#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017485.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_2017485
loop_
_publ_author_name
'Sridhar, B.'
'Ravikumar, K.'
'Krishnan, Harihara'
'Singh, A. N.'
_publ_section_title
;
 Multicomponent crystals of erlotinib
;
_journal_coeditor_code           SF3120
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o33
_journal_page_last               o38
_journal_paper_doi               10.1107/S0108270109052470
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H23 N3 O4, 0.5C4 H4 O4, 2H2 O'
_chemical_formula_moiety         'C22 H23 N3 O4, 0.5(C4 H4 O4), 2(H2 O)'
_chemical_formula_sum            'C24 H29 N3 O8'
_chemical_formula_weight         487.50
_chemical_name_common
'Erlotinib fumaric acid hemisolvate  dihydrate'
_chemical_name_systematic
;
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine fumaric
acid hemisolvate dihydrate
;
_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                108.916(5)
_cell_angle_beta                 106.673(5)
_cell_angle_gamma                101.909(5)
_cell_formula_units_Z            2
_cell_length_a                   7.967(2)
_cell_length_b                   13.248(4)
_cell_length_c                   13.745(4)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.68
_cell_volume                     1240.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12036
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4364
_refine_ls_number_restraints     56
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0535
_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)+(0.0633P)²+0.2675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                3501
_reflns_number_total             4364
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3120.cif
_cod_data_source_block           III
_cod_database_code               2017485
_cod_database_fobs_code          2017485
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
C C1 0.2800(3) 0.44849(18) 0.56122(17) 0.0551(5) Uani d . 1 . .
H H1 0.3265 0.4260 0.6179 0.066 Uiso calc R 1 . .
C C2 0.3112(3) 0.58402(16) 0.49437(15) 0.0484(5) Uani d . 1 . .
C C3 0.1450(3) 0.51298(16) 0.39735(15) 0.0458(4) Uani d . 1 . .
C C4 0.0631(3) 0.54320(16) 0.31014(16) 0.0496(5) Uani d . 1 . .
H H4 0.1194 0.6130 0.3120 0.060 Uiso calc R 1 . .
C C5 -0.0975(3) 0.47109(16) 0.22336(16) 0.0476(5) Uani d . 1 . .
C C6 -0.1837(3) 0.36345(16) 0.21897(15) 0.0467(5) Uani d . 1 . .
C C7 -0.1073(3) 0.33366(16) 0.30337(16) 0.0492(5) Uani d . 1 . .
H H7 -0.1644 0.2638 0.3012 0.059 Uiso calc R 1 . .
C C8 0.0572(3) 0.40835(16) 0.39349(15) 0.0458(4) Uani d . 1 . .
C C12 -0.4317(3) 0.18723(17) 0.11728(17) 0.0555(5) Uani d . 1 . .
H H12A -0.4733 0.1932 0.1781 0.067 Uiso calc R 1 . .
H H12B -0.3468 0.1443 0.1197 0.067 Uiso calc R 1 . .
C C13 -0.5933(3) 0.12983(18) 0.00898(18) 0.0593(5) Uani d . 1 . .
H H13A -0.6699 0.0602 0.0048 0.071 Uiso calc R 1 . .
H H13B -0.6683 0.1782 0.0024 0.071 Uiso calc R 1 . .
C C14 -0.6716(4) 0.0597(3) -0.1849(2) 0.0907(8) Uani d . 1 . .
H H14A -0.7614 -0.0065 -0.1934 0.136 Uiso calc R 1 . .
H H14B -0.6203 0.0397 -0.2408 0.136 Uiso calc R 1 . .
H H14C -0.7305 0.1145 -0.1928 0.136 Uiso calc R 1 . .
C C9 -0.1095(3) 0.59846(18) 0.13531(18) 0.0638(6) Uani d . 1 . .
H H9A 0.0111 0.6038 0.1307 0.077 Uiso calc R 1 . .
