N-methylimidazole promotes the reaction of homophthalic anhydride with imines.
Liu, Jian; Wang, Zheng; Levin, Aaron; Emge, Thomas J.; Rablen, Paul R.; Floyd, David M.; Knapp, Spencer; The Journal of organic chemistry 79 (2014) 7593–7599; doi:10.1021/jo501316m

data_4029827
_publ_section_title
;
 N-methylimidazole promotes the reaction of homophthalic anhydride with
 imines.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7593
_journal_page_last               7599
_journal_paper_doi               10.1021/jo501316m
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H12 F3 N2 O3, C8 H12 N O, C3 H8 O'
_chemical_formula_sum            'C28 H32 F3 N3 O5'
_chemical_formula_weight         547.57
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 118.149(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6288(6)
_cell_length_b                   9.4968(5)
_cell_length_c                   13.1535(7)
_cell_measurement_reflns_used    3694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.44
_cell_measurement_theta_min      3.80
_cell_volume                     1390.96(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7917
_diffrn_reflns_theta_full        64.37
_diffrn_reflns_theta_max         64.37
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0773
_reflns_number_gt                3533
_reflns_number_total             3686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501316m_si_001.cif
_cod_data_source_block           (\/D)-10_APE_salt
_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/rss-feeds/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029827--4029828.cif.
;
_cod_original_cell_volume        1390.95(12)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4029827