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_7247608
_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         'C54 H40 Br2 O2 P2'
_chemical_formula_sum            'C54 H40 Br2 O2 P2'
_chemical_formula_weight         942.62
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-24 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                101.507(3)
_cell_angle_beta                 108.532(3)
_cell_angle_gamma                108.298(4)
_cell_formula_units_Z            3
_cell_length_a                   14.3800(5)
_cell_length_b                   15.4793(7)
_cell_length_c                   17.3460(6)
_cell_measurement_reflns_used    7811
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.1800
_cell_measurement_theta_min      2.8590
_cell_volume                     3278.1(3)
_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      149.99(10)
_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 0.964
_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    -65.00  34.00   1.00    1.00    --  -40.36  38.00  60.00   99
  2  \w    -60.00  32.00   1.00    1.00    --  -40.36  57.00 150.00   92
  3  \w    -88.00  -5.00   1.00    1.00    --  -40.36 125.00 150.00   83
  4  \w     57.00  91.00   1.00    1.00    --   40.36-125.00  30.00   34
  5  \w     38.00  67.00   1.00    2.00    --  108.83-125.00 -30.00   29
  6  \w     82.00 109.00   1.00    2.00    --  108.83-125.00 -30.00   27
  7  \w     49.00 120.00   1.00    2.00    --  108.83-125.00-150.00   71
  8  \w     47.00 120.00   1.00    2.00    --  108.83 -15.00 -60.00   73
  9  \w     80.00 113.00   1.00    2.00    --  108.83  61.00   0.00   33
 10  \w    145.00 173.00   1.00    2.00    --  108.83  61.00   0.00   28
 11  \w    146.00 175.00   1.00    2.00    --  108.83  77.00-120.00   29
 12  \w     98.00 125.00   1.00    2.00    --  108.83 125.00-120.00   27
 13  \w     94.00 140.00   1.00    2.00    --  108.83 125.00 -90.00   46
 14  \w     80.00 178.00   1.00    2.00    --  108.83  61.00 -30.00   98
 15  \w     89.00 172.00   1.00    2.00    --  108.83  45.00  90.00   83
 16  \w     77.00 122.00   1.00    2.00    --  108.83  77.00-120.00   45
 17  \w     36.00 131.00   1.00    2.00    --  108.83 -77.00  30.00   95
 18  \w     40.00 116.00   1.00    2.00    --  108.83-125.00  60.00   76
 19  \w     36.00 140.00   1.00    2.00    --  108.83 -77.00-150.00  104
 20  \w   -106.00 -16.00   1.00    1.00    --  -40.36 -38.00-120.00   90
;
_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      0.0247570000
_diffrn_orient_matrix_UB_12      0.1083484000
_diffrn_orient_matrix_UB_13      0.0313067000
_diffrn_orient_matrix_UB_21      0.1088964000
_diffrn_orient_matrix_UB_22      0.0243251000
_diffrn_orient_matrix_UB_23      -0.0068249000
_diffrn_orient_matrix_UB_31      -0.0530833000
_diffrn_orient_matrix_UB_32      -0.0047215000
_diffrn_orient_matrix_UB_33      -0.0940094000
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23821
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.450
_diffrn_reflns_theta_min         2.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47449
_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    1.432
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.416
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         12906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0787P)^2^+2.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9761
_reflns_number_total             12906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03165a2.cif
_cod_data_source_block           glj-p
_cod_depositor_comments
'Adding full bibliography for 7247605--7247608.cif.'
_cod_original_cell_volume        3278.1(2)
_cod_database_code               7247608
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.708
_shelx_estimated_absorpt_t_min   0.650
_reflns_odcompleteness_completeness 99.75
_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
2. Others
 Sof(H47A)=Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=1-FVAR(1)
 Sof(H47)=Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C31(H31), C71(H71), C72(H72)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39),
 C40(H40), C41(H41), C42(H42), C45(H45), C46(H46), C47(H47), C47(H47A),
 C48(H48), C49(H49), C50(H50), C51(H51), C53(H53), C54(H54), C55(H55), C56(H56),
  C57(H57), C60(H60), C61(H61), C62(H62), C63(H63), C64(H64), C66(H66),
 C67(H67), C68(H68), C69(H69), C70(H70), C75(H75), C76(H76), C78(H78), C79(H79),
  C82(H82), C83(H83), C84(H84), C85(H85)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              83553
_shelx_fab_checksum              5877
_olex2_date_sample_data_collection 2021-11-23
_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 1.727
_oxdiff_exptl_absorpt_empirical_full_min 0.444