#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/63/2226348.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_2226348
loop_
_publ_author_name
'Villalpando, Andrés'
'Fronczek, Frank R.'
'Isovitsch, Ralph'
_publ_section_title
;
 2-(9-Anthrylmethylideneamino)-4-methylphenol
;
_journal_coeditor_code           ZQ2039
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1353
_journal_paper_doi               10.1107/S1600536810016715
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H17 N O'
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.37
_chemical_name_systematic
;
2-(9-Anthrylmethylideneamino)-4-methylphenol
;
_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                94.508(9)
_cell_angle_beta                 97.164(11)
_cell_angle_gamma                106.490(11)
_cell_formula_units_Z            4
_cell_length_a                   8.6037(15)
_cell_length_b                   12.839(3)
_cell_length_c                   15.015(3)
_cell_measurement_reflns_used    7377
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.5
_cell_volume                     1566.6(6)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Nonius KappaCCD diffractometer with Oxford Cryostream'
_diffrn_measurement_method       'ω scans with κ offsets'
_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  0.057
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            35942
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         27.9
_diffrn_reflns_theta_min         2.5
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.108
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0571P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.110
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                4454
_reflns_number_total             7462
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2039.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_database_code               2226348
_cod_database_fobs_code          2226348
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_disorder_assembly
_atom_site_disorder_group
O O1 0.30490(15) 0.14730(11) 0.20434(9) 0.0223(3) Uani d . 1 . .
H H10H 0.261(2) 0.1946(17) 0.2172(14) 0.033 Uiso d . 1 . .
N N1 0.13998(16) 0.26290(12) 0.10202(10) 0.0177(3) Uani d . 1 . .
C C1 0.0939(2) 0.44058(15) 0.09855(11) 0.0164(4) Uani d . 1 . .
C C2 -0.0671(2) 0.42007(15) 0.11964(11) 0.0167(4) Uani d . 1 . .
C C3 -0.1820(2) 0.31351(16) 0.10892(12) 0.0215(4) Uani d . 1 . .
H H3 -0.1516 0.2527 0.0851 0.026 Uiso calc R 1 . .
C C4 -0.3344(2) 0.29700(16) 0.13208(13) 0.0246(5) Uani d . 1 . .
H H4 -0.4084 0.2251 0.1244 0.029 Uiso calc R 1 . .
C C5 -0.3837(2) 0.38605(17) 0.16758(13) 0.0249(5) Uani d . 1 . .
H H5 -0.4894 0.3733 0.1850 0.030 Uiso calc R 1 . .
C C6 -0.2806(2) 0.48933(16) 0.17677(12) 0.0213(4) Uani d . 1 . .
H H6 -0.3157 0.5486 0.1994 0.026 Uiso calc R 1 . .
C C7 -0.1195(2) 0.51040(15) 0.15290(11) 0.0170(4) Uani d . 1 . .
C C8 -0.0120(2) 0.61631(15) 0.16377(12) 0.0196(4) Uani d . 1 . .
H H8 -0.0473 0.6754 0.1867 0.023 Uiso calc R 1 . .
C C9 0.1462(2) 0.63784(15) 0.14184(12) 0.0181(4) Uani d . 1 . .
C C10 0.2576(2) 0.74645(16) 0.15396(13) 0.0237(4) Uani d . 1 . .
H H10 0.2225 0.8059 0.1763 0.028 Uiso calc R 1 . .
C C11 0.4120(2) 0.76605(17) 0.13417(14) 0.0289(5) Uani d . 1 . .
H H11 0.4841 0.8386 0.1425 0.035 Uiso calc R 1 . .
C C12 0.4657(2) 0.67730(16) 0.10083(13) 0.0262(5) Uani d . 1 . .
H H12 0.5740 0.6911 0.0870 0.031 Uiso calc R 1 . .
C C13 0.3642(2) 0.57331(16) 0.08864(13) 0.0222(4) Uani d . 1 . .
H H13 0.4031 0.5156 0.0665 0.027 Uiso calc R 1 . .
C C14 0.2004(2) 0.54824(15) 0.10823(12) 0.0178(4) Uani d . 1 . .
C C15 0.1512(2) 0.34955(15) 0.06342(12) 0.0181(4) Uani d . 1 . .
