# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20107_a
_database_code_depnum_ccdc_archive 'CCDC 2077243'
loop_
_audit_author_name
_audit_author_address
'Jeff Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8533(12)
_cell_length_b                   7.9653(17)
_cell_length_c                   34.781(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1621.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4143
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.77
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.258
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96852
_exptl_absorpt_correction_T_max  0.98350
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10590
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         26.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3340
_reflns_number_gt                3069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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
O1 O 0.0105(2) 0.28107(18) 0.36271(4) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.1327(2) 0.55170(16) 0.36054(4) 0.0229(3) Uani 1 1 d . . . . .
O3 O 0.7043(2) 0.49418(17) 0.29992(4) 0.0256(3) Uani 1 1 d . . . . .
O4 O 0.9492(2) 0.3373(2) 0.27085(4) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.3496(3) 0.3595(2) 0.33364(5) 0.0216(4) Uani 1 1 d . . . . .
H1 H 0.430(4) 0.448(3) 0.3286(7) 0.032 Uiso 1 1 d . U . . .
N2 N 0.7692(3) 0.3543(2) 0.28848(5) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.1487(4) 0.3852(2) 0.35340(5) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.4272(3) 0.2101(2) 0.31724(5) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.6294(3) 0.2055(2) 0.29556(5) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.7110(4) 0.0564(3) 0.27922(5) 0.0223(4) Uani 1 1 d . . . . .
H4 H 0.848337 0.057155 0.264678 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5924(4) -0.0915(3) 0.28419(5) 0.0243(5) Uani 1 1 d . . . . .
H5 H 0.647216 -0.193151 0.273307 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3906(4) -0.0893(3) 0.30547(6) 0.0251(5) Uani 1 1 d . . . . .
H6 H 0.307335 -0.190572 0.308917 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3093(4) 0.0578(2) 0.32167(6) 0.0238(4) Uani 1 1 d . . . . .
H7 H 0.171295 0.055630 0.336041 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0650(3) 0.6035(3) 0.38372(5) 0.0219(5) Uani 1 1 d . . . . .
H8 H -0.201182 0.534742 0.376415 0.026 Uiso 1 1 calc R U . . .
C9 C -0.0121(3) 0.5775(2) 0.42575(5) 0.0183(4) Uani 1 1 d . . . . .
C10 C -0.1631(3) 0.4956(2) 0.44919(5) 0.0176(4) Uani 1 1 d . . . . .
H10 H -0.301982 0.454251 0.438696 0.021 Uiso 1 1 calc R U . . .
C11 C -0.1169(3) 0.4709(2) 0.48884(5) 0.0171(4) Uani 1 1 d . . . . .
C12 C -0.2715(3) 0.3871(2) 0.51357(6) 0.0201(4) Uani 1 1 d . . . . .
H12 H -0.413862 0.348843 0.503793 0.024 Uiso 1 1 calc R U . . .
C13 C -0.2181(4) 0.3607(3) 0.55143(6) 0.0246(5) Uani 1 1 d . . . . .
H13 H -0.323784 0.304934 0.567769 0.030 Uiso 1 1 calc R U . . .
C14 C -0.0067(4) 0.4159(3) 0.56626(6) 0.0256(5) Uani 1 1 d . . . . .
H14 H 0.030204 0.395808 0.592462 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1454(4) 0.4981(2) 0.54314(5) 0.0223(4) Uani 1 1 d . . . . .
H15 H 0.286822 0.535228 0.553492 0.027 Uiso 1 1 calc R U . . .
C16 C 0.0948(3) 0.5287(2) 0.50400(5) 0.0179(4) Uani 1 1 d . . . . .
C17 C 0.2479(3) 0.6139(2) 0.47922(6) 0.0199(4) Uani 1 1 d . . . . .
H17 H 0.388605 0.654641 0.489132 0.024 Uiso 1 1 calc R U . . .
C18 C 0.1969(3) 0.6384(2) 0.44136(6) 0.0202(4) Uani 1 1 d . . . . .
H18 H 0.301572 0.696641 0.425292 0.024 Uiso 1 1 calc R U . . .
C19 C -0.1064(4) 0.7859(3) 0.37308(6) 0.0289(5) Uani 1 1 d . . . . .
H19A H -0.118494 0.796134 0.345071 0.043 Uiso 1 1 calc R U . . .
H19B H 0.021215 0.854670 0.382281 0.043 Uiso 1 1 calc R U . . .
