#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:09:08 +0200 (lun 05 de jul de 2021) $
#$Revision: 267118 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/27/7242719.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242719
loop_
_publ_author_name
'Thorat, Shridhar H.'
'George, Christy P.'
'Shaligram, Parth S.'
'P. R., Suresha'
'Gonnade, Rajesh G.'
_publ_section_title
;
 Polymorphs and hydrates of the anticancer drug erlotinib: X-ray
 crystallography, phase transition and biopharmaceutical studies
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3961
_journal_page_last               3974
_journal_paper_doi               10.1039/D1CE00032B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C22 H23 N3 O4'
_chemical_formula_sum            'C22 H23 N3 O4'
_chemical_formula_weight         393.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-28 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9641(6)
_cell_length_b                   13.0136(5)
_cell_length_c                   11.2102(5)
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      38.68
_cell_measurement_theta_min      2.43
_cell_volume                     1997.38(15)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            61579
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.889
_diffrn_reflns_theta_min         2.425
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Incoatech I\mS HB'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 8987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         20962
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0511
_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)+(0.0888P)²+0.3311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                19979
_reflns_number_total             20962
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00032b2.cif
_cod_data_source_block           ETB_FORM_I
_cod_depositor_comments
'Adding full bibliography for 7242719--7242721.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7242719
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22849(8) 0.67963(8) 0.30326(10) 0.01516(17) Uani 1 1 d . . . . .
O2 O 0.13450(11) 0.75529(13) 0.06087(12) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.28451(8) 0.49693(8) 0.31776(10) 0.01517(18) Uani 1 1 d . . . . .
O4 O 0.15535(8) 0.34574(10) 0.22111(11) 0.01779(19) Uani 1 1 d . . . . .
N1 N 0.50040(9) 0.78747(9) 0.61309(11) 0.01337(18) Uani 1 1 d . . . . .
N2 N 0.60728(9) 0.65942(9) 0.72034(11) 0.01392(18) Uani 1 1 d . . . . .
N3 N 0.58446(9) 0.48635(9) 0.68147(11) 0.01350(18) Uani 1 1 d . . . . .
H3N H 0.550411 0.436791 0.639634 0.016 Uiso 1 1 calc R U . . .
C1 C 0.57671(11) 0.75621(10) 0.69352(13) 0.0151(2) Uani 1 1 d . . . . .
H1 H 0.615091 0.808817 0.738339 0.018 Uiso 1 1 calc R U . . .
C2 C 0.55599(9) 0.58419(10) 0.65633(11) 0.01083(17) Uani 1 1 d . . . . .
C3 C 0.41865(9) 0.53097(10) 0.48731(12) 0.01187(18) Uani 1 1 d . . . . .
H3 H 0.437043 0.460722 0.496909 0.014 Uiso 1 1 calc R U . . .
C4 C 0.33984(9) 0.55945(10) 0.40012(12) 0.01211(19) Uani 1 1 d . . . . .
C5 C 0.30956(9) 0.66490(10) 0.38847(12) 0.01178(18) Uani 1 1 d . . . . .
C6 C 0.36325(10) 0.73950(10) 0.45879(12) 0.01239(19) Uani 1 1 d . . . . .
H6 H 0.344476 0.809615 0.448743 0.015 Uiso 1 1 calc R U . . .
C7 C 0.44656(9) 0.71113(9) 0.54611(11) 0.01074(18) Uani 1 1 d . . . . .
C8 C 0.47253(9) 0.60674(9) 0.56300(11) 0.01037(17) Uani 1 1 d . . . . .
C9 C 0.66705(9) 0.45906(10) 0.77251(12) 0.01199(18) Uani 1 1 d . . . . .
C10 C 0.65228(10) 0.41210(11) 0.87910(12) 0.0147(2) Uani 1 1 d . . . . .
H10 H 0.587812 0.401038 0.891887 0.018 Uiso 1 1 calc R U . . .
C11 C 0.73204(11) 0.38140(12) 0.96681(13) 0.0162(2) Uani 1 1 d . . . . .
