H2G 109.3 . . ?
C2G C1G H2G 109.3 . . ?
N2G C1G H1G 109.3 . . ?
C2G C1G H1G 109.3 . . ?
H2G C1G H1G 108.0 . . ?
C4 C5 C6 121.83(15) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C4 C3 C2 120.87(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C2 C1 119.33(13) . . ?
C3 C2 C9 118.88(14) . . ?
C1 C2 C9 121.79(13) . . ?
C6 C1 N1 122.08(14) . . ?
C6 C1 C2 118.94(14) . . ?
N1 C1 C2 118.98(12) . . ?
C7 N1 C1 129.32(13) . . ?
C7 N1 H1N 115.3 . . ?
C1 N1 H1N 115.3 . . ?
C5 C6 C1 119.67(15) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C5 C4 C3 119.30(15) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C12 C13 C14 115.08(13) . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 112.52(14) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
O1 C7 N1 124.09(15) . . ?
O1 C7 C8 121.65(16) . . ?
N1 C7 C8 114.26(15) . . ?
O1G C2G O2G 123.53(15) . . ?
O1G C2G C1G 124.91(15) . . ?
O2G C2G C1G 111.52(13) . . ?
C7 C8 H82 109.5 . . ?
C7 C8 H81 109.5 . . ?
H82 C8 H81 109.5 . . ?
C7 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
C11 C12 C13 110.68(13) . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
H12B C12 H12A 108.1 . . ?
C14 C15 C16 113.87(16) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O2G C11 C12 109.28(13) . . ?
O2G C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O2G C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?

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
O3 C10 C9 O2 136.40(15) . . . . ?
N2G C10 C9 O2 -39.83(19) . . . . ?
O3 C10 C9 C2 -40.3(2) . . . . ?
N2G C10 C9 C2 143.42(13) . . . . ?
O3 C10 N2G C1G 3.0(2) . . . . ?
C9 C10 N2G C1G 179.23(12) . . . . ?
C10 N2G C1G C2G -64.53(17) . . . . ?
C4 C3 C2 C1 -2.3(2) . . . . ?
C4 C3 C2 C9 178.51(15) . . . . ?
O2 C9 C2 C3 162.05(15) . . . . ?
C10 C9 C2 C3 -21.5(2) . . . . ?
O2 C9 C2 C1 -17.1(2) . . . . ?
C10 C9 C2 C1 159.32(13) . . . . ?
C3 C2 C1 C6 3.1(2) . . . . ?
C9 C2 C1 C6 -177.72(15) . . . . ?
C3 C2 C1 N1 -176.93(14) . . . . ?
C9 C2 C1 N1 2.3(2) . . . . ?
C6 C1 N1 C7 13.0(2) . . . . ?
C2 C1 N1 C7 -167.03(15) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
N1 C1 C6 C5 177.92(15) . . . . ?
C2 C1 C6 C5 -2.1(2) . . . . ?
C6 C5 C4 C3 0.6(3) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C12 C13 C14 C15 -178.37(15) . . . . ?
C1 N1 C7 O1 -1.0(3) . . . . ?
C1 N1 C7 C8 178.51(15) . . . . ?
C11 O2G C2G O1G 1.6(2) . . . . ?
C11 O2G C2G C1G 179.31(14) . . . . ?
N2G C1G C2G O1G -39.9(2) . . . . ?
N2G C1G C2G O2G 142.46(12) . . . . ?
C14 C13 C12 C11 -179.47(16) . . . . ?
C13 C14 C15 C16 178.31(16) . . . . ?
C2G O2G C11 C12 176.05(14) . . . . ?
C13 C12 C11 O2G 177.00(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.031


data_ventyc
_database_code_depnum_ccdc_archive 'CCDC 887276'
#TrackingRef 'Venty5a_C_Deposition_12June12.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N2 O3'
_chemical_formula_sum            'C16 H22 N2 O3'
_chemical_formula_weight         290.36

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

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                   36.447(7)
_cell_length_b                   5.0120(10)
_cell_length_c                   17.294(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.65(3)
_cell_angle_gamma                90.00
_cell_volume                     3069.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      22.5

_exptl_crystal_description       'Thin plates'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9913
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Synchrotron BM'
_diffrn_radiation_monochromator  Si<111>
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       '\f scans'
_diffrn_detector_area_resol_mean 'ADSC Q210'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31592
_diffrn_reflns_av_R_equivalents  0.1015
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5360
_reflns_number_gt                4467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BLU-ICE (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;ORTEP-3 (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;

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

There is an Alert level A, 'The value of the weighted R factor is > 0.45',
the source of which is not clear to us. These were very small
crystals, which were used for diffraction in the synchrrotron beam.
This could be a case of pseudo symmetry (structure is solved in
Monoclinic P2(1)/c with two molecules in the asymmetric unit).
However, the packing of the molecules do not show any bad short contacts,
so we have
accepted the solution in the monoclinic space group.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+94.8045P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5360
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2143
_refine_ls_R_factor_gt           0.2000
_refine_ls_wR_factor_ref         0.4524
_refine_ls_wR_factor_gt          0.4452
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_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
O1A O 0.0456(2) 0.6772(17) -0.0465(4) 0.0298(19) Uani 1 1 d . . .
O2A O 0.11410(19) 0.1964(15) 0.1894(4) 0.0219(16) Uani 1 1 d . . .
O3A O 0.1454(2) 0.6565(17) 0.3369(4) 0.0294(18) Uani 1 1 d . . .
N1A N 0.0670(2) 0.4344(17) 0.0687(5) 0.0181(18) Uani 1 1 d . . .
H1NA H 0.0773 0.2847 0.0857 0.022 Uiso 1 1 calc R . .
N2A N 0.1522(2) 0.214(2) 0.3429(5) 0.022(2) Uani 1 1 d . . .
H2NA H 0.1449 0.0643 0.3198 0.027 Uiso 1 1 calc R . .
C1A C 0.0568(3) 0.607(2) 0.1258(6) 0.021(2) Uani 1 1 d . . .
C2A C 0.0765(3) 0.574(2) 0.2062(6) 0.017(2) Uani 1 1 d . . .
C3A C 0.0649(3) 0.731(2) 0.2649(6) 0.018(2) Uani 1 1 d . . .
H3A H 0.0774 0.7149 0.3182 0.022 Uiso 1 1 calc R . .
C4A C 0.0356(3) 0.906(2) 0.2434(6) 0.021(2) Uani 1 1 d . . .
H4A H 0.0271 0.9979 0.2825 0.026 Uiso 1 1 calc R . .
C5A C 0.0179(3) 0.950(2) 0.1624(6) 0.018(2) Uani 1 1 d . . .
H5A H -0.0004 1.0813 0.1480 0.021 Uiso 1 1 calc R . .
C6A C 0.0282(3) 0.794(2) 0.1046(6) 0.018(2) Uani 1 1 d . . .
H6A H 0.0158 0.8145 0.0514 0.022 Uiso 1 1 calc R . .
C7A C 0.0617(3) 0.487(2) -0.0120(6) 0.025(2) Uani 1 1 d . . .
C8A C 0.0793(3) 0.268(3) -0.0543(6) 0.026(3) Uani 1 1 d . . .
H81A H 0.0670 0.2663 -0.1099 0.039 Uiso 1 1 calc R . .
H83A H 0.0760 0.0972 -0.0314 0.039 Uiso 1 1 calc R . .
H82A H 0.1057 0.3026 -0.0478 0.039 Uiso 1 1 calc R . .
C9A C 0.1081(3) 0.383(2) 0.2300(6) 0.020(2) Uani 1 1 d . . .
C10A C 0.1376(3) 0.430(2) 0.3110(6) 0.019(2) Uani 1 1 d . . .
C11A C 0.1811(3) 0.213(3) 0.4178(6) 0.026(3) Uani 1 1 d . . .
H11B H 0.1779 0.0542 0.4475 0.031 Uiso 1 1 calc R . .
H11A H 0.1770 0.3664 0.4490 0.031 Uiso 1 1 calc R . .
C12A C 0.2207(3) 0.222(3) 0.4081(6) 0.027(3) Uani 1 1 d . . .
H12A H 0.2231 0.3721 0.3743 0.032 Uiso 1 1 calc R . .
H12B H 0.2254 0.0608 0.3809 0.032 Uiso 1 1 calc R . .
C13A C 0.2504(3) 0.245(3) 0.4845(6) 0.040(4) Uani 1 1 d . . .
H13A H 0.2481 0.4215 0.5061 0.049 Uiso 1 1 calc R . .
H13B H 0.2443 0.1173 0.5216 0.049 Uiso 1 1 calc R . .
C14A C 0.2902(3) 0.207(4) 0.4832(7) 0.057(5) Uani 1 1 d . . .
H14A H 0.3050 0.2853 0.5319 0.068 Uiso 1 1 calc R . .
H14B H 0.2948 0.0158 0.4877 0.068 Uiso 1 1 calc R . .
C15A C 0.3070(3) 0.298(3) 0.4203(6) 0.039(3) Uani 1 1 d . . .
H15A H 0.3043 0.4905 0.4171 0.047 Uiso 1 1 calc R . .
H15B H 0.2922 0.2254 0.3706 0.047 Uiso 1 1 calc R . .
C16A C 0.3471(3) 0.234(3) 0.4256(7) 0.039(3) Uani 1 1 d . . .
H16B H 0.3624 0.3057 0.4741 0.059 Uiso 1 1 calc R . .
H16C H 0.3548 0.3103 0.3810 0.059 Uiso 1 1 calc R . .
H16A H 0.3503 0.0436 0.4252 0.059 Uiso 1 1 calc R . .
O1B O 0.4544(2) 0.3150(18) -0.0923(4) 0.032(2) Uani 1 1 d . . .
O2B O 0.38592(19) 0.8053(16) 0.0740(4) 0.0239(17) Uani 1 1 d . . .
O3B O 0.3551(2) 0.354(2) 0.1913(5) 0.038(2) Uani 1 1 d . . .
N1B N 0.4334(3) 0.566(2) 0.0011(5) 0.027(2) Uani 1 1 d . . .
H1NB H 0.4238 0.7186 0.0077 0.033 Uiso 1 1 calc R . .
N2B N 0.3478(2) 0.805(2) 0.1902(5) 0.023(2) Uani 1 1 d . . .
H2NB H 0.3550 0.9560 0.1750 0.027 Uiso 1 1 calc R . .
C1B C 0.4432(3) 0.394(2) 0.0688(6) 0.024(2) Uani 1 1 d . . .
C2B C 0.4237(3) 0.434(2) 0.1286(6) 0.020(2) Uani 1 1 d . . .
C3B C 0.4352(3) 0.287(2) 0.1993(6) 0.020(2) Uani 1 1 d . . .
H3B H 0.4235 0.3123 0.2409 0.024 Uiso 1 1 calc R . .
C4B C 0.4640(3) 0.104(2) 0.2066(6) 0.025(2) Uani 1 1 d . . .
H4B H 0.4718 0.0091 0.2539 0.030 Uiso 1 1 calc R . .
C5B C 0.4817(3) 0.057(3) 0.1442(6) 0.027(3) Uani 1 1 d . . .
H5B H 0.4996 -0.0774 0.1482 0.033 Uiso 1 1 calc R . .
C6B C 0.4719(3) 0.217(2) 0.0755(6) 0.022(2) Uani 1 1 d . . .
H6B H 0.4849 0.2014 0.0354 0.026 Uiso 1 1 calc R . .
C7B C 0.4380(3) 0.508(3) -0.0740(6) 0.027(3) Uani 1 1 d . . .
C8B C 0.4204(3) 0.720(2) -0.1344(6) 0.025(2) Uani 1 1 d . . .
H84B H 0.4301 0.8922 -0.1156 0.037 Uiso 1 1 calc R . .
H83B H 0.3935 0.7190 -0.1412 0.037 Uiso 1 1 calc R . .
H82B H 0.4264 0.6829 -0.1844 0.037 Uiso 1 1 calc R . .
C9B C 0.3923(3) 0.621(2) 0.1209(6) 0.022(2) Uani 1 1 d . . .
C10B C 0.3632(3) 0.587(3) 0.1721(6) 0.028(3) Uani 1 1 d . . .
C11B C 0.3187(3) 0.802(3) 0.2354(6) 0.023(2) Uani 1 1 d . . .
H11D H 0.3195 0.9709 0.2634 0.028 Uiso 1 1 calc R . .
H11C H 0.3247 0.6625 0.2752 0.028 Uiso 1 1 calc R . .
C12B C 0.2791(3) 0.759(3) 0.1869(6) 0.030(3) Uani 1 1 d . . .
H12C H 0.2771 0.5800 0.1650 0.035 Uiso 1 1 calc R . .
H12D H 0.2740 0.8837 0.1428 0.035 Uiso 1 1 calc R . .
C13B C 0.2496(3) 0.794(3) 0.2345(6) 0.025(2) Uani 1 1 d . . .
H13D H 0.2483 0.9822 0.2469 0.030 Uiso 1 1 calc R . .
H13C H 0.2580 0.6996 0.2844 0.030 Uiso 1 1 calc R . .
C14B C 0.2102(3) 0.699(3) 0.1949(6) 0.036(3) Uani 1 1 d . . .
H14D H 0.2108 0.5066 0.1903 0.043 Uiso 1 1 calc R . .
H14C H 0.1937 0.7415 0.2298 0.043 Uiso 1 1 calc R . .
C15B C 0.1931(3) 0.811(3) 0.1150(6) 0.032(3) Uani 1 1 d . . .
H15D H 0.2084 0.7568 0.0789 0.038 Uiso 1 1 calc R . .
H15C H 0.1941 1.0038 0.1185 0.038 Uiso 1 1 calc R . .
C16B C 0.1530(3) 0.728(3) 0.0798(7) 0.040(3) Uani 1 1 d . . .
H16E H 0.1514 0.5372 0.0778 0.060 Uiso 1 1 calc R . .
H16D H 0.1449 0.7995 0.0270 0.060 Uiso 1 1 calc R . .
H16F H 0.1370 0.7959 0.1122 0.060 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.041(5) 0.034(5) 0.012(3) 0.008(3) 0.003(3) 0.006(4)
O2A 0.026(4) 0.019(4) 0.017(3) 0.001(3) -0.002(3) 0.005(3)
O3A 0.034(4) 0.028(5) 0.022(4) -0.002(3) -0.001(3) -0.003(4)
N1A 0.026(4) 0.011(4) 0.017(4) 0.003(3) 0.003(3) -0.001(4)
N2A 0.018(4) 0.028(5) 0.019(4) 0.004(4) 0.002(3) 0.002(4)
C1A 0.028(5) 0.021(6) 0.014(5) 0.003(4) 0.004(4) 0.005(5)
C2A 0.027(5) 0.008(5) 0.015(5) 0.000(4) 0.006(4) 0.003(4)
C3A 0.013(4) 0.025(6) 0.016(5) -0.004(4) 0.003(4) -0.007(4)
C4A 0.025(5) 0.023(6) 0.018(5) -0.003(4) 0.009(4) -0.002(5)
C5A 0.023(5) 0.009(5) 0.022(5) 0.004(4) 0.006(4) 0.005(4)
C6A 0.014(5) 0.021(6) 0.017(5) -0.006(4) -0.002(4) 0.005(4)
C7A 0.034(6) 0.026(6) 0.018(5) 0.000(5) 0.012(4) -0.010(5)
C8A 0.023(5) 0.042(7) 0.015(5) 0.008(5) 0.006(4) 0.006(5)
C9A 0.020(5) 0.020(6) 0.017(5) 0.001(4) -0.001(4) 0.004(4)
C10A 0.024(5) 0.020(6) 0.015(5) -0.001(4) 0.008(4) -0.002(4)
C11A 0.023(5) 0.041(7) 0.011(5) 0.007(5) -0.002(4) 0.002(5)
C12A 0.016(5) 0.049(8) 0.013(5) 0.003(5) -0.001(4) 0.001(5)
C13A 0.017(5) 0.088(12) 0.013(5) -0.002(6) -0.001(4) 0.006(6)
C14A 0.021(6) 0.128(16) 0.017(6) 0.027(8) -0.007(4) -0.007(8)
C15A 0.018(5) 0.075(10) 0.023(6) -0.012(6) 0.002(4) -0.001(6)
C16A 0.019(6) 0.063(10) 0.034(6) -0.016(7) 0.001(5) -0.003(6)
O1B 0.039(5) 0.040(5) 0.018(4) -0.003(4) 0.012(3) 0.011(4)
O2B 0.020(4) 0.028(4) 0.026(4) -0.002(4) 0.008(3) 0.005(3)
O3B 0.022(4) 0.065(7) 0.030(4) 0.003(4) 0.012(3) 0.007(4)
N1B 0.029(5) 0.036(6) 0.016(4) -0.008(4) 0.003(4) 0.003(4)
N2B 0.014(4) 0.037(6) 0.017(4) -0.004(4) 0.002(3) 0.005(4)
C1B 0.027(5) 0.027(6) 0.019(5) -0.008(5) 0.009(4) -0.009(5)
C2B 0.018(5) 0.029(6) 0.014(5) 0.001(4) 0.001(4) -0.002(4)
C3B 0.015(5) 0.029(6) 0.015(5) 0.000(4) -0.001(4) -0.004(4)
C4B 0.028(5) 0.031(7) 0.014(5) 0.000(5) 0.003(4) 0.005(5)
C5B 0.023(5) 0.039(7) 0.019(5) 0.005(5) 0.001(4) -0.001(5)
C6B 0.013(5) 0.032(6) 0.019(5) 0.012(5) 0.004(4) 0.003(4)
C7B 0.022(5) 0.045(8) 0.014(5) 0.013(5) 0.004(4) 0.004(5)
C8B 0.022(5) 0.036(7) 0.016(5) 0.007(5) 0.003(4) 0.009(5)
C9B 0.018(5) 0.024(6) 0.024(5) -0.007(5) 0.006(4) -0.002(4)
C10B 0.033(6) 0.040(8) 0.010(5) 0.011(5) 0.003(4) 0.001(5)
C11B 0.017(5) 0.041(7) 0.014(5) -0.010(5) 0.009(4) 0.000(5)
C12B 0.014(5) 0.060(9) 0.016(5) -0.010(5) 0.006(4) -0.004(5)
C13B 0.017(5) 0.041(7) 0.020(5) 0.000(5) 0.008(4) 0.004(5)
C14B 0.021(5) 0.068(10) 0.023(5) 0.008(6) 0.012(4) -0.006(6)
C15B 0.014(5) 0.055(8) 0.025(6) 0.015(6) 0.002(4) 0.002(5)
C16B 0.015(5) 0.072(10) 0.032(6) -0.007(7) 0.004(4) 0.001(6)

