data_2203337
loop_
_publ_author_name
'Din\,cer, Muharrem'
'\"Ozdemir, Nam\?ik'
'Y\?ild\?ir\?im, \.Ismail'
'Demir, Elif'
'Ak\,camur, Yunus'
'I\,s\?ik, \,Samil'
_publ_section_title
;
Methyl 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylate
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o317
_journal_page_last             o319
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C24 H18 N2 O3'
_chemical_formula_moiety       'C24 H18 N2 O3'
_chemical_formula_structural   'C24 H18 N2 O3'
_chemical_formula_sum          'C24 H18 N2 O3'
_chemical_formula_weight       382.40
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
Methyl 4-benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylate
;
_symmetry_cell_setting         monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90.00
_cell_angle_beta               100.297(6)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 8.6467(6)
_cell_length_b                 20.5855(13)
_cell_length_c                 10.9985(8)
_cell_measurement_reflns_used  20375
_cell_measurement_temperature  293(2)
_cell_measurement_theta_max    29.49
_cell_measurement_theta_min    1.98
_cell_volume                   1926.2(2)
_computing_cell_refinement     X-AREA
_computing_data_collection     'SX-AREA (Stoe & Cie, 2002)'
_computing_data_reduction      'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics  'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Stoe IPDS 2'
_diffrn_measurement_method     \f
_diffrn_radiation_monochromator 'plane graphite'
_diffrn_radiation_source       'sealed X-ray tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.1343
_diffrn_reflns_av_sigmaI/netI  0.0411
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_number          37508
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_reflns_theta_min       1.98
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.088
_exptl_absorpt_correction_T_max 0.9817
_exptl_absorpt_correction_T_min 0.9481
_exptl_absorpt_correction_type integration
_exptl_absorpt_process_details '(X-RED; Stoe & Cie, 2002)'
_exptl_crystal_colour          colourless
_exptl_crystal_density_diffrn  1.319
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           800
_exptl_crystal_size_max        0.50
_exptl_crystal_size_mid        0.36
_exptl_crystal_size_min        0.19
_refine_diff_density_max       0.127
_refine_diff_density_min       -0.111
_refine_ls_extinction_coef     0.0090(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL97
_refine_ls_goodness_of_fit_ref 1.005
_refine_ls_hydrogen_treatment  refall
_refine_ls_matrix_type         full
_refine_ls_number_parameters   335
_refine_ls_number_reflns       3385
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.005
_refine_ls_R_factor_all        0.0438
_refine_ls_R_factor_gt         0.0262
_refine_ls_shift/su_max        0.001
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0121P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.0438
_refine_ls_wR_factor_ref       0.0447
_reflns_number_gt              2148
