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_7156394
_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         'C16 H15 Cl O2'
_chemical_formula_sum            'C16 H15 Cl O2'
_chemical_formula_weight         274.73
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2018-01-03 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.880(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.07129(17)
_cell_length_b                   18.3833(5)
_cell_length_c                   12.0370(3)
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4130
_cell_measurement_theta_min      4.4670
_cell_volume                     1314.68(6)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_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     21.00  53.00   1.00    1.00    --   40.98  57.00 120.00   32
  2  \w    104.00 178.00   1.00    1.00    --  106.95  84.00 -44.00   74
  3  \w     97.00 172.00   1.00    1.00    --  106.95 125.00-180.00   75
  4  \w     82.00 159.00   1.00    1.00    --  106.95  45.00 -60.00   77
  5  \w     64.00 136.00   1.00    1.00    --  106.95 -61.00-150.00   72
  6  \w     50.00  89.00   1.00    1.00    --  106.95 -61.00-180.00   39
  7  \w     35.00 121.00   1.00    1.00    --  106.95-125.00-180.00   86
  8  \w     29.00  69.00   1.00    1.00    --   40.98-125.00  60.00   40
  9  \w   -108.00 -22.00   1.00    1.00    --  -40.98 -37.00 120.00   86
 10  \w    -75.00  -2.00   1.00    1.00    --  -40.98 125.00-150.00   73
;
_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      -0.2494561000
_diffrn_orient_matrix_UB_12      0.0187393000
_diffrn_orient_matrix_UB_13      -0.0463609000
_diffrn_orient_matrix_UB_21      0.0293337000
_diffrn_orient_matrix_UB_22      0.0714883000
_diffrn_orient_matrix_UB_23      0.0682168000
_diffrn_orient_matrix_UB_31      0.0645960000
_diffrn_orient_matrix_UB_32      0.0395143000
_diffrn_orient_matrix_UB_33      -0.1014952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4776
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.261
_diffrn_reflns_theta_min         4.458
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14790
_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            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.703
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       0.0052(15)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0815
_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^)+(0.1662P)^2^+1.6926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2494
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01799a2.cif
_cod_data_source_block           exp_795
_cod_depositor_comments
'Adding full bibliography for 7156393--7156394.cif.'
_cod_original_cell_volume        1314.67(7)
_cod_database_code               7156394
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.703
_shelx_estimated_absorpt_t_min   0.619
_reflns_odcompleteness_completeness 99.88
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C4(H4), C5(H5)
;
_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 2.053
_oxdiff_exptl_absorpt_empirical_full_min 0.313