Acylpyrazolones possessing a heterocyclic moiety in the acyl fragment: intramolecular vs. intermolecular zwitterionic structures
Todorova, Stanislava E.; Rusew, Rusi I.; Petkova, Zhanina S.; Shivachev, Boris L.; Nikolova, Rositsa P.; Kurteva, Vanya B.; New Journal of Chemistry 46 (2022) 1080–1086; doi:10.1039/D1NJ05458A

data_7061114
_publ_section_title
;
 Acylpyrazolones possessing a heterocyclic moiety in the acyl fragment:
 intramolecular vs. intermolecular zwitterionic structures
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1080
_journal_page_last               1086
_journal_paper_doi               10.1039/D1NJ05458A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C13 H10 Cl Cs N2 O5'
_chemical_formula_sum            'C13 H10 Cl Cs N2 O5'
_chemical_formula_weight         442.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-10-13
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2021-11-02 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   48.4669(10)
_cell_length_b                   32.2650(5)
_cell_length_c                   4.40930(10)
_cell_measurement_reflns_used    15288
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.8460
_cell_measurement_theta_min      2.1020
_cell_volume                     6895.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -130.61  53.59   0.60   10.00  14.61  -8.96 -28.85    --   307
  2  \w   -104.62  19.58   0.60   10.00    --   -8.96 -59.25 -51.92  207
  3  \w   -104.62  19.58   0.60   10.00    --   -8.96 -59.25  92.08  207
  4  \w   -104.62  19.58   0.60   10.00    --   -8.96 -59.25 164.08  207
  5  \w   -104.62  19.58   0.60   10.00    --   -8.96 -59.25-123.92  207
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            33825
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_min         1.516
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       plate
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+34.1559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3270
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05458a2.cif
_cod_data_source_block           mo_b_0144
_cod_depositor_comments
'Adding full bibliography for 7061108--7061121.cif.'
_cod_database_code               7061114
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.893
_shelx_estimated_absorpt_t_min   0.542
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              70456
_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
;