# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
# this file and to allow appropriate attribution of the data. 
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data_cha2402
_database_code_depnum_ccdc_archive 'CCDC 2116653'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2021-10-19 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_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
lea.thai-savard@umontreal.ca
thierry.maris@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        
'((1R,2R)-2-Methoxycyclobutyl)methyl 4-nitrobenzoate'
_chemical_formula_moiety         'C13 H15 N O5'
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26
_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      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                   6.2791(1)
_cell_length_b                   26.4160(6)
_cell_length_c                   8.3767(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.284(1)
_cell_angle_gamma                90
_cell_volume                     1311.48(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6349
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.959
_cell_measurement_theta_min      3.346
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_T_max  0.3857
_exptl_absorpt_correction_T_min  0.2792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0485 after correction.
The Ratio of minimum to maximum transmission is 0.7239.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'crystallized from diethylether/Hexanes'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.102
_diffrn_reflns_theta_min         3.346
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2408
_reflns_number_total             2574
_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 (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     182
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.079
_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)+(0.0509P)²+0.7649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1A-C2A \\sim C1B-C2B
 with sigma of 0.02
 C2A-C3A \\sim C2B-C3B
 with sigma of 0.02
 C3A-C4A \\sim C3B-C4B
 with sigma of 0.02
 C1A-C4A \\sim C1B-C4B
 with sigma of 0.02
 C1A-C3A \\sim C1A-C3B \\sim C2A-C4A \\sim C2B-C4B
 with sigma of 0.002
 O1A-C5A \\sim O1B-C5B
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O1A \\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim O1B \\sim C1B \\sim
C2B \\sim C3B \\sim C4B: within 1.7A with sigma of 0.002 and sigma for terminal
atoms of 0.02 within 1.7A
N1 \\sim O4A \\sim O5A \\sim O4B \\sim O5B: within 1.7A with sigma of 0.002 and
sigma for terminal atoms of 0.02 within 1.7A
Uanis(C5A) = Uanis(C5B)
Uanis(O4A) = Uanis(O4B)
Uanis(O5A) = Uanis(O5B)
4. Others
 Sof(H6BC)=Sof(H6BD)=Sof(O1B)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=
 Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=
 Sof(H5BC)=1-FVAR(1)
 Sof(H6A)=Sof(H6B)=Sof(O1A)=Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=
 Sof(H5AC)=FVAR(1)
 Sof(O4B)=Sof(O5B)=1-FVAR(2)
 Sof(O4A)=Sof(O5A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1A(H1A), C2A(H2A), C1B(H1B), C2B(H2B)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6(H6BC,H6BD), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C3B(H3BA,H3BB),
 C4B(H4BA,H4BB)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
5.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC)
;
_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
O2 O 0.5016(2) 0.56670(5) 0.36950(18) 0.0405(3) Uani 1 1 d . . . . .
O3 O 0.1495(2) 0.54382(6) 0.2290(2) 0.0528(4) Uani 1 1 d . . . . .
N1 N 0.7189(3) 0.36382(5) 0.04540(19) 0.0365(3) Uani 1 1 d . U . . .
C6 C 0.4186(3) 0.61119(7) 0.4338(2) 0.0374(4) Uani 1 1 d . . . . .
H6A H 0.309257 0.601383 0.490514 0.045 Uiso 0.8694(17) 1 calc R U P A 1
H6B H 0.344588 0.635057 0.340925 0.045 Uiso 0.8694(17) 1 calc R U P A 1
H6BC H 0.419590 0.604976 0.550580 0.045 Uiso 0.1306(17) 1 calc R U P A 2
H6BD H 0.262098 0.618918 0.361795 0.045 Uiso 0.1306(17) 1 calc R U P A 2
C7 C 0.3477(3) 0.53633(6) 0.2695(2) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.4514(3) 0.49164(6) 0.21343(19) 0.0266(3) Uani 1 1 d . . . . .
C9 C 0.6831(3) 0.48321(6) 0.2717(2) 0.0328(4) Uani 1 1 d . . . . .
H9 H 0.780397 0.506387 0.348549 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7724(3) 0.44108(7) 0.2181(2) 0.0357(4) Uani 1 1 d . . . . .
H10 H 0.930165 0.434728 0.257941 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6250(3) 0.40849(6) 0.1046(2) 0.0293(3) Uani 1 1 d . . . . .
