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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.38

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   'P 2(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                   11.3698(18)
_cell_length_b                   6.2439(9)
_cell_length_c                   21.563(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.206(4)
_cell_angle_gamma                90.00
_cell_volume                     1521.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11929
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2818
_reflns_number_gt                2237
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.6059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.32020(12) 0.8761(2) 0.04213(6) 0.0211(3) Uani 1 1 d . . .
N2 N 0.20198(12) 0.5936(2) -0.02572(6) 0.0201(3) Uani 1 1 d . . .
O1 O 0.39537(10) 0.19398(19) 0.12432(6) 0.0266(3) Uani 1 1 d . . .
H1 H 0.3891 0.0862 0.1009 0.040 Uiso 1 1 calc R . .
O2 O 1.13577(10) 0.25016(18) 0.40416(5) 0.0256(3) Uani 1 1 d . . .
H2 H 1.1486 0.1353 0.4240 0.038 Uiso 1 1 calc R . .
C1 C 0.50120(14) 0.1876(3) 0.16043(7) 0.0190(4) Uani 1 1 d . . .
C2 C 0.57529(14) 0.0090(3) 0.16503(7) 0.0190(4) Uani 1 1 d . . .
H2A H 0.5528 -0.1169 0.1420 0.023 Uiso 1 1 calc R . .
C3 C 0.68145(14) 0.0143(3) 0.20301(7) 0.0189(4) Uani 1 1 d . . .
H3 H 0.7311 -0.1084 0.2055 0.023 Uiso 1 1 calc R . .
C4 C 0.71707(14) 0.1966(3) 0.23777(7) 0.0183(4) Uani 1 1 d . . .
C5 C 0.64079(14) 0.3737(3) 0.23276(7) 0.0197(4) Uani 1 1 d . . .
H5 H 0.6627 0.4997 0.2559 0.024 Uiso 1 1 calc R . .
C6 C 0.53480(14) 0.3696(3) 0.19508(7) 0.0210(4) Uani 1 1 d . . .
H6 H 0.4845 0.4915 0.1928 0.025 Uiso 1 1 calc R . .
C7 C 0.82924(14) 0.2043(3) 0.27951(7) 0.0177(4) Uani 1 1 d . . .
C8 C 0.86872(14) 0.0299(3) 0.31642(7) 0.0202(4) Uani 1 1 d . . .
H8 H 0.8240 -0.0990 0.3135 0.024 Uiso 1 1 calc R . .
C9 C 0.97114(14) 0.0395(3) 0.35712(7) 0.0196(4) Uani 1 1 d . . .
H9 H 0.9966 -0.0825 0.3813 0.024 Uiso 1 1 calc R . .
C10 C 1.03744(14) 0.2284(3) 0.36289(7) 0.0191(4) Uani 1 1 d . . .
C11 C 1.00103(14) 0.4026(3) 0.32555(7) 0.0202(4) Uani 1 1 d . . .
H11 H 1.0465 0.5305 0.3281 0.024 Uiso 1 1 calc R . .
C12 C 0.89900(14) 0.3904(3) 0.28476(7) 0.0196(4) Uani 1 1 d . . .
H12 H 0.8753 0.5110 0.2596 0.023 Uiso 1 1 calc R . .
C13 C 0.34686(16) 0.6593(3) 0.06664(8) 0.0259(4) Uani 1 1 d . . .
H13A H 0.3324 0.6528 0.1111 0.031 Uiso 1 1 calc R . .
H13B H 0.4313 0.6260 0.0640 0.031 Uiso 1 1 calc R . .
C14 C 0.26865(15) 0.4925(3) 0.02896(8) 0.0252(4) Uani 1 1 d . . .
H14A H 0.3190 0.3765 0.0150 0.030 Uiso 1 1 calc R . .
H14B H 0.2127 0.4283 0.0559 0.030 Uiso 1 1 calc R . .
C15 C 0.34948(15) 0.8858(3) -0.02270(8) 0.0253(4) Uani 1 1 d . . .
H15A H 0.4360 0.8705 -0.0233 0.030 Uiso 1 1 calc R . .
H15B H 0.3256 1.0266 -0.0410 0.030 Uiso 1 1 calc R . .