_reflns_number_total           3385
_reflns_threshold_expression   I>2\s(I)
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_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
_atom_site_type_symbol
O1 -0.34673(11) 0.70366(5) 0.88187(9) 0.0595(3) Uani d . 1 . . O
O2 -0.20483(10) 0.78817(5) 0.96654(9) 0.0572(3) Uani d . 1 . . O
O3 -0.17917(11) 0.56173(5) 0.71550(9) 0.0553(3) Uani d . 1 . . O
N1 0.09818(12) 0.73669(5) 0.74424(9) 0.0365(3) Uani d . 1 . . N
N2 -0.00082(12) 0.76718(5) 0.80882(9) 0.0389(3) Uani d . 1 . . N
C1 -0.09371(14) 0.72013(6) 0.83661(11) 0.0363(3) Uani d . 1 . . C
C2 -0.05709(14) 0.65941(6) 0.79023(11) 0.0364(3) Uani d . 1 . . C
C3 0.06721(14) 0.67144(6) 0.73022(11) 0.0352(3) Uani d . 1 . . C
C4 -0.22881(16) 0.73551(7) 0.89646(12) 0.0425(3) Uani d . 1 . . C
C5 -0.3344(2) 0.80831(12) 1.0251(2) 0.0704(6) Uani d . 1 . . C
H5A -0.3009(19) 0.8498(9) 1.0655(15) 0.090(6) Uiso d . 1 . . H
H5B -0.431(2) 0.8116(8) 0.9608(15) 0.093(6) Uiso d . 1 . . H
H5C -0.354(2) 0.7749(10) 1.0848(18) 0.115(8) Uiso d . 1 . . H
C6 -0.13252(15) 0.59555(6) 0.80590(13) 0.0402(3) Uani d . 1 . . C
C7 -0.14970(15) 0.57401(6) 0.93156(12) 0.0399(3) Uani d . 1 . . C
C8 -0.24976(19) 0.52308(7) 0.94402(15) 0.0560(4) Uani d . 1 . . C
H8 -0.3091(17) 0.5049(7) 0.8674(14) 0.076(5) Uiso d . 1 . . H
C9 -0.2697(2) 0.50265(8) 1.05931(16) 0.0667(5) Uani d . 1 . . C
H9 -0.3415(19) 0.4659(8) 1.0655(14) 0.087(5) Uiso d . 1 . . H
C10 -0.1890(2) 0.53203(8) 1.16331(17) 0.0613(5) Uani d . 1 . . C
H10 -0.2042(17) 0.5177(7) 1.2456(14) 0.071(5) Uiso d . 1 . . H
C11 -0.0894(2) 0.58216(9) 1.15251(15) 0.0652(5) Uani d . 1 . . C
H11 -0.0339(19) 0.6028(7) 1.2264(14) 0.080(5) Uiso d . 1 . . H
C12 -0.06882(19) 0.60292(8) 1.03714(14) 0.0559(4) Uani d . 1 . . C
H12 0.0007(17) 0.6365(7) 1.0292(12) 0.061(4) Uiso d . 1 . . H
C13 0.21291(15) 0.77547(6) 0.69826(12) 0.0369(3) Uani d . 1 . . C
C14 0.28754(17) 0.82445(7) 0.77186(14) 0.0501(4) Uani d . 1 . . C
H14 0.2558(15) 0.8324(6) 0.8514(12) 0.056(4) Uiso d . 1 . . H
C15 0.3977(2) 0.86196(9) 0.72680(17) 0.0641(5) Uani d . 1 . . C
H15 0.4432(18) 0.8951(8) 0.7767(14) 0.076(5) Uiso d . 1 . . H
C16 0.4332(2) 0.85036(9) 0.61206(17) 0.0640(5) Uani d . 1 . . C
H16 0.5137(19) 0.8764(8) 0.5828(14) 0.086(5) Uiso d . 1 . . H
C17 0.35633(18) 0.80223(8) 0.53947(16) 0.0549(4) Uani d . 1 . . C
H17 0.3824(17) 0.7945(7) 0.4576(13) 0.071(5) Uiso d . 1 . . H
C18 0.24444(17) 0.76467(7) 0.58165(13) 0.0436(4) Uani d . 1 . . C
H18 0.1853(15) 0.7322(6) 0.5279(12) 0.052(4) Uiso d . 1 . . H
C19 0.15771(15) 0.62722(6) 0.66364(11) 0.0364(3) Uani d . 1 . . C
C20 0.08115(18) 0.59455(7) 0.56014(13) 0.0438(4) Uani d . 1 . . C
H20 -0.0301(17) 0.6017(6) 0.5356(11) 0.055(4) Uiso d . 1 . . H
C21 0.16214(19) 0.55299(7) 0.49587(14) 0.0510(4) Uani d . 1 . . C
H21 0.1065(17) 0.5308(7) 0.4205(13) 0.069(5) Uiso d . 1 . . H
C22 0.3199(2) 0.54393(8) 0.53373(16) 0.0574(4) Uani d . 1 . . C
H22 0.3780(16) 0.5154(7) 0.4871(12) 0.065(4) Uiso d . 1 . . H
C23 0.39875(19) 0.57638(8) 0.63600(15) 0.0549(4) Uani d . 1 . . C
