#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240878.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_2240878
loop_
_publ_author_name
'Tatsız, Ramazan'
'Kasumov, Veli T.'
'Tunc, Tuncay'
'Hökelek, Tuncer'
_publ_section_title
;
 Crystal structure of
 4-({5-[(E)-(3,5-difluorophenyl)diazenyl]-2-hydroxybenzylidene}amino)-2,2,6,6-tetramethylpiperidin-1-oxyl
;
_journal_coeditor_code           XU5856
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              864
_journal_page_last               866
_journal_paper_doi               10.1107/S2056989015012049
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C22 H25 F2 N4 O2'
_chemical_formula_moiety         'C22 H25 F2 N4 O2'
_chemical_formula_sum            'C22 H25 F2 N4 O2'
_chemical_formula_weight         415.46
_chemical_name_systematic
4-({5-[(E)-(3,5-Difluorophenyl)diazenyl]-2-hydroxybenzylidene}amino)-2,2,6,6-tetramethylpiperidin-1-oxyl
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.639(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.5115(3)
_cell_length_b                   23.1062(5)
_cell_length_c                   13.8677(3)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.99
_cell_volume                     4255.06(17)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART BREEZE CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1005
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            73169
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         10597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.0733
_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)+(0.0380P)²+2.7618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1631
_reflns_number_gt                5159
_reflns_number_total             10597
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu5856sup1.cf
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240878
_cod_database_fobs_code          2240878
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
O O1 1.15807(13) 0.31895(8) 0.67257(16) 0.0571(6) Uani d . 1 1
H H1 1.182(3) 0.277(2) 0.689(3) 0.147(17) Uiso d . 1 1
O O2 1.33270(17) -0.00335(9) 0.6821(2) 0.1014(10) Uani d . 1 1
O O3 0.35009(14) 0.31846(10) 0.84490(19) 0.0700(7) Uani d . 1 1
H H3 0.330(3) 0.3547(17) 0.837(3) 0.110(15) Uiso d . 1 1
O O4 0.10773(14) 0.61906(8) 0.74731(15) 0.0621(6) Uani d . 1 1
N N1 0.69757(16) 0.36539(9) 0.60396(16) 0.0447(5) Uani d . 1 1
N N2 0.74088(15) 0.31783(9) 0.61875(16) 0.0436(5) Uani d . 1 1
N N3 1.14968(15) 0.20870(8) 0.70174(16) 0.0395(5) Uani d . 1 1
N N4 1.28781(16) 0.04498(9) 0.6852(2) 0.0555(7) Uani d . 1 1
N N5 0.81042(17) 0.26830(10) 0.88903(17) 0.0496(6) Uani d . 1 1
N N6 0.76620(16) 0.31481(9) 0.87086(16) 0.0458(6) Uani d . 1 1
N N7 0.36191(15) 0.43076(9) 0.81433(16) 0.0440(5) Uani d . 1 1
