# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_180141LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1825212'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-11-01 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            'C20 H14 N2'
_chemical_formula_weight         282.33

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                   3.9188(4)
_cell_length_b                   12.5127(13)
_cell_length_c                   15.3057(15)
_cell_angle_alpha                101.080(5)
_cell_angle_beta                 96.416(5)
_cell_angle_gamma                92.665(5)
_cell_volume                     730.13(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8090
_cell_measurement_theta_min      2.3526
_cell_measurement_theta_max      26.3494

_exptl_crystal_description       Lump
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8530
_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            25856
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.366
_diffrn_reflns_theta_max         26.623
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2993
_reflns_number_gt                2581
_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       '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    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0677P)²+0.3791P] 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     SHELXL
_refine_ls_extinction_coef       0.010(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_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
C20 C 0.7466(4) 0.45112(11) 0.24368(9) 0.0171(3) Uani 1 1 d . . . . .
H20 H 0.7915 0.3929 0.1975 0.021 Uiso 1 1 calc R U . . .
N2 N 0.5872(3) 0.51288(11) 0.39073(9) 0.0241(3) Uani 1 1 d . . . . .
N1 N 0.6665(4) -0.09095(11) 0.39874(10) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.7078(4) 0.64169(12) 0.29913(10) 0.0221(3) Uani 1 1 d . . . . .
H1 H 0.7287 0.7151 0.2912 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7728(4) 0.55657(13) 0.23266(11) 0.0262(4) Uani 1 1 d . . . . .
H13 H 0.8373 0.5718 0.1780 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6541(4) 0.43114(12) 0.32268(9) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.6430(4) 0.31721(12) 0.33730(9) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.4939(4) 0.22806(12) 0.27086(9) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.3194(4) 0.24351(12) 0.18429(10) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.2192 0.3110 0.1831 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2910(4) 0.17132(12) 0.10820(10) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.3819 0.1027 0.1107 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1333(4) 0.18611(12) 0.02010(9) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.1648(4) 0.10700(14) -0.05528(10) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.2757 0.0427 -0.0482 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0375(4) 0.12000(14) -0.14053(10) 0.0267(4) Uani 1 1 d . . . . .
H7 H 0.0668 0.0658 -0.1913 0.032 Uiso 1 1 calc R U . . .
C11 C -0.1306(4) 0.21116(15) -0.15163(11) 0.0281(4) Uani 1 1 d . . . . .
H2 H -0.2198 0.2199 -0.2099 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6115(4) 0.61727(12) 0.37752(10) 0.0206(3) Uani 1 1 d . . . . .
H3 H 0.5608 0.6749 0.4234 0.025 Uiso 1 1 calc R U . . .
C13 C 0.7965(4) 0.29864(12) 0.41947(10) 0.0194(3) Uani 1 1 d . . . . .
H4 H 0.8954 0.3591 0.4640 0.023 Uiso 1 1 calc R U . . .
C14 C 0.8085(4) 0.19509(12) 0.43773(10) 0.0208(3) Uani 1 1 d . . . . .
H5 H 0.9145 0.1840 0.4939 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6615(4) 0.10684(12) 0.37190(10) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.6656(4) -0.00287(13) 0.38795(10) 0.0244(4) Uani 1 1 d . . . . .
C17 C 0.5060(4) 0.12369(12) 0.28981(10) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.4062 0.0628 0.2458 0.022 Uiso 1 1 calc R U . . .
C18 C -0.1693(4) 0.29014(14) -0.07743(11) 0.0292(4) Uani 1 1 d . . . . .
H9 H -0.2870 0.3531 -0.0849 0.035 Uiso 1 1 calc R U . . .
C19 C -0.0379(4) 0.27830(13) 0.00777(10) 0.0230(3) Uani 1 1 d . . . . .
H8 H -0.0647 0.3334 0.0582 0.028 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
C20 C2 1.363(2) . ?
C20 C3 1.364(2) . ?
C20 H20 0.9500 . ?
N2 C12 1.3602(19) . ?
N2 C3 1.3696(19) . ?
N1 C16 1.146(2) . ?
C1 C2 1.379(2) . ?
