# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_g1063
_database_code_depnum_ccdc_archive 'CCDC 1500185'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H13 N'
_chemical_formula_sum            'C19 H13 N'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         255.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.4892(6)
_cell_length_b                   17.7731(15)
_cell_length_c                   9.0884(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.345(8)
_cell_angle_gamma                90
_cell_volume                     1308.89(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1020
_cell_measurement_theta_min      3.3970
_cell_measurement_theta_max      28.5770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6020
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.763
_diffrn_reflns_theta_max         29.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3031
_reflns_number_gt                1885
_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       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0566P)²+0.0496P] 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         3031
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1252
_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_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
N N -0.21711(19) 0.13981(10) 0.03014(19) 0.0271(4) Uani 1 1 d . . . . .
C1 C -0.2340(2) 0.15445(12) 0.1701(2) 0.0251(5) Uani 1 1 d . . . . .
C2 C -0.3898(2) 0.18129(12) 0.1768(2) 0.0312(5) Uani 1 1 d . . . . .
H2A H -0.4787 0.1857 0.0845 0.037 Uiso 1 1 calc R U . . .
C3 C -0.4130(2) 0.20067(13) 0.3132(3) 0.0355(6) Uani 1 1 d . . . . .
H3A H -0.5172 0.2194 0.3152 0.043 Uiso 1 1 calc R U . . .
C4 C -0.2831(2) 0.19319(13) 0.4528(3) 0.0330(5) Uani 1 1 d . . . . .
H4A H -0.3008 0.2070 0.5476 0.040 Uiso 1 1 calc R U . . .
C5 C -0.1333(2) 0.16630(12) 0.4520(2) 0.0283(5) Uani 1 1 d . . . . .
H5A H -0.0480 0.1608 0.5467 0.034 Uiso 1 1 calc R U . . .
C6 C -0.1022(2) 0.14622(11) 0.3109(2) 0.0225(5) Uani 1 1 d . . . . .
C7 C 0.0506(2) 0.11936(12) 0.3029(2) 0.0225(5) Uani 1 1 d . . . . .
C8 C 0.0706(2) 0.10515(11) 0.1577(2) 0.0225(5) Uani 1 1 d . . . . .
C9 C 0.2228(2) 0.08113(12) 0.1360(2) 0.0282(5) Uani 1 1 d . . . . .
H9A H 0.3161 0.0734 0.2233 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2362(3) 0.06914(13) -0.0069(2) 0.0323(5) Uani 1 1 d . . . . .
H10A H 0.3387 0.0533 -0.0187 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0980(3) 0.08005(13) -0.1395(2) 0.0332(5) Uani 1 1 d . . . . .
H11A H 0.1087 0.0709 -0.2390 0.040 Uiso 1 1 calc R U . . .
C12 C -0.0495(2) 0.10348(12) -0.1251(2) 0.0297(5) Uani 1 1 d . . . . .
H12A H -0.1405 0.1110 -0.2147 0.036 Uiso 1 1 calc R U . . .
C13 C -0.0681(2) 0.11669(12) 0.0230(2) 0.0249(5) Uani 1 1 d . . . . .
C14 C 0.1910(2) 0.10522(12) 0.4458(2) 0.0225(5) Uani 1 1 d . . . . .
C15 C 0.2805(2) 0.16457(13) 0.5308(2) 0.0279(5) Uani 1 1 d . . . . .
H15A H 0.2516 0.2149 0.4990 0.033 Uiso 1 1 calc R U . . .
C16 C 0.4119(2) 0.15052(14) 0.6619(2) 0.0317(5) Uani 1 1 d . . . . .
H16A H 0.4721 0.1914 0.7195 0.038 Uiso 1 1 calc R U . . .
C17 C 0.4553(2) 0.07762(14) 0.7088(2) 0.0315(6) Uani 1 1 d . . . . .
H17A H 0.5460 0.0683 0.7977 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3668(2) 0.01827(14) 0.6263(2) 0.0315(5) Uani 1 1 d . . . . .
H18A H 0.3959 -0.0319 0.6592 0.038 Uiso 1 1 calc R U . . .
C19 C 0.2348(2) 0.03175(13) 0.4948(2) 0.0280(5) Uani 1 1 d . . . . .
H19A H 0.1745 -0.0093 0.4383 0.034 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
N C1 1.347(2) . ?
