# CIF-file generated for annra1_0maP 21 21 2    R = 0.03
 
#==============================================================================
data_global
#==============================================================================
 
# 0. AUDIT DETAILS
 
_audit_creation_date                              'Friday, 29 March 2019   '
_audit_creation_method                            'PLATON <TABLE ACC> option'
_audit_update_record
;
March 10th 2020: CIF updated for publication by author C.J.
;
 
#===============================================================================
 
# 1. SUBMISSION DETAILS
 
# Name and address of author for X-ray correspondence

_publ_contact_author_name                    # Name of author for correspondence
;
Prof. Dr. Thorsten Bach
;
_publ_contact_author_address              # address of author for correspondence
;
Lehrstuhl für Organische Chemie I
Technische Universität München
Lichtenbergstr. 4
85747 Garching
Germany
;
 
_publ_contact_author_email                    thorsten.bach@ch.tum.de
_publ_contact_author_fax                      '+49(0)89 289 13330'
_publ_contact_author_phone                    '+49(0)89 289 13315'
 
_publ_requested_journal                       'J. Am. Chem. Soc.'
# Publication choise FI, CI or EI for Inorganic
#                    FM, CM or EM for Metal-organic
#                    FO, CO or EO for Organic
_publ_requested_category                      ?
_publ_requested_coeditor_name                 ?
 
_publ_contact_letter                         # Include date of submission
;
Date of submission: Match 2020
;
 
#===============================================================================
 
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
 
#===============================================================================
 
# 3. TITLE AND AUTHOR LIST
 
_publ_section_title
;
A Chiral Phenanthroline Ligand with a Hydrogen Bonding Site: Application
to the Enantioselective Amination of Methylene Groups
;
_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
       'Annapureddy, R. S.'
;   # author related footnote
?
;
;
       Department Chemie and Catalysis Research Center (CRC),
       Technische Universität München,
       Lichtenbergstr. 4,
       D-85747 Garching,
       Germany.
;
       'Jandl, C.'
;   # author related footnote
?
;
;
       Department Chemie and Catalysis Research Center (CRC),
       Technische Universität München,
       Lichtenbergstr. 4,
       D-85747 Garching,
       Germany.
;
       'Bach, T.'
;   # author related footnote
?
;
;
       Department Chemie and Catalysis Research Center (CRC),
       Technische Universität München,
       Lichtenbergstr. 4,
       D-85747 Garching,
       Germany.
;
 
#===============================================================================
 
# 4. TEXT
 
_publ_section_synopsis
;
 ?
;
_publ_section_abstract
;
A silver-catalyzed amination is reported which occurs at the aliphatic
C3-substituent of various quinolones and pyridones. The C-H activation
reaction proceeded with high site- and enantioselectivity (14 examples,
83-97% ee). Key to its success is the use of a chiral phenanthroline ligand
that is attached via an ethynyl linker to the 8-position of octahydro-
1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol%) served as the silver source,
PhINNs as the nitrene precursor and 1,10-phenanthroline as the coligand.
The reaction outcome can be understood by assuming a nitrene C-H insertion
within a hydrogen-bonded silver complex in which a single C-H bond is
exposed to the catalytic reaction center.
;
 
# Insert blank lines between paragraphs
 
_publ_section_comment
;
;
_publ_section_exptl_prep
;
 The crystal was fixed on the top of a kapton micro sampler with
 perfluorinated ether and transferred to the diffractometer.
;
_publ_section_exptl_refinement
;
 Solution and refinements with the program APEX (Bruker 2016) 
 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 (2016). APEX suite of crystallographic software.
 APEX 3 Version 2016.9-0. Bruker AXS Inc., Madison, Wisconsin, USA.

 Bruker (2017). SAINT, Version 8.38A. Bruker AXS Inc., Madison,
 Wisconsin, USA.

 Bruker (2016). SADABS, Version 2016/2. 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.   

 Parsons, S; Flack, H. D.; Wagner, T. (2013). Acta Cryst. B69, 249-259.

 Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
 
 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_compound_2
 
#===============================================================================
 
# 5. CHEMICAL DATA
 
_chemical_name_systematic
;
;
_chemical_name_common                             ?
_chemical_melting_point                           ?
_chemical_formula_moiety
'C23 H19 N3 O, C6 H6'
_chemical_formula_structural                      ?
_chemical_formula_sum
'C29 H25 N3 O'
_chemical_formula_iupac                           ?
_chemical_formula_weight                             431.52
_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                            orthorhombic
_symmetry_space_group_name_Hall                   'P 2 2ab'
_symmetry_space_group_name_H-M                    'P 21 21 2'
_symmetry_Int_Tables_number                              18
 
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
   1 x,y,z
   2 -x,-y,z
   3 1/2+x,1/2-y,-z
   4 1/2-x,1/2+y,-z
 
_cell_length_a                                      11.8165(10)
_cell_length_b                                      19.5724(16)
_cell_length_c                                       10.8469(9)
_cell_angle_alpha                                            90
_cell_angle_beta                                             90
_cell_angle_gamma                                            90
_cell_volume                                          2508.6(4)
_cell_formula_units_Z                                 4
_cell_measurement_temperature                       100
_cell_measurement_reflns_used     9934 
_cell_measurement_theta_min       2.5489
_cell_measurement_theta_max       26.3296
_cell_special_details
;
;
 
_exptl_crystal_description        'fragment'
_exptl_crystal_colour             'colourless'

_exptl_crystal_size_max                               0.347
_exptl_crystal_size_mid                               0.260
_exptl_crystal_size_min                               0.216
_exptl_crystal_size_rad                           ?
_exptl_crystal_density_meas                       ?
_exptl_crystal_density_diffrn                         1.143
_exptl_crystal_density_method                    'Not Measured'
_exptl_crystal_F_000                                    912
_exptl_absorpt_coefficient_mu                         0.070
_exptl_crystal_density_meas_temp                  ?
 
_exptl_absorpt_correction_type 'multi-scan'
_exptl_absorpt_process_details 'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min                   0.6778    
_exptl_absorpt_correction_T_max                   0.7454
 
#===============================================================================
 
# 7. EXPERIMENTAL DATA
 
_exptl_special_details
;
Diffractometer operator             C. Jandl
scanspeed                           2-20 s per frame
dx                                  80 mm
1195 frames measured in 4 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          '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                             19905
_diffrn_reflns_av_R_equivalents                    0.0259
_diffrn_reflns_av_unetI/netI                       0.0221
_diffrn_reflns_limit_h_min                          -14
_diffrn_reflns_limit_h_max                           14
_diffrn_reflns_limit_k_min                          -22
_diffrn_reflns_limit_k_max                           24
_diffrn_reflns_limit_l_min                          -13
_diffrn_reflns_limit_l_max                           13
_diffrn_reflns_theta_min                           2.01
_diffrn_reflns_theta_max                          26.02
_diffrn_reflns_theta_full                         25.24
_diffrn_measured_fraction_theta_max               0.999
_diffrn_measured_fraction_theta_full              0.999
_diffrn_reflns_reduction_process
;
;
 
# number of unique reflections
_reflns_number_total                                 4956
# number of observed reflections (> n sig(I))
_reflns_number_gt                                    4831
_reflns_threshold_expression                      I>2σ(I)
 
_computing_data_collection       'APEX III Control Software (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2017)'
_computing_data_reduction        'SAINT (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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)+(0.0297P)²+0.7799P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary                     'iterative'
_atom_sites_solution_secondary                   'difmap'
_atom_sites_solution_hydrogens                   'geom'
 
 
_refine_ls_hydrogen_treatment                    'constr'
 
_refine_ls_extinction_method                      'none'
_refine_ls_abs_structure_details
 'Flack (1983)'
_refine_ls_abs_structure_Flack                            0.1(16)
 
# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration                 unk
 
_refine_ls_number_reflns                               4956
_refine_ls_number_parameters                            299
_refine_ls_number_restraints                              0
_refine_ls_number_constraints                     ?
_refine_ls_R_factor_all                              0.0351
_refine_ls_R_factor_gt                               0.0340
_refine_ls_wR_factor_ref                             0.0800
_refine_ls_wR_factor_gt                              0.0794
_refine_ls_goodness_of_fit_ref                        1.061
_refine_ls_restrained_S_all                           1.061
_refine_ls_shift/su_max                               0.000
_refine_ls_shift/su_mean                              0.000
_refine_diff_density_max                              0.159
_refine_diff_density_min                             -0.140
_refine_diff_density_rms                              0.031
 
#===============================================================================
 
# 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 0.33264(14) 0.68411(7) 0.30388(14) 1.000 0.0335(5) d . . .
N1 N Uani 0.66442(14) 0.44798(8) 0.51595(15) 1.000 0.0222(5) d . . .
N2 N Uani 0.67610(14) 0.39256(8) 0.74546(15) 1.000 0.0232(5) d . . .
N3 N Uani 0.35502(14) 0.70042(8) 0.51126(16) 1.000 0.0226(5) d . . .
C1 C Uani 0.65868(19) 0.47462(10) 0.40417(19) 1.000 0.0264(6) d . . .
C2 C Uani 0.64461(18) 0.54423(10) 0.38144(19) 1.000 0.0268(6) d . . .
C3 C Uani 0.63496(16) 0.58916(10) 0.47869(19) 1.000 0.0215(5) d . . .
C4 C Uani 0.63899(15) 0.56214(9) 0.60039(18) 1.000 0.0192(5) d . . .
C5 C Uani 0.65489(15) 0.49085(10) 0.61358(18) 1.000 0.0193(5) d . . .
C6 C Uani 0.62671(16) 0.60353(9) 0.70822(19) 1.000 0.0218(6) d . . .
C7 C Uani 0.62954(17) 0.57601(10) 0.82190(19) 1.000 0.0236(6) d . . .
C8 C Uani 0.64596(17) 0.50380(10) 0.83914(18) 1.000 0.0219(5) d . . .
C9 C Uani 0.65978(15) 0.46122(9) 0.73581(18) 1.000 0.0183(5) d . . .
C10 C Uani 0.64792(19) 0.47312(11) 0.9566(2) 1.000 0.0288(6) d . . .
C11 C Uani 0.66262(19) 0.40404(11) 0.9663(2) 1.000 0.0291(6) d . . .
C12 C Uani 0.67693(19) 0.36616(10) 0.8573(2) 1.000 0.0277(6) d . . .
C13 C Uani 0.62036(16) 0.66110(10) 0.45694(19) 1.000 0.0218(6) d . . .
C14 C Uani 0.60519(16) 0.72031(10) 0.43517(19) 1.000 0.0216(6) d . . .
C15 C Uani 0.58851(17) 0.79305(10) 0.40599(19) 1.000 0.0228(6) d . . .
C16 C Uani 0.49295(17) 0.81120(10) 0.31368(18) 1.000 0.0232(6) d . . .
C17 C Uani 0.50641(19) 0.88935(10) 0.3085(2) 1.000 0.0303(6) d . . .
C18 C Uani 0.53901(19) 0.90825(11) 0.4434(2) 1.000 0.0306(7) d . . .
C19 C Uani 0.54070(17) 0.83873(10) 0.5106(2) 1.000 0.0247(6) d . . .
C20 C Uani 0.41603(16) 0.81574(10) 0.52198(18) 1.000 0.0214(5) d . . .
C21 C Uani 0.39309(17) 0.75074(10) 0.59966(19) 1.000 0.0224(6) d . . .
C22 C Uani 0.35441(17) 0.72018(10) 0.39392(19) 1.000 0.0222(5) d . . .
C23 C Uani 0.38513(16) 0.79576(10) 0.38745(19) 1.000 0.0214(5) d . . .
C24 C Uani 0.2681(2) 0.77662(12) 0.0683(2) 1.000 0.0345(7) d . . .
C25 C Uani 0.30731(19) 0.82032(12) -0.0218(2) 1.000 0.0348(7) d . . .
C26 C Uani 0.2352(2) 0.84247(12) -0.1147(2) 1.000 0.0322(7) d . . .
C27 C Uani 0.1234(2) 0.82162(11) -0.1156(2) 1.000 0.0308(6) d . . .
C28 C Uani 0.0842(2) 0.77869(12) -0.0239(2) 1.000 0.0355(7) d . . .
C29 C Uani 0.1565(2) 0.75548(11) 0.0672(2) 1.000 0.0357(8) d . . .
H1 H Uiso 0.66440 0.44470 0.33550 1.000 0.0320 c RU . .
H2 H Uiso 0.64170 0.56060 0.29910 1.000 0.0320 c RU . .
H3 H Uiso 0.33350 0.65920 0.53370 1.000 0.0270 c RU . .
H6 H Uiso 0.61630 0.65140 0.69940 1.000 0.0260 c RU . .
H7 H Uiso 0.62050 0.60470 0.89180 1.000 0.0280 c RU . .
H10 H Uiso 0.63910 0.50020 1.02860 1.000 0.0350 c RU . .
H11 H Uiso 0.66310 0.38220 1.04450 1.000 0.0350 c RU . .
H12 H Uiso 0.68800 0.31830 0.86470 1.000 0.0330 c RU . .
H15 H Uiso 0.66150 0.81280 0.37600 1.000 0.0270 c RU . .
H16 H Uiso 0.49810 0.78760 0.23210 1.000 0.0280 c RU . .
H17A H Uiso 0.43470 0.91170 0.28380 1.000 0.0360 c RU . .
H17B H Uiso 0.56680 0.90270 0.25000 1.000 0.0360 c RU . .
H18A H Uiso 0.61420 0.93040 0.44650 1.000 0.0370 c RU . .
H18B H Uiso 0.48220 0.93930 0.48030 1.000 0.0370 c RU . .
H19 H Uiso 0.58490 0.83790 0.58920 1.000 0.0300 c RU . .
H20 H Uiso 0.36760 0.85440 0.55090 1.000 0.0260 c RU . .
