Cs2CO3-mediated ring-opening reactions of nitrocyclopropanes via in situ generated allenes with phosphite triesters: stereoselective construction of (E)-vinylphosphonates
Wei, Jian-Sheng; Du, Xiu-Ru; Du, Zhi-Qiang; Zhong, Ling-Yi; Ma, Ao-Qiang; Wang, Jian; Xia, Ai-Bao; Xu, Dan-Qian; New Journal of Chemistry 49 (2025) 19945–19949; doi:10.1039/D5NJ02982A

data_7064110
_publ_section_title
;
 Cs2CO3-mediated ring-opening reactions of nitrocyclopropanes via in situ
 generated allenes with phosphite triesters: stereoselective construction
 of (E)-vinylphosphonates
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19945
_journal_page_last               19949
_journal_paper_doi               10.1039/D5NJ02982A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         '2(C30 H33 O7 P), C6 H6 O'
_chemical_formula_sum            'C66 H72 O15 P2'
_chemical_formula_weight         1167.17
_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             2023-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-21 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                91.4370(10)
_cell_angle_beta                 100.122(2)
_cell_angle_gamma                97.3260(10)
_cell_formula_units_Z            1
_cell_length_a                   8.4069(3)
_cell_length_b                   9.1212(3)
_cell_length_c                   20.3453(8)
_cell_measurement_reflns_used    4858
_cell_measurement_temperature    205.30
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.25
_cell_volume                     1521.48(10)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      205.30
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18392
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         2.254
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1354 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8327.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             618
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         9234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0440P)^2^+0.6405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5611
_reflns_number_total             9234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02982a2.cif
_cod_data_source_block           231208lu_lgpz049652_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7064110.cif.
;
_cod_database_code               7064110
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.984
_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, All O(H) groups
2. Others
 Fixed Sof: O8(0.5) H8A(0.5) H31(0.5)
3.a Ternary CH refined with riding coordinates:
 C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C29(H29A,H29B)
3.c 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), C18(H18), C23(H23), C31(H31), C32(H32), C33(H33)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C27(H27A,H27B,
 H27C), C30(H30A,H30B,H30C)
3.e Idealised tetrahedral OH refined as rotating group:
 O8(H8A)
;
_shelx_res_checksum              59052
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU