# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_130938lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1419576'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N O0.50'
_chemical_formula_weight         290.35

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 1 2/c 1'
_symmetry_space_group_name_hall  '-C 2yc'

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                   15.8693(8)
_cell_length_b                   9.9218(5)
_cell_length_c                   20.1836(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.4240(10)
_cell_angle_gamma                90.00
_cell_volume                     3103.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2500
_cell_measurement_theta_min      2.4374
_cell_measurement_theta_max      26.4131

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8850
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            12498
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3210
_reflns_number_gt                2325
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0401P)²+1.4539P] 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         3210
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.0000 0.18207(15) 0.2500 0.0346(4) Uani 1 2 d S . .
H1A H 0.0232 0.2428 0.2874 0.050 Uiso 1 1 d . . .
N1 N 0.07567(8) 0.32841(13) 0.36966(6) 0.0249(3) Uani 1 1 d . . .
C1 C 0.13108(10) 0.67260(16) 0.33316(7) 0.0289(4) Uani 1 1 d . . .
H1 H 0.1312 0.7276 0.2946 0.035 Uiso 1 1 calc R . .
C2 C 0.10246(9) 0.54303(16) 0.32474(7) 0.0268(3) Uani 1 1 d . . .
H2 H 0.0822 0.5085 0.2803 0.032 Uiso 1 1 calc R . .
C3 C 0.10257(9) 0.45937(15) 0.38137(7) 0.0229(3) Uani 1 1 d . . .
C4 C 0.07752(9) 0.25104(15) 0.42281(7) 0.0233(3) Uani 1 1 d . . .
H4 H 0.0592 0.1603 0.4145 0.028 Uiso 1 1 calc R . .
C5 C 0.10460(9) 0.29166(14) 0.49144(7) 0.0213(3) Uani 1 1 d . . .
C6 C 0.10070(9) 0.19030(14) 0.54518(7) 0.0217(3) Uani 1 1 d . . .
C7 C 0.05838(9) 0.21816(16) 0.59744(7) 0.0254(3) Uani 1 1 d . . .
H7 H 0.0331 0.3043 0.6001 0.030 Uiso 1 1 calc R . .
C8 C 0.05299(10) 0.12102(16) 0.64545(8) 0.0279(4) Uani 1 1 d . . .
H8 H 0.0235 0.1407 0.6806 0.033 Uiso 1 1 calc R . .
C9 C 0.09026(10) -0.00491(16) 0.64291(8) 0.0289(4) Uani 1 1 d . . .
H9 H 0.0867 -0.0710 0.6763 0.035 Uiso 1 1 calc R . .
C10 C 0.13227(8) 0.42335(14) 0.50438(7) 0.0199(3) Uani 1 1 d . . .
C11 C 0.13135(8) 0.51145(15) 0.44795(7) 0.0209(3) Uani 1 1 d . . .
C12 C 0.16061(9) 0.64716(15) 0.45476(7) 0.0231(3) Uani 1 1 d . . .
H12 H 0.1805 0.6842 0.4987 0.028 Uiso 1 1 calc R . .
C13 C 0.16046(10) 0.72523(16) 0.39890(7) 0.0273(3) Uani 1 1 d . . .
H13 H 0.1803 0.8157 0.4045 0.033 Uiso 1 1 calc R . .
C14 C 0.16685(9) 0.47065(14) 0.57525(7) 0.0198(3) Uani 1 1 d . . .
C15 C 0.12757(9) 0.57477(14) 0.60382(7) 0.0222(3) Uani 1 1 d . . .
H15 H 0.0783 0.6186 0.5776 0.027 Uiso 1 1 calc R . .
C16 C 0.15989(10) 0.61489(15) 0.67027(7) 0.0263(3) Uani 1 1 d . . .
H16 H 0.1321 0.6848 0.6896 0.032 Uiso 1 1 calc R . .
C17 C 0.23260(10) 0.55332(16) 0.70858(7) 0.0272(3) Uani 1 1 d . . .
H17 H 0.2550 0.5815 0.7539 0.033 Uiso 1 1 calc R . .
C18 C 0.27264(9) 0.45033(16) 0.68040(7) 0.0271(4) Uani 1 1 d . . .
H18 H 0.3229 0.4085 0.7064 0.033 Uiso 1 1 calc R . .
C19 C 0.23941(9) 0.40836(15) 0.61442(7) 0.0234(3) Uani 1 1 d . . .
H19 H 0.2664 0.3365 0.5958 0.028 Uiso 1 1 calc R . .
C20 C 0.13734(10) 0.06309(15) 0.54240(8) 0.0280(4) Uani 1 1 d . . .
H20 H 0.1657 0.0424 0.5068 0.034 Uiso 1 1 calc R . .
C21 C 0.13264(10) -0.03338(16) 0.59126(8) 0.0308(4) Uani 1 1 d . . .
H21 H 0.1585 -0.1192 0.5893 0.037 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
O1 H1A 0.9741 . ?