N N8 0.16577(15) 0.57475(9) 0.76354(16) 0.0413(5) Uani d . 1 1
F F1 0.38227(15) 0.26409(9) 0.5857(2) 0.1154(9) Uani d . 1 1
F F2 0.38710(13) 0.46381(8) 0.54690(17) 0.0887(6) Uani d . 1 1
F F3 1.12098(14) 0.37687(9) 0.91031(17) 0.0940(7) Uani d . 1 1
F F4 1.12618(13) 0.17533(8) 0.93352(14) 0.0785(6) Uani d . 1 1
C C1 0.58988(18) 0.36132(11) 0.59137(19) 0.0406(6) Uani d . 1 1
C C2 0.53935(19) 0.41297(12) 0.5745(2) 0.0476(7) Uani d . 1 1
H H2 0.5743 0.4474 0.5714 0.057 Uiso calc R 1 1
C C3 0.4371(2) 0.41268(13) 0.5624(2) 0.0542(8) Uani d . 1 1
C C4 0.3814(2) 0.36392(14) 0.5667(2) 0.0593(8) Uani d . 1 1
H H4 0.3115 0.3649 0.5589 0.071 Uiso calc R 1 1
C C5 0.4345(2) 0.31360(14) 0.5831(3) 0.0634(9) Uani d . 1 1
C C6 0.5379(2) 0.31004(12) 0.5959(2) 0.0552(8) Uani d . 1 1
H H6 0.5712 0.2748 0.6071 0.066 Uiso calc R 1 1
C C7 0.84776(17) 0.32118(10) 0.63156(18) 0.0370(6) Uani d . 1 1
C C8 0.90275(19) 0.37183(11) 0.6247(2) 0.0457(7) Uani d . 1 1
H H8 0.8691 0.4068 0.6109 0.055 Uiso calc R 1 1
C C9 1.00523(19) 0.37041(11) 0.6379(2) 0.0491(7) Uani d . 1 1
H H9 1.0406 0.4045 0.6329 0.059 Uiso calc R 1 1
C C10 1.05804(18) 0.31848(10) 0.65898(19) 0.0396(6) Uani d . 1 1
C C11 1.00326(17) 0.26725(10) 0.66530(17) 0.0326(5) Uani d . 1 1
C C12 0.89906(18) 0.26979(10) 0.65085(18) 0.0368(6) Uani d . 1 1
H H12 0.8629 0.2359 0.6543 0.044 Uiso calc R 1 1
C C13 1.05423(19) 0.21225(11) 0.68549(19) 0.0365(6) Uani d . 1 1
H H13 1.0106(17) 0.1798(10) 0.6857(17) 0.037(7) Uiso d . 1 1
C C14 1.20161(17) 0.15317(10) 0.72328(19) 0.0377(6) Uani d . 1 1
H H14 1.2333 0.1528 0.7928 0.045 Uiso calc R 1 1
C C15 1.28355(18) 0.15037(11) 0.6628(2) 0.0457(7) Uani d . 1 1
H H15A 1.3253 0.1846 0.6763 0.055 Uiso calc R 1 1
H H15B 1.2525 0.1514 0.5939 0.055 Uiso calc R 1 1
C C16 1.35082(18) 0.09733(11) 0.6807(2) 0.0444(7) Uani d . 1 1
C C17 1.19288(19) 0.04364(11) 0.7258(2) 0.0475(7) Uani d . 1 1
C C18 1.13575(18) 0.09998(10) 0.7027(2) 0.0416(6) Uani d . 1 1
H H18A 1.1040 0.1000 0.6340 0.050 Uiso calc R 1 1
H H18B 1.0828 0.1020 0.7412 0.050 Uiso calc R 1 1
C C19 1.4049(2) 0.08989(14) 0.5944(3) 0.0702(9) Uani d . 1 1
H H19A 1.3563 0.0836 0.5355 0.105 Uiso calc R 1 1
H H19B 1.4494 0.0572 0.6060 0.105 Uiso calc R 1 1
H H19C 1.4431 0.1241 0.5872 0.105 Uiso calc R 1 1
C C20 1.4281(2) 0.10201(14) 0.7758(2) 0.0651(9) Uani d . 1 1
H H20A 1.4610 0.0654 0.7901 0.098 Uiso calc R 1 1
H H20B 1.3947 0.1126 0.8285 0.098 Uiso calc R 1 1
H H20C 1.4772 0.1309 0.7684 0.098 Uiso calc R 1 1
C C21 1.2180(2) 0.03272(14) 0.8364(3) 0.0711(10) Uani d . 1 1
H H21A 1.2575 0.0643 0.8679 0.107 Uiso calc R 1 1
H H21B 1.2555 -0.0026 0.8489 0.107 Uiso calc R 1 1
H H21C 1.1568 0.0296 0.8618 0.107 Uiso calc R 1 1
C C22 1.1290(2) -0.00633(12) 0.6769(3) 0.0732(10) Uani d . 1 1
H H22A 1.1649 -0.0420 0.6919 0.110 Uiso calc R 1 1
H H22B 1.1151 -0.0006 0.6072 0.110 Uiso calc R 1 1
