# Supplementary Information (SI) for Chemical Communications.
# 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_5s
_database_code_depnum_ccdc_archive 'CCDC 2373554'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_audit_creation_date             2024-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
''
enrico.podda@unica.it
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33
_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/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                   9.6259(3)
_cell_length_b                   11.2341(3)
_cell_length_c                   13.6882(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.5000(10)
_cell_angle_gamma                90
_cell_volume                     1395.32(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.241
_cell_measurement_theta_min      2.272
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0924 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.9261.
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    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.272
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3013
_reflns_number_total             3460
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.077
_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)+(0.0529P)²+1.3926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1509
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C9(H9A,H9B)
1.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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
O1 O 0.07829(13) 0.43690(12) 0.63881(10) 0.0249(3) Uani 1 1 d . . . . .
H1 H 0.008(3) 0.421(2) 0.585(2) 0.037 Uiso 1 1 d . U . . .
O2 O 0.49381(14) 1.15663(11) 0.29337(10) 0.0258(3) Uani 1 1 d . . . . .
H2 H 0.517(3) 1.132(2) 0.242(2) 0.039 Uiso 1 1 d . U . . .
N1 N 0.18947(16) 0.60686(14) 0.50220(12) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.26067(18) 0.53490(16) 0.57092(14) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.20856(18) 0.42585(15) 0.61458(13) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.35380(19) 0.43707(17) 0.71033(14) 0.0278(4) Uani 1 1 d . . . . .
C4 C 0.41722(19) 0.52103(17) 0.64463(14) 0.0278(4) Uani 1 1 d . . . . .
H4A H 0.461129 0.595433 0.680522 0.033 Uiso 1 1 calc R U . . .
H4B H 0.484393 0.481082 0.613779 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2015(2) 0.31696(18) 0.54684(17) 0.0359(5) Uani 1 1 d . . . . .
H5A H 0.187479 0.245413 0.583433 0.054 Uiso 1 1 calc R U . . .
H5B H 0.293711 0.310094 0.531612 0.054 Uiso 1 1 calc R U . . .
H5C H 0.118839 0.325295 0.481878 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4409(2) 0.3261(2) 0.7549(2) 0.0441(6) Uani 1 1 d . . . . .
H6A H 0.385851 0.277803 0.789146 0.066 Uiso 1 1 calc R U . . .
H6B H 0.536153 0.348697 0.805545 0.066 Uiso 1 1 calc R U . . .
H6C H 0.457285 0.279859 0.699033 0.066 Uiso 1 1 calc R U . . .
C7 C 0.3242(2) 0.5083(2) 0.79686(15) 0.0381(5) Uani 1 1 d . . . . .
H7A H 0.271360 0.581752 0.768002 0.057 Uiso 1 1 calc R U . . .
H7B H 0.418020 0.528298 0.850310 0.057 Uiso 1 1 calc R U . . .
H7C H 0.264188 0.460550 0.827568 0.057 Uiso 1 1 calc R U . . .
C8 C 0.27032(19) 0.70253(17) 0.47242(15) 0.0302(4) Uani 1 1 d . . . . .
H8A H 0.304375 0.674498 0.415668 0.036 Uiso 1 1 calc R U . . .
H8B H 0.358305 0.723406 0.532264 0.036 Uiso 1 1 calc R U . . .
C9 C 0.17454(19) 0.81273(16) 0.43685(14) 0.0250(4) Uani 1 1 d . . . . .
H9A H 0.081504 0.790085 0.382119 0.030 Uiso 1 1 calc R U . . .
H9B H 0.149450 0.845859 0.495879 0.030 Uiso 1 1 calc R U . . .
C10 C 0.25224(17) 0.90670(15) 0.39528(13) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.29192(18) 1.01615(15) 0.44402(13) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.264936 1.034387 0.503053 0.027 Uiso 1 1 calc R U . . .
C12 C 0.37017(18) 1.09939(15) 0.40821(13) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.395025 1.174035 0.442180 0.027 Uiso 1 1 calc R U . . .
C13 C 0.41205(17) 1.07372(14) 0.32300(13) 0.0201(3) Uani 1 1 d . . . . .
C14 C 0.37016(19) 0.96604(15) 0.27145(13) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.395740 0.948552 0.211706 0.029 Uiso 1 1 calc R U . . .
C15 C 0.29081(19) 0.88423(16) 0.30766(13) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.262116 0.811089 0.271743 0.029 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 H1 0.84(3) . ?
O1 C2 1.406(2) . ?
O2 H2 0.85(3) . ?
O2 C13 1.3654(19) . ?
N1 C1 1.256(2) . ?
N1 C8 1.462(2) . ?
C1 C2 1.520(2) . ?
C1 C4 1.516(2) . ?
C2 C3 1.570(2) . ?
C2 C5 1.523(2) . ?
C3 C4 1.561(2) . ?
C3 C6 1.513(3) . ?
C3 C7 1.533(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.510(2) . ?
C10 C11 1.390(2) . ?
C10 C15 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 C14 1.391(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 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
C2 O1 H1 107.6(16) . . ?
C13 O2 H2 110.8(17) . . ?
C1 N1 C8 118.27(15) . . ?
