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_7061113
_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         'C16 H19 N3 O2, 0.5(C2 H3 N)'
_chemical_formula_sum            'C17 H20.5 N3.5 O2'
_chemical_formula_weight         305.87
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-14
_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                86.844(4)
_cell_angle_beta                 89.823(4)
_cell_angle_gamma                69.381(5)
_cell_formula_units_Z            4
_cell_length_a                   9.9053(5)
_cell_length_b                   11.6377(6)
_cell_length_c                   15.0249(6)
_cell_measurement_reflns_used    6093
_cell_measurement_temperature    290
_cell_measurement_theta_max      30.7950
_cell_measurement_theta_min      2.3190
_cell_volume                     1618.34(14)
_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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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     -9.39 350.61   0.40   10.00  83.13  -7.74  28.85    --   900
  2  \w   -101.52  19.68   0.40   10.00    --   -7.74 -59.25  92.08  303
  3  \w   -101.52  19.68   0.40   10.00    --   -7.74 -59.25 -51.92  303
  4  \w   -101.52  19.68   0.40   20.00    --   -7.74 -59.25 164.08  303
  5  \w   -101.52  19.68   0.40   20.00    --   -7.74 -59.25  20.08  303
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350329000
_diffrn_orient_matrix_UB_12      0.0132691000
_diffrn_orient_matrix_UB_13      0.0414221000
_diffrn_orient_matrix_UB_21      -0.0328093000
_diffrn_orient_matrix_UB_22      -0.0442269000
_diffrn_orient_matrix_UB_23      -0.0063682000
_diffrn_orient_matrix_UB_31      0.0595952000
_diffrn_orient_matrix_UB_32      -0.0460721000
_diffrn_orient_matrix_UB_33      0.0219026000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11782
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.873
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73176
_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    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         11782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0626
_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/[\s^2^(Fo^2^)+(0.1047P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1781
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5754
_reflns_number_total             11782
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9640\% 
around [0.92 0.38 0.00] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;
_cod_data_source_file            d1nj05458a2.cif
_cod_data_source_block           mo_b_0124_twin1_hklf4
_cod_depositor_comments
;
Adding full bibliography for 7061108--7061121.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H41 N7 O4'
_cod_original_formula_weight         611.74
_cod_original_formula_moiety         '2(C16 H19 N3 O2), C2 H3 N'
_cod_original_formula_units_Z            2
_cod_database_code               7061113
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4899(13)
 0.5101(13)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C132(H13A,H13B), C122(H12A,H12B), C162(H16A,H16B), C121(H12C,H12D), C152(H15A,
 H15B), C142(H14A,H14B), C131(H13C,H13D), C161(H16C,H16D), C151(H15C,H15D),
 C141(H14C,H14D)
3.b Aromatic/amide H refined with riding coordinates:
 C62(H62), C102(H102), C101(H101), C92(H92), C82(H82), C61(H61), C72(H72),
 C91(H91), C81(H81), C71(H71)
3.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              65181
_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 1.723
_oxdiff_exptl_absorpt_empirical_full_min 0.372
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2