# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_mo_21144_0m
_database_code_depnum_ccdc_archive 'CCDC 2084268'
loop_
_audit_author_name
_audit_author_address
'Maren Pink'
;Indiana University
United States of America
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-07-06 downloaded from the CCDC.
;
_audit_creation_date             2021-05-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
shaspaul@iu.edu
vcarta@iu.edu
brownmkb@indiana.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_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                   7.2901(2)
_cell_length_b                   10.5132(3)
_cell_length_c                   11.8680(4)
_cell_angle_alpha                71.2030(10)
_cell_angle_beta                 79.0020(10)
_cell_angle_gamma                83.4110(10)
_cell_volume                     843.87(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    143.0
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_preparation       synthesized
_exptl_crystal_recrystallization_method 
'Slow evaporation of a mixture of ethyl acetate and pentane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            57033
_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         27.484
_diffrn_reflns_theta_min         2.050
_diffrn_ambient_temperature      143.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_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                3014
_reflns_number_total             3879
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.026
_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)+(0.0579P)²+0.3404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C6-C5 \\sim C6-C5A
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C6-C1 \\sim C6-C1A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C6-C2 \\sim C6-C2A
 with sigma of 0.04
 C6-C4 \\sim C6-C4A
 with sigma of 0.04
 C5-C3 \\sim C5A-C3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C3A) = Uanis(C3)
Uanis(C5A) = Uanis(C5)
Uanis(C1A) = Uanis(C1)
Uanis(C4) = Uanis(C4A)
Uanis(C2A) = Uanis(C2)
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=
 Sof(C1A)=Sof(H1AA)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(C1)=Sof(H1A)=Sof(C3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(C4)=
 Sof(H4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C7(H7), C11(H11), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C17(H17), C20(H20), C16(H16), C21(H21), C22(H22), C5(H5),
 C1(H1A), C3(H3), C2(H2), C4(H4), C5A(H5A), C4A(H4A), C3A(H3A), C2A(H2A),
 C1A(H1AA)
;
_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 0.65680(16) 0.71456(11) 0.87180(10) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.58854(17) 0.53163(11) 0.82803(11) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.502116 0.500714 0.802759 0.031 Uiso 1 1 calc R U . . .
N2 N 0.57374(17) 0.28160(12) 0.82354(12) 0.0283(3) Uani 1 1 d . . . . .
C14 C 0.7499(2) 0.44710(14) 0.84762(12) 0.0233(3) Uani 1 1 d . . . . .
C19 C 0.73558(19) 0.31209(14) 0.84847(12) 0.0228(3) Uani 1 1 d . . . . .
C18 C 0.8880(2) 0.21691(14) 0.87374(12) 0.0243(3) Uani 1 1 d . . . . .
C13 C 0.5477(2) 0.65575(14) 0.84299(12) 0.0258(3) Uani 1 1 d . . . . .
C15 C 0.9129(2) 0.48332(15) 0.86747(13) 0.0281(3) Uani 1 1 d . . . . .
H15 H 0.924868 0.573545 0.864141 0.034 Uiso 1 1 calc R U . . .
C17 C 1.0516(2) 0.25691(15) 0.89705(13) 0.0290(3) Uani 1 1 d . . . . .
H17 H 1.153672 0.193316 0.915647 0.035 Uiso 1 1 calc R U . . .
C20 C 0.8646(2) 0.08457(15) 0.87533(14) 0.0304(3) Uani 1 1 d . . . . .
H20 H 0.962877 0.017098 0.892069 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3499(2) 0.71075(14) 0.82647(13) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.259684 0.658695 0.896188 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4086(2) 0.83345(14) 0.61101(13) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.338656 0.887570 0.544754 0.033 Uiso 1 1 calc R U . . .
C16 C 1.0630(2) 0.38648(16) 0.89286(14) 0.0303(3) Uani 1 1 d . . . . .
H16 H 1.174611 0.412635 0.907364 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4319(2) 0.92669(15) 0.68580(13) 0.0301(3) Uani 1 1 d . . . . .
H8A H 0.562568 0.922189 0.699615 0.036 Uiso 1 1 calc R U . . .
H8B H 0.391595 1.021368 0.646632 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5819(2) 0.76798(15) 0.55435(13) 0.0292(3) Uani 1 1 d D . . . .
C11 C 0.2711(2) 0.73680(15) 0.70743(14) 0.0277(3) Uani 1 1 d . . . . .
H11 H 0.224538 0.660907 0.689193 0.033 Uiso 1 1 calc R U . . .