N1 C4 1.3144(18) . ?
N1 C3 1.3722(19) . ?
C1 C2 1.362(2) . ?
C1 C13 1.409(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.412(2) . ?
C2 H2 0.9500 . ?
C3 C11 1.4204(19) . ?
C4 C5 1.418(2) . ?
C4 H4 0.9500 . ?
C5 C10 1.385(2) . ?
C5 C6 1.4901(19) . ?
C6 C7 1.3946(19) . ?
C6 C20 1.396(2) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C21 1.386(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4333(19) . ?
C10 C14 1.4931(19) . ?
C11 C12 1.421(2) . ?
C12 C13 1.367(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3934(19) . ?
C14 C15 1.394(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C4 N1 C3 117.45(12) . . ?
C2 C1 C13 120.09(14) . . ?
C2 C1 H1 120.0 . . ?
C13 C1 H1 120.0 . . ?
C1 C2 C3 120.76(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
N1 C3 C2 118.10(13) . . ?
N1 C3 C11 122.15(13) . . ?
C2 C3 C11 119.74(14) . . ?
N1 C4 C5 125.47(14) . . ?
N1 C4 H4 117.3 . . ?
C5 C4 H4 117.3 . . ?
C10 C5 C4 118.00(13) . . ?
C10 C5 C6 124.09(12) . . ?
C4 C5 C6 117.90(13) . . ?
C7 C6 C20 118.83(13) . . ?
C7 C6 C5 121.26(13) . . ?
C20 C6 C5 119.87(13) . . ?
C8 C7 C6 120.30(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.70(14) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C21 C9 C8 119.40(14) . . ?
C21 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C5 C10 C11 118.48(13) . . ?
C5 C10 C14 120.88(12) . . ?
C11 C10 C14 120.56(12) . . ?
C3 C11 C12 117.90(13) . . ?
C3 C11 C10 118.44(13) . . ?
C12 C11 C10 123.62(13) . . ?
C13 C12 C11 120.96(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C1 120.53(15) . . ?
C12 C13 H13 119.7 . . ?
C1 C13 H13 119.7 . . ?
C19 C14 C15 118.84(13) . . ?
C19 C14 C10 119.52(13) . . ?
C15 C14 C10 121.63(13) . . ?
C16 C15 C14 120.50(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.23(14) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.72(14) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.10(14) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.59(14) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C6 120.57(14) . . ?
C21 C20 H20 119.7 . . ?
C6 C20 H20 119.7 . . ?
C9 C21 C20 120.19(15) . . ?
C9 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ch16647
_database_code_depnum_ccdc_archive 'CCDC 1419577'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N'
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.40

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.6366(11)
_cell_length_b                   9.9502(13)
_cell_length_c                   11.2433(15)
_cell_angle_alpha                101.660(2)
_cell_angle_beta                 94.005(2)
_cell_angle_gamma                111.536(2)
_cell_volume                     869.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_T_max  0.9706
_exptl_absorpt_process_details   ?

_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  ?
_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            7792
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3089
_reflns_number_gt                2576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0799P)²+0.0757P] 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         3089
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.03504(16) 0.86147(14) 0.06458(12) 0.0327(3) Uani 1 1 d . . .
H1 H -0.0440 0.9073 0.0637 0.039 Uiso 1 1 calc R . .
C2 C 0.03196(15) 0.77851(13) 0.15275(11) 0.0303(3) Uani 1 1 d . . .
C3 C -0.09529(15) 0.76474(14) 0.23742(11) 0.0319(3) Uani 1 1 d . . .
C4 C -0.09782(18) 0.89183(15) 0.31503(13) 0.0421(4) Uani 1 1 d . . .
H4 H -0.0169 0.9872 0.3148 0.050 Uiso 1 1 calc R . .
C5 C -0.2178(2) 0.88037(18) 0.39289(14) 0.0515(4) Uani 1 1 d . . .
H5 H -0.2171 0.9678 0.4465 0.062 Uiso 1 1 calc R . .
C6 C -0.33767(18) 0.74341(19) 0.39287(13) 0.0504(4) Uani 1 1 d . . .
H6 H -0.4202 0.7362 0.4455 0.060 Uiso 1 1 calc R . .
C7 C -0.33724(17) 0.61632(17) 0.31576(13) 0.0457(4) Uani 1 1 d . . .
H7 H -0.4201 0.5216 0.3152 0.055 Uiso 1 1 calc R . .
C8 C -0.21641(16) 0.62651(15) 0.23932(12) 0.0371(3) Uani 1 1 d . . .
H8 H -0.2161 0.5384 0.1877 0.045 Uiso 1 1 calc R . .
C9 C 0.14864(15) 0.71229(13) 0.15584(11) 0.0292(3) Uani 1 1 d . . .
C10 C 0.15212(15) 0.62100(14) 0.24598(11) 0.0307(3) Uani 1 1 d . . .