H23 0.5123(18) 0.5703(7) 0.6621(12) 0.065(4) Uiso d . 1 . . H
C24 0.31827(17) 0.61820(7) 0.70064(14) 0.0446(4) Uani d . 1 . . C
H24 0.3693(14) 0.6397(6) 0.7700(11) 0.041(4) Uiso d . 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0434(6) 0.0619(7) 0.0784(7) -0.0109(5) 0.0248(5) -0.0197(6)
O2 0.0438(6) 0.0643(7) 0.0679(7) -0.0065(5) 0.0218(5) -0.0295(6)
O3 0.0660(7) 0.0507(6) 0.0508(6) -0.0157(5) 0.0144(5) -0.0116(5)
N1 0.0368(6) 0.0358(7) 0.0394(6) -0.0004(5) 0.0139(5) -0.0014(5)
N2 0.0391(6) 0.0394(7) 0.0404(6) 0.0019(6) 0.0133(5) -0.0023(5)
C1 0.0342(7) 0.0390(8) 0.0366(8) -0.0015(6) 0.0091(6) -0.0017(6)
C2 0.0361(8) 0.0359(8) 0.0378(8) -0.0024(6) 0.0078(6) -0.0011(6)
C3 0.0364(7) 0.0321(8) 0.0372(8) -0.0005(6) 0.0073(6) -0.0006(6)
C4 0.0404(8) 0.0453(9) 0.0427(8) 0.0001(7) 0.0097(7) -0.0028(7)
C5 0.0474(11) 0.0907(16) 0.0773(14) -0.0005(11) 0.0223(11) -0.0403(13)
C6 0.0356(8) 0.0383(8) 0.0481(9) 0.0003(6) 0.0108(7) -0.0032(7)
C7 0.0386(8) 0.0344(8) 0.0479(9) -0.0024(6) 0.0106(7) 0.0005(6)
C8 0.0644(11) 0.0516(10) 0.0519(10) -0.0184(8) 0.0099(9) -0.0007(8)
C9 0.0787(12) 0.0569(11) 0.0664(12) -0.0255(10) 0.0178(10) 0.0092(9)
C10 0.0763(12) 0.0559(11) 0.0534(11) -0.0058(9) 0.0158(10) 0.0121(9)
C11 0.0833(13) 0.0628(11) 0.0458(10) -0.0186(10) 0.0016(9) 0.0035(9)
C12 0.0619(10) 0.0524(10) 0.0508(10) -0.0204(8) 0.0034(8) 0.0055(8)
C13 0.0353(7) 0.0348(8) 0.0420(8) 0.0014(6) 0.0110(6) 0.0059(6)
C14 0.0570(10) 0.0463(9) 0.0487(9) -0.0083(8) 0.0144(8) 0.0007(7)
C15 0.0661(11) 0.0533(11) 0.0720(12) -0.0204(9) 0.0101(10) 0.0021(9)
C16 0.0573(11) 0.0605(12) 0.0786(13) -0.0071(9) 0.0239(10) 0.0201(10)
C17 0.0578(10) 0.0567(10) 0.0566(10) 0.0074(8) 0.0273(9) 0.0162(8)
C18 0.0455(9) 0.0435(9) 0.0438(9) 0.0037(8) 0.0131(7) 0.0047(7)
C19 0.0379(8) 0.0339(8) 0.0395(8) 0.0004(6) 0.0129(6) 0.0020(6)
C20 0.0386(9) 0.0443(9) 0.0496(9) 0.0024(7) 0.0108(7) -0.0037(7)
C21 0.0554(10) 0.0498(9) 0.0504(10) 0.0024(8) 0.0161(8) -0.0093(8)
C22 0.0571(11) 0.0534(10) 0.0680(11) 0.0082(9) 0.0280(9) -0.0102(9)
C23 0.0377(9) 0.0588(10) 0.0712(11) 0.0094(8) 0.0180(9) 0.0029(9)
C24 0.0396(9) 0.0458(9) 0.0486(9) -0.0010(7) 0.0083(7) -0.0007(8)
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
C4 O2 C5 . . 116.08(12) ?
N2 N1 C3 . . 112.46(10) ?
N2 N1 C13 . . 117.84(10) ?
C3 N1 C13 . . 129.67(10) ?
C1 N2 N1 . . 104.28(10) ?
N2 C1 C2 . . 112.32(10) ?
N2 C1 C4 . . 120.41(11) ?
C2 C1 C4 . . 126.89(12) ?
C3 C2 C1 . . 105.00(10) ?
C3 C2 C6 . . 127.40(11) ?
C1 C2 C6 . . 127.57(11) ?
N1 C3 C2 . . 105.95(10) ?
N1 C3 C19 . . 123.28(11) ?
C2 C3 C19 . . 130.77(11) ?
O1 C4 O2 . . 124.50(12) ?
O1 C4 C1 . . 123.07(13) ?
O2 C4 C1 . . 112.42(12) ?
O2 C5 H5A . . 105.1(10) ?
O2 C5 H5B . . 108.6(10) ?
H5A C5 H5B . . 113.8(14) ?
O2 C5 H5C . . 109.4(12) ?
H5A C5 H5C . . 112.1(15) ?
H5B C5 H5C . . 107.7(16) ?
O3 C6 C7 . . 120.94(12) ?
O3 C6 C2 . . 119.74(12) ?
C7 C6 C2 . . 119.32(12) ?
C12 C7 C8 . . 118.44(14) ?
C12 C7 C6 . . 122.36(12) ?
C8 C7 C6 . . 119.20(13) ?
C9 C8 C7 . . 120.48(16) ?