N C13 1.350(2) . ?
C1 C2 1.424(3) . ?
C1 C6 1.434(3) . ?
C2 C3 1.356(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.418(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.361(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.429(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.405(3) . ?
C7 C8 1.403(3) . ?
C7 C14 1.499(3) . ?
C8 C9 1.429(3) . ?
C8 C13 1.438(3) . ?
C9 C10 1.354(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.422(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.362(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.421(3) . ?
C12 H12A 0.9500 . ?
C14 C19 1.394(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.391(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.394(3) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
C1 N C13 118.00(16) . . ?
N C1 C2 117.82(18) . . ?
N C1 C6 123.26(17) . . ?
C2 C1 C6 118.91(19) . . ?
C3 C2 C1 120.94(19) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C2 C3 C4 120.52(19) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 121.01(19) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C7 C6 C5 123.46(17) . . ?
C7 C6 C1 118.41(18) . . ?
C5 C6 C1 118.13(17) . . ?
C6 C7 C8 118.83(17) . . ?
C6 C7 C14 121.40(18) . . ?
C8 C7 C14 119.78(16) . . ?
C7 C8 C9 123.47(17) . . ?
C7 C8 C13 118.52(17) . . ?
C9 C8 C13 118.00(17) . . ?
C10 C9 C8 121.19(18) . . ?
C10 C9 H9A 119.4 . . ?
C8 C9 H9A 119.4 . . ?
C9 C10 C11 120.44(19) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C12 C11 C10 120.68(19) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 120.41(18) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
N C13 C12 117.80(17) . . ?
N C13 C8 122.92(18) . . ?
C12 C13 C8 119.28(17) . . ?
C19 C14 C15 118.89(18) . . ?
C19 C14 C7 120.10(18) . . ?
C15 C14 C7 121.00(19) . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C18 C17 C16 119.89(19) . . ?
C18 C17 H17A 120.1 . . ?
C16 C17 H17A 120.1 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C14 C19 C18 120.3(2) . . ?
C14 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


####################################################################### 
# 
# 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_g1025
_database_code_depnum_ccdc_archive 'CCDC 1500186'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H12 Cl N'
_chemical_formula_sum            'C19 H12 Cl N'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         289.75

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'
Cl Cl 0.1484 0.1585 '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                   7.5233(11)
_cell_length_b                   9.2661(15)
_cell_length_c                   11.5013(15)
_cell_angle_alpha                109.068(14)
_cell_angle_beta                 96.475(12)
_cell_angle_gamma                105.036(13)
_cell_volume                     714.49(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    672
_cell_measurement_theta_min      3.6210
_cell_measurement_theta_max      22.8050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.259
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5453
_diffrn_reflns_av_unetI/netI     0.1369
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.090
_diffrn_reflns_theta_max         29.197
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3251
_reflns_number_gt                1184
_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       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1066P)²] 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         3251
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2208
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2825
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
Cl1 Cl 1.1899(2) 1.51573(17) 0.41433(14) 0.0880(6) Uani 1 1 d . . . . .
N N 0.7758(6) 1.0491(5) -0.0884(4) 0.0596(11) Uani 1 1 d . . . . .
C1 C 0.8683(6) 1.1523(6) 0.0306(5) 0.0544(13) Uani 1 1 d . . . . .
C2 C 0.9868(7) 1.3068(6) 0.0464(5) 0.0659(15) Uani 1 1 d . . . . .
H2A H 0.9989 1.3341 -0.0239 0.079 Uiso 1 1 calc R U . . .
C3 C 1.0831(7) 1.4159(6) 0.1624(5) 0.0660(15) Uani 1 1 d . . . . .
H3A H 1.1594 1.5174 0.1718 0.079 Uiso 1 1 calc R U . . .
C4 C 1.0653(7) 1.3729(6) 0.2678(5) 0.0615(13) Uani 1 1 d . . . . .
C5 C 0.9590(6) 1.2278(6) 0.2594(5) 0.0566(13) Uani 1 1 d . . . . .
H5A H 0.9516 1.2045 0.3318 0.068 Uiso 1 1 calc R U . . .
C6 C 0.8569(6) 1.1087(6) 0.1389(5) 0.0509(12) Uani 1 1 d . . . . .