C16 C 0.28517(15) 0.7055(3) -0.06210(8) 0.0261(4) Uani 1 1 d . . .
H16A H 0.2417 0.7675 -0.1002 0.031 Uiso 1 1 calc R . .
H16B H 0.3439 0.6025 -0.0751 0.031 Uiso 1 1 calc R . .
C17 C 0.19102(14) 0.9122(3) 0.04185(8) 0.0237(4) Uani 1 1 d . . .
H17A H 0.1716 1.0613 0.0289 0.028 Uiso 1 1 calc R . .
H17B H 0.1682 0.8918 0.0845 0.028 Uiso 1 1 calc R . .
C18 C 0.12078(14) 0.7549(3) -0.00338(8) 0.0241(4) Uani 1 1 d . . .
H18A H 0.0594 0.6822 0.0182 0.029 Uiso 1 1 calc R . .
H18B H 0.0808 0.8347 -0.0393 0.029 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C13 1.473(2) . ?
N1 C15 1.473(2) . ?
N1 C17 1.485(2) . ?
N2 C16 1.469(2) . ?
N2 C14 1.473(2) . ?
N2 C18 1.481(2) . ?
O1 C1 1.3614(19) . ?
O2 C10 1.3584(19) . ?
C1 C6 1.390(2) . ?
C1 C2 1.395(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.402(2) . ?
C4 C7 1.480(2) . ?
C5 C6 1.379(2) . ?
C7 C8 1.394(2) . ?
C7 C12 1.404(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.390(2) . ?
C11 C12 1.380(2) . ?
C13 C14 1.542(2) . ?
C15 C16 1.545(2) . ?
C17 C18 1.544(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
C13 N1 C15 108.63(13) . . ?
C13 N1 C17 107.83(13) . . ?
C15 N1 C17 108.34(13) . . ?
C16 N2 C14 109.02(13) . . ?
C16 N2 C18 108.07(13) . . ?
C14 N2 C18 108.42(13) . . ?
O1 C1 C6 117.25(14) . . ?
O1 C1 C2 123.63(14) . . ?
C6 C1 C2 119.12(15) . . ?
C3 C2 C1 120.29(15) . . ?
C2 C3 C4 121.33(15) . . ?
C3 C4 C5 117.37(14) . . ?
C3 C4 C7 122.19(14) . . ?
C5 C4 C7 120.43(14) . . ?
C6 C5 C4 121.64(15) . . ?
C5 C6 C1 120.24(15) . . ?
C8 C7 C12 117.13(15) . . ?
C8 C7 C4 121.67(14) . . ?
C12 C7 C4 121.18(14) . . ?
C9 C8 C7 121.72(15) . . ?
C8 C9 C10 120.18(15) . . ?
O2 C10 C11 118.29(14) . . ?
O2 C10 C9 122.72(14) . . ?
C11 C10 C9 118.99(15) . . ?
C12 C11 C10 120.23(15) . . ?
C11 C12 C7 121.70(15) . . ?
N1 C13 C14 110.31(13) . . ?
N2 C14 C13 110.45(13) . . ?
N1 C15 C16 110.47(13) . . ?
N2 C16 C15 110.27(13) . . ?
N1 C17 C18 110.46(13) . . ?
N2 C18 C17 109.86(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 995687'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.38

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   'C 2/c'

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

_cell_length_a                   11.819(2)
_cell_length_b                   6.2786(11)
_cell_length_c                   21.136(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.707(6)
_cell_angle_gamma                90.00
_cell_volume                     1554.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6092
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1436
_reflns_number_gt                911
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.7284P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0096(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1436
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.13103(17) 0.4675(3) 0.11317(11) 0.0997(7) Uani 1 1 d . . .
H1 H 0.1193 0.3547 0.0919 0.150 Uiso 1 1 calc R . .
C1 C 0.2331(3) 0.4551(3) 0.15039(13) 0.0772(8) Uani 1 1 d . . .
C2 C 0.2704(2) 0.6309(3) 0.18718(12) 0.0739(8) Uani 1 1 d . . .
H2 H 0.2241 0.7549 0.1859 0.089 Uiso 1 1 calc R . .