C1 C12 1.381(2) . ?
C1 H1 0.9500 . ?
C2 H13 0.9500 . ?
C3 C4 1.484(2) . ?
C4 C13 1.3977(19) . ?
C4 C5 1.411(2) . ?
C5 C17 1.393(2) . ?
C5 C6 1.4726(19) . ?
C6 C7 1.320(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4679(19) . ?
C7 H11 0.9500 . ?
C8 C9 1.389(2) . ?
C8 C19 1.394(2) . ?
C9 C10 1.386(2) . ?
C9 H10 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H7 0.9500 . ?
C11 C18 1.382(3) . ?
C11 H2 0.9500 . ?
C12 H3 0.9500 . ?
C13 C14 1.379(2) . ?
C13 H4 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H5 0.9500 . ?
C15 C17 1.392(2) . ?
C15 C16 1.441(2) . ?
C17 H12 0.9500 . ?
C18 C19 1.385(2) . ?
C18 H9 0.9500 . ?
C19 H8 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
C2 C20 C3 118.36(13) . . ?
C2 C20 H20 120.8 . . ?
C3 C20 H20 120.8 . . ?
C12 N2 C3 117.95(13) . . ?
C2 C1 C12 118.13(14) . . ?
C2 C1 H1 120.9 . . ?
C12 C1 H1 120.9 . . ?
C20 C2 C1 121.37(14) . . ?
C20 C2 H13 119.3 . . ?
C1 C2 H13 119.3 . . ?
C20 C3 N2 122.45(13) . . ?
C20 C3 C4 118.78(12) . . ?
N2 C3 C4 118.69(13) . . ?
C13 C4 C5 119.52(13) . . ?
C13 C4 C3 117.93(12) . . ?
C5 C4 C3 122.52(12) . . ?
C17 C5 C4 118.32(13) . . ?
C17 C5 C6 119.99(13) . . ?
C4 C5 C6 121.66(13) . . ?
C7 C6 C5 125.36(14) . . ?
C7 C6 H6 117.3 . . ?
C5 C6 H6 117.3 . . ?
C6 C7 C8 126.68(14) . . ?
C6 C7 H11 116.7 . . ?
C8 C7 H11 116.7 . . ?
C9 C8 C19 117.97(14) . . ?
C9 C8 C7 119.04(13) . . ?
C19 C8 C7 122.95(14) . . ?
C10 C9 C8 121.30(15) . . ?
C10 C9 H10 119.4 . . ?
C8 C9 H10 119.4 . . ?
C11 C10 C9 120.06(15) . . ?
C11 C10 H7 120.0 . . ?
C9 C10 H7 120.0 . . ?
C10 C11 C18 119.59(14) . . ?
C10 C11 H2 120.2 . . ?
C18 C11 H2 120.2 . . ?
N2 C12 C1 121.72(13) . . ?
N2 C12 H3 119.1 . . ?
C1 C12 H3 119.1 . . ?
C14 C13 C4 121.88(13) . . ?
C14 C13 H4 119.1 . . ?
C4 C13 H4 119.1 . . ?
C13 C14 C15 118.59(13) . . ?
C13 C14 H5 120.7 . . ?
C15 C14 H5 120.7 . . ?
C17 C15 C14 120.39(13) . . ?
C17 C15 C16 118.92(13) . . ?
C14 C15 C16 120.69(13) . . ?
N1 C16 C15 178.49(16) . . ?
C15 C17 C5 121.29(13) . . ?
C15 C17 H12 119.4 . . ?
C5 C17 H12 119.4 . . ?
C11 C18 C19 120.55(15) . . ?
C11 C18 H9 119.7 . . ?
C19 C18 H9 119.7 . . ?
C18 C19 C8 120.51(15) . . ?
C18 C19 H8 119.7 . . ?