C12 C 0.3952(3) 0.41613(6) 0.0430(2) 0.0316(4) Uani 1 1 d . . . . .
H12 H 0.298623 0.393091 -0.034876 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3092(3) 0.45846(6) 0.0982(2) 0.0309(4) Uani 1 1 d . . . . .
H13 H 0.151458 0.464830 0.056768 0.037 Uiso 1 1 calc R U . . .
O1A O 0.3532(2) 0.69114(5) 0.62994(18) 0.0358(3) Uani 0.8694(17) 1 d D U P A 1
O4A O 0.5866(6) 0.33411(12) -0.0508(4) 0.0441(6) Uani 0.855(8) 1 d . U P B 1
O5A O 0.9279(4) 0.35819(9) 0.0959(4) 0.0435(6) Uani 0.855(8) 1 d . U P B 1
C1A C 0.5747(3) 0.68571(7) 0.6271(3) 0.0334(4) Uani 0.8694(17) 1 d D U P A 1
H1A H 0.687090 0.692824 0.741091 0.040 Uiso 0.8694(17) 1 calc R U P A 1
C2A C 0.6256(3) 0.63459(6) 0.5577(2) 0.0314(4) Uani 0.8694(17) 1 d D U P A 1
H2A H 0.715669 0.610721 0.647237 0.038 Uiso 0.8694(17) 1 calc R U P A 1
C3A C 0.7682(3) 0.66412(7) 0.4689(3) 0.0347(4) Uani 0.8694(17) 1 d D U P A 1
H3AA H 0.740194 0.653914 0.349991 0.042 Uiso 0.8694(17) 1 calc R U P A 1
H3AB H 0.931680 0.664837 0.533395 0.042 Uiso 0.8694(17) 1 calc R U P A 1
C4A C 0.6398(4) 0.71272(7) 0.4888(3) 0.0377(4) Uani 0.8694(17) 1 d D U P A 1
H4AA H 0.738635 0.742500 0.529345 0.045 Uiso 0.8694(17) 1 calc R U P A 1
H4AB H 0.509841 0.721206 0.387366 0.045 Uiso 0.8694(17) 1 calc R U P A 1
C5A C 0.3159(4) 0.74131(9) 0.6757(3) 0.0433(6) Uani 0.8694(17) 1 d D U P A 1
H5AA H 0.324730 0.764838 0.587612 0.065 Uiso 0.8694(17) 1 calc R U P A 1
H5AB H 0.431027 0.750161 0.783337 0.065 Uiso 0.8694(17) 1 calc R U P A 1
H5AC H 0.166033 0.743551 0.687556 0.065 Uiso 0.8694(17) 1 calc R U P A 1
O1B O 0.3421(16) 0.7161(3) 0.5229(12) 0.0355(8) Uani 0.1306(17) 1 d D U P A 2
O4B O 0.589(4) 0.3291(9) -0.005(2) 0.0441(6) Uani 0.145(8) 1 d . U P B 2
O5B O 0.884(2) 0.3698(5) 0.025(2) 0.0435(6) Uani 0.145(8) 1 d . U P B 2
C1B C 0.554(2) 0.7066(5) 0.5315(17) 0.0340(7) Uani 0.1306(17) 1 d D U P A 2
H1B H 0.622227 0.737584 0.499702 0.041 Uiso 0.1306(17) 1 calc R U P A 2
C2B C 0.593(2) 0.6606(5) 0.4310(12) 0.0340(7) Uani 0.1306(17) 1 d D U P A 2
H2B H 0.615738 0.667926 0.320792 0.041 Uiso 0.1306(17) 1 calc R U P A 2
C3B C 0.803(2) 0.6455(5) 0.5795(16) 0.0339(8) Uani 0.1306(17) 1 d D U P A 2
H3BA H 0.947312 0.655382 0.564555 0.041 Uiso 0.1306(17) 1 calc R U P A 2
H3BB H 0.805339 0.609437 0.612718 0.041 Uiso 0.1306(17) 1 calc R U P A 2
C4B C 0.723(2) 0.6823(5) 0.6931(11) 0.0338(8) Uani 0.1306(17) 1 d D U P A 2
H4BA H 0.841661 0.705787 0.759967 0.041 Uiso 0.1306(17) 1 calc R U P A 2
H4BB H 0.649068 0.665080 0.766013 0.041 Uiso 0.1306(17) 1 calc R U P A 2
C5B C 0.338(3) 0.7582(5) 0.627(2) 0.0433(6) Uani 0.1306(17) 1 d D . P A 2
H5BA H 0.389428 0.788516 0.583712 0.065 Uiso 0.1306(17) 1 calc R U P A 2
H5BB H 0.437426 0.751532 0.743048 0.065 Uiso 0.1306(17) 1 calc R U P A 2
H5BC H 0.183350 0.763477 0.627585 0.065 Uiso 0.1306(17) 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
O2 C6 1.459(2) . ?
