# Electronic Supplementary Material (ESI) for Organic .
# 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_2q_Chiba



_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_absolute_configuration unk

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C17 H17 N O2'

_chemical_formula_sum            'C17 H17 N O2'

_chemical_formula_weight         267.32



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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'



_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   P2(1)2(1)2(1)



loop_

_symmetry_equiv_pos_as_xyz




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



_cell_length_a                   8.6589(7)

_cell_length_b                   10.1791(6)

_cell_length_c                   15.9766(12)

_cell_angle_alpha                90.00

_cell_angle_beta                 90.00

_cell_angle_gamma                90.00

_cell_volume                     1408.17(18)

_cell_formula_units_Z            4

_cell_measurement_temperature    103(2)

_cell_measurement_reflns_used    2359

_cell_measurement_theta_min      2.55

_cell_measurement_theta_max      29.23



_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.40

_exptl_crystal_size_mid          0.40

_exptl_crystal_size_min          0.36

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.261

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             568

_exptl_absorpt_coefficient_mu    0.083

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.9677

_exptl_absorpt_correction_T_max  0.9709

_exptl_absorpt_process_details   sadabs



_exptl_special_details           
;

?

;



_diffrn_ambient_temperature      103(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            8907

_diffrn_reflns_av_R_equivalents  0.0406

_diffrn_reflns_av_sigmaI/netI    0.0410

_diffrn_reflns_limit_h_min       -12

_diffrn_reflns_limit_h_max       10

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -17

_diffrn_reflns_limit_l_max       23

_diffrn_reflns_theta_min         2.68

_diffrn_reflns_theta_max         31.10

_reflns_number_total             2570

_reflns_number_gt                2326

_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, 2008)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0584P)²+0.1256P] where P=(Fo²+2Fc²)/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         2570

_refine_ls_number_parameters     184

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0458

_refine_ls_R_factor_gt           0.0401

_refine_ls_wR_factor_ref         0.1029

_refine_ls_wR_factor_gt          0.0991

_refine_ls_goodness_of_fit_ref   1.044

_refine_ls_restrained_S_all      1.044

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000



loop_

_atom_site_label

_atom_site_type_symbol

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_occupancy

_atom_site_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group





































C1 C 0.84962(17) 0.12726(15) 0.07019(10) 0.0126(3) Uani 1 1 d . . .
C2 C 0.92688(17) 0.08389(14) 0.15344(9) 0.0117(3) Uani 1 1 d . . .
C3 C 0.9432(2) -0.06694(15) 0.15782(11) 0.0172(3) Uani 1 1 d . . .
H3A H 1.0000 -0.0911 0.2086 0.026 Uiso 1 1 calc R . .
H3B H 0.9995 -0.0983 0.1085 0.026 Uiso 1 1 calc R . .
H3C H 0.8404 -0.1071 0.1591 0.026 Uiso 1 1 calc R . .
C4 C 0.84289(19) 0.13480(17) 0.23032(10) 0.0182(3) Uani 1 1 d . . .
H4A H 0.8989 0.1079 0.2808 0.027 Uiso 1 1 calc R . .
H4B H 0.7381 0.0984 0.2318 0.027 Uiso 1 1 calc R . .
H4C H 0.8374 0.2309 0.2280 0.027 Uiso 1 1 calc R . .
C5 C 1.08660(18) 0.14148(14) 0.13705(10) 0.0126(3) Uani 1 1 d . . .
C6 C 1.20921(18) 0.17167(15) 0.19845(10) 0.0146(3) Uani 1 1 d . . .
C7 C 1.31277(19) 0.27400(17) 0.18152(11) 0.0186(3) Uani 1 1 d . . .
H7 H 1.3017 0.3243 0.1318 0.022 Uiso 1 1 calc R . .
C8 C 1.4317(2) 0.30234(18) 0.23708(12) 0.0235(4) Uani 1 1 d . . .
H8 H 1.5021 0.3713 0.2250 0.028 Uiso 1 1 calc R . .
C9 C 1.4478(2) 0.22989(19) 0.31039(12) 0.0243(4) Uani 1 1 d . . .
H9 H 1.5293 0.2493 0.3482 0.029 Uiso 1 1 calc R . .
C10 C 1.3450(2) 0.12933(19) 0.32823(12) 0.0230(4) Uani 1 1 d . . .
H10 H 1.3560 0.0801 0.3784 0.028 Uiso 1 1 calc R . .
C11 C 1.22564(19) 0.10033(17) 0.27283(11) 0.0190(3) Uani 1 1 d . . .
H11 H 1.1550 0.0318 0.2856 0.023 Uiso 1 1 calc R . .
C12 C 0.72713(18) 0.03693(14) 0.03461(10) 0.0129(3) Uani 1 1 d . . .
C13 C 0.76502(18) -0.06835(15) -0.01765(10) 0.0158(3) Uani 1 1 d . . .
H13 H 0.8696 -0.0826 -0.0332 0.019 Uiso 1 1 calc R . .
C14 C 0.6508(2) -0.15238(16) -0.04709(11) 0.0180(3) Uani 1 1 d . . .
H14 H 0.6778 -0.2246 -0.0818 0.022 Uiso 1 1 calc R . .
C15 C 0.49695(19) -0.13085(16) -0.02583(11) 0.0182(3) Uani 1 1 d . . .
H15 H 0.4186 -0.1874 -0.0467 0.022 Uiso 1 1 calc R . .
C16 C 0.45857(19) -0.02611(16) 0.02611(12) 0.0202(3) Uani 1 1 d . . .
H16 H 0.3537 -0.0114 0.0409 0.024 Uiso 1 1 calc R . .
C17 C 0.57298(19) 0.05713(15) 0.05643(11) 0.0169(3) Uani 1 1 d . . .
H17 H 0.5460 0.1281 0.0922 0.020 Uiso 1 1 calc R . .
N1 N 1.11362(15) 0.16008(13) 0.05870(9) 0.0149(3) Uani 1 1 d . . .
O1 O 0.97919(13) 0.12708(11) 0.01205(7) 0.0153(2) Uani 1 1 d . . .
O2 O 0.79704(14) 0.25559(11) 0.08080(8) 0.0165(2) Uani 1 1 d . . .
H2 H 0.7473 0.2789 0.0382 0.025 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







