H21A H Uiso 0.46290 0.73520 0.64160 1.000 0.0270 c RU . .
H21B H Uiso 0.33410 0.75950 0.66250 1.000 0.0270 c RU . .
H23 H Uiso 0.31990 0.82350 0.35660 1.000 0.0260 c RU . .
H24 H Uiso 0.31780 0.76100 0.13110 1.000 0.0410 c RU . .
H25 H Uiso 0.38380 0.83530 -0.02030 1.000 0.0420 c RU . .
H26 H Uiso 0.26270 0.87190 -0.17760 1.000 0.0390 c RU . .
H27 H Uiso 0.07370 0.83670 -0.17880 1.000 0.0370 c RU . .
H28 H Uiso 0.00710 0.76500 -0.02340 1.000 0.0430 c RU . .
H29 H Uiso 0.12950 0.72510 0.12880 1.000 0.0430 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      C22        1.232(3)                     .       .                   yes
 N1      C1         1.322(3)                     .       .                   yes
 N1      C5         1.356(3)                     .       .                   yes
 N2      C9         1.362(2)                     .       .                   yes
 N2      C12        1.319(3)                     .       .                   yes
 N3      C21        1.446(3)                     .       .                   yes
 N3      C22        1.330(3)                     .       .                   yes
 C1      C2         1.395(3)                     .       .                   no
 C2      C3         1.378(3)                     .       .                   no
 C3      C4         1.423(3)                     .       .                   no
 C3      C13        1.438(3)                     .       .                   no
 N3      H3           0.8800                     .       .                   no
 C4      C6         1.430(3)                     .       .                   no
 C4      C5         1.415(3)                     .       .                   no
 C5      C9         1.448(3)                     .       .                   no
 C6      C7         1.346(3)                     .       .                   no
 C7      C8         1.439(3)                     .       .                   no
 C8      C9         1.406(3)                     .       .                   no
 C8      C10        1.409(3)                     .       .                   no
 C10     C11        1.367(3)                     .       .                   no
 C11     C12        1.406(3)                     .       .                   no
 C13     C14        1.196(3)                     .       .                   no
 C14     C15        1.472(3)                     .       .                   no
 C15     C19        1.551(3)                     .       .                   no
 C15     C16        1.550(3)                     .       .                   no
 C16     C17        1.539(3)                     .       .                   no
 C16     C23        1.535(3)                     .       .                   no
 C17     C18        1.558(3)                     .       .                   no
 C18     C19        1.544(3)                     .       .                   no
 C19     C20        1.545(3)                     .       .                   no
 C20     C23        1.554(3)                     .       .                   no
 C20     C21        1.550(3)                     .       .                   no
 C22     C23        1.525(3)                     .       .                   no
 C1      H1           0.9500                     .       .                   no
 C2      H2           0.9500                     .       .                   no
 C6      H6           0.9500                     .       .                   no
 C7      H7           0.9500                     .       .                   no
 C10     H10          0.9500                     .       .                   no
 C11     H11          0.9500                     .       .                   no
 C12     H12          0.9500                     .       .                   no
 C15     H15          1.0000                     .       .                   no
 C16     H16          1.0000                     .       .                   no
 C17     H17A         0.9900                     .       .                   no
 C17     H17B         0.9900                     .       .                   no
 C18     H18A         0.9900                     .       .                   no
 C18     H18B         0.9900                     .       .                   no
 C19     H19          1.0000                     .       .                   no