O2 C7 1.321(2) . ?
O3 C7 1.193(2) . ?
N1 C11 1.476(2) . ?
N1 O4A 1.230(4) . ?
N1 O5A 1.248(3) . ?
N1 O4B 1.21(2) . ?
N1 O5B 1.116(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 C2A 1.502(3) . ?
C6 C2B 1.707(13) . ?
C7 C8 1.497(2) . ?
C8 C9 1.391(2) . ?
C8 C13 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 C12 1.378(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13 0.9500 . ?
O1A C1A 1.406(2) . ?
O1A C5A 1.420(2) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.545(2) . ?
C1A C4A 1.527(3) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.550(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.553(3) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
O1B C1B 1.331(17) . ?
O1B C5B 1.420(3) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.542(13) . ?
C1B C4B 1.557(14) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.539(14) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.556(13) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?

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
C7 O2 C6 116.62(13) . . ?
O4A N1 C11 118.1(2) . . ?
O4A N1 O5A 123.6(2) . . ?
O5A N1 C11 118.28(15) . . ?
O4B N1 C11 115.3(12) . . ?
O5B N1 C11 115.6(6) . . ?
O5B N1 O4B 127.5(13) . . ?
O2 C6 H6A 110.8 . . ?
O2 C6 H6B 110.8 . . ?
O2 C6 H6BC 110.2 . . ?
O2 C6 H6BD 110.2 . . ?
O2 C6 C2A 104.69(14) . . ?
O2 C6 C2B 107.6(4) . . ?
H6A C6 H6B 108.9 . . ?
H6BC C6 H6BD 108.5 . . ?
C2A C6 H6A 110.8 . . ?
C2A C6 H6B 110.8 . . ?
C2B C6 H6BC 110.2 . . ?
C2B C6 H6BD 110.2 . . ?
O2 C7 C8 112.03(13) . . ?
O3 C7 O2 123.73(15) . . ?
O3 C7 C8 124.23(15) . . ?
C9 C8 C7 121.94(14) . . ?
C13 C8 C7 117.99(14) . . ?
C13 C8 C9 120.06(15) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.18(15) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.11(16) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 N1 118.46(15) . . ?
C12 C11 N1 118.48(15) . . ?
C12 C11 C10 123.06(15) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 117.96(15) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.60(15) . . ?
C12 C13 H13 119.7 . . ?
C1A O1A C5A 110.62(16) . . ?
O1A C1A H1A 110.8 . . ?
O1A C1A C2A 115.12(16) . . ?
O1A C1A C4A 118.65(18) . . ?
C2A C1A H1A 110.8 . . ?
C4A C1A H1A 110.8 . . ?
C4A C1A C2A 88.95(11) . . ?
C6 C2A C1A 112.34(16) . . ?
C6 C2A H2A 113.9 . . ?
C6 C2A C3A 112.38(16) . . ?
C1A C2A H2A 113.9 . . ?
C1A C2A C3A 87.99(11) . . ?
C3A C2A H2A 113.9 . . ?
C2A C3A H3AA 114.0 . . ?
C2A C3A H3AB 114.0 . . ?
C2A C3A C4A 87.85(11) . . ?
H3AA C3A H3AB 111.2 . . ?
C4A C3A H3AA 114.0 . . ?
C4A C3A H3AB 114.0 . . ?
C1A C4A C3A 88.50(11) . . ?
C1A C4A H4AA 113.9 . . ?
C1A C4A H4AB 113.9 . . ?
C3A C4A H4AA 113.9 . . ?
C3A C4A H4AB 113.9 . . ?
H4AA C4A H4AB 111.1 . . ?
O1A C5A H5AA 109.5 . . ?
O1A C5A H5AB 109.5 . . ?
O1A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C1B O1B C5B 109.6(12) . . ?
O1B C1B H1B 109.9 . . ?
O1B C1B C2B 117.0(11) . . ?
