# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_harfr2_0m
_database_code_depnum_ccdc_archive 'CCDC 2247008'
loop_
_audit_author_name
_audit_author_address
'Alexandra A. Heidecker'
;Technical University of Munich
Germany
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2023-05-08 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 N O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C25 H31 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         377.51
_chemical_compound_source        'see text'

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   10.2906(8)
_cell_length_b                   10.4146(8)
_cell_length_c                   10.5305(7)
_cell_angle_alpha                115.040(3)
_cell_angle_beta                 94.445(3)
_cell_angle_gamma                99.671(3)
_cell_volume                     993.93(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      2.2138
_cell_measurement_theta_max      28.3102
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.129
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_T_max  0.7457

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             A. A. Heidecker
scanspeed                           2 s per frame
dx                                  40 mm
3427 frames measured in 11 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' Bruker Photon-II CPAD '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            55199
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4723
# number of observed reflections (> n sig(I))
_reflns_number_gt                4255
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX 4 Control Software (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0699P)²+0.3783P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom


# Permitted for _refine_ls_hydrogen_treatment :
# refall            - refined all H-atom parameters
# refxyz            - refined H-atom coordinates only
# refU              - refined H-atom U only
# noref             - no refinement of H-atom parameters
# constr            - H-atom parameters constrained
# hetero            - H-atom parameters constrained for H on C,
#                     all H-atom parameters refined for H on
#                     heteroatoms
# heteroxyz         - H-atom parameters constrained for H on C,
#                     refined H-atom coordinates only for H
#                     on heteroatoms
# heteroU           - H-atom parameters constrained for H on C,
#                     refined H-atom U's only for H on
#                     heteroatoms
# heteronoref       - H-atom parameters constrained for H on C,
#                     no refinement of H-atom parameters for
#                     H on heteroatoms
# hetero-mixed      - H-atom parameters constrained for H on C
#                     and some heteroatoms, all H-atom
#                     parameters refined for H on remaining
#                     heteroatoms.
# heteroxyz-mixed   - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     coordinates only for H on remaining
#                     heteroatoms.
# heteroU-mixed     - H-atom parameters constrained for H on C
#                     and some heteroatoms, refined H-atom
#                     U's only for H on remaining heteroatoms
# heteronoref-mixed - H-atom parameters constrained for H on C
#                     and some heteroatoms, no refinement of
#                     H-atom parameters for H on remaining
#                     heteroatoms
# mixed   - some constrained, some independent
# undef   - H-atom parameters not defined
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         4723
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1224
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.076

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.61761(8) 0.74549(10) -0.07206(9) 1.000 0.0206(2) d . . .
O2 O Uani 0.27549(8) 0.53467(9) 0.41511(9) 1.000 0.0191(2) d . . .
N1 N Uani 0.47572(9) 0.69312(10) 0.48882(10) 1.000 0.0150(2) d . . .
C1 C Uani 0.74633(12) 0.75898(14) -0.11274(13) 1.000 0.0220(3) d . . .
C2 C Uani 0.60610(11) 0.71158(12) 0.03946(12) 1.000 0.0159(3) d . . .
C3 C Uani 0.71251(11) 0.70437(13) 0.12363(12) 1.000 0.0177(3) d . . .
C4 C Uani 0.68769(11) 0.66727(13) 0.23344(12) 1.000 0.0175(3) d . . .
C5 C Uani 0.47617(11) 0.68279(12) 0.06666(12) 1.000 0.0175(3) d . . .
C6 C Uani 0.45374(11) 0.64520(12) 0.17523(12) 1.000 0.0171(3) d . . .
C7 C Uani 0.55932(11) 0.63584(12) 0.26053(12) 1.000 0.0156(3) d . . .
C8 C Uani 0.53388(11) 0.59041(12) 0.37665(12) 1.000 0.0166(3) d . . .
C9 C Uani 0.34424(11) 0.65523(12) 0.49659(11) 1.000 0.0136(3) d . . .
C10 C Uani 0.56463(11) 0.83679(13) 0.56908(13) 1.000 0.0191(3) d . . .
C11 C Uani 0.51290(12) 0.93551(12) 0.69778(13) 1.000 0.0191(3) d . . .
