# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_256-2
_database_code_depnum_ccdc_archive 'CCDC 2240182'
loop_
_audit_author_name
_audit_author_address
LFYzznhz
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-02-06 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_audit_creation_date             2021-06-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_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 0.0033 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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9803(9)
_cell_length_b                   10.5194(6)
_cell_length_c                   12.5582(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.748(11)
_cell_angle_gamma                90
_cell_volume                     1337.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2043
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.3370
_cell_measurement_theta_min      2.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6236
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.011
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  59.00   1.00    2.00    --  -11.27  38.00 150.00   93
  2  ω    -73.00  13.00   1.00    2.00    --  -11.27 -38.00 150.00   86
  3  ω     35.00  68.00   1.00    2.00    --   11.90 178.00 120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0136496000
_diffrn_orient_matrix_UB_12      -0.0218477000
_diffrn_orient_matrix_UB_13      -0.0477192000
_diffrn_orient_matrix_UB_21      -0.0682120000
_diffrn_orient_matrix_UB_22      -0.0118560000
_diffrn_orient_matrix_UB_23      -0.0311388000
_diffrn_orient_matrix_UB_31      -0.0081893000
_diffrn_orient_matrix_UB_32      0.0626679000
_diffrn_orient_matrix_UB_33      -0.0224448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1818
_reflns_number_total             2354
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.069
_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)+(0.0363P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.45646(13) 0.99634(11) 0.34911(11) 0.0375(4) Uani 1 1 d . . . . .
O2 O 0.61466(12) 0.89778(11) 0.30717(11) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.47107(14) 0.78759(15) 0.49514(14) 0.0288(4) Uani 1 1 d . . . . .
H1 H 0.4869(18) 0.854(2) 0.5397(18) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.53108(13) 0.79501(13) 0.41621(12) 0.0251(4) Uani 1 1 d . . . . .
C1 C 0.34157(16) 0.73999(15) 0.45477(15) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.28620(16) 0.67177(16) 0.35501(15) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.331881 0.662385 0.306696 0.033 Uiso 1 1 calc R U . . .
C3 C 0.16059(17) 0.61529(16) 0.32423(17) 0.0301(4) Uani 1 1 d . . . . .
C4 C 0.10342(18) 0.53936(18) 0.22450(18) 0.0389(5) Uani 1 1 d . . . . .
H4 H 0.147935 0.528167 0.175455 0.047 Uiso 1 1 calc R U . . .
C5 C -0.0160(2) 0.48213(19) 0.1989(2) 0.0494(6) Uani 1 1 d . . . . .
H5 H -0.051659 0.431732 0.133226 0.059 Uiso 1 1 calc R U . . .
C6 C -0.0855(2) 0.4988(2) 0.2711(2) 0.0522(6) Uani 1 1 d . . . . .
H6 H -0.167124 0.459842 0.253005 0.063 Uiso 1 1 calc R U . . .
C7 C -0.03361(18) 0.57196(19) 0.3672(2) 0.0453(6) Uani 1 1 d . . . . .
H7 H -0.080650 0.583071 0.414260 0.054 Uiso 1 1 calc R U . . .
C8 C 0.09038(17) 0.63142(17) 0.39720(18) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.14936(18) 0.70494(18) 0.49873(18) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.103972 0.717739 0.546870 0.045 Uiso 1 1 calc R U . . .
C10 C 0.27105(18) 0.75711(17) 0.52710(17) 0.0325(5) Uani 1 1 d . . . . .
H10 H 0.308263 0.804428 0.594573 0.039 Uiso 1 1 calc R U . . .
C11 C 0.52670(17) 0.90424(17) 0.35797(16) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.67347(18) 0.77129(17) 0.32874(17) 0.0343(5) Uani 1 1 d . . . . .
H12A H 0.766659 0.775360 0.342717 0.041 Uiso 1 1 calc R U . . .
H12B H 0.629705 0.715729 0.263402 0.041 Uiso 1 1 calc R U . . .
C13 C 0.65378(16) 0.72341(16) 0.43588(16) 0.0264(4) Uani 1 1 d . . . . .
C14 C 0.62909(18) 0.58217(17) 0.43387(18) 0.0350(5) Uani 1 1 d . . . . .
H14A H 0.606463 0.559539 0.498000 0.053 Uiso 1 1 calc R U . . .
H14B H 0.707382 0.537252 0.439315 0.053 Uiso 1 1 calc R U . . .
H14C H 0.557708 0.559851 0.363036 0.053 Uiso 1 1 calc R U . . .
C15 C 0.76256(18) 0.7659(2) 0.54705(18) 0.0448(5) Uani 1 1 d . . . . .
