Efficient and Mild Microwave-Assisted Stepwise Functionalization of Naphthalenediimide with -Amino Acids
Paolo Pengo; G. Dan Pantoş; Sijbren Otto; Jeremy K. M. Sanders; Journal of Organic Chemistry 71 (2006) 7063–7066; doi:10.1021/jo061195h

data_4021948
_publ_section_title
;
 Efficient and Mild Microwave-Assisted Stepwise Functionalization
 of Naphthalenediimide with -Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7063
_journal_page_last               7066
_journal_paper_doi               10.1021/jo061195h
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration
;
 1524 Friedel pairs were averaged for the refinement.
;
_chemical_formula_moiety         'C34 H26 N2 O8,C3 H6 O'
_chemical_formula_sum            'C37 H32 N2 O9'
_chemical_formula_weight         648.65
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2755(2)
_cell_length_b                   13.5333(3)
_cell_length_c                   25.1099(7)
_cell_measurement_reflns_used    18305
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3152.00(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice \w and \f scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13658
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.001
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_coef       0.0057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+1.3945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                1403
_reflns_number_total             2015
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061195hsi20060609_104834.cif
_cod_database_code               4021948