# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ga_210416ea_a
_database_code_depnum_ccdc_archive 'CCDC 2162446'
loop_
_audit_author_name
_audit_author_address
'Renhua Fan'
;Fudan University
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   17.0936(9)
_cell_length_b                   9.1661(5)
_cell_length_c                   9.2363(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1447.16(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9071
_cell_measurement_theta_min      4.20
_cell_measurement_theta_max      57.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.462
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            24217
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.501
_diffrn_reflns_theta_max         57.983
_diffrn_reflns_theta_full        53.594
_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             3063
_reflns_number_gt                2946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     1.000
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0410P)²+0.2453P] 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_abs_structure_details 
; 
 Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.07(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.43717(10) 0.73563(19) 0.50405(19) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.35662(11) 0.68998(19) 0.5594(2) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.32547(12) 0.7459(2) 0.6810(2) 0.0285(4) Uani 1 1 d . . . . .
H3 H 0.274770 0.715161 0.710022 0.034 Uiso 1 1 calc R U . . .
C4 C 0.36728(12) 0.8529(2) 0.7703(2) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.44329(12) 0.9043(2) 0.7163(2) 0.0321(4) Uani 1 1 d . . . . .
H5 H 0.470062 0.978931 0.767665 0.039 Uiso 1 1 calc R U . . .
C6 C 0.47554(11) 0.8490(2) 0.5975(2) 0.0296(4) Uani 1 1 d . . . . .
H6 H 0.525850 0.883238 0.569983 0.035 Uiso 1 1 calc R U . . .
C7 C 0.37787(12) 0.9048(2) 0.3335(2) 0.0327(4) Uani 1 1 d . . . . .
H7A H 0.326807 0.878936 0.374360 0.049 Uiso 1 1 calc R U . . .
H7B H 0.372551 0.921263 0.229138 0.049 Uiso 1 1 calc R U . . .
H7C H 0.397205 0.993895 0.379948 0.049 Uiso 1 1 calc R U . . .
C8 C 0.50829(11) 0.5190(2) 0.5923(2) 0.0260(4) Uani 1 1 d . . . . .
C9 C 0.55511(14) 0.3870(2) 0.5489(2) 0.0380(5) Uani 1 1 d . . . . .
H9A H 0.562490 0.386880 0.443717 0.057 Uiso 1 1 calc R U . . .
H9B H 0.606229 0.389713 0.596886 0.057 Uiso 1 1 calc R U . . .
H9C H 0.527085 0.298414 0.577956 0.057 Uiso 1 1 calc R U . . .
C10 C 0.31872(11) 0.5822(2) 0.4724(2) 0.0283(4) Uani 1 1 d . . . . .
C11 C 0.29360(12) 0.4908(2) 0.3946(2) 0.0299(4) Uani 1 1 d . . . . .
C12 C 0.26470(12) 0.3788(2) 0.2992(2) 0.0287(4) Uani 1 1 d . . . . .
C13 C 0.18446(13) 0.3543(2) 0.2863(3) 0.0383(5) Uani 1 1 d . . . . .
H13 H 0.148531 0.411264 0.340735 0.046 Uiso 1 1 calc R U . . .
C14 C 0.15752(15) 0.2470(3) 0.1944(3) 0.0480(6) Uani 1 1 d . . . . .
H14 H 0.102887 0.230513 0.185034 0.058 Uiso 1 1 calc R U . . .
C15 C 0.20954(17) 0.1636(2) 0.1161(3) 0.0465(6) Uani 1 1 d . . . . .
H15 H 0.190496 0.089132 0.053826 0.056 Uiso 1 1 calc R U . . .
C16 C 0.28894(16) 0.1873(2) 0.1272(2) 0.0409(5) Uani 1 1 d . . . . .
H16 H 0.324387 0.130001 0.071976 0.049 Uiso 1 1 calc R U . . .
C17 C 0.31682(13) 0.2943(2) 0.2187(2) 0.0337(4) Uani 1 1 d . . . . .
H17 H 0.371541 0.310440 0.226851 0.040 Uiso 1 1 calc R U . . .
N1 N 0.48768(9) 0.60899(18) 0.48374(17) 0.0247(3) Uani 1 1 d . . . . .
H1 H 0.4912(15) 0.573(3) 0.394(3) 0.040(7) Uiso 1 1 d . . . . .
O1 O 0.34025(11) 0.89597(18) 0.88565(17) 0.0467(4) Uani 1 1 d . . . . .
O2 O 0.43198(8) 0.78831(14) 0.35845(14) 0.0275(3) Uani 1 1 d . . . . .
O3 O 0.49091(9) 0.54466(16) 0.71927(15) 0.0332(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 O2 1.432(2) . ?
C1 N1 1.459(2) . ?
C1 C6 1.502(3) . ?
C1 C2 1.527(3) . ?
C2 C3 1.345(3) . ?
C2 C10 1.429(3) . ?
C3 C4 1.467(3) . ?
C3 H3 0.9500 . ?
C4 O1 1.227(2) . ?
C4 C5 1.469(3) . ?
C5 C6 1.329(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.431(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O3 1.232(2) . ?
C8 N1 1.346(2) . ?
C8 C9 1.505(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.184(3) . ?
C11 C12 1.440(3) . ?
C12 C17 1.395(3) . ?
C12 C13 1.395(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 H1 0.90(3) . ?

