#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:12:03 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291049 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159848.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_7159848
loop_
_publ_author_name
'Feng, Yang'
'Ren, Yuanyuan'
'Tang, Duoduo'
'Wang, Ke-Hu'
'Wang, Junjiao'
'Huang, Danfeng'
'Lv, Xiaobo'
'Hu, Yulai'
_publ_section_title
;
 Synthesis of difluoromethylated spiropyrazolones via [3 + 2]
 cycloaddition of difluoroacetohydrazonoyl bromides with alkylidene
 pyrazolones.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2797
_journal_page_last               2812
_journal_paper_doi               10.1039/d4ob00044g
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C25 H18 Cl2 F2 N4 O'
_chemical_formula_sum            'C25 H18 Cl2 F2 N4 O'
_chemical_formula_weight         499.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-03 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8243(4)
_cell_length_b                   7.18030(10)
_cell_length_c                   16.7155(3)
_cell_measurement_reflns_used    11936
_cell_measurement_temperature    274.7(3)
_cell_measurement_theta_max      76.0480
_cell_measurement_theta_min      2.7180
_cell_volume                     2308.48(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      274.7(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    134.00 173.00   0.50    0.05    --  109.62  45.00 150.00   78
  2  ω    135.00 162.00   0.50    0.05    --  109.62 125.00  90.00   54
  3  ω     81.00 122.00   0.50    0.05    --  109.62 125.00  90.00   82
  4  ω    100.00 125.00   0.50    0.05    --  109.62 123.00 -13.00   50
  5  ω     60.00 117.00   0.50    0.05    --   44.26 148.00 150.00  114
  6  ω     91.00 118.00   0.50    0.05    --  109.62  45.00 150.00   54
  7  ω   -174.00 -74.00   0.50    0.05    -- -100.00 -77.00 -90.00  200
  8  ω   -132.00 -89.00   0.50    0.05    -- -100.00-125.00-150.00   86
  9  ω   -153.00-128.00   0.50    0.05    -- -100.00-123.00 -93.00   50
 10  ω   -117.00 -69.00   0.50    0.05    --  -44.26-148.00 102.00   96
 11  ω   -128.00-102.00   0.50    0.05    -- -100.00 148.00 150.00   52
 12  ω    -94.00 -50.00   0.50    0.05    --  -44.26 123.00 -13.00   88
 13  ω   -109.00 -35.00   0.50    0.05    -- -100.00  77.00   0.00  148
 14  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00 150.00   50
 15  ω    -54.00 -29.00   0.50    0.05    -- -100.00  45.00  30.00   50
 16  ω    -54.00 -27.00   0.50    0.05    -- -100.00  61.00-150.00   54
 17  ω    -53.00 -28.00   0.50    0.05    -- -100.00  45.00-150.00   50
 18  ω    -53.00 -25.00   0.50    0.05    -- -100.00  45.00-180.00   56
 19  ω    -32.00  39.00   0.50    0.05    --   44.26 -37.00 -60.00  142
 20  ω    -18.00  23.00   0.50    0.05    --   44.26 -19.00 -30.00   82
 21  ω    -30.00  -3.00   0.50    0.05    --   44.26 -19.00 -90.00   54
 22  ω    -28.00  -3.00   0.50    0.05    --   44.26 -19.00-120.00   50
 23  ω     54.00  80.00   0.50    0.05    --   44.26-123.00 -93.00   52
 24  ω     37.00 107.00   0.50    0.05    --  109.62-123.00 -93.00  140
 25  ω     57.00 107.00   0.50    0.05    --  109.62-125.00 -30.00  100
 26  ω     62.00 128.00   0.50    0.05    --  109.62-148.00 102.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0626219000
_diffrn_orient_matrix_UB_12      -0.1283177000
_diffrn_orient_matrix_UB_13      0.0342479000
_diffrn_orient_matrix_UB_21      0.0485778000
_diffrn_orient_matrix_UB_22      0.1706154000
_diffrn_orient_matrix_UB_23      0.0146697000
_diffrn_orient_matrix_UB_31      -0.0116085000
_diffrn_orient_matrix_UB_32      0.0216543000
_diffrn_orient_matrix_UB_33      0.0873664000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14610
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_min         5.382
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0533
_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)+(0.0894P)²+0.6323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4214
_reflns_number_total             4553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00044g2.cif
_cod_data_source_block           fy_0328_auto
_cod_depositor_comments
'Adding full bibliography for 7159847--7159850.cif.'
_cod_database_code               7159848
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C13(H13), C14(H14), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.260
_oxdiff_exptl_absorpt_empirical_full_min 0.558
loop_
_space_group_symop_operation_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_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
Cl1 Cl 0.49634(3) 0.37955(8) 0.40333(3) 0.05760(18) Uani 1 1 d . . . . .
Cl2 Cl 0.45803(3) 0.39395(8) 0.07404(3) 0.05870(18) Uani 1 1 d . . . . .
F1 F 0.07876(8) 0.6250(2) 0.08188(9) 0.0767(5) Uani 1 1 d . . . . .