H H22C 1.0668 -0.0078 0.7009 0.110 Uiso calc R 1 1
C C23 0.91854(18) 0.27444(12) 0.89988(18) 0.0422(6) Uani d . 1 1
C C24 0.9677(2) 0.32733(12) 0.8995(2) 0.0493(7) Uani d . 1 1
H H24 0.9322 0.3620 0.8917 0.059 Uiso calc R 1 1
C C25 1.0708(2) 0.32625(13) 0.9110(2) 0.0552(8) Uani d . 1 1
C C26 1.1267(2) 0.27622(14) 0.9232(2) 0.0548(8) Uani d . 1 1
H H26 1.1966 0.2766 0.9310 0.066 Uiso calc R 1 1
C C27 1.0737(2) 0.22591(13) 0.9234(2) 0.0509(7) Uani d . 1 1
C C28 0.9715(2) 0.22356(12) 0.91185(19) 0.0464(7) Uani d . 1 1
H H28 0.9384 0.1883 0.9121 0.056 Uiso calc R 1 1
C C29 0.65870(18) 0.31143(11) 0.86313(19) 0.0410(6) Uani d . 1 1
C C30 0.60837(18) 0.36318(11) 0.84394(18) 0.0385(6) Uani d . 1 1
H H30 0.6449 0.3962 0.8348 0.046 Uiso calc R 1 1
C C31 0.50519(17) 0.36772(10) 0.83778(18) 0.0364(6) Uani d . 1 1
C C32 0.45009(19) 0.31767(11) 0.8503(2) 0.0479(7) Uani d . 1 1
C C33 0.5006(2) 0.26487(12) 0.8682(2) 0.0594(8) Uani d . 1 1
H H33 0.4645 0.2314 0.8757 0.071 Uiso calc R 1 1
C C34 0.6032(2) 0.26191(12) 0.8748(2) 0.0558(8) Uani d . 1 1
H H34 0.6360 0.2265 0.8871 0.067 Uiso calc R 1 1
C C35 0.45585(19) 0.42366(11) 0.81786(19) 0.0386(6) Uani d . 1 1
H H35 0.4994(18) 0.4552(11) 0.8064(17) 0.042(7) Uiso d . 1 1
C C36 0.32030(18) 0.48883(10) 0.79230(19) 0.0399(6) Uani d . 1 1
H H36 0.3724 0.5145 0.7756 0.048 Uiso calc R 1 1
C C37 0.23279(19) 0.48515(11) 0.7065(2) 0.0446(7) Uani d . 1 1
H H37A 0.1816 0.4599 0.7242 0.054 Uiso calc R 1 1
H H37B 0.2562 0.4679 0.6510 0.054 Uiso calc R 1 1
C C38 0.18551(18) 0.54383(11) 0.67565(19) 0.0403(6) Uani d . 1 1
C C39 0.23265(19) 0.57273(12) 0.8622(2) 0.0453(7) Uani d . 1 1
C C40 0.2808(2) 0.51305(12) 0.8792(2) 0.0498(7) Uani d . 1 1
H H40A 0.3361 0.5152 0.9347 0.060 Uiso calc R 1 1
H H40B 0.2314 0.4863 0.8963 0.060 Uiso calc R 1 1
C C41 0.2535(2) 0.58093(13) 0.6231(2) 0.0565(8) Uani d . 1 1
H H41A 0.2251 0.6189 0.6115 0.085 Uiso calc R 1 1
H H41B 0.2587 0.5633 0.5615 0.085 Uiso calc R 1 1
H H41C 0.3193 0.5838 0.6633 0.085 Uiso calc R 1 1
C C42 0.0843(2) 0.53434(13) 0.6073(2) 0.0603(8) Uani d . 1 1
H H42A 0.0554 0.5711 0.5855 0.090 Uiso calc R 1 1
H H42B 0.0396 0.5141 0.6420 0.090 Uiso calc R 1 1
H H42C 0.0943 0.5119 0.5517 0.090 Uiso calc R 1 1
C C43 0.1667(2) 0.58384(14) 0.9378(2) 0.0681(9) Uani d . 1 1
H H43A 0.1417 0.6228 0.9311 0.102 Uiso calc R 1 1
H H43B 0.2056 0.5785 1.0024 0.102 Uiso calc R 1 1
H H43C 0.1111 0.5573 0.9276 0.102 Uiso calc R 1 1
C C44 0.3117(2) 0.62071(13) 0.8681(2) 0.0645(9) Uani d . 1 1
H H44A 0.2788 0.6570 0.8503 0.097 Uiso calc R 1 1
H H44B 0.3566 0.6121 0.8239 0.097 Uiso calc R 1 1
H H44C 0.3492 0.6231 0.9339 0.097 Uiso calc R 1 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'
F F 0.0171 0.0103 '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_publ_flag
C10 O1 H1 107(2) ?
