#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/15/2221570.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_2221570
loop_
_publ_author_name
'Kia, Reza'
'Fun, Hoong-Kun'
'Etemadi, Bijan'
'Kargar, Hadi'
_publ_section_title
N-[1-(Biphenyl-4-yl)ethylidene]-N'-(2,4-dinitrophenyl)hydrazine
_journal_coeditor_code           AT2742
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o966
_journal_page_last               o967
_journal_paper_doi               10.1107/S1600536809009593
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H16 N4 O4'
_chemical_formula_moiety         'C20 H16 N4 O4'
_chemical_formula_sum            'C20 H16 N4 O4'
_chemical_formula_weight         376.37
_chemical_name_systematic
;
N-[1-(Biphenyl-4-yl)ethylidene]-N'-(2,4-dinitrophenyl)hydrazine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.871(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.0108(5)
_cell_length_b                   14.9422(8)
_cell_length_c                   23.3401(14)
_cell_measurement_reflns_used    5139
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.51
_cell_volume                     3439.6(3)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38703
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.63
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         10018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0698
_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)+(0.0656P)²+1.1266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                6820
_reflns_number_total             10018
_reflns_threshold_expression     I>2Ĭ)
_cod_data_source_file            at2742.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221570
_cod_database_fobs_code          2221570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O O1A 0.76069(14) 0.22620(9) 0.23590(6) 0.0246(3) Uani d . 1 . .
O O2A 0.58648(18) 0.23537(10) 0.16763(8) 0.0485(5) Uani d . 1 . .
O O3A 0.32139(14) -0.01433(9) 0.09644(7) 0.0278(3) Uani d . 1 . .
O O4A 0.37325(14) -0.14680(9) 0.13206(7) 0.0280(3) Uani d . 1 . .
N N1A 0.86347(15) 0.07099(11) 0.26819(7) 0.0172(3) Uani d . 1 . .
H H1NA 0.866(2) 0.1289(17) 0.2702(11) 0.039(7) Uiso d . 1 . .
N N2A 0.94751(15) 0.01368(10) 0.30306(7) 0.0171(3) Uani d . 1 . .
N N3A 0.66711(17) 0.19105(10) 0.20141(8) 0.0243(4) Uani d . 1 . .
N N4A 0.39718(16) -0.06641(11) 0.12752(7) 0.0209(3) Uani d . 1 . .
C C1A 0.75102(18) 0.03800(12) 0.23386(8) 0.0163(4) Uani d . 1 . .
C C2A 0.72659(18) -0.05521(12) 0.22963(8) 0.0185(4) Uani d . 1 . .
H H2AA 0.7896 -0.0951 0.2515 0.022 Uiso calc R 1 . .
C C3A 0.61413(19) -0.08917(12) 0.19472(8) 0.0196(4) Uani d . 1 . .
H H3AA 0.5996 -0.1520 0.1924 0.024 Uiso calc R 1 . .
C C4A 0.52048(18) -0.03081(12) 0.16247(8) 0.0189(4) Uani d . 1 . .
C C5A 0.53958(18) 0.06021(12) 0.16430(8) 0.0195(4) Uani d . 1 . .
H H5AA 0.4764 0.0990 0.1415 0.023 Uiso calc R 1 . .
C C6A 0.65363(18) 0.09453(12) 0.20027(9) 0.0187(4) Uani d . 1 . .
C C7A 1.05071(18) 0.04897(12) 0.33658(8) 0.0172(4) Uani d . 1 . .
C C8A 1.13686(18) -0.01546(12) 0.37413(8) 0.0173(4) Uani d . 1 . .
C C9A 1.08960(19) -0.10274(12) 0.37967(8) 0.0200(4) Uani d . 1 . .
H H9AA 1.0000 -0.1179 0.3617 0.024 Uiso calc R 1 . .
C C10A 1.17056(19) -0.16714(12) 0.41074(9) 0.0203(4) Uani d . 1 . .
H H10A 1.1364 -0.2261 0.4132 0.024 Uiso calc R 1 . .
C C11A 1.30261(18) -0.14688(12) 0.43877(8) 0.0180(4) Uani d . 1 . .
