#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/74/2017483.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_2017483
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, H2 O'
_chemical_formula_moiety         'C22 H23 N3 O4, H2 O'
_chemical_formula_sum            'C22 H25 N3 O5'
_chemical_formula_weight         411.45
_chemical_name_common            'Erlotinib monohydrate'
_chemical_name_systematic
;
N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)quinazolin-4-amine
monohydrate
;
_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                98.705(2)
_cell_angle_beta                 108.738(2)
_cell_angle_gamma                111.873(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0227(10)
_cell_length_b                   10.4548(11)
_cell_length_c                   13.2014(14)
_cell_measurement_reflns_used    5228
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.21
_cell_volume                     1041.1(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10097
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.1660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3169
_reflns_number_total             3666
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3120.cif
_cod_data_source_block           I
_cod_original_cell_volume        1041.05(19)
_cod_database_code               2017483
_cod_database_fobs_code          2017483
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 0.75210(19) 1.01314(16) 1.11192(14) 0.0571(4) Uani d . 1 . .
H H1 0.7162 1.0809 1.1345 0.068 Uiso calc R 1 . .
C C2 0.98121(17) 0.96540(14) 1.11893(11) 0.0435(3) Uani d . 1 . .
C C3 0.85915(16) 0.82402(14) 1.04030(11) 0.0413(3) Uani d . 1 . .
C C4 0.90549(17) 0.72113(14) 0.99468(11) 0.0448(3) Uani d . 1 . .
H H4 1.0231 0.7435 1.0151 0.054 Uiso calc R 1 . .
C C5 0.77919(17) 0.58952(14) 0.92095(12) 0.0458(3) Uani d . 1 . .
C C6 0.59847(17) 0.55081(14) 0.89195(11) 0.0450(3) Uani d . 1 . .
C C7 0.55111(17) 0.64950(15) 0.93433(11) 0.0467(3) Uani d . 1 . .
H H7 0.4332 0.6250 0.9148 0.056 Uiso calc R 1 . .
C C8 0.68000(17) 0.78811(14) 1.00743(11) 0.0436(3) Uani d . 1 . .
C C9 0.95945(19) 0.52836(17) 0.84211(14) 0.0584(4) Uani d . 1 . .
H H9B 1.0536 0.5198 0.8974 0.070 Uiso calc R 1 . .
H H9A 1.0007 0.6283 0.8422 0.070 Uiso calc R 1 . .
C C10 0.9051(3) 0.4313(2) 0.72896(16) 0.0751(5) Uani d U 1 . .
H H10A 0.8068 0.4366 0.6749 0.090 Uiso calc R 1 . .
H H10B 1.0011 0.4622 0.7058 0.090 Uiso calc R 1 . .
C C11 0.7474(4) 0.1821(3) 0.6302(2) 0.1361(11) Uani d U 1 . .
H H11A 0.7222 0.0885 0.6404 0.204 Uiso calc R 1 . .
H H11B 0.8031 0.1942 0.5791 0.204 Uiso calc R 1 . .
H H11C 0.6402 0.1899 0.6001 0.204 Uiso calc R 1 . .
C C12 0.30426(18) 0.37191(17) 0.77667(13) 0.0591(4) Uani d D 1 . .
H H12A 0.2753 0.4369 0.7381 0.071 Uiso calc R 1 A 1
H H12B 0.2617 0.3679 0.8355 0.071 Uiso calc R 1 A 1
C C13 0.2314(18) 0.2233(8) 0.6960(8) 0.073(3) Uani d PD 0.554(7) B 1
H H13A 0.2869 0.1690 0.7322 0.087 Uiso calc PR 0.554(7) B 1
H H13B 0.1066 0.1718 0.6757 0.087 Uiso calc PR 0.554(7) B 1
O O2 0.2608(13) 0.2329(9) 0.5980(8) 0.077(2) Uani d PD 0.554(7) B 1
C C14 0.2189(9) 0.1003(5) 0.5236(4) 0.122(2) Uani d PD 0.554(7) B 1
H H14A 0.2581 0.1185 0.4654 0.183 Uiso calc PR 0.554(7) B 1
H H14B 0.0943 0.0412 0.4907 0.183 Uiso calc PR 0.554(7) B 1
H H14C 0.2757 0.0508 0.5642 0.183 Uiso calc PR 0.554(7) B 1
C C131 0.196(2) 0.2216(11) 0.6928(11) 0.069(3) Uani d PD 0.446(7) B 2
H H13C 0.2303 0.1539 0.7243 0.083 Uiso calc PR 0.446(7) B 2
H H13D 0.0729 0.1908 0.6767 0.083 Uiso calc PR 0.446(7) B 2
O O21 0.2208(16) 0.2218(13) 0.5925(11) 0.085(3) Uani d PD 0.446(7) B 2
C C141 0.3550(8) 0.1845(7) 0.5906(5) 0.0836(18) Uani d PD 0.446(7) B 2
H H14D 0.3673 0.1874 0.5213 0.125 Uiso calc PR 0.446(7) B 2
H H14E 0.3257 0.0886 0.5966 0.125 Uiso calc PR 0.446(7) B 2
H H14F 0.4633 0.2521 0.6526 0.125 Uiso calc PR 0.446(7) B 2
C C15 1.30051(17) 1.13446(14) 1.23772(11) 0.0449(3) Uani d . 1 . .
