#------------------------------------------------------------------------------
#$Date: 2021-10-05 13:03:19 +0300 (Tue, 05 Oct 2021) $
#$Revision: 269575 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038959.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038959
loop_
_publ_author_name
'Vasin, V..'
'Popkova, Yu..'
'Bezrukova, Ye.V.'
'Razin, V.V.'
'Somov, N.V.'
_publ_section_title
;
 Thermal Rearrangements of 3- and 4-Pyrazoles Prepared by Reactions of
 9-Diazofluoren with Methyl Tetrolate and Methyl 3-Phenylpropiolate
;
_journal_issue                   8
_journal_name_full
;
 Russian Journal of Organic Chemistry
;
_journal_page_first              1189
_journal_page_last               1199
_journal_paper_doi               10.1134/S1070428018080122
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C23 H16 N2 O2'
_chemical_formula_weight         352.38
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2016-06-30T13:47:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.285(8)
_cell_angle_beta                 105.762(7)
_cell_angle_gamma                110.957(8)
_cell_formula_units_Z            2
_cell_length_a                   8.5710(6)
_cell_length_b                   8.9793(10)
_cell_length_c                   12.5804(11)
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.566
_cell_measurement_theta_min      4.103
_cell_volume                     857.21(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6b (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0090316
_diffrn_orient_matrix_UB_12      0.0041828
_diffrn_orient_matrix_UB_13      -0.0573678
_diffrn_orient_matrix_UB_21      0.0026027
_diffrn_orient_matrix_UB_22      -0.0777902
_diffrn_orient_matrix_UB_23      -0.008156
_diffrn_orient_matrix_UB_31      -0.0928424
_diffrn_orient_matrix_UB_32      -0.0361125
_diffrn_orient_matrix_UB_33      -0.0133772
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.94
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7310
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.94
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.416
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.24128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.6b (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0836P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0
_reflns_number_gt                2651
_reflns_number_total             3296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tmpq8kkat1s
_cod_data_source_block           mu-37
_cod_database_code               4038959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 1.046(2) 0.133(2) 0.1369(14) 0.048(4) Uiso 1 1 d . . . . .
H2 H 1.017(2) -0.125(2) 0.0608(16) 0.058(5) Uiso 1 1 d . . . . .
H3 H 0.872(2) -0.357(3) 0.1334(17) 0.068(5) Uiso 1 1 d . . . . .
H4 H 0.758(2) -0.324(2) 0.2842(15) 0.059(5) Uiso 1 1 d . . . . .
H5 H 0.596(2) -0.300(2) 0.3773(15) 0.054(5) Uiso 1 1 d . . . . .
H6 H 0.526(3) -0.264(3) 0.5448(18) 0.079(6) Uiso 1 1 d . . . . .
H7 H 0.650(2) -0.002(2) 0.6573(17) 0.068(5) Uiso 1 1 d . . . . .
H8 H 0.832(2) 0.223(2) 0.6013(16) 0.060(5) Uiso 1 1 d . . . . .
H9 H 0.730(2) 0.371(2) 0.3693(16) 0.056(5) Uiso 1 1 d . . . . .
H10 H 0.472(3) 0.404(3) 0.2854(18) 0.074(6) Uiso 1 1 d . . . . .
H11 H 0.325(2) 0.307(2) 0.0885(14) 0.053(4) Uiso 1 1 d . . . . .
H12 H 0.441(3) 0.173(3) -0.015(2) 0.081(6) Uiso 1 1 d . . . . .
H13 H 0.705(2) 0.126(2) 0.0789(16) 0.063(5) Uiso 1 1 d . . . . .
H14 H 1.201(3) 0.676(3) 0.095(2) 0.083(7) Uiso 1 1 d . . . . .
H15 H 1.351(3) 0.620(3) 0.113(2) 0.103(9) Uiso 1 1 d . . . . .
H16 H 1.379(3) 0.783(3) 0.1871(19) 0.085(7) Uiso 1 1 d . . . . .
C1 C 0.65487(18) 0.1854(2) 0.11994(12) 0.0439(4) Uani 1 1 d . . . . .
C2 C 0.50358(19) 0.2093(2) 0.06630(13) 0.0504(4) Uani 1 1 d . . . . .
C3 C 0.43417(17) 0.2891(2) 0.12541(13) 0.0466(4) Uani 1 1 d . . . . .