C3 C 0.3736(3) 0.6268(3) 0.22541(12) 0.0709(8) Uani 1 1 d . . .
H3 H 0.3980 0.7494 0.2499 0.085 Uiso 1 1 calc R . .
C4 C 0.4440(2) 0.4472(3) 0.22942(9) 0.0696(8) Uani 1 1 d . . .
C5 C 0.4040(3) 0.2707(3) 0.19309(11) 0.0769(8) Uani 1 1 d . . .
H5 H 0.4494 0.1453 0.1951 0.092 Uiso 1 1 calc R . .
C6 C 0.3009(3) 0.2732(3) 0.15445(12) 0.0784(8) Uani 1 1 d . . .
H6 H 0.2757 0.1502 0.1304 0.094 Uiso 1 1 calc R . .
N1 N 0.0432(14) 0.149(2) 0.0282(8) 0.049(3) Uani 0.50 1 d P . .
C7 C -0.0171(4) 0.0104(8) 0.0644(2) 0.0617(12) Uani 0.50 1 d P . .
H7A H -0.0706 0.0927 0.0828 0.092 Uiso 0.50 1 d PR . .
H7B H 0.0316 -0.0601 0.0980 0.092 Uiso 0.50 1 d PR . .
C8 C -0.0102(5) 0.2348(7) -0.0262(2) 0.0709(13) Uani 0.50 1 d P . .
H8A H -0.0637 0.3318 -0.0136 0.106 Uiso 0.50 1 d PR . .
H8B H 0.0406 0.3095 -0.0488 0.106 Uiso 0.50 1 d PR . .
C9 C 0.1367(4) -0.0219(7) 0.0038(2) 0.0727(14) Uani 0.50 1 d P . .
H9A H 0.1812 -0.0947 0.0387 0.109 Uiso 0.50 1 d PR . .
H9B H 0.1843 0.0584 -0.0195 0.109 Uiso 0.50 1 d PR . .
N2 N 0.0721(14) 0.128(3) 0.0436(9) 0.052(3) Uani 0.50 1 d P . .
C10 C 0.0848(5) 0.1579(7) -0.0219(2) 0.0597(12) Uani 0.50 1 d P . .
H10A H 0.1618 0.1323 -0.0251 0.090 Uiso 0.50 1 d PR . .
H10B H 0.0653 0.2991 -0.0357 0.090 Uiso 0.50 1 d PR . .
C11 C 0.0854(5) -0.0733(6) 0.0677(2) 0.0727(14) Uani 0.50 1 d P . .
H11A H 0.1618 -0.1156 0.0696 0.109 Uiso 0.50 1 d PR . .
H11B H 0.0660 -0.0734 0.1102 0.109 Uiso 0.50 1 d PR . .
C12 C -0.0669(4) 0.1796(7) 0.0430(2) 0.0720(14) Uani 0.50 1 d P . .
H12A H -0.0851 0.3176 0.0257 0.108 Uiso 0.50 1 d PR . .
H12B H -0.0827 0.1727 0.0862 0.108 Uiso 0.50 1 d PR . .


_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 C1 1.352(3) . ?
O1 H1 0.8400 . ?
C1 C2 1.387(3) . ?
C1 C6 1.391(4) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 C4 1.483(5) 2_655 ?
C5 C6 1.374(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C8 1.349(14) . ?
N1 C7 1.41(2) . ?
N1 C9 1.67(2) . ?
C7 C10 1.540(5) 5 ?
C7 C8 1.788(7) 5 ?
C7 C9 1.880(7) 5 ?
C7 H7A 0.9404 . ?
C7 H7B 0.9606 . ?
C7 H11B 1.3879 . ?
C7 H12B 1.3961 . ?
C8 C11 1.542(6) 5 ?
C8 C7 1.788(7) 5 ?
C8 H8A 0.9410 . ?
C8 H8B 0.9414 . ?
C8 H10B 1.0239 . ?
C8 H12A 1.5863 . ?
C9 C12 1.556(6) 5 ?
C9 C7 1.880(7) 5 ?
C9 H9A 0.9615 . ?
C9 H9B 0.9427 . ?
C9 H10A 1.2035 . ?
C9 H11A 1.5018 . ?
