#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/72/2017250.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_2017250
loop_
_publ_author_name
'Yanover, Diana'
'Kaftory, Menahem'
_publ_section_title
;
 Structural comparisons between methylated and unmethylated nitrophenyl
 lophines
;
_journal_coeditor_code           GG3195
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o365
_journal_page_last               o370
_journal_paper_doi               10.1107/S0108270109022203
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H17 N3 O2'
_chemical_formula_moiety         'C22 H17 N3 O2'
_chemical_formula_sum            'C22 H17 N3 O2'
_chemical_formula_weight         355.39
_chemical_name_systematic
;
1-methyl-2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole
;
_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                111.95(3)
_cell_angle_beta                 99.56(3)
_cell_angle_gamma                109.63(3)
_cell_formula_units_Z            4
_cell_length_a                   11.855(2)
_cell_length_b                   12.384(2)
_cell_length_c                   14.791(3)
_cell_measurement_reflns_used    14497
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.05
_cell_volume                     1788.2(10)
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.091
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14497
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.891
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0437
_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)+(0.0865P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                4081
_reflns_number_total             6250
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg3195.cif
_cod_data_source_block           VI
_cod_database_code               2017250
_cod_database_fobs_code          2017250
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
O O1A 0.62167(16) 0.94566(16) 0.69731(11) 0.0669(4) Uani d . 1 . .
O O2A 0.59949(15) 1.03422(16) 0.59954(11) 0.0643(4) Uani d . 1 . .
N N1A 0.85884(13) 0.57836(15) 0.34194(11) 0.0410(4) Uani d . 1 . .
N N2A 0.70651(14) 0.57110(15) 0.22603(11) 0.0429(4) Uani d . 1 . .
N N3A 0.62593(14) 0.95609(15) 0.61876(11) 0.0445(4) Uani d . 1 . .
C C1A 0.73778(16) 0.70946(17) 0.40577(13) 0.0386(4) Uani d . 1 . .
C C2A 0.68118(17) 0.78033(18) 0.37790(13) 0.0423(4) Uani d . 1 . .
H H2A 0.6671 0.7727 0.3095 0.051 Uiso d R 1 . .
C C3A 0.64459(17) 0.86116(18) 0.44639(13) 0.0421(4) Uani d . 1 . .
H H3A 0.6062 0.9105 0.4282 0.051 Uiso d R 1 . .
C C4A 0.66476(16) 0.87126(17) 0.54479(12) 0.0387(4) Uani d . 1 . .
C C5A 0.72008(18) 0.80324(19) 0.57544(13) 0.0455(5) Uani d . 1 . .
H H5A 0.7337 0.8130 0.6444 0.055 Uiso d R 1 . .
C C6A 0.75653(19) 0.72307(19) 0.50591(14) 0.0472(5) Uani d . 1 . .
H H6A 0.7955 0.6755 0.5264 0.057 Uiso d R 1 . .
C C7A 0.76783(16) 0.62080(17) 0.32623(13) 0.0398(4) Uani d . 1 . .
C C8A 0.85512(16) 0.49840(18) 0.24490(13) 0.0409(4) Uani d . 1 . .
C C9A 0.76005(16) 0.49490(18) 0.17504(13) 0.0408(4) Uani d . 1 . .
C C10A 0.71068(17) 0.42251(18) 0.06087(13) 0.0426(4) Uani d . 1 . .
C C11A 0.71765(19) 0.3076(2) 0.00647(15) 0.0539(5) Uani d . 1 . .
H H11A 0.7571 0.2734 0.0437 0.065 Uiso d R 1 . .
C C12A 0.6692(2) 0.2419(2) -0.10071(16) 0.0643(6) Uani d . 1 . .
H H12A 0.6761 0.1632 -0.1370 0.077 Uiso d R 1 . .
C C13A 0.6102(2) 0.2886(3) -0.15481(16) 0.0691(7) Uani d . 1 . .
H H13A 0.5766 0.2431 -0.2290 0.083 Uiso d R 1 . .
C C14A 0.6006(2) 0.4011(2) -0.10233(15) 0.0654(6) Uani d . 1 . .
H H14A 0.5595 0.4344 -0.1393 0.078 Uiso d R 1 . .
C C15A 0.65086(19) 0.4683(2) 0.00475(14) 0.0532(5) Uani d . 1 . .
