# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_190103xj_0m
_database_code_depnum_ccdc_archive 'CCDC 1959603'
loop_
_audit_author_name
_audit_author_address
QASWQ
;hangzhou normal university
China
;
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2020-05-17 downloaded from the CCDC.
;
_audit_creation_date             2019-01-04
_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         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9529(7)
_cell_length_b                   11.1696(16)
_cell_length_c                   13.2334(19)
_cell_angle_alpha                112.6230(10)
_cell_angle_beta                 99.490(2)
_cell_angle_gamma                94.354(2)
_cell_volume                     658.67(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1994
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.971
_cell_measurement_theta_min      3.108
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0404 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.9309. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5331
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.744
_diffrn_reflns_theta_min         1.705
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1970
_reflns_number_total             2834
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.137
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.064
_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)+(0.0610P)²+0.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1277
_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.a Riding coordinates:
 O2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_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 0.1856(2) 0.97550(10) 0.32623(10) 0.0550(3) Uani 1 1 d . . . . .
O2 O 0.4652(3) 0.80300(11) 0.51109(10) 0.0646(4) Uani 1 1 d . . . . .
H2 H 0.581826 0.858038 0.562846 0.097 Uiso 1 1 d R . . . .
N1 N 0.1944(2) 0.76015(11) 0.29237(10) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.4098(3) 0.62277(11) 0.15324(10) 0.0447(3) Uani 1 1 d . . . . .
C1 C 0.2644(3) 0.87149(13) 0.27310(12) 0.0416(4) Uani 1 1 d . . . . .
C2 C 0.2692(3) 0.64033(13) 0.23012(12) 0.0387(4) Uani 1 1 d . . . . .
C3 C 0.4993(3) 0.73102(13) 0.13293(12) 0.0408(4) Uani 1 1 d . . . . .
C4 C 0.4321(3) 0.85495(13) 0.19027(12) 0.0402(4) Uani 1 1 d . . . . .
C5 C 0.5300(4) 0.96172(15) 0.16784(14) 0.0521(4) Uani 1 1 d . . . . .
H5 H 0.484405 1.044315 0.205407 0.062 Uiso 1 1 calc R . . . .
C6 C 0.6919(4) 0.94377(17) 0.09089(15) 0.0589(5) Uani 1 1 d . . . . .
H6 H 0.758819 1.014680 0.076891 0.071 Uiso 1 1 calc R . . . .
C7 C 0.7579(4) 0.81984(18) 0.03293(14) 0.0587(5) Uani 1 1 d . . . . .
H7 H 0.868018 0.808820 -0.019585 0.070 Uiso 1 1 calc R . . . .
C8 C 0.6621(4) 0.71410(16) 0.05263(13) 0.0518(4) Uani 1 1 d . . . . .
H8 H 0.704985 0.631561 0.012927 0.062 Uiso 1 1 calc R . . . .
C9 C 0.1824(3) 0.52270(13) 0.25232(12) 0.0427(4) Uani 1 1 d . . . . .
C10 C -0.0563(4) 0.43821(16) 0.18994(16) 0.0628(5) Uani 1 1 d . . . . .
H10 H -0.171280 0.456434 0.136323 0.075 Uiso 1 1 calc R . . . .
C11 C -0.1265(5) 0.32601(18) 0.20652(19) 0.0727(6) Uani 1 1 d . . . . .
H11 H -0.290431 0.270026 0.164728 0.087 Uiso 1 1 calc R . . . .
C12 C 0.0410(5) 0.29647(17) 0.28313(16) 0.0670(6) Uani 1 1 d . . . . .
H12 H -0.006752 0.220345 0.293297 0.080 Uiso 1 1 calc R . . . .
C13 C 0.2801(5) 0.3796(2) 0.34504(19) 0.0828(7) Uani 1 1 d . . . . .
H13 H 0.396110 0.360057 0.397529 0.099 Uiso 1 1 calc R . . . .
C14 C 0.3505(4) 0.49315(19) 0.32990(17) 0.0734(6) Uani 1 1 d . . . . .
H14 H 0.513032 0.549669 0.372724 0.088 Uiso 1 1 calc R . . . .
C15 C 0.0420(3) 0.77613(16) 0.38230(13) 0.0480(4) Uani 1 1 d . . . . .
