Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization of norbornene and norbornadiene.
Tao, Mengna; Li, Wenbo; Zhang, Junliang; Chemical communications (Cambridge, England) 56 (2020) 13125–13128; doi:10.1039/d0cc04996d

data_7127293
_publ_section_title
;
 Pd/Xiang-Phos-catalyzed enantioselective intermolecular
 carboheterofunctionalization of norbornene and norbornadiene.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13125
_journal_page_last               13128
_journal_paper_doi               10.1039/d0cc04996d
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H16 O3'
_chemical_formula_sum            'C15 H16 O3'
_chemical_formula_weight         244.29
_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'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-02 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0733(2)
_cell_length_b                   11.5230(3)
_cell_length_c                   17.1932(4)
_cell_measurement_reflns_used    10275
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.1490
_cell_measurement_theta_min      4.6190
_cell_volume                     1203.23(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_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    -56.00 -30.00   1.00    1.00    --    0.00 -38.00 120.00   26
  2  \w     48.00  88.00   1.00    1.00    --    0.00  82.00   0.00   40
  3  \w    -19.00  33.00   1.00    1.00    --    0.00  38.00 150.00   52
  4  \w     63.00  88.00   1.00    1.00    --    0.00  38.00 -30.00   25
  5  \w    -76.00 -30.00   1.00    1.00    --    0.00 -19.00-180.00   46
  6  \w    -18.00  47.00   1.00    1.00    --    0.00  38.00 -30.00   65
  7  \w    -30.00  40.00   1.00    1.00    --    0.00  82.00   0.00   70
  8  \w     -8.00  17.00   1.00    1.00    --    0.00 -19.00-180.00   25
  9  \w    -20.00   6.00   1.00    1.00    --    0.00 -38.00 120.00   26
 10  \w    -86.00 -20.00   1.00    1.00    --    0.00 -38.00 -90.00   66
 11  \w     16.00  57.00   1.00    1.00    --    0.00  82.00-120.00   41
 12  \w    -32.00  14.00   1.00    1.00    --    0.00  82.00-120.00   46
 13  \w     44.00  87.00   1.00    1.00    --    0.00  38.00 150.00   43
 14  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  30.00   25
 15  \w    127.00 184.00   1.00    2.00    --   95.80  82.00-120.00   57
 16  \w     65.00  96.00   1.00    2.00    --   95.80  77.00  82.81   31
 17  \w      6.00 120.00   1.00    2.00    --   95.80 -61.00-180.00  114
 18  \w      6.00 128.00   1.00    2.00    --   95.80 -82.00-180.00  122
 19  \w     69.00  95.00   1.00    2.00    --   95.80  67.00 156.33   26
 20  \w     69.00 137.00   1.00    2.00    --   95.80  66.00-179.54   68
 21  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 120.00   25
 22  \w     63.00  98.00   1.00    2.00    --   95.80  82.00 -30.00   35
 23  \w     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 24  \w     72.00  99.00   1.00    2.00    --   95.80  61.00 -60.00   27
 25  \w     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 26  \w     63.00  89.00   1.00    2.00    --   95.80  82.00-120.00   26
 27  \w    109.00 185.00   1.00    2.00    --   95.80  82.00 120.00   76
 28  \w     53.00 128.00   1.00    2.00    --   95.80 -82.00  30.00   75
 29  \w     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 30  \w     75.00 144.00   1.00    2.00    --   95.80  45.00 -60.00   69
 31  \w     63.00  89.00   1.00    2.00    --   95.80  82.00   0.00   26
 32  \w     71.00 113.00   1.00    2.00    --   95.80  61.00-120.00   42
 33  \w    130.00 179.00   1.00    2.00    --   95.80  82.00 -90.00   49
 34  \w    159.00 185.00   1.00    2.00    --   95.80  44.00 164.83   26
 35  \w    122.00 185.00   1.00    2.00    --   95.80  62.00-105.72   63
 36  \w    109.00 176.00   1.00    2.00    --   95.80  77.00-150.00   67
 37  \w     65.00  91.00   1.00    2.00    --   95.80  77.00-150.00   26
 38  \w     64.00  89.00   1.00    2.00    --   95.80  82.00 -90.00   25
