# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2373505'
loop_
_audit_author_name
_audit_author_address
R
;China,Jilin
China
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;
_audit_creation_date             2021-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_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 R
_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 0.0181 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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   20.291(2)
_cell_length_b                   5.8861(6)
_cell_length_c                   14.4945(14)
_cell_angle_alpha                90
_cell_angle_beta                 128.653(4)
_cell_angle_gamma                90
_cell_volume                     1351.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5364
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.83
_cell_measurement_theta_min      5.58
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10141
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.058
_diffrn_reflns_theta_min         5.583
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2030
_reflns_number_total             2449
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.0038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.046
_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)+(0.0541P)²+0.1802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.52651(15) 0.5918(4) 0.37703(19) 0.0667(6) Uani 1 1 d . . . . .
O2 O 0.59728(14) 0.2489(4) 0.5223(2) 0.0837(6) Uani 1 1 d . . . . .
C1 C 0.90943(19) 0.7149(7) 0.7601(3) 0.0892(10) Uani 1 1 d . . . . .
H1A H 0.9329 0.6913 0.7187 0.134 Uiso 1 1 calc GR . . . .
H1B H 0.9489 0.6558 0.8408 0.134 Uiso 1 1 calc GR . . . .
H1C H 0.9006 0.8777 0.7627 0.134 Uiso 1 1 calc GR . . . .
C2 C 0.82618(17) 0.5916(5) 0.6953(2) 0.0695(7) Uani 1 1 d . . . . .
C3 C 0.75274(17) 0.6840(5) 0.5958(2) 0.0649(7) Uani 1 1 d . . . . .
H3 H 0.7553 0.8267 0.5676 0.078 Uiso 1 1 calc R . . . .
C4 C 0.67497(17) 0.5745(5) 0.5354(2) 0.0605(6) Uani 1 1 d . . . . .
C5 C 0.59917(18) 0.6828(5) 0.4337(2) 0.0647(7) Uani 1 1 d . . . . .
H5 H 0.6040 0.8266 0.4086 0.078 Uiso 1 1 calc R . . . .
C6 C 0.45298(17) 0.7131(5) 0.2757(2) 0.0674(7) Uani 1 1 d . . . . .
H6 H 0.4731 0.8519 0.2602 0.081 Uiso 1 1 calc R . . . .
C7 C 0.40965(16) 0.5584(5) 0.1689(2) 0.0656(7) Uani 1 1 d . . . . .
C8 C 0.4121(2) 0.6059(6) 0.0776(3) 0.0790(8) Uani 1 1 d . . . . .
H8 H 0.4392 0.7399 0.0801 0.095 Uiso 1 1 calc R . . . .
C9 C 0.3751(3) 0.4588(8) -0.0174(3) 0.0968(11) Uani 1 1 d . . . . .
H9 H 0.3769 0.4938 -0.0798 0.116 Uiso 1 1 calc R . . . .
C10 C 0.3361(2) 0.2636(8) -0.0228(3) 0.0934(11) Uani 1 1 d . . . . .
H10 H 0.3116 0.1625 -0.0877 0.112 Uiso 1 1 calc R . . . .
C11 C 0.8200(2) 0.3815(6) 0.7335(3) 0.0751(8) Uani 1 1 d . . . . .
H11 H 0.8695 0.3140 0.8015 0.090 Uiso 1 1 calc R . . . .
C12 C 0.3968(2) 0.7860(6) 0.3058(3) 0.0843(9) Uani 1 1 d . . . . .
H12A H 0.3815 0.6529 0.3295 0.126 Uiso 1 1 calc GR . . . .
H12B H 0.3454 0.8566 0.2364 0.126 Uiso 1 1 calc GR . . . .
H12C H 0.4270 0.8957 0.3709 0.126 Uiso 1 1 calc GR . . . .
C13 C 0.3698(2) 0.3610(6) 0.1620(3) 0.0773(8) Uani 1 1 d . . . . .
H13 H 0.3679 0.3244 0.2241 0.093 Uiso 1 1 calc R . . . .
C14 C 0.3328(2) 0.2164(6) 0.0668(3) 0.0885(9) Uani 1 1 d . . . . .
H14 H 0.3049 0.0831 0.0633 0.106 Uiso 1 1 calc R . . . .
C15 C 0.67110(19) 0.3615(5) 0.5763(2) 0.0662(7) Uani 1 1 d . . . . .
C16 C 0.74437(19) 0.2689(5) 0.6756(3) 0.0754(8) Uani 1 1 d . . . . .
H16 H 0.7425 0.1258 0.7042 0.090 Uiso 1 1 calc R . . . .
H2 H 0.552(2) 0.350(8) 0.456(3) 0.103(11) Uiso 1 1 d . . . . .


