#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229073.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_2229073
loop_
_publ_author_name
'Duangthongyou, Tanwawan'
'Makarasen, Arthit'
'Techasakul, Supanna'
'Chimnoi, Nitirat'
'Siripaisarnpipat, Sutatip'
_publ_section_title
;
 ({-})-Crebanine
;
_journal_coeditor_code           HG2768
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o402
_journal_paper_doi               10.1107/S1600536811001231
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H21 N O4'
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38
_chemical_name_common
;
(-)-Crebanine
;
_chemical_name_systematic
;
9,10-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-
benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.4029(3)
_cell_length_b                   20.5847(15)
_cell_length_c                   39.612(3)
_cell_measurement_reflns_used    254
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      25
_cell_volume                     3590.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Mo K\a'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            31211
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.251
_refine_ls_extinction_coef       0.0011(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   1.2
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2
_refine_ls_R_factor_gt           0.105
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1020P)²+1.8904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2493
_reflns_number_gt                3592
_reflns_number_total             5054
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            hg2768.cif
_cod_data_source_block           I
_cod_original_cell_volume        3590.2(4)
_cod_database_code               2229073
_cod_database_fobs_code          2229073
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 -0.0157(14) -0.29778(18) 0.91783(10) 0.0651(14) Uani d . 1 . .
O O2 0.2100(12) -0.22350(17) 0.88249(9) 0.0559(12) Uani d . 1 . .
O O3 0.4781(12) 0.06920(18) 0.82737(10) 0.0585(12) Uani d . 1 . .
O O4 0.1040(10) 0.09746(18) 0.87877(11) 0.0541(11) Uani d . 1 . .
O O5 0.6133(16) 1.07654(18) 0.71607(10) 0.0742(17) Uani d . 1 . .
O O6 0.4220(18) 1.14827(19) 0.67722(12) 0.089(2) Uani d . 1 . .
O O7 0.9437(13) 0.78611(19) 0.77372(10) 0.0602(13) Uani d . 1 . .
O O8 0.5931(10) 0.75386(17) 0.72165(10) 0.0479(10) Uani d . 1 . .
N N1 -0.2107(12) -0.0207(2) 0.98698(12) 0.0476(12) Uani d . 1 . .
N N2 0.2578(11) 0.8658(2) 0.61320(11) 0.0434(11) Uani d . 1 . .
C C1 0.1036(14) -0.1925(2) 0.91134(12) 0.0401(13) Uani d . 1 . .
C C2 -0.0304(15) -0.2372(2) 0.93191(14) 0.0451(14) Uani d . 1 . .
C C3 -0.1577(16) -0.2198(3) 0.96193(15) 0.0521(16) Uani d . 1 . .
H H3A -0.2482 -0.2506 0.9758 0.062 Uiso calc R 1 . .
C C4 -0.1484(14) -0.1539(3) 0.97130(14) 0.0448(14) Uani d . 1 . .
C C5 -0.2810(18) -0.1329(3) 1.00402(14) 0.0589(17) Uani d . 1 . .
H H5A -0.225 -0.1638 1.0214 0.071 Uiso calc R 1 . .
H H5B -0.5008 -0.1327 1.0022 0.071 Uiso calc R 1 . .
C C6 -0.1727(17) -0.0660(3) 1.01402(15) 0.065(2) Uani d . 1 . .
H H6A -0.2863 -0.0512 1.0335 0.078 Uiso calc R 1 . .
H H6B 0.0402 -0.068 1.0203 0.078 Uiso calc R 1 . .
C C7 -0.0060(13) -0.0364(3) 0.95844(12) 0.0386(12) Uani d . 1 . .
H H7A 0.2024 -0.0261 0.9653 0.046 Uiso calc R 1 . .
C C8 -0.0189(12) -0.1080(2) 0.94904(13) 0.0364(12) Uani d . 1 . .
C C9 0.1075(13) -0.1262(2) 0.91788(12) 0.0349(12) Uani d . 1 . .
C C10 0.173(2) -0.2903(3) 0.88925(18) 0.082(3) Uani d . 1 . .
H H10A 0.3693 -0.3101 0.8935 0.098 Uiso calc R 1 . .
H H10B 0.0819 -0.3117 0.8699 0.098 Uiso calc R 1 . .
C C11 -0.0825(13) 0.0045(2) 0.92741(13) 0.0407(13) Uani d . 1 . .
