#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:44:10 +0300 (Sat, 06 May 2023) $
#$Revision: 283576 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/42/2244222.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_2244222
loop_
_publ_author_name
'Kurbanova, Malahat Musrat'
'Faizi, Md Serajul Haque'
'Cinar, Emine Berrin'
'Jamal, Asif'
'Çemberci, Mustafa'
'Sadigova, Arzu'
'Askerov, Rizvan'
'Dege, Necmi'
'Nabi, Tahera'
_publ_section_title
;
 Crystal structure, Hirshfeld surface analysis and DFT study of
 (5E,5'E,6Z,6'Z)-6,6'-[ethane-1,2-diyl-bis(aza-nylyl-idene)]bis-{5-[2-(4-fluoro-phen-yl)hydra-zono]-3,3-di-methyl-cyclo-hexa-none}
 2.5-hydrate.
;
_journal_coeditor_code           ZV2022
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              297
_journal_page_last               301
_journal_paper_doi               10.1107/S2056989023001895
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C30 H34 F2 N6 O2, 2.5H2 O'
_chemical_formula_moiety         'C30 H34 F2 N6 O2, 2.5(H2 O)'
_chemical_formula_sum            'C30 H39 F2 N6 O4.5'
_chemical_formula_weight         593.67
_chemical_name_systematic
'(5E,5'E,6Z,6'Z)-6,6'-[Ethane-1,2-diylbis(azanylylidene)]bis{5-[2-(4-fluorophenyl)hydrazono]-3,3-dimethylcyclohexanone} 2.5-hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.2970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   22.7715(19)
_cell_length_b                   17.2794(15)
_cell_length_c                   25.640(3)
_cell_measurement_reflns_used    2620
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.80
_cell_measurement_theta_min      2.51
_cell_volume                     9334.4(16)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2013/1 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37069
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         1.921
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             3780
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.286
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         8249
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0584
_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)+(0.0988P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                4099
_reflns_number_total             8249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zv2022sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2244222.cif.'
_cod_original_cell_volume        9334.2(16)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2244222
_cod_database_fobs_code          2244222
_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   0.967
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F2 1.09554(9) 0.57702(14) 0.53005(9) 0.0952(7) Uani d 1 . .
O O6 0.89907(11) 0.85004(13) 0.36530(9) 0.0707(7) Uani d 1 . .
N N9 0.95271(11) 0.63828(14) 0.27726(10) 0.0497(6) Uani d 1 . .
H H9 0.914706 0.638997 0.252226 0.060 Uiso calc 1 . .
F F3 0.76710(10) 0.32116(12) 0.48211(10) 0.1025(8) Uani d 1 . .
N N10 0.86237(11) 0.75960(14) 0.27290(10) 0.0519(6) Uani d 1 . .
N N2 0.75280(11) 0.67741(14) 0.31652(10) 0.0521(6) Uani d 1 . .
H H2 0.791352 0.677251 0.340527 0.063 Uiso calc 1 . .
N N3 0.78027(11) 0.76386(14) 0.41673(10) 0.0530(7) Uani d 1 . .
H H3 0.771048 0.715792 0.417904 0.064 Uiso calc 1 . .
N N1 0.84455(11) 0.71070(15) 0.23249(10) 0.0539(7) Uani d 1 . .
N N7 0.83957(12) 0.55075(15) 0.32396(11) 0.0557(7) Uani d 1 . .
N N6 0.85905(12) 0.60375(15) 0.36126(11) 0.0550(7) Uani d 1 . .
N N4 0.82821(12) 0.67186(16) 0.51854(11) 0.0588(7) Uani d 1 . .
O O7 0.79621(12) 0.44357(15) 0.24172(11) 0.0846(8) Uani d 1 . .
N N5 0.79668(12) 0.63644(15) 0.47308(11) 0.0581(7) Uani d 1 . .
F F4 0.60711(11) 0.74370(16) 0.06565(10) 0.1250(9) Uani d 1 . .
O O3 0.89386(14) 0.75091(17) 0.61336(10) 0.0977(9) Uani d 1 . .
C C12 0.96907(13) 0.69768(16) 0.31285(11) 0.0446(7) Uani d 1 . .
C C7 0.92362(13) 0.75336(17) 0.31220(12) 0.0460(7) Uani d 1 . .
C C8 0.93933(15) 0.80892(17) 0.35815(12) 0.0492(7) Uani d 1 . .
C C20 0.73494(14) 0.61741(17) 0.28199(12) 0.0499(8) Uani d 1 . .
C C10 1.05603(13) 0.78558(17) 0.37729(12) 0.0509(8) Uani d 1 . .
C C13 0.99160(14) 0.57224(16) 0.27573(12) 0.0514(8) Uani d 1 . .
