# CIF-file generated for mo_ModSa2aP 21/c       R = 0.03
 
#==============================================================================
data_global
#==============================================================================
 
# 0. AUDIT DETAILS
 
_audit_creation_date                              'Thursday, 11 January 201'
_audit_creation_method                            'PLATON <TABLE ACC> option'
_audit_update_record
;
;
 
#===============================================================================
 
# 1. SUBMISSION DETAILS
 
# Name and address of author for X-ray correspondence

_publ_contact_author_name                    # Name of author for correspondence
;
Dr. Alexander Pöthig
;
_publ_contact_author_address              # address of author for correspondence
;
Catalysis Research Center
Technische Universität München
Ernst-Otto-Fischer-Str. 1
85747 Garching bei München
Germany
;
 
_publ_contact_author_email                    alexander.poethig@tum.de
_publ_contact_author_fax                      '+49(0)89 289 54128'
_publ_contact_author_phone                    '+49(0)89 289 54149'
 
_publ_requested_journal                       'J. Organ. Chem.'

_publ_contact_letter                         # Include date of submission
;
Date of submission: November 2018
;
 
#===============================================================================
 
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
 
#===============================================================================
 
# 3. TITLE AND AUTHOR LIST
 
_publ_section_title
;
[6 pi] Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification 
Mechanism and Scope
;
_publ_section_title_footnote
;
;
 
# The loop structure below should contain the names and adresses of all
# authors, in the required order of publication. Repeat as necessary.
 
 
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
       'Modha, S. G.'
;   # author related footnote
?
;
;
Catalysis Research Center & Department Chemie
Technische Universität München
Lichtenbergstr. 4
85747 Garching bei München
Germany
;
       'Pöthig, A.'
;   # author related footnote
?
;
;
Catalysis Research Center & Department Chemie
Technische Universität München
Lichtenbergstr. 4
85747 Garching bei München
Germany
;
       'Dreuw, A.'
;   # author related footnote
?
;
;
Interdisciplinary Center for Scientific Computing 
Ruprecht-Karls University 
Im Neuenheimer Feld 205A 
69120 Heidelberg 
Germany
;
       'Bach, Th.'
;   # author related footnote
?
;
;
Catalysis Research Center & Department Chemie
Technische Universität München
Lichtenbergstr. 4
85747 Garching bei München
Germany
; 
#===============================================================================
 
# 4. TEXT
 
_publ_section_synopsis
;
 ?
;
_publ_section_abstract
;
Upon irradiation at 366 nm, tertiary N-alkoxycarbonyl-N-aryl-beta-enaminones 
furnished exclusively the trans-hexahydrocarbazol-4-ones via conrotatory 
[6 pi] photocyclization, but epimerized on silica to cis-hexahydrocarbazol-4
-ones. Acceptor substitution on the nitrogen atom enhanced the stability of 
the cyclized products compared to N-alkyl-N-aryl-beta-enaminones reported 
previously. The mechanism of this [6 pi] photocyclization was investigated by 
quenching experiments, deuterium labelling experiments and DFT calculations 
suggesting a triplet pathway for the conrotatory ring closure followed by 
a suprafacial [1,4]-hydrogen migration.
;
 
# Insert blank lines between paragraphs
 
_publ_section_comment
;
;
_publ_section_exptl_prep
;
 The crystal was fixed on the top of a microsampler with
 perfluorinated ether and transferred to the diffractometer.
;
_publ_section_exptl_refinement
;
 Solution and refinements with the program APEX (Bruker 2013) 
 and SHELXL2014 (Sheldrick, 2014)in conjunction with SHELXLE (Huebschle, 2011).
 Hydrogen atoms could not be located in the difference Fourier maps
 and were calculated in ideal positions (riding model).
;
 
# Insert blank lines between references
 
_publ_section_references
;
 Allen, F. H.(2004). ENCIFER. J. Applied Cryst. 37, 335-338. 

 Bruker (2013). APEX suite of crystallographic software.
 APEX 2 Version 2013.4. Bruker AXS Inc., Madison, Wisconsin, USA.

