# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cu_220705_xjq_0m
_database_code_depnum_ccdc_archive 'CCDC 2350769'
loop_
_audit_author_name
_audit_author_address
'Ren-Xiao Liang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-07-07
_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 H15 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.2774(3)
_cell_length_b                   11.2639(4)
_cell_length_c                   12.0479(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1259.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.92
_shelx_estimated_absorpt_T_max   0.790
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.7528.
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    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10268
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.315
_diffrn_reflns_theta_min         5.376
_diffrn_ambient_temperature      169.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2282
_reflns_number_total             2293
_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         0.344
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 
;
 Flack x determined using 949 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.256
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.256
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+0.1218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1199
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.0091(2) 0.62687(15) 0.62028(16) 0.0273(4) Uani 1 1 d . . . . .
O2 O 0.02493(19) 0.37085(15) 0.88633(16) 0.0259(4) Uani 1 1 d . . . . .
H2 H -0.003222 0.301307 0.873523 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.16375(19) 0.54014(16) 0.74675(15) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.0140(2) 0.3727(2) 0.51644(19) 0.0198(5) Uani 1 1 d . . . . .
H1 H -0.049294 0.419681 0.472722 0.024 Uiso 1 1 calc R . . . .
C2 C 0.0420(3) 0.2546(2) 0.48959(19) 0.0208(5) Uani 1 1 d . . . . .
H2A H -0.002124 0.220402 0.426024 0.025 Uiso 1 1 calc R . . . .
C3 C 0.1338(3) 0.1861(2) 0.5547(2) 0.0216(5) Uani 1 1 d . . . . .
H3 H 0.150692 0.105589 0.535135 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2014(2) 0.2335(2) 0.64804(19) 0.0187(5) Uani 1 1 d . . . . .
H4 H 0.264175 0.186745 0.692428 0.022 Uiso 1 1 calc R . . . .
C5 C 0.1741(2) 0.35075(19) 0.67373(18) 0.0150(4) Uani 1 1 d . . . . .
C6 C 0.0821(2) 0.41919(18) 0.60946(18) 0.0151(5) Uani 1 1 d . . . . .
C7 C 0.0772(2) 0.5410(2) 0.65668(19) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.2310(2) 0.42418(18) 0.77011(18) 0.0152(5) Uani 1 1 d . . . . .
C9 C 0.1920(3) 0.64377(19) 0.8149(2) 0.0221(5) Uani 1 1 d . . . . .
H9A H 0.289840 0.672614 0.800450 0.033 Uiso 1 1 calc GR . . . .
H9B H 0.182783 0.622429 0.893436 0.033 Uiso 1 1 calc GR . . . .
H9C H 0.122318 0.706273 0.796837 0.033 Uiso 1 1 calc GR . . . .
C10 C 0.1772(3) 0.3748(2) 0.88192(18) 0.0200(5) Uani 1 1 d . . . . .
H10A H 0.216232 0.293875 0.892871 0.024 Uiso 1 1 calc R . . . .
H10B H 0.213580 0.425576 0.942908 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3963(2) 0.43399(19) 0.76581(19) 0.0170(5) Uani 1 1 d . . . . .
C12 C 0.4603(3) 0.5053(2) 0.6846(2) 0.0233(5) Uani 1 1 d . . . . .
H12 H 0.401257 0.548788 0.634624 0.028 Uiso 1 1 calc R . . . .
C13 C 0.6091(3) 0.5133(2) 0.6760(2) 0.0310(6) Uani 1 1 d . . . . .
H13 H 0.651253 0.561738 0.620271 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6970(3) 0.4500(2) 0.7494(2) 0.0335(7) Uani 1 1 d . . . . .
H14 H 0.798982 0.455207 0.743795 0.040 Uiso 1 1 calc R . . . .
C15 C 0.6347(3) 0.3804(3) 0.8294(2) 0.0334(6) Uani 1 1 d . . . . .
H15 H 0.694282 0.337769 0.879611 0.040 Uiso 1 1 calc R . . . .
C16 C 0.4849(3) 0.3711(2) 0.8383(2) 0.0252(5) Uani 1 1 d . . . . .
H16 H 0.443520 0.321874 0.893770 0.030 Uiso 1 1 calc R . . . .


