# 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_AX2094
_database_code_depnum_ccdc_archive 'CCDC 2079475'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT
Germany
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-06-29 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            'C21 H20 N2 O3'
_chemical_formula_weight         348.39

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                   14.1183(11)
_cell_length_b                   5.6152(4)
_cell_length_c                   21.6543(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.796(2)
_cell_angle_gamma                90
_cell_volume                     1700.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            36217
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         28.812
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4443
_reflns_number_gt                4033
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0557P)²+0.5827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_number_reflns         4443
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.39684(7) 1.31663(18) 0.85905(5) 0.0206(2) Uani 1 1 d . . . . .
C2 C 0.34857(7) 1.34566(18) 0.79708(5) 0.0195(2) Uani 1 1 d . . . . .
C3 C 0.23875(8) 1.2055(2) 0.71782(5) 0.0266(2) Uani 1 1 d . . . . .
H3 H 0.193352 1.088422 0.701859 0.032 Uiso 1 1 calc R U . . .
C4 C 0.25469(8) 1.3983(2) 0.67878(5) 0.0275(2) Uani 1 1 d . . . . .
H4 H 0.220220 1.410284 0.638057 0.033 Uiso 1 1 calc R U . . .
C5 C 0.32033(8) 1.5675(2) 0.70036(5) 0.0251(2) Uani 1 1 d . . . . .
H5 H 0.332126 1.698858 0.674829 0.030 Uiso 1 1 calc R U . . .
C6 C 0.37072(7) 1.54490(18) 0.76129(5) 0.0211(2) Uani 1 1 d . . . . .
C7 C 0.44221(8) 1.70682(19) 0.78703(5) 0.0244(2) Uani 1 1 d . . . . .
H7 H 0.457534 1.841058 0.763590 0.029 Uiso 1 1 calc R U . . .
C8 C 0.48923(8) 1.6695(2) 0.84581(5) 0.0262(2) Uani 1 1 d . . . . .
H8 H 0.538220 1.776941 0.862293 0.031 Uiso 1 1 calc R U . . .
C9 C 0.46652(7) 1.4748(2) 0.88252(5) 0.0244(2) Uani 1 1 d . . . . .
H9 H 0.499509 1.453585 0.923388 0.029 Uiso 1 1 calc R U . . .
C10 C 0.37636(7) 1.07799(19) 0.95340(5) 0.0208(2) Uani 1 1 d . . . . .
C11 C 0.34054(8) 0.83731(19) 0.97111(5) 0.0226(2) Uani 1 1 d . . . . .
H11A H 0.394756 0.743769 0.992496 0.027 Uiso 1 1 calc R U . . .
H11B H 0.314308 0.750273 0.932820 0.027 Uiso 1 1 calc R U . . .
C12 C 0.26331(8) 0.85881(19) 1.01378(5) 0.0228(2) Uani 1 1 d . . . . .
H12A H 0.290845 0.934431 1.053490 0.027 Uiso 1 1 calc R U . . .
H12B H 0.211221 0.962414 0.993796 0.027 Uiso 1 1 calc R U . . .
C13 C 0.22233(7) 0.61580(18) 1.02733(5) 0.0210(2) Uani 1 1 d . . . . .
H13 H 0.203273 0.529197 0.987215 0.025 Uiso 1 1 calc R U . . .
C14 C 0.13614(7) 0.63867(19) 1.06212(5) 0.0226(2) Uani 1 1 d . . . . .
H14A H 0.158382 0.682291 1.105986 0.027 Uiso 1 1 calc R U . . .
H14B H 0.094764 0.769155 1.043262 0.027 Uiso 1 1 calc R U . . .
C15 C 0.07763(7) 0.41180(19) 1.06094(5) 0.0214(2) Uani 1 1 d . . . . .
C16 C 0.00915(7) 0.38019(19) 1.10760(5) 0.0225(2) Uani 1 1 d . . . . .
C17 C -0.04598(8) 0.1723(2) 1.10430(6) 0.0269(2) Uani 1 1 d . . . . .
H17 H -0.038656 0.055457 1.073573 0.032 Uiso 1 1 calc R U . . .
C18 C -0.11152(8) 0.1364(2) 1.14595(6) 0.0323(3) Uani 1 1 d . . . . .
H18 H -0.148934 -0.004762 1.143545 0.039 Uiso 1 1 calc R U . . .
C19 C -0.12232(9) 0.3062(2) 1.19097(6) 0.0347(3) Uani 1 1 d . . . . .
H19 H -0.167352 0.281513 1.219199 0.042 Uiso 1 1 calc R U . . .
C20 C -0.06757(9) 0.5119(2) 1.19487(6) 0.0349(3) Uani 1 1 d . . . . .
H20 H -0.074746 0.627330 1.225965 0.042 Uiso 1 1 calc R U . . .
C21 C -0.00203(8) 0.5495(2) 1.15323(5) 0.0283(2) Uani 1 1 d . . . . .
H21 H 0.035213 0.690930 1.155904 0.034 Uiso 1 1 calc R U . . .
N1 N 0.36920(7) 1.11561(16) 0.89100(4) 0.02297(19) Uani 1 1 d . . . . .
N2 N 0.28279(6) 1.17739(16) 0.77500(4) 0.02307(19) Uani 1 1 d . . . . .
O1 O 0.40899(6) 1.22636(15) 0.99226(4) 0.02771(18) Uani 1 1 d . . . . .
O2 O 0.29093(6) 0.47694(16) 1.06661(4) 0.02904(19) Uani 1 1 d . . . . .
O3 O 0.08311(6) 0.25957(15) 1.02145(4) 0.02961(19) Uani 1 1 d . . . . .
H1 H 0.3392(11) 1.009(3) 0.8671(7) 0.034(4) Uiso 1 1 d . . . . .
H2 H 0.3305(14) 0.398(4) 1.0414(9) 0.063(6) 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
C1 C9 1.3709(15) . ?
C1 N1 1.4065(13) . ?
C1 C2 1.4294(14) . ?
C2 N2 1.3650(13) . ?
C2 C6 1.4199(14) . ?
C3 N2 1.3176(14) . ?
C3 C4 1.4103(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3645(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4171(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4155(15) . ?
C7 C8 1.3693(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4142(15) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.2285(13) . ?
C10 N1 1.3579(13) . ?
C10 C11 1.5106(14) . ?
C11 C12 1.5267(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5260(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O2 1.4304(13) . ?
C13 C14 1.5210(14) . ?
C13 H13 1.0000 . ?
C14 C15 1.5166(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.2188(13) . ?
C15 C16 1.5009(14) . ?
C16 C21 1.3953(16) . ?
C16 C17 1.3995(15) . ?
C17 C18 1.3916(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3868(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3859(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3929(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
N1 H1 0.863(17) . ?
O2 H2 0.94(2) . ?