 Bruker (2012). SAINT, Version 8.27b and SADABS Version 2012/1.
 Bruker AXS Inc., Madison, Wisconsin, USA.

 Bruker (2008b). SAINT, Version 7.56a and TWINABS Version 2008/1.
 Bruker AXS Inc., Madison, Wisconsin, USA.

 Flack, H.D. (1983). Acta Cryst. A39, 876-881.
 
 Huebschle, C. B.; Sheldrick, G. M.; Dittrich, B. (2011). SHELXLE. 
 J. Appl. Cryst., 44, (2011) 1281 - 1284.   

 Sheldrick, G. M. (1997). SHELXS97. University of Göttingen, Germany.
 
 Sheldrick, G. M. (2014). SHELXL2014. University of Göttingen, Germany.

 Spek, A. L. (2011). PLATON, A Multipurpose Crystallographic Tool, Utrecht
 University, Utrecht, The Netherlands.
  
 Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
 
 Wilson, A.J.C. (1992). Ed. International Tables for Crystallography,
 Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;

_publ_section_acknowledgements
;
;
_publ_section_figure_captions
; View of the title compound with the atom numbering scheme.
Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
;

 
#===============================================================================
 
data_compound8a
 
#===============================================================================
 
# 5. CHEMICAL DATA
 
_chemical_formula_moiety
'C14 H15 N O3'
_chemical_formula_sum
'C14 H15 N O3'
_chemical_formula_weight                             245.27
_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                              monoclinic
_symmetry_space_group_name_Hall                   '-P 2ybc'
_symmetry_space_group_name_H-M                    'P 21/c'
_symmetry_Int_Tables_number                              14
 
loop_
_space_group_symop_id
_space_group_symop_operation_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                                        9.3380(4)
_cell_length_b                                       15.7753(7)
_cell_length_c                                        8.6495(4)
_cell_angle_alpha                                            90
_cell_angle_beta                                     112.182(2)
_cell_angle_gamma                                            90
_cell_volume                                         1179.86(9)
_cell_formula_units_Z                                 4
_cell_measurement_temperature                       100
_cell_measurement_reflns_used     9923    
_cell_measurement_theta_min       2.6862        
_cell_measurement_theta_max       28.3167              

_exptl_crystal_description        'block'
_exptl_crystal_colour             'clear colourless'
 
_exptl_crystal_size_max                               0.515
_exptl_crystal_size_mid                               0.228
_exptl_crystal_size_min                               0.208
_exptl_crystal_size_rad                           ?
_exptl_crystal_density_meas                       ?
_exptl_crystal_density_diffrn                         1.381
_exptl_crystal_density_method                    'Not Measured'
_exptl_crystal_F_000                                    520
_exptl_absorpt_coefficient_mu                         0.097
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_process_details 'SADABS 2014/5, Bruker, 2014'
_exptl_absorpt_correction_T_min                   0.7253     
_exptl_absorpt_correction_T_max                   0.7457
 
#===============================================================================
 
# 7. EXPERIMENTAL DATA
 
_exptl_special_details
;
Diffractometer operator             A. Poethig
scanspeed                           20 s per frame
dx                                  34 mm
391 frames measured in 3 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
;
_diffrn_ambient_temperature                         100
_diffrn_radiation_wavelength                        0.71073
_diffrn_radiation_probe                           'x-ray'
_diffrn_radiation_type                            'MoK\a'
_diffrn_radiation_source          'IMS microsource'
_diffrn_radiation_monochromator   'HELIOS optic'


_diffrn_measurement_device        ' κ-geometry diffractometer '
_diffrn_measurement_device_type   ' Bruker Photon CMOS '
_diffrn_measurement_method        ' phi- and omega-rotation '
_diffrn_detector                  ' CMOS plate '
_diffrn_detector_area_resol_mean  16
 
