# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_9279
_database_code_depnum_ccdc_archive 'CCDC 2090953'
loop_
_audit_author_name
_audit_author_address
'Li Xue'
;HuaQiao university
China
;
_audit_update_record             
;
2021-06-19 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2021-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_formula_moiety         'C11 H11 N O3'
_chemical_formula_sum            'C11 H11 N O3'
_chemical_formula_weight         205.21
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.3443(15)
_cell_length_b                   5.3107(6)
_cell_length_c                   15.7486(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.862(12)
_cell_angle_gamma                90
_cell_volume                     1073.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2682
_cell_measurement_theta_max      26.2050
_cell_measurement_theta_min      4.1480
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_crystal_description       block
_exptl_absorpt_correction_T_min  0.50254
_diffrn_ambient_temperature      298
_exptl_absorpt_correction_type   multi-scan
_cell_measurement_temperature    298
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2696
_exptl_crystal_F_000             432.2516
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8208
_diffrn_reflns_theta_full        24.9940
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.56
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  70.00   1.00    5.00    --   15.65  57.00 -30.00   48
  2  ω     50.00  83.00   1.00    5.00    --   15.65  77.00 -30.00   33
  3  ω      1.00  41.00   1.00    5.00    --   15.65  57.00-180.00   40
  4  ω     -9.00  17.00   1.00    5.00    --   15.65  77.00 -30.00   26
  5  ω    -51.00  32.00   1.00    5.00    --   15.65 -57.00-180.00   83
  6  ω    -17.00  17.00   1.00    5.00    --  -16.59 -99.00-150.00   34
  7  ω    -16.00  15.00   1.00    5.00    --  -16.59 -99.00   0.00   31
  8  ω    -50.00  31.00   1.00    5.00    --   15.65 -57.00  60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0134386000
_diffrn_orient_matrix_UB_12      0.1281417000
_diffrn_orient_matrix_UB_13      -0.0093164000
_diffrn_orient_matrix_UB_21      0.0321108000
_diffrn_orient_matrix_UB_22      0.0346020000
_diffrn_orient_matrix_UB_23      0.0421893000
_diffrn_orient_matrix_UB_31      0.0429590000
_diffrn_orient_matrix_UB_32      0.0144737000
_diffrn_orient_matrix_UB_33      -0.0179995000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -15
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                1542
_reflns_number_total             1886
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2556
_refine_diff_density_min         -0.1691
_refine_diff_density_rms         0.0416
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             5.7296
_refine_ls_goodness_of_fit_ref   1.1032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.1032
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1587
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00C(H00C), C009(H009), N004(H004),
 C008(H008)
2.b Idealised Me refined as rotating group:
 C00F(H00a,H00f,H00g)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O001 O 0.40164(9) 0.1886(3) 0.46178(8) 0.0596(4) Uani 1.000000 .
O002 O 0.51681(10) 0.2124(3) 0.59431(8) 0.0653(5) Uani 1.000000 .
O003 O 0.17415(12) 0.8870(3) 0.38117(9) 0.0765(5) Uani 1.000000 .
N004 N 0.23335(11) 0.5038(3) 0.43714(9) 0.0564(5) Uani 1.000000 .
C005 C 0.43066(12) 0.2832(3) 0.53574(12) 0.0483(5) Uani 1.000000 .
C006 C 0.22399(12) 0.7508(3) 0.56710(11) 0.0458(5) Uani 1.000000 .
C007 C 0.28182(12) 0.5768(3) 0.52331(11) 0.0442(5) Uani 1.000000 .
C008 C 0.37255(12) 0.4741(3) 0.56905(12) 0.0480(5) Uani 1.000000 .
C009 C 0.27573(15) 0.9317(3) 0.62599(12) 0.0542(5) Uani 1.000000 .
C00A C 0.18343(14) 0.6629(4) 0.37019(12) 0.0610(6) Uani 1.000000 .
C00B C 0.11771(14) 0.7218(4) 0.55362(14) 0.0628(6) Uani 1.000000 .
C00C C 0.2213(2) 1.0838(4) 0.66939(13) 0.0713(6) Uani 1.000000 .
C00D C 0.06434(17) 0.8729(5) 0.59834(16) 0.0755(7) Uani 1.000000 .
C00E C 0.1154(2) 1.0531(5) 0.65514(14) 0.0775(7) Uani 1.000000 .
