Organocatalytic Enantioselective Cross-Aldol Reaction of o-Hydroxyarylketones and Trifluoromethyl Ketones.
Wang, Pei; Li, Hong-Feng; Zhao, Jia-Zhen; Du, Zhi-Hong; Da, Chao-Shan; Organic letters 19 (2017) 2634–2637; doi:10.1021/acs.orglett.7b00828

data_1556039
_publ_section_title
;
 Organocatalytic Enantioselective Cross-Aldol Reaction of
 o-Hydroxyarylketones and Trifluoromethyl Ketones.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2634
_journal_page_last               2637
_journal_paper_doi               10.1021/acs.orglett.7b00828
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H13 Br F3 N O3'
_chemical_formula_sum            'C16 H13 Br F3 N O3'
_chemical_formula_weight         404.18
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8132(14)
_cell_length_b                   8.851(2)
_cell_length_c                   31.166(8)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.61
_cell_volume                     1603.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9138
_diffrn_reflns_theta_full        26.57
_diffrn_reflns_theta_max         26.57
_diffrn_reflns_theta_min         1.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_T_max  0.6233
_exptl_absorpt_correction_T_min  0.5081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+0.3616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                2431
_reflns_number_total             3330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00828_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value ' unk ' was
changed to 'unk' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1603.5(7)
_cod_database_code               1556039
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'