C4 C 0.51880(19) 0.3479(2) 0.23892(14) 0.0452(4) Uani 1 1 d . . . . .
C5 C 0.67177(17) 0.32573(17) 0.29284(12) 0.0386(3) Uani 1 1 d . . . . .
C6 C 0.74027(15) 0.24323(15) 0.23449(10) 0.0307(3) Uani 1 1 d . . . . .
C7 C 0.91235(15) 0.22125(15) 0.29447(10) 0.0310(3) Uani 1 1 d . . . . .
C8 C 1.06837(15) 0.37717(16) 0.30386(11) 0.0347(3) Uani 1 1 d . . . . .
C9 C 0.94005(15) 0.22919(16) 0.41871(10) 0.0325(3) Uani 1 1 d . . . . .
C10 C 0.82856(15) 0.09459(17) 0.45878(10) 0.0347(3) Uani 1 1 d . . . . .
C11 C 0.76265(16) -0.05907(17) 0.39164(11) 0.0361(3) Uani 1 1 d . . . . .
C12 C 0.65085(19) -0.1902(2) 0.42563(14) 0.0466(4) Uani 1 1 d . . . . .
C13 C 0.6090(2) -0.1689(2) 0.52265(15) 0.0534(4) Uani 1 1 d . . . . .
C14 C 0.6787(2) -0.0187(2) 0.58916(14) 0.0526(4) Uani 1 1 d . . . . .
C15 C 0.78765(18) 0.1146(2) 0.55730(12) 0.0431(4) Uani 1 1 d . . . . .
C16 C 0.82489(15) -0.07795(16) 0.29447(11) 0.0351(3) Uani 1 1 d . . . . .
C17 C 0.81284(19) -0.22935(19) 0.25031(13) 0.0449(4) Uani 1 1 d . . . . .
C18 C 0.8819(2) -0.2479(2) 0.16525(13) 0.0507(4) Uani 1 1 d . . . . .
C19 C 0.9697(2) -0.1136(2) 0.12460(12) 0.0483(4) Uani 1 1 d . . . . .
C20 C 0.98291(18) 0.03847(19) 0.16680(11) 0.0410(3) Uani 1 1 d . . . . .
C21 C 0.90963(15) 0.05806(16) 0.24966(10) 0.0328(3) Uani 1 1 d . . . . .
C22 C 1.11494(16) 0.45180(18) 0.20795(12) 0.0389(3) Uani 1 1 d . . . . .
C23 C 1.2999(3) 0.6760(3) 0.15268(19) 0.0641(5) Uani 1 1 d . . . . .
N1 N 1.14976(14) 0.45128(14) 0.40570(10) 0.0417(3) Uani 1 1 d . . . . .
N2 N 1.07086(14) 0.35525(14) 0.47971(9) 0.0406(3) Uani 1 1 d . . . . .
O1 O 1.04047(15) 0.38785(14) 0.11137(9) 0.0580(4) Uani 1 1 d . . . . .
O2 O 1.24629(13) 0.59562(14) 0.24104(9) 0.0545(3) Uani 1 1 d . . . . .
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.44(15) . . ?
C2 C1 H13 121.6(11) . . ?
C6 C1 H13 117.9(11) . . ?
C3 C2 C1 120.55(14) . . ?
C3 C2 H12 116.1(14) . . ?
C1 C2 H12 123.3(14) . . ?
C2 C3 C4 119.38(14) . . ?
C2 C3 H11 121.9(11) . . ?
C4 C3 H11 118.7(11) . . ?
C3 C4 C5 120.24(16) . . ?
C3 C4 H10 122.3(12) . . ?
C5 C4 H10 117.4(12) . . ?
C6 C5 C4 120.66(13) . . ?
C6 C5 H9 120.5(12) . . ?
C4 C5 H9 118.8(12) . . ?
C5 C6 C1 118.71(13) . . ?
C5 C6 C7 120.47(11) . . ?
C1 C6 C7 120.79(13) . . ?
C9 C7 C8 96.30(10) . . ?
C9 C7 C21 107.30(11) . . ?
C8 C7 C21 120.34(11) . . ?
C9 C7 C6 110.88(11) . . ?
C8 C7 C6 108.79(10) . . ?
C21 C7 C6 112.00(9) . . ?
N1 C8 C22 121.28(11) . . ?
N1 C8 C7 112.61(11) . . ?
C22 C8 C7 125.72(11) . . ?
N2 C9 C10 126.42(12) . . ?