N1 C1 C2 130.10(16) . . ?
N1 C1 C4 137.50(16) . . ?
C4 C1 C2 92.33(13) . . ?
O1 C2 C1 117.34(14) . . ?
O1 C2 C3 114.32(14) . . ?
O1 C2 C5 110.66(15) . . ?
C1 C2 C3 86.84(13) . . ?
C1 C2 C5 111.20(15) . . ?
C5 C2 C3 114.77(15) . . ?
C4 C3 C2 88.74(13) . . ?
C6 C3 C2 119.34(16) . . ?
C6 C3 C4 117.36(17) . . ?
C6 C3 C7 109.85(18) . . ?
C7 C3 C2 110.08(15) . . ?
C7 C3 C4 109.80(16) . . ?
C1 C4 C3 87.28(13) . . ?
C1 C4 H4A 114.1 . . ?
C1 C4 H4B 114.1 . . ?
C3 C4 H4A 114.1 . . ?
C3 C4 H4B 114.1 . . ?
H4A C4 H4B 111.3 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.40(14) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.44(14) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C11 C10 C9 121.91(15) . . ?
C11 C10 C15 117.67(15) . . ?
C15 C10 C9 120.39(15) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.37(15) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.10(15) . . ?
C13 C12 H12 119.9 . . ?
O2 C13 C12 117.81(15) . . ?
O2 C13 C14 122.75(15) . . ?
C12 C13 C14 119.44(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.72(15) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.63(16) . . ?
C14 C15 H15 119.2 . . ?

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
O1 C2 C3 C4 -134.88(15) . . . . ?
O1 C2 C3 C6 104.1(2) . . . . ?
O1 C2 C3 C7 -24.2(2) . . . . ?
O2 C13 C14 C15 178.05(16) . . . . ?
N1 C1 C2 O1 -44.7(3) . . . . ?
N1 C1 C2 C3 -160.6(2) . . . . ?
N1 C1 C2 C5 84.0(2) . . . . ?
N1 C1 C4 C3 160.1(2) . . . . ?
N1 C8 C9 C10 -173.89(15) . . . . ?
C1 N1 C8 C9 -150.04(17) . . . . ?
C1 C2 C3 C4 -16.21(13) . . . . ?
C1 C2 C3 C6 -137.21(19) . . . . ?
C1 C2 C3 C7 94.44(16) . . . . ?
C2 C1 C4 C3 -16.81(14) . . . . ?
C2 C3 C4 C1 16.25(13) . . . . ?
C4 C1 C2 O1 132.56(16) . . . . ?
C4 C1 C2 C3 16.72(14) . . . . ?
C4 C1 C2 C5 -98.66(17) . . . . ?
C5 C2 C3 C4 95.71(17) . . . . ?
C5 C2 C3 C6 -25.3(2) . . . . ?
C5 C2 C3 C7 -153.64(17) . . . . ?
C6 C3 C4 C1 138.97(18) . . . . ?
C7 C3 C4 C1 -94.68(16) . . . . ?
C8 N1 C1 C2 -177.67(18) . . . . ?
C8 N1 C1 C4 6.3(3) . . . . ?
C8 C9 C10 C11 -114.86(18) . . . . ?
C8 C9 C10 C15 63.0(2) . . . . ?
C9 C10 C11 C12 176.56(16) . . . . ?
C9 C10 C15 C14 -176.00(16) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C10 C15 C14 2.0(3) . . . . ?
C11 C12 C13 O2 -177.47(15) . . . . ?
C11 C12 C13 C14 2.5(2) . . . . ?
C12 C13 C14 C15 -1.9(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?

_olex2_submission_original_sample_id FS1
_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_2024cesar178
_database_code_depnum_ccdc_archive 'CCDC 2387960'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-09-30 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_audit_creation_date             2024-09-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
''
enrico.podda@unica.it
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N O'
_chemical_formula_sum            'C12 H11 N O'
_chemical_formula_weight         185.22
_chemical_absolute_configuration unk
_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.4979(5)
_cell_length_b                   11.2676(6)
_cell_length_c                   22.4890(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1899.95(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.378
_cell_measurement_theta_min      2.559
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1631 before and 0.0926 after correction.
The Ratio of minimum to maximum transmission is 0.7851.
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    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.559
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2955
_reflns_number_total             3863
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1170 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.033
_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)+(0.0530P)²+0.4707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1285
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C5(H5), C2(H2), C8(H8), C20(H20), C4(H4), C14(H14), C3(H3),
 C15(H15), C16(H16), C17(H17), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.4058(5) 0.1605(3) 0.58528(15) 0.0320(9) Uani 1 1 d . . . . .
O1 O 0.1563(5) 0.6633(3) 0.41382(14) 0.0323(9) Uani 1 1 d . . . . .
N1 N 0.2193(6) 0.9466(4) 0.35283(16) 0.0196(10) Uani 1 1 d . . . . .
N2 N 0.4670(6) 0.4453(4) 0.64495(17) 0.0216(10) Uani 1 1 d . . . . .
C21 C 0.4203(6) 0.3667(4) 0.6050(2) 0.0217(10) Uani 1 1 d . . . . .
