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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       jon.steed@durham.ac.uk
_publ_contact_author_name        'Jonathan Steed'
loop_
_publ_author_name
'John Davenport'
'Osama Musa'
'Martin Paterson'
'Marc-Oliver Piepenbrock'
'Katharina Fucke'
'Jonathan Steed'

data_JDIMER
_database_code_depnum_ccdc_archive 'CCDC 830351'
#TrackingRef '- 1.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Unsat Dimer from acetone'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.6087(14)
_cell_length_b                   9.292(2)
_cell_length_c                   13.114(3)
_cell_angle_alpha                109.100(10)
_cell_angle_beta                 98.253(11)
_cell_angle_gamma                91.170(8)
_cell_volume                     751.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9698
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3445
_reflns_number_gt                2598
_reflns_threshold_expression     >2sigma(I)

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

_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^)+(0.0664P)^2^+0.1483P] 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         3445
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31438(15) 0.75724(11) 0.34497(9) 0.0272(2) Uani 1 1 d . . .
O2 O -0.17986(15) 0.13744(12) 0.22419(9) 0.0306(3) Uani 1 1 d . . .
N3 N 0.15195(17) 0.08885(13) 0.20804(10) 0.0211(3) Uani 1 1 d . . .
N4 N 0.51247(17) 0.56201(12) 0.34764(9) 0.0201(3) Uani 1 1 d . . .
C5 C 0.3818(2) 0.30515(15) 0.21828(12) 0.0218(3) Uani 1 1 d . . .
H5 H 0.4917 0.2441 0.2063 0.026 Uiso 1 1 calc R . .
C6 C 0.2005(2) 0.24262(15) 0.22050(11) 0.0208(3) Uani 1 1 d . . .
H6 H 0.0943 0.3074 0.2315 0.025 Uiso 1 1 calc R . .
C7 C -0.0964(2) -0.11987(16) 0.19582(12) 0.0248(3) Uani 1 1 d . . .
H7A H -0.2309 -0.1312 0.2149 0.030 Uiso 1 1 calc R . .
H7B H 0.0026 -0.1512 0.2451 0.030 Uiso 1 1 calc R . .
C8 C 0.4131(2) 0.47244(15) 0.23472(11) 0.0215(3) Uani 1 1 d . . .
H8 H 0.2777 0.5105 0.2226 0.026 Uiso 1 1 calc R . .
C9 C 0.5635(2) 0.80045(16) 0.50486(12) 0.0236(3) Uani 1 1 d . . .
H9A H 0.5756 0.7392 0.5525 0.028 Uiso 1 1 calc R . .
H9B H 0.4832 0.8855 0.5359 0.028 Uiso 1 1 calc R . .
C10 C 0.8981(2) 0.60008(16) 0.40059(12) 0.0241(3) Uani 1 1 d . . .
H10A H 1.0117 0.5365 0.4042 0.029 Uiso 1 1 calc R . .
H10B H 0.8925 0.6243 0.3337 0.029 Uiso 1 1 calc R . .
C11 C -0.0938(2) -0.22502(17) 0.07788(13) 0.0281(3) Uani 1 1 d . . .
H11A H -0.1799 -0.3173 0.0641 0.034 Uiso 1 1 calc R . .
H11B H -0.1532 -0.1741 0.0281 0.034 Uiso 1 1 calc R . .
C12 C 0.6987(2) 0.50799(16) 0.39461(12) 0.0226(3) Uani 1 1 d . . .
H12A H 0.7095 0.4024 0.3512 0.027 Uiso 1 1 calc R . .
H12B H 0.6847 0.5107 0.4678 0.027 Uiso 1 1 calc R . .
C13 C 0.7788(2) 0.86238(16) 0.50051(12) 0.0251(3) Uani 1 1 d . . .
H13A H 0.7727 0.8926 0.4361 0.030 Uiso 1 1 calc R . .
H13B H 0.8193 0.9529 0.5640 0.030 Uiso 1 1 calc R . .
C14 C -0.0469(2) 0.04591(16) 0.21126(11) 0.0225(3) Uani 1 1 d . . .
C15 C 0.4526(2) 0.70443(15) 0.39319(12) 0.0209(3) Uani 1 1 d . . .