C8 C19 H8 119.7 . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.050

_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_180303LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1831607'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-11-01 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            'C22 H19 N3'
_chemical_formula_weight         325.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.5762(7)
_cell_length_b                   7.8869(6)
_cell_length_c                   19.9879(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.535(3)
_cell_angle_gamma                90
_cell_volume                     1666.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4321
_cell_measurement_theta_min      2.7765
_cell_measurement_theta_max      26.2830

_exptl_crystal_description       tabullar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8664
_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            13644
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.038
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3412
_reflns_number_gt                2836
_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       '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    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0325P)²+0.6081P] 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         3412
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_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 0.61711(10) 0.75878(14) 0.17384(5) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.66803(9) 0.64589(13) 0.27934(5) 0.0162(2) Uani 1 1 d . . . . .
N3 N 0.46317(10) 0.61058(15) 0.23688(6) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.40468(13) 0.73464(19) 0.13215(7) 0.0286(3) Uani 1 1 d . . . . .
H1 H 0.3423 0.7586 0.0984 0.034 Uiso 1 1 calc R U . . .
C2 C 0.52774(13) 0.78961(18) 0.12704(7) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.5499 0.8522 0.0885 0.031 Uiso 1 1 calc R U . . .
C3 C 0.57825(11) 0.67183(16) 0.22643(6) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.79950(11) 0.62547(15) 0.27226(6) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.85111(11) 0.53818(15) 0.21416(6) 0.0152(3) Uani 1 1 d . . . . .
C6 C 0.78392(11) 0.41306(15) 0.18481(6) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.7076 0.3834 0.2059 0.020 Uiso 1 1 calc R U . . .
C7 C 0.81255(11) 0.31585(16) 0.12437(6) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.86062(12) 0.39199(17) 0.06755(6) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.8806 0.5094 0.0685 0.023 Uiso 1 1 calc R U . . .
C9 C 0.87978(12) 0.29997(18) 0.00978(7) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.9127 0.3545 -0.0284 0.027 Uiso 1 1 calc R U . . .
C10 C 0.85109(12) 0.12842(18) 0.00740(7) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.8646 0.0648 -0.0321 0.028 Uiso 1 1 calc R U . . .
C11 C 0.37673(13) 0.64374(19) 0.18833(7) 0.0266(3) Uani 1 1 d . . . . .
H19 H 0.2930 0.6027 0.1930 0.032 Uiso 1 1 calc R U . . .
C12 C 0.64785(12) 0.70846(15) 0.34382(6) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.76674(12) 0.72917(15) 0.37580(6) 0.0167(3) Uani 1 1 d . . . . .
C14 C 0.85978(12) 0.67532(16) 0.32980(6) 0.0171(3) Uani 1 1 d . . . . .
H14 H 0.9487 0.6745 0.3381 0.021 Uiso 1 1 calc R U . . .
C15 C 0.98287(11) 0.59060(16) 0.19556(6) 0.0175(3) Uani 1 1 d . . . . .
H5 H 1.0170 0.5055 0.1644 0.021 Uiso 1 1 calc R U . . .
H4 H 1.0379 0.5911 0.2364 0.021 Uiso 1 1 calc R U . . .
C16 C 0.98807(13) 0.76500(16) 0.16280(7) 0.0228(3) Uani 1 1 d . . . . .
H6 H 0.9430 0.7615 0.1193 0.034 Uiso 1 1 calc R U . . .
H7 H 1.0765 0.7969 0.1564 0.034 Uiso 1 1 calc R U . . .
H8 H 0.9480 0.8487 0.1917 0.034 Uiso 1 1 calc R U . . .
C17 C 0.78303(11) 0.14248(16) 0.12108(7) 0.0188(3) Uani 1 1 d . . . . .
H13 H 0.7493 0.0875 0.1589 0.023 Uiso 1 1 calc R U . . .
C18 C 0.80263(12) 0.05101(17) 0.06332(7) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.7826 -0.0664 0.0620 0.026 Uiso 1 1 calc R U . . .
C19 C 0.77252(12) 0.79368(16) 0.44107(7) 0.0197(3) Uani 1 1 d . . . . .
H18 H 0.8518 0.8091 0.4637 0.024 Uiso 1 1 calc R U . . .
C20 C 0.66154(13) 0.83460(17) 0.47203(7) 0.0223(3) Uani 1 1 d . . . . .
H17 H 0.6648 0.8794 0.5162 0.027 Uiso 1 1 calc R U . . .