H19C H -0.248631 0.824620 0.385007 0.043 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Two 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0890
1.00 0.00 -1.00 0.1680
1.00 -1.00 1.00 0.2040
0.00 0.00 -1.00 0.0690
0.00 0.00 1.00 0.1290
0.00 1.00 0.00 0.2130
0.00 -1.00 0.00 0.1930
1.00 1.00 0.00 0.1020
0.00 -1.00 2.00 0.1820

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 C1 1.203(2) . ?
O2 C1 1.352(2) . ?
O2 C8 1.470(2) . ?
O3 N2 1.243(2) . ?
O4 N2 1.227(2) . ?
N1 C1 1.378(3) . ?
N1 C2 1.395(3) . ?
N1 H1 0.86(2) . ?
N2 C3 1.461(3) . ?
C2 C7 1.404(3) . ?
C2 C3 1.404(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.508(3) . ?
C8 C19 1.519(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.368(3) . ?
C9 C18 1.424(3) . ?
C10 C11 1.419(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(3) . ?
C11 C16 1.423(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(3) . ?
C17 C18 1.364(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C1 O2 C8 115.49(15) . . ?
C1 N1 C2 127.49(18) . . ?
C1 N1 H1 116.4(16) . . ?
C2 N1 H1 115.7(16) . . ?
O4 N2 O3 121.45(17) . . ?
O4 N2 C3 118.41(17) . . ?
O3 N2 C3 120.13(16) . . ?
O1 C1 O2 125.49(18) . . ?
O1 C1 N1 127.25(19) . . ?
O2 C1 N1 107.26(17) . . ?
N1 C2 C7 122.15(17) . . ?
N1 C2 C3 121.04(18) . . ?
C7 C2 C3 116.81(18) . . ?
C4 C3 C2 121.80(19) . . ?
C4 C3 N2 115.39(17) . . ?
C2 C3 N2 122.81(17) . . ?
C5 C4 C3 120.15(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 118.88(19) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 121.17(19) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
O2 C8 C9 109.37(16) . . ?
O2 C8 C19 105.09(16) . . ?
C9 C8 C19 113.61(16) . . ?
O2 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C19 C8 H8 109.5 . . ?
C10 C9 C18 119.38(17) . . ?
C10 C9 C8 120.70(18) . . ?
C18 C9 C8 119.92(18) . . ?
C9 C10 C11 121.46(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 122.23(18) . . ?
C12 C11 C16 118.96(17) . . ?
C10 C11 C16 118.78(17) . . ?
C13 C12 C11 120.69(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.24(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.36(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.84(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 122.40(18) . . ?
C15 C16 C11 118.89(17) . . ?
C17 C16 C11 118.71(17) . . ?
C18 C17 C16 121.16(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C9 120.47(18) . . ?
C17 C18 H18 119.8 . . ?
C9 C18 H18 119.8 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C8 O2 C1 O1 4.0(3) . . . . ?
C8 O2 C1 N1 -176.29(14) . . . . ?
C2 N1 C1 O1 6.1(3) . . . . ?
C2 N1 C1 O2 -173.68(17) . . . . ?
C1 N1 C2 C7 -4.8(3) . . . . ?
C1 N1 C2 C3 175.54(18) . . . . ?
N1 C2 C3 C4 179.35(18) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
N1 C2 C3 N2 -0.5(3) . . . . ?
C7 C2 C3 N2 179.81(17) . . . . ?
O4 N2 C3 C4 -3.5(2) . . . . ?
O3 N2 C3 C4 175.90(17) . . . . ?
O4 N2 C3 C2 176.40(17) . . . . ?
O3 N2 C3 C2 -4.2(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N2 C3 C4 C5 179.87(16) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
N1 C2 C7 C6 -179.34(18) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C1 O2 C8 C9 82.3(2) . . . . ?
C1 O2 C8 C19 -155.37(17) . . . . ?
O2 C8 C9 C10 -131.04(18) . . . . ?
C19 C8 C9 C10 111.9(2) . . . . ?
O2 C8 C9 C18 48.9(2) . . . . ?
C19 C8 C9 C18 -68.1(2) . . . . ?
C18 C9 C10 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -179.58(17) . . . . ?
C9 C10 C11 C12 179.72(18) . . . . ?
C9 C10 C11 C16 -1.9(3) . . . . ?
C10 C11 C12 C13 177.84(18) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 179.84(18) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 1.0(3) . . . . ?
C10 C11 C16 C15 -177.39(17) . . . . ?