C12 C Uani 0.36443(11) 0.92177(12) 0.65804(12) 1.000 0.0171(3) d . . .
C13 C Uani 0.28805(11) 0.76630(11) 0.61586(11) 1.000 0.0136(3) d . . .
C14 C Uani 0.29466(12) 0.72610(12) 0.74607(12) 1.000 0.0164(3) d . . .
C15 C Uani 0.25158(13) 0.84711(13) 0.86601(12) 1.000 0.0197(3) d . . .
C16 C Uani 0.12120(13) 0.83276(13) 0.83003(12) 1.000 0.0202(3) d . . .
C17 C Uani 0.16718(12) 0.60517(12) 0.69917(12) 1.000 0.0186(3) d . . .
C18 C Uani 0.07391(12) 0.70162(13) 0.68600(12) 1.000 0.0178(3) d . . .
C19 C Uani 0.13671(11) 0.74480(12) 0.57866(12) 1.000 0.0149(3) d . . .
C20 C Uani 0.06964(11) 0.75575(12) 0.47243(12) 1.000 0.0169(3) d . . .
C21 C Uani 0.12397(11) 0.78273(12) 0.35582(12) 1.000 0.0162(3) d . . .
C22 C Uani 0.06979(11) 0.65653(12) 0.20787(12) 1.000 0.0176(3) d . . .
C23 C Uani 0.10078(12) 0.72176(13) 0.10473(13) 1.000 0.0202(3) d . . .
C24 C Uani 0.10314(13) 0.88517(13) 0.18723(13) 1.000 0.0214(3) d . . .
C25 C Uani 0.08414(12) 0.91115(13) 0.33903(12) 1.000 0.0189(3) d . . .
H1A H Uiso 0.77694 0.66881 -0.13509 1.000 0.0330 c RU . .
H1B H Uiso 0.80964 0.84007 -0.03439 1.000 0.0330 c RU . .
H1C H Uiso 0.74085 0.77734 -0.19670 1.000 0.0330 c RU . .
H3 H Uiso 0.80125 0.72448 0.10663 1.000 0.0210 c RU . .
H4 H Uiso 0.76087 0.66338 0.29150 1.000 0.0210 c RU . .
H5 H Uiso 0.40319 0.68914 0.01022 1.000 0.0210 c RU . .
H6 H Uiso 0.36502 0.62533 0.19234 1.000 0.0210 c RU . .
H8A H Uiso 0.47248 0.49334 0.33428 1.000 0.0200 c RU . .
H8B H Uiso 0.61929 0.58208 0.41939 1.000 0.0200 c RU . .
H10A H Uiso 0.57742 0.88397 0.50536 1.000 0.0230 c RU . .
H10B H Uiso 0.65302 0.82481 0.60070 1.000 0.0230 c RU . .
H11A H Uiso 0.56146 1.03748 0.73096 1.000 0.0230 c RU . .
H11B H Uiso 0.52804 0.90789 0.77595 1.000 0.0230 c RU . .
H12A H Uiso 0.34926 0.94616 0.57766 1.000 0.0200 c RU . .
H12B H Uiso 0.33118 0.99087 0.73979 1.000 0.0200 c RU . .
H14 H Uiso 0.37957 0.70104 0.77109 1.000 0.0200 c RU . .
H15 H Uiso 0.30735 0.91960 0.95094 1.000 0.0240 c RU . .
H16 H Uiso 0.06720 0.89374 0.88473 1.000 0.0240 c RU . .
H17A H Uiso 0.14909 0.57200 0.77267 1.000 0.0220 c RU . .
H17B H Uiso 0.16682 0.52125 0.60749 1.000 0.0220 c RU . .
H18 H Uiso -0.02407 0.65692 0.66089 1.000 0.0210 c RU . .
H20 H Uiso -0.02417 0.74524 0.46990 1.000 0.0200 c RU . .
H21 H Uiso 0.22368 0.80004 0.37357 1.000 0.0190 c RU . .
H22A H Uiso 0.11497 0.57543 0.19138 1.000 0.0210 c RU . .
H22B H Uiso -0.02767 0.62014 0.19690 1.000 0.0210 c RU . .
H23A H Uiso 0.03100 0.67546 0.01884 1.000 0.0240 c RU . .