H H13A 0.968891 0.524959 0.276294 0.062 Uiso calc 1 . .
H H13B 1.030349 0.572808 0.309210 0.062 Uiso calc 1 . .
C C11 1.03605(13) 0.70393(17) 0.35377(12) 0.0498(7) Uani d 1 . .
H H11A 1.063950 0.686857 0.335369 0.060 Uiso calc 1 . .
H H11B 1.041915 0.669060 0.385002 0.060 Uiso calc 1 . .
C C40 0.92104(14) 0.59354(18) 0.40252(13) 0.0524(8) Uani d 1 . .
C C21 0.77828(15) 0.55750(17) 0.28450(13) 0.0526(8) Uani d 1 . .
C C31 0.83760(14) 0.75046(19) 0.51517(12) 0.0538(8) Uani d 1 . .
C C26 0.81638(13) 0.79584(17) 0.46495(13) 0.0506(8) Uani d 1 . .
C C4 0.78281(14) 0.72419(19) 0.19112(12) 0.0523(8) Uani d 1 . .
C C34 0.79058(14) 0.55572(19) 0.47871(14) 0.0556(8) Uani d 1 . .
C C39 0.76263(15) 0.5143(2) 0.42909(14) 0.0607(9) Uani d 1 . .
H H39 0.749549 0.540146 0.394719 0.073 Uiso calc 1 . .
C C25 0.75416(15) 0.80125(18) 0.36141(12) 0.0580(8) Uani d 1 . .
H H25A 0.788441 0.819537 0.350919 0.070 Uiso calc 1 . .
H H25B 0.728565 0.845438 0.362886 0.070 Uiso calc 1 . .
C C24 0.71388(14) 0.74392(18) 0.31816(12) 0.0559(8) Uani d 1 . .
H H24A 0.678742 0.726986 0.327934 0.067 Uiso calc 1 . .
H H24B 0.696646 0.768255 0.281344 0.067 Uiso calc 1 . .
C C9 1.00665(14) 0.81378(18) 0.39906(12) 0.0544(8) Uani d 1 . .
H H9A 1.010664 0.783819 0.432237 0.065 Uiso calc 1 . .
H H9B 1.015934 0.867263 0.410773 0.065 Uiso calc 1 . .
C C22 0.75933(17) 0.4957(2) 0.24298(14) 0.0634(9) Uani d 1 . .
C C45 0.96325(16) 0.53591(19) 0.40083(14) 0.0595(9) Uani d 1 . .
H H45 0.951641 0.500797 0.371137 0.071 Uiso calc 1 . .
C C41 0.93867(14) 0.64476(19) 0.44682(14) 0.0581(8) Uani d 1 . .
H H41 0.910566 0.683324 0.447703 0.070 Uiso calc 1 . .
C C35 0.80994(15) 0.5166(2) 0.53017(14) 0.0626(9) Uani d 1 . .
H H35 0.828554 0.543580 0.563835 0.075 Uiso calc 1 . .
C C36 0.80127(16) 0.4373(2) 0.53080(17) 0.0724(10) Uani d 1 . .
H H36 0.813723 0.410494 0.564756 0.087 Uiso calc 1 . .
C C44 1.02267(16) 0.5316(2) 0.44389(16) 0.0675(10) Uani d 1 . .
H H44 1.051675 0.494183 0.443113 0.081 Uiso calc 1 . .
C C19 0.66830(15) 0.61617(18) 0.23968(13) 0.0621(9) Uani d 1 . .
H H19A 0.665624 0.649403 0.208368 0.075 Uiso calc 1 . .
H H19B 0.640637 0.637650 0.256904 0.075 Uiso calc 1 . .
C C43 1.03795(16) 0.5828(2) 0.48728(16) 0.0666(10) Uani d 1 . .
C C30 0.87277(17) 0.7878(2) 0.56849(15) 0.0678(9) Uani d 1 . .
C C28 0.89082(16) 0.90513(19) 0.51674(14) 0.0659(9) Uani d 1 . .
C C27 0.83332(15) 0.87873(17) 0.46489(13) 0.0607(9) Uani d 1 . .
H H27A 0.796896 0.909788 0.462471 0.073 Uiso calc 1 . .
H H27B 0.842091 0.888947 0.431352 0.073 Uiso calc 1 . .
C C18 0.64399(16) 0.5357(2) 0.21674(14) 0.0680(10) Uani d 1 . .
C C38 0.75398(16) 0.4358(2) 0.42995(16) 0.0693(10) Uani d 1 . .
H H38 0.734767 0.408362 0.396538 0.083 Uiso calc 1 . .