H H15 0.1987 0.3556 0.0095 0.022 Uiso calc R 1 . .
C C16 0.1843(2) 0.17612(14) 0.05799(12) 0.0165(4) Uani d . 1 . .
C C17 0.2645(2) 0.11812(15) 0.11268(12) 0.0170(4) Uani d . 1 . .
C C18 0.3106(2) 0.03190(15) 0.07482(12) 0.0191(4) Uani d . 1 . .
H H18 0.3682 -0.0058 0.1120 0.023 Uiso calc R 1 . .
C C19 0.2723(2) 0.00072(15) -0.01782(13) 0.0218(4) Uani d . 1 . .
H H19 0.3061 -0.0577 -0.0435 0.026 Uiso calc R 1 . .
C C20 0.1853(2) 0.05329(15) -0.07398(12) 0.0202(4) Uani d . 1 . .
C C21 0.1432(2) 0.14129(16) -0.03464(12) 0.0198(4) Uani d . 1 . .
H H21 0.0850 0.1787 -0.0718 0.024 Uiso calc R 1 . .
C C22 0.1364(2) 0.01475(18) -0.17348(13) 0.0316(5) Uani d . 1 . .
H H22A 0.0264 -0.0380 -0.1843 0.047 Uiso calc R 1 . .
H H22B 0.2149 -0.0203 -0.1943 0.047 Uiso calc R 1 . .
H H22C 0.1359 0.0774 -0.2067 0.047 Uiso calc R 1 . .
O O2 0.53743(15) 0.04269(11) 0.27603(8) 0.0207(3) Uani d . 1 . .
H H20H 0.488(2) 0.0923(17) 0.2760(13) 0.031 Uiso d . 1 . .
N N2 0.52578(16) 0.20557(12) 0.39729(10) 0.0168(3) Uani d . 1 . .
C C23 0.48926(19) 0.38573(14) 0.40197(11) 0.0142(4) Uani d . 1 . .
C C24 0.3154(2) 0.35684(14) 0.38026(11) 0.0150(4) Uani d . 1 . .
C C25 0.2085(2) 0.25083(15) 0.38727(11) 0.0175(4) Uani d . 1 . .
H H25 0.2540 0.1949 0.4049 0.021 Uiso calc R 1 . .
C C26 0.0420(2) 0.22873(15) 0.36905(12) 0.0197(4) Uani d . 1 . .
H H26 -0.0263 0.1578 0.3746 0.024 Uiso calc R 1 . .
C C27 -0.0304(2) 0.30931(16) 0.34210(12) 0.0205(4) Uani d . 1 . .
H H27 -0.1463 0.2922 0.3290 0.025 Uiso calc R 1 . .
C C28 0.0661(2) 0.41141(16) 0.33494(12) 0.0195(4) Uani d . 1 . .
H H28 0.0167 0.4656 0.3175 0.023 Uiso calc R 1 . .
C C29 0.2409(2) 0.43844(15) 0.35330(11) 0.0161(4) Uani d . 1 . .
C C30 0.3395(2) 0.54295(15) 0.34506(11) 0.0172(4) Uani d . 1 . .
H H30 0.2891 0.5956 0.3249 0.021 Uiso calc R 1 . .
C C31 0.5098(2) 0.57245(14) 0.36561(11) 0.0167(4) Uani d . 1 . .
C C32 0.6089(2) 0.67977(15) 0.35648(13) 0.0229(4) Uani d . 1 . .
H H32 0.5579 0.7320 0.3359 0.027 Uiso calc R 1 . .
C C33 0.7750(2) 0.70842(15) 0.37681(13) 0.0236(4) Uani d . 1 . .
H H33 0.8392 0.7804 0.3709 0.028 Uiso calc R 1 . .
C C34 0.8524(2) 0.63117(15) 0.40679(12) 0.0211(4) Uani d . 1 . .
H H34 0.9686 0.6519 0.4210 0.025 Uiso calc R 1 . .
C C35 0.7631(2) 0.52775(15) 0.41557(12) 0.0188(4) Uani d . 1 . .
H H35 0.8181 0.4771 0.4350 0.023 Uiso calc R 1 . .
