# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_platon
_database_code_depnum_ccdc_archive 'CCDC 1947123'
loop_
_audit_author_name
_audit_author_address
'Subhra Kanti Roy'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-((5-methyl-1H-indol-3-yl)methyl)aniline
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H16 N2'
_chemical_formula_sum            'C16 H16 N2'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         236.31

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   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?

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                   20.126(4)
_cell_length_b                   7.6043(4)
_cell_length_c                   19.1043(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.182(10)
_cell_angle_gamma                90.00
_cell_volume                     2667.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5096
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.00
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_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            4654
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2339
_reflns_number_gt                1614
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0642P)²+1.1425P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2339
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.22557(11) 0.5304(3) 0.00355(13) 0.0499(6) Uani 1 1 d . . .
H1 H 0.2578 0.5049 -0.0137 0.060 Uiso 1 1 calc R . .
N2 N 0.14476(11) 1.0461(3) 0.04189(12) 0.0549(6) Uani 1 1 d . . .
H2A H 0.1721 1.1373 0.0578 0.066 Uiso 1 1 calc R . .
H2B H 0.1536 0.9536 0.0702 0.066 Uiso 1 1 calc R . .
C7 C 0.12444(12) 0.6419(3) 0.00903(13) 0.0397(6) Uani 1 1 d . . .
C6 C 0.16260(12) 0.5421(3) 0.07705(13) 0.0388(6) Uani 1 1 d . . .
C5 C 0.14958(13) 0.5025(3) 0.14212(14) 0.0441(6) Uani 1 1 d . . .
H5 H 0.1075 0.5436 0.1457 0.053 Uiso 1 1 calc R . .
C4 C 0.19897(14) 0.4026(3) 0.20098(14) 0.0500(7) Uani 1 1 d . . .
C3 C 0.26234(14) 0.3420(3) 0.19446(16) 0.0565(8) Uani 1 1 d . . .
H3 H 0.2958 0.2762 0.2344 0.068 Uiso 1 1 calc R . .
C2 C 0.27658(14) 0.3763(3) 0.13161(16) 0.0545(7) Uani 1 1 d . . .
H2 H 0.3186 0.3338 0.1285 0.065 Uiso 1 1 calc R . .
C1 C 0.22656(13) 0.4762(3) 0.07245(15) 0.0430(6) Uani 1 1 d . . .
C8 C 0.16476(13) 0.6321(3) -0.03346(15) 0.0469(7) Uani 1 1 d . . .
H8 H 0.1528 0.6864 -0.0807 0.056 Uiso 1 1 calc R . .
C9 C 0.05356(12) 0.7370(3) -0.00981(15) 0.0469(7) Uani 1 1 d . . .
H9A H 0.0140 0.6557 -0.0362 0.056 Uiso 1 1 calc R . .
H9B H 0.0506 0.7695 0.0379 0.056 Uiso 1 1 calc R . .
C10 C 0.04173(12) 0.8998(3) -0.05832(13) 0.0387(6) Uani 1 1 d . . .
C15 C 0.08582(12) 1.0483(3) -0.03002(14) 0.0399(6) Uani 1 1 d . . .
C14 C 0.07245(15) 1.1991(3) -0.07485(17) 0.0552(7) Uani 1 1 d . . .
H14 H 0.1019 1.2976 -0.0564 0.066 Uiso 1 1 calc R . .
C13 C 0.01587(18) 1.2035(4) -0.14642(19) 0.0693(9) Uani 1 1 d . . .
H13 H 0.0073 1.3051 -0.1759 0.083 Uiso 1 1 calc R . .
C12 C -0.02809(17) 1.0599(5) -0.17488(17) 0.0702(9) Uani 1 1 d . . .
H12 H -0.0664 1.0635 -0.2232 0.084 Uiso 1 1 calc R . .
C11 C -0.01450(14) 0.9098(4) -0.13057(15) 0.0558(7) Uani 1 1 d . . .
H11 H -0.0442 0.8120 -0.1500 0.067 Uiso 1 1 calc R . .
C16 C 0.18616(17) 0.3594(4) 0.27203(15) 0.0684(9) Uani 1 1 d . . .
H16A H 0.2212 0.4206 0.3154 0.103 Uiso 1 1 calc R . .
H16B H 0.1913 0.2350 0.2813 0.103 Uiso 1 1 calc R . .
H16C H 0.1379 0.3953 0.2643 0.103 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0469(12) 0.0493(12) 0.0629(15) -0.0027(11) 0.0319(12) 0.0021(10)
N2 0.0458(12) 0.0556(13) 0.0555(14) -0.0106(11) 0.0129(11) -0.0078(10)
C7 0.0398(13) 0.0357(13) 0.0460(14) -0.0006(11) 0.0201(12) -0.0032(10)
C6 0.0369(12) 0.0332(12) 0.0443(14) -0.0041(11) 0.0146(11) -0.0057(10)
C5 0.0433(14) 0.0412(13) 0.0481(15) -0.0028(12) 0.0190(12) -0.0034(11)
C4 0.0525(15) 0.0459(14) 0.0427(15) 0.0003(12) 0.0106(13) -0.0062(12)
C3 0.0498(16) 0.0501(16) 0.0539(17) 0.0061(13) 0.0053(14) 0.0048(13)
C2 0.0386(14) 0.0508(15) 0.0684(19) -0.0040(14) 0.0162(14) 0.0052(12)
C1 0.0390(13) 0.0370(13) 0.0525(16) -0.0048(12) 0.0182(12) -0.0022(10)
C8 0.0484(15) 0.0443(14) 0.0504(16) 0.0017(12) 0.0227(13) -0.0018(12)
C9 0.0392(13) 0.0469(14) 0.0560(16) 0.0049(12) 0.0210(12) -0.0020(11)
C10 0.0324(12) 0.0467(14) 0.0385(13) 0.0000(11) 0.0161(11) 0.0039(10)
C15 0.0356(12) 0.0451(14) 0.0427(14) -0.0018(11) 0.0198(11) 0.0051(11)
C14 0.0621(17) 0.0460(15) 0.072(2) 0.0037(14) 0.0422(16) 0.0065(13)
C13 0.076(2) 0.071(2) 0.078(2) 0.0316(18) 0.049(2) 0.0289(18)
C12 0.0572(18) 0.106(3) 0.0463(17) 0.0224(18) 0.0196(15) 0.0209(18)
C11 0.0442(14) 0.0728(18) 0.0464(16) -0.0010(14) 0.0147(13) -0.0017(14)
C16 0.079(2) 0.071(2) 0.0490(17) 0.0070(15) 0.0199(16) -0.0053(16)

