#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224745.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_2224745
loop_
_publ_author_name
'Lu, Pingping'
'Lian, Chaomei'
'Zhu, Yulin'
_publ_section_title
;
 8-Methyl-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
;
_journal_coeditor_code           RK2180
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o17
_journal_paper_doi               10.1107/S1600536809051125
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N O'
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_name_systematic
;
8-Methyl-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.426(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.751(4)
_cell_length_b                   17.780(5)
_cell_length_c                   17.516(4)
_cell_measurement_reflns_used    1233
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.26
_cell_measurement_theta_min      2.33
_cell_volume                     2931.3(15)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII area-detector diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0674
_diffrn_reflns_av_sigmaI/netI    0.0885
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14911
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.1749
_refine_ls_R_factor_gt           0.0690
_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)+(0.045P)²+0.45P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                2114
_reflns_number_total             5280
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2180.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224745
_cod_database_fobs_code          2224745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.6400(3) 0.92041(17) 0.1751(2) 0.0704(9) Uani d . 1 . .
H H1 0.6805 0.8939 0.1601 0.084 Uiso d R 1 . .
C C1 0.8237(5) 1.2230(2) 0.3116(3) 0.1063(16) Uani d . 1 . .
H H1A 0.8247 1.2483 0.2637 0.159 Uiso calc R 1 . .
H H1B 0.9177 1.2230 0.3790 0.159 Uiso calc R 1 . .
H H1C 0.7600 1.2485 0.3144 0.159 Uiso calc R 1 . .
C C2 0.7734(4) 1.14134(12) 0.2756(2) 0.0783(12) Uani d G 1 . .
C C3 0.8651(2) 1.08924(18) 0.28789(19) 0.0806(12) Uani d G 1 . .
H H3 0.9558 1.1038 0.3175 0.097 Uiso calc R 1 . .
C C4 0.8212(3) 1.01531(16) 0.2559(2) 0.0746(11) Uani d G 1 . .
H H4 0.8825 0.9804 0.2641 0.090 Uiso calc R 1 . .
C C5 0.6856(3) 0.99347(11) 0.2116(2) 0.0636(10) Uani d G 1 . .
C C6 0.5939(2) 1.04557(16) 0.19939(19) 0.0698(11) Uani d G 1 . .
C C7 0.6378(3) 1.11950(14) 0.2314(2) 0.0787(12) Uani d G 1 . .
H H7 0.5765 1.1544 0.2232 0.094 Uiso calc R 1 . .
O O1 0.3443(3) 1.07237(16) 0.0794(3) 0.1021(10) Uani d . 1 . .
C C8 0.4479(5) 1.0230(2) 0.1582(3) 0.0808(12) Uani d . 1 . .
H H8 0.4482 1.0236 0.2143 0.097 Uiso calc R 1 . .
C C9 0.4029(4) 0.9456(2) 0.1070(3) 0.0746(11) Uani d . 1 . .
H H9 0.3305 0.9255 0.1061 0.090 Uiso calc R 1 . .
C C10 0.3334(5) 0.9635(2) -0.0018(3) 0.0834(12) Uani d . 1 . .
H H10A 0.2570 0.9284 -0.0501 0.100 Uiso calc R 1 . .
H H10B 0.4017 0.9616 -0.0097 0.100 Uiso calc R 1 . .
C C11 0.2772(5) 1.0417(3) -0.0188(4) 0.1070(15) Uani d . 1 . .
H H11A 0.2980 1.0721 -0.0532 0.128 Uiso calc R 1 . .
H H11B 0.1750 1.0405 -0.0618 0.128 Uiso calc R 1 . .
C C12 0.5249(4) 0.8892(2) 0.1623(3) 0.0691(11) Uani d . 1 . .
H H12 0.5598 0.8810 0.2315 0.083 Uiso calc R 1 . .
C C13 0.4766(3) 0.81442(12) 0.10806(19) 0.0670(10) Uani d G 1 . .
C C14 0.4233(3) 0.76150(17) 0.13274(19) 0.0819(12) Uani d G 1 . .
H H14 0.4225 0.7717 0.1844 0.098 Uiso calc R 1 . .
C C15 0.3711(3) 0.69334(14) 0.0802(2) 0.0932(14) Uani d G 1 . .
H H15 0.3354 0.6579 0.0967 0.112 Uiso calc R 1 . .
C C16 0.3723(3) 0.67811(13) 0.0029(2) 0.0945(14) Uani d G 1 . .
H H16 0.3374 0.6325 -0.0322 0.113 Uiso calc R 1 . .
C C17 0.4257(3) 0.73103(17) -0.02174(18) 0.0928(14) Uani d G 1 . .
