#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024469.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024469
loop_
_publ_author_name
'Sylvaine Cren'
'Pascal Schär'
'Philippe Renaud'
'Kurt Schenk'
_publ_section_title
;
Diastereoselectivity Control of the Radical Carboazidation of Substituted
Methylenecyclohexanes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2942
_journal_page_last               2946
_journal_paper_doi               10.1021/jo900088x
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C13 H23 N1 O1'
_chemical_formula_sum            'C13 H23 N O'
_chemical_formula_weight         209.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_author_name               'Kurt J. Schenk'
_audit_contact_author_address
;
   Kurt J. Schenk
   LCr1 - IPMC - FSB - EPFL
   Le Cubtron, Bureau 521
   Dorigny
   CH-1015 Lausanne
;
_audit_contact_author_email      Kurt.Schenk@EPFL.CH
_audit_contact_author_fax        '+41 (0)21 693 0504'
_audit_contact_author_phone      '+41 (0)21 693 0635'
_audit_creation_date             '2nd February 2008'
_audit_creation_method           'SHELXL-97 & Stoe X-Red'
_cell_angle_alpha                104.22(3)
_cell_angle_beta                 100.83(3)
_cell_angle_gamma                96.08(3)
_cell_formula_units_Z            4
_cell_length_a                   6.4933(13)
_cell_length_b                   13.379(3)
_cell_length_c                   15.515(3)
_cell_measurement_reflns_used    8621
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      29.52
_cell_measurement_theta_min      2.38
_cell_volume                     1266.8(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SHELXtl (Bruker, 1996)'
_computing_publication_material  'SHELXtl (Bruker, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8867
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_diffrn_source_current           45
_diffrn_source_power             2.48
_diffrn_source_voltage           55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Stoe, X_Red32, Version 1.31 (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelets
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.041(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.2118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                3289
_reflns_number_total             4596
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900088x_si_001.cif
_cod_data_source_block           PS5j
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C13 H23 N1 O1'
_cod_database_code               4024469
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7463(2) -0.08602(10) 0.71534(12) 0.0712(5) Uani 1 1 d . . .
N1 N 0.6297(2) 0.06651(11) 0.70486(12) 0.0537(4) Uani 1 1 d . . .
H1N H 0.5355 0.0621 0.7366 0.064 Uiso 1 1 calc R . .
C2 C 0.7536(3) -0.00610(13) 0.68903(14) 0.0538(5) Uani 1 1 d . . .
C3 C 0.9057(3) 0.02663(15) 0.63504(15) 0.0579(5) Uani 1 1 d . . .
H3A H 0.8999 -0.0288 0.5805 0.069 Uiso 1 1 calc R . .
H3B H 1.0500 0.0436 0.6713 0.069 Uiso 1 1 calc R . .
C4 C 0.8336(3) 0.12220(14) 0.61026(14) 0.0547(5) Uani 1 1 d . . .
H4A H 0.7739 0.1060 0.5453 0.066 Uiso 1 1 calc R . .
H4B H 0.9525 0.1787 0.6263 0.066 Uiso 1 1 calc R . .
C5 C 0.6619(3) 0.15406(13) 0.66546(13) 0.0489(4) Uani 1 1 d . . .
C6 C 0.7177(3) 0.26252(13) 0.73829(13) 0.0486(4) Uani 1 1 d . . .
H6 H 0.5921 0.2696 0.7644 0.058 Uiso 1 1 calc R . .
C7 C 0.7285(3) 0.34776(15) 0.68789(16) 0.0645(5) Uani 1 1 d . . .
H7A H 0.7664 0.4156 0.7323 0.077 Uiso 1 1 calc R . .
H7B H 0.8395 0.3393 0.6539 0.077 Uiso 1 1 calc R . .
C8 C 0.5187(4) 0.34471(19) 0.62227(18) 0.0794(7) Uani 1 1 d . . .
H8A H 0.4091 0.3584 0.6563 0.095 Uiso 1 1 calc R . .
H8B H 0.5348 0.3987 0.5911 0.095 Uiso 1 1 calc R . .
C9 C 0.4535(4) 0.2391(2) 0.55312(17) 0.0805(7) Uani 1 1 d . . .
H9A H 0.5528 0.2299 0.5133 0.097 Uiso 1 1 calc R . .
H9B H 0.3137 0.2357 0.5159 0.097 Uiso 1 1 calc R . .