C21 C 0.54426(13) 0.81096(17) 0.43931(7) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.4691 0.8387 0.4619 0.027 Uiso 1 1 calc R U . . .
C22 C 0.53548(12) 0.74807(16) 0.37483(7) 0.0199(3) Uani 1 1 d . . . . .
H15 H 0.4558 0.7325 0.3526 0.024 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 C3 1.3295(17) . ?
N1 C2 1.3342(18) . ?
N2 C12 1.4017(16) . ?
N2 C4 1.4107(15) . ?
N2 C3 1.4171(16) . ?
N3 C3 1.3312(16) . ?
N3 C11 1.3409(18) . ?
C1 C11 1.371(2) . ?
C1 C2 1.378(2) . ?
C1 H1 0.9500 . ?
C2 H3 0.9500 . ?
C4 C14 1.3582(18) . ?
C4 C5 1.4677(17) . ?
C5 C6 1.3419(18) . ?
C5 C15 1.5096(16) . ?
C6 C7 1.4691(17) . ?
C6 H9 0.9500 . ?
C7 C8 1.3928(18) . ?
C7 C17 1.4037(18) . ?
C8 C9 1.3834(18) . ?
C8 H10 0.9500 . ?
C9 C10 1.3872(19) . ?
C9 H11 0.9500 . ?
C10 C18 1.3839(19) . ?
C10 H2 0.9500 . ?
C11 H19 0.9500 . ?
C12 C22 1.3906(17) . ?
C12 C13 1.4047(18) . ?
C13 C19 1.4001(18) . ?
C13 C14 1.4292(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.5250(18) . ?
C15 H5 0.9900 . ?
C15 H4 0.9900 . ?
C16 H6 0.9800 . ?
C16 H7 0.9800 . ?
C16 H8 0.9800 . ?
C17 C18 1.3817(18) . ?
C17 H13 0.9500 . ?
C18 H12 0.9500 . ?
C19 C20 1.3797(18) . ?
C19 H18 0.9500 . ?
C20 C21 1.3991(19) . ?
C20 H17 0.9500 . ?
C21 C22 1.3818(19) . ?
C21 H16 0.9500 . ?
C22 H15 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
C3 N1 C2 114.85(12) . . ?
C12 N2 C4 107.90(10) . . ?
C12 N2 C3 121.33(10) . . ?
C4 N2 C3 125.74(10) . . ?
C3 N3 C11 115.10(12) . . ?
C11 C1 C2 116.74(13) . . ?
C11 C1 H1 121.6 . . ?
C2 C1 H1 121.6 . . ?
N1 C2 C1 122.91(13) . . ?
N1 C2 H3 118.5 . . ?
C1 C2 H3 118.5 . . ?
N1 C3 N3 127.92(12) . . ?
N1 C3 N2 116.71(11) . . ?
N3 C3 N2 115.32(11) . . ?
C14 C4 N2 108.87(11) . . ?
C14 C4 C5 129.03(11) . . ?
N2 C4 C5 121.43(11) . . ?
C6 C5 C4 119.14(11) . . ?
C6 C5 C15 125.12(11) . . ?
C4 C5 C15 115.58(11) . . ?
C5 C6 C7 128.67(11) . . ?
C5 C6 H9 115.7 . . ?
C7 C6 H9 115.7 . . ?
C8 C7 C17 117.86(12) . . ?
C8 C7 C6 122.23(12) . . ?
C17 C7 C6 119.77(11) . . ?
C9 C8 C7 121.29(12) . . ?
C9 C8 H10 119.4 . . ?
C7 C8 H10 119.4 . . ?
C8 C9 C10 120.23(13) . . ?
C8 C9 H11 119.9 . . ?
C10 C9 H11 119.9 . . ?
C18 C10 C9 119.21(13) . . ?
C18 C10 H2 120.4 . . ?
C9 C10 H2 120.4 . . ?
N3 C11 C1 122.47(13) . . ?
N3 C11 H19 118.8 . . ?
C1 C11 H19 118.8 . . ?
C22 C12 N2 129.94(12) . . ?
C22 C12 C13 122.44(12) . . ?
