# 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_hufang-hxp_0302_auto
_database_code_depnum_ccdc_archive 'CCDC 2156144'
loop_
_audit_author_name
_audit_author_address
'Xin-Ping Hui'
;Lanzhou University
China
;
_audit_update_record             
;
2022-03-03 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2864(3)
_cell_length_b                   10.8028(3)
_cell_length_c                   11.5140(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.190(4)
_cell_angle_gamma                90
_cell_volume                     1090.89(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    274.64(16)
_cell_measurement_theta_max      76.4470
_cell_measurement_theta_min      5.7700
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6938
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.638
_diffrn_reflns_theta_min         5.773
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      274.64(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00  97.00   0.50    0.05    --   47.57  48.00 113.00  106
  2  ω     97.00 175.00   0.50    0.05    --  107.75  48.00 113.00  156
  3  ω    143.00 169.00   0.50    0.05    --  107.75  57.00  30.00   52
  4  ω     93.00 120.00   0.50    0.05    --  107.75  57.00  30.00   54
  5  ω    104.00 161.00   0.50    0.05    --  107.75  37.00-150.00  114
  6  ω    -11.00  14.00   0.50    0.05    --   47.57 -48.00 -34.00   50
  7  ω    -24.00  15.00   0.50    0.05    --   47.57 -19.00 -30.00   78
  8  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00  90.00   50
  9  ω     36.00  90.00   0.50    0.05    --  107.75 -77.00 -30.00  108
 10  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00 -90.00   50
 11  ω     59.00  85.00   0.50    0.05    --  107.75 -77.00-180.00   52
 12  ω     36.00  62.00   0.50    0.05    --  107.75 -57.00-150.00   52
 13  ω    -21.00  39.00   0.50    0.05    --   47.57 -37.00-180.00  120
 14  ω    -39.00  13.00   0.50    0.05    --  -47.57  48.00 113.00  104
 15  ω    -69.00 -37.00   0.50    0.05    -- -100.00  57.00 150.00   64
 16  ω    -68.00 -37.00   0.50    0.05    -- -100.00  57.00 -60.00   62
 17  ω    -69.00 -29.00   0.50    0.05    -- -100.00  57.00-120.00   80
 18  ω    -67.00 -41.00   0.50    0.05    -- -100.00  57.00-150.00   52
 19  ω    -69.00 -27.00   0.50    0.05    -- -100.00  57.00-180.00   84
 20  ω    -57.00 -28.00   0.50    0.05    -- -100.00  48.00 113.00   58
 21  ω   -173.00 -88.00   0.50    0.05    -- -100.00 -37.00  30.00  170
 22  ω   -153.00-128.00   0.50    0.05    -- -100.00 -48.00 -34.00   50
 23  ω   -119.00 -35.00   0.50    0.05    --  -47.57 -48.00 -34.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1560265000
_diffrn_orient_matrix_UB_12      0.0653443000
_diffrn_orient_matrix_UB_13      -0.0434909000
_diffrn_orient_matrix_UB_21      0.0370121000
_diffrn_orient_matrix_UB_22      0.0538139000
_diffrn_orient_matrix_UB_23      -0.1108793000
_diffrn_orient_matrix_UB_31      -0.0715724000
_diffrn_orient_matrix_UB_32      -0.1147654000
_diffrn_orient_matrix_UB_33      -0.0767833000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1820
_reflns_number_total             2192
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1184P)²+0.1760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C11-C10
 1.32 with sigma of 0.005
3.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10)
3.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.36764(18) 0.37318(17) -0.01703(13) 0.0831(6) Uani 1 1 d . . . . .
O2 O 0.41739(17) 0.24725(14) 0.14223(13) 0.0713(5) Uani 1 1 d . . . . .
N1 N 0.55331(19) 0.42793(16) 0.15649(13) 0.0609(5) Uani 1 1 d . . . . .
H1 H 0.571201 0.492524 0.119757 0.073 Uiso 1 1 calc R U . . .
C1 C 0.7970(3) 0.5483(2) 0.45699(18) 0.0701(6) Uani 1 1 d . . . . .
H1A H 0.862010 0.481240 0.484997 0.084 Uiso 1 1 calc R U . . .
C2 C 0.8268(3) 0.6585(3) 0.5210(2) 0.0858(7) Uani 1 1 d . . . . .
H2 H 0.911274 0.664859 0.591888 0.103 Uiso 1 1 calc R U . . .
C3 C 0.7340(3) 0.7577(2) 0.4815(2) 0.0839(7) Uani 1 1 d . . . . .
H3 H 0.755429 0.832148 0.524291 0.101 Uiso 1 1 calc R U . . .
C4 C 0.6091(3) 0.7472(2) 0.3786(2) 0.0843(7) Uani 1 1 d . . . . .
H4 H 0.544539 0.814727 0.351844 0.101 Uiso 1 1 calc R U . . .
C5 C 0.5773(3) 0.6366(2) 0.3131(2) 0.0692(6) Uani 1 1 d . . . . .
H5 H 0.491755 0.630495 0.243036 0.083 Uiso 1 1 calc R U . . .
C6 C 0.67202(19) 0.53621(16) 0.35192(15) 0.0520(4) Uani 1 1 d . . . . .
C7 C 0.6455(2) 0.41333(17) 0.28575(16) 0.0545(5) Uani 1 1 d . . . . .
H7 H 0.744923 0.379912 0.289098 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5685(2) 0.31903(18) 0.34377(17) 0.0600(5) Uani 1 1 d . . . . .
H8A H 0.637260 0.294321 0.423792 0.072 Uiso 1 1 calc R U . . .
H8B H 0.477759 0.354548 0.354413 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5268(3) 0.20864(19) 0.25940(18) 0.0650(5) Uani 1 1 d . . . . .
H9 H 0.619045 0.179392 0.244496 0.078 Uiso 1 1 calc R U . . .
C10 C 0.4620(3) 0.1041(2) 0.3100(2) 0.0839(7) Uani 1 1 d D . . . .
H10 H 0.523825 0.071662 0.384550 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3309(4) 0.0533(3) 0.2630(3) 0.1019(9) Uani 1 1 d D . . . .
H11A H 0.264157 0.081805 0.188551 0.122 Uiso 1 1 calc R U . . .
H11B H 0.302522 -0.012119 0.303376 0.122 Uiso 1 1 calc R U . . .
C12 C 0.4450(2) 0.35242(19) 0.08955(17) 0.0624(5) 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
O1 C12 1.222(2) . ?
O2 C9 1.458(2) . ?
O2 C12 1.351(2) . ?
N1 H1 0.8600 . ?
N1 C7 1.461(2) . ?
N1 C12 1.327(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(3) . ?
C6 C7 1.510(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.520(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.506(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.486(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.282(3) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?