C10 C 0.4496(3) 0.15245(17) 0.60016(16) 0.0655(6) Uani 1 1 d . . .
H10A H 0.4132 0.0858 0.5541 0.079 Uiso 1 1 calc R . .
H10B H 0.3388 0.1579 0.6344 0.079 Uiso 1 1 calc R . .
C11 C 0.9101(3) 0.28328(14) 0.82292(14) 0.0568(5) Uani 1 1 d . . .
C12 C 1.1282(3) 0.2911(2) 0.79853(17) 0.0759(7) Uani 1 1 d . . .
H12A H 1.1362 0.3388 0.7617 0.102(10) Uiso 1 1 calc R . .
H12B H 1.1477 0.2234 0.7652 0.116(10) Uiso 1 1 calc R . .
H12C H 1.2372 0.3159 0.8534 0.111(9) Uiso 1 1 calc R . .
C13 C 0.8971(4) 0.20213(19) 0.87590(16) 0.0742(6) Uani 1 1 d . . .
H13A H 0.7561 0.1903 0.8858 0.087(8) Uiso 1 1 calc R . .
H13B H 0.9969 0.2268 0.9336 0.103(9) Uiso 1 1 calc R . .
H13C H 0.9302 0.1380 0.8418 0.107(10) Uiso 1 1 calc R . .
C14 C 0.9005(5) 0.3885(2) 0.88943(17) 0.0872(8) Uani 1 1 d . . .
H14A H 0.9339 0.4443 0.8631 0.111(11) Uiso 1 1 calc R . .
H14B H 1.0014 0.3981 0.9458 0.093(8) Uiso 1 1 calc R . .
H14C H 0.7603 0.3885 0.9009 0.082(8) Uiso 1 1 calc R . .
O101 O 0.3559(3) 1.05420(11) 0.83256(13) 0.0799(5) Uani 1 1 d . . .
N101 N 0.4198(2) 0.88655(11) 0.81473(12) 0.0566(4) Uani 1 1 d . . .
H1NB H 0.5164 0.8918 0.7843 0.068 Uiso 1 1 calc R . .
C102 C 0.3219(3) 0.96622(15) 0.84479(14) 0.0583(5) Uani 1 1 d . . .
C103 C 0.1643(4) 0.93104(16) 0.89510(17) 0.0700(6) Uani 1 1 d . . .
H3C H 0.0273 0.9507 0.8754 0.084 Uiso 1 1 calc R . .
H3D H 0.2135 0.9615 0.9603 0.084 Uiso 1 1 calc R . .
C104 C 0.1497(4) 0.81354(16) 0.87106(17) 0.0691(6) Uani 1 1 d . . .
H4C H 0.0238 0.7804 0.8238 0.083 Uiso 1 1 calc R . .
H4D H 0.1433 0.7884 0.9242 0.083 Uiso 1 1 calc R . .
C105 C 0.3530(3) 0.78923(14) 0.83664(13) 0.0533(5) Uani 1 1 d . . .
C106 C 0.3230(3) 0.69215(13) 0.75366(13) 0.0511(5) Uani 1 1 d . . .
H6B H 0.4630 0.6920 0.7387 0.061 Uiso 1 1 calc R . .
C107 C 0.2843(4) 0.59265(16) 0.78508(18) 0.0724(6) Uani 1 1 d . . .
H7C H 0.1554 0.5922 0.8081 0.087 Uiso 1 1 calc R . .
H7D H 0.2629 0.5321 0.7330 0.087 Uiso 1 1 calc R . .
C108 C 0.4656(5) 0.5840(2) 0.8582(2) 0.0946(9) Uani 1 1 d . . .
H8C H 0.4337 0.5203 0.8757 0.113 Uiso 1 1 calc R . .
H8D H 0.5942 0.5813 0.8351 0.113 Uiso 1 1 calc R . .
C109 C 0.4986(5) 0.6771(2) 0.9399(2) 0.1004(9) Uani 1 1 d . . .
H9C H 0.6215 0.6743 0.9852 0.121 Uiso 1 1 calc R . .
H9D H 0.3757 0.6751 0.9670 0.121 Uiso 1 1 calc R . .
C110 C 0.5317(4) 0.7786(2) 0.91276(17) 0.0808(7) Uani 1 1 d . . .
H10C H 0.6645 0.7836 0.8929 0.097 Uiso 1 1 calc R . .