H23B H Uiso 0.18842 0.70764 0.07534 1.000 0.0240 c RU . .
H24A H Uiso 0.18949 0.94478 0.18864 1.000 0.0260 c RU . .
H24B H Uiso 0.03010 0.91098 0.14241 1.000 0.0260 c RU . .
H25A H Uiso 0.14210 1.00449 0.40995 1.000 0.0230 c RU . .
H25B H Uiso -0.01007 0.91296 0.35123 1.000 0.0230 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4263(15) . . yes
O1 C2 1.3698(16) . . yes
O2 C9 1.2283(15) . . yes
N1 C8 1.4672(15) . . yes
N1 C9 1.3631(15) . . yes
N1 C10 1.4629(17) . . yes
C2 C3 1.3870(17) . . no
C2 C5 1.3989(17) . . no
C3 C4 1.3937(18) . . no
C4 C7 1.3877(17) . . no
C5 C6 1.3795(17) . . no
C6 C7 1.3983(17) . . no
C7 C8 1.5118(17) . . no
C9 C13 1.5354(16) . . no
C10 C11 1.5144(18) . . no
C11 C12 1.5188(17) . . no
C12 C13 1.5318(18) . . no
C13 C14 1.5941(17) . . no
C13 C19 1.5307(16) . . no
C14 C15 1.5189(17) . . no
C14 C17 1.5392(18) . . no
C15 C16 1.3311(19) . . no
C16 C18 1.5203(17) . . no
C17 C18 1.5397(19) . . no
C18 C19 1.5308(18) . . no
C19 C20 1.3250(17) . . no
C20 C21 1.4984(17) . . no
C21 C22 1.5334(17) . . no
C21 C25 1.5366(19) . . no
C22 C23 1.5324(19) . . no
C23 C24 1.544(2) . . no
C24 C25 1.5385(17) . . no
C1 H1A 0.9800 . . no
C1 H1B 0.9800 . . no
C1 H1C 0.9800 . . no
C3 H3 0.9500 . . no
C4 H4 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C8 H8A 0.9900 . . no
C8 H8B 0.9900 . . no
C10 H10A 0.9900 . . no
C10 H10B 0.9900 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C14 H14 1.0000 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C17 H17A 0.9900 . . no
C17 H17B 0.9900 . . no
C18 H18 1.0000 . . no
C20 H20 0.9500 . . no
C21 H21 1.0000 . . no
C22 H22A 0.9900 . . no
C22 H22B 0.9900 . . no
C23 H23A 0.9900 . . no
C23 H23B 0.9900 . . no
C24 H24A 0.9900 . . no
C24 H24B 0.9900 . . no
C25 H25A 0.9900 . . no
C25 H25B 0.9900 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 116.99(10) . . . yes
C8 N1 C9 119.20(10) . . . yes
C8 N1 C10 113.68(9) . . . yes
C9 N1 C10 126.51(10) . . . yes
O1 C2 C3 124.62(11) . . . yes
O1 C2 C5 115.72(10) . . . yes
C3 C2 C5 119.66(11) . . . no
C2 C3 C4 119.20(11) . . . no
C3 C4 C7 122.00(11) . . . no
C2 C5 C6 120.18(11) . . . no
C5 C6 C7 121.15(11) . . . no
C4 C7 C6 117.79(11) . . . no
C4 C7 C8 121.23(11) . . . no
C6 C7 C8 120.97(10) . . . no
N1 C8 C7 112.76(11) . . . yes
O2 C9 N1 121.10(10) . . . yes
O2 C9 C13 121.58(10) . . . yes
N1 C9 C13 117.25(10) . . . yes
N1 C10 C11 113.55(10) . . . yes
C10 C11 C12 109.23(10) . . . no
C11 C12 C13 109.91(10) . . . no
C9 C13 C12 111.09(10) . . . no
C9 C13 C14 107.86(10) . . . no
C9 C13 C19 111.87(9) . . . no
C12 C13 C14 112.27(9) . . . no
C12 C13 C19 113.09(10) . . . no
C14 C13 C19 100.11(9) . . . no
C13 C14 C15 105.85(10) . . . no
C13 C14 C17 101.01(9) . . . no