C10 C 0.1892(6) 0.7404(4) 0.3779(2) 0.0230(11) Uani 1 1 d . . . . .
C19 C 0.3311(8) 0.5133(4) 0.5340(3) 0.0244(13) Uani 1 1 d . . . . .
H19 H 0.284647 0.535050 0.496198 0.029 Uiso 1 1 calc R U . . .
C23 C 0.5000(7) 0.2116(4) 0.6841(2) 0.0243(11) Uani 1 1 d . . . . .
H23A H 0.412086 0.245267 0.712288 0.029 Uiso 1 1 calc R U . . .
H23B H 0.615701 0.251409 0.691303 0.029 Uiso 1 1 calc R U . . .
C1 C 0.2030(7) 1.0644(5) 0.3668(2) 0.0203(11) Uani 1 1 d . . . . .
C18 C 0.3762(6) 0.6017(4) 0.5762(2) 0.0232(11) Uani 1 1 d . . . . .
C13 C 0.4486(7) 0.5627(5) 0.6311(2) 0.0203(11) Uani 1 1 d . . . . .
C5 C 0.1233(6) 1.2284(4) 0.4326(2) 0.0261(10) Uani 1 1 d . . . . .
H5 H 0.074807 1.255928 0.469102 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1333(7) 1.1050(4) 0.4217(2) 0.0229(10) Uani 1 1 d . . . . .
C2 C 0.2632(6) 1.1489(4) 0.32495(18) 0.0224(9) Uani 1 1 d . . . . .
H2 H 0.311232 1.122828 0.288118 0.027 Uiso 1 1 calc R U . . .
C8 C 0.0913(6) 0.9006(5) 0.4492(2) 0.0247(10) Uani 1 1 d . . . . .
H8 H 0.052969 0.841288 0.476307 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3551(7) 0.3968(5) 0.5482(2) 0.0276(11) Uani 1 1 d . . . . .
H20 H 0.328151 0.336480 0.520098 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1816(6) 1.3079(6) 0.3919(2) 0.0263(12) Uani 1 1 d . . . . .
H4 H 0.174733 1.390459 0.400164 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5056(6) 0.6477(4) 0.67367(18) 0.0250(10) Uani 1 1 d . . . . .
H14 H 0.555898 0.622469 0.710324 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2534(6) 1.2679(4) 0.3367(2) 0.0226(11) Uani 1 1 d . . . . .
H3 H 0.294338 1.323754 0.308206 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4876(7) 0.7660(5) 0.6616(3) 0.0285(12) Uani 1 1 d . . . . .
H15 H 0.526197 0.822438 0.690250 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4135(7) 0.8057(6) 0.6080(2) 0.0294(13) Uani 1 1 d . . . . .
H16 H 0.402134 0.888358 0.600533 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3574(6) 0.7248(4) 0.5662(2) 0.0284(11) Uani 1 1 d . . . . .
H17 H 0.305361 0.752036 0.530169 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0760(8) 1.0183(5) 0.4628(3) 0.0287(13) Uani 1 1 d . . . . .
H7 H 0.026818 1.041850 0.499901 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2581(7) 0.7135(4) 0.3166(2) 0.0240(11) Uani 1 1 d . . . . .
H11A H 0.374952 0.753097 0.311448 0.029 Uiso 1 1 calc R U . . .
H11B H 0.174954 0.747831 0.287025 0.029 Uiso 1 1 calc R U . . .
C22 C 0.4405(6) 0.2376(4) 0.6218(2) 0.0233(11) Uani 1 1 d . . . . .
C9 C 0.1654(6) 0.8696(5) 0.3937(2) 0.0224(10) Uani 1 1 d . . . . .
C12 C 0.2801(7) 0.5820(4) 0.3037(2) 0.0321(11) Uani 1 1 d . . . . .
H12A H 0.322012 0.571418 0.262743 0.048 Uiso 1 1 calc R U . . .
H12B H 0.165151 0.541823 0.308666 0.048 Uiso 1 1 calc R U . . .
H12C H 0.367313 0.547956 0.331282 0.048 Uiso 1 1 calc R U . . .
C24 C 0.5204(7) 0.0800(4) 0.6964(2) 0.0310(11) Uani 1 1 d . . . . .
H24A H 0.600853 0.044876 0.666933 0.047 Uiso 1 1 calc R U . . .
H24B H 0.403470 0.041412 0.693954 0.047 Uiso 1 1 calc R U . . .
H24C H 0.569982 0.068631 0.736332 0.047 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 C22 1.224(5) . ?
O1 C10 1.212(6) . ?
N1 C1 1.369(8) . ?
N1 C9 1.328(6) . ?
N2 C21 1.309(6) . ?
N2 C13 1.367(8) . ?
C21 C20 1.409(6) . ?
C21 C22 1.510(7) . ?
C10 C11 1.502(7) . ?
C10 C9 1.510(7) . ?
C19 H19 0.9500 . ?
C19 C18 1.417(7) . ?
C19 C20 1.364(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.499(6) . ?
C23 C24 1.516(6) . ?
C1 C6 1.417(7) . ?
C1 C2 1.413(7) . ?
C18 C13 1.419(7) . ?
C18 C17 1.413(7) . ?
