Rh(III)-Catalyzed olefination to build diverse oxazole derivatives from functional alkynes.
He, Yuan; Zheng, Ting; Huang, Yin-Hui; Dong, Lin; Organic & biomolecular chemistry 19 (2021) 4937–4942; doi:10.1039/d1ob00507c

data_7158071
_publ_section_title
;
 Rh(III)-Catalyzed olefination to build diverse oxazole derivatives from
 functional alkynes.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4937
_journal_page_last               4942
_journal_paper_doi               10.1039/d1ob00507c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C33 H30.905 N O'
_chemical_formula_sum            'C33 H31 N O'
_chemical_formula_weight         457.59
_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_block_doi                 10.5517/ccdc.csd.cc27sj6s
_audit_creation_date             2021-04-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-21 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                65.998(3)
_cell_angle_beta                 84.345(3)
_cell_angle_gamma                84.332(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8028(4)
_cell_length_b                   11.5069(5)
_cell_length_c                   12.8022(6)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.385
_cell_measurement_theta_min      3.788
_cell_volume                     1310.06(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33779
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.053
_diffrn_reflns_theta_max         67.053
_diffrn_reflns_theta_min         3.787
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1435 before and 0.0886 after correction.
The Ratio of minimum to maximum transmission is 0.7266.
The \l/2 correction factor is Not present.
;
_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    1.160
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.047(4)
_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   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0556
_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^)+(0.1118P)^2^+0.0505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3652
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00507c2.cif
_cod_data_source_block           cu_dl_hy_0419_0m_a
_cod_depositor_comments          'Adding full bibliography for 7158071.cif.'
_cod_database_code               7158071
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.767
_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. Uiso/Uaniso restraints and constraints
Uanis(N4A) = Uanis(N4)
Uanis(O3) = Uanis(O3A)
3. Others
 Sof(O3A)=1-FVAR(1)
 Sof(O3)=Sof(H25)=FVAR(1)
 Sof(H25A)=Sof(N4A)=1-FVAR(2)
 Sof(N4)=Sof(H26)=FVAR(2)
 Sof(C20A)=Sof(H20C)=Sof(H20D)=1-FVAR(3)
 Sof(C20)=Sof(H20A)=Sof(H20B)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C27(H27A,H27B)
4.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C31(H31), C3(H3), C5(H5), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C25(H25),
  C25(H25A), C26(H26)
4.c X=CH2 refined with riding coordinates:
 C2(H2A,H2B), C20(H20A,H20B), C20A(H20C,H20D)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              39196
_olex2_submission_special_instructions 'No special instructions were received'