Combining palladium and ammonium halide catalysts for Morita−Baylis−Hillman carbonates of methyl vinyl ketone: From 1,4-carbodipoles to ion pairs
Yang, Yang; Zhu, Bo; Zhu, Lei; Jiang, Ying; Guo, Chun-Ling; Gu, Jing; ouyang, qin; Du, Wei; Chen, Ying-Chun; Chemical Science  (2021) –; doi:10.1039/D1SC03517G

data_1564241
_publ_section_title
;
 Combining palladium and ammonium halide catalysts for
 Morita&#x2212;Baylis&#x2212;Hillman carbonates of methyl vinyl ketone:
 From 1,4-carbodipoles to ion pairs
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03517G
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 Br N2 O3'
_chemical_formula_sum            'C26 H27 Br N2 O3'
_chemical_formula_weight         495.40
_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_Hall           'P 62'
_space_group_name_H-M_alt        'P 62'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-26 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   19.5054(4)
_cell_length_b                   19.5054(4)
_cell_length_c                   10.8702(2)
_cell_measurement_reflns_used    7300
_cell_measurement_temperature    296.8(5)
_cell_measurement_theta_max      71.1020
_cell_measurement_theta_min      4.5090
_cell_volume                     3581.61(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      air
_diffrn_ambient_temperature      296.8(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -81.00  37.00   1.00    2.67    --  -35.10  15.00 -89.00  118
  2  \w   -108.00 -39.00   1.00    2.67    --  -35.10-173.00-150.00   69
  3  \w     -5.00  21.00   1.00    2.67    --   35.10  98.00  49.73   26
  4  \w     25.00  66.00   1.00    2.67    --   35.10  57.00  30.00   41
  5  \w     62.00  97.00   1.00    2.67    --   35.10 173.00-140.00   35
  6  \w     82.00 112.00   1.00    2.67    --   35.10-170.00 145.00   30
  7  \w     62.00  88.00   1.00    2.67    --   35.10  19.00  90.00   26
  8  \w     22.00  53.00   1.00    2.67    --   35.10  57.00   0.00   31
  9  \w     -2.00  25.00   1.00    2.67    --   35.10  95.00 -61.67   27
 10  \w     77.00 103.00   1.00    2.67    --   35.10  57.00  90.00   26
 11  \w      1.00  53.00   1.00    2.67    --   35.10  19.00  90.00   52
 12  \w     14.00  63.00   1.00    2.67    --   35.10  38.00   0.00   49
 13  \w     49.00  75.00   1.00    2.67    --   35.10-170.00 145.00   26
 14  \w     87.00 113.00   1.00   10.70    --  106.90  45.00 -30.00   26
 15  \w    149.00 175.00   1.00   10.70    --  106.90  77.00  30.00   26
 16  \w     78.00 103.00   1.00   10.70    --  106.90  77.00  30.00   25
 17  \w     83.00 164.00   1.00   10.70    --  106.90  30.00 -30.00   81
 18  \w     78.00 104.00   1.00   10.70    --  106.90  77.00 -60.00   26
 19  \w     78.00 104.00   1.00   10.70    --  106.90  77.00   0.00   26
 20  \w     57.00 100.00   1.00   10.70    --  106.90 -94.00-150.00   43
 21  \w     81.00 107.00   1.00   10.70    --  106.90  30.00  30.00   26
 22  \w    109.00 175.00   1.00   10.70    --  106.90  77.00 -30.00   66
 23  \w     87.00 115.00   1.00   10.70    --  106.90  61.00  30.00   28
 24  \w     83.00 109.00   1.00   10.70    --  106.90  30.00  60.00   26
 25  \w     82.00 108.00   1.00   10.70    --  106.90  30.00   0.00   26
 26  \w     78.00 104.00   1.00   10.70    --  106.90  77.00 -30.00   26
 27  \w     87.00 114.00   1.00   10.70    --  106.90  61.00 -30.00   27
 28  \w     87.00 116.00   1.00   10.70    --  106.90  45.00  60.00   29
 29  \w     38.00 108.00   1.00   10.70    --  106.90 -94.00 -90.00   70
 30  \w     90.00 166.00   1.00   10.70    --  106.90  61.00 -60.00   76
 31  \w    140.00 166.00   1.00   10.70    --  106.90  61.00   0.00   26
 32  \w    148.00 177.00   1.00   10.70    --  106.90  45.00  30.00   29
 33  \w     87.00  98.00   1.00   10.70    --  106.90  61.00   0.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0805225000
_diffrn_orient_matrix_UB_12      0.0065373000
_diffrn_orient_matrix_UB_13      -0.0275223000
_diffrn_orient_matrix_UB_21      -0.0400250000
_diffrn_orient_matrix_UB_22      -0.0909732000
_diffrn_orient_matrix_UB_23      -0.0026290000
_diffrn_orient_matrix_UB_31      -0.0151033000
_diffrn_orient_matrix_UB_32      0.0004495000
_diffrn_orient_matrix_UB_33      -0.1390452000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20115
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.293
_diffrn_reflns_theta_min         4.534
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.378
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4217
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0913P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                3943
_reflns_number_total             4217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03517g2.cif
_cod_data_source_block           9c
_cod_original_cell_volume        3581.62(16)
_cod_database_code               1564241
_reflns_odcompleteness_completeness 99.96
_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:
 C007(H007), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00O(H00I,H00M), C00P(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00R(H00S), C00S(H00T), C00T(H00U),
 C00U(H00V), C00W(H00Z)
2.d X=CH2 refined with riding coordinates:
 C00E(H00D,H00E)
2.e Idealised Me refined as rotating group:
 C00M(H00F,H00G,H00H), C00Q(H00P,H00Q,H00R), C00V(H00W,H00X,H00Y)
;
_shelx_res_checksum              31865
_shelx_hkl_checksum              89110
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-04-21
_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 1.776
_oxdiff_exptl_absorpt_empirical_full_min 0.658