Unexpected Reactivity of the 9-Aminoacridine Chromophore in Guanidylation Reactions
Zhidong Ma; Cynthia S. Day; Ulrich Bierbach; Journal of Organic Chemistry 72 (2007) 5387–5390; doi:10.1021/jo0705972

data_4023992
_publ_contact_author_address
; 
Department of Chemistry 
Wake Forest University
Winston-Salem, N.C. 27109
U.S.A.
;
_publ_contact_author_email       bierbau@wfu.edu
_publ_contact_author_fax         '336 758 4656'
_publ_contact_author_name        'Ulrich Bierbach'
_publ_contact_author_phone       '336 758 3507'
_publ_section_title
;
 Unexpected Reactivity of the 9-Aminoacridine Chromophore
 in Guanidylation Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5387
_journal_page_last               5390
_journal_paper_doi               10.1021/jo0705972
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C17 H17 Br N4'
_chemical_formula_weight         357.26
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-PC
_cell_angle_alpha                90.00
_cell_angle_beta                 111.158(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1235(12)
_cell_length_b                   20.633(2)
_cell_length_c                   7.1005(8)
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      4.21
_cell_volume                     1519.8(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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7851
_diffrn_reflns_theta_full        30.48
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         4.21
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  0.8994
_exptl_absorpt_correction_T_min  0.5749
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
Data were corrected for absorption effects using the 
multi-scan technique (SADABS).  The ratio of minimum
to maximum apparent transmission:  0.681302. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                3858
_reflns_number_total             4117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705972si20070322_112507.cif
_cod_data_source_block           a15i2f
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4023992