# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_20190520a
_database_code_depnum_ccdc_archive 'CCDC 2045428'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-11-19 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;
_audit_creation_date             2019-05-21
_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         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_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                   5.6716(5)
_cell_length_b                   11.2488(11)
_cell_length_c                   11.2777(10)
_cell_angle_alpha                71.977(4)
_cell_angle_beta                 78.405(4)
_cell_angle_gamma                83.669(4)
_cell_volume                     669.34(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7722
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      3.672
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0596 before and 0.0464 after correction. The Ratio of minimum to maximum transmission is 0.9426. 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    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20030
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.562
_diffrn_reflns_theta_min         3.672
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                2398
_reflns_number_total             3082
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.240
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.036
_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)+(0.0551P)²+0.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1145
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 0.05941(16) 0.77181(9) 0.60418(9) 0.0398(2) Uani 1 1 d . . . . .
O2 O -0.1492(2) 0.71130(11) 0.48380(11) 0.0585(3) Uani 1 1 d . . . . .
O3 O 0.7849(2) 0.73689(10) 0.92616(11) 0.0528(3) Uani 1 1 d . . . . .
N1 N 0.23896(19) 0.71457(10) 0.67308(10) 0.0344(3) Uani 1 1 d . . . . .
C1 C 0.0084(3) 0.68136(14) 0.54692(13) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.1646(3) 0.57607(14) 0.58374(13) 0.0407(3) Uani 1 1 d . . . . .
H2 H 0.173793 0.503631 0.559439 0.049 Uiso 1 1 calc R . . . .
C3 C 0.3004(2) 0.59788(12) 0.66108(12) 0.0326(3) Uani 1 1 d . . . . .
C4 C 0.4807(2) 0.52695(12) 0.73119(12) 0.0325(3) Uani 1 1 d . . . . .
C5 C 0.5509(3) 0.40505(13) 0.72600(14) 0.0422(3) Uani 1 1 d . . . . .
H5 H 0.480893 0.370388 0.677359 0.051 Uiso 1 1 calc R . . . .
C6 C 0.7224(3) 0.33714(14) 0.79247(15) 0.0485(4) Uani 1 1 d . . . . .
H6 H 0.771378 0.256790 0.787811 0.058 Uiso 1 1 calc R . . . .
C7 C 0.8234(3) 0.38792(14) 0.86679(15) 0.0461(4) Uani 1 1 d . . . . .
H7 H 0.938587 0.340731 0.912603 0.055 Uiso 1 1 calc R . . . .
C8 C 0.7558(2) 0.50722(13) 0.87383(13) 0.0388(3) Uani 1 1 d . . . . .
H8 H 0.824897 0.539025 0.925031 0.047 Uiso 1 1 calc R . . . .
C9 C 0.5837(2) 0.58198(11) 0.80487(11) 0.0304(3) Uani 1 1 d . . . . .
C10 C 0.5058(2) 0.70964(11) 0.80680(11) 0.0296(3) Uani 1 1 d . . . . .
C11 C 0.6072(2) 0.77598(12) 0.87755(12) 0.0340(3) Uani 1 1 d . . . . .
C12 C 0.4807(3) 0.89715(13) 0.89064(13) 0.0418(3) Uani 1 1 d . . . . .
H12A H 0.591209 0.943443 0.912728 0.050 Uiso 1 1 calc R . . . .
H12B H 0.345763 0.878123 0.960435 0.050 Uiso 1 1 calc R . . . .
C13 C 0.3870(2) 0.98144(12) 0.77301(12) 0.0344(3) Uani 1 1 d . . . . .
C14 C 0.2278(2) 0.90410(12) 0.73440(14) 0.0370(3) Uani 1 1 d . . . . .
H14A H 0.071984 0.898407 0.789786 0.044 Uiso 1 1 calc R . . . .
H14B H 0.202108 0.947311 0.648750 0.044 Uiso 1 1 calc R . . . .
C15 C 0.3311(2) 0.77452(11) 0.73980(11) 0.0305(3) Uani 1 1 d . . . . .
C16 C 0.2357(3) 1.09226(14) 0.80488(15) 0.0491(4) Uani 1 1 d . . . . .
H16A H 0.175512 1.144616 0.731154 0.074 Uiso 1 1 calc GR . . . .
H16B H 0.333796 1.139838 0.831774 0.074 Uiso 1 1 calc GR . . . .
H16C H 0.102895 1.061931 0.871726 0.074 Uiso 1 1 calc GR . . . .
C17 C 0.5948(3) 1.02955(14) 0.66490(15) 0.0476(4) Uani 1 1 d . . . . .
H17A H 0.683198 0.960198 0.641066 0.071 Uiso 1 1 calc GR . . . .
H17B H 0.699881 1.073303 0.691970 0.071 Uiso 1 1 calc GR . . . .
H17C H 0.532137 1.085457 0.593554 0.071 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 N1 1.3854(13) . ?
O1 C1 1.4431(16) . ?
O2 C1 1.2084(17) . ?
O3 C11 1.2185(15) . ?
N1 C3 1.3612(16) . ?
N1 C15 1.3578(16) . ?
C1 C2 1.404(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3634(18) . ?
C3 C4 1.4361(18) . ?
