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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a_a
_database_code_depnum_ccdc_archive 'CCDC 2420907'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;Tyumen State University
Russia
;
_audit_update_record             
;
2025-02-01 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-29
_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         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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                   16.533(3)
_cell_length_b                   5.8462(9)
_cell_length_c                   14.439(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.450(6)
_cell_angle_gamma                90
_cell_volume                     1362.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2780
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.24
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0923 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.8130.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2682
_reflns_number_total             4124
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    ?
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.024
_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)+(0.0520P)²+0.5416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O1 O 0.20075(8) 0.4087(2) 0.81117(8) 0.0328(3) Uani 1 1 d . . . . .
H1 H 0.2266 0.5154 0.7735 0.039 Uiso 1 1 d R U . . .
O2 O 0.11559(8) 0.0794(2) 0.86996(9) 0.0349(3) Uani 1 1 d . . . . .
N1 N 0.25373(8) 0.6012(2) 0.67581(10) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.21575(10) 0.4493(3) 0.61813(12) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.2201 0.4524 0.5550 0.028 Uiso 1 1 calc R U . . .
C2 C 0.16624(10) 0.2732(3) 0.64993(11) 0.0219(3) Uani 1 1 d . . . . .
C3 C 0.16175(10) 0.2586(3) 0.74580(11) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.11496(10) 0.0822(3) 0.77499(12) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.07185(11) -0.0685(3) 0.70917(12) 0.0270(4) Uani 1 1 d . . . . .
H5 H 0.0406 -0.1840 0.7286 0.032 Uiso 1 1 calc R U . . .
C6 C 0.07457(11) -0.0497(3) 0.61358(12) 0.0275(4) Uani 1 1 d . . . . .
H6 H 0.0443 -0.1507 0.5696 0.033 Uiso 1 1 calc R U . . .
C7 C 0.12166(10) 0.1170(3) 0.58430(12) 0.0253(4) Uani 1 1 d . . . . .
H7 H 0.1241 0.1269 0.5207 0.030 Uiso 1 1 calc R U . . .
C8 C 0.29872(10) 0.7830(3) 0.64615(11) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.29229(11) 0.8455(3) 0.55299(12) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.2598 0.7585 0.5051 0.034 Uiso 1 1 calc R U . . .
C10 C 0.33397(11) 1.0383(3) 0.52904(13) 0.0306(4) Uani 1 1 d . . . . .
H10 H 0.3297 1.0762 0.4656 0.037 Uiso 1 1 calc R U . . .
C11 C 0.38071(11) 1.1706(3) 0.59833(13) 0.0289(4) Uani 1 1 d . . . . .
H11 H 0.4075 1.2993 0.5817 0.035 Uiso 1 1 calc R U . . .
C12 C 0.38886(10) 1.1141(3) 0.69519(12) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.43577(10) 1.2515(3) 0.76816(13) 0.0286(4) Uani 1 1 d . . . . .
H13 H 0.4606 1.3844 0.7524 0.034 Uiso 1 1 calc R U . . .
C14 C 0.44508(11) 1.1924(3) 0.86107(13) 0.0314(4) Uani 1 1 d . . . . .
H14 H 0.4760 1.2847 0.9082 0.038 Uiso 1 1 calc R U . . .
C15 C 0.40793(11) 0.9918(3) 0.88566(13) 0.0309(4) Uani 1 1 d . . . . .
H15 H 0.4157 0.9498 0.9491 0.037 Uiso 1 1 calc R U . . .
C16 C 0.36049(11) 0.8578(3) 0.81735(12) 0.0272(4) Uani 1 1 d . . . . .
H16 H 0.3354 0.7273 0.8350 0.033 Uiso 1 1 calc R U . . .
C17 C 0.34903(10) 0.9151(3) 0.72005(12) 0.0220(3) Uani 1 1 d . . . . .
C18 C 0.06861(13) -0.0976(4) 0.90118(14) 0.0381(5) Uani 1 1 d . . . . .
H18A H 0.0118 -0.0858 0.8682 0.057 Uiso 1 1 calc R U . . .