C13 C14 1.419(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(7) . ?
C5 C4 1.353(7) . ?
C6 C7 1.412(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.366(7) . ?
C8 C9 1.408(7) . ?
C20 H20 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.426(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.366(7) . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.402(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(8) . ?
C17 H17 0.9500 . ?
C7 H7 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C9 N1 C1 116.6(4) . . ?
C21 N2 C13 118.2(4) . . ?
N2 C21 C20 123.5(5) . . ?
N2 C21 C22 116.9(4) . . ?
C20 C21 C22 119.6(5) . . ?
O1 C10 C11 122.5(5) . . ?
O1 C10 C9 120.6(5) . . ?
C11 C10 C9 116.8(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C20 C19 C18 119.2(5) . . ?
H23A C23 H23B 107.8 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 113.1(4) . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
N1 C1 C6 123.1(4) . . ?
N1 C1 C2 118.2(4) . . ?
C2 C1 C6 118.7(5) . . ?
C19 C18 C13 117.3(5) . . ?
C17 C18 C19 124.0(5) . . ?
C17 C18 C13 118.8(5) . . ?
N2 C13 C18 122.4(4) . . ?
N2 C13 C14 118.0(4) . . ?
C18 C13 C14 119.6(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C5 C6 C1 119.2(5) . . ?
C7 C6 C1 117.4(5) . . ?
C7 C6 C5 123.4(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.2(5) . . ?
C9 C8 H8 120.9 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.4(5) . . ?
C19 C20 H20 120.3 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(5) . . ?
C3 C4 H4 120.0 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.2 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(5) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.8(5) . . ?
C17 C16 H16 120.1 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.7(5) . . ?
C16 C17 H17 119.6 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9(6) . . ?
C8 C7 H7 120.0 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.1(4) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
O2 C22 C21 119.6(5) . . ?
O2 C22 C23 123.5(5) . . ?
C23 C22 C21 116.9(4) . . ?
N1 C9 C10 115.5(4) . . ?
N1 C9 C8 124.8(5) . . ?
C8 C9 C10 119.7(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 0.8(7) . . . . ?
O1 C10 C9 N1 174.6(4) . . . . ?
O1 C10 C9 C8 -5.0(7) . . . . ?
N1 C1 C6 C5 179.2(4) . . . . ?
N1 C1 C6 C7 -1.2(7) . . . . ?
N1 C1 C2 C3 -178.8(4) . . . . ?
N2 C21 C20 C19 -2.9(7) . . . . ?
N2 C21 C22 O2 -177.0(4) . . . . ?
N2 C21 C22 C23 4.1(6) . . . . ?
N2 C13 C14 C15 -179.3(4) . . . . ?
C21 N2 C13 C18 2.0(6) . . . . ?
C21 N2 C13 C14 -177.7(5) . . . . ?
C19 C18 C13 N2 -3.3(7) . . . . ?
C19 C18 C13 C14 176.4(5) . . . . ?
C19 C18 C17 C16 -176.2(5) . . . . ?
C1 N1 C9 C10 -178.5(3) . . . . ?
C1 N1 C9 C8 1.0(6) . . . . ?
C1 C6 C7 C8 0.9(8) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C18 C19 C20 C21 1.4(8) . . . . ?
C18 C13 C14 C15 0.9(7) . . . . ?
C13 N2 C21 C20 1.1(6) . . . . ?
C13 N2 C21 C22 -179.4(4) . . . . ?
C13 C18 C17 C16 2.1(7) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C5 C6 C7 C8 -179.5(4) . . . . ?
C5 C4 C3 C2 0.0(7) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C6 C5 C4 C3 0.5(7) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C1 C6 C7 -179.3(5) . . . . ?
C20 C21 C22 O2 2.5(7) . . . . ?
C20 C21 C22 C23 -176.4(4) . . . . ?
C20 C19 C18 C13 1.4(8) . . . . ?
C20 C19 C18 C17 179.8(5) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C4 C5 C6 C7 179.4(5) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C15 C16 C17 C18 -1.1(7) . . . . ?
C17 C18 C13 N2 178.3(4) . . . . ?
C17 C18 C13 C14 -2.0(7) . . . . ?
C7 C8 C9 N1 -1.2(7) . . . . ?
C7 C8 C9 C10 178.3(4) . . . . ?
C11 C10 C9 N1 -4.2(6) . . . . ?
C11 C10 C9 C8 176.2(4) . . . . ?
C22 C21 C20 C19 177.6(5) . . . . ?
C9 N1 C1 C6 0.2(5) . . . . ?
C9 N1 C1 C2 178.4(5) . . . . ?
C9 C10 C11 C12 179.6(4) . . . . ?
C9 C8 C7 C6 0.2(8) . . . . ?
C24 C23 C22 O2 2.4(7) . . . . ?
C24 C23 C22 C21 -178.7(4) . . . . ?

_olex2_submission_original_sample_id FRS229
_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_4q
_database_code_depnum_ccdc_archive 'CCDC 2373555'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_audit_creation_date             2024-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
loop_
_audit_author_email
''
enrico.podda@unica.it
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30
_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.2850(3)
_cell_length_b                   14.3459(4)
_cell_length_c                   18.9431(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2523.25(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8072
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.265
_cell_measurement_theta_min      2.825
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0733 after correction.