C C42 0.99769(16) 0.6397(2) 0.49014(14) 0.0666(9) Uani d 1 . .
H H42 1.009572 0.674041 0.520310 0.080 Uiso calc 1 . .
C C3 0.74440(16) 0.7869(2) 0.19078(14) 0.0655(9) Uani d 1 . .
H H3A 0.758677 0.824248 0.218897 0.079 Uiso calc 1 . .
C C5 0.76179(16) 0.6708(2) 0.14840(14) 0.0672(9) Uani d 1 . .
H H5 0.787844 0.629339 0.148330 0.081 Uiso calc 1 . .
C C15 1.06016(17) 0.83952(19) 0.33173(14) 0.0701(10) Uani d 1 . .
H H15A 1.088826 0.818125 0.316115 0.105 Uiso calc 1 . .
H H15B 1.075407 0.889248 0.347916 0.105 Uiso calc 1 . .
H H15C 1.018841 0.845162 0.302490 0.105 Uiso calc 1 . .
C C29 0.88290(17) 0.8731(2) 0.56898(14) 0.0710(10) Uani d 1 . .
H H29A 0.920447 0.886039 0.601720 0.085 Uiso calc 1 . .
H H29B 0.847052 0.898716 0.573198 0.085 Uiso calc 1 . .
C C37 0.77395(16) 0.3988(2) 0.48037(19) 0.0713(10) Uani d 1 . .
C C23 0.69345(16) 0.4967(2) 0.19936(14) 0.0726(10) Uani d 1 . .
H H23A 0.680241 0.443726 0.188760 0.087 Uiso calc 1 . .
H H23B 0.694256 0.522801 0.166131 0.087 Uiso calc 1 . .
C C14 1.12089(15) 0.7801(2) 0.42564(14) 0.0742(10) Uani d 1 . .
H H14A 1.118189 0.745758 0.454065 0.111 Uiso calc 1 . .
H H14B 1.133661 0.830553 0.441640 0.111 Uiso calc 1 . .
H H14C 1.151542 0.760639 0.411575 0.111 Uiso calc 1 . .
C C46 0.66604(18) 0.7378(3) 0.10724(16) 0.0812(11) Uani d 1 . .
C C6 0.70266(19) 0.6772(3) 0.10544(15) 0.0791(11) Uani d 1 . .
H H6 0.688639 0.641151 0.076380 0.095 Uiso calc 1 . .
C C33 0.95173(17) 0.8743(2) 0.51310(16) 0.0831(11) Uani d 1 . .
H H33A 0.949259 0.818939 0.509510 0.125 Uiso calc 1 . .
H H33B 0.987162 0.888138 0.546644 0.125 Uiso calc 1 . .
H H33C 0.957199 0.896237 0.480848 0.125 Uiso calc 1 . .
C C17 0.63175(18) 0.4872(2) 0.26157(17) 0.0875(12) Uani d 1 . .
H H17A 0.670640 0.481196 0.293764 0.131 Uiso calc 1 . .
H H17B 0.616002 0.437181 0.246323 0.131 Uiso calc 1 . .
H H17C 0.600946 0.512764 0.272725 0.131 Uiso calc 1 . .
C C2 0.68508(18) 0.7934(2) 0.14860(16) 0.0795(11) Uani d 1 . .
H H2A 0.658518 0.834447 0.148160 0.095 Uiso calc 1 . .
C C16 0.58150(18) 0.5454(2) 0.16554(17) 0.0996(14) Uani d 1 . .
H H16A 0.550401 0.569113 0.177259 0.149 Uiso calc 1 . .
H H16B 0.566489 0.495546 0.149430 0.149 Uiso calc 1 . .
H H16C 0.588558 0.577506 0.137932 0.149 Uiso calc 1 . .
C C32 0.8926(2) 0.9931(2) 0.51835(18) 0.0964(13) Uani d 1 . .
H H32A 0.896750 1.012411 0.484791 0.145 Uiso calc 1 . .
H H32B 0.928180 1.010059 0.550779 0.145 Uiso calc 1 . .
H H32C 0.854080 1.012447 0.520502 0.145 Uiso calc 1 . .
O O2W 0.85971(16) 0.5119(2) 0.17268(14) 0.1381(12) Uani d 1 . .
H H2WA 0.840883 0.493144 0.192778 0.207 Uiso d 1 . .
H H2WB 0.879123 0.473704 0.165798 0.207 Uiso d 1 . .
O O1W 0.93443(17) 0.6011(2) 0.65403(17) 0.1587(15) Uani d 1 . .
H H1WA 0.970580 0.620651 0.672785 0.238 Uiso d 1 . .
H H1WB 0.910130 0.639951 0.641847 0.238 Uiso d 1 . .
