# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ad_ap_214_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2394938'
loop_
_audit_author_name
_audit_author_address
'Anit Pal'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_audit_creation_date             2024-06-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5367(3)
_cell_length_b                   7.7309(4)
_cell_length_c                   29.9149(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1280.47(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9081
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1230 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.9143.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6813
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            28487
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.334
_diffrn_reflns_theta_min         2.721
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1931
_reflns_number_total             2347
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      1.143
_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)+(0.0546P)²+1.5615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.1829
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O2 O 0.6625(9) 0.7262(6) 0.51908(15) 0.0654(14) Uani 1 1 d . . . . .
H2 H 0.783(15) 0.721(13) 0.507(3) 0.098 Uiso 1 1 d . U . . .
N1 N 0.2653(8) 0.3530(6) 0.62243(15) 0.0431(11) Uani 1 1 d . . . . .
C1 C 0.1211(10) 0.6050(6) 0.66775(16) 0.0358(12) Uani 1 1 d . . . . .
C2 C -0.0501(10) 0.7306(8) 0.67677(19) 0.0483(14) Uani 1 1 d . . . . .
H2A H -0.185706 0.739799 0.658593 0.058 Uiso 1 1 calc R U . . .
C3 C -0.0226(13) 0.8421(8) 0.7122(2) 0.0614(19) Uani 1 1 d . . . . .
H3 H -0.140638 0.924642 0.718028 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1765(13) 0.8325(9) 0.7390(2) 0.0612(19) Uani 1 1 d . . . . .
H4 H 0.194609 0.907979 0.762929 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3496(12) 0.7107(9) 0.73013(18) 0.0558(16) Uani 1 1 d . . . . .
H5 H 0.486230 0.703591 0.748108 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3220(10) 0.5988(8) 0.69480(17) 0.0434(14) Uani 1 1 d . . . . .
H6 H 0.441481 0.517273 0.689047 0.052 Uiso 1 1 calc R U . . .
C7 C 0.0774(10) 0.4781(8) 0.63014(18) 0.0456(14) Uani 1 1 d . . . . .
H7A H -0.071379 0.416361 0.636313 0.055 Uiso 1 1 calc R U . . .
H7B H 0.053207 0.543235 0.602780 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2347(12) 0.1889(8) 0.6446(2) 0.0596(18) Uani 1 1 d . . . . .
H8A H 0.103381 0.126356 0.630453 0.072 Uiso 1 1 calc R U . . .
H8B H 0.190346 0.209073 0.675508 0.072 Uiso 1 1 calc R U . . .
C9 C 0.4565(17) 0.0805(10) 0.6432(3) 0.091(3) Uani 1 1 d . . . . .
H9A H 0.576517 0.130583 0.662956 0.109 Uiso 1 1 calc R U . . .
H9B H 0.418090 -0.034042 0.654389 0.109 Uiso 1 1 calc R U . . .
C10 C 0.5605(13) 0.0642(7) 0.59813(18) 0.0522(16) Uani 1 1 d . . . . .
H10A H 0.455032 -0.005879 0.579638 0.063 Uiso 1 1 calc R U . . .
H10B H 0.715951 0.006791 0.599963 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5919(10) 0.2404(7) 0.57701(15) 0.0371(12) Uani 1 1 d . . . . .
C12 C 0.4393(10) 0.3763(7) 0.59011(16) 0.0360(12) Uani 1 1 d . . . . .
C13 C 0.7646(10) 0.2705(7) 0.54511(17) 0.0433(13) Uani 1 1 d . . . . .
H13 H 0.864868 0.179752 0.536591 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7960(11) 0.4312(8) 0.52494(17) 0.0453(14) Uani 1 1 d . . . . .
H14 H 0.914298 0.448446 0.503319 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6479(11) 0.5622(7) 0.53793(16) 0.0430(14) Uani 1 1 d . . . . .
C16 C 0.4738(11) 0.5397(7) 0.57027(17) 0.0406(13) Uani 1 1 d . . . . .