C12 C11 C16 C17 -179.41(17) . . . . ?
C10 C11 C16 C17 2.2(2) . . . . ?
C15 C16 C17 C18 178.53(18) . . . . ?
C11 C16 C17 C18 -1.0(3) . . . . ?
C16 C17 C18 C9 -0.5(3) . . . . ?
C10 C9 C18 C17 0.8(3) . . . . ?
C8 C9 C18 C17 -179.20(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86(2) 1.93(3) 2.614(2) 136(2) . yes

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_20100_a
_database_code_depnum_ccdc_archive 'CCDC 2077244'
loop_
_audit_author_name
_audit_author_address
'Jeff Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-05-25 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         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.64130(10)
_cell_length_b                   11.0456(3)
_cell_length_c                   13.6158(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.422(2)
_cell_angle_gamma                90
_cell_volume                     693.65(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5088
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      68.12
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    0.804
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73996
_exptl_absorpt_correction_T_max  0.97629
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9430
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         68.334
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2503
_reflns_number_gt                2409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.969
_reflns_Friedel_fraction_full    0.973

_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the unambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1259
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O1 O 0.6858(4) 0.5547(2) 0.39601(16) 0.0221(5) Uani 1 1 d . . . . .
O2 O -0.1242(5) 0.3702(2) 0.20838(17) 0.0236(5) Uani 1 1 d . . . . .
O3 O -0.0027(6) 0.2903(2) 0.0737(2) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.2450(6) 0.5243(2) 0.30486(19) 0.0172(6) Uani 1 1 d . . . . .
H1 H 0.065(10) 0.502(4) 0.314(3) 0.026 Uiso 1 1 d . U . . .
N2 N 0.2733(6) 0.5533(3) 0.47164(19) 0.0191(6) Uani 1 1 d . . . . .
H2 H 0.089(10) 0.551(4) 0.464(3) 0.029 Uiso 1 1 d . U . . .
N3 N 0.0219(6) 0.3703(2) 0.13853(19) 0.0213(6) Uani 1 1 d . . . . .
C1 C 0.4192(6) 0.5457(3) 0.3933(2) 0.0162(6) Uani 1 1 d . . . . .
C2 C 0.3345(6) 0.5390(3) 0.2114(2) 0.0162(6) Uani 1 1 d . . . . .
C3 C 0.2281(6) 0.4677(3) 0.1292(2) 0.0178(6) Uani 1 1 d . . . . .
C4 C 0.3162(7) 0.4854(3) 0.0364(2) 0.0234(7) Uani 1 1 d . . . . .
H4 H 0.242205 0.435037 -0.017094 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5108(7) 0.5759(4) 0.0214(2) 0.0264(7) Uani 1 1 d . . . . .
H5 H 0.568687 0.589318 -0.042507 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6215(7) 0.6473(3) 0.1009(3) 0.0231(7) Uani 1 1 d . . . . .
H6 H 0.758278 0.709045 0.091443 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5343(6) 0.6294(3) 0.1938(2) 0.0193(6) Uani 1 1 d . . . . .
H7 H 0.611918 0.679565 0.246896 0.023 Uiso 1 1 calc R U . . .
C8 C 0.4165(6) 0.5739(3) 0.5719(2) 0.0180(6) Uani 1 1 d . . . . .
H8 H 0.605742 0.529732 0.578072 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2298(6) 0.5176(3) 0.6450(2) 0.0166(6) Uani 1 1 d . . . . .
C10 C 0.1258(7) 0.3996(3) 0.6295(2) 0.0198(7) Uani 1 1 d . . . . .
H10 H 0.174023 0.355154 0.573912 0.024 Uiso 1 1 calc R U . . .
C11 C -0.0469(7) 0.3465(3) 0.6944(2) 0.0228(7) Uani 1 1 d . . . . .
H11 H -0.117837 0.266569 0.682696 0.027 Uiso 1 1 calc R U . . .
C12 C -0.1159(7) 0.4103(3) 0.7764(2) 0.0242(7) Uani 1 1 d . . . . .
H12 H -0.234888 0.374420 0.820811 0.029 Uiso 1 1 calc R U . . .
C13 C -0.0106(7) 0.5261(3) 0.7929(2) 0.0237(7) Uani 1 1 d . . . . .
H13 H -0.056033 0.569724 0.849277 0.028 Uiso 1 1 calc R U . . .
C14 C 0.1609(6) 0.5795(3) 0.7279(2) 0.0197(6) Uani 1 1 d . . . . .