H H17 0.4265 0.7208 -0.0734 0.111 Uiso calc R 1 . .
C C18 0.4778(3) 0.79919(15) 0.0308(2) 0.0805(12) Uani d G 1 . .
H H18 0.5135 0.8346 0.0143 0.097 Uiso calc R 1 . .
O O2 0.8981(3) 0.82604(14) 0.2907(2) 0.0841(8) Uani d . 1 . .
N N2 0.7998(3) 0.68166(16) 0.3925(2) 0.0739(9) Uani d . 1 . .
H H2 0.7892 0.6442 0.4179 0.089 Uiso d R 1 . .
C C19 0.7740(5) 0.9864(2) 0.4799(4) 0.1011(15) Uani d . 1 . .
H H19A 0.7976 0.9903 0.5447 0.152 Uiso calc R 1 . .
H H19B 0.6787 1.0040 0.4252 0.152 Uiso calc R 1 . .
H H19C 0.8387 1.0164 0.4823 0.152 Uiso calc R 1 . .
C C20 0.7851(3) 0.90401(11) 0.46008(18) 0.0713(11) Uani d G 1 . .
C C21 0.7154(3) 0.84833(16) 0.46715(19) 0.0805(12) Uani d G 1 . .
H H21 0.6648 0.8609 0.4861 0.097 Uiso calc R 1 . .
C C22 0.7215(3) 0.77394(14) 0.4459(2) 0.0766(12) Uani d G 1 . .
H H22 0.6749 0.7367 0.4507 0.092 Uiso calc R 1 . .
C C23 0.7971(3) 0.75522(10) 0.41766(18) 0.0646(10) Uani d G 1 . .
C C24 0.8668(2) 0.81089(14) 0.41060(18) 0.0607(10) Uani d G 1 . .
C C25 0.8607(2) 0.88529(12) 0.43181(19) 0.0695(11) Uani d G 1 . .
H H25 0.9073 0.9225 0.4271 0.083 Uiso calc R 1 . .
C C26 0.9540(4) 0.7911(2) 0.3858(3) 0.0722(11) Uani d . 1 . .
H H26 1.0510 0.8094 0.4417 0.087 Uiso calc R 1 . .
C C27 0.9609(4) 0.7077(2) 0.3691(3) 0.0779(12) Uani d . 1 . .
H H27 1.0399 0.6837 0.4350 0.093 Uiso calc R 1 . .
C C28 0.9901(5) 0.7086(2) 0.2974(4) 0.1086(16) Uani d . 1 . .
H H28A 1.0894 0.6983 0.3359 0.130 Uiso calc R 1 . .
H H28B 0.9324 0.6713 0.2431 0.130 Uiso calc R 1 . .
C C29 0.9512(6) 0.7860(3) 0.2531(4) 0.1208(19) Uani d . 1 . .
H H29A 1.0341 0.8114 0.2733 0.145 Uiso calc R 1 . .
H H29B 0.8796 0.7836 0.1782 0.145 Uiso calc R 1 . .
C C30 0.8210(4) 0.67054(19) 0.3224(3) 0.0657(10) Uani d . 1 . .
H H30 0.7451 0.6977 0.2586 0.079 Uiso calc R 1 . .
C C31 0.8059(4) 0.58845(13) 0.2948(3) 0.0754(12) Uani d G 1 . .
C C32 0.6928(3) 0.56536(18) 0.1940(2) 0.1154(18) Uani d G 1 . .
H H32 0.6292 0.6007 0.1436 0.138 Uiso calc R 1 . .
C C33 0.6748(4) 0.4895(2) 0.1684(3) 0.140(2) Uani d G 1 . .
H H33 0.5992 0.4741 0.1009 0.168 Uiso calc R 1 . .
C C34 0.7699(5) 0.43679(13) 0.2437(4) 0.1257(19) Uani d G 1 . .
H H34 0.7579 0.3861 0.2266 0.151 Uiso calc R 1 . .
C C35 0.8830(4) 0.45988(17) 0.3446(3) 0.133(2) Uani d G 1 . .
H H35 0.9466 0.4246 0.3950 0.159 Uiso calc R 1 . .
C C36 0.9010(3) 0.5357(2) 0.3702(2) 0.1198(18) Uani d G 1 . .
H H36 0.9766 0.5511 0.4377 0.144 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
N2 C23 C24 . . 119.3(2) ?
N2 C23 C22 . . 120.7(2) ?
C24 C23 C22 . . 120.0 ?
C25 C24 C23 . . 120.0 ?
C25 C24 C26 . . 119.5(2) ?