O O3W 0.92308(17) 0.3840(2) 0.2815(2) 0.1847(19) Uani d 1 . .
H H3WA 0.935932 0.338346 0.279348 0.277 Uiso d 1 . .
H H3WB 0.882892 0.380027 0.269188 0.277 Uiso d 1 . .
O O4W 0.9769(4) 0.2282(5) 0.2984(4) 0.180(3) Uani d 0.5 A 1
H H4WA 0.985140 0.227073 0.268724 0.270 Uiso d 0.5 A 1
H H4WB 0.962601 0.273503 0.298895 0.270 Uiso d 0.5 A 1
O O5W 0.9411(16) 0.241(2) 0.2313(14) 0.175(4) Uani d 0.125 B 2
H H5WA 0.911013 0.265707 0.236069 0.263 Uiso d 0.125 B 2
H H5WB 0.969813 0.275397 0.236599 0.263 Uiso d 0.125 B 2
O O6W 0.9656(16) 0.1682(18) 0.2174(11) 0.152(11) Uani d 0.125 C 3
H H6WA 0.942959 0.192682 0.187885 0.229 Uiso d 0.125 C 3
H H6WB 0.949669 0.123032 0.212835 0.229 Uiso d 0.125 C 3
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 N9 C13 . . 127.6(3) ?
C12 N9 H9 . . 116.2 ?
C13 N9 H9 . . 116.2 ?
N1 N10 C7 . . 117.5(2) ?
C20 N2 C24 . . 126.8(3) ?
C20 N2 H2 . . 116.6 ?
C24 N2 H2 . . 116.6 ?
C26 N3 C25 . . 127.1(3) ?
C26 N3 H3 . . 116.5 ?
C25 N3 H3 . . 116.5 ?
N10 N1 C4 . . 114.6(3) ?
N6 N7 C21 . . 117.1(3) ?
N7 N6 C40 . . 115.8(3) ?
N5 N4 C31 . . 117.6(3) ?
N4 N5 C34 . . 115.1(3) ?
N9 C12 C7 . . 120.4(3) ?
N9 C12 C11 . . 119.0(3) ?
C7 C12 C11 . . 120.6(3) ?
N10 C7 C12 . . 126.6(3) ?
N10 C7 C8 . . 114.2(3) ?
C12 C7 C8 . . 119.2(3) ?
O6 C8 C7 . . 122.3(3) ?
O6 C8 C9 . . 119.2(3) ?
C7 C8 C9 . . 118.5(3) ?
N2 C20 C21 . . 120.7(3) ?
N2 C20 C19 . . 117.8(3) ?
C21 C20 C19 . . 121.4(3) ?
C9 C10 C15 . . 110.9(3) ?
C9 C10 C14 . . 110.2(2) ?
C15 C10 C14 . . 109.7(3) ?
C9 C10 C11 . . 106.8(2) ?
C15 C10 C11 . . 110.9(2) ?
C14 C10 C11 . . 108.3(2) ?
N9 C13 C13 . 2_755 112.5(2) ?
N9 C13 H13A . . 109.1 ?
C13 C13 H13A 2_755 . 109.1 ?
N9 C13 H13B . . 109.1 ?
C13 C13 H13B 2_755 . 109.1 ?
H13A C13 H13B . . 107.8 ?
C12 C11 C10 . . 114.5(2) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.6 ?
C41 C40 C45 . . 119.8(3) ?
C41 C40 N6 . . 115.6(3) ?
C45 C40 N6 . . 124.6(3) ?
N7 C21 C20 . . 126.0(3) ?
N7 C21 C22 . . 114.2(3) ?
C20 C21 C22 . . 119.8(3) ?
N4 C31 C26 . . 126.1(3) ?
N4 C31 C30 . . 115.0(3) ?
C26 C31 C30 . . 118.9(3) ?
N3 C26 C31 . . 119.6(3) ?
N3 C26 C27 . . 118.3(3) ?
C31 C26 C27 . . 122.2(3) ?
C5 C4 C3 . . 119.4(3) ?
C5 C4 N1 . . 115.6(3) ?
C3 C4 N1 . . 125.0(3) ?
C39 C34 C35 . . 119.2(3) ?
C39 C34 N5 . . 116.3(3) ?
C35 C34 N5 . . 124.5(3) ?
C38 C39 C34 . . 120.9(3) ?
C38 C39 H39 . . 119.5 ?
C34 C39 H39 . . 119.5 ?
N3 C25 C24 . . 109.4(2) ?
N3 C25 H25A . . 109.8 ?
C24 C25 H25A . . 109.8 ?
N3 C25 H25B . . 109.8 ?
C24 C25 H25B . . 109.8 ?
