# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2263570'
loop_
_audit_author_name
_audit_author_address
'Yulei Zhao'
;Qufu Normal University
China
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   5.8326(8)
_cell_length_b                   17.478(3)
_cell_length_c                   24.849(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.997(4)
_cell_angle_gamma                90
_cell_volume                     2531.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4990
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.14

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51542
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.012
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4970
_reflns_number_gt                2582
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex3'
_computing_cell_refinement       Saint
_computing_data_reduction        Saint
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0858P)²+0.9439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0080(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4970
_refine_ls_number_parameters     346
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2028(5) 0.37508(18) 0.44656(12) 0.0496(8) Uani 1 1 d . . . . .
C2 C 0.3966(5) 0.37307(19) 0.41250(12) 0.0546(8) Uani 1 1 d . . . . .
H2 H 0.432044 0.415846 0.392142 0.065 Uiso 1 1 calc R U . . .
C3 C 0.5269(5) 0.31015(19) 0.40977(12) 0.0547(8) Uani 1 1 d . . . . .
H3 H 0.652963 0.311060 0.387861 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4812(5) 0.24173(17) 0.43896(12) 0.0496(8) Uani 1 1 d . . . . .
C5 C 0.6274(6) 0.1778(2) 0.43703(15) 0.0643(9) Uani 1 1 d . . . . .
H5 H 0.755621 0.179480 0.415848 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5834(7) 0.1140(2) 0.46566(17) 0.0762(11) Uani 1 1 d . . . . .
H6 H 0.681879 0.072253 0.464258 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3921(7) 0.1107(2) 0.49706(16) 0.0718(10) Uani 1 1 d . . . . .
H7 H 0.362308 0.066348 0.516313 0.086 Uiso 1 1 calc R U . . .
C8 C 0.2458(6) 0.17188(18) 0.50012(13) 0.0580(9) Uani 1 1 d . . . . .
H8 H 0.117570 0.168735 0.521231 0.070 Uiso 1 1 calc R U . . .
C9 C 0.2894(5) 0.23929(17) 0.47144(12) 0.0465(7) Uani 1 1 d . . . . .
C10 C 0.1472(5) 0.30722(16) 0.47591(11) 0.0438(7) Uani 1 1 d . . . . .
C11 C -0.3355(5) 0.35535(17) 0.55301(11) 0.0450(7) Uani 1 1 d . . . . .
C12 C -0.4759(5) 0.41852(18) 0.55921(12) 0.0521(8) Uani 1 1 d . . . . .
H12 H -0.445313 0.463892 0.541277 0.062 Uiso 1 1 calc R U . . .
C13 C -0.6604(5) 0.4139(2) 0.59192(14) 0.0608(9) Uani 1 1 d . . . . .
H13 H -0.754845 0.456207 0.595968 0.073 Uiso 1 1 calc R U . . .
C14 C -0.7064(5) 0.3470(2) 0.61877(13) 0.0620(9) Uani 1 1 d . . . . .
H14 H -0.831831 0.344045 0.640783 0.074 Uiso 1 1 calc R U . . .
C15 C -0.5657(6) 0.2846(2) 0.61281(14) 0.0636(9) Uani 1 1 d . . . . .
H15 H -0.596164 0.239495 0.631076 0.076 Uiso 1 1 calc R U . . .
C16 C -0.3810(5) 0.28823(19) 0.58022(13) 0.0553(8) Uani 1 1 d . . . . .
H16 H -0.286718 0.245796 0.576420 0.066 Uiso 1 1 calc R U . . .
C17 C 0.8103(6) 0.4784(2) 0.28599(14) 0.0596(9) Uani 1 1 d . . . . .
C18 C 1.0199(6) 0.4949(2) 0.31540(14) 0.0690(10) Uani 1 1 d . . . . .
H18 H 1.069451 0.461983 0.342852 0.083 Uiso 1 1 calc R U . . .
C19 C 1.1463(6) 0.5564(2) 0.30433(14) 0.0671(10) Uani 1 1 d . U . . .
H19 H 1.282816 0.564345 0.324020 0.081 Uiso 1 1 calc R U . . .
C20 C 1.0805(5) 0.61039(18) 0.26360(12) 0.0516(8) Uani 1 1 d . U . . .
C21 C 1.2147(6) 0.6752(2) 0.25333(15) 0.0680(10) Uani 1 1 d . . . . .
H21 H 1.351842 0.682642 0.272838 0.082 Uiso 1 1 calc R U . . .