 C20     H20          1.0000                     .       .                   no
 C21     H21A         0.9900                     .       .                   no
 C21     H21B         0.9900                     .       .                   no
 C23     H23          1.0000                     .       .                   no
 C24     C25        1.379(3)                     .       .                   no
 C24     C29        1.382(3)                     .       .                   no
 C25     C26        1.389(3)                     .       .                   no
 C26     C27        1.383(3)                     .       .                   no
 C27     C28        1.382(3)                     .       .                   no
 C28     C29        1.383(3)                     .       .                   no
 C24     H24          0.9500                     .       .                   no
 C25     H25          0.9500                     .       .                   no
 C26     H26          0.9500                     .       .                   no
 C27     H27          0.9500                     .       .                   no
 C28     H28          0.9500                     .       .                   no
 C29     H29          0.9500                     .       .                   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      N1      C5       117.92(17)             .       .       .           yes
 C9      N2      C12      117.29(17)             .       .       .           yes
 C21     N3      C22      115.98(16)             .       .       .           yes
 N1      C1      C2       123.63(19)             .       .       .           yes
 C1      C2      C3       119.87(19)             .       .       .           no
 C2      C3      C4       118.05(18)             .       .       .           no
 C2      C3      C13      120.61(19)             .       .       .           no
 C4      C3      C13      121.34(18)             .       .       .           no
 C22     N3      H3           122.00             .       .       .           no
 C21     N3      H3           122.00             .       .       .           no
 C3      C4      C6       123.01(17)             .       .       .           no
 C3      C4      C5       117.69(17)             .       .       .           no
 C5      C4      C6       119.29(17)             .       .       .           no
 N1      C5      C9       117.64(17)             .       .       .           yes
 C4      C5      C9       119.52(17)             .       .       .           no
 N1      C5      C4       122.84(18)             .       .       .           yes
 C4      C6      C7       121.33(17)             .       .       .           no
 C6      C7      C8       121.03(18)             .       .       .           no
 C7      C8      C9       119.62(18)             .       .       .           no
 C9      C8      C10      117.80(18)             .       .       .           no
 C7      C8      C10      122.58(18)             .       .       .           no
 C5      C9      C8       119.19(17)             .       .       .           no
 N2      C9      C8       122.69(17)             .       .       .           yes
 N2      C9      C5       118.11(17)             .       .       .           yes
 C8      C10     C11        119.6(2)             .       .       .           no
 C10     C11     C12        118.2(2)             .       .       .           no
 N2      C12     C11      124.49(18)             .       .       .           yes
 C3      C13     C14        177.4(2)             .       .       .           no
 C13     C14     C15        178.6(2)             .       .       .           no
 C14     C15     C19      116.68(17)             .       .       .           no
 C16     C15     C19       94.31(15)             .       .       .           no
 C14     C15     C16      117.26(17)             .       .       .           no
 C17     C16     C23      107.49(16)             .       .       .           no
 C15     C16     C17      100.14(16)             .       .       .           no
 C15     C16     C23      102.87(16)             .       .       .           no
 C16     C17     C18      103.14(16)             .       .       .           no
 C17     C18     C19      103.74(16)             .       .       .           no