H11 H 0.721818 0.349834 1.039688 0.019 Uiso 1 1 calc R U . . .
C12 C 0.82649(11) 0.39666(12) 0.94841(13) 0.0161(2) Uani 1 1 d . . . . .
H12 H 0.880722 0.375934 1.008771 0.019 Uiso 1 1 calc R U . . .
C13 C 0.84164(10) 0.44268(11) 0.84063(13) 0.0140(2) Uani 1 1 d . . . . .
C14 C 0.76128(10) 0.47398(11) 0.75239(13) 0.0139(2) Uani 1 1 d . . . . .
H14 H 0.771130 0.505246 0.679174 0.017 Uiso 1 1 calc R U . . .
C15 C 0.93876(10) 0.45701(12) 0.81859(15) 0.0175(2) Uani 1 1 d . . . . .
C16 C 1.01997(11) 0.47105(14) 0.80075(17) 0.0219(3) Uani 1 1 d . . . . .
H16 H 1.084074 0.482130 0.786663 0.026 Uiso 1 1 calc R U . . .
C17 C 0.19103(10) 0.78209(11) 0.27980(13) 0.0147(2) Uani 1 1 d . . . . .
H17A H 0.242069 0.827983 0.259516 0.018 Uiso 1 1 calc R U . . .
H17B H 0.169183 0.809919 0.352191 0.018 Uiso 1 1 calc R U . . .
C18 C 0.10606(11) 0.77441(12) 0.17371(14) 0.0180(2) Uani 1 1 d . . . . .
H18A H 0.062313 0.718393 0.189748 0.022 Uiso 1 1 calc R U . . .
H18B H 0.068472 0.839355 0.167420 0.022 Uiso 1 1 calc R U . . .
C19 C 0.14282(16) 0.6497(2) 0.03296(18) 0.0314(4) Uani 1 1 d . . . . .
H19A H 0.203607 0.622059 0.081065 0.047 Uiso 1 1 calc R U . . .
H19B H 0.143488 0.642110 -0.053855 0.047 Uiso 1 1 calc R U . . .
H19C H 0.087118 0.611929 0.052387 0.047 Uiso 1 1 calc R U . . .
C20 C 0.31667(10) 0.39339(11) 0.30793(13) 0.0145(2) Uani 1 1 d . . . . .
H20A H 0.310916 0.353452 0.381360 0.017 Uiso 1 1 calc R U . . .
H20B H 0.385606 0.391999 0.298223 0.017 Uiso 1 1 calc R U . . .
C21 C 0.25083(11) 0.34978(11) 0.19715(12) 0.0151(2) Uani 1 1 d . . . . .
H21A H 0.252160 0.393896 0.125554 0.018 Uiso 1 1 calc R U . . .
H21B H 0.272873 0.280013 0.179847 0.018 Uiso 1 1 calc R U . . .
C22 C 0.08468(14) 0.31888(15) 0.11687(17) 0.0255(3) Uani 1 1 d . . . . .
H22A H 0.079154 0.374338 0.056759 0.038 Uiso 1 1 calc R U . . .
H22B H 0.021340 0.308340 0.140187 0.038 Uiso 1 1 calc R U . . .
H22C H 0.104671 0.255401 0.081578 0.038 Uiso 1 1 calc R U . . .
O1' O 0.76938(8) 0.18282(8) 0.43739(11) 0.01570(17) Uani 1 1 d . . . . .
O2' O 0.86897(12) 0.27073(14) 0.24850(14) 0.0299(3) Uani 1 1 d . . . . .
O3' O 0.71264(8) -0.00172(8) 0.42315(11) 0.01590(18) Uani 1 1 d . . . . .
O4' O 0.83842(9) -0.15319(10) 0.37745(12) 0.0199(2) Uani 1 1 d . . . . .
N1' N 0.49517(9) 0.28855(9) 0.61030(12) 0.01399(18) Uani 1 1 d . . . . .
N2' N 0.38954(9) 0.16010(9) 0.66738(12) 0.01489(19) Uani 1 1 d . . . . .
N3' N 0.41488(9) -0.01262(9) 0.64470(12) 0.01418(18) Uani 1 1 d . . . . .
H3'N H 0.450787 -0.062348 0.623380 0.017 Uiso 1 1 calc R U . . .
C1' C 0.41904(11) 0.25709(10) 0.65350(14) 0.0157(2) Uani 1 1 d . . . . .
H1' H 0.379859 0.309665 0.678058 0.019 Uiso 1 1 calc R U . . .
C2' C 0.44183(9) 0.08501(10) 0.63027(12) 0.01143(18) Uani 1 1 d . . . . .
C3' C 0.57922(9) 0.03193(10) 0.52770(12) 0.01224(19) Uani 1 1 d . . . . .
H3' H 0.561470 -0.038481 0.528903 0.015 Uiso 1 1 calc R U . . .
C4' C 0.65775(10) 0.06117(10) 0.47847(12) 0.01272(19) Uani 1 1 d . . . . .
C5' C 0.68753(9) 0.16658(10) 0.48154(12) 0.01222(19) Uani 1 1 d . . . . .
C6' C 0.63313(10) 0.24074(10) 0.52462(12) 0.01264(19) Uani 1 1 d . . . . .
H6' H 0.651345 0.310993 0.523104 0.015 Uiso 1 1 calc R U . . .
C7' C 0.54982(9) 0.21218(9) 0.57130(11) 0.01138(18) Uani 1 1 d . . . . .
C8' C 0.52486(9) 0.10767(9) 0.57671(12) 0.01091(18) Uani 1 1 d . . . . .
C9' C 0.33079(10) -0.03980(10) 0.69296(12) 0.01292(19) Uani 1 1 d . . . . .
C10' C 0.34271(11) -0.09000(12) 0.80459(13) 0.0161(2) Uani 1 1 d . . . . .
H10' H 0.406356 -0.103950 0.849781 0.019 Uiso 1 1 calc R U . . .
C11' C 0.26060(12) -0.11971(12) 0.84971(14) 0.0178(2) Uani 1 1 d . . . . .
H11' H 0.268658 -0.154239 0.925698 0.021 Uiso 1 1 calc R U . . .
C12' C 0.16743(12) -0.09933(12) 0.78477(14) 0.0177(2) Uani 1 1 d . . . . .
H12' H 0.111945 -0.118710 0.816825 0.021 Uiso 1 1 calc R U . . .
C13' C 0.15533(10) -0.05000(11) 0.67154(14) 0.0159(2) Uani 1 1 d . . . . .
C14' C 0.23777(10) -0.02012(11) 0.62598(13) 0.0150(2) Uani 1 1 d . . . . .
H14' H 0.230043 0.013511 0.549468 0.018 Uiso 1 1 calc R U . . .
C15' C 0.06012(11) -0.03061(13) 0.60036(16) 0.0204(3) Uani 1 1 d . . . . .
C16' C -0.01933(13) -0.01231(16) 0.53958(19) 0.0261(3) Uani 1 1 d . . . . .
H16' H -0.081909 0.002114 0.491706 0.031 Uiso 1 1 calc R U . . .
C17' C 0.80607(10) 0.28630(11) 0.43683(13) 0.0156(2) Uani 1 1 d . . . . .
H17C H 0.825172 0.312503 0.521065 0.019 Uiso 1 1 calc R U . . .
H17D H 0.755295 0.332195 0.391005 0.019 Uiso 1 1 calc R U . . .
C18' C 0.89379(11) 0.28274(13) 0.37652(16) 0.0203(3) Uani 1 1 d . . . . .
H18C H 0.931612 0.347045 0.395395 0.024 Uiso 1 1 calc R U . . .
H18D H 0.936362 0.224936 0.411322 0.024 Uiso 1 1 calc R U . . .
C19' C 0.85674(17) 0.1676(2) 0.2089(2) 0.0350(4) Uani 1 1 d . . . . .
H19D H 0.911122 0.126130 0.252367 0.052 Uiso 1 1 calc R U . . .
H19E H 0.855523 0.164377 0.121287 0.052 Uiso 1 1 calc R U . . .
