Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with Benzenediazonium Salts
Thore Wendler; Christian Schütt; Christian Näther; Rainer Herges; Journal of Organic Chemistry 77 (2012) 3284–3287; doi:10.1021/jo202688x

data_4027107
_publ_section_title
;
 Photoswitchable Azoheterocycles via Coupling of Lithiated Imidazoles with
 Benzenediazonium Salts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3284
_journal_page_last               3287
_journal_paper_doi               10.1021/jo202688x
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C11 H13 N5 O2 S'
_chemical_formula_weight         279.32
_chemical_name_common            1-Dimethylsulfamoyl-5-phenylazoimidazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.082(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0124(9)
_cell_length_b                   6.3282(3)
_cell_length_c                   15.2728(10)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      10.8
_cell_volume                     1301.29(14)
_computing_cell_refinement       'STOE IPDS-1 program package'
_computing_data_collection       'STOE IPDS-1 program package'
_computing_data_reduction        'STOE IPDS-1 program package'
_computing_molecular_graphics    'XP in SHELXTL'
_computing_publication_material  'XCIF in SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_measurement_method       'Phi 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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14575
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.048(5)
_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   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0622P)^2^+0.3409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                2739
_reflns_number_total             3148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202688x_si_001.cif
_cod_data_source_block           herges76
_cod_original_cell_volume        1301.29(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027107