Synthesis of 1-aryl-2,3-diaroyl cyclopropanes from 1,3,5-triaryl-1,5-diketones and their transformation into E,E-1,4-diaryl-1,3-butadienes
Britto, Kashpar John; Meenakshi, Maniarasu; Srinivasan, Kannupal; RSC Advances 14 (2024) 22076–22085; doi:10.1039/D4RA02525C

data_7249044
_publ_section_title
;
 Synthesis of 1-aryl-2,3-diaroyl cyclopropanes from
 1,3,5-triaryl-1,5-diketones and their transformation into
 E,E-1,4-diaryl-1,3-butadienes
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              22076
_journal_page_last               22085
_journal_paper_doi               10.1039/D4RA02525C
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         '0.1(C18 H18)'
_chemical_formula_sum            'C H N'
_chemical_formula_weight         27.03
_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             2023-02-01
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.930(4)
_cell_angle_gamma                90
_cell_formula_units_Z            20
_cell_length_a                   12.3661(6)
_cell_length_b                   7.7969(4)
_cell_length_c                   7.2005(3)
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      25.0110
_cell_measurement_theta_min      3.2880
_cell_volume                     693.34(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_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    -37.00  22.00   0.50    3.00    --  -14.97 -94.00  30.00  118
  2  \w     10.00  71.00   0.50    3.00    --   16.22-125.00  30.00  122
  3  \w     34.00  97.00   0.50    3.00    --   16.22-171.00 113.00  126
  4  \w     32.00  69.00   0.50    3.00    --   16.22-125.00 150.00   74
  5  \w    -14.00  39.00   0.50    3.00    --   16.22 -30.00 120.00  106
  6  \w    -10.00  90.00   0.50    3.00    --   16.22  30.00 120.00  200
  7  \w     43.00  95.00   0.50    3.00    --   16.22 171.00 127.00  104
  8  \w    -63.00  -2.00   0.50    3.00    --  -14.97 114.00 -14.00  122
  9  \w    -85.00  10.00   0.50    3.00    --  -14.97 -45.00  60.00  190
 10  \w    -55.00 -20.00   0.50    3.00    --   16.22 -30.00 120.00   70
 11  \w    -94.00 -43.00   0.50    3.00    --  -14.97-171.00 113.00  102
 12  \w      2.00  64.00   0.50    3.00    --   16.22-114.00-104.00  124
 13  \w    -37.00  22.00   0.50    3.00    --  -14.97 -94.00-180.00  118
 14  \w     -6.00  84.00   0.50    3.00    --   16.22  61.00-150.00  180
 15  \w     25.00  60.00   0.50    3.00    --   16.22  77.00-180.00   70
 16  \w    -95.00 -34.00   0.50    3.00    --  -14.97 171.00 127.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0496122000
_diffrn_orient_matrix_UB_12      0.0457771000
_diffrn_orient_matrix_UB_13      0.0048505000
_diffrn_orient_matrix_UB_21      0.0282360000
_diffrn_orient_matrix_UB_22      -0.0770678000
_diffrn_orient_matrix_UB_23      0.0224416000
_diffrn_orient_matrix_UB_31      0.0060806000
_diffrn_orient_matrix_UB_32      -0.0157064000
_diffrn_orient_matrix_UB_33      -0.0959382000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8436
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.940
_diffrn_reflns_theta_min         3.090
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             280
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0758P)^2^+0.0806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                936
_reflns_number_total             1441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra02525c1.cif
_cod_data_source_block           rn30
_cod_database_code               7249044
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C002(H002), C004(H004), C005(H005), C006(H006), C007(H007), C008(H008)
2.b Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C)
;
_shelx_res_checksum              56628
_shelx_hkl_checksum              52815
_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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.436