C22 C 1.1465(7) 0.7276(2) 0.21505(16) 0.0746(11) Uani 1 1 d . . . . .
H22 H 1.234967 0.770852 0.209108 0.089 Uiso 1 1 calc R U . . .
C23 C 0.9453(7) 0.7156(2) 0.18535(16) 0.0745(11) Uani 1 1 d . . . . .
H23 H 0.900456 0.750851 0.158993 0.089 Uiso 1 1 calc R U . . .
C24 C 0.8103(6) 0.65304(19) 0.19379(14) 0.0602(9) Uani 1 1 d . . . . .
H24 H 0.674732 0.646582 0.173464 0.072 Uiso 1 1 calc R U . . .
C25 C 0.8752(5) 0.59832(18) 0.23310(12) 0.0494(8) Uani 1 1 d . . . . .
C26 C 0.7390(5) 0.53103(17) 0.24316(12) 0.0472(7) Uani 1 1 d . . . . .
C27 C 0.2382(5) 0.44446(19) 0.18350(13) 0.0534(8) Uani 1 1 d . . . . .
C28 C 0.1130(6) 0.3783(2) 0.19250(15) 0.0673(10) Uani 1 1 d . . . . .
H28 H 0.158422 0.344598 0.219829 0.081 Uiso 1 1 calc R U . . .
C29 C -0.0799(7) 0.3631(3) 0.16038(19) 0.0835(12) Uani 1 1 d . . . . .
H29 H -0.164021 0.318827 0.166242 0.100 Uiso 1 1 calc R U . . .
C30 C -0.1489(7) 0.4121(3) 0.12012(18) 0.0822(12) Uani 1 1 d . . . . .
H30 H -0.278686 0.401128 0.098715 0.099 Uiso 1 1 calc R U . . .
C31 C -0.0253(7) 0.4776(2) 0.11145(16) 0.0779(11) Uani 1 1 d . . . . .
H31 H -0.073220 0.511203 0.084279 0.093 Uiso 1 1 calc R U . . .
C32 C 0.1701(6) 0.4944(2) 0.14275(14) 0.0663(10) Uani 1 1 d . . . . .
H32 H 0.253977 0.538532 0.136431 0.080 Uiso 1 1 calc R U . . .
N1 N -0.0265(4) 0.30146(14) 0.50977(9) 0.0464(6) Uani 1 1 d . . . . .
N2 N -0.1525(4) 0.36190(14) 0.51750(10) 0.0470(6) Uani 1 1 d . . . . .
N3 N 0.5551(4) 0.51926(14) 0.21039(10) 0.0511(7) Uani 1 1 d . . . . .
N4 N 0.4310(4) 0.45750(15) 0.21817(11) 0.0564(7) Uani 1 1 d . . . . .
O1 O 0.0852(4) 0.43650(13) 0.45018(10) 0.0649(7) Uani 1 1 d . . . . .
H1 H -0.011667 0.430940 0.472982 0.097 Uiso 1 1 calc R U . . .
O2 O 0.6903(4) 0.41945(14) 0.29760(10) 0.0734(7) Uani 1 1 d . . . . .
H2A H 0.578830 0.416557 0.276674 0.110 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
C1 O1 1.279(3) . ?
C1 C10 1.435(4) . ?
C1 C2 1.436(4) . ?
C2 C3 1.340(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.429(4) . ?
C3 H3 0.9300 . ?
C4 C9 1.403(4) . ?
C4 C5 1.407(4) . ?
C5 C6 1.352(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.455(4) . ?
C10 N1 1.343(4) . ?
C11 C16 1.384(4) . ?
C11 C12 1.387(4) . ?
C11 N2 1.413(4) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.284(4) . ?
C17 C18 1.432(5) . ?
C17 C26 1.456(4) . ?
C18 C19 1.338(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.427(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.405(5) . ?
C20 C25 1.410(4) . ?
C21 C22 1.369(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.409(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.446(4) . ?
C26 N3 1.340(4) . ?
C27 C32 1.385(5) . ?
C27 C28 1.391(5) . ?
C27 N4 1.411(4) . ?
C28 C29 1.382(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.367(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.375(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.388(5) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N1 N2 1.305(3) . ?
N3 N4 1.318(3) . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?

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
O1 C1 C10 121.8(3) . . ?
O1 C1 C2 119.8(3) . . ?
C10 C1 C2 118.4(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C9 C4 C5 119.5(3) . . ?
C9 C4 C3 119.0(3) . . ?