C32 O3 H3 108(3) ?
N2 N1 C1 113.4(2) ?
N1 N2 C7 114.1(2) ?
C13 N3 C14 121.6(2) yes
O2 N4 C16 115.5(2) ?
O2 N4 C17 116.2(2) ?
C16 N4 C17 124.8(2) ?
N6 N5 C23 112.2(2) ?
N5 N6 C29 114.4(2) ?
C35 N7 C36 117.9(2) yes
O4 N8 C38 116.0(2) ?
O4 N8 C39 115.6(2) ?
C38 N8 C39 124.67(19) ?
C2 C1 N1 115.1(2) ?
C2 C1 C6 120.7(2) ?
C6 C1 N1 124.2(2) ?
C1 C2 H2 120.7 ?
C3 C2 C1 118.6(3) ?
C3 C2 H2 120.7 ?
F2 C3 C2 118.7(3) ?
F2 C3 C4 117.6(3) ?
C2 C3 C4 123.8(3) ?
C3 C4 C5 115.7(3) ?
C3 C4 H4 122.1 ?
C5 C4 H4 122.1 ?
F1 C5 C4 117.8(3) ?
F1 C5 C6 118.0(3) ?
C4 C5 C6 124.2(3) ?
C1 C6 H6 121.5 ?
C5 C6 C1 117.0(3) ?
C5 C6 H6 121.5 ?
C8 C7 N2 125.2(2) ?
C12 C7 N2 116.1(2) ?
C12 C7 C8 118.7(2) ?
C7 C8 H8 119.7 ?
C9 C8 C7 120.6(2) ?
C9 C8 H8 119.7 ?
C8 C9 C10 121.0(2) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
O1 C10 C9 119.2(2) ?
O1 C10 C11 122.0(2) ?
C9 C10 C11 118.7(2) ?
C10 C11 C13 120.9(2) ?
C12 C11 C10 119.1(2) ?
C12 C11 C13 120.0(2) ?
C7 C12 C11 121.8(2) ?
C7 C12 H12 119.1 ?
C11 C12 H12 119.1 ?
N3 C13 C11 121.5(2) ?
N3 C13 H13 123.8(14) ?
C11 C13 H13 114.7(14) ?
N3 C14 C15 107.3(2) ?
N3 C14 C18 115.44(19) ?
N3 C14 H14 108.3 ?
C15 C14 C18 109.0(2) ?
C15 C14 H14 108.3 ?
C18 C14 H14 108.3 ?
C14 C15 C16 115.0(2) ?
C14 C15 H15A 108.5 ?
C14 C15 H15B 108.5 ?
C16 C15 H15A 108.5 ?
C16 C15 H15B 108.5 ?
H15A C15 H15B 107.5 ?
N4 C16 C15 109.5(2) ?
N4 C16 C19 107.7(2) ?
