#------------------------------------------------------------------------------
#$Date: 2022-11-08 21:40:13 +0200 (Tue, 08 Nov 2022) $
#$Revision: 279111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022674.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_2022674
loop_
_publ_author_name
'Wójcicka, Anna'
'Becan, Lilianna'
'Rembiałkowska, Nina'
'Pyra, Anna'
'Bryndal, Iwona'
_publ_section_title
;
 Structure and cytotoxic properties of
 1-hydroxy-5-methyl-7-phenylpyrido[3,4-d]pyridazin-4(3H)-one
 and its mono- and disubstituted ethyl acetates
;
_journal_coeditor_code           QF3056
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              559
_journal_page_last               569
_journal_paper_doi               10.1107/S2053229622009202
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H23 N3 O6'
_chemical_formula_moiety         'C22 H23 N3 O6'
_chemical_formula_sum            'C22 H23 N3 O6'
_chemical_formula_weight         425.43
_chemical_name_systematic
;Ethyl
[(5-methyl-4-oxo-7-phenyl-3,4-dihydropyrido[3,4-d]pyridazin-1-yl)oxy]acetate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                92.24(2)
_cell_angle_beta                 106.06(3)
_cell_angle_gamma                109.46(3)
_cell_formula_units_Z            2
_cell_length_a                   8.679(2)
_cell_length_b                   8.751(2)
_cell_length_c                   15.137(4)
_cell_measurement_reflns_used    1514
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4
_cell_measurement_theta_min      3.1
_cell_volume                     1030.7(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2014)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Rigaku Xcalibur Onyx'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7128
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.255
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.385
_refine_ls_extinction_coef       0.0037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0627
_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)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                2089
_reflns_number_total             4142
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qf3056sup1.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 2022672--2022674.cif.'
_cod_database_code               2022674
_cod_database_fobs_code          2022674
_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   0.928
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2620(4) 0.4605(4) 0.3410(2) 0.0254(7) Uani d 1 . .
O O1 0.1154(3) 0.4540(3) 0.35841(16) 0.0280(5) Uani d 1 . .
C C11 -0.0362(4) 0.3256(4) 0.3014(2) 0.0278(7) Uani d 1 . .
H H111 -0.131455 0.312960 0.327715 0.033 Uiso calc 1 . .
H H112 -0.015212 0.221076 0.301129 0.033 Uiso calc 1 . .
C C12 -0.0874(4) 0.3619(4) 0.2024(2) 0.0271(7) Uani d 1 . .
O O12 -0.0317(3) 0.4891(3) 0.17669(17) 0.0319(6) Uani d 1 . .
C C13 -0.2667(5) 0.2383(5) 0.0501(3) 0.0419(10) Uani d 1 . .
H H131 -0.284006 0.343818 0.042431 0.050 Uiso calc 1 . .
H H132 -0.377843 0.148709 0.019592 0.050 Uiso calc 1 . .
O O13 -0.2094(3) 0.2259(3) 0.14844(17) 0.0335(6) Uani d 1 . .
C C14 -0.1360(6) 0.2276(6) 0.0046(3) 0.0553(12) Uani d 1 . .
H H141 -0.025470 0.315251 0.035544 0.083 Uiso calc 1 . .
H H142 -0.174650 0.239485 -0.061125 0.083 Uiso calc 1 . .
H H143 -0.122656 0.121111 0.009848 0.083 Uiso calc 1 . .
N N2 0.2563(3) 0.3601(3) 0.27490(19) 0.0255(6) Uani d 1 . .
N N3 0.4096(3) 0.3724(3) 0.26150(19) 0.0250(6) Uani d 1 . .
C C31 0.3876(5) 0.2649(4) 0.1803(2) 0.0291(7) Uani d 1 . .
H H311 0.294619 0.158906 0.175297 0.035 Uiso calc 1 . .
H H312 0.494912 0.243630 0.186311 0.035 Uiso calc 1 . .
C C32 0.3434(4) 0.3423(4) 0.0937(2) 0.0259(7) Uani d 1 . .
O O32 0.3488(3) 0.4824(3) 0.09355(17) 0.0342(6) Uani d 1 . .
C C33 0.2566(5) 0.2991(4) -0.0702(2) 0.0340(8) Uani d 1 . .
H H331 0.355936 0.394237 -0.072688 0.041 Uiso calc 1 . .
H H332 0.157605 0.334695 -0.076461 0.041 Uiso calc 1 . .
O O33 0.2984(3) 0.2349(3) 0.01799(16) 0.0303(6) Uani d 1 . .
C C34 0.2136(7) 0.1640(6) -0.1464(3) 0.0586(13) Uani d 1 . .
H H341 0.190424 0.204147 -0.206420 0.088 Uiso calc 1 . .
H H342 0.111686 0.072779 -0.145100 0.088 Uiso calc 1 . .
H H343 0.310542 0.126304 -0.137717 0.088 Uiso calc 1 . .
C C4 0.5693(4) 0.4836(4) 0.3110(2) 0.0267(7) Uani d 1 . .
O O4 0.6969(3) 0.4861(3) 0.28866(18) 0.0376(6) Uani d 1 . .
C C5 0.7260(4) 0.7091(4) 0.4497(2) 0.0294(8) Uani d 1 . .
C C51 0.9019(4) 0.7287(5) 0.4444(3) 0.0377(9) Uani d 1 . .
H H511 0.909036 0.754376 0.382928 0.057 Uiso calc 1 . .
H H512 0.922899 0.626558 0.454786 0.057 Uiso calc 1 . .
H H513 0.988388 0.817905 0.492179 0.057 Uiso calc 1 . .
N N6 0.7226(3) 0.8078(3) 0.51761(19) 0.0277(6) Uani d 1 . .
C C7 0.5707(4) 0.8014(4) 0.5292(2) 0.0257(7) Uani d 1 . .
C C71 0.5809(4) 0.9194(4) 0.6049(2) 0.0248(7) Uani d 1 . .
C C72 0.7405(4) 1.0315(4) 0.6607(2) 0.0289(8) Uani d 1 . .
H H72 0.843074 1.028627 0.650965 0.035 Uiso calc 1 . .
C C73 0.7501(5) 1.1461(4) 0.7300(2) 0.0345(8) Uani d 1 . .
H H73 0.858905 1.221882 0.766524 0.041 Uiso calc 1 . .
C C74 0.6019(5) 1.1506(4) 0.7460(2) 0.0338(8) Uani d 1 . .
H H74 0.608836 1.229495 0.793324 0.041 Uiso calc 1 . .
C C75 0.4441(5) 1.0397(4) 0.6929(2) 0.0337(8) Uani d 1 . .
H H75 0.342569 1.041059 0.704692 0.040 Uiso calc 1 . .
C C76 0.4330(5) 0.9267(4) 0.6228(2) 0.0302(8) Uani d 1 . .
H H76 0.323325 0.852674 0.586150 0.036 Uiso calc 1 . .
C C8 0.4162(4) 0.6887(4) 0.4729(2) 0.0257(7) Uani d 1 . .
H H8 0.310806 0.683071 0.482375 0.031 Uiso calc 1 . .
C C9 0.4185(4) 0.5840(4) 0.4022(2) 0.0232(7) Uani d 1 . .
C C10 0.5727(4) 0.5921(4) 0.3879(2) 0.0261(7) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N2 C1 O1 . . 119.9(3) ?
N2 C1 C9 . . 124.7(3) ?
O1 C1 C9 . . 115.4(3) ?
C1 O1 C11 . . 114.7(2) ?
O1 C11 C12 . . 111.2(3) ?
O1 C11 H111 . . 109.4 ?
C12 C11 H111 . . 109.4 ?
O1 C11 H112 . . 109.4 ?
C12 C11 H112 . . 109.4 ?
H111 C11 H112 . . 108.0 ?
O12 C12 O13 . . 125.3(3) ?
O12 C12 C11 . . 126.0(3) ?
O13 C12 C11 . . 108.6(3) ?
O13 C13 C14 . . 110.4(3) ?
O13 C13 H131 . . 109.6 ?
C14 C13 H131 . . 109.6 ?
O13 C13 H132 . . 109.6 ?
C14 C13 H132 . . 109.6 ?
H131 C13 H132 . . 108.1 ?
C12 O13 C13 . . 115.4(3) ?
C13 C14 H141 . . 109.5 ?
C13 C14 H142 . . 109.5 ?
H141 C14 H142 . . 109.5 ?
C13 C14 H143 . . 109.5 ?
H141 C14 H143 . . 109.5 ?
H142 C14 H143 . . 109.5 ?
C1 N2 N3 . . 116.9(3) ?
N2 N3 C4 . . 126.5(3) ?
N2 N3 C31 . . 112.5(3) ?
C4 N3 C31 . . 120.7(3) ?
N3 C31 C32 . . 110.2(3) ?
N3 C31 H311 . . 109.6 ?
C32 C31 H311 . . 109.6 ?
N3 C31 H312 . . 109.6 ?
C32 C31 H312 . . 109.6 ?
H311 C31 H312 . . 108.1 ?
O32 C32 O33 . . 125.0(3) ?
O32 C32 C31 . . 124.6(3) ?
O33 C32 C31 . . 110.4(3) ?
