# 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_200821_s2_lwj
_database_code_depnum_ccdc_archive 'CCDC 2055782'
loop_
_audit_author_name
_audit_author_address
Wenjing
;Sichuan University
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1154(7)
_cell_length_b                   9.6387(8)
_cell_length_c                   10.8333(9)
_cell_angle_alpha                93.473(7)
_cell_angle_beta                 98.583(7)
_cell_angle_gamma                109.416(8)
_cell_volume                     688.03(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5657
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.086
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2806
_reflns_number_gt                1992
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.0615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2806
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.1878(2) 0.78294(14) 0.44800(11) 0.0416(3) Uani 1 1 d . . . . .
C5 C 0.2754(2) 0.75734(17) 0.55856(15) 0.0411(4) Uani 1 1 d . . . . .
C13 C 0.1431(2) 0.71237(17) 0.65356(14) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.2094(3) 0.86674(19) 0.24237(15) 0.0484(4) Uani 1 1 d . . . . .
C18 C -0.0596(2) 0.62474(18) 0.61712(15) 0.0460(4) Uani 1 1 d . . . . .
H18 H -0.1135 0.5947 0.5322 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0134(3) 0.80557(18) 0.19781(14) 0.0427(4) Uani 1 1 d . . . . .
C1 C 0.3058(3) 0.82889(17) 0.36220(14) 0.0436(4) Uani 1 1 d . . . . .
O1 O 0.31792(19) 0.95024(16) 0.18090(12) 0.0715(4) Uani 1 1 d . . . . .
C8 C -0.1314(3) 0.66351(18) 0.21519(15) 0.0465(4) Uani 1 1 d . . . . .
H8 H -0.0738 0.6062 0.2632 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2188(3) 0.7581(2) 0.78120(15) 0.0500(4) Uani 1 1 d . . . . .
H14 H 0.3541 0.8170 0.8074 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4790(3) 0.7728(2) 0.58331(16) 0.0505(4) Uani 1 1 d . . . . .
H4 H 0.5351 0.7523 0.6601 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5972(3) 0.8186(2) 0.49384(17) 0.0555(5) Uani 1 1 d . . . . .
H3 H 0.7334 0.8286 0.5089 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5102(3) 0.8495(2) 0.38171(16) 0.0512(5) Uani 1 1 d . . . . .
H2 H 0.5872 0.8834 0.3203 0.061 Uiso 1 1 calc R U . . .
C9 C -0.3341(3) 0.6073(2) 0.16130(16) 0.0528(5) Uani 1 1 d . . . . .
H9 H -0.4120 0.5114 0.1716 0.063 Uiso 1 1 calc R U . . .
C15 C 0.0953(3) 0.7171(2) 0.86901(16) 0.0577(5) Uani 1 1 d . . . . .
H15 H 0.1472 0.7490 0.9539 0.069 Uiso 1 1 calc R U . . .
C16 C -0.1040(3) 0.6292(2) 0.83162(18) 0.0588(5) Uani 1 1 d . . . . .
H16 H -0.1869 0.6015 0.8912 0.071 Uiso 1 1 calc R U . . .
C12 C -0.1039(3) 0.8897(2) 0.12735(15) 0.0532(5) Uani 1 1 d . . . . .
H12 H -0.0264 0.9849 0.1149 0.064 Uiso 1 1 calc R U . . .
C10 C -0.4216(3) 0.6924(2) 0.09237(17) 0.0587(5) Uani 1 1 d . . . . .
H10 H -0.5586 0.6543 0.0570 0.070 Uiso 1 1 calc R U . . .
C17 C -0.1818(3) 0.5818(2) 0.70563(18) 0.0552(5) Uani 1 1 d . . . . .
H17 H -0.3165 0.5211 0.6805 0.066 Uiso 1 1 calc R U . . .
C11 C -0.3067(3) 0.8339(2) 0.07572(17) 0.0607(5) Uani 1 1 d . . . . .