_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 C1 1.372(3) . ?
N1 C8 1.373(3) . ?
N1 H1 0.8600 . ?
N2 C15 1.400(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C7 C8 1.365(3) . ?
C7 C6 1.427(3) . ?
C7 C9 1.505(3) . ?
C6 C5 1.404(3) . ?
C6 C1 1.417(3) . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.409(4) . ?
C4 C16 1.518(4) . ?
C3 C2 1.369(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.391(3) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.383(3) . ?
C10 C15 1.401(3) . ?
C15 C14 1.390(3) . ?
C14 C13 1.375(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.370(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.380(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N1 C8 108.84(19) . . ?
C1 N1 H1 125.6 . . ?
C8 N1 H1 125.6 . . ?
C15 N2 H2A 120.0 . . ?
C15 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 C7 C6 106.4(2) . . ?
C8 C7 C9 128.3(2) . . ?
C6 C7 C9 125.2(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.0(2) . . ?
C1 C6 C7 107.2(2) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C16 121.1(2) . . ?
C3 C4 C16 120.0(2) . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
N1 C1 C2 131.7(2) . . ?
N1 C1 C6 107.3(2) . . ?
C2 C1 C6 121.1(2) . . ?
C7 C8 N1 110.3(2) . . ?
C7 C8 H8 124.9 . . ?
N1 C8 H8 124.9 . . ?
C10 C9 C7 115.93(19) . . ?
C10 C9 H9A 108.3 . . ?
C7 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C7 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C9 121.2(2) . . ?
C15 C10 C9 120.7(2) . . ?
C14 C15 C10 119.7(2) . . ?
C14 C15 N2 119.1(2) . . ?
C10 C15 N2 121.2(2) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C11 C10 122.2(3) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C7 C6 C5 179.9(2) . . . . ?
C9 C7 C6 C5 -0.2(4) . . . . ?
C8 C7 C6 C1 0.6(3) . . . . ?
C9 C7 C6 C1 -179.6(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C7 C6 C5 C4 -178.5(2) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C6 C5 C4 C16 179.6(2) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?
C16 C4 C3 C2 179.7(3) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C8 N1 C1 C2 -178.0(3) . . . . ?
C8 N1 C1 C6 2.0(3) . . . . ?
C3 C2 C1 N1 -179.6(2) . . . . ?
C3 C2 C1 C6 0.4(4) . . . . ?
C5 C6 C1 N1 179.0(2) . . . . ?
C7 C6 C1 N1 -1.6(2) . . . . ?
C5 C6 C1 C2 -1.1(3) . . . . ?
C7 C6 C1 C2 178.4(2) . . . . ?
C6 C7 C8 N1 0.6(3) . . . . ?
C9 C7 C8 N1 -179.2(2) . . . . ?
C1 N1 C8 C7 -1.6(3) . . . . ?
C8 C7 C9 C10 -30.2(4) . . . . ?
C6 C7 C9 C10 150.0(2) . . . . ?
C7 C9 C10 C11 116.8(2) . . . . ?
C7 C9 C10 C15 -65.8(3) . . . . ?
C11 C10 C15 C14 -0.5(3) . . . . ?
C9 C10 C15 C14 -177.9(2) . . . . ?
C11 C10 C15 N2 -178.5(2) . . . . ?
C9 C10 C15 N2 4.1(3) . . . . ?
C10 C15 C14 C13 0.5(4) . . . . ?
N2 C15 C14 C13 178.6(2) . . . . ?
C15 C14 C13 C12 -0.1(4) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C13 C12 C11 C10 0.3(4) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C9 C10 C11 C12 177.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_exp_5406
_database_code_depnum_ccdc_archive 'CCDC 1947126'
loop_
_audit_author_name
_audit_author_address
'Subhra Kanti Roy'
;IIT Guwahati
India
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-((1H-indol-3-yl)methyl)aniline
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H14 N2'
_chemical_formula_sum            'C15 H14 N2'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         222.28