H H9B -0.0932 0.6599 0.2030 0.077 Uiso calc R 1 . .
C C10 -0.2369(3) 0.6057(2) 0.03653(19) 0.0663(6) Uani d . 1 . .
H H10A -0.3587 0.5967 0.0399 0.080 Uiso calc R 1 . .
H H10B -0.1900 0.6792 0.0364 0.080 Uiso calc R 1 . .
C C11 -0.3634(4) 0.5249(2) -0.1587(2) 0.0797(7) Uani d . 1 . .
H H11A -0.4837 0.5224 -0.1569 0.120 Uiso calc R 1 . .
H H11B -0.3760 0.4613 -0.2223 0.120 Uiso calc R 1 . .
H H11C -0.3072 0.5936 -0.1636 0.120 Uiso calc R 1 . .
C C15 0.5458(3) 0.77727(17) 0.59997(17) 0.0553(5) Uani d . 1 . .
C C16 0.5613(3) 0.88594(19) 0.6070(2) 0.0713(6) Uani d . 1 . .
H H16 0.4797 0.8964 0.5504 0.086 Uiso calc R 1 . .
C C17 0.6960(4) 0.9783(2) 0.6969(2) 0.0823(8) Uani d . 1 . .
H H17 0.7052 1.0506 0.7004 0.099 Uiso calc R 1 . .
C C18 0.8174(3) 0.9643(2) 0.7817(2) 0.0756(7) Uani d . 1 . .
H H18 0.9070 1.0270 0.8428 0.091 Uiso calc R 1 . .
C C19 0.8060(3) 0.85712(19) 0.77568(17) 0.0593(6) Uani d . 1 . .
C C20 0.6707(3) 0.76300(18) 0.68390(16) 0.0543(5) Uani d . 1 . .
H H20 0.6646 0.6906 0.6792 0.065 Uiso calc R 1 . .
C C21 0.9283(3) 0.8393(2) 0.86379(19) 0.0658(6) Uani d . 1 . .
C C22 1.0233(4) 0.8218(2) 0.9342(2) 0.0820(8) Uani d . 1 . .
H H22 1.0990 0.8078 0.9903 0.098 Uiso calc R 1 . .
N N1 0.1286(2) 0.37666(14) 0.47802(13) 0.0524(4) Uani d . 1 . .
N N2 0.3760(2) 0.55060(14) 0.57453(13) 0.0552(4) Uani d . 1 . .
N N3 0.4026(3) 0.68781(15) 0.50581(15) 0.0588(5) Uani d . 1 . .
O O1 -0.34075(18) 0.29763(11) 0.12739(11) 0.0546(4) Uani d . 1 . .
O O2 -0.5279(2) 0.10611(14) -0.07815(12) 0.0694(4) Uani d . 1 . .
O O3 -0.19004(18) 0.49268(11) 0.13647(11) 0.0571(4) Uani d . 1 . .
O O4 -0.2505(2) 0.52116(15) -0.06071(13) 0.0739(5) Uani d . 1 . .
H H3N 0.366(3) 0.7032(18) 0.4514(18) 0.058(6) Uiso d . 1 . .
O O5 -0.049(2) 0.1910(14) 0.4751(14) 0.094(3) Uani d PDU 0.55(2) A 1
O O6 0.210(2) 0.2101(11) 0.6014(15) 0.115(4) Uani d PDU 0.55(2) A 1
C C23 0.0506(17) 0.1556(12) 0.5382(14) 0.080(3) Uani d PDU 0.55(2) A 1
C C24 -0.0502(17) 0.0355(9) 0.5190(15) 0.095(3) Uani d PDU 0.55(2) . 1
H H24 -0.1588 0.0124 0.5303 0.114 Uiso calc PR 0.55(2) A 1
O O51 -0.003(3) 0.1757(14) 0.4677(15) 0.092(4) Uani d PDU 0.45(2) A 2
O O61 0.233(3) 0.2406(13) 0.6283(14) 0.105(3) Uani d PDU 0.45(2) A 2
C C231 0.108(3) 0.1610(13) 0.5486(17) 0.104(7) Uani d PDU 0.45(2) A 2
C C241 0.057(4) 0.0461(8) 0.5511(7) 0.129(6) Uani d PDU 0.45(2) . 2
H H241 0.0986 0.0365 0.6169 0.155 Uiso calc PR 0.45(2) A 2
H H5O 0.033(5) 0.256(3) 0.476(3) 0.137(13) Uiso d . 1 . .