C16 C 0.9411(2) 0.74838(16) 0.49762(12) 0.0262(3) Uani 1 1 d . . .
H16A H 0.9536 0.7238 0.5646 0.031 Uiso 1 1 calc R . .
H16B H 1.0718 0.7964 0.4960 0.031 Uiso 1 1 calc R . .
C17 C 0.3087(2) -0.02287(16) 0.18736(13) 0.0244(3) Uani 1 1 d . . .
H17A H 0.3095 -0.0793 0.2379 0.029 Uiso 1 1 calc R . .
H17B H 0.4422 0.0314 0.2017 0.029 Uiso 1 1 calc R . .
C18 C 0.5365(2) 0.49937(18) 0.15207(13) 0.0295(3) Uani 1 1 d . . .
H18A H 0.5531 0.6069 0.1643 0.044 Uiso 1 1 calc R . .
H18B H 0.4652 0.4481 0.0794 0.044 Uiso 1 1 calc R . .
H18C H 0.6687 0.4600 0.1605 0.044 Uiso 1 1 calc R . .
C19 C 0.2741(2) -0.13550(18) 0.07084(14) 0.0312(4) Uani 1 1 d . . .
H19A H 0.4041 -0.1752 0.0532 0.037 Uiso 1 1 calc R . .
H19B H 0.2265 -0.0814 0.0210 0.037 Uiso 1 1 calc R . .
C20 C 0.1190(2) -0.26969(17) 0.05259(14) 0.0319(4) Uani 1 1 d . . .
H20A H 0.1056 -0.3354 -0.0231 0.038 Uiso 1 1 calc R . .
H20B H 0.1730 -0.3287 0.0978 0.038 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0242(5) 0.0255(5) 0.0320(6) 0.0102(4) 0.0026(4) 0.0078(4)
O2 0.0178(5) 0.0274(6) 0.0436(7) 0.0072(5) 0.0064(5) 0.0045(4)
N3 0.0157(6) 0.0185(6) 0.0289(7) 0.0076(5) 0.0036(5) 0.0027(4)
N4 0.0189(6) 0.0180(6) 0.0228(6) 0.0067(5) 0.0017(5) 0.0029(4)
C5 0.0189(7) 0.0209(7) 0.0246(7) 0.0067(5) 0.0023(5) 0.0036(5)
C6 0.0206(7) 0.0196(7) 0.0214(7) 0.0061(5) 0.0020(5) 0.0042(5)
C7 0.0196(7) 0.0262(7) 0.0278(8) 0.0084(6) 0.0034(6) -0.0017(5)
C8 0.0191(7) 0.0212(7) 0.0233(7) 0.0075(5) 0.0009(5) 0.0006(5)
C9 0.0253(7) 0.0204(7) 0.0251(7) 0.0062(5) 0.0068(6) 0.0050(5)
C10 0.0185(7) 0.0243(7) 0.0287(8) 0.0077(6) 0.0036(6) 0.0049(5)
C11 0.0266(7) 0.0243(7) 0.0300(8) 0.0063(6) 0.0007(6) -0.0012(6)
C12 0.0208(7) 0.0201(7) 0.0263(7) 0.0079(5) 0.0005(5) 0.0042(5)
C13 0.0266(8) 0.0195(7) 0.0270(8) 0.0046(6) 0.0045(6) 0.0009(6)
C14 0.0186(7) 0.0248(7) 0.0223(7) 0.0055(5) 0.0026(5) 0.0024(5)
C15 0.0183(6) 0.0204(7) 0.0269(7) 0.0100(5) 0.0074(5) 0.0029(5)
C16 0.0211(7) 0.0256(7) 0.0288(8) 0.0057(6) 0.0024(6) -0.0004(6)
C17 0.0158(6) 0.0224(7) 0.0368(8) 0.0119(6) 0.0045(6) 0.0049(5)
C18 0.0307(8) 0.0310(8) 0.0262(8) 0.0088(6) 0.0050(6) -0.0034(6)
C19 0.0295(8) 0.0287(8) 0.0381(9) 0.0112(7) 0.0128(7) 0.0092(6)
C20 0.0324(8) 0.0258(8) 0.0330(9) 0.0031(6) 0.0067(7) 0.0049(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
O1 C15 1.2372(17) . ?
O2 C14 1.2258(17) . ?