C1 O2 1.3937(18) . ?
C1 O1 1.4566(18) . ?
C1 C12 1.514(2) . ?
C1 C2 1.553(2) . ?
C2 C4 1.519(2) . ?
C2 C5 1.525(2) . ?
C2 C3 1.543(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.287(2) . ?
C5 C6 1.478(2) . ?
C6 C11 1.400(2) . ?
C6 C7 1.401(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.395(2) . ?
C12 C13 1.398(2) . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 O1 1.4225(17) . ?
O2 H2 0.8400 . ?



loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle_publ_flag


































































O2 C1 O1 109.29(12) . . ?
O2 C1 C12 112.71(12) . . ?
O1 C1 C12 107.42(12) . . ?
O2 C1 C2 107.64(12) . . ?
O1 C1 C2 102.36(11) . . ?
C12 C1 C2 116.78(13) . . ?
C4 C2 C5 116.24(13) . . ?
C4 C2 C3 110.28(13) . . ?
C5 C2 C3 107.90(13) . . ?
C4 C2 C1 112.92(13) . . ?
C5 C2 C1 97.72(11) . . ?
C3 C2 C1 111.16(13) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 118.96(14) . . ?
N1 C5 C2 112.86(14) . . ?
C6 C5 C2 128.14(14) . . ?
C11 C6 C7 118.98(15) . . ?
C11 C6 C5 121.91(15) . . ?
C7 C6 C5 119.11(14) . . ?
C8 C7 C6 120.35(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.14(17) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.01(16) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.17(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.34(16) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C17 C12 C13 119.14(14) . . ?
C17 C12 C1 119.14(14) . . ?
C13 C12 C1 121.70(14) . . ?
C14 C13 C12 120.49(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.10(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.65(15) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.30(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.32(15) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C5 N1 O1 109.03(12) . . ?
N1 O1 C1 107.21(11) . . ?
C1 O2 H2 109.5 . . ?