C C36 0.5874(2) 0.49345(14) 0.39604(11) 0.0152(4) Uani d . 1 . .
C C37 0.5733(2) 0.30621(15) 0.43076(12) 0.0157(4) Uani d . 1 . .
H H37 0.6671 0.3307 0.4763 0.019 Uiso calc R 1 . .
C C38 0.61304(19) 0.13383(14) 0.42820(12) 0.0145(4) Uani d . 1 . .
C C39 0.61383(19) 0.05028(15) 0.36290(12) 0.0157(4) Uani d . 1 . .
C C40 0.69549(19) -0.02469(14) 0.38538(12) 0.0164(4) Uani d . 1 . .
H H40 0.6983 -0.0807 0.3409 0.020 Uiso calc R 1 . .
C C41 0.77342(19) -0.01782(15) 0.47339(12) 0.0172(4) Uani d . 1 . .
H H41 0.8307 -0.0690 0.4881 0.021 Uiso calc R 1 . .
C C42 0.76957(19) 0.06220(15) 0.54060(12) 0.0172(4) Uani d . 1 . .
C C43 0.68877(19) 0.13757(14) 0.51648(12) 0.0161(4) Uani d . 1 . .
H H43 0.6850 0.1930 0.5612 0.019 Uiso calc R 1 . .
C C44 0.8441(2) 0.06293(16) 0.63718(12) 0.0219(4) Uani d . 1 . .
H H44A 0.8793 0.1379 0.6678 0.033 Uiso calc R 1 . .
H H44B 0.9391 0.0350 0.6380 0.033 Uiso calc R 1 . .
H H44C 0.7624 0.0163 0.6685 0.033 Uiso calc R 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 O1 H10H . . 106.8(15) ?
C15 N1 C16 . . 118.53(15) ?
C14 C1 C2 . . 120.64(16) ?
C14 C1 C15 . . 118.97(15) ?
C2 C1 C15 . . 120.36(16) ?
C1 C2 C3 . . 123.32(16) ?
C1 C2 C7 . . 119.01(16) ?
C3 C2 C7 . . 117.67(15) ?
C4 C3 C2 . . 121.46(18) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 120.64(18) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.15(17) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 121.02(18) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 121.19(17) ?
C8 C7 C2 . . 119.78(15) ?
C6 C7 C2 . . 119.00(16) ?
C7 C8 C9 . . 121.78(17) ?
C7 C8 H8 . . 119.1 ?
C9 C8 H8 . . 119.1 ?
C8 C9 C10 . . 121.89(17) ?
C8 C9 C14 . . 119.11(16) ?
C10 C9 C14 . . 118.98(16) ?
C11 C10 C9 . . 121.35(18) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C12 . . 119.68(18) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 120.79(17) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 121.78(18) ?
C12 C13 H13 . . 119.1 ?
C14 C13 H13 . . 119.1 ?
C1 C14 C13 . . 122.90(17) ?
C1 C14 C9 . . 119.66(15) ?
C13 C14 C9 . . 117.42(16) ?
N1 C15 C1 . . 123.23(16) ?
N1 C15 H15 . . 118.4 ?
C1 C15 H15 . . 118.4 ?
C21 C16 C17 . . 118.71(16) ?
C21 C16 N1 . . 124.14(16) ?
C17 C16 N1 . . 117.01(15) ?
O1 C17 C18 . . 118.31(16) ?
O1 C17 C16 . . 121.24(16) ?
C18 C17 C16 . . 120.41(16) ?
C17 C18 C19 . . 119.72(17) ?
C17 C18 H18 . . 120.1 ?
C19 C18 H18 . . 120.1 ?
C18 C19 C20 . . 121.45(17) ?
C18 C19 H19 . . 119.3 ?
C20 C19 H19 . . 119.3 ?
C21 C20 C19 . . 117.80(17) ?
C21 C20 C22 . . 121.23(18) ?
C19 C20 C22 . . 120.97(17) ?
C20 C21 C16 . . 121.79(17) ?
C20 C21 H21 . . 119.1 ?
C16 C21 H21 . . 119.1 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C39 O2 H20H . . 105.9(14) ?
C37 N2 C38 . . 119.84(15) ?
