#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2238607
loop_
_publ_author_name
'Lakshmi, S. H. Anjana'
'Kandaswamy, M.'
'Ramkumar, V.'
_publ_section_title
;
 2,2'-{[(1E,1'E)-(Cyclohexane-1,4-diyl)bis(azanylylidene)]bis(ethan-1-yl-1-ylidene)}diphenol
;
_journal_coeditor_code           CV5426
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1593
_journal_paper_doi               10.1107/S1600536813026123
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C22 H26 N2 O2'
_chemical_formula_moiety         'C22 H26 N2 O2'
_chemical_formula_sum            'C22 H26 N2 O2'
_chemical_formula_weight         350.45
_chemical_name_systematic
2,2'-{[(1E,1'E)-(Cyclohexane-1,4-diyl)bis(azanylylidene)]bis(ethan-1-yl-1-ylidene)}diphenol
_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_creation_method           SHELXL-97
_cell_angle_alpha                92.946(3)
_cell_angle_beta                 95.521(4)
_cell_angle_gamma                91.204(3)
_cell_formula_units_Z            4
_cell_length_a                   9.0299(6)
_cell_length_b                   11.4718(8)
_cell_length_c                   17.9652(13)
_cell_measurement_reflns_used    5628
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     1849.3(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20050
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0873P)²+2.2422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.2389
_reflns_number_gt                2646
_reflns_number_total             6387
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5426.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C22 H26 N2 O2 '
_cod_database_code               2238607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.8319(7) 1.1440(5) 0.6061(3) 0.0575(17) Uani d . 1 1
H H1 0.8150 1.2200 0.6233 0.069 Uiso calc R 1 1
C C2 0.9279(7) 1.0768(6) 0.6478(3) 0.0603(18) Uani d . 1 1
H H2 0.9765 1.1078 0.6927 0.072 Uiso calc R 1 1
C C3 0.9532(6) 0.9640(6) 0.6240(3) 0.0594(17) Uani d . 1 1
H H3 1.0188 0.9187 0.6525 0.071 Uiso calc R 1 1
C C4 0.8809(6) 0.9185(5) 0.5577(3) 0.0464(14) Uani d . 1 1
H H4 0.8989 0.8422 0.5416 0.056 Uiso calc R 1 1
C C5 0.7805(6) 0.9842(4) 0.5136(3) 0.0362(13) Uani d . 1 1
C C6 0.7589(6) 1.1000(4) 0.5381(3) 0.0439(14) Uani d . 1 1
C C7 0.7032(6) 0.9339(4) 0.4427(3) 0.0365(12) Uani d . 1 1
C C8 0.7086(7) 0.8049(4) 0.4243(3) 0.0579(17) Uani d . 1 1