_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        31.10

_diffrn_measured_fraction_theta_full 0.994

_refine_diff_density_max         0.300

_refine_diff_density_min         -0.232

_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 926979'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         276.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7331(6)
_cell_length_b                   14.7237(11)
_cell_length_c                   11.9048(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.545(3)
_cell_angle_gamma                90
_cell_volume                     1529.25(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4966
_cell_measurement_theta_min      2.7137
_cell_measurement_theta_max      28.4459
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            23276
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.75
_diffrn_reflns_theta_full        28.75
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3955
_reflns_number_gt                2927
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1448
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.2572P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.00915(16) 0.15643(10) 0.57761(11) 0.0191(3) Uani d . . . 1 . .
H H1 -0.0657 0.0981 0.5874 0.023 Uiso calc U . R 1 . .
C C2 -0.06411(16) 0.20055(9) 0.46391(11) 0.0179(3) Uani d . . . 1 . .
C C3 0.04761(15) 0.15389(9) 0.38735(11) 0.0168(3) Uani d . . . 1 . .
C C4 0.24786(15) 0.08352(9) 0.62861(11) 0.0171(3) Uani d . . . 1 . .
C C5 0.39822(16) 0.06685(10) 0.59865(11) 0.0201(3) Uani d . . . 1 . .
H H5 0.4333 0.0899 0.5298 0.024 Uiso calc U . R 1 . .
C C6 0.49581(17) 0.01685(10) 0.66907(12) 0.0238(3) Uani d . . . 1 . .
H H6 0.5976 0.0054 0.6478 0.029 Uiso calc U . R 1 . .
C C7 0.44737(17) -0.01697(10) 0.77057(12) 0.0245(3) Uani d . . . 1 . .
H H7 0.5153 -0.0511 0.8187 0.029 Uiso calc U . R 1 . .
C C8 0.29868(17) -0.00013(10) 0.80034(12) 0.0228(3) Uani d . . . 1 . .
H H8 0.2645 -0.0231 0.8695 0.027 Uiso calc U . R 1 . .
C C9 0.19847(17) 0.04994(9) 0.73058(11) 0.0195(3) Uani d . . . 1 . .
H H9 0.0968 0.0613 0.7522 0.023 Uiso calc U . R 1 . .
C C10 -0.02929(18) 0.21505(11) 0.67849(12) 0.0266(3) Uani d . . . 1 . .
H H10 0.0457 0.2605 0.6947 0.032 Uiso calc U . R 1 . .
C C11 -0.1437(2) 0.20807(13) 0.74640(13) 0.0375(4) Uani d . . . 1 . .
H H11A -0.2208 0.1634 0.7327 0.045 Uiso calc U . R 1 . .
H H11B -0.1492 0.2477 0.8091 0.045 Uiso calc U . R 1 . .
C C12 -0.23328(16) 0.18025(11) 0.43944(12) 0.0248(3) Uani d . . . 1 . .
H H12A -0.2706 0.2157 0.3741 0.037 Uiso calc U . R 1 . .
H H12B -0.2916 0.1967 0.5049 0.037 Uiso calc U . R 1 . .
H H12C -0.2465 0.1153 0.4235 0.037 Uiso calc U . R 1 . .
C C13 -0.03244(19) 0.30333(10) 0.46301(13) 0.0259(3) Uani d . . . 1 . .
H H13A -0.0533 0.3272 0.387 0.039 Uiso calc U . R 1 . .
H H13B 0.0751 0.3145 0.4859 0.039 Uiso calc U . R 1 . .
H H13C -0.0989 0.3338 0.5155 0.039 Uiso calc U . R 1 . .
C C14 0.03697(15) 0.14696(9) 0.26372(11) 0.0172(3) Uani d . . . 1 . .
C C15 0.12563(16) 0.08182(10) 0.21039(11) 0.0195(3) Uani d . . . 1 . .
H H15 0.1907 0.0428 0.2546 0.023 Uiso calc U . R 1 . .
C C16 0.12007(17) 0.07337(10) 0.09468(12) 0.0219(3) Uani d . . . 1 . .
H H16 0.1813 0.029 0.0601 0.026 Uiso calc U . R 1 . .
C C17 0.02495(17) 0.12970(10) 0.02868(12) 0.0231(3) Uani d . . . 1 . .
H H17 0.0211 0.1241 -0.0509 0.028 Uiso calc U . R 1 . .
C C18 -0.06380(17) 0.19393(10) 0.08008(12) 0.0232(3) Uani d . . . 1 . .
H H18 -0.1291 0.2324 0.0354 0.028 Uiso calc U . R 1 . .
C C19 -0.05844(17) 0.20276(10) 0.19657(12) 0.0210(3) Uani d . . . 1 . .
H H19 -0.1202 0.2471 0.2307 0.025 Uiso calc U . R 1 . .
N N1 0.15113(13) 0.13602(8) 0.55632(9) 0.0191(3) Uani d . . . 1 . .
N N2 0.16676(13) 0.12147(8) 0.44152(9) 0.0193(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.4648(18) ?
C1 C10 . 1.4957(19) ?
C1 C2 . 1.5578(19) ?
C1 H1 . 1.0 ?
C2 C12 . 1.523(2) ?
C2 C3 . 1.5276(19) ?
C2 C13 . 1.538(2) ?
C3 N2 . 1.2910(17) ?
C3 C14 . 1.4741(18) ?
C4 C9 . 1.3967(19) ?
C4 C5 . 1.398(2) ?
C4 N1 . 1.4096(17) ?
C5 C6 . 1.3812(19) ?
C5 H5 . 0.95 ?
C6 C7 . 1.390(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.384(2) ?
C7 H7 . 0.95 ?
C8 C9 . 1.3908(19) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.317(2) ?
C10 H10 . 0.95 ?
C11 H11A . 0.95 ?
C11 H11B . 0.95 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C19 . 1.3961(19) ?
C14 C15 . 1.4023(19) ?
C15 C16 . 1.3819(19) ?
C15 H15 . 0.95 ?
C16 C17 . 1.392(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.383(2) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3917(19) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
N1 N2 . 1.3960(15) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C10 . . 113.87(12) ?
N1 C1 C2 . . 101.25(10) ?
C10 C1 C2 . . 114.48(12) ?
N1 C1 H1 . . 109.0 ?
C10 C1 H1 . . 109.0 ?
C2 C1 H1 . . 109.0 ?
C12 C2 C3 . . 115.94(11) ?
C12 C2 C13 . . 111.40(12) ?
C3 C2 C13 . . 108.57(12) ?
C12 C2 C1 . . 110.08(12) ?
C3 C2 C1 . . 98.66(10) ?
C13 C2 C1 . . 111.58(11) ?
N2 C3 C14 . . 119.13(12) ?
N2 C3 C2 . . 112.97(11) ?
C14 C3 C2 . . 127.82(12) ?
C9 C4 C5 . . 119.31(12) ?
C9 C4 N1 . . 121.66(12) ?
C5 C4 N1 . . 119.00(12) ?
C6 C5 C4 . . 120.01(13) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 121.01(13) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 118.93(13) ?
C8 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
C7 C8 C9 . . 120.99(13) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C8 C9 C4 . . 119.75(13) ?
C8 C9 H9 . . 120.1 ?
C4 C9 H9 . . 120.1 ?
C11 C10 C1 . . 124.56(16) ?
C11 C10 H10 . . 117.7 ?
C1 C10 H10 . . 117.7 ?
C10 C11 H11A . . 120.0 ?
C10 C11 H11B . . 120.0 ?
H11A C11 H11B . . 120.0 ?
C2 C12 H12A . . 109.5 ?
C2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C19 C14 C15 . . 118.09(12) ?
C19 C14 C3 . . 122.72(12) ?
C15 C14 C3 . . 119.19(12) ?
C16 C15 C14 . . 121.15(13) ?
C16 C15 H15 . . 119.4 ?
C14 C15 H15 . . 119.4 ?
C15 C16 C17 . . 120.19(13) ?
C15 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C18 C17 C16 . . 119.34(13) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
C17 C18 C19 . . 120.68(13) ?
C17 C18 H18 . . 119.7 ?
C19 C18 H18 . . 119.7 ?
C18 C19 C14 . . 120.56(13) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
N2 N1 C4 . . 115.57(11) ?
N2 N1 C1 . . 109.67(10) ?
C4 N1 C1 . . 123.94(11) ?
C3 N2 N1 . . 108.70(11) ?