H25A C25 H25B . . 108.2 ?
N2 C24 C25 . . 109.3(2) ?
N2 C24 H24A . . 109.8 ?
C25 C24 H24A . . 109.8 ?
N2 C24 H24B . . 109.8 ?
C25 C24 H24B . . 109.8 ?
H24A C24 H24B . . 108.3 ?
C8 C9 C10 . . 115.5(2) ?
C8 C9 H9A . . 108.4 ?
C10 C9 H9A . . 108.4 ?
C8 C9 H9B . . 108.4 ?
C10 C9 H9B . . 108.4 ?
H9A C9 H9B . . 107.5 ?
O7 C22 C21 . . 122.5(3) ?
O7 C22 C23 . . 119.2(3) ?
C21 C22 C23 . . 118.3(3) ?
C44 C45 C40 . . 119.3(3) ?
C44 C45 H45 . . 120.4 ?
C40 C45 H45 . . 120.4 ?
C40 C41 C42 . . 120.9(3) ?
C40 C41 H41 . . 119.6 ?
C42 C41 H41 . . 119.6 ?
C36 C35 C34 . . 119.7(3) ?
C36 C35 H35 . . 120.2 ?
C34 C35 H35 . . 120.2 ?
C37 C36 C35 . . 118.9(3) ?
C37 C36 H36 . . 120.6 ?
C35 C36 H36 . . 120.6 ?
C43 C44 C45 . . 119.1(3) ?
C43 C44 H44 . . 120.5 ?
C45 C44 H44 . . 120.5 ?
C20 C19 C18 . . 114.3(3) ?
C20 C19 H19A . . 108.7 ?
C18 C19 H19A . . 108.7 ?
C20 C19 H19B . . 108.7 ?
C18 C19 H19B . . 108.7 ?
H19A C19 H19B . . 107.6 ?
F2 C43 C44 . . 118.8(3) ?
F2 C43 C42 . . 118.2(4) ?
C44 C43 C42 . . 123.0(3) ?
O3 C30 C31 . . 121.8(3) ?
O3 C30 C29 . . 119.7(3) ?
C31 C30 C29 . . 118.5(3) ?
C32 C28 C33 . . 109.7(3) ?
C32 C28 C29 . . 110.5(3) ?
C33 C28 C29 . . 110.0(3) ?
C32 C28 C27 . . 109.0(3) ?
C33 C28 C27 . . 109.9(3) ?
C29 C28 C27 . . 107.8(3) ?
C26 C27 C28 . . 114.9(3) ?
C26 C27 H27A . . 108.5 ?
C28 C27 H27A . . 108.5 ?
C26 C27 H27B . . 108.5 ?
C28 C27 H27B . . 108.5 ?
H27A C27 H27B . . 107.5 ?
C23 C18 C19 . . 108.4(3) ?
C23 C18 C17 . . 110.1(3) ?
C19 C18 C17 . . 110.6(3) ?
C23 C18 C16 . . 110.3(3) ?
C19 C18 C16 . . 108.2(3) ?
C17 C18 C16 . . 109.1(3) ?
C37 C38 C39 . . 118.9(3) ?
C37 C38 H38 . . 120.6 ?
C39 C38 H38 . . 120.6 ?
C43 C42 C41 . . 118.0(3) ?
C43 C42 H42 . . 121.0 ?
C41 C42 H42 . . 121.0 ?
C2 C3 C4 . . 119.7(3) ?
C2 C3 H3A . . 120.1 ?
C4 C3 H3A . . 120.1 ?
C4 C5 C6 . . 121.4(3) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C10 C15 H15A . . 109.5 ?
C10 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C10 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C30 C29 C28 . . 114.9(3) ?
C30 C29 H29A . . 108.5 ?
C28 C29 H29A . . 108.5 ?
C30 C29 H29B . . 108.5 ?
C28 C29 H29B . . 108.5 ?
H29A C29 H29B . . 107.5 ?
F3 C37 C38 . . 119.8(4) ?
F3 C37 C36 . . 117.7(4) ?
C38 C37 C36 . . 122.5(3) ?
C22 C23 C18 . . 115.6(3) ?
C22 C23 H23A . . 108.4 ?
C18 C23 H23A . . 108.4 ?
C22 C23 H23B . . 108.4 ?
C18 C23 H23B . . 108.4 ?
H23A C23 H23B . . 107.4 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C6 C46 F4 . . 117.9(4) ?
C6 C46 C2 . . 123.4(3) ?
F4 C46 C2 . . 118.7(4) ?
C46 C6 C5 . . 117.6(4) ?
C46 C6 H6 . . 121.2 ?
C5 C6 H6 . . 121.2 ?
C28 C33 H33A . . 109.5 ?
