#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017859.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017859
loop_
_publ_author_name
'Andrade, L. C. R.'
'Paixão, J. A.'
'de Almeida, M. J. M.'
'Neves, M. A. C.'
'Sá e Melo, M. L.'
_publ_section_title
;
 6-[(4-Fluorophenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol
 and
 6-[(4-methoxyphenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol
;
_journal_coeditor_code           SK3380
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o499
_journal_page_last               o502
_journal_paper_doi               10.1107/S0108270110034773
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H16 N2 O4'
_chemical_formula_moiety         'C18 H16 N2 O4'
_chemical_formula_sum            'C18 H16 N2 O4'
_chemical_formula_weight         324.33
_chemical_name_systematic
;
6-[(4-methoxyphenyl)(1H-imidazol-1-yl)methyl]-1,3-benzodioxol-5-ol
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                100.6270(10)
_cell_angle_beta                 91.1130(10)
_cell_angle_gamma                109.8040(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6404(2)
_cell_length_b                   8.8734(2)
_cell_length_c                   13.0368(3)
_cell_measurement_reflns_used    4810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.41
_cell_measurement_theta_min      2.49
_cell_volume                     814.10(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15530
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0556P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                2069
_reflns_number_total             3738
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3380.cif
_cod_data_source_block           II
_cod_database_code               2017859
_cod_database_fobs_code          2017859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O13 0.49733(18) 1.15049(13) 0.22814(10) 0.0577(4) Uani d . 1 . .
H H13 0.4974 1.2395 0.2191 0.087 Uiso calc R 1 . .
O O14 0.13395(17) 0.94471(15) -0.10950(10) 0.0622(4) Uani d . 1 . .
O O16 0.05646(19) 0.67605(15) -0.09199(10) 0.0682(4) Uani d . 1 . .
O O23 -0.0574(3) 0.7416(3) 0.58414(13) 0.1065(6) Uani d . 1 . .
N N2 0.4919(2) 0.69716(15) 0.23070(11) 0.0472(4) Uani d . 1 . .
N N4 0.5113(2) 0.45188(18) 0.20989(14) 0.0669(5) Uani d . 1 . .
C C1 0.4238(2) 0.83622(19) 0.25755(14) 0.0476(4) Uani d . 1 . .
H H1 0.5323 0.9331 0.2875 0.057 Uiso calc R 1 . .
C C3 0.4171(3) 0.5454(2) 0.24840(16) 0.0621(5) Uani d . 1 . .
H H3 0.3110 0.5103 0.2838 0.075 Uiso calc R 1 . .
C C5 0.6532(3) 0.5489(2) 0.16444(16) 0.0651(5) Uani d . 1 . .
H H5 0.7437 0.5161 0.1300 0.078 Uiso calc R 1 . .
C C6 0.6430(3) 0.7001(2) 0.17692(15) 0.0592(5) Uani d . 1 . .
H H6 0.7238 0.7889 0.1533 0.071 Uiso calc R 1 . .
C C7 0.3479(2) 0.86956(19) 0.15922(13) 0.0435(4) Uani d . 1 . .
C C8 0.3884(2) 1.03001(19) 0.14862(13) 0.0429(4) Uani d . 1 . .
C C9 0.3228(2) 1.0678(2) 0.05937(13) 0.0474(4) Uani d . 1 . .
H H9 0.3519 1.1753 0.0514 0.057 Uiso calc R 1 . .
C C10 0.2141(2) 0.9394(2) -0.01539(13) 0.0449(4) Uani d . 1 . .
C C11 0.1697(2) 0.7798(2) -0.00520(13) 0.0476(4) Uani d . 1 . .
C C12 0.2360(2) 0.7413(2) 0.08036(13) 0.0510(5) Uani d . 1 . .
H H12 0.2077 0.6329 0.0862 0.061 Uiso calc R 1 . .
C C15 0.0440(3) 0.7790(2) -0.16043(16) 0.0662(6) Uani d . 1 . .
H H15A -0.0861 0.7594 -0.1802 0.079 Uiso calc R 1 . .
H H15B 0.1032 0.7554 -0.2236 0.079 Uiso calc R 1 . .
C C17 0.2891(3) 0.8083(2) 0.34184(14) 0.0501(5) Uani d . 1 . .
C C18 0.1052(3) 0.7880(3) 0.32508(17) 0.0879(8) Uani d . 1 . .
H H18 0.0592 0.7903 0.2590 0.105 Uiso calc R 1 . .
C C19 -0.0156(3) 0.7643(4) 0.40342(19) 0.1056(10) Uani d . 1 . .
H H19 -0.1406 0.7502 0.3896 0.127 Uiso calc R 1 . .
C C20 0.0499(3) 0.7615(3) 0.50094(16) 0.0764(7) Uani d . 1 . .
C C21 0.2334(3) 0.7827(3) 0.52024(16) 0.0750(6) Uani d . 1 . .
H H21 0.2791 0.7813 0.5866 0.090 Uiso calc R 1 . .
C C22 0.3509(3) 0.8060(3) 0.44160(16) 0.0680(6) Uani d . 1 . .