F2 F 0.08160(8) 0.9263(3) 0.08993(10) 0.0813(5) Uani 1 1 d . . . . .
O1 O 0.21892(7) 0.41685(16) 0.29786(8) 0.0409(3) Uani 1 1 d . . . . .
N1 N 0.29495(8) 0.7782(2) 0.42838(9) 0.0374(3) Uani 1 1 d . . . . .
N2 N 0.28863(7) 0.7087(2) 0.21818(8) 0.0337(3) Uani 1 1 d . . . . .
N3 N 0.23845(7) 0.7010(2) 0.14420(8) 0.0347(3) Uani 1 1 d . . . . .
N4 N 0.26033(8) 0.60435(19) 0.41188(9) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.25664(8) 0.7418(2) 0.28714(9) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.38934(9) 0.5513(2) 0.30174(11) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.375650 0.583446 0.349346 0.044 Uiso 1 1 calc R . . . .
C3 C 0.24186(8) 0.5625(2) 0.32979(10) 0.0317(3) Uani 1 1 d . . . . .
C4 C 0.18157(9) 0.7651(2) 0.15612(10) 0.0349(3) Uani 1 1 d . . . . .
C5 C 0.29611(8) 0.8545(2) 0.35973(10) 0.0336(3) Uani 1 1 d . . . . .
C6 C 0.37099(9) 0.5581(2) 0.15339(11) 0.0363(4) Uani 1 1 d . . . . .
H6 H 0.345137 0.594131 0.101565 0.044 Uiso 1 1 calc R . . . .
C7 C 0.34958(8) 0.6044(2) 0.22452(10) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.18738(8) 0.8408(2) 0.24183(10) 0.0328(3) Uani 1 1 d . . . . .
H8 H 0.197686 0.974074 0.240135 0.039 Uiso 1 1 calc R . . . .
C9 C 0.25544(10) 0.4893(2) 0.47907(10) 0.0376(4) Uani 1 1 d . . . . .
C10 C 0.12828(8) 0.8218(3) 0.28371(10) 0.0371(4) Uani 1 1 d . . . . .
C11 C 0.43175(10) 0.4571(2) 0.16224(11) 0.0401(4) Uani 1 1 d . . . . .
C12 C 0.44964(9) 0.4497(2) 0.30648(11) 0.0394(4) Uani 1 1 d . . . . .
C13 C 0.30991(12) 0.4852(3) 0.54877(12) 0.0500(5) Uani 1 1 d . . . . .
H13 H 0.350294 0.552889 0.550776 0.060 Uiso 1 1 calc R . . . .
C14 C 0.47217(10) 0.4004(3) 0.23776(12) 0.0430(4) Uani 1 1 d . . . . .
H14 H 0.512726 0.332127 0.241912 0.052 Uiso 1 1 calc R . . . .
C15 C 0.33015(11) 1.0367(3) 0.35453(13) 0.0501(5) Uani 1 1 d . . . . .
H15A H 0.350736 1.081342 0.409116 0.075 Uiso 1 1 calc GR . . . .
H15B H 0.296131 1.124637 0.326329 0.075 Uiso 1 1 calc GR . . . .
H15C H 0.365585 1.021944 0.324767 0.075 Uiso 1 1 calc GR . . . .
C16 C 0.08600(10) 0.6649(3) 0.27434(12) 0.0474(4) Uani 1 1 d . . . . .
H16 H 0.092362 0.569147 0.239438 0.057 Uiso 1 1 calc R . . . .
C17 C 0.12000(10) 0.7752(3) 0.08347(12) 0.0462(4) Uani 1 1 d . . . . .
H17 H 0.135778 0.781489 0.032318 0.055 Uiso 1 1 calc R . . . .
C18 C 0.11750(11) 0.9630(3) 0.33554(12) 0.0507(5) Uani 1 1 d . . . . .
H18 H 0.145157 1.069209 0.341846 0.061 Uiso 1 1 calc R . . . .
C19 C 0.19586(13) 0.3858(3) 0.47477(14) 0.0526(5) Uani 1 1 d . . . . .
H19 H 0.159579 0.388096 0.427577 0.063 Uiso 1 1 calc R . . . .
C20 C 0.02455(11) 0.7922(5) 0.36879(14) 0.0681(7) Uani 1 1 d . . . . .
H20 H -0.010069 0.781946 0.397434 0.082 Uiso 1 1 calc R . . . .
C21 C 0.30325(17) 0.3787(3) 0.61546(14) 0.0644(7) Uani 1 1 d . . . . .
H21 H 0.339239 0.376198 0.662939 0.077 Uiso 1 1 calc R . . . .
C22 C 0.03424(11) 0.6513(4) 0.31715(14) 0.0612(6) Uani 1 1 d . . . . .
H22 H 0.005996 0.546295 0.310780 0.073 Uiso 1 1 calc R . . . .
C23 C 0.06575(13) 0.9477(4) 0.37824(14) 0.0670(7) Uani 1 1 d . . . . .
