P<sup>III</sup>-Mediated intramolecular cyclopropanation and metal-free synthesis of cyclopropane-fused heterocycles.
Zhang, Jiayong; Hao, Jiahang; Huang, Zhiqiang; Han, Jie; He, Zhengjie; Chemical communications (Cambridge, England) 56 (2020) 10251–10254; doi:10.1039/d0cc04086j

data_7126987
_publ_section_title
;
 P<sup>III</sup>-Mediated intramolecular cyclopropanation and metal-free
 synthesis of cyclopropane-fused heterocycles.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10251
_journal_page_last               10254
_journal_paper_doi               10.1039/d0cc04086j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C23 H25 N O6 S'
_chemical_formula_sum            'C23 H25 N O6 S'
_chemical_formula_weight         443.50
_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             2018-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-16 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                80.848(2)
_cell_angle_beta                 87.645(2)
_cell_angle_gamma                69.047(2)
_cell_formula_units_Z            4
_cell_length_a                   8.7393(2)
_cell_length_b                   9.8405(3)
_cell_length_c                   28.4880(6)
_cell_measurement_reflns_used    15318
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.8670
_cell_measurement_theta_min      4.8750
_cell_volume                     2258.48(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.933
_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    -62.00 -14.00   0.50    1.00    --  -39.10  68.00-167.32   96
  2  \w    -42.00  24.00   0.50    1.00    --  -39.10  56.00  12.56  132
  3  \w    -40.00  37.00   0.50    1.00    --  -39.10  72.00  30.00  154
  4  \w    -51.00 -10.00   0.50    1.00    --  -39.10  72.00 -90.00   82
  5  \w      0.00  30.00   0.50    1.00    --  -39.10  72.00 -90.00   60
  6  \w    -56.00  43.00   0.50    1.00    --  -39.10  38.00-180.00  198
  7  \w    -62.00  46.00   0.50    1.00    --  -39.10  22.00 -53.57  216
  8  \w   -126.00 -85.00   0.50    4.00    -- -110.00  37.00  72.64   82
  9  \w   -132.00 -88.00   0.50    4.00    -- -110.00  66.00-123.27   88
 10  \w    -56.00 -22.00   0.50    4.00    -- -110.00  64.00  21.51   68
 11  \w   -135.00-109.00   0.50    4.00    -- -110.00 -30.00 122.22   52
 12  \w   -118.00 -82.00   0.50    4.00    -- -110.00  42.00 -84.06   72
 13  \w    -56.00 -30.00   0.50    4.00    -- -110.00  42.00 -84.06   52
 14  \w   -194.00-167.00   0.50    4.00    -- -110.00 -29.00 -45.56   54
 15  \w   -179.00-153.00   0.50    4.00    -- -110.00 -30.00 122.22   52
 16  \w   -127.00 -89.00   0.50    4.00    -- -110.00 -31.00 -62.62   76
 17  \w   -112.00 -86.00   0.50    4.00    -- -110.00  63.00   7.43   52
 18  \w   -188.00-151.00   0.50    4.00    -- -110.00 -19.00  30.00   74
 19  \w   -133.00-107.00   0.50    4.00    -- -110.00 -19.00  30.00   52
 20  \w    -56.00 -22.00   0.50    4.00    -- -110.00  19.00-150.00   68
 21  \w   -133.00 -24.00   0.50    4.00    -- -110.00  72.00  90.00  218
 22  \w   -132.00 -24.00   0.50    4.00    -- -110.00  57.00 -90.00  216
 23  \w   -127.00 -22.00   0.50    4.00    -- -110.00  72.00   0.00  210
 24  \w   -118.00 -92.00   0.50    4.00    -- -110.00  57.00 150.00   52
 25  \w    -57.00 -31.00   0.50    4.00    -- -110.00  38.00 -30.00   52
 26  \w   -127.00 -43.00   0.50    4.00    -- -110.00  72.00-150.00  168
 27  \w   -124.00 -28.00   0.50    4.00    -- -110.00  72.00  60.00  192
 28  \w   -160.00-124.00   0.50    4.00    -- -110.00 -22.00 163.72   72
 29  \w   -132.00 -72.00   0.50    4.00    -- -110.00  72.00-120.00  120
 30  \w    -85.00 -33.00   0.50    4.00    -- -110.00  72.00 -60.00  104
 31  \w   -133.00-106.00   0.50    4.00    -- -110.00  38.00-180.00   54
 32  \w   -199.00-172.00   0.50    4.00    -- -110.00 -31.00 -62.62   54
 33  \w    -49.00 -22.00   0.50    4.00    -- -110.00  72.00  30.00   54
 34  \w   -106.00 -62.00   0.50    4.00    -- -110.00  72.00  30.00   88
 35  \w   -115.00 -90.00   0.50    4.00    -- -110.00  72.00 150.00   50
 36  \w    -96.00 -71.00   0.50    4.00    -- -110.00  38.00-180.00   50
 37  \w    -97.00 -46.00   0.50    4.00    -- -110.00  72.00 120.00  102
 38  \w   -123.00 -97.00   0.50    4.00    -- -110.00  38.00  30.00   52
 39  \w    -82.00 -57.00   0.50    4.00    -- -110.00  38.00  30.00   50
 40  \w   -130.00-105.00   0.50    4.00    -- -110.00  19.00-150.00   50
 41  \w   -118.00 -93.00   0.50    4.00    -- -110.00 -29.00 -45.56   50
 42  \w   -167.00-142.00   0.50    4.00    -- -110.00 -19.00-180.00   50
 43  \w   -132.00 -96.00   0.50    4.00    -- -110.00 -19.00-180.00   72