H H22 0.4760 0.8209 0.4560 0.082 Uiso calc R 1 . .
C C24 -0.2414(4) 0.7415(5) 0.5700(2) 0.1374(14) Uani d . 1 . .
H H24A -0.3141 0.6462 0.5193 0.206 Uiso calc R 1 . .
H H24B -0.2382 0.8380 0.5456 0.206 Uiso calc R 1 . .
H H24C -0.2967 0.7402 0.6354 0.206 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O13 H13 . . 109.5 ?
C10 O14 C15 . . 105.45(13) ?
C11 O16 C15 . . 105.17(13) ?
C20 O23 C24 . . 117.20(19) ?
C3 N2 C6 . . 106.36(15) ?
C3 N2 C1 . . 128.74(16) ?
C6 N2 C1 . . 124.82(14) ?
C3 N4 C5 . . 105.14(16) ?
N2 C1 C7 . . 110.22(13) ?
N2 C1 C17 . . 110.41(13) ?
C7 C1 C17 . . 114.79(14) ?
N2 C1 H1 . . 107.0 ?
C7 C1 H1 . . 107.0 ?
C17 C1 H1 . . 107.0 ?
N4 C3 N2 . . 112.08(17) ?
N4 C3 H3 . . 124.0 ?
N2 C3 H3 . . 124.0 ?
C6 C5 N4 . . 109.75(18) ?
C6 C5 H5 . . 125.1 ?
N4 C5 H5 . . 125.1 ?
C5 C6 N2 . . 106.66(17) ?
C5 C6 H6 . . 126.7 ?
N2 C6 H6 . . 126.7 ?
C8 C7 C12 . . 119.92(15) ?
C8 C7 C1 . . 119.03(14) ?
C12 C7 C1 . . 121.05(14) ?
O13 C8 C7 . . 117.53(15) ?
O13 C8 C9 . . 121.03(14) ?
C7 C8 C9 . . 121.44(15) ?
C10 C9 C8 . . 116.74(15) ?
C10 C9 H9 . . 121.6 ?
C8 C9 H9 . . 121.6 ?
C9 C10 C11 . . 122.55(16) ?
C9 C10 O14 . . 127.69(15) ?
C11 C10 O14 . . 109.76(15) ?
C12 C11 C10 . . 121.24(16) ?
C12 C11 O16 . . 128.81(15) ?
C10 C11 O16 . . 109.95(15) ?
C11 C12 C7 . . 118.08(15) ?
C11 C12 H12 . . 121.0 ?
C7 C12 H12 . . 121.0 ?
O16 C15 O14 . . 109.33(15) ?
O16 C15 H15A . . 109.8 ?
O14 C15 H15A . . 109.8 ?
O16 C15 H15B . . 109.8 ?
O14 C15 H15B . . 109.8 ?
H15A C15 H15B . . 108.3 ?
C18 C17 C22 . . 116.68(19) ?
C18 C17 C1 . . 122.86(17) ?
C22 C17 C1 . . 120.44(17) ?
C17 C18 C19 . . 122.1(2) ?
C17 C18 H18 . . 119.0 ?
C19 C18 H18 . . 119.0 ?
C20 C19 C18 . . 119.7(2) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C21 C20 C19 . . 119.5(2) ?
C21 C20 O23 . . 116.27(19) ?
C19 C20 O23 . . 124.2(2) ?
C20 C21 C22 . . 119.91(19) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C21 C22 C17 . . 122.09(19) ?
C21 C22 H22 . . 119.0 ?
C17 C22 H22 . . 119.0 ?
O23 C24 H24A . . 109.5 ?
O23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O13 C8 . 1.3657(19) ?
O13 H13 . 0.8200 ?
O14 C10 . 1.376(2) ?
O14 C15 . 1.419(2) ?
O16 C11 . 1.383(2) ?
O16 C15 . 1.413(2) ?
O23 C20 . 1.373(2) ?
O23 C24 . 1.414(3) ?
N2 C3 . 1.339(2) ?
N2 C6 . 1.358(2) ?
N2 C1 . 1.483(2) ?
N4 C3 . 1.312(2) ?
N4 C5 . 1.360(3) ?
C1 C7 . 1.515(2) ?
C1 C17 . 1.516(2) ?
C1 H1 . 0.9800 ?
C3 H3 . 0.9300 ?
C5 C6 . 1.350(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.385(2) yes
C7 C12 . 1.399(2) yes
C8 C9 . 1.397(2) yes
C9 C10 . 1.362(2) yes
C9 H9 . 0.9300 ?
C10 C11 . 1.372(2) yes
C11 C12 . 1.361(2) yes
C12 H12 . 0.9300 ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C17 C18 . 1.363(3) yes
C17 C22 . 1.381(2) yes
C18 C19 . 1.387(3) yes
C18 H18 . 0.9300 ?
C19 C20 . 1.364(3) yes
C19 H19 . 0.9300 ?
C20 C21 . 1.362(3) yes
C21 C22 . 1.374(3) yes
C21 H21 . 0.9300 ?
C22 H22 . 0.9300 ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O13 H13 N4 1_565 0.82 1.88 2.6949(19) 175
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 301421