C C12A 1.34820(19) -0.05927(12) 0.43486(8) 0.0196(4) Uani d . 1 . .
H H12A 1.4364 -0.0436 0.4542 0.024 Uiso calc R 1 . .
C C13A 1.26710(18) 0.00583(12) 0.40313(8) 0.0186(4) Uani d . 1 . .
H H13A 1.3006 0.0650 0.4012 0.022 Uiso calc R 1 . .
C C14A 1.38924(18) -0.21713(12) 0.47113(8) 0.0194(4) Uani d . 1 . .
C C15A 1.3764(2) -0.30658(13) 0.45349(9) 0.0234(4) Uani d . 1 . .
H H15A 1.3121 -0.3224 0.4202 0.028 Uiso calc R 1 . .
C C16A 1.4563(2) -0.37248(14) 0.48411(10) 0.0277(5) Uani d . 1 . .
H H16A 1.4457 -0.4330 0.4718 0.033 Uiso calc R 1 . .
C C17A 1.5511(2) -0.35083(14) 0.53224(10) 0.0287(5) Uani d . 1 . .
H H17A 1.6069 -0.3960 0.5525 0.034 Uiso calc R 1 . .
C C18A 1.5644(2) -0.26259(14) 0.55081(10) 0.0297(5) Uani d . 1 . .
H H18A 1.6286 -0.2474 0.5843 0.036 Uiso calc R 1 . .
C C19A 1.4841(2) -0.19649(14) 0.52056(9) 0.0246(4) Uani d . 1 . .
H H19A 1.4938 -0.1363 0.5336 0.029 Uiso calc R 1 . .
C C20A 1.08413(19) 0.14713(12) 0.33820(9) 0.0214(4) Uani d . 1 . .
H H20A 1.0061 0.1814 0.3464 0.032 Uiso calc R 1 . .
H H20B 1.1055 0.1656 0.3005 0.032 Uiso calc R 1 . .
H H20C 1.1625 0.1584 0.3687 0.032 Uiso calc R 1 . .
O O1B 0.24703(15) 0.26357(9) 0.23255(7) 0.0323(4) Uani d . 1 . .
O O2B 0.4466(2) 0.24962(11) 0.28413(10) 0.0599(6) Uani d . 1 . .
O O3B 0.66656(15) 0.48817(10) 0.39824(7) 0.0307(3) Uani d . 1 . .
O O4B 0.60838(14) 0.62418(9) 0.37192(6) 0.0278(3) Uani d . 1 . .
N N1B 0.13039(16) 0.41932(11) 0.21771(8) 0.0203(4) Uani d . 1 . .
H H1NB 0.126(2) 0.3682(15) 0.2101(10) 0.025(6) Uiso d . 1 . .
N N2B 0.03856(15) 0.48109(10) 0.19137(7) 0.0189(3) Uani d . 1 . .
N N3B 0.34763(19) 0.29565(11) 0.26485(9) 0.0306(4) Uani d . 1 . .
N N4B 0.58899(16) 0.54278(11) 0.37022(7) 0.0230(4) Uani d . 1 . .
C C1B 0.24162(18) 0.44779(12) 0.25439(8) 0.0184(4) Uani d . 1 . .
C C2B 0.25660(19) 0.53943(12) 0.27013(9) 0.0200(4) Uani d . 1 . .
H H2BA 0.1880 0.5808 0.2543 0.024 Uiso calc R 1 . .
C C3B 0.36773(19) 0.56955(13) 0.30758(9) 0.0210(4) Uani d . 1 . .
H H3BA 0.3763 0.6313 0.3171 0.025 Uiso calc R 1 . .
C C4B 0.46877(19) 0.50923(12) 0.33182(8) 0.0198(4) Uani d . 1 . .
C C5B 0.46021(19) 0.41996(13) 0.31842(9) 0.0215(4) Uani d . 1 . .
H H5BA 0.5293 0.3797 0.3354 0.026 Uiso calc R 1 . .
C C6B 0.34862(19) 0.38920(12) 0.27952(9) 0.0206(4) Uani d . 1 . .
C C7B -0.06623(19) 0.45005(12) 0.15687(8) 0.0190(4) Uani d . 1 . .