H16 H 0.378460 0.632734 0.579050 0.049 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
O2 H2 0.76(8) . ?
O2 C15 1.390(7) . ?
N1 C7 1.439(7) . ?
N1 C8 1.442(7) . ?
N1 C12 1.377(7) . ?
C1 C2 1.384(7) . ?
C1 C6 1.376(7) . ?
C1 C7 1.512(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.375(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(8) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.487(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.472(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(8) . ?
C11 C12 1.403(7) . ?
C11 C13 1.371(7) . ?
C12 C16 1.409(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.360(8) . ?
C15 C16 1.377(8) . ?
C16 H16 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
C15 O2 H2 102(7) . . ?
C7 N1 C8 115.7(5) . . ?
C12 N1 C7 122.1(5) . . ?
C12 N1 C8 121.3(5) . . ?
C2 C1 C7 119.4(5) . . ?
C6 C1 C2 117.6(5) . . ?
C6 C1 C7 123.0(5) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.0(6) . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(6) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(6) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(6) . . ?
C5 C6 H6 119.3 . . ?
N1 C7 C1 116.1(5) . . ?
N1 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
N1 C8 C9 112.7(5) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.4(7) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 C11 110.6(5) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C12 C11 C10 119.2(5) . . ?
C13 C11 C10 121.6(5) . . ?
C13 C11 C12 119.2(5) . . ?
N1 C12 C11 121.3(5) . . ?
N1 C12 C16 120.5(5) . . ?
C11 C12 C16 118.2(5) . . ?
C11 C13 H13 118.7 . . ?
C11 C13 C14 122.7(5) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.7(5) . . ?
C15 C14 H14 121.1 . . ?
C14 C15 O2 121.9(5) . . ?
C14 C15 C16 121.9(5) . . ?
C16 C15 O2 116.2(5) . . ?
C12 C16 H16 119.9 . . ?
C15 C16 C12 120.3(5) . . ?
C15 C16 H16 119.9 . . ?

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
O2 C15 C16 C12 177.6(5) . . . . ?
N1 C8 C9 C10 -49.9(9) . . . . ?
N1 C12 C16 C15 -179.9(5) . . . . ?
C1 C2 C3 C4 0.9(9) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
C2 C1 C7 N1 179.1(5) . . . . ?
C2 C3 C4 C5 0.1(9) . . . . ?
C3 C4 C5 C6 -0.3(9) . . . . ?
C4 C5 C6 C1 -0.5(9) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C6 C1 C7 N1 -2.9(8) . . . . ?
C7 N1 C8 C9 -167.8(6) . . . . ?
C7 N1 C12 C11 -167.5(5) . . . . ?
C7 N1 C12 C16 14.6(7) . . . . ?
C7 C1 C2 C3 176.4(5) . . . . ?
C7 C1 C6 C5 -176.6(5) . . . . ?
C8 N1 C7 C1 94.1(6) . . . . ?
C8 N1 C12 C11 0.9(8) . . . . ?
C8 N1 C12 C16 -177.1(6) . . . . ?
C8 C9 C10 C11 51.0(9) . . . . ?
C9 C10 C11 C12 -27.2(9) . . . . ?
C9 C10 C11 C13 153.3(6) . . . . ?
C10 C11 C12 N1 1.3(8) . . . . ?
C10 C11 C12 C16 179.4(5) . . . . ?
C10 C11 C13 C14 179.6(5) . . . . ?
C11 C12 C16 C15 2.0(8) . . . . ?
C11 C13 C14 C15 0.1(8) . . . . ?
C12 N1 C7 C1 -97.0(6) . . . . ?
C12 N1 C8 C9 23.1(9) . . . . ?
C12 C11 C13 C14 0.1(8) . . . . ?
C13 C11 C12 N1 -179.1(5) . . . . ?
C13 C11 C12 C16 -1.1(7) . . . . ?
C13 C14 C15 O2 -178.7(5) . . . . ?
