#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229107.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229107
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Kayarmar, Reshma'
'Viveka, S.'
'Nagaraja, G. K.'
_publ_section_title
;
 1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine
;
_journal_coeditor_code           IS2656
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o405
_journal_paper_doi               10.1107/S160053681100153X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H20 N4'
_chemical_formula_moiety         'C16 H20 N4'
_chemical_formula_sum            'C16 H20 N4'
_chemical_formula_weight         268.36
_chemical_name_systematic
;
1-Isobutyl-N,N-dimethyl-1H-
imidazo[4,5-c]quinolin-4-amine
;
_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                 101.051(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2804(2)
_cell_length_b                   18.5492(6)
_cell_length_c                   8.5147(2)
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.20
_cell_volume                     1438.57(7)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker SMART 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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13134
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0550
_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/[σ²(Fo²)+(0.0604P)²+0.3608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1456
_reflns_number_gt                2271
_reflns_number_total             3456
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2656.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229107
_cod_database_fobs_code          2229107
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.44302(15) 0.08084(8) 0.74563(17) 0.0430(4) Uani d . 1 . .
N N3 0.31258(17) 0.18631(8) 0.3740(2) 0.0512(4) Uani d . 1 . .
N N2 0.51431(15) 0.14182(8) 0.30069(17) 0.0418(4) Uani d . 1 . .
N N4 0.22238(16) 0.14021(9) 0.68830(19) 0.0520(4) Uani d . 1 . .
C C7 0.35046(18) 0.12102(9) 0.6440(2) 0.0400(4) Uani d . 1 . .
C C6 0.57198(17) 0.05715(9) 0.7062(2) 0.0386(4) Uani d . 1 . .
C C5 0.66567(19) 0.01562(10) 0.8208(2) 0.0467(5) Uani d . 1 . .
H H5A 0.6387 0.0059 0.9184 0.056 Uiso calc R 1 . .
C C4 0.7957(2) -0.01084(11) 0.7918(2) 0.0500(5) Uani d . 1 . .
H H4A 0.8563 -0.0378 0.8698 0.060 Uiso calc R 1 . .
C C3 0.8376(2) 0.00247(10) 0.6460(2) 0.0499(5) Uani d . 1 . .
H H3A 0.9262 -0.0155 0.6269 0.060 Uiso calc R 1 . .
C C2 0.74870(18) 0.04200(9) 0.5307(2) 0.0428(4) Uani d . 1 . .
H H2A 0.7771 0.0500 0.4333 0.051 Uiso calc R 1 . .
C C1 0.61517(17) 0.07070(8) 0.55699(19) 0.0358(4) Uani d . 1 . .
C C9 0.51360(17) 0.11474(8) 0.45202(19) 0.0363(4) Uani d . 1 . .
C C8 0.38711(18) 0.14192(9) 0.4938(2) 0.0395(4) Uani d . 1 . .
C C10 0.3921(2) 0.18403(10) 0.2632(2) 0.0510(5) Uani d . 1 . .
H H10A 0.3677 0.2090 0.1670 0.061 Uiso calc R 1 . .
C C11 0.61699(19) 0.12704(10) 0.1942(2) 0.0449(4) Uani d . 1 . .
H H11A 0.5682 0.1362 0.0848 0.054 Uiso calc R 1 . .
H H11B 0.6434 0.0764 0.2024 0.054 Uiso calc R 1 . .
C C12 0.7563(2) 0.17189(10) 0.2307(2) 0.0466(4) Uani d . 1 . .
H H12A 0.7980 0.1669 0.3450 0.056 Uiso calc R 1 . .
C C13 0.8672(2) 0.14245(12) 0.1367(3) 0.0684(6) Uani d . 1 . .
H H13A 0.8840 0.0923 0.1609 0.103 Uiso calc R 1 . .
H H13B 0.9579 0.1684 0.1657 0.103 Uiso calc R 1 . .
H H13C 0.8298 0.1481 0.0242 0.103 Uiso calc R 1 . .
C C14 0.7246(3) 0.25132(11) 0.1958(3) 0.0689(6) Uani d . 1 . .
H H14A 0.8137 0.2785 0.2254 0.103 Uiso calc R 1 . .
H H14B 0.6539 0.2680 0.2564 0.103 Uiso calc R 1 . .
H H14C 0.6862 0.2576 0.0837 0.103 Uiso calc R 1 . .
C C15 0.1048(2) 0.17851(13) 0.5909(3) 0.0690(6) Uani d . 1 . .
H H15A 0.1212 0.1807 0.4830 0.103 Uiso calc R 1 . .
H H15B 0.1002 0.2265 0.6318 0.103 Uiso calc R 1 . .
H H15C 0.0139 0.1540 0.5923 0.103 Uiso calc R 1 . .
C C16 0.1954(2) 0.11825(15) 0.8435(3) 0.0716(7) Uani d . 1 . .
H H16A 0.2865 0.1175 0.9193 0.107 Uiso calc R 1 . .
H H16B 0.1527 0.0709 0.8355 0.107 Uiso calc R 1 . .
H H16C 0.1292 0.1517 0.8784 0.107 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'
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
C7 N1 C6 . . 120.37(15) ?
C10 N3 C8 . . 103.93(14) ?
C10 N2 C9 . . 105.91(14) ?
C10 N2 C11 . . 125.01(15) ?
C9 N2 C11 . . 129.00(14) ?
C7 N4 C15 . . 125.46(16) ?
C7 N4 C16 . . 119.42(16) ?
C15 N4 C16 . . 115.06(16) ?
N1 C7 N4 . . 117.22(16) ?
N1 C7 C8 . . 119.85(15) ?
N4 C7 C8 . . 122.93(16) ?
N1 C6 C5 . . 117.17(15) ?
N1 C6 C1 . . 124.58(15) ?
C5 C6 C1 . . 118.24(15) ?
C4 C5 C6 . . 121.37(17) ?
C4 C5 H5A . . 119.3 ?
C6 C5 H5A . . 119.3 ?
C5 C4 C3 . . 120.26(17) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C2 C3 C4 . . 120.10(17) ?
C2 C3 H3A . . 119.9 ?
C4 C3 H3A . . 119.9 ?
C3 C2 C1 . . 121.20(16) ?
C3 C2 H2A . . 119.4 ?
C1 C2 H2A . . 119.4 ?
C2 C1 C9 . . 127.93(15) ?
C2 C1 C6 . . 118.81(15) ?
C9 C1 C6 . . 113.24(14) ?
N2 C9 C8 . . 105.21(14) ?
N2 C9 C1 . . 132.15(15) ?
C8 C9 C1 . . 122.60(15) ?
C9 C8 N3 . . 110.77(15) ?
C9 C8 C7 . . 119.13(15) ?
N3 C8 C7 . . 130.09(15) ?
N3 C10 N2 . . 114.14(16) ?
N3 C10 H10A . . 122.9 ?
N2