H23 H 0.059072 1.042946 0.413229 0.080 Uiso 1 1 calc R . . . .
C24 C 0.24413(19) 0.2766(3) 0.61225(15) 0.0721(8) Uani 1 1 d . . . . .
H24 H 0.239970 0.206408 0.657555 0.087 Uiso 1 1 calc R . . . .
C25 C 0.19129(17) 0.2785(3) 0.54223(17) 0.0705(7) Uani 1 1 d . . . . .
H25 H 0.151782 0.206812 0.539861 0.085 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 N4 108.42(13) . . ?
N3 N2 C1 110.76(12) . . ?
N3 N2 C7 117.66(13) . . ?
C7 N2 C1 123.81(13) . . ?
C4 N3 N2 108.41(13) . . ?
C3 N4 N1 112.85(13) . . ?
C3 N4 C9 127.98(14) . . ?
C9 N4 N1 118.80(13) . . ?
N2 C1 C3 113.45(12) . . ?
N2 C1 C5 118.74(13) . . ?
N2 C1 C8 100.89(12) . . ?
C3 C1 C8 111.19(13) . . ?
C5 C1 C3 101.34(12) . . ?
C5 C1 C8 111.55(12) . . ?
C12 C2 C7 118.93(15) . . ?
O1 C3 N4 127.85(15) . . ?
O1 C3 C1 127.83(14) . . ?
N4 C3 C1 104.32(13) . . ?
N3 C4 C8 114.22(14) . . ?
N3 C4 C17 117.82(15) . . ?
C17 C4 C8 127.63(15) . . ?
N1 C5 C1 111.93(14) . . ?
N1 C5 C15 122.57(16) . . ?
C15 C5 C1 125.45(15) . . ?
C11 C6 C7 118.06(16) . . ?
C2 C7 N2 119.99(14) . . ?
C2 C7 C6 120.23(15) . . ?
C6 C7 N2 119.77(15) . . ?
C4 C8 C1 98.71(12) . . ?
C10 C8 C1 114.96(13) . . ?
C10 C8 C4 121.18(14) . . ?
C13 C9 N4 119.37(18) . . ?
C19 C9 N4 119.60(17) . . ?
C19 C9 C13 121.01(18) . . ?
C16 C10 C8 122.39(16) . . ?
C18 C10 C8 118.62(17) . . ?
C18 C10 C16 118.95(17) . . ?
C6 C11 Cl2 118.58(15) . . ?
C14 C11 Cl2 118.10(14) . . ?
C14 C11 C6 123.31(16) . . ?
C2 C12 Cl1 117.68(14) . . ?
C14 C12 Cl1 119.80(14) . . ?
C14 C12 C2 122.50(17) . . ?
C9 C13 C21 118.8(2) . . ?
C12 C14 C11 116.95(16) . . ?
C22 C16 C10 120.0(2) . . ?
F1 C17 C4 110.34(16) . . ?
F2 C17 F1 107.10(17) . . ?
F2 C17 C4 109.83(16) . . ?
C10 C18 C23 120.6(2) . . ?
C9 C19 C25 118.7(2) . . ?
C23 C20 C22 120.2(2) . . ?
C24 C21 C13 120.7(2) . . ?
C20 C22 C16 120.4(2) . . ?
C20 C23 C18 120.0(2) . . ?
C25 C24 C21 119.9(2) . . ?
C24 C25 C19 120.9(3) . . ?
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
Cl1 C12 1.7336(19) . ?
Cl2 C11 1.7386(17) . ?
F1 C17 1.350(2) . ?
F2 C17 1.345(3) . ?
O1 C3 1.211(2) . ?
N1 N4 1.4191(19) . ?
N1 C5 1.277(2) . ?
N2 N3 1.3878(19) . ?
N2 C1 1.4634(19) . ?
N2 C7 1.403(2) . ?
N3 C4 1.278(2) . ?
N4 C3 1.365(2) . ?
N4 C9 1.416(2) . ?
C1 C3 1.534(2) . ?
C1 C5 1.510(2) . ?
C1 C8 1.569(2) . ?
C2 C7 1.393(2) . ?
C2 C12 1.386(2) . ?
C4 C8 1.511(2) . ?
C4 C17 1.500(2) . ?
C5 C15 1.484(2) . ?
C6 C7 1.396(2) . ?
C6 C11 1.383(3) . ?
C8 C10 1.510(2) . ?
C9 C13 1.384(3) . ?
C9 C19 1.382(3) . ?
C10 C16 1.390(3) . ?
C10 C18 1.384(3) . ?
C11 C14 1.382(3) . ?
C12 C14 1.376(3) . ?
C13 C21 1.385(3) . ?
C16 C22 1.389(3) . ?
C18 C23 1.389(3) . ?
C19 C25 1.387(3) . ?
C20 C22 1.373(4) . ?
C20 C23 1.370(4) . ?
C21 C24 1.372(4) . ?
C24 C25 1.369(4) . ?