C13 C14 C15 C16 0.8(8) . . . . ?
C14 C15 C16 C12 -1.9(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ad_ap_209_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2394939'
loop_
_audit_author_name
_audit_author_address
'Anit Pal'
;IIT Guwahati
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_audit_creation_date             2024-06-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 N'
_chemical_formula_sum            'C24 H21 N'
_chemical_formula_weight         323.42
_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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.1945(9)
_cell_length_b                   21.100(2)
_cell_length_c                   11.3760(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.258(3)
_cell_angle_gamma                90
_cell_volume                     1878.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6858
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1233 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.9203.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   0.7452
_exptl_transmission_factor_min   0.6858
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41672
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.036
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2281
_reflns_number_total             3314
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0711
_refine_ls_restrained_S_all      1.131
_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)+(0.0429P)²+1.0797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1700
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N 0.3279(3) 0.55152(12) 0.6298(2) 0.0751(7) Uani 1 1 d . . . . .
C1 C 0.7873(3) 0.68590(12) 0.2263(2) 0.0590(7) Uani 1 1 d . . . . .
C2 C 0.9265(4) 0.72521(13) 0.2413(3) 0.0736(8) Uani 1 1 d . . . . .
H2 H 0.991703 0.736953 0.320051 0.088 Uiso 1 1 calc R U . . .
C3 C 0.9693(5) 0.74702(16) 0.1412(4) 0.0925(11) Uani 1 1 d . . . . .
H3 H 1.062802 0.773796 0.152079 0.111 Uiso 1 1 calc R U . . .
C4 C 0.8754(6) 0.72964(18) 0.0252(4) 0.0982(12) Uani 1 1 d . . . . .
H4 H 0.904506 0.744567 -0.042857 0.118 Uiso 1 1 calc R U . . .
C5 C 0.7380(5) 0.69011(18) 0.0097(3) 0.0927(11) Uani 1 1 d . . . . .
H5 H 0.674962 0.677829 -0.069265 0.111 Uiso 1 1 calc R U . . .
C6 C 0.6925(4) 0.66851(15) 0.1087(3) 0.0752(8) Uani 1 1 d . . . . .
H6 H 0.598081 0.642160 0.097019 0.090 Uiso 1 1 calc R U . . .
C7 C 0.7444(3) 0.66346(13) 0.3324(3) 0.0655(7) Uani 1 1 d . . . . .
C8 C 0.7111(3) 0.64417(13) 0.4214(3) 0.0630(7) Uani 1 1 d . . . . .
C9 C 0.6775(3) 0.62058(12) 0.5307(2) 0.0558(6) Uani 1 1 d . . . . .
C10 C 0.5155(3) 0.59728(11) 0.5237(2) 0.0541(6) Uani 1 1 d . . . . .
C11 C 0.4864(3) 0.57379(12) 0.6314(2) 0.0577(7) Uani 1 1 d . . . . .
C12 C 0.6216(4) 0.57468(13) 0.7414(3) 0.0683(8) Uani 1 1 d . . . . .
H12 H 0.603800 0.559509 0.813341 0.082 Uiso 1 1 calc R U . . .
C13 C 0.7801(4) 0.59761(15) 0.7446(3) 0.0727(8) Uani 1 1 d . . . . .
H13 H 0.868019 0.597357 0.818339 0.087 Uiso 1 1 calc R U . . .
C14 C 0.8097(3) 0.62073(14) 0.6407(3) 0.0672(8) Uani 1 1 d . . . . .
H14 H 0.916848 0.636378 0.643476 0.081 Uiso 1 1 calc R U . . .
C15 C 0.3732(3) 0.59834(14) 0.4048(2) 0.0684(8) Uani 1 1 d . . . . .
H15A H 0.381675 0.636492 0.359358 0.082 Uiso 1 1 calc R U . . .
H15B H 0.384007 0.562134 0.355032 0.082 Uiso 1 1 calc R U . . .