H H8A 0.6480 0.7854 0.3783 0.087 Uiso calc R 1 1
H H8B 0.6718 0.7631 0.4640 0.087 Uiso calc R 1 1
H H8C 0.8095 0.7838 0.4189 0.087 Uiso calc R 1 1
C C9 0.5504(6) 0.9694(4) 0.3276(3) 0.0353(13) Uani d . 1 1
H H9 0.5033 0.8923 0.3307 0.042 Uiso calc R 1 1
C C10 0.6546(6) 0.9646(4) 0.2661(3) 0.0408(13) Uani d . 1 1
H H10A 0.7259 0.9037 0.2754 0.049 Uiso calc R 1 1
H H10B 0.7095 1.0383 0.2669 0.049 Uiso calc R 1 1
C C11 0.5697(6) 0.9406(4) 0.1895(3) 0.0398(13) Uani d . 1 1
H H11A 0.6391 0.9416 0.1516 0.048 Uiso calc R 1 1
H H11B 0.5234 0.8632 0.1873 0.048 Uiso calc R 1 1
C C12 0.4503(6) 1.0297(4) 0.1724(3) 0.0389(13) Uani d . 1 1
H H12 0.4978 1.1067 0.1694 0.047 Uiso calc R 1 1
C C13 0.3456(6) 1.0352(4) 0.2340(3) 0.0418(13) Uani d . 1 1
H H13A 0.2750 1.0966 0.2247 0.050 Uiso calc R 1 1
H H13B 0.2899 0.9618 0.2332 0.050 Uiso calc R 1 1
C C14 0.4303(6) 1.0587(4) 0.3110(3) 0.0396(13) Uani d . 1 1
H H14A 0.3608 1.0570 0.3488 0.048 Uiso calc R 1 1
H H14B 0.4763 1.1362 0.3136 0.048 Uiso calc R 1 1
C C15 0.2981(6) 1.0670(4) 0.0578(3) 0.0405(13) Uani d . 1 1
C C16 0.2927(7) 1.1947(4) 0.0751(3) 0.0628(18) Uani d . 1 1
H H16A 0.3690 1.2176 0.1144 0.094 Uiso calc R 1 1
H H16B 0.1971 1.2134 0.0909 0.094 Uiso calc R 1 1
H H16C 0.3085 1.2356 0.0311 0.094 Uiso calc R 1 1
C C17 0.2196(6) 1.0170(5) -0.0128(3) 0.0425(14) Uani d . 1 1
C C18 0.2409(7) 0.9003(5) -0.0371(3) 0.0507(15) Uani d . 1 1
C C19 0.1686(7) 0.8566(5) -0.1058(3) 0.0591(17) Uani d . 1 1
H H19 0.1866 0.7810 -0.1233 0.071 Uiso calc R 1 1
C C20 0.0720(7) 0.9235(6) -0.1473(3) 0.0608(18) Uani d . 1 1
H H20 0.0233 0.8924 -0.1921 0.073 Uiso calc R 1 1
C C21 0.0462(7) 1.0362(6) -0.1235(3) 0.0608(18) Uani d . 1 1
H H21 -0.0203 1.0811 -0.1517 0.073 Uiso calc R 1 1
C C22 0.1200(6) 1.0821(5) -0.0574(3) 0.0509(15) Uani d . 1 1
H H22 0.1029 1.1588 -0.0419 0.061 Uiso calc R 1 1
C C23 0.3019(7) 0.3440(5) 0.3478(3) 0.0517(15) Uani d . 1 1
H H23 0.2733 0.2697 0.3603 0.062 Uiso calc R 1 1
C C24 0.4097(6) 0.4066(5) 0.3931(3) 0.0570(17) Uani d . 1 1
H H24 0.4552 0.3738 0.4354 0.068 Uiso calc R 1 1
C C25 0.4508(6) 0.5175(5) 0.3762(3) 0.0584(17) Uani d . 1 1
H H25 0.5239 0.5595 0.4071 0.070 Uiso calc R 1 1
C C26 0.3841(6) 0.5662(5) 0.3139(3) 0.0487(15) Uani d . 1 1
H H26 0.4127 0.6415 0.3034 0.058 Uiso calc R 1 1
C C27 0.2739(6) 0.5058(4) 0.2651(3) 0.0378(12) Uani d . 1 1