C9 C8 H8 . . 122.9(9) ?
C7 C8 H8 . . 116.5(9) ?
C10 C9 C8 . . 120.39(16) ?
C10 C9 H9 . . 120.8(9) ?
C8 C9 H9 . . 118.8(9) ?
C11 C10 C9 . . 119.80(16) ?
C11 C10 H10 . . 119.8(9) ?
C9 C10 H10 . . 120.3(9) ?
C10 C11 C12 . . 120.13(17) ?
C10 C11 H11 . . 119.1(9) ?
C12 C11 H11 . . 120.8(9) ?
C7 C12 C11 . . 120.74(15) ?
C7 C12 H12 . . 118.7(9) ?
C11 C12 H12 . . 120.6(9) ?
C18 C13 C14 . . 121.02(13) ?
C18 C13 N1 . . 120.23(12) ?
C14 C13 N1 . . 118.73(12) ?
C13 C14 C15 . . 118.50(15) ?
C13 C14 H14 . . 118.2(8) ?
C15 C14 H14 . . 123.2(8) ?
C16 C15 C14 . . 120.89(17) ?
C16 C15 H15 . . 122.4(10) ?
C14 C15 H15 . . 116.7(10) ?
C17 C16 C15 . . 119.84(16) ?
C17 C16 H16 . . 120.4(9) ?
C15 C16 H16 . . 119.8(9) ?
C16 C17 C18 . . 120.38(15) ?
C16 C17 H17 . . 119.1(9) ?
C18 C17 H17 . . 120.5(9) ?
C13 C18 C17 . . 119.32(15) ?
C13 C18 H18 . . 120.4(8) ?
C17 C18 H18 . . 120.2(7) ?
C20 C19 C24 . . 118.84(12) ?
C20 C19 C3 . . 119.29(12) ?
C24 C19 C3 . . 121.86(12) ?
C21 C20 C19 . . 120.74(14) ?
C21 C20 H20 . . 121.7(8) ?
C19 C20 H20 . . 117.6(8) ?
C22 C21 C20 . . 119.98(15) ?
C22 C21 H21 . . 120.1(8) ?
C20 C21 H21 . . 119.9(9) ?
C21 C22 C23 . . 120.24(15) ?
C21 C22 H22 . . 120.1(9) ?
C23 C22 H22 . . 119.6(8) ?
C22 C23 C24 . . 120.04(15) ?
C22 C23 H23 . . 120.0(8) ?
C24 C23 H23 . . 119.9(8) ?
C23 C24 C19 . . 120.14(15) ?
C23 C24 H24 . . 120.9(8) ?
C19 C24 H24 . . 119.0(8) ?
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
O1 C4 . 1.1986(15) ?
O2 C4 . 1.3248(15) ?
O2 C5 . 1.4494(17) ?
O3 C6 . 1.2218(15) ?
N1 N2 . 1.3596(13) ?
N1 C3 . 1.3727(15) ?
N1 C13 . 1.4342(15) ?
N2 C1 . 1.3284(15) ?
C1 C2 . 1.4073(16) ?
C1 C4 . 1.4741(17) ?
C2 C3 . 1.3806(16) ?
C2 C6 . 1.4910(17) ?
C3 C19 . 1.4773(17) ?
C5 H5A . 0.981(18) ?
C5 H5B . 0.993(18) ?
C5 H5C . 0.984(19) ?
C6 C7 . 1.4840(17) ?
C7 C12 . 1.3789(19) ?
C7 C8 . 1.3817(18) ?
C8 C9 . 1.376(2) ?
C8 H8 . 0.979(15) ?
C9 C10 . 1.369(2) ?
C9 H9 . 0.989(17) ?
C10 C11 . 1.363(2) ?
C10 H10 . 0.982(14) ?
C11 C12 . 1.380(2) ?
C11 H11 . 0.965(16) ?
C12 H12 . 0.930(14) ?
C13 C18 . 1.3761(17) ?
C13 C14 . 1.3790(18) ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.976(13) ?
C15 C16 . 1.372(2) ?
C15 H15 . 0.918(16) ?
C16 C17 . 1.368(2) ?
C16 H16 . 0.978(16) ?
C17 C18 . 1.382(2) ?
C17 H17 . 0.979(14) ?
C18 H18 . 0.975(13) ?
C19 C20 . 1.3845(18) ?
C19 C24 . 1.3876(18) ?
C20 C21 . 1.3780(19) ?
C20 H20 . 0.963(14) ?
C21 C22 . 1.366(2) ?