The Ratio of minimum to maximum transmission is 0.8334.
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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30814
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_min         2.826
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2574
_reflns_number_total             3122
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+1.2276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B), C2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C13(H13), C10(H10), C11(H11), C12(H12)
1.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O1 O 0.04591(10) 0.51957(7) 0.78265(4) 0.0280(2) Uani 1 1 d . . . . .
N2 N 0.19407(11) 0.46481(7) 0.49097(5) 0.0204(2) Uani 1 1 d . . . . .
N1 N 0.06792(11) 0.48480(8) 0.59382(5) 0.0231(2) Uani 1 1 d . . . . .
H1 H -0.0031(18) 0.5020(11) 0.5663(8) 0.028 Uiso 1 1 d . U . . .
C8 C 0.30157(12) 0.40766(8) 0.59852(6) 0.0205(2) Uani 1 1 d . . . . .
H8 H 0.296804 0.400453 0.648315 0.025 Uiso 1 1 calc R U . . .
C14 C 0.42625(12) 0.38941(8) 0.48684(6) 0.0192(2) Uani 1 1 d . . . . .
C4 C 0.02968(12) 0.46555(8) 0.66512(6) 0.0203(2) Uani 1 1 d . . . . .
C3 C 0.07985(12) 0.53147(8) 0.72137(6) 0.0206(2) Uani 1 1 d . . . . .
C9 C 0.42190(12) 0.37444(8) 0.56080(6) 0.0193(2) Uani 1 1 d . . . . .
C15 C 0.30833(13) 0.43624(8) 0.45599(6) 0.0204(2) Uani 1 1 d . . . . .
H15 H 0.311631 0.447930 0.406657 0.024 Uiso 1 1 calc R U . . .
C7 C 0.19075(12) 0.45071(8) 0.56262(6) 0.0192(2) Uani 1 1 d . . . . .
C6 C -0.11790(13) 0.42301(9) 0.67764(7) 0.0256(3) Uani 1 1 d . . . . .
H6A H -0.171297 0.442749 0.720342 0.031 Uiso 1 1 calc R U . . .
H6B H -0.178870 0.410383 0.635850 0.031 Uiso 1 1 calc R U . . .
C13 C 0.54464(13) 0.35742(8) 0.44637(7) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.547447 0.368566 0.396951 0.028 Uiso 1 1 calc R U . . .
C5 C 0.01233(14) 0.36435(9) 0.68773(7) 0.0259(3) Uani 1 1 d . . . . .
H5A H 0.032093 0.315433 0.652160 0.031 Uiso 1 1 calc R U . . .
H5B H 0.039666 0.347805 0.736666 0.031 Uiso 1 1 calc R U . . .
C10 C 0.53831(13) 0.32561(8) 0.59222(7) 0.0236(3) Uani 1 1 d . . . . .
H10 H 0.538292 0.314575 0.641670 0.028 Uiso 1 1 calc R U . . .
C2 C 0.17242(15) 0.61211(9) 0.69857(7) 0.0290(3) Uani 1 1 d . . . . .
H2A H 0.116674 0.651689 0.665608 0.035 Uiso 1 1 calc R U . . .
H2B H 0.256941 0.587697 0.672618 0.035 Uiso 1 1 calc R U . . .
C11 C 0.65037(14) 0.29435(9) 0.55198(7) 0.0260(3) Uani 1 1 d . . . . .
H11 H 0.726771 0.261099 0.573844 0.031 Uiso 1 1 calc R U . . .
C12 C 0.65485(14) 0.31052(9) 0.47843(7) 0.0265(3) Uani 1 1 d . . . . .
H12 H 0.734198 0.288868 0.451353 0.032 Uiso 1 1 calc R U . . .
C1 C 0.22488(18) 0.67194(10) 0.75962(8) 0.0383(4) Uani 1 1 d . . . . .
H1A H 0.280781 0.724527 0.741187 0.058 Uiso 1 1 calc R U . . .
H1B H 0.285747 0.634342 0.790851 0.058 Uiso 1 1 calc R U . . .
H1C H 0.141932 0.695513 0.786160 0.058 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 C3 1.2149(14) . ?
N2 C15 1.3163(15) . ?
N2 C7 1.3725(14) . ?
N1 H1 0.876(17) . ?
N1 C4 1.4236(15) . ?
N1 C7 1.3745(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.4092(16) . ?
C8 C7 1.3793(16) . ?
C14 C9 1.4180(16) . ?
C14 C15 1.4113(16) . ?
C14 C13 1.4165(16) . ?
C4 C3 1.4989(17) . ?
C4 C6 1.5186(17) . ?
C4 C5 1.5222(17) . ?
C3 C2 1.5045(17) . ?
C9 C10 1.4188(16) . ?
C15 H15 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.4856(18) . ?
C13 H13 0.9500 . ?
C13 C12 1.3670(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3656(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.5203(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.4129(18) . ?
C12 H12 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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 N2 C7 118.03(10) . . ?
C4 N1 H1 115.6(10) . . ?
C7 N1 H1 117.9(10) . . ?