_database_code_depnum_ccdc_archive 'CCDC 996573'
#######################################################################
#
#                 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_I

_chemical_name_systematic        ?

_chemical_name_common            ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C23 H20 N2'

_chemical_formula_iupac          ?

_chemical_formula_weight         324.41




_chemical_melting_point          ?




_space_group_crystal_system      monoclinic

_space_group_name_H-M_alt        'P 1 21/c 1'

_space_group_name_Hall           '-P 2ybc'

loop_

_space_group_symop_operation_xyz




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




_cell_length_a                   20.6660(16)

_cell_length_b                   9.5448(6)

_cell_length_c                   20.3329(18)

_cell_angle_alpha                90

_cell_angle_beta                 117.451(5)

_cell_angle_gamma                90

_cell_volume                     3559.1(5)

_cell_formula_units_Z            8

_cell_measurement_reflns_used    2508

_cell_measurement_theta_min      2.2575

_cell_measurement_theta_max      22.6929

_cell_measurement_temperature    103.(2)




_exptl_crystal_description       block

_exptl_crystal_colour            yellow

_exptl_crystal_size_max          0.340

_exptl_crystal_size_mid          0.320

_exptl_crystal_size_min          0.240

_exptl_crystal_density_diffrn    1.211

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1376




_exptl_absorpt_coefficient_mu    0.071

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_absorpt_correction_T_min  0.85

_exptl_absorpt_correction_T_max  0.98




_exptl_special_details           
;
 
;




_diffrn_ambient_temperature      103.(2)




_diffrn_source                   ?

_diffrn_source_type              ?




_diffrn_radiation_type           ?

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  ?




_diffrn_measurement_device_type  ?

_diffrn_measurement_method       ?




_diffrn_detector_area_resol_mean 8.3333




_diffrn_reflns_number            25014

_diffrn_reflns_av_R_equivalents  0.0719

_diffrn_reflns_av_unetI/netI     0.0819

_diffrn_reflns_theta_min         2.00

_diffrn_reflns_theta_max         26.07

_diffrn_reflns_theta_full        26.07

_diffrn_measured_fraction_theta_max 0.988

_diffrn_measured_fraction_theta_full 0.988

_diffrn_reflns_limit_h_min       -25

_diffrn_reflns_limit_h_max       24

_diffrn_reflns_limit_k_min       -11

_diffrn_reflns_limit_k_max       11

_diffrn_reflns_limit_l_min       -24

_diffrn_reflns_limit_l_max       25




_refine_special_details          
;
 
;




_reflns_number_total             6970

_reflns_number_gt                4434

_reflns_threshold_expression     'I > 2σ(I)'




_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_R_factor_all          0.0946

_refine_ls_R_factor_gt           0.0517

_refine_ls_wR_factor_gt          0.1089

_refine_ls_wR_factor_ref         0.1293

_refine_ls_goodness_of_fit_ref   0.998

_refine_ls_restrained_S_all      0.998

_refine_ls_number_reflns         6970

_refine_ls_number_parameters     451

_refine_ls_number_restraints     0

_refine_ls_hydrogen_treatment    constr

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.2944P] where P=(Fo²+2Fc²)/3'




_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     ?

_atom_sites_solution_secondary   ?




_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.226

_refine_diff_density_min         -0.230

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?




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'




_computing_data_collection       ?

_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'

_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'

_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

_computing_molecular_graphics    ?