_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
O1A C7A 1.202(14) . ?
O2A C9A 1.220(13) . ?
O3A C10A 1.231(13) . ?
N1A C7A 1.388(13) . ?
N1A C1A 1.426(13) . ?
N1A H1NA 0.8600 . ?
N2A C10A 1.272(14) . ?
N2A C11A 1.464(12) . ?
N2A H2NA 0.8600 . ?
C1A C6A 1.384(14) . ?
C1A C2A 1.416(13) . ?
C2A C3A 1.427(14) . ?
C2A C9A 1.479(14) . ?
C3A C4A 1.363(15) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.413(14) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.389(14) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C8A 1.541(16) . ?
C8A H81A 0.9600 . ?
C8A H83A 0.9600 . ?
C8A H82A 0.9600 . ?
C9A C10A 1.568(13) . ?
C11A C12A 1.493(14) . ?
C11A H11B 0.9700 . ?
C11A H11A 0.9700 . ?
C12A C13A 1.502(13) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C14A 1.470(16) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.441(16) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A C16A 1.480(15) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16A H16A 0.9600 . ?
O1B C7B 1.218(15) . ?
O2B C9B 1.214(13) . ?
O3B C10B 1.270(15) . ?
N1B C7B 1.378(13) . ?
N1B C1B 1.430(15) . ?
N1B H1NB 0.8600 . ?
N2B C10B 1.299(16) . ?
N2B C11B 1.460(12) . ?
N2B H2NB 0.8600 . ?
C1B C6B 1.357(15) . ?
C1B C2B 1.401(14) . ?
C2B C3B 1.405(14) . ?
C2B C9B 1.459(15) . ?
C3B C4B 1.376(15) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.401(15) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.408(14) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B C8B 1.522(15) . ?
C8B H84B 0.9600 . ?
C8B H83B 0.9600 . ?
C8B H82B 0.9600 . ?
C9B C10B 1.542(14) . ?
C11B C12B 1.504(13) . ?
C11B H11D 0.9700 . ?
C11B H11C 0.9700 . ?
C12B C13B 1.510(13) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C14B 1.515(15) . ?
C13B H13D 0.9700 . ?
C13B H13C 0.9700 . ?
C14B C15B 1.483(15) . ?
C14B H14D 0.9700 . ?
C14B H14C 0.9700 . ?
C15B C16B 1.504(15) . ?
C15B H15D 0.9700 . ?
C15B H15C 0.9700 . ?
C16B H16E 0.9600 . ?
C16B H16D 0.9600 . ?
C16B H16F 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
C7A N1A C1A 125.8(9) . . ?
C7A N1A H1NA 117.1 . . ?
C1A N1A H1NA 117.1 . . ?
C10A N2A C11A 121.6(10) . . ?
C10A N2A H2NA 119.2 . . ?
C11A N2A H2NA 119.2 . . ?
C6A C1A C2A 121.0(9) . . ?
C6A C1A N1A 121.9(9) . . ?
C2A C1A N1A 117.1(9) . . ?
C1A C2A C3A 117.8(9) . . ?
C1A C2A C9A 122.0(9) . . ?
C3A C2A C9A 120.2(9) . . ?
C4A C3A C2A 120.4(9) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C5A 121.0(9) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C6A C5A C4A 119.3(9) . . ?
C6A C5A H5A 120.3 . . ?
C4A C5A H5A 120.3 . . ?
C1A C6A C5A 120.2(9) . . ?
C1A C6A H6A 119.9 . . ?
C5A C6A H6A 119.9 . . ?
O1A C7A N1A 125.8(10) . . ?
O1A C7A C8A 122.7(9) . . ?
N1A C7A C8A 111.5(9) . . ?
C7A C8A H81A 109.5 . . ?
C7A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
C7A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
H83A C8A H82A 109.5 . . ?
O2A C9A C2A 124.7(9) . . ?
O2A C9A C10A 116.8(9) . . ?
C2A C9A C10A 118.4(9) . . ?
O3A C10A N2A 126.2(9) . . ?
O3A C10A C9A 120.9(9) . . ?
N2A C10A C9A 112.8(9) . . ?
N2A C11A C12A 114.4(8) . . ?
N2A C11A H11B 108.7 . . ?
C12A C11A H11B 108.7 . . ?
N2A C11A H11A 108.7 . . ?
C12A C11A H11A 108.7 . . ?
H11B C11A H11A 107.6 . . ?
C11A C12A C13A 114.8(9) . . ?
C11A C12A H12A 108.6 . . ?
C13A C12A H12A 108.6 . . ?
C11A C12A H12B 108.6 . . ?
C13A C12A H12B 108.6 . . ?
H12A C12A H12B 107.5 . . ?
C14A C13A C12A 119.1(10) . . ?
C14A C13A H13A 107.5 . . ?
C12A C13A H13A 107.5 . . ?
C14A C13A H13B 107.5 . . ?
C12A C13A H13B 107.5 . . ?
H13A C13A H13B 107.0 . . ?
C15A C14A C13A 124.4(11) . . ?
C15A C14A H14A 106.2 . . ?
C13A C14A H14A 106.2 . . ?
C15A C14A H14B 106.2 . . ?
C13A C14A H14B 106.2 . . ?
H14A C14A H14B 106.4 . . ?
C14A C15A C16A 118.2(12) . . ?
C14A C15A H15A 107.8 . . ?
C16A C15A H15A 107.8 . . ?
C14A C15A H15B 107.8 . . ?
C16A C15A H15B 107.8 . . ?
H15A C15A H15B 107.1 . . ?
C15A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15A C16A H16A 109.5 . . ?
H16B C16A H16A 109.5 . . ?
H16C C16A H16A 109.5 . . ?
C7B N1B C1B 125.6(10) . . ?
C7B N1B H1NB 117.2 . . ?
C1B N1B H1NB 117.2 . . ?
C10B N2B C11B 122.0(10) . . ?
C10B N2B H2NB 119.0 . . ?
C11B N2B H2NB 119.0 . . ?
C6B C1B C2B 123.2(10) . . ?
C6B C1B N1B 120.2(9) . . ?
C2B C1B N1B 116.5(10) . . ?
C1B C2B C3B 117.8(10) . . ?
C1B C2B C9B 123.2(10) . . ?
C3B C2B C9B 119.0(9) . . ?
C4B C3B C2B 119.7(9) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 121.4(10) . . ?
C3B C4B H4B 119.3 . . ?
C5B C4B H4B 119.3 . . ?
C4B C5B C6B 118.9(11) . . ?
C4B C5B H5B 120.5 . . ?
C6B C5B H5B 120.5 . . ?
C1B C6B C5B 118.8(10) . . ?
C1B C6B H6B 120.6 . . ?
C5B C6B H6B 120.6 . . ?
O1B C7B N1B 126.0(10) . . ?
O1B C7B C8B 122.0(9) . . ?
N1B C7B C8B 112.0(10) . . ?
C7B C8B H84B 109.5 . . ?
C7B C8B H83B 109.5 . . ?
H84B C8B H83B 109.5 . . ?
C7B C8B H82B 109.5 . . ?
H84B C8B H82B 109.5 . . ?
H83B C8B H82B 109.5 . . ?
O2B C9B C2B 124.9(9) . . ?
O2B C9B C10B 114.7(9) . . ?
C2B C9B C10B 120.4(10) . . ?
O3B C10B N2B 124.7(10) . . ?
O3B C10B C9B 119.1(11) . . ?
N2B C10B C9B 116.2(10) . . ?
N2B C11B C12B 115.2(8) . . ?
N2B C11B H11D 108.5 . . ?
C12B C11B H11D 108.5 . . ?
N2B C11B H11C 108.5 . . ?
C12B C11B H11C 108.5 . . ?
H11D C11B H11C 107.5 . . ?
C11B C12B C13B 113.1(8) . . ?
C11B C12B H12C 109.0 . . ?
C13B C12B H12C 109.0 . . ?
C11B C12B H12D 109.0 . . ?
C13B C12B H12D 109.0 . . ?
H12C C12B H12D 107.8 . . ?
C12B C13B C14B 116.0(9) . . ?
C12B C13B H13D 108.3 . . ?
C14B C13B H13D 108.3 . . ?
C12B C13B H13C 108.3 . . ?
C14B C13B H13C 108.3 . . ?
H13D C13B H13C 107.4 . . ?
C15B C14B C13B 116.6(10) . . ?
C15B C14B H14D 108.1 . . ?
C13B C14B H14D 108.1 . . ?
C15B C14B H14C 108.1 . . ?
C13B C14B H14C 108.1 . . ?
H14D C14B H14C 107.3 . . ?
C14B C15B C16B 115.4(10) . . ?
C14B C15B H15D 108.4 . . ?
C16B C15B H15D 108.4 . . ?
C14B C15B H15C 108.4 . . ?
C16B C15B H15C 108.4 . . ?
H15D C15B H15C 107.5 . . ?
C15B C16B H16E 109.5 . . ?
C15B C16B H16D 109.5 . . ?
H16E C16B H16D 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?