N2 C11 1.365(17) . ?
N2 C10 1.42(2) . ?
N2 C12 1.673(19) . ?
C10 C7 1.540(5) 5 ?
C10 H8B 1.1929 . ?
C10 H9B 1.3263 . ?
C10 H10A 0.9345 . ?
C10 H10B 0.9524 . ?
C11 C8 1.542(6) 5 ?
C11 H7B 0.9645 . ?
C11 H9A 1.3640 . ?
C11 H11A 0.9368 . ?
C11 H11B 0.9569 . ?
C12 C9 1.556(6) 5 ?
C12 H7A 1.0087 . ?
C12 H8A 1.5355 . ?
C12 H12A 0.9534 . ?
C12 H12B 0.9584 . ?

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 O1 H1 109.5 . . ?
O1 C1 C2 118.2(2) . . ?
O1 C1 C6 123.0(2) . . ?
C2 C1 C6 118.8(3) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.9(2) . . ?
C5 C4 C4 122.22(18) . 2_655 ?
C3 C4 C4 120.85(16) . 2_655 ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 N1 C7 119.7(12) . . ?
C8 N1 C9 104.3(13) . . ?
C7 N1 C9 100.1(9) . . ?
N1 C7 C10 111.6(7) . 5 ?
N1 C7 C8 98.7(8) . 5 ?
C10 C7 C8 42.0(3) 5 5 ?
N1 C7 C9 86.8(6) . 5 ?
C10 C7 C9 45.6(3) 5 5 ?
C8 C7 C9 81.4(3) 5 5 ?
N1 C7 H7A 107.6 . . ?
C10 C7 H7A 107.0 5 . ?
C8 C7 H7A 146.3 5 . ?
C9 C7 H7A 79.6 5 . ?
N1 C7 H7B 112.8 . . ?
C10 C7 H7B 109.2 5 . ?
C8 C7 H7B 79.0 5 . ?
C9 C7 H7B 154.1 5 . ?
H7A C7 H7B 108.5 . . ?
N1 C7 H11B 104.4 . . ?
C10 C7 H11B 114.3 5 . ?
C8 C7 H11B 80.5 5 . ?
C9 C7 H11B 159.9 5 . ?
H7A C7 H11B 111.8 . . ?
H7B C7 H11B 8.4 . . ?
N1 C7 H12B 94.2 . . ?
C10 C7 H12B 115.2 5 . ?
C8 C7 H12B 156.9 5 . ?
C9 C7 H12B 80.3 5 . ?
H7A C7 H12B 13.6 . . ?
H7B C7 H12B 113.3 . . ?
H11B C7 H12B 114.7 . . ?
N1 C8 C11 112.9(8) . 5 ?
N1 C8 C7 87.0(8) . 5 ?
C11 C8 C7 45.7(3) 5 5 ?
N1 C8 H8A 105.9 . . ?
C11 C8 H8A 103.2 5 . ?
C7 C8 H8A 148.6 5 . ?
N1 C8 H8B 112.0 . . ?
C11 C8 H8B 113.4 5 . ?
C7 C8 H8B 92.0 5 . ?
H8A C8 H8B 108.6 . . ?
N1 C8 H10B 90.3 . . ?
C11 C8 H10B 126.7 5 . ?
C7 C8 H10B 92.0 5 . ?
H8A C8 H10B 115.9 . . ?
H8B C8 H10B 21.7 . . ?
N1 C8 H12A 77.4 . . ?
C11 C8 H12A 106.0 5 . ?
C7 C8 H12A 138.2 5 . ?
H8A C8 H12A 30.1 . . ?
H8B C8 H12A 129.8 . . ?
H10B C8 H12A 126.1 . . ?
C12 C9 N1 106.8(6) 5 . ?
C12 C9 C7 42.0(2) 5 5 ?
N1 C9 C7 75.6(5) . 5 ?
C12 C9 H9A 112.0 5 . ?
N1 C9 H9A 112.7 . . ?
C7 C9 H9A 152.1 5 . ?
C12 C9 H9B 108.1 5 . ?
N1 C9 H9B 106.5 . . ?
C7 C9 H9B 91.1 5 . ?