H H11A -0.292 -0.0029 0.9209 0.049 Uiso calc R 1 . .
H H11B -0.0597 0.0503 0.9328 0.049 Uiso calc R 1 . .
C C12 0.1226(12) -0.0127(2) 0.89867(13) 0.0353(12) Uani d . 1 . .
C C13 0.2230(12) -0.0770(2) 0.89452(12) 0.0320(11) Uani d . 1 . .
C C14 0.4221(14) -0.0913(3) 0.86779(13) 0.0398(13) Uani d . 1 . .
H H14A 0.4952 -0.1333 0.8652 0.048 Uiso calc R 1 . .
C C15 0.5107(15) -0.0432(3) 0.84522(13) 0.0444(14) Uani d . 1 . .
H H15A 0.6409 -0.0535 0.8275 0.053 Uiso calc R 1 . .
C C16 0.4091(14) 0.0190(2) 0.84870(13) 0.0387(13) Uani d . 1 . .
C C17 0.2161(13) 0.0345(2) 0.87532(14) 0.0389(12) Uani d . 1 . .
C C18 -0.158(2) 0.0464(3) 0.99844(17) 0.077(2) Uani d . 1 . .
H H18A -0.2857 0.0555 1.0175 0.115 Uiso calc R 1 . .
H H18B -0.2052 0.076 0.9805 0.115 Uiso calc R 1 . .
H H18C 0.0509 0.0514 1.0048 0.115 Uiso calc R 1 . .
C C19 0.674(2) 0.0563(3) 0.80014(17) 0.070(2) Uani d . 1 . .
H H19A 0.7034 0.0953 0.7872 0.105 Uiso calc R 1 . .
H H19B 0.5868 0.0234 0.786 0.105 Uiso calc R 1 . .
H H19C 0.8666 0.0415 0.8086 0.105 Uiso calc R 1 . .
C C20 0.319(2) 0.1428(3) 0.8904(2) 0.083(2) Uani d . 1 . .
H H20A 0.226 0.1849 0.8921 0.124 Uiso calc R 1 . .
H H20B 0.4864 0.1448 0.8749 0.124 Uiso calc R 1 . .
H H20C 0.3915 0.1298 0.9123 0.124 Uiso calc R 1 . .
C C21 0.5342(18) 1.0426(3) 0.68717(13) 0.0518(16) Uani d . 1 . .
C C22 0.413(2) 1.0858(3) 0.66409(16) 0.064(2) Uani d . 1 . .
C C23 0.3093(19) 1.0661(3) 0.63356(16) 0.0607(19) Uani d . 1 . .
H H23A 0.2322 1.0957 0.618 0.073 Uiso calc R 1 . .
C C24 0.3227(15) 0.9997(3) 0.62627(14) 0.0482(15) Uani d . 1 . .
C C25 0.2002(17) 0.9756(3) 0.59241(15) 0.0595(18) Uani d . 1 . .
H H25A -0.02 0.976 0.593 0.071 Uiso calc R 1 . .
H H25B 0.2653 1.005 0.5747 0.071 Uiso calc R 1 . .
C C26 0.3056(17) 0.9090(3) 0.58427(13) 0.0528(16) Uani d . 1 . .
H H26A 0.1947 0.8926 0.5649 0.063 Uiso calc R 1 . .
H H26B 0.5197 0.91 0.5785 0.063 Uiso calc R 1 . .
C C27 0.4581(12) 0.8834(2) 0.64149(12) 0.0350(12) Uani d . 1 . .
H H27A 0.6677 0.8731 0.6351 0.042 Uiso calc R 1 . .
C C28 0.4386(13) 0.9565(2) 0.64921(12) 0.0382(13) Uani d . 1 . .
C C29 0.5500(14) 0.9766(2) 0.68092(13) 0.0400(13) Uani d . 1 . .
C C30 0.525(4) 1.1408(3) 0.7099(2) 0.126(5) Uani d . 1 . .
H H30A 0.366 1.153 0.7255 0.152 Uiso calc R 1 . .
H H30B 0.6971 1.1694 0.7136 0.152 Uiso calc R 1 . .
C C31 0.3784(14) 0.8450(2) 0.67290(12) 0.0396(13) Uani d . 1 . .
H H31A 0.1685 0.8532 0.679 0.048 Uiso calc R 1 . .