_computing_publication_material  ?




loop_

_atom_site_type_symbol

_atom_site_label

_atom_site_fract_x

_atom_site_fract_y

_atom_site_fract_z

_atom_site_U_iso_or_equiv

_atom_site_adp_type

_atom_site_calc_flag

_atom_site_refinement_flags_adp

_atom_site_refinement_flags_occupancy

_atom_site_refinement_flags_posn

_atom_site_occupancy

_atom_site_disorder_assembly

_atom_site_disorder_group


























































































C C1 0.38871(12) 0.2598(2) 0.26351(12) 0.0217(5) Uani d . . . 1 . .
H H1 0.339 0.2853 0.2239 0.026 Uiso calc U . R 1 . .
C C2 0.44347(11) 0.2484(2) 0.23067(12) 0.0198(5) Uani d . . . 1 . .
H H2 0.4562 0.148 0.2286 0.024 Uiso calc U . R 1 . .
C C3 0.50863(11) 0.32492(19) 0.29081(12) 0.0174(5) Uani d . . . 1 . .
C C4 0.38857(11) 0.44352(19) 0.35512(11) 0.0183(5) Uani d . . . 1 . .
C C5 0.31524(12) 0.4208(2) 0.33697(12) 0.0217(5) Uani d . . . 1 . .
H H5 0.2871 0.3558 0.2991 0.026 Uiso calc U . R 1 . .
C C6 0.28363(12) 0.4927(2) 0.37397(12) 0.0267(5) Uani d . . . 1 . .
H H6 0.2338 0.4766 0.361 0.032 Uiso calc U . R 1 . .
C C7 0.32306(12) 0.5872(2) 0.42915(13) 0.0303(6) Uani d . . . 1 . .
H H7 0.3008 0.6364 0.454 0.036 Uiso calc U . R 1 . .
C C8 0.39607(13) 0.6096(2) 0.44792(13) 0.0304(6) Uani d . . . 1 . .
H H8 0.4239 0.6742 0.4861 0.036 Uiso calc U . R 1 . .
C C9 0.42859(12) 0.5388(2) 0.41160(12) 0.0231(5) Uani d . . . 1 . .
H H9 0.4785 0.555 0.4251 0.028 Uiso calc U . R 1 . .
C C10 0.38613(13) 0.1235(2) 0.29976(14) 0.0291(6) Uani d . . . 1 . .
H H10 0.3541 0.053 0.2689 0.035 Uiso calc U . R 1 . .
C C11 0.42472(14) 0.0944(2) 0.37063(15) 0.0379(7) Uani d . . . 1 . .
H H11A 0.4574 0.1621 0.4033 0.045 Uiso calc U . R 1 . .
H H11B 0.4199 0.0057 0.3891 0.045 Uiso calc U . R 1 . .
C C12 0.41683(12) 0.3156(2) 0.15456(12) 0.0210(5) Uani d . . . 1 . .
C C13 0.39750(13) 0.4559(2) 0.14374(13) 0.0320(6) Uani d . . . 1 . .
H H13 0.4012 0.5111 0.1842 0.038 Uiso calc U . R 1 . .
C C14 0.37286(15) 0.5162(2) 0.07447(14) 0.0393(7) Uani d . . . 1 . .
H H14 0.3594 0.6123 0.0677 0.047 Uiso calc U . R 1 . .
C C15 0.36761(14) 0.4379(2) 0.01496(13) 0.0363(6) Uani d . . . 1 . .
H H15 0.3511 0.4801 -0.0324 0.044 Uiso calc U . R 1 . .
C C16 0.38660(13) 0.2972(2) 0.02499(13) 0.0303(6) Uani d . . . 1 . .
H H16 0.3829 0.2421 -0.0155 0.036 Uiso calc U . R 1 . .
C C17 0.41106(12) 0.2374(2) 0.09470(12) 0.0252(5) Uani d . . . 1 . .
H H17 0.4241 0.141 0.1015 0.03 Uiso calc U . R 1 . .
C C18 0.58345(11) 0.32019(19) 0.30094(12) 0.0178(5) Uani d . . . 1 . .
C C19 0.60019(12) 0.25704(19) 0.24844(12) 0.0213(5) Uani d . . . 1 . .
H H19 0.5621 0.2202 0.2041 0.026 Uiso calc U . R 1 . .
C C20 0.67192(12) 0.2478(2) 0.26068(13) 0.0234(5) Uani d . . . 1 . .
H H20 0.6826 0.2045 0.2247 0.028 Uiso calc U . R 1 . .
C C21 0.72783(12) 0.3013(2) 0.32478(13) 0.0253(5) Uani d . . . 1 . .
H H21 0.7769 0.2941 0.3331 0.03 Uiso calc U . R 1 . .
C C22 0.71215(12) 0.3657(2) 0.37734(13) 0.0240(5) Uani d . . . 1 . .
H H22 0.7505 0.4035 0.4212 0.029 Uiso calc U . R 1 . .
C C23 0.64096(11) 0.37446(19) 0.36557(12) 0.0197(5) Uani d . . . 1 . .