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
O2 C1 N1 100.62(14) . . ?
O2 C1 C6 109.47(15) . . ?
N1 C1 C6 111.47(15) . . ?
O2 C1 C2 110.55(14) . . ?
N1 C1 C2 111.01(14) . . ?
C6 C1 C2 113.03(15) . . ?
C3 C2 C10 123.63(18) . . ?
C3 C2 C1 122.14(17) . . ?
C10 C2 C1 114.22(16) . . ?
C2 C3 C4 122.11(18) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
O1 C4 C3 121.3(2) . . ?
O1 C4 C5 121.6(2) . . ?
C3 C4 C5 117.03(17) . . ?
C6 C5 C4 121.66(18) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 123.88(18) . . ?
C5 C6 H6 118.1 . . ?
C1 C6 H6 118.1 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 N1 121.95(18) . . ?
O3 C8 C9 122.34(18) . . ?
N1 C8 C9 115.70(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 174.1(2) . . ?
C10 C11 C12 178.8(2) . . ?
C17 C12 C13 119.53(19) . . ?
C17 C12 C11 120.19(18) . . ?
C13 C12 C11 120.28(19) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C8 N1 C1 123.15(16) . . ?
C8 N1 H1 116.5(17) . . ?
C1 N1 H1 116.9(17) . . ?
C1 O2 C7 116.29(14) . . ?

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
O2 C1 C2 C3 -124.13(18) . . . . ?
N1 C1 C2 C3 125.09(18) . . . . ?
C6 C1 C2 C3 -1.0(2) . . . . ?
O2 C1 C2 C10 56.86(19) . . . . ?
N1 C1 C2 C10 -53.9(2) . . . . ?
C6 C1 C2 C10 179.97(16) . . . . ?
C10 C2 C3 C4 177.88(18) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 O1 -175.3(2) . . . . ?
C2 C3 C4 C5 3.8(3) . . . . ?
O1 C4 C5 C6 174.4(2) . . . . ?
C3 C4 C5 C6 -4.7(3) . . . . ?
C4 C5 C6 C1 2.8(3) . . . . ?
O2 C1 C6 C5 123.8(2) . . . . ?
N1 C1 C6 C5 -125.7(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C14 179.8(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 -179.87(19) . . . . ?
O3 C8 N1 C1 -6.1(3) . . . . ?
C9 C8 N1 C1 175.01(18) . . . . ?
O2 C1 N1 C8 -178.15(17) . . . . ?
C6 C1 N1 C8 65.9(2) . . . . ?
C2 C1 N1 C8 -61.1(2) . . . . ?
N1 C1 O2 C7 172.52(15) . . . . ?
C6 C1 O2 C7 -70.00(19) . . . . ?
C2 C1 O2 C7 55.1(2) . . . . ?

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
N1 H1 O3 0.90(3) 1.96(3) 2.843(2) 167(2) 2_664

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033