C7 N1 C4 123.09(10) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.53(10) . . ?
C15 C14 C9 117.33(10) . . ?
C15 C14 C13 122.15(11) . . ?
C13 C14 C9 120.52(11) . . ?
N1 C4 C3 118.33(10) . . ?
N1 C4 C6 116.82(10) . . ?
N1 C4 C5 118.58(10) . . ?
C3 C4 C6 115.02(10) . . ?
C3 C4 C5 115.76(10) . . ?
C6 C4 C5 58.49(8) . . ?
O1 C3 C4 120.66(11) . . ?
O1 C3 C2 122.05(11) . . ?
C4 C3 C2 117.30(10) . . ?
C8 C9 C14 118.19(10) . . ?
C8 C9 C10 123.93(11) . . ?
C14 C9 C10 117.87(11) . . ?
N2 C15 C14 124.41(11) . . ?
N2 C15 H15 117.8 . . ?
C14 C15 H15 117.8 . . ?
N2 C7 N1 113.04(10) . . ?
N2 C7 C8 122.46(10) . . ?
N1 C7 C8 124.49(10) . . ?
C4 C6 H6A 117.7 . . ?
C4 C6 H6B 117.7 . . ?
H6A C6 H6B 114.8 . . ?
C5 C6 C4 60.88(8) . . ?
C5 C6 H6A 117.7 . . ?
C5 C6 H6B 117.7 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 119.98(11) . . ?
C12 C13 H13 120.0 . . ?
C4 C5 H5A 117.7 . . ?
C4 C5 H5B 117.7 . . ?
C6 C5 C4 60.64(8) . . ?
C6 C5 H5A 117.7 . . ?
C6 C5 H5B 117.7 . . ?
H5A C5 H5B 114.8 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.55(12) . . ?
C11 C10 H10 119.7 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C3 C2 C1 113.50(11) . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.26(12) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.79(11) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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 C3 C2 C1 3.47(18) . . . . ?
N1 C4 C3 O1 177.58(11) . . . . ?
N1 C4 C3 C2 -2.18(16) . . . . ?
N1 C4 C6 C5 108.59(12) . . . . ?
N1 C4 C5 C6 -105.59(12) . . . . ?
C8 C9 C10 C11 179.04(11) . . . . ?
C14 C9 C10 C11 0.00(17) . . . . ?
C14 C13 C12 C11 -0.18(18) . . . . ?
C4 N1 C7 N2 169.74(11) . . . . ?
C4 N1 C7 C8 -11.08(19) . . . . ?
C4 C3 C2 C1 -176.77(11) . . . . ?
C3 C4 C6 C5 -106.05(11) . . . . ?
C3 C4 C5 C6 104.77(11) . . . . ?
C9 C8 C7 N2 -1.61(18) . . . . ?
C9 C8 C7 N1 179.29(11) . . . . ?
C9 C14 C15 N2 -1.58(17) . . . . ?
C9 C14 C13 C12 0.97(18) . . . . ?
C9 C10 C11 C12 0.80(19) . . . . ?
C15 N2 C7 N1 178.83(10) . . . . ?
C15 N2 C7 C8 -0.36(17) . . . . ?
C15 C14 C9 C8 -0.47(16) . . . . ?
C15 C14 C9 C10 178.63(10) . . . . ?
C15 C14 C13 C12 -178.51(11) . . . . ?
C7 N2 C15 C14 2.01(17) . . . . ?
C7 N1 C4 C3 91.03(14) . . . . ?
C7 N1 C4 C6 -124.78(12) . . . . ?
C7 N1 C4 C5 -57.83(16) . . . . ?
C7 C8 C9 C14 1.95(17) . . . . ?
C7 C8 C9 C10 -177.09(11) . . . . ?
C6 C4 C3 O1 32.77(16) . . . . ?
C6 C4 C3 C2 -146.99(11) . . . . ?
C13 C14 C9 C8 -179.97(11) . . . . ?
C13 C14 C9 C10 -0.87(16) . . . . ?
C13 C14 C15 N2 177.91(11) . . . . ?
C5 C4 C3 O1 -32.70(16) . . . . ?
C5 C4 C3 C2 147.54(11) . . . . ?
C10 C11 C12 C13 -0.71(19) . . . . ?

_olex2_submission_original_sample_id FS13
_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_5t
_database_code_depnum_ccdc_archive 'CCDC 2373556'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2024-07-25 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_audit_creation_date             2024-07-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 N2 O'
_chemical_formula_sum            'C17 H22 N2 O'
_chemical_formula_weight         270.36
_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                   10.9369(3)
_cell_length_b                   16.1988(5)
_cell_length_c                   8.7551(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.1140(10)
_cell_angle_gamma                90
_cell_volume                     1522.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.280
_cell_measurement_theta_min      2.276
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
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    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            37962
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3361
_reflns_number_total             3780
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.050
_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)+(0.0393P)²+0.6721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C4(H4A,H4B), C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C11(H11), C14(H14), C15(H15)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_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
O1 O 0.02560(7) 0.58590(5) 0.85713(9) 0.01862(17) Uani 1 1 d . . . . .
H1 H -0.0295(14) 0.5815(9) 0.9213(18) 0.028 Uiso 1 1 d . U . . .