N2 C12 C13 107.63(10) . . ?
C19 C13 C12 118.85(11) . . ?
C19 C13 C14 133.93(12) . . ?
C12 C13 C14 107.22(11) . . ?
C4 C14 C13 108.37(11) . . ?
C4 C14 H14 125.8 . . ?
C13 C14 H14 125.8 . . ?
C5 C15 C16 113.38(10) . . ?
C5 C15 H5 108.9 . . ?
C16 C15 H5 108.9 . . ?
C5 C15 H4 108.9 . . ?
C16 C15 H4 108.9 . . ?
H5 C15 H4 107.7 . . ?
C15 C16 H6 109.5 . . ?
C15 C16 H7 109.5 . . ?
H6 C16 H7 109.5 . . ?
C15 C16 H8 109.5 . . ?
H6 C16 H8 109.5 . . ?
H7 C16 H8 109.5 . . ?
C18 C17 C7 120.64(12) . . ?
C18 C17 H13 119.7 . . ?
C7 C17 H13 119.7 . . ?
C17 C18 C10 120.77(12) . . ?
C17 C18 H12 119.6 . . ?
C10 C18 H12 119.6 . . ?
C20 C19 C13 119.11(12) . . ?
C20 C19 H18 120.4 . . ?
C13 C19 H18 120.4 . . ?
C19 C20 C21 120.89(12) . . ?
C19 C20 H17 119.6 . . ?
C21 C20 H17 119.6 . . ?
C22 C21 C20 121.36(12) . . ?
C22 C21 H16 119.3 . . ?
C20 C21 H16 119.3 . . ?
C21 C22 C12 117.35(12) . . ?
C21 C22 H15 121.3 . . ?
C12 C22 H15 121.3 . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040

_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_180446lt_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1841353'
_audit_update_record             
;
2018-05-04 deposited with the CCDC.
2018-11-01 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            'C25 H20 N4 O2'
_chemical_formula_weight         408.45

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'

_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                   9.1577(9)
_cell_length_b                   10.7173(7)
_cell_length_c                   13.3021(10)
_cell_angle_alpha                106.893(3)
_cell_angle_beta                 91.497(4)
_cell_angle_gamma                91.349(3)
_cell_volume                     1248.12(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7232
_cell_measurement_theta_min      2.2259
_cell_measurement_theta_max      26.2943

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8548
_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            19906
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.601
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5120
_reflns_number_gt                4080
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       '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    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0225P)²+4.6686P] 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         5120
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.1087
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.2187
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.4103(6) 0.5204(9) 0.1081(4) 0.080(2) Uani 1 1 d . . . . .
C2 C 0.5162(4) 0.4903(5) 0.1861(3) 0.0436(11) Uani 1 1 d . . . . .
H2 H 0.5534 0.4001 0.1587 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4389(4) 0.5068(4) 0.2872(3) 0.0358(9) Uani 1 1 d . . . . .
C4 C 0.3210(4) 0.4276(4) 0.3074(3) 0.0394(10) Uani 1 1 d . . . . .
C5 C 0.2465(5) 0.3149(5) 0.2451(4) 0.0505(12) Uani 1 1 d . . . . .
H5 H 0.2722 0.2762 0.1744 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1353(6) 0.2614(5) 0.2884(4) 0.0544(12) Uani 1 1 d . . . . .
H6 H 0.0845 0.1844 0.2473 0.065 Uiso 1 1 calc R U . . .
C7 C 0.0962(5) 0.3188(4) 0.3918(4) 0.0463(11) Uani 1 1 d . . . . .
H7 H 0.0193 0.2797 0.4198 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1666(4) 0.4312(4) 0.4547(3) 0.0373(9) Uani 1 1 d . . . . .
H8 H 0.1380 0.4711 0.5246 0.045 Uiso 1 1 calc R U . . .
C9 C 0.2812(4) 0.4833(4) 0.4111(3) 0.0337(9) Uani 1 1 d . . . . .
C10 C 0.4698(4) 0.6062(4) 0.3758(3) 0.0312(8) Uani 1 1 d . . . . .