 C15     C19     C20      103.76(16)             .       .       .           no
 C18     C19     C20      106.38(16)             .       .       .           no
 C15     C19     C18       99.63(16)             .       .       .           no
 C21     C20     C23      105.24(15)             .       .       .           no
 C19     C20     C21      116.69(16)             .       .       .           no
 C19     C20     C23      102.84(15)             .       .       .           no
 N3      C21     C20      104.65(16)             .       .       .           yes
 O1      C22     C23      124.68(18)             .       .       .           yes
 N3      C22     C23      108.95(17)             .       .       .           yes
 O1      C22     N3       126.36(18)             .       .       .           yes
 C20     C23     C22      104.88(16)             .       .       .           no
 C16     C23     C20      104.18(15)             .       .       .           no
 C16     C23     C22      114.38(16)             .       .       .           no
 N1      C1      H1           118.00             .       .       .           no
 C2      C1      H1           118.00             .       .       .           no
 C1      C2      H2           120.00             .       .       .           no
 C3      C2      H2           120.00             .       .       .           no
 C4      C6      H6           119.00             .       .       .           no
 C7      C6      H6           119.00             .       .       .           no
 C6      C7      H7           119.00             .       .       .           no
 C8      C7      H7           119.00             .       .       .           no
 C8      C10     H10          120.00             .       .       .           no
 C11     C10     H10          120.00             .       .       .           no
 C10     C11     H11          121.00             .       .       .           no
 C12     C11     H11          121.00             .       .       .           no
 N2      C12     H12          118.00             .       .       .           no
 C11     C12     H12          118.00             .       .       .           no
 C14     C15     H15          109.00             .       .       .           no
 C16     C15     H15          109.00             .       .       .           no
 C19     C15     H15          109.00             .       .       .           no
 C15     C16     H16          115.00             .       .       .           no
 C17     C16     H16          115.00             .       .       .           no
 C23     C16     H16          115.00             .       .       .           no
 C16     C17     H17A         111.00             .       .       .           no
 C16     C17     H17B         111.00             .       .       .           no
 C18     C17     H17A         111.00             .       .       .           no
 C18     C17     H17B         111.00             .       .       .           no
 H17A    C17     H17B         109.00             .       .       .           no
 C17     C18     H18A         111.00             .       .       .           no
 C17     C18     H18B         111.00             .       .       .           no
 C19     C18     H18A         111.00             .       .       .           no
 C19     C18     H18B         111.00             .       .       .           no
 H18A    C18     H18B         109.00             .       .       .           no
 C15     C19     H19          115.00             .       .       .           no
 C18     C19     H19          115.00             .       .       .           no
 C20     C19     H19          115.00             .       .       .           no
 C19     C20     H20          111.00             .       .       .           no
 C21     C20     H20          111.00             .       .       .           no
 C23     C20     H20          111.00             .       .       .           no
 N3      C21     H21A         111.00             .       .       .           no
 N3      C21     H21B         111.00             .       .       .           no
 C20     C21     H21A         111.00             .       .       .           no
 C20     C21     H21B         111.00             .       .       .           no