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
C7A N1A C1A C6A 25.6(16) . . . . ?
C7A N1A C1A C2A -156.2(10) . . . . ?
C6A C1A C2A C3A 2.6(15) . . . . ?
N1A C1A C2A C3A -175.6(9) . . . . ?
C6A C1A C2A C9A -177.7(10) . . . . ?
N1A C1A C2A C9A 4.1(15) . . . . ?
C1A C2A C3A C4A 0.3(15) . . . . ?
C9A C2A C3A C4A -179.4(10) . . . . ?
C2A C3A C4A C5A -4.7(15) . . . . ?
C3A C4A C5A C6A 6.2(15) . . . . ?
C2A C1A C6A C5A -1.1(16) . . . . ?
N1A C1A C6A C5A 177.1(9) . . . . ?
C4A C5A C6A C1A -3.3(15) . . . . ?
C1A N1A C7A O1A -5.1(17) . . . . ?
C1A N1A C7A C8A 174.9(9) . . . . ?
C1A C2A C9A O2A -19.0(17) . . . . ?
C3A C2A C9A O2A 160.7(10) . . . . ?
C1A C2A C9A C10A 157.5(10) . . . . ?
C3A C2A C9A C10A -22.8(14) . . . . ?
C11A N2A C10A O3A 0.4(16) . . . . ?
C11A N2A C10A C9A 178.5(8) . . . . ?
O2A C9A C10A O3A 145.3(10) . . . . ?
C2A C9A C10A O3A -31.5(14) . . . . ?
O2A C9A C10A N2A -32.9(13) . . . . ?
C2A C9A C10A N2A 150.3(9) . . . . ?
C10A N2A C11A C12A -92.0(13) . . . . ?
N2A C11A C12A C13A 175.0(12) . . . . ?
C11A C12A C13A C14A 169.0(14) . . . . ?
C12A C13A C14A C15A 38(3) . . . . ?
C13A C14A C15A C16A -177.4(15) . . . . ?
C7B N1B C1B C6B 29.3(16) . . . . ?
C7B N1B C1B C2B -155.4(10) . . . . ?
C6B C1B C2B C3B 1.3(16) . . . . ?
N1B C1B C2B C3B -173.9(9) . . . . ?
C6B C1B C2B C9B -178.8(10) . . . . ?
N1B C1B C2B C9B 6.0(15) . . . . ?
C1B C2B C3B C4B -2.1(15) . . . . ?
C9B C2B C3B C4B 178.0(10) . . . . ?
C2B C3B C4B C5B -1.3(17) . . . . ?
C3B C4B C5B C6B 5.4(17) . . . . ?
C2B C1B C6B C5B 2.8(17) . . . . ?
N1B C1B C6B C5B 177.8(10) . . . . ?
C4B C5B C6B C1B -6.1(16) . . . . ?
C1B N1B C7B O1B -7.9(18) . . . . ?
C1B N1B C7B C8B 173.2(10) . . . . ?
C1B C2B C9B O2B -19.9(17) . . . . ?
C3B C2B C9B O2B 160.0(10) . . . . ?
C1B C2B C9B C10B 157.8(10) . . . . ?
C3B C2B C9B C10B -22.3(15) . . . . ?
C11B N2B C10B O3B -0.1(16) . . . . ?
C11B N2B C10B C9B 177.4(8) . . . . ?
O2B C9B C10B O3B 145.2(10) . . . . ?
C2B C9B C10B O3B -32.7(15) . . . . ?
O2B C9B C10B N2B -32.5(13) . . . . ?
C2B C9B C10B N2B 149.6(10) . . . . ?
C10B N2B C11B C12B -84.9(14) . . . . ?
N2B C11B C12B C13B -172.3(11) . . . . ?
C11B C12B C13B C14B -167.9(12) . . . . ?
C12B C13B C14B C15B -54.9(17) . . . . ?
C13B C14B C15B C16B -175.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.178


data_inp1bar
_database_code_depnum_ccdc_archive 'CCDC 887277'
#TrackingRef 'Venty5b1_2_18Oct11_Depostion.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H27 Br N2 O3'
_chemical_formula_weight         411.34

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'
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

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

_cell_length_a                   8.8992(12)
_cell_length_b                   9.9071(17)
_cell_length_c                   12.299(2)
_cell_angle_alpha                75.265(7)
_cell_angle_beta                 81.633(7)
_cell_angle_gamma                76.227(7)
_cell_volume                     1014.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3403
_cell_measurement_theta_min      2.174
_cell_measurement_theta_max      23.095

_exptl_crystal_description       Needles
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    2.045
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5223
_exptl_absorpt_correction_T_max  0.8486
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12828
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3548
_reflns_number_gt                2328
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       '<i>APEX2 </i>(Bruker, 2007)'
_computing_cell_refinement       '<i>APEX2 </i>(Bruker, 2007)'
_computing_data_reduction        '<i>APEX2 </i>(Bruker, 2007)'
_computing_structure_solution    '<i>SHELXS-97</i> (Sheldrick, 2008)'
_computing_structure_refinement  '<i>SHELXL-97</i> (Sheldrick, 2008)'
_computing_molecular_graphics    '<i>SHELXTL-Plus</i> (Sheldrick, 2008)'