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
C9 C1 N1 124.79(10) . . ?
C9 C1 C2 120.06(9) . . ?
N1 C1 C2 115.12(9) . . ?
N2 C2 C6 122.95(9) . . ?
N2 C2 C1 117.71(9) . . ?
C6 C2 C1 119.34(9) . . ?
N2 C3 C4 124.20(11) . . ?
N2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C5 C4 C3 119.03(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 119.23(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 123.39(10) . . ?
C7 C6 C2 119.29(10) . . ?
C5 C6 C2 117.31(10) . . ?
C8 C7 C6 119.85(10) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 121.49(10) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C1 C9 C8 119.91(10) . . ?
C1 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O1 C10 N1 123.12(10) . . ?
O1 C10 C11 122.70(9) . . ?
N1 C10 C11 114.17(9) . . ?
C10 C11 C12 111.97(9) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.48(9) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O2 C13 C14 105.91(8) . . ?
O2 C13 C12 110.98(8) . . ?
C14 C13 C12 111.67(9) . . ?
O2 C13 H13 109.4 . . ?
C14 C13 H13 109.4 . . ?
C12 C13 H13 109.4 . . ?
C15 C14 C13 113.03(9) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
O3 C15 C16 119.82(9) . . ?
O3 C15 C14 120.98(9) . . ?
C16 C15 C14 119.15(9) . . ?
C21 C16 C17 119.27(10) . . ?
C21 C16 C15 122.77(10) . . ?
C17 C16 C15 117.96(10) . . ?
C18 C17 C16 120.12(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.14(11) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.14(11) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.06(12) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.26(11) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C10 N1 C1 128.77(9) . . ?
C10 N1 H1 116.9(10) . . ?
C1 N1 H1 114.0(10) . . ?
C3 N2 C2 117.27(9) . . ?
C13 O2 H2 108.6(12) . . ?

