# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1539489'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-08-15 downloaded from the CCDC.
;

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O3'
# 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            'C22 H23 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         349.41
_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
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   14.557(8)
_cell_length_b                   7.392(4)
_cell_length_c                   18.717(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.45(3)
_cell_angle_gamma                90
_cell_volume                     1847.7(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.3
_cell_special_details            
;
;

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.992

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            9815
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_sigmaI/netI    0.1205
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.33
_reflns_number_total             3236
_reflns_number_gt                1507
_reflns_threshold_expression     >2sigma(I)

_diffrn_reflns_theta_full        25.33
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'


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

# 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     
'calc w=1/[σ²(Fo²)+(0.0857P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2001
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.057

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

# 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
O1 O Uani 0.6190(2) 0.8051(4) 0.72052(16) 1.000 0.0531(11) . .
O2 O Uani 0.87566(19) 0.5019(4) 0.72135(19) 1.000 0.0582(10) . .
O3 O Uani 0.81368(19) 0.7839(3) 0.71629(17) 1.000 0.0508(10) . .
N1 N Uani 0.7007(2) 0.3450(4) 0.72609(18) 1.000 0.0379(11) . .
C1 C Uani 0.4999(4) 0.2360(5) 0.4873(3) 1.000 0.0552(17) . .
C2 C Uani 0.3978(4) 0.2240(6) 0.4665(3) 1.000 0.0591(17) . .
C3 C Uani 0.3592(3) 0.2460(6) 0.5212(3) 1.000 0.0638(19) . .
C4 C Uani 0.4224(3) 0.2791(6) 0.5983(3) 1.000 0.0504(17) . .
C5 C Uani 0.5247(3) 0.2909(5) 0.6203(2) 1.000 0.0423(16) . .
C6 C Uani 0.5871(3) 0.3250(5) 0.7060(2) 1.000 0.0436(14) . .
C7 C Uani 0.7300(3) 0.2199(5) 0.6738(2) 1.000 0.0443(16) . .
C8 C Uani 0.6755(3) 0.2747(6) 0.5891(2) 1.000 0.0504(17) . .
C9 C Uani 0.5648(3) 0.2680(5) 0.5645(3) 1.000 0.0438(16) . .
C10 C Uani 0.5618(3) 0.5029(6) 0.7335(3) 1.000 0.0525(16) . .
C11 C Uani 0.6330(3) 0.6390(6) 0.7217(2) 1.000 0.0396(14) . .
C12 C Uani 0.7121(3) 0.5421(5) 0.7138(2) 1.000 0.0369(14) . .
C13 C Uani 0.8063(3) 0.5993(5) 0.7168(2) 1.000 0.0411(16) . .
C14 C Uani 0.9091(3) 0.8527(6) 0.7213(3) 1.000 0.0508(16) . .
C15 C Uani 0.9105(4) 0.8740(7) 0.6419(3) 1.000 0.076(2) . .
C16 C Uani 0.7576(3) 0.2898(6) 0.8104(2) 1.000 0.0437(14) . .
C17 C Uani 0.8050(3) 0.4184(6) 0.8664(3) 1.000 0.0569(17) . .
C18 C Uani 0.8574(3) 0.3667(7) 0.9439(3) 1.000 0.0652(17) . .
C19 C Uani 0.8626(3) 0.1877(7) 0.9665(3) 1.000 0.0594(17) . .
C20 C Uani 0.8144(4) 0.0634(7) 0.9093(3) 1.000 0.0648(17) . .
C21 C Uani 0.7634(3) 0.1105(6) 0.8316(3) 1.000 0.0554(17) . .
C22 C Uani 0.9215(4) 0.1315(8) 1.0509(3) 1.000 0.084(2) . .
H1 H Uiso 0.52580 0.22270 0.44940 1.000 0.0660 calc R
H2 H Uiso 0.35540 0.20080 0.41500 1.000 0.0710 calc R
H3 H Uiso 0.29040 0.23900 0.50700 1.000 0.0760 calc R
H4 H Uiso 0.39550 0.29340 0.63550 1.000 0.0610 calc R
H6 H Uiso 0.57660 0.22620 0.73690 1.000 0.0520 calc R
H7A H Uiso 0.80170 0.22630 0.68830 1.000 0.0530 calc R
H7B H Uiso 0.71300 0.09610 0.68070 1.000 0.0530 calc R
H8A H Uiso 0.69520 0.39650 0.58200 1.000 0.0600 calc R
H8B H Uiso 0.69460 0.19410 0.55650 1.000 0.0600 calc R
H10A H Uiso 0.57220 0.49620 0.78800 1.000 0.0630 calc R
H10B H Uiso 0.49260 0.53590 0.70300 1.000 0.0630 calc R
H14A H Uiso 0.96190 0.77020 0.75200 1.000 0.0610 calc R
H14B H Uiso 0.92200 0.96890 0.74750 1.000 0.0610 calc R
H15A H Uiso 0.90190 0.75790 0.61710 1.000 0.1140 calc R
H15B H Uiso 0.97350 0.92480 0.64690 1.000 0.1140 calc R
H15C H Uiso 0.85710 0.95300 0.61090 1.000 0.1140 calc R
H17 H Uiso 0.80200 0.53970 0.85250 1.000 0.0680 calc R
H18 H Uiso 0.88940 0.45460 0.98100 1.000 0.0780 calc R
H20 H Uiso 0.81590 -0.05770 0.92330 1.000 0.0780 calc R
H21 H Uiso 0.73350 0.02180 0.79420 1.000 0.0660 calc R
H22A H Uiso 0.87740 0.07300 1.07050 1.000 0.1250 calc R
H22B H Uiso 0.95030 0.23670 1.08170 1.000 0.1250 calc R
H22C H Uiso 0.97380 0.04940 1.05350 1.000 0.1250 calc R


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

# 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 C11 1.243(5) . . yes
O2 C13 1.215(5) . . yes
O3 C13 1.369(4) . . yes
O3 C14 1.447(6) . . yes
N1 C6 1.550(6) . . yes
N1 C7 1.526(5) . . yes
N1 C12 1.495(5) . . yes
N1 C16 1.517(5) . . yes
C1 C2 1.381(9) . . no
C1 C9 1.396(7) . . no
C2 C3 1.360(8) . . no
C3 C4 1.390(7) . . no
C4 C5 1.381(7) . . no
C5 C6 1.517(5) . . no
C5 C9 1.395(7) . . no
C6 C10 1.510(6) . . no
C7 C8 1.519(5) . . no
C8 C9 1.490(7) . . no
C10 C11 1.522(7) . . no
C11 C12 1.413(6) . . no
C12 C13 1.415(6) . . no
C14 C15 1.503(7) . . no
C16 C17 1.379(6) . . no
C16 C21 1.376(6) . . no
C17 C18 1.397(7) . . no
C18 C19 1.382(7) . . no
C19 C20 1.373(7) . . no
C19 C22 1.525(7) . . no
C20 C21 1.389(7) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C6 H6 0.9800 . . no
C7 H7A 0.9700 . . no
C7 H7B 0.9700 . . no
C8 H8A 0.9700 . . no
C8 H8B 0.9700 . . no
C10 H10A 0.9700 . . no
C10 H10B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no
C15 H15A 0.9600 . . no
C15 H15B 0.9600 . . no
C15 H15C 0.9600 . . no
C17 H17 0.9300 . . no
C18 H18 0.9300 . . no
C20 H20 0.9300 . . no
C21 H21 0.9300 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . 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
C13 O3 C14 115.2(3) . . . yes
C6 N1 C7 109.3(3) . . . yes
C6 N1 C12 103.2(3) . . . yes
C6 N1 C16 108.4(3) . . . yes
C7 N1 C12 114.6(3) . . . yes
C7 N1 C16 109.1(3) . . . yes
C12 N1 C16 112.0(3) . . . yes
C2 C1 C9 120.8(5) . . . no
C1 C2 C3 120.1(5) . . . no
C2 C3 C4 120.1(5) . . . no
C3 C4 C5 120.7(4) . . . no
C4 C5 C6 116.5(4) . . . no
C4 C5 C9 119.5(4) . . . no
C6 C5 C9 124.0(4) . . . no
N1 C6 C5 113.9(3) . . . yes
N1 C6 C10 102.5(3) . . . yes
C5 C6 C10 112.4(3) . . . no
N1 C7 C8 110.2(3) . . . yes
C7 C8 C9 111.4(4) . . . no
C1 C9 C5 118.9(5) . . . no
C1 C9 C8 121.9(5) . . . no
C5 C9 C8 119.2(4) . . . no
C6 C10 C11 104.7(4) . . . no
O1 C11 C10 122.6(4) . . . yes
O1 C11 C12 129.3(4) . . . yes
C10 C11 C12 108.1(4) . . . no
N1 C12 C11 109.5(4) . . . yes
N1 C12 C13 116.8(3) . . . yes
C11 C12 C13 131.4(4) . . . no
O2 C13 O3 121.7(4) . . . yes
O2 C13 C12 126.2(4) . . . yes
O3 C13 C12 112.0(4) . . . yes
O3 C14 C15 111.3(4) . . . yes
N1 C16 C17 120.4(4) . . . yes
N1 C16 C21 120.3(4) . . . yes
C17 C16 C21 119.3(4) . . . no
C16 C17 C18 120.1(4) . . . no
C17 C18 C19 121.4(5) . . . no
C18 C19 C20 117.0(5) . . . no
C18 C19 C22 121.2(5) . . . no
C20 C19 C22 121.9(5) . . . no
C19 C20 C21 122.9(5) . . . no
C16 C21 C20 119.3(4) . . . no
C2 C1 H1 120.00 . . . no
C9 C1 H1 120.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
N1 C6 H6 109.00 . . . no
C5 C6 H6 109.00 . . . no
C10 C6 H6 109.00 . . . no
N1 C7 H7A 110.00 . . . no
N1 C7 H7B 110.00 . . . no
C8 C7 H7A 110.00 . . . no
C8 C7 H7B 110.00 . . . no
H7A C7 H7B 108.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
C9 C8 H8A 109.00 . . . no
C9 C8 H8B 109.00 . . . no
H8A C8 H8B 108.00 . . . no
C6 C10 H10A 111.00 . . . no
C6 C10 H10B 111.00 . . . no
C11 C10 H10A 111.00 . . . no
C11 C10 H10B 111.00 . . . no
H10A C10 H10B 109.00 . . . no
O3 C14 H14A 109.00 . . . no
O3 C14 H14B 109.00 . . . no
C15 C14 H14A 109.00 . . . no
C15 C14 H14B 109.00 . . . no
H14A C14 H14B 108.00 . . . no
C14 C15 H15A 110.00 . . . no
C14 C15 H15B 109.00 . . . no
C14 C15 H15C 110.00 . . . no
H15A C15 H15B 109.00 . . . no
H15A C15 H15C 109.00 . . . no
H15B C15 H15C 109.00 . . . no
C16 C17 H17 120.00 . . . no
C18 C17 H17 120.00 . . . no
C17 C18 H18 119.00 . . . no
C19 C18 H18 119.00 . . . no
C19 C20 H20 118.00 . . . no
C21 C20 H20 119.00 . . . no
C16 C21 H21 120.00 . . . no
C20 C21 H21 120.00 . . . no
C19 C22 H22A 109.00 . . . no
C19 C22 H22B 109.00 . . . no
C19 C22 H22C 109.00 . . . no
H22A C22 H22B 110.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 110.00 . . . 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
C14 O3 C13 C12 178.5(3) . . . . no
C13 O3 C14 C15 89.2(4) . . . . no
C14 O3 C13 O2 0.2(5) . . . . no
C16 N1 C6 C5 -153.5(3) . . . . no
C7 N1 C6 C10 -156.3(3) . . . . no
C7 N1 C12 C11 142.9(3) . . . . no
C16 N1 C12 C11 -92.2(4) . . . . no
C6 N1 C12 C11 24.2(4) . . . . no
C7 N1 C12 C13 -52.5(4) . . . . no
C16 N1 C12 C13 72.5(4) . . . . no
C16 N1 C7 C8 -178.9(3) . . . . no
C6 N1 C16 C17 -108.0(4) . . . . no
C12 N1 C6 C10 -33.9(4) . . . . no
C16 N1 C6 C10 84.9(4) . . . . no
C6 N1 C12 C13 -171.2(3) . . . . no
C12 N1 C16 C21 -174.1(4) . . . . no
C7 N1 C6 C5 -34.7(4) . . . . no
C12 N1 C6 C5 87.6(3) . . . . no
C7 N1 C16 C21 -46.2(5) . . . . no
C6 N1 C16 C21 72.7(5) . . . . no
C7 N1 C16 C17 133.1(4) . . . . no
C12 N1 C7 C8 -52.5(4) . . . . no
C12 N1 C16 C17 5.1(6) . . . . no
C6 N1 C7 C8 62.8(4) . . . . no
C2 C1 C9 C8 177.7(4) . . . . no
C2 C1 C9 C5 -1.1(6) . . . . no
C9 C1 C2 C3 1.0(6) . . . . no
C1 C2 C3 C4 -0.5(7) . . . . no
C2 C3 C4 C5 0.3(7) . . . . no
C3 C4 C5 C9 -0.5(6) . . . . no
C3 C4 C5 C6 -179.2(4) . . . . no
C4 C5 C9 C8 -178.0(4) . . . . no
C9 C5 C6 C10 119.7(4) . . . . no
C6 C5 C9 C1 179.5(3) . . . . no
C4 C5 C9 C1 0.9(6) . . . . no
C4 C5 C6 N1 -177.5(3) . . . . no
C9 C5 C6 N1 3.8(5) . . . . no
C6 C5 C9 C8 0.7(6) . . . . no
C4 C5 C6 C10 -61.6(5) . . . . no
C5 C6 C10 C11 -91.0(4) . . . . no
N1 C6 C10 C11 31.6(4) . . . . no
N1 C7 C8 C9 -58.9(4) . . . . no
C7 C8 C9 C5 26.5(5) . . . . no
C7 C8 C9 C1 -152.3(4) . . . . no
C6 C10 C11 O1 162.6(3) . . . . no
C6 C10 C11 C12 -17.9(4) . . . . no
C10 C11 C12 N1 -4.4(4) . . . . no
C10 C11 C12 C13 -166.0(4) . . . . no
O1 C11 C12 C13 13.4(7) . . . . no
O1 C11 C12 N1 175.1(4) . . . . no
N1 C12 C13 O2 7.1(5) . . . . no
C11 C12 C13 O3 -10.5(5) . . . . no
N1 C12 C13 O3 -171.1(3) . . . . no
C11 C12 C13 O2 167.7(4) . . . . no
N1 C16 C17 C18 -179.9(4) . . . . no
C21 C16 C17 C18 -0.7(7) . . . . no
N1 C16 C21 C20 -178.9(4) . . . . no
C17 C16 C21 C20 1.9(7) . . . . no
C16 C17 C18 C19 -0.5(8) . . . . no
C17 C18 C19 C20 0.3(8) . . . . no
C17 C18 C19 C22 178.9(5) . . . . no
C18 C19 C20 C21 1.0(8) . . . . no
C22 C19 C20 C21 -177.6(5) . . . . no
C19 C20 C21 C16 -2.1(8) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 O3 2.871(5) . . no
O1 C21 3.219(6) . 1_565 no
O1 C2 3.417(6) . 3_666 no
O1 C10 3.407(6) . 2_656 no
O2 C15 3.285(7) . 2_746 no
O2 C17 3.322(6) . . no
O2 C15 3.261(6) . . no
O2 C14 3.084(6) . 2_746 no
O2 N1 2.832(5) . . no
O2 C7 2.852(5) . . no
O2 C16 3.236(6) . . no
O3 O1 2.871(5) . . no
O1 H4 2.7900 . 2_656 no
O1 H21 2.3300 . 1_565 no
O1 H7B 2.8000 . 1_565 no
O1 H2 2.7100 . 3_666 no
O2 H7A 2.2700 . . no
O2 H14A 2.2900 . . no
O2 H14A 2.8000 . 2_746 no
O2 H14B 2.7800 . 2_746 no
O2 H15B 2.6300 . 2_746 no
O2 H22A 2.8900 . 4_554 no
O2 H15A 2.8500 . . no
O3 H7B 2.6700 . 1_565 no
O3 H21 2.8200 . 1_565 no
O3 H2 2.7000 . 3_666 no
N1 O2 2.832(5) . . no
C1 C1 3.521(6) . 3_656 no
C2 O1 3.417(6) . 3_666 no
C2 C11 3.518(7) . 3_666 no
C2 C12 3.555(6) . 3_666 no
C7 O2 2.852(5) . . no
C8 C13 3.387(6) . . no
C9 C12 3.427(6) . . no
C10 O1 3.407(6) . 2_646 no
C10 C17 3.479(7) . . no
C11 C17 3.296(7) . . no
C11 C2 3.518(7) . 3_666 no
C12 C9 3.427(6) . . no
C12 C2 3.555(6) . 3_666 no
C13 C8 3.387(6) . . no
C13 C17 3.110(6) . . no
C14 O2 3.084(6) . 2_756 no
C15 O2 3.261(6) . . no
C15 O2 3.285(7) . 2_756 no
