# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_sf-2
_database_code_depnum_ccdc_archive 'CCDC 2117224'
loop_
_audit_author_name
_audit_author_address
'Changsheng Yao'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2021-11-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N O'
_chemical_formula_weight         160.19

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.400(2)
_cell_length_b                   10.406(3)
_cell_length_c                   17.607(5)
_cell_angle_alpha                76.185(4)
_cell_angle_beta                 87.097(4)
_cell_angle_gamma                74.538(4)
_cell_volume                     1097.4(6)
_cell_formula_units_Z            5
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             425
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5844
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.191
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4077
_reflns_number_gt                2815
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1004P)²+0.0850P]
 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4077
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1762
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
O2 O 0.9849(2) 0.73176(15) 0.32677(9) 0.0677(4) Uani 1 1 d . . . . .
C13 C 1.1061(3) 0.79811(19) 0.13809(11) 0.0491(5) Uani 1 1 d . . . . .
C11 C 0.8074(3) 0.90835(19) 0.22311(11) 0.0490(5) Uani 1 1 d . . . . .
C22 C 0.6301(3) 0.9458(2) 0.16591(12) 0.0529(5) Uani 1 1 d . . . . .
C16 C 1.3563(3) 0.5667(2) 0.13478(11) 0.0513(5) Uani 1 1 d . . . . .
C24 C 0.8308(3) 0.7631(2) 0.27336(12) 0.0532(5) Uani 1 1 d . . . . .
O1 O 0.7297(3) 0.68702(16) 0.26380(10) 0.0800(5) Uani 1 1 d . . . . .
C15 C 1.2702(3) 0.6891(2) 0.16567(11) 0.0519(5) Uani 1 1 d . . . . .
H15 H 1.3391 0.6909 0.2105 0.062 Uiso 1 1 calc R U . . .
C12 C 1.0245(3) 0.91218(19) 0.17949(12) 0.0521(5) Uani 1 1 d . . . . .
H12A H 1.0040 0.9992 0.1415 0.063 Uiso 1 1 calc R U . . .
H12B H 1.1339 0.9072 0.2170 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7670(3) 1.0164(2) 0.27354(13) 0.0604(5) Uani 1 1 d . . . . .
H10A H 0.8850 0.9898 0.3113 0.073 Uiso 1 1 calc R U . . .
H10B H 0.7719 1.1039 0.2396 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5563(4) 1.0359(2) 0.31701(12) 0.0610(5) Uani 1 1 d . . . . .
C14 C 1.0059(3) 0.8133(2) 0.06351(13) 0.0575(5) Uani 1 1 d . . . . .
C21 C 1.2252(4) 0.5051(2) 0.10405(13) 0.0620(5) Uani 1 1 d . . . . .
H21 H 1.0757 0.5417 0.1024 0.074 Uiso 1 1 calc R U . . .
C23 C 0.4934(4) 0.9860(2) 0.11782(14) 0.0673(6) Uani 1 1 d . . . . .
H23 H 0.3846 1.0180 0.0796 0.081 Uiso 1 1 calc R U . . .
N2 N 0.9332(3) 0.8309(2) 0.00295(12) 0.0791(6) Uani 1 1 d . . . . .
C17 C 1.5787(3) 0.5075(2) 0.13747(13) 0.0651(6) Uani 1 1 d . . . . .
H17 H 1.6699 0.5454 0.1595 0.078 Uiso 1 1 calc R U . . .
C18 C 1.6658(4) 0.3940(2) 0.10812(15) 0.0744(7) Uani 1 1 d . . . . .
H18 H 1.8151 0.3570 0.1093 0.089 Uiso 1 1 calc R U . . .
C5 C -0.1800(4) 1.3204(3) 0.33060(16) 0.0789(7) Uani 1 1 d . . . . .
H5 H -0.2956 1.3827 0.3008 0.095 Uiso 1 1 calc R U . . .
C20 C 1.3139(4) 0.3894(2) 0.07564(14) 0.0742(7) Uani 1 1 d . . . . .
H20 H 1.2239 0.3483 0.0555 0.089 Uiso 1 1 calc R U . . .
C19 C 1.5336(4) 0.3353(2) 0.07713(14) 0.0734(7) Uani 1 1 d . . . . .
H19 H 1.5930 0.2587 0.0571 0.088 Uiso 1 1 calc R U . . .
C1 C 0.1902(4) 1.1886(2) 0.33889(13) 0.0643(6) Uani 1 1 d . . . . .
C7 C 0.3967(4) 1.1508(2) 0.29940(13) 0.0663(6) Uani 1 1 d . . . . .
H7 H 0.4196 1.2163 0.2559 0.080 Uiso 1 1 calc R U . . .
C6 C 0.0164(4) 1.2824(2) 0.29639(14) 0.0703(6) Uani 1 1 d . . . . .