C28 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C28 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C18 C17 H17A . . 109.5 ?
C18 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C18 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C46 C2 C3 . . 118.5(4) ?
C46 C2 H2A . . 120.7 ?
C3 C2 H2A . . 120.7 ?
C18 C16 H16A . . 109.5 ?
C18 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C18 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C28 C32 H32A . . 109.5 ?
C28 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C28 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
H2WA O2W H2WB . . 104.5 ?
H1WA O1W H1WB . . 104.5 ?
H3WA O3W H3WB . . 104.5 ?
H4WA O4W H4WB . . 104.5 ?
H5WA O5W H5WB . . 104.5 ?
O6W O6W H6WA 2_755 . 147.7 ?
O6W O6W H6WB 2_755 . 107.6 ?
H6WA O6W H6WB . . 104.5 ?
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
F2 C43 . 1.357(4) ?
O6 C8 . 1.227(3) ?
N9 C12 . 1.329(3) ?
N9 C13 . 1.454(4) ?
N9 H9 . 0.8600 ?
F3 C37 . 1.353(4) ?
N10 N1 . 1.278(3) ?
N10 C7 . 1.380(3) ?
N2 C20 . 1.323(3) ?
N2 C24 . 1.461(4) ?
N2 H2 . 0.8600 ?
N3 C26 . 1.319(3) ?
N3 C25 . 1.464(3) ?
N3 H3 . 0.8600 ?
N1 C4 . 1.423(4) ?
N7 N6 . 1.276(3) ?
N7 C21 . 1.383(4) ?
N6 C40 . 1.418(4) ?
N4 N5 . 1.270(3) ?
N4 C31 . 1.383(4) ?
O7 C22 . 1.240(4) ?
N5 C34 . 1.414(4) ?
F4 C46 . 1.365(4) ?
O3 C30 . 1.242(4) ?
C12 C7 . 1.409(4) ?
C12 C11 . 1.491(4) ?
C7 C8 . 1.455(4) ?
C8 C9 . 1.496(4) ?
C20 C21 . 1.415(4) ?
C20 C19 . 1.494(4) ?
C10 C9 . 1.513(4) ?
C10 C15 . 1.525(4) ?
C10 C14 . 1.529(4) ?
C10 C11 . 1.534(4) ?
C13 C13 2_755 1.507(6) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C40 C41 . 1.374(4) ?
C40 C45 . 1.396(4) ?
C21 C22 . 1.453(4) ?
C31 C26 . 1.426(4) ?
C31 C30 . 1.448(4) ?
C26 C27 . 1.483(4) ?
C4 C5 . 1.372(4) ?
C4 C3 . 1.390(4) ?
C34 C39 . 1.386(4) ?
C34 C35 . 1.397(4) ?
C39 C38 . 1.374(4) ?
C39 H39 . 0.9300 ?
C25 C24 . 1.510(4) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C22 C23 . 1.493(4) ?
C45 C44 . 1.386(4) ?
C45 H45 . 0.9300 ?
C41 C42 . 1.384(4) ?
C41 H41 . 0.9300 ?
C35 C36 . 1.385(5) ?
C35 H35 . 0.9300 ?
C36 C37 . 1.375(5) ?
C36 H36 . 0.9300 ?
C44 C43 . 1.360(5) ?
C44 H44 . 0.9300 ?
C19 C18 . 1.529(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C43 C42 . 1.365(5) ?
C30 C29 . 1.491(5) ?
C28 C32 . 1.521(5) ?
C28 C33 . 1.522(5) ?
C28 C29 . 1.522(5) ?
C28 C27 . 1.539(4) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C18 C23 . 1.517(5) ?
C18 C17 . 1.531(5) ?
C18 C16 . 1.536(4) ?
C38 C37 . 1.357(5) ?
C38 H38 . 0.9300 ?
C42 H42 . 0.9300 ?
C3 C2 . 1.378(5) ?
C3 H3A . 0.9300 ?
C5 C6 . 1.383(5) ?
C5 H5 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C46 C6 . 1.350(5) ?
C46 C2 . 1.373(5) ?
C6 H6 . 0.9300 ?
C33 H33A . 0.9600 ?
C33 H33B . 0.9600 ?
C33 H33C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C2 H2A . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C32 H32A . 0.9600 ?
C32 H32B . 0.9600 ?
C32 H32C . 0.9600 ?
O2W H2WA . 0.8500 ?
O2W H2WB . 0.8497 ?
O1W H1WA . 0.8499 ?
O1W H1WB . 0.8500 ?
O3W H3WA . 0.8500 ?
O3W H3WB . 0.8500 ?
O4W H4WA . 0.8503 ?
