Chiral Primary Amine-Catalyzed Divergent Coupling of α-Substituted Acrylaldehydes with α-Diazoesters
Xue, Zaikun; Li, Yao; Luo, Sanzhong; ACS Catalysis  (2020) 10989–; doi:10.1021/acscatal.0c02405

data_4518040
_publ_section_title
;
 Chiral Primary Amine-Catalyzed Divergent Coupling of \a-Substituted
 Acrylaldehydes with \a-Diazoesters
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10989
_journal_paper_doi               10.1021/acscatal.0c02405
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O4'
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.38
_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
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.48220(10)
_cell_length_b                   15.0713(2)
_cell_length_c                   16.8103(2)
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      75.4230
_cell_measurement_theta_min      2.6300
_cell_volume                     1642.29(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_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     31.00 120.00   0.50    0.05    --   47.20  62.00  20.00  178
  2  \w   -110.00 -26.00   0.50    0.05    --  -99.00 106.00 105.00  168
  3  \w   -116.00 -26.00   0.50    0.05    --  -99.00  63.00-131.00  180
  4  \w     87.00 169.00   0.50    0.05    --  103.25  62.00  20.00  164
  5  \w     16.00  95.00   0.50    0.05    --   47.20-125.00 -30.00  158
  6  \w     35.00 123.00   0.50    0.05    --   47.20  19.00 -30.00  176
  7  \w   -168.00 -82.00   0.50    0.05    --  -99.00 -61.00 -30.00  172
  8  \w   -112.00 -27.00   0.50    0.05    --  -99.00  45.00-120.00  170
  9  \w   -168.00 -86.00   0.50    0.05    --  -99.00 -45.00 -60.00  164
 10  \w     91.00 169.00   0.50    0.05    --  103.25  30.00 -30.00  156
 11  \w     28.00 116.00   0.50    0.05    --  103.25 -30.00-120.00  176
 12  \w     32.00 120.00   0.50    0.05    --   47.20  57.00 120.00  176
 13  \w     32.00 120.00   0.50    0.05    --   47.20  57.00-150.00  176
 14  \w   -168.00 -82.00   0.50    0.05    --  -99.00 -62.00-117.00  172
 15  \w     90.00 160.00   0.50    0.05    --  103.25  15.00 120.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1148003000
_diffrn_orient_matrix_UB_12      -0.0698521000
_diffrn_orient_matrix_UB_13      -0.0501442000
_diffrn_orient_matrix_UB_21      0.1291061000
_diffrn_orient_matrix_UB_22      0.0262349000
_diffrn_orient_matrix_UB_23      -0.0732714000
_diffrn_orient_matrix_UB_31      0.1632819000
_diffrn_orient_matrix_UB_32      -0.0698541000
_diffrn_orient_matrix_UB_33      0.0226434000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15127
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.576
_diffrn_reflns_theta_min         3.939
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0419P)^2^+0.3542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3226
_reflns_number_total             3280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02405_si_003.cif
_cod_data_source_block           tx1480
_cod_depositor_comments
;

2025-09-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C1.74 H1.74 O0.35'
_cod_original_formula_weight         28.21
_cod_original_formula_moiety         '0.09(C20 H20 O4)'
_cod_original_formula_units_Z            46
_cod_database_code               4518040
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_reflns_odcompleteness_completeness 99.77
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              75609
_shelx_hkl_checksum              33868
_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 2.118
_oxdiff_exptl_absorpt_empirical_full_min 0.498