H14 H 0.231998 0.659373 0.740351 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4812(8) 0.7081(3) 0.5884(2) 0.0281(8) Uani 1 1 d . . . . .
H15A H 0.597460 0.737579 0.537546 0.042 Uiso 1 1 calc R U . . .
H15B H 0.589151 0.719711 0.653833 0.042 Uiso 1 1 calc R U . . .
H15C H 0.298723 0.753409 0.584546 0.042 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  nineteen 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 1.00 0.0170
0.00 1.00 0.00 0.0170
0.00 -1.00 0.00 0.0410
1.00 0.00 0.00 0.3220
-1.00 0.00 0.00 0.5100
0.00 0.00 1.00 0.0130
0.00 0.00 -1.00 0.0170

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 C1 1.238(4) . ?
O2 N3 1.228(4) . ?
O3 N3 1.245(4) . ?
N1 C2 1.392(4) . ?
N1 C1 1.394(4) . ?
N1 H1 0.89(5) . ?
N2 C1 1.328(4) . ?
N2 C8 1.467(4) . ?
N2 H2 0.85(5) . ?
N3 C3 1.455(4) . ?
C2 C7 1.401(4) . ?
C2 C3 1.412(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.377(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.523(4) . ?
C8 C15 1.525(5) . ?
C8 H8 1.0000 . ?
C9 C14 1.388(4) . ?
C9 C10 1.398(4) . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.387(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C2 N1 C1 124.5(2) . . ?
C2 N1 H1 123(3) . . ?
C1 N1 H1 113(3) . . ?
C1 N2 C8 122.6(3) . . ?
C1 N2 H2 120(3) . . ?
C8 N2 H2 118(3) . . ?
O2 N3 O3 122.3(3) . . ?
O2 N3 C3 119.6(2) . . ?
O3 N3 C3 118.2(3) . . ?
O1 C1 N2 124.7(3) . . ?
O1 C1 N1 121.4(3) . . ?
N2 C1 N1 114.0(3) . . ?
N1 C2 C7 120.7(3) . . ?
N1 C2 C3 123.1(3) . . ?
C7 C2 C3 116.2(3) . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 N3 116.7(3) . . ?
C2 C3 N3 121.2(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 121.7(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N2 C8 C9 108.2(2) . . ?
N2 C8 C15 110.4(3) . . ?
C9 C8 C15 114.7(3) . . ?
N2 C8 H8 107.7 . . ?
C9 C8 H8 107.7 . . ?
C15 C8 H8 107.7 . . ?
C14 C9 C10 118.3(3) . . ?
C14 C9 C8 122.0(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C8 N2 C1 O1 0.2(5) . . . . ?
C8 N2 C1 N1 179.2(3) . . . . ?
C2 N1 C1 O1 -15.8(5) . . . . ?
C2 N1 C1 N2 165.2(3) . . . . ?
C1 N1 C2 C7 -33.1(4) . . . . ?
C1 N1 C2 C3 148.4(3) . . . . ?
N1 C2 C3 C4 178.8(3) . . . . ?
C7 C2 C3 C4 0.2(4) . . . . ?
N1 C2 C3 N3 -2.0(4) . . . . ?
C7 C2 C3 N3 179.4(3) . . . . ?
O2 N3 C3 C4 -159.9(3) . . . . ?
O3 N3 C3 C4 19.0(4) . . . . ?
O2 N3 C3 C2 20.8(4) . . . . ?
O3 N3 C3 C2 -160.2(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
N3 C3 C4 C5 179.9(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
N1 C2 C7 C6 -178.6(3) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
C1 N2 C8 C9 -152.3(3) . . . . ?
C1 N2 C8 C15 81.4(4) . . . . ?
N2 C8 C9 C14 -132.7(3) . . . . ?
C15 C8 C9 C14 -8.9(4) . . . . ?
N2 C8 C9 C10 48.1(4) . . . . ?
C15 C8 C9 C10 171.8(3) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C8 C9 C10 C11 -179.4(3) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C9 0.1(5) . . . . ?
C10 C9 C14 C13 -1.0(4) . . . . ?
C8 C9 C14 C13 179.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.89(5) 2.26(4) 3.018(3) 143(4) 1_455 yes
N1 H1 O2 0.89(5) 2.17(4) 2.656(4) 114(3) . yes
N2 H2 O1 0.85(5) 1.99(5) 2.805(3) 159(4) 1_455 yes

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053



