# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_220107_yxj001
_database_code_depnum_ccdc_archive 'CCDC 2133499'
loop_
_audit_author_name
_audit_author_address
'Xinjie Yang' 'Zhejiang University of Technology'
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_audit_creation_date             2022-01-09
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.4030(5)
_cell_length_b                   7.2153(2)
_cell_length_c                   29.2429(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2616.99(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1448 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            37137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2446
_reflns_number_total             2890
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.311
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.8866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1113
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 0.68134(8) 0.21946(14) 0.85638(3) 0.0371(2) Uani 1 1 d . . . . .
O2 O 0.67832(11) 0.43721(19) 0.49518(4) 0.0595(4) Uani 1 1 d . . . . .
N1 N 0.82127(9) 0.35702(17) 0.59707(4) 0.0362(3) Uani 1 1 d . . . . .
N2 N 0.73559(10) 0.37814(16) 0.56717(4) 0.0347(3) Uani 1 1 d . . . . .
C1 C 0.69127(10) 0.17985(17) 0.73342(5) 0.0283(3) Uani 1 1 d . . . . .
H1 H 0.735962 0.120574 0.711458 0.034 Uiso 1 1 calc R . . . .
C2 C 0.71349(10) 0.15843(17) 0.77924(5) 0.0302(3) Uani 1 1 d . . . . .
H2 H 0.773053 0.084580 0.788472 0.036 Uiso 1 1 calc R . . . .
C3 C 0.64943(10) 0.24407(17) 0.81224(4) 0.0288(3) Uani 1 1 d . . . . .
C4 C 0.56087(10) 0.34870(17) 0.79837(5) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.515486 0.405580 0.820456 0.034 Uiso 1 1 calc R . . . .
C5 C 0.53941(10) 0.36927(17) 0.75206(5) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.478986 0.441179 0.742909 0.034 Uiso 1 1 calc R . . . .
C6 C 0.60385(10) 0.28758(16) 0.71853(4) 0.0263(3) Uani 1 1 d . . . . .
C7 C 0.58035(10) 0.31509(16) 0.66929(4) 0.0274(3) Uani 1 1 d . . . . .
C8 C 0.47490(10) 0.32940(18) 0.65308(5) 0.0320(3) Uani 1 1 d . . . . .
H8 H 0.416910 0.317261 0.674088 0.038 Uiso 1 1 calc R . . . .
C9 C 0.45171(11) 0.3610(2) 0.60692(5) 0.0372(3) Uani 1 1 d . . . . .
H9 H 0.378465 0.369696 0.597661 0.045 Uiso 1 1 calc R . . . .
C10 C 0.53142(12) 0.38011(19) 0.57441(5) 0.0365(3) Uani 1 1 d . . . . .
H10 H 0.515278 0.402592 0.543137 0.044 Uiso 1 1 calc R . . . .
C11 C 0.63719(11) 0.36442(18) 0.59015(5) 0.0310(3) Uani 1 1 d . . . . .
C12 C 0.66260(10) 0.33220(16) 0.63620(4) 0.0275(3) Uani 1 1 d . . . . .
C13 C 0.77833(10) 0.33039(18) 0.63731(5) 0.0314(3) Uani 1 1 d . . . . .
H13 H 0.819247 0.311826 0.664384 0.038 Uiso 1 1 calc R . . . .
C14 C 0.75384(14) 0.4141(2) 0.52078(5) 0.0434(4) Uani 1 1 d . . . . .
C15 C 0.86966(15) 0.4221(3) 0.50679(6) 0.0541(4) Uani 1 1 d . . . . .
H15A H 0.903618 0.531680 0.520401 0.081 Uiso 1 1 calc GR . . . .
H15B H 0.874463 0.429749 0.473396 0.081 Uiso 1 1 calc GR . . . .
H15C H 0.906837 0.310283 0.517413 0.081 Uiso 1 1 calc GR . . . .
C16 C 0.62339(14) 0.3169(2) 0.89114(5) 0.0466(4) Uani 1 1 d . . . . .
H16A H 0.629778 0.450627 0.885942 0.070 Uiso 1 1 calc GR . . . .
H16B H 0.653453 0.285838 0.921167 0.070 Uiso 1 1 calc GR . . . .
H16C H 0.547222 0.281019 0.890129 0.070 Uiso 1 1 calc GR . . . .


_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 C3 1.3618(16) . ?
O1 C16 1.4297(18) . ?
O2 C14 1.211(2) . ?
N1 N2 1.3845(16) . ?
N1 C13 1.3058(17) . ?