C21 H21 . 0.992(14) ?
C22 C23 . 1.379(2) ?
C22 H22 . 0.976(14) ?
C23 C24 . 1.3812(19) ?
C23 H23 . 0.980(15) ?
C24 H24 . 0.923(12) ?
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
C5 H5A O3 4_576 0.981(18) 2.556(19) 3.513(2) 165.1(13)
C21 H21 O3 3_566 0.992(14) 2.569(14) 3.3355(18) 134.0(11)
C10 H10 Cg4 3_765 0.982(14) 2.783(15) 3.6514(19) 147.6(11)
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
C3 N1 N2 C1 . . . . 0.67(14) ?
C13 N1 N2 C1 . . . . 178.78(11) ?
N1 N2 C1 C2 . . . . -0.39(14) ?
N1 N2 C1 C4 . . . . -173.71(11) ?
N2 C1 C2 C3 . . . . -0.02(15) ?
C4 C1 C2 C3 . . . . 172.77(13) ?
N2 C1 C2 C6 . . . . 178.19(12) ?
C4 C1 C2 C6 . . . . -9.0(2) ?
N2 N1 C3 C2 . . . . -0.70(14) ?
C13 N1 C3 C2 . . . . -178.53(12) ?
N2 N1 C3 C19 . . . . 179.97(11) ?
C13 N1 C3 C19 . . . . 2.1(2) ?
C1 C2 C3 N1 . . . . 0.42(13) ?
C6 C2 C3 N1 . . . . -177.79(12) ?
C1 C2 C3 C19 . . . . 179.68(13) ?
C6 C2 C3 C19 . . . . 1.5(2) ?
C5 O2 C4 O1 . . . . -1.9(2) ?
C5 O2 C4 C1 . . . . 177.66(15) ?
N2 C1 C4 O1 . . . . 150.13(14) ?
C2 C1 C4 O1 . . . . -22.1(2) ?
N2 C1 C4 O2 . . . . -29.48(18) ?
C2 C1 C4 O2 . . . . 158.25(12) ?
C3 C2 C6 O3 . . . . -52.9(2) ?
C1 C2 C6 O3 . . . . 129.28(14) ?
C3 C2 C6 C7 . . . . 127.07(14) ?
C1 C2 C6 C7 . . . . -50.75(19) ?
O3 C6 C7 C12 . . . . 165.08(14) ?
C2 C6 C7 C12 . . . . -14.89(19) ?
O3 C6 C7 C8 . . . . -14.74(19) ?
C2 C6 C7 C8 . . . . 165.29(13) ?
C12 C7 C8 C9 . . . . 1.1(2) ?
C6 C7 C8 C9 . . . . -179.09(14) ?
C7 C8 C9 C10 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 0.6(3) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
C8 C7 C12 C11 . . . . -1.1(2) ?
C6 C7 C12 C11 . . . . 179.10(14) ?
C10 C11 C12 C7 . . . . 0.8(3) ?
N2 N1 C13 C18 . . . . -138.75(12) ?
C3 N1 C13 C18 . . . . 39.0(2) ?
N2 N1 C13 C14 . . . . 39.72(18) ?
C3 N1 C13 C14 . . . . -142.55(13) ?
C18 C13 C14 C15 . . . . -1.2(2) ?
N1 C13 C14 C15 . . . . -179.70(13) ?
C13 C14 C15 C16 . . . . -0.7(2) ?
C14 C15 C16 C17 . . . . 1.7(3) ?
C15 C16 C17 C18 . . . . -0.8(2) ?
C14 C13 C18 C17 . . . . 2.1(2) ?
N1 C13 C18 C17 . . . . -179.48(13) ?
C16 C17 C18 C13 . . . . -1.0(2) ?
N1 C3 C19 C20 . . . . -119.06(14) ?
C2 C3 C19 C20 . . . . 61.79(19) ?
N1 C3 C19 C24 . . . . 59.86(18) ?
C2 C3 C19 C24 . . . . -119.29(16) ?
C24 C19 C20 C21 . . . . 1.0(2) ?
C3 C19 C20 C21 . . . . 179.94(13) ?
C19 C20 C21 C22 . . . . -0.3(2) ?
C20 C21 C22 C23 . . . . -0.2(2) ?
C21 C22 C23 C24 . . . . 0.0(2) ?
C22 C23 C24 C19 . . . . 0.6(2) ?
C20 C19 C24 C23 . . . . -1.1(2) ?
C3 C19 C24 C23 . . . . 179.96(12) ?