C15 C14 C17 99.79(10) . . . no
C14 C15 C16 107.30(11) . . . no
C15 C16 C18 107.98(11) . . . no
C14 C17 C18 94.02(10) . . . no
C16 C18 C17 99.49(10) . . . no
C16 C18 C19 105.95(11) . . . no
C17 C18 C19 99.32(10) . . . no
C13 C19 C18 106.66(10) . . . no
C13 C19 C20 127.99(11) . . . no
C18 C19 C20 125.32(11) . . . no
C19 C20 C21 127.80(11) . . . no
C20 C21 C22 113.02(11) . . . no
C20 C21 C25 114.16(10) . . . no
C22 C21 C25 102.07(9) . . . no
C21 C22 C23 104.56(10) . . . no
C22 C23 C24 105.68(10) . . . no
C23 C24 C25 106.10(11) . . . no
C21 C25 C24 105.07(10) . . . no
O1 C1 H1A 109.00 . . . no
O1 C1 H1B 109.00 . . . no
O1 C1 H1C 109.00 . . . no
H1A C1 H1B 109.00 . . . no
H1A C1 H1C 109.00 . . . no
H1B C1 H1C 109.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 119.00 . . . no
C7 C4 H4 119.00 . . . no
C2 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C5 C6 H6 119.00 . . . no
C7 C6 H6 119.00 . . . no
N1 C8 H8A 109.00 . . . no
N1 C8 H8B 109.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
H8A C8 H8B 108.00 . . . no
N1 C10 H10A 109.00 . . . no
N1 C10 H10B 109.00 . . . no
C11 C10 H10A 109.00 . . . no
C11 C10 H10B 109.00 . . . no
H10A C10 H10B 108.00 . . . no
C10 C11 H11A 110.00 . . . no
C10 C11 H11B 110.00 . . . no
C12 C11 H11A 110.00 . . . no
C12 C11 H11B 110.00 . . . no
H11A C11 H11B 108.00 . . . no
C11 C12 H12A 110.00 . . . no
C11 C12 H12B 110.00 . . . no
C13 C12 H12A 110.00 . . . no
C13 C12 H12B 110.00 . . . no
H12A C12 H12B 108.00 . . . no
C13 C14 H14 116.00 . . . no
C15 C14 H14 116.00 . . . no
C17 C14 H14 116.00 . . . no
C14 C15 H15 126.00 . . . no
C16 C15 H15 126.00 . . . no
C15 C16 H16 126.00 . . . no
C18 C16 H16 126.00 . . . no
C14 C17 H17A 113.00 . . . no
C14 C17 H17B 113.00 . . . no
C18 C17 H17A 113.00 . . . no
C18 C17 H17B 113.00 . . . no
H17A C17 H17B 110.00 . . . no
C16 C18 H18 116.00 . . . no
C17 C18 H18 116.00 . . . no
C19 C18 H18 116.00 . . . no
C19 C20 H20 116.00 . . . no
C21 C20 H20 116.00 . . . no
C20 C21 H21 109.00 . . . no
C22 C21 H21 109.00 . . . no
C25 C21 H21 109.00 . . . no
C21 C22 H22A 111.00 . . . no
C21 C22 H22B 111.00 . . . no
C23 C22 H22A 111.00 . . . no
C23 C22 H22B 111.00 . . . no
H22A C22 H22B 109.00 . . . no
C22 C23 H23A 111.00 . . . no
C22 C23 H23B 111.00 . . . no
C24 C23 H23A 111.00 . . . no
C24 C23 H23B 111.00 . . . no
H23A C23 H23B 109.00 . . . no
C23 C24 H24A 111.00 . . . no
C23 C24 H24B 111.00 . . . no
C25 C24 H24A 111.00 . . . no
C25 C24 H24B 111.00 . . . no
H24A C24 H24B 109.00 . . . no
C21 C25 H25A 111.00 . . . no
C21 C25 H25B 111.00 . . . no
C24 C25 H25A 111.00 . . . no
C24 C25 H25B 111.00 . . . no
H25A C25 H25B 109.00 . . . no

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