N3 C14 1.3763(18) . ?
N3 C6 1.4087(17) . ?
N3 C17 1.4711(17) . ?
N4 C15 1.3552(18) . ?
N4 C12 1.4684(17) . ?
N4 C8 1.4861(18) . ?
C5 C6 1.3289(19) . ?
C5 C8 1.5034(19) . ?
C7 C14 1.509(2) . ?
C7 C11 1.538(2) . ?
C8 C18 1.525(2) . ?
C9 C15 1.513(2) . ?
C9 C13 1.539(2) . ?
C10 C16 1.527(2) . ?
C10 C12 1.534(2) . ?
C11 C20 1.525(2) . ?
C13 C16 1.519(2) . ?
C17 C19 1.525(2) . ?
C19 C20 1.532(2) . ?

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
C14 N3 C6 118.12(11) . . ?
C14 N3 C17 121.45(11) . . ?
C6 N3 C17 120.37(11) . . ?
C15 N4 C12 122.18(12) . . ?
C15 N4 C8 117.80(11) . . ?
C12 N4 C8 118.58(11) . . ?
C6 C5 C8 121.44(13) . . ?
C5 C6 N3 127.01(13) . . ?
C14 C7 C11 112.54(12) . . ?
N4 C8 C5 112.31(11) . . ?
N4 C8 C18 110.04(11) . . ?
C5 C8 C18 111.44(12) . . ?
C15 C9 C13 112.37(12) . . ?
C16 C10 C12 114.62(12) . . ?
C20 C11 C7 114.37(12) . . ?
N4 C12 C10 114.74(11) . . ?
C16 C13 C9 113.74(12) . . ?
O2 C14 N3 121.67(13) . . ?
O2 C14 C7 121.08(13) . . ?
N3 C14 C7 117.24(12) . . ?
O1 C15 N4 121.74(13) . . ?
O1 C15 C9 120.18(12) . . ?
N4 C15 C9 118.07(12) . . ?
C13 C16 C10 114.53(12) . . ?
N3 C17 C19 113.32(12) . . ?
C17 C19 C20 113.69(13) . . ?
C11 C20 C19 114.97(13) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048

# Attachment '- 2.cif'

data_vcl
_database_code_depnum_ccdc_archive 'CCDC 830352'
#TrackingRef '- 2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H28 N2 O2'
_chemical_formula_sum            'C16 H28 N2 O2'
_chemical_formula_weight         280.40

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   P21/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                   12.540(3)
_cell_length_b                   12.897(3)
_cell_length_c                   9.964(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.050(3)
_cell_angle_gamma                90.00
_cell_volume                     1602.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6622
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.36

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.001
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Diamond Light Source, Didcot, UK'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15488
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         27.37
_reflns_number_total             3955
_reflns_number_gt                3085
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0792P)^2^+0.1857P] 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     SHELXL
_refine_ls_extinction_coef       0.24(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
N1 N 0.74433(8) 0.84023(8) 0.12954(11) 0.0324(3) Uani 1 1 d . . .
O1 O 0.69749(10) 0.68431(8) 0.03595(12) 0.0550(3) Uani 1 1 d . . .
C8 C 0.83989(10) 0.84526(10) 0.05514(13) 0.0361(3) Uani 1 1 d . . .
H8 H 0.8456 0.7771 0.0086 0.043 Uiso 1 1 calc R . .
C6 C 0.72293(9) 0.92711(9) 0.21801(13) 0.0333(3) Uani 1 1 d . . .
H6A H 0.7849 0.9750 0.2239 0.040 Uiso 1 1 calc R . .
H6B H 0.7171 0.8998 0.3098 0.040 Uiso 1 1 calc R . .
O2 O 1.11179(9) 0.63672(8) 0.28865(13) 0.0576(3) Uani 1 1 d . . .
C10 C 0.95080(10) 0.78141(11) 0.26458(15) 0.0403(3) Uani 1 1 d . . .
H10A H 0.8889 0.7909 0.3174 0.048 Uiso 1 1 calc R . .
H10B H 0.9463 0.7106 0.2259 0.048 Uiso 1 1 calc R . .
C1 C 0.68061(11) 0.75556(10) 0.11391(14) 0.0384(3) Uani 1 1 d . . .