C9 C 0.2997(2) 0.86315(14) 0.80267(14) 0.0290(3) Uani 1 1 d . . . . .
H9 H 0.280289 0.902699 0.870521 0.035 Uiso 1 1 calc R U . . .
C21 C 0.7017(2) 0.05372(15) 0.85292(15) 0.0341(4) Uani 1 1 d . . . . .
H21 H 0.683523 -0.035292 0.855516 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1301(2) 0.83889(15) 0.75354(14) 0.0317(3) Uani 1 1 d . . . . .
H10A H 0.087106 0.916757 0.689286 0.038 Uiso 1 1 calc R U . . .
H10B H 0.024691 0.797969 0.816147 0.038 Uiso 1 1 calc R U . . .
C22 C 0.5608(2) 0.15663(16) 0.82585(15) 0.0337(4) Uani 1 1 d . . . . .
H22 H 0.448997 0.134759 0.808038 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7632(5) 0.786(3) 0.562(2) 0.0425(8) Uani 0.856(13) 1 d D . P A 1
H5 H 0.786762 0.839399 0.608329 0.051 Uiso 0.856(13) 1 calc R U P A 1
C1 C 0.5507(6) 0.6921(3) 0.4829(2) 0.0343(6) Uani 0.856(13) 1 d D . P A 1
H1A H 0.426399 0.680339 0.476161 0.041 Uiso 0.856(13) 1 calc R U P A 1
C3 C 0.8818(7) 0.6505(4) 0.4306(2) 0.0413(10) Uani 0.856(13) 1 d D . P A 1
H3 H 0.984685 0.610663 0.388971 0.050 Uiso 0.856(13) 1 calc R U P A 1
C2 C 0.7015(7) 0.6336(3) 0.4216(2) 0.0415(8) Uani 0.856(13) 1 d D . P A 1
H2 H 0.679645 0.581955 0.373357 0.050 Uiso 0.856(13) 1 calc R U P A 1
C4 C 0.9117(5) 0.7255(5) 0.5004(3) 0.0493(9) Uani 0.856(13) 1 d D . P A 1
H4 H 1.036356 0.736374 0.506969 0.059 Uiso 0.856(13) 1 calc R U P A 1
C5A C 0.761(3) 0.793(17) 0.564(14) 0.0425(8) Uani 0.144(13) 1 d D . P A 2
H5A H 0.764138 0.838634 0.620182 0.051 Uiso 0.144(13) 1 calc R U P A 2
C4A C 0.939(3) 0.762(3) 0.504(3) 0.0493(9) Uani 0.144(13) 1 d D . P A 2
H4A H 1.048222 0.798601 0.509870 0.059 Uiso 0.144(13) 1 calc R U P A 2
C3A C 0.946(3) 0.676(2) 0.4358(17) 0.0413(10) Uani 0.144(13) 1 d D . P A 2
H3A H 1.059082 0.651765 0.391331 0.050 Uiso 0.144(13) 1 calc R U P A 2
C2A C 0.776(4) 0.6295(19) 0.4372(19) 0.0415(8) Uani 0.144(13) 1 d D . P A 2
H2A H 0.775678 0.561160 0.400843 0.050 Uiso 0.144(13) 1 calc R U P A 2
C1A C 0.610(3) 0.6758(19) 0.4878(18) 0.0343(6) Uani 0.144(13) 1 d D . P A 2
H1AA H 0.501190 0.642539 0.477364 0.041 Uiso 0.144(13) 1 calc R U P A 2


_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 C13 1.2183(18) . ?
N1 H1 0.8800 . ?
N1 C14 1.3999(18) . ?
N1 C13 1.3648(18) . ?
N2 C19 1.3650(19) . ?
N2 C22 1.3191(19) . ?
C14 C19 1.4318(19) . ?
C14 C15 1.371(2) . ?
C19 C18 1.4161(19) . ?
C18 C17 1.411(2) . ?
C18 C20 1.415(2) . ?
C13 C12 1.515(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.413(2) . ?
C17 H17 0.9500 . ?
C17 C16 1.359(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.361(2) . ?
C12 H12 1.0000 . ?
C12 C11 1.557(2) . ?
C12 C9 1.5473(19) . ?
C7 H7 1.0000 . ?
C7 C8 1.560(2) . ?
C7 C6 1.515(2) . ?
C7 C11 1.547(2) . ?
C16 H16 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(2) . ?
C6 C5 1.381(4) . ?
C6 C1 1.400(3) . ?
C6 C5A 1.391(18) . ?