H H31B 0.4002 0.7989 0.6683 0.048 Uiso calc R 1 . .
C C32 0.5819(13) 0.8637(2) 0.70186(12) 0.0357(12) Uani d . 1 . .
C C33 0.6691(13) 0.9292(2) 0.70569(12) 0.0367(12) Uani d . 1 . .
C C34 0.8646(16) 0.9456(3) 0.73220(13) 0.0463(15) Uani d . 1 . .
H H34A 0.9318 0.9883 0.7343 0.056 Uiso calc R 1 . .
C C35 0.9600(16) 0.8996(3) 0.75542(14) 0.0502(15) Uani d . 1 . .
H H35A 1.0848 0.9116 0.7733 0.06 Uiso calc R 1 . .
C C36 0.8682(15) 0.8351(3) 0.75186(13) 0.0440(14) Uani d . 1 . .
C C37 0.6859(14) 0.8179(2) 0.72494(13) 0.0382(13) Uani d . 1 . .
C C38 0.310(2) 0.7977(3) 0.60256(18) 0.075(2) Uani d . 1 . .
H H38A 0.1769 0.7873 0.5841 0.112 Uiso calc R 1 . .
H H38B 0.2695 0.7691 0.6212 0.112 Uiso calc R 1 . .
H H38C 0.5171 0.7926 0.5955 0.112 Uiso calc R 1 . .
C C39 1.115(2) 0.8034(4) 0.80296(16) 0.082(3) Uani d . 1 . .
H H39A 1.1537 0.7652 0.8162 0.123 Uiso calc R 1 . .
H H39B 1.0024 0.8342 0.8162 0.123 Uiso calc R 1 . .
H H39C 1.3046 0.8224 0.7962 0.123 Uiso calc R 1 . .
C C40 0.8261(19) 0.7140(3) 0.7071(2) 0.070(2) Uani d . 1 . .
H H40A 0.7537 0.6701 0.7051 0.105 Uiso calc R 1 . .
H H40B 1.0026 0.7148 0.7213 0.105 Uiso calc R 1 . .
H H40C 0.8778 0.7303 0.6851 0.105 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
C2 O1 C10 . . 104.8(4) ?
C1 O2 C10 . . 104.6(5) ?
C16 O3 C19 . . 117.8(5) ?
C17 O4 C20 . . 114.3(5) ?
C21 O5 C30 . . 105.2(5) ?
C22 O6 C30 . . 104.9(5) ?
C36 O7 C39 . . 117.2(5) ?
C37 O8 C40 . . 111.8(5) ?
C6 N1 C18 . . 111.2(5) ?
C6 N1 C7 . . 111.0(5) ?
C18 N1 C7 . . 110.1(5) ?
C26 N2 C27 . . 111.1(4) ?
C26 N2 C38 . . 109.2(5) ?
C27 N2 C38 . . 110.9(5) ?
C2 C1 C9 . . 123.8(5) ?
C2 C1 O2 . . 109.1(4) ?
C9 C1 O2 . . 126.9(5) ?
C3 C2 O1 . . 128.0(5) ?
C3 C2 C1 . . 121.5(5) ?
O1 C2 C1 . . 110.5(5) ?
C2 C3 C4 . . 118.2(5) ?
C2 C3 H3A . . 120.9 ?
C4 C3 H3A . . 120.9 ?
C3 C4 C8 . . 119.4(5) ?
C3 C4 C5 . . 120.0(5) ?
C8 C4 C5 . . 120.6(5) ?
C4 C5 C6 . . 111.7(5) ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 107.9 ?
N1 C6 C5 . . 111.1(5) ?
N1 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
N1 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108 ?
N1 C7 C8 . . 112.0(5) ?
N1 C7 C11 . . 111.1(4) ?
C8 C7 C11 . . 109.2(4) ?
N1 C7 H7A . . 108.1 ?
C8 C7 H7A . . 108.1 ?
C11 C7 H7A . . 108.1 ?
C9 C8 C4 . . 122.1(5) ?
C9 C8 C7 . . 117.3(5) ?
C4 C8 C7 . . 120.7(5) ?
C1 C9 C8 . . 114.9(5) ?
C1 C9 C13 . . 124.5(5) ?
C8 C9 C13 . . 120.6(4) ?
O2 C10 O1 . . 109.0(5) ?