O O1W -0.2816(3) 0.2842(2) -0.09821(16) 0.0854(6) Uani d . 1 . .
H H1W -0.353(5) 0.249(3) -0.078(3) 0.102 Uiso d . 1 . .
H H2W -0.279(5) 0.352(3) -0.074(3) 0.103 Uiso d . 1 . .
O O2W 0.4029(4) 0.77270(19) 0.3289(2) 0.0933(7) Uani d . 1 . .
H H3W 0.361(5) 0.753(3) 0.260(3) 0.112 Uiso d . 1 . .
H H4W 0.518(7) 0.779(4) 0.347(4) 0.119 Uiso d . 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
N1 C1 N2 . . 127.57(18) ?
N1 C1 H1 . . 116.2 ?
N2 C1 H1 . . 116.2 ?
N2 C2 N3 . . 118.73(18) ?
N2 C2 C3 . . 121.38(18) ?
N3 C2 C3 . . 119.88(17) ?
C8 C3 C4 . . 118.71(17) ?
C8 C3 C2 . . 116.10(17) ?
C4 C3 C2 . . 125.14(18) ?
C5 C4 C3 . . 120.65(18) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 O3 . . 125.43(18) ?
C4 C5 C6 . . 120.17(17) ?
O3 C5 C6 . . 114.40(16) ?
O1 C6 C7 . . 125.14(17) ?
O1 C6 C5 . . 115.04(16) ?
C7 C6 C5 . . 119.82(17) ?
C6 C7 C8 . . 120.08(17) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
N1 C8 C3 . . 120.83(17) ?
N1 C8 C7 . . 118.63(17) ?
C3 C8 C7 . . 120.54(17) ?
O1 C12 C13 . . 107.70(16) ?
O1 C12 H12A . . 110.2 ?
C13 C12 H12A . . 110.2 ?
O1 C12 H12B . . 110.2 ?
C13 C12 H12B . . 110.2 ?
H12A C12 H12B . . 108.5 ?
O2 C13 C12 . . 109.01(16) ?
O2 C13 H13A . . 109.9 ?
C12 C13 H13A . . 109.9 ?
O2 C13 H13B . . 109.9 ?
C12 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
O3 C9 C10 . . 107.79(17) ?
O3 C9 H9A . . 110.1 ?
C10 C9 H9A . . 110.1 ?
O3 C9 H9B . . 110.1 ?
C10 C9 H9B . . 110.1 ?
H9A C9 H9B . . 108.5 ?
O4 C10 C9 . . 109.78(18) ?
O4 C10 H10A . . 109.7 ?
C9 C10 H10A . . 109.7 ?
O4 C10 H10B . . 109.7 ?
C9 C10 H10B . . 109.7 ?
H10A C10 H10B . . 108.2 ?
O4 C11 H11A . . 109.5 ?
O4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C20 C15 C16 . . 118.9(2) ?
C20 C15 N3 . . 124.16(19) ?
C16 C15 N3 . . 116.9(2) ?
C17 C16 C15 . . 120.7(2) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C16 C17 C18 . . 120.4(2) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C19 . . 119.8(2) ?
C17 C18 H18 . . 120.1 ?
C19 C18 H18 . . 120.1 ?
C18 C19 C20 . . 120.0(2) ?
C18 C19 C21 . . 121.4(2) ?
C20 C19 C21 . . 118.7(2) ?
