Asymmetric Formal [5 + 3] Cycloadditions with Unmodified Morita–Baylis–Hillman Alcohols via Double Activation Catalysis
Yang, Qian-Qian; Yin, Xiang; He, Xiao-Long; Du, Wei; Chen, Ying-Chun; ACS Catalysis 9 (2019) 1258–; doi:10.1021/acscatal.8b04942

data_4514753
_publ_section_title
;
 Asymmetric Formal [5 + 3] Cycloadditions with Unmodified
 Morita--Baylis--Hillman Alcohols via Double Activation Catalysis
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1258
_journal_paper_doi               10.1021/acscatal.8b04942
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 Br N2 O2'
_chemical_formula_sum            'C22 H19 Br N2 O2'
_chemical_formula_weight         423.30
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3331(4)
_cell_length_b                   9.8564(5)
_cell_length_c                   25.7259(12)
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    297.32(11)
_cell_measurement_theta_max      72.8980
_cell_measurement_theta_min      5.6660
_cell_volume                     1859.42(16)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      297.32(11)
_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 0.982
_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   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-180.00   84
  2  \w      1.00  75.00   1.00    1.00    --   36.29 -99.00  60.00   74
  3  \w    -31.00  53.00   1.00    1.00    --   36.29 -57.00  30.00   84
  4  \w     23.00  90.00   1.00    1.00    --   36.29-125.00-180.00   67
  5  \w    -31.00  53.00   1.00    1.00    --   36.29 -57.00 -90.00   84
  6  \w    100.00 178.00   1.00    2.01    --  108.71 111.00-120.00   78
  7  \w     40.00 126.00   1.00    2.01    --  108.71 -45.00 -30.00   86
  8  \w    100.00 178.00   1.00    2.01    --  108.71 111.00 150.00   78
  9  \w    100.00 178.00   1.00    2.01    --  108.71 111.00   0.00   78
 10  \w    100.00 178.00   1.00    2.01    --  108.71 111.00  60.00   78
 11  \w     42.00 127.00   1.00    2.01    --  108.71 -61.00  90.00   85
 12  \w     87.00 178.00   1.00    2.01    --  108.71  30.00-150.00   91
 13  \w   -104.00 -79.00   1.00    1.00    --  -36.29 -57.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0307326000
_diffrn_orient_matrix_UB_12      0.0586223000
_diffrn_orient_matrix_UB_13      0.0548461000
_diffrn_orient_matrix_UB_21      -0.2032313000
_diffrn_orient_matrix_UB_22      0.0385121000
_diffrn_orient_matrix_UB_23      0.0031638000
_diffrn_orient_matrix_UB_31      -0.0434444000
_diffrn_orient_matrix_UB_32      -0.1396983000
_diffrn_orient_matrix_UB_33      0.0238168000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8719
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.980
_diffrn_reflns_theta_min         4.805
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1244 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.048(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0590
_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^)+(0.1072P)^2^+0.3382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3364
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04942_si_002.cif
_cod_data_source_block           4c
_cod_original_cell_volume        1859.41(16)
_cod_database_code               4514753
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.80
_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
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00A(H00A), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00E), C00K(H00F,H00J), C00P(H00K,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00H(H00H), C00I(H00I), C00L(H00L),
 C00M(H00M), C00O(H00O), C00Q(H00Q), C00R(H00R)
;
_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 2.356
_oxdiff_exptl_absorpt_empirical_full_min 0.584