C C28 0.2345(6) 0.3910(4) 0.2828(3) 0.0418(14) Uani d . 1 1
C C29 0.2037(6) 0.5571(4) 0.1977(3) 0.0398(13) Uani d . 1 1
C C30 0.2285(6) 0.6845(4) 0.1877(3) 0.0567(16) Uani d . 1 1
H H30A 0.1619 0.7084 0.1467 0.085 Uiso calc R 1 1
H H30B 0.3294 0.6986 0.1773 0.085 Uiso calc R 1 1
H H30C 0.2100 0.7284 0.2327 0.085 Uiso calc R 1 1
C C31 0.0496(6) 0.5264(4) 0.0803(3) 0.0379(13) Uani d . 1 1
H H31 0.0089 0.6039 0.0888 0.045 Uiso calc R 1 1
C C32 0.1573(6) 0.5315(4) 0.0199(3) 0.0424(13) Uani d . 1 1
H H32A 0.2344 0.5905 0.0350 0.051 Uiso calc R 1 1
H H32B 0.2046 0.4568 0.0146 0.051 Uiso calc R 1 1
C C33 -0.0771(6) 0.4398(4) 0.0546(3) 0.0420(13) Uani d . 1 1
H H33A -0.0377 0.3619 0.0502 0.050 Uiso calc R 1 1
H H33B -0.1476 0.4398 0.0921 0.050 Uiso calc R 1 1
C C34 0.6985(7) 0.6551(5) 0.1526(3) 0.0535(16) Uani d . 1 1
H H34 0.7273 0.7295 0.1404 0.064 Uiso calc R 1 1
C C35 0.5913(7) 0.5937(6) 0.1067(3) 0.0614(18) Uani d . 1 1
H H35 0.5471 0.6267 0.0641 0.074 Uiso calc R 1 1
C C36 0.5488(6) 0.4827(6) 0.1238(3) 0.0605(18) Uani d . 1 1
H H36 0.4750 0.4411 0.0932 0.073 Uiso calc R 1 1
C C37 0.6156(6) 0.4339(5) 0.1860(3) 0.0521(15) Uani d . 1 1
H H37 0.5873 0.3585 0.1964 0.063 Uiso calc R 1 1
C C38 0.7259(6) 0.4945(4) 0.2347(3) 0.0403(13) Uani d . 1 1
C C39 0.7655(6) 0.6083(4) 0.2172(3) 0.0450(14) Uani d . 1 1
C C40 0.7956(6) 0.4409(4) 0.3026(3) 0.0382(13) Uani d . 1 1
C C41 0.7717(7) 0.3141(4) 0.3121(3) 0.0582(18) Uani d . 1 1
H H41A 0.8326 0.2915 0.3555 0.087 Uiso calc R 1 1
H H41B 0.7982 0.2703 0.2686 0.087 Uiso calc R 1 1
H H41C 0.6689 0.2987 0.3184 0.087 Uiso calc R 1 1
C C42 0.9513(5) 0.4732(4) 0.4197(3) 0.0382(13) Uani d . 1 1
H H42 0.9922 0.3957 0.4113 0.046 Uiso calc R 1 1
C C43 0.8430(5) 0.4678(4) 0.4798(3) 0.0398(13) Uani d . 1 1
H H43A 0.7947 0.5422 0.4846 0.048 Uiso calc R 1 1
H H43B 0.7666 0.4083 0.4647 0.048 Uiso calc R 1 1
C C44 1.0776(6) 0.5597(4) 0.4452(3) 0.0391(13) Uani d . 1 1
H H44A 1.1486 0.5588 0.4079 0.047 Uiso calc R 1 1
H H44B 1.0383 0.6376 0.4489 0.047 Uiso calc R 1 1
N N1 0.6309(5) 1.0050(3) 0.3999(2) 0.0394(11) Uani d . 1 1
N N2 0.3692(5) 0.9952(3) 0.1003(2) 0.0408(11) Uani d . 1 1
N N3 0.1238(5) 0.4889(3) 0.1507(2) 0.0397(11) Uani d . 1 1
N N4 0.8768(5) 0.5101(3) 0.3495(2) 0.0406(11) Uani d . 1 1
O O1 0.6695(6) 1.1708(3) 0.4976(2) 0.0688(13) Uani d . 1 1
