# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_lbz_b130
_database_code_depnum_ccdc_archive 'CCDC 2144495'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_audit_creation_date             2021-10-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_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                   5.8248(4)
_cell_length_b                   28.7309(17)
_cell_length_c                   8.8878(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.165(2)
_cell_angle_gamma                90
_cell_volume                     1428.58(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1280 before and 0.0562 after correction.
The Ratio of minimum to maximum transmission is 0.9586.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            72974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.523
_diffrn_reflns_theta_min         2.489
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3755
_reflns_number_total             4356
_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+ Ver. 8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT+ Ver. 8.40B (Bruker, 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0052(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.040
_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)+(0.0456P)²+0.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1024
_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:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.07705(13) 0.40972(2) -0.02948(9) 0.02323(16) Uani 1 1 d . . . . .
O2 O 0.72079(14) 0.32891(3) 0.26265(10) 0.02757(18) Uani 1 1 d . . . . .
N1 N 0.42223(14) 0.37858(3) 0.13351(9) 0.01427(15) Uani 1 1 d . . . . .
N2 N 0.31310(17) 0.35494(3) 0.67460(10) 0.02505(19) Uani 1 1 d . . . . .
C1 C 0.13534(17) 0.32557(3) -0.00829(11) 0.01760(18) Uani 1 1 d . . . . .
H1A H 0.116529 0.318525 -0.120111 0.021 Uiso 1 1 calc R U . . .
H1B H -0.015790 0.317799 0.016366 0.021 Uiso 1 1 calc R U . . .
C2 C 0.19623(16) 0.37625(3) 0.02509(10) 0.01523(17) Uani 1 1 d . . . . .
C3 C 0.52217(17) 0.33489(3) 0.17634(11) 0.01650(17) Uani 1 1 d . . . . .
C4 C 0.34404(16) 0.29748(3) 0.09659(11) 0.01643(17) Uani 1 1 d . . . . .
C5 C 0.46590(19) 0.26566(4) 0.00425(14) 0.0271(2) Uani 1 1 d . . . . .
H5A H 0.354679 0.241078 -0.046746 0.041 Uiso 1 1 calc R U . . .
H5B H 0.608107 0.251592 0.075775 0.041 Uiso 1 1 calc R U . . .
H5C H 0.513011 0.283909 -0.075458 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2677(2) 0.27020(4) 0.22268(13) 0.0268(2) Uani 1 1 d . . . . .
H6A H 0.187603 0.291211 0.278765 0.040 Uiso 1 1 calc R U . . .
H6B H 0.409139 0.256668 0.296674 0.040 Uiso 1 1 calc R U . . .
H6C H 0.157678 0.245264 0.173280 0.040 Uiso 1 1 calc R U . . .
C7 C 0.54351(16) 0.42124(3) 0.19100(11) 0.01541(17) Uani 1 1 d . . . . .
C8 C 0.64311(17) 0.44647(3) 0.09179(11) 0.01919(19) Uani 1 1 d . . . . .
H8 H 0.628871 0.435479 -0.011223 0.023 Uiso 1 1 calc R U . . .
C9 C 0.76390(18) 0.48786(3) 0.14294(13) 0.0222(2) Uani 1 1 d . . . . .
H9 H 0.831583 0.505273 0.075046 0.027 Uiso 1 1 calc R U . . .
C10 C 0.78464(18) 0.50346(3) 0.29371(13) 0.0227(2) Uani 1 1 d . . . . .
H10 H 0.862895 0.532122 0.328269 0.027 Uiso 1 1 calc R U . . .
C11 C 0.69160(17) 0.47738(3) 0.39444(12) 0.02054(19) Uani 1 1 d . . . . .
H11 H 0.712431 0.487929 0.498689 0.025 Uiso 1 1 calc R U . . .
C12 C 0.56757(16) 0.43581(3) 0.34540(11) 0.01612(17) Uani 1 1 d . . . . .
C13 C 0.47442(16) 0.40850(3) 0.45742(11) 0.01652(17) Uani 1 1 d . . . . .
C14 C 0.62178(17) 0.39921(3) 0.60787(11) 0.02004(19) Uani 1 1 d . . . . .
H14 H 0.780407 0.410975 0.639742 0.024 Uiso 1 1 calc R U . . .
C15 C 0.53456(19) 0.37273(4) 0.70988(12) 0.0234(2) Uani 1 1 d . . . . .
H15 H 0.638091 0.366788 0.811290 0.028 Uiso 1 1 calc R U . . .
C16 C 0.17054(18) 0.36491(4) 0.53141(12) 0.0216(2) Uani 1 1 d . . . . .
H16 H 0.011699 0.353232 0.503918 0.026 Uiso 1 1 calc R U . . .
C17 C 0.24117(17) 0.39127(3) 0.42100(11) 0.01834(18) Uani 1 1 d . . . . .
H17 H 0.131943 0.397509 0.321753 0.022 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
O1 C2 1.2059(11) . ?
O2 C3 1.2093(12) . ?
N1 C2 1.3999(11) . ?
N1 C3 1.3914(11) . ?
N1 C7 1.4358(11) . ?
N2 C15 1.3410(14) . ?
N2 C16 1.3426(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5085(12) . ?
C1 C4 1.5384(13) . ?
C3 C4 1.5247(12) . ?