C9 C 0.94283(10) 0.85953(10) 0.15029(14) 0.0378(3) Uani 1 1 d . . .
H9A H 1.0056 0.8517 0.0986 0.045 Uiso 1 1 calc R . .
H9B H 0.9444 0.9305 0.1883 0.045 Uiso 1 1 calc R . .
N2 N 1.04986(9) 0.79040(9) 0.35545(11) 0.0381(3) Uani 1 1 d . . .
C12 C 1.22476(12) 0.72981(11) 0.45511(16) 0.0453(4) Uani 1 1 d . . .
H12A H 1.2660 0.6642 0.4613 0.054 Uiso 1 1 calc R . .
H12B H 1.2047 0.7460 0.5462 0.054 Uiso 1 1 calc R . .
C11 C 1.12368(11) 0.71463(10) 0.35978(14) 0.0395(3) Uani 1 1 d . . .
C5 C 0.62144(11) 0.98842(12) 0.17223(15) 0.0436(3) Uani 1 1 d . . .
H5A H 0.6277 1.0583 0.2133 0.052 Uiso 1 1 calc R . .
H5B H 0.6164 0.9972 0.0731 0.052 Uiso 1 1 calc R . .
C7 C 0.82866(12) 0.92844(12) -0.05342(15) 0.0453(4) Uani 1 1 d . . .
H7A H 0.7644 0.9148 -0.1158 0.068 Uiso 1 1 calc R . .
H7B H 0.8920 0.9276 -0.1032 0.068 Uiso 1 1 calc R . .
H7C H 0.8223 0.9965 -0.0113 0.068 Uiso 1 1 calc R . .
C16 C 1.06393(12) 0.88576(11) 0.43629(15) 0.0457(4) Uani 1 1 d . . .
H16A H 1.0794 0.8664 0.5325 0.055 Uiso 1 1 calc R . .
H16B H 0.9956 0.9248 0.4266 0.055 Uiso 1 1 calc R . .
C2 C 0.58471(12) 0.75148(12) 0.19322(16) 0.0486(4) Uani 1 1 d . . .
H2A H 0.6090 0.7633 0.2898 0.058 Uiso 1 1 calc R . .
H2B H 0.5529 0.6812 0.1847 0.058 Uiso 1 1 calc R . .
C13 C 1.29630(12) 0.81683(12) 0.41026(18) 0.0498(4) Uani 1 1 d . . .
H13A H 1.3714 0.8029 0.4471 0.060 Uiso 1 1 calc R . .
H13B H 1.2934 0.8159 0.3106 0.060 Uiso 1 1 calc R . .
C15 C 1.15251(13) 0.95650(11) 0.39830(18) 0.0505(4) Uani 1 1 d . . .
H15A H 1.1391 1.0274 0.4309 0.061 Uiso 1 1 calc R . .
H15B H 1.1492 0.9595 0.2987 0.061 Uiso 1 1 calc R . .
C4 C 0.51874(11) 0.93828(14) 0.20871(18) 0.0542(4) Uani 1 1 d . . .
H4A H 0.4575 0.9840 0.1782 0.065 Uiso 1 1 calc R . .
H4B H 0.5222 0.9324 0.3081 0.065 Uiso 1 1 calc R . .
C3 C 0.49825(11) 0.83143(14) 0.14695(17) 0.0544(4) Uani 1 1 d . . .
H3A H 0.4935 0.8376 0.0475 0.065 Uiso 1 1 calc R . .
H3B H 0.4282 0.8059 0.1706 0.065 Uiso 1 1 calc R . .
C14 C 1.26504(13) 0.92343(12) 0.45464(19) 0.0541(4) Uani 1 1 d . . .
H14A H 1.3171 0.9744 0.4261 0.065 Uiso 1 1 calc R . .
