Distinct reactivities of ortho-chalcone-substituted organophosphines with activated alkynes: skeletal editing or periphery modification
Li, Chaoyang; Niu, Xinyue; Xu, Wan; Bu, Zhanwei; Zhang, Wenjing; Wang, Qilin; Green Chemistry 25 (2023) 10587–10595; doi:10.1039/D3GC03165A

data_7247607
_publ_section_title
;
 Distinct reactivities of ortho-chalcone-substituted organophosphines with
 activated alkynes: skeletal editing or periphery modification
;
_journal_issue                   24
_journal_name_full               'Green Chemistry'
_journal_page_first              10587
_journal_page_last               10595
_journal_paper_doi               10.1039/D3GC03165A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C33 H26 Cl O5 P'
_chemical_formula_sum            'C33 H26 Cl O5 P'
_chemical_formula_weight         568.96
_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             2022-07-03
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-05 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.572(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9304(2)
_cell_length_b                   9.09920(10)
_cell_length_c                   21.2031(3)
_cell_measurement_reflns_used    7992
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      71.3010
_cell_measurement_theta_min      3.0820
_cell_volume                     2760.89(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_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    -47.00  60.00   0.50    0.50    --   42.30 -57.00 -30.00  214
  2  \w     80.00 105.00   0.50    0.50    --   42.30  77.00 120.00   50
  3  \w     15.00  86.00   0.50    0.50    --   42.30 -82.00 120.00  142
  4  \w    -26.00   9.00   0.50    0.50    --   42.30 -82.00 120.00   70
  5  \w     86.00 132.00   0.50    0.50    --   42.30  77.00  30.00   92
  6  \w     96.00 122.00   0.50    0.50    --   42.30  77.00-180.00   52
  7  \w     14.00  55.00   0.50    0.50    --  101.60 -38.00 -30.00   82
  8  \w     92.00 127.00   0.50    0.50    --  101.60 -82.00-120.00   70
  9  \w     58.00  97.00   0.50    0.50    --  101.60 -82.00 150.00   78
 10  \w     30.00 191.00   0.50    0.50    --  101.60  25.00 150.00  322
 11  \w     17.00 132.00   0.50    0.50    --  101.60 -63.00-150.00  230
 12  \w     42.00 142.00   0.50    0.50    --  101.60 -82.00-150.00  200
 13  \w     12.00 146.00   0.50    0.50    --  101.60 -25.00-180.00  268
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1062183000
_diffrn_orient_matrix_UB_12      0.0033419000
_diffrn_orient_matrix_UB_13      0.0330293000
_diffrn_orient_matrix_UB_21      0.0174581000
_diffrn_orient_matrix_UB_22      -0.0201478000
_diffrn_orient_matrix_UB_23      -0.0677353000
_diffrn_orient_matrix_UB_31      0.0000831000
_diffrn_orient_matrix_UB_32      0.1679071000
_diffrn_orient_matrix_UB_33      -0.0088286000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13610
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.650
_diffrn_reflns_theta_min         3.088
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0502P)^2^+1.0773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4775
_reflns_number_total             5251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03165a2.cif
_cod_data_source_block           lcy-64
_cod_depositor_comments
'Adding full bibliography for 7247605--7247608.cif.'
_cod_database_code               7247607
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H O N P Cl'
_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:
 C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C29(H29), C30(H30), C32(H32),
  C33(H33)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              9664
_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 2.216
_oxdiff_exptl_absorpt_empirical_full_min 0.586