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_7247605
_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         'C32 H28 Br O4 P'
_chemical_formula_sum            'C32 H28 Br O4 P'
_chemical_formula_weight         587.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-11-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-24 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.321(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1054(10)
_cell_length_b                   11.2350(3)
_cell_length_c                   24.6803(12)
_cell_measurement_reflns_used    4999
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      73.0080
_cell_measurement_theta_min      2.4110
_cell_volume                     5616.3(4)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_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      1.00  27.00   1.00    1.00    --   41.11 -99.00  60.00   26
  2  \w     50.00 109.00   1.00    2.00    --  106.95 -95.00  30.00   59
  3  \w     61.00 140.00   1.00    2.00    --  106.95 -77.00  90.00   79
  4  \w     42.00 132.00   1.00    2.00    --  106.95 -45.00  30.00   90
  5  \w     80.00 178.00   1.00    2.00    --  106.95  30.00-150.00   98
  6  \w    147.00 172.00   1.00    2.00    --  106.95 100.00  -7.00   25
  7  \w     26.00  96.00   1.00    2.00    --  106.95 -95.00 -90.00   70
  8  \w    -89.00 -21.00   1.00    1.00    --  -41.11 -57.00  90.00   68
  9  \w   -115.00 -20.00   1.00    1.00    --  -41.11 -38.00-180.00   95
 10  \w    -93.00 -34.00   1.00    1.00    --  -41.11 125.00  90.00   59
;
_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      0.0546729000
_diffrn_orient_matrix_UB_12      0.0033369000
_diffrn_orient_matrix_UB_13      -0.0302622000
_diffrn_orient_matrix_UB_21      0.0487184000
_diffrn_orient_matrix_UB_22      0.0500367000
_diffrn_orient_matrix_UB_23      0.0538653000
_diffrn_orient_matrix_UB_31      0.0205459000
_diffrn_orient_matrix_UB_32      -0.1275993000
_diffrn_orient_matrix_UB_33      0.0203295000
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.671
_diffrn_reflns_theta_min         2.440
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59820
_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    1.389
_exptl_crystal_description       block
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         11000
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0807
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1233P)^2^+4.2337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2286
_refine_ls_wR_factor_ref         0.2568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7356
_reflns_number_total             11000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03165a2.cif
_cod_data_source_block           lcy-10
_cod_depositor_comments
'Adding full bibliography for 7247605--7247608.cif.'
_cod_database_code               7247605
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.785
_shelx_estimated_absorpt_t_min   0.677
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.756(4)
 0.244(4)
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. Restrained distances
 O3-C30 \\sim O3-C0
 with sigma of 0.02
 C30-C31 \\sim C0-C34
 with sigma of 0.02
 O3-C31 \\sim O3-C34
 with sigma of 0.04
4. Rigid body (RIGU) restrains
 O00C, C020, C024
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O00C, C024, C32
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O3, C30, C31
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O3, C0, C34
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C024)=Sof(H02C)=Sof(H02D)=Sof(H02E)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C0)=
 Sof(H0A)=Sof(H0B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=1-FVAR(1)
 Sof(C020)=Sof(H02A)=Sof(H02B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C30)=
 Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00J(H00J), C00L(H00L), C13(H13), C14(H14), C15(H15)
6.b Secondary CH2 refined with riding coordinates:
 C013(H01C,H01D), C020(H02A,H02B), C32(H32A,H32B), C0(H0A,H0B), C22(H22A,H22B),
  C30(H30A,H30B)
6.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C01A(H01A), C01B(H01B), C01H(H01H), C01I(H01I), C01K(H01K),
 C01N(H01N), C01Q(H01Q), C01S(H01S), C01W(H01W), C01X(H01X), C01Y(H01Y),
 C01Z(H01Z), C010(H010), C015(H015), C017(H017), C018(H018), C021(H021), C2(H2),
  C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26), C28(H28), C29(H29)
6.d Idealised Me refined as rotating group:
 C024(H02C,H02D,H02E), C33(H33A,H33B,H33C), C31(H31A,H31B,H31C), C34(H34A,H34B,
 H34C)
;
_shelx_res_checksum              34076
_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 1.499
_oxdiff_exptl_absorpt_empirical_full_min 0.583