H18B H 0.0722 -0.0826 0.9682 0.057 Uiso 1 1 calc R U . . .
H18C H 0.0902 -0.2437 0.8882 0.057 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 0.9830 . ?
O1 C3 1.3470(19) . ?
O2 C4 1.369(2) . ?
O2 C18 1.424(2) . ?
N1 C1 1.285(2) . ?
N1 C8 1.416(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.450(2) . ?
C2 C3 1.405(2) . ?
C2 C7 1.405(2) . ?
C3 C4 1.407(2) . ?
C4 C5 1.377(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(2) . ?
C8 C17 1.430(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.403(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.415(2) . ?
C12 C13 1.416(2) . ?
C12 C17 1.420(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.361(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.404(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.417(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 103.0 . . ?
C4 O2 C18 116.05(14) . . ?
C1 N1 C8 122.55(15) . . ?
N1 C1 H1A 119.5 . . ?
N1 C1 C2 121.05(15) . . ?
C2 C1 H1A 119.5 . . ?
C3 C2 C1 120.56(14) . . ?
C7 C2 C1 119.85(15) . . ?
C7 C2 C3 119.59(15) . . ?
O1 C3 C2 122.14(15) . . ?
O1 C3 C4 118.59(15) . . ?
C2 C3 C4 119.28(15) . . ?
O2 C4 C3 115.04(14) . . ?
O2 C4 C5 125.06(16) . . ?
C5 C4 C3 119.89(16) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.69(16) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.19(16) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.31(16) . . ?
C6 C7 H7 119.8 . . ?
N1 C8 C17 116.03(14) . . ?
C9 C8 N1 124.08(15) . . ?
C9 C8 C17 119.75(15) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.06(16) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.35(17) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.67(16) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.53(16) . . ?
C11 C12 C17 119.39(15) . . ?
C13 C12 C17 119.08(16) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.11(17) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.89(16) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.69(17) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.88(17) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C8 118.71(15) . . ?
C16 C17 C8 122.98(15) . . ?
C16 C17 C12 118.30(15) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C4 O2 -1.4(2) . . . . ?
O1 C3 C4 C5 177.53(16) . . . . ?
O2 C4 C5 C6 179.34(16) . . . . ?
N1 C1 C2 C3 -2.9(2) . . . . ?
N1 C1 C2 C7 176.45(15) . . . . ?
N1 C8 C9 C10 175.10(16) . . . . ?
N1 C8 C17 C12 -173.51(14) . . . . ?
N1 C8 C17 C16 5.9(2) . . . . ?
C1 N1 C8 C9 14.6(3) . . . . ?
C1 N1 C8 C17 -169.74(15) . . . . ?
C1 C2 C3 O1 1.8(2) . . . . ?
C1 C2 C3 C4 -178.35(15) . . . . ?
C1 C2 C7 C6 -179.87(15) . . . . ?
C2 C3 C4 O2 178.78(15) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
C7 C2 C3 O1 -177.55(15) . . . . ?
C7 C2 C3 C4 2.3(2) . . . . ?
C8 N1 C1 C2 -176.36(14) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C8 C17 C12 2.4(2) . . . . ?
C9 C8 C17 C16 -178.21(16) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 -178.78(16) . . . . ?
C10 C11 C12 C17 1.1(3) . . . . ?
C11 C12 C13 C14 -178.23(17) . . . . ?
C11 C12 C17 C8 -2.7(2) . . . . ?
C11 C12 C17 C16 177.85(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C8 177.19(15) . . . . ?
C13 C12 C17 C16 -2.2(2) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
C14 C15 C16 C17 1.3(3) . . . . ?
C15 C16 C17 C8 -178.74(16) . . . . ?
C15 C16 C17 C12 0.7(3) . . . . ?
C17 C8 C9 C10 -0.4(3) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C18 O2 C4 C3 179.97(16) . . . . ?
C18 O2 C4 C5 1.1(3) . . . . ?