H H23 0.6307 0.4179 0.4018 0.024 Uiso calc U . R 1 . .
C C24 0.02687(11) 0.64560(19) 0.37415(11) 0.0166(5) Uani d . . . 1 . .
H H24 -0.0096 0.6296 0.3928 0.02 Uiso calc U . R 1 . .
C C25 -0.01106(11) 0.64895(19) 0.28830(11) 0.0165(5) Uani d . . . 1 . .
H H25 -0.0147 0.7478 0.2706 0.02 Uiso calc U . R 1 . .
C C26 0.04521(11) 0.56956(18) 0.27417(11) 0.0151(5) Uani d . . . 1 . .
C C27 0.11402(11) 0.45840(19) 0.45771(11) 0.0168(5) Uani d . . . 1 . .
C C28 0.16548(11) 0.35426(19) 0.46821(12) 0.0189(5) Uani d . . . 1 . .
H H28 0.176 0.3297 0.4289 0.023 Uiso calc U . R 1 . .
C C29 0.20125(12) 0.2866(2) 0.53632(13) 0.0253(5) Uani d . . . 1 . .
H H29 0.2358 0.2153 0.5429 0.03 Uiso calc U . R 1 . .
C C30 0.18725(12) 0.3216(2) 0.59459(13) 0.0266(6) Uani d . . . 1 . .
H H30 0.2117 0.2744 0.6408 0.032 Uiso calc U . R 1 . .
C C31 0.13723(12) 0.4265(2) 0.58482(12) 0.0238(5) Uani d . . . 1 . .
H H31 0.1276 0.4516 0.6247 0.029 Uiso calc U . R 1 . .
C C32 0.10097(11) 0.4953(2) 0.51713(12) 0.0194(5) Uani d . . . 1 . .
H H32 0.0672 0.5677 0.5112 0.023 Uiso calc U . R 1 . .
C C33 0.06843(13) 0.7791(2) 0.40544(12) 0.0230(5) Uani d . . . 1 . .
H H33 0.0407 0.8591 0.4047 0.028 Uiso calc U . R 1 . .
C C34 0.13923(13) 0.7958(2) 0.43369(13) 0.0303(6) Uani d . . . 1 . .
H H34A 0.1693 0.7189 0.4357 0.036 Uiso calc U . R 1 . .
H H34B 0.1604 0.8848 0.4521 0.036 Uiso calc U . R 1 . .
C C35 -0.08560(11) 0.57987(19) 0.25125(11) 0.0161(5) Uani d . . . 1 . .
C C36 -0.09382(12) 0.4377(2) 0.26131(12) 0.0199(5) Uani d . . . 1 . .
H H36 -0.0521 0.383 0.2914 0.024 Uiso calc U . R 1 . .
C C37 -0.16196(12) 0.3750(2) 0.22807(12) 0.0235(5) Uani d . . . 1 . .
H H37 -0.1666 0.278 0.2354 0.028 Uiso calc U . R 1 . .
C C38 -0.22319(12) 0.4529(2) 0.18427(13) 0.0255(5) Uani d . . . 1 . .
H H38 -0.27 0.4102 0.1619 0.031 Uiso calc U . R 1 . .
C C39 -0.21563(12) 0.5942(2) 0.17328(13) 0.0263(6) Uani d . . . 1 . .
H H39 -0.2573 0.6485 0.1427 0.032 Uiso calc U . R 1 . .
C C40 -0.14718(12) 0.6562(2) 0.20693(12) 0.0211(5) Uani d . . . 1 . .
H H40 -0.1426 0.7532 0.1993 0.025 Uiso calc U . R 1 . .
C C41 0.04919(11) 0.57182(18) 0.20445(11) 0.0159(5) Uani d . . . 1 . .
C C42 0.10843(12) 0.51188(19) 0.19844(12) 0.0212(5) Uani d . . . 1 . .
H H42 0.1449 0.4627 0.2394 0.025 Uiso calc U . R 1 . .
C C43 0.11419(13) 0.5237(2) 0.13391(13) 0.0265(5) Uani d . . . 1 . .
H H43 0.1546 0.4827 0.1308 0.032 Uiso calc U . R 1 . .
C C44 0.06168(13) 0.5947(2) 0.07352(13) 0.0283(6) Uani d . . . 1 . .
H H44 0.0664 0.6037 0.0294 0.034 Uiso calc U . R 1 . .
C C45 0.00216(13) 0.6525(2) 0.07778(12) 0.0237(5) Uani d . . . 1 . .
H H45 -0.0344 0.7001 0.0362 0.028 Uiso calc U . R 1 . .
C C46 -0.00398(12) 0.64108(19) 0.14269(12) 0.0195(5) Uani d . . . 1 . .
H H46 -0.0449 0.6809 0.1452 0.023 Uiso calc U . R 1 . .
N N1 0.42015(9) 0.37578(17) 0.31651(10) 0.0212(4) Uani d . . . 1 . .
N N2 0.49264(9) 0.39657(16) 0.33568(10) 0.0191(4) Uani d . . . 1 . .
N N3 0.07473(9) 0.52311(16) 0.38915(9) 0.0188(4) Uani d . . . 1 . .
N N4 0.09017(9) 0.49716(15) 0.33118(9) 0.0166(4) Uani d . . . 1 . .