C7 C 0.7439(6) 0.9560(6) 0.1236(4) 0.0502(12) Uani 1 1 d . . . . .
C8 C 0.6410(6) 0.8501(6) 0.0002(5) 0.0559(13) Uani 1 1 d . . . . .
C9 C 0.5181(6) 0.6921(6) -0.0266(5) 0.0611(14) Uani 1 1 d . . . . .
H9A H 0.5000 0.6559 0.0390 0.073 Uiso 1 1 calc R U . . .
C10 C 0.4258(7) 0.5922(7) -0.1482(5) 0.0744(16) Uani 1 1 d . . . . .
H10A H 0.3463 0.4894 -0.1641 0.089 Uiso 1 1 calc R U . . .
C11 C 0.4514(8) 0.6451(7) -0.2485(5) 0.0756(16) Uani 1 1 d . . . . .
H11A H 0.3892 0.5768 -0.3304 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5658(8) 0.7946(7) -0.2265(5) 0.0712(16) Uani 1 1 d . . . . .
H12A H 0.5804 0.8278 -0.2939 0.085 Uiso 1 1 calc R U . . .
C13 C 0.6654(7) 0.9034(6) -0.1015(4) 0.0558(13) Uani 1 1 d . . . . .
C14 C 0.7345(7) 0.9006(5) 0.2312(4) 0.0539(12) Uani 1 1 d . . . . .
C15 C 0.8919(7) 0.8730(6) 0.2834(5) 0.0621(14) Uani 1 1 d . . . . .
H15A H 1.0009 0.8898 0.2518 0.074 Uiso 1 1 calc R U . . .
C16 C 0.8850(9) 0.8197(7) 0.3839(5) 0.0778(16) Uani 1 1 d . . . . .
H16A H 0.9896 0.7997 0.4184 0.093 Uiso 1 1 calc R U . . .
C17 C 0.7276(10) 0.7968(6) 0.4319(5) 0.0784(18) Uani 1 1 d . . . . .
H17A H 0.7234 0.7596 0.4978 0.094 Uiso 1 1 calc R U . . .
C18 C 0.5746(9) 0.8293(6) 0.3819(6) 0.0805(18) Uani 1 1 d . . . . .
H18A H 0.4687 0.8180 0.4169 0.097 Uiso 1 1 calc R U . . .
C19 C 0.5755(7) 0.8785(6) 0.2802(5) 0.0678(15) Uani 1 1 d . . . . .
H19A H 0.4694 0.8965 0.2455 0.081 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
Cl1 C4 1.735(5) . ?
N C1 1.363(6) . ?
N C13 1.339(6) . ?
C1 C2 1.418(6) . ?
C1 C6 1.434(6) . ?
C2 C3 1.359(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.340(6) . ?
C5 C6 1.432(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(6) . ?
C7 C8 1.423(6) . ?
C7 C14 1.488(6) . ?
C8 C9 1.425(6) . ?
C8 C13 1.423(7) . ?
C9 C10 1.377(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.406(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.352(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.436(7) . ?
C12 H12A 0.9300 . ?
C14 C19 1.376(7) . ?
C14 C15 1.387(6) . ?
C15 C16 1.399(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.359(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.387(7) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C13 117.2(4) . . ?
N C1 C2 118.1(5) . . ?
N C1 C6 122.9(4) . . ?
C2 C1 C6 119.0(5) . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 118.9(5) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 123.0(5) . . ?
C5 C4 Cl1 119.5(4) . . ?
C3 C4 Cl1 117.5(4) . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C1 119.3(4) . . ?
C7 C6 C5 122.9(4) . . ?
C1 C6 C5 117.8(4) . . ?
C6 C7 C8 118.0(4) . . ?
C6 C7 C14 121.7(4) . . ?
C8 C7 C14 120.2(4) . . ?
C7 C8 C9 123.1(5) . . ?
C7 C8 C13 118.4(5) . . ?
C9 C8 C13 118.5(5) . . ?
C10 C9 C8 121.0(5) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C9 C10 C11 120.2(6) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 121.5(5) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
N C13 C8 124.2(5) . . ?
N C13 C12 117.6(5) . . ?
C8 C13 C12 118.3(5) . . ?
C19 C14 C15 119.9(5) . . ?
C19 C14 C7 121.6(5) . . ?
C15 C14 C7 118.5(4) . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15A 120.4 . . ?