C16 C 0.2038(4) 0.5965(2) 0.4278(4) 0.1102(13) Uani 1 1 d . . . . .
H16A H 0.179007 0.638455 0.452818 0.132 Uiso 1 1 calc R U . . .
H16B H 0.117541 0.586622 0.350949 0.132 Uiso 1 1 calc R U . . .
C17 C 0.1888(4) 0.5520(2) 0.5190(4) 0.0999(11) Uani 1 1 d . . . . .
H17A H 0.084597 0.561103 0.539685 0.120 Uiso 1 1 calc R U . . .
H17B H 0.177297 0.509838 0.483313 0.120 Uiso 1 1 calc R U . . .
C18 C 0.3038(5) 0.51523(15) 0.7310(3) 0.0866(10) Uani 1 1 d . . . . .
H18A H 0.404913 0.489572 0.765419 0.104 Uiso 1 1 calc R U . . .
H18B H 0.208485 0.486530 0.698766 0.104 Uiso 1 1 calc R U . . .
C19 C 0.2701(3) 0.55361(14) 0.8342(3) 0.0677(7) Uani 1 1 d . . . . .
C20 C 0.2682(3) 0.61859(14) 0.8351(3) 0.0705(8) Uani 1 1 d . . . . .
H20 H 0.288273 0.640745 0.770033 0.085 Uiso 1 1 calc R U . . .
C21 C 0.2370(4) 0.65162(16) 0.9307(3) 0.0796(9) Uani 1 1 d . . . . .
H21 H 0.236527 0.695696 0.929887 0.096 Uiso 1 1 calc R U . . .
C22 C 0.2065(4) 0.6196(2) 1.0271(3) 0.0909(10) Uani 1 1 d . . . . .
H22 H 0.185730 0.641882 1.091782 0.109 Uiso 1 1 calc R U . . .
C23 C 0.2070(5) 0.5551(2) 1.0276(3) 0.1015(12) Uani 1 1 d . . . . .
H23 H 0.185845 0.533180 1.092442 0.122 Uiso 1 1 calc R U . . .
C24 C 0.2388(4) 0.52225(17) 0.9320(3) 0.0909(10) Uani 1 1 d . . . . .
H24 H 0.239076 0.478177 0.933289 0.109 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 C11 1.376(3) . ?
N1 C17 1.427(4) . ?
N1 C18 1.444(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.382(4) . ?
C1 C7 1.434(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.196(4) . ?
C8 C9 1.439(4) . ?
C9 C10 1.396(3) . ?
C9 C14 1.391(4) . ?
C10 C11 1.406(3) . ?
C10 C15 1.501(4) . ?
C11 C12 1.404(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.488(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.432(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.517(4) . ?
C19 C20 1.371(4) . ?
C19 C24 1.383(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.361(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(5) . ?
C24 H24 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
C11 N1 C17 120.8(3) . . ?
C11 N1 C18 121.5(3) . . ?
C17 N1 C18 116.4(3) . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 C7 119.6(3) . . ?
C6 C1 C7 121.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C1 178.9(3) . . ?
C7 C8 C9 177.9(3) . . ?
C10 C9 C8 119.7(2) . . ?
C14 C9 C8 118.6(2) . . ?
C14 C9 C10 121.7(2) . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 C15 121.1(2) . . ?
C11 C10 C15 120.2(2) . . ?
N1 C11 C10 120.8(2) . . ?
N1 C11 C12 120.6(3) . . ?
C12 C11 C10 118.6(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 C10 110.9(2) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C15 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 115.5(3) . . ?
C17 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
N1 C17 C16 115.2(3) . . ?
N1 C17 H17A 108.5 . . ?
N1 C17 H17B 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
N1 C18 H18A 108.4 . . ?
N1 C18 H18B 108.4 . . ?
N1 C18 C19 115.6(3) . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
C20 C19 C18 123.0(3) . . ?
C20 C19 C24 117.9(3) . . ?