# number of measured reflections (redundant set)
_diffrn_reflns_number                             28281
_diffrn_reflns_av_R_equivalents                    0.0318
_diffrn_reflns_av_unetI/netI                       0.0126
_diffrn_reflns_limit_h_min                          -11
_diffrn_reflns_limit_h_max                           11
_diffrn_reflns_limit_k_min                          -18
_diffrn_reflns_limit_k_max                           18
_diffrn_reflns_limit_l_min                          -10
_diffrn_reflns_limit_l_max                           10
_diffrn_reflns_theta_min                           2.36
_diffrn_reflns_theta_max                          25.02
_diffrn_reflns_theta_full                         25.02
_diffrn_measured_fraction_theta_max               1.000
_diffrn_measured_fraction_theta_full              1.000
_diffrn_reflns_reduction_process
;
;
 
# number of unique reflections
_reflns_number_total                                 2081
# number of observed reflections (> n sig(I))
_reflns_number_gt                                    1861
_reflns_threshold_expression                      I>2σ(I)
 
_computing_data_collection       'APEX III Control Software (Bruker, 2015)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  
'SHELXL2014 (Sheldrick, 2014), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2014)'
 
#===============================================================================
 
# 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)+(0.0298P)²+0.6920P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary                     '?'
_atom_sites_solution_secondary                   '?'
_atom_sites_solution_hydrogens                   'geom'

_refine_ls_hydrogen_treatment                    'constr'
 
_refine_ls_extinction_method                   'shelxl-2014/7 (sheldrick 2014'
_refine_ls_extinction_coef                             0.0266(18)
_refine_ls_extinction_expression
'FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^'
_refine_ls_abs_structure_details                  ?
_refine_ls_abs_structure_Flack                   .
_refine_ls_number_reflns                               2081
_refine_ls_number_parameters                            165
_refine_ls_number_restraints                              0
_refine_ls_number_constraints                     ?
_refine_ls_R_factor_all                              0.0365
_refine_ls_R_factor_gt                               0.0318
_refine_ls_wR_factor_ref                             0.0783
_refine_ls_wR_factor_gt                              0.0751
_refine_ls_goodness_of_fit_ref                        1.074
_refine_ls_restrained_S_all                           1.074
_refine_ls_shift/su_max                               0.000
_refine_ls_shift/su_mean                              0.000
_refine_diff_density_max                              0.274
_refine_diff_density_min                             -0.204
_refine_diff_density_rms                              0.039
 
