Cu-catalyzed tandem cross-coupling/cyclization of aryl diazophosphonates with phenylacetylene derivatives.
Du, Jiahui; Ruan, Chengkai; Cui, Guifa; Zhao, Hongping; He, Chengyu; Chemical communications (Cambridge, England) 62 (2026) 2268–2271; doi:10.1039/d5cc04967a

data_7135539
_publ_section_title
;
 Cu-catalyzed tandem cross-coupling/cyclization of aryl diazophosphonates
 with phenylacetylene derivatives.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2268
_journal_page_last               2271
_journal_paper_doi               10.1039/d5cc04967a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C17 H18 N O3 P'
_chemical_formula_sum            'C17 H17 N O3 P'
_chemical_formula_weight         314.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-02-24 deposited with the CCDC.	2025-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.625(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.4243(4)
_cell_length_b                   13.8932(2)
_cell_length_c                   11.1722(2)
_cell_measurement_reflns_used    7617
_cell_measurement_temperature    297.32(10)
_cell_measurement_theta_max      76.4760
_cell_measurement_theta_min      3.7680
_cell_volume                     3287.82(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.32(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.951
_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     94.00 138.00   0.50    0.14    --  106.81  37.00   0.00   88
  2  \w    150.00 176.00   0.50    0.14    --  106.81  57.00   0.00   52
  3  \w    145.00 170.00   0.50    0.14    --  106.81  37.00   0.00   50
  4  \w     97.00 129.00   0.50    0.14    --  106.81  57.00   0.00   64
  5  \w     94.00 177.00   0.50    0.14    --  106.81  37.00 120.00  166
  6  \w     85.00 159.00   0.50    0.14    --  106.81  93.00  47.00  148
  7  \w     82.00 107.00   0.50    0.14    --  106.81 -77.00 -90.00   50
  8  \w     37.00  62.00   0.50    0.14    --  106.81 -57.00 -90.00   50
  9  \w     34.00  59.00   0.50    0.14    --  106.81 -57.00 -30.00   50
 10  \w     35.00  61.00   0.50    0.14    --  106.81 -57.00   0.00   52
 11  \w     38.00  63.00   0.50    0.14    --  106.81 -57.00 120.00   50
 12  \w    -12.00  71.00   0.50    0.05    --   47.63 -93.00 -64.00  166
 13  \w     50.00  89.00   0.50    0.14    --  106.81 -93.00 -64.00   78
 14  \w    -62.00 -33.00   0.50    0.14    -- -102.00  57.00 -90.00   58
 15  \w    -64.00 -39.00   0.50    0.14    -- -102.00  57.00-150.00   50
 16  \w    -64.00 -38.00   0.50    0.14    -- -102.00  57.00-180.00   52
 17  \w    -64.00 -39.00   0.50    0.14    -- -102.00  57.00-120.00   50
 18  \w    -63.00 -29.00   0.50    0.14    -- -102.00  57.00   0.00   68
 19  \w    -61.00 -29.00   0.50    0.14    -- -102.00  57.00 120.00   64
 20  \w   -152.00-127.00   0.50    0.14    -- -102.00 -93.00 -64.00   50
 21  \w   -116.00 -71.00   0.50    0.05    --  -47.63-125.00  60.00   90
 22  \w   -117.00 -71.00   0.50    0.05    --  -47.63-125.00   0.00   92
 23  \w   -118.00 -73.00   0.50    0.05    --  -47.63-125.00-180.00   90
 24  \w    -61.00  23.00   0.50    0.05    --  -47.63  93.00  47.00  168
 25  \w   -108.00 -38.00   0.50    0.14    -- -102.00  93.00  47.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0178527000
_diffrn_orient_matrix_UB_12      -0.1013948000
_diffrn_orient_matrix_UB_13      -0.0496258000
_diffrn_orient_matrix_UB_21      -0.0682113000
_diffrn_orient_matrix_UB_22      0.0155611000
_diffrn_orient_matrix_UB_23      0.0240511000
_diffrn_orient_matrix_UB_31      -0.0177605000
_diffrn_orient_matrix_UB_32      0.0421916000
_diffrn_orient_matrix_UB_33      -0.1280948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.557
_diffrn_reflns_theta_min         3.805
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0594P)^2^+0.9339P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2806
_reflns_number_total             3289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04967a2.cif
_cod_data_source_block           exp_4767_auto
_cod_database_code               7135539
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CHPNO
_shelx_estimated_absorpt_t_max   0.786
_shelx_estimated_absorpt_t_min   0.743
_diffrn_oxdiff_digest_frames
;
0108e115e54f6932d2423dba7962db12fc000579f26
;
_diffrn_oxdiff_digest_hkl
;
01dbfbc6ff449313704d8ad8f146be5d9aa658
;
_reflns_odcompleteness_completeness 99.90
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              76161
_shelx_hkl_checksum              99785
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.830