 39  \w     63.00  96.00   1.00    2.00    --   95.80  82.00-180.00   33
 40  \w    122.00 181.00   1.00    2.00    --   95.80  45.00 150.00   59
 41  \w     75.00 103.00   1.00    2.00    --   95.80  45.00 150.00   28
 42  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 43  \w     75.00 113.00   1.00    2.00    --   95.80  44.00 164.83   38
 44  \w     67.00  93.00   1.00    2.00    --   95.80  82.00  30.00   26
 45  \w     64.00  90.00   1.00    2.00    --   95.80  82.00  60.00   26
 46  \w     65.00  90.00   1.00    2.00    --   95.80  77.00 -90.00   25
 47  \w     63.00 116.00   1.00    2.00    --   95.80 -82.00 -30.00   53
 48  \w     76.00 107.00   1.00    2.00    --   95.80  45.00  90.00   31
 49  \w     63.00 185.00   1.00    2.00    --   95.80  82.00  90.00  122
 50  \w    106.00 155.00   1.00    2.00    --   95.80  61.00 -60.00   49
 51  \w    112.00 179.00   1.00    2.00    --   95.80  45.00  60.00   67
 52  \w     75.00 108.00   1.00    2.00    --   95.80  45.00  60.00   33
 53  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 -60.00   26
 54  \w     64.00  90.00   1.00    2.00    --   95.80  82.00 120.00   26
 55  \w     65.00  91.00   1.00    2.00    --   95.80  82.00-150.00   26
 56  \w     76.00 102.00   1.00    2.00    --   95.80  45.00-120.00   26
 57  \w    132.00 157.00   1.00    2.00    --   95.80  45.00-120.00   25
 58  \w     75.00 128.00   1.00    2.00    --   95.80  45.00   0.00   53
 59  \w     63.00  89.00   1.00    2.00    --   95.80  82.00 150.00   26
 60  \w    143.00 168.00   1.00    2.00    --   95.80  77.00  82.81   25
 61  \w     70.00  95.00   1.00    2.00    --   95.80  62.00-105.72   25
 62  \w    142.00 169.00   1.00    2.00    --   95.80  43.00  79.28   27
 63  \w     75.00 101.00   1.00    2.00    --   95.80  45.00-180.00   26
 64  \w    141.00 185.00   1.00    2.00    --   95.80  45.00-180.00   44
 65  \w     75.00 183.00   1.00    2.00    --   95.80  45.00  30.00  108
 66  \w     95.00 124.00   1.00    2.00    --   95.80 -82.00-120.00   29
 67  \w     75.00 101.00   1.00    2.00    --   95.80  43.00  79.28   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186179000
_diffrn_orient_matrix_UB_12      -0.0163705000
_diffrn_orient_matrix_UB_13      -0.0886632000
_diffrn_orient_matrix_UB_21      -0.0161237000
_diffrn_orient_matrix_UB_22      0.1323341000
_diffrn_orient_matrix_UB_23      -0.0113753000
_diffrn_orient_matrix_UB_31      0.2525294000
_diffrn_orient_matrix_UB_32      0.0096834000
_diffrn_orient_matrix_UB_33      0.0058400000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25516
_diffrn_reflns_theta_full        67.0457
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         4.62
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.3485
_exptl_crystal_description       block
_exptl_crystal_F_000             521.7237
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.1678
_refine_diff_density_min         -0.1762
_refine_diff_density_rms         0.0436
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.24(14)
_refine_ls_d_res_high            0.8372
_refine_ls_d_res_low             9.5720
_refine_ls_goodness_of_fit_ref   1.0590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0590
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0863
_reflns_Friedel_coverage         0.994
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                2075
_reflns_number_total             2130
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0cc04996d2.cif
_cod_data_source_block           exp_1057
_cod_depositor_comments
'Adding full bibliography for 7127292--7127293.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7127293
_reflns_odcompleteness_completeness 99.69
_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:
 C7(H7), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C2(H2)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_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 4.032
_oxdiff_exptl_absorpt_empirical_full_min 0.439