H19F H 0.795094 0.140927 0.225612 0.052 Uiso 1 1 calc R U . . .
C20' C 0.67951(10) -0.10537(11) 0.39897(13) 0.0151(2) Uani 1 1 d . . . . .
H20C H 0.609430 -0.106464 0.360094 0.018 Uiso 1 1 calc R U . . .
H20D H 0.688592 -0.145507 0.475392 0.018 Uiso 1 1 calc R U . . .
C21' C 0.74053(11) -0.14933(11) 0.31467(13) 0.0160(2) Uani 1 1 d . . . . .
H21C H 0.717395 -0.219217 0.288571 0.019 Uiso 1 1 calc R U . . .
H21D H 0.735142 -0.105605 0.241382 0.019 Uiso 1 1 calc R U . . .
C22' C 0.90346(15) -0.17591(16) 0.2991(2) 0.0278(4) Uani 1 1 d . . . . .
H22D H 0.885569 -0.241930 0.258773 0.042 Uiso 1 1 calc R U . . .
H22E H 0.970265 -0.179857 0.346502 0.042 Uiso 1 1 calc R U . . .
H22F H 0.899639 -0.121698 0.237655 0.042 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C17 119.19(11) . . ?
C19 O2 C18 114.54(14) . . ?
C4 O3 C20 118.22(11) . . ?
C21 O4 C22 112.51(13) . . ?
C1 N1 C7 115.60(11) . . ?
C2 N2 C1 116.96(12) . . ?
C2 N3 C9 123.29(11) . . ?
C2 N3 H3N 118.4 . . ?
C9 N3 H3N 118.4 . . ?
N1 C1 N2 128.36(13) . . ?
N1 C1 H1 115.8 . . ?
N2 C1 H1 115.8 . . ?
N2 C2 N3 118.38(11) . . ?
N2 C2 C8 120.97(11) . . ?
N3 C2 C8 120.65(11) . . ?
C4 C3 C8 119.74(11) . . ?
C4 C3 H3 120.1 . . ?
C8 C3 H3 120.1 . . ?
O3 C4 C3 126.47(12) . . ?
O3 C4 C5 113.24(11) . . ?
C3 C4 C5 120.29(11) . . ?
O1 C5 C6 126.49(12) . . ?
O1 C5 C4 113.16(11) . . ?
C6 C5 C4 120.34(11) . . ?
C5 C6 C7 119.59(12) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
N1 C7 C8 121.60(11) . . ?
N1 C7 C6 118.43(11) . . ?
C8 C7 C6 119.97(11) . . ?
C7 C8 C3 119.87(11) . . ?
C7 C8 C2 116.47(11) . . ?
C3 C8 C2 123.63(11) . . ?
C14 C9 C10 120.30(12) . . ?
C14 C9 N3 120.42(12) . . ?
C10 C9 N3 119.19(12) . . ?
C11 C10 C9 119.94(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.38(13) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.86(13) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.78(13) . . ?
C12 C13 C15 120.73(13) . . ?
C14 C13 C15 119.48(13) . . ?
C9 C14 C13 119.74(12) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C13 178.69(17) . . ?
C15 C16 H16 180.0 . . ?
O1 C17 C18 106.51(12) . . ?
O1 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O1 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
O2 C18 C17 113.53(13) . . ?
O2 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
O2 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 105.59(11) . . ?
O3 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
O3 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.8 . . ?
O4 C21 C20 107.69(11) . . ?
O4 C21 H21A 110.2 . . ?
C20 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
C20 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5' O1' C17' 118.41(11) . . ?
C19' O2' C18' 114.41(16) . . ?
C4' O3' C20' 117.70(11) . . ?
C21' O4' C22' 112.06(14) . . ?
C1' N1' C7' 115.50(11) . . ?
C2' N2' C1' 116.87(12) . . ?
C2' N3' C9' 123.32(12) . . ?
C2' N3' H3'N 118.3 . . ?
C9' N3' H3'N 118.3 . . ?
N1' C1' N2' 128.42(13) . . ?
N1' C1' H1' 115.8 . . ?
N2' C1' H1' 115.8 . . ?
N2' C2' N3' 118.14(12) . . ?
N2' C2' C8' 121.05(11) . . ?
N3' C2' C8' 120.81(11) . . ?
C4' C3' C8' 119.52(12) . . ?
C4' C3' H3' 120.2 . . ?
C8' C3' H3' 120.2 . . ?
O3' C4' C3' 125.82(12) . . ?
O3' C4' C5' 113.74(11) . . ?
C3' C4' C5' 120.43(12) . . ?
O1' C5' C6' 125.89(12) . . ?
O1' C5' C4' 113.86(11) . . ?
C6' C5' C4' 120.23(12) . . ?
C5' C6' C7' 119.80(12) . . ?
C5' C6' H6' 120.1 . . ?
C7' C6' H6' 120.1 . . ?
N1' C7' C8' 121.77(11) . . ?
N1' C7' C6' 118.38(11) . . ?
C8' C7' C6' 119.85(11) . . ?
C7' C8' C3' 119.90(11) . . ?
C7' C8' C2' 116.29(11) . . ?
C3' C8' C2' 123.79(11) . . ?
C14' C9' C10' 120.37(12) . . ?
C14' C9' N3' 119.96(12) . . ?
C10' C9' N3' 119.61(13) . . ?
C9' C10' C11' 119.62(14) . . ?
C9' C10' H10' 120.2 . . ?
C11' C10' H10' 120.2 . . ?
C12' C11' C10' 120.66(14) . . ?
C12' C11' H11' 119.7 . . ?
C10' C11' H11' 119.7 . . ?
C11' C12' C13' 119.77(13) . . ?
C11' C12' H12' 120.1 . . ?
C13' C12' H12' 120.1 . . ?
C12' C13' C14' 119.65(14) . . ?
C12' C13' C15' 121.22(14) . . ?
C14' C13' C15' 119.12(14) . . ?
C9' C14' C13' 119.92(13) . . ?
C9' C14' H14' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C16' C15' C13' 178.58(19) . . ?
C15' C16' H16' 180.0 . . ?
O1' C17' C18' 107.05(12) . . ?
O1' C17' H17C 110.3 . . ?
C18' C17' H17C 110.3 . . ?
O1' C17' H17D 110.3 . . ?
C18' C17' H17D 110.3 . . ?
H17C C17' H17D 108.6 . . ?
O2' C18' C17' 113.44(13) . . ?
O2' C18' H18C 108.9 . . ?
C17' C18' H18C 108.9 . . ?
O2' C18' H18D 108.9 . . ?
C17' C18' H18D 108.9 . . ?
H18C C18' H18D 107.7 . . ?
O2' C19' H19D 109.5 . . ?
O2' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
O2' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
O3' C20' C21' 105.95(11) . . ?
O3' C20' H20C 110.5 . . ?
C21' C20' H20C 110.5 . . ?
O3' C20' H20D 110.5 . . ?
C21' C20' H20D 110.5 . . ?
H20C C20' H20D 108.7 . . ?
O4' C21' C20' 108.26(12) . . ?
O4' C21' H21C 110.0 . . ?
C20' C21' H21C 110.0 . . ?
O4' C21' H21D 110.0 . . ?
C20' C21' H21D 110.0 . . ?
H21C C21' H21D 108.4 . . ?
O4' C22' H22D 109.5 . . ?
O4' C22' H22E 109.5 . . ?
H22D C22' H22E 109.5 . . ?
O4' C22' H22F 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3437(16) . ?
O1 C17 1.4376(17) . ?
O2 C19 1.419(3) . ?
O2 C18 1.420(2) . ?
O3 C4 1.3531(16) . ?
O3 C20 1.4314(17) . ?
O4 C21 1.4118(18) . ?
O4 C22 1.417(2) . ?
N1 C1 1.3176(18) . ?
N1 C7 1.3763(17) . ?
N2 C2 1.3357(17) . ?
N2 C1 1.3448(18) . ?