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           orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_int_tables_number      56
_chemical_absolute_configuration ?

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

_cell_length_a                   20.3252(11)
_cell_length_b                   17.4919(13)
_cell_length_c                   7.6118(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2706.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7432
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      24.99
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_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            7088
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2375
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2375
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1657
_refine_ls_R_factor_gt           0.1227
_refine_ls_wR_factor_ref         0.3975
_refine_ls_wR_factor_gt          0.3538
_refine_ls_goodness_of_fit_ref   1.346
_refine_ls_restrained_S_all      1.346
_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
N N 0.72398(19) 0.4579(2) 0.0752(4) 0.0650(12) Uani 1 1 d . . .
H H 0.7652 0.4657 0.0572 0.078 Uiso 1 1 calc R . .
N17 N 0.6238(2) 0.4491(2) 0.5826(5) 0.0714(13) Uani 1 1 d . . .
H17A H 0.6234 0.4155 0.6767 0.086 Uiso 1 1 d R . .
H17B H 0.6127 0.4163 0.4882 0.086 Uiso 1 1 d R . .
C12 C 0.6029(2) 0.5243(3) 0.5760(5) 0.0578(13) Uani 1 1 d . . .
C7 C 0.6872(2) 0.3993(3) 0.0039(5) 0.0617(13) Uani 1 1 d . . .
C2 C 0.6224(2) 0.4073(3) 0.0637(5) 0.0577(13) Uani 1 1 d . . .
C11 C 0.5746(2) 0.5540(3) 0.4222(5) 0.0600(14) Uani 1 1 d . . .
C1 C 0.6212(2) 0.4731(3) 0.1760(5) 0.0603(13) Uani 1 1 d . . .
C9 C 0.6841(2) 0.5015(3) 0.1790(5) 0.0678(14) Uani 1 1 d . . .
H9 H 0.6976 0.5441 0.2425 0.081 Uiso 1 1 calc R . .
C3 C 0.5757(2) 0.3553(3) 0.0069(6) 0.0750(16) Uani 1 1 d . . .
H3 H 0.5324 0.3594 0.0454 0.090 Uiso 1 1 calc R . .
C13 C 0.6131(2) 0.5719(4) 0.7203(6) 0.0849(19) Uani 1 1 d . . .
H13 H 0.6322 0.5517 0.8212 0.102 Uiso 1 1 calc R . .
C6 C 0.7057(3) 0.3414(3) -0.1101(6) 0.0737(16) Uani 1 1 d . . .
H6 H 0.7489 0.3365 -0.1488 0.088 Uiso 1 1 calc R . .
C10 C 0.5603(2) 0.5046(4) 0.2668(6) 0.0778(17) Uani 1 1 d . . .
H10A H 0.5351 0.5340 0.1823 0.093 Uiso 1 1 calc R . .
H10B H 0.5331 0.4621 0.3046 0.093 Uiso 1 1 calc R . .
C4 C 0.5935(3) 0.2968(4) -0.1082(7) 0.0827(16) Uani 1 1 d . . .
H4 H 0.5622 0.2619 -0.1469 0.099 Uiso 1 1 calc R . .
C5 C 0.6573(3) 0.2912(3) -0.1638(7) 0.0821(17) Uani 1 1 d . . .
H5 H 0.6686 0.2520 -0.2408 0.098 Uiso 1 1 calc R . .
C16 C 0.5581(3) 0.6309(4) 0.4254(8) 0.0932(19) Uani 1 1 d . . .
H16 H 0.5390 0.6523 0.3258 0.112 Uiso 1 1 calc R . .
C14 C 0.5954(3) 0.6485(5) 0.7172(11) 0.104(2) Uani 1 1 d . . .
H14 H 0.6021 0.6793 0.8152 0.125 Uiso 1 1 calc R . .
C15 C 0.5687(4) 0.6775(4) 0.5707(13) 0.110(2) Uani 1 1 d . . .
H15 H 0.5572 0.7289 0.5662 0.133 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N 0.041(2) 0.093(3) 0.061(2) 0.003(2) 0.0063(16) 0.001(2)
N17 0.060(3) 0.085(3) 0.069(2) 0.019(2) -0.0024(19) 0.011(2)
C12 0.039(2) 0.082(3) 0.052(3) 0.004(2) 0.0042(17) 0.004(2)
C7 0.053(3) 0.084(3) 0.048(2) 0.015(3) 0.0012(19) 0.010(2)
C2 0.046(2) 0.084(3) 0.044(2) 0.012(2) -0.0045(17) 0.002(2)
C11 0.039(2) 0.084(4) 0.057(3) 0.012(2) 0.0080(17) 0.013(2)
C1 0.044(2) 0.093(3) 0.044(2) 0.007(2) -0.0012(18) 0.007(2)
C9 0.050(3) 0.099(4) 0.055(3) -0.003(3) 0.001(2) 0.004(3)
C3 0.054(3) 0.102(4) 0.069(3) 0.022(3) -0.010(2) -0.006(3)
C13 0.059(3) 0.137(6) 0.059(3) -0.007(3) 0.003(2) -0.005(3)
C6 0.069(3) 0.084(4) 0.068(3) 0.012(3) 0.003(2) 0.021(3)
C10 0.048(3) 0.132(5) 0.053(3) -0.001(3) -0.001(2) 0.018(3)
C4 0.080(4) 0.081(4) 0.088(3) 0.007(3) -0.018(3) 0.006(3)
C5 0.083(4) 0.081(4) 0.082(3) 0.004(3) -0.016(3) 0.018(3)
C16 0.080(4) 0.105(5) 0.094(4) 0.032(4) 0.019(3) 0.030(4)
C14 0.080(4) 0.110(6) 0.121(5) -0.036(5) 0.026(4) 0.001(4)
C15 0.092(5) 0.082(4) 0.157(7) -0.007(5) 0.037(5) 0.021(4)

