Palladium-catalyzed cascade reaction of haloalkynes with unactivated alkenes for assembly of functionalized oxetanes
Li, Jianxiao; Hu, Weigao; Li, Chunsheng; Yang, Shaorong; Wu, Wanqing; Jiang, Huanfeng; Organic Chemistry Frontiers 4 (2017) 373–; doi:10.1039/C6QO00633G

data_1553576
_publ_section_title
;
 Palladium-catalyzed cascade reaction of haloalkynes with unactivated
 alkenes for assembly of functionalized oxetanes
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              373
_journal_paper_doi               10.1039/C6QO00633G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C21 H21 Cl F N O2'
_chemical_formula_sum            'C21 H21 Cl F N O2'
_chemical_formula_weight         373.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2016-07-07 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.752(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4639(2)
_cell_length_b                   21.8249(5)
_cell_length_c                   9.3192(2)
_cell_measurement_reflns_used    7506
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4360
_cell_measurement_theta_min      4.0510
_cell_volume                     1861.42(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00 -90.00  101
  2  \w    -66.00  33.00   1.00    1.00    --  -41.89  37.00  60.00   99
  3  \w     23.00  98.00   1.00    1.00    --   41.89-125.00-180.00   75
  4  \w    -34.00  74.00   1.00    1.00    --   41.89 -77.00 120.00  108
  5  \w     82.00 178.00   1.00    1.28    --  107.79  45.00-120.00   96
  6  \w     82.00 178.00   1.00    1.28    --  107.79  45.00 -60.00   96
  7  \w     94.00 178.00   1.00    1.28    --  107.79 125.00-120.00   84
  8  \w     94.00 178.00   1.00    1.28    --  107.79 125.00  60.00   84
  9  \w     25.00 109.00   1.00    1.28    --  107.79 -94.00   0.00   84
 10  \w     25.00 109.00   1.00    1.28    --  107.79 -94.00  30.00   84
 11  \w     36.00 137.00   1.00    1.28    --  107.79 -61.00 150.00  101
 12  \w   -115.00 -14.00   1.00    1.00    --  -41.89 -57.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1034517000
_diffrn_orient_matrix_UB_12      -0.0513593000
_diffrn_orient_matrix_UB_13      0.0773739000
_diffrn_orient_matrix_UB_21      -0.0948818000
_diffrn_orient_matrix_UB_22      -0.0477172000
_diffrn_orient_matrix_UB_23      -0.1029604000
_diffrn_orient_matrix_UB_31      0.0928421000
_diffrn_orient_matrix_UB_32      0.0084076000
_diffrn_orient_matrix_UB_33      -0.1124295000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12068
_diffrn_reflns_theta_full        74.11
_diffrn_reflns_theta_max         74.11
_diffrn_reflns_theta_min         4.05
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+1.2809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                3400
_reflns_number_total             3691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00633g2.cif
_cod_data_source_block           1606227
_cod_original_cell_volume        1861.42(8)
_cod_database_code               1553576
_chemical_oxdiff_formula         'C20 H20 O6 N2 Cl F'
_chemical_oxdiff_usercomment     CA-104
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C21(H21), C22(H22)
;
_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.575