H H15A 0.6430 0.5465 0.0408 0.064 Uiso d R 1 . .
C C16A 0.94456(17) 0.43948(19) 0.22948(14) 0.0467(5) Uani d . 1 . .
C C17A 0.95771(19) 0.3611(2) 0.27347(17) 0.0603(6) Uani d . 1 . .
H H17A 0.9100 0.3479 0.3180 0.072 Uiso d R 1 . .
C C18A 1.0370(3) 0.3016(3) 0.2537(2) 0.0867(9) Uani d . 1 . .
H H18A 1.0454 0.2493 0.2863 0.104 Uiso d R 1 . .
C C19A 1.1043(3) 0.3195(3) 0.1898(3) 0.0984(11) Uani d . 1 . .
H H19A 1.1554 0.2735 0.1755 0.118 Uiso d R 1 . .
C C20A 1.0947(2) 0.3985(3) 0.1463(2) 0.0892(9) Uani d . 1 . .
H H20A 1.1446 0.4120 0.1033 0.107 Uiso d R 1 . .
C C21A 1.0151(2) 0.4588(2) 0.16582(17) 0.0644(6) Uani d . 1 . .
H H21A 1.0070 0.5133 0.1355 0.077 Uiso d R 1 . .
C C22A 0.95606(18) 0.6224(2) 0.43956(14) 0.0566(6) Uani d . 1 . .
H H22A 0.9786 0.7114 0.4843 0.068 Uiso calc R 1 . .
H H22B 1.0299 0.6140 0.4260 0.068 Uiso calc R 1 . .
H H22C 0.9234 0.5708 0.4723 0.068 Uiso calc R 1 . .
O O1B 0.60201(18) 0.55568(17) 0.60989(12) 0.0793(5) Uani d . 1 . .
O O2B 0.59878(16) 0.44631(16) 0.69425(12) 0.0727(5) Uani d . 1 . .
N N1B 0.68974(13) 0.07110(14) 0.21385(10) 0.0388(4) Uani d . 1 . .
N N2B 0.82065(14) 0.08117(15) 0.34619(10) 0.0418(4) Uani d . 1 . .
N N3B 0.61307(15) 0.46610(17) 0.62150(12) 0.0508(4) Uani d . 1 . .
C C1B 0.70423(16) 0.21269(17) 0.39443(13) 0.0379(4) Uani d . 1 . .
C C2B 0.67065(18) 0.30358(18) 0.37796(14) 0.0451(5) Uani d . 1 . .
H H2B 0.6683 0.3085 0.3145 0.054 Uiso d R 1 . .
C C3B 0.64123(18) 0.38684(19) 0.45237(14) 0.0465(5) Uani d . 1 . .
H H3B 0.6169 0.4476 0.4393 0.056 Uiso d R 1 . .
C C4B 0.64727(16) 0.37980(18) 0.54354(13) 0.0402(4) Uani d . 1 . .
C C5B 0.68125(17) 0.29272(19) 0.56329(13) 0.0443(5) Uani d . 1 . .
H H5B 0.6856 0.2894 0.6276 0.053 Uiso d R 1 . .
C C6B 0.70952(17) 0.21002(18) 0.48863(13) 0.0422(4) Uani d . 1 . .
H H6B 0.7344 0.1498 0.5021 0.051 Uiso d R 1 . .
C C7B 0.73725(16) 0.12227(18) 0.31916(12) 0.0381(4) Uani d . 1 . .
C C8B 0.74718(16) -0.00671(17) 0.17279(12) 0.0381(4) Uani d . 1 . .
C C9B 0.82804(16) 0.00061(18) 0.25551(12) 0.0393(4) Uani d . 1 . .
C C10B 0.91252(17) -0.06312(18) 0.25763(13) 0.0426(5) Uani d . 1 . .
C C11B 0.9414(2) -0.1261(2) 0.17135(16) 0.0677(7) Uani d . 1 . .
H H11B 0.9072 -0.1262 0.1077 0.081 Uiso d R 1 . .
C C12B 1.0199(2) -0.1873(3) 0.1764(2) 0.0817(8) Uani d . 1 . .
H H12B 1.0390 -0.2294 0.1159 0.098 Uiso d R 1 . .
C C13B 1.0707(2) -0.1862(2) 0.2673(2) 0.0686(7) Uani d . 1 . .