O33 C33 C34 . . 107.2(3) ?
O33 C33 H331 . . 110.3 ?
C34 C33 H331 . . 110.3 ?
O33 C33 H332 . . 110.3 ?
C34 C33 H332 . . 110.3 ?
H331 C33 H332 . . 108.5 ?
C32 O33 C33 . . 114.8(3) ?
C33 C34 H341 . . 109.5 ?
C33 C34 H342 . . 109.5 ?
H341 C34 H342 . . 109.5 ?
C33 C34 H343 . . 109.5 ?
H341 C34 H343 . . 109.5 ?
H342 C34 H343 . . 109.5 ?
O4 C4 N3 . . 119.8(3) ?
O4 C4 C10 . . 124.8(3) ?
N3 C4 C10 . . 115.4(3) ?
N6 C5 C10 . . 121.6(3) ?
N6 C5 C51 . . 115.3(3) ?
C10 C5 C51 . . 123.0(3) ?
C5 C51 H511 . . 109.5 ?
C5 C51 H512 . . 109.5 ?
H511 C51 H512 . . 109.5 ?
C5 C51 H513 . . 109.5 ?
H511 C51 H513 . . 109.5 ?
H512 C51 H513 . . 109.5 ?
C5 N6 C7 . . 120.7(3) ?
N6 C7 C8 . . 121.1(3) ?
N6 C7 C71 . . 116.3(3) ?
C8 C7 C71 . . 122.6(3) ?
C76 C71 C72 . . 117.5(3) ?
C76 C71 C7 . . 121.7(3) ?
C72 C71 C7 . . 120.8(3) ?
C73 C72 C71 . . 120.9(3) ?
C73 C72 H72 . . 119.6 ?
C71 C72 H72 . . 119.6 ?
C74 C73 C72 . . 120.4(3) ?
C74 C73 H73 . . 119.8 ?
C72 C73 H73 . . 119.8 ?
C75 C74 C73 . . 119.6(3) ?
C75 C74 H74 . . 120.2 ?
C73 C74 H74 . . 120.2 ?
C74 C75 C76 . . 120.5(4) ?
C74 C75 H75 . . 119.8 ?
C76 C75 H75 . . 119.8 ?
C75 C76 C71 . . 121.2(3) ?
C75 C76 H76 . . 119.4 ?
C71 C76 H76 . . 119.4 ?
C7 C8 C9 . . 118.6(3) ?
C7 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
C8 C9 C10 . . 120.9(3) ?
C8 C9 C1 . . 122.0(3) ?
C10 C9 C1 . . 117.1(3) ?
C9 C10 C5 . . 117.1(3) ?
C9 C10 C4 . . 119.2(3) ?
C5 C10 C4 . . 123.7(3) ?
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
C1 N2 . 1.285(4) ?
C1 O1 . 1.353(4) ?
C1 C9 . 1.456(4) ?
O1 C11 . 1.432(4) ?
C11 C12 . 1.519(5) ?
C11 H111 . 0.9900 ?
C11 H112 . 0.9900 ?
C12 O12 . 1.185(4) ?
C12 O13 . 1.345(4) ?
C13 O13 . 1.454(4) ?
C13 C14 . 1.506(6) ?
C13 H131 . 0.9900 ?
C13 H132 . 0.9900 ?
C14 H141 . 0.9800 ?
C14 H142 . 0.9800 ?
C14 H143 . 0.9800 ?
N2 N3 . 1.371(4) ?
N3 C4 . 1.378(4) ?
N3 C31 . 1.447(4) ?
C31 C32 . 1.512(5) ?
C31 H311 . 0.9900 ?
C31 H312 . 0.9900 ?
C32 O32 . 1.211(4) ?
C32 O33 . 1.331(4) ?
C33 O33 . 1.468(4) ?
C33 C34 . 1.493(5) ?
C33 H331 . 0.9900 ?
C33 H332 . 0.9900 ?
C34 H341 . 0.9800 ?
C34 H342 . 0.9800 ?
C34 H343 . 0.9800 ?
C4 O4 . 1.238(4) ?
C4 C10 . 1.461(5) ?
C5 N6 . 1.329(4) ?
C5 C10 . 1.422(5) ?
C5 C51 . 1.504(5) ?
C51 H511 . 0.9800 ?
C51 H512 . 0.9800 ?
C51 H513 . 0.9800 ?
N6 C7 . 1.361(4) ?
C7 C8 . 1.385(5) ?
C7 C71 . 1.475(5) ?
C71 C76 . 1.405(5) ?
C71 C72 . 1.406(5) ?
C72 C73 . 1.387(5) ?
C72 H72 . 0.9500 ?
C73 C74 . 1.387(5) ?