H10D H 0.5450 0.8367 0.9662 0.097 Uiso 1 1 calc R . .
C111 C 0.1653(3) 0.68261(15) 0.66069(15) 0.0608(5) Uani 1 1 d . . .
C112 C -0.0658(4) 0.6400(3) 0.6560(2) 0.0977(9) Uani 1 1 d . . .
H12D H -0.1189 0.6869 0.7011 0.067(7) Uiso 1 1 calc R . .
H12E H -0.0735 0.5726 0.6676 0.167(17) Uiso 1 1 calc R . .
H12F H -0.1500 0.6338 0.5965 0.099(9) Uiso 1 1 calc R . .
C113 C 0.1677(4) 0.78476(18) 0.63316(16) 0.0726(6) Uani 1 1 d . . .
H13D H 0.1045 0.8328 0.6731 0.083(7) Uiso 1 1 calc R . .
H13E H 0.0885 0.7711 0.5715 0.083(7) Uiso 1 1 calc R . .
H13F H 0.3117 0.8146 0.6375 0.085(8) Uiso 1 1 calc R . .
C114 C 0.2407(6) 0.6051(2) 0.58581(18) 0.0982(9) Uani 1 1 d . . .
H14D H 0.1529 0.6001 0.5273 0.130(11) Uiso 1 1 calc R . .
H14E H 0.2306 0.5376 0.5972 0.130(12) Uiso 1 1 calc R . .
H14F H 0.3856 0.6297 0.5865 0.160(17) Uiso 1 1 calc R . .
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0280
0 1 0 0.0520
-1 1 0 0.2280
0 0 1 0.1650
1 0 -6 0.1750
1 0 -1 0.2750
7 -1 -2 0.2770
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 116.55(15) . . ?
C2 N1 H1N 121.7 . . ?
C5 N1 H1N 121.7 . . ?
O1 C2 N1 125.52(18) . . ?
O1 C2 C3 125.93(17) . . ?
N1 C2 C3 108.55(16) . . ?
C2 C3 C4 105.49(15) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
C3 C4 C5 106.56(16) . . ?
C3 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
C5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C5 C10 106.63(15) . . ?
N1 C5 C4 101.96(14) . . ?
C10 C5 C4 110.39(16) . . ?
N1 C5 C6 113.13(15) . . ?
C10 C5 C6 107.71(15) . . ?
C4 C5 C6 116.58(14) . . ?
C7 C6 C5 108.03(15) . . ?
C7 C6 C11 112.38(15) . . ?
C5 C6 C11 120.09(15) . . ?
C7 C6 H6 105.0 . . ?
C5 C6 H6 105.0 . . ?
C11 C6 H6 105.0 . . ?
C8 C7 C6 112.77(18) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 110.29(18) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 110.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C5 113.92(17) . . ?
C9 C10 H10A 108.8 . . ?
C5 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C5 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C13 C11 C12 108.2(2) . . ?
C13 C11 C14 106.16(19) . . ?
C12 C11 C14 107.65(18) . . ?
C13 C11 C6 113.09(16) . . ?
C12 C11 C6 113.82(18) . . ?
C14 C11 C6 107.51(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C102 N101 C105 115.95(16) . . ?
C102 N101 H1NB 122.0 . . ?
C105 N101 H1NB 122.0 . . ?
O101 C102 N101 125.25(19) . . ?
O101 C102 C103 126.39(19) . . ?
N101 C102 C103 108.35(17) . . ?
C102 C103 C104 104.57(17) . . ?
C102 C103 H3C 110.8 . . ?
C104 C103 H3C 110.8 . . ?
C102 C103 H3D 110.8 . . ?
C104 C103 H3D 110.8 . . ?
H3C C103 H3D 108.9 . . ?
C103 C104 C105 106.06(17) . . ?
C103 C104 H4C 110.5 . . ?
C105 C104 H4C 110.5 . . ?
C103 C104 H4D 110.5 . . ?
C105 C104 H4D 110.5 . . ?
H4C C104 H4D 108.7 . . ?
N101 C105 C110 106.71(16) . . ?
N101 C105 C104 101.03(15) . . ?
C110 C105 C104 112.3(2) . . ?
N101 C105 C106 112.06(16) . . ?
C110 C105 C106 108.29(17) . . ?
C104 C105 C106 115.94(16) . . ?