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

Atoms in the flexible side chain exhibit disorder, which is modelled
over two positions of slightly unequal (56:44) occupancies.The starting and
the end atoms are not affected by this disorder, but positions of four atoms
C12, C13, C14 and C15 are influenced by this to a varying degree.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0701P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3548
_refine_ls_number_parameters     264
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.094
_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 1.07244(7) 0.38919(7) 0.32988(5) 0.0651(3) Uani 1 1 d . . .
O1 O 0.6416(4) 0.8148(4) -0.0940(3) 0.0464(9) Uani 1 1 d . . .
O2 O 0.6570(4) 0.8576(4) 0.1462(3) 0.0457(9) Uani 1 1 d . B .
O3 O 0.3984(4) 0.6609(4) 0.1150(3) 0.0472(9) Uani 1 1 d . . .
N1 N 0.6526(5) 0.5774(4) -0.0536(3) 0.0363(10) Uani 1 1 d . . .
H1N H 0.6233 0.5085 -0.0729 0.044 Uiso 1 1 calc R . .
N2 N 0.3601(5) 0.8984(4) 0.1020(4) 0.0418(11) Uani 1 1 d . . .
H2N H 0.4040 0.9689 0.1027 0.050 Uiso 1 1 calc R A 1
C4 C 0.9383(6) 0.4477(5) 0.2112(4) 0.0376(12) Uani 1 1 d . . .
C5 C 0.9473(6) 0.3614(5) 0.1378(4) 0.0387(12) Uani 1 1 d . . .
H5 H 1.0180 0.2716 0.1462 0.046 Uiso 1 1 calc R . .
C6 C 0.8507(6) 0.4089(5) 0.0515(4) 0.0352(12) Uani 1 1 d . . .
H6 H 0.8576 0.3515 -0.0010 0.042 Uiso 1 1 calc R . .
C1 C 0.7429(5) 0.5387(5) 0.0391(4) 0.0295(10) Uani 1 1 d . . .
C2 C 0.7333(5) 0.6232(5) 0.1167(4) 0.0298(11) Uani 1 1 d . B .
C3 C 0.8341(6) 0.5774(5) 0.2006(4) 0.0341(11) Uani 1 1 d . . .
H3 H 0.8316 0.6357 0.2516 0.041 Uiso 1 1 calc R . .
C7 C 0.6072(6) 0.7119(6) -0.1152(4) 0.0411(13) Uani 1 1 d . . .
C8 C 0.5123(7) 0.7281(7) -0.2103(5) 0.0579(16) Uani 1 1 d . . .
H83 H 0.4055 0.7769 -0.1924 0.087 Uiso 1 1 calc R . .
H81 H 0.5121 0.6336 -0.2214 0.087 Uiso 1 1 calc R . .
H82 H 0.5570 0.7844 -0.2796 0.087 Uiso 1 1 calc R . .
C9 C 0.6198(6) 0.7592(5) 0.1218(4) 0.0361(12) Uani 1 1 d . . .
C10 C 0.4480(6) 0.7680(5) 0.1112(4) 0.0361(12) Uani 1 1 d . B .
C11A C 0.1955(7) 0.9288(6) 0.0908(6) 0.0609(17) Uani 0.566(11) 1 d PDU B 1
H11A H 0.1690 0.8566 0.0584 0.073 Uiso 0.566(11) 1 calc PR B 1
H11B H 0.1627 1.0243 0.0412 0.073 Uiso 0.566(11) 1 calc PR B 1
C12A C 0.1129(13) 0.9236(16) 0.2149(10) 0.056(4) Uani 0.566(11) 1 d PDU B 1
H12A H 0.1517 0.8294 0.2644 0.067 Uiso 0.566(11) 1 calc PR B 1
H12B H 0.1390 0.9978 0.2453 0.067 Uiso 0.566(11) 1 calc PR B 1
C13A C -0.0579(12) 0.9478(11) 0.2151(9) 0.055(3) Uani 0.566(11) 1 d PDU B 1
H13A H -0.0806 0.8847 0.1715 0.066 Uiso 0.566(11) 1 calc PR B 1
H13B H -0.0961 1.0475 0.1744 0.066 Uiso 0.566(11) 1 calc PR B 1
C14A C -0.1486(15) 0.9235(14) 0.3270(10) 0.064(3) Uani 0.566(11) 1 d PDU B 1
H14A H -0.0990 0.8312 0.3743 0.076 Uiso 0.566(11) 1 calc PR B 1
H14B H -0.2546 0.9169 0.3167 0.076 Uiso 0.566(11) 1 calc PR B 1
C15A C -0.159(2) 1.0387(15) 0.3867(13) 0.056(4) Uani 0.566(11) 1 d PDU B 1
H15A H -0.1988 1.1340 0.3390 0.067 Uiso 0.566(11) 1 calc PR B 1
H15B H -0.0577 1.0369 0.4114 0.067 Uiso 0.566(11) 1 calc PR B 1
C16A C -0.2779(11) 0.9979(11) 0.4892(10) 0.136(4) Uani 0.566(11) 1 d PDU B 1
H16A H -0.2939 1.0660 0.5375 0.204 Uiso 0.566(11) 1 calc PR B 1
H16B H -0.2375 0.9015 0.5327 0.204 Uiso 0.566(11) 1 calc PR B 1
H16C H -0.3770 1.0006 0.4620 0.204 Uiso 0.566(11) 1 calc PR B 1
C11B C 0.1955(7) 0.9288(6) 0.0908(6) 0.0609(17) Uani 0.434(11) 1 d PDU B 2
H11C H 0.1837 0.9053 0.0194 0.073 Uiso 0.434(11) 1 calc PR B 2
H11D H 0.1592 1.0335 0.0801 0.073 Uiso 0.434(11) 1 calc PR B 2
C12B C 0.0819(14) 0.8618(13) 0.1793(10) 0.039(3) Uani 0.434(11) 1 d PDU B 2
H12C H -0.0255 0.8927 0.1564 0.047 Uiso 0.434(11) 1 calc PR B 2
H12D H 0.1118 0.7563 0.1972 0.047 Uiso 0.434(11) 1 calc PR B 2
C13B C 0.101(2) 0.9225(18) 0.2757(13) 0.054(4) Uani 0.434(11) 1 d PDU B 2
H13C H 0.0918 1.0269 0.2486 0.065 Uiso 0.434(11) 1 calc PR B 2
H13D H 0.2061 0.8807 0.3007 0.065 Uiso 0.434(11) 1 calc PR B 2
C14B C -0.0187(18) 0.8941(15) 0.3764(12) 0.063(4) Uani 0.434(11) 1 d PDU B 2
H14C H -0.0370 0.7972 0.3842 0.076 Uiso 0.434(11) 1 calc PR B 2
H14D H 0.0281 0.8928 0.4450 0.076 Uiso 0.434(11) 1 calc PR B 2
C15B C -0.172(3) 0.994(3) 0.375(2) 0.086(9) Uani 0.434(11) 1 d PDU B 2
H15C H -0.2325 0.9729 0.3223 0.103 Uiso 0.434(11) 1 calc PR B 2
H15D H -0.1538 1.0920 0.3422 0.103 Uiso 0.434(11) 1 calc PR B 2
C16B C -0.2779(11) 0.9979(11) 0.4892(10) 0.136(4) Uani 0.434(11) 1 d PDU B 2
H16D H -0.3736 1.0705 0.4748 0.204 Uiso 0.434(11) 1 calc PR B 2
H16E H -0.2220 1.0212 0.5427 0.204 Uiso 0.434(11) 1 calc PR B 2
H16F H -0.3040 0.9042 0.5211 0.204 Uiso 0.434(11) 1 calc PR B 2
C1H C 0.4994(10) 0.6273(9) 0.4100(8) 0.093(3) Uani 1 1 d . . .
H1H1 H 0.5367 0.5859 0.3432 0.112 Uiso 1 1 calc R . .
H1H2 H 0.4793 0.7326 0.3845 0.112 Uiso 1 1 calc R . .
C2H C 0.3483(10) 0.5794(10) 0.4679(9) 0.114(4) Uani 1 1 d . . .
H2H1 H 0.3090 0.6240 0.5328 0.137 Uiso 1 1 calc R . .
H2H2 H 0.2678 0.6104 0.4138 0.137 Uiso 1 1 calc R . .
C3H C 0.3802(11) 0.4223(10) 0.5073(6) 0.088(3) Uani 1 1 d . . .
H3H1 H 0.4168 0.3781 0.4418 0.105 Uiso 1 1 calc R . .
H3H2 H 0.2831 0.3916 0.5433 0.105 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0458(4) 0.0868(5) 0.0493(4) 0.0005(3) -0.0171(3) 0.0024(3)
O1 0.050(2) 0.035(2) 0.045(2) 0.0007(16) -0.0032(17) -0.0026(17)
O2 0.048(2) 0.033(2) 0.054(2) -0.0101(17) 0.0019(17) -0.0084(17)
O3 0.036(2) 0.035(2) 0.066(3) -0.0052(17) -0.0009(18) -0.0067(17)
N1 0.029(2) 0.039(2) 0.039(2) -0.0034(19) -0.0039(18) -0.0097(18)
N2 0.034(3) 0.028(2) 0.051(3) 0.0016(18) 0.006(2) 0.0010(18)
C4 0.030(3) 0.041(3) 0.034(3) 0.004(2) -0.001(2) -0.005(2)
C5 0.031(3) 0.028(3) 0.047(3) 0.000(2) 0.001(2) 0.001(2)
C6 0.033(3) 0.030(3) 0.043(3) -0.010(2) 0.006(2) -0.010(2)
C1 0.022(3) 0.029(2) 0.034(3) -0.002(2) 0.0012(19) -0.0065(19)
C2 0.024(3) 0.028(2) 0.032(2) 0.0003(19) 0.0029(19) -0.0060(19)
C3 0.028(3) 0.038(3) 0.035(3) -0.008(2) 0.001(2) -0.008(2)
C7 0.031(3) 0.048(3) 0.034(3) 0.002(2) 0.004(2) -0.005(2)
C8 0.045(4) 0.082(4) 0.041(3) -0.001(3) -0.011(3) -0.012(3)
C9 0.041(3) 0.030(3) 0.031(3) -0.001(2) 0.004(2) -0.005(2)
C10 0.032(3) 0.033(3) 0.033(3) 0.001(2) 0.005(2) -0.001(2)
C11A 0.030(3) 0.043(3) 0.081(4) 0.015(3) 0.009(3) 0.006(2)
C12A 0.042(6) 0.053(7) 0.056(7) 0.011(7) 0.012(6) -0.014(5)
C13A 0.042(6) 0.053(6) 0.065(6) -0.011(5) 0.006(5) -0.012(5)
C14A 0.050(7) 0.071(8) 0.065(7) -0.015(6) 0.006(5) -0.009(6)
C15A 0.036(7) 0.057(8) 0.068(7) 0.001(6) -0.004(5) -0.012(6)
C16A 0.059(6) 0.139(8) 0.141(8) 0.028(6) 0.039(5) 0.015(5)
C11B 0.030(3) 0.043(3) 0.081(4) 0.015(3) 0.009(3) 0.006(2)
C12B 0.032(7) 0.030(6) 0.060(7) -0.007(5) -0.008(5) -0.017(5)
C13B 0.056(8) 0.036(7) 0.066(8) -0.006(8) 0.005(7) -0.013(6)
C14B 0.069(9) 0.057(8) 0.060(8) -0.008(6) -0.002(7) -0.016(7)
C15B 0.065(12) 0.072(14) 0.107(14) 0.000(12) 0.009(11) -0.021(10)
C16B 0.059(6) 0.139(8) 0.141(8) 0.028(6) 0.039(5) 0.015(5)
C1H 0.090(6) 0.081(5) 0.091(6) 0.009(4) -0.001(5) -0.021(5)
C2H 0.059(5) 0.108(7) 0.130(8) 0.036(6) 0.008(5) -0.009(5)
C3H 0.115(7) 0.135(7) 0.038(4) -0.017(4) 0.006(4) -0.085(6)

_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 C4 1.908(5) . ?
O1 C7 1.228(6) . ?
O2 C9 1.217(6) . ?
O3 C10 1.231(6) . ?
N1 C7 1.354(7) . ?
N1 C1 1.411(6) . ?
N1 H1N 0.8800 . ?
N2 C10 1.328(6) . ?
N2 C11A 1.443(7) . ?
N2 H2N 0.8800 . ?
C4 C5 1.375(7) . ?
C4 C3 1.383(7) . ?
C5 C6 1.380(7) . ?
C5 H5 0.9500 . ?
C6 C1 1.398(6) . ?
C6 H6 0.9500 . ?
C1 C2 1.403(7) . ?
C2 C3 1.383(7) . ?
C2 C9 1.488(7) . ?
C3 H3 0.9500 . ?
C7 C8 1.495(8) . ?
C8 H83 0.9800 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C9 C10 1.533(7) . ?
C11A C12A 1.588(13) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.481(14) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.485(14) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.485(19) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.557(15) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C12B C13B 1.505(16) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.524(17) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.48(2) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H151 0.9900 . ?
C15B H152 0.9900 . ?
C1H C3H 1.495(11) 2_666 ?
C1H C2H 1.547(11) . ?
C1H H1H1 0.9900 . ?
C1H H1H2 0.9900 . ?
C2H C3H 1.477(12) . ?
C2H H2H1 0.9900 . ?
C2H H2H2 0.9900 . ?
C3H C1H 1.495(11) 2_666 ?
C3H H3H1 0.9900 . ?
C3H H3H2 0.9900 . ?

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 C1 125.3(4) . . ?
C7 N1 H1N 117.4 . . ?
C1 N1 H1N 117.4 . . ?
C10 N2 C11A 122.5(5) . . ?
C10 N2 H2N 118.8 . . ?
C11A N2 H2N 118.8 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 Br1 119.8(4) . . ?
C3 C4 Br1 118.8(4) . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 122.0(4) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C6 C1 C2 118.8(4) . . ?
C6 C1 N1 116.9(4) . . ?
C2 C1 N1 124.2(4) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 C9 114.5(4) . . ?
C1 C2 C9 126.6(4) . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O1 C7 N1 121.9(5) . . ?
O1 C7 C8 121.9(5) . . ?
N1 C7 C8 116.2(5) . . ?
C7 C8 H83 109.5 . . ?
C7 C8 H81 109.5 . . ?
H83 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H83 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
O2 C9 C2 121.5(5) . . ?
O2 C9 C10 119.1(4) . . ?
C2 C9 C10 118.9(4) . . ?
O3 C10 N2 124.3(5) . . ?
O3 C10 C9 121.6(4) . . ?
N2 C10 C9 114.1(4) . . ?
N2 C11A C12A 105.9(7) . . ?
N2 C11A H11A 110.6 . . ?
C12A C11A H11A 110.6 . . ?
N2 C11A H11B 110.6 . . ?
C12A C11A H11B 110.6 . . ?
H11A C11A H11B 108.7 . . ?
C13A C12A C11A 111.0(9) . . ?
C13A C12A H12A 109.4 . . ?
C11A C12A H12A 109.4 . . ?
C13A C12A H12B 109.4 . . ?
C11A C12A H12B 109.4 . . ?
H12A C12A H12B 108.0 . . ?
C12A C13A C14A 116.8(10) . . ?
C12A C13A H13A 108.1 . . ?
C14A C13A H13A 108.1 . . ?
C12A C13A H13B 108.1 . . ?
C14A C13A H13B 108.1 . . ?
H13A C13A H13B 107.3 . . ?
C13A C14A C15A 112.7(11) . . ?
C13A C14A H14A 109.1 . . ?
C15A C14A H14A 109.1 . . ?
C13A C14A H14B 109.1 . . ?
C15A C14A H14B 109.1 . . ?
H14A C14A H14B 107.8 . . ?
C14A C15A C16A 101.2(12) . . ?
C14A C15A H15A 111.5 . . ?
C16A C15A H15A 111.5 . . ?
C14A C15A H15B 111.5 . . ?
C16A C15A H15B 111.5 . . ?
H15A C15A H15B 109.3 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C13B C12B H12C 111.9 . . ?
C13B C12B H12D 111.9 . . ?
H12C C12B H12D 109.6 . . ?
C12B C13B C14B 113.4(12) . . ?
C12B C13B H13C 108.9 . . ?
C14B C13B H13C 108.9 . . ?
C12B C13B H13D 108.9 . . ?
C14B C13B H13D 108.9 . . ?
H13C C13B H13D 107.7 . . ?
C15B C14B C13B 117.9(14) . . ?
C15B C14B H14C 107.8 . . ?
C13B C14B H14C 107.8 . . ?
C15B C14B H14D 107.8 . . ?
C13B C14B H14D 107.8 . . ?
H14C C14B H14D 107.2 . . ?
C14B C15B H151 107.5 . . ?
C14B C15B H152 107.5 . . ?
H151 C15B H152 107.0 . . ?
C3H C1H C2H 108.8(7) 2_666 . ?
C3H C1H H1H1 109.9 2_666 . ?
C2H C1H H1H1 109.9 . . ?
C3H C1H H1H2 109.9 2_666 . ?
C2H C1H H1H2 109.9 . . ?
H1H1 C1H H1H2 108.3 . . ?
C3H C2H C1H 109.5(7) . . ?
C3H C2H H2H1 109.8 . . ?
C1H C2H H2H1 109.8 . . ?
C3H C2H H2H2 109.8 . . ?
C1H C2H H2H2 109.8 . . ?
H2H1 C2H H2H2 108.2 . . ?
C2H C3H C1H 110.8(7) . 2_666 ?
C2H C3H H3H1 109.5 . . ?
C1H C3H H3H1 109.5 2_666 . ?
C2H C3H H3H2 109.5 . . ?
C1H C3H H3H2 109.5 2_666 . ?
H3H1 C3H H3H2 108.1 . . ?