C24 C19 C18 119.1(3) . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.1(3) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.2(3) . . ?
C23 C24 H24 119.4 . . ?

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
N1 C11 C12 C13 -179.1(3) . . . . ?
N1 C18 C19 C20 -2.2(4) . . . . ?
N1 C18 C19 C24 177.4(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C7 C1 C2 C3 180.0(3) . . . . ?
C7 C1 C6 C5 -179.2(3) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C8 C9 C10 C15 -2.1(4) . . . . ?
C8 C9 C14 C13 -179.0(3) . . . . ?
C9 C10 C11 N1 178.6(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C15 C16 -157.1(3) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C15 C16 C17 -44.1(4) . . . . ?
C11 N1 C17 C16 -22.6(5) . . . . ?
C11 N1 C18 C19 87.7(4) . . . . ?
C11 C10 C15 C16 21.6(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C14 C9 C10 C15 179.0(2) . . . . ?
C15 C10 C11 N1 -0.1(4) . . . . ?
C15 C10 C11 C12 -178.8(2) . . . . ?
C15 C16 C17 N1 45.7(5) . . . . ?
C17 N1 C11 C10 -0.3(4) . . . . ?
C17 N1 C11 C12 178.4(3) . . . . ?
C17 N1 C18 C19 -104.8(3) . . . . ?
C18 N1 C11 C10 166.7(2) . . . . ?
C18 N1 C11 C12 -14.6(4) . . . . ?
C18 N1 C17 C16 169.8(3) . . . . ?
C18 C19 C20 C21 180.0(3) . . . . ?
C18 C19 C24 C23 -179.8(3) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C20 C19 C24 C23 -0.2(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 0.3(6) . . . . ?
C22 C23 C24 C19 -0.2(6) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AP_581_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2469969'
loop_
_audit_author_name
_audit_author_address
'ANIT PAL'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-07-04 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_audit_creation_date             2025-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C18 H21 N'
_chemical_formula_sum            'C18 H21 N'
_chemical_formula_weight         251.374
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.355(3)
_cell_length_b                   16.065(5)
_cell_length_c                   11.289(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.475(7)
_cell_angle_gamma                90
_cell_volume                     1437.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8244
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.57
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1448 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.9324.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_description       block
_exptl_crystal_F_000             544.274
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33923
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9948
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.15
_diffrn_reflns_theta_min         2.29
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9948
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2176
_reflns_number_total             2851
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4823
_refine_diff_density_min         -0.3270
_refine_diff_density_rms         0.0805
_refine_ls_d_res_high            0.8064
_refine_ls_d_res_low             8.9098
_refine_ls_goodness_of_fit_ref   1.1043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0881
_refine_ls_restrained_S_all      1.1043
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0057P)²+2.2964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1568
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
N1 N 0.3527(3) 0.40386(17) 0.6952(2) 0.0437(6) Uani 1.000000 .
C1 C 0.5746(4) 0.49107(18) 0.8381(2) 0.0386(7) Uani 1.000000 .
C2 C 0.4933(4) 0.5674(2) 0.8367(3) 0.0455(8) Uani 1.000000 .
C3 C 0.5886(5) 0.6398(2) 0.8554(3) 0.0613(10) Uani 1.000000 .
H3 H 0.5356(5) 0.6907(2) 0.8553(3) 0.0736(12) Uiso 1.000000 R
C4 C 0.7593(6) 0.6383(3) 0.8740(3) 0.0672(11) Uani 1.000000 .
H4 H 0.8205(6) 0.6877(3) 0.8860(3) 0.0806(13) Uiso 1.000000 R
C5 C 0.8386(5) 0.5640(3) 0.8748(3) 0.0617(10) Uani 1.000000 .
H5 H 0.9541(5) 0.5626(3) 0.8874(3) 0.0740(12) Uiso 1.000000 R
C6 C 0.7467(4) 0.4905(2) 0.8568(3) 0.0510(8) Uani 1.000000 .
