Redox-neutral rhodium(III)-catalyzed [4 + 1] annulation of <i>N</i>-aryl phthalazinediones with alkynes.
Jia, Xiuwen; Li, Pinyi; Zhao, Fei; Liu, Siyu; Organic & biomolecular chemistry 23 (2025) 10315–10320; doi:10.1039/d5ob01380a

data_7160823
_publ_section_title
;
 Redox-neutral rhodium(III)-catalyzed [4 + 1] annulation of <i>N</i>-aryl
 phthalazinediones with alkynes.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10315
_journal_page_last               10320
_journal_paper_doi               10.1039/d5ob01380a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C25 H25 F N2 O2'
_chemical_formula_sum            'C25 H25 F N2 O2'
_chemical_formula_weight         404.47
_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             2021-11-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-07-03 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.994(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.086(2)
_cell_length_b                   8.3538(9)
_cell_length_c                   22.882(4)
_cell_measurement_reflns_used    1156
_cell_measurement_temperature    100.1(5)
_cell_measurement_theta_max      72.7140
_cell_measurement_theta_min      3.8060
_cell_volume                     2111.1(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -78.00 -19.00   1.00    4.00    --  -41.11 -38.00 120.00   59
  2  \w   -120.00 -16.00   1.00    4.00    --  -41.11 -19.00  30.00  104
  3  \w    -62.00 -12.00   1.00    4.00    --  -41.11 125.00-180.00   50
  4  \w     35.00 109.00   1.00    5.00    --  107.58 -45.00-120.00   74
  5  \w     50.00  89.00   1.00    5.00    --  107.58 -95.00-180.00   39
  6  \w    113.00 178.00   1.00    5.00    --  107.58  61.00  30.00   65
  7  \w    137.00 164.00   1.00    5.00    --  107.58  15.00  60.00   27
  8  \w     73.00 122.00   1.00    5.00    --  107.58-125.00 150.00   49
  9  \w     37.00 131.00   1.00    5.00    --  107.58 -45.00  60.00   94
 10  \w     55.00 111.00   1.00    5.00    --  107.58  15.00  60.00   56
 11  \w     25.00  91.00   1.00    5.00    --  107.58 -95.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0976278000
_diffrn_orient_matrix_UB_12      0.0105218000
_diffrn_orient_matrix_UB_13      0.0521039000
_diffrn_orient_matrix_UB_21      0.0775359000
_diffrn_orient_matrix_UB_22      -0.1234365000
_diffrn_orient_matrix_UB_23      -0.0299933000
_diffrn_orient_matrix_UB_31      0.0625583000
_diffrn_orient_matrix_UB_32      0.1364674000
_diffrn_orient_matrix_UB_33      -0.0309613000
_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  0.0959
_diffrn_reflns_av_unetI/netI     0.1241
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8224
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.940
_diffrn_reflns_theta_min         3.878
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4139
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2376
_reflns_number_total             4139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01380a2.cif
_cod_data_source_block           fa-32
_cod_depositor_comments          'Adding full bibliography for 7160823.cif.'
_cod_database_code               7160823
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C23, C24, C26
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Sof(H24C)=Sof(H24D)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=1-FVAR(1)
 Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C24(H24C,H24D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20)
4.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              26170
_olex2_date_sample_data_collection 2021-11-22
_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 1.540
_oxdiff_exptl_absorpt_empirical_full_min 0.603