# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 2042085'
loop_
_audit_author_name
_audit_author_address
asqwg
;hangzhou normal university
China
;
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2021-02-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.6894(13)
_cell_length_b                   10.6948(14)
_cell_length_c                   13.7194(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.046(2)
_cell_angle_gamma                90
_cell_volume                     1568.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0496 before and 0.0345 after correction.
The Ratio of minimum to maximum transmission is 0.9268.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7788
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.694
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2185
_reflns_number_total             2767
_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         0.235
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.038
_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)+(0.0511P)²+0.5541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1121
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_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 0.51048(13) 0.45401(12) 0.21431(9) 0.0519(4) Uani 1 1 d . . . . .
O2 O 0.62539(13) 0.67669(12) 0.52404(9) 0.0527(4) Uani 1 1 d . . . . .
N1 N 0.62602(12) 0.30154(13) 0.28850(9) 0.0349(3) Uani 1 1 d . . . . .
N2 N 0.65639(12) 0.45335(13) 0.44870(9) 0.0359(3) Uani 1 1 d . . . . .
H2 H 0.6671 0.5006 0.4989 0.043 Uiso 1 1 calc R . . . .
C1 C 0.4307(2) -0.19484(18) 0.09834(16) 0.0565(5) Uani 1 1 d . . . . .
H1A H 0.4755 -0.2580 0.1344 0.085 Uiso 1 1 calc GR . . . .
H1B H 0.4742 -0.1766 0.0394 0.085 Uiso 1 1 calc GR . . . .
H1C H 0.3480 -0.2243 0.0825 0.085 Uiso 1 1 calc GR . . . .
C2 C 0.42218(16) -0.07787(16) 0.15917(12) 0.0394(4) Uani 1 1 d . . . . .
C3 C 0.32159(17) -0.05827(17) 0.22026(13) 0.0433(4) Uani 1 1 d . . . . .
H3 H 0.2573 -0.1167 0.2222 0.052 Uiso 1 1 calc R . . . .
C4 C 0.31652(16) 0.04736(17) 0.27804(13) 0.0437(4) Uani 1 1 d . . . . .
H4 H 0.2493 0.0586 0.3192 0.052 Uiso 1 1 calc R . . . .
C5 C 0.40993(16) 0.13660(16) 0.27554(12) 0.0378(4) Uani 1 1 d . . . . .
H5 H 0.4057 0.2070 0.3151 0.045 Uiso 1 1 calc R . . . .
C6 C 0.51007(15) 0.12068(15) 0.21363(11) 0.0332(4) Uani 1 1 d . . . . .
C7 C 0.51537(15) 0.01325(16) 0.15683(12) 0.0381(4) Uani 1 1 d . . . . .
H7 H 0.5830 0.0018 0.1161 0.046 Uiso 1 1 calc R . . . .
C8 C 0.60951(16) 0.22026(16) 0.20224(12) 0.0387(4) Uani 1 1 d . . . . .
H8A H 0.6886 0.1798 0.1889 0.046 Uiso 1 1 calc R . . . .
H8B H 0.5876 0.2719 0.1464 0.046 Uiso 1 1 calc R . . . .
C9 C 0.57185(15) 0.41772(15) 0.28481(12) 0.0354(4) Uani 1 1 d . . . . .
C10 C 0.59444(14) 0.50156(15) 0.37085(11) 0.0326(4) Uani 1 1 d . . . . .
C11 C 0.55426(16) 0.62342(16) 0.36665(12) 0.0385(4) Uani 1 1 d . . . . .
H11 H 0.5107 0.6507 0.3113 0.046 Uiso 1 1 calc R . . . .
C12 C 0.57725(16) 0.71027(16) 0.44488(13) 0.0408(4) Uani 1 1 d . . . . .
C13 C 0.5430(2) 0.84489(18) 0.43029(17) 0.0588(6) Uani 1 1 d . . . . .
H13A H 0.4542 0.8520 0.4203 0.088 Uiso 1 1 calc GR . . . .
H13B H 0.5851 0.8769 0.3743 0.088 Uiso 1 1 calc GR . . . .
H13C H 0.5680 0.8920 0.4869 0.088 Uiso 1 1 calc GR . . . .
C14 C 0.70391(14) 0.33293(15) 0.45336(11) 0.0329(4) Uani 1 1 d . . . . .
C15 C 0.76511(16) 0.29041(16) 0.53717(12) 0.0409(4) Uani 1 1 d . . . . .
H15 H 0.7730 0.3424 0.5913 0.049 Uiso 1 1 calc R . . . .
C16 C 0.81426(17) 0.17090(18) 0.54031(13) 0.0454(5) Uani 1 1 d . . . . .
H16 H 0.8555 0.1425 0.5964 0.054 Uiso 1 1 calc R . . . .
C17 C 0.80199(17) 0.09362(17) 0.45986(14) 0.0477(5) Uani 1 1 d . . . . .
H17 H 0.8356 0.0134 0.4619 0.057 Uiso 1 1 calc R . . . .
C18 C 0.74002(17) 0.13470(17) 0.37633(13) 0.0430(4) Uani 1 1 d . . . . .
H18 H 0.7317 0.0817 0.3229 0.052 Uiso 1 1 calc R . . . .
C19 C 0.69013(14) 0.25480(15) 0.37193(11) 0.0333(4) 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
O1 C9 1.2220(19) . ?
O2 C12 1.246(2) . ?
N1 C8 1.476(2) . ?
N1 C9 1.371(2) . ?
N1 C19 1.415(2) . ?
N2 H2 0.8600 . ?
N2 C10 1.349(2) . ?
N2 C14 1.385(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.507(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.394(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 C7 1.390(2) . ?
C6 C8 1.515(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.498(2) . ?
C10 C11 1.373(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.437(2) . ?
C12 C13 1.498(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.389(2) . ?
C14 C19 1.401(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.392(2) . ?

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
C9 N1 C8 117.37(13) . . ?
C9 N1 C19 123.24(13) . . ?
C19 N1 C8 119.31(13) . . ?
C10 N2 H2 117.8 . . ?
C10 N2 C14 124.48(14) . . ?
C14 N2 H2 117.8 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.92(16) . . ?
C3 C2 C7 117.97(16) . . ?
C7 C2 C1 121.11(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.50(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.96(16) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.71(16) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 118.94(15) . . ?
C5 C6 C8 121.80(14) . . ?
C7 C6 C8 119.17(14) . . ?
C2 C7 H7 119.1 . . ?
C6 C7 C2 121.89(15) . . ?
C6 C7 H7 119.1 . . ?
N1 C8 C6 113.90(13) . . ?
N1 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C6 C8 H8A 108.8 . . ?
C6 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O1 C9 N1 122.49(15) . . ?
O1 C9 C10 120.66(15) . . ?
N1 C9 C10 116.82(14) . . ?
N2 C10 C9 117.70(14) . . ?
N2 C10 C11 123.00(15) . . ?
C11 C10 C9 119.29(14) . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.21(16) . . ?
C12 C11 H11 118.9 . . ?
O2 C12 C11 121.80(16) . . ?
O2 C12 C13 119.30(17) . . ?
C11 C12 C13 118.91(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 120.62(15) . . ?
N2 C14 C19 118.99(14) . . ?
C15 C14 C19 120.39(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.10(16) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.82(16) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.51(17) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.39(17) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 N1 118.48(14) . . ?
C18 C19 N1 122.75(15) . . ?
C18 C19 C14 118.78(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