N2 C11 1.3969(17) . ?
N2 C14 1.3993(19) . ?
C1 H1 0.9500 . ?
C1 C2 1.3769(19) . ?
C1 C6 1.4033(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3943(19) . ?
C3 C4 1.3931(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3881(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3956(17) . ?
C6 C7 1.4823(18) . ?
C7 C8 1.3950(18) . ?
C7 C12 1.4114(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3948(19) . ?
C11 C12 1.4026(18) . ?
C12 C13 1.4359(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.495(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C3 O1 C16 117.62(11) . . ?
C13 N1 N2 105.80(11) . . ?
N1 N2 C11 111.04(11) . . ?
N1 N2 C14 120.56(12) . . ?
C11 N2 C14 128.37(13) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.25(12) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.64(12) . . ?
C3 C2 H2 119.7 . . ?
O1 C3 C2 115.63(11) . . ?
O1 C3 C4 125.15(12) . . ?
C4 C3 C2 119.21(12) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.55(12) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.04(12) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 121.83(11) . . ?
C5 C6 C1 117.28(12) . . ?
C5 C6 C7 120.89(11) . . ?
C8 C7 C6 121.62(12) . . ?
C8 C7 C12 115.99(12) . . ?
C12 C7 C6 122.38(11) . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.20(13) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.30(13) . . ?
C10 C9 H9 118.9 . . ?
C9 C10 H10 122.0 . . ?
C9 C10 C11 116.02(13) . . ?
C11 C10 H10 122.0 . . ?
N2 C11 C12 106.10(11) . . ?
C10 C11 N2 131.09(13) . . ?
C10 C11 C12 122.80(13) . . ?
C7 C12 C13 134.94(12) . . ?
C11 C12 C7 120.69(12) . . ?
C11 C12 C13 104.34(11) . . ?
N1 C13 C12 112.72(12) . . ?
N1 C13 H13 123.6 . . ?
C12 C13 H13 123.6 . . ?
O2 C14 N2 119.99(15) . . ?
O2 C14 C15 124.67(15) . . ?
N2 C14 C15 115.33(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 C3 C4 C5 177.34(11) . . . . ?
N1 N2 C11 C10 178.59(14) . . . . ?
N1 N2 C11 C12 -0.40(14) . . . . ?
N1 N2 C14 O2 -178.02(14) . . . . ?
N1 N2 C14 C15 1.52(19) . . . . ?
N2 N1 C13 C12 0.07(15) . . . . ?
N2 C11 C12 C7 178.69(11) . . . . ?
N2 C11 C12 C13 0.41(13) . . . . ?
C1 C2 C3 O1 -177.48(11) . . . . ?
C1 C2 C3 C4 1.41(19) . . . . ?
C1 C6 C7 C8 145.23(13) . . . . ?
C1 C6 C7 C12 -36.11(18) . . . . ?
C2 C1 C6 C5 -1.09(18) . . . . ?
C2 C1 C6 C7 178.68(11) . . . . ?
C2 C3 C4 C5 -1.44(18) . . . . ?
C3 C4 C5 C6 0.20(19) . . . . ?
C4 C5 C6 C1 1.05(18) . . . . ?
C4 C5 C6 C7 -178.72(11) . . . . ?
C5 C6 C7 C8 -35.00(17) . . . . ?
C5 C6 C7 C12 143.65(12) . . . . ?
C6 C1 C2 C3 -0.13(19) . . . . ?
C6 C7 C8 C9 177.99(12) . . . . ?
C6 C7 C12 C11 -177.81(11) . . . . ?
C6 C7 C12 C13 -0.2(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C12 C13 N1 -178.22(13) . . . . ?
C8 C7 C12 C11 0.92(17) . . . . ?
C8 C7 C12 C13 178.56(14) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 N2 -179.18(13) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C7 -0.40(19) . . . . ?
C10 C11 C12 C13 -178.68(12) . . . . ?
C11 N2 C14 O2 -0.2(2) . . . . ?
C11 N2 C14 C15 179.31(13) . . . . ?
C11 C12 C13 N1 -0.32(15) . . . . ?
C12 C7 C8 C9 -0.74(18) . . . . ?
C13 N1 N2 C11 0.21(14) . . . . ?
C13 N1 N2 C14 178.35(12) . . . . ?
C14 N2 C11 C10 0.6(2) . . . . ?
C14 N2 C11 C12 -178.36(13) . . . . ?
C16 O1 C3 C2 175.03(12) . . . . ?
C16 O1 C3 C4 -3.79(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