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
C12 O2 C9 118.60(15) . . ?
C7 N1 H1 116.4 . . ?
C12 N1 H1 116.4 . . ?
C12 N1 C7 127.13(16) . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 118.42(17) . . ?
C5 C6 C1 118.32(18) . . ?
C5 C6 C7 123.26(16) . . ?
N1 C7 C6 111.27(14) . . ?
N1 C7 H7 108.0 . . ?
N1 C7 C8 108.49(14) . . ?
C6 C7 H7 108.0 . . ?
C6 C7 C8 112.94(15) . . ?
C8 C7 H7 108.0 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C7 107.81(16) . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
O2 C9 C8 108.90(16) . . ?
O2 C9 H9 108.3 . . ?
O2 C9 C10 109.37(18) . . ?
C8 C9 H9 108.3 . . ?
C10 C9 C8 113.62(18) . . ?
C10 C9 H9 108.3 . . ?
C9 C10 H10 116.2 . . ?
C11 C10 C9 127.6(3) . . ?
C11 C10 H10 116.2 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
O1 C12 O2 118.01(17) . . ?
O1 C12 N1 123.61(19) . . ?
N1 C12 O2 118.38(17) . . ?

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 C9 C10 C11 -0.9(4) . . . . ?
N1 C7 C8 C9 47.6(2) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C1 C6 C7 N1 -156.64(17) . . . . ?
C1 C6 C7 C8 81.1(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C5 C6 C7 N1 23.8(3) . . . . ?
C5 C6 C7 C8 -98.5(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C7 C8 C9 171.43(15) . . . . ?
C7 N1 C12 O1 176.7(2) . . . . ?
C7 N1 C12 O2 -2.6(3) . . . . ?
C7 C8 C9 O2 -62.8(2) . . . . ?
C7 C8 C9 C10 175.08(18) . . . . ?
C8 C9 C10 C11 121.0(3) . . . . ?
C9 O2 C12 O1 167.95(19) . . . . ?
C9 O2 C12 N1 -12.6(3) . . . . ?
C12 O2 C9 C8 45.9(2) . . . . ?
C12 O2 C9 C10 170.62(18) . . . . ?
C12 N1 C7 C6 -141.4(2) . . . . ?
C12 N1 C7 C8 -16.6(3) . . . . ?

_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 5.847
_oxdiff_exptl_absorpt_empirical_full_min 0.400