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
C3 C4 C5 C6 1.0(7) . . . . ?
Br1 C4 C5 C6 -178.6(4) . . . . ?
C4 C5 C6 C1 -1.7(7) . . . . ?
C5 C6 C1 C2 0.1(7) . . . . ?
C5 C6 C1 N1 178.8(4) . . . . ?
C7 N1 C1 C6 -143.7(5) . . . . ?
C7 N1 C1 C2 34.9(7) . . . . ?
C6 C1 C2 C3 2.1(7) . . . . ?
N1 C1 C2 C3 -176.5(4) . . . . ?
C6 C1 C2 C9 -175.8(4) . . . . ?
N1 C1 C2 C9 5.7(7) . . . . ?
C5 C4 C3 C2 1.2(7) . . . . ?
Br1 C4 C3 C2 -179.2(3) . . . . ?
C1 C2 C3 C4 -2.7(7) . . . . ?
C9 C2 C3 C4 175.4(4) . . . . ?
C1 N1 C7 O1 -0.5(8) . . . . ?
C1 N1 C7 C8 179.7(5) . . . . ?
C3 C2 C9 O2 39.3(6) . . . . ?
C1 C2 C9 O2 -142.8(5) . . . . ?
C3 C2 C9 C10 -132.7(5) . . . . ?
C1 C2 C9 C10 45.2(6) . . . . ?
C11A N2 C10 O3 -2.6(8) . . . . ?
C11A N2 C10 C9 179.8(5) . . . . ?
O2 C9 C10 O3 -161.5(5) . . . . ?
C2 C9 C10 O3 10.7(7) . . . . ?
O2 C9 C10 N2 16.2(6) . . . . ?
C2 C9 C10 N2 -171.7(4) . . . . ?
C10 N2 C11A C12A 95.1(8) . . . . ?
N2 C11A C12A C13A -177.7(9) . . . . ?
C11A C12A C13A C14A 170.7(10) . . . . ?
C12A C13A C14A C15A 74.1(16) . . . . ?
C13A C14A C15A C16A 171.9(11) . . . . ?
C12B C13B C14B C15B -85(2) . . . . ?
C3H C1H C2H C3H -58.7(11) 2_666 . . . ?
C1H C2H C3H C1H 59.9(11) . . . 2_666 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.091


data_inp1bar_2
_database_code_depnum_ccdc_archive 'CCDC 887278'
#TrackingRef 'Venty5b2_3_18Oct11_Deposition.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 Br N2 O3'
_chemical_formula_weight         369.26

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

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

_cell_length_a                   8.5713(11)
_cell_length_b                   9.9041(11)
_cell_length_c                   11.2296(14)
_cell_angle_alpha                97.717(4)
_cell_angle_beta                 108.250(4)
_cell_angle_gamma                101.874(4)
_cell_volume                     865.48(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4588
_cell_measurement_theta_min      2.594
_cell_measurement_theta_max      16.145

_exptl_crystal_description       Plates
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    2.388
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_T_max  0.9022
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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 kappa APEXII CCD Diffractometer'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11690
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3012
_reflns_number_gt                2430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       '<i>APEX2 </i>(Bruker, 2007)'
_computing_cell_refinement       '<i>APEX2 </i>(Bruker, 2007)'
_computing_data_reduction        '<i>APEX2 </i>(Bruker, 2007)'
_computing_structure_solution    '<i>SHELXS-97</i> (Sheldrick, 2008)'
_computing_structure_refinement  '<i>SHELXL-97</i> (Sheldrick, 2008)'
_computing_molecular_graphics    '<i>SHELXTL-Plus</i> (Sheldrick, 2008)'


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

Atoms in the flexible side chains exhibit disorder, which is modelled over
two positions of almost equal occupancies (51:49). The start and the end
atoms are not affected by this disorder, but the atoms along the chain,
C12, C13, C14 and C15 are influenced to a varying degree.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4403P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     228
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.915
_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
C12B C 0.5019(5) 0.5338(5) 0.2873(5) 0.0604(11) Uani 0.489(10) 1 d PDU A 2
H12C H 0.4122 0.5581 0.3174 0.073 Uiso 0.489(10) 1 calc PR A 2
H12D H 0.5420 0.6105 0.2472 0.073 Uiso 0.489(10) 1 calc PR A 2
C13B C 0.4259(13) 0.4027(8) 0.1892(10) 0.0623(17) Uani 0.489(10) 1 d PDU A 2
H13C H 0.3798 0.3242 0.2251 0.075 Uiso 0.489(10) 1 calc PR A 2
H13D H 0.5112 0.3768 0.1546 0.075 Uiso 0.489(10) 1 calc PR A 2
C14B C 0.2817(11) 0.4352(9) 0.0838(8) 0.046(3) Uani 0.489(10) 1 d PD A 2
H14C H 0.1920 0.4520 0.1174 0.055 Uiso 0.489(10) 1 calc PR A 2
H14D H 0.3271 0.5212 0.0565 0.055 Uiso 0.489(10) 1 calc PR A 2
C15B C 0.2069(12) 0.3088(9) -0.0308(8) 0.054(3) Uani 0.489(10) 1 d PD A 2
H15C H 0.1312 0.3334 -0.1067 0.065 Uiso 0.489(10) 1 calc PR A 2
H15D H 0.2985 0.2777 -0.0535 0.065 Uiso 0.489(10) 1 calc PR A 2
C16B C 0.1064(8) 0.1935(6) 0.0147(6) 0.0828(17) Uani 0.489(10) 1 d PD A 2
H16D H 0.0538 0.1086 -0.0542 0.124 Uiso 0.489(10) 1 calc PR A 2
H16E H 0.0174 0.2268 0.0377 0.124 Uiso 0.489(10) 1 calc PR A 2
H16F H 0.1834 0.1711 0.0900 0.124 Uiso 0.489(10) 1 calc PR A 2
Br1 Br 1.43751(5) 0.91846(5) 0.11427(4) 0.0483(2) Uani 1 1 d . . .
O1 O 1.1798(3) 0.7306(2) 0.5995(2) 0.0292(5) Uani 1 1 d . . .
O2 O 1.0955(3) 0.5563(2) 0.3251(2) 0.0302(6) Uani 1 1 d . . .
O3 O 0.8438(3) 0.7771(2) 0.3706(2) 0.0301(5) Uani 1 1 d . . .
N1 N 1.1736(3) 0.9461(3) 0.5579(3) 0.0243(6) Uani 1 1 d . . .
H1N H 1.1518 1.0262 0.5823 0.029 Uiso 1 1 calc R . .
N2 N 0.8085(3) 0.5462(3) 0.3795(3) 0.0239(6) Uani 1 1 d . A .
H2N H 0.8500 0.4725 0.3723 0.029 Uiso 1 1 calc R . .
C4 C 1.3494(4) 0.9266(4) 0.2501(3) 0.0310(8) Uani 1 1 d . . .
C5 C 1.3872(4) 1.0529(4) 0.3359(3) 0.0316(8) Uani 1 1 d . . .
H5 H 1.4544 1.1370 0.3262 0.038 Uiso 1 1 calc R . .
C6 C 1.3259(4) 1.0551(3) 0.4353(3) 0.0278(7) Uani 1 1 d . . .
H6 H 1.3536 1.1413 0.4954 0.033 Uiso 1 1 calc R . .
C1 C 1.2238(4) 0.9334(3) 0.4506(3) 0.0224(7) Uani 1 1 d . . .
C2 C 1.1827(4) 0.8059(3) 0.3606(3) 0.0232(7) Uani 1 1 d . . .
C3 C 1.2502(4) 0.8048(3) 0.2629(3) 0.0259(7) Uani 1 1 d . . .
H3 H 1.2275 0.7187 0.2040 0.031 Uiso 1 1 calc R . .
C7 C 1.1554(4) 0.8468(3) 0.6275(3) 0.0246(7) Uani 1 1 d . . .
C8 C 1.1006(5) 0.8852(4) 0.7391(4) 0.0367(8) Uani 1 1 d . . .
H83 H 0.9859 0.8264 0.7223 0.055 Uiso 1 1 calc R . .
H82 H 1.1001 0.9849 0.7511 0.055 Uiso 1 1 calc R . .
H81 H 1.1801 0.8693 0.8169 0.055 Uiso 1 1 calc R . .
C9 C 1.0665(4) 0.6686(3) 0.3550(3) 0.0217(7) Uani 1 1 d . . .
C10 C 0.8940(4) 0.6688(3) 0.3701(3) 0.0218(7) Uani 1 1 d . . .
C11 C 0.6473(4) 0.5293(4) 0.4012(4) 0.0381(9) Uani 1 1 d . . .
H11A H 0.6612 0.6052 0.4738 0.046 Uiso 1 1 calc R A 1
H11B H 0.6193 0.4379 0.4265 0.046 Uiso 1 1 calc R A 1
C12A C 0.5019(5) 0.5338(5) 0.2873(5) 0.0604(11) Uani 0.511(10) 1 d PDU A 1
H12A H 0.5226 0.6286 0.2670 0.073 Uiso 0.511(10) 1 calc PR A 1
H12B H 0.3957 0.5161 0.3071 0.073 Uiso 0.511(10) 1 calc PR A 1
C13A C 0.4817(13) 0.4206(9) 0.1700(8) 0.0628(16) Uani 0.511(10) 1 d PDU A 1
H13A H 0.4527 0.3276 0.1923 0.075 Uiso 0.511(10) 1 calc PR A 1
H13B H 0.5955 0.4328 0.1625 0.075 Uiso 0.511(10) 1 calc PR A 1
C14A C 0.3520(11) 0.4098(14) 0.0321(10) 0.072(4) Uani 0.511(10) 1 d PD A 1
H14A H 0.3688 0.5040 0.0102 0.086 Uiso 0.511(10) 1 calc PR A 1
H14B H 0.3753 0.3448 -0.0313 0.086 Uiso 0.511(10) 1 calc PR A 1
C15A C 0.1665(11) 0.3564(9) 0.0226(11) 0.074(4) Uani 0.511(10) 1 d PD A 1
H15A H 0.0918 0.3797 -0.0545 0.089 Uiso 0.511(10) 1 calc PR A 1
H15B H 0.1516 0.4079 0.0984 0.089 Uiso 0.511(10) 1 calc PR A 1
C16A C 0.1064(8) 0.1935(6) 0.0147(6) 0.0828(17) Uani 0.511(10) 1 d PD A 1
H16A H -0.0119 0.1688 0.0113 0.124 Uiso 0.511(10) 1 calc PR A 1
H16B H 0.1791 0.1690 0.0907 0.124 Uiso 0.511(10) 1 calc PR A 1
H16C H 0.1143 0.1411 -0.0627 0.124 Uiso 0.511(10) 1 calc PR A 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C12B 0.0269(19) 0.052(2) 0.096(3) 0.0396(19) 0.009(2) 0.0013(16)
C13B 0.029(3) 0.052(3) 0.095(4) 0.039(2) 0.007(3) -0.002(2)
C14B 0.036(6) 0.059(6) 0.056(6) 0.024(5) 0.025(5) 0.019(5)
C15B 0.044(6) 0.091(8) 0.021(5) -0.006(5) 0.018(4) 0.008(5)
C16B 0.067(4) 0.095(4) 0.071(4) 0.022(3) 0.011(3) 0.006(3)
Br1 0.0389(3) 0.0732(4) 0.0386(3) 0.0239(2) 0.0229(2) 0.0048(2)
O1 0.0372(14) 0.0245(12) 0.0294(13) 0.0108(10) 0.0137(11) 0.0094(10)
O2 0.0292(13) 0.0240(12) 0.0434(15) 0.0072(10) 0.0196(11) 0.0090(10)
O3 0.0269(13) 0.0203(12) 0.0457(15) 0.0086(10) 0.0139(11) 0.0088(9)
N1 0.0243(14) 0.0220(13) 0.0295(15) 0.0066(11) 0.0102(12) 0.0104(11)
N2 0.0190(14) 0.0221(14) 0.0336(16) 0.0105(11) 0.0111(12) 0.0062(11)
C4 0.0193(17) 0.047(2) 0.031(2) 0.0221(16) 0.0098(15) 0.0071(15)
C5 0.0199(17) 0.0346(19) 0.041(2) 0.0201(16) 0.0083(15) 0.0042(14)
C6 0.0217(17) 0.0246(17) 0.036(2) 0.0126(14) 0.0054(15) 0.0058(13)
C1 0.0156(15) 0.0249(16) 0.0282(18) 0.0107(13) 0.0065(13) 0.0072(12)
C2 0.0167(15) 0.0272(17) 0.0268(17) 0.0118(13) 0.0063(13) 0.0062(12)
C3 0.0187(16) 0.0336(18) 0.0244(18) 0.0066(14) 0.0064(14) 0.0061(13)
C7 0.0169(15) 0.0288(18) 0.0262(18) 0.0075(13) 0.0052(13) 0.0048(13)
C8 0.034(2) 0.047(2) 0.031(2) 0.0091(16) 0.0136(17) 0.0108(16)
C9 0.0210(16) 0.0242(17) 0.0203(16) 0.0060(12) 0.0074(13) 0.0058(13)
C10 0.0206(16) 0.0206(16) 0.0219(16) 0.0031(12) 0.0063(13) 0.0034(13)
C11 0.0259(19) 0.041(2) 0.062(3) 0.0273(19) 0.0266(19) 0.0114(16)
C12A 0.0269(19) 0.052(2) 0.096(3) 0.0396(19) 0.009(2) 0.0013(16)
C13A 0.028(3) 0.049(3) 0.097(4) 0.037(2) 0.006(3) -0.006(2)
C14A 0.044(6) 0.101(9) 0.060(7) 0.036(6) 0.006(5) 0.005(6)
C15A 0.041(6) 0.102(9) 0.038(7) 0.008(6) -0.013(5) -0.021(6)
C16A 0.067(4) 0.095(4) 0.071(4) 0.022(3) 0.011(3) 0.006(3)