N3 C2 1.3471(17) . ?
N3 C9 1.4265(17) . ?
N3 H3N 0.8800 . ?
C1 H1 0.9500 . ?
C2 C8 1.4351(17) . ?
C3 C4 1.3714(17) . ?
C3 C8 1.4168(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4344(18) . ?
C5 C6 1.3760(18) . ?
C6 C7 1.4141(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4092(17) . ?
C9 C14 1.3916(19) . ?
C9 C10 1.3930(19) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4025(19) . ?
C13 C15 1.438(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.204(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.509(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5035(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1' C5' 1.3485(16) . ?
O1' C17' 1.4412(18) . ?
O2' C19' 1.413(3) . ?
O2' C18' 1.417(2) . ?
O3' C4' 1.3525(16) . ?
O3' C20' 1.4344(17) . ?
O4' C21' 1.410(2) . ?
O4' C22' 1.413(2) . ?
N1' C1' 1.3172(19) . ?
N1' C7' 1.3756(17) . ?
N2' C2' 1.3344(17) . ?
N2' C1' 1.3461(18) . ?
N3' C2' 1.3438(17) . ?
N3' C9' 1.4306(18) . ?
N3' H3'N 0.8800 . ?
C1' H1' 0.9500 . ?
C2' C8' 1.4373(17) . ?
C3' C4' 1.3748(18) . ?
C3' C8' 1.4190(18) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.4318(18) . ?
C5' C6' 1.3733(19) . ?
C6' C7' 1.4159(18) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.4083(17) . ?
C9' C14' 1.390(2) . ?
C9' C10' 1.392(2) . ?
C10' C11' 1.396(2) . ?
C10' H10' 0.9500 . ?
C11' C12' 1.386(2) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.403(2) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.4031(19) . ?
C13' C15' 1.432(2) . ?
C14' H14' 0.9500 . ?
C15' C16' 1.206(2) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.512(2) . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?
C20' C21' 1.504(2) . ?
C20' H20C 0.9900 . ?
C20' H20D 0.9900 . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 N2 -1.7(2) . . . . ?
C2 N2 C1 N1 1.7(2) . . . . ?
C1 N2 C2 N3 -179.67(13) . . . . ?
C1 N2 C2 C8 0.33(19) . . . . ?
C9 N3 C2 N2 -0.4(2) . . . . ?
C9 N3 C2 C8 179.59(12) . . . . ?
C20 O3 C4 C3 -8.7(2) . . . . ?
C20 O3 C4 C5 170.43(12) . . . . ?
C8 C3 C4 O3 176.62(13) . . . . ?
C8 C3 C4 C5 -2.4(2) . . . . ?
C17 O1 C5 C6 -0.1(2) . . . . ?
C17 O1 C5 C4 -178.59(12) . . . . ?
O3 C4 C5 O1 4.03(17) . . . . ?
C3 C4 C5 O1 -176.81(12) . . . . ?
O3 C4 C5 C6 -174.59(13) . . . . ?
C3 C4 C5 C6 4.6(2) . . . . ?
O1 C5 C6 C7 179.17(13) . . . . ?
C4 C5 C6 C7 -2.41(19) . . . . ?
C1 N1 C7 C8 -0.32(19) . . . . ?
C1 N1 C7 C6 179.55(13) . . . . ?
C5 C6 C7 N1 178.37(12) . . . . ?
C5 C6 C7 C8 -1.76(19) . . . . ?
N1 C7 C8 C3 -176.25(12) . . . . ?
C6 C7 C8 C3 3.88(18) . . . . ?
N1 C7 C8 C2 2.01(18) . . . . ?
C6 C7 C8 C2 -177.86(11) . . . . ?
C4 C3 C8 C7 -1.75(19) . . . . ?
C4 C3 C8 C2 -179.88(12) . . . . ?
N2 C2 C8 C7 -2.01(18) . . . . ?
N3 C2 C8 C7 177.98(12) . . . . ?
N2 C2 C8 C3 176.18(13) . . . . ?
N3 C2 C8 C3 -3.83(19) . . . . ?