H9A C9 H9B 110.5 . . ?
C12 C9 H10A 109.5 5 . ?
N1 C9 H10A 81.9 . . ?
C7 C9 H10A 77.9 5 . ?
H9A C9 H10A 128.7 . . ?
H9B C9 H10A 25.7 . . ?
C12 C9 H11A 111.2 5 . ?
N1 C9 H11A 91.3 . . ?
C7 C9 H11A 139.5 5 . ?
H9A C9 H11A 23.8 . . ?
H9B C9 H11A 129.5 . . ?
H10A C9 H11A 138.9 . . ?
C11 N2 C10 117.5(14) . . ?
C11 N2 C12 104.2(13) . . ?
C10 N2 C12 101.5(8) . . ?
N2 C10 C7 111.3(8) . 5 ?
N2 C10 H8B 118.1 . . ?
C7 C10 H8B 96.3 5 . ?
N2 C10 H9B 96.3 . . ?
C7 C10 H9B 95.0 5 . ?
H8B C10 H9B 136.3 . . ?
N2 C10 H10A 106.2 . . ?
C7 C10 H10A 105.9 5 . ?
H8B C10 H10A 118.1 . . ?
H9B C10 H10A 19.3 . . ?
N2 C10 H10B 111.6 . . ?
C7 C10 H10B 111.9 5 . ?
H8B C10 H10B 15.8 . . ?
H9B C10 H10B 128.9 . . ?
H10A C10 H10B 109.6 . . ?
N2 C11 C8 111.6(7) . 5 ?
N2 C11 H7B 96.6 . . ?
C8 C11 H7B 93.0 5 . ?
N2 C11 H9A 89.1 . . ?
C8 C11 H9A 97.4 5 . ?
H7B C11 H9A 165.3 . . ?
N2 C11 H11A 109.9 . . ?
C8 C11 H11A 108.5 5 . ?
H7B C11 H11A 135.4 . . ?
H9A C11 H11A 30.5 . . ?
N2 C11 H11B 108.7 . . ?
C8 C11 H11B 110.0 5 . ?
H7B C11 H11B 27.7 . . ?
H9A C11 H11B 137.7 . . ?
H11A C11 H11B 108.0 . . ?
C9 C12 N2 108.6(7) 5 . ?
C9 C12 H7A 96.2 5 . ?
N2 C12 H7A 92.4 . . ?
C9 C12 H8A 88.1 5 . ?
N2 C12 H8A 89.9 . . ?
H7A C12 H8A 174.2 . . ?
C9 C12 H12A 105.1 5 . ?
N2 C12 H12A 110.4 . . ?
H7A C12 H12A 141.1 . . ?
H8A C12 H12A 33.3 . . ?
C9 C12 H12B 115.1 5 . ?
N2 C12 H12B 107.5 . . ?
H7A C12 H12B 31.1 . . ?
H8A C12 H12B 143.1 . . ?
H12A C12 H12B 110.1 . . ?

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
O1 C1 C2 C3 -179.60(19) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C4 179.3(2) . . . 2_655 ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C4 C5 C6 -179.1(2) 2_655 . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
O1 C1 C6 C5 179.9(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C8 N1 C7 C10 46.9(17) . . . 5 ?
C9 N1 C7 C10 -66.1(8) . . . 5 ?
C8 N1 C7 C8 88.5(14) . . . 5 ?
C9 N1 C7 C8 -24.5(7) . . . 5 ?
C8 N1 C7 C9 7.8(14) . . . 5 ?
C9 N1 C7 C9 -105.2(6) . . . 5 ?
C7 N1 C8 C11 -43.1(18) . . . 5 ?
C9 N1 C8 C11 67.7(11) . . . 5 ?
C7 N1 C8 C7 -81.7(14) . . . 5 ?
C9 N1 C8 C7 29.0(8) . . . 5 ?
C8 N1 C9 C12 -56.9(11) . . . 5 ?
C7 N1 C9 C12 67.5(8) . . . 5 ?
C8 N1 C9 C7 -28.4(8) . . . 5 ?
C7 N1 C9 C7 96.0(7) . . . 5 ?
C11 N2 C10 C7 47.2(14) . . . 5 ?
