# 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. 
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data_cu_tp_yz_1_300k_cu_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2221385'
loop_
_audit_author_name
_audit_author_address
'Yang Meng'
;Sichuan University
China
;
_audit_update_record             
;
2022-11-22 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 N2 O2'
_chemical_formula_sum            'C7 H10 N2 O2'
_chemical_formula_weight         154.17
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.3586(2)
_cell_length_b                   6.1328(3)
_cell_length_c                   11.1471(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.5290(10)
_cell_angle_gamma                90
_cell_volume                     362.28(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5881
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      7.22
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1268 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.6781.
The λ/2 correction factor is Not present.
;
_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    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5724
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.156
_diffrn_reflns_theta_min         8.729
_diffrn_ambient_temperature      302.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                1305
_reflns_number_total             1310
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.098
_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)+(0.0462P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0832
_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.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_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 0.7287(3) 0.2361(3) 0.48794(13) 0.0470(4) Uani 1 1 d . . . . .
O3 O 0.7762(4) 0.8479(3) 0.25792(18) 0.0610(5) Uani 1 1 d . . . . .
N1 N 0.4614(3) 0.3767(3) 0.32585(13) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.8029(3) 0.5640(3) 0.39465(15) 0.0395(4) Uani 1 1 d . . . . .
H2 H 0.9407 0.6001 0.4400 0.047 Uiso 1 1 calc R U . . .
C1 C 0.6674(4) 0.3746(4) 0.41107(16) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.4453(4) 0.5728(3) 0.25198(17) 0.0326(5) Uani 1 1 d . . . . .
H2A H 0.3043 0.6629 0.2699 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4080(4) 0.5178(4) 0.11735(18) 0.0384(5) Uani 1 1 d . . . . .
H3A H 0.3700 0.6496 0.0701 0.046 Uiso 1 1 calc R U . . .
H3B H 0.5620 0.4556 0.0960 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1928(4) 0.3559(4) 0.08806(18) 0.0431(5) Uani 1 1 d . . . . .
H4A H 0.1745 0.3174 0.0028 0.052 Uiso 1 1 calc R U . . .
H4B H 0.0366 0.4229 0.1033 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6928(4) 0.6855(4) 0.29881(18) 0.0384(5) Uani 1 1 d . . . . .
C6 C 0.2794(4) 0.2018(4) 0.30003(17) 0.0357(5) Uani 1 1 d . . . . .
H6A H 0.1199 0.2449 0.3243 0.043 Uiso 1 1 calc R U . . .
H6B H 0.3394 0.0729 0.3458 0.043 Uiso 1 1 calc R U . . .
C7 C 0.2414(4) 0.1506(4) 0.16461(19) 0.0435(6) Uani 1 1 d . . . . .
H7A H 0.3904 0.0777 0.1445 0.052 Uiso 1 1 calc R U . . .
H7B H 0.0995 0.0520 0.1456 0.052 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 1.217(3) . ?
O3 C5 1.208(3) . ?
N1 C1 1.345(2) . ?
N1 C2 1.453(3) . ?
N1 C6 1.450(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.396(3) . ?
N2 C5 1.363(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.522(3) . ?
C2 C5 1.518(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C7 1.521(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.526(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C1 N1 C2 112.44(17) . . ?
C1 N1 C6 126.20(18) . . ?
C6 N1 C2 121.21(15) . . ?
C1 N2 H2 123.7 . . ?
C5 N2 H2 123.7 . . ?
C5 N2 C1 112.60(17) . . ?
O1 C1 N1 127.7(2) . . ?
O1 C1 N2 125.59(18) . . ?
N1 C1 N2 106.72(17) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 C3 111.31(16) . . ?
N1 C2 C5 101.92(16) . . ?
C3 C2 H2A 109.5 . . ?
C5 C2 H2A 109.5 . . ?
C5 C2 C3 114.86(16) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.95(16) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C7 111.04(17) . . ?
H4A C4 H4B 108.0 . . ?
C7 C4 H4A 109.4 . . ?
C7 C4 H4B 109.4 . . ?
O3 C5 N2 127.2(2) . . ?
O3 C5 C2 126.8(2) . . ?
N2 C5 C2 105.98(18) . . ?
N1 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
N1 C6 C7 109.63(16) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C4 C7 C6 111.78(19) . . ?
C4 C7 H7A 109.3 . . ?
C4 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?

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
N1 C2 C3 C4 49.9(2) . . . . ?
N1 C2 C5 O3 173.3(2) . . . . ?
N1 C2 C5 N2 -5.6(2) . . . . ?
N1 C6 C7 C4 -49.2(2) . . . . ?
C1 N1 C2 C3 127.95(17) . . . . ?
C1 N1 C2 C5 5.0(2) . . . . ?
C1 N1 C6 C7 -128.5(2) . . . . ?
C1 N2 C5 O3 -174.2(2) . . . . ?
C1 N2 C5 C2 4.7(2) . . . . ?
C2 N1 C1 O1 177.99(19) . . . . ?
C2 N1 C1 N2 -2.4(2) . . . . ?
C2 N1 C6 C7 46.7(2) . . . . ?
C2 C3 C4 C7 -57.0(3) . . . . ?
C3 C2 C5 O3 52.8(3) . . . . ?
C3 C2 C5 N2 -126.12(19) . . . . ?
C3 C4 C7 C6 57.5(2) . . . . ?
C5 N2 C1 O1 177.9(2) . . . . ?
C5 N2 C1 N1 -1.6(2) . . . . ?
C5 C2 C3 C4 165.10(19) . . . . ?
C6 N1 C1 O1 -6.4(3) . . . . ?
C6 N1 C1 N2 173.15(16) . . . . ?
C6 N1 C2 C3 -47.9(2) . . . . ?
C6 N1 C2 C5 -170.83(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