O1B C1B C4B 120.4(13) . . ?
C2B C1B H1B 109.9 . . ?
C2B C1B C4B 87.9(7) . . ?
C4B C1B H1B 109.9 . . ?
C6 C2B H2B 116.7 . . ?
C1B C2B C6 112.2(9) . . ?
C1B C2B H2B 116.7 . . ?
C1B C2B C3B 90.7(7) . . ?
C3B C2B C6 99.9(8) . . ?
C3B C2B H2B 116.7 . . ?
C2B C3B H3BA 114.0 . . ?
C2B C3B H3BB 114.0 . . ?
C2B C3B C4B 88.1(6) . . ?
H3BA C3B H3BB 111.2 . . ?
C4B C3B H3BA 114.0 . . ?
C4B C3B H3BB 114.0 . . ?
C1B C4B H4BA 113.7 . . ?
C1B C4B H4BB 113.7 . . ?
C3B C4B C1B 89.5(7) . . ?
C3B C4B H4BA 113.7 . . ?
C3B C4B H4BB 113.7 . . ?
H4BA C4B H4BB 111.0 . . ?
O1B C5B H5BA 109.5 . . ?
O1B C5B H5BB 109.5 . . ?
O1B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 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
O2 C6 C2A C1A 174.37(14) . . . . ?
O2 C6 C2A C3A 77.00(17) . . . . ?
O2 C6 C2B C1B -167.5(7) . . . . ?
O2 C6 C2B C3B -72.7(6) . . . . ?
O2 C7 C8 C9 3.6(2) . . . . ?
O2 C7 C8 C13 -175.61(14) . . . . ?
O3 C7 C8 C9 -176.38(18) . . . . ?
O3 C7 C8 C13 4.4(3) . . . . ?
N1 C11 C12 C13 -179.37(14) . . . . ?
C6 O2 C7 O3 0.9(3) . . . . ?
C6 O2 C7 C8 -179.08(14) . . . . ?
C6 C2A C3A C4A 94.17(16) . . . . ?
C6 C2B C3B C4B -98.0(8) . . . . ?
C7 O2 C6 C2A 173.47(15) . . . . ?
C7 O2 C6 C2B -140.5(4) . . . . ?
C7 C8 C9 C10 179.36(15) . . . . ?
C7 C8 C13 C12 -179.32(14) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C8 C13 C12 1.5(2) . . . . ?
C9 C10 C11 N1 179.37(15) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C8 -0.7(2) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
O1A C1A C2A C6 27.5(2) . . . . ?
O1A C1A C2A C3A 140.94(17) . . . . ?
O1A C1A C4A C3A -137.77(17) . . . . ?
O4A N1 C11 C10 177.6(2) . . . . ?
O4A N1 C11 C12 -3.1(3) . . . . ?
O5A N1 C11 C10 -2.3(3) . . . . ?
O5A N1 C11 C12 177.0(2) . . . . ?
C1A C2A C3A C4A -19.21(15) . . . . ?
C2A C1A C4A C3A -19.48(15) . . . . ?
C2A C3A C4A C1A 19.44(15) . . . . ?
C4A C1A C2A C6 -93.88(17) . . . . ?
C4A C1A C2A C3A 19.54(16) . . . . ?
C5A O1A C1A C2A -172.77(17) . . . . ?
C5A O1A C1A C4A -69.3(2) . . . . ?
O1B C1B C2B C6 -37.0(14) . . . . ?
O1B C1B C2B C3B -138.1(13) . . . . ?
O1B C1B C4B C3B 134.8(11) . . . . ?
O4B N1 C11 C10 156.8(10) . . . . ?
O4B N1 C11 C12 -23.9(10) . . . . ?
O5B N1 C11 C10 -36.8(12) . . . . ?
O5B N1 C11 C12 142.5(12) . . . . ?
C1B C2B C3B C4B 14.7(10) . . . . ?
C2B C1B C4B C3B 14.5(10) . . . . ?
C2B C3B C4B C1B -14.5(10) . . . . ?
C4B C1B C2B C6 86.4(10) . . . . ?
C4B C1B C2B C3B -14.7(10) . . . . ?
C5B O1B C1B C2B 177.6(12) . . . . ?
C5B O1B C1B C4B 73.0(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id 'ABC-LTS-1204 '
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cha2562
_database_code_depnum_ccdc_archive 'CCDC 2175205'
loop_
_audit_author_name
_audit_author_address
' Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
_exptl_crystal_preparation       ?