C2 N3 C9 C14 -74.37(18) . . . . ?
C2 N3 C9 C10 109.12(16) . . . . ?
C14 C9 C10 C11 1.0(2) . . . . ?
N3 C9 C10 C11 177.54(13) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C11 C12 C13 C15 -178.56(14) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
N3 C9 C14 C13 -177.26(12) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C15 C13 C14 C9 179.14(13) . . . . ?
C5 O1 C17 C18 175.29(12) . . . . ?
C19 O2 C18 C17 89.06(18) . . . . ?
O1 C17 C18 O2 -72.22(16) . . . . ?
C4 O3 C20 C21 -170.83(12) . . . . ?
C22 O4 C21 C20 171.96(13) . . . . ?
O3 C20 C21 O4 -65.29(14) . . . . ?
C7' N1' C1' N2' 2.0(2) . . . . ?
C2' N2' C1' N1' -1.9(2) . . . . ?
C1' N2' C2' N3' 179.03(13) . . . . ?
C1' N2' C2' C8' -0.8(2) . . . . ?
C9' N3' C2' N2' 2.7(2) . . . . ?
C9' N3' C2' C8' -177.47(13) . . . . ?
C20' O3' C4' C3' 8.7(2) . . . . ?
C20' O3' C4' C5' -170.61(12) . . . . ?
C8' C3' C4' O3' -176.32(13) . . . . ?
C8' C3' C4' C5' 2.9(2) . . . . ?
C17' O1' C5' C6' 1.5(2) . . . . ?
C17' O1' C5' C4' -179.70(12) . . . . ?
O3' C4' C5' O1' -4.92(17) . . . . ?
C3' C4' C5' O1' 175.77(13) . . . . ?
O3' C4' C5' C6' 173.93(13) . . . . ?
C3' C4' C5' C6' -5.4(2) . . . . ?
O1' C5' C6' C7' -178.41(13) . . . . ?
C4' C5' C6' C7' 2.9(2) . . . . ?
C1' N1' C7' C8' 0.5(2) . . . . ?
C1' N1' C7' C6' -179.55(13) . . . . ?
C5' C6' C7' N1' -178.04(13) . . . . ?
C5' C6' C7' C8' 1.92(19) . . . . ?
N1' C7' C8' C3' 175.59(12) . . . . ?
C6' C7' C8' C3' -4.36(19) . . . . ?
N1' C7' C8' C2' -2.72(18) . . . . ?
C6' C7' C8' C2' 177.32(12) . . . . ?
C4' C3' C8' C7' 1.91(19) . . . . ?
C4' C3' C8' C2' -179.91(13) . . . . ?
N2' C2' C8' C7' 2.86(19) . . . . ?
N3' C2' C8' C7' -176.93(12) . . . . ?
N2' C2' C8' C3' -175.38(13) . . . . ?
N3' C2' C8' C3' 4.8(2) . . . . ?
C2' N3' C9' C14' 68.99(19) . . . . ?
C2' N3' C9' C10' -113.83(16) . . . . ?
C14' C9' C10' C11' -0.6(2) . . . . ?
N3' C9' C10' C11' -177.79(13) . . . . ?
C9' C10' C11' C12' -0.3(2) . . . . ?
C10' C11' C12' C13' 1.1(2) . . . . ?
C11' C12' C13' C14' -1.1(2) . . . . ?
C11' C12' C13' C15' 178.07(15) . . . . ?
C10' C9' C14' C13' 0.7(2) . . . . ?
N3' C9' C14' C13' 177.81(13) . . . . ?
C12' C13' C14' C9' 0.2(2) . . . . ?
C15' C13' C14' C9' -178.98(14) . . . . ?
C5' O1' C17' C18' -176.79(12) . . . . ?
C19' O2' C18' C17' -86.34(19) . . . . ?
O1' C17' C18' O2' 74.68(17) . . . . ?
C4' O3' C20' C21' 167.96(12) . . . . ?
C22' O4' C21' C20' -169.32(14) . . . . ?
O3' C20' C21' O4' 64.58(15) . . . . ?