C6 C1A 1.410(14) . ?
C11 H11 1.0000 . ?
C11 C10 1.555(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.542(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.405(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.397(5) . ?
C1 H1A 0.9500 . ?
C1 C2 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.375(3) . ?
C3 C4 1.372(4) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.409(17) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.380(16) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.377(15) . ?
C2A H2A 0.9500 . ?
C2A C1A 1.356(15) . ?
C1A H1AA 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
C14 N1 H1 115.8 . . ?
C13 N1 H1 115.8 . . ?
C13 N1 C14 128.46(13) . . ?
C22 N2 C19 117.34(13) . . ?
N1 C14 C19 115.03(12) . . ?
C15 C14 N1 125.37(13) . . ?
C15 C14 C19 119.59(13) . . ?
N2 C19 C14 117.73(12) . . ?
N2 C19 C18 122.92(13) . . ?
C18 C19 C14 119.34(13) . . ?
C17 C18 C19 119.46(13) . . ?
C17 C18 C20 123.72(13) . . ?
C20 C18 C19 116.82(13) . . ?
O1 C13 N1 123.40(14) . . ?
O1 C13 C12 122.98(13) . . ?
N1 C13 C12 113.55(12) . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.02(13) . . ?
C16 C15 H15 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.92(14) . . ?
C16 C17 H17 120.0 . . ?
C18 C20 H20 119.9 . . ?
C21 C20 C18 120.14(14) . . ?
C21 C20 H20 119.9 . . ?
C13 C12 H12 109.4 . . ?
C13 C12 C11 123.73(12) . . ?
C13 C12 C9 119.59(12) . . ?
C11 C12 H12 109.4 . . ?
C9 C12 H12 109.4 . . ?
C9 C12 C11 82.70(11) . . ?
C8 C7 H7 107.6 . . ?
C6 C7 H7 107.6 . . ?
C6 C7 C8 118.96(13) . . ?
C6 C7 C11 116.17(12) . . ?
C11 C7 H7 107.6 . . ?
C11 C7 C8 98.23(11) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.62(14) . . ?
C17 C16 H16 119.2 . . ?
C7 C8 H8A 111.7 . . ?
C7 C8 H8B 111.7 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 C7 100.12(11) . . ?
C9 C8 H8A 111.7 . . ?
C9 C8 H8B 111.7 . . ?
C5 C6 C7 124.7(3) . . ?
C5 C6 C1 119.4(3) . . ?
C1 C6 C7 115.7(2) . . ?
C5A C6 C7 121.8(17) . . ?
C5A C6 C1A 105(2) . . ?
C1A C6 C7 133.5(9) . . ?
C12 C11 H11 120.2 . . ?
C7 C11 C12 103.81(12) . . ?
C7 C11 H11 120.2 . . ?
C7 C11 C10 100.77(12) . . ?
C10 C11 C12 84.91(11) . . ?
C10 C11 H11 120.2 . . ?
C12 C9 H9 120.1 . . ?
C8 C9 C12 102.86(12) . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 101.44(12) . . ?
C10 C9 C12 85.70(11) . . ?
C10 C9 H9 120.1 . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.44(14) . . ?
C22 C21 H21 120.8 . . ?
C11 C10 H10A 114.8 . . ?
C11 C10 H10B 114.8 . . ?
C9 C10 C11 82.96(11) . . ?
C9 C10 H10A 114.8 . . ?
C9 C10 H10B 114.8 . . ?
H10A C10 H10B 111.9 . . ?
N2 C22 C21 124.31(14) . . ?
N2 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.2(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C1 H1A 119.9 . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 H1A 119.9 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C6 C5A H5A 114.3 . . ?
C6 C5A C4A 131(2) . . ?
C4A C5A H5A 114.3 . . ?
C5A C4A H4A 121.6 . . ?
C3A C4A C5A 117(2) . . ?
C3A C4A H4A 121.6 . . ?
C4A C3A H3A 122.4 . . ?
C2A C3A C4A 115.1(14) . . ?
C2A C3A H3A 122.4 . . ?
C3A C2A H2A 118.4 . . ?
C1A C2A C3A 123.2(16) . . ?
C1A C2A H2A 118.4 . . ?
C6 C1A H1AA 116.3 . . ?
C2A C1A C6 127.3(14) . . ?
C2A C1A H1AA 116.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15 O1 0.95 2.32 2.8982(19) 118.7 . yes
C21 H21 O1 0.95 2.60 3.5492(18) 175.4 1_545 yes

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 C13 C12 C11 122.75(16) . . . . ?