N4 C16 C20 109.0(2) ?
C15 C16 C19 108.8(2) ?
C15 C16 C20 112.1(2) ?
C19 C16 C20 109.6(2) ?
N4 C17 C18 109.9(2) ?
N4 C17 C22 107.7(2) ?
N4 C17 C21 109.5(2) ?
C18 C17 C22 109.4(2) ?
C18 C17 C21 111.4(2) ?
C22 C17 C21 108.9(2) ?
C14 C18 C17 113.5(2) ?
C14 C18 H18A 108.9 ?
C14 C18 H18B 108.9 ?
C17 C18 H18A 108.9 ?
C17 C18 H18B 108.9 ?
H18A C18 H18B 107.7 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19B 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C16 C20 H20A 109.5 ?
C16 C20 H20B 109.5 ?
C16 C20 H20C 109.5 ?
H20A C20 H20B 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C17 C21 H21A 109.5 ?
C17 C21 H21B 109.5 ?
C17 C21 H21C 109.5 ?
H21A C21 H21B 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C17 C22 H22A 109.5 ?
C17 C22 H22B 109.5 ?
C17 C22 H22C 109.5 ?
H22A C22 H22B 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
C24 C23 N5 124.0(2) ?
C28 C23 N5 115.0(2) ?
C28 C23 C24 121.0(2) ?
C23 C24 H24 121.4 ?
C25 C24 C23 117.3(3) ?
C25 C24 H24 121.4 ?
F3 C25 C24 118.8(3) ?
F3 C25 C26 117.6(3) ?
C24 C25 C26 123.5(3) ?
C25 C26 H26 121.9 ?
C27 C26 C25 116.1(3) ?
C27 C26 H26 122.0 ?
F4 C27 C28 118.4(3) ?
F4 C27 C26 117.9(3) ?
C28 C27 C26 123.7(3) ?
C23 C28 H28 120.8 ?
C27 C28 C23 118.4(3) ?
C27 C28 H28 120.8 ?
C30 C29 N6 115.0(2) ?
C30 C29 C34 118.6(2) ?
C34 C29 N6 126.4(2) ?
C29 C30 C31 122.2(2) ?
C29 C30 H30 118.9 ?
C31 C30 H30 118.9 ?
C30 C31 C32 118.7(2) ?
C30 C31 C35 119.9(2) ?
C32 C31 C35 121.3(2) ?
O3 C32 C31 122.3(2) ?
O3 C32 C33 118.5(2) ?
C33 C32 C31 119.2(2) ?
C32 C33 H33 119.7 ?
C34 C33 C32 120.6(3) ?
C34 C33 H33 119.7 ?
C29 C34 H34 119.7 ?
C33 C34 C29 120.6(2) ?
C33 C34 H34 119.7 ?
N7 C35 C31 122.7(2) ?
N7 C35 H35 122.0(14) ?
C31 C35 H35 115.3(14) ?
N7 C36 C40 110.6(2) ?
N7 C36 C37 109.0(2) ?
N7 C36 H36 109.8 ?
C37 C36 H36 109.8 ?
C40 C36 C37 107.9(2) ?
C40 C36 H36 109.8 ?
C36 C37 C38 113.3(2) ?
C36 C37 H37A 108.9 ?
C36 C37 H37B 108.9 ?
C38 C37 H37A 108.9 ?
C38 C37 H37B 108.9 ?
H37A C37 H37B 107.7 ?
N8 C38 C37 109.2(2) ?
N8 C38 C42 107.6(2) ?
N8 C38 C41 109.7(2) ?
C37 C38 C42 109.1(2) ?
C37 C38 C41 111.9(2) ?
C42 C38 C41 109.3(2) ?
N8 C39 C43 107.1(2) ?
N8 C39 C40 109.7(2) ?
N8 C39 C44 108.9(2) ?
C43 C39 C40 109.6(2) ?
C43 C39 C44 109.5(2) ?