C11 C 0.20628(17) 0.68660(16) 0.37103(12) 0.0400(3) Uani 1 1 d . . .
H11 H 0.2438 0.7916 0.4006 0.048 Uiso 1 1 calc R . .
C12 C 0.20553(19) 0.59885(19) 0.45264(13) 0.0509(4) Uani 1 1 d . . .
H12 H 0.2444 0.6443 0.5378 0.061 Uiso 1 1 calc R . .
C13 C 0.14865(18) 0.44576(19) 0.41087(15) 0.0509(4) Uani 1 1 d . . .
H13 H 0.1472 0.3861 0.4673 0.061 Uiso 1 1 calc R . .
C14 C 0.09398(18) 0.37980(16) 0.28705(14) 0.0445(4) Uani 1 1 d . . .
H14 H 0.0536 0.2745 0.2581 0.053 Uiso 1 1 calc R . .
C15 C 0.09810(16) 0.46745(14) 0.20489(13) 0.0372(3) Uani 1 1 d . . .
H15 H 0.0635 0.4219 0.1194 0.045 Uiso 1 1 calc R . .
C16 C 0.26532(15) 0.73377(13) 0.07176(11) 0.0295(3) Uani 1 1 d . . .
C17 C 0.39640(16) 0.67701(14) 0.07307(12) 0.0356(3) Uani 1 1 d . . .
H17 H 0.4060 0.6230 0.1319 0.043 Uiso 1 1 calc R . .
C18 C 0.50586(16) 0.69923(15) -0.00794(13) 0.0387(3) Uani 1 1 d . . .
H18 H 0.5921 0.6617 -0.0041 0.046 Uiso 1 1 calc R . .
C19 C 0.49516(16) 0.77791(14) -0.09956(12) 0.0360(3) Uani 1 1 d . . .
C20 C 0.60757(17) 0.79857(16) -0.18590(14) 0.0444(4) Uani 1 1 d . . .
H20 H 0.6916 0.7582 -0.1843 0.053 Uiso 1 1 calc R . .
C21 C 0.59729(18) 0.87571(17) -0.27176(14) 0.0477(4) Uani 1 1 d . . .
H21 H 0.6732 0.8878 -0.3297 0.057 Uiso 1 1 calc R . .
C22 C 0.47524(18) 0.93697(16) -0.27451(13) 0.0463(4) Uani 1 1 d . . .
H22 H 0.4696 0.9914 -0.3339 0.056 Uiso 1 1 calc R . .
C23 C 0.36323(17) 0.91889(15) -0.19187(12) 0.0383(3) Uani 1 1 d . . .
H23 H 0.2807 0.9608 -0.1947 0.046 Uiso 1 1 calc R . .
C24 C 0.37027(15) 0.83874(13) -0.10318(12) 0.0322(3) Uani 1 1 d . . .
C25 C 0.25506(15) 0.81765(13) -0.01429(11) 0.0296(3) Uani 1 1 d . . .
N1 N 0.13924(13) 0.88070(11) -0.01712(10) 0.0329(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3230(16) . ?
C1 C2 1.4083(18) . ?
C1 H1 0.9500 . ?
C2 C9 1.3938(18) . ?
C2 C3 1.4903(17) . ?
C3 C4 1.3921(18) . ?
C3 C8 1.3947(18) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3859(19) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C16 1.4182(17) . ?
C9 C10 1.4970(17) . ?
C10 C15 1.3880(18) . ?
C10 C11 1.3909(18) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3867(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C25 1.4175(18) . ?
C16 C17 1.4392(18) . ?
C17 C18 1.3492(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4312(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.4118(19) . ?
C19 C24 1.4193(19) . ?
C20 C21 1.366(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.3772(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.4081(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.4503(18) . ?
C25 N1 1.3636(16) . ?

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
N1 C1 C2 125.18(11) . . ?
N1 C1 H1 117.4 . . ?
C2 C1 H1 117.4 . . ?
C9 C2 C1 117.90(12) . . ?
C9 C2 C3 123.15(12) . . ?
C1 C2 C3 118.94(11) . . ?
C4 C3 C8 118.36(12) . . ?
C4 C3 C2 120.08(11) . . ?
C8 C3 C2 121.54(11) . . ?
C5 C4 C3 120.53(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.48(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.60(13) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.30(14) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 120.72(13) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C2 C9 C16 118.50(12) . . ?
C2 C9 C10 121.08(11) . . ?
C16 C9 C10 120.42(11) . . ?
C15 C10 C11 118.97(12) . . ?
C15 C10 C9 119.68(11) . . ?
C11 C10 C9 121.35(12) . . ?
C12 C11 C10 120.05(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.45(14) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.84(14) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.86(14) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.81(13) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C25 C16 C9 118.70(11) . . ?
C25 C16 C17 118.95(12) . . ?
C9 C16 C17 122.33(12) . . ?