_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 C7 1.236(3) . ?
O2 H2 0.8400 . ?
O2 C10 1.415(3) . ?
N1 C7 1.350(3) . ?
N1 C8 1.475(3) . ?
N1 C9 1.451(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(3) . ?
C1 C6 1.389(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 C6 1.386(3) . ?
C5 C8 1.520(3) . ?
C6 C7 1.486(3) . ?
C8 C10 1.540(3) . ?
C8 C11 1.538(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.399(3) . ?
C11 C16 1.393(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.370(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(4) . ?
C16 H16 0.9500 . ?

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
C10 O2 H2 109.5 . . ?
C7 N1 C8 114.29(18) . . ?
C7 N1 C9 123.81(19) . . ?
C9 N1 C8 121.89(17) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C6 C1 C2 117.5(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 C8 128.9(2) . . ?
C6 C5 C8 109.75(19) . . ?
C1 C6 C7 130.0(2) . . ?
C5 C6 C1 121.39(19) . . ?
C5 C6 C7 108.56(18) . . ?
O1 C7 N1 126.5(2) . . ?
O1 C7 C6 127.0(2) . . ?
N1 C7 C6 106.44(18) . . ?
N1 C8 C5 100.91(17) . . ?
N1 C8 C10 110.47(17) . . ?
N1 C8 C11 110.58(16) . . ?
C5 C8 C10 111.07(17) . . ?
C5 C8 C11 111.06(18) . . ?
C11 C8 C10 112.21(18) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C8 111.57(18) . . ?
O2 C10 H10A 109.3 . . ?
O2 C10 H10B 109.3 . . ?
C8 C10 H10A 109.3 . . ?
C8 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C8 119.2(2) . . ?
C16 C11 C8 122.1(2) . . ?
C16 C11 C12 118.6(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

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
N1 C8 C10 O2 53.7(2) . . . . ?
N1 C8 C11 C12 -39.1(3) . . . . ?
N1 C8 C11 C16 143.0(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 O1 -0.1(4) . . . . ?
C1 C6 C7 N1 -179.3(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 178.1(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 C8 179.3(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C8 N1 178.6(2) . . . . ?
C4 C5 C8 C10 -64.3(3) . . . . ?
C4 C5 C8 C11 61.4(3) . . . . ?
C5 C6 C7 O1 178.4(2) . . . . ?
C5 C6 C7 N1 -0.7(2) . . . . ?
C5 C8 C10 O2 -57.4(2) . . . . ?
C5 C8 C11 C12 72.1(2) . . . . ?
C5 C8 C11 C16 -105.9(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C5 C8 N1 -2.3(2) . . . . ?
C6 C5 C8 C10 114.8(2) . . . . ?
C6 C5 C8 C11 -119.6(2) . . . . ?
C7 N1 C8 C5 1.9(2) . . . . ?
C7 N1 C8 C10 -115.6(2) . . . . ?
C7 N1 C8 C11 119.5(2) . . . . ?
C8 N1 C7 O1 180.0(2) . . . . ?
C8 N1 C7 C6 -0.9(2) . . . . ?
C8 C5 C6 C1 -179.33(19) . . . . ?
C8 C5 C6 C7 2.0(2) . . . . ?
C8 C11 C12 C13 -178.0(2) . . . . ?
C8 C11 C16 C15 178.3(2) . . . . ?
C9 N1 C7 O1 -1.1(4) . . . . ?
C9 N1 C7 C6 178.08(19) . . . . ?
C9 N1 C8 C5 -177.03(19) . . . . ?
C9 N1 C8 C10 65.4(2) . . . . ?
C9 N1 C8 C11 -59.4(3) . . . . ?
C10 C8 C11 C12 -162.9(2) . . . . ?
C10 C8 C11 C16 19.1(3) . . . . ?
C11 C8 C10 O2 177.61(18) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C11 -0.6(4) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
