# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_220509_zyf_1
_database_code_depnum_ccdc_archive 'CCDC 2279999'
loop_
_audit_author_name
_audit_author_address
HS-a
;Univerisity of South China
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_audit_creation_date             2022-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o'
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                   10.2374(7)
_cell_length_b                   9.6937(5)
_cell_length_c                   17.3010(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.152(7)
_cell_angle_gamma                90
_cell_volume                     1657.24(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1557
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2293
_cell_measurement_theta_min      2.0568
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.294
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   56.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  -90.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   78.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  150.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0664398000
_diffrn_orient_matrix_UB_12      0.0218258000
_diffrn_orient_matrix_UB_13      0.0006632000
_diffrn_orient_matrix_UB_21      -0.0240026000
_diffrn_orient_matrix_UB_22      0.0682215000
_diffrn_orient_matrix_UB_23      -0.0092030000
_diffrn_orient_matrix_UB_31      0.0128345000
_diffrn_orient_matrix_UB_32      0.0148440000
_diffrn_orient_matrix_UB_33      0.0414613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2205
_reflns_number_total             3858
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.023
_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)+(0.0726P)²+0.3581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C2(H2A), C3(H3A), C4(H4), C7(H7), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.02587(18) 0.79207(15) 0.19489(9) 0.0711(5) Uani 1 1 d . . . . .
N1 N -0.01074(18) 0.83666(18) 0.45489(10) 0.0586(5) Uani 1 1 d . . . . .
N2 N 0.2108(2) 1.05323(18) 0.29372(12) 0.0694(6) Uani 1 1 d . . . . .
H2 H 0.205393 1.110034 0.330939 0.083 Uiso 1 1 calc R . . . .
N3 N -0.0491(2) 1.02302(19) 0.19226(13) 0.0748(6) Uani 1 1 d . . . . .
H3 H -0.016275 1.100243 0.213040 0.090 Uiso 1 1 calc R . . . .
C1 C 0.1798(3) 0.8315(2) 0.57961(15) 0.0724(7) Uani 1 1 d . . . . .
H1 H 0.127098 0.812677 0.614726 0.087 Uiso 1 1 calc R . . . .
C2 C 0.3170(3) 0.8462(3) 0.60632(18) 0.0914(9) Uani 1 1 d . . . . .
H2A H 0.358076 0.838038 0.660820 0.110 Uiso 1 1 calc R . . . .
C3 C 0.3964(3) 0.8728(3) 0.5544(2) 0.0935(10) Uani 1 1 d . . . . .
H3A H 0.489752 0.878728 0.574574 0.112 Uiso 1 1 calc R . . . .
C4 C 0.3406(3) 0.8906(2) 0.47380(18) 0.0756(7) Uani 1 1 d . . . . .
H4 H 0.394936 0.910622 0.439750 0.091 Uiso 1 1 calc R . . . .
C5 C 0.2001(2) 0.8781(2) 0.44394(14) 0.0578(6) Uani 1 1 d . . . . .
C6 C 0.1221(2) 0.8459(2) 0.49768(14) 0.0576(6) Uani 1 1 d . . . . .
C7 C -0.0183(2) 0.8640(2) 0.37652(13) 0.0586(6) Uani 1 1 d . . . . .
H7 H -0.097927 0.864415 0.335563 0.070 Uiso 1 1 calc R . . . .
C8 C 0.1070(2) 0.8905(2) 0.36647(13) 0.0566(6) Uani 1 1 d . . . . .
C9 C -0.1232(2) 0.7970(3) 0.48618(14) 0.0718(7) Uani 1 1 d . . . . .
H9A H -0.204527 0.840021 0.455109 0.108 Uiso 1 1 calc GR . . . .
H9B H -0.106092 0.826049 0.540962 0.108 Uiso 1 1 calc GR . . . .
H9C H -0.133756 0.698562 0.483218 0.108 Uiso 1 1 calc GR . . . .
C10 C 0.1417(2) 0.9219(2) 0.28906(13) 0.0588(6) Uani 1 1 d . . . . .
H10 H 0.205453 0.850783 0.281696 0.071 Uiso 1 1 calc R . . . .
C11 C 0.2852(2) 1.0913(2) 0.24082(13) 0.0576(6) Uani 1 1 d . . . . .
C12 C 0.3051(2) 1.0041(3) 0.18151(15) 0.0705(7) Uani 1 1 d . . . . .
H12 H 0.263356 0.918179 0.174309 0.085 Uiso 1 1 calc R . . . .
C13 C 0.3865(3) 1.0434(3) 0.13286(17) 0.0885(9) Uani 1 1 d . . . . .
H13 H 0.399821 0.982901 0.093880 0.106 Uiso 1 1 calc R . . . .
C14 C 0.4470(3) 1.1687(4) 0.1413(2) 0.0994(10) Uani 1 1 d . . . . .
H14 H 0.502425 1.193949 0.108781 0.119 Uiso 1 1 calc R . . . .
C15 C 0.4256(3) 1.2584(3) 0.19848(19) 0.0891(9) Uani 1 1 d . . . . .
H15 H 0.465217 1.345382 0.203600 0.107 Uiso 1 1 calc R . . . .
C16 C 0.3460(2) 1.2208(2) 0.24833(15) 0.0696(7) Uani 1 1 d . . . . .