H H13B 1.1228 -0.2304 0.2706 0.082 Uiso d R 1 . .
C C14B 1.04414(19) -0.1236(2) 0.35344(18) 0.0600(6) Uani d . 1 . .
H H14B 1.0806 -0.1209 0.4177 0.072 Uiso d R 1 . .
C C15B 0.96599(17) -0.0632(2) 0.34841(15) 0.0498(5) Uani d . 1 . .
H H15B 0.9490 -0.0194 0.4096 0.060 Uiso d R 1 . .
C C16B 0.71506(17) -0.07747(18) 0.05848(13) 0.0389(4) Uani d . 1 . .
C C17B 0.76997(19) -0.0133(2) 0.00666(14) 0.0510(5) Uani d . 1 . .
H H17B 0.8305 0.0760 0.0448 0.061 Uiso d R 1 . .
C C18B 0.7374(2) -0.0775(2) -0.09958(15) 0.0586(6) Uani d . 1 . .
H H18B 0.7758 -0.0327 -0.1352 0.070 Uiso d R 1 . .
C C19B 0.6497(2) -0.2045(2) -0.15436(15) 0.0573(6) Uani d . 1 . .
H H19B 0.6265 -0.2483 -0.2283 0.069 Uiso d R 1 . .
C C20B 0.5952(2) -0.2689(2) -0.10402(15) 0.0574(6) Uani d . 1 . .
H H20B 0.5348 -0.3582 -0.1426 0.069 Uiso d R 1 . .
C C21B 0.62762(19) -0.20544(19) 0.00266(14) 0.0511(5) Uani d . 1 . .
H H21B 0.5890 -0.2503 0.0382 0.061 Uiso d R 1 . .
C C22B 0.58548(19) 0.0805(2) 0.15301(14) 0.0544(6) Uani d . 1 . .
H H22D 0.5398 0.0024 0.0888 0.065 Uiso calc R 1 . .
H H22E 0.6196 0.1526 0.1392 0.065 Uiso calc R 1 . .
H H22F 0.5289 0.0929 0.1912 0.065 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'
O O 0.0106 0.0060 '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
C7A N1A C8A . . 106.88(14) ?
C7A N1A C22A . . 127.75(15) ?
C8A N1A C22A . . 124.73(15) ?
C7A N2A C9A . . 106.11(14) ?
O2A N3A O1A . . 122.90(16) ?
O2A N3A C4A . . 118.73(15) ?
O1A N3A C4A . . 118.36(16) ?
C6A C1A C2A . . 117.99(16) ?
C6A C1A C7A . . 124.10(17) ?
C2A C1A C7A . . 117.83(15) ?
C3A C2A C1A . . 121.57(16) ?
C3A C2A H2A . . 118.7 ?
C1A C2A H2A . . 119.7 ?
C2A C3A C4A . . 118.37(17) ?
C2A C3A H3A . . 122.2 ?
C4A C3A H3A . . 119.4 ?
C5A C4A C3A . . 121.98(16) ?
C5A C4A N3A . . 118.70(15) ?
C3A C4A N3A . . 119.33(16) ?
C6A C5A C4A . . 118.85(16) ?
C6A C5A H5A . . 121.1 ?
C4A C5A H5A . . 120.1 ?
C5A C6A C1A . . 121.24(17) ?
C5A C6A H6A . . 119.6 ?
C1A C6A H6A . . 119.1 ?
N2A C7A N1A . . 111.05(15) ?
N2A C7A C1A . . 122.00(16) ?
N1A C7A C1A . . 126.94(15) ?
C9A C8A N1A . . 105.76(15) ?
C9A C8A C16A . . 131.11(16) ?
N1A C8A C16A . . 123.07(16) ?
C8A C9A N2A . . 110.19(15) ?
C8A C9A C10A . . 130.01(17) ?
N2A C9A C10A . . 119.79(15) ?
C11A C10A C15A . . 117.99(16) ?
C11A C10A C9A . . 122.71(17) ?
C15A C10A C9A . . 119.27(17) ?
C12A C11A C10A . . 120.96(19) ?
C12A C11A H11A . . 119.7 ?
C10A C11A H11A . . 119.4 ?
C13A C12A C11A . . 120.2(2) ?
C13A C12A H12A . . 120.1 ?