_audit_creation_date             2022-05-10

loop_
_audit_author_email
lea.thai-savard@umontreal.ca
andre.charette@umontreal.ca
thierry.maris@umontreal.ca
_diffrn_source_power             0.1993706
_audit_creation_method           
;
FinalCif V104 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C21 H23 N3 O2'
_chemical_formula_moiety         'C21 H23 N3 O2'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_chemical_formula_weight         349.42
_chemical_melting_point          337
_space_group_crystal_system      monoclinic
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_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 Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_olex2_submission_original_sample_id ABC-LTS-1488
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                   15.3404(6)
_cell_length_b                   5.5177(2)
_cell_length_c                   21.3195(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.548(2)
_cell_angle_gamma                90
_cell_volume                     1788.93(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7985
_cell_measurement_theta_min      3.304
_cell_measurement_theta_max      55.511
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_recrystallization_method 'crystallised from Et2O/Hexanes'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_T_max  0.6573
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.991
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon III CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_diffrn_ambient_temperature      150
_diffrn_ambient_environment      ?
_diffrn_radiation_type           'Ga K\a'
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 700'
_diffrn_radiation_probe          X-ray
_diffrn_source                   'Metal Jet'
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_diffrn_source_target            Ga
_diffrn_source_voltage           69.71
_diffrn_source_current           2.86
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_type            'Bruker CMOS Photon III '
_diffrn_detector_area_resol_mean 10.42
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            16661
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_theta_min         3.303
_diffrn_reflns_theta_max         55.915
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3493
_reflns_number_gt                2711
_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       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_cell_refinement       
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2020) V8.40B; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_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)+(0.0556P)²+0.3054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3493
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.20977(6) 0.74850(17) 0.49399(4) 0.0306(2) Uani 1 1 d . . . . .
O2 O 0.45016(6) 0.62324(17) 0.42673(4) 0.0283(2) Uani 1 1 d . . . . .
N1 N 0.29062(7) 0.33350(19) 0.34242(5) 0.0219(3) Uani 1 1 d . . . . .
N2 N 0.29700(7) 0.0899(2) 0.34684(5) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.34484(7) 0.0179(2) 0.30317(5) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.25823(8) 0.4765(2) 0.39158(6) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.245452 0.641743 0.376217 0.028 Uiso 1 1 calc R U . . .
C2 C 0.18257(9) 0.3842(3) 0.42599(6) 0.0278(3) Uani 1 1 d . . . . .
H2A H 0.178143 0.208970 0.427693 0.033 Uiso 1 1 calc R U . . .
H2B H 0.126034 0.457399 0.411466 0.033 Uiso 1 1 calc R U . . .
C3 C 0.23144(9) 0.5004(3) 0.48706(6) 0.0274(3) Uani 1 1 d . . . . .
H3 H 0.231412 0.402451 0.525413 0.033 Uiso 1 1 calc R U . . .
C4 C 0.31672(8) 0.4851(3) 0.45627(6) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.343736 0.325734 0.465210 0.029 Uiso 1 1 calc R U . . .
C5 C 0.13413(10) 0.7797(3) 0.52460(8) 0.0409(4) Uani 1 1 d . . . . .
H5A H 0.085768 0.692376 0.501959 0.061 Uiso 1 1 calc R U . . .
H5B H 0.119694 0.948861 0.525537 0.061 Uiso 1 1 calc R U . . .
H5C H 0.145592 0.719099 0.567097 0.061 Uiso 1 1 calc R U . . .
C6 C 0.33473(8) 0.4171(2) 0.29645(6) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.340477 0.577479 0.284211 0.027 Uiso 1 1 calc R U . . .
C7 C 0.36943(8) 0.2156(2) 0.27145(6) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.42850(8) 0.2003(2) 0.22262(6) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.43012(9) 0.3850(3) 0.17834(6) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.390989 0.513900 0.178002 0.033 Uiso 1 1 calc R U . . .
C10 C 0.48952(9) 0.3784(3) 0.13478(7) 0.0314(3) Uani 1 1 d . . . . .
H10 H 0.490166 0.503130 0.105505 0.038 Uiso 1 1 calc R U . . .
C11 C 0.54781(9) 0.1879(3) 0.13448(7) 0.0326(3) Uani 1 1 d . . . . .