N2 C9 C7 114.08(11) . . ?
C10 C9 C7 119.38(11) . . ?
C15 C10 C11 121.15(12) . . ?
C15 C10 C9 122.75(13) . . ?
C11 C10 C9 116.09(12) . . ?
C12 C11 C10 117.67(13) . . ?
C12 C11 C16 122.82(14) . . ?
C10 C11 C16 119.31(11) . . ?
C13 C12 C11 120.80(16) . . ?
C13 C12 H5 119.5(10) . . ?
C11 C12 H5 119.7(10) . . ?
C14 C13 C12 120.82(14) . . ?
C14 C13 H6 119.5(13) . . ?
C12 C13 H6 119.7(13) . . ?
C13 C14 C15 120.06(15) . . ?
C13 C14 H7 121.6(12) . . ?
C15 C14 H7 118.3(12) . . ?
C14 C15 C10 119.45(16) . . ?
C14 C15 H8 121.1(11) . . ?
C10 C15 H8 119.4(11) . . ?
C17 C16 C21 118.23(13) . . ?
C17 C16 C11 120.55(12) . . ?
C21 C16 C11 121.05(13) . . ?
C18 C17 C16 121.56(14) . . ?
C18 C17 H4 120.4(12) . . ?
C16 C17 H4 117.9(12) . . ?
C19 C18 C17 119.80(16) . . ?
C19 C18 H3 119.1(11) . . ?
C17 C18 H3 121.0(11) . . ?
C18 C19 C20 119.77(15) . . ?
C18 C19 H2 120.8(11) . . ?
C20 C19 H2 119.3(11) . . ?
C21 C20 C19 121.00(13) . . ?
C21 C20 H1 120.2(11) . . ?
C19 C20 H1 118.8(11) . . ?
C20 C21 C16 119.57(13) . . ?
C20 C21 C7 122.96(11) . . ?
C16 C21 C7 117.45(11) . . ?
O1 C22 O2 124.06(12) . . ?
O1 C22 C8 123.46(12) . . ?
O2 C22 C8 112.48(12) . . ?
O2 C23 H14 111.0(13) . . ?
O2 C23 H15 113.0(16) . . ?
H14 C23 H15 103(2) . . ?
O2 C23 H16 106.4(14) . . ?
H14 C23 H16 111(2) . . ?
H15 C23 H16 112(2) . . ?
C8 N1 N2 109.17(10) . . ?
C9 N2 N1 107.73(10) . . ?
C22 O2 C23 115.87(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(2) . ?
C1 C6 1.3969(19) . ?
C1 H13 1.00(2) . ?
C2 C3 1.380(2) . ?
C2 H12 0.99(2) . ?
C3 C4 1.386(2) . ?
C3 H11 1.001(18) . ?
C4 C5 1.392(2) . ?
C4 H10 1.00(2) . ?
C5 C6 1.384(2) . ?
C5 H9 0.943(19) . ?
C6 C7 1.5506(17) . ?
C7 C9 1.5093(17) . ?
C7 C8 1.5226(16) . ?
C7 C21 1.5294(19) . ?
C8 N1 1.2867(18) . ?
C8 C22 1.4924(18) . ?
C9 N2 1.2855(16) . ?
C9 C10 1.4606(17) . ?
C10 C15 1.3954(19) . ?
C10 C11 1.409(2) . ?
C11 C12 1.4001(18) . ?
C11 C16 1.4842(19) . ?
C12 C13 1.384(2) . ?
C12 H5 1.004(19) . ?
C13 C14 1.378(3) . ?
C13 H6 1.01(2) . ?
C14 C15 1.387(2) . ?
C14 H7 0.97(2) . ?
C15 H8 0.98(2) . ?
C16 C17 1.396(2) . ?
C16 C21 1.4156(18) . ?
C17 C18 1.384(2) . ?
C17 H4 0.993(18) . ?
C18 C19 1.383(2) . ?
C18 H3 1.00(2) . ?
C19 C20 1.390(2) . ?
C19 H2 1.011(19) . ?
C20 C21 1.3877(19) . ?
C20 H1 0.985(16) . ?
C22 O1 1.2041(18) . ?
C22 O2 1.3237(17) . ?
C23 O2 1.449(2) . ?
C23 H14 0.95(2) . ?
C23 H15 0.98(3) . ?
C23 H16 0.95(2) . ?
N1 N2 1.4439(16) . ?