C11A C12A H12A . . 119.7 ?
C14A C13A C12A . . 119.73(19) ?
C14A C13A H13A . . 120.0 ?
C12A C13A H13A . . 120.2 ?
C13A C14A C15A . . 120.3(2) ?
C13A C14A H14A . . 120.4 ?
C15A C14A H14A . . 119.3 ?
C14A C15A C10A . . 120.8(2) ?
C14A C15A H15A . . 119.7 ?
C10A C15A H15A . . 119.5 ?
C17A C16A C21A . . 118.40(19) ?
C17A C16A C8A . . 122.23(19) ?
C21A C16A C8A . . 119.33(19) ?
C18A C17A C16A . . 121.3(3) ?
C18A C17A H17A . . 119.7 ?
C16A C17A H17A . . 119.0 ?
C19A C18A C17A . . 119.8(3) ?
C19A C18A H18A . . 120.7 ?
C17A C18A H18A . . 119.4 ?
C18A C19A C20A . . 120.2(3) ?
C18A C19A H19A . . 117.4 ?
C20A C19A H19A . . 122.4 ?
C19A C20A C21A . . 120.3(3) ?
C19A C20A H20A . . 119.0 ?
C21A C20A H20A . . 120.7 ?
C20A C21A C16A . . 120.0(3) ?
C20A C21A H21A . . 121.1 ?
C16A C21A H21A . . 118.9 ?
N1A C22A H22A . . 109.5 ?
N1A C22A H22B . . 109.5 ?
H22A C22A H22B . . 109.5 ?
N1A C22A H22C . . 109.5 ?
H22A C22A H22C . . 109.5 ?
H22B C22A H22C . . 109.5 ?
C7B N1B C8B . . 106.94(13) ?
C7B N1B C22B . . 127.83(15) ?
C8B N1B C22B . . 124.76(14) ?
C7B N2B C9B . . 106.31(13) ?
O2B N3B O1B . . 123.56(18) ?
O2B N3B C4B . . 118.61(18) ?
O1B N3B C4B . . 117.81(17) ?
C6B C1B C2B . . 118.21(17) ?
C6B C1B C7B . . 118.27(16) ?
C2B C1B C7B . . 123.51(15) ?
C3B C2B C1B . . 120.74(17) ?
C3B C2B H2B . . 119.6 ?
C1B C2B H2B . . 119.6 ?
C4B C3B C2B . . 118.74(18) ?
C4B C3B H3B . . 121.6 ?
C2B C3B H3B . . 119.7 ?
C3B C4B C5B . . 122.35(17) ?
C3B C4B N3B . . 118.71(17) ?
C5B C4B N3B . . 118.93(16) ?
C6B C5B C4B . . 118.41(16) ?
C6B C5B H5B . . 120.3 ?
C4B C5B H5B . . 121.3 ?
C5B C6B C1B . . 121.54(18) ?
C5B C6B H6B . . 119.0 ?
C1B C6B H6B . . 119.4 ?
N2B C7B N1B . . 111.03(15) ?
N2B C7B C1B . . 123.14(14) ?
N1B C7B C1B . . 125.82(15) ?
C9B C8B N1B . . 106.27(14) ?
C9B C8B C16B . . 133.56(16) ?
N1B C8B C16B . . 120.17(14) ?
C8B C9B N2B . . 109.45(15) ?
C8B C9B C10B . . 130.01(16) ?
N2B C9B C10B . . 120.54(15) ?
C15B C10B C11B . . 117.15(18) ?
C15B C10B C9B . . 119.84(17) ?
C11B C10B C9B . . 123.00(17) ?
C10B C11B C12B . . 121.1(2) ?
C10B C11B H11B . . 119.1 ?
C12B C11B H11B . . 119.8 ?
C13B C12B C11B . . 120.3(2) ?
C13B C12B H12B . . 120.2 ?
C11B C12B H12B . . 119.5 ?
C12B C13B C14B . . 119.5(2) ?
C12B C13B H13B . . 120.7 ?
C14B C13B H13B . . 119.9 ?
C13B C14B C15B . . 120.2(2) ?
C13B C14B H14B . . 120.1 ?
C15B C14B H14B . . 119.7 ?
C14B C15B C10B . . 121.8(2) ?
C14B C15B H15B . . 119.0 ?
C10B C15B H15B . . 119.2 ?