H11 H 0.587874 0.184565 0.105323 0.039 Uiso 1 1 calc R U . . .
C12 C 0.54623(9) 0.0022(3) 0.17780(7) 0.0321(3) Uani 1 1 d . . . . .
H12 H 0.585149 -0.126929 0.177523 0.039 Uiso 1 1 calc R U . . .
C13 C 0.48709(9) 0.0069(3) 0.22166(6) 0.0275(3) Uani 1 1 d . . . . .
H13 H 0.486394 -0.119121 0.250550 0.033 Uiso 1 1 calc R U . . .
C14 C 0.38632(8) 0.6768(3) 0.46767(6) 0.0264(3) Uani 1 1 d . . . . .
H14A H 0.361079 0.835900 0.458253 0.032 Uiso 1 1 calc R U . . .
H14B H 0.413105 0.674273 0.511486 0.032 Uiso 1 1 calc R U . . .
C15 C 0.51198(9) 0.8125(3) 0.42575(6) 0.0274(3) Uani 1 1 d . . . . .
H15A H 0.540081 0.843571 0.468455 0.033 Uiso 1 1 calc R U . . .
H15B H 0.481965 0.959287 0.409970 0.033 Uiso 1 1 calc R U . . .
C16 C 0.58071(8) 0.7473(2) 0.38437(6) 0.0250(3) Uani 1 1 d . . . . .
C17 C 0.65274(9) 0.8999(3) 0.38297(6) 0.0303(3) Uani 1 1 d . . . . .
H17 H 0.658398 1.037440 0.408399 0.036 Uiso 1 1 calc R U . . .
C18 C 0.71592(9) 0.8492(3) 0.34421(7) 0.0336(4) Uani 1 1 d . . . . .
H18 H 0.763584 0.952966 0.343606 0.040 Uiso 1 1 calc R U . . .
C19 C 0.70852(9) 0.6452(3) 0.30639(7) 0.0345(4) Uani 1 1 d . . . . .
H19 H 0.751169 0.610959 0.280436 0.041 Uiso 1 1 calc R U . . .
C20 C 0.63739(9) 0.4920(3) 0.30729(7) 0.0341(4) Uani 1 1 d . . . . .
H20 H 0.631990 0.354905 0.281702 0.041 Uiso 1 1 calc R U . . .
C21 C 0.57391(9) 0.5424(3) 0.34635(6) 0.0294(3) Uani 1 1 d . . . . .
H21 H 0.526476 0.437904 0.347001 0.035 Uiso 1 1 calc R U . . .


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 C3 1.4212(17) . ?
O1 C5 1.4146(16) . ?
O2 C14 1.4257(15) . ?
O2 C15 1.4125(16) . ?
N1 N2 1.3502(15) . ?
N1 C1 1.4506(16) . ?
N1 C6 1.3436(16) . ?
N2 N3 1.3201(15) . ?
N3 C7 1.3628(17) . ?
C1 H1 0.9800 . ?
C1 C2 1.5390(17) . ?
C1 C4 1.5443(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.5531(19) . ?
C3 H3 0.9800 . ?
C3 C4 1.5410(18) . ?
C4 H4 0.9800 . ?
C4 C14 1.4998(18) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.3705(18) . ?
C7 C8 1.4696(18) . ?
C8 C9 1.3916(19) . ?
C8 C13 1.3970(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.3844(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.3861(19) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5044(18) . ?
C16 C17 1.3926(19) . ?
C16 C21 1.387(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3823(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.3901(19) . ?
C21 H21 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
C5 O1 C3 112.49(11) . . ?
C15 O2 C14 111.87(10) . . ?
N2 N1 C1 121.30(10) . . ?
C6 N1 N2 110.73(10) . . ?
C6 N1 C1 126.39(11) . . ?
N3 N2 N1 106.99(10) . . ?
N2 N3 C7 108.96(11) . . ?
N1 C1 H1 109.7 . . ?
N1 C1 C2 121.05(11) . . ?
N1 C1 C4 116.62(10) . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C4 88.31(9) . . ?
C4 C1 H1 109.7 . . ?
C1 C2 H2A 114.1 . . ?
C1 C2 H2B 114.1 . . ?
C1 C2 C3 87.24(10) . . ?
H2A C2 H2B 111.3 . . ?
C3 C2 H2A 114.1 . . ?
C3 C2 H2B 114.1 . . ?