C107 C106 C105 109.05(17) . . ?
C107 C106 C111 110.68(16) . . ?
C105 C106 C111 121.56(15) . . ?
C107 C106 H6B 104.7 . . ?
C105 C106 H6B 104.7 . . ?
C111 C106 H6B 104.7 . . ?
C108 C107 C106 112.92(19) . . ?
C108 C107 H7C 109.0 . . ?
C106 C107 H7C 109.0 . . ?
C108 C107 H7D 109.0 . . ?
C106 C107 H7D 109.0 . . ?
H7C C107 H7D 107.8 . . ?
C109 C108 C107 109.5(2) . . ?
C109 C108 H8C 109.8 . . ?
C107 C108 H8C 109.8 . . ?
C109 C108 H8D 109.8 . . ?
C107 C108 H8D 109.8 . . ?
H8C C108 H8D 108.2 . . ?
C108 C109 C110 110.8(2) . . ?
C108 C109 H9C 109.5 . . ?
C110 C109 H9C 109.5 . . ?
C108 C109 H9D 109.5 . . ?
C110 C109 H9D 109.5 . . ?
H9C C109 H9D 108.1 . . ?
C109 C110 C105 114.44(19) . . ?
C109 C110 H10C 108.7 . . ?
C105 C110 H10C 108.7 . . ?
C109 C110 H10D 108.7 . . ?
C105 C110 H10D 108.7 . . ?
H10C C110 H10D 107.6 . . ?
C113 C111 C112 107.7(2) . . ?
C113 C111 C114 106.2(2) . . ?
C112 C111 C114 107.1(2) . . ?
C113 C111 C106 113.73(16) . . ?
C112 C111 C106 114.7(2) . . ?
C114 C111 C106 106.88(18) . . ?
C111 C112 H12D 109.5 . . ?
C111 C112 H12E 109.5 . . ?
H12D C112 H12E 109.5 . . ?
C111 C112 H12F 109.5 . . ?
H12D C112 H12F 109.5 . . ?
H12E C112 H12F 109.5 . . ?
C111 C113 H13D 109.5 . . ?
C111 C113 H13E 109.5 . . ?
H13D C113 H13E 109.5 . . ?
C111 C113 H13F 109.5 . . ?
H13D C113 H13F 109.5 . . ?
H13E C113 H13F 109.5 . . ?
C111 C114 H14D 109.5 . . ?
C111 C114 H14E 109.5 . . ?
H14D C114 H14E 109.5 . . ?
C111 C114 H14F 109.5 . . ?
H14D C114 H14F 109.5 . . ?
H14E C114 H14F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.234(2) . ?
N1 C2 1.332(2) . ?
N1 C5 1.462(2) . ?
N1 H1N 0.8600 . ?
C2 C3 1.506(3) . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.562(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.545(3) . ?
C5 C6 1.563(2) . ?
C6 C7 1.536(3) . ?
C6 C11 1.579(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.519(3) . ?
C11 C12 1.532(3) . ?
C11 C14 1.542(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O101 C102 1.241(2) . ?
N101 C102 1.330(2) . ?
N101 C105 1.467(2) . ?
N101 H1NB 0.8600 . ?
C102 C103 1.502(3) . ?
C103 C104 1.512(3) . ?
C103 H3C 0.9700 . ?
C103 H3D 0.9700 . ?
C104 C105 1.550(3) . ?
C104 H4C 0.9700 . ?
C104 H4D 0.9700 . ?
C105 C110 1.538(3) . ?
C105 C106 1.553(3) . ?
C106 C107 1.538(3) . ?
C106 C111 1.572(3) . ?
C106 H6B 0.9800 . ?
C107 C108 1.509(3) . ?
C107 H7C 0.9700 . ?
C107 H7D 0.9700 . ?
C108 C109 1.507(4) . ?
C108 H8C 0.9700 . ?
C108 H8D 0.9700 . ?
C109 C110 1.523(4) . ?
C109 H9C 0.9700 . ?
C109 H9D 0.9700 . ?
C110 H10C 0.9700 . ?
C110 H10D 0.9700 . ?
C111 C113 1.528(3) . ?
C111 C112 1.529(3) . ?
C111 C114 1.547(3) . ?
C112 H12D 0.9600 . ?
C112 H12E 0.9600 . ?
C112 H12F 0.9600 . ?