_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
C12B C13B 1.463(9) . ?
C12B C11 1.494(6) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.543(7) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.534(7) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.528(7) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
Br1 C4 1.902(3) . ?
O1 C7 1.229(4) . ?
O2 C9 1.215(4) . ?
O3 C10 1.235(4) . ?
N1 C7 1.349(4) . ?
N1 C1 1.400(4) . ?
N1 H1N 0.8800 . ?
N2 C10 1.318(4) . ?
N2 C11 1.458(4) . ?
N2 H2N 0.8800 . ?
C4 C3 1.378(5) . ?
C4 C5 1.383(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9500 . ?
C6 C1 1.402(5) . ?
C6 H6 0.9500 . ?
C1 C2 1.411(5) . ?
C2 C3 1.391(5) . ?
C2 C9 1.492(4) . ?
C3 H3 0.9500 . ?
C7 C8 1.500(5) . ?
C8 H83 0.9800 . ?
C8 H82 0.9800 . ?
C8 H81 0.9800 . ?
C9 C10 1.540(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13A C14A 1.573(8) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.533(8) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?

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
C13B C12B C11 115.2(5) . . ?
C13B C12B H12C 108.5 . . ?
C11 C12B H12C 108.5 . . ?
C13B C12B H12D 108.5 . . ?
C11 C12B H12D 108.5 . . ?
H12C C12B H12D 107.5 . . ?
C12B C13B C14B 104.8(7) . . ?
C12B C13B H13C 110.8 . . ?
C14B C13B H13C 110.8 . . ?
C12B C13B H13D 110.8 . . ?
C14B C13B H13D 110.8 . . ?
H13C C13B H13D 108.9 . . ?
C15B C14B C13B 108.7(7) . . ?
C15B C14B H14C 109.9 . . ?
C13B C14B H14C 109.9 . . ?
C15B C14B H14D 109.9 . . ?
C13B C14B H14D 109.9 . . ?
H14C C14B H14D 108.3 . . ?
C16B C15B C14B 104.7(6) . . ?
C16B C15B H15C 110.8 . . ?
C14B C15B H15C 110.8 . . ?
C16B C15B H15D 110.8 . . ?
C14B C15B H15D 110.8 . . ?
H15C C15B H15D 108.9 . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C7 N1 C1 126.0(3) . . ?
C7 N1 H1N 117.0 . . ?
C1 N1 H1N 117.0 . . ?
C10 N2 C11 121.9(3) . . ?
C10 N2 H2N 119.1 . . ?
C11 N2 H2N 119.1 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 Br1 119.1(3) . . ?
C5 C4 Br1 120.2(3) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
N1 C1 C6 117.1(3) . . ?
N1 C1 C2 124.2(3) . . ?
C6 C1 C2 118.7(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C9 114.6(3) . . ?
C1 C2 C9 126.6(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
O1 C7 N1 121.8(3) . . ?
O1 C7 C8 121.9(3) . . ?
N1 C7 C8 116.3(3) . . ?
C7 C8 H83 109.5 . . ?
C7 C8 H82 109.5 . . ?
H83 C8 H82 109.5 . . ?
C7 C8 H81 109.5 . . ?
H83 C8 H81 109.5 . . ?
H82 C8 H81 109.5 . . ?
O2 C9 C2 121.8(3) . . ?
O2 C9 C10 119.1(3) . . ?
C2 C9 C10 118.6(3) . . ?
O3 C10 N2 124.9(3) . . ?
O3 C10 C9 120.5(3) . . ?
N2 C10 C9 114.6(3) . . ?
N2 C11 C12B 113.9(3) . . ?
N2 C11 H11A 108.8 . . ?
C12B C11 H11A 108.8 . . ?
N2 C11 H11B 108.8 . . ?
C12B C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C14A C13A H13A 106.8 . . ?
C14A C13A H13B 106.8 . . ?
H13A C13A H13B 106.6 . . ?
C15A C14A C13A 112.2(9) . . ?
C15A C14A H14A 109.2 . . ?
C13A C14A H14A 109.2 . . ?
C15A C14A H14B 109.2 . . ?
C13A C14A H14B 109.2 . . ?
H14A C14A H14B 107.9 . . ?
C14A C15A H15A 108.6 . . ?
C14A C15A H15B 108.6 . . ?
H15A C15A H15B 107.6 . . ?

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
C11 C12B C13B C14B -179.8(6) . . . . ?
C12B C13B C14B C15B 173.7(8) . . . . ?
C13B C14B C15B C16B 72.2(10) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
Br1 C4 C5 C6 -178.1(2) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C7 N1 C1 C6 -144.2(3) . . . . ?
C7 N1 C1 C2 33.6(5) . . . . ?
C5 C6 C1 N1 177.7(3) . . . . ?
C5 C6 C1 C2 -0.3(5) . . . . ?
N1 C1 C2 C3 -175.5(3) . . . . ?
C6 C1 C2 C3 2.3(4) . . . . ?
N1 C1 C2 C9 6.8(5) . . . . ?
C6 C1 C2 C9 -175.4(3) . . . . ?
C5 C4 C3 C2 1.2(5) . . . . ?
Br1 C4 C3 C2 -179.8(2) . . . . ?
C1 C2 C3 C4 -2.8(5) . . . . ?
C9 C2 C3 C4 175.2(3) . . . . ?
C1 N1 C7 O1 -1.4(5) . . . . ?
C1 N1 C7 C8 179.8(3) . . . . ?
C3 C2 C9 O2 39.3(4) . . . . ?
C1 C2 C9 O2 -143.0(3) . . . . ?
C3 C2 C9 C10 -132.5(3) . . . . ?
C1 C2 C9 C10 45.2(4) . . . . ?
C11 N2 C10 O3 -4.7(5) . . . . ?
C11 N2 C10 C9 176.6(3) . . . . ?
O2 C9 C10 O3 -163.0(3) . . . . ?
C2 C9 C10 O3 9.0(4) . . . . ?
O2 C9 C10 N2 15.7(4) . . . . ?
C2 C9 C10 N2 -172.3(3) . . . . ?
C10 N2 C11 C12B 72.4(4) . . . . ?
C13B C12B C11 N2 79.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.070


data_venty3a_pc
_database_code_depnum_ccdc_archive 'CCDC 887279'
#TrackingRef 'Venty_5d_3a_Deposition_16May12.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H34 N2 O3'
_chemical_formula_sum            'C23 H34 N2 O3'
_chemical_formula_weight         374.51

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

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                   24.240(5)
_cell_length_b                   5.0210(10)
_cell_length_c                   17.387(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.28(3)
_cell_angle_gamma                90.00
_cell_volume                     2115.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      22.5

_exptl_crystal_description       'Thin plates'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816.0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9924
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Synchrotron BM'
_diffrn_radiation_monochromator  Si<111>
_diffrn_measurement_device_type  '3-BM1 Australian Synchrotron'
_diffrn_measurement_method       '\f scans'
_diffrn_detector_area_resol_mean 'ADSC Q210'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24994
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3480
_reflns_number_gt                3413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BLU-ICE (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;ORTEP-3 (Farrugia, 1997)
WINGX-32 (Farrugia, 1999)
;

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

Alert level A '_diffrn_measured_fraction_theta_full Low 0.939' arises because
the data collection at the synchrotron beam line is carried out
on one circle goniometer, which leaves gaps in the reciprocal space.