C5 C4 C3 121.6(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 118.7(3) . . ?
C4 C9 C10 119.2(3) . . ?
C8 C9 C10 122.1(3) . . ?
N1 C10 C1 124.7(3) . . ?
N1 C10 C9 115.5(3) . . ?
C1 C10 C9 119.7(3) . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 N2 122.4(3) . . ?
C12 C11 N2 117.8(3) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
O2 C17 C18 120.6(3) . . ?
O2 C17 C26 121.8(3) . . ?
C18 C17 C26 117.6(3) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 122.7(3) . . ?
C18 C19 H19 118.6 . . ?
C20 C19 H19 118.6 . . ?
C21 C20 C25 119.4(3) . . ?
C21 C20 C19 121.6(3) . . ?
C25 C20 C19 119.0(3) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 119.4(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 121.5(4) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 118.2(3) . . ?
C24 C25 C26 122.4(3) . . ?
C20 C25 C26 119.3(3) . . ?
N3 C26 C25 116.9(3) . . ?
N3 C26 C17 123.3(3) . . ?
C25 C26 C17 119.7(3) . . ?
C32 C27 C28 120.2(3) . . ?
C32 C27 N4 123.2(3) . . ?
C28 C27 N4 116.6(3) . . ?
C29 C28 C27 119.2(4) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C30 C29 C28 121.0(4) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.6(4) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 120.8(4) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C27 C32 C31 119.1(4) . . ?
C27 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
N2 N1 C10 118.2(2) . . ?
N1 N2 C11 117.9(2) . . ?
N4 N3 C26 118.0(3) . . ?
N3 N4 C27 118.2(3) . . ?
C1 O1 H1 109.5 . . ?
C17 O2 H2A 109.5 . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2268663'
loop_
_audit_author_name
_audit_author_address
'Yulei Zhao'
;Qufu Normal University
China
;
_audit_update_record             
;
2023-06-09 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   4.7435(7)
_cell_length_b                   16.733(2)
_cell_length_c                   20.701(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.221(4)
_cell_angle_gamma                90
_cell_volume                     1643.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    6622
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6709
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19601
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         27.769
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3852
_reflns_number_gt                2723
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3852
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1780(4) 0.50134(11) 0.23819(8) 0.0771(5) Uani 1 1 d . . . . .
H1A H 1.269796 0.453467 0.223762 0.116 Uiso 1 1 calc R U . . .
H1B H 1.317362 0.540808 0.248948 0.116 Uiso 1 1 calc R U . . .
H1C H 1.058235 0.521425 0.204404 0.116 Uiso 1 1 calc R U . . .
C2 C 0.8693(3) 0.41555(8) 0.29458(7) 0.0572(3) Uani 1 1 d . . . . .
C3 C 0.6942(3) 0.40457(8) 0.35337(6) 0.0516(3) Uani 1 1 d . . . . .
C4 C 0.5677(3) 0.47236(9) 0.37989(7) 0.0603(4) Uani 1 1 d . . . . .
H4 H 0.609873 0.522505 0.363124 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3818(4) 0.46606(9) 0.43037(7) 0.0684(4) Uani 1 1 d . . . . .
H5 H 0.293609 0.511412 0.446595 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3270(4) 0.39219(10) 0.45678(8) 0.0681(4) Uani 1 1 d . . . . .
H6 H 0.202199 0.387522 0.491113 0.082 Uiso 1 1 calc R U . . .
C7 C 0.4577(3) 0.32502(9) 0.43222(7) 0.0589(3) Uani 1 1 d . . . . .
H7 H 0.422345 0.275669 0.451194 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6404(3) 0.32901(8) 0.37996(6) 0.0507(3) Uani 1 1 d . . . . .
C9 C 0.7806(3) 0.25170(8) 0.35828(8) 0.0592(3) Uani 1 1 d . . . . .
H9A H 0.897501 0.262622 0.320971 0.071 Uiso 1 1 calc R U . . .
H9B H 0.902382 0.232393 0.392641 0.071 Uiso 1 1 calc R U . . .
C10 C 0.5704(3) 0.18737(8) 0.34112(6) 0.0530(3) Uani 1 1 d . . . . .
C11 C 0.5209(3) 0.12365(8) 0.38924(7) 0.0595(3) Uani 1 1 d . . . . .
C12 C 0.2781(5) 0.00561(11) 0.41638(9) 0.0935(6) Uani 1 1 d . . . . .
H12A H 0.450337 -0.017002 0.432626 0.140 Uiso 1 1 calc R U . . .