H H1A 0.6349 1.1355 0.4588 0.103 Uiso calc R 1 1
O O2 0.3297(6) 0.8290(3) 0.0025(2) 0.0714(13) Uani d . 1 1
H H2A 0.3707 0.8653 0.0397 0.107 Uiso calc R 1 1
O O5 0.1332(5) 0.3254(3) 0.2392(2) 0.0574(11) Uani d . 1 1
H H5 0.1070 0.3598 0.2014 0.086 Uiso calc R 1 1
O O6 0.8666(5) 0.6742(3) 0.2608(2) 0.0581(11) Uani d . 1 1
H H6 0.8922 0.6402 0.2987 0.087 Uiso calc R 1 1
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C2 C1 C6 . 120.8(6)
C2 C1 H1 . 119.4
C6 C1 H1 . 119.8
C3 C2 C1 . 120.6(5)
C3 C2 H2 . 119.7
C1 C2 H2 . 119.7
C2 C3 C4 . 119.5(5)
C2 C3 H3 . 120.4
C4 C3 H3 . 120.1
C3 C4 C5 . 121.7(5)
C3 C4 H4 . 119.2
C5 C4 H4 . 119.1
C4 C5 C6 . 117.9(4)
C4 C5 C7 . 121.1(4)
C6 C5 C7 . 121.0(4)
O1 C6 C1 . 118.7(5)
O1 C6 C5 . 121.8(4)
C1 C6 C5 . 119.5(5)
N1 C7 C5 . 117.1(4)
N1 C7 C8 . 123.3(4)
C5 C7 C8 . 119.6(4)
C7 C8 H8A . 109.6
C7 C8 H8B . 109.5
H8A C8 H8B . 109.5
C7 C8 H8C . 109.4
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
N1 C9 C10 . 110.9(4)
N1 C9 C14 . 107.6(4)
C10 C9 C14 . 110.1(4)
N1 C9 H9 . 109.4
C10 C9 H9 . 109.4
C14 C9 H9 . 109.3
C9 C10 C11 . 111.4(4)
C9 C10 H10A . 109.2
C11 C10 H10A . 109.4
C9 C10 H10B . 109.6
C11 C10 H10B . 109.3
H10A C10 H10B . 107.9
C12 C11 C10 . 112.4(4)
C12 C11 H11A . 109.1
C10 C11 H11A . 109.1
C12 C11 H11B . 109.1
C10 C11 H11B . 109.2
H11A C11 H11B . 107.9
N2 C12 C11 . 108.3(4)
N2 C12 C13 . 110.7(4)
C11 C12 C13 . 110.0(4)
N2 C12 H12 . 109.2
C11 C12 H12 . 109.3
C13 C12 H12 . 109.2
C14 C13 C12 . 111.6(4)
C14 C13 H13A . 109.3
C12 C13 H13A . 109.5
C14 C13 H13B . 109.3
C12 C13 H13B . 109.1
H13A C13 H13B . 108.0
C13 C14 C9 . 112.3(4)
C13 C14 H14A . 109.2
C9 C14 H14A . 109.2
C13 C14 H14B . 109.0
C9 C14 H14B . 109.2
H14A C14 H14B . 107.8
N2 C15 C17 . 116.7(4)
N2 C15 C16 . 124.4(5)
C17 C15 C16 . 118.9(4)
C15 C16 H16A . 109.4
C15 C16 H16B . 109.5
H16A C16 H16B . 109.5
C15 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
C22 C17 C18 . 117.5(5)
C22 C17 C15 . 121.7(5)
C18 C17 C15 . 120.7(5)
O2 C18 C19 . 118.2(5)
O2 C18 C17 . 122.5(5)
C19 C18 C17 . 119.3(5)
C20 C19 C18 . 120.9(6)
C20 C19 H19 . 119.8
C18 C19 H19 . 119.4
C19 C20 C21 . 120.7(5)
C19 C20 H20 . 119.7
C21 C20 H20 . 119.6
C20 C21 C22 . 119.3(6)
C20 C21 H21 . 120.2
C22 C21 H21 . 120.5
C21 C22 C17 . 122.2(6)
C21 C22 H22 . 118.8
C17 C22 H22 . 119.0
C24 C23 C28 . 120.6(5)
C24 C23 H23 . 119.8
C28 C23 H23 . 119.6