The alkyl side chain exhibits orientational disorder over two almost equally
populated sites. The end atoms C11 and C22 are not affected by this disorder,
but atoms C12 - C21 are influcenced in a gradually decreasing manner.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1765P)^2^+25.7773P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     300
_refine_ls_number_restraints     356
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.1295
_refine_ls_wR_factor_ref         0.4101
_refine_ls_wR_factor_gt          0.4097
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.009
_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 0.4390(2) 0.6581(11) 0.5592(2) 0.0318(12) Uani 1 1 d . . .
O2 O 0.33279(16) 0.2298(8) 0.3488(2) 0.0182(10) Uani 1 1 d . . .
O3 O 0.29039(18) 0.6851(9) 0.2141(3) 0.0251(11) Uani 1 1 d . . .
N1 N 0.39859(19) 0.4678(11) 0.4523(3) 0.0190(12) Uani 1 1 d . . .
H1 H 0.3783 0.3350 0.4385 0.023 Uiso 1 1 calc R . .
N2 N 0.28041(19) 0.2376(10) 0.2113(3) 0.0153(11) Uani 1 1 d . B .
H2 H 0.2913 0.0882 0.2305 0.018 Uiso 1 1 calc R . .
C1 C 0.4146(2) 0.6387(13) 0.3924(3) 0.0170(13) Uani 1 1 d . . .
C2 C 0.3883(2) 0.6076(12) 0.3193(3) 0.0156(12) Uani 1 1 d . . .
C3 C 0.4065(2) 0.7641(12) 0.2581(3) 0.0162(13) Uani 1 1 d . . .
H3 H 0.3904 0.7422 0.2095 0.019 Uiso 1 1 calc R . .
C4 C 0.4480(2) 0.9501(13) 0.2686(3) 0.0198(13) Uani 1 1 d . . .
H4 H 0.4600 1.0509 0.2274 0.024 Uiso 1 1 calc R . .
C5 C 0.4714(2) 0.9849(13) 0.3414(3) 0.0207(13) Uani 1 1 d . . .
H5 H 0.4985 1.1143 0.3489 0.025 Uiso 1 1 calc R . .
C6 C 0.4555(2) 0.8317(13) 0.4030(3) 0.0188(13) Uani 1 1 d . . .
H6 H 0.4720 0.8571 0.4513 0.023 Uiso 1 1 calc R . .
C7 C 0.4109(2) 0.4841(14) 0.5290(3) 0.0207(14) Uani 1 1 d . . .
C8 C 0.3858(3) 0.2633(14) 0.5752(3) 0.0265(15) Uani 1 1 d . . .
H83 H 0.4138 0.1349 0.5886 0.040 Uiso 1 1 calc R . .
H81 H 0.3571 0.1785 0.5452 0.040 Uiso 1 1 calc R . .
H82 H 0.3707 0.3356 0.6213 0.040 Uiso 1 1 calc R . .
C9 C 0.3429(2) 0.4150(12) 0.3067(3) 0.0158(12) Uani 1 1 d . . .
C10 C 0.3024(2) 0.4621(12) 0.2383(3) 0.0161(12) Uani 1 1 d . . .
C11 C 0.2387(2) 0.2378(10) 0.1506(3) 0.0134(10) Uani 1 1 d DU . .
H11A H 0.2327 0.0559 0.1336 0.016 Uiso 1 1 calc R A 1
H11B H 0.2524 0.3378 0.1073 0.016 Uiso 1 1 calc R A 1
C12A C 0.1844(3) 0.354(2) 0.1733(5) 0.0134(11) Uani 0.496(7) 1 d PDU B 1
H12A H 0.1897 0.5438 0.1813 0.016 Uiso 0.496(7) 1 calc PR B 1
H12B H 0.1588 0.3339 0.1300 0.016 Uiso 0.496(7) 1 calc PR B 1
C12B C 0.1850(3) 0.123(2) 0.1748(5) 0.0133(11) Uani 0.504(7) 1 d PDU B 2
H12C H 0.1594 0.1327 0.1312 0.016 Uiso 0.504(7) 1 calc PR B 2
H12D H 0.1908 -0.0642 0.1861 0.016 Uiso 0.504(7) 1 calc PR B 2
C13 C 0.1579(2) 0.2456(11) 0.2419(3) 0.0171(12) Uani 1 1 d DU . .
H13A H 0.1816 0.2838 0.2863 0.020 Uiso 1 1 calc R B 1
H13B H 0.1561 0.0535 0.2366 0.020 Uiso 1 1 calc R B 1
C14A C 0.1016(3) 0.343(3) 0.2587(5) 0.022(2) Uani 0.496(7) 1 d PDU B 1
H14A H 0.1036 0.5361 0.2616 0.026 Uiso 0.496(7) 1 calc PR B 1
H14B H 0.0781 0.3007 0.2145 0.026 Uiso 0.496(7) 1 calc PR B 1
C14B C 0.1019(3) 0.149(2) 0.2594(5) 0.019(2) Uani 0.504(7) 1 d PDU B 2
H14C H 0.1040 -0.0429 0.2643 0.022 Uiso 0.504(7) 1 calc PR B 2
H14D H 0.0785 0.1862 0.2147 0.022 Uiso 0.504(7) 1 calc PR B 2
C15 C 0.0730(2) 0.2507(13) 0.3274(3) 0.0217(13) Uani 1 1 d DU . .
H15A H 0.0957 0.2998 0.3719 0.026 Uiso 1 1 calc R B 1
H15B H 0.0722 0.0576 0.3256 0.026 Uiso 1 1 calc R B 1
C16A C 0.0162(3) 0.343(3) 0.3417(5) 0.020(2) Uani 0.496(7) 1 d PDU B 1
H16A H 0.0172 0.5359 0.3434 0.024 Uiso 0.496(7) 1 calc PR B 1
H16B H -0.0063 0.2938 0.2971 0.024 Uiso 0.496(7) 1 calc PR B 1
C16B C 0.0166(3) 0.157(3) 0.3418(5) 0.020(2) Uani 0.504(7) 1 d PDU B 2
H16C H 0.0179 -0.0360 0.3446 0.024 Uiso 0.504(7) 1 calc PR B 2
H16D H -0.0060 0.2022 0.2970 0.024 Uiso 0.504(7) 1 calc PR B 2
C17 C -0.0129(2) 0.2517(12) 0.4103(3) 0.0204(13) Uani 1 1 d DU . .
H17A H 0.0090 0.3052 0.4551 0.024 Uiso 1 1 calc R B 1
H17B H -0.0131 0.0586 0.4094 0.024 Uiso 1 1 calc R B 1
C18A C -0.0701(3) 0.340(3) 0.4226(5) 0.021(2) Uani 0.496(7) 1 d PDU B 1
H18A H -0.0698 0.5336 0.4235 0.025 Uiso 0.496(7) 1 calc PR B 1
H18B H -0.0919 0.2875 0.3778 0.025 Uiso 0.496(7) 1 calc PR B 1
C18B C -0.0695(3) 0.159(3) 0.4227(5) 0.020(2) Uani 0.504(7) 1 d PDU B 2
H18C H -0.0685 -0.0338 0.4244 0.023 Uiso 0.504(7) 1 calc PR B 2
H18D H -0.0914 0.2082 0.3775 0.023 Uiso 0.504(7) 1 calc PR B 2
C19 C -0.0998(2) 0.2506(13) 0.4909(3) 0.0221(14) Uani 1 1 d DU . .
H19A H -0.0800 0.3183 0.5359 0.026 Uiso 1 1 calc R B 1
H19B H -0.0973 0.0579 0.4928 0.026 Uiso 1 1 calc R B 1
C20A C -0.1585(4) 0.323(4) 0.4986(8) 0.030(4) Uani 0.496(7) 1 d PD B 1
H20A H -0.1781 0.2599 0.4529 0.036 Uiso 0.496(7) 1 calc PR B 1
H20B H -0.1609 0.5156 0.4983 0.036 Uiso 0.496(7) 1 calc PR B 1
C20B C -0.1577(4) 0.169(4) 0.4995(7) 0.023(3) Uani 0.504(7) 1 d PD B 2
H20C H -0.1585 -0.0244 0.4994 0.027 Uiso 0.504(7) 1 calc PR B 2
H20D H -0.1779 0.2272 0.4538 0.027 Uiso 0.504(7) 1 calc PR B 2
C21A C -0.1886(4) 0.226(7) 0.5661(11) 0.055(5) Uani 0.496(7) 1 d PDU B 1
H21A H -0.1771 0.0432 0.5749 0.066 Uiso 0.496(7) 1 calc PR B 1
H21B H -0.1753 0.3282 0.6101 0.066 Uiso 0.496(7) 1 calc PR B 1
C21B C -0.1888(4) 0.259(7) 0.5669(11) 0.054(5) Uani 0.504(7) 1 d PDU B 2
H21C H -0.1738 0.1658 0.6115 0.065 Uiso 0.504(7) 1 calc PR B 2
H21D H -0.1806 0.4467 0.5744 0.065 Uiso 0.504(7) 1 calc PR B 2
C22 C -0.2491(3) 0.230(3) 0.5678(5) 0.069(3) Uani 1 1 d DU . .
H22A H -0.2610 0.1573 0.6157 0.104 Uiso 1 1 calc R B 1
H22B H -0.2638 0.1245 0.5260 0.104 Uiso 1 1 calc R B 1
H22C H -0.2620 0.4098 0.5626 0.104 Uiso 1 1 calc R B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.043(3) 0.035(3) 0.017(2) -0.003(2) -0.0074(18) -0.014(2)
O2 0.019(2) 0.016(2) 0.019(2) 0.0030(16) -0.0016(15) -0.0053(16)
O3 0.028(2) 0.013(2) 0.034(2) 0.0015(19) -0.0118(18) -0.0013(18)
N1 0.019(2) 0.020(3) 0.018(2) -0.002(2) -0.0012(18) -0.004(2)
N2 0.015(2) 0.011(3) 0.020(2) -0.0007(18) -0.0011(18) -0.0004(18)
C1 0.015(3) 0.020(3) 0.016(3) -0.005(2) 0.003(2) 0.001(2)
C2 0.013(2) 0.012(3) 0.022(3) 0.000(2) 0.001(2) 0.001(2)
C3 0.018(3) 0.014(3) 0.017(3) -0.001(2) 0.002(2) 0.003(2)
C4 0.016(3) 0.020(4) 0.023(3) 0.000(2) 0.004(2) 0.001(2)
C5 0.015(3) 0.017(3) 0.029(3) -0.002(2) 0.003(2) -0.004(2)
C6 0.019(3) 0.020(3) 0.018(3) -0.008(2) -0.001(2) 0.001(2)
C7 0.018(3) 0.027(4) 0.016(3) -0.001(2) 0.000(2) 0.004(2)
C8 0.028(3) 0.034(4) 0.018(3) 0.003(3) 0.000(2) -0.006(3)
C9 0.016(3) 0.015(3) 0.016(3) -0.006(2) 0.003(2) 0.003(2)
C10 0.013(3) 0.015(3) 0.020(3) -0.001(2) -0.001(2) 0.001(2)
C11 0.019(2) 0.003(2) 0.019(2) 0.0012(16) -0.0029(17) -0.0008(16)
C12A 0.019(2) 0.003(2) 0.019(2) 0.0013(17) -0.0030(18) -0.0005(17)
C12B 0.019(2) 0.003(2) 0.019(2) 0.0011(17) -0.0029(18) -0.0007(17)
C13 0.016(3) 0.015(3) 0.020(3) -0.003(2) -0.002(2) 0.002(2)
C14A 0.022(4) 0.020(5) 0.022(5) 0.001(4) -0.001(4) 0.004(4)
C14B 0.017(4) 0.018(5) 0.021(4) -0.003(4) -0.001(3) 0.002(4)
C15 0.019(3) 0.027(3) 0.020(3) -0.004(2) -0.003(2) 0.003(2)
C16A 0.022(4) 0.018(5) 0.021(4) -0.002(4) -0.001(4) 0.000(4)
C16B 0.020(4) 0.022(5) 0.019(4) -0.001(4) 0.000(3) 0.007(4)
C17 0.018(3) 0.023(3) 0.019(3) -0.003(2) -0.003(2) 0.004(2)
C18A 0.022(4) 0.020(6) 0.020(4) -0.002(4) 0.001(4) -0.003(4)
C18B 0.018(4) 0.022(5) 0.018(4) 0.001(4) 0.002(3) 0.010(4)
C19 0.018(3) 0.030(4) 0.018(3) -0.002(2) -0.002(2) 0.005(2)
C20A 0.033(8) 0.033(11) 0.023(7) 0.010(7) 0.004(5) -0.007(7)
C20B 0.023(7) 0.025(9) 0.021(6) -0.004(6) 0.006(5) -0.001(6)
C21A 0.030(6) 0.100(11) 0.034(8) 0.019(8) 0.012(7) 0.015(8)
C21B 0.029(6) 0.096(11) 0.037(8) -0.007(8) 0.016(7) 0.009(8)
C22 0.038(4) 0.118(8) 0.052(4) -0.004(5) 0.021(3) -0.004(4)