O2 C10 H10A . . 109.9 ?
O1 C10 H10A . . 109.9 ?
O2 C10 H10B . . 109.9 ?
O1 C10 H10B . . 109.9 ?
H10A C10 H10B . . 108.3 ?
C12 C11 C7 . . 110.4(4) ?
C12 C11 H11A . . 109.6 ?
C7 C11 H11A . . 109.6 ?
C12 C11 H11B . . 109.6 ?
C7 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
C17 C12 C13 . . 118.9(5) ?
C17 C12 C11 . . 121.0(5) ?
C13 C12 C11 . . 120.2(5) ?
C14 C13 C12 . . 118.8(5) ?
C14 C13 C9 . . 123.2(5) ?
C12 C13 C9 . . 118.0(5) ?
C15 C14 C13 . . 120.7(5) ?
C15 C14 H14A . . 119.7 ?
C13 C14 H14A . . 119.7 ?
C16 C15 C14 . . 120.8(5) ?
C16 C15 H15A . . 119.6 ?
C14 C15 H15A . . 119.6 ?
C15 C16 O3 . . 125.0(5) ?
C15 C16 C17 . . 119.6(5) ?
O3 C16 C17 . . 115.4(5) ?
O4 C17 C16 . . 120.3(5) ?
O4 C17 C12 . . 118.4(5) ?
C16 C17 C12 . . 121.3(5) ?
N1 C18 H18A . . 109.5 ?
N1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O3 C19 H19A . . 109.5 ?
O3 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O3 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O4 C20 H20A . . 109.5 ?
O4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C29 C21 O5 . . 129.1(5) ?
C29 C21 C22 . . 122.2(6) ?
O5 C21 C22 . . 108.6(5) ?
C23 C22 C21 . . 121.9(6) ?
C23 C22 O6 . . 128.4(6) ?
C21 C22 O6 . . 109.7(6) ?
C22 C23 C24 . . 117.5(5) ?
C22 C23 H23A . . 121.3 ?
C24 C23 H23A . . 121.3 ?
C28 C24 C23 . . 120.9(6) ?
C28 C24 C25 . . 120.2(5) ?
C23 C24 C25 . . 118.9(5) ?
C26 C25 C24 . . 112.4(5) ?
C26 C25 H25A . . 109.1 ?
C24 C25 H25A . . 109.1 ?
C26 C25 H25B . . 109.1 ?
C24 C25 H25B . . 109.1 ?
H25A C25 H25B . . 107.9 ?
N2 C26 C25 . . 110.3(5) ?
N2 C26 H26A . . 109.6 ?
C25 C26 H26A . . 109.6 ?
N2 C26 H26B . . 109.6 ?
C25 C26 H26B . . 109.6 ?
H26A C26 H26B . . 108.1 ?
N2 C27 C31 . . 111.0(4) ?
N2 C27 C28 . . 111.1(4) ?
C31 C27 C28 . . 109.5(4) ?
N2 C27 H27A . . 108.4 ?
C31 C27 H27A . . 108.4 ?
C28 C27 H27A . . 108.4 ?
C24 C28 C29 . . 122.0(5) ?
C24 C28 C27 . . 121.6(5) ?
C29 C28 C27 . . 116.4(4) ?
C21 C29 C28 . . 115.5(5) ?
C21 C29 C33 . . 123.2(5) ?
C28 C29 C33 . . 121.3(4) ?
O6 C30 O5 . . 111.1(5) ?
O6 C30 H30A . . 109.4 ?
O5 C30 H30A . . 109.4 ?
O6 C30 H30B . . 109.4 ?
O5 C30 H30B . . 109.4 ?
H30A C30 H30B . . 108 ?
C32 C31 C27 . . 110.8(4) ?
C32 C31 H31A . . 109.5 ?
C27 C31 H31A . . 109.5 ?
C32 C31 H31B . . 109.5 ?
C27 C31 H31B . . 109.5 ?
H31A C31 H31B . . 108.1 ?
C37 C32 C33 . . 119.2(5) ?
C37 C32 C31 . . 121.5(5) ?
C33 C32 C31 . . 119.3(5) ?
C34 C33 C32 . . 118.7(5) ?
C34 C33 C29 . . 123.7(5) ?
C32 C33 C29 . . 117.6(5) ?
C35 C34 C33 . . 121.3(5) ?
