Evaluating hydrogen bonding control in the diastereoselective Diels-Alder reactions of 9-(2-aminoethyl)-anthracene derivatives.
Bawa, R. A.; Gautier, F.-M.; Adams, H.; Meijer, A. J. H. M.; Jones, S.; Organic & biomolecular chemistry 13 (2015) 10569–10577; doi:10.1039/c5ob01343g

data_7154677
_publ_section_title
;
 Evaluating hydrogen bonding control in the diastereoselective Diels-Alder
 reactions of 9-(2-aminoethyl)-anthracene derivatives.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10569
_journal_page_last               10577
_journal_paper_doi               10.1039/c5ob01343g
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H18 F3 N2 O3'
_chemical_formula_sum            'C23 H18 F3 N2 O3'
_chemical_formula_weight         427.39
_chemical_melting_point          523
_chemical_name_systematic
'(?)-(3aS,9aS)-3a,4,9,9a-Tetrahydro-4-[(1R)-ethyl-trifluoroacetamido]-2-methyl-4,9-[1?,2?]benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione '
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.275(3)
_cell_length_b                   14.422(2)
_cell_length_c                   17.487(3)
_cell_measurement_reflns_used    2794
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      43.793
_cell_measurement_theta_min      4.528
_cell_volume                     3852.3(11)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker smart4000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3594
_diffrn_reflns_av_unetI/netI     0.1782
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            79754
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.924
_diffrn_reflns_theta_min         2.265
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane / hexane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0718P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2592
_reflns_number_total             5993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01343g3.cif
_cod_data_source_block           osj51redo_a
_cod_depositor_comments
'Adding full bibliography for 7154676--7154679.cif.'
_cod_original_cell_volume        3852.6(11)
_cod_database_code               7154677
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014/6
_shelx_res_checksum              2558