C15 C20 C19 . . 120.2(2) ?
C15 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C22 C21 C19 . . 177.9(3) ?
C21 C22 H22 . . 180.0 ?
C1 N1 C8 . . 117.16(17) ?
C2 N2 C1 . . 116.97(17) ?
C2 N3 C15 . . 129.22(19) ?
C2 N3 H3N . . 116.3(15) ?
C15 N3 H3N . . 114.3(15) ?
C6 O1 C12 . . 117.56(15) ?
C13 O2 C14 . . 113.15(18) ?
C5 O3 C9 . . 117.08(15) ?
C10 O4 C11 . . 113.38(18) ?
C23 O5 H5O . . 107(3) ?
O6 C23 O5 . . 122.9(12) ?
O6 C23 C24 . . 124.8(10) ?
O5 C23 C24 . . 112.2(10) ?
C24 C24 C23 2_556 . 108.4(10) ?
C24 C24 H24 2_556 . 125.8 ?
C23 C24 H24 . . 125.8 ?
C231 O51 H5O . . 113(2) ?
O61 C231 O51 . . 121.5(14) ?
O61 C231 C241 . . 120.1(13) ?
O51 C231 C241 . . 117.6(12) ?
C241 C241 C231 2_556 . 116.8(11) ?
C241 C241 H241 2_556 . 121.6 ?
C231 C241 H241 . . 121.6 ?
H1W O1W H2W . . 108(3) ?
H3W O2W H4W . . 105(4) ?
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
C1 N1 . 1.303(3) ?
C1 N2 . 1.334(3) ?
C1 H1 . 0.9300 ?
C2 N2 . 1.327(2) ?
C2 N3 . 1.351(3) ?
C2 C3 . 1.441(3) ?
C3 C8 . 1.394(3) ?
C3 C4 . 1.412(3) ?
C4 C5 . 1.361(3) ?
C4 H4 . 0.9300 ?
C5 O3 . 1.362(2) ?
C5 C6 . 1.423(3) ?
C6 O1 . 1.358(2) ?
C6 C7 . 1.365(3) ?
C7 C8 . 1.403(3) ?
C7 H7 . 0.9300 ?
C8 N1 . 1.373(2) ?
C12 O1 . 1.434(2) ?
C12 C13 . 1.488(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 O2 . 1.409(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 O2 . 1.415(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C9 O3 . 1.423(2) ?
C9 C10 . 1.489(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 O4 . 1.395(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O4 . 1.411(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C15 C20 . 1.385(3) ?
C15 C16 . 1.388(3) ?
C15 N3 . 1.408(3) ?
C16 C17 . 1.376(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.376(3) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.377(3) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.397(3) ?
C19 C21 . 1.441(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.166(3) ?
C22 H22 . 0.9300 ?
N3 H3N . 0.83(2) ?
O5 C23 . 1.273(11) ?
O5 H5O . 0.96(4) ?
O6 C23 . 1.214(11) ?
C23 C24 . 1.525(11) ?
C24 C24 2_556 1.424(13) ?
C24 H24 . 0.9300 ?
O51 C231 . 1.303(13) ?
O51 H5O . 1.01(4) ?
O61 C231 . 1.223(14) ?
C231 C241 . 1.507(13) ?
C241 C241 2_556 1.409(16) ?
C241 H241 . 0.9300 ?
O1W H1W . 0.83(4) ?
O1W H2W . 0.85(4) ?
O2W H3W . 0.83(4) ?
O2W H4W . 0.86(5) ?
