# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2117809'
loop_
_audit_author_name
_audit_author_address
'JAYANTA SAMANTA'
;Dartmouth College
United States of America
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_audit_creation_date             2021-10-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N O'
_chemical_formula_sum            'C14 H17 N O'
_chemical_formula_weight         215.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2601(17)
_cell_length_b                   6.3866(8)
_cell_length_c                   15.0670(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.852(4)
_cell_angle_gamma                90
_cell_volume                     1192.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2949
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8471.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24583
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.773
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  
'Bruker D8 Venture PHOTON 100 CMOS diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2520
_reflns_number_total             2949
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+0.3347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.42531(8) -0.04411(15) 0.37282(8) 0.0550(3) Uani 1 1 d . . . . .
N1 N 0.31506(9) 0.55501(16) 0.30801(8) 0.0421(3) Uani 1 1 d . . . . .
H1 H 0.356912 0.658044 0.333988 0.050 Uiso 1 1 calc R U . . .
C1 C 0.20823(10) 0.6028(2) 0.25015(9) 0.0395(3) Uani 1 1 d . . . . .
C2 C 0.14194(12) 0.4599(2) 0.18644(11) 0.0482(3) Uani 1 1 d . . . . .
H2 H 0.167069 0.325829 0.181934 0.058 Uiso 1 1 calc R U . . .
C3 C 0.03816(12) 0.5173(3) 0.12951(11) 0.0544(4) Uani 1 1 d . . . . .
H3 H -0.006028 0.419340 0.088038 0.065 Uiso 1 1 calc R U . . .
C4 C -0.00127(11) 0.7161(3) 0.13277(11) 0.0526(4) Uani 1 1 d . . . . .
C5 C 0.06595(12) 0.8566(2) 0.19660(11) 0.0525(4) Uani 1 1 d . . . . .
H5 H 0.041142 0.991367 0.200165 0.063 Uiso 1 1 calc R U . . .
C6 C 0.16900(11) 0.8018(2) 0.25519(11) 0.0477(3) Uani 1 1 d . . . . .
H6 H 0.212103 0.898766 0.298100 0.057 Uiso 1 1 calc R U . . .
C7 C -0.11365(15) 0.7793(4) 0.06930(16) 0.0815(6) Uani 1 1 d . . . . .
H7A H -0.132721 0.909072 0.091411 0.122 Uiso 1 1 calc R U . . .
H7B H -0.164029 0.672624 0.070761 0.122 Uiso 1 1 calc R U . . .
H7C H -0.115584 0.796436 0.005414 0.122 Uiso 1 1 calc R U . . .
C8 C 0.35711(10) 0.36005(19) 0.32599(9) 0.0396(3) Uani 1 1 d . . . . .
H8 H 0.309094 0.248161 0.309937 0.047 Uiso 1 1 calc R U . . .
C9 C 0.46361(10) 0.31471(18) 0.36552(9) 0.0375(3) Uani 1 1 d . . . . .
C10 C 0.49326(10) 0.09531(19) 0.38378(9) 0.0397(3) Uani 1 1 d . . . . .
C11 C 0.61079(11) 0.0358(2) 0.41446(11) 0.0490(3) Uani 1 1 d . . . . .
H11A H 0.623338 -0.028360 0.360952 0.059 Uiso 1 1 calc R U . . .
H11B H 0.625767 -0.069078 0.464063 0.059 Uiso 1 1 calc R U . . .
C12 C 0.69052(11) 0.2154(2) 0.45099(12) 0.0540(4) Uani 1 1 d . . . . .
H12A H 0.695469 0.251773 0.514911 0.065 Uiso 1 1 calc R U . . .
H12B H 0.761439 0.170909 0.453516 0.065 Uiso 1 1 calc R U . . .
C13 C 0.65600(11) 0.4052(2) 0.38780(11) 0.0493(3) Uani 1 1 d . . . . .
H13A H 0.650520 0.368991 0.323720 0.059 Uiso 1 1 calc R U . . .
H13B H 0.709757 0.514643 0.410705 0.059 Uiso 1 1 calc R U . . .
C14 C 0.54783(11) 0.4845(2) 0.38691(11) 0.0449(3) Uani 1 1 d . . . . .
H14A H 0.557190 0.545396 0.448317 0.054 Uiso 1 1 calc R U . . .
H14B H 0.522530 0.594093 0.339559 0.054 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 C10 1.2353(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.4073(16) . ?
N1 C8 1.3517(16) . ?
C1 C2 1.3878(19) . ?
C1 C6 1.3858(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(2) . ?
C4 C5 1.383(2) . ?
C4 C7 1.511(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.3543(17) . ?
C9 C10 1.4549(17) . ?
C9 C14 1.5069(17) . ?
C10 C11 1.5081(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.524(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.508(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5168(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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 H1 117.4 . . ?
C8 N1 H1 117.4 . . ?
C8 N1 C1 125.19(11) . . ?
C2 C1 N1 122.41(12) . . ?
C6 C1 N1 118.66(12) . . ?
C6 C1 C2 118.91(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.90(13) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.75(14) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 117.55(13) . . ?
C3 C4 C7 121.60(16) . . ?
C5 C4 C7 120.85(16) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.73(14) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.14(13) . . ?
C5 C6 H6 119.9 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8 117.4 . . ?
N1 C8 C9 125.19(12) . . ?
C9 C8 H8 117.4 . . ?
C8 C9 C10 117.28(11) . . ?
C8 C9 C14 121.17(11) . . ?
C10 C9 C14 121.52(11) . . ?
O1 C10 C9 122.26(12) . . ?
O1 C10 C11 118.96(12) . . ?
C9 C10 C11 118.75(11) . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C10 C11 C12 115.43(11) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.18(12) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 C14 110.34(13) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C9 C14 C13 112.83(11) . . ?
C9 C14 H14A 109.0 . . ?
C9 C14 H14B 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?

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
O1 C10 C11 C12 -164.70(14) . . . . ?
N1 C1 C2 C3 -178.40(13) . . . . ?
N1 C1 C6 C5 177.38(13) . . . . ?
N1 C8 C9 C10 177.01(12) . . . . ?
N1 C8 C9 C14 -4.8(2) . . . . ?
C1 N1 C8 C9 166.26(12) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C3 C4 C7 178.83(17) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C7 C4 C5 C6 -179.95(17) . . . . ?
C8 N1 C1 C2 -16.5(2) . . . . ?
C8 N1 C1 C6 165.32(13) . . . . ?
C8 C9 C10 O1 -6.9(2) . . . . ?
C8 C9 C10 C11 171.34(12) . . . . ?
C8 C9 C14 C13 -154.08(13) . . . . ?
C9 C10 C11 C12 17.0(2) . . . . ?
C10 C9 C14 C13 24.08(19) . . . . ?
C10 C11 C12 C13 -44.61(19) . . . . ?
C11 C12 C13 C14 62.06(17) . . . . ?
C12 C13 C14 C9 -51.08(17) . . . . ?
C14 C9 C10 O1 174.89(13) . . . . ?
C14 C9 C10 C11 -6.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
