# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2207019'
loop_
_audit_author_name
_audit_author_address
'Ying Yang'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-09-13 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_audit_creation_date             2022-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_chemical_absolute_configuration ?
_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                   3.9580(2)
_cell_length_b                   18.2868(8)
_cell_length_c                   20.5693(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1488.79(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5611
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      78.72
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1325 before and 0.0966 after correction.
The Ratio of minimum to maximum transmission is 0.8702.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       strip
_exptl_crystal_F_000             648
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14572
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.913
_diffrn_reflns_theta_min         3.234
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2726
_reflns_number_total             3158
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.134
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.099
_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)+(0.0353P)²+0.1797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O3 O 1.0914(6) 0.71077(11) 0.44535(10) 0.0572(5) Uani 1 1 d . . . . .
O2 O 0.9043(6) 0.09354(11) 0.44962(10) 0.0578(6) Uani 1 1 d . . . . .
O0AA O 0.4626(8) 0.49944(11) 0.21483(11) 0.0704(7) Uani 1 1 d . . . . .
O1 O 0.3761(7) 0.38134(11) 0.19595(10) 0.0619(6) Uani 1 1 d . . . . .
C10 C 0.5817(7) 0.26735(15) 0.39428(14) 0.0470(6) Uani 1 1 d . . . . .
N4 N 0.4260(8) 0.31233(13) 0.22921(12) 0.0569(7) Uani 1 1 d . . . . .
C12 C 0.7769(7) 0.43487(15) 0.34616(13) 0.0420(6) Uani 1 1 d . . . . .
C13 C 0.8510(7) 0.50884(14) 0.36651(13) 0.0411(6) Uani 1 1 d . . . . .
C5 C 0.6558(7) 0.26633(14) 0.32796(13) 0.0426(6) Uani 1 1 d . . . . .
C6 C 0.8109(8) 0.20451(15) 0.30240(14) 0.0464(6) Uani 1 1 d . . . . .
C9 C 0.6641(8) 0.20865(16) 0.43300(14) 0.0490(7) Uani 1 1 d . . . . .
C14 C 0.7518(7) 0.57299(16) 0.33359(14) 0.0457(6) Uani 1 1 d . . . . .
C3 C 0.5648(7) 0.32721(14) 0.28442(13) 0.0436(6) Uani 1 1 d . . . . .
C15 C 0.8267(7) 0.64116(15) 0.35867(13) 0.0442(6) Uani 1 1 d . . . . .
C7 C 0.8982(8) 0.14556(15) 0.34091(14) 0.0485(6) Uani 1 1 d . . . . .
C19 C 1.0020(10) 0.77793(18) 0.41385(18) 0.0566(7) Uani 1 1 d . . . . .
C18 C 1.0227(7) 0.51688(15) 0.42579(14) 0.0462(6) Uani 1 1 d . . . . .
C8 C 0.8255(7) 0.14797(15) 0.40684(14) 0.0450(6) Uani 1 1 d . . . . .
C2 C 0.6181(7) 0.40480(14) 0.29430(13) 0.0431(6) Uani 1 1 d . . . . .
C17 C 1.0960(8) 0.58433(16) 0.45098(14) 0.0504(7) Uani 1 1 d . . . . .
C1 C 0.4850(8) 0.43776(16) 0.23452(14) 0.0514(7) Uani 1 1 d . . . . .
C16 C 0.9993(7) 0.64728(15) 0.41700(13) 0.0436(6) Uani 1 1 d . . . . .
C11 C 1.0643(9) 0.03005(18) 0.4238(2) 0.0604(8) Uani 1 1 d . . . . .
H9 H 0.617(8) 0.2096(15) 0.4796(15) 0.056(9) Uiso 1 1 d . . . . .
H17 H 1.221(8) 0.5902(16) 0.4930(15) 0.054(9) Uiso 1 1 d . . . . .
H12 H 0.857(8) 0.4002(14) 0.3773(14) 0.045(8) Uiso 1 1 d . . . . .
H19A H 1.091(9) 0.7799(16) 0.3675(17) 0.060(9) Uiso 1 1 d . . . . .