O1 C13 C12 C9 21.0(2) . . . . ?
N1 C14 C19 N2 3.74(18) . . . . ?
N1 C14 C19 C18 -176.78(12) . . . . ?
N1 C14 C15 C16 176.44(13) . . . . ?
N1 C13 C12 C11 -60.13(18) . . . . ?
N1 C13 C12 C9 -161.87(12) . . . . ?
N2 C19 C18 C17 179.15(13) . . . . ?
N2 C19 C18 C20 -1.6(2) . . . . ?
C14 N1 C13 O1 3.7(2) . . . . ?
C14 N1 C13 C12 -173.46(13) . . . . ?
C14 C19 C18 C17 -0.3(2) . . . . ?
C14 C19 C18 C20 178.96(13) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C19 N2 C22 C21 0.4(2) . . . . ?
C19 C14 C15 C16 -2.3(2) . . . . ?
C19 C18 C17 C16 -1.2(2) . . . . ?
C19 C18 C20 C21 0.2(2) . . . . ?
C18 C17 C16 C15 1.1(2) . . . . ?
C18 C20 C21 C22 1.4(2) . . . . ?
C13 N1 C14 C19 167.41(13) . . . . ?
C13 N1 C14 C15 -11.3(2) . . . . ?
C13 C12 C11 C7 -56.47(16) . . . . ?
C13 C12 C11 C10 -156.33(14) . . . . ?
C13 C12 C9 C8 59.81(16) . . . . ?
C13 C12 C9 C10 160.58(13) . . . . ?
C15 C14 C19 N2 -177.42(13) . . . . ?
C15 C14 C19 C18 2.1(2) . . . . ?
C17 C18 C20 C21 179.40(15) . . . . ?
C20 C18 C17 C16 179.55(14) . . . . ?
C20 C21 C22 N2 -1.8(3) . . . . ?
C12 C11 C10 C9 35.58(10) . . . . ?
C12 C9 C10 C11 -35.80(10) . . . . ?
C7 C8 C9 C12 44.94(14) . . . . ?
C7 C8 C9 C10 -43.22(13) . . . . ?
C7 C6 C5 C4 -176.7(14) . . . . ?
C7 C6 C1 C2 176.6(2) . . . . ?
C7 C6 C5A C4A -168(13) . . . . ?
C7 C6 C1A C2A 176.8(15) . . . . ?
C7 C11 C10 C9 -67.54(12) . . . . ?
C8 C7 C6 C5 -1.2(17) . . . . ?
C8 C7 C6 C1 -176.44(18) . . . . ?
C8 C7 C6 C5A -2(10) . . . . ?
C8 C7 C6 C1A 176.6(13) . . . . ?
C8 C7 C11 C12 -41.96(13) . . . . ?
C8 C7 C11 C10 45.39(13) . . . . ?
C8 C9 C10 C11 66.46(12) . . . . ?
C6 C7 C8 C9 -127.63(13) . . . . ?
C6 C7 C11 C12 86.08(14) . . . . ?
C6 C7 C11 C10 173.42(12) . . . . ?
C6 C5 C4 C3 1(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C5A C4A C3A -11(23) . . . . ?
C11 C12 C9 C8 -65.01(12) . . . . ?
C11 C12 C9 C10 35.76(10) . . . . ?
C11 C7 C8 C9 -1.52(13) . . . . ?
C11 C7 C6 C5 -118.2(17) . . . . ?
C11 C7 C6 C1 66.5(2) . . . . ?
C11 C7 C6 C5A -119(10) . . . . ?
C11 C7 C6 C1A 59.5(13) . . . . ?
C9 C12 C11 C7 64.40(12) . . . . ?
C9 C12 C11 C10 -35.46(10) . . . . ?
C22 N2 C19 C14 -179.25(13) . . . . ?
C22 N2 C19 C18 1.3(2) . . . . ?
C5 C6 C1 C2 1.1(16) . . . . ?
C1 C6 C5 C4 -2(3) . . . . ?
C2 C3 C4 C5 -0.5(17) . . . . ?
C4 C3 C2 C1 -0.1(4) . . . . ?
C5A C6 C1A C2A -4(9) . . . . ?
C5A C4A C3A C2A -1(10) . . . . ?
C4A C3A C2A C1A 8(4) . . . . ?
C3A C2A C1A C6 -6(4) . . . . ?
C1A C6 C5A C4A 12(21) . . . . ?

_olex2_submission_original_sample_id SHP-II-171
_olex2_submission_special_instructions 'No special instructions were received'