H11 H -0.3660 0.8917 0.0296 0.073 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
N1 C5 1.3414(19) . ?
N1 C1 1.3420(19) . ?
C5 C4 1.388(2) . ?
C5 C13 1.485(2) . ?
C13 C18 1.389(2) . ?
C13 C14 1.394(2) . ?
C6 O1 1.2219(18) . ?
C6 C7 1.486(2) . ?
C6 C1 1.499(2) . ?
C18 C17 1.380(2) . ?
C18 H18 0.9300 . ?
C7 C8 1.389(2) . ?
C7 C12 1.389(2) . ?
C1 C2 1.382(2) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9300 . ?
C14 C15 1.378(2) . ?
C14 H14 0.9300 . ?
C4 C3 1.375(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.374(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C9 C10 1.376(2) . ?
C9 H9 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C12 C11 1.375(3) . ?
C12 H12 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C11 H11 0.9300 . ?

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
C5 N1 C1 117.51(14) . . ?
N1 C5 C4 121.91(14) . . ?
N1 C5 C13 116.37(14) . . ?
C4 C5 C13 121.71(14) . . ?
C18 C13 C14 118.45(15) . . ?
C18 C13 C5 120.72(14) . . ?
C14 C13 C5 120.83(15) . . ?
O1 C6 C7 119.85(15) . . ?
O1 C6 C1 118.63(16) . . ?
C7 C6 C1 121.52(13) . . ?
C17 C18 C13 120.64(16) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C8 C7 C12 118.83(16) . . ?
C8 C7 C6 122.58(15) . . ?
C12 C7 C6 118.39(15) . . ?
N1 C1 C2 123.51(14) . . ?
N1 C1 C6 117.03(15) . . ?
C2 C1 C6 119.39(14) . . ?
C9 C8 C7 120.04(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C15 C14 C13 120.67(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C3 C4 C5 119.76(15) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C2 C3 C4 118.75(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C2 C1 118.51(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C10 C9 C8 120.39(17) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C16 C15 C14 120.17(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.10(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C11 C12 C7 120.82(17) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C9 C10 C11 120.05(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C18 C17 C16 119.96(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C11 C10 119.87(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

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
C1 N1 C5 C4 -2.0(2) . . . . ?
C1 N1 C5 C13 177.66(14) . . . . ?
N1 C5 C13 C18 34.7(2) . . . . ?
C4 C5 C13 C18 -145.67(17) . . . . ?
N1 C5 C13 C14 -144.72(16) . . . . ?
C4 C5 C13 C14 34.9(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
C5 C13 C18 C17 179.36(15) . . . . ?
O1 C6 C7 C8 144.86(18) . . . . ?
C1 C6 C7 C8 -35.3(2) . . . . ?
O1 C6 C7 C12 -29.8(3) . . . . ?
C1 C6 C7 C12 149.94(16) . . . . ?
C5 N1 C1 C2 0.6(2) . . . . ?
C5 N1 C1 C6 -176.08(14) . . . . ?
O1 C6 C1 N1 157.26(17) . . . . ?
C7 C6 C1 N1 -22.5(2) . . . . ?
O1 C6 C1 C2 -19.6(3) . . . . ?
C7 C6 C1 C2 160.63(16) . . . . ?
C12 C7 C8 C9 1.0(3) . . . . ?
C6 C7 C8 C9 -173.71(15) . . . . ?
C18 C13 C14 C15 0.1(3) . . . . ?
C5 C13 C14 C15 179.52(15) . . . . ?
N1 C5 C4 C3 1.4(3) . . . . ?
C13 C5 C4 C3 -178.21(15) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C4 C3 C2 C1 -1.9(3) . . . . ?
N1 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C2 C3 177.93(16) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C6 C7 C12 C11 175.04(16) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C13 C18 C17 C16 1.6(3) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C7 C12 C11 C10 -0.8(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046