O4W H4WB . 0.8499 ?
O5W H5WA . 0.8501 ?
O5W H5WB . 0.8501 ?
O6W O6W 2_755 1.80(6) ?
O6W H6WA . 0.8499 ?
O6W H6WB . 0.8500 ?
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
N9 H9 N1 . 0.86 1.93 2.609(3) 134.7 yes
N2 H2 N6 . 0.86 1.91 2.585(3) 134.3 yes
N3 H3 N5 . 0.86 1.90 2.582(3) 135.6 yes
C13 H13B O2W 2_755 0.97 2.59 3.302(4) 130.4 yes
C25 H25A O6 . 0.97 2.46 3.370(4) 156.1 yes
C24 H24A O3 7_666 0.97 2.65 3.518(4) 148.9 yes
C24 H24A O5W 4_655 0.97 2.58 3.27(4) 127.6 yes
C27 H27B O6 . 0.97 2.58 3.451(4) 149.0 yes
C42 H42 F4 8_566 0.93 2.52 3.218(4) 132.2 yes
C5 H5 O2W . 0.93 2.53 3.441(5) 165.8 yes
C23 H23A O6 4_645 0.97 2.43 3.311(4) 150.8 yes
O2W H2WA O7 . 0.85 2.08 2.926(4) 178.0 yes
O2W H2WB O1W 6_565 0.85 1.91 2.749(5) 170.6 yes
O1W H1WA O3W 5_766 0.85 2.26 3.042(5) 153.9 yes
O1W H1WB O3 . 0.85 2.03 2.812(4) 151.6 yes
O3W H3WA O4W . 0.85 2.09 2.921(10) 164.0 yes
O3W H3WA O5W . 0.85 2.11 2.88(4) 150.7 yes
O3W H3WB O7 . 0.85 2.13 2.866(4) 144.4 yes
O4W H4WA O4W 2_755 0.85 2.20 3.04(2) 170.3 yes
O4W H4WB O3W . 0.85 2.08 2.921(10) 167.7 yes
O5W H5WA O3W . 0.85 2.32 2.88(4) 124.0 yes
O5W H5WB O5W 2_755 0.85 1.97 2.48(7) 118.1 yes
O6W H6WA O3 6_565 0.85 2.06 2.90(2) 174.9 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N10 N1 C4 . . . . -175.2(2) ?
C21 N7 N6 C40 . . . . 177.4(2) ?
C31 N4 N5 C34 . . . . 177.7(3) ?
C13 N9 C12 C7 . . . . -173.7(2) ?
C13 N9 C12 C11 . . . . 5.7(4) ?
N1 N10 C7 C12 . . . . -0.6(4) ?
N1 N10 C7 C8 . . . . -177.4(2) ?
N9 C12 C7 N10 . . . . -8.4(4) ?
C11 C12 C7 N10 . . . . 172.2(3) ?
N9 C12 C7 C8 . . . . 168.2(2) ?
C11 C12 C7 C8 . . . . -11.2(4) ?
N10 C7 C8 O6 . . . . 9.6(4) ?
C12 C7 C8 O6 . . . . -167.4(3) ?
N10 C7 C8 C9 . . . . -172.5(2) ?
C12 C7 C8 C9 . . . . 10.4(4) ?
C24 N2 C20 C21 . . . . 178.8(3) ?
C24 N2 C20 C19 . . . . 0.2(4) ?
C12 N9 C13 C13 . . . 2_755 -111.6(3) ?
N9 C12 C11 C10 . . . . 159.0(3) ?
C7 C12 C11 C10 . . . . -21.6(4) ?
C9 C10 C11 C12 . . . . 51.5(3) ?
C15 C10 C11 C12 . . . . -69.4(3) ?
C14 C10 C11 C12 . . . . 170.2(3) ?
N7 N6 C40 C41 . . . . -171.5(3) ?
N7 N6 C40 C45 . . . . 7.8(4) ?
N6 N7 C21 C20 . . . . -0.6(4) ?
N6 N7 C21 C22 . . . . 179.5(3) ?
N2 C20 C21 N7 . . . . 5.5(5) ?
C19 C20 C21 N7 . . . . -175.9(3) ?
N2 C20 C21 C22 . . . . -174.6(3) ?
C19 C20 C21 C22 . . . . 4.0(4) ?
N5 N4 C31 C26 . . . . -1.5(5) ?
N5 N4 C31 C30 . . . . 178.8(3) ?
C25 N3 C26 C31 . . . . 179.9(3) ?
C25 N3 C26 C27 . . . . 0.1(4) ?
N4 C31 C26 N3 . . . . 5.5(5) ?
C30 C31 C26 N3 . . . . -174.9(3) ?