 44  \w    -48.00 -23.00   0.50    4.00    -- -110.00  72.00-180.00   50
 45  \w   -185.00-156.00   0.50    4.00    -- -110.00 -19.00 120.00   58
 46  \w    -94.00 -55.00   0.50    4.00    -- -110.00  27.00 -84.85   78
 47  \w   -109.00 -83.00   0.50    4.00    -- -110.00  57.00  30.00   52
 48  \w   -116.00 -91.00   0.50    4.00    -- -110.00  57.00 120.00   50
 49  \w    -64.00 -27.00   0.50    4.00    -- -110.00  57.00 120.00   74
 50  \w   -119.00 -82.00   0.50    4.00    -- -110.00  38.00 -30.00   74
 51  \w   -108.00 -66.00   0.50    4.00    -- -110.00  72.00-180.00   84
 52  \w   -174.00-148.00   0.50    4.00    -- -110.00 -72.00  60.00   52
 53  \w   -126.00-100.00   0.50    4.00    -- -110.00 -72.00  60.00   52
 54  \w   -128.00-103.00   0.50    4.00    -- -110.00  13.00  14.28   50
 55  \w    -96.00 -23.00   0.50    4.00    -- -110.00  13.00  14.28  146
 56  \w   -100.00 -21.00   0.50    4.00    -- -110.00  72.00 -90.00  158
 57  \w   -109.00 -71.00   0.50    4.00    -- -110.00  72.00 -30.00   76
 58  \w   -133.00 -85.00   0.50    4.00    -- -110.00  38.00-120.00   96
 59  \w    -47.00 -22.00   0.50    4.00    -- -110.00  38.00-120.00   50
 60  \w    -86.00 -56.00   0.50    4.00    -- -110.00  38.00  90.00   60
 61  \w   -195.00-122.00   0.50    4.00    -- -110.00 -19.00-150.00  146
 62  \w   -188.00-140.00   0.50    4.00    -- -110.00 -19.00  60.00   96
 63  \w   -147.00-121.00   0.50    4.00    -- -110.00 -29.00 -45.56   52
 64  \w    -78.00 -37.00   0.50    4.00    -- -110.00  37.00  72.64   82
 65  \w   -134.00-109.00   0.50    4.00    -- -110.00 -19.00 120.00   50
 66  \w   -186.00-155.00   0.50    4.00    -- -110.00 -72.00-120.00   62
 67  \w   -133.00 -48.00   0.50    4.00    -- -110.00   8.00-145.29  170
 68  \w   -125.00-100.00   0.50    4.00    -- -110.00  23.00-138.89   50
 69  \w    -79.00 -54.00   0.50    4.00    -- -110.00  23.00-138.89   50
 70  \w    -91.00 -65.00   0.50    4.00    -- -110.00  71.00 -75.70   52
 71  \w   -113.00 -88.00   0.50    4.00    -- -110.00  64.00  21.51   50
 72  \w    -93.00 -67.00   0.50    4.00    -- -110.00  57.00  90.00   52
 73  \w   -104.00 -79.00   0.50    4.00    -- -110.00  19.00  30.00   50
 74  \w   -117.00 -90.00   0.50    4.00    -- -110.00 -19.00  90.00   54
 75  \w   -173.00-147.00   0.50    4.00    -- -110.00 -38.00-120.00   52
 76  \w   -197.00-113.00   0.50    4.00    -- -110.00 -72.00-180.00  168
 77  \w    -79.00 -53.00   0.50    4.00    -- -110.00  46.00-133.76   52
 78  \w    -93.00 -40.00   0.50    4.00    -- -110.00  72.00 152.47  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_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
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8595
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.331
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.304
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         8595
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0766
_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^)+(0.0984P)^2^+2.1291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2291
_refine_ls_wR_factor_ref         0.2315
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7774
_reflns_number_total             8595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04086j2.cif
_cod_data_source_block           p20181113b2_tw
_cod_depositor_comments
'Adding full bibliography for 7126985--7126988.cif.'
_cod_database_code               7126987
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.894(3)
 0.106(3)
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
 C12-C13 = C12A-C13A = C35-C36 = C35A-C36A
 1.54 with sigma of 0.01
 O2-C12 \\sim O2-C12A \\sim O8-C35 \\sim O8-C35A
 with sigma of 0.01
 O2-C13 \\sim O2-C13A \\sim O8-C36 \\sim O8-C36A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C35A) \\sim Ueq,
Uanis(C36A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
 Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(2)
 Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C25(H25), C26(H26)
6.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C15(H15A,H15B), C24(H24A,H24B), C35(H35A,H35B),
 C38(H38A,H38B), C12A(H12C,H12D), C35A(H35C,H35D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21), C22(H22),
 C30(H30), C31(H31), C32(H32), C33(H33), C41(H41), C42(H42), C44(H44), C45(H45)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C36(H36A,H36B,
 H36C), C39(H39A,H39B,H39C), C46(H46A,H46B,H46C), C13A(H13D,H13E,H13F),
 C36A(H36D,H36E,H36F)
;
_shelx_res_checksum              69304
_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 1.919
_oxdiff_exptl_absorpt_empirical_full_min 0.507