#------------------------------------------------------------------------------
#$Date: 2021-10-05 13:47:37 +0300 (Tue, 05 Oct 2021) $
#$Revision: 269584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/89/4038964.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_4038964
loop_
_publ_author_name
'Vasin, V.A.'
'Razin, V.V.'
'Bezrukova, E.V.'
'Popkova, Yu.A.'
'Somov, N.V.'
_publ_section_title
;
 Rearrangements of 3H-PyrazolesAdducts of Dimethyl Acetylenedicarboxylate
 with Diphenyldiazomethane and 9-Diazofluorene
;
_journal_issue                   6
_journal_name_full
;
 Russian Journal of Organic Chemistry
;
_journal_page_first              892
_journal_page_last               900
_journal_paper_doi               10.1134/S1070428018060118
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_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             2017-03-28T15:28:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                117.634(4)
_cell_angle_beta                 110.058(4)
_cell_angle_gamma                94.538(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6641(4)
_cell_length_b                   10.3573(4)
_cell_length_c                   10.5328(5)
_cell_measurement_reflns_used    8526
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.119
_cell_measurement_theta_min      2.306
_cell_volume                     840.65(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.8e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8e (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 1
_diffrn_measured_fraction_theta_max 0.997
_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      0.058131
_diffrn_orient_matrix_UB_12      0.069782
_diffrn_orient_matrix_UB_13      0.0586458
_diffrn_orient_matrix_UB_21      -0.0470743
_diffrn_orient_matrix_UB_22      0.0233587
_diffrn_orient_matrix_UB_23      0.0405856
_diffrn_orient_matrix_UB_31      0.0324747
_diffrn_orient_matrix_UB_32      -0.0330676
_diffrn_orient_matrix_UB_33      0.0447368
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32735
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.82336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.8e (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0827P)²+0.0526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0
_reflns_number_gt                3568
_reflns_number_total             5110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tmppc21nn2s
_cod_data_source_block           b-01
_cod_database_code               4038964
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
C1 C 0.04758(12) 0.69954(12) 0.38944(13) 0.0361(2) Uani 1 1 d . . . . .
C2 C -0.09324(12) 0.64293(12) 0.38594(13) 0.0352(2) Uani 1 1 d . . . . .
C3 C -0.10418(12) 0.76281(12) 0.51200(13) 0.0354(2) Uani 1 1 d . . . . .
C4 C -0.23212(13) 0.77518(13) 0.55951(13) 0.0390(3) Uani 1 1 d . . . . .
C5 C -0.30525(17) 0.88664(18) 0.5646(2) 0.0556(3) Uani 1 1 d . . . . .
C6 C -0.4266(2) 0.8962(2) 0.6079(2) 0.0724(5) Uani 1 1 d . . . . .
C7 C -0.4745(2) 0.7973(2) 0.6467(2) 0.0736(5) Uani 1 1 d . . . . .
C8 C -0.4030(2) 0.6865(2) 0.6415(2) 0.0698(5) Uani 1 1 d . . . . .
C9 C -0.28280(17) 0.67382(17) 0.59651(17) 0.0529(3) Uani 1 1 d . . . . .
C10 C -0.20966(13) 0.49326(12) 0.26669(13) 0.0364(2) Uani 1 1 d . . . . .
C11 C -0.17581(16) 0.35718(15) 0.23692(18) 0.0500(3) Uani 1 1 d . . . . .
C12 C -0.2883(2) 0.21879(15) 0.1221(2) 0.0599(4) Uani 1 1 d . . . . .
C13 C -0.43505(18) 0.21554(16) 0.03780(18) 0.0561(4) Uani 1 1 d . . . . .
C14 C -0.47078(16) 0.35000(16) 0.06839(16) 0.0507(3) Uani 1 1 d . . . . .
C15 C -0.35897(14) 0.48822(14) 0.18168(15) 0.0423(3) Uani 1 1 d . . . . .
C16 C 0.08710(14) 1.02767(14) 0.72876(14) 0.0432(3) Uani 1 1 d . . . . .
C17 C 0.0603(3) 1.1695(3) 0.9647(2) 0.0884(7) Uani 1 1 d . . . . .
C18 C 0.11342(15) 0.62260(15) 0.27711(16) 0.0470(3) Uani 1 1 d . . . . .
C19 C 0.2925(3) 0.6527(3) 0.1816(3) 0.0863(6) Uani 1 1 d . . . . .
N1 N 0.02865(11) 0.88129(11) 0.58360(12) 0.0416(2) Uani 1 1 d . . . . .
N2 N 0.12098(11) 0.84349(12) 0.50821(12) 0.0418(2) Uani 1 1 d . . . . .
O1A O 0.0860(6) 0.4852(4) 0.2000(6) 0.0792(11) Uani 0.725(12) 1 d . . P A 1
O1B O 0.0411(14) 0.5050(9) 0.1571(14) 0.0792(11) Uani 0.275(12) 1 d . . P A 2
O2 O 0.21728(13) 0.71850(13) 0.28457(14) 0.0685(3) Uani 1 1 d . . . . .
O3 O 0.18176(13) 1.13080(12) 0.75765(13) 0.0674(3) Uani 1 1 d . . . . .
O4 O 0.02353(13) 1.02547(12) 0.82012(12) 0.0635(3) Uani 1 1 d . . . . .