H6 H 0.8015(4) 0.4401(2) 0.8572(3) 0.0612(10) Uiso 1.000000 R
C7 C 0.4729(4) 0.41052(19) 0.8224(3) 0.0409(7) Uani 1.000000 .
H7 H 0.4053(4) 0.41442(19) 0.8791(3) 0.0491(9) Uiso 1.000000 R
C8 C 0.4138(4) 0.4270(2) 0.5926(3) 0.0536(9) Uani 1.000000 .
H8a H 0.4061(4) 0.4869(2) 0.5822(3) 0.0643(11) Uiso 1.000000 R
H8b H 0.5319(4) 0.4117(2) 0.6140(3) 0.0643(11) Uiso 1.000000 R
C9 C 0.3191(4) 0.3870(3) 0.4726(3) 0.0638(10) Uani 1.000000 .
H9a H 0.3548(4) 0.4107(3) 0.4061(3) 0.0766(13) Uiso 1.000000 R
H9b H 0.3445(4) 0.3279(3) 0.4771(3) 0.0766(13) Uiso 1.000000 R
C10 C 0.1325(4) 0.3990(2) 0.4433(3) 0.0550(9) Uani 1.000000 .
H10a H 0.1048(4) 0.4575(2) 0.4281(3) 0.0661(11) Uiso 1.000000 R
H10b H 0.0730(4) 0.3682(2) 0.3684(3) 0.0661(11) Uiso 1.000000 R
C11 C 0.0778(4) 0.36904(18) 0.5505(3) 0.0406(7) Uani 1.000000 .
C12 C 0.1926(4) 0.37122(17) 0.6732(3) 0.0370(7) Uani 1.000000 .
C13 C 0.3062(4) 0.5719(2) 0.8161(3) 0.0635(10) Uani 1.000000 .
H13a H 0.2461(4) 0.5496(15) 0.7353(10) 0.0952(15) Uiso 1.000000 GR
H13b H 0.2796(6) 0.5400(13) 0.8793(14) 0.0952(15) Uiso 1.000000 GR
H13c H 0.2738(7) 0.6288(3) 0.821(2) 0.0952(15) Uiso 1.000000 GR
C14 C 0.5777(4) 0.3314(2) 0.8578(3) 0.0553(9) Uani 1.000000 .
H14a H 0.5044(5) 0.2849(3) 0.855(2) 0.0829(14) Uiso 1.000000 GR
H14b H 0.639(2) 0.3225(8) 0.8000(13) 0.0829(14) Uiso 1.000000 GR
H14c H 0.656(2) 0.3369(6) 0.9407(9) 0.0829(14) Uiso 1.000000 GR
C15 C -0.0820(4) 0.3369(2) 0.5310(3) 0.0512(8) Uani 1.000000 .
H15 H -0.1568(4) 0.3351(2) 0.4500(3) 0.0615(10) Uiso 1.000000 R
C16 C -0.1347(4) 0.3075(2) 0.6274(4) 0.0572(9) Uani 1.000000 .
H16 H -0.2436(4) 0.2872(2) 0.6120(4) 0.0687(11) Uiso 1.000000 R
C17 C -0.0226(4) 0.3088(2) 0.7466(3) 0.0538(9) Uani 1.000000 .
H17 H -0.0559(4) 0.2886(2) 0.8124(3) 0.0645(10) Uiso 1.000000 R
C18 C 0.1384(4) 0.3397(2) 0.7701(3) 0.0465(8) Uani 1.000000 .
H18 H 0.2123(4) 0.3396(2) 0.8514(3) 0.0558(9) Uiso 1.000000 R


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 C7 1.473(4) . ?
N1 C8 1.454(4) . ?
N1 C12 1.384(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.386(4) . ?
C1 C7 1.527(4) . ?
C2 C3 1.387(5) . ?
C2 C13 1.508(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C14 1.523(4) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 C9 1.481(4) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C9 C10 1.500(5) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 C11 1.502(4) . ?