#===============================================================================
 
# 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
O10 O Uani -0.04929(10) 0.52784(6) 0.30667(11) 1.000 0.0205(3) d . . .
O12 O Uani 0.72476(10) 0.64778(6) 0.63334(11) 1.000 0.0173(3) d . . .
O13 O Uani 0.61317(10) 0.64207(6) 0.82545(11) 1.000 0.0168(3) d . . .
N9 N Uani 0.46963(12) 0.61387(7) 0.56035(13) 1.000 0.0132(3) d . . .
C1 C Uani 0.27040(15) 0.69598(9) 0.61965(17) 1.000 0.0182(4) d . . .
C2 C Uani 0.10714(15) 0.69233(9) 0.61890(17) 1.000 0.0181(4) d . . .
C3 C Uani -0.00504(15) 0.65901(9) 0.45165(17) 1.000 0.0177(4) d . . .
C4 C Uani 0.04478(15) 0.57703(8) 0.39864(15) 1.000 0.0142(4) d . . .
C4A C Uani 0.21613(14) 0.55630(8) 0.45506(15) 1.000 0.0124(3) d . . .
C4B C Uani 0.27708(15) 0.57151(8) 0.31753(16) 1.000 0.0124(3) d . . .
C5 C Uani 0.20898(16) 0.55422(8) 0.14881(16) 1.000 0.0160(4) d . . .
C6 C Uani 0.29442(16) 0.56616(9) 0.04867(16) 1.000 0.0186(4) d . . .
C7 C Uani 0.44535(16) 0.59535(9) 0.11868(17) 1.000 0.0182(4) d . . .
C8 C Uani 0.51486(15) 0.61414(8) 0.28852(16) 1.000 0.0158(4) d . . .
C8A C Uani 0.42835(15) 0.60174(8) 0.38677(15) 1.000 0.0125(3) d . . .
C9A C Uani 0.32973(14) 0.60758(8) 0.60318(16) 1.000 0.0133(4) d . . .
C11 C Uani 0.61283(15) 0.63587(8) 0.66972(16) 1.000 0.0129(4) d . . .
C14 C Uani 0.76031(15) 0.66019(9) 0.95705(17) 1.000 0.0190(4) d . . .
H1A H Uiso 0.34040 0.72230 0.72500 1.000 0.0220 c RU . .
H1B H Uiso 0.27080 0.73190 0.52590 1.000 0.0220 c RU . .
H2A H Uiso 0.07480 0.74970 0.63890 1.000 0.0220 c RU . .
H2B H Uiso 0.10540 0.65470 0.70980 1.000 0.0220 c RU . .
H3A H Uiso -0.10750 0.65070 0.45860 1.000 0.0210 c RU . .
H3B H Uiso -0.01700 0.70230 0.36490 1.000 0.0210 c RU . .
H4A H Uiso 0.23000 0.49480 0.48540 1.000 0.0150 c RU . .
H5 H Uiso 0.10530 0.53440 0.10160 1.000 0.0190 c RU . .
H6 H Uiso 0.24920 0.55430 -0.06750 1.000 0.0220 c RU . .
H7 H Uiso 0.50280 0.60280 0.04950 1.000 0.0220 c RU . .
H8 H Uiso 0.61800 0.63470 0.33550 1.000 0.0190 c RU . .
H9A H Uiso 0.35440 0.57530 0.70970 1.000 0.0160 c RU . .
H14A H Uiso 0.84310 0.65360 0.91440 1.000 0.0280 c RU . .
H14B H Uiso 0.77750 0.62080 1.05000 1.000 0.0280 c RU . .
H14C H Uiso 0.76020 0.71850 0.99620 1.000 0.0280 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
 O10     C4       1.2161(16)                     .       .                   yes
 O12     C11      1.2145(18)                     .       .                   yes
 O13     C11      1.3493(16)                     .       .                   yes
 O13     C14      1.4437(17)                     .       .                   yes
 N9      C8A      1.4150(16)                     .       .                   yes
 N9      C9A      1.4897(18)                     .       .                   yes
 N9      C11      1.3595(18)                     .       .                   yes
 C1      C2         1.523(2)                     .       .                   no
 C1      C9A      1.5270(19)                     .       .                   no
 C2      C3         1.524(2)                     .       .                   no
 C3      C4       1.5034(19)                     .       .                   no
 C4      C4A        1.522(2)                     .       .                   no
 C4A     C4B      1.5192(19)                     .       .                   no
 C4A     C9A      1.5475(18)                     .       .                   no
 C4B     C5       1.3812(18)                     .       .                   no
 C4B     C8A        1.394(2)                     .       .                   no
 C5      C6         1.394(2)                     .       .                   no
 C6      C7         1.386(2)                     .       .                   no
 C7      C8       1.3954(19)                     .       .                   no
 C8      C8A        1.390(2)                     .       .                   no
 C1      H1A          0.9900                     .       .                   no
 C1      H1B          0.9900                     .       .                   no
 C2      H2A          0.9900                     .       .                   no
 C2      H2B          0.9900                     .       .                   no
 C3      H3A          0.9900                     .       .                   no
 C3      H3B          0.9900                     .       .                   no
 C4A     H4A          1.0000                     .       .                   no
 C5      H5           0.9500                     .       .                   no
 C6      H6           0.9500                     .       .                   no
 C7      H7           0.9500                     .       .                   no
 C8      H8           0.9500                     .       .                   no