C36 C23 C24 . . 120.39(16) ?
C36 C23 C37 . . 117.76(15) ?
C24 C23 C37 . . 121.85(16) ?
C23 C24 C25 . . 123.46(16) ?
C23 C24 C29 . . 119.12(16) ?
C25 C24 C29 . . 117.37(15) ?
C26 C25 C24 . . 121.06(17) ?
C26 C25 H25 . . 119.5 ?
C24 C25 H25 . . 119.5 ?
C25 C26 C27 . . 121.23(17) ?
C25 C26 H26 . . 119.4 ?
C27 C26 H26 . . 119.4 ?
C28 C27 C26 . . 119.87(16) ?
C28 C27 H27 . . 120.1 ?
C26 C27 H27 . . 120.1 ?
C27 C28 C29 . . 120.93(17) ?
C27 C28 H28 . . 119.5 ?
C29 C28 H28 . . 119.5 ?
C30 C29 C28 . . 120.78(16) ?
C30 C29 C24 . . 119.70(15) ?
C28 C29 C24 . . 119.53(16) ?
C31 C30 C29 . . 121.87(16) ?
C31 C30 H30 . . 119.1 ?
C29 C30 H30 . . 119.1 ?
C30 C31 C32 . . 121.12(17) ?
C30 C31 C36 . . 119.56(16) ?
C32 C31 C36 . . 119.32(16) ?
C33 C32 C31 . . 121.00(18) ?
C33 C32 H32 . . 119.5 ?
C31 C32 H32 . . 119.5 ?
C32 C33 C34 . . 120.05(17) ?
C32 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
C35 C34 C33 . . 120.98(17) ?
C35 C34 H34 . . 119.5 ?
C33 C34 H34 . . 119.5 ?
C34 C35 C36 . . 121.33(17) ?
C34 C35 H35 . . 119.3 ?
C36 C35 H35 . . 119.3 ?
C23 C36 C35 . . 123.36(16) ?
C23 C36 C31 . . 119.28(15) ?
C35 C36 C31 . . 117.32(16) ?
N2 C37 C23 . . 122.99(16) ?
N2 C37 H37 . . 118.5 ?
C23 C37 H37 . . 118.5 ?
C43 C38 C39 . . 119.36(16) ?
C43 C38 N2 . . 125.80(16) ?
C39 C38 N2 . . 114.77(16) ?
O2 C39 C40 . . 119.20(16) ?
O2 C39 C38 . . 120.91(16) ?
C40 C39 C38 . . 119.88(16) ?
C39 C40 C41 . . 119.70(17) ?
C39 C40 H40 . . 120.2 ?
C41 C40 H40 . . 120.2 ?
C40 C41 C42 . . 121.63(17) ?
C40 C41 H41 . . 119.2 ?
C42 C41 H41 . . 119.2 ?
C43 C42 C41 . . 117.83(17) ?
C43 C42 C44 . . 121.43(17) ?
C41 C42 C44 . . 120.68(16) ?
C42 C43 C38 . . 121.54(17) ?
C42 C43 H43 . . 119.2 ?
C38 C43 H43 . . 119.2 ?
C42 C44 H44A . . 109.5 ?
C42 C44 H44B . . 109.5 ?
H44A C44 H44B . . 109.5 ?
C42 C44 H44C . . 109.5 ?
H44A C44 H44C . . 109.5 ?
H44B C44 H44C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 . 1.371(2) ?
O1 H10H . 0.82(2) ?
N1 C15 . 1.280(2) ?
N1 C16 . 1.419(2) ?
C1 C14 . 1.410(2) ?
C1 C2 . 1.416(2) ?
C1 C15 . 1.477(2) ?
C2 C3 . 1.426(2) ?
C2 C7 . 1.435(2) ?
C3 C4 . 1.361(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.417(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.356(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.431(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.395(2) ?
C8 C9 . 1.396(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.433(3) ?
C9 C14 . 1.438(2) ?
C10 C11 . 1.355(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.425(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.356(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.427(2) ?
C13 H13 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 C21 . 1.396(2) ?
C16 C17 . 1.397(2) ?
C17 C18 . 1.383(2) ?