C11 C 0.5964(4) 0.7004(4) 0.3907(3) 0.0318(8) Uani 1 1 d . . . . .
H11A H 0.6386 0.7196 0.4631 0.038 Uiso 1 1 calc R U . . .
H11B H 0.5645 0.7831 0.3795 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7114(4) 0.6379(4) 0.3102(3) 0.0330(8) Uani 1 1 d . . . . .
H12 H 0.7387 0.5558 0.3265 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6401(5) 0.5939(4) 0.1987(3) 0.0402(10) Uani 1 1 d . . . . .
H13 H 0.7175 0.5545 0.1486 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5679(8) 0.6981(5) 0.1591(4) 0.075(2) Uani 1 1 d . . . . .
C15 C 0.3581(4) 0.6886(4) 0.5517(3) 0.0306(8) Uani 1 1 d . . . . .
C16 C 0.2675(6) 0.7405(4) 0.7140(3) 0.0532(13) Uani 1 1 d . . . . .
H16 H 0.2144 0.7176 0.7669 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3211(7) 0.8662(5) 0.7338(4) 0.0644(16) Uani 1 1 d . . . . .
H17 H 0.3068 0.9305 0.7988 0.077 Uiso 1 1 calc R U . . .
C18 C 0.3966(5) 0.8939(4) 0.6545(4) 0.0474(11) Uani 1 1 d . . . . .
H18 H 0.4381 0.9793 0.6668 0.057 Uiso 1 1 calc R U . . .
C19 C 0.8519(4) 0.7183(4) 0.3212(3) 0.0343(9) Uani 1 1 d . . . . .
C20 C 0.8583(5) 0.8532(4) 0.3539(4) 0.0505(12) Uani 1 1 d . . . . .
H20 H 0.7704 0.8993 0.3691 0.061 Uiso 1 1 calc R U . . .
C21 C 0.9902(5) 0.9227(5) 0.3650(4) 0.0551(13) Uani 1 1 d . . . . .
H21 H 0.9905 1.0153 0.3874 0.066 Uiso 1 1 calc R U . . .
C22 C 1.1214(5) 0.8608(5) 0.3443(4) 0.0479(11) Uani 1 1 d . . . . .
C23 C 1.1155(5) 0.7253(4) 0.3104(4) 0.0423(10) Uani 1 1 d . . . . .
H23 H 1.2035 0.6796 0.2939 0.051 Uiso 1 1 calc R U . . .
C24 C 0.9841(4) 0.6556(4) 0.3000(3) 0.0374(9) Uani 1 1 d . . . . .
H24 H 0.9840 0.5630 0.2779 0.045 Uiso 1 1 calc R U . . .
C25 C 1.2666(5) 0.9361(5) 0.3565(5) 0.0608(14) Uani 1 1 d . . . . .
H25A H 1.2493 1.0299 0.3768 0.091 Uiso 1 1 calc R U . . .
H25B H 1.3165 0.9111 0.2896 0.091 Uiso 1 1 calc R U . . .
H25C H 1.3278 0.9160 0.4109 0.091 Uiso 1 1 calc R U . . .
N1 N 0.4393(6) 0.6437(7) 0.1044(3) 0.093(2) Uani 1 1 d . . . . .
H1 H 0.3826 0.6849 0.0710 0.112 Uiso 1 1 calc R U . . .
N2 N 0.3731(3) 0.5952(3) 0.4538(2) 0.0311(7) Uani 1 1 d . . . . .
N3 N 0.2873(4) 0.6488(3) 0.6231(3) 0.0383(8) Uani 1 1 d . . . . .
N4 N 0.4146(4) 0.8074(3) 0.5614(3) 0.0371(8) Uani 1 1 d . . . . .
O1 O 0.3095(4) 0.4528(7) 0.0579(3) 0.114(2) Uani 1 1 d . . . . .
O2 O 0.6087(8) 0.8076(4) 0.1721(3) 0.126(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 O1 1.216(8) . ?
C1 N1 1.356(10) . ?
C1 C2 1.510(7) . ?
C2 C3 1.502(6) . ?
C2 C13 1.540(6) . ?
C2 H2 1.0000 . ?