C C16 1.2899(2) 1.25678(16) 1.28597(12) 0.0535(4) Uani d . 1 . .
H H16 1.1814 1.2566 1.2684 0.064 Uiso calc R 1 . .
C C17 1.4412(2) 1.37874(17) 1.36015(13) 0.0616(4) Uani d . 1 . .
H H17 1.4330 1.4604 1.3913 0.074 Uiso calc R 1 . .
C C18 1.6036(2) 1.38200(16) 1.38890(12) 0.0602(4) Uani d . 1 . .
H H18 1.7037 1.4647 1.4394 0.072 Uiso calc R 1 . .
C C19 1.61654(18) 1.26067(16) 1.34183(12) 0.0534(4) Uani d . 1 . .
C C20 1.46473(18) 1.13763(15) 1.26602(12) 0.0502(3) Uani d . 1 . .
H H20 1.4734 1.0566 1.2339 0.060 Uiso calc R 1 . .
C C21 1.7847(2) 1.26054(18) 1.37171(14) 0.0641(4) Uani d . 1 . .
C C22 1.9222(2) 1.2602(2) 1.39920(19) 0.0876(6) Uani d . 1 . .
H H22 2.0309 1.2600 1.4209 0.105 Uiso calc R 1 . .
N N1 0.62628(15) 0.88598(13) 1.04533(11) 0.0531(3) Uani d . 1 . .
N N2 0.92649(15) 1.05919(13) 1.15217(11) 0.0535(3) Uani d . 1 . .
N N3 1.15649(14) 1.00449(13) 1.15992(10) 0.0470(3) Uani d . 1 . .
H H3N 1.1848(19) 0.9423(17) 1.1363(13) 0.050(4) Uiso d . 1 . .
O O1 0.48834(12) 0.41491(10) 0.82075(8) 0.0555(3) Uani d . 1 B .
O O3 0.81022(14) 0.48559(11) 0.86847(11) 0.0688(3) Uani d . 1 . .
O O4 0.8565(2) 0.28741(14) 0.73162(11) 0.0847(4) Uani d U 1 . .
O O1W 1.32150(16) 0.80957(14) 1.09388(13) 0.0706(4) Uani d . 1 . .
H H1W 1.316(3) 0.745(3) 1.120(2) 0.085 Uiso d . 1 . .
H H2W 1.405(3) 0.828(2) 1.0738(17) 0.086 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 . . 128.76(13) ?
N1 C1 H1 . . 115.6 ?
N2 C1 H1 . . 115.6 ?
N2 C2 N3 . . 119.37(12) ?
N2 C2 C3 . . 121.15(12) ?
N3 C2 C3 . . 119.49(12) ?
C8 C3 C4 . . 118.78(12) ?
C8 C3 C2 . . 116.14(12) ?
C4 C3 C2 . . 125.08(12) ?
C5 C4 C3 . . 120.43(12) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 O3 . . 124.87(12) ?
C4 C5 C6 . . 120.72(12) ?
O3 C5 C6 . . 114.40(12) ?
O1 C6 C7 . . 126.28(12) ?
O1 C6 C5 . . 114.10(12) ?
C7 C6 C5 . . 119.61(12) ?
C6 C7 C8 . . 120.33(12) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
N1 C8 C7 . . 118.42(12) ?
N1 C8 C3 . . 121.56(12) ?
C7 C8 C3 . . 120.02(12) ?