H6 H 0.858(8) 0.2055(16) 0.2525(15) 0.054(8) Uiso 1 1 d . . . . .
H11A H 1.272(10) 0.0434(18) 0.4004(18) 0.073(11) Uiso 1 1 d . . . . .
H14 H 0.631(10) 0.5671(17) 0.2907(16) 0.068(10) Uiso 1 1 d . . . . .
H11B H 0.906(11) 0.0033(18) 0.3931(18) 0.076(11) Uiso 1 1 d . . . . .
H15 H 0.750(7) 0.6832(16) 0.3359(13) 0.042(8) Uiso 1 1 d . . . . .
H19B H 1.099(10) 0.8164(18) 0.4419(17) 0.071(11) Uiso 1 1 d . . . . .
H7 H 1.008(9) 0.1033(16) 0.3225(15) 0.057(9) Uiso 1 1 d . . . . .
H11C H 1.095(9) -0.0032(17) 0.4612(16) 0.062(10) Uiso 1 1 d . . . . .
H19C H 0.755(10) 0.7809(18) 0.4109(16) 0.067(10) Uiso 1 1 d . . . . .
H18 H 1.085(9) 0.4736(16) 0.4499(16) 0.060(9) Uiso 1 1 d . . . . .
H10 H 0.467(8) 0.3106(16) 0.4150(14) 0.053(8) Uiso 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
O3 C19 1.433(4) . ?
O3 C16 1.349(3) . ?
O2 C8 1.365(3) . ?
O2 C11 1.425(4) . ?
O0AA C1 1.202(3) . ?
O1 N4 1.449(3) . ?
O1 C1 1.371(3) . ?
C10 C5 1.396(4) . ?
C10 C9 1.376(4) . ?
N4 C3 1.290(4) . ?
C12 C13 1.446(4) . ?
C12 C2 1.355(4) . ?
C13 C14 1.410(4) . ?
C13 C18 1.404(4) . ?
C5 C6 1.390(4) . ?
C5 C3 1.474(4) . ?
C6 C7 1.382(4) . ?
C9 C8 1.389(4) . ?
C14 C15 1.381(4) . ?
C3 C2 1.449(4) . ?
C15 C16 1.385(4) . ?
C7 C8 1.387(4) . ?
C18 C17 1.369(4) . ?
C2 C1 1.467(4) . ?
C17 C16 1.400(4) . ?

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
C16 O3 C19 118.4(2) . . ?
C8 O2 C11 117.1(2) . . ?
C1 O1 N4 109.8(2) . . ?
C9 C10 C5 120.4(3) . . ?
C3 N4 O1 106.9(2) . . ?
C2 C12 C13 134.6(3) . . ?
C14 C13 C12 125.6(3) . . ?
C18 C13 C12 116.6(2) . . ?
C18 C13 C14 117.7(2) . . ?
C10 C5 C3 122.2(2) . . ?
C6 C5 C10 118.3(3) . . ?
C6 C5 C3 119.5(2) . . ?
C7 C6 C5 121.9(3) . . ?
C10 C9 C8 120.5(3) . . ?
C15 C14 C13 120.8(3) . . ?
N4 C3 C5 118.7(2) . . ?
N4 C3 C2 113.1(2) . . ?
C2 C3 C5 128.2(2) . . ?
C14 C15 C16 120.1(3) . . ?
C6 C7 C8 118.9(3) . . ?
C17 C18 C13 121.7(3) . . ?
O2 C8 C9 116.0(2) . . ?
O2 C8 C7 124.1(3) . . ?
C7 C8 C9 120.0(3) . . ?
C12 C2 C3 125.1(3) . . ?
C12 C2 C1 131.3(3) . . ?
C3 C2 C1 103.4(2) . . ?
C18 C17 C16 119.6(3) . . ?
O0AA C1 O1 119.2(3) . . ?
O0AA C1 C2 134.0(3) . . ?
O1 C1 C2 106.8(2) . . ?
O3 C16 C15 125.2(3) . . ?
O3 C16 C17 114.7(2) . . ?
C15 C16 C17 120.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