_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 C9 1.365(6) . ?
N C7 1.380(6) . ?
N H 0.8600 . ?
N17 C12 1.383(6) . ?
N17 H17A 0.9273 . ?
N17 H17B 0.9473 . ?
C12 C13 1.393(7) . ?
C12 C11 1.404(6) . ?
C7 C6 1.385(6) . ?
C7 C2 1.400(6) . ?
C2 C3 1.385(7) . ?
C2 C1 1.433(7) . ?
C11 C16 1.385(8) . ?
C11 C10 1.494(7) . ?
C1 C9 1.372(6) . ?
C1 C10 1.521(6) . ?
C9 H9 0.9300 . ?
C3 C4 1.394(8) . ?
C3 H3 0.9300 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9300 . ?
C6 C5 1.379(7) . ?
C6 H6 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 C5 1.368(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C15 1.391(10) . ?
C16 H16 0.9300 . ?
C14 C15 1.340(9) . ?
C14 H14 0.9300 . ?
C15 H15 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
C9 N C7 108.7(4) . . ?
C9 N H 125.6 . . ?
C7 N H 125.6 . . ?
C12 N17 H17A 129.0 . . ?
C12 N17 H17B 118.4 . . ?
H17A N17 H17B 101.4 . . ?
N17 C12 C13 119.6(5) . . ?
N17 C12 C11 120.6(4) . . ?
C13 C12 C11 119.8(5) . . ?
N C7 C6 130.0(4) . . ?
N C7 C2 107.8(4) . . ?
C6 C7 C2 122.1(5) . . ?
C3 C2 C7 118.5(5) . . ?
C3 C2 C1 134.5(4) . . ?
C7 C2 C1 107.0(4) . . ?
C16 C11 C12 116.4(5) . . ?
C16 C11 C10 121.9(5) . . ?
C12 C11 C10 121.7(5) . . ?
C9 C1 C2 106.5(4) . . ?
C9 C1 C10 128.3(5) . . ?
C2 C1 C10 125.2(4) . . ?
N C9 C1 110.0(4) . . ?
N C9 H9 125.0 . . ?
C1 C9 H9 125.0 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C14 C13 C12 121.7(6) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C5 C6 C7 117.3(5) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C11 C10 C1 114.3(4) . . ?
C11 C10 H10A 108.7 . . ?
C1 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C1 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 122.5(6) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C11 C16 C15 123.0(6) . . ?
C11 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C15 C14 C13 119.0(7) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 120.2(7) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.121