C4 C5 1.4007(18) . ?
C4 C9 1.4172(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.4083(17) . ?
C9 C10 1.4606(17) . ?
C10 C11 1.4737(17) . ?
C10 C15 1.3735(16) . ?
C11 C12 1.5034(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5282(18) . ?
C13 C14 1.5257(18) . ?
C13 C16 1.5287(18) . ?
C13 C17 1.524(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.4975(17) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
N1 O1 C1 105.33(10) . . ?
C3 N1 O1 110.51(10) . . ?
C15 N1 O1 121.00(10) . . ?
C15 N1 C3 128.48(11) . . ?
O2 C1 O1 116.55(13) . . ?
O2 C1 C2 136.65(14) . . ?
C2 C1 O1 106.80(11) . . ?
C1 C2 H2 125.7 . . ?
C3 C2 C1 108.55(12) . . ?
C3 C2 H2 125.7 . . ?
N1 C3 C2 108.80(12) . . ?
N1 C3 C4 116.04(11) . . ?
C2 C3 C4 135.15(12) . . ?
C5 C4 C3 119.67(12) . . ?
C5 C4 C9 121.26(12) . . ?
C9 C4 C3 119.07(11) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.93(13) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.01(13) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.95(13) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.17(13) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C10 119.31(11) . . ?
C8 C9 C4 116.65(12) . . ?
C8 C9 C10 124.03(11) . . ?
C9 C10 C11 123.27(11) . . ?
C15 C10 C9 120.20(11) . . ?
C15 C10 C11 116.53(11) . . ?
O3 C11 C10 123.33(12) . . ?
O3 C11 C12 119.18(12) . . ?
C10 C11 C12 117.48(11) . . ?
C11 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C11 C12 C13 115.31(11) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C12 C13 C16 109.57(11) . . ?
C14 C13 C12 107.62(11) . . ?
C14 C13 C16 109.09(11) . . ?
C17 C13 C12 110.93(12) . . ?
C17 C13 C14 110.06(11) . . ?
C17 C13 C16 109.52(12) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 C13 113.72(10) . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
N1 C15 C10 116.87(11) . . ?
N1 C15 C14 116.38(11) . . ?
C10 C15 C14 126.75(11) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 N1 C3 C2 0.40(15) . . . . ?
O1 N1 C3 C4 -178.29(10) . . . . ?
O1 N1 C15 C10 179.02(11) . . . . ?
O1 N1 C15 C14 0.08(18) . . . . ?
O1 C1 C2 C3 1.27(15) . . . . ?
O2 C1 C2 C3 -177.95(18) . . . . ?
O3 C11 C12 C13 141.27(14) . . . . ?
N1 O1 C1 O2 178.40(12) . . . . ?
N1 O1 C1 C2 -1.00(14) . . . . ?
N1 C3 C4 C5 178.78(12) . . . . ?
N1 C3 C4 C9 -1.01(17) . . . . ?
C1 O1 N1 C3 0.39(13) . . . . ?
C1 O1 N1 C15 179.95(11) . . . . ?
C1 C2 C3 N1 -1.05(16) . . . . ?
C1 C2 C3 C4 177.28(14) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C9 -179.24(14) . . . . ?
C3 N1 C15 C10 -1.5(2) . . . . ?
C3 N1 C15 C14 179.55(12) . . . . ?
C3 C4 C5 C6 179.99(13) . . . . ?
C3 C4 C9 C8 178.65(11) . . . . ?
C3 C4 C9 C10 -0.57(17) . . . . ?
C4 C5 C6 C7 1.2(2) . . . . ?
C4 C9 C10 C11 -178.22(11) . . . . ?
C4 C9 C10 C15 1.29(18) . . . . ?
C5 C4 C9 C8 -1.13(18) . . . . ?
C5 C4 C9 C10 179.65(12) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C4 1.56(19) . . . . ?
C7 C8 C9 C10 -179.26(12) . . . . ?
C8 C9 C10 C11 2.62(19) . . . . ?
C8 C9 C10 C15 -177.87(12) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
C9 C10 C11 O3 10.1(2) . . . . ?
C9 C10 C11 C12 -169.20(12) . . . . ?
C9 C10 C15 N1 -0.35(18) . . . . ?
C9 C10 C15 C14 178.46(12) . . . . ?
C10 C11 C12 C13 -39.42(18) . . . . ?
C11 C10 C15 N1 179.20(11) . . . . ?
C11 C10 C15 C14 -1.99(19) . . . . ?
C11 C12 C13 C14 54.30(16) . . . . ?
C11 C12 C13 C16 172.80(12) . . . . ?
C11 C12 C13 C17 -66.16(16) . . . . ?
C12 C13 C14 C15 -43.32(15) . . . . ?
C13 C14 C15 N1 -161.24(11) . . . . ?
C13 C14 C15 C10 19.95(19) . . . . ?
C15 N1 C3 C2 -179.12(13) . . . . ?
C15 N1 C3 C4 2.2(2) . . . . ?
C15 C10 C11 O3 -169.45(13) . . . . ?
C15 C10 C11 C12 11.27(17) . . . . ?
C16 C13 C14 C15 -162.13(12) . . . . ?
C17 C13 C14 C15 77.68(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