C40 C39 C44 111.9(2) ?
C36 C40 C39 114.6(2) ?
C36 C40 H40A 108.6 ?
C36 C40 H40B 108.6 ?
C39 C40 H40A 108.6 ?
C39 C40 H40B 108.6 ?
H40A C40 H40B 107.6 ?
C38 C41 H41A 109.5 ?
C38 C41 H41B 109.5 ?
C38 C41 H41C 109.5 ?
H41A C41 H41B 109.5 ?
H41A C41 H41C 109.5 ?
H41B C41 H41C 109.5 ?
C38 C42 H42A 109.5 ?
C38 C42 H42B 109.5 ?
C38 C42 H42C 109.5 ?
H42A C42 H42B 109.5 ?
H42A C42 H42C 109.5 ?
H42B C42 H42C 109.5 ?
C39 C43 H43A 109.5 ?
C39 C43 H43B 109.5 ?
C39 C43 H43C 109.5 ?
H43A C43 H43B 109.5 ?
H43A C43 H43C 109.5 ?
H43B C43 H43C 109.5 ?
C39 C44 H44A 109.5 ?
C39 C44 H44B 109.5 ?
C39 C44 H44C 109.5 ?
H44A C44 H44B 109.5 ?
H44A C44 H44C 109.5 ?
H44B C44 H44C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.330(3) ?
O1 H1 1.03(5) ?
O3 C32 1.339(3) ?
O3 H3 0.88(4) ?
O4 N8 1.284(2) ?
N1 C1 1.436(3) ?
N2 N1 1.244(3) ?
N2 C7 1.424(3) ?
N3 C13 1.270(3) yes
N3 C14 1.466(3) ?
N4 O2 1.275(3) ?
N4 C16 1.487(3) ?
N4 C17 1.493(3) ?
N5 C23 1.448(3) ?
N6 N5 1.233(3) ?
N6 C29 1.439(3) ?
N7 C35 1.272(3) yes
N7 C36 1.465(3) ?
N8 C38 1.479(3) ?
N8 C39 1.495(3) ?
F1 C5 1.348(3) ?
F2 C3 1.358(3) ?
F3 C25 1.353(3) ?
F4 C27 1.360(3) ?
C1 C2 1.373(3) ?
C1 C6 1.385(4) ?
C2 C3 1.360(4) ?
C2 H2 0.9300 ?
C3 C4 1.363(4) ?
C4 C5 1.363(4) ?
C4 H4 0.9300 ?
C6 C5 1.377(4) ?
C6 H6 0.9300 ?
C7 C8 1.399(3) ?
C8 C9 1.363(3) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 C9 1.399(3) ?
C11 C10 1.408(3) ?
C11 C12 1.386(3) ?
C11 C13 1.448(3) ?
C12 C7 1.376(3) ?
C12 H12 0.9300 ?
C13 H13 0.96(2) ?
C14 C15 1.509(3) ?
C14 C18 1.513(3) ?
C14 H14 0.9800 ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 C15 1.519(3) ?
C16 C19 1.523(4) ?
C16 C20 1.528(4) ?
C17 C21 1.528(4) ?
C17 C22 1.524(4) ?
C18 C17 1.517(3) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C21 H21A 0.9600 ?
C21 H21B 0.9600 ?
C21 H21C 0.9600 ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
C23 C24 1.392(4) ?
C23 C28 1.370(4) ?
C24 C25 1.373(4) ?
C24 H24 0.9300 ?
C26 C25 1.374(4) ?
C26 H26 0.9300 ?
C27 C26 1.365(4) ?
C28 C27 1.362(4) ?
C28 H28 0.9300 ?
C29 C34 1.393(4) ?
C30 C29 1.377(3) ?
C30 H30 0.9300 ?
C31 C30 1.385(3) ?
C31 C32 1.403(3) ?
C32 C33 1.398(4) ?
C33 H33 0.9300 ?
C34 C33 1.374(4) ?
C34 H34 0.9300 ?
