A new type of δ-vinylvalerolactone for palladium-catalyzed cycloaddition: synthesis of nine-membered heterocycles
Li, Kuan; Yang, Sen; Zheng, Bing; Wang, Wei; Wu, Yongjun; Li, Jing; Guo, Hongchao; Chemical Communications  (2022) –; doi:10.1039/D2CC01134D

data_7130134
_publ_section_title
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 A new type of \d-vinylvalerolactone for palladium-catalyzed
 cycloaddition: synthesis of nine-membered heterocycles
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01134D
_journal_year                    2022
_chemical_formula_moiety         'C29 H29 N3 O4 S'
_chemical_formula_sum            'C29 H29 N3 O4 S'
_chemical_formula_weight         515.61
_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
_audit_creation_date             2021-09-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                103.579(2)
_cell_angle_beta                 101.602(2)
_cell_angle_gamma                97.418(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4935(6)
_cell_length_b                   11.0890(5)
_cell_length_c                   12.2484(6)
_cell_measurement_reflns_used    8527
_cell_measurement_temperature    281(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.98
_cell_volume                     1333.64(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      281.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         3.053
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0598 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.9182.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6117
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0514P)^2^+0.4762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4519
_reflns_number_total             6117
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01134d2.cif
_cod_data_source_block           20210901_13_0m_a
_cod_original_cell_volume        1333.63(12)
_cod_database_code               7130134
_shelxl_version_number           2014-3
_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. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              18893
_olex2_submission_special_instructions 'No special instructions were received'