C18 C17 C16 121.08(13) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.61(12) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C24 118.87(13) . . ?
C20 C19 C18 121.62(13) . . ?
C24 C19 C18 119.51(12) . . ?
C21 C20 C19 120.96(14) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.16(13) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.53(15) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.40(13) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 119.08(12) . . ?
C23 C24 C25 122.10(12) . . ?
C19 C24 C25 118.81(12) . . ?
N1 C25 C16 122.21(11) . . ?
N1 C25 C24 117.84(12) . . ?
C16 C25 C24 119.95(11) . . ?
C1 N1 C25 117.48(11) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.098
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_141206LT
_database_code_depnum_ccdc_archive 'CCDC 1419578'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N'
_chemical_formula_weight         219.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8347(5)
_cell_length_b                   8.6813(5)
_cell_length_c                   9.1755(8)
_cell_angle_alpha                82.727(3)
_cell_angle_beta                 73.371(3)
_cell_angle_gamma                78.005(2)
_cell_volume                     583.42(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2475
_cell_measurement_theta_min      3.2220
_cell_measurement_theta_max      26.2939

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8564
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_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            8929
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2381
_reflns_number_gt                1748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_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-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1160P)²+0.3890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2345
_refine_ls_wR_factor_gt          0.1961
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1207(3) 0.3061(2) 0.6664(2) 0.0382(6) Uani 1 1 d . . . . .
C1 C 0.2181(4) 0.4174(4) 0.8131(3) 0.0535(8) Uani 1 1 d . . . . .
H1 H 0.2247 0.4555 0.9036 0.064 Uiso 1 1 calc R U . . .
C2 C 0.0584(3) 0.3879(3) 0.8033(3) 0.0430(7) Uani 1 1 d . . . . .
H13 H -0.0459 0.4055 0.8874 0.052 Uiso 1 1 calc R U . . .
C3 C 0.0449(3) 0.3317(3) 0.6712(3) 0.0310(6) Uani 1 1 d . . . . .
C4 C 0.2026(3) 0.3020(2) 0.5468(2) 0.0279(5) Uani 1 1 d . . . . .
C5 C 0.1872(3) 0.2401(3) 0.4157(3) 0.0305(6) Uani 1 1 d . . . . .
C6 C 0.3517(3) 0.2030(3) 0.2852(3) 0.0323(6) Uani 1 1 d . . . . .
C7 C 0.3996(4) 0.3165(4) 0.1689(3) 0.0595(9) Uani 1 1 d . . . . .
H7 H 0.3277 0.4193 0.1717 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5526(4) 0.2815(4) 0.0477(3) 0.0636(10) Uani 1 1 d . . . . .
H6 H 0.5841 0.3600 -0.0321 0.076 Uiso 1 1 calc R U . . .
C9 C 0.6578(3) 0.1338(3) 0.0434(3) 0.0458(7) Uani 1 1 d . . . . .
H2 H 0.7586 0.1079 -0.0417 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1274(3) 0.2517(3) 0.5418(3) 0.0428(7) Uani 1 1 d . . . . .
H3 H -0.2420 0.2351 0.5380 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0204(3) 0.2150(3) 0.4120(3) 0.0396(6) Uani 1 1 d . . . . .
C12 C 0.6168(4) 0.0247(4) 0.1620(4) 0.0648(10) Uani 1 1 d . . . . .
H5 H 0.6931 -0.0759 0.1620 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4644(4) 0.0591(3) 0.2829(4) 0.0595(9) Uani 1 1 d . . . . .
H4 H 0.4377 -0.0182 0.3651 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3659(3) 0.3346(3) 0.5606(3) 0.0325(6) Uani 1 1 d . . . . .
H9 H 0.4722 0.3163 0.4785 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3745(4) 0.3918(4) 0.6895(3) 0.0458(7) Uani 1 1 d . . . . .
H8 H 0.4855 0.4145 0.6961 0.055 Uiso 1 1 calc R U . . .
C16 C -0.0134(4) 0.1514(4) 0.2801(4) 0.0580(9) Uani 1 1 d . . . . .
H12 H 0.0489 0.2037 0.1845 0.087 Uiso 1 1 calc R U . . .
H11 H -0.1438 0.1716 0.2896 0.087 Uiso 1 1 calc R U . . .
H10 H 0.0326 0.0375 0.2800 0.087 Uiso 1 1 calc R U . . .


_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 C10 1.309(3) . ?
N1 C3 1.375(3) . ?
C1 C2 1.358(4) . ?
C1 C15 1.412(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(4) . ?
C2 H13 0.9500 . ?
C3 C4 1.425(3) . ?
C4 C14 1.410(3) . ?
C4 C5 1.423(3) . ?
C5 C11 1.379(4) . ?
C5 C6 1.496(3) . ?
C6 C13 1.371(3) . ?
C6 C7 1.382(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(4) . ?
C8 H6 0.9500 . ?
C9 C12 1.360(4) . ?