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
C9 C1 C2 N2 177.16(10) . . . . ?
N1 C1 C2 N2 -0.94(13) . . . . ?
C9 C1 C2 C6 -2.63(15) . . . . ?
N1 C1 C2 C6 179.26(9) . . . . ?
N2 C3 C4 C5 0.74(18) . . . . ?
C3 C4 C5 C6 0.04(16) . . . . ?
C4 C5 C6 C7 177.93(10) . . . . ?
C4 C5 C6 C2 -0.77(15) . . . . ?
N2 C2 C6 C7 -177.90(9) . . . . ?
C1 C2 C6 C7 1.88(14) . . . . ?
N2 C2 C6 C5 0.85(15) . . . . ?
C1 C2 C6 C5 -179.36(9) . . . . ?
C5 C6 C7 C8 -178.49(10) . . . . ?
C2 C6 C7 C8 0.19(15) . . . . ?
C6 C7 C8 C9 -1.57(16) . . . . ?
N1 C1 C9 C8 179.21(10) . . . . ?
C2 C1 C9 C8 1.30(16) . . . . ?
C7 C8 C9 C1 0.83(17) . . . . ?
O1 C10 C11 C12 55.86(13) . . . . ?
N1 C10 C11 C12 -124.07(10) . . . . ?
C10 C11 C12 C13 175.66(9) . . . . ?
C11 C12 C13 O2 70.10(11) . . . . ?
C11 C12 C13 C14 -171.98(9) . . . . ?
O2 C13 C14 C15 -74.82(11) . . . . ?
C12 C13 C14 C15 164.26(9) . . . . ?
C13 C14 C15 O3 -20.49(14) . . . . ?
C13 C14 C15 C16 162.06(9) . . . . ?
O3 C15 C16 C21 -178.73(11) . . . . ?
C14 C15 C16 C21 -1.25(15) . . . . ?
O3 C15 C16 C17 0.68(15) . . . . ?
C14 C15 C16 C17 178.16(10) . . . . ?
C21 C16 C17 C18 0.37(17) . . . . ?
C15 C16 C17 C18 -179.05(10) . . . . ?
C16 C17 C18 C19 -0.13(18) . . . . ?
C17 C18 C19 C20 -0.31(19) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C16 -0.26(19) . . . . ?
C17 C16 C21 C20 -0.18(17) . . . . ?
C15 C16 C21 C20 179.22(11) . . . . ?
O1 C10 N1 C1 1.01(17) . . . . ?
C11 C10 N1 C1 -179.05(10) . . . . ?
C9 C1 N1 C10 25.43(17) . . . . ?
C2 C1 N1 C10 -156.57(10) . . . . ?
C4 C3 N2 C2 -0.68(16) . . . . ?
C6 C2 N2 C3 -0.14(15) . . . . ?
C1 C2 N2 C3 -179.92(9) . . . . ?

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
O2 H2 O1 0.94(2) 1.90(2) 2.8423(12) 178(2) 1_545 yes

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043