N1 N 0.16946(8) 0.42678(5) 0.98626(10) 0.01731(18) Uani 1 1 d . . . . .
N2 N 0.11551(9) 0.40661(6) 0.46282(11) 0.0203(2) Uani 1 1 d . . . . .
H2 H 0.0605(14) 0.4180(9) 0.3745(18) 0.024 Uiso 1 1 d . U . . .
C1 C 0.21057(10) 0.49678(6) 0.95888(11) 0.0166(2) Uani 1 1 d . . . . .
C12 C 0.24239(10) 0.40185(6) 0.47632(12) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.14763(10) 0.58142(6) 0.94564(12) 0.0171(2) Uani 1 1 d . . . . .
C13 C 0.31778(11) 0.42816(7) 0.37434(12) 0.0201(2) Uani 1 1 d . . . . .
H13 H 0.2836 0.4558 0.2801 0.024 Uiso 1 1 calc R U . . .
C17 C 0.29164(10) 0.36148(6) 0.61811(12) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.18779(10) 0.34123(6) 0.69010(12) 0.0192(2) Uani 1 1 d . . . . .
C16 C 0.42022(11) 0.34683(7) 0.65674(13) 0.0219(2) Uani 1 1 d . . . . .
H16 H 0.4555 0.3199 0.7514 0.026 Uiso 1 1 calc R U . . .
C9 C 0.19438(12) 0.29934(7) 0.84401(13) 0.0228(2) Uani 1 1 d . . . . .
H9A H 0.2460 0.2490 0.8470 0.027 Uiso 1 1 calc R U . . .
H9B H 0.1095 0.2821 0.8541 0.027 Uiso 1 1 calc R U . . .
C4 C 0.32893(10) 0.53186(7) 0.91691(14) 0.0223(2) Uani 1 1 d . . . . .
H4A H 0.3599 0.5004 0.8352 0.027 Uiso 1 1 calc R U . . .
H4B H 0.3965 0.5423 1.0077 0.027 Uiso 1 1 calc R U . . .
C11 C 0.08389(11) 0.36890(7) 0.59143(13) 0.0222(2) Uani 1 1 d . . . . .
H11 H 0.0012 0.3631 0.6087 0.027 Uiso 1 1 calc R U . . .
C8 C 0.24929(11) 0.35448(6) 0.98245(12) 0.0204(2) Uani 1 1 d . . . . .
H8A H 0.2559 0.3229 1.0805 0.024 Uiso 1 1 calc R U . . .
H8B H 0.3340 0.3725 0.9731 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25182(10) 0.61022(7) 0.85554(13) 0.0207(2) Uani 1 1 d . . . . .
C14 C 0.44397(11) 0.41250(7) 0.41524(14) 0.0243(2) Uani 1 1 d . . . . .
H14 H 0.4974 0.4294 0.3475 0.029 Uiso 1 1 calc R U . . .
C5 C 0.15489(12) 0.62004(7) 1.10600(13) 0.0253(2) Uani 1 1 d . . . . .
H5A H 0.1309 0.6783 1.0943 0.038 Uiso 1 1 calc R U . . .
H5B H 0.2403 0.6157 1.1653 0.038 Uiso 1 1 calc R U . . .
H5C H 0.0981 0.5909 1.1615 0.038 Uiso 1 1 calc R U . . .
C15 C 0.49480(11) 0.37216(7) 0.55501(14) 0.0259(2) Uani 1 1 d . . . . .
H15 H 0.5820 0.3621 0.5800 0.031 Uiso 1 1 calc R U . . .
C7 C 0.20602(11) 0.60481(8) 0.68014(13) 0.0250(2) Uani 1 1 d . . . . .
H7A H 0.1668 0.5510 0.6537 0.038 Uiso 1 1 calc R U . . .
H7B H 0.2767 0.6113 0.6273 0.038 Uiso 1 1 calc R U . . .
H7C H 0.1451 0.6487 0.6465 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31368(12) 0.69321(8) 0.89940(17) 0.0319(3) Uani 1 1 d . . . . .
H6A H 0.2524 0.7375 0.8713 0.048 Uiso 1 1 calc R U . . .
H6B H 0.3823 0.7010 0.8434 0.048 Uiso 1 1 calc R U . . .
H6C H 0.3463 0.6947 1.0118 0.048 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 H1 0.903(15) . ?
O1 C2 1.4101(12) . ?
N1 C1 1.2598(14) . ?
N1 C8 1.4650(13) . ?
N2 H2 0.903(15) . ?
N2 C12 1.3720(14) . ?
N2 C11 1.3822(14) . ?
C1 C2 1.5285(14) . ?
C1 C4 1.5221(15) . ?
C12 C13 1.3937(15) . ?
C12 C17 1.4146(14) . ?
C2 C3 1.5763(15) . ?
C2 C5 1.5251(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3808(16) . ?
C17 C10 1.4391(15) . ?
C17 C16 1.4017(15) . ?
C10 C9 1.4979(14) . ?
C10 C11 1.3638(16) . ?
C16 H16 0.9500 . ?
C16 C15 1.3809(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5320(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5610(15) . ?
