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_7154678
_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_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50
_chemical_melting_point          508
_chemical_name_systematic
'(?)-(3aS,9aS)-3a,4,9,9a-Tetrahydro-4-[(1R)-ethyl-tert-butylcarbamato]-2-methyl-4,9-[1?,2?]benzeno-1H-benzo[f]isoindole-1,3-(2H)-dione '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 107.913(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9540(12)
_cell_length_b                   9.4917(8)
_cell_length_c                   16.5072(13)
_cell_measurement_reflns_used    2324
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.51
_cell_volume                     2229.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24715
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.507
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane / hexane'
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2225
_reflns_number_total             3916
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01343g3.cif
_cod_data_source_block           osj53
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154676--7154679.cif.
;
_cod_database_code               7154678
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014/6
_shelx_res_checksum              62754