C11 C12 1.414(4) . ?
C11 C15 1.383(4) . ?
C12 C18 1.404(4) . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.380(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(4) . ?
C18 H18 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
C8 N1 C7 117.1(2) . . ?
C12 N1 C7 121.6(2) . . ?
C12 N1 C8 121.2(2) . . ?
C6 C1 C2 118.9(3) . . ?
C7 C1 C2 119.4(3) . . ?
C7 C1 C6 121.7(3) . . ?
C3 C2 C1 118.7(3) . . ?
C13 C2 C1 121.3(3) . . ?
C13 C2 C3 120.0(3) . . ?
H3 C3 C2 119.1(2) . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.1(2) . . ?
H4 C4 C3 120.2(2) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2(2) . . ?
H5 C5 C4 120.0(2) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0(2) . . ?
C5 C6 C1 121.1(3) . . ?
H6 C6 C1 119.45(19) . . ?
H6 C6 C5 119.4(2) . . ?
C1 C7 N1 110.9(2) . . ?
H7 C7 N1 106.54(15) . . ?
H7 C7 C1 106.54(15) . . ?
C14 C7 N1 110.6(3) . . ?
C14 C7 C1 115.1(2) . . ?
C14 C7 H7 106.54(18) . . ?
H8a C8 N1 108.89(19) . . ?
H8b C8 N1 108.89(17) . . ?
H8b C8 H8a 107.7 . . ?
C9 C8 N1 113.4(3) . . ?
C9 C8 H8a 108.9(2) . . ?
C9 C8 H8b 108.9(2) . . ?
H9a C9 C8 109.38(18) . . ?
H9b C9 C8 109.4(2) . . ?
H9b C9 H9a 108.0 . . ?
C10 C9 C8 111.2(3) . . ?
C10 C9 H9a 109.38(18) . . ?
C10 C9 H9b 109.4(2) . . ?
H10a C10 C9 109.7(2) . . ?
H10b C10 C9 109.67(19) . . ?
H10b C10 H10a 108.2 . . ?
C11 C10 C9 110.0(3) . . ?
C11 C10 H10a 109.67(19) . . ?
C11 C10 H10b 109.67(17) . . ?
C12 C11 C10 119.8(3) . . ?
C15 C11 C10 121.1(3) . . ?
C15 C11 C12 119.1(3) . . ?
C11 C12 N1 120.1(3) . . ?
C18 C12 N1 122.0(3) . . ?
C18 C12 C11 117.9(3) . . ?
H13a C13 C2 109.5 . . ?
H13b C13 C2 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C2 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 C7 109.5 . . ?
H14b C14 C7 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C7 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15 C15 C11 118.81(19) . . ?
C16 C15 C11 122.4(3) . . ?
C16 C15 H15 118.8(2) . . ?
H16 C16 C15 120.7(2) . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 H16 120.7(2) . . ?
H17 C17 C16 119.5(2) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.5(2) . . ?
C17 C18 C12 121.1(3) . . ?
H18 C18 C12 119.46(18) . . ?
H18 C18 C17 119.5(2) . . ?

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
N1 C7 C1 C2 68.2(3) . . . . ?
N1 C7 C1 C6 -113.3(3) . . . . ?
N1 C8 C9 C10 51.0(3) . . . . ?
N1 C12 C11 C10 2.5(3) . . . . ?
N1 C12 C11 C15 -179.3(3) . . . . ?
N1 C12 C18 C17 178.8(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C8 C9 C10 C11 -54.3(3) . . . . ?
C9 C10 C11 C12 28.4(4) . . . . ?
C9 C10 C11 C15 -149.7(3) . . . . ?
C10 C11 C12 C18 -177.6(3) . . . . ?
C10 C11 C15 C16 178.7(3) . . . . ?
C11 C12 C18 C17 -1.0(3) . . . . ?
C11 C15 C16 C17 -1.3(4) . . . . ?
C12 C18 C17 C16 0.4(4) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
