# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_221010b_a
_audit_block_doi                 10.5517/ccdc.csd.cc2h7hv3
_database_code_depnum_ccdc_archive 'CCDC 2301125'
loop_
_audit_author_name
_audit_author_address
'Haijie Zhou'
;FDU
China
;
_audit_update_record             
;
2023-10-13 deposited with the CCDC.	2024-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 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           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                   7.7270(4)
_cell_length_b                   11.6009(6)
_cell_length_c                   19.1442(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1716.09(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      4.28
_cell_measurement_theta_max      58.12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.424
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_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            32396
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.876
_diffrn_reflns_theta_max         57.106
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3507
_reflns_number_gt                3423
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.995

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0434P)²+0.2179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0087(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1431 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3507
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0756
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.84775(14) 0.21260(9) 0.83513(6) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.97624(15) 0.35129(11) 0.65234(6) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.55658(16) 0.25256(10) 0.81640(6) 0.0243(3) Uani 1 1 d . . . . .
N2 N 0.45545(16) 0.30252(11) 0.76266(6) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.73015(19) 0.25600(12) 0.80169(8) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.55898(19) 0.33982(12) 0.71534(8) 0.0240(3) Uani 1 1 d . . . . .
C3 C 0.74653(18) 0.32415(12) 0.73396(7) 0.0228(3) Uani 1 1 d . . . . .
C4 C 0.8369(2) 0.44486(13) 0.74508(8) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.7706 0.5040 0.7181 0.032 Uiso 1 1 calc R U . . .
C5 C 1.0118(2) 0.42721(16) 0.70919(9) 0.0355(4) Uani 1 1 d . . . . .
H5A H 1.0586 0.5015 0.6921 0.043 Uiso 1 1 calc R U . . .
H5B H 1.0964 0.3923 0.7418 0.043 Uiso 1 1 calc R U . . .
C6 C 0.87082(19) 0.26251(13) 0.68131(8) 0.0268(3) Uani 1 1 d . . . . .
H6 H 0.9476 0.2098 0.7086 0.032 Uiso 1 1 calc R U . . .
C7 C 0.46895(19) 0.20373(11) 0.87444(7) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.2885(2) 0.19657(13) 0.87295(8) 0.0269(3) Uani 1 1 d . . . . .
H8 H 0.2259 0.2246 0.8338 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2017(2) 0.14824(15) 0.92907(8) 0.0326(4) Uani 1 1 d . . . . .
H9 H 0.0789 0.1436 0.9284 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2922(2) 0.10650(16) 0.98629(9) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.2321 0.0729 1.0245 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4706(2) 0.11420(16) 0.98734(8) 0.0350(4) Uani 1 1 d . . . . .
H11 H 0.5325 0.0857 1.0266 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5610(2) 0.16296(14) 0.93197(8) 0.0289(3) Uani 1 1 d . . . . .
H12 H 0.6836 0.1684 0.9333 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4915(2) 0.39564(15) 0.65100(9) 0.0326(3) Uani 1 1 d . . . . .
H13A H 0.4987 0.3413 0.6119 0.049 Uiso 1 1 calc R U . . .
H13B H 0.5608 0.4642 0.6404 0.049 Uiso 1 1 calc R U . . .
H13C H 0.3706 0.4182 0.6582 0.049 Uiso 1 1 calc R U . . .
C14 C 0.8502(2) 0.48519(13) 0.81935(8) 0.0304(3) Uani 1 1 d . . . . .
H14 H 0.9161 0.4401 0.8511 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7757(3) 0.57965(15) 0.84299(11) 0.0442(4) Uani 1 1 d . . . . .
H15A H 0.7091 0.6264 0.8124 0.053 Uiso 1 1 calc R U . . .
H15B H 0.7886 0.6010 0.8906 0.053 Uiso 1 1 calc R U . . .
C16 C 0.78676(19) 0.19283(13) 0.62444(8) 0.0265(3) Uani 1 1 d . . . . .
C17 C 0.7129(2) 0.08726(14) 0.64072(10) 0.0349(4) Uani 1 1 d . . . . .
H17 H 0.7168 0.0596 0.6874 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6331(3) 0.02159(15) 0.58914(12) 0.0437(4) Uani 1 1 d . . . . .
H18 H 0.5820 -0.0504 0.6007 0.052 Uiso 1 1 calc R U . . .
C19 C 0.6281(2) 0.06108(17) 0.52108(11) 0.0435(4) Uani 1 1 d . . . . .
H19 H 0.5739 0.0162 0.4858 0.052 Uiso 1 1 calc R U . . .
C20 C 0.7020(2) 0.16595(18) 0.50442(9) 0.0406(4) Uani 1 1 d . . . . .
H20 H 0.6987 0.1931 0.4576 0.049 Uiso 1 1 calc R U . . .
C21 C 0.7808(2) 0.23173(15) 0.55588(8) 0.0339(4) Uani 1 1 d . . . . .
H21 H 0.8312 0.3039 0.5441 0.041 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
O1 C1 1.2202(18) . ?
O2 C6 1.4255(19) . ?
O2 C5 1.427(2) . ?
N1 C1 1.3710(19) . ?
N1 N2 1.4161(17) . ?
N1 C7 1.4191(18) . ?
N2 C2 1.2836(19) . ?
C1 C3 1.5239(19) . ?
C2 C13 1.486(2) . ?
C2 C3 1.503(2) . ?
C3 C6 1.565(2) . ?
C3 C4 1.579(2) . ?
C4 C14 1.500(2) . ?
C4 C5 1.530(2) . ?
C6 C16 1.504(2) . ?
C7 C12 1.394(2) . ?
C7 C8 1.397(2) . ?
C8 C9 1.385(2) . ?
