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_2014663
_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 H19 Cl N2 O3'
_chemical_formula_moiety         'C17 H19 Cl N2 O3'
_chemical_formula_sum            'C17 H19 Cl N2 O3'
_chemical_formula_weight         334.79
_chemical_melting_point          385
_chemical_name_common
;
2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole-
5-carboxaldehyde
;
_chemical_name_systematic
;
2-butyl-4-chloro-1-(6-methyl-1,3-benzodioxol-5-ylmethyl)-1H-imidazole-
5-carboxaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.3190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4899(5)
_cell_length_b                   9.4887(3)
_cell_length_c                   14.1018(5)
_cell_measurement_reflns_used    1237
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      23.6
_cell_measurement_theta_min      5.5
_cell_volume                     1666.50(10)
_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      130(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens 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  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6694
_diffrn_reflns_theta_full        23.29
_diffrn_reflns_theta_max         23.29
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.165
_refine_ls_extinction_coef       0.0166(15)
_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   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0354P)^2^+0.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2090
_reflns_number_total             2401
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg1810.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014663
_cod_database_fobs_code          2014663