# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_cu_210604lcz_0m
_database_code_depnum_ccdc_archive 'CCDC 2249151'
loop_
_audit_author_name
_audit_author_address
'Qing-Hai Deng'
;Shanghai Normal University
China
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N5 O'
_chemical_formula_sum            'C18 H16 N5 O'
_chemical_formula_weight         318.36
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9211(2)
_cell_length_b                   8.4929(2)
_cell_length_c                   24.4236(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1643.05(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.079
_cell_measurement_theta_min      5.870
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1480 before and 0.0624 after correction. The Ratio of minimum to maximum transmission is 0.7944. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14493
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.106
_diffrn_reflns_theta_min         5.872
_diffrn_ambient_temperature      293.42
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2628
_reflns_number_total             3087
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0406
_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)+(0.0661P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1139
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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
O1 O -0.7266(3) -0.65663(19) -0.52818(8) 0.0711(6) Uani 1 1 d . . . . .
N1 N -0.6060(3) -0.7849(2) -0.41619(8) 0.0497(5) Uani 1 1 d . . . . .
N2 N -0.7890(3) -0.56554(19) -0.44459(8) 0.0470(5) Uani 1 1 d . . . . .
N3 N -0.9587(3) -0.8460(3) -0.34769(11) 0.0651(6) Uani 1 1 d . . . . .
N4 N -0.8880(3) -0.9746(3) -0.34744(10) 0.0650(6) Uani 1 1 d . . . . .
N5 N -0.8363(5) -1.0980(3) -0.34503(17) 0.1084(11) Uani 1 1 d . . . . .
C1 C -0.7778(3) -0.7267(2) -0.42293(10) 0.0473(5) Uani 1 1 d . . . . .
H1 H -0.846053 -0.799794 -0.444670 0.057 Uiso 1 1 calc R . . . .
C2 C -0.8479(3) -0.7111(3) -0.36354(11) 0.0494(6) Uani 1 1 d . . . . .
C3 C -0.6885(3) -0.7035(3) -0.32991(10) 0.0475(5) Uani 1 1 d . . . . .
C4 C -0.6656(4) -0.6689(4) -0.27480(11) 0.0625(7) Uani 1 1 d . . . . .
C5 C -0.5012(4) -0.6720(4) -0.25506(14) 0.0740(8) Uani 1 1 d . . . . .
H5 H -0.480887 -0.646405 -0.218624 0.089 Uiso 1 1 calc R . . . .
C6 C -0.3674(4) -0.7122(4) -0.28843(13) 0.0684(8) Uani 1 1 d . . . . .
H6 H -0.258956 -0.712710 -0.273818 0.082 Uiso 1 1 calc R . . . .
C7 C -0.3892(3) -0.7518(3) -0.34293(11) 0.0551(6) Uani 1 1 d . . . . .
H7 H -0.298766 -0.781061 -0.364958 0.066 Uiso 1 1 calc R . . . .
C8 C -0.5523(3) -0.7456(2) -0.36301(10) 0.0454(5) Uani 1 1 d . . . . .
C9 C -0.8108(5) -0.6320(5) -0.23717(13) 0.0895(11) Uani 1 1 d . . . . .
H9A H -0.903635 -0.700983 -0.245206 0.134 Uiso 1 1 calc GR . . . .
H9B H -0.845363 -0.524759 -0.242436 0.134 Uiso 1 1 calc GR . . . .
H9C H -0.776130 -0.646881 -0.199863 0.134 Uiso 1 1 calc GR . . . .
C10 C -0.9562(3) -0.5634(3) -0.36607(13) 0.0611(7) Uani 1 1 d . . . . .
H10A H -1.067285 -0.586617 -0.380658 0.073 Uiso 1 1 calc R . . . .
H10B H -0.968400 -0.516381 -0.330088 0.073 Uiso 1 1 calc R . . . .
C11 C -0.8594(3) -0.4561(3) -0.40398(11) 0.0547(6) Uani 1 1 d . . . . .
H11A H -0.933527 -0.379788 -0.421137 0.066 Uiso 1 1 calc R . . . .
H11B H -0.770492 -0.400856 -0.384567 0.066 Uiso 1 1 calc R . . . .