 H21A    C21     H21B         109.00             .       .       .           no
 C16     C23     H23          111.00             .       .       .           no
 C20     C23     H23          111.00             .       .       .           no
 C22     C23     H23          111.00             .       .       .           no
 C25     C24     C29        120.0(2)             .       .       .           no
 C24     C25     C26        120.1(2)             .       .       .           no
 C25     C26     C27        119.9(2)             .       .       .           no
 C26     C27     C28        119.6(2)             .       .       .           no
 C27     C28     C29        120.5(2)             .       .       .           no
 C24     C29     C28        119.8(2)             .       .       .           no
 C25     C24     H24          120.00             .       .       .           no
 C29     C24     H24          120.00             .       .       .           no
 C24     C25     H25          120.00             .       .       .           no
 C26     C25     H25          120.00             .       .       .           no
 C25     C26     H26          120.00             .       .       .           no
 C27     C26     H26          120.00             .       .       .           no
 C26     C27     H27          120.00             .       .       .           no
 C28     C27     H27          120.00             .       .       .           no
 C27     C28     H28          120.00             .       .       .           no
 C29     C28     H28          120.00             .       .       .           no
 C24     C29     H29          120.00             .       .       .           no
 C28     C29     H29          120.00             .       .       .           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
 C5      N1      C1      C2           0.7(3)     .       .       .       .   no
 C1      N1      C5      C4           0.1(3)     .       .       .       .   no
 C1      N1      C5      C9       179.22(18)     .       .       .       .   no
 C12     N2      C9      C5      -178.01(18)     .       .       .       .   no
 C12     N2      C9      C8           1.0(3)     .       .       .       .   no
 C9      N2      C12     C11         -0.3(3)     .       .       .       .   no
 C22     N3      C21     C20          2.8(2)     .       .       .       .   no
 C21     N3      C22     O1         174.7(2)     .       .       .       .   no
 C21     N3      C22     C23         -5.4(2)     .       .       .       .   no
 N1      C1      C2      C3          -0.5(3)     .       .       .       .   no
 C1      C2      C3      C4          -0.5(3)     .       .       .       .   no
 C1      C2      C3      C13     -179.97(19)     .       .       .       .   no
 C2      C3      C4      C5           1.2(3)     .       .       .       .   no
 C2      C3      C4      C6      -178.20(18)     .       .       .       .   no
 C13     C3      C4      C5      -179.29(17)     .       .       .       .   no
 C13     C3      C4      C6           1.3(3)     .       .       .       .   no
 C3      C4      C5      N1          -1.1(3)     .       .       .       .   no
 C3      C4      C5      C9       179.85(17)     .       .       .       .   no
 C6      C4      C5      N1       178.34(17)     .       .       .       .   no
 C6      C4      C5      C9          -0.7(3)     .       .       .       .   no
 C3      C4      C6      C7       179.13(18)     .       .       .       .   no
 C5      C4      C6      C7          -0.3(3)     .       .       .       .   no
 N1      C5      C9      N2           1.4(3)     .       .       .       .   no
 N1      C5      C9      C8      -177.65(17)     .       .       .       .   no
 C4      C5      C9      N2      -179.46(16)     .       .       .       .   no
 C4      C5      C9      C8           1.5(3)     .       .       .       .   no
 C4      C6      C7      C8           0.5(3)     .       .       .       .   no
 C6      C7      C8      C9           0.3(3)     .       .       .       .   no
 C6      C7      C8      C10       -179.2(2)     .       .       .       .   no
 C7      C8      C9      N2       179.73(18)     .       .       .       .   no
 C7      C8      C9      C5          -1.3(3)     .       .       .       .   no
 C10     C8      C9      N2          -0.8(3)     .       .       .       .   no
