# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_5481
_database_code_depnum_ccdc_archive 'CCDC 1859531'
loop_
_audit_author_name
_audit_author_address
'Saghir Ali'
;IIT Guwahati
India
;
_audit_update_record             
;
2018-08-01 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N'
_chemical_formula_weight         227.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.4928(7)
_cell_length_b                   8.7755(11)
_cell_length_c                   11.1633(11)
_cell_angle_alpha                84.247(9)
_cell_angle_beta                 78.666(8)
_cell_angle_gamma                76.675(10)
_cell_volume                     699.17(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    899
_cell_measurement_theta_min      4.0760
_cell_measurement_theta_max      23.7040

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4702
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2481
_reflns_number_gt                1274
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0689P)²+0.0292P] 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         2481
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_gt          0.1354
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.1893(2) 0.6268(2) 0.60382(17) 0.0497(6) Uani 1 1 d . . . . .
C3 C 0.3008(3) 0.3929(3) 0.4884(2) 0.0449(6) Uani 1 1 d . . . . .
C2 C 0.2229(3) 0.5581(3) 0.4994(2) 0.0453(6) Uani 1 1 d . . . . .
C5 C 0.3031(3) 0.3748(3) 0.7052(2) 0.0493(6) Uani 1 1 d . . . . .
C10 C 0.2294(3) 0.5369(3) 0.7074(2) 0.0490(6) Uani 1 1 d . . . . .
C4 C 0.3382(3) 0.3062(3) 0.5920(2) 0.0503(7) Uani 1 1 d . . . . .
H4 H 0.3882 0.1991 0.5880 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1775(3) 0.6595(3) 0.3878(2) 0.0490(6) Uani 1 1 d . . . . .
H11A H 0.0872 0.6198 0.3553 0.059 Uiso 1 1 calc R U . . .
H11B H 0.2898 0.6491 0.3261 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3360(3) 0.3234(3) 0.3656(2) 0.0531(7) Uani 1 1 d . . . . .
H14A H 0.4026 0.3880 0.3057 0.064 Uiso 1 1 calc R U . . .
H14B H 0.2167 0.3289 0.3421 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2350(3) 0.5262(4) 0.9255(2) 0.0626(8) Uani 1 1 d . . . . .
C9 C 0.1989(3) 0.6092(3) 0.8190(2) 0.0586(7) Uani 1 1 d . . . . .
H9 H 0.1526 0.7170 0.8205 0.070 Uiso 1 1 calc R U . . .
C7 C 0.3044(3) 0.3619(4) 0.9241(2) 0.0647(8) Uani 1 1 d . . . . .
C6 C 0.3383(3) 0.2905(3) 0.8160(2) 0.0618(8) Uani 1 1 d . . . . .
H6 H 0.3862 0.1829 0.8154 0.074 Uiso 1 1 calc R U . . .
C12 C 0.1009(4) 0.8321(3) 0.4081(2) 0.0646(8) Uani 1 1 d . . . . .
H12A H 0.1889 0.8724 0.4424 0.078 Uiso 1 1 calc R U . . .
H12B H -0.0145 0.8441 0.4672 0.078 Uiso 1 1 calc R U . . .
C15 C 0.4453(4) 0.1552(3) 0.3589(2) 0.0707(8) Uani 1 1 d . . . . .
H15A H 0.4637 0.1232 0.2768 0.106 Uiso 1 1 calc R U . . .
H15B H 0.3773 0.0884 0.4138 0.106 Uiso 1 1 calc R U . . .
H15C H 0.5641 0.1476 0.3819 0.106 Uiso 1 1 calc R U . . .
C16 C 0.1997(4) 0.6099(4) 1.0427(2) 0.0877(10) Uani 1 1 d . . . . .
H16A H 0.3142 0.5952 1.0730 0.132 Uiso 1 1 calc R U . . .
H16B H 0.1103 0.5677 1.1027 0.132 Uiso 1 1 calc R U . . .
H16C H 0.1520 0.7198 1.0269 0.132 Uiso 1 1 calc R U . . .
C13 C 0.0643(4) 0.9279(3) 0.2911(3) 0.0885(10) Uani 1 1 d . . . . .
H13A H 0.1787 0.9188 0.2331 0.133 Uiso 1 1 calc R U . . .
H13B H 0.0152 1.0360 0.3087 0.133 Uiso 1 1 calc R U . . .
H13C H -0.0243 0.8895 0.2574 0.133 Uiso 1 1 calc R U . . .
C17 C 0.3409(4) 0.2656(4) 1.0413(2) 0.0924(11) Uani 1 1 d . . . . .
H17A H 0.4228 0.3082 1.0781 0.139 Uiso 1 1 calc R U . . .
H17B H 0.3977 0.1589 1.0226 0.139 Uiso 1 1 calc R U . . .
H17C H 0.2251 0.2688 1.0971 0.139 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 C2 1.320(3) . ?
N1 C10 1.376(3) . ?
C3 C4 1.360(3) . ?
C3 C2 1.440(3) . ?
C3 C14 1.508(3) . ?
C2 C11 1.505(3) . ?
C5 C10 1.403(3) . ?
C5 C4 1.405(3) . ?
C5 C6 1.415(3) . ?
C10 C9 1.410(3) . ?
C4 H4 0.9300 . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C8 C9 1.371(3) . ?
C8 C7 1.416(4) . ?
C8 C16 1.513(4) . ?
C9 H9 0.9300 . ?
C7 C6 1.367(3) . ?
C7 C17 1.521(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.518(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 N1 C10 118.7(2) . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 C14 122.9(2) . . ?
C2 C3 C14 119.8(2) . . ?
N1 C2 C3 123.0(2) . . ?
N1 C2 C11 117.5(2) . . ?
C3 C2 C11 119.5(2) . . ?
C10 C5 C4 117.6(2) . . ?
C10 C5 C6 118.4(2) . . ?
C4 C5 C6 124.0(2) . . ?
N1 C10 C5 122.0(2) . . ?
N1 C10 C9 119.4(2) . . ?
C5 C10 C9 118.6(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C2 C11 C12 115.5(2) . . ?
C2 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
C2 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C3 C14 C15 115.9(2) . . ?
C3 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
C3 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 C16 120.0(3) . . ?
C7 C8 C16 120.8(3) . . ?
C8 C9 C10 122.3(3) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 C17 120.2(3) . . ?
C8 C7 C17 120.5(3) . . ?
C7 C6 C5 122.2(3) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C11 C12 C13 112.6(2) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 H16A 109.5 . . ?
C8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034

