Palladium-catalyzed intramolecular asymmetric hydrocyclopropanylation of alkynes: synthesis of cyclopropane-fused γ-lactams.
Lin, Han-Ze; Qi, Zhuang; Wu, Qi-Min; Jiang, Yong-Yu; Peng, Jin-Bao; Chemical science 14 (2023) 7564–7568; doi:10.1039/d3sc02168h

data_1569346
_publ_section_title
;
 Palladium-catalyzed intramolecular asymmetric hydrocyclopropanylation of
 alkynes: synthesis of cyclopropane-fused &#x3b3;-lactams.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              7564
_journal_page_last               7568
_journal_paper_doi               10.1039/d3sc02168h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C23 H25 N O3 S'
_chemical_formula_sum            'C23 H25 N O3 S'
_chemical_formula_weight         395.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-04-18 deposited with the CCDC.	2023-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4147(5)
_cell_length_b                   10.4118(4)
_cell_length_c                   12.7924(4)
_cell_measurement_reflns_used    4192
_cell_measurement_temperature    298.37(10)
_cell_measurement_theta_max      75.8170
_cell_measurement_theta_min      5.1380
_cell_volume                     2053.11(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.37(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.931
_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     39.00  64.00   0.50    1.79    --  108.86 -57.00 -30.00   50
  2  \w     37.00  62.00   0.50    1.79    --  108.86 -57.00 -60.00   50
  3  \w     38.00  65.00   0.50    1.79    --  108.86 -57.00 -90.00   54
  4  \w     41.00  66.00   0.50    1.79    --  108.86 -57.00-180.00   50
  5  \w    -17.00  27.00   0.50    0.45    --  -48.55  19.00-120.00   88
  6  \w    -73.00 -21.00   0.50    0.45    --  -48.55 125.00-180.00  104
  7  \w    -70.00 -24.00   0.50    1.79    --  -91.75 105.00-122.00   92
  8  \w    -83.00 -30.00   0.50    1.79    --  -91.75 139.00 128.00  106
  9  \w    -65.00 -39.00   0.50    1.79    --  -91.75  57.00  60.00   52
 10  \w   -118.00 -43.00   0.50    0.45    --  -48.55 -20.00 -69.00  150
 11  \w   -158.00 -90.00   0.50    1.79    --  -91.75 -20.00 -69.00  136
 12  \w     78.00 108.00   0.50    1.79    --  108.86-125.00 -90.00   60
 13  \w     38.00  63.00   0.50    1.79    --  108.86-125.00 -90.00   50
 14  \w     41.00 101.00   0.50    1.79    --  108.86 -99.00 150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0142064000
_diffrn_orient_matrix_UB_12      -0.1416127000
_diffrn_orient_matrix_UB_13      0.0302636000
_diffrn_orient_matrix_UB_21      -0.0989024000
_diffrn_orient_matrix_UB_22      -0.0193657000
_diffrn_orient_matrix_UB_23      0.0073517000
_diffrn_orient_matrix_UB_31      -0.0025638000
_diffrn_orient_matrix_UB_32      -0.0380900000
_diffrn_orient_matrix_UB_33      -0.1163564000
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7909
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.098
_diffrn_reflns_theta_min         5.126
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0548
_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^)+(0.1190P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.352
_reflns_Friedel_fraction_full    0.418
_reflns_Friedel_fraction_max     0.360
_reflns_number_gt                2534
_reflns_number_total             2859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02168h2.cif
_cod_data_source_block           exp_4329_auto
_cod_depositor_comments
'Adding full bibliography for 1569346--1569347.cif.'
_cod_database_code               1569346
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H23 O3 N1 S1'
_reflns_odcompleteness_completeness 98.25
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 C00C, C00I, C00G, C00H, C00O, C00F, C006, C008
 with sigma of 0.1
3.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00K(H00K)
3.b Secondary CH2 refined with riding coordinates:
 C00P(H00H,H00M)
3.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00I(H00I), C00O(H00O), C00F(H00F), C008(H008), C00E(H00E),
 C00J(H00J), C00L(H00L), C00N(H00N)
3.d Fitted hexagon refined as free rotating group:
 C006(C00C,C00I,C00G,C00O,C00F)
3.e Idealised Me refined as rotating group:
 C00M(H00A,H00B,H00G), C00Q(H00P,H00Q,H00R), C00R(H00S,H00T,H00U), C00S(H00V,
 H00W,H00X)
;
_shelx_res_checksum              30271
_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 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.517