_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_a_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2420908'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;Tyumen State University
Russia
;
_audit_update_record             
;
2025-02-01 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-29
_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         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_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                   6.1678(4)
_cell_length_b                   14.2905(10)
_cell_length_c                   31.0405(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2735.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8239
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1296 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.8713.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            30006
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2708
_reflns_number_total             3641
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.047
_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)+(0.0442P)²+1.8398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16)
1.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.3962(2) 0.36705(8) 0.34937(4) 0.0348(3) Uani 1 1 d . . . . .
H1 H 0.507(4) 0.3282(19) 0.3626(8) 0.076(8) Uiso 1 1 d . . . . .
O2 O 0.0599(2) 0.43711(8) 0.30798(4) 0.0381(3) Uani 1 1 d . . . . .
N1 N 0.6081(2) 0.22197(8) 0.37643(4) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.4661(2) 0.16964(11) 0.35807(5) 0.0250(3) Uani 1 1 d . . . . .
H1A H 0.4773 0.1050 0.3608 0.030 Uiso 1 1 calc R U . . .
C2 C 0.2892(2) 0.20862(10) 0.33327(4) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.2580(3) 0.30606(11) 0.33065(5) 0.0250(3) Uani 1 1 d . . . . .
C4 C 0.0791(3) 0.34130(11) 0.30780(5) 0.0276(3) Uani 1 1 d . . . . .
C5 C -0.0590(3) 0.28072(12) 0.28673(5) 0.0302(4) Uani 1 1 d . . . . .
H5 H -0.1765 0.3043 0.2714 0.036 Uiso 1 1 calc R U . . .
C6 C -0.0237(3) 0.18431(12) 0.28823(5) 0.0321(4) Uani 1 1 d . . . . .
H6 H -0.1155 0.1442 0.2732 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1455(3) 0.14821(11) 0.31169(5) 0.0295(3) Uani 1 1 d . . . . .
H7 H 0.1650 0.0838 0.3133 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7878(2) 0.18404(10) 0.39898(5) 0.0230(3) Uani 1 1 d . . . . .
C9 C 0.8506(3) 0.09155(11) 0.39639(5) 0.0293(3) Uani 1 1 d . . . . .
H9 H 0.7678 0.0497 0.3804 0.035 Uiso 1 1 calc R U . . .
C10 C 1.0381(3) 0.05969(11) 0.41755(5) 0.0320(4) Uani 1 1 d . . . . .
H10 H 1.0773 -0.0030 0.4157 0.038 Uiso 1 1 calc R U . . .
C11 C 1.1630(3) 0.12030(11) 0.44076(5) 0.0291(3) Uani 1 1 d . . . . .
H11 H 1.2868 0.0984 0.4546 0.035 Uiso 1 1 calc R U . . .
C12 C 1.1068(2) 0.21585(11) 0.44405(5) 0.0235(3) Uani 1 1 d . . . . .
C13 C 1.2368(3) 0.27991(12) 0.46753(5) 0.0282(3) Uani 1 1 d . . . . .
H13 H 1.3645 0.2592 0.4803 0.034 Uiso 1 1 calc R U . . .
C14 C 1.1775(3) 0.37167(12) 0.47173(5) 0.0310(4) Uani 1 1 d . . . . .
H14 H 1.2640 0.4127 0.4874 0.037 Uiso 1 1 calc R U . . .
C15 C 0.9851(3) 0.40392(11) 0.45228(5) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.9439 0.4661 0.4556 0.038 Uiso 1 1 calc R U . . .
C16 C 0.8578(3) 0.34451(11) 0.42850(5) 0.0271(3) Uani 1 1 d . . . . .
H16 H 0.7326 0.3672 0.4155 0.033 Uiso 1 1 calc R U . . .
C17 C 0.9146(2) 0.24911(10) 0.42354(4) 0.0223(3) Uani 1 1 d . . . . .
C18 C -0.1181(3) 0.47498(14) 0.28450(7) 0.0458(5) Uani 1 1 d . . . . .
H18A H -0.1107 0.4544 0.2551 0.069 Uiso 1 1 calc R U . . .