C21B C16B C17B . . 119.14(17) ?
C21B C16B C8B . . 120.90(17) ?
C17B C16B C8B . . 119.92(17) ?
C18B C17B C16B . . 120.05(19) ?
C18B C17B H17B . . 120.3 ?
C16B C17B H17B . . 119.7 ?
C19B C18B C17B . . 120.3(2) ?
C19B C18B H18B . . 119.9 ?
C17B C18B H18B . . 119.8 ?
C20B C19B C18B . . 120.14(19) ?
C20B C19B H19B . . 119.9 ?
C18B C19B H19B . . 119.9 ?
C19B C20B C21B . . 120.0(2) ?
C19B C20B H20B . . 119.8 ?
C21B C20B H20B . . 120.2 ?
C16B C21B C20B . . 120.36(19) ?
C16B C21B H21B . . 119.5 ?
C20B C21B H21B . . 120.2 ?
N1B C22B H22D . . 109.5 ?
N1B C22B H22E . . 109.5 ?
H22D C22B H22E . . 109.5 ?
N1B C22B H22F . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 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 . 1.2234(19) ?
O2A N3A . 1.223(2) ?
N1A C7A . 1.372(2) ?
N1A C8A . 1.389(2) ?
N1A C22A . 1.465(2) ?
N2A C7A . 1.328(2) ?
N2A C9A . 1.375(2) ?
N3A C4A . 1.465(2) ?
C1A C6A . 1.397(2) ?
C1A C2A . 1.402(2) ?
C1A C7A . 1.467(2) ?
C2A C3A . 1.377(3) ?
C2A H2A . 0.9600 ?
C3A C4A . 1.385(2) ?
C3A H3A . 0.9600 ?
C4A C5A . 1.380(2) ?
C5A C6A . 1.379(3) ?
C5A H5A . 0.9599 ?
C6A H6A . 0.9599 ?
C8A C9A . 1.374(2) ?
C8A C16A . 1.478(3) ?
C9A C10A . 1.478(2) ?
C10A C11A . 1.388(3) ?
C10A C15A . 1.393(3) ?
C11A C12A . 1.387(3) ?
C11A H11A . 0.9601 ?
C12A C13A . 1.376(3) ?
C12A H12A . 0.9600 ?
C13A C14A . 1.373(3) ?
C13A H13A . 0.9600 ?
C14A C15A . 1.387(3) ?
C14A H14A . 0.9599 ?
C15A H15A . 0.9601 ?
C16A C17A . 1.389(3) ?
C16A C21A . 1.392(3) ?
C17A C18A . 1.381(3) ?
C17A H17A . 0.9600 ?
C18A C19A . 1.367(4) ?
C18A H18A . 0.9600 ?
C19A C20A . 1.380(4) ?
C19A H19A . 0.9601 ?
C20A C21A . 1.391(3) ?
C20A H20A . 0.9599 ?
C21A H21A . 0.9598 ?
C22A H22A . 0.9600 ?
C22A H22B . 0.9600 ?
C22A H22C . 0.9600 ?
O1B N3B . 1.229(2) ?
O2B N3B . 1.215(2) ?
N1B C7B . 1.370(2) ?
N1B C8B . 1.379(2) ?
N1B C22B . 1.469(2) ?
N2B C7B . 1.325(2) ?
N2B C9B . 1.378(2) ?
N3B C4B . 1.470(2) ?
C1B C6B . 1.398(2) ?
C1B C2B . 1.399(2) ?
C1B C7B . 1.468(2) ?
C2B C3B . 1.384(3) ?
C2B H2B . 0.9600 ?
C3B C4B . 1.375(2) ?
C3B H3B . 0.9600 ?
C4B C5B . 1.378(3) ?
C5B C6B . 1.374(3) ?
C5B H5B . 0.9600 ?
C6B H6B . 0.9600 ?
C8B C9B . 1.376(2) ?
C8B C16B . 1.492(2) ?
C9B C10B . 1.472(2) ?
C10B C15B . 1.387(2) ?
C10B C11B . 1.391(3) ?
C11B C12B . 1.392(3) ?
C11B H11B . 0.9601 ?
C12B C13B . 1.372(3) ?
C12B H12B . 0.9599 ?
C13B C14B . 1.372(3) ?
C13B H13B . 0.9600 ?