H16 H 0.333084 1.282130 0.286999 0.084 Uiso 1 1 calc R . . . .
C17 C 0.0154(2) 0.9078(2) 0.22013(14) 0.0584(6) Uani 1 1 d . . . . .
C18 C -0.1724(3) 1.0246(3) 0.12841(19) 0.1022(10) Uani 1 1 d . . . . .
H18A H -0.155292 1.066076 0.081636 0.153 Uiso 1 1 calc GR . . . .
H18B H -0.240124 1.076967 0.144842 0.153 Uiso 1 1 calc GR . . . .
H18C H -0.203895 0.931793 0.116297 0.153 Uiso 1 1 calc GR . . . .


_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 C17 1.237(2) . ?
N1 C6 1.370(3) . ?
N1 C7 1.364(3) . ?
N1 C9 1.447(3) . ?
N2 H2 0.8600 . ?
N2 C10 1.448(3) . ?
N2 C11 1.385(3) . ?
N3 H3 0.8600 . ?
N3 C17 1.323(3) . ?
N3 C18 1.444(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.366(4) . ?
C1 C6 1.393(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.372(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(3) . ?
C5 C6 1.410(3) . ?
C5 C8 1.432(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(3) . ?
C8 C10 1.504(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C17 1.519(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.393(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.354(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9300 . ?
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
C6 N1 C9 126.13(19) . . ?
C7 N1 C6 108.35(18) . . ?
C7 N1 C9 125.44(19) . . ?
C10 N2 H2 118.6 . . ?
C11 N2 H2 118.6 . . ?
C11 N2 C10 122.82(18) . . ?
C17 N3 H3 118.6 . . ?
C17 N3 C18 122.8(2) . . ?
C18 N3 H3 118.6 . . ?
C2 C1 H1 121.3 . . ?
C2 C1 C6 117.3(3) . . ?
C6 C1 H1 121.3 . . ?
C1 C2 H2A 119.1 . . ?
C1 C2 C3 121.7(3) . . ?
C3 C2 H2A 119.1 . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 C8 134.9(2) . . ?
C6 C5 C8 106.44(19) . . ?
N1 C6 C1 129.8(2) . . ?
N1 C6 C5 108.13(19) . . ?
C1 C6 C5 122.0(2) . . ?
N1 C7 H7 124.7 . . ?
C8 C7 N1 110.7(2) . . ?
C8 C7 H7 124.7 . . ?
C5 C8 C10 126.6(2) . . ?
C7 C8 C5 106.42(19) . . ?
C7 C8 C10 126.9(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C8 110.72(18) . . ?
N2 C10 H10 107.1 . . ?
N2 C10 C17 115.21(18) . . ?
C8 C10 H10 107.1 . . ?
C8 C10 C17 109.28(18) . . ?
C17 C10 H10 107.1 . . ?
N2 C11 C12 122.7(2) . . ?
N2 C11 C16 119.2(2) . . ?
C12 C11 C16 118.0(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
O1 C17 N3 123.0(2) . . ?
O1 C17 C10 120.06(19) . . ?
N3 C17 C10 116.86(19) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 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
N1 C7 C8 C5 0.4(2) . . . . ?
N1 C7 C8 C10 178.53(18) . . . . ?
N2 C10 C17 O1 156.83(19) . . . . ?
N2 C10 C17 N3 -26.2(3) . . . . ?
N2 C11 C12 C13 -176.3(2) . . . . ?
N2 C11 C16 C15 177.1(2) . . . . ?
C1 C2 C3 C4 2.4(5) . . . . ?
C2 C1 C6 N1 180.0(2) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 179.2(2) . . . . ?
C4 C5 C6 N1 -178.91(19) . . . . ?
C4 C5 C6 C1 2.5(3) . . . . ?
C4 C5 C8 C7 179.1(2) . . . . ?
C4 C5 C8 C10 1.0(4) . . . . ?
C5 C8 C10 N2 -59.2(3) . . . . ?
C5 C8 C10 C17 172.90(19) . . . . ?
C6 N1 C7 C8 0.3(2) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C5 C8 C7 -0.9(2) . . . . ?
C6 C5 C8 C10 -179.05(19) . . . . ?
C7 N1 C6 C1 177.6(2) . . . . ?
C7 N1 C6 C5 -0.9(2) . . . . ?
C7 C8 C10 N2 123.1(2) . . . . ?
C7 C8 C10 C17 -4.8(3) . . . . ?
C8 C5 C6 N1 1.1(2) . . . . ?
C8 C5 C6 C1 -177.5(2) . . . . ?
C8 C10 C17 O1 -77.8(2) . . . . ?
C8 C10 C17 N3 99.2(2) . . . . ?
C9 N1 C6 C1 -5.7(4) . . . . ?
C9 N1 C6 C5 175.9(2) . . . . ?
C9 N1 C7 C8 -176.5(2) . . . . ?
C10 N2 C11 C12 -3.3(3) . . . . ?
C10 N2 C11 C16 178.6(2) . . . . ?
C11 N2 C10 C8 162.5(2) . . . . ?
C11 N2 C10 C17 -72.9(3) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C14 C15 C16 C11 -0.6(4) . . . . ?
C16 C11 C12 C13 1.9(3) . . . . ?
C18 N3 C17 O1 -1.4(4) . . . . ?
C18 N3 C17 C10 -178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