C18 C19 . 1.388(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.395(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.392(2) ?
C20 C22 . 1.504(3) ?
C21 H21 . 0.9500 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
O2 C39 . 1.368(2) ?
O2 H20H . 0.86(2) ?
N2 C37 . 1.279(2) ?
N2 C38 . 1.414(2) ?
C23 C36 . 1.417(2) ?
C23 C24 . 1.423(2) ?
C23 C37 . 1.470(2) ?
C24 C25 . 1.430(2) ?
C24 C29 . 1.434(2) ?
C25 C26 . 1.366(2) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.411(3) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.359(3) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.429(2) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.393(2) ?
C30 C31 . 1.393(2) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.427(2) ?
C31 C36 . 1.437(2) ?
C32 C33 . 1.359(3) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.414(3) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.358(2) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.434(2) ?
C35 H35 . 0.9500 ?
C37 H37 . 0.9500 ?
C38 C43 . 1.393(2) ?
C38 C39 . 1.397(2) ?
C39 C40 . 1.382(2) ?
C40 C41 . 1.389(2) ?
C40 H40 . 0.9500 ?
C41 C42 . 1.393(2) ?
C41 H41 . 0.9500 ?
C42 C43 . 1.388(2) ?
C42 C44 . 1.509(2) ?
C43 H43 . 0.9500 ?
C44 H44A . 0.9800 ?
C44 H44B . 0.9800 ?
C44 H44C . 0.9800 ?
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
O1 H10H N1 . 0.82(2) 2.27(2) 2.754(2) 118.0(17)
O2 H20H O1 . 0.86(2) 2.11(2) 2.8602(18) 144.9(18)
O2 H20H N2 . 0.86(2) 2.17(2) 2.695(2) 119.1(17)
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14 C1 C2 C3 . . . . 178.20(16) ?
C15 C1 C2 C3 . . . . 0.0(3) ?
C14 C1 C2 C7 . . . . -1.3(3) ?
C15 C1 C2 C7 . . . . -179.45(16) ?
C1 C2 C3 C4 . . . . 178.37(17) ?
C7 C2 C3 C4 . . . . -2.1(3) ?
C2 C3 C4 C5 . . . . 0.2(3) ?
C3 C4 C5 C6 . . . . 1.6(3) ?
C4 C5 C6 C7 . . . . -1.4(3) ?
C5 C6 C7 C8 . . . . -178.84(17) ?
C5 C6 C7 C2 . . . . -0.6(3) ?
C1 C2 C7 C8 . . . . 0.1(2) ?
C3 C2 C7 C8 . . . . -179.44(16) ?
C1 C2 C7 C6 . . . . -178.15(16) ?
C3 C2 C7 C6 . . . . 2.3(2) ?
C6 C7 C8 C9 . . . . 179.17(17) ?
C2 C7 C8 C9 . . . . 1.0(3) ?
C7 C8 C9 C10 . . . . -179.25(17) ?
C7 C8 C9 C14 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 178.62(18) ?
C14 C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . -0.2(3) ?
C10 C11 C12 C13 . . . . 0.0(3) ?
C11 C12 C13 C14 . . . . 0.2(3) ?
C2 C1 C14 C13 . . . . 179.46(16) ?
C15 C1 C14 C13 . . . . -2.3(3) ?
C2 C1 C14 C9 . . . . 1.5(3) ?
C15 C1 C14 C9 . . . . 179.64(16) ?
C12 C13 C14 C1 . . . . -178.18(17) ?
C12 C13 C14 C9 . . . . -0.1(3) ?
C8 C9 C14 C1 . . . . -0.4(3) ?
C10 C9 C14 C1 . . . . 178.07(16) ?
C8 C9 C14 C13 . . . . -178.52(17) ?
C10 C9 C14 C13 . . . . 0.0(2) ?
C16 N1 C15 C1 . . . . 174.06(15) ?
C14 C1 C15 N1 . . . . 130.13(19) ?
C2 C1 C15 N1 . . . . -51.7(3) ?
C15 N1 C16 C21 . . . . -41.7(2) ?
C15 N1 C16 C17 . . . . 142.73(16) ?
C21 C16 C17 O1 . . . . -178.70(15) ?