C14B C15B . 1.381(3) ?
C14B H14B . 0.9601 ?
C15B H15B . 0.9601 ?
C16B C21B . 1.379(3) ?
C16B C17B . 1.384(3) ?
C17B C18B . 1.382(3) ?
C17B H17B . 0.9601 ?
C18B C19B . 1.371(3) ?
C18B H18B . 0.9598 ?
C19B C20B . 1.365(3) ?
C19B H19B . 0.9600 ?
C20B C21B . 1.387(3) ?
C20B H20B . 0.9602 ?
C21B H21B . 0.9600 ?
C22B H22D . 0.9600 ?
C22B H22E . 0.9600 ?
C22B H22F . 0.9600 ?
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
C12a H12a O1a 1_544 0.96 2.66 3.544(3) 154 no
C14a H14a O2b 1_554 0.96 2.63 3.258(3) 124 no
C18b H18b O1a 1_544 0.96 2.69 3.245(3) 118 no
C19b H19b O1b 1_544 0.96 2.58 3.431(3) 148 no
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
C6A C1A C2A C3A . . . . -0.1(3) ?
C7A C1A C2A C3A . . . . 176.97(17) ?
C1A C2A C3A C4A . . . . -0.1(3) ?
C2A C3A C4A C5A . . . . 0.1(3) ?
C2A C3A C4A N3A . . . . -179.65(16) ?
O2A N3A C4A C5A . . . . 166.38(17) ?
O1A N3A C4A C5A . . . . -13.5(2) ?
O2A N3A C4A C3A . . . . -13.9(2) ?
O1A N3A C4A C3A . . . . 166.25(17) ?
C3A C4A C5A C6A . . . . 0.1(3) ?
N3A C4A C5A C6A . . . . 179.87(17) ?
C4A C5A C6A C1A . . . . -0.3(3) ?
C2A C1A C6A C5A . . . . 0.3(3) ?
C7A C1A C6A C5A . . . . -176.55(18) ?
C9A N2A C7A N1A . . . . -0.5(2) ?
C9A N2A C7A C1A . . . . 179.23(16) ?
C8A N1A C7A N2A . . . . 0.9(2) ?
C22A N1A C7A N2A . . . . 172.01(17) ?
C8A N1A C7A C1A . . . . -178.80(17) ?
C22A N1A C7A C1A . . . . -7.7(3) ?
C6A C1A C7A N2A . . . . 152.45(18) ?
C2A C1A C7A N2A . . . . -24.4(3) ?
C6A C1A C7A N1A . . . . -27.8(3) ?
C2A C1A C7A N1A . . . . 155.31(18) ?
C7A N1A C8A C9A . . . . -0.9(2) ?
C22A N1A C8A C9A . . . . -172.36(17) ?
C7A N1A C8A C16A . . . . 176.44(17) ?
C22A N1A C8A C16A . . . . 5.0(3) ?
N1A C8A C9A N2A . . . . 0.7(2) ?
C16A C8A C9A N2A . . . . -176.43(19) ?
N1A C8A C9A C10A . . . . -177.95(18) ?
C16A C8A C9A C10A . . . . 5.0(4) ?
C7A N2A C9A C8A . . . . -0.1(2) ?
C7A N2A C9A C10A . . . . 178.66(16) ?
C8A C9A C10A C11A . . . . 26.5(3) ?
N2A C9A C10A C11A . . . . -151.96(19) ?
C8A C9A C10A C15A . . . . -155.6(2) ?
N2A C9A C10A C15A . . . . 25.9(3) ?
C15A C10A C11A C12A . . . . 1.5(3) ?
C9A C10A C11A C12A . . . . 179.43(19) ?
C10A C11A C12A C13A . . . . -1.6(3) ?
C11A C12A C13A C14A . . . . 0.6(4) ?
C12A C13A C14A C15A . . . . 0.5(4) ?
C13A C14A C15A C10A . . . . -0.6(3) ?
C11A C10A C15A C14A . . . . -0.4(3) ?
C9A C10A C15A C14A . . . . -178.37(19) ?
C9A C8A C16A C17A . . . . -126.2(2) ?
N1A C8A C16A C17A . . . . 57.2(3) ?
C9A C8A C16A C21A . . . . 51.4(3) ?
N1A C8A C16A C21A . . . . -125.2(2) ?