 C9A     H9A          1.0000                     .       .                   no
 C14     H14A         0.9800                     .       .                   no
 C14     H14B         0.9800                     .       .                   no
 C14     H14C         0.9800                     .       .                   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
 C11     O13     C14      116.38(11)             .       .       .           yes
 C8A     N9      C9A      109.98(11)             .       .       .           yes
 C8A     N9      C11      125.11(12)             .       .       .           yes
 C9A     N9      C11      124.65(11)             .       .       .           yes
 C2      C1      C9A      111.28(12)             .       .       .           no
 C1      C2      C3       110.20(12)             .       .       .           no
 C2      C3      C4       113.91(12)             .       .       .           no
 O10     C4      C3       121.21(13)             .       .       .           yes
 O10     C4      C4A      119.01(12)             .       .       .           yes
 C3      C4      C4A      119.74(11)             .       .       .           no
 C4      C4A     C4B      111.99(10)             .       .       .           no
 C4      C4A     C9A      117.53(11)             .       .       .           no
 C4B     C4A     C9A      102.91(11)             .       .       .           no
 C4A     C4B     C5       129.57(13)             .       .       .           no
 C4A     C4B     C8A      109.64(11)             .       .       .           no
 C5      C4B     C8A      120.61(13)             .       .       .           no
 C4B     C5      C6       119.11(14)             .       .       .           no
 C5      C6      C7       119.97(12)             .       .       .           no
 C6      C7      C8       121.51(14)             .       .       .           no
 C7      C8      C8A      117.85(13)             .       .       .           no
 N9      C8A     C4B      109.15(12)             .       .       .           yes
 N9      C8A     C8       129.89(13)             .       .       .           yes
 C4B     C8A     C8       120.94(12)             .       .       .           no
 N9      C9A     C1       110.21(11)             .       .       .           yes
 N9      C9A     C4A      102.73(10)             .       .       .           yes
 C1      C9A     C4A      113.28(11)             .       .       .           no
 O12     C11     O13      124.72(12)             .       .       .           yes
 O12     C11     N9       125.16(12)             .       .       .           yes
 O13     C11     N9       110.13(12)             .       .       .           yes
 C2      C1      H1A          109.00             .       .       .           no
 C2      C1      H1B          109.00             .       .       .           no
 C9A     C1      H1A          109.00             .       .       .           no
 C9A     C1      H1B          109.00             .       .       .           no
 H1A     C1      H1B          108.00             .       .       .           no
 C1      C2      H2A          110.00             .       .       .           no
 C1      C2      H2B          110.00             .       .       .           no
 C3      C2      H2A          110.00             .       .       .           no
 C3      C2      H2B          110.00             .       .       .           no
 H2A     C2      H2B          108.00             .       .       .           no
 C2      C3      H3A          109.00             .       .       .           no
 C2      C3      H3B          109.00             .       .       .           no
 C4      C3      H3A          109.00             .       .       .           no
 C4      C3      H3B          109.00             .       .       .           no
 H3A     C3      H3B          108.00             .       .       .           no
 C4      C4A     H4A          108.00             .       .       .           no
 C4B     C4A     H4A          108.00             .       .       .           no
 C9A     C4A     H4A          108.00             .       .       .           no
 C4B     C5      H5           120.00             .       .       .           no
 C6      C5      H5           120.00             .       .       .           no
 C5      C6      H6           120.00             .       .       .           no
 C7      C6      H6           120.00             .       .       .           no
 C6      C7      H7           119.00             .       .       .           no
 C8      C7      H7           119.00             .       .       .           no
 C7      C8      H8           121.00             .       .       .           no
 C8A     C8      H8           121.00             .       .       .           no