O3 C9 C10 . . 107.48(13) ?
O3 C9 H9B . . 110.2 ?
C10 C9 H9B . . 110.2 ?
O3 C9 H9A . . 110.2 ?
C10 C9 H9A . . 110.2 ?
H9B C9 H9A . . 108.5 ?
O4 C10 C9 . . 109.79(15) ?
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 ?
O1 C12 C13 . . 101.7(6) ?
O1 C12 C131 . . 113.2(7) ?
O1 C12 H12A . . 111.4 ?
C13 C12 H12A . . 111.4 ?
C131 C12 H12A . . 106.4 ?
O1 C12 H12B . . 111.4 ?
C13 C12 H12B . . 111.4 ?
C131 C12 H12B . . 104.8 ?
H12A C12 H12B . . 109.3 ?
O2 C13 C12 . . 110.8(7) ?
O2 C13 H13A . . 109.5 ?
C12 C13 H13A . . 109.5 ?
O2 C13 H13B . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C14 O2 C13 . . 115.3(6) ?
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 ?
O21 C131 C12 . . 109.8(10) ?
O21 C131 H13C . . 109.7 ?
C12 C131 H13C . . 109.7 ?
O21 C131 H13D . . 109.7 ?
C12 C131 H13D . . 109.7 ?
H13C C131 H13D . . 108.2 ?
C141 O21 C131 . . 112.9(11) ?
O21 C141 H14D . . 109.5 ?
O21 C141 H14E . . 109.5 ?
H14D C141 H14E . . 109.5 ?
O21 C141 H14F . . 109.5 ?
H14D C141 H14F . . 109.5 ?
H14E C141 H14F . . 109.5 ?
C16 C15 C20 . . 118.82(13) ?
C16 C15 N3 . . 125.21(13) ?
C20 C15 N3 . . 115.97(12) ?
C17 C16 C15 . . 119.80(14) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C18 C17 C16 . . 121.56(15) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 119.39(14) ?
C17 C18 H18 . . 120.3 ?
C19 C18 H18 . . 120.3 ?
C18 C19 C20 . . 119.46(14) ?
C18 C19 C21 . . 120.49(13) ?
C20 C19 C21 . . 120.05(14) ?
C15 C20 C19 . . 120.97(14) ?
C15 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C22 C21 C19 . . 178.02(19) ?
C21 C22 H22 . . 180.0 ?
C1 N1 C8 . . 115.44(12) ?
C2 N2 C1 . . 116.78(12) ?
C2 N3 C15 . . 130.25(12) ?
C2 N3 H3N . . 116.0(11) ?
C15 N3 H3N . . 113.7(11) ?
C6 O1 C12 . . 118.19(12) ?
C5 O3 C9 . . 119.26(11) ?
C11 O4 C10 . . 115.55(17) ?
H1W O1W H2W . . 106(2) ?
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 . 1.3075(19) ?
C1 N2 . 1.3457(18) ?
C1 H1 . 0.9300 ?
C2 N2 . 1.3295(18) ?
C2 N3 . 1.3647(17) ?
C2 C3 . 1.4364(19) ?
C3 C8 . 1.4107(18) ?
C3 C4 . 1.4127(19) ?
C4 C5 . 1.3612(19) ?
C4 H4 . 0.9300 ?
C5 O3 . 1.3647(17) ?
C5 C6 . 1.4246(18) ?
C6 O1 . 1.3540(16) ?
C6 C7 . 1.367(2) ?
C7 C8 . 1.408(2) ?
C7 H7 . 0.9300 ?
C8 N1 . 1.3794(18) ?
C9 O3 . 1.4261(18) ?
C9 C10 . 1.483(2) ?
C9 H9B . 0.9700 ?
C9 H9A . 0.9700 ?
C10 O4 . 1.411(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 O4 . 1.368(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 O1 . 1.4293(18) ?
C12 C13 . 1.506(7) ?
C12 C131 . 1.511(8) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 O2 . 1.413(7) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
O2 C14 . 1.410(8) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C131 O21 . 1.413(8) ?
C131 H13C . 0.9700 ?
C131 H13D . 0.9700 ?
O21 C141 . 1.409(9) ?
C141 H14D . 0.9600 ?
C141 H14E . 0.9600 ?
C141 H14F . 0.9600 ?
C15 C16 . 1.391(2) ?
C15 C20 . 1.393(2) ?