_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 C5 1.274(3) . ?
N1 C6 1.468(3) . ?
O2 C15 1.353(3) . ?
O2 H2 1.01(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.510(4) . ?
C2 C3 1.383(4) . ?
C2 C11 1.392(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(4) . ?
C4 C5 1.454(4) . ?
C4 C15 1.410(4) . ?
C5 H5 0.9500 . ?
C6 H6 1.0000 . ?
C6 C7 1.516(4) . ?
C6 C12 1.516(4) . ?
C7 C8 1.383(4) . ?
C7 C13 1.384(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.370(6) . ?
C10 H10 0.9500 . ?
C10 C14 1.369(5) . ?
C11 H11 0.9500 . ?
C11 C16 1.375(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9500 . ?

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
C5 N1 C6 119.0(2) . . ?
C15 O2 H2 107(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.2(3) . . ?
C3 C2 C11 117.3(3) . . ?
C11 C2 C1 121.6(3) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.2(3) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 C15 119.0(2) . . ?
C15 C4 C5 121.0(2) . . ?
N1 C5 C4 122.3(3) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
N1 C6 H6 108.6 . . ?
N1 C6 C7 108.0(2) . . ?
N1 C6 C12 109.1(2) . . ?
C7 C6 H6 108.6 . . ?
C7 C6 C12 113.8(2) . . ?
C12 C6 H6 108.6 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 C13 118.0(3) . . ?
C13 C7 C6 121.2(2) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.5 . . ?
C14 C10 C9 119.0(4) . . ?
C14 C10 H10 120.5 . . ?
C2 C11 H11 119.0 . . ?
C16 C11 C2 122.0(3) . . ?
C16 C11 H11 119.0 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13 119.4 . . ?
C14 C13 C7 121.3(3) . . ?
C14 C13 H13 119.4 . . ?
C10 C14 C13 120.4(4) . . ?
C10 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
O2 C15 C4 121.7(3) . . ?
O2 C15 C16 119.4(3) . . ?
C16 C15 C4 118.9(3) . . ?
C11 C16 C15 120.7(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

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 C6 C7 C8 -109.8(3) . . . . ?
N1 C6 C7 C13 67.4(3) . . . . ?
O2 C15 C16 C11 -178.8(3) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
C1 C2 C11 C16 179.5(3) . . . . ?
C2 C3 C4 C5 177.8(2) . . . . ?
C2 C3 C4 C15 -0.7(4) . . . . ?
C2 C11 C16 C15 0.1(5) . . . . ?
C3 C2 C11 C16 -0.1(4) . . . . ?
C3 C4 C5 N1 -178.6(2) . . . . ?
C3 C4 C15 O2 179.1(2) . . . . ?
C3 C4 C15 C16 0.6(4) . . . . ?
C4 C15 C16 C11 -0.3(4) . . . . ?
C5 N1 C6 C7 123.6(3) . . . . ?
C5 N1 C6 C12 -112.2(3) . . . . ?
C5 C4 C15 O2 0.6(4) . . . . ?
C5 C4 C15 C16 -177.9(3) . . . . ?
C6 N1 C5 C4 179.6(2) . . . . ?
C6 C7 C8 C9 177.5(3) . . . . ?
C6 C7 C13 C14 -177.8(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C7 C13 C14 C10 1.1(5) . . . . ?
C8 C7 C13 C14 -0.6(4) . . . . ?
C8 C9 C10 C14 0.9(5) . . . . ?
C9 C10 C14 C13 -1.3(5) . . . . ?
C11 C2 C3 C4 0.4(4) . . . . ?
C12 C6 C7 C8 129.0(3) . . . . ?
C12 C6 C7 C13 -53.9(4) . . . . ?
C13 C7 C8 C9 0.2(4) . . . . ?
C15 C4 C5 N1 -0.1(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_2
_database_code_depnum_ccdc_archive 'CCDC 2373506'
loop_
_audit_author_name
_audit_author_address
S
;China,Jilin
China
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;
_audit_creation_date             2021-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2014/7
_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 s
_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 0.0181 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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   20.0857(12)
_cell_length_b                   5.8189(4)
_cell_length_c                   14.3076(9)
_cell_angle_alpha                90
_cell_angle_beta                 128.517(2)
_cell_angle_gamma                90
_cell_volume                     1308.39(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9149
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.59
_cell_measurement_theta_min      3.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.586
_diffrn_reflns_theta_min         3.949
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2489
_reflns_number_total             2639
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.081
_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)+(0.0423P)²+0.4572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.63308(14) 0.6416(4) 0.8391(2) 0.0314(5) Uani 1 1 d . . . . .
H1 H 0.6352 0.6765 0.7761 0.038 Uiso 1 1 calc R . . . .
C2 C 0.66980(14) 0.7910(4) 0.9352(2) 0.0353(5) Uani 1 1 d . . . . .
H2 H 0.6977 0.9259 0.9380 0.042 Uiso 1 1 calc R . . . .
C3 C 0.66625(14) 0.7455(4) 1.0269(2) 0.0369(5) Uani 1 1 d . . . . .
H3 H 0.6904 0.8499 1.0917 0.044 Uiso 1 1 calc R . . . .
C4 C 0.62689(16) 0.5450(4) 1.0232(2) 0.0370(5) Uani 1 1 d . . . . .
H4 H 0.6247 0.5112 1.0862 0.044 Uiso 1 1 calc R . . . .
C5 C 0.59084(14) 0.3940(4) 0.9278(2) 0.0326(5) Uani 1 1 d . . . . .
H5 H 0.5644 0.2572 0.9263 0.039 Uiso 1 1 calc R . . . .
C6 C 0.59301(13) 0.4404(4) 0.8343(2) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.54924(13) 0.2809(4) 0.72703(19) 0.0292(5) Uani 1 1 d . . . . .
H7 H 0.5296 0.1404 0.7437 0.035 Uiso 1 1 calc R . . . .
C8 C 0.60546(15) 0.2086(4) 0.6950(2) 0.0350(5) Uani 1 1 d . . . . .
H8A H 0.5747 0.0985 0.6288 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.6574 0.1365 0.7645 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.6206 0.3440 0.6711 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.40123(14) 0.3083(4) 0.5680(2) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.3966 0.1634 0.5941 0.034 Uiso 1 1 calc R . . . .
C10 C 0.32455(13) 0.4187(4) 0.46464(19) 0.0266(4) Uani 1 1 d . . . . .
C11 C 0.32810(14) 0.6338(4) 0.4229(2) 0.0287(4) Uani 1 1 d . . . . .
C12 C 0.25360(14) 0.7287(4) 0.3217(2) 0.0320(5) Uani 1 1 d . . . . .
H12 H 0.2552 0.8735 0.2925 0.038 Uiso 1 1 calc R . . . .
C13 C 0.17699(14) 0.6120(4) 0.2636(2) 0.0317(5) Uani 1 1 d . . . . .
H13 H 0.1268 0.6792 0.1947 0.038 Uiso 1 1 calc R . . . .
C14 C 0.17139(14) 0.3987(4) 0.3033(2) 0.0302(5) Uani 1 1 d . . . . .
C15 C 0.24598(13) 0.3062(4) 0.4041(2) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.2438 0.1620 0.4332 0.034 Uiso 1 1 calc R . . . .
C16 C 0.08765(14) 0.2742(4) 0.2395(2) 0.0374(5) Uani 1 1 d . . . . .
H16A H 0.0970 0.1085 0.2408 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.0484 0.3273 0.1565 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.0631 0.3058 0.2797 0.056 Uiso 1 1 calc GR . . . .
N1 N 0.47465(11) 0.4025(3) 0.62424(16) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.40225(10) 0.7491(3) 0.47669(15) 0.0352(4) Uani 1 1 d . . . . .
H1A H 0.445(2) 0.654(7) 0.539(3) 0.061(10) Uiso 1 1 d . . . . .