H12B H 0.167762 -0.035462 0.396048 0.140 Uiso 1 1 calc R U . . .
H12C H 0.173475 0.028398 0.451449 0.140 Uiso 1 1 calc R U . . .
C13 C 0.3074(3) 0.24087(8) 0.18639(6) 0.0544(3) Uani 1 1 d . . . . .
C14 C 0.1009(3) 0.18495(9) 0.17345(7) 0.0642(4) Uani 1 1 d . . . . .
H14 H 0.062127 0.144682 0.203080 0.077 Uiso 1 1 calc R U . . .
C15 C -0.0479(4) 0.18943(11) 0.11590(9) 0.0792(5) Uani 1 1 d . . . . .
H15 H -0.188391 0.152104 0.107265 0.095 Uiso 1 1 calc R U . . .
C16 C 0.0083(4) 0.24798(12) 0.07141(8) 0.0835(5) Uani 1 1 d . . . . .
H16 H -0.092828 0.250272 0.032874 0.100 Uiso 1 1 calc R U . . .
C17 C 0.2139(4) 0.30284(11) 0.08418(8) 0.0799(5) Uani 1 1 d . . . . .
H17 H 0.252599 0.342635 0.054128 0.096 Uiso 1 1 calc R U . . .
C18 C 0.3648(4) 0.29990(9) 0.14117(7) 0.0692(4) Uani 1 1 d . . . . .
H18 H 0.505119 0.337439 0.149329 0.083 Uiso 1 1 calc R U . . .
N1 N 0.4612(3) 0.24131(7) 0.24424(6) 0.0581(3) Uani 1 1 d . . . . .
H1 H 0.581110 0.278827 0.251473 0.070 Uiso 1 1 calc R U . . .
N2 N 0.4235(2) 0.18398(6) 0.28834(5) 0.0529(3) Uani 1 1 d . . . . .
O1 O 0.6319(3) 0.12233(7) 0.44167(6) 0.0886(4) Uani 1 1 d . . . . .
O2 O 0.3423(3) 0.06708(6) 0.36979(5) 0.0757(3) Uani 1 1 d . . . . .
O3 O 0.8778(3) 0.36977(7) 0.24950(6) 0.0887(4) Uani 1 1 d . . . . .
O4 O 1.0103(2) 0.48379(6) 0.29453(5) 0.0663(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O4 1.4445(18) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O3 1.2081(17) . ?
C2 O4 1.3233(17) . ?
C2 C3 1.488(2) . ?
C3 C4 1.3968(19) . ?
C3 C8 1.4028(19) . ?
C4 C5 1.374(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.5228(18) . ?
C9 C10 1.5088(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.2950(17) . ?
C10 C11 1.478(2) . ?
C11 O1 1.2046(18) . ?
C11 O2 1.3316(18) . ?
C12 O2 1.4433(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.380(2) . ?
C13 C18 1.389(2) . ?
C13 N1 1.3997(18) . ?
C14 C15 1.385(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 N2 1.3367(15) . ?
N1 H1 0.8600 . ?

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
O4 C1 H1A 109.5 . . ?
O4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O4 121.88(14) . . ?
O3 C2 C3 125.04(13) . . ?
O4 C2 C3 113.01(12) . . ?
C4 C3 C8 119.91(13) . . ?
C4 C3 C2 117.61(12) . . ?
C8 C3 C2 122.37(12) . . ?
C5 C4 C3 120.97(14) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.59(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.90(14) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 121.96(14) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C7 C8 C3 117.61(12) . . ?
C7 C8 C9 117.57(12) . . ?
C3 C8 C9 124.72(12) . . ?
C10 C9 C8 112.74(11) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C11 116.79(12) . . ?
N2 C10 C9 125.65(13) . . ?
C11 C10 C9 117.53(12) . . ?
O1 C11 O2 122.32(14) . . ?
O1 C11 C10 123.39(14) . . ?
O2 C11 C10 114.28(12) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.50(14) . . ?
C14 C13 N1 122.46(13) . . ?
C18 C13 N1 118.04(13) . . ?
C13 C14 C15 119.31(15) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 121.11(18) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 119.42(17) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.68(16) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.98(16) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
N2 N1 C13 120.66(11) . . ?
N2 N1 H1 119.7 . . ?
C13 N1 H1 119.7 . . ?
C10 N2 N1 118.16(12) . . ?
C11 O2 C12 116.12(13) . . ?
C2 O4 C1 117.12(12) . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028