H15A H -0.026341 0.690186 0.377918 0.058 Uiso 1 1 calc R . . . .
H15B H -0.116725 0.818851 0.371085 0.058 Uiso 1 1 calc R . . . .
C16 C 0.2203(4) 0.85639(17) 0.49797(14) 0.0523(4) Uani 1 1 d . . . . .
H16A H 0.265464 0.946584 0.507334 0.063 Uiso 1 1 calc R . . . .
H16B H 0.119026 0.855929 0.554660 0.063 Uiso 1 1 calc R . . . .


_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 1.2358(17) . ?
O2 H2 0.8201 . ?
O2 C16 1.406(2) . ?
N1 C1 1.3927(18) . ?
N1 C2 1.3910(18) . ?
N1 C15 1.473(2) . ?
N2 C2 1.2881(19) . ?
N2 C3 1.3923(18) . ?
C1 C4 1.447(2) . ?
C2 C9 1.500(2) . ?
C3 C4 1.396(2) . ?
C3 C8 1.403(2) . ?
C4 C5 1.406(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(2) . ?
C9 C14 1.370(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.518(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 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
C16 O2 H2 109.5 . . ?
C1 N1 C15 116.90(12) . . ?
C2 N1 C1 121.07(13) . . ?
C2 N1 C15 122.02(12) . . ?
C2 N2 C3 118.13(12) . . ?
O1 C1 N1 119.87(15) . . ?
O1 C1 C4 124.60(14) . . ?
N1 C1 C4 115.53(12) . . ?
N1 C2 C9 118.92(13) . . ?
N2 C2 N1 124.15(13) . . ?
N2 C2 C9 116.93(12) . . ?
N2 C3 C4 121.88(14) . . ?
N2 C3 C8 118.61(13) . . ?
C4 C3 C8 119.51(14) . . ?
C3 C4 C1 119.11(13) . . ?
C3 C4 C5 119.83(15) . . ?
C5 C4 C1 121.05(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.78(16) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.51(16) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(17) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.69(16) . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C2 120.55(14) . . ?
C14 C9 C2 120.36(14) . . ?
C14 C9 C10 118.94(15) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.18(17) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.82(18) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.35(17) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.22(19) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.48(18) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
N1 C15 C16 112.52(13) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
O2 C16 C15 109.69(13) . . ?
O2 C16 H16A 109.7 . . ?
O2 C16 H16B 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?

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
O1 C1 C4 C3 -177.68(14) . . . . ?
O1 C1 C4 C5 3.0(2) . . . . ?
N1 C1 C4 C3 3.00(19) . . . . ?
N1 C1 C4 C5 -176.29(13) . . . . ?
N1 C2 C9 C10 94.33(19) . . . . ?
N1 C2 C9 C14 -90.3(2) . . . . ?
N1 C15 C16 O2 -52.84(18) . . . . ?
N2 C2 C9 C10 -85.5(2) . . . . ?
N2 C2 C9 C14 89.8(2) . . . . ?
N2 C3 C4 C1 -0.1(2) . . . . ?
N2 C3 C4 C5 179.24(13) . . . . ?
N2 C3 C8 C7 -178.55(15) . . . . ?
C1 N1 C2 N2 1.4(2) . . . . ?
C1 N1 C2 C9 -178.49(12) . . . . ?
C1 N1 C15 C16 -70.01(17) . . . . ?
C1 C4 C5 C6 178.75(14) . . . . ?
C2 N1 C1 O1 176.96(13) . . . . ?
C2 N1 C1 C4 -3.69(19) . . . . ?
C2 N1 C15 C16 109.12(16) . . . . ?
C2 N2 C3 C4 -2.4(2) . . . . ?
C2 N2 C3 C8 177.41(14) . . . . ?
C2 C9 C10 C11 176.24(17) . . . . ?
C2 C9 C14 C13 -175.48(19) . . . . ?
C3 N2 C2 N1 1.8(2) . . . . ?
C3 N2 C2 C9 -178.34(12) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C4 C3 C8 C7 1.3(2) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C3 -0.9(3) . . . . ?
C8 C3 C4 C1 -179.88(13) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C15 N1 C1 O1 -3.9(2) . . . . ?
C15 N1 C1 C4 175.45(12) . . . . ?
C15 N1 C2 N2 -177.72(14) . . . . ?
C15 N1 C2 C9 2.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