C14 C15 H15A 120.4 . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C16 C17 C18 119.2(5) . . ?
C16 C17 H17A 120.4 . . ?
C18 C17 H17A 120.4 . . ?
C19 C18 C17 121.2(6) . . ?
C19 C18 H18A 119.4 . . ?
C17 C18 H18A 119.4 . . ?
C14 C19 C18 119.5(5) . . ?
C14 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.058

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


####################################################################### 
# 
# 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_int1
_database_code_depnum_ccdc_archive 'CCDC 1500187'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H17 N'
_chemical_formula_sum            'C19 H17 N'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         259.33

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                   9.0735(9)
_cell_length_b                   9.1093(10)
_cell_length_c                   9.1688(9)
_cell_angle_alpha                71.085(3)
_cell_angle_beta                 75.202(3)
_cell_angle_gamma                85.168(4)
_cell_volume                     693.13(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      3.241
_cell_measurement_theta_max      26.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7223
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6313
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.311
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2788
_reflns_number_gt                1834
_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 V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0972P)²+0.5125P] 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         2788
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2090
_refine_ls_wR_factor_gt          0.1792
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.2980(2) 0.6733(2) -0.0565(2) 0.0359(5) Uani 1 1 d . . . . .
C1 C 0.3180(3) 0.6901(3) 0.0801(3) 0.0348(6) Uani 1 1 d . . . . .
C2 C 0.3560(3) 0.8388(3) 0.0781(3) 0.0435(7) Uani 1 1 d . . . . .
H2 H 0.3677 0.9233 -0.0176 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3762(3) 0.8624(3) 0.2117(4) 0.0450(7) Uani 1 1 d . . . . .
H3 H 0.3996 0.9632 0.2089 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3622(3) 0.7372(3) 0.3534(3) 0.0420(7) Uani 1 1 d . . . . .
H4 H 0.3783 0.7535 0.4454 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3254(3) 0.5916(3) 0.3595(3) 0.0368(6) Uani 1 1 d . . . . .
H5 H 0.3169 0.5081 0.4557 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2999(3) 0.5642(3) 0.2237(3) 0.0301(6) Uani 1 1 d . . . . .
C7 C 0.2527(3) 0.4194(3) 0.2253(3) 0.0273(5) Uani 1 1 d . . . . .
C8 C 0.2291(3) 0.4045(3) 0.0874(3) 0.0300(6) Uani 1 1 d . . . . .
C9 C 0.1694(4) 0.2564(3) 0.0857(3) 0.0418(7) Uani 1 1 d . . . . .
H9A H 0.2225 0.1678 0.1473 0.050 Uiso 1 1 calc R U . . .
H9B H 0.0596 0.2475 0.1399 0.050 Uiso 1 1 calc R U . . .
C10 C 0.1884(4) 0.2440(4) -0.0769(4) 0.0569(9) Uani 1 1 d . . . . .
H10A H 0.2960 0.2186 -0.1182 0.068 Uiso 1 1 calc R U . . .
H10B H 0.1244 0.1580 -0.0697 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1456(4) 0.3900(4) -0.1905(3) 0.0487(8) Uani 1 1 d . . . . .
H11A H 0.0367 0.4133 -0.1522 0.058 Uiso 1 1 calc R U . . .
H11B H 0.1594 0.3756 -0.2956 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2416(3) 0.5241(3) -0.2071(3) 0.0440(7) Uani 1 1 d . . . . .
H12A H 0.3446 0.5138 -0.2728 0.053 Uiso 1 1 calc R U . . .
H12B H 0.1964 0.6215 -0.2646 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2569(3) 0.5366(3) -0.0528(3) 0.0344(6) Uani 1 1 d . . . . .
C14 C 0.2224(3) 0.2856(3) 0.3765(3) 0.0269(5) Uani 1 1 d . . . . .
C15 C 0.3411(3) 0.1963(3) 0.4286(3) 0.0353(6) Uani 1 1 d . . . . .
H15 H 0.4431 0.2198 0.3684 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3119(3) 0.0719(3) 0.5691(3) 0.0391(7) Uani 1 1 d . . . . .
H16 H 0.3942 0.0117 0.6042 0.047 Uiso 1 1 calc R U . . .
C17 C 0.1658(3) 0.0357(3) 0.6568(3) 0.0358(6) Uani 1 1 d . . . . .