C9 C10 1.387(2) . ?
C10 C11 1.381(3) . ?
C11 C12 1.390(2) . ?
C14 C15 1.318(3) . ?
C16 C17 1.387(2) . ?
C16 C21 1.389(2) . ?
C17 C18 1.391(3) . ?
C18 C19 1.382(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.387(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
C6 O2 C5 105.03(12) . . ?
C1 N1 N2 112.25(11) . . ?
C1 N1 C7 129.73(12) . . ?
N2 N1 C7 117.97(12) . . ?
C2 N2 N1 107.86(11) . . ?
O1 C1 N1 127.50(14) . . ?
O1 C1 C3 126.76(14) . . ?
N1 C1 C3 105.73(12) . . ?
N2 C2 C13 120.88(13) . . ?
N2 C2 C3 113.12(12) . . ?
C13 C2 C3 125.97(13) . . ?
C2 C3 C1 100.63(11) . . ?
C2 C3 C6 119.60(12) . . ?
C1 C3 C6 111.22(12) . . ?
C2 C3 C4 110.54(12) . . ?
C1 C3 C4 112.46(11) . . ?
C6 C3 C4 102.75(11) . . ?
C14 C4 C5 114.00(13) . . ?
C14 C4 C3 115.76(12) . . ?
C5 C4 C3 102.20(12) . . ?
O2 C5 C4 104.78(12) . . ?
O2 C6 C16 110.71(12) . . ?
O2 C6 C3 105.73(12) . . ?
C16 C6 C3 116.55(12) . . ?
C12 C7 C8 120.34(14) . . ?
C12 C7 N1 120.72(13) . . ?
C8 C7 N1 118.94(13) . . ?
C9 C8 C7 119.46(14) . . ?
C8 C9 C10 120.62(16) . . ?
C11 C10 C9 119.49(16) . . ?
C10 C11 C12 121.11(16) . . ?
C11 C12 C7 118.98(15) . . ?
C15 C14 C4 123.69(17) . . ?
C17 C16 C21 119.07(15) . . ?
C17 C16 C6 119.33(14) . . ?
C21 C16 C6 121.59(14) . . ?
C16 C17 C18 120.44(17) . . ?
C19 C18 C17 120.00(17) . . ?
C20 C19 C18 119.89(17) . . ?
C19 C20 C21 120.14(17) . . ?
C20 C21 C16 120.46(16) . . ?

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
C1 N1 N2 C2 -1.51(17) . . . . ?
C7 N1 N2 C2 -179.20(12) . . . . ?
N2 N1 C1 O1 -174.16(14) . . . . ?
C7 N1 C1 O1 3.2(3) . . . . ?
N2 N1 C1 C3 5.05(15) . . . . ?
C7 N1 C1 C3 -177.60(13) . . . . ?
N1 N2 C2 C13 179.02(13) . . . . ?
N1 N2 C2 C3 -2.95(17) . . . . ?
N2 C2 C3 C1 5.68(16) . . . . ?
C13 C2 C3 C1 -176.41(14) . . . . ?
N2 C2 C3 C6 127.69(14) . . . . ?
C13 C2 C3 C6 -54.4(2) . . . . ?
N2 C2 C3 C4 -113.36(14) . . . . ?
C13 C2 C3 C4 64.55(19) . . . . ?
O1 C1 C3 C2 173.15(14) . . . . ?
N1 C1 C3 C2 -6.07(14) . . . . ?
O1 C1 C3 C6 45.4(2) . . . . ?
N1 C1 C3 C6 -133.80(12) . . . . ?
O1 C1 C3 C4 -69.22(19) . . . . ?
N1 C1 C3 C4 111.57(13) . . . . ?
C2 C3 C4 C14 96.85(15) . . . . ?
C1 C3 C4 C14 -14.74(19) . . . . ?
C6 C3 C4 C14 -134.42(14) . . . . ?
C2 C3 C4 C5 -138.65(13) . . . . ?
C1 C3 C4 C5 109.76(14) . . . . ?
C6 C3 C4 C5 -9.92(14) . . . . ?
C6 O2 C5 C4 -45.97(16) . . . . ?
C14 C4 C5 O2 159.03(13) . . . . ?
C3 C4 C5 O2 33.37(16) . . . . ?
C5 O2 C6 C16 165.78(13) . . . . ?
C5 O2 C6 C3 38.71(15) . . . . ?
C2 C3 C6 O2 106.47(14) . . . . ?
C1 C3 C6 O2 -136.90(12) . . . . ?
C4 C3 C6 O2 -16.37(14) . . . . ?
C2 C3 C6 C16 -16.99(19) . . . . ?
C1 C3 C6 C16 99.63(15) . . . . ?
C4 C3 C6 C16 -139.83(13) . . . . ?
C1 N1 C7 C12 8.8(2) . . . . ?
N2 N1 C7 C12 -173.98(13) . . . . ?
C1 N1 C7 C8 -170.90(14) . . . . ?
N2 N1 C7 C8 6.33(19) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
N1 C7 C8 C9 179.49(13) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C8 C7 C12 C11 0.6(2) . . . . ?
N1 C7 C12 C11 -179.07(14) . . . . ?
C5 C4 C14 C15 124.07(19) . . . . ?
C3 C4 C14 C15 -117.79(17) . . . . ?
O2 C6 C16 C17 164.97(14) . . . . ?
C3 C6 C16 C17 -74.17(18) . . . . ?
O2 C6 C16 C21 -15.2(2) . . . . ?
C3 C6 C16 C21 105.68(17) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
C6 C16 C17 C18 179.46(15) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C17 C16 C21 C20 0.1(2) . . . . ?
C6 C16 C21 C20 -179.77(16) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035



