# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2036636'
loop_
_audit_author_name
_audit_author_address
'Wen-Kui Dong'
;LanZhou JiaoTong University
China
;
_audit_update_record             
;
2020-10-12 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 N2 O3'
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_weight         260.29
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.7978(18)
_cell_length_b                   4.4776(3)
_cell_length_c                   16.8590(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.713(4)
_cell_angle_gamma                90
_cell_volume                     2506.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3162
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14459
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.843
_diffrn_reflns_theta_min         2.453
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1946
_reflns_number_total             2683
_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 V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0724
_refine_ls_restrained_S_all      1.140
_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)+(0.0672P)²+8.6925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1876
_refine_ls_wR_factor_ref         0.2028
_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 O(H) groups
2. Restrained distances
 H2B-N2 = N2-H2A
 0.87 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
C1 C 0.64430(9) 0.4722(7) 0.49314(19) 0.0300(7) Uani 1 1 d . . . . .
C2 C 0.63698(9) 0.5238(7) 0.41019(19) 0.0269(7) Uani 1 1 d . . . . .
C3 C 0.66128(8) 0.3706(7) 0.36111(19) 0.0276(7) Uani 1 1 d . . . . .
C4 C 0.65536(9) 0.3996(8) 0.2760(2) 0.0315(7) Uani 1 1 d . . . . .
H4 H 0.634217 0.522975 0.249002 0.038 Uiso 1 1 calc R . . . .
C5 C 0.67967(10) 0.2522(8) 0.2319(2) 0.0356(8) Uani 1 1 d . . . . .
H5 H 0.675234 0.278333 0.175025 0.043 Uiso 1 1 calc R . . . .
C6 C 0.71062(10) 0.0657(8) 0.2688(2) 0.0383(8) Uani 1 1 d . . . . .
H6 H 0.727099 -0.035063 0.237399 0.046 Uiso 1 1 calc R . . . .
C7 C 0.71710(10) 0.0288(8) 0.3516(2) 0.0375(8) Uani 1 1 d . . . . .
H7 H 0.738169 -0.098503 0.377093 0.045 Uiso 1 1 calc R . . . .
C8 C 0.69279(9) 0.1778(7) 0.3991(2) 0.0315(7) Uani 1 1 d . . . . .
C9 C 0.69886(10) 0.1373(8) 0.4841(2) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.719894 0.010072 0.509735 0.045 Uiso 1 1 calc R . . . .
C10 C 0.67514(10) 0.2773(8) 0.5293(2) 0.0368(8) Uani 1 1 d . . . . .
H10 H 0.679387 0.243417 0.585922 0.044 Uiso 1 1 calc R . . . .
C11 C 0.60540(9) 0.7305(7) 0.37349(18) 0.0275(7) Uani 1 1 d . . . . .
H11 H 0.600888 0.764759 0.316908 0.033 Uiso 1 1 calc R . . . .
C12 C 0.53299(9) 1.2011(8) 0.42432(18) 0.0286(7) Uani 1 1 d . . . . .
H12A H 0.551044 1.335502 0.461201 0.034 Uiso 1 1 calc R . . . .
H12B H 0.521320 1.053411 0.457146 0.034 Uiso 1 1 calc R . . . .
C13 C 0.49980(9) 1.3794(8) 0.3722(2) 0.0323(7) Uani 1 1 d . . . . .
H13A H 0.488880 1.524990 0.406713 0.039 Uiso 1 1 calc R . . . .
H13B H 0.511547 1.493813 0.331935 0.039 Uiso 1 1 calc R . . . .
C14 C 0.46551(9) 1.1903(8) 0.32815(18) 0.0302(7) Uani 1 1 d . . . . .
H14A H 0.446988 1.313187 0.288821 0.036 Uiso 1 1 calc R . . . .
H14B H 0.476023 1.025803 0.298735 0.036 Uiso 1 1 calc R . . . .
N1 N 0.58389(7) 0.8652(6) 0.41670(16) 0.0291(6) Uani 1 1 d . . . . .
N2 N 0.41321(9) 0.8776(8) 0.34847(18) 0.0373(7) Uani 1 1 d D . . . .
H2A H 0.3916(8) 0.983(9) 0.351(3) 0.058(13) Uiso 1 1 d D . . . .
H2B H 0.4147(14) 0.732(7) 0.383(2) 0.067(15) Uiso 1 1 d D . . . .
O1 O 0.62268(7) 0.6024(6) 0.54406(13) 0.0350(6) Uani 1 1 d . . . . .
H1 H 0.604561 0.709907 0.517468 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.55502(6) 1.0516(5) 0.37072(12) 0.0296(5) Uani 1 1 d . . . . .
O3 O 0.44503(6) 1.0734(6) 0.38805(13) 0.0356(6) 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
C1 C2 1.393(4) . ?
C1 C10 1.408(5) . ?
C1 O1 1.358(4) . ?
C2 C3 1.443(4) . ?
C2 C11 1.460(4) . ?
C3 C4 1.417(5) . ?
C3 C8 1.427(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.416(5) . ?
C8 C9 1.422(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.358(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 N1 1.273(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.518(4) . ?
C12 O2 1.438(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.514(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 O3 1.426(4) . ?
N1 O2 1.403(3) . ?
N2 H2A 0.876(10) . ?
N2 H2B 0.874(10) . ?
N2 O3 1.451(4) . ?
O1 H1 0.8400 . ?

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
C2 C1 C10 121.1(3) . . ?
O1 C1 C2 123.2(3) . . ?
O1 C1 C10 115.7(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 C11 120.7(3) . . ?
C3 C2 C11 120.5(3) . . ?
C4 C3 C2 123.3(3) . . ?
C4 C3 C8 117.6(3) . . ?
C8 C3 C2 119.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 119.7(3) . . ?
C7 C8 C9 121.3(3) . . ?
C9 C8 C3 119.0(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 H10 119.7 . . ?
C9 C10 C1 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C2 C11 H11 119.7 . . ?
N1 C11 C2 120.5(3) . . ?
N1 C11 H11 119.7 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
O2 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
O2 C12 C13 107.1(2) . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.9(3) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 110.4 . . ?
C13 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O3 C14 C13 106.6(2) . . ?
O3 C14 H14A 110.4 . . ?
O3 C14 H14B 110.4 . . ?
C11 N1 O2 112.2(2) . . ?
H2A N2 H2B 108(4) . . ?
O3 N2 H2A 102(3) . . ?
O3 N2 H2B 101(3) . . ?
C1 O1 H1 109.5 . . ?
N1 O2 C12 108.5(2) . . ?
C14 O3 N2 108.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