H17 H 0.1463 -0.0501 0.7516 0.043 Uiso 1 1 calc R U . . .
C18 C 0.0475(3) 0.1247(4) 0.6064(3) 0.0467(8) Uani 1 1 d . . . . .
H18 H -0.0543 0.1008 0.6672 0.056 Uiso 1 1 calc R U . . .
C19 C 0.0757(3) 0.2496(3) 0.4671(3) 0.0426(7) Uani 1 1 d . . . . .
H19 H -0.0070 0.3108 0.4339 0.051 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 C13 1.317(3) . ?
N1 C1 1.367(3) . ?
C1 C2 1.419(4) . ?
C1 C6 1.421(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.422(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(3) . ?
C7 C8 1.384(3) . ?
C7 C14 1.500(3) . ?
C8 C13 1.431(3) . ?
C8 C9 1.502(4) . ?
C9 C10 1.496(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.492(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.505(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.497(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C19 1.379(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(4) . ?
C18 H18 0.9500 . ?
C19 H19 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
C13 N1 C1 118.5(2) . . ?
N1 C1 C2 118.7(2) . . ?
N1 C1 C6 122.1(2) . . ?
C2 C1 C6 119.2(2) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C1 118.1(2) . . ?
C7 C6 C5 123.5(2) . . ?
C1 C6 C5 118.3(2) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 C14 120.5(2) . . ?
C6 C7 C14 120.2(2) . . ?
C7 C8 C13 118.2(2) . . ?
C7 C8 C9 121.3(2) . . ?
C13 C8 C9 120.5(2) . . ?
C10 C9 C8 114.3(2) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 111.1(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 114.4(2) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N1 C13 C8 123.6(2) . . ?
N1 C13 C12 116.1(2) . . ?
C8 C13 C12 120.3(2) . . ?
C19 C14 C15 118.6(2) . . ?
C19 C14 C7 120.7(2) . . ?
C15 C14 C7 120.7(2) . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.7(2) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.056

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


####################################################################### 
# 
# 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_int2
_database_code_depnum_ccdc_archive 'CCDC 1500188'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         273.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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                   8.2767(7)
_cell_length_b                   8.6984(6)
_cell_length_c                   11.4987(9)
_cell_angle_alpha                110.318(2)
_cell_angle_beta                 90.656(3)
_cell_angle_gamma                115.299(3)
_cell_volume                     689.29(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6282
_cell_measurement_theta_min      3.062
_cell_measurement_theta_max      26.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8323
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11650
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.149
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2813
_reflns_number_gt                2375
_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 V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1001P)²+0.2821P] 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         2813
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O O 0.1790(2) 0.49565(19) 0.26265(12) 0.0482(4) Uani 1 1 d . . . . .
N N 0.39201(18) 0.69798(18) 0.49577(12) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.4829(2) 0.8015(2) 0.61702(14) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.6069(2) 0.9913(2) 0.64990(17) 0.0303(4) Uani 1 1 d . . . . .
H2 H 0.6263 1.0411 0.5868 0.036 Uiso 1 1 calc R U . . .
C3 C 0.6979(2) 1.1019(2) 0.77075(17) 0.0347(4) Uani 1 1 d . . . . .
H3 H 0.7800 1.2283 0.7914 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6705(2) 1.0294(2) 0.86570(16) 0.0338(4) Uani 1 1 d . . . . .
H4 H 0.7349 1.1075 0.9498 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5521(2) 0.8477(2) 0.83755(15) 0.0280(4) Uani 1 1 d . . . . .
H5 H 0.5349 0.8014 0.9025 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4548(2) 0.7279(2) 0.71263(14) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.33094(19) 0.5381(2) 0.67739(14) 0.0212(3) Uani 1 1 d . . . . .
C8 C 0.2374(2) 0.4344(2) 0.55436(14) 0.0222(3) Uani 1 1 d . . . . .
C9 C 0.0992(2) 0.2338(2) 0.51249(15) 0.0283(4) Uani 1 1 d . . . . .
H9A H 0.1632 0.1568 0.4912 0.034 Uiso 1 1 calc R U . . .
H9B H 0.0378 0.2152 0.5834 0.034 Uiso 1 1 calc R U . . .
C10 C -0.0422(2) 0.1702(2) 0.39980(17) 0.0356(4) Uani 1 1 d . . . . .