C16 O2 3.236(6) . . no
C17 O2 3.322(6) . . no
C17 C11 3.296(7) . . no
C17 C10 3.479(7) . . no
C17 C13 3.110(6) . . no
C21 O1 3.219(6) . 1_545 no
C2 H8A 3.0900 . 3_666 no
C4 H10A 2.9600 . 2_646 no
C4 H10B 2.6300 . . no
C5 H7B 2.9000 . . no
C6 H21 3.0800 . . no
C7 H21 2.6700 . . no
C10 H6 2.8200 . 2_656 no
C10 H4 2.8400 . . no
C11 H17 2.7900 . . no
C11 H4 3.0800 . 2_656 no
C11 H2 2.8800 . 3_666 no
C12 H8A 2.6100 . . no
C12 H17 2.4000 . . no
C12 H2 2.9200 . 3_666 no
C13 H15A 2.9800 . . no
C13 H7A 2.8000 . . no
C13 H2 3.0300 . 3_666 no
C13 H8A 2.8300 . . no
C13 H17 2.6000 . . no
C16 H10A 2.9800 . . no
C19 H22C 3.1000 . 3_757 no
C20 H22C 3.0000 . 3_757 no
C21 H6 2.7300 . . no
C21 H7A 3.0700 . . no
C21 H7B 2.6200 . . no
H1 H8B 2.4900 . . no
H2 O1 2.7100 . 3_666 no
H2 O3 2.7000 . 3_666 no
H2 C11 2.8800 . 3_666 no
H2 C12 2.9200 . 3_666 no
H2 C13 3.0300 . 3_666 no
H4 C10 2.8400 . . no
H4 H10B 2.3200 . . no
H4 O1 2.7900 . 2_646 no
H4 C11 3.0800 . 2_646 no
H4 H10A 2.5600 . 2_646 no
H6 C21 2.7300 . . no
H6 H21 2.5900 . . no
H6 C10 2.8200 . 2_646 no
H6 H10B 2.2700 . 2_646 no
H7A O2 2.2700 . . no
H7A C13 2.8000 . . no
H7A C21 3.0700 . . no
H7A H14B 2.5200 . 1_545 no
H7B O1 2.8000 . 1_545 no
H7B O3 2.6700 . 1_545 no
H7B C5 2.9000 . . no
H7B C21 2.6200 . . no
H7B H21 2.1000 . . no
H8A C12 2.6100 . . no
H8A C13 2.8300 . . no
H8A C2 3.0900 . 3_666 no
H8B H1 2.4900 . . no
H10A C16 2.9800 . . no
H10A C4 2.9600 . 2_656 no
H10A H4 2.5600 . 2_656 no
H10B C4 2.6300 . . no
H10B H4 2.3200 . . no
H10B H6 2.2700 . 2_656 no
H14A O2 2.2900 . . no
H14A O2 2.8000 . 2_756 no
H14B H7A 2.5200 . 1_565 no
H14B O2 2.7800 . 2_756 no
H15A O2 2.8500 . . no
H15A C13 2.9800 . . no
H15A H22A 2.5700 . 4_554 no
H15B O2 2.6300 . 2_756 no
H17 C11 2.7900 . . no
H17 C12 2.4000 . . no
H17 C13 2.6000 . . no
H18 H22B 2.3700 . . no
H21 O1 2.3300 . 1_545 no
H21 O3 2.8200 . 1_545 no
H21 C6 3.0800 . . no
H21 C7 2.6700 . . no
H21 H6 2.5900 . . no
H21 H7B 2.1000 . . no
H22A O2 2.8900 . 4_555 no
H22A H15A 2.5700 . 4_555 no
H22B H18 2.3700 . . no
H22C C19 3.1000 . 3_757 no
H22C C20 3.0000 . 3_757 no
H22C H22C 2.5200 . 3_757 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)
#
C7 H7A O2 0.9700 2.2700 2.852(5) 117.00 . yes
C14 H14A O2 0.9700 2.2900 2.639(6) 100.00 . yes
C21 H21 O1 0.9300 2.3300 3.219(6) 160.00 1_545 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
#;
# ?
#;


#===END
