H-Bond-Directing Organocatalyst for Enantioselective [4 + 2] Cycloadditions via Dienamine Catalysis.
Wang, Shoulei; Rodriguez-Escrich, Carles; Pericàs, Miquel A; Organic letters 18 (2016) 556–559; doi:10.1021/acs.orglett.5b03575

data_1542683
_publ_section_title
;
 H-Bond-Directing Organocatalyst for Enantioselective [4 + 2]
 Cycloadditions via Dienamine Catalysis.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              556
_journal_page_last               559
_journal_paper_doi               10.1021/acs.orglett.5b03575
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H36 Br N2 O4.5 S'
_chemical_formula_weight         680.64
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.5644(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.2716(8)
_cell_length_b                   10.7113(3)
_cell_length_c                   11.2422(3)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.73
_cell_volume                     3283.85(16)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32138
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.527
_diffrn_reflns_theta_min         1.493
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         10074
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.1316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                8804
_reflns_number_total             10074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03575_si_002.cif
_cod_data_source_block           mo_SW148_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C36 H36 Br N2 O4.50 S'
_cod_database_code               1542683
_shelx_estimated_absorpt_t_min   0.580
_shelx_estimated_absorpt_t_max   0.822
_shelxl_version_number           2014-3
_shelx_res_checksum              94137
_shelx_hkl_checksum              38370