C73 H73 . 0.9500 ?
C74 C75 . 1.381(5) ?
C74 H74 . 0.9500 ?
C75 C76 . 1.382(5) ?
C75 H75 . 0.9500 ?
C76 H76 . 0.9500 ?
C8 C9 . 1.390(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.393(4) ?
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
C11 H111 O4 1_455 0.99 2.44 3.053(4) 119.6 yes
C13 H131 O32 2_565 0.99 2.65 3.454(5) 138.1 yes
C14 H141 O12 . 0.98 2.60 3.113(5) 112.9 yes
C33 H331 O32 2_665 0.99 2.54 3.445(5) 151.6 yes
C33 H332 O12 2_565 0.99 2.50 3.278(4) 135.1 yes
C73 H73 O12 2_676 0.95 2.44 3.271(4) 145.4 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
N2 C1 O1 C11 . . . . 2.7(4) ?
C9 C1 O1 C11 . . . . -176.4(3) ?
C1 O1 C11 C12 . . . . -72.1(3) ?
O1 C11 C12 O12 . . . . -12.4(5) ?
O1 C11 C12 O13 . . . . 168.7(3) ?
O12 C12 O13 C13 . . . . 3.9(5) ?
C11 C12 O13 C13 . . . . -177.2(3) ?
C14 C13 O13 C12 . . . . 76.7(4) ?
O1 C1 N2 N3 . . . . -179.5(3) ?
C9 C1 N2 N3 . . . . -0.5(5) ?
C1 N2 N3 C4 . . . . -1.1(5) ?
C1 N2 N3 C31 . . . . -174.5(3) ?
N2 N3 C31 C32 . . . . 81.7(3) ?
C4 N3 C31 C32 . . . . -92.2(4) ?
N3 C31 C32 O32 . . . . 9.4(5) ?
N3 C31 C32 O33 . . . . -170.9(3) ?
O32 C32 O33 C33 . . . . 1.1(5) ?
C31 C32 O33 C33 . . . . -178.6(3) ?
C34 C33 O33 C32 . . . . 178.7(3) ?
N2 N3 C4 O4 . . . . -176.6(3) ?
C31 N3 C4 O4 . . . . -3.7(5) ?
N2 N3 C4 C10 . . . . 3.3(5) ?
C31 N3 C4 C10 . . . . 176.2(3) ?
C10 C5 N6 C7 . . . . -1.0(5) ?
C51 C5 N6 C7 . . . . 179.9(3) ?
C5 N6 C7 C8 . . . . 2.2(5) ?
C5 N6 C7 C71 . . . . -178.2(3) ?
N6 C7 C71 C76 . . . . 179.0(3) ?
C8 C7 C71 C76 . . . . -1.5(5) ?
N6 C7 C71 C72 . . . . 0.2(5) ?
C8 C7 C71 C72 . . . . 179.7(3) ?
C76 C71 C72 C73 . . . . -0.9(5) ?
C7 C71 C72 C73 . . . . 177.9(3) ?
C71 C72 C73 C74 . . . . 0.9(5) ?
C72 C73 C74 C75 . . . . 0.3(5) ?
C73 C74 C75 C76 . . . . -1.3(5) ?
C74 C75 C76 C71 . . . . 1.2(5) ?
C72 C71 C76 C75 . . . . -0.1(5) ?
C7 C71 C76 C75 . . . . -178.9(3) ?
N6 C7 C8 C9 . . . . -1.6(5) ?
C71 C7 C8 C9 . . . . 178.9(3) ?
C7 C8 C9 C10 . . . . -0.1(5) ?
C7 C8 C9 C1 . . . . 179.0(3) ?
N2 C1 C9 C8 . . . . -179.7(3) ?
O1 C1 C9 C8 . . . . -0.6(5) ?
N2 C1 C9 C10 . . . . -0.5(5) ?
O1 C1 C9 C10 . . . . 178.5(3) ?
C8 C9 C10 C5 . . . . 1.2(5) ?
C1 C9 C10 C5 . . . . -178.0(3) ?
C8 C9 C10 C4 . . . . -178.0(3) ?
C1 C9 C10 C4 . . . . 2.8(4) ?
N6 C5 C10 C9 . . . . -0.6(5) ?
C51 C5 C10 C9 . . . . 178.3(3) ?
N6 C5 C10 C4 . . . . 178.5(3) ?
C51 C5 C10 C4 . . . . -2.5(6) ?
O4 C4 C10 C9 . . . . 175.9(3) ?
N3 C4 C10 C9 . . . . -4.1(5) ?
O4 C4 C10 C5 . . . . -3.3(6) ?
N3 C4 C10 C5 . . . . 176.8(3) ?
