Palladium-catalyzed cascade carboesterification of norbornene with alkynes.
Wu, Wanqing; Li, Can; Li, Jianxiao; Jiang, Huanfeng; Organic & biomolecular chemistry 16 (2018) 8495–8504; doi:10.1039/c8ob01799a

data_7156393
_publ_section_title
;
 Palladium-catalyzed cascade carboesterification of norbornene with
 alkynes.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8495
_journal_page_last               8504
_journal_paper_doi               10.1039/c8ob01799a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C18 H19 Cl O2'
_chemical_formula_sum            'C18 H19 Cl O2'
_chemical_formula_weight         302.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1zqfgl
_audit_creation_date             2018-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-23 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.813(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9261(3)
_cell_length_b                   10.6284(3)
_cell_length_c                   12.9254(4)
_cell_measurement_reflns_used    4076
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7340
_cell_measurement_theta_min      5.3010
_cell_volume                     1500.84(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_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    -24.00  69.00   1.00    1.00    --   41.11 -57.00  60.00   93
  2  \w     67.00 132.00   1.00    1.00    --  106.95 -45.00   0.00   65
  3  \w     55.00  97.00   1.00    1.00    --   41.11-125.00-180.00   42
  4  \w     32.00  86.00   1.00    1.00    --  106.95 -95.00 -90.00   54
  5  \w    -75.00 -35.00   1.00    1.00    --  -41.11 -38.00-180.00   40
  6  \w    106.00 167.00   1.00    1.00    --  106.95 125.00 -90.00   61
  7  \w     99.00 167.00   1.00    1.00    --  106.95 125.00-180.00   68
  8  \w    137.00 164.00   1.00    1.00    --  106.95 125.00  90.00   27
  9  \w    -66.00 -17.00   1.00    1.00    --  -41.23 -38.00 -30.00   49
 10  \w   -114.00 -88.00   1.00    1.00    --  -41.23 -38.00 -30.00   26
 11  \w      3.00  46.00   1.00    1.00    --   41.23 -99.00-180.00   43
 12  \w     47.00  73.00   1.00    1.00    --   41.23 -99.00-180.00   26
 13  \w     95.00 121.00   1.00    1.00    --  106.95 125.00-150.00   26
 14  \w     35.00  61.00   1.00    1.00    --  106.95 -95.00-150.00   26
 15  \w     84.00 109.00   1.00    1.00    --  106.95 -95.00-120.00   25
 16  \w     54.00 132.00   1.00    1.00    --  106.95 -30.00  90.00   78
 17  \w     75.00 106.00   1.00    1.00    --  106.95 -95.00 -30.00   31
;
_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      0.0981095000
_diffrn_orient_matrix_UB_12      -0.1033193000
_diffrn_orient_matrix_UB_13      -0.0118742000
_diffrn_orient_matrix_UB_21      0.0918134000
_diffrn_orient_matrix_UB_22      0.0994209000
_diffrn_orient_matrix_UB_23      -0.0376042000
_diffrn_orient_matrix_UB_31      0.0432019000
_diffrn_orient_matrix_UB_32      0.0219488000
_diffrn_orient_matrix_UB_33      0.1122781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6356
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.182
_diffrn_reflns_theta_min         5.264
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.260
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0561
_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^)+(0.1090P)^2^+0.4885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2687
_reflns_number_total             2939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01799a2.cif
_cod_data_source_block           lc-0328
_cod_depositor_comments
'Adding full bibliography for 7156393--7156394.cif.'
_cod_database_code               7156393
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.93
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C14(H14), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C2(H2)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              78351
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.750
_oxdiff_exptl_absorpt_empirical_full_min 0.605