C23 C24 C25 . 120.4(5)
C23 C24 H24 . 119.6
C25 C24 H24 . 120.0
C26 C25 C24 . 120.0(5)
C26 C25 H25 . 120.0
C24 C25 H25 . 120.0
C25 C26 C27 . 122.1(5)
C25 C26 H26 . 119.0
C27 C26 H26 . 118.9
C26 C27 C28 . 117.1(5)
C26 C27 C29 . 122.2(5)
C28 C27 C29 . 120.6(4)
O5 C28 C23 . 118.5(5)
O5 C28 C27 . 121.8(5)
C23 C28 C27 . 119.8(5)
N3 C29 C27 . 117.3(4)
N3 C29 C30 . 123.8(5)
C27 C29 C30 . 118.9(4)
C29 C30 H30A . 109.5
C29 C30 H30B . 109.7
H30A C30 H30B . 109.5
C29 C30 H30C . 109.2
H30A C30 H30C . 109.5
H30B C30 H30C . 109.5
N3 C31 C33 . 108.2(4)
N3 C31 C32 . 111.4(4)
C33 C31 C32 . 109.6(4)
N3 C31 H31 . 109.3
C33 C31 H31 . 109.1
C32 C31 H31 . 109.2
C33 C32 C31 2_565 111.1(4)
C33 C32 H32A 2_565 109.4
C31 C32 H32A . 109.3
C33 C32 H32B 2_565 109.6
C31 C32 H32B . 109.4
H32A C32 H32B . 108.0
C32 C33 C31 2_565 112.3(4)
C32 C33 H33A 2_565 109.3
C31 C33 H33A . 109.0
C32 C33 H33B 2_565 109.1
C31 C33 H33B . 109.2
H33A C33 H33B . 107.9
C35 C34 C39 . 121.3(5)
C35 C34 H34 . 119.3
C39 C34 H34 . 119.4
C34 C35 C36 . 119.8(5)
C34 C35 H35 . 120.3
C36 C35 H35 . 119.9
C37 C36 C35 . 119.9(5)
C37 C36 H36 . 120.0
C35 C36 H36 . 120.1
C36 C37 C38 . 122.0(5)
C36 C37 H37 . 119.0
C38 C37 H37 . 119.1
C39 C38 C37 . 117.3(5)
C39 C38 C40 . 121.4(4)
C37 C38 C40 . 121.3(5)
O6 C39 C34 . 118.3(5)
O6 C39 C38 . 122.0(5)
C34 C39 C38 . 119.7(5)
N4 C40 C38 . 116.0(4)
N4 C40 C41 . 124.3(5)
C38 C40 C41 . 119.7(4)
C40 C41 H41A . 109.4
C40 C41 H41B . 109.8
H41A C41 H41B . 109.5
C40 C41 H41C . 109.2
H41A C41 H41C . 109.5
H41B C41 H41C . 109.5
N4 C42 C44 . 108.4(4)
N4 C42 C43 . 111.0(4)
C44 C42 C43 . 109.9(4)
N4 C42 H42 . 109.1
C44 C42 H42 . 109.2
C43 C42 H42 . 109.2
C44 C43 C42 2_766 111.3(4)
C44 C43 H43A 2_766 109.2
C42 C43 H43A . 109.4
C44 C43 H43B 2_766 109.4
C42 C43 H43B . 109.4
H43A C43 H43B . 108.0
C43 C44 C42 2_766 112.3(4)
C43 C44 H44A 2_766 109.2
C42 C44 H44A . 109.1
C43 C44 H44B 2_766 109.0
C42 C44 H44B . 109.3
H44A C44 H44B . 107.9
C7 N1 C9 . 123.8(4)
C15 N2 C12 . 123.8(4)
C29 N3 C31 . 123.6(4)
C40 N4 C42 . 123.5(4)
C6 O1 H1A . 109.4
C18 O2 H2A . 109.6
C28 O5 H5 . 109.4
C39 O6 H6 . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.367(8)
C1 C6 . 1.397(7)
C1 H1 . 0.9300
C2 C3 . 1.373(8)
C2 H2 . 0.9300
C3 C4 . 1.375(7)
C3 H3 . 0.9300
C4 C5 . 1.403(6)
C4 H4 . 0.9300
C5 C6 . 1.402(6)
C5 C7 . 1.476(6)
C6 O1 . 1.346(6)
C7 N1 . 1.293(6)