_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_site_symmetry_2

_geom_bond_distance

_geom_bond_publ_flag
































































































C1 N1 . 1.471(3) ?
C1 C10 . 1.508(3) ?
C1 C2 . 1.560(3) ?
C1 H1 . 1.0 ?
C2 C3 . 1.524(3) ?
C2 C12 . 1.524(3) ?
C2 H2 . 1.0 ?
C3 N2 . 1.299(3) ?
C3 C18 . 1.463(3) ?
C4 N1 . 1.390(3) ?
C4 C9 . 1.398(3) ?
C4 C5 . 1.401(3) ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.376(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.392(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.382(3) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.315(3) ?
C10 H10 . 0.95 ?
C11 H11A . 0.95 ?
C11 H11B . 0.95 ?
C12 C17 . 1.386(3) ?
C12 C13 . 1.386(3) ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.383(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.95 ?
C16 C17 . 1.389(3) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.401(3) ?
C18 C23 . 1.403(3) ?
C19 C20 . 1.388(3) ?
C19 H19 . 0.95 ?
C20 C21 . 1.380(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.395(3) ?
C21 H21 . 0.95 ?
C22 C23 . 1.380(3) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 N3 . 1.470(2) ?
C24 C33 . 1.504(3) ?
C24 C25 . 1.549(3) ?
C24 H24 . 1.0 ?
C25 C35 . 1.518(3) ?
C25 C26 . 1.522(3) ?
C25 H25 . 1.0 ?
C26 N4 . 1.301(2) ?
C26 C41 . 1.458(3) ?
C27 N3 . 1.393(2) ?
C27 C28 . 1.398(3) ?
C27 C32 . 1.399(3) ?
C28 C29 . 1.392(3) ?
C28 H28 . 0.95 ?
C29 C30 . 1.384(3) ?
C29 H29 . 0.95 ?
C30 C31 . 1.386(3) ?
C30 H30 . 0.95 ?
C31 C32 . 1.392(3) ?
C31 H31 . 0.95 ?
C32 H32 . 0.95 ?
C33 C34 . 1.312(3) ?
C33 H33 . 0.95 ?
C34 H34A . 0.95 ?
C34 H34B . 0.95 ?
C35 C40 . 1.380(3) ?
C35 C36 . 1.395(3) ?
C36 C37 . 1.386(3) ?
C36 H36 . 0.95 ?
C37 C38 . 1.381(3) ?
C37 H37 . 0.95 ?
C38 C39 . 1.388(3) ?
C38 H38 . 0.95 ?
C39 C40 . 1.388(3) ?
C39 H39 . 0.95 ?
C40 H40 . 0.95 ?
C41 C46 . 1.396(3) ?
C41 C42 . 1.407(3) ?
C42 C43 . 1.376(3) ?
C42 H42 . 0.95 ?
C43 C44 . 1.384(3) ?
C43 H43 . 0.95 ?
C44 C45 . 1.387(3) ?
C44 H44 . 0.95 ?
C45 C46 . 1.387(3) ?
C45 H45 . 0.95 ?
C46 H46 . 0.95 ?
N1 N2 . 1.377(2) ?
N3 N4 . 1.378(2) ?