C4 C5 1.5290(14) . ?
C4 C6 1.5313(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3872(13) . ?
C7 C12 1.4038(13) . ?
C8 H8 0.9500 . ?
C8 C9 1.3920(13) . ?
C9 H9 0.9500 . ?
C9 C10 1.3860(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3880(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.4012(12) . ?
C12 C13 1.4839(13) . ?
C13 C14 1.3989(13) . ?
C13 C17 1.3967(13) . ?
C14 H14 0.9500 . ?
C14 C15 1.3840(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.3895(14) . ?
C17 H17 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
C2 N1 C7 124.13(7) . . ?
C3 N1 C2 112.75(7) . . ?
C3 N1 C7 123.08(7) . . ?
C15 N2 C16 116.18(9) . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
C2 C1 C4 106.51(7) . . ?
C4 C1 H1A 110.4 . . ?
C4 C1 H1B 110.4 . . ?
O1 C2 N1 124.36(8) . . ?
O1 C2 C1 127.81(8) . . ?
N1 C2 C1 107.82(7) . . ?
O2 C3 N1 123.73(8) . . ?
O2 C3 C4 127.00(8) . . ?
N1 C3 C4 109.27(7) . . ?
C3 C4 C1 103.45(7) . . ?
C3 C4 C5 108.27(8) . . ?
C3 C4 C6 108.62(8) . . ?
C5 C4 C1 113.27(8) . . ?
C5 C4 C6 111.06(8) . . ?
C6 C4 C1 111.75(8) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 118.11(8) . . ?
C8 C7 C12 121.33(8) . . ?
C12 C7 N1 120.51(8) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.10(9) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.48(9) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.29(9) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.30(9) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C13 122.86(8) . . ?
C11 C12 C7 117.43(9) . . ?
C11 C12 C13 119.68(8) . . ?
C14 C13 C12 120.04(8) . . ?
C17 C13 C12 123.07(8) . . ?
C17 C13 C14 116.89(9) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.45(9) . . ?
C15 C14 H14 120.3 . . ?
N2 C15 C14 124.12(9) . . ?
N2 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
N2 C16 H16 118.0 . . ?
N2 C16 C17 123.99(9) . . ?
C17 C16 H16 118.0 . . ?
C13 C17 H17 120.3 . . ?
C16 C17 C13 119.32(9) . . ?
C16 C17 H17 120.3 . . ?

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
O2 C3 C4 C1 -175.14(10) . . . . ?
O2 C3 C4 C5 -54.70(13) . . . . ?
O2 C3 C4 C6 66.00(13) . . . . ?
N1 C3 C4 C1 4.27(10) . . . . ?
N1 C3 C4 C5 124.72(9) . . . . ?
N1 C3 C4 C6 -114.58(9) . . . . ?
N1 C7 C8 C9 -179.53(8) . . . . ?
N1 C7 C12 C11 178.92(8) . . . . ?
N1 C7 C12 C13 0.79(13) . . . . ?
N2 C16 C17 C13 0.68(15) . . . . ?
C2 N1 C3 O2 176.31(9) . . . . ?
C2 N1 C3 C4 -3.13(11) . . . . ?
C2 N1 C7 C8 -74.32(12) . . . . ?
C2 N1 C7 C12 108.06(10) . . . . ?
C2 C1 C4 C3 -3.86(10) . . . . ?
C2 C1 C4 C5 -120.85(9) . . . . ?
C2 C1 C4 C6 112.80(9) . . . . ?
C3 N1 C2 O1 -179.37(9) . . . . ?
C3 N1 C2 C1 0.50(11) . . . . ?
C3 N1 C7 C8 103.37(10) . . . . ?
C3 N1 C7 C12 -74.25(12) . . . . ?
C4 C1 C2 O1 -177.87(10) . . . . ?
C4 C1 C2 N1 2.27(10) . . . . ?
C7 N1 C2 O1 -1.46(15) . . . . ?
C7 N1 C2 C1 178.40(8) . . . . ?
C7 N1 C3 O2 -1.61(15) . . . . ?
C7 N1 C3 C4 178.95(8) . . . . ?
C7 C8 C9 C10 0.31(14) . . . . ?
C7 C12 C13 C14 130.63(10) . . . . ?
C7 C12 C13 C17 -49.81(13) . . . . ?
C8 C7 C12 C11 1.38(13) . . . . ?
C8 C7 C12 C13 -176.75(9) . . . . ?
C8 C9 C10 C11 1.80(15) . . . . ?
C9 C10 C11 C12 -2.35(15) . . . . ?
C10 C11 C12 C7 0.76(14) . . . . ?
C10 C11 C12 C13 178.95(9) . . . . ?
C11 C12 C13 C14 -47.46(12) . . . . ?
C11 C12 C13 C17 132.10(10) . . . . ?
C12 C7 C8 C9 -1.92(14) . . . . ?
C12 C13 C14 C15 -178.42(9) . . . . ?
C12 C13 C17 C16 178.22(9) . . . . ?
C13 C14 C15 N2 -0.22(16) . . . . ?
C14 C13 C17 C16 -2.20(13) . . . . ?
C15 N2 C16 C17 1.11(15) . . . . ?
C16 N2 C15 C14 -1.35(16) . . . . ?
C17 C13 C14 C15 1.99(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
