# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_gz-6-14
_database_code_depnum_ccdc_archive 'CCDC 2217984'
loop_
_audit_author_name
_audit_author_address
'benzyl aniline acetone'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2022-11-05 deposited with the CCDC.	2023-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.1534(5)
_cell_length_b                   14.2426(10)
_cell_length_c                   7.9499(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.172(7)
_cell_angle_gamma                90
_cell_volume                     695.66(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6709
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.573
_diffrn_reflns_theta_max         71.720
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2605
_reflns_number_gt                2228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_max     0.913
_reflns_Friedel_fraction_full    0.945

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1513P)²+0.0151P] 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_abs_structure_details 
;
 Flack x determined using 794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.2125
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O -0.1010(7) -0.2981(3) -0.1991(8) 0.0951(15) Uani 1 1 d . . . . .
N1 N -0.7142(7) -0.4154(3) -0.2719(5) 0.0603(10) Uani 1 1 d . . . . .
H1 H -0.8057 -0.3742 -0.3112 0.072 Uiso 1 1 calc R U . . .
C1 C -0.9761(9) -0.5344(5) -0.3497(7) 0.0728(14) Uani 1 1 d . . . . .
H1A H -1.0799 -0.4877 -0.3705 0.087 Uiso 1 1 calc R U . . .
C2 C -1.0316(12) -0.6277(6) -0.3778(11) 0.096(2) Uani 1 1 d . . . . .
H2 H -1.1725 -0.6432 -0.4162 0.115 Uiso 1 1 calc R U . . .
C3 C -0.8797(12) -0.6974(6) -0.3494(11) 0.100(2) Uani 1 1 d . . . . .
H3 H -0.9176 -0.7599 -0.3688 0.120 Uiso 1 1 calc R U . . .
C4 C -0.6702(12) -0.6745(4) -0.2916(9) 0.0860(17) Uani 1 1 d . . . . .
H4 H -0.5673 -0.7217 -0.2731 0.103 Uiso 1 1 calc R U . . .
C5 C -0.6121(10) -0.5815(4) -0.2610(7) 0.0704(12) Uani 1 1 d . . . . .
H5 H -0.4713 -0.5669 -0.2209 0.084 Uiso 1 1 calc R U . . .
C6 C -0.7655(8) -0.5099(4) -0.2905(5) 0.0571(10) Uani 1 1 d . . . . .
C7 C -0.5111(7) -0.3834(3) -0.1881(5) 0.0541(9) Uani 1 1 d . . . . .
H7 H -0.3923 -0.4169 -0.2393 0.065 Uiso 1 1 calc R U . . .
C8 C -0.4952(7) -0.4052(3) -0.0001(5) 0.0525(9) Uani 1 1 d . . . . .
C9 C -0.3038(8) -0.4443(4) 0.0723(6) 0.0618(11) Uani 1 1 d . . . . .
H9 H -0.1880 -0.4579 0.0059 0.074 Uiso 1 1 calc R U . . .
C10 C -0.2878(9) -0.4626(4) 0.2440(7) 0.0746(14) Uani 1 1 d . . . . .
H10 H -0.1621 -0.4903 0.2917 0.090 Uiso 1 1 calc R U . . .
C11 C -0.4539(9) -0.4407(4) 0.3437(6) 0.0721(13) Uani 1 1 d . . . . .
H11 H -0.4398 -0.4521 0.4590 0.087 Uiso 1 1 calc R U . . .
C12 C -0.6432(8) -0.4014(4) 0.2733(6) 0.0659(12) Uani 1 1 d . . . . .
H12 H -0.7574 -0.3871 0.3408 0.079 Uiso 1 1 calc R U . . .
C13 C -0.6622(8) -0.3834(3) 0.1012(6) 0.0586(10) Uani 1 1 d . . . . .
H13 H -0.7890 -0.3563 0.0541 0.070 Uiso 1 1 calc R U . . .
C14 C -0.4818(9) -0.2788(3) -0.2235(7) 0.0652(12) Uani 1 1 d . . . . .
H14A H -0.5317 -0.2661 -0.3391 0.078 Uiso 1 1 calc R U . . .
H14B H -0.5731 -0.2432 -0.1509 0.078 Uiso 1 1 calc R U . . .
C15 C -0.2525(9) -0.2452(4) -0.1968(7) 0.0669(12) Uani 1 1 d . . . . .
C16 C -0.2157(14) -0.1411(5) -0.1775(13) 0.104(2) Uani 1 1 d . . . . .
H16A H -0.1848 -0.1264 -0.0608 0.155 Uiso 1 1 calc R U . . .
H16B H -0.3439 -0.1080 -0.2182 0.155 Uiso 1 1 calc R U . . .
H16C H -0.0948 -0.1226 -0.2413 0.155 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
O1 C15 1.200(6) . ?
N1 C6 1.388(7) . ?
N1 C7 1.456(6) . ?
C1 C2 1.387(10) . ?
C1 C6 1.399(7) . ?
C2 C3 1.374(12) . ?
C3 C4 1.384(10) . ?
C4 C5 1.389(9) . ?
C5 C6 1.401(7) . ?
C7 C8 1.524(6) . ?
C7 C14 1.529(6) . ?
C8 C13 1.376(7) . ?
C8 C9 1.398(6) . ?
C9 C10 1.388(7) . ?
C10 C11 1.364(9) . ?
C11 C12 1.383(8) . ?
C12 C13 1.391(7) . ?
C14 C15 1.494(8) . ?
C15 C16 1.506(8) . ?

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
C6 N1 C7 122.4(3) . . ?
C2 C1 C6 120.6(6) . . ?
C3 C2 C1 120.5(6) . . ?
C2 C3 C4 119.8(7) . . ?
C3 C4 C5 120.7(6) . . ?
C4 C5 C6 120.0(6) . . ?
N1 C6 C1 118.6(4) . . ?
N1 C6 C5 122.8(5) . . ?
C1 C6 C5 118.5(5) . . ?
N1 C7 C8 113.1(4) . . ?
N1 C7 C14 109.1(4) . . ?
C8 C7 C14 112.1(4) . . ?
C13 C8 C9 119.3(4) . . ?
C13 C8 C7 121.2(4) . . ?
C9 C8 C7 119.5(4) . . ?
C10 C9 C8 119.5(5) . . ?
C11 C10 C9 120.9(5) . . ?
C10 C11 C12 119.9(5) . . ?
C11 C12 C13 119.7(5) . . ?
C8 C13 C12 120.6(4) . . ?
C15 C14 C7 114.0(4) . . ?
O1 C15 C14 121.7(5) . . ?
O1 C15 C16 120.5(6) . . ?
C14 C15 C16 117.8(5) . . ?

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-1