H18B H -0.1121 0.5421 0.2855 0.069 Uiso 1 1 calc R U . . .
H18C H -0.2516 0.4540 0.2971 0.069 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 0.97(3) . ?
O1 C3 1.3505(18) . ?
O2 C4 1.3743(19) . ?
O2 C18 1.425(2) . ?
N1 C1 1.2852(19) . ?
N1 C8 1.4186(18) . ?
C1 H1A 0.9300 . ?
C1 C2 1.446(2) . ?
C2 C3 1.408(2) . ?
C2 C7 1.407(2) . ?
C3 C4 1.405(2) . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.373(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(2) . ?
C8 C17 1.434(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.406(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.412(2) . ?
C12 C13 1.419(2) . ?
C12 C17 1.427(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.368(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.416(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 104.9(15) . . ?
C4 O2 C18 116.29(14) . . ?
C1 N1 C8 121.95(13) . . ?
N1 C1 H1A 119.1 . . ?
N1 C1 C2 121.73(14) . . ?
C2 C1 H1A 119.1 . . ?
C3 C2 C1 120.97(13) . . ?
C7 C2 C1 119.49(14) . . ?
C7 C2 C3 119.53(14) . . ?
O1 C3 C2 121.81(14) . . ?
O1 C3 C4 118.79(14) . . ?
C4 C3 C2 119.40(14) . . ?
O2 C4 C3 115.01(14) . . ?
O2 C4 C5 125.02(14) . . ?
C5 C4 C3 119.96(15) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.50(15) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.46(15) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.06(15) . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C17 116.13(13) . . ?
C9 C8 N1 123.83(14) . . ?
C9 C8 C17 119.94(14) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.94(15) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.36(15) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.87(14) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 121.48(14) . . ?
C11 C12 C17 119.58(14) . . ?
C13 C12 C17 118.93(14) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.10(15) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.88(15) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.67(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.86(15) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C8 118.29(13) . . ?
C16 C17 C8 123.18(14) . . ?
C16 C17 C12 118.53(14) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C4 O2 -1.8(2) . . . . ?
O1 C3 C4 C5 177.05(14) . . . . ?
O2 C4 C5 C6 179.35(15) . . . . ?
N1 C1 C2 C3 -4.2(2) . . . . ?
N1 C1 C2 C7 176.25(14) . . . . ?
N1 C8 C9 C10 176.15(14) . . . . ?
N1 C8 C17 C12 -175.15(12) . . . . ?
N1 C8 C17 C16 5.0(2) . . . . ?
C1 N1 C8 C9 13.1(2) . . . . ?
C1 N1 C8 C17 -170.57(13) . . . . ?
C1 C2 C3 O1 3.1(2) . . . . ?
C1 C2 C3 C4 -177.27(13) . . . . ?
C1 C2 C7 C6 179.65(14) . . . . ?
C2 C3 C4 O2 178.50(14) . . . . ?
C2 C3 C4 C5 -2.6(2) . . . . ?
C3 C2 C7 C6 0.1(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 1.8(2) . . . . ?
C5 C6 C7 C2 -2.2(2) . . . . ?
C7 C2 C3 O1 -177.38(14) . . . . ?
C7 C2 C3 C4 2.3(2) . . . . ?
C8 N1 C1 C2 -176.80(13) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C8 C17 C12 1.3(2) . . . . ?
C9 C8 C17 C16 -178.52(14) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -179.05(15) . . . . ?
C10 C11 C12 C17 1.3(2) . . . . ?
C11 C12 C13 C14 -177.84(15) . . . . ?
C11 C12 C17 C8 -1.9(2) . . . . ?
C11 C12 C17 C16 177.93(14) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C12 C17 C8 178.39(13) . . . . ?
C13 C12 C17 C16 -1.8(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C8 -179.85(14) . . . . ?
C15 C16 C17 C12 0.3(2) . . . . ?
C17 C8 C9 C10 0.0(2) . . . . ?
C17 C12 C13 C14 1.9(2) . . . . ?
C18 O2 C4 C3 179.04(15) . . . . ?
C18 O2 C4 C5 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