C11 H11 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C3 C7 1.5232(16) . ?
C3 C6 1.5206(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.4040(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 O1 H1 109.2(10) . . ?
C1 N1 C8 118.62(9) . . ?
C12 N2 H2 125.5(9) . . ?
C12 N2 C11 108.22(9) . . ?
C11 N2 H2 123.9(9) . . ?
N1 C1 C2 130.52(10) . . ?
N1 C1 C4 137.17(10) . . ?
C4 C1 C2 92.20(8) . . ?
N2 C12 C13 129.87(10) . . ?
N2 C12 C17 108.02(9) . . ?
C13 C12 C17 122.09(10) . . ?
O1 C2 C1 116.91(8) . . ?
O1 C2 C3 114.12(8) . . ?
O1 C2 C5 111.13(9) . . ?
C1 C2 C3 86.85(8) . . ?
C5 C2 C1 110.81(8) . . ?
C5 C2 C3 115.15(9) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.57(10) . . ?
C14 C13 H13 121.2 . . ?
C12 C17 C10 106.89(9) . . ?
C16 C17 C12 118.99(10) . . ?
C16 C17 C10 134.07(10) . . ?
C17 C10 C9 126.30(10) . . ?
C11 C10 C17 106.22(9) . . ?
C11 C10 C9 127.48(10) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 118.94(10) . . ?
C15 C16 H16 120.5 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C10 C9 C8 113.03(9) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C1 C4 H4A 114.0 . . ?
C1 C4 H4B 114.0 . . ?
C1 C4 C3 87.62(8) . . ?
H4A C4 H4B 111.2 . . ?
C3 C4 H4A 114.0 . . ?
C3 C4 H4B 114.0 . . ?
N2 C11 H11 124.7 . . ?
C10 C11 N2 110.64(10) . . ?
C10 C11 H11 124.7 . . ?
N1 C8 C9 109.86(9) . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C4 C3 C2 88.95(8) . . ?
C7 C3 C2 111.01(9) . . ?
C7 C3 C4 110.56(10) . . ?
C6 C3 C2 117.69(10) . . ?
C6 C3 C4 116.58(9) . . ?
C6 C3 C7 110.45(10) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.30(11) . . ?
C15 C14 H14 119.3 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C15 C14 121.10(11) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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 C2 C3 C4 -133.65(9) . . . . ?
O1 C2 C3 C7 -21.98(12) . . . . ?
O1 C2 C3 C6 106.64(11) . . . . ?
N1 C1 C2 O1 -45.16(15) . . . . ?
N1 C1 C2 C3 -160.69(11) . . . . ?
N1 C1 C2 C5 83.56(14) . . . . ?
N1 C1 C4 C3 160.14(13) . . . . ?
N2 C12 C13 C14 -177.53(11) . . . . ?
N2 C12 C17 C10 0.43(11) . . . . ?
N2 C12 C17 C16 178.14(9) . . . . ?
C1 N1 C8 C9 -112.16(11) . . . . ?
C1 C2 C3 C4 -15.48(8) . . . . ?
C1 C2 C3 C7 96.18(10) . . . . ?
C1 C2 C3 C6 -135.20(10) . . . . ?
C1 C4 C3 C2 15.54(8) . . . . ?
C1 C4 C3 C7 -96.55(9) . . . . ?
C1 C4 C3 C6 136.24(10) . . . . ?
C12 N2 C11 C10 1.30(13) . . . . ?
C12 C13 C14 C15 -0.51(17) . . . . ?
C12 C17 C10 C9 -178.75(10) . . . . ?
C12 C17 C10 C11 0.34(12) . . . . ?
C12 C17 C16 C15 -0.10(15) . . . . ?
C2 C1 C4 C3 -16.05(8) . . . . ?
C13 C12 C17 C10 -178.26(9) . . . . ?
C13 C12 C17 C16 -0.55(15) . . . . ?
C13 C14 C15 C16 -0.12(18) . . . . ?
C17 C12 C13 C14 0.85(15) . . . . ?
C17 C10 C9 C8 71.11(14) . . . . ?
C17 C10 C11 N2 -1.00(12) . . . . ?
C17 C16 C15 C14 0.43(17) . . . . ?
C10 C17 C16 C15 176.85(11) . . . . ?
C10 C9 C8 N1 62.47(12) . . . . ?
C16 C17 C10 C9 4.03(19) . . . . ?
C16 C17 C10 C11 -176.87(12) . . . . ?
C9 C10 C11 N2 178.08(10) . . . . ?
C4 C1 C2 O1 131.43(9) . . . . ?
C4 C1 C2 C3 15.90(8) . . . . ?
C4 C1 C2 C5 -99.85(10) . . . . ?
C11 N2 C12 C13 177.51(11) . . . . ?
C11 N2 C12 C17 -1.04(12) . . . . ?
C11 C10 C9 C8 -107.79(13) . . . . ?
C8 N1 C1 C2 176.15(10) . . . . ?
C8 N1 C1 C4 1.16(18) . . . . ?
C5 C2 C3 C4 96.06(10) . . . . ?
C5 C2 C3 C7 -152.27(10) . . . . ?
C5 C2 C3 C6 -23.66(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
