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_1564242
_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         'C42 H38 N2 O6'
_chemical_formula_sum            'C42 H38 N2 O6'
_chemical_formula_weight         666.74
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-11
_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                90
_cell_formula_units_Z            4
_cell_length_a                   9.66433(13)
_cell_length_b                   12.43414(15)
_cell_length_c                   28.7610(4)
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.3780
_cell_measurement_theta_min      4.5680
_cell_volume                     3456.14(8)
_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      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -53.00  33.00   1.00    1.00    --  -34.98  57.00  90.00   86
  2  \w      1.00  75.00   1.00    1.00    --   34.98 -99.00-120.00   74
  3  \w    -36.00 106.00   1.00    1.00    --   34.98   0.00 150.00  142
  4  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 -60.00   67
  5  \w    -36.00  57.00   1.00    1.00    --   34.98 -38.00 120.00   93
  6  \w     23.00  90.00   1.00    1.00    --   34.98-125.00 -30.00   67
  7  \w     23.00  90.00   1.00    1.00    --   34.98-125.00  30.00   67
  8  \w     37.00 127.00   1.00    2.22    --  106.90 -45.00   0.00   90
  9  \w     36.00 113.00   1.00    2.22    --  106.90-111.00-150.00   77
 10  \w     87.00 175.00   1.00    2.22    --  106.90  61.00 120.00   88
 11  \w     87.00 175.00   1.00    2.22    --  106.90  61.00 -60.00   88
 12  \w     56.00 126.00   1.00    2.22    --  106.90 -45.00 -30.00   70
 13  \w     47.00  73.00   1.00    2.22    --  106.90 -94.00-180.00   26
 14  \w     89.00 163.00   1.00    2.22    --  106.90  45.00  60.00   74
 15  \w     75.00 119.00   1.00    2.22    --  106.90 -61.00 -90.00   44
;
_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      0.0667568000
_diffrn_orient_matrix_UB_12      0.0408910000
_diffrn_orient_matrix_UB_13      0.0453248000
_diffrn_orient_matrix_UB_21      -0.1418542000
_diffrn_orient_matrix_UB_22      -0.0045378000
_diffrn_orient_matrix_UB_23      0.0243698000
_diffrn_orient_matrix_UB_31      0.0289018000
_diffrn_orient_matrix_UB_32      -0.1168350000
_diffrn_orient_matrix_UB_33      0.0149025000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18584
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.502
_diffrn_reflns_theta_min         3.873
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79439
_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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0919P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1274
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                6289
_reflns_number_total             6621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03517g2.cif
_cod_data_source_block           14
_cod_database_code               1564242
_reflns_odcompleteness_completeness 99.18
_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:
 C00B(H00B), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00C), C00L(H00D,H00E), C00M(H00F,H00H), C00Q(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C010(H010), C011(H011), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C019(H019), C01B(H01G)
2.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C), C01A(H01D,H01E,H01F), C01D(H01H,H01I,H01J), C01E(H01K,
 H01L,H01M)
;
_shelx_res_checksum              20208
_shelx_hkl_checksum              1888
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-06-11
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.756