C C8B -0.15944(18) 0.51924(12) 0.12712(8) 0.0186(4) Uani d . 1 . .
C C9B -0.14824(19) 0.60798(12) 0.14622(8) 0.0191(4) Uani d . 1 . .
H H9BA -0.0812 0.6235 0.1786 0.023 Uiso calc R 1 . .
C C10B -0.23311(18) 0.67353(12) 0.11872(8) 0.0191(4) Uani d . 1 . .
H H10B -0.2242 0.7332 0.1330 0.023 Uiso calc R 1 . .
C C11B -0.33207(18) 0.65396(12) 0.07024(9) 0.0190(4) Uani d . 1 . .
C C12B -0.34157(19) 0.56507(13) 0.05072(9) 0.0214(4) Uani d . 1 . .
H H12B -0.4066 0.5498 0.0175 0.026 Uiso calc R 1 . .
C C13B -0.25785(19) 0.49892(13) 0.07897(9) 0.0207(4) Uani d . 1 . .
H H13B -0.2677 0.4390 0.0653 0.025 Uiso calc R 1 . .
C C14B -0.42078(19) 0.72507(13) 0.03980(8) 0.0198(4) Uani d . 1 . .
C C15B -0.3711(2) 0.81216(13) 0.03623(9) 0.0228(4) Uani d . 1 . .
H H15B -0.2814 0.8263 0.0547 0.027 Uiso calc R 1 . .
C C16B -0.4522(2) 0.87809(14) 0.00587(9) 0.0272(5) Uani d . 1 . .
H H16B -0.4173 0.9368 0.0033 0.033 Uiso calc R 1 . .
C C17B -0.5834(2) 0.85851(14) -0.02069(9) 0.0289(5) Uani d . 1 . .
H H17B -0.6381 0.9037 -0.0416 0.035 Uiso calc R 1 . .
C C18B -0.6353(2) 0.77304(14) -0.01678(9) 0.0280(5) Uani d . 1 . .
H H18B -0.7258 0.7598 -0.0345 0.034 Uiso calc R 1 . .
C C19B -0.5540(2) 0.70702(14) 0.01314(9) 0.0235(4) Uani d . 1 . .
H H19B -0.5897 0.6485 0.0155 0.028 Uiso calc R 1 . .
C C20B -0.0951(2) 0.35244(12) 0.14521(9) 0.0233(4) Uani d . 1 . .
H H20D -0.0688 0.3184 0.1813 0.035 Uiso calc R 1 . .
H H20E -0.0432 0.3311 0.1159 0.035 Uiso calc R 1 . .
H H20F -0.1922 0.3441 0.1308 0.035 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
C1A N1A N2A . . 119.17(15) ?
C1A N1A H1NA . . 114.3(17) ?
N2A N1A H1NA . . 125.6(17) ?
C7A N2A N1A . . 116.74(15) ?
O2A N3A O1A . . 122.02(16) ?
O2A N3A C6A . . 118.59(17) ?
O1A N3A C6A . . 119.38(16) ?
O3A N4A O4A . . 123.82(16) ?
O3A N4A C4A . . 118.40(15) ?
O4A N4A C4A . . 117.75(16) ?
N1A C1A C2A . . 120.97(17) ?
N1A C1A C6A . . 122.09(16) ?
C2A C1A C6A . . 116.93(17) ?
C3A C2A C1A . . 121.40(17) ?
C3A C2A H2AA . . 119.3 ?
C1A C2A H2AA . . 119.3 ?
C2A C3A C4A . . 119.68(17) ?
C2A C3A H3AA . . 120.2 ?
C4A C3A H3AA . . 120.2 ?
C5A C4A C3A . . 121.53(18) ?
C5A C4A N4A . . 118.60(17) ?
C3A C4A N4A . . 119.84(16) ?
C4A C5A C6A . . 118.58(17) ?
C4A C5A H5AA . . 120.7 ?
C6A C5A H5AA . . 120.7 ?
C5A C6A C1A . . 121.85(16) ?
C5A C6A N3A . . 116.20(16) ?
C1A C6A N3A . . 121.94(16) ?
N2A C7A C8A . . 114.65(16) ?