C12 C -0.7620(3) -0.5437(2) -0.49880(10) 0.0509(6) Uani 1 1 d . . . . .
C13 C -0.7790(3) -0.3813(2) -0.52188(10) 0.0498(6) Uani 1 1 d . . . . .
C14 C -0.7280(4) -0.2470(3) -0.49374(12) 0.0607(7) Uani 1 1 d . . . . .
H14 H -0.679213 -0.256365 -0.459253 0.073 Uiso 1 1 calc R . . . .
C15 C -0.7492(4) -0.1002(3) -0.51669(14) 0.0718(8) Uani 1 1 d . . . . .
H15 H -0.713966 -0.010956 -0.497803 0.086 Uiso 1 1 calc R . . . .
C16 C -0.8226(4) -0.0852(3) -0.56760(14) 0.0713(9) Uani 1 1 d . . . . .
H16 H -0.840227 0.014215 -0.582492 0.086 Uiso 1 1 calc R . . . .
C17 C -0.8694(4) -0.2165(4) -0.59618(13) 0.0702(8) Uani 1 1 d . . . . .
H17 H -0.916466 -0.206098 -0.630879 0.084 Uiso 1 1 calc R . . . .
C18 C -0.8472(4) -0.3647(3) -0.57380(11) 0.0611(7) Uani 1 1 d . . . . .
H18 H -0.878145 -0.453491 -0.593686 0.073 Uiso 1 1 calc R . . . .


_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 C12 1.230(3) . ?
N1 C1 1.457(3) . ?
N1 C8 1.407(3) . ?
N2 C1 1.470(3) . ?
N2 C11 1.469(3) . ?
N2 C12 1.354(3) . ?
N3 N4 1.227(3) . ?
N3 C2 1.495(3) . ?
N4 N5 1.127(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.559(3) . ?
C2 C3 1.508(3) . ?
C2 C10 1.521(3) . ?
C3 C4 1.390(4) . ?
C3 C8 1.395(3) . ?
C4 C5 1.389(4) . ?
C4 C9 1.505(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.508(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.496(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.385(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 107.81(18) . . ?
C11 N2 C1 111.66(18) . . ?
C12 N2 C1 118.03(17) . . ?
C12 N2 C11 129.31(18) . . ?
N4 N3 C2 114.5(2) . . ?
N5 N4 N3 173.5(3) . . ?
N1 C1 N2 114.43(19) . . ?
N1 C1 H1 111.2 . . ?
N1 C1 C2 104.86(18) . . ?
N2 C1 H1 111.2 . . ?
N2 C1 C2 103.54(17) . . ?
C2 C1 H1 111.2 . . ?
N3 C2 C1 112.6(2) . . ?
N3 C2 C3 112.56(19) . . ?
N3 C2 C10 108.16(19) . . ?
C3 C2 C1 102.25(18) . . ?
C3 C2 C10 117.3(2) . . ?
C10 C2 C1 103.48(19) . . ?
C4 C3 C2 130.2(2) . . ?
C4 C3 C8 121.0(2) . . ?
C8 C3 C2 108.7(2) . . ?
C3 C4 C9 122.4(3) . . ?
C5 C4 C3 117.0(3) . . ?
C5 C4 C9 120.6(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.1(3) . . ?
C7 C6 H6 118.9 . . ?
C6 C7 H7 121.7 . . ?
C8 C7 C6 116.7(2) . . ?
C8 C7 H7 121.7 . . ?
C3 C8 N1 111.23(19) . . ?
C7 C8 N1 126.9(2) . . ?
C7 C8 C3 121.8(2) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 111.0 . . ?
C2 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C2 103.7(2) . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
N2 C11 C10 103.0(2) . . ?
N2 C11 H11A 111.2 . . ?
N2 C11 H11B 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
O1 C12 N2 120.0(2) . . ?
O1 C12 C13 121.3(2) . . ?
N2 C12 C13 118.7(2) . . ?
C14 C13 C12 122.9(2) . . ?
C18 C13 C12 118.3(2) . . ?
C18 C13 C14 118.8(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(3) . . ?
C17 C18 H18 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