N4 C31 C26 C27 . . . . -174.8(3) ?
C30 C31 C26 C27 . . . . 4.8(4) ?
N10 N1 C4 C5 . . . . -177.7(3) ?
N10 N1 C4 C3 . . . . 3.6(4) ?
N4 N5 C34 C39 . . . . -173.0(3) ?
N4 N5 C34 C35 . . . . 7.8(4) ?
C35 C34 C39 C38 . . . . -0.2(5) ?
N5 C34 C39 C38 . . . . -179.4(3) ?
C26 N3 C25 C24 . . . . -178.3(3) ?
C20 N2 C24 C25 . . . . -176.4(3) ?
N3 C25 C24 N2 . . . . -59.1(3) ?
O6 C8 C9 C10 . . . . -158.5(3) ?
C7 C8 C9 C10 . . . . 23.6(4) ?
C15 C10 C9 C8 . . . . 68.3(3) ?
C14 C10 C9 C8 . . . . -170.0(3) ?
C11 C10 C9 C8 . . . . -52.6(3) ?
N7 C21 C22 O7 . . . . -3.2(5) ?
C20 C21 C22 O7 . . . . 176.8(3) ?
N7 C21 C22 C23 . . . . 178.6(3) ?
C20 C21 C22 C23 . . . . -1.3(4) ?
C41 C40 C45 C44 . . . . -0.4(4) ?
N6 C40 C45 C44 . . . . -179.7(3) ?
C45 C40 C41 C42 . . . . -0.5(5) ?
N6 C40 C41 C42 . . . . 178.9(3) ?
C39 C34 C35 C36 . . . . 0.4(5) ?
N5 C34 C35 C36 . . . . 179.5(3) ?
C34 C35 C36 C37 . . . . 0.4(5) ?
C40 C45 C44 C43 . . . . 1.2(5) ?
N2 C20 C19 C18 . . . . -158.9(3) ?
C21 C20 C19 C18 . . . . 22.5(4) ?
C45 C44 C43 F2 . . . . 178.3(3) ?
C45 C44 C43 C42 . . . . -1.1(5) ?
N4 C31 C30 O3 . . . . 1.6(5) ?
C26 C31 C30 O3 . . . . -178.1(3) ?
N4 C31 C30 C29 . . . . -177.7(3) ?
C26 C31 C30 C29 . . . . 2.7(5) ?
N3 C26 C27 C28 . . . . -161.6(3) ?
C31 C26 C27 C28 . . . . 18.7(4) ?
C32 C28 C27 C26 . . . . -166.1(3) ?
C33 C28 C27 C26 . . . . 73.8(4) ?
C29 C28 C27 C26 . . . . -46.1(4) ?
C20 C19 C18 C23 . . . . -48.5(4) ?
C20 C19 C18 C17 . . . . 72.4(4) ?
C20 C19 C18 C16 . . . . -168.1(3) ?
C34 C39 C38 C37 . . . . -0.7(5) ?
F2 C43 C42 C41 . . . . -179.1(3) ?
C44 C43 C42 C41 . . . . 0.3(5) ?
C40 C41 C42 C43 . . . . 0.5(5) ?
C5 C4 C3 C2 . . . . 1.9(5) ?
N1 C4 C3 C2 . . . . -179.4(3) ?
C3 C4 C5 C6 . . . . -1.1(5) ?
N1 C4 C5 C6 . . . . -179.9(3) ?
O3 C30 C29 C28 . . . . 146.9(3) ?
C31 C30 C29 C28 . . . . -33.8(4) ?
C32 C28 C29 C30 . . . . 173.0(3) ?
C33 C28 C29 C30 . . . . -65.8(4) ?
C27 C28 C29 C30 . . . . 54.0(4) ?
C39 C38 C37 F3 . . . . -178.6(3) ?
C39 C38 C37 C36 . . . . 1.5(5) ?
C35 C36 C37 F3 . . . . 178.8(3) ?
C35 C36 C37 C38 . . . . -1.3(5) ?
O7 C22 C23 C18 . . . . 153.5(3) ?
C21 C22 C23 C18 . . . . -28.2(5) ?
C19 C18 C23 C22 . . . . 51.9(4) ?
C17 C18 C23 C22 . . . . -69.2(4) ?
C16 C18 C23 C22 . . . . 170.2(3) ?
F4 C46 C6 C5 . . . . -178.7(3) ?
C2 C46 C6 C5 . . . . 1.3(6) ?
C4 C5 C6 C46 . . . . -0.5(5) ?
C6 C46 C2 C3 . . . . -0.5(6) ?
F4 C46 C2 C3 . . . . 179.5(3) ?
C4 C3 C2 C46 . . . . -1.2(5) ?