N2A C7A C20A . . 124.26(17) ?
C8A C7A C20A . . 121.09(16) ?
C13A C8A C9A . . 117.93(17) ?
C13A C8A C7A . . 122.70(16) ?
C9A C8A C7A . . 119.32(16) ?
C10A C9A C8A . . 121.34(18) ?
C10A C9A H9AA . . 119.3 ?
C8A C9A H9AA . . 119.3 ?
C9A C10A C11A . . 121.02(17) ?
C9A C10A H10A . . 119.5 ?
C11A C10A H10A . . 119.5 ?
C12A C11A C10A . . 117.69(17) ?
C12A C11A C14A . . 121.89(17) ?
C10A C11A C14A . . 120.42(16) ?
C11A C12A C13A . . 121.46(17) ?
C11A C12A H12A . . 119.3 ?
C13A C12A H12A . . 119.3 ?
C12A C13A C8A . . 120.50(17) ?
C12A C13A H13A . . 119.8 ?
C8A C13A H13A . . 119.8 ?
C19A C14A C15A . . 118.00(18) ?
C19A C14A C11A . . 121.30(17) ?
C15A C14A C11A . . 120.69(18) ?
C16A C15A C14A . . 120.7(2) ?
C16A C15A H15A . . 119.6 ?
C14A C15A H15A . . 119.6 ?
C17A C16A C15A . . 120.6(2) ?
C17A C16A H16A . . 119.7 ?
C15A C16A H16A . . 119.7 ?
C16A C17A C18A . . 119.57(19) ?
C16A C17A H17A . . 120.2 ?
C18A C17A H17A . . 120.2 ?
C17A C18A C19A . . 120.1(2) ?
C17A C18A H18A . . 120.0 ?
C19A C18A H18A . . 120.0 ?
C18A C19A C14A . . 121.0(2) ?
C18A C19A H19A . . 119.5 ?
C14A C19A H19A . . 119.5 ?
C7A C20A H20A . . 109.5 ?
C7A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C7A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C1B N1B N2B . . 119.21(16) ?
C1B N1B H1NB . . 117.1(17) ?
N2B N1B H1NB . . 123.4(17) ?
C7B N2B N1B . . 116.56(16) ?
O2B N3B O1B . . 121.65(18) ?
O2B N3B C6B . . 119.03(18) ?
O1B N3B C6B . . 119.32(17) ?
O4B N4B O3B . . 123.70(17) ?
O4B N4B C4B . . 117.88(16) ?
O3B N4B C4B . . 118.41(16) ?
N1B C1B C2B . . 120.45(17) ?
N1B C1B C6B . . 123.04(17) ?
C2B C1B C6B . . 116.52(17) ?
C3B C2B C1B . . 121.41(18) ?
C3B C2B H2BA . . 119.3 ?
C1B C2B H2BA . . 119.3 ?
C2B C3B C4B . . 119.92(18) ?
C2B C3B H3BA . . 120.0 ?
C4B C3B H3BA . . 120.0 ?
C5B C4B C3B . . 121.48(18) ?
C5B C4B N4B . . 119.16(17) ?
C3B C4B N4B . . 119.30(17) ?
C4B C5B C6B . . 118.86(18) ?
C4B C5B H5BA . . 120.6 ?
C6B C5B H5BA . . 120.6 ?
C5B C6B C1B . . 121.79(17) ?
C5B C6B N3B . . 116.63(17) ?
C1B C6B N3B . . 121.56(18) ?
N2B C7B C8B . . 114.79(16) ?
N2B C7B C20B . . 124.82(18) ?
C8B C7B C20B . . 120.38(17) ?
C13B C8B C9B . . 118.07(17) ?
C13B C8B C7B . . 121.75(17) ?
C9B C8B C7B . . 120.16(17) ?
C10B C9B C8B . . 121.04(18) ?
C10B C9B H9BA . . 119.5 ?
C8B C9B H9BA . . 119.5 ?
C9B C10B C11B . . 121.39(17) ?
C9B C10B H10B . . 119.3 ?
C11B C10B H10B . . 119.3 ?
C10B C11B C12B . . 117.35(17) ?