C23 C24 C26 . . 120.5(2) ?
C24 C25 C20 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C20 C25 H25 . . 120.0 ?
C21 C20 C25 . . 120.0 ?
C21 C20 C19 . . 119.9(2) ?
C25 C20 C19 . . 120.1(2) ?
C20 C21 C22 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C21 C22 C23 . . 120.0 ?
C21 C22 H22 . . 120.0 ?
C23 C22 H22 . . 120.0 ?
C6 C5 C4 . . 120.0 ?
C6 C5 N1 . . 120.3(2) ?
C4 C5 N1 . . 119.6(2) ?
C5 C6 C7 . . 120.0 ?
C5 C6 C8 . . 121.8(2) ?
C7 C6 C8 . . 118.0(2) ?
C2 C7 C6 . . 120.0 ?
C2 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C2 C3 . . 120.0 ?
C7 C2 C1 . . 120.6(3) ?
C3 C2 C1 . . 119.4(3) ?
C4 C3 C2 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C14 C13 C18 . . 120.0 ?
C14 C13 C12 . . 118.6(2) ?
C18 C13 C12 . . 121.3(2) ?
C15 C14 C13 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C17 C16 C15 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C15 C16 H16 . . 120.0 ?
C16 C17 C18 . . 120.0 ?
C16 C17 H17 . . 120.0 ?
C18 C17 H17 . . 120.0 ?
C17 C18 C13 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C13 C18 H18 . . 120.0 ?
C36 C31 C32 . . 120.0 ?
C36 C31 C30 . . 120.5(3) ?
C32 C31 C30 . . 119.5(3) ?
C31 C36 C35 . . 120.0 ?
C31 C36 H36 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C34 C35 C36 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C36 C35 H35 . . 120.0 ?
C35 C34 C33 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C32 C33 C34 . . 120.0 ?
C32 C33 H33 . . 120.0 ?
C34 C33 H33 . . 120.0 ?
C33 C32 C31 . . 120.0 ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C8 O1 C11 . . 110.5(3) ?
C5 N1 C12 . . 119.9(3) ?
C5 N1 H1 . . 120.1 ?
C12 N1 H1 . . 120.1 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C8 C9 . . 104.8(3) ?
O1 C8 C6 . . 109.8(3) ?
C9 C8 C6 . . 111.7(3) ?
O1 C8 H8 . . 110.1 ?
C9 C8 H8 . . 110.1 ?
C6 C8 H8 . . 110.1 ?
C10 C9 C8 . . 102.8(3) ?
C10 C9 C12 . . 114.9(3) ?
C8 C9 C12 . . 113.6(3) ?
C10 C9 H9 . . 108.4 ?
C8 C9 H9 . . 108.4 ?
C12 C9 H9 . . 108.4 ?
C9 C10 C11 . . 104.0(3) ?
C9 C10 H10A . . 111.0 ?
C11 C10 H10A . . 111.0 ?
C9 C10 H10B . . 111.0 ?
C11 C10 H10B . . 111.0 ?
H10A C10 H10B . . 109.0 ?
O1 C11 C10 . . 107.5(4) ?
O1 C11 H11A . . 110.2 ?
C10 C11 H11A . . 110.2 ?
O1 C11 H11B . . 110.2 ?
C10 C11 H11B . . 110.2 ?
H11A C11 H11B . . 108.5 ?
N1 C12 C13 . . 112.3(3) ?
N1 C12 C9 . . 109.9(3) ?
C13 C12 C9 . . 111.9(3) ?
N1 C12 H12 . . 107.5 ?
C13 C12 H12 . . 107.5 ?
C9 C12 H12 . . 107.5 ?
C29 O2 C26 . . 107.6(3) ?
C23 N2 C30 . . 117.3(3) ?
C23 N2 H2 . . 121.3 ?
C30 N2 H2 . . 121.3 ?
C20 C19 H19A . . 109.5 ?
C20 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C20 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 C26 C24 . . 110.7(3) ?
O2 C26 C27 . . 104.3(3) ?
C24 C26 C27 . . 116.0(3) ?
O2 C26 H26 . . 108.6 ?
C24 C26 H26 . . 108.6 ?
C27 C26 H26 . . 108.6 ?
C30 C27 C26 . . 109.1(3) ?
C30 C27 C28 . . 114.1(4) ?
C26 C27 C28 . . 102.9(3) ?
C30 C27 H27 . . 110.2 ?
C26 C27 H27 . . 110.2 ?
C28 C27 H27 . . 110.2 ?
C29 C28 C27 . . 104.9(3) ?
C29 C28 H28A . . 110.8 ?
C27 C28 H28A . . 110.8 ?