_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 C7 1.220(8) . ?
O2 C9 1.212(7) . ?
O3 C10 1.229(7) . ?
N1 C7 1.362(7) . ?
N1 C1 1.411(8) . ?
N1 H1 0.8600 . ?
N2 C10 1.328(7) . ?
N2 C11 1.445(7) . ?
N2 H2 0.8600 . ?
C1 C6 1.395(8) . ?
C1 C2 1.419(8) . ?
C2 C3 1.401(8) . ?
C2 C9 1.479(8) . ?
C3 C4 1.381(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.505(9) . ?
C8 H83 0.9600 . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C9 C10 1.544(7) . ?
C11 C12B 1.493(6) . ?
C11 C12A 1.501(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12A C13 1.473(6) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12B C13 1.485(6) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13 C14B 1.479(7) . ?
C13 C14A 1.485(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14A C15 1.471(7) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14B C15 1.479(7) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15 C16B 1.474(7) . ?
C15 C16A 1.478(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16A C17 1.473(7) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16B C17 1.481(7) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17 C18B 1.469(7) . ?
C17 C18A 1.476(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18A C19 1.473(7) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18B C19 1.482(7) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19 C20B 1.473(7) . ?
C19 C20A 1.477(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20A C21A 1.477(8) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C20B C21B 1.479(8) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21A C22 1.468(7) . ?
C21A H21A 0.9700 . ?
C21A H21B 0.9700 . ?
C21B C22 1.470(7) . ?
C21B H21C 0.9700 . ?
C21B H21D 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C7 N1 C1 128.9(5) . . ?
C7 N1 H1 115.5 . . ?
C1 N1 H1 115.5 . . ?
C10 N2 C11 121.7(5) . . ?
C10 N2 H2 119.1 . . ?
C11 N2 H2 119.1 . . ?
C6 C1 N1 122.1(5) . . ?
C6 C1 C2 119.9(5) . . ?
N1 C1 C2 118.0(5) . . ?
C3 C2 C1 118.4(5) . . ?
C3 C2 C9 120.1(5) . . ?
C1 C2 C9 121.5(5) . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.5(6) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.6(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O1 C7 N1 124.9(6) . . ?
O1 C7 C8 121.7(5) . . ?
N1 C7 C8 113.3(5) . . ?
C7 C8 H83 109.5 . . ?
C7 C8 H81 109.5 . . ?
H83 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H83 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
O2 C9 C2 124.9(5) . . ?
O2 C9 C10 116.7(5) . . ?
C2 C9 C10 118.2(5) . . ?
O3 C10 N2 124.2(5) . . ?
O3 C10 C9 123.1(5) . . ?
N2 C10 C9 112.6(5) . . ?
N2 C11 C12B 113.2(5) . . ?
N2 C11 C12A 114.3(5) . . ?
C12B C11 C12A 45.7(6) . . ?
N2 C11 H11A 108.7 . . ?
C12B C11 H11A 66.2 . . ?
C12A C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C12B C11 H11B 137.3 . . ?
C12A C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12A C11 118.0(6) . . ?
C13 C12A H12A 107.8 . . ?
C11 C12A H12A 107.8 . . ?
C13 C12A H12B 107.8 . . ?
C11 C12A H12B 107.8 . . ?
H12A C12A H12B 107.1 . . ?
C13 C12B C11 117.7(6) . . ?
C13 C12B H12C 107.9 . . ?
C11 C12B H12C 107.9 . . ?
C13 C12B H12D 107.9 . . ?
C11 C12B H12D 107.9 . . ?
H12C C12B H12D 107.2 . . ?
C12A C13 C14B 134.9(7) . . ?
C12A C13 C14A 117.1(6) . . ?
C14B C13 C14A 38.4(7) . . ?
C12A C13 C12B 46.2(6) . . ?
C14B C13 C12B 116.7(6) . . ?
C14A C13 C12B 135.7(7) . . ?
C12A C13 H13A 108.0 . . ?
C14B C13 H13A 115.6 . . ?
C14A C13 H13A 108.0 . . ?
C12B C13 H13A 116.2 . . ?
C12A C13 H13B 108.0 . . ?
C14B C13 H13B 69.9 . . ?
C14A C13 H13B 108.0 . . ?
C12B C13 H13B 62.1 . . ?
H13A C13 H13B 107.3 . . ?
C15 C14A C13 120.4(7) . . ?
C15 C14A H14A 107.2 . . ?
C13 C14A H14A 107.2 . . ?
C15 C14A H14B 107.2 . . ?
C13 C14A H14B 107.2 . . ?
H14A C14A H14B 106.9 . . ?
C13 C14B C15 120.3(7) . . ?
C13 C14B H14C 107.3 . . ?
C15 C14B H14C 107.3 . . ?
C13 C14B H14D 107.3 . . ?
C15 C14B H14D 107.3 . . ?
H14C C14B H14D 106.9 . . ?
C14A C15 C16B 134.0(7) . . ?
C14A C15 C16A 119.6(6) . . ?
C16B C15 C16A 36.9(7) . . ?
C14A C15 C14B 38.6(7) . . ?
C16B C15 C14B 118.9(6) . . ?
C16A C15 C14B 134.5(7) . . ?
C14A C15 H15A 107.4 . . ?
C16B C15 H15A 117.2 . . ?
C16A C15 H15A 107.4 . . ?
C14B C15 H15A 117.2 . . ?
C14A C15 H15B 107.4 . . ?
C16B C15 H15B 70.6 . . ?
C16A C15 H15B 107.4 . . ?
C14B C15 H15B 68.8 . . ?
H15A C15 H15B 107.0 . . ?
C17 C16A C15 120.2(7) . . ?
C17 C16A H16A 107.3 . . ?
C15 C16A H16A 107.3 . . ?
C17 C16A H16B 107.3 . . ?
C15 C16A H16B 107.3 . . ?
H16A C16A H16B 106.9 . . ?
C15 C16B C17 120.0(7) . . ?
C15 C16B H16C 107.3 . . ?
C17 C16B H16C 107.3 . . ?
C15 C16B H16D 107.3 . . ?
C17 C16B H16D 107.3 . . ?
H16C C16B H16D 106.9 . . ?
C18B C17 C16A 133.1(7) . . ?
C18B C17 C18A 36.0(7) . . ?
C16A C17 C18A 119.5(6) . . ?
C18B C17 C16B 119.0(6) . . ?
C16A C17 C16B 36.9(7) . . ?
C18A C17 C16B 133.2(7) . . ?
C18B C17 H17A 117.8 . . ?
C16A C17 H17A 107.4 . . ?
C18A C17 H17A 107.4 . . ?
C16B C17 H17A 117.9 . . ?
C18B C17 H17B 71.5 . . ?
C16A C17 H17B 107.4 . . ?
C18A C17 H17B 107.4 . . ?
C16B C17 H17B 70.6 . . ?
H17A C17 H17B 107.0 . . ?
C19 C18A C17 120.1(7) . . ?
C19 C18A H18A 107.3 . . ?
C17 C18A H18A 107.3 . . ?
C19 C18A H18B 107.3 . . ?
C17 C18A H18B 107.3 . . ?
H18A C18A H18B 106.9 . . ?
C17 C18B C19 120.0(7) . . ?
C17 C18B H18C 107.3 . . ?
C19 C18B H18C 107.3 . . ?
C17 C18B H18D 107.3 . . ?
C19 C18B H18D 107.3 . . ?
H18C C18B H18D 106.9 . . ?
C18A C19 C20B 130.6(8) . . ?
C18A C19 C20A 119.1(7) . . ?
C20B C19 C20A 30.4(7) . . ?
C18A C19 C18B 35.9(7) . . ?
C20B C19 C18B 119.0(7) . . ?
C20A C19 C18B 130.1(8) . . ?
C18A C19 H19A 107.5 . . ?
C20B C19 H19A 118.1 . . ?
C20A C19 H19A 107.5 . . ?
C18B C19 H19A 120.6 . . ?
C18A C19 H19B 107.5 . . ?
C20B C19 H19B 77.1 . . ?
C20A C19 H19B 107.5 . . ?
C18B C19 H19B 71.7 . . ?
H19A C19 H19B 107.0 . . ?
C19 C20A C21A 119.0(10) . . ?
C19 C20A H20A 107.6 . . ?
C21A C20A H20A 107.6 . . ?
C19 C20A H20B 107.6 . . ?
C21A C20A H20B 107.6 . . ?
H20A C20A H20B 107.0 . . ?
C19 C20B C21B 119.9(9) . . ?
C19 C20B H20C 107.4 . . ?
C21B C20B H20C 107.4 . . ?
C19 C20B H20D 107.4 . . ?
C21B C20B H20D 107.4 . . ?
H20C C20B H20D 106.9 . . ?
C22 C21A C20A 121.5(12) . . ?
C22 C21A H21A 107.0 . . ?
C20A C21A H21A 107.0 . . ?
C22 C21A H21B 107.0 . . ?
C20A C21A H21B 107.0 . . ?
H21A C21A H21B 106.7 . . ?
C22 C21B C20B 120.1(11) . . ?
C22 C21B H21C 107.3 . . ?
C20B C21B H21C 107.3 . . ?
C22 C21B H21D 107.3 . . ?
C20B C21B H21D 107.3 . . ?
H21C C21B H21D 106.9 . . ?
C21A C22 C21B 7(3) . . ?
C21A C22 H22A 109.5 . . ?
C21B C22 H22A 111.5 . . ?
C21A C22 H22B 109.5 . . ?
C21B C22 H22B 113.7 . . ?
H22A C22 H22B 109.5 . . ?
C21A C22 H22C 109.5 . . ?
C21B C22 H22C 103.0 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C7 N1 C1 C6 12.2(9) . . . . ?
C7 N1 C1 C2 -168.6(5) . . . . ?
C6 C1 C2 C3 3.4(8) . . . . ?
N1 C1 C2 C3 -175.8(5) . . . . ?
C6 C1 C2 C9 -176.8(5) . . . . ?
N1 C1 C2 C9 4.0(8) . . . . ?
C1 C2 C3 C4 -1.8(8) . . . . ?
C9 C2 C3 C4 178.4(5) . . . . ?
C2 C3 C4 C5 -0.9(9) . . . . ?
C3 C4 C5 C6 2.1(9) . . . . ?
C4 C5 C6 C1 -0.6(9) . . . . ?
N1 C1 C6 C5 176.9(5) . . . . ?
C2 C1 C6 C5 -2.2(9) . . . . ?
C1 N1 C7 O1 0.1(10) . . . . ?
C1 N1 C7 C8 179.8(5) . . . . ?
C3 C2 C9 O2 161.6(5) . . . . ?
C1 C2 C9 O2 -18.2(9) . . . . ?
C3 C2 C9 C10 -23.1(7) . . . . ?
C1 C2 C9 C10 157.1(5) . . . . ?
C11 N2 C10 O3 -1.3(8) . . . . ?
C11 N2 C10 C9 175.9(4) . . . . ?
O2 C9 C10 O3 144.8(6) . . . . ?
C2 C9 C10 O3 -31.0(8) . . . . ?
O2 C9 C10 N2 -32.4(7) . . . . ?
C2 C9 C10 N2 151.8(5) . . . . ?
C10 N2 C11 C12B -117.9(6) . . . . ?
C10 N2 C11 C12A -67.8(7) . . . . ?
N2 C11 C12A C13 -53.8(10) . . . . ?
C12B C11 C12A C13 45.6(7) . . . . ?
N2 C11 C12B C13 57.0(9) . . . . ?
C12A C11 C12B C13 -44.9(7) . . . . ?
C11 C12A C13 C14B -130.9(9) . . . . ?
C11 C12A C13 C14A -173.8(8) . . . . ?
C11 C12A C13 C12B -45.3(7) . . . . ?
C11 C12B C13 C12A 45.4(7) . . . . ?
C11 C12B C13 C14B 173.3(8) . . . . ?
C11 C12B C13 C14A 131.0(9) . . . . ?
C12A C13 C14A C15 -178.2(9) . . . . ?
C14B C13 C14A C15 52.7(8) . . . . ?
C12B C13 C14A C15 127.9(10) . . . . ?
C12A C13 C14B C15 -129.4(9) . . . . ?
C14A C13 C14B C15 -52.2(8) . . . . ?
C12B C13 C14B C15 176.9(8) . . . . ?
C13 C14A C15 C16B -134.8(10) . . . . ?
C13 C14A C15 C16A -177.8(9) . . . . ?
C13 C14A C15 C14B -52.4(8) . . . . ?
C13 C14B C15 C14A 52.6(8) . . . . ?
C13 C14B C15 C16B 178.1(9) . . . . ?
C13 C14B C15 C16A 135.7(10) . . . . ?
C14A C15 C16A C17 -180.0(9) . . . . ?
C16B C15 C16A C17 54.9(9) . . . . ?
C14B C15 C16A C17 134.6(10) . . . . ?
C14A C15 C16B C17 -136.1(10) . . . . ?
C16A C15 C16B C17 -54.4(8) . . . . ?
C14B C15 C16B C17 178.9(9) . . . . ?
C15 C16A C17 C18B -136.5(10) . . . . ?
C15 C16A C17 C18A -178.5(9) . . . . ?
C15 C16A C17 C16B -54.6(8) . . . . ?
C15 C16B C17 C18B 178.9(9) . . . . ?
C15 C16B C17 C16A 54.7(9) . . . . ?
C15 C16B C17 C18A 137.3(10) . . . . ?
C18B C17 C18A C19 56.1(9) . . . . ?
C16A C17 C18A C19 179.9(9) . . . . ?
C16B C17 C18A C19 136.8(10) . . . . ?
C16A C17 C18B C19 -137.4(10) . . . . ?
C18A C17 C18B C19 -55.5(8) . . . . ?
C16B C17 C18B C19 179.8(9) . . . . ?
C17 C18A C19 C20B -140.1(12) . . . . ?
C17 C18A C19 C20A -174.7(11) . . . . ?
C17 C18A C19 C18B -55.6(9) . . . . ?
C17 C18B C19 C18A 55.9(9) . . . . ?
C17 C18B C19 C20B 176.2(10) . . . . ?
C17 C18B C19 C20A 141.5(12) . . . . ?
C18A C19 C20A C21A 178.3(19) . . . . ?
C20B C19 C20A C21A 57(2) . . . . ?
C18B C19 C20A C21A 136.3(19) . . . . ?
C18A C19 C20B C21B -137.8(19) . . . . ?
C20A C19 C20B C21B -59(2) . . . . ?
C18B C19 C20B C21B -179.6(19) . . . . ?
C19 C20A C21A C22 -164(2) . . . . ?
C19 C20B C21B C22 166.5(19) . . . . ?
C20A C21A C22 C21B -72(11) . . . . ?
C20B C21B C22 C21A 61(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.939
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.142