C3 C10 1.357(5) . ?
C3 C4 1.436(6) . ?
C4 C9 1.397(6) . ?
C4 C5 1.400(6) . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(6) . ?
C8 H8 0.9500 . ?
C9 N2 1.415(5) . ?
C10 N2 1.411(5) . ?
C10 C11 1.489(5) . ?
C11 C12 1.542(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C19 1.512(6) . ?
C12 C13 1.542(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.524(6) . ?
C13 H13 1.0000 . ?
C14 O2 1.186(8) . ?
C14 N1 1.390(9) . ?
C15 N3 1.326(5) . ?
C15 N4 1.332(5) . ?
C15 N2 1.405(5) . ?
C16 N3 1.338(5) . ?
C16 C17 1.371(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(6) . ?
C17 H17 0.9500 . ?
C18 N4 1.331(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(6) . ?
C19 C24 1.394(5) . ?
C20 C21 1.386(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(6) . ?
C22 C25 1.520(7) . ?
C23 C24 1.384(6) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 H1 0.8800 . ?

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
O1 C1 N1 122.6(6) . . ?
O1 C1 C2 128.6(8) . . ?
N1 C1 C2 108.7(6) . . ?
C3 C2 C1 108.0(3) . . ?
C3 C2 C13 111.5(3) . . ?
C1 C2 C13 103.5(5) . . ?
C3 C2 H2 111.2 . . ?
C1 C2 H2 111.2 . . ?
C13 C2 H2 111.2 . . ?
C10 C3 C4 108.7(3) . . ?
C10 C3 C2 123.4(4) . . ?
C4 C3 C2 127.9(4) . . ?
C9 C4 C5 119.8(4) . . ?
C9 C4 C3 107.4(4) . . ?
C5 C4 C3 132.8(4) . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 121.8(5) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 117.1(4) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
C8 C9 C4 121.8(4) . . ?
C8 C9 N2 130.9(4) . . ?
C4 C9 N2 107.3(4) . . ?
C3 C10 N2 108.5(4) . . ?
C3 C10 C11 125.0(3) . . ?
N2 C10 C11 126.2(3) . . ?
C10 C11 C12 107.9(3) . . ?
C10 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C19 C12 C13 115.2(3) . . ?
C19 C12 C11 114.0(3) . . ?
C13 C12 C11 109.8(3) . . ?
C19 C12 H12 105.7 . . ?
C13 C12 H12 105.7 . . ?
C11 C12 H12 105.7 . . ?
C14 C13 C2 102.9(4) . . ?
C14 C13 C12 117.1(4) . . ?
C2 C13 C12 113.2(3) . . ?
C14 C13 H13 107.7 . . ?
C2 C13 H13 107.7 . . ?
C12 C13 H13 107.7 . . ?
O2 C14 N1 124.0(6) . . ?
O2 C14 C13 128.1(6) . . ?
N1 C14 C13 107.9(5) . . ?
N3 C15 N4 127.5(4) . . ?
N3 C15 N2 116.3(3) . . ?
N4 C15 N2 116.2(3) . . ?
N3 C16 C17 122.5(4) . . ?
N3 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C18 116.3(4) . . ?
C16 C17 H17 121.9 . . ?
C18 C17 H17 121.9 . . ?
N4 C18 C17 123.5(4) . . ?
N4 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C20 C19 C24 116.9(4) . . ?
C20 C19 C12 123.6(4) . . ?
C24 C19 C12 119.5(4) . . ?
C19 C20 C21 121.4(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 117.1(4) . . ?
C21 C22 C25 122.1(4) . . ?
C23 C22 C25 120.8(4) . . ?
C24 C23 C22 121.3(4) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C19 121.5(4) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C14 112.9(5) . . ?
C1 N1 H1 123.6 . . ?
C14 N1 H1 123.6 . . ?
C15 N2 C10 125.6(3) . . ?
C15 N2 C9 125.8(3) . . ?
C10 N2 C9 108.2(3) . . ?
C15 N3 C16 115.6(4) . . ?
C18 N4 C15 114.7(4) . . ?

_refine_diff_density_max         0.974
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6