C21A C16A C17A C18A . . . . -1.0(3) ?
C8A C16A C17A C18A . . . . 176.61(19) ?
C16A C17A C18A C19A . . . . 0.0(4) ?
C17A C18A C19A C20A . . . . 1.0(4) ?
C18A C19A C20A C21A . . . . -1.0(4) ?
C19A C20A C21A C16A . . . . -0.1(4) ?
C17A C16A C21A C20A . . . . 1.1(3) ?
C8A C16A C21A C20A . . . . -176.65(19) ?
C6B C1B C2B C3B . . . . -1.2(3) ?
C7B C1B C2B C3B . . . . -179.60(17) ?
C1B C2B C3B C4B . . . . 0.9(3) ?
C2B C3B C4B C5B . . . . -0.2(3) ?
C2B C3B C4B N3B . . . . -178.56(17) ?
O2B N3B C4B C3B . . . . 168.45(18) ?
O1B N3B C4B C3B . . . . -12.4(3) ?
O2B N3B C4B C5B . . . . -10.0(3) ?
O1B N3B C4B C5B . . . . 169.13(18) ?
C3B C4B C5B C6B . . . . -0.2(3) ?
N3B C4B C5B C6B . . . . 178.17(16) ?
C4B C5B C6B C1B . . . . -0.1(3) ?
C2B C1B C6B C5B . . . . 0.8(3) ?
C7B C1B C6B C5B . . . . 179.29(16) ?
C9B N2B C7B N1B . . . . 0.1(2) ?
C9B N2B C7B C1B . . . . -178.86(16) ?
C8B N1B C7B N2B . . . . 0.0(2) ?
C22B N1B C7B N2B . . . . 172.35(18) ?
C8B N1B C7B C1B . . . . 178.92(17) ?
C22B N1B C7B C1B . . . . -8.7(3) ?
C6B C1B C7B N2B . . . . -30.7(3) ?
C2B C1B C7B N2B . . . . 147.70(19) ?
C6B C1B C7B N1B . . . . 150.49(18) ?
C2B C1B C7B N1B . . . . -31.1(3) ?
C7B N1B C8B C9B . . . . -0.09(19) ?
C22B N1B C8B C9B . . . . -172.74(17) ?
C7B N1B C8B C16B . . . . 179.86(16) ?
C22B N1B C8B C16B . . . . 7.2(3) ?
N1B C8B C9B N2B . . . . 0.2(2) ?
C16B C8B C9B N2B . . . . -179.79(19) ?
N1B C8B C9B C10B . . . . 179.49(18) ?
C16B C8B C9B C10B . . . . -0.4(4) ?
C7B N2B C9B C8B . . . . -0.2(2) ?
C7B N2B C9B C10B . . . . -179.57(16) ?
C8B C9B C10B C15B . . . . -166.60(19) ?
N2B C9B C10B C15B . . . . 12.7(3) ?
C8B C9B C10B C11B . . . . 12.6(3) ?
N2B C9B C10B C11B . . . . -168.1(2) ?
C15B C10B C11B C12B . . . . 0.5(3) ?
C9B C10B C11B C12B . . . . -178.8(2) ?
C10B C11B C12B C13B . . . . -0.1(4) ?
C11B C12B C13B C14B . . . . -0.5(4) ?
C12B C13B C14B C15B . . . . 0.6(4) ?
C13B C14B C15B C10B . . . . -0.2(3) ?
C11B C10B C15B C14B . . . . -0.3(3) ?
C9B C10B C15B C14B . . . . 178.95(18) ?
C9B C8B C16B C21B . . . . 82.2(3) ?
N1B C8B C16B C21B . . . . -97.8(2) ?
C9B C8B C16B C17B . . . . -100.1(3) ?
N1B C8B C16B C17B . . . . 79.9(2) ?
C21B C16B C17B C18B . . . . -0.2(3) ?
C8B C16B C17B C18B . . . . -177.97(17) ?
C16B C17B C18B C19B . . . . 0.7(3) ?
C17B C18B C19B C20B . . . . -0.9(3) ?
C18B C19B C20B C21B . . . . 0.6(3) ?
C17B C16B C21B C20B . . . . 0.0(3) ?
C8B C16B C21B C20B . . . . 177.69(16) ?
C19B C20B C21B C16B . . . . -0.2(3) ?