 C10     C8      C9      C5       178.22(18)     .       .       .       .   no
 C7      C8      C10     C11        179.3(2)     .       .       .       .   no
 C9      C8      C10     C11         -0.2(3)     .       .       .       .   no
 C8      C10     C11     C12          0.9(3)     .       .       .       .   no
 C10     C11     C12     N2          -0.7(3)     .       .       .       .   no
 C14     C15     C16     C17     -179.06(17)     .       .       .       .   no
 C14     C15     C16     C23         70.2(2)     .       .       .       .   no
 C19     C15     C16     C17       57.89(17)     .       .       .       .   no
 C19     C15     C16     C23      -52.85(17)     .       .       .       .   no
 C14     C15     C19     C18      179.04(17)     .       .       .       .   no
 C14     C15     C19     C20        -71.3(2)     .       .       .       .   no
 C16     C15     C19     C18      -57.46(17)     .       .       .       .   no
 C16     C15     C19     C20       52.18(17)     .       .       .       .   no
 C15     C16     C17     C18      -36.32(19)     .       .       .       .   no
 C23     C16     C17     C18         70.8(2)     .       .       .       .   no
 C15     C16     C23     C20       34.99(18)     .       .       .       .   no
 C15     C16     C23     C22        -78.9(2)     .       .       .       .   no
 C17     C16     C23     C20      -70.17(19)     .       .       .       .   no
 C17     C16     C23     C22      175.92(17)     .       .       .       .   no
 C16     C17     C18     C19          0.1(2)     .       .       .       .   no
 C17     C18     C19     C15       36.11(19)     .       .       .       .   no
 C17     C18     C19     C20        -71.4(2)     .       .       .       .   no
 C15     C19     C20     C21         82.2(2)     .       .       .       .   no
 C15     C19     C20     C23      -32.45(19)     .       .       .       .   no
 C18     C19     C20     C21     -173.28(17)     .       .       .       .   no
 C18     C19     C20     C23       72.12(19)     .       .       .       .   no
 C19     C20     C21     N3      -112.32(18)     .       .       .       .   no
 C23     C20     C21     N3         0.93(19)     .       .       .       .   no
 C19     C20     C23     C16       -1.56(19)     .       .       .       .   no
 C19     C20     C23     C22      118.95(16)     .       .       .       .   no
 C21     C20     C23     C16     -124.21(16)     .       .       .       .   no
 C21     C20     C23     C22       -3.71(19)     .       .       .       .   no
 O1      C22     C23     C16        -61.1(3)     .       .       .       .   no
 O1      C22     C23     C20     -174.60(19)     .       .       .       .   no
 N3      C22     C23     C16      119.00(19)     .       .       .       .   no
 N3      C22     C23     C20          5.5(2)     .       .       .       .   no
 C29     C24     C25     C26         -0.8(3)     .       .       .       .   no
 C25     C24     C29     C28         -0.5(3)     .       .       .       .   no
 C24     C25     C26     C27          1.1(3)     .       .       .       .   no
 C25     C26     C27     C28         -0.1(3)     .       .       .       .   no
 C26     C27     C28     C29         -1.2(3)     .       .       .       .   no
 C27     C28     C29     C24          1.5(3)     .       .       .       .   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)
#
N3      H3      N1          0.8800     2.1100   2.914(2)     152.00   2_665 yes
N3      H3      N2          0.8800     2.5100   3.147(2)     129.00   2_665 yes
C1      H1      O1          0.9500     2.5400   3.293(2)     136.00   2_665 yes
C15     H15     N3          1.0000     2.6100   3.277(3)     124.00   3_566 yes
C24     H24     O1          0.9500     2.4100   3.223(3)     143.00     .   yes
 

# SQUEEZE RESULTS (Version = 140518)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.500  0.126       185        44 ' '
   2  0.500  1.000 -0.126       185        44 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details
;
The unit cell contains 2 disordered molecules of benzene on special positions
which were treated as a diffuse contribution to the overall scattering without
specific atom positions by SQUEEZE/PLATON.
; 
 
 
#===END