C35 C34 H34A . . 119.4 ?
C33 C34 H34A . . 119.4 ?
C34 C35 C36 . . 119.7(6) ?
C34 C35 H35A . . 120.1 ?
C36 C35 H35A . . 120.1 ?
O7 C36 C37 . . 116.0(5) ?
O7 C36 C35 . . 124.5(5) ?
C37 C36 C35 . . 119.5(5) ?
C36 C37 O8 . . 119.3(5) ?
C36 C37 C32 . . 121.6(5) ?
O8 C37 C32 . . 119.1(5) ?
N2 C38 H38A . . 109.5 ?
N2 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
N2 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
O7 C39 H39A . . 109.5 ?
O7 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
O7 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
O8 C40 H40A . . 109.5 ?
O8 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
O8 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 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 C2 . 1.367(6) ?
O1 C10 . 1.413(9) ?
O2 C1 . 1.390(7) ?
O2 C10 . 1.411(7) ?
O3 C16 . 1.370(6) ?
O3 C19 . 1.407(8) ?
O4 C17 . 1.393(6) ?
O4 C20 . 1.408(8) ?
O5 C21 . 1.386(7) ?
O5 C30 . 1.400(8) ?
O6 C22 . 1.389(7) ?
O6 C30 . 1.380(9) ?
O7 C36 . 1.371(6) ?
O7 C39 . 1.428(8) ?
O8 C37 . 1.385(6) ?
O8 C40 . 1.435(8) ?
N1 C6 . 1.430(8) ?
N1 C18 . 1.472(8) ?
N1 C7 . 1.481(7) ?
N2 C26 . 1.466(7) ?
N2 C27 . 1.472(7) ?
N2 C38 . 1.481(8) ?
C1 C2 . 1.364(7) ?
C1 C9 . 1.390(7) ?
C2 C3 . 1.362(8) ?
C3 C4 . 1.406(8) ?
C3 H3A . 0.93 ?
C4 C8 . 1.412(7) ?
C4 C5 . 1.486(8) ?
C5 C6 . 1.511(9) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.523(7) ?
C7 C11 . 1.528(7) ?
C7 H7A . 0.98 ?
C8 C9 . 1.405(7) ?
C9 C13 . 1.464(7) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 C12 . 1.496(7) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 C17 . 1.403(7) ?
C12 C13 . 1.404(7) ?
C13 C14 . 1.406(7) ?
C14 C15 . 1.390(7) ?
C14 H14A . 0.93 ?
C15 C16 . 1.362(7) ?
C15 H15A . 0.93 ?
C16 C17 . 1.391(8) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 C29 . 1.382(7) ?
C21 C22 . 1.383(9) ?
C22 C23 . 1.354(9) ?
C23 C24 . 1.399(8) ?
C23 H23A . 0.93 ?
C24 C28 . 1.370(7) ?
C24 C25 . 1.529(8) ?
C25 C26 . 1.482(8) ?
C25 H25A . 0.97 ?
C25 H25B . 0.97 ?
C26 H26A . 0.97 ?
C26 H26B . 0.97 ?
C27 C31 . 1.515(7) ?
C27 C28 . 1.538(7) ?
C27 H27A . 0.98 ?
C28 C29 . 1.410(8) ?
C29 C33 . 1.480(7) ?
C30 H30A . 0.97 ?
C30 H30B . 0.97 ?
C31 C32 . 1.506(7) ?
C31 H31A . 0.97 ?
C31 H31B . 0.97 ?
C32 C37 . 1.391(7) ?
C32 C33 . 1.409(7) ?
C33 C34 . 1.400(8) ?
C34 C35 . 1.386(8) ?
C34 H34A . 0.93 ?
C35 C36 . 1.394(8) ?
C35 H35A . 0.93 ?
C36 C37 . 1.381(8) ?
C38 H38A . 0.96 ?
C38 H38B . 0.96 ?
C38 H38C . 0.96 ?
C39 H39A . 0.96 ?
C39 H39B . 0.96 ?
C39 H39C . 0.96 ?
C40 H40A . 0.96 ?
C40 H40B . 0.96 ?
C40 H40C . 0.96 ?
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
C10 O2 C1 C2 . . . . -8.6(8) ?
C10 O2 C1 C9 . . . . 176.2(7) ?
C10 O1 C2 C3 . . . . -172.4(7) ?
