C—halogen···π dimer and C—H···π interactions in 1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1<i>H</i>-imidazole-5-carbaldehyde and 2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1<i>H</i>-imidazole-5-carbaldehyde
Nagaraj, B.; Narasimhamurthy, T.; Yathirajan, H. S.; Nagaraja, P.; Narasegowda, R. S.; Rathore, Ravindranath S.; Acta Crystallographica Section C 61 (2005) o177–o180; doi:10.1107/S0108270105001794

data_2014662
_publ_section_title
;C---halogen&#x00B7;&#x00B7;&#x00B7;\p dimer and
 C---H&#x00B7;&#x00B7;&#x00B7;\p interactions in
 1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1<i>H</i>-imidazole-5-carbaldehyde
 and
 2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1<i>H</i>-imidazole-5-carbaldehyde
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o177
_journal_page_last               o180
_journal_paper_doi               10.1107/S0108270105001794
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H20 Br Cl N2 O3'
_chemical_formula_moiety         'C17 H20 Br Cl N2 O3'
_chemical_formula_sum            'C17 H20 Br Cl N2 O3'
_chemical_formula_weight         415.72
_chemical_melting_point          360
_chemical_name_common
1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde
_chemical_name_systematic
1-(2-bromo-4,5-dimethoxybenzyl)-2-butyl-4-chloro-1H-imidazole-5-carboxaldehyde
_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_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.654(4)
_cell_angle_beta                 100.667(4)
_cell_angle_gamma                93.623(3)
_cell_formula_units_Z            2
_cell_length_a                   8.547(2)
_cell_length_b                   10.308(2)
_cell_length_c                   10.611(2)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.4
_cell_volume                     916.1(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'WinGx (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7830
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.406
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.664
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0839P)^2^+0.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1697
_reflns_number_gt                2655
_reflns_number_total             4087
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg1810.cif
_cod_data_source_block           I
_cod_original_cell_volume        916.2(4)
_cod_original_sg_symbol_H-M      P_-1
_cod_database_code               2014662
_cod_database_fobs_code          2014662