C10B C11B C14B . . 121.27(17) ?
C12B C11B C14B . . 121.37(18) ?
C13B C12B C11B . . 121.24(18) ?
C13B C12B H12B . . 119.4 ?
C11B C12B H12B . . 119.4 ?
C12B C13B C8B . . 120.90(18) ?
C12B C13B H13B . . 119.6 ?
C8B C13B H13B . . 119.6 ?
C19B C14B C15B . . 118.31(18) ?
C19B C14B C11B . . 121.43(17) ?
C15B C14B C11B . . 120.25(17) ?
C16B C15B C14B . . 120.41(19) ?
C16B C15B H15B . . 119.8 ?
C14B C15B H15B . . 119.8 ?
C17B C16B C15B . . 120.31(19) ?
C17B C16B H16B . . 119.8 ?
C15B C16B H16B . . 119.8 ?
C16B C17B C18B . . 120.1(2) ?
C16B C17B H17B . . 119.9 ?
C18B C17B H17B . . 119.9 ?
C17B C18B C19B . . 119.6(2) ?
C17B C18B H18B . . 120.2 ?
C19B C18B H18B . . 120.2 ?
C18B C19B C14B . . 121.25(19) ?
C18B C19B H19B . . 119.4 ?
C14B C19B H19B . . 119.4 ?
C7B C20B H20D . . 109.5 ?
C7B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C7B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 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
O1A N3A . 1.242(2) ?
O2A N3A . 1.222(2) ?
O3A N4A . 1.232(2) ?
O4A N4A . 1.233(2) ?
N1A C1A . 1.358(2) ?
N1A N2A . 1.367(2) ?
N1A H1NA . 0.87(2) ?
N2A C7A . 1.296(2) ?
N3A C6A . 1.448(2) ?
N4A C4A . 1.458(2) ?
C1A C2A . 1.415(2) ?
C1A C6A . 1.420(2) ?
C2A C3A . 1.369(3) ?
C2A H2AA . 0.9500 ?
C3A C4A . 1.401(3) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.373(3) ?
C5A C6A . 1.394(3) ?
C5A H5AA . 0.9500 ?
C7A C8A . 1.476(3) ?
C7A C20A . 1.504(2) ?
C8A C13A . 1.399(3) ?
C8A C9A . 1.401(2) ?
C9A C10A . 1.381(3) ?
C9A H9AA . 0.9500 ?
C10A C11A . 1.404(3) ?
C10A H10A . 0.9500 ?
C11A C12A . 1.394(3) ?
C11A C14A . 1.483(3) ?
C12A C13A . 1.395(3) ?
C12A H12A . 0.9500 ?
C13A H13A . 0.9500 ?
C14A C19A . 1.397(3) ?
C14A C15A . 1.398(3) ?
C15A C16A . 1.387(3) ?
C15A H15A . 0.9500 ?
C16A C17A . 1.379(3) ?
C16A H16A . 0.9500 ?
C17A C18A . 1.387(3) ?
C17A H17A . 0.9500 ?
C18A C19A . 1.388(3) ?
C18A H18A . 0.9500 ?
C19A H19A . 0.9500 ?
C20A H20A . 0.9800 ?
C20A H20B . 0.9800 ?
C20A H20C . 0.9800 ?
O1B N3B . 1.246(2) ?
O2B N3B . 1.226(2) ?
O3B N4B . 1.234(2) ?
O4B N4B . 1.231(2) ?
N1B C1B . 1.352(2) ?
N1B N2B . 1.372(2) ?
N1B H1NB . 0.78(2) ?
N2B C7B . 1.294(2) ?
N3B C6B . 1.439(2) ?
N4B C4B . 1.461(3) ?
C1B C2B . 1.419(3) ?
C1B C6B . 1.429(3) ?
C2B C3B . 1.368(3) ?
C2B H2BA . 0.9500 ?
C3B C4B . 1.400(3) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.369(3) ?
C5B C6B . 1.391(3) ?
C5B H5BA . 0.9500 ?
C7B C8B . 1.483(3) ?
C7B C20B . 1.503(3) ?
C8B C13B . 1.395(3) ?
C8B C9B . 1.397(3) ?