C12 N2 C10 C7 -65.6(11) . . . 5 ?
C10 N2 C11 C8 -51.9(15) . . . 5 ?
C12 N2 C11 C8 59.4(12) . . . 5 ?
C11 N2 C12 C9 -63.8(11) . . . 5 ?
C10 N2 C12 C9 58.7(11) . . . 5 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 995688'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.38

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   'C 2/c'

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

_cell_length_a                   12.1356(18)
_cell_length_b                   6.3400(11)
_cell_length_c                   21.054(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.846(5)
_cell_angle_gamma                90.00
_cell_volume                     1600.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6873
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.48
_reflns_number_total             1488
_reflns_number_gt                1145
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0796P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1488
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.13245(8) 0.46324(17) 0.11505(6) 0.0783(4) Uani 1 1 d . . .
H1 H 0.1204 0.3554 0.0936 0.117 Uiso 1 1 calc R . .
C1 C 0.23444(11) 0.4499(2) 0.15204(6) 0.0527(4) Uani 1 1 d . . .
C2 C 0.27277(11) 0.6241(2) 0.18860(6) 0.0554(4) Uani 1 1 d . . .
H2 H 0.2287 0.7444 0.1875 0.067 Uiso 1 1 calc R . .
C3 C 0.37573(11) 0.6199(2) 0.22658(6) 0.0511(4) Uani 1 1 d . . .
H3 H 0.4003 0.7384 0.2507 0.061 Uiso 1 1 calc R . .
C4 C 0.44425(10) 0.4422(2) 0.22981(5) 0.0450(4) Uani 1 1 d . . .
C5 C 0.40360(11) 0.2675(2) 0.19350(6) 0.0514(4) Uani 1 1 d . . .
H5 H 0.4468 0.1459 0.1951 0.062 Uiso 1 1 calc R . .
C6 C 0.30040(11) 0.2708(2) 0.15518(6) 0.0535(4) Uani 1 1 d . . .
H6 H 0.2751 0.1521 0.1314 0.064 Uiso 1 1 calc R . .
N1 N 0.0579(14) 0.129(2) 0.0350(7) 0.062(4) Uani 0.50 1 d P . .
C7 C -0.0041(3) -0.0037(6) 0.06874(15) 0.0669(9) Uani 0.50 1 d P . .
H7A H -0.0575 0.0786 0.0872 0.100 Uiso 0.50 1 d PR . .
H7B H 0.0447 -0.0742 0.1024 0.100 Uiso 0.50 1 d PR . .
C8 C -0.0002(3) 0.2251(5) -0.02143(18) 0.0716(10) Uani 0.50 1 d P . .
H8A H -0.0537 0.3221 -0.0089 0.107 Uiso 0.50 1 d PR . .
H8B H 0.0506 0.2999 -0.0440 0.107 Uiso 0.50 1 d PR . .
C9 C 0.1439(2) -0.0286(5) 0.00726(15) 0.0683(9) Uani 0.50 1 d P . .
H9A H 0.1884 -0.1013 0.0421 0.102 Uiso 0.50 1 d PR . .
H9B H 0.1915 0.0517 -0.0161 0.102 Uiso 0.50 1 d PR . .
N2 N 0.0552(15) 0.144(3) 0.0398(9) 0.073(4) Uani 0.50 1 d P . .
C10 C 0.0710(3) 0.1676(6) -0.02444(16) 0.0682(9) Uani 0.50 1 d P . .
H10A H 0.1480 0.1421 -0.0276 0.102 Uiso 0.50 1 d PR . .
H10B H 0.0515 0.3088 -0.0383 0.102 Uiso 0.50 1 d PR . .
C11 C 0.0705(3) -0.0633(5) 0.06438(17) 0.0712(9) Uani 0.50 1 d P . .
H11A H 0.1469 -0.1056 0.0663 0.107 Uiso 0.50 1 d PR . .
H11B H 0.0512 -0.0634 0.1069 0.107 Uiso 0.50 1 d PR . .
C12 C -0.0762(2) 0.1861(5) 0.03902(15) 0.0676(8) Uani 0.50 1 d P . .
H12A H -0.0945 0.3240 0.0217 0.101 Uiso 0.50 1 d PR . .
