1,2,3-triazoles as conjugative pi-linkers in push-pull chromophores: importance of substituent positioning on intramolecular charge-transfer.
Jarowski, Peter D.; Wu, Yi-Lin; Schweizer, W. Bernd; Diederich, François; Organic letters 10 (2008) 3347–3350; doi:10.1021/ol801253z

data_1504795
_publ_section_title
;
 1,2,3-triazoles as conjugative pi-linkers in push-pull chromophores:
 importance of substituent positioning on intramolecular charge-transfer.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3347
_journal_page_last               3350
_journal_paper_doi               10.1021/ol801253z
_journal_volume                  10
_journal_year                    2008
_chemical_compound_source        'Diederich laboratory'
_chemical_formula_moiety         'C11 H12 N4 O, C H Cl3 '
_chemical_formula_sum            'C12 H13 Cl3 N4 O'
_chemical_formula_weight         335.622
_chemical_name_systematic
;
1-(4-(dimethylamino)phenyl)-1H-1,2,3-triazole-4-carbaldehyde chloroform
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                107.758(4)
_cell_angle_beta                 96.195(5)
_cell_angle_gamma                96.976(4)
_cell_formula_units_Z            2
_cell_length_a                   5.6317(5)
_cell_length_b                   11.7114(11)
_cell_length_c                   12.2524(14)
_cell_measurement_reflns_used    10169
_cell_measurement_temperature    223
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.425
_cell_volume                     754.87(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97(Altomare et al., J. Appl. Cryst.,1999)'
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.07296
_diffrn_orient_matrix_UB_12      -0.13143
_diffrn_orient_matrix_UB_13      0.10087
_diffrn_orient_matrix_UB_21      -0.03277
_diffrn_orient_matrix_UB_22      -0.05299
_diffrn_orient_matrix_UB_23      -0.06615
_diffrn_orient_matrix_UB_31      0.05743
_diffrn_orient_matrix_UB_32      -0.06286
_diffrn_orient_matrix_UB_33      -0.01650
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4035
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         5.21
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344.0
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .06
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+ (0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1782
_reflns_number_gt                1970
_reflns_number_total             2567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801253z-file003.cif
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C12 H13 Cl3 N4 O '
_cod_database_code               1504795