C29 C28 H28B . . 110.8 ?
C27 C28 H28B . . 110.8 ?
H28A C28 H28B . . 108.8 ?
O2 C29 C28 . . 108.5(4) ?
O2 C29 H29A . . 110.0 ?
C28 C29 H29A . . 110.0 ?
O2 C29 H29B . . 110.0 ?
C28 C29 H29B . . 110.0 ?
H29A C29 H29B . . 108.4 ?
N2 C30 C31 . . 110.4(3) ?
N2 C30 C27 . . 108.0(3) ?
C31 C30 C27 . . 116.2(3) ?
N2 C30 H30 . . 107.3 ?
C31 C30 H30 . . 107.3 ?
C27 C30 H30 . . 107.3 ?
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
C23 N2 . 1.388(3) ?
C23 C24 . 1.3900 ?
C23 C22 . 1.3900 ?
C24 C25 . 1.3900 ?
C24 C26 . 1.484(4) ?
C25 C20 . 1.3900 ?
C25 H25 . 0.9300 ?
C20 C21 . 1.3900 ?
C20 C19 . 1.534(4) ?
C21 C22 . 1.3900 ?
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C5 C6 . 1.3900 ?
C5 C4 . 1.3900 ?
C5 N1 . 1.391(3) ?
C6 C7 . 1.3900 ?
C6 C8 . 1.528(5) ?
C7 C2 . 1.3900 ?
C7 H7 . 0.9300 ?
C2 C3 . 1.3900 ?
C2 C1 . 1.539(4) ?
C3 C4 . 1.3900 ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9300 ?
C13 C14 . 1.3900 ?
C13 C18 . 1.3900 ?
C13 C12 . 1.504(4) ?
C14 C15 . 1.3900 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.3900 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3900 ?
C16 H16 . 0.9300 ?
C17 C18 . 1.3900 ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C31 C36 . 1.3900 ?
C31 C32 . 1.3900 ?
C31 C30 . 1.508(4) ?
C36 C35 . 1.3900 ?
C36 H36 . 0.9300 ?
C35 C34 . 1.3900 ?
C35 H35 . 0.9300 ?
C34 C33 . 1.3900 ?
C34 H34 . 0.9300 ?
C33 C32 . 1.3900 ?
C33 H33 . 0.9300 ?
C32 H32 . 0.9300 ?
O1 C8 . 1.400(4) ?
O1 C11 . 1.415(5) ?
N1 C12 . 1.438(4) ?
N1 H1 . 0.8600 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C8 C9 . 1.526(5) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.497(5) ?
C9 C12 . 1.527(5) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.500(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12 . 0.9800 ?
O2 C29 . 1.415(9) ?
O2 C26 . 1.438(4) ?
N2 C30 . 1.438(4) ?
N2 H2 . 0.8599 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C26 C27 . 1.525(5) ?
C26 H26 . 0.9800 ?
C27 C30 . 1.522(5) ?
C27 C28 . 1.532(5) ?
C27 H27 . 0.9800 ?
C28 C29 . 1.491(5) ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C30 H30 . 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
N1 H1 O2 . 0.86 2.41 2.959(4) 121.9
N2 H2 O1 2_645 0.86 2.15 2.934(4) 150.7
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
N2 C23 C24 C25 . . . . 177.6(2) ?
C22 C23 C24 C25 . . . . 0.0 ?
N2 C23 C24 C26 . . . . -5.5(3) ?
C22 C23 C24 C26 . . . . 176.8(3) ?
C23 C24 C25 C20 . . . . 0.0 ?
C26 C24 C25 C20 . . . . -176.9(3) ?
C24 C25 C20 C21 . . . . 0.0 ?
C24 C25 C20 C19 . . . . -177.9(3) ?
C25 C20 C21 C22 . . . . 0.0 ?
C19 C20 C21 C22 . . . . 177.9(3) ?
C20 C21 C22 C23 . . . . 0.0 ?
N2 C23 C22 C21 . . . . -177.6(2) ?
C24 C23 C22 C21 . . . . 0.0 ?
C4 C5 C6 C7 . . . . 0.0 ?
N1 C5 C6 C7 . . . . -176.7(3) ?
C4 C5 C6 C8 . . . . -175.7(3) ?
N1 C5 C6 C8 . . . . 7.6(3) ?
C5 C6 C7 C2 . . . . 0.0 ?
C8 C6 C7 C2 . . . . 175.8(3) ?
C6 C7 C2 C3 . . . . 0.0 ?
C6 C7 C2 C1 . . . . -179.9(3) ?
C7 C2 C3 C4 . . . . 0.0 ?