_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
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.519(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.519(3) . ?
C7 N1 1.471(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.461(3) . ?
C9 N1 1.283(3) . ?
C10 C11 1.408(3) . ?
C10 C15 1.402(3) . ?
C11 C12 1.394(3) . ?
C11 O1 1.354(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 C15 1.387(3) . ?
C14 C16 1.508(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1 H1A 0.94(4) . ?

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 C1 H1 119.7 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 121.0(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 120.50(19) . . ?
C6 C7 H7 108.9 . . ?
C8 C7 C6 113.74(18) . . ?
C8 C7 H7 108.9 . . ?
N1 C7 C6 107.72(17) . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C8 108.51(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9 119.2 . . ?
N1 C9 H9 119.2 . . ?
N1 C9 C10 121.5(2) . . ?
C11 C10 C9 121.34(19) . . ?
C15 C10 C9 119.44(19) . . ?
C15 C10 C11 119.2(2) . . ?
C12 C11 C10 119.20(19) . . ?
O1 C11 C10 121.87(19) . . ?
O1 C11 C12 118.91(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(2) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C16 121.5(2) . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 C16 121.2(2) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.2(2) . . ?
C14 C15 H15 118.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 N1 C7 118.60(18) . . ?
C11 O1 H1A 106(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
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 52.9(3) . . . . ?
C1 C6 C7 N1 -67.4(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 177.29(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -176.6(2) . . . . ?
C5 C6 C7 C8 -129.9(2) . . . . ?
C5 C6 C7 N1 109.8(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C7 N1 C9 -123.81(19) . . . . ?
C8 C7 N1 C9 112.6(2) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C11 O1 -0.5(3) . . . . ?
C9 C10 C15 C14 -177.94(19) . . . . ?
C10 C9 N1 C7 -179.57(18) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C16 179.8(2) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C15 C10 C11 O1 -179.16(19) . . . . ?
C16 C14 C15 C10 179.83(19) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
N1 C9 C10 C15 178.37(19) . . . . ?
O1 C11 C12 C13 178.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