C9 H2 0.9500 . ?
C10 C11 1.419(4) . ?
C10 H3 0.9500 . ?
C11 C16 1.501(4) . ?
C12 C13 1.387(4) . ?
C12 H5 0.9500 . ?
C13 H4 0.9500 . ?
C14 C15 1.363(3) . ?
C14 H9 0.9500 . ?
C15 H8 0.9500 . ?
C16 H12 0.9800 . ?
C16 H11 0.9800 . ?
C16 H10 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C3 116.9(2) . . ?
C2 C1 C15 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C15 C1 H1 119.8 . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 H13 119.5 . . ?
C3 C2 H13 119.5 . . ?
N1 C3 C2 118.7(2) . . ?
N1 C3 C4 122.1(2) . . ?
C2 C3 C4 119.2(2) . . ?
C14 C4 C5 123.4(2) . . ?
C14 C4 C3 118.2(2) . . ?
C5 C4 C3 118.4(2) . . ?
C11 C5 C4 119.0(2) . . ?
C11 C5 C6 121.4(2) . . ?
C4 C5 C6 119.6(2) . . ?
C13 C6 C7 118.3(2) . . ?
C13 C6 C5 120.9(2) . . ?
C7 C6 C5 120.7(2) . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H6 120.0 . . ?
C7 C8 H6 120.0 . . ?
C12 C9 C8 119.5(2) . . ?
C12 C9 H2 120.2 . . ?
C8 C9 H2 120.2 . . ?
N1 C10 C11 126.2(2) . . ?
N1 C10 H3 116.9 . . ?
C11 C10 H3 116.9 . . ?
C5 C11 C10 117.4(2) . . ?
C5 C11 C16 124.1(2) . . ?
C10 C11 C16 118.5(2) . . ?
C9 C12 C13 120.5(3) . . ?
C9 C12 H5 119.7 . . ?
C13 C12 H5 119.7 . . ?
C6 C13 C12 120.9(3) . . ?
C6 C13 H4 119.6 . . ?
C12 C13 H4 119.6 . . ?
C15 C14 C4 121.3(2) . . ?
C15 C14 H9 119.3 . . ?
C4 C14 H9 119.3 . . ?
C14 C15 C1 119.8(3) . . ?
C14 C15 H8 120.1 . . ?
C1 C15 H8 120.1 . . ?
C11 C16 H12 109.5 . . ?
C11 C16 H11 109.5 . . ?
H12 C16 H11 109.5 . . ?
C11 C16 H10 109.5 . . ?
H12 C16 H10 109.5 . . ?
H11 C16 H10 109.5 . . ?

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.097

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a16797
_database_code_depnum_ccdc_archive 'CCDC 1419579'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N'
_chemical_formula_sum            'C17 H15 N'
_chemical_formula_weight         233.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   8.1521(7)
_cell_length_b                   25.648(2)
_cell_length_c                   18.4479(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.064(4)
_cell_angle_gamma                90.00
_cell_volume                     3827.8(6)
_cell_formula_units_Z            12
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   ?

_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  ?
_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            21787
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6688
_reflns_number_gt                4776
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0514P)²+0.3217P] 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         6688
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.5194(2) 0.44520(6) 0.43196(7) 0.0306(4) Uani 1 1 d . . .
C2 C 0.5938(2) 0.40015(7) 0.46584(8) 0.0384(4) Uani 1 1 d . . .
H2 H 0.5263 0.3739 0.4832 0.046 Uiso 1 1 calc R . .
C3 C 0.7609(2) 0.39391(7) 0.47389(9) 0.0419(5) Uani 1 1 d . . .
H3 H 0.8091 0.3634 0.4966 0.050 Uiso 1 1 calc R . .
C4 C 0.8626(2) 0.43253(7) 0.44862(9) 0.0414(5) Uani 1 1 d . . .
H4 H 0.9790 0.4278 0.4538 0.050 Uiso 1 1 calc R . .
C5 C 0.7944(2) 0.47683(7) 0.41670(8) 0.0349(4) Uani 1 1 d . . .
H5 H 0.8645 0.5028 0.4003 0.042 Uiso 1 1 calc R . .
C6 C 0.6208(2) 0.48477(6) 0.40753(7) 0.0275(4) Uani 1 1 d . . .
C7 C 0.5434(2) 0.53052(6) 0.37453(7) 0.0272(4) Uani 1 1 d . . .
C8 C 0.64758(19) 0.57330(6) 0.34963(7) 0.0279(4) Uani 1 1 d . . .
C9 C 0.7520(2) 0.60212(6) 0.40041(8) 0.0322(4) Uani 1 1 d . . .
H9 H 0.7555 0.5947 0.4510 0.039 Uiso 1 1 calc R . .
C10 C 0.8502(2) 0.64126(7) 0.37778(9) 0.0355(4) Uani 1 1 d . . .
