# Electronic Supplementary Material (ESI) for ChemComm.
# 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_sust_2837_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2049499'
loop_
_audit_author_name
_audit_author_address
'Yan Hu'
;Shaan Xi University of Science and Technology
China
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.6333(12)
_cell_length_b                   5.5710(5)
_cell_length_c                   20.8717(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.874(3)
_cell_angle_gamma                90
_cell_volume                     1437.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4158
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      26.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22330
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.296
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3547
_reflns_number_gt                1806
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.6035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1368
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.2311
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_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
O2 O 0.60419(15) 0.1606(3) 0.12876(8) 0.0644(5) Uani 1 1 d . . . . .
O1 O 0.54789(16) 0.1074(3) 0.42240(9) 0.0663(6) Uani 1 1 d . . . . .
H1 H 0.553651 0.135035 0.461554 0.099 Uiso 1 1 calc R U . . .
N1 N 0.60891(16) 0.3293(4) 0.53300(10) 0.0554(5) Uani 1 1 d . . . . .
C1 C 0.72753(18) 0.6700(4) 0.54060(12) 0.0495(6) Uani 1 1 d . . . . .
C12 C 0.59904(19) 0.1770(4) 0.19343(11) 0.0503(6) Uani 1 1 d . . . . .
C13 C 0.60112(18) 0.2408(4) 0.32695(11) 0.0482(6) Uani 1 1 d . . . . .
C2 C 0.66470(18) 0.4825(4) 0.50127(12) 0.0492(6) Uani 1 1 d . . . . .
C10 C 0.65969(19) 0.4503(4) 0.43494(12) 0.0518(6) Uani 1 1 d . . . . .
H10 H 0.697455 0.553883 0.412798 0.062 Uiso 1 1 d R U . . .
C11 C 0.60101(19) 0.2620(4) 0.39766(12) 0.0516(6) Uani 1 1 d . . . . .
C3 C 0.7274(2) 0.6812(5) 0.60792(13) 0.0558(6) Uani 1 1 d . . . . .
C4 C 0.7891(2) 0.8366(5) 0.51376(14) 0.0598(7) Uani 1 1 d . . . . .
H4 H 0.789206 0.830971 0.469239 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6489(2) 0.4044(4) 0.29164(12) 0.0553(6) Uani 1 1 d . . . . .
H14 H 0.682431 0.539335 0.312967 0.066 Uiso 1 1 calc R U . . .
C15 C 0.6486(2) 0.3745(5) 0.22664(12) 0.0581(7) Uani 1 1 d . . . . .
H15 H 0.681878 0.487755 0.204665 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5502(2) 0.0116(5) 0.22650(14) 0.0667(8) Uani 1 1 d . . . . .
H16 H 0.516294 -0.122018 0.204684 0.080 Uiso 1 1 calc R U . . .
C5 C 0.6081(2) 0.3446(5) 0.59771(14) 0.0658(7) Uani 1 1 d . . . . .
H5 H 0.567073 0.235895 0.616129 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5515(2) 0.0439(5) 0.29195(13) 0.0683(8) Uani 1 1 d . . . . .
H17 H 0.518098 -0.069983 0.313667 0.082 Uiso 1 1 calc R U . . .
C6 C 0.6654(2) 0.5136(5) 0.63577(14) 0.0662(7) Uani 1 1 d . . . . .
H6 H 0.664422 0.520721 0.680156 0.079 Uiso 1 1 calc R U . . .
C7 C 0.7903(2) 0.8602(6) 0.64607(15) 0.0718(8) Uani 1 1 d . . . . .
H7 H 0.791277 0.869537 0.690681 0.086 Uiso 1 1 calc R U . . .
C8 C 0.8492(2) 1.0078(5) 0.55208(16) 0.0730(8) Uani 1 1 d . . . . .
H8 H 0.889992 1.116680 0.533568 0.088 Uiso 1 1 calc R U . . .
C18 C 0.5588(3) -0.0470(6) 0.09381(14) 0.0772(9) Uani 1 1 d . . . . .
H18A H 0.591919 -0.188267 0.115507 0.116 Uiso 1 1 calc R U . . .
H18B H 0.571371 -0.041524 0.050026 0.116 Uiso 1 1 calc R U . . .
H18C H 0.482322 -0.051292 0.092344 0.116 Uiso 1 1 calc R U . . .
C9 C 0.8493(2) 1.0189(6) 0.61839(17) 0.0781(9) Uani 1 1 d . . . . .
H9 H 0.890025 1.135806 0.644172 0.094 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
O2 C12 1.368(3) . ?
O2 C18 1.424(3) . ?
O1 C11 1.265(3) . ?
O1 H1 0.8200 . ?
N1 C5 1.355(3) . ?
N1 C2 1.362(3) . ?
C1 C4 1.400(3) . ?
C1 C3 1.407(3) . ?
C1 C2 1.459(3) . ?
C12 C16 1.371(4) . ?
C12 C15 1.380(3) . ?
C13 C14 1.386(3) . ?
C13 C17 1.394(3) . ?
C13 C11 1.481(3) . ?
C2 C10 1.385(3) . ?
C10 C11 1.421(3) . ?
C10 H10 0.9300 . ?
C3 C7 1.414(4) . ?
C3 C6 1.418(4) . ?
C4 C8 1.370(4) . ?
C4 H4 0.9300 . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C5 C6 1.344(4) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.359(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 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
C12 O2 C18 117.6(2) . . ?
C11 O1 H1 109.5 . . ?
C5 N1 C2 123.8(2) . . ?
C4 C1 C3 119.0(2) . . ?
C4 C1 C2 122.2(2) . . ?
C3 C1 C2 118.8(2) . . ?
O2 C12 C16 124.7(2) . . ?
O2 C12 C15 116.1(2) . . ?
C16 C12 C15 119.2(2) . . ?
C14 C13 C17 115.9(2) . . ?
C14 C13 C11 124.6(2) . . ?
C17 C13 C11 119.5(2) . . ?
N1 C2 C10 118.9(2) . . ?
N1 C2 C1 116.8(2) . . ?
C10 C2 C1 124.3(2) . . ?
C2 C10 C11 123.7(2) . . ?
C2 C10 H10 119.6 . . ?
C11 C10 H10 116.7 . . ?
O1 C11 C10 122.7(2) . . ?
O1 C11 C13 117.5(2) . . ?
C10 C11 C13 119.8(2) . . ?
C1 C3 C7 118.5(3) . . ?
C1 C3 C6 119.7(2) . . ?
C7 C3 C6 121.8(3) . . ?
C8 C4 C1 121.0(3) . . ?
C8 C4 H4 119.5 . . ?
C1 C4 H4 119.5 . . ?
C15 C14 C13 122.4(2) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C14 C15 C12 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C12 C15 H15 119.9 . . ?
C12 C16 C17 119.8(2) . . ?
C12 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C6 C5 N1 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
N1 C5 H5 119.4 . . ?
C16 C17 C13 122.4(2) . . ?
C16 C17 H17 118.8 . . ?
C13 C17 H17 118.8 . . ?
C5 C6 C3 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C3 C6 H6 120.2 . . ?
C9 C7 C3 120.9(3) . . ?
C9 C7 H7 119.6 . . ?
C3 C7 H7 119.6 . . ?
C4 C8 C9 120.1(3) . . ?
C4 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C9 C8 120.5(3) . . ?
C7 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045



