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_7247606
_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         'C30 H23 Cl N O2 P'
_chemical_formula_sum            'C30 H23 Cl N O2 P'
_chemical_formula_weight         495.91
_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             2022-04-25
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-04-03 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                89.918(4)
_cell_angle_beta                 88.573(4)
_cell_angle_gamma                81.090(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7322(16)
_cell_length_b                   10.0029(16)
_cell_length_c                   12.561(2)
_cell_measurement_reflns_used    3945
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.23
_cell_measurement_theta_min      2.62
_cell_volume                     1207.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.074
_diffrn_reflns_theta_max         25.074
_diffrn_reflns_theta_min         2.061
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.7393
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.9344.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0259P)^2^+0.8579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2464
_reflns_number_total             4274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03165a2.cif
_cod_data_source_block           43_2
_cod_depositor_comments
'Adding full bibliography for 7247605--7247608.cif.'
_cod_database_code               7247606
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 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), C18(H18), C19(H19), C20(H20), C26(H26),
  C27(H27), C29(H29), C30(H30)
;
_shelx_res_checksum              69825
_olex2_submission_special_instructions 'No special instructions were received'