H10 H 0.9207 0.6606 0.4129 0.043 Uiso 1 1 calc R . .
C11 C 0.8465(2) 0.65247(7) 0.30426(9) 0.0396(4) Uani 1 1 d . . .
H11 H 0.9141 0.6795 0.2888 0.048 Uiso 1 1 calc R . .
C12 C 0.7441(2) 0.62422(7) 0.25338(9) 0.0431(5) Uani 1 1 d . . .
H12 H 0.7414 0.6318 0.2028 0.052 Uiso 1 1 calc R . .
C13 C 0.6457(2) 0.58498(7) 0.27579(8) 0.0370(4) Uani 1 1 d . . .
H13 H 0.5759 0.5657 0.2404 0.044 Uiso 1 1 calc R . .
C14 C 0.3728(2) 0.53380(6) 0.36753(8) 0.0304(4) Uani 1 1 d . . .
C15 C 0.2732(2) 0.57954(7) 0.33473(8) 0.0375(4) Uani 1 1 d . . .
H15A H 0.3469 0.6101 0.3338 0.045 Uiso 1 1 calc R . .
H15B H 0.1873 0.5883 0.3663 0.045 Uiso 1 1 calc R . .
C16 C 0.1900(2) 0.56905(8) 0.25734(9) 0.0530(5) Uani 1 1 d . . .
H16A H 0.1280 0.6000 0.2389 0.080 Uiso 1 1 calc R . .
H16B H 0.1143 0.5394 0.2580 0.080 Uiso 1 1 calc R . .
H16C H 0.2745 0.5610 0.2255 0.080 Uiso 1 1 calc R . .
C17 C 0.2851(2) 0.49145(7) 0.39366(8) 0.0364(4) Uani 1 1 d . . .
H17 H 0.1680 0.4942 0.3883 0.044 Uiso 1 1 calc R . .
C18 C 0.8547(2) 0.23909(6) 0.62401(8) 0.0301(4) Uani 1 1 d . . .
C19 C 0.7610(2) 0.25243(7) 0.55708(9) 0.0389(4) Uani 1 1 d . . .
H19 H 0.8075 0.2481 0.5127 0.047 Uiso 1 1 calc R . .
C20 C 0.6052(2) 0.27138(7) 0.55543(9) 0.0442(5) Uani 1 1 d . . .
H20 H 0.5427 0.2796 0.5100 0.053 Uiso 1 1 calc R . .
C21 C 0.5359(2) 0.27890(7) 0.62082(10) 0.0449(5) Uani 1 1 d . . .
H21 H 0.4267 0.2922 0.6192 0.054 Uiso 1 1 calc R . .
C22 C 0.6245(2) 0.26726(7) 0.68679(9) 0.0365(4) Uani 1 1 d . . .
H22 H 0.5768 0.2731 0.7305 0.044 Uiso 1 1 calc R . .
C23 C 0.7868(2) 0.24663(6) 0.69050(8) 0.0276(4) Uani 1 1 d . . .
C24 C 0.8836(2) 0.23130(6) 0.75745(8) 0.0270(4) Uani 1 1 d . . .
C25 C 0.8158(2) 0.23826(6) 0.82870(8) 0.0296(4) Uani 1 1 d . . .
C26 C 0.7938(2) 0.28767(7) 0.85684(9) 0.0433(5) Uani 1 1 d . . .
H26 H 0.8217 0.3176 0.8305 0.052 Uiso 1 1 calc R . .
C27 C 0.7317(2) 0.29376(9) 0.92303(10) 0.0510(5) Uani 1 1 d . . .
H27 H 0.7175 0.3278 0.9416 0.061 Uiso 1 1 calc R . .
C28 C 0.6905(2) 0.25104(9) 0.96204(9) 0.0466(5) Uani 1 1 d . . .
H28 H 0.6485 0.2554 1.0075 0.056 Uiso 1 1 calc R . .
C29 C 0.7106(2) 0.20206(8) 0.93460(8) 0.0438(5) Uani 1 1 d . . .
H29 H 0.6817 0.1724 0.9612 0.053 Uiso 1 1 calc R . .
C30 C 0.7730(2) 0.19521(7) 0.86834(8) 0.0343(4) Uani 1 1 d . . .
H30 H 0.7863 0.1610 0.8501 0.041 Uiso 1 1 calc R . .
C31 C 1.0376(2) 0.21022(6) 0.75390(8) 0.0305(4) Uani 1 1 d . . .
C32 C 1.1556(2) 0.19439(8) 0.81945(9) 0.0442(5) Uani 1 1 d . . .
H32A H 1.2142 0.1622 0.8078 0.053 Uiso 1 1 calc R . .
H32B H 1.0921 0.1865 0.8606 0.053 Uiso 1 1 calc R . .
C33 C 1.2805(3) 0.23632(11) 0.84255(11) 0.0753(7) Uani 1 1 d . . .
H33A H 1.3549 0.2244 0.8851 0.113 Uiso 1 1 calc R . .