C9B C10B . 1.381(3) ?
C9B H9BA . 0.9500 ?
C10B C11B . 1.401(3) ?
C10B H10B . 0.9500 ?
C11B C12B . 1.402(3) ?
C11B C14B . 1.485(3) ?
C12B C13B . 1.387(3) ?
C12B H12B . 0.9500 ?
C13B H13B . 0.9500 ?
C14B C19B . 1.398(3) ?
C14B C15B . 1.401(3) ?
C15B C16B . 1.391(3) ?
C15B H15B . 0.9500 ?
C16B C17B . 1.385(3) ?
C16B H16B . 0.9500 ?
C17B C18B . 1.387(3) ?
C17B H17B . 0.9500 ?
C18B C19B . 1.388(3) ?
C18B H18B . 0.9500 ?
C19B H19B . 0.9500 ?
C20B H20D . 0.9800 ?
C20B H20E . 0.9800 ?
C20B H20F . 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
_geom_hbond_publ_flag
N1A H1NA O1A . 0.87(3) 1.89(2) 2.596(2) 137(2) y
N1B H1NB O1B . 0.78(2) 1.99(2) 2.600(2) 134(2) y
C9A H9AA O2A 2_645 0.95 2.4100 3.084(2) 127 y
C3B H3BA O1B 2_555 0.95 2.5100 3.199(2) 130 y
C9B H9BA O2B 2_555 0.95 2.3900 3.174(3) 139 y
C17A H17A O3A 4_756 0.95 2.5900 3.498(3) 161 y
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
C1A N1A N2A C7A . . . . -177.50(16) ?
N2A N1A C1A C2A . . . . -6.0(2) ?
N2A N1A C1A C6A . . . . 174.68(16) ?
N1A C1A C2A C3A . . . . -179.39(17) ?
C6A C1A C2A C3A . . . . 0.0(3) ?
C1A C2A C3A C4A . . . . -0.2(3) ?
C2A C3A C4A C5A . . . . 1.0(3) ?
C2A C3A C4A N4A . . . . -176.91(16) ?
O3A N4A C4A C5A . . . . 7.1(3) ?
O4A N4A C4A C5A . . . . -171.05(17) ?
O3A N4A C4A C3A . . . . -174.96(17) ?
O4A N4A C4A C3A . . . . 6.9(3) ?
C3A C4A C5A C6A . . . . -1.5(3) ?
N4A C4A C5A C6A . . . . 176.43(16) ?
C4A C5A C6A C1A . . . . 1.3(3) ?
C4A C5A C6A N3A . . . . -178.73(17) ?
N1A C1A C6A C5A . . . . 178.84(17) ?
C2A C1A C6A C5A . . . . -0.5(3) ?
N1A C1A C6A N3A . . . . -1.2(3) ?
C2A C1A C6A N3A . . . . 179.46(16) ?
O2A N3A C6A C5A . . . . -6.5(3) ?
O1A N3A C6A C5A . . . . 174.46(17) ?
O2A N3A C6A C1A . . . . 173.51(19) ?
O1A N3A C6A C1A . . . . -5.5(3) ?
N1A N2A C7A C8A . . . . 178.93(15) ?
N1A N2A C7A C20A . . . . -1.4(3) ?
N2A C7A C8A C13A . . . . 165.23(17) ?
C20A C7A C8A C13A . . . . -14.4(3) ?
N2A C7A C8A C9A . . . . -12.4(2) ?
C20A C7A C8A C9A . . . . 167.97(17) ?
C13A C8A C9A C10A . . . . -2.7(3) ?
C7A C8A C9A C10A . . . . 175.07(17) ?
C8A C9A C10A C11A . . . . 1.1(3) ?
C9A C10A C11A C12A . . . . 1.0(3) ?
C9A C10A C11A C14A . . . . -178.94(17) ?
C10A C11A C12A C13A . . . . -1.5(3) ?
C14A C11A C12A C13A . . . . 178.42(17) ?
C11A C12A C13A C8A . . . . -0.1(3) ?
C9A C8A C13A C12A . . . . 2.1(3) ?
C7A C8A C13A C12A . . . . -175.51(17) ?