C7 C8 . 1.502(6)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
C9 N1 . 1.460(5)
C9 C10 . 1.519(7)
C9 C14 . 1.526(6)
C9 H9 . 0.9800
C10 C11 . 1.519(6)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C12 . 1.522(6)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 N2 . 1.457(6)
C12 C13 . 1.524(7)
C12 H12 . 0.9800
C13 C14 . 1.523(6)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 H14A . 0.9700
C14 H14B . 0.9700
C15 N2 . 1.291(6)
C15 C17 . 1.474(7)
C15 C16 . 1.484(7)
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
C17 C22 . 1.400(7)
C17 C18 . 1.409(7)
C18 O2 . 1.341(6)
C18 C19 . 1.403(7)
C19 C20 . 1.367(8)
C19 H19 . 0.9300
C20 C21 . 1.372(8)
C20 H20 . 0.9300
C21 C22 . 1.379(7)
C21 H21 . 0.9300
C22 H22 . 0.9300
C23 C24 . 1.373(7)
C23 C28 . 1.402(7)
C23 H23 . 0.9300
C24 C25 . 1.374(7)
C24 H24 . 0.9300
C25 C26 . 1.370(7)
C25 H25 . 0.9300
C26 C27 . 1.407(6)
C26 H26 . 0.9300
C27 C28 . 1.417(7)
C27 C29 . 1.468(7)
C28 O5 . 1.338(5)
C29 N3 . 1.279(6)
C29 C30 . 1.497(6)
C30 H30A . 0.9600
C30 H30B . 0.9600
C30 H30C . 0.9600
C31 N3 . 1.462(6)
C31 C33 . 1.522(6)
C31 C32 . 1.528(7)
C31 H31 . 0.9800
C32 C33 2_565 1.514(6)
C32 H32A . 0.9700
C32 H32B . 0.9700
C33 C32 2_565 1.514(6)
C33 H33A . 0.9700
C33 H33B . 0.9700
C34 C35 . 1.367(7)
C34 C39 . 1.394(7)
C34 H34 . 0.9300
C35 C36 . 1.381(8)
C35 H35 . 0.9300
C36 C37 . 1.368(7)
C36 H36 . 0.9300
C37 C38 . 1.407(7)
C37 H37 . 0.9300
C38 C39 . 1.406(7)
C38 C40 . 1.485(7)
C39 O6 . 1.338(6)
C40 N4 . 1.290(6)
C40 C41 . 1.487(6)
C41 H41A . 0.9600
C41 H41B . 0.9600
C41 H41C . 0.9600
C42 N4 . 1.459(6)
C42 C44 . 1.517(6)
C42 C43 . 1.528(6)
C42 H42 . 0.9800
C43 C44 2_766 1.516(6)
C43 H43A . 0.9700
C43 H43B . 0.9700
C44 C43 2_766 1.516(6)
C44 H44A . 0.9700
C44 H44B . 0.9700
O1 H1A . 0.8200
O2 H2A . 0.8200
O5 H5 . 0.8201
O6 H6 . 0.8201
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O6 H6 N4 1_555 0.82 1.79 2.526(5) 146.6
O5 H5 N3 1_555 0.82 1.80 2.523(5) 147.0
O2 H2A N2 1_555 0.82 1.80 2.516(5) 145.4
O1 H1A N1 1_555 0.82 1.79 2.520(5) 147.2
C11 H11A Cg1 2_655 0.97 2.64 3.552(3) 155
C14 H14A Cg2 2_656 0.97 2.63 3.5400(10) 156
C33 H33B Cg3 1_455 0.97 2.62 3.510(4) 151
C44 H44A Cg4 1_655 0.97 2.61 3.504(4) 152
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_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . -0.8(9)
C1 C2 C3 C4 . -0.1(9)
C2 C3 C4 C5 . -0.4(9)