loop_

_geom_angle_atom_site_label_1

_geom_angle_atom_site_label_2

_geom_angle_atom_site_label_3

_geom_angle_site_symmetry_1

_geom_angle_site_symmetry_3

_geom_angle

_geom_angle_publ_flag






























































































































































N1 C1 C10 . . 113.23(19) ?
N1 C1 C2 . . 101.72(16) ?
C10 C1 C2 . . 110.21(17) ?
N1 C1 H1 . . 110.5 ?
C10 C1 H1 . . 110.5 ?
C2 C1 H1 . . 110.5 ?
C3 C2 C12 . . 112.65(17) ?
C3 C2 C1 . . 99.80(16) ?
C12 C2 C1 . . 114.30(17) ?
C3 C2 H2 . . 109.9 ?
C12 C2 H2 . . 109.9 ?
C1 C2 H2 . . 109.9 ?
N2 C3 C18 . . 120.79(19) ?
N2 C3 C2 . . 113.51(19) ?
C18 C3 C2 . . 125.69(19) ?
N1 C4 C9 . . 120.83(19) ?
N1 C4 C5 . . 120.76(19) ?
C9 C4 C5 . . 118.4(2) ?
C6 C5 C4 . . 120.3(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 121.2(2) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 C8 . . 118.9(2) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C9 C8 C7 . . 120.7(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C4 . . 120.5(2) ?
C8 C9 H9 . . 119.7 ?
C4 C9 H9 . . 119.7 ?
C11 C10 C1 . . 125.3(2) ?
C11 C10 H10 . . 117.4 ?
C1 C10 H10 . . 117.4 ?
C10 C11 H11A . . 120.0 ?
C10 C11 H11B . . 120.0 ?
H11A C11 H11B . . 120.0 ?
C17 C12 C13 . . 118.7(2) ?
C17 C12 C2 . . 120.63(18) ?
C13 C12 C2 . . 120.70(19) ?
C14 C13 C12 . . 120.5(2) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 120.6(2) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C16 . . 119.4(2) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C15 C16 C17 . . 119.5(2) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C12 C17 C16 . . 121.2(2) ?
C12 C17 H17 . . 119.4 ?
C16 C17 H17 . . 119.4 ?
C19 C18 C23 . . 118.2(2) ?
C19 C18 C3 . . 121.47(19) ?
C23 C18 C3 . . 120.3(2) ?
C20 C19 C18 . . 120.6(2) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C21 C20 C19 . . 120.4(2) ?
C21 C20 H20 . . 119.8 ?
C19 C20 H20 . . 119.8 ?
C20 C21 C22 . . 119.8(2) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.0(2) ?
C23 C22 H22 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C22 C23 C18 . . 121.0(2) ?
C22 C23 H23 . . 119.5 ?
C18 C23 H23 . . 119.5 ?
N3 C24 C33 . . 112.82(17) ?
N3 C24 C25 . . 101.11(15) ?
C33 C24 C25 . . 110.65(16) ?
N3 C24 H24 . . 110.6 ?
C33 C24 H24 . . 110.6 ?
C25 C24 H24 . . 110.6 ?
C35 C25 C26 . . 112.26(16) ?
C35 C25 C24 . . 114.88(17) ?
C26 C25 C24 . . 99.70(15) ?
C35 C25 H25 . . 109.9 ?
C26 C25 H25 . . 109.9 ?
C24 C25 H25 . . 109.9 ?
N4 C26 C41 . . 122.50(18) ?
N4 C26 C25 . . 112.98(18) ?
C41 C26 C25 . . 124.52(17) ?
N3 C27 C28 . . 121.3(2) ?
N3 C27 C32 . . 119.82(18) ?
C28 C27 C32 . . 118.87(19) ?
C29 C28 C27 . . 120.0(2) ?
C29 C28 H28 . . 120.0 ?
C27 C28 H28 . . 120.0 ?
C30 C29 C28 . . 121.0(2) ?
C30 C29 H29 . . 119.5 ?
C28 C29 H29 . . 119.5 ?
C29 C30 C31 . . 119.2(2) ?
C29 C30 H30 . . 120.4 ?
C31 C30 H30 . . 120.4 ?
C30 C31 C32 . . 120.6(2) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
C31 C32 C27 . . 120.3(2) ?
C31 C32 H32 . . 119.8 ?
C27 C32 H32 . . 119.8 ?
C34 C33 C24 . . 126.3(2) ?
C34 C33 H33 . . 116.8 ?
C24 C33 H33 . . 116.8 ?
C33 C34 H34A . . 120.0 ?
C33 C34 H34B . . 120.0 ?
H34A C34 H34B . . 120.0 ?
C40 C35 C36 . . 118.14(19) ?
C40 C35 C25 . . 120.92(17) ?
C36 C35 C25 . . 120.94(18) ?
C37 C36 C35 . . 120.91(19) ?
C37 C36 H36 . . 119.5 ?
C35 C36 H36 . . 119.5 ?
C38 C37 C36 . . 120.33(19) ?
C38 C37 H37 . . 119.8 ?
C36 C37 H37 . . 119.8 ?
C37 C38 C39 . . 119.3(2) ?
C37 C38 H38 . . 120.4 ?
C39 C38 H38 . . 120.4 ?
C38 C39 C40 . . 120.0(2) ?
C38 C39 H39 . . 120.0 ?
C40 C39 H39 . . 120.0 ?
C35 C40 C39 . . 121.33(18) ?
C35 C40 H40 . . 119.3 ?
C39 C40 H40 . . 119.3 ?
C46 C41 C42 . . 118.0(2) ?
C46 C41 C26 . . 120.53(19) ?
C42 C41 C26 . . 121.33(18) ?
C43 C42 C41 . . 120.7(2) ?
C43 C42 H42 . . 119.6 ?
C41 C42 H42 . . 119.6 ?
C42 C43 C44 . . 120.6(2) ?
C42 C43 H43 . . 119.7 ?
C44 C43 H43 . . 119.7 ?
C43 C44 C45 . . 119.7(2) ?
C43 C44 H44 . . 120.2 ?
C45 C44 H44 . . 120.2 ?
C44 C45 C46 . . 120.0(2) ?
C44 C45 H45 . . 120.0 ?
C46 C45 H45 . . 120.0 ?
C45 C46 C41 . . 120.9(2) ?
C45 C46 H46 . . 119.5 ?
C41 C46 H46 . . 119.5 ?
N2 N1 C4 . . 120.38(17) ?
N2 N1 C1 . . 111.79(16) ?
C4 N1 C1 . . 126.87(17) ?
C3 N2 N1 . . 108.73(17) ?
N4 N3 C27 . . 121.22(16) ?
N4 N3 C24 . . 111.38(15) ?
C27 N3 C24 . . 125.89(17) ?
C26 N4 N3 . . 108.35(16) ?





_database_code_depnum_ccdc_archive 'CCDC 995494'