H10A H -0.1202 0.2319 0.4245 0.043 Uiso 1 1 calc R U . . .
H10B H -0.1205 0.0354 0.3705 0.043 Uiso 1 1 calc R U . . .
C11 C 0.0469(3) 0.2146(2) 0.29321(16) 0.0396(5) Uani 1 1 d . . . . .
H11A H 0.1200 0.1478 0.2659 0.048 Uiso 1 1 calc R U . . .
H11B H -0.0485 0.1713 0.2203 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1677(2) 0.4182(2) 0.33286(15) 0.0292(4) Uani 1 1 d . . . . .
C13 C 0.2735(2) 0.5233(2) 0.46709(14) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.30141(19) 0.45389(19) 0.77366(13) 0.0223(3) Uani 1 1 d . . . . .
C15 C 0.1977(2) 0.4901(2) 0.86355(15) 0.0290(4) Uani 1 1 d . . . . .
H15 H 0.1453 0.5682 0.8635 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1702(2) 0.4130(2) 0.95361(16) 0.0328(4) Uani 1 1 d . . . . .
H16 H 0.0999 0.4390 1.0153 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2457(2) 0.2980(2) 0.95307(15) 0.0309(4) Uani 1 1 d . . . . .
H17 H 0.2259 0.2438 1.0139 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3493(2) 0.2620(2) 0.86457(15) 0.0301(4) Uani 1 1 d . . . . .
H18 H 0.4015 0.1838 0.8650 0.036 Uiso 1 1 calc R U . . .
C19 C 0.3780(2) 0.3395(2) 0.77461(14) 0.0263(4) Uani 1 1 d . . . . .
H19 H 0.4498 0.3145 0.7139 0.032 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
O C12 1.200(2) . ?
N C13 1.323(2) . ?
N C1 1.359(2) . ?
C1 C2 1.425(2) . ?
C1 C6 1.429(2) . ?
C2 C3 1.361(2) . ?
C3 C4 1.415(2) . ?
C4 C5 1.370(2) . ?
C5 C6 1.419(2) . ?
C6 C7 1.421(2) . ?
C7 C8 1.381(2) . ?
C7 C14 1.4961(19) . ?
C8 C13 1.429(2) . ?
C8 C9 1.511(2) . ?
C9 C10 1.507(2) . ?
C10 C11 1.517(3) . ?
C11 C12 1.503(2) . ?
C12 C13 1.513(2) . ?
C14 C15 1.389(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.390(2) . ?
C16 C17 1.386(2) . ?
C17 C18 1.378(2) . ?
C18 C19 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N C1 117.98(13) . . ?
N C1 C2 118.49(14) . . ?
N C1 C6 122.28(14) . . ?
C2 C1 C6 119.21(14) . . ?
C3 C2 C1 120.73(15) . . ?
C2 C3 C4 120.23(15) . . ?
C5 C4 C3 120.63(15) . . ?
C4 C5 C6 120.83(15) . . ?
C5 C6 C7 123.49(13) . . ?
C5 C6 C1 118.36(14) . . ?
C7 C6 C1 118.15(13) . . ?
C8 C7 C6 119.18(13) . . ?
C8 C7 C14 120.86(13) . . ?
C6 C7 C14 119.95(13) . . ?
C7 C8 C13 117.90(13) . . ?
C7 C8 C9 121.55(13) . . ?
C13 C8 C9 120.55(13) . . ?
C10 C9 C8 112.81(13) . . ?
C9 C10 C11 110.80(15) . . ?
C12 C11 C10 111.67(14) . . ?
O C12 C11 122.10(15) . . ?
O C12 C13 121.00(15) . . ?
C11 C12 C13 116.90(13) . . ?
N C13 C8 124.46(14) . . ?
N C13 C12 115.61(13) . . ?
C8 C13 C12 119.89(13) . . ?
C15 C14 C19 119.35(13) . . ?
C15 C14 C7 120.13(13) . . ?
C19 C14 C7 120.52(13) . . ?
C14 C15 C16 120.51(15) . . ?
C17 C16 C15 119.70(15) . . ?
C18 C17 C16 120.13(14) . . ?
C17 C18 C19 120.39(15) . . ?
C18 C19 C14 119.91(14) . . ?

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.056

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?


