From Tetrahydrofurans to Tetrahydrobenzo[ d]oxepines via a Regioselective Control of Alkyne Insertion in Rhodium-Catalyzed Arylative Cyclization.
Selmani, Aymane; Serpier, Fabien; Darses, Sylvain; The Journal of organic chemistry 84 (2019) 4566–4574; doi:10.1021/acs.joc.9b00442

data_4034258
_publ_section_title
;
 From Tetrahydrofurans to Tetrahydrobenzo[ d]oxepines via a Regioselective
 Control of Alkyne Insertion in Rhodium-Catalyzed Arylative Cyclization.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4566
_journal_page_last               4574
_journal_paper_doi               10.1021/acs.joc.9b00442
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.07930(10)
_cell_length_b                   8.16110(10)
_cell_length_c                   20.7538(3)
_cell_measurement_reflns_used    7588
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      66.54
_cell_measurement_theta_min      4.27
_cell_volume                     1368.42(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_source         micro-source
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8571
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.536
_diffrn_reflns_theta_min         5.826
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(10)
_refine_ls_extinction_coef       0.0194(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0644P)^2^+0.1229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2390
_reflns_number_total             2414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00442_si_002.cif
_cod_data_source_block           as978
_cod_database_code               4034258
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              20589
_shelx_hkl_checksum              85831