H33B H 1.2231 0.2680 0.8553 0.113 Uiso 1 1 calc R . .
H33C H 1.3447 0.2439 0.8023 0.113 Uiso 1 1 calc R . .
C34 C 1.0920(2) 0.20516(7) 0.68412(8) 0.0366(4) Uani 1 1 d . . .
H34 H 1.1989 0.1908 0.6826 0.044 Uiso 1 1 calc R . .
C35 C 0.1069(2) -0.07386(7) 0.56681(7) 0.0323(4) Uani 1 1 d . . .
C36 C 0.1652(2) -0.12182(7) 0.54181(8) 0.0416(5) Uani 1 1 d . . .
H36 H 0.0887 -0.1482 0.5242 0.050 Uiso 1 1 calc R . .
C37 C 0.3305(3) -0.13026(8) 0.54297(9) 0.0459(5) Uani 1 1 d . . .
H37 H 0.3684 -0.1627 0.5265 0.055 Uiso 1 1 calc R . .
C38 C 0.4455(2) -0.09171(7) 0.56811(9) 0.0443(5) Uani 1 1 d . . .
H38 H 0.5604 -0.0981 0.5683 0.053 Uiso 1 1 calc R . .
C39 C 0.3929(2) -0.04513(7) 0.59236(8) 0.0373(4) Uani 1 1 d . . .
H39 H 0.4720 -0.0193 0.6093 0.045 Uiso 1 1 calc R . .
C40 C 0.2220(2) -0.03460(6) 0.59276(7) 0.0293(4) Uani 1 1 d . . .
C41 C 0.1615(2) 0.01347(6) 0.61765(7) 0.0289(4) Uani 1 1 d . . .
C42 C 0.28210(19) 0.05477(6) 0.64616(8) 0.0297(4) Uani 1 1 d . . .
C43 C 0.3550(2) 0.05375(7) 0.71855(9) 0.0394(4) Uani 1 1 d . . .
H43 H 0.3268 0.0269 0.7502 0.047 Uiso 1 1 calc R . .
C44 C 0.4679(2) 0.09153(7) 0.74463(10) 0.0450(5) Uani 1 1 d . . .
H44 H 0.5158 0.0907 0.7942 0.054 Uiso 1 1 calc R . .
C45 C 0.5114(2) 0.13033(7) 0.69917(10) 0.0431(5) Uani 1 1 d . . .
H45 H 0.5898 0.1560 0.7172 0.052 Uiso 1 1 calc R . .
C46 C 0.4405(2) 0.13175(7) 0.62732(9) 0.0425(5) Uani 1 1 d . . .
H46 H 0.4702 0.1586 0.5959 0.051 Uiso 1 1 calc R . .
C47 C 0.3260(2) 0.09415(7) 0.60067(9) 0.0378(4) Uani 1 1 d . . .
H47 H 0.2776 0.0954 0.5511 0.045 Uiso 1 1 calc R . .
C48 C -0.0068(2) 0.02080(7) 0.61426(8) 0.0316(4) Uani 1 1 d . . .
C49 C -0.0834(2) 0.06968(7) 0.63987(9) 0.0398(4) Uani 1 1 d . . .
H49A H -0.1981 0.0726 0.6154 0.048 Uiso 1 1 calc R . .
H49B H -0.0208 0.1002 0.6252 0.048 Uiso 1 1 calc R . .
C50 C -0.0858(2) 0.07096(8) 0.72265(9) 0.0491(5) Uani 1 1 d . . .
H50A H -0.1371 0.1035 0.7363 0.074 Uiso 1 1 calc R . .
H50B H 0.0277 0.0690 0.7472 0.074 Uiso 1 1 calc R . .
H50C H -0.1494 0.0412 0.7374 0.074 Uiso 1 1 calc R . .
C51 C -0.1096(2) -0.02100(7) 0.58638(8) 0.0383(4) Uani 1 1 d . . .
H51 H -0.2255 -0.0156 0.5834 0.046 Uiso 1 1 calc R . .
N1 N 0.34995(18) 0.44872(6) 0.42457(7) 0.0368(4) Uani 1 1 d . . .
N2 N 1.00851(18) 0.21851(6) 0.62136(7) 0.0364(4) Uani 1 1 d . . .
N3 N -0.06055(18) -0.06670(6) 0.56422(7) 0.0393(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.374(2) . ?
C1 C2 1.414(2) . ?
C1 C6 1.417(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.407(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.419(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.432(2) . ?
C7 C14 1.384(2) . ?
C7 C8 1.494(2) . ?
C8 C13 1.393(2) . ?
C8 C9 1.398(2) . ?
C9 C10 1.380(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C17 1.417(2) . ?
C14 C15 1.510(2) . ?
C15 C16 1.527(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N1 1.316(2) . ?
C17 H17 0.9500 . ?
C18 N2 1.367(2) . ?
C18 C19 1.412(2) . ?
C18 C23 1.420(2) . ?
C19 C20 1.356(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.418(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.436(2) . ?
C24 C31 1.376(2) . ?
C24 C25 1.498(2) . ?
C25 C26 1.389(2) . ?
C25 C30 1.392(2) . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.372(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C34 1.418(2) . ?
C31 C32 1.505(2) . ?
C32 C33 1.506(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 N2 1.314(2) . ?
C34 H34 0.9500 . ?
C35 N3 1.372(2) . ?
C35 C36 1.416(2) . ?
C35 C40 1.419(2) . ?
C36 C37 1.363(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.402(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.363(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.420(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.425(2) . ?
C41 C48 1.379(2) . ?
C41 C42 1.496(2) . ?
C42 C47 1.388(2) . ?
C42 C43 1.394(2) . ?
C43 C44 1.381(2) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.380(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.389(2) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C51 1.418(2) . ?
C48 C49 1.503(2) . ?
C49 C50 1.530(2) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 N3 1.319(2) . ?
C51 H51 0.9500 . ?

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
N1 C1 C2 117.98(15) . . ?
N1 C1 C6 122.69(15) . . ?
C2 C1 C6 119.33(16) . . ?
C3 C2 C1 120.91(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.20(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.24(17) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.16(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.15(15) . . ?
C1 C6 C7 118.55(15) . . ?
C5 C6 C7 123.29(15) . . ?
C14 C7 C6 118.35(14) . . ?
C14 C7 C8 121.97(14) . . ?
C6 C7 C8 119.67(14) . . ?
C13 C8 C9 118.31(15) . . ?
C13 C8 C7 121.36(14) . . ?
C9 C8 C7 120.33(13) . . ?
C10 C9 C8 120.68(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.28(16) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.70(16) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.21(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.82(15) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C7 C14 C17 117.71(15) . . ?
C7 C14 C15 124.71(15) . . ?
C17 C14 C15 117.57(15) . . ?
C14 C15 C16 113.12(14) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C14 126.38(16) . . ?
N1 C17 H17 116.8 . . ?
C14 C17 H17 116.8 . . ?
N2 C18 C19 117.56(14) . . ?
N2 C18 C23 122.72(13) . . ?
C19 C18 C23 119.71(16) . . ?
C20 C19 C18 120.74(16) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.23(15) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.55(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.74(16) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 118.01(14) . . ?
C22 C23 C24 123.65(14) . . ?
C18 C23 C24 118.30(14) . . ?
C31 C24 C23 118.34(13) . . ?
C31 C24 C25 121.73(13) . . ?
C23 C24 C25 119.93(14) . . ?
C26 C25 C30 118.34(15) . . ?
C26 C25 C24 121.00(14) . . ?
C30 C25 C24 120.66(14) . . ?
C27 C26 C25 120.64(17) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 120.67(18) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 119.24(16) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C28 C29 C30 120.87(17) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 120.24(17) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C24 C31 C34 117.91(14) . . ?
C24 C31 C32 124.35(14) . . ?
C34 C31 C32 117.68(15) . . ?
C31 C32 C33 112.18(16) . . ?
C31 C32 H32A 109.2 . . ?
C33 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
C33 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N2 C34 C31 126.16(16) . . ?
N2 C34 H34 116.9 . . ?
C31 C34 H34 116.9 . . ?
N3 C35 C36 118.51(16) . . ?
N3 C35 C40 122.04(15) . . ?
C36 C35 C40 119.45(16) . . ?
C37 C36 C35 120.26(17) . . ?
C37 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C36 C37 C38 120.86(17) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C39 C38 C37 120.16(18) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 121.11(17) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C35 C40 C39 118.16(15) . . ?
C35 C40 C41 118.82(15) . . ?
C39 C40 C41 123.03(15) . . ?
C48 C41 C40 119.03(15) . . ?
C48 C41 C42 121.78(15) . . ?
C40 C41 C42 119.18(14) . . ?
C47 C42 C43 118.80(15) . . ?
C47 C42 C41 120.65(14) . . ?
C43 C42 C41 120.54(14) . . ?
C44 C43 C42 120.52(16) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C45 C44 C43 120.37(16) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 119.74(17) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C47 120.35(16) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C42 C47 C46 120.21(15) . . ?
C42 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C41 C48 C51 117.01(16) . . ?
C41 C48 C49 123.32(15) . . ?
C51 C48 C49 119.65(16) . . ?
C48 C49 C50 112.86(14) . . ?
C48 C49 H49A 109.0 . . ?
C50 C49 H49A 109.0 . . ?
C48 C49 H49B 109.0 . . ?
C50 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N3 C51 C48 126.55(17) . . ?
N3 C51 H51 116.7 . . ?
C48 C51 H51 116.7 . . ?
C17 N1 C1 116.32(14) . . ?
C34 N2 C18 116.56(13) . . ?
C51 N3 C35 116.51(15) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