C10 O1 C2 C1 . . . . 7.9(8) ?
C9 C1 C2 C3 . . . . -3.8(10) ?
O2 C1 C2 C3 . . . . -179.3(6) ?
C9 C1 C2 O1 . . . . 175.9(6) ?
O2 C1 C2 O1 . . . . 0.4(7) ?
O1 C2 C3 C4 . . . . -179.5(6) ?
C1 C2 C3 C4 . . . . 0.2(10) ?
C2 C3 C4 C8 . . . . 2.3(9) ?
C2 C3 C4 C5 . . . . -179.2(6) ?
C3 C4 C5 C6 . . . . 163.8(6) ?
C8 C4 C5 C6 . . . . -17.8(8) ?
C18 N1 C6 C5 . . . . 169.7(6) ?
C7 N1 C6 C5 . . . . -67.3(7) ?
C4 C5 C6 N1 . . . . 50.5(8) ?
C6 N1 C7 C8 . . . . 48.1(6) ?
C18 N1 C7 C8 . . . . 171.7(5) ?
C6 N1 C7 C11 . . . . 170.5(5) ?
C18 N1 C7 C11 . . . . -65.9(6) ?
C3 C4 C8 C9 . . . . -1.3(9) ?
C5 C4 C8 C9 . . . . -179.8(6) ?
C3 C4 C8 C7 . . . . 179.9(5) ?
C5 C4 C8 C7 . . . . 1.4(8) ?
N1 C7 C8 C9 . . . . 165.5(5) ?
C11 C7 C8 C9 . . . . 42.0(7) ?
N1 C7 C8 C4 . . . . -15.6(7) ?
C11 C7 C8 C4 . . . . -139.1(5) ?
C2 C1 C9 C8 . . . . 4.6(9) ?
O2 C1 C9 C8 . . . . 179.2(5) ?
C2 C1 C9 C13 . . . . -173.5(5) ?
O2 C1 C9 C13 . . . . 1.1(10) ?
C4 C8 C9 C1 . . . . -2.0(8) ?
C7 C8 C9 C1 . . . . 176.8(5) ?
C4 C8 C9 C13 . . . . 176.2(5) ?
C7 C8 C9 C13 . . . . -4.9(7) ?
C1 O2 C10 O1 . . . . 13.5(8) ?
C2 O1 C10 O2 . . . . -13.3(8) ?
N1 C7 C11 C12 . . . . -179.0(4) ?
C8 C7 C11 C12 . . . . -55.0(6) ?
C7 C11 C12 C17 . . . . -146.2(5) ?
C7 C11 C12 C13 . . . . 34.3(7) ?
C17 C12 C13 C14 . . . . 2.2(7) ?
C11 C12 C13 C14 . . . . -178.3(5) ?
C17 C12 C13 C9 . . . . -176.2(5) ?
C11 C12 C13 C9 . . . . 3.3(7) ?
C1 C9 C13 C14 . . . . -19.7(8) ?
C8 C9 C13 C14 . . . . 162.3(5) ?
C1 C9 C13 C12 . . . . 158.6(6) ?
C8 C9 C13 C12 . . . . -19.4(7) ?
C12 C13 C14 C15 . . . . -2.0(8) ?
C9 C13 C14 C15 . . . . 176.3(5) ?
C13 C14 C15 C16 . . . . 0.6(9) ?
C14 C15 C16 O3 . . . . -178.5(5) ?
C14 C15 C16 C17 . . . . 0.5(9) ?
C19 O3 C16 C15 . . . . -1.5(9) ?
C19 O3 C16 C17 . . . . 179.5(6) ?
C20 O4 C17 C16 . . . . -74.0(7) ?
C20 O4 C17 C12 . . . . 107.8(6) ?
C15 C16 C17 O4 . . . . -178.4(5) ?
O3 C16 C17 O4 . . . . 0.6(8) ?
C15 C16 C17 C12 . . . . -0.3(8) ?
O3 C16 C17 C12 . . . . 178.8(5) ?
C13 C12 C17 O4 . . . . 177.1(5) ?
C11 C12 C17 O4 . . . . -2.4(8) ?
C13 C12 C17 C16 . . . . -1.1(8) ?
C11 C12 C17 C16 . . . . 179.4(5) ?
C30 O5 C21 C29 . . . . -174.6(9) ?
C30 O5 C21 C22 . . . . 2.0(11) ?