C3 C4 C5 C6 . 1.9(8)
C3 C4 C5 C7 . -179.7(5)
C2 C1 C6 O1 . -177.6(6)
C2 C1 C6 C5 . 2.2(9)
C4 C5 C6 O1 . 177.1(5)
C7 C5 C6 O1 . -1.3(8)
C4 C5 C6 C1 . -2.7(8)
C7 C5 C6 C1 . 178.9(5)
C4 C5 C7 N1 . -169.6(5)
C6 C5 C7 N1 . 8.8(7)
C4 C5 C7 C8 . 11.7(8)
C6 C5 C7 C8 . -169.9(5)
N1 C9 C10 C11 . -173.8(4)
C14 C9 C10 C11 . -54.9(5)
C9 C10 C11 C12 . 56.3(5)
C10 C11 C12 N2 . -176.4(4)
C10 C11 C12 C13 . -55.2(5)
N2 C12 C13 C14 . 174.1(4)
C11 C12 C13 C14 . 54.3(5)
C12 C13 C14 C9 . -55.5(5)
N1 C9 C14 C13 . 176.0(4)
C10 C9 C14 C13 . 55.0(5)
N2 C15 C17 C22 . 169.6(5)
C16 C15 C17 C22 . -11.2(8)
N2 C15 C17 C18 . -9.4(8)
C16 C15 C17 C18 . 169.9(5)
C22 C17 C18 O2 . -177.6(5)
C15 C17 C18 O2 . 1.4(9)
C22 C17 C18 C19 . 3.2(8)
C15 C17 C18 C19 . -177.8(5)
O2 C18 C19 C20 . 177.3(6)
C17 C18 C19 C20 . -3.4(9)
C18 C19 C20 C21 . 1.5(10)
C19 C20 C21 C22 . 0.6(9)
C20 C21 C22 C17 . -0.8(9)
C18 C17 C22 C21 . -1.1(9)
C15 C17 C22 C21 . 179.9(5)
C28 C23 C24 C25 . 1.4(8)
C23 C24 C25 C26 . 0.0(9)
C24 C25 C26 C27 . -0.5(9)
C25 C26 C27 C28 . -0.5(8)
C25 C26 C27 C29 . -179.1(5)
C24 C23 C28 O5 . 178.0(5)
C24 C23 C28 C27 . -2.4(8)
C26 C27 C28 O5 . -178.5(5)
C29 C27 C28 O5 . 0.1(8)
C26 C27 C28 C23 . 1.9(8)
C29 C27 C28 C23 . -179.5(5)
C26 C27 C29 N3 . 168.5(5)
C28 C27 C29 N3 . -10.1(8)
C26 C27 C29 C30 . -11.7(8)
C28 C27 C29 C30 . 169.7(5)
N3 C31 C32 C33 2_565 175.1(4)
C33 C31 C32 C33 2_565 55.4(6)
N3 C31 C33 C32 2_565 -177.7(4)
C32 C31 C33 C32 2_565 -56.0(6)
C39 C34 C35 C36 . -0.7(9)
C34 C35 C36 C37 . -0.9(9)
C35 C36 C37 C38 . 1.2(9)
C36 C37 C38 C39 . 0.1(8)
C36 C37 C38 C40 . 179.1(6)
C35 C34 C39 O6 . -178.1(5)
C35 C34 C39 C38 . 2.0(8)
C37 C38 C39 O6 . 178.4(5)
C40 C38 C39 O6 . -0.6(8)
C37 C38 C39 C34 . -1.6(8)
C40 C38 C39 C34 . 179.4(5)
C39 C38 C40 N4 . 9.9(8)
C37 C38 C40 N4 . -169.1(5)
C39 C38 C40 C41 . -169.0(5)
C37 C38 C40 C41 . 12.0(8)
N4 C42 C43 C44 2_766 -174.8(4)
C44 C42 C43 C44 2_766 -54.9(6)
N4 C42 C44 C43 2_766 176.9(4)
C43 C42 C44 C43 2_766 55.4(6)
C5 C7 N1 C9 . 179.2(4)
C8 C7 N1 C9 . -2.2(8)
C10 C9 N1 C7 . -83.5(6)
C14 C9 N1 C7 . 156.0(5)
C17 C15 N2 C12 . -178.9(5)
C16 C15 N2 C12 . 1.8(9)
C11 C12 N2 C15 . -155.7(5)
C13 C12 N2 C15 . 83.6(6)
C27 C29 N3 C31 . -178.6(5)
C30 C29 N3 C31 . 1.6(8)
C33 C31 N3 C29 . -158.9(5)
C32 C31 N3 C29 . 80.6(6)
C38 C40 N4 C42 . 178.8(5)
C41 C40 N4 C42 . -2.4(8)
C44 C42 N4 C40 . 159.2(5)
C43 C42 N4 C40 . -80.0(6)