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
N3 H3N O2W . 0.83(2) 2.22(2) 2.993(3) 155(2)
O5 H5O N1 . 0.96(4) 1.60(4) 2.560(3) 166(4)
O1W H1W O2 . 0.83(4) 2.10(4) 2.884(3) 157(3)
O1W H2W O4 . 0.85(4) 2.14(4) 2.956(3) 161(4)
O2W H3W O1W 2_565 0.83(4) 1.99(4) 2.819(3) 175(3)
O2W H4W O6 2_666 0.86(5) 2.03(6) 2.889(17) 176(5)
C9 H9A O1W 2_565 0.97 2.59 3.436(4) 146
C20 H20 N2 . 0.93 2.33 2.863(4) 116
C22 H22 O1W 2_666 0.93 2.54 3.444(4) 164
C12 H12A Cg3 2_667 0.97 2.76 3.642(2) 151
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 C2 C3 C8 . . . . 0.3(3) ?
N3 C2 C3 C8 . . . . -178.57(17) ?
N2 C2 C3 C4 . . . . 177.75(18) ?
N3 C2 C3 C4 . . . . -1.1(3) ?
C8 C3 C4 C5 . . . . -0.7(3) ?
C2 C3 C4 C5 . . . . -178.10(18) ?
C3 C4 C5 O3 . . . . 178.50(17) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
C4 C5 C6 O1 . . . . -178.56(16) ?
O3 C5 C6 O1 . . . . 2.1(2) ?
C4 C5 C6 C7 . . . . 1.6(3) ?
O3 C5 C6 C7 . . . . -177.77(16) ?
O1 C6 C7 C8 . . . . 179.23(17) ?
C5 C6 C7 C8 . . . . -0.9(3) ?
C4 C3 C8 N1 . . . . -178.03(16) ?
C2 C3 C8 N1 . . . . -0.4(3) ?
C4 C3 C8 C7 . . . . 1.4(3) ?
C2 C3 C8 C7 . . . . 178.99(16) ?
C6 C7 C8 N1 . . . . 178.84(16) ?
C6 C7 C8 C3 . . . . -0.6(3) ?
O1 C12 C13 O2 . . . . 69.0(2) ?
O3 C9 C10 O4 . . . . -63.4(2) ?
C20 C15 C16 C17 . . . . -1.3(4) ?
N3 C15 C16 C17 . . . . 179.3(2) ?
C15 C16 C17 C18 . . . . -0.3(4) ?
C16 C17 C18 C19 . . . . 1.0(4) ?
C17 C18 C19 C20 . . . . -0.3(3) ?
C17 C18 C19 C21 . . . . -178.8(2) ?
C16 C15 C20 C19 . . . . 2.0(3) ?
N3 C15 C20 C19 . . . . -178.55(19) ?
C18 C19 C20 C15 . . . . -1.3(3) ?
C21 C19 C20 C15 . . . . 177.28(19) ?
N2 C1 N1 C8 . . . . -0.2(3) ?
C3 C8 N1 C1 . . . . 0.3(3) ?
C7 C8 N1 C1 . . . . -179.06(17) ?
N3 C2 N2 C1 . . . . 178.75(18) ?
C3 C2 N2 C1 . . . . -0.1(3) ?
N1 C1 N2 C2 . . . . 0.1(3) ?
N2 C2 N3 C15 . . . . -11.0(3) ?
C3 C2 N3 C15 . . . . 167.90(19) ?
C20 C15 N3 C2 . . . . 27.6(3) ?
C16 C15 N3 C2 . . . . -152.9(2) ?
C7 C6 O1 C12 . . . . -1.3(3) ?
C5 C6 O1 C12 . . . . 178.78(16) ?
C13 C12 O1 C6 . . . . -177.36(15) ?
C12 C13 O2 C14 . . . . -175.09(19) ?
C4 C5 O3 C9 . . . . 1.5(3) ?
C6 C5 O3 C9 . . . . -179.18(17) ?
C10 C9 O3 C5 . . . . -177.68(17) ?
C9 C10 O4 C11 . . . . -177.61(19) ?
O6 C23 C24 C24 . . . 2_556 -59(3) ?
O5 C23 C24 C24 . . . 2_556 118(2) ?
O61 C231 C241 C241 . . . 2_556 -166(4) ?
O51 C231 C241 C241 . . . 2_556 24(4) ?