C15 N3 . 1.4122(17) ?
C16 C17 . 1.384(2) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.376(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.388(2) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.3962(19) ?
C19 C21 . 1.440(2) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.177(2) ?
C22 H22 . 0.9300 ?
N3 H3N . 0.836(16) ?
O1W H1W . 0.80(2) ?
O1W H2W . 0.85(2) ?
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 O1W . 0.836(16) 2.290(17) 3.1123(18) 167.9(14)
O1W H1W O3 2_767 0.80(2) 2.30(2) 3.0485(18) 156(2)
O1W H2W N1 1_655 0.85(2) 2.03(2) 2.8742(18) 173(2)
C4 H4 O1W . 0.93 2.33 3.248(2) 171
C16 H16 N2 . 0.93 2.27 2.874(2) 122
C20 H20 O1W . 0.93 2.50 3.323(2) 148
C12 H12B Cg2 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 . . . . -4.29(19) ?
N3 C2 C3 C8 . . . . 175.99(11) ?
N2 C2 C3 C4 . . . . 175.60(12) ?
N3 C2 C3 C4 . . . . -4.1(2) ?
C8 C3 C4 C5 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . 179.68(12) ?
C3 C4 C5 O3 . . . . 176.88(13) ?
C3 C4 C5 C6 . . . . -2.6(2) ?
C4 C5 C6 O1 . . . . -177.87(12) ?
O3 C5 C6 O1 . . . . 2.63(18) ?
C4 C5 C6 C7 . . . . 3.2(2) ?
O3 C5 C6 C7 . . . . -176.27(12) ?
O1 C6 C7 C8 . . . . -179.58(12) ?
C5 C6 C7 C8 . . . . -0.8(2) ?
C6 C7 C8 N1 . . . . 177.91(12) ?
C6 C7 C8 C3 . . . . -2.2(2) ?
C4 C3 C8 N1 . . . . -177.28(12) ?
C2 C3 C8 N1 . . . . 2.62(19) ?
C4 C3 C8 C7 . . . . 2.80(19) ?
C2 C3 C8 C7 . . . . -177.30(11) ?
O3 C9 C10 O4 . . . . -63.80(18) ?
O1 C12 C13 O2 . . . . -74.6(10) ?
C131 C12 C13 O2 . . . . 110(5) ?
C12 C13 O2 C14 . . . . 171.8(9) ?
O1 C12 C131 O21 . . . . -70.2(13) ?
C13 C12 C131 O21 . . . . -65(4) ?
C12 C131 O21 C141 . . . . 92.9(14) ?
C20 C15 C16 C17 . . . . 0.3(2) ?
N3 C15 C16 C17 . . . . -179.07(13) ?
C15 C16 C17 C18 . . . . -0.8(2) ?
C16 C17 C18 C19 . . . . 0.5(2) ?
C17 C18 C19 C20 . . . . 0.1(2) ?
C17 C18 C19 C21 . . . . -179.13(14) ?
C16 C15 C20 C19 . . . . 0.3(2) ?
N3 C15 C20 C19 . . . . 179.78(12) ?
C18 C19 C20 C15 . . . . -0.6(2) ?
C21 C19 C20 C15 . . . . 178.70(13) ?
N2 C1 N1 C8 . . . . -3.1(2) ?
C7 C8 N1 C1 . . . . -179.29(13) ?
C3 C8 N1 C1 . . . . 0.8(2) ?
N3 C2 N2 C1 . . . . -177.87(12) ?
C3 C2 N2 C1 . . . . 2.4(2) ?
N1 C1 N2 C2 . . . . 1.6(2) ?
N2 C2 N3 C15 . . . . 1.0(2) ?
C3 C2 N3 C15 . . . . -179.23(12) ?
C16 C15 N3 C2 . . . . -3.3(2) ?
C20 C15 N3 C2 . . . . 177.24(13) ?
C7 C6 O1 C12 . . . . 5.8(2) ?
C5 C6 O1 C12 . . . . -172.97(12) ?
C13 C12 O1 C6 . . . . 175.3(4) ?
C131 C12 O1 C6 . . . . 176.4(6) ?
C4 C5 O3 C9 . . . . -31.4(2) ?
C6 C5 O3 C9 . . . . 148.11(13) ?
C10 C9 O3 C5 . . . . -139.61(15) ?
C9 C10 O4 C11 . . . . 157.4(2) ?