H5 H -0.268(2) 0.960(2) 0.539(2) 0.069(5) Uiso 1 1 d . . . . .
H6 H -0.483(3) 0.977(3) 0.609(3) 0.104(7) Uiso 1 1 d . . . . .
H7 H -0.558(3) 0.804(3) 0.676(3) 0.097(7) Uiso 1 1 d . . . . .
H8 H -0.430(2) 0.615(2) 0.665(3) 0.083(6) Uiso 1 1 d . . . . .
H9 H -0.2357(18) 0.5954(18) 0.5860(18) 0.050(4) Uiso 1 1 d . . . . .
H11 H -0.073(2) 0.3582(19) 0.298(2) 0.064(5) Uiso 1 1 d . . . . .
H12 H -0.262(2) 0.125(2) 0.095(2) 0.074(5) Uiso 1 1 d . . . . .
H13 H -0.510(2) 0.119(2) -0.043(3) 0.083(6) Uiso 1 1 d . . . . .
H14 H -0.574(2) 0.357(2) 0.016(2) 0.077(5) Uiso 1 1 d . . . . .
H15 H -0.3833(17) 0.5813(18) 0.2016(19) 0.051(4) Uiso 1 1 d . . . . .
H17A H 0.005(4) 1.157(3) 1.010(4) 0.135(6) Uiso 1 1 d . . . . .
H17B H 0.061(4) 1.252(4) 0.949(4) 0.135(6) Uiso 1 1 d . . . . .
H17C H 0.159(4) 1.185(3) 1.024(4) 0.135(6) Uiso 1 1 d . . . . .
H19C H 0.361(4) 0.731(4) 0.201(4) 0.146(7) Uiso 1 1 d . . . . .
H19A H 0.216(4) 0.588(4) 0.068(4) 0.146(7) Uiso 1 1 d . . . . .
H19B H 0.344(4) 0.584(4) 0.213(4) 0.146(7) Uiso 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -1 -12 0.0717
2 -11 13 0.0604
-2 11 -13 0.0604
13 1 -3 0.0376
-10 -9 10 0.0274
12 0 -10 0.0648
-8 -4 14 0.0719
3 0 10 0.0794
-3 -1 -10 0.0967
-5 10 4 0.119
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
N2 C1 C2 112.75(10) . . ?
N2 C1 C18 118.99(10) . . ?
C2 C1 C18 128.19(11) . . ?
C3 C2 C1 104.68(10) . . ?
C3 C2 C10 127.03(10) . . ?
C1 C2 C10 128.12(10) . . ?
C2 C3 N1 105.84(10) . . ?
C2 C3 C4 129.26(10) . . ?
N1 C3 C4 124.71(10) . . ?
C9 C4 C5 119.12(13) . . ?
C9 C4 C3 120.42(12) . . ?
C5 C4 C3 120.45(12) . . ?
C4 C5 C6 119.92(16) . . ?
C7 C6 C5 120.67(17) . . ?
C6 C7 C8 119.75(15) . . ?
C7 C8 C9 120.44(16) . . ?
C4 C9 C8 120.08(16) . . ?
C11 C10 C15 118.56(11) . . ?
C11 C10 C2 122.30(11) . . ?
C15 C10 C2 119.14(10) . . ?
C10 C11 C12 120.42(13) . . ?
C13 C12 C11 120.37(13) . . ?
C14 C13 C12 119.72(12) . . ?
C13 C14 C15 120.21(13) . . ?
C14 C15 C10 120.70(12) . . ?
O3 C16 O4 127.35(12) . . ?
O3 C16 N1 122.90(13) . . ?
O4 C16 N1 109.73(11) . . ?
O1B C18 O2 120.1(5) . . ?
O1A C18 O2 124.30(17) . . ?
O1B C18 C1 121.0(4) . . ?
O1A C18 C1 122.90(17) . . ?
O2 C18 C1 112.32(11) . . ?
N2 N1 C3 112.61(9) . . ?
N2 N1 C16 116.52(10) . . ?
C3 N1 C16 130.60(10) . . ?
C1 N2 N1 104.11(9) . . ?
C18 O2 C19 116.33(14) . . ?
C16 O4 C17 116.11(15) . . ?
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 N2 1.3359(14) . ?
C1 C2 1.4201(15) . ?
C1 C18 1.4703(16) . ?
C2 C3 1.3797(16) . ?
C2 C10 1.4815(15) . ?
C3 N1 1.3967(14) . ?
C3 C4 1.4783(15) . ?
C4 C9 1.3868(19) . ?
C4 C5 1.3902(19) . ?
C5 C6 1.392(2) . ?
C6 C7 1.368(3) . ?
C7 C8 1.376(3) . ?
C8 C9 1.391(2) . ?
C10 C11 1.3875(17) . ?
C10 C15 1.3947(17) . ?
C11 C12 1.394(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.378(2) . ?
C14 C15 1.3882(18) . ?
C16 O3 1.1930(16) . ?
C16 O4 1.3144(17) . ?
C16 N1 1.4412(15) . ?
C17 O4 1.4519(19) . ?
C18 O1B 1.184(10) . ?
C18 O1A 1.215(4) . ?
C18 O2 1.3100(17) . ?
C19 O2 1.450(2) . ?
N1 N2 1.3538(14) . ?