H12B H -0.0920 0.1792 0.0823 0.101 Uiso 0.50 1 d PR . .


_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 C1 1.3598(16) . ?
O1 H1 0.8200 . ?
C1 C6 1.3849(19) . ?
C1 C2 1.3849(19) . ?
C2 C3 1.3763(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3957(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3924(17) . ?
C4 C4 1.483(2) 2_655 ?
C5 C6 1.3816(17) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C7 1.394(18) . ?
N1 C8 1.422(17) . ?
N1 C9 1.62(2) . ?
C7 C10 1.542(4) 5 ?
C7 C8 1.727(5) 5 ?
C7 H7A 0.9599 . ?
C7 H7B 0.9601 . ?
C7 H11B 1.0358 . ?
C8 C11 1.537(5) 5 ?
C8 C7 1.727(5) 5 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H10B 0.9330 . ?
C9 C12 1.541(4) 5 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9601 . ?
C9 H10A 1.3130 . ?
C9 H11A 1.3311 . ?
N2 C10 1.40(2) . ?
N2 C11 1.416(19) . ?
N2 C12 1.61(2) . ?
C10 C7 1.542(4) 5 ?
C10 C11 1.911(5) 5 ?
C10 H8B 0.9501 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 C8 1.537(5) 5 ?
C11 C10 1.911(5) 5 ?
C11 H7B 0.9054 . ?
C11 H11A 0.9599 . ?
C11 H11B 0.9601 . ?
C12 C9 1.541(4) 5 ?
C12 H7A 1.2136 . ?
C12 H8A 1.3857 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9602 . ?

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 O1 H1 109.5 . . ?
O1 C1 C6 123.16(12) . . ?
O1 C1 C2 117.83(12) . . ?
C6 C1 C2 119.01(13) . . ?
C3 C2 C1 120.32(13) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.65(12) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.21(11) . . ?
C5 C4 C4 121.99(8) . 2_655 ?
C3 C4 C4 120.81(8) . 2_655 ?
C6 C5 C4 121.42(12) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 120.38(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C7 N1 C8 116.6(10) . . ?
C7 N1 C9 103.8(10) . . ?
C8 N1 C9 103.1(11) . . ?
N1 C7 C10 112.0(6) . 5 ?
N1 C7 C8 97.5(7) . 5 ?
C10 C7 C8 33.17(17) 5 5 ?
N1 C7 H7A 109.2 . . ?
C10 C7 H7A 106.5 5 . ?
C8 C7 H7A 139.2 5 . ?
N1 C7 H7B 109.7 . . ?
C10 C7 H7B 109.8 5 . ?
C8 C7 H7B 88.7 5 . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H11B 106.3 . . ?
C10 C7 H11B 116.2 5 . ?
C8 C7 H11B 94.4 5 . ?
H7A C7 H11B 106.4 . . ?
H7B C7 H11B 6.3 . . ?
N1 C8 C11 111.4(5) . 5 ?
N1 C8 C7 94.5(7) . 5 ?
C11 C8 C7 35.01(17) 5 5 ?
N1 C8 H8A 108.2 . . ?
C11 C8 H8A 104.6 5 . ?
C7 C8 H8A 139.6 5 . ?
N1 C8 H8B 110.6 . . ?
C11 C8 H8B 112.3 5 . ?
C7 C8 H8B 92.1 5 . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H10B 106.6 . . ?
C11 C8 H10B 120.1 5 . ?
C7 C8 H10B 99.3 5 . ?
H8A C8 H10B 105.3 . . ?
H8B C8 H10B 7.8 . . ?
C12 C9 N1 108.6(4) 5 . ?
C12 C9 H9A 110.8 5 . ?
N1 C9 H9A 109.8 . . ?
C12 C9 H9B 108.9 5 . ?
N1 C9 H9B 109.2 . . ?
H9A C9 H9B 109.5 . . ?
C12 C9 H10A 104.0 5 . ?
N1 C9 H10A 77.0 . . ?
H9A C9 H10A 139.4 . . ?
H9B C9 H10A 36.8 . . ?
C12 C9 H11A 106.8 5 . ?
N1 C9 H11A 79.4 . . ?