C1 C2 C3 C4 . . . . 179.9(3) ?
C2 C3 C4 C5 . . . . 0.0 ?
C6 C5 C4 C3 . . . . 0.0 ?
N1 C5 C4 C3 . . . . 176.8(3) ?
C18 C13 C14 C15 . . . . 0.0 ?
C12 C13 C14 C15 . . . . 176.7(3) ?
C13 C14 C15 C16 . . . . 0.0 ?
C14 C15 C16 C17 . . . . 0.0 ?
C15 C16 C17 C18 . . . . 0.0 ?
C16 C17 C18 C13 . . . . 0.0 ?
C14 C13 C18 C17 . . . . 0.0 ?
C12 C13 C18 C17 . . . . -176.6(3) ?
C32 C31 C36 C35 . . . . 0.0 ?
C30 C31 C36 C35 . . . . 177.7(3) ?
C31 C36 C35 C34 . . . . 0.0 ?
C36 C35 C34 C33 . . . . 0.0 ?
C35 C34 C33 C32 . . . . 0.0 ?
C34 C33 C32 C31 . . . . 0.0 ?
C36 C31 C32 C33 . . . . 0.0 ?
C30 C31 C32 C33 . . . . -177.7(3) ?
C6 C5 N1 C12 . . . . -24.4(4) ?
C4 C5 N1 C12 . . . . 158.8(3) ?
C11 O1 C8 C9 . . . . -23.5(5) ?
C11 O1 C8 C6 . . . . 96.6(4) ?
C5 C6 C8 O1 . . . . -131.3(3) ?
C7 C6 C8 O1 . . . . 53.0(4) ?
C5 C6 C8 C9 . . . . -15.4(4) ?
C7 C6 C8 C9 . . . . 168.8(3) ?
O1 C8 C9 C10 . . . . 32.1(4) ?
C6 C8 C9 C10 . . . . -86.8(4) ?
O1 C8 C9 C12 . . . . 157.0(3) ?
C6 C8 C9 C12 . . . . 38.1(4) ?
C8 C9 C10 C11 . . . . -28.3(4) ?
C12 C9 C10 C11 . . . . -152.3(4) ?
C8 O1 C11 C10 . . . . 5.3(5) ?
C9 C10 C11 O1 . . . . 15.4(5) ?
C5 N1 C12 C13 . . . . 171.8(3) ?
C5 N1 C12 C9 . . . . 46.5(4) ?
C14 C13 C12 N1 . . . . 148.6(2) ?
C18 C13 C12 N1 . . . . -34.7(4) ?
C14 C13 C12 C9 . . . . -87.2(3) ?
C18 C13 C12 C9 . . . . 89.4(3) ?
C10 C9 C12 N1 . . . . 64.8(4) ?
C8 C9 C12 N1 . . . . -53.2(4) ?
C10 C9 C12 C13 . . . . -60.6(4) ?
C8 C9 C12 C13 . . . . -178.7(3) ?
C24 C23 N2 C30 . . . . -25.0(4) ?
C22 C23 N2 C30 . . . . 152.6(2) ?
C29 O2 C26 C24 . . . . -160.0(3) ?
C29 O2 C26 C27 . . . . -34.6(4) ?
C25 C24 C26 O2 . . . . -64.7(3) ?
C23 C24 C26 O2 . . . . 118.5(3) ?
C25 C24 C26 C27 . . . . 176.9(3) ?
C23 C24 C26 C27 . . . . 0.1(4) ?
O2 C26 C27 C30 . . . . -89.9(4) ?
C24 C26 C27 C30 . . . . 32.0(5) ?
O2 C26 C27 C28 . . . . 31.6(4) ?
C24 C26 C27 C28 . . . . 153.5(4) ?
C30 C27 C28 C29 . . . . 100.3(4) ?
C26 C27 C28 C29 . . . . -17.7(5) ?
C26 O2 C29 C28 . . . . 23.5(5) ?
C27 C28 C29 O2 . . . . -2.5(6) ?
C23 N2 C30 C31 . . . . -174.1(3) ?
C23 N2 C30 C27 . . . . 57.8(4) ?
C36 C31 C30 N2 . . . . -64.4(3) ?
C32 C31 C30 N2 . . . . 113.3(3) ?
C36 C31 C30 C27 . . . . 59.0(4) ?
C32 C31 C30 C27 . . . . -123.2(3) ?
C26 C27 C30 N2 . . . . -58.8(4) ?
C28 C27 C30 N2 . . . . -173.2(3) ?
C26 C27 C30 C31 . . . . 176.5(3) ?
C28 C27 C30 C31 . . . . 62.1(4) ?