O1 C3 C2 113.02(11) . . ?
O1 C3 H3 114.8 . . ?
O1 C3 C4 108.68(11) . . ?
C2 C3 H3 114.8 . . ?
C4 C3 C2 87.91(10) . . ?
C4 C3 H3 114.8 . . ?
C1 C4 H4 109.1 . . ?
C3 C4 C1 87.48(10) . . ?
C3 C4 H4 109.1 . . ?
C14 C4 C1 118.95(11) . . ?
C14 C4 C3 121.23(11) . . ?
C14 C4 H4 109.1 . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6 127.4 . . ?
N1 C6 C7 105.29(11) . . ?
C7 C6 H6 127.4 . . ?
N3 C7 C6 108.02(11) . . ?
N3 C7 C8 122.84(11) . . ?
C6 C7 C8 128.99(12) . . ?
C9 C8 C7 120.40(12) . . ?
C9 C8 C13 118.73(12) . . ?
C13 C8 C7 120.79(12) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.51(13) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.46(14) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.56(13) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.49(13) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.24(13) . . ?
C12 C13 H13 119.9 . . ?
O2 C14 C4 106.65(10) . . ?
O2 C14 H14A 110.4 . . ?
O2 C14 H14B 110.4 . . ?
C4 C14 H14A 110.4 . . ?
C4 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 C16 110.83(11) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C17 C16 C15 119.16(12) . . ?
C21 C16 C15 122.19(12) . . ?
C21 C16 C17 118.63(12) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.74(14) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.24(14) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.66(13) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.16(14) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.56(13) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?

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 C3 C4 C1 -91.21(11) . . . . ?
O1 C3 C4 C14 31.47(16) . . . . ?
O2 C15 C16 C17 -173.00(11) . . . . ?
O2 C15 C16 C21 8.42(18) . . . . ?
N1 N2 N3 C7 0.53(13) . . . . ?
N1 C1 C2 C3 142.80(12) . . . . ?
N1 C1 C4 C3 -146.84(11) . . . . ?
N1 C1 C4 C14 88.49(15) . . . . ?
N1 C6 C7 N3 0.12(14) . . . . ?
N1 C6 C7 C8 -175.58(12) . . . . ?
N2 N1 C1 C2 -37.79(17) . . . . ?
N2 N1 C1 C4 67.46(15) . . . . ?
N2 N1 C6 C7 0.21(14) . . . . ?
N2 N3 C7 C6 -0.41(14) . . . . ?
N2 N3 C7 C8 175.61(11) . . . . ?
N3 C7 C8 C9 159.62(12) . . . . ?
N3 C7 C8 C13 -23.62(18) . . . . ?
C1 N1 N2 N3 -167.01(10) . . . . ?
C1 N1 C6 C7 165.91(11) . . . . ?
C1 C2 C3 O1 86.94(12) . . . . ?
C1 C2 C3 C4 -22.49(10) . . . . ?
C1 C4 C14 O2 -67.07(15) . . . . ?
C2 C1 C4 C3 -22.62(10) . . . . ?
C2 C1 C4 C14 -147.29(12) . . . . ?
C2 C3 C4 C1 22.41(10) . . . . ?
C2 C3 C4 C14 145.09(12) . . . . ?
C3 C4 C14 O2 -173.14(11) . . . . ?
C4 C1 C2 C3 22.44(10) . . . . ?
C5 O1 C3 C2 86.81(14) . . . . ?
C5 O1 C3 C4 -177.34(11) . . . . ?
C6 N1 N2 N3 -0.46(13) . . . . ?
C6 N1 C1 C2 157.89(12) . . . . ?
C6 N1 C1 C4 -96.86(15) . . . . ?
C6 C7 C8 C9 -25.3(2) . . . . ?
C6 C7 C8 C13 151.51(13) . . . . ?
C7 C8 C9 C10 175.96(12) . . . . ?
C7 C8 C13 C12 -175.99(12) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C8 C13 C12 0.83(19) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C13 C8 C9 C10 -0.87(19) . . . . ?
C14 O2 C15 C16 177.66(10) . . . . ?
C15 O2 C14 C4 170.61(10) . . . . ?
C15 C16 C17 C18 -178.23(13) . . . . ?
C15 C16 C21 C20 178.04(13) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C16 C21 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C20 C21 C16 0.5(2) . . . . ?
C21 C16 C17 C18 0.4(2) . . . . ?