H9A C9 H11A 34.7 . . ?
H9B C9 H11A 137.7 . . ?
H10A C9 H11A 145.8 . . ?
C10 N2 C11 114.9(13) . . ?
C10 N2 C12 104.7(10) . . ?
C11 N2 C12 103.3(12) . . ?
N2 C10 C7 112.0(6) . 5 ?
N2 C10 C11 98.1(7) . 5 ?
C7 C10 C11 31.34(17) 5 5 ?
N2 C10 H8B 116.5 . . ?
C7 C10 H8B 104.7 5 . ?
C11 C10 H8B 87.6 5 . ?
N2 C10 H10A 109.2 . . ?
C7 C10 H10A 105.8 5 . ?
C11 C10 H10A 136.8 5 . ?
H8B C10 H10A 108.1 . . ?
N2 C10 H10B 109.1 . . ?
C7 C10 H10B 111.2 5 . ?
C11 C10 H10B 91.5 5 . ?
H8B C10 H10B 7.9 . . ?
H10A C10 H10B 109.5 . . ?
N2 C11 C8 112.1(6) . 5 ?
N2 C11 C10 95.9(7) . 5 ?
C8 C11 C10 29.50(19) 5 5 ?
N2 C11 H7B 110.5 . . ?
C8 C11 H7B 103.4 5 . ?
C10 C11 H7B 87.2 5 . ?
N2 C11 H11A 110.3 . . ?
C8 C11 H11A 106.5 5 . ?
C10 C11 H11A 136.0 5 . ?
H7B C11 H11A 113.9 . . ?
N2 C11 H11B 107.7 . . ?
C8 C11 H11B 110.8 5 . ?
C10 C11 H11B 94.5 5 . ?
H7B C11 H11B 7.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C12 N2 109.3(5) 5 . ?
C9 C12 H7A 100.2 5 . ?
N2 C12 H7A 80.9 . . ?
C9 C12 H8A 95.1 5 . ?
N2 C12 H8A 78.7 . . ?
H7A C12 H8A 157.7 . . ?
C9 C12 H12A 106.3 5 . ?
N2 C12 H12A 108.8 . . ?
H7A C12 H12A 146.2 . . ?
H8A C12 H12A 38.4 . . ?
C9 C12 H12B 113.9 5 . ?
N2 C12 H12B 108.9 . . ?
H7A C12 H12B 38.8 . . ?
H8A C12 H12B 144.0 . . ?
H12A C12 H12B 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
O1 C1 C2 C3 -179.55(12) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.74(18) . . . . ?
C2 C3 C4 C4 178.95(13) . . . 2_655 ?
C3 C4 C5 C6 0.86(18) . . . . ?
C4 C4 C5 C6 -178.83(13) 2_655 . . . ?
O1 C1 C6 C5 179.71(12) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C8 N1 C7 C10 50.1(14) . . . 5 ?
C9 N1 C7 C10 -62.5(8) . . . 5 ?
C8 N1 C7 C8 81.0(12) . . . 5 ?
C9 N1 C7 C8 -31.5(7) . . . 5 ?
C7 N1 C8 C11 -47.6(15) . . . 5 ?
C9 N1 C8 C11 65.4(8) . . . 5 ?
C7 N1 C8 C7 -79.2(12) . . . 5 ?
C9 N1 C8 C7 33.8(7) . . . 5 ?
C7 N1 C9 C12 62.7(8) . . . 5 ?
C8 N1 C9 C12 -59.3(8) . . . 5 ?
C11 N2 C10 C7 50.5(15) . . . 5 ?
C12 N2 C10 C7 -62.1(10) . . . 5 ?
C11 N2 C10 C11 79.7(12) . . . 5 ?
C12 N2 C10 C11 -32.9(9) . . . 5 ?
C10 N2 C11 C8 -52.7(15) . . . 5 ?
C12 N2 C11 C8 60.7(11) . . . 5 ?
C10 N2 C11 C10 -78.3(12) . . . 5 ?
C12 N2 C11 C10 35.2(8) . . . 5 ?
C10 N2 C12 C9 57.8(10) . . . 5 ?
C11 N2 C12 C9 -62.8(10) . . . 5 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 995689'