C35 C31 1.457(3) ?
C35 H35 0.97(2) ?
C36 C37 1.517(3) ?
C36 C40 1.512(4) ?
C36 H36 0.9800 ?
C37 H37A 0.9700 ?
C37 H37B 0.9700 ?
C38 C37 1.526(3) ?
C38 C41 1.536(4) ?
C38 C42 1.529(4) ?
C39 C40 1.525(3) ?
C39 C43 1.517(4) ?
C39 C44 1.531(4) ?
C40 H40A 0.9700 ?
C40 H40B 0.9700 ?
C41 H41A 0.9600 ?
C41 H41B 0.9600 ?
C41 H41C 0.9600 ?
C42 H42A 0.9600 ?
C42 H42B 0.9600 ?
C42 H42C 0.9600 ?
C43 H43A 0.9600 ?
C43 H43B 0.9600 ?
C43 H43C 0.9600 ?
C44 H44A 0.9600 ?
C44 H44B 0.9600 ?
C44 H44C 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
O1 H1 N3 . 1.03(5) 1.66(5) 2.585(3) 147(4) yes
O3 H3 N7 . 0.88(4) 1.85(4) 2.639(3) 148(4) yes
C13 H13 O4 2_646 0.96(2) 2.44(2) 3.324(3) 154.5(2) yes
C15 H15A F1 1_655 0.97 2.43 3.218(3) 138 yes
C30 H30 O2 2_756 0.93 2.36 3.222(3) 154 yes
C35 H35 O2 2_756 0.97(2) 2.44(2) 3.318(3) 150.5(2) yes
C37 H37B F2 . 0.9700 2.48 3.346(3) 148 yes
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_publ_flag
N2 N1 C1 C2 -179.8(2) ?
N2 N1 C1 C6 0.6(4) ?
C7 N2 N1 C1 -179.9(2) ?
N1 N2 C7 C8 -2.7(4) ?
N1 N2 C7 C12 178.3(2) ?
C14 N3 C13 C11 179.3(2) ?
C13 N3 C14 C15 134.9(3) ?
C13 N3 C14 C18 13.1(4) ?
O2 N4 C16 C15 167.8(3) ?
O2 N4 C16 C19 49.6(3) ?
O2 N4 C16 C20 -69.2(3) ?
C17 N4 C16 C15 -33.9(4) yes
C17 N4 C16 C19 -152.1(3) ?
C17 N4 C16 C20 89.1(3) ?
O2 N4 C17 C18 -166.4(3) ?
O2 N4 C17 C21 70.9(3) ?
O2 N4 C17 C22 -47.4(4) ?
C16 N4 C17 C18 35.4(4) yes
C16 N4 C17 C21 -87.3(3) ?
C16 N4 C17 C22 154.5(3) ?
N6 N5 C23 C24 5.9(4) ?
N6 N5 C23 C28 -174.7(2) ?
C29 N6 N5 C23 -177.7(2) ?
N5 N6 C29 C30 179.3(2) ?
N5 N6 C29 C34 0.5(4) ?
C36 N7 C35 C31 -179.1(2) ?
C35 N7 C36 C37 126.6(3) ?
C35 N7 C36 C40 -115.0(3) ?
O4 N8 C38 C37 -166.1(2) ?
O4 N8 C38 C41 71.0(3) ?
O4 N8 C38 C42 -47.9(3) ?
C39 N8 C38 C37 36.8(3) yes
C39 N8 C38 C41 -86.1(3) ?
C39 N8 C38 C42 155.1(2) ?
O4 N8 C39 C40 168.5(2) ?
O4 N8 C39 C43 49.6(3) ?
O4 N8 C39 C44 -68.6(3) ?
C38 N8 C39 C40 -34.3(3) yes
C38 N8 C39 C43 -153.2(2) ?
C38 N8 C39 C44 88.5(3) ?
N1 C1 C2 C3 -179.6(2) ?