C29 C21 C22 C23 . . . . -1.8(13) ?
O5 C21 C22 C23 . . . . -178.7(8) ?
C29 C21 C22 O6 . . . . 179.1(7) ?
O5 C21 C22 O6 . . . . 2.2(10) ?
C30 O6 C22 C23 . . . . 175.5(11) ?
C30 O6 C22 C21 . . . . -5.4(11) ?
C21 C22 C23 C24 . . . . 1.5(13) ?
O6 C22 C23 C24 . . . . -179.6(8) ?
C22 C23 C24 C28 . . . . -0.5(11) ?
C22 C23 C24 C25 . . . . 178.4(7) ?
C28 C24 C25 C26 . . . . -17.2(9) ?
C23 C24 C25 C26 . . . . 163.9(6) ?
C27 N2 C26 C25 . . . . -67.8(7) ?
C38 N2 C26 C25 . . . . 169.5(6) ?
C24 C25 C26 N2 . . . . 48.9(8) ?
C26 N2 C27 C31 . . . . 172.1(5) ?
C38 N2 C27 C31 . . . . -66.2(6) ?
C26 N2 C27 C28 . . . . 50.0(6) ?
C38 N2 C27 C28 . . . . 171.7(5) ?
C23 C24 C28 C29 . . . . -0.3(9) ?
C25 C24 C28 C29 . . . . -179.1(6) ?
C23 C24 C28 C27 . . . . -179.4(6) ?
C25 C24 C28 C27 . . . . 1.8(9) ?
N2 C27 C28 C24 . . . . -17.9(7) ?
C31 C27 C28 C24 . . . . -140.8(5) ?
N2 C27 C28 C29 . . . . 163.0(5) ?
C31 C27 C28 C29 . . . . 40.0(7) ?
O5 C21 C29 C28 . . . . 177.2(7) ?
C22 C21 C29 C28 . . . . 1.0(10) ?
O5 C21 C29 C33 . . . . -1.6(12) ?
C22 C21 C29 C33 . . . . -177.8(7) ?
C24 C28 C29 C21 . . . . 0.0(9) ?
C27 C28 C29 C21 . . . . 179.2(6) ?
C24 C28 C29 C33 . . . . 178.8(6) ?
C27 C28 C29 C33 . . . . -2.0(8) ?
C22 O6 C30 O5 . . . . 6.8(14) ?
C21 O5 C30 O6 . . . . -5.5(14) ?
N2 C27 C31 C32 . . . . -179.4(4) ?
C28 C27 C31 C32 . . . . -56.4(6) ?
C27 C31 C32 C37 . . . . -142.4(5) ?
C27 C31 C32 C33 . . . . 37.6(7) ?
C37 C32 C33 C34 . . . . 1.6(8) ?
C31 C32 C33 C34 . . . . -178.4(5) ?
C37 C32 C33 C29 . . . . -179.1(5) ?
C31 C32 C33 C29 . . . . 0.9(7) ?
C21 C29 C33 C34 . . . . -22.0(9) ?
C28 C29 C33 C34 . . . . 159.3(6) ?
C21 C29 C33 C32 . . . . 158.8(6) ?
C28 C29 C33 C32 . . . . -19.9(8) ?
C32 C33 C34 C35 . . . . -3.3(9) ?
C29 C33 C34 C35 . . . . 177.6(6) ?
C33 C34 C35 C36 . . . . 2.1(10) ?
C39 O7 C36 C37 . . . . -176.0(6) ?
C39 O7 C36 C35 . . . . 3.4(10) ?
C34 C35 C36 O7 . . . . -178.5(6) ?
C34 C35 C36 C37 . . . . 0.8(10) ?
O7 C36 C37 O8 . . . . -0.1(8) ?
C35 C36 C37 O8 . . . . -179.5(6) ?
O7 C36 C37 C32 . . . . 177.0(5) ?
C35 C36 C37 C32 . . . . -2.4(9) ?
C40 O8 C37 C36 . . . . -80.1(7) ?
C40 O8 C37 C32 . . . . 102.8(6) ?
C33 C32 C37 C36 . . . . 1.2(8) ?
C31 C32 C37 C36 . . . . -178.8(5) ?
C33 C32 C37 O8 . . . . 178.2(5) ?
C31 C32 C37 O8 . . . . -1.8(8) ?