C1 O1 C2 C3 6.92(18) . . . . no
C1 O1 C2 C5 -173.00(11) . . . . no
C9 N1 C8 C7 106.74(13) . . . . no
C10 N1 C8 C7 -64.85(13) . . . . no
C8 N1 C9 O2 3.00(18) . . . . no
C8 N1 C9 C13 179.96(10) . . . . no
C10 N1 C9 O2 173.40(12) . . . . no
C10 N1 C9 C13 -9.65(17) . . . . no
C8 N1 C10 C11 -171.66(10) . . . . no
C9 N1 C10 C11 17.48(17) . . . . no
O1 C2 C3 C4 -179.40(12) . . . . no
C5 C2 C3 C4 0.52(19) . . . . no
O1 C2 C5 C6 178.92(11) . . . . no
C3 C2 C5 C6 -1.01(19) . . . . no
C2 C3 C4 C7 0.6(2) . . . . no
C3 C4 C7 C6 -1.24(19) . . . . no
C3 C4 C7 C8 177.71(12) . . . . no
C2 C5 C6 C7 0.37(19) . . . . no
C5 C6 C7 C4 0.73(19) . . . . no
C5 C6 C7 C8 -178.22(12) . . . . no
C4 C7 C8 N1 117.54(13) . . . . no
C6 C7 C8 N1 -63.55(15) . . . . no
O2 C9 C13 C12 -155.13(11) . . . . no
O2 C9 C13 C14 81.44(13) . . . . no
O2 C9 C13 C19 -27.71(16) . . . . no
N1 C9 C13 C12 27.93(14) . . . . no
N1 C9 C13 C14 -95.51(12) . . . . no
N1 C9 C13 C19 155.35(11) . . . . no
N1 C10 C11 C12 -43.01(15) . . . . no
C10 C11 C12 C13 63.12(13) . . . . no
C11 C12 C13 C9 -55.05(12) . . . . no
C11 C12 C13 C14 65.83(12) . . . . no
C11 C12 C13 C19 178.21(9) . . . . no
C9 C13 C14 C15 174.40(10) . . . . no
C9 C13 C14 C17 -81.99(11) . . . . no
C12 C13 C14 C15 51.69(13) . . . . no
C12 C13 C14 C17 155.29(10) . . . . no
C19 C13 C14 C15 -68.54(11) . . . . no
C19 C13 C14 C17 35.06(11) . . . . no
C9 C13 C19 C18 115.61(11) . . . . no
C9 C13 C19 C20 -62.33(17) . . . . no
C12 C13 C19 C18 -118.06(11) . . . . no
C12 C13 C19 C20 64.00(16) . . . . no
C14 C13 C19 C18 1.58(12) . . . . no
C14 C13 C19 C20 -176.36(13) . . . . no
C13 C14 C15 C16 70.55(13) . . . . no
C17 C14 C15 C16 -33.95(14) . . . . no
C13 C14 C17 C18 -57.46(10) . . . . no
C15 C14 C17 C18 50.95(10) . . . . no
C14 C15 C16 C18 0.35(15) . . . . no
C15 C16 C18 C17 33.33(14) . . . . no
C15 C16 C18 C19 -69.29(14) . . . . no
C14 C17 C18 C16 -50.52(10) . . . . no
C14 C17 C18 C19 57.52(10) . . . . no
C16 C18 C19 C13 65.25(12) . . . . no
C16 C18 C19 C20 -116.74(14) . . . . no
C17 C18 C19 C13 -37.50(12) . . . . no
C17 C18 C19 C20 140.51(13) . . . . no
C13 C19 C20 C21 4.3(2) . . . . no
C18 C19 C20 C21 -173.33(12) . . . . no
C19 C20 C21 C22 116.98(14) . . . . no
C19 C20 C21 C25 -126.95(14) . . . . no
C20 C21 C22 C23 163.18(10) . . . . no
C25 C21 C22 C23 40.12(11) . . . . no
C20 C21 C25 C24 -159.67(10) . . . . no
C22 C21 C25 C24 -37.39(12) . . . . no
C21 C22 C23 C24 -27.64(12) . . . . no
C22 C23 C24 C25 4.24(13) . . . . no
C23 C24 C25 C21 20.68(13) . . . . no

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C8 H8A O2 0.9900 2.3000 2.7237(15) 105.00 . yes
C17 H17B O2 0.9900 2.4300 3.1083(15) 125.00 . yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;