H14B H 1.2699 0.9249 0.5544 0.065 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
N1 0.0364(5) 0.0267(5) 0.0343(6) -0.0026(4) 0.0049(4) -0.0009(4)
O1 0.0723(7) 0.0351(6) 0.0572(7) -0.0140(5) 0.0052(5) -0.0069(5)
C8 0.0427(6) 0.0331(6) 0.0336(7) 0.0016(5) 0.0085(5) 0.0030(5)
C6 0.0340(6) 0.0295(6) 0.0359(7) -0.0053(5) 0.0017(5) -0.0007(4)
O2 0.0645(7) 0.0371(6) 0.0665(8) -0.0111(5) -0.0155(6) 0.0153(5)
C10 0.0381(6) 0.0398(7) 0.0429(8) 0.0085(6) 0.0037(5) 0.0037(5)
C1 0.0460(7) 0.0309(6) 0.0368(7) 0.0005(5) -0.0027(5) -0.0040(5)
C9 0.0362(6) 0.0388(7) 0.0396(7) 0.0060(5) 0.0094(5) 0.0047(5)
N2 0.0409(6) 0.0354(6) 0.0377(6) 0.0009(5) 0.0031(4) 0.0084(4)
C12 0.0493(8) 0.0352(7) 0.0490(8) 0.0044(6) -0.0063(6) 0.0081(6)
C11 0.0471(7) 0.0310(6) 0.0394(7) 0.0034(5) 0.0005(5) 0.0078(5)
C5 0.0434(7) 0.0406(7) 0.0459(8) -0.0047(6) -0.0007(6) 0.0080(5)
C7 0.0511(8) 0.0473(8) 0.0378(8) 0.0091(6) 0.0059(6) 0.0026(6)
C16 0.0526(8) 0.0420(8) 0.0433(8) -0.0067(6) 0.0089(6) 0.0138(6)
C2 0.0511(8) 0.0476(8) 0.0466(9) 0.0003(6) 0.0031(6) -0.0186(6)
C13 0.0418(7) 0.0503(9) 0.0566(9) 0.0053(7) 0.0017(6) 0.0063(6)
C15 0.0611(9) 0.0323(7) 0.0574(10) -0.0022(6) 0.0033(7) 0.0072(6)
C4 0.0356(7) 0.0706(11) 0.0558(10) -0.0098(8) 0.0019(6) 0.0089(7)
C3 0.0343(7) 0.0762(11) 0.0519(9) -0.0083(8) 0.0016(6) -0.0112(7)
C14 0.0572(9) 0.0411(8) 0.0623(11) 0.0013(7) -0.0018(7) -0.0035(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3524(16) . ?
N1 C6 1.4679(16) . ?
N1 C8 1.4754(16) . ?
O1 C1 1.2358(17) . ?
C8 C7 1.5194(19) . ?
C8 C9 1.5300(19) . ?
C8 H8 1.0000 . ?
C6 C5 1.5266(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O2 C11 1.2296(17) . ?
C10 N2 1.4626(17) . ?
C10 C9 1.5159(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C1 C2 1.508(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N2 C11 1.3436(16) . ?
N2 C16 1.4706(18) . ?
C12 C11 1.5144(19) . ?
C12 C13 1.533(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 C4 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C16 C15 1.516(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C2 C3 1.532(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C13 C14 1.509(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C15 C14 1.524(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C4 C3 1.520(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 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
C1 N1 C6 122.84(11) . . ?
C1 N1 C8 118.62(11) . . ?
C6 N1 C8 118.54(10) . . ?
N1 C8 C7 111.68(11) . . ?
N1 C8 C9 111.77(11) . . ?
C7 C8 C9 111.41(11) . . ?
N1 C8 H8 107.2 . . ?
C7 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
N1 C6 C5 114.54(10) . . ?
N1 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
N1 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
N2 C10 C9 113.38(11) . . ?
N2 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
O1 C1 N1 122.31(13) . . ?
O1 C1 C2 120.16(12) . . ?
N1 C1 C2 117.52(12) . . ?
C10 C9 C8 111.72(11) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 N2 C10 119.97(12) . . ?
C11 N2 C16 123.24(12) . . ?
C10 N2 C16 116.77(11) . . ?
C11 C12 C13 112.88(12) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
O2 C11 N2 122.31(13) . . ?
O2 C11 C12 120.65(12) . . ?
N2 C11 C12 117.03(12) . . ?
C4 C5 C6 114.15(13) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C16 C15 114.54(12) . . ?
N2 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
N2 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C1 C2 C3 113.40(13) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C14 C13 C12 113.81(14) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C16 C15 C14 114.46(13) . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C5 C4 C3 113.61(13) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C4 C3 C2 113.85(12) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C13 C14 C15 113.97(14) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054