C6 C1 C2 C3 0.1(4) ?
N1 C1 C6 C5 179.4(3) ?
C2 C1 C6 C5 -0.2(4) ?
C1 C2 C3 F2 179.2(3) ?
C1 C2 C3 C4 0.4(5) ?
F2 C3 C4 C5 -179.5(3) ?
C2 C3 C4 C5 -0.7(5) ?
C3 C4 C5 F1 -178.6(3) ?
C3 C4 C5 C6 0.6(5) ?
C1 C6 C5 F1 179.0(3) ?
C1 C6 C5 C4 -0.1(5) ?
N2 C7 C8 C9 -179.8(3) ?
C12 C7 C8 C9 -0.8(4) ?
C7 C8 C9 C10 -0.2(4) ?
O1 C10 C9 C8 -179.2(3) ?
C11 C10 C9 C8 0.7(4) ?
C12 C11 C10 O1 179.7(2) ?
C12 C11 C10 C9 -0.2(4) ?
C13 C11 C10 O1 -1.0(4) ?
C13 C11 C10 C9 179.1(2) ?
C10 C11 C12 C7 -0.7(4) ?
C13 C11 C12 C7 180.0(2) ?
C10 C11 C13 N3 2.7(4) ?
C12 C11 C13 N3 -178.0(2) ?
C11 C12 C7 N2 -179.6(2) ?
C11 C12 C7 C8 1.2(4) ?
N3 C14 C15 C16 175.9(2) ?
C18 C14 C15 C16 -58.4(3) yes
N3 C14 C18 C17 179.9(2) ?
C15 C14 C18 C17 59.1(3) yes
N4 C16 C15 C14 44.0(3) yes
C19 C16 C15 C14 161.5(2) ?
C20 C16 C15 C14 -77.1(3) ?
C14 C18 C17 N4 -46.1(3) yes
C14 C18 C17 C21 75.5(3) ?
C14 C18 C17 C22 -164.1(2) ?
N5 C23 C24 C25 179.7(2) ?
C28 C23 C24 C25 0.3(4) ?
N5 C23 C28 C27 -179.5(2) ?
C24 C23 C28 C27 0.0(4) ?
C23 C24 C25 F3 179.6(3) ?
C23 C24 C25 C26 -0.3(4) ?
C27 C26 C25 F3 -179.9(3) ?
C27 C26 C25 C24 0.1(4) ?
F4 C27 C26 C25 178.9(2) ?
C28 C27 C26 C25 0.3(4) ?
C23 C28 C27 F4 -178.9(2) ?
C23 C28 C27 C26 -0.3(4) ?
N6 C29 C34 C33 178.2(3) ?
C30 C29 C34 C33 -0.6(4) ?
C31 C30 C29 N6 -177.7(2) ?
C31 C30 C29 C34 1.3(4) ?
C32 C31 C30 C29 -0.8(4) ?
C35 C31 C30 C29 179.6(2) ?
C30 C31 C32 O3 -179.6(3) ?
C30 C31 C32 C33 -0.2(4) ?
C35 C31 C32 O3 -0.1(4) ?
C35 C31 C32 C33 179.3(3) ?
O3 C32 C33 C34 -179.7(3) ?
C31 C32 C33 C34 0.9(5) ?
C29 C34 C33 C32 -0.4(5) ?
N7 C35 C31 C30 -177.8(3) ?
N7 C35 C31 C32 2.7(4) ?
N7 C36 C37 C38 -178.5(2) ?
C40 C36 C37 C38 61.4(3) yes
N7 C36 C40 C39 -178.1(2) ?
C37 C36 C40 C39 -59.0(3) yes
N8 C38 C37 C36 -48.9(3) yes
C41 C38 C37 C36 72.6(3) ?
C42 C38 C37 C36 -166.3(2) ?
N8 C39 C40 C36 44.0(3) yes
C43 C39 C40 C36 161.4(2) ?
C44 C39 C40 C36 -77.0(3) ?