H6 H 0.0332 1.3204 0.2437 0.084 Uiso 1 1 calc R U . . .
C9 C 0.5403(4) 0.9225(3) 0.37984(16) 0.0781(7) Uani 1 1 d . . . . .
C4 C -0.2079(4) 1.2680(3) 0.40758(17) 0.0824(7) Uani 1 1 d . . . . .
H4 H -0.3424 1.2927 0.4304 0.099 Uiso 1 1 calc R U . . .
C26 C 1.2443(6) 0.5503(4) 0.4052(3) 0.1444(16) Uani 1 1 d . . . . .
H26A H 1.3366 0.5339 0.3620 0.217 Uiso 1 1 calc R U . . .
H26B H 1.2634 0.4666 0.4448 0.217 Uiso 1 1 calc R U . . .
H26C H 1.2814 0.6182 0.4265 0.217 Uiso 1 1 calc R U . . .
C2 C 0.1579(5) 1.1391(3) 0.41711(15) 0.1051(11) Uani 1 1 d . . . . .
H2 H 0.2720 1.0769 0.4478 0.126 Uiso 1 1 calc R U . . .
N1 N 0.5331(5) 0.8284(3) 0.42788(16) 0.1215(10) Uani 1 1 d . . . . .
C25 C 1.0298(5) 0.5968(3) 0.37984(19) 0.1051(10) Uani 1 1 d . . . . .
H25A H 0.9361 0.6007 0.4247 0.126 Uiso 1 1 calc R U . . .
H25B H 0.9973 0.5324 0.3535 0.126 Uiso 1 1 calc R U . . .
C3 C -0.0380(5) 1.1796(3) 0.45052(17) 0.1166(12) Uani 1 1 d . . . . .
H3 H -0.0547 1.1457 0.5037 0.140 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
O2 C24 1.319(2) . ?
O2 C25 1.454(3) . ?
C13 C15 1.334(3) . ?
C13 C14 1.447(3) . ?
C13 C12 1.502(3) . ?
C11 C22 1.465(3) . ?
C11 C24 1.531(3) . ?
C11 C10 1.555(3) . ?
C11 C12 1.558(3) . ?
C22 C23 1.170(3) . ?
C16 C21 1.381(3) . ?
C16 C17 1.391(3) . ?
C16 C15 1.465(3) . ?
C24 O1 1.192(2) . ?
C10 C8 1.506(3) . ?
C8 C7 1.332(3) . ?
C8 C9 1.434(3) . ?
C14 N2 1.140(3) . ?
C21 C20 1.384(3) . ?
C17 C18 1.372(3) . ?
C18 C19 1.367(4) . ?
C5 C4 1.357(4) . ?
C5 C6 1.368(3) . ?
C20 C19 1.367(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.381(3) . ?
C1 C7 1.465(3) . ?
C9 N1 1.140(3) . ?
C4 C3 1.349(4) . ?
C26 C25 1.387(4) . ?
C2 C3 1.363(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
C24 O2 C25 117.93(19) . . ?
C15 C13 C14 119.94(18) . . ?
C15 C13 C12 122.79(18) . . ?
C14 C13 C12 117.21(17) . . ?
C22 C11 C24 110.63(15) . . ?
C22 C11 C10 109.36(15) . . ?
C24 C11 C10 111.98(16) . . ?
C22 C11 C12 109.53(16) . . ?
C24 C11 C12 108.26(15) . . ?
C10 C11 C12 106.98(15) . . ?
C23 C22 C11 174.3(2) . . ?
C21 C16 C17 117.93(19) . . ?
C21 C16 C15 122.75(18) . . ?
C17 C16 C15 119.31(18) . . ?
O1 C24 O2 124.65(19) . . ?
O1 C24 C11 124.84(18) . . ?
O2 C24 C11 110.45(16) . . ?
C13 C15 C16 128.66(18) . . ?
C13 C12 C11 113.76(15) . . ?
C8 C10 C11 115.71(16) . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 C10 122.7(2) . . ?
C9 C8 C10 115.27(19) . . ?
N2 C14 C13 176.0(2) . . ?
C16 C21 C20 120.7(2) . . ?
C18 C17 C16 121.0(2) . . ?
C19 C18 C17 120.2(2) . . ?
C4 C5 C6 120.7(2) . . ?
C19 C20 C21 120.2(2) . . ?
C18 C19 C20 120.0(2) . . ?
C2 C1 C6 117.0(2) . . ?
C2 C1 C7 124.2(2) . . ?
C6 C1 C7 118.9(2) . . ?
C8 C7 C1 129.1(2) . . ?
C5 C6 C1 121.0(2) . . ?
N1 C9 C8 176.9(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C2 C1 121.3(3) . . ?
C26 C25 O2 112.0(3) . . ?
C4 C3 C2 121.0(3) . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-2

