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_1564239
_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         'C31 H28 O3'
_chemical_formula_sum            'C31 H28 O3'
_chemical_formula_weight         448.53
_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             2019-12-03
_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                   9.4508(3)
_cell_length_b                   10.5895(3)
_cell_length_c                   24.6688(6)
_cell_measurement_reflns_used    3984
_cell_measurement_temperature    289.62(18)
_cell_measurement_theta_max      71.3430
_cell_measurement_theta_min      4.5040
_cell_volume                     2468.83(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      289.62(18)
_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 1.000
_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   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00  60.00   84
  2  \w   -105.00 -48.00   1.00    1.00    --  -36.04-161.00-149.00   57
  3  \w   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00  60.00   88
  4  \w    -89.00  -2.00   1.00    1.00    --  -36.04 125.00-150.00   87
  5  \w     39.00 124.00   1.00    2.52    --  106.21 -61.00 -60.00   85
  6  \w     39.00 124.00   1.00    2.52    --  106.21 -61.00-180.00   85
  7  \w     38.00 124.00   1.00    2.52    --  106.21 -45.00-150.00   86
  8  \w    100.00 176.00   1.00    2.52    --  106.21 111.00-120.00   76
  9  \w     37.00 109.00   1.00    2.52    --  106.21 -94.00 -90.00   72
 10  \w     37.00 109.00   1.00    2.52    --  106.21 -94.00 150.00   72
 11  \w     37.00 138.00   1.00    2.52    --  106.21   0.00 120.00  101
;
_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      -0.0355481000
_diffrn_orient_matrix_UB_12      -0.1012815000
_diffrn_orient_matrix_UB_13      0.0427346000
_diffrn_orient_matrix_UB_21      0.0652527000
_diffrn_orient_matrix_UB_22      -0.1022627000
_diffrn_orient_matrix_UB_23      -0.0367019000
_diffrn_orient_matrix_UB_31      0.1451035000
_diffrn_orient_matrix_UB_32      0.0211522000
_diffrn_orient_matrix_UB_33      0.0269635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.051
_diffrn_reflns_theta_max         67.051
_diffrn_reflns_theta_min         4.544
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54294
_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    1.207
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0632
_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^)+(0.1283P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1746
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4038
_reflns_number_total             4401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03517g2.cif
_cod_data_source_block           3s
_cod_original_cell_volume        2468.84(12)
_cod_database_code               1564239
_reflns_odcompleteness_completeness 99.92
_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. Rigid bond restraints
 C00Q, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00Q, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00Q, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C00Q \\sim C2: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
C00Q \\sim C1: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
C00Q \\sim C3: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
4.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B)
4.b Secondary CH2 refined with riding coordinates:
 C00I(H00C,H00D)
4.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V)
4.d X=CH2 refined with riding coordinates:
 C00R(H00F,H00I)
4.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              35272
_shelx_hkl_checksum              88402
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-12-03
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.664