C113 H13D 0.9600 . ?
C113 H13E 0.9600 . ?
C113 H13F 0.9600 . ?
C114 H14D 0.9600 . ?
C114 H14E 0.9600 . ?
C114 H14F 0.9600 . ?
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
N1 H1N O101 0.86 2.07 2.921(2) 169.5 1_545
N101 H1NB O1 0.86 2.03 2.889(2) 176.4 1_565
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 C2 O1 -178.60(18) . . . . ?
C5 N1 C2 C3 2.2(2) . . . . ?
O1 C2 C3 C4 173.40(19) . . . . ?
N1 C2 C3 C4 -7.4(2) . . . . ?
C2 C3 C4 C5 9.5(2) . . . . ?
C2 N1 C5 C10 119.57(18) . . . . ?
C2 N1 C5 C4 3.8(2) . . . . ?
C2 N1 C5 C6 -122.22(17) . . . . ?
C3 C4 C5 N1 -8.07(18) . . . . ?
C3 C4 C5 C10 -121.08(18) . . . . ?
C3 C4 C5 C6 115.63(18) . . . . ?
N1 C5 C6 C7 -175.20(15) . . . . ?
C10 C5 C6 C7 -57.61(19) . . . . ?
C4 C5 C6 C7 67.1(2) . . . . ?
N1 C5 C6 C11 54.2(2) . . . . ?
C10 C5 C6 C11 171.75(17) . . . . ?
C4 C5 C6 C11 -63.6(2) . . . . ?
C5 C6 C7 C8 60.1(2) . . . . ?
C11 C6 C7 C8 -165.17(17) . . . . ?
C6 C7 C8 C9 -57.8(3) . . . . ?
C7 C8 C9 C10 53.4(3) . . . . ?
C8 C9 C10 C5 -56.1(3) . . . . ?
N1 C5 C10 C9 179.68(17) . . . . ?
C4 C5 C10 C9 -70.3(2) . . . . ?
C6 C5 C10 C9 58.0(2) . . . . ?
C7 C6 C11 C13 177.61(17) . . . . ?
C5 C6 C11 C13 -53.7(2) . . . . ?
C7 C6 C11 C12 -58.4(2) . . . . ?
C5 C6 C11 C12 70.3(2) . . . . ?
C7 C6 C11 C14 60.7(2) . . . . ?
C5 C6 C11 C14 -170.54(18) . . . . ?
C105 N101 C102 O101 -179.6(2) . . . . ?
C105 N101 C102 C103 0.2(2) . . . . ?
O101 C102 C103 C104 167.1(2) . . . . ?
N101 C102 C103 C104 -12.7(2) . . . . ?
C102 C103 C104 C105 19.5(3) . . . . ?
C102 N101 C105 C110 -105.7(2) . . . . ?
C102 N101 C105 C104 11.9(2) . . . . ?
C102 N101 C105 C106 135.96(18) . . . . ?
C103 C104 C105 N101 -18.8(2) . . . . ?
C103 C104 C105 C110 94.6(2) . . . . ?
C103 C104 C105 C106 -140.13(19) . . . . ?
N101 C105 C106 C107 172.08(16) . . . . ?
C110 C105 C106 C107 54.6(2) . . . . ?
C104 C105 C106 C107 -72.7(2) . . . . ?
N101 C105 C106 C111 -57.3(2) . . . . ?
C110 C105 C106 C111 -174.77(19) . . . . ?
C104 C105 C106 C111 57.9(2) . . . . ?
C105 C106 C107 C108 -59.8(3) . . . . ?
C111 C106 C107 C108 164.0(2) . . . . ?
C106 C107 C108 C109 59.4(3) . . . . ?
C107 C108 C109 C110 -55.0(3) . . . . ?
C108 C109 C110 C105 55.5(3) . . . . ?
N101 C105 C110 C109 -175.6(2) . . . . ?
C104 C105 C110 C109 74.6(3) . . . . ?
C106 C105 C110 C109 -54.7(3) . . . . ?
C107 C106 C111 C113 170.13(19) . . . . ?
C105 C106 C111 C113 40.2(3) . . . . ?
C107 C106 C111 C112 45.5(3) . . . . ?
C105 C106 C111 C112 -84.4(3) . . . . ?
C107 C106 C111 C114 -73.1(2) . . . . ?
C105 C106 C111 C114 157.0(2) . . . . ?