H15A H 0.777457 0.855387 0.543311 0.067 Uiso 1 1 calc R U . . .
H15B H 0.842200 0.720312 0.557733 0.067 Uiso 1 1 calc R U . . .
H15C H 0.737108 0.748873 0.610689 0.067 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 C11 1.216(2) . ?
O2 C11 1.349(2) . ?
O2 C12 1.458(2) . ?
N1 H1 0.87(2) . ?
N1 N2 1.3885(19) . ?
N1 C1 1.404(2) . ?
N2 C11 1.353(2) . ?
N2 C13 1.479(2) . ?
C1 C2 1.366(2) . ?
C1 C10 1.415(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(2) . ?
C3 C4 1.412(3) . ?
C3 C8 1.417(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.358(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.411(3) . ?
C8 C9 1.416(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(3) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.528(3) . ?
C13 C14 1.509(2) . ?
C13 C15 1.512(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C11 O2 C12 107.73(13) . . ?
N2 N1 H1 112.4(13) . . ?
N2 N1 C1 117.13(15) . . ?
C1 N1 H1 116.2(12) . . ?
N1 N2 C13 120.36(14) . . ?
C11 N2 N1 120.41(14) . . ?
C11 N2 C13 111.26(13) . . ?
N1 C1 C10 116.88(16) . . ?
C2 C1 N1 123.23(16) . . ?
C2 C1 C10 119.72(16) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.91(17) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C8 119.39(17) . . ?
C4 C3 C2 122.23(17) . . ?
C4 C3 C8 118.35(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.95(19) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.2(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C3 119.0(2) . . ?
C7 C8 C9 122.72(19) . . ?
C9 C8 C3 118.29(16) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.19(17) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 H10 119.8 . . ?
C9 C10 C1 120.49(18) . . ?
C9 C10 H10 119.8 . . ?
O1 C11 O2 122.77(16) . . ?
O1 C11 N2 127.93(17) . . ?
O2 C11 N2 109.30(15) . . ?
O2 C12 H12A 110.7 . . ?
O2 C12 H12B 110.7 . . ?
O2 C12 C13 105.14(14) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
N2 C13 C12 96.61(13) . . ?
N2 C13 C14 110.65(13) . . ?
N2 C13 C15 110.32(14) . . ?
C14 C13 C12 113.30(16) . . ?
C14 C13 C15 112.27(16) . . ?
C15 C13 C12 112.67(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 C12 C13 N2 29.39(16) . . . . ?
O2 C12 C13 C14 145.26(14) . . . . ?
O2 C12 C13 C15 -85.90(17) . . . . ?
N1 N2 C11 O1 -13.9(3) . . . . ?
N1 N2 C11 O2 166.47(14) . . . . ?
N1 N2 C13 C12 -177.98(14) . . . . ?
N1 N2 C13 C14 64.0(2) . . . . ?
N1 N2 C13 C15 -60.8(2) . . . . ?
N1 C1 C2 C3 173.60(15) . . . . ?
N1 C1 C10 C9 -174.66(16) . . . . ?
N2 N1 C1 C2 17.6(2) . . . . ?
N2 N1 C1 C10 -167.10(14) . . . . ?
C1 N1 N2 C11 94.29(19) . . . . ?
C1 N1 N2 C13 -119.51(16) . . . . ?
C1 C2 C3 C4 -177.00(17) . . . . ?
C1 C2 C3 C8 1.0(3) . . . . ?
C2 C1 C10 C9 0.8(3) . . . . ?
C2 C3 C4 C5 177.62(17) . . . . ?
C2 C3 C8 C7 -178.41(16) . . . . ?
C2 C3 C8 C9 0.4(2) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C3 C8 C9 C10 -1.1(3) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
C4 C3 C8 C9 178.42(16) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C6 C7 C8 C9 -177.93(18) . . . . ?
C7 C8 C9 C10 177.60(17) . . . . ?
C8 C3 C4 C5 -0.4(3) . . . . ?
C8 C9 C10 C1 0.6(3) . . . . ?
C10 C1 C2 C3 -1.5(3) . . . . ?
C11 O2 C12 C13 -22.42(19) . . . . ?
C11 N2 C13 C12 -28.96(17) . . . . ?
C11 N2 C13 C14 -146.94(16) . . . . ?
C11 N2 C13 C15 88.20(18) . . . . ?
C12 O2 C11 O1 -175.74(17) . . . . ?
C12 O2 C11 N2 3.88(19) . . . . ?
C13 N2 C11 O1 -162.94(18) . . . . ?
C13 N2 C11 O2 17.47(19) . . . . ?

_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 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.455