C00F C 0.1413(2) 0.5377(6) 0.28257(14) 0.0958(9) Uani 1.000000 .
H00B H 0.08193(14) 0.6004(4) 0.51436(14) 0.0754(7) Uiso 1.000000 R
H00D H -0.00693(17) 0.8508(5) 0.58940(16) 0.0906(8) Uiso 1.000000 R
H00E H 0.0789(2) 1.1554(5) 0.68433(14) 0.0930(9) Uiso 1.000000 R
H00C H 0.2564(2) 1.2069(4) 0.70827(13) 0.0856(8) Uiso 1.000000 R
H009 H 0.34733(15) 0.9514(3) 0.63649(12) 0.0651(6) Uiso 1.000000 R
H002 H 0.5416(11) 0.090(3) 0.5755(7) 0.0980(7) Uiso 1.000000 GR
H004 H 0.23473(11) 0.3464(3) 0.42473(9) 0.0677(6) Uiso 1.000000 R
H008 H 0.40062(12) 0.5293(3) 0.62671(12) 0.0576(6) Uiso 1.000000 R
H00a H 0.0975(13) 0.6535(13) 0.2422(4) 0.1436(13) Uiso 1.000000 GR
H00f H 0.1979(2) 0.487(3) 0.2599(6) 0.1436(13) Uiso 1.000000 GR
H00g H 0.1013(13) 0.393(2) 0.2894(3) 0.1436(13) Uiso 1.000000 GR


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
O001 C005 1.230(2) . ?
O002 C005 1.317(2) . ?
O002 H002 0.8200 . ?
O003 C00A 1.214(2) . ?
N004 C007 1.389(2) . ?
N004 C00A 1.373(2) . ?
N004 H004 0.8600 . ?
C005 C008 1.458(2) . ?
C006 C007 1.489(2) . ?
C006 C009 1.382(2) . ?
C006 C00B 1.384(2) . ?
C007 C008 1.344(2) . ?
C008 H008 0.9300 . ?
C009 C00C 1.385(3) . ?
C009 H009 0.9300 . ?
C00A C00F 1.496(3) . ?
C00B C00D 1.386(3) . ?
C00B H00B 0.9300 . ?
C00C C00E 1.380(3) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.359(3) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00F H00a 0.9600 . ?
C00F H00f 0.9600 . ?
C00F H00g 0.9600 . ?

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
H002 O002 C005 109.5 . . ?
C00A N004 C007 125.24(17) . . ?
H004 N004 C007 117.38(10) . . ?
H004 N004 C00A 117.38(11) . . ?
O002 C005 O001 122.38(16) . . ?
C008 C005 O001 124.33(15) . . ?
C008 C005 O002 113.24(16) . . ?
C009 C006 C007 121.02(15) . . ?
C00B C006 C007 119.94(16) . . ?
C00B C006 C009 118.90(17) . . ?
C006 C007 N004 117.63(14) . . ?
C008 C007 N004 121.41(15) . . ?
C008 C007 C006 120.59(15) . . ?
C007 C008 C005 125.39(16) . . ?
H008 C008 C005 117.31(10) . . ?
H008 C008 C007 117.31(10) . . ?
C00C C009 C006 120.24(19) . . ?
H009 C009 C006 119.88(10) . . ?
H009 C009 C00C 119.88(13) . . ?
N004 C00A O003 122.75(18) . . ?
C00F C00A O003 122.7(2) . . ?
C00F C00A N004 114.6(2) . . ?
C00D C00B C006 120.3(2) . . ?
H00B C00B C006 119.83(11) . . ?
H00B C00B C00D 119.83(14) . . ?
C00E C00C C009 120.2(2) . . ?
H00C C00C C009 119.90(13) . . ?
H00C C00C C00E 119.90(13) . . ?
C00E C00D C00B 120.5(2) . . ?
H00D C00D C00B 119.75(14) . . ?
H00D C00D C00E 119.75(13) . . ?
C00D C00E C00C 119.81(19) . . ?
H00E C00E C00C 120.09(13) . . ?
H00E C00E C00D 120.09(13) . . ?
H00a C00F C00A 109.5 . . ?
H00f C00F C00A 109.5 . . ?
H00f C00F H00a 109.5 . . ?
H00g C00F C00A 109.5 . . ?
H00g C00F H00a 109.5 . . ?
H00g C00F H00f 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.620