N1 C16 C17 O1 . . . . -2.9(2) ?
C21 C16 C17 C18 . . . . 3.7(2) ?
N1 C16 C17 C18 . . . . 179.53(15) ?
O1 C17 C18 C19 . . . . -179.66(15) ?
C16 C17 C18 C19 . . . . -2.0(2) ?
C17 C18 C19 C20 . . . . -1.2(3) ?
C18 C19 C20 C21 . . . . 2.4(2) ?
C18 C19 C20 C22 . . . . -176.54(16) ?
C19 C20 C21 C16 . . . . -0.6(2) ?
C22 C20 C21 C16 . . . . 178.34(16) ?
C17 C16 C21 C20 . . . . -2.4(2) ?
N1 C16 C21 C20 . . . . -177.88(15) ?
C36 C23 C24 C25 . . . . -178.08(15) ?
C37 C23 C24 C25 . . . . 2.1(3) ?
C36 C23 C24 C29 . . . . -0.7(2) ?
C37 C23 C24 C29 . . . . 179.52(16) ?
C23 C24 C25 C26 . . . . 177.33(16) ?
C29 C24 C25 C26 . . . . -0.1(2) ?
C24 C25 C26 C27 . . . . 0.5(3) ?
C25 C26 C27 C28 . . . . -0.8(3) ?
C26 C27 C28 C29 . . . . 0.8(3) ?
C27 C28 C29 C30 . . . . 179.40(17) ?
C27 C28 C29 C24 . . . . -0.4(2) ?
C23 C24 C29 C30 . . . . 2.7(2) ?
C25 C24 C29 C30 . . . . -179.73(16) ?
C23 C24 C29 C28 . . . . -177.46(15) ?
C25 C24 C29 C28 . . . . 0.1(2) ?
C28 C29 C30 C31 . . . . 177.71(15) ?
C24 C29 C30 C31 . . . . -2.5(3) ?
C29 C30 C31 C32 . . . . 179.78(16) ?
C29 C30 C31 C36 . . . . 0.1(3) ?
C30 C31 C32 C33 . . . . 179.82(17) ?
C36 C31 C32 C33 . . . . -0.5(3) ?
C31 C32 C33 C34 . . . . 0.5(3) ?
C32 C33 C34 C35 . . . . 0.2(3) ?
C33 C34 C35 C36 . . . . -0.9(3) ?
C24 C23 C36 C35 . . . . -179.05(15) ?
C37 C23 C36 C35 . . . . 0.8(2) ?
C24 C23 C36 C31 . . . . -1.6(2) ?
C37 C23 C36 C31 . . . . 178.21(16) ?
C34 C35 C36 C23 . . . . 178.33(16) ?
C34 C35 C36 C31 . . . . 0.8(2) ?
C30 C31 C36 C23 . . . . 1.9(2) ?
C32 C31 C36 C23 . . . . -177.74(15) ?
C30 C31 C36 C35 . . . . 179.50(15) ?
C32 C31 C36 C35 . . . . -0.1(2) ?
C38 N2 C37 C23 . . . . 179.85(14) ?
C36 C23 C37 N2 . . . . -142.22(16) ?
C24 C23 C37 N2 . . . . 37.6(2) ?
C37 N2 C38 C43 . . . . 35.3(2) ?
C37 N2 C38 C39 . . . . -147.70(15) ?
C43 C38 C39 O2 . . . . 178.51(14) ?
N2 C38 C39 O2 . . . . 1.3(2) ?
C43 C38 C39 C40 . . . . -2.8(2) ?
N2 C38 C39 C40 . . . . 179.93(14) ?
O2 C39 C40 C41 . . . . -179.96(14) ?
C38 C39 C40 C41 . . . . 1.4(2) ?
C39 C40 C41 C42 . . . . 1.0(2) ?
C40 C41 C42 C43 . . . . -1.8(2) ?
C40 C41 C42 C44 . . . . 175.37(15) ?
C41 C42 C43 C38 . . . . 0.2(2) ?
C44 C42 C43 C38 . . . . -176.88(15) ?
C39 C38 C43 C42 . . . . 2.0(2) ?
N2 C38 C43 C42 . . . . 178.95(15) ?