C12A C11A C14A C19A . . . . 32.5(3) ?
C10A C11A C14A C19A . . . . -147.56(19) ?
C12A C11A C14A C15A . . . . -148.62(18) ?
C10A C11A C14A C15A . . . . 31.3(3) ?
C19A C14A C15A C16A . . . . -0.4(3) ?
C11A C14A C15A C16A . . . . -179.29(17) ?
C14A C15A C16A C17A . . . . -0.7(3) ?
C15A C16A C17A C18A . . . . 1.3(3) ?
C16A C17A C18A C19A . . . . -0.9(3) ?
C17A C18A C19A C14A . . . . -0.1(3) ?
C15A C14A C19A C18A . . . . 0.8(3) ?
C11A C14A C19A C18A . . . . 179.68(18) ?
C1B N1B N2B C7B . . . . -179.75(16) ?
N2B N1B C1B C2B . . . . 6.4(3) ?
N2B N1B C1B C6B . . . . -174.03(17) ?
N1B C1B C2B C3B . . . . 179.40(17) ?
C6B C1B C2B C3B . . . . -0.2(3) ?
C1B C2B C3B C4B . . . . -0.8(3) ?
C2B C3B C4B C5B . . . . 0.8(3) ?
C2B C3B C4B N4B . . . . 177.97(16) ?
O4B N4B C4B C5B . . . . 164.84(17) ?
O3B N4B C4B C5B . . . . -13.8(3) ?
O4B N4B C4B C3B . . . . -12.4(2) ?
O3B N4B C4B C3B . . . . 168.92(17) ?
C3B C4B C5B C6B . . . . 0.4(3) ?
N4B C4B C5B C6B . . . . -176.81(16) ?
C4B C5B C6B C1B . . . . -1.5(3) ?
C4B C5B C6B N3B . . . . 177.20(17) ?
N1B C1B C6B C5B . . . . -178.20(18) ?
C2B C1B C6B C5B . . . . 1.4(3) ?
N1B C1B C6B N3B . . . . 3.2(3) ?
C2B C1B C6B N3B . . . . -177.22(17) ?
O2B N3B C6B C5B . . . . -4.2(3) ?
O1B N3B C6B C5B . . . . 176.37(18) ?
O2B N3B C6B C1B . . . . 174.5(2) ?
O1B N3B C6B C1B . . . . -4.9(3) ?
N1B N2B C7B C8B . . . . -177.16(15) ?
N1B N2B C7B C20B . . . . 1.7(3) ?
N2B C7B C8B C13B . . . . 164.50(17) ?
C20B C7B C8B C13B . . . . -14.4(3) ?
N2B C7B C8B C9B . . . . -14.0(2) ?
C20B C7B C8B C9B . . . . 167.14(17) ?
C13B C8B C9B C10B . . . . 0.8(3) ?
C7B C8B C9B C10B . . . . 179.31(17) ?
C8B C9B C10B C11B . . . . -1.0(3) ?
C9B C10B C11B C12B . . . . 0.0(3) ?
C9B C10B C11B C14B . . . . -178.35(17) ?
C10B C11B C12B C13B . . . . 1.1(3) ?
C14B C11B C12B C13B . . . . 179.48(17) ?
C11B C12B C13B C8B . . . . -1.3(3) ?
C9B C8B C13B C12B . . . . 0.4(3) ?
C7B C8B C13B C12B . . . . -178.16(17) ?
C10B C11B C14B C19B . . . . -147.87(18) ?
C12B C11B C14B C19B . . . . 33.8(3) ?
C10B C11B C14B C15B . . . . 33.4(3) ?
C12B C11B C14B C15B . . . . -144.91(18) ?
C19B C14B C15B C16B . . . . -1.2(3) ?
C11B C14B C15B C16B . . . . 177.55(18) ?
C14B C15B C16B C17B . . . . 0.6(3) ?
C15B C16B C17B C18B . . . . 0.5(3) ?
C16B C17B C18B C19B . . . . -1.0(3) ?
C17B C18B C19B C14B . . . . 0.4(3) ?
C15B C14B C19B C18B . . . . 0.7(3) ?
C11B C14B C19B C18B . . . . -178.02(18) ?