 N9      C9A     H9A          110.00             .       .       .           no
 C1      C9A     H9A          110.00             .       .       .           no
 C4A     C9A     H9A          110.00             .       .       .           no
 O13     C14     H14A         109.00             .       .       .           no
 O13     C14     H14B         109.00             .       .       .           no
 O13     C14     H14C         109.00             .       .       .           no
 H14A    C14     H14B         109.00             .       .       .           no
 H14A    C14     H14C         109.00             .       .       .           no
 H14B    C14     H14C         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
 C14     O13     C11     O12       -3.14(18)     .       .       .       .   no
 C14     O13     C11     N9       176.45(11)     .       .       .       .   no
 C9A     N9      C8A     C4B      -11.59(14)     .       .       .       .   no
 C9A     N9      C8A     C8       169.55(13)     .       .       .       .   no
 C11     N9      C8A     C4B      174.10(12)     .       .       .       .   no
 C11     N9      C8A     C8          -4.8(2)     .       .       .       .   no
 C8A     N9      C9A     C1       -99.22(12)     .       .       .       .   no
 C8A     N9      C9A     C4A       21.77(13)     .       .       .       .   no
 C11     N9      C9A     C1        75.12(15)     .       .       .       .   no
 C11     N9      C9A     C4A     -163.89(11)     .       .       .       .   no
 C8A     N9      C11     O12         -0.3(2)     .       .       .       .   no
 C8A     N9      C11     O13     -179.87(11)     .       .       .       .   no
 C9A     N9      C11     O12     -173.78(12)     .       .       .       .   no
 C9A     N9      C11     O13        6.63(17)     .       .       .       .   no
 C9A     C1      C2      C3       -63.86(14)     .       .       .       .   no
 C2      C1      C9A     N9       165.44(10)     .       .       .       .   no
 C2      C1      C9A     C4A       50.99(15)     .       .       .       .   no
 C1      C2      C3      C4        51.80(16)     .       .       .       .   no
 C2      C3      C4      O10      153.37(12)     .       .       .       .   no
 C2      C3      C4      C4A      -29.03(17)     .       .       .       .   no
 O10     C4      C4A     C4B       75.62(15)     .       .       .       .   no
 O10     C4      C4A     C9A     -165.56(11)     .       .       .       .   no
 C3      C4      C4A     C4B     -102.03(13)     .       .       .       .   no
 C3      C4      C4A     C9A       16.79(17)     .       .       .       .   no
 C4      C4A     C4B     C5       -40.47(18)     .       .       .       .   no
 C4      C4A     C4B     C8A      144.48(11)     .       .       .       .   no
 C9A     C4A     C4B     C5      -167.62(13)     .       .       .       .   no
 C9A     C4A     C4B     C8A       17.32(14)     .       .       .       .   no
 C4      C4A     C9A     N9      -146.20(11)     .       .       .       .   no
 C4      C4A     C9A     C1       -27.33(16)     .       .       .       .   no
 C4B     C4A     C9A     N9       -22.65(12)     .       .       .       .   no
 C4B     C4A     C9A     C1        96.22(13)     .       .       .       .   no
 C4A     C4B     C5      C6      -173.61(13)     .       .       .       .   no
 C8A     C4B     C5      C6           1.0(2)     .       .       .       .   no
 C4A     C4B     C8A     N9        -4.26(15)     .       .       .       .   no
 C4A     C4B     C8A     C8       174.72(12)     .       .       .       .   no
 C5      C4B     C8A     N9      -179.83(12)     .       .       .       .   no
 C5      C4B     C8A     C8          -0.9(2)     .       .       .       .   no
 C4B     C5      C6      C7          -0.3(2)     .       .       .       .   no
 C5      C6      C7      C8          -0.6(2)     .       .       .       .   no
 C6      C7      C8      C8A          0.7(2)     .       .       .       .   no
 C7      C8      C8A     N9       178.74(13)     .       .       .       .   no
 C7      C8      C8A     C4B        0.00(19)     .       .       .       .   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)
#
C3      H3A     O12         0.9900     2.5500 3.4440(18)     149.00   1_455 yes
C4A     H4A     O12         1.0000     2.5700 3.4019(16)     140.00   3_666 yes
C6      H6      O10         0.9500     2.5500 3.4019(16)     149.00   3_565 yes
C7      H7      O13         0.9500     2.5900 3.5261(18)     168.00   1_554 yes
C8      H8      O12         0.9500     2.3900 2.9334(16)     116.00     .   yes
C14     H14A    O12         0.9800     2.2600 2.6993(16)     106.00     .   yes
C14     H14C    O12         0.9800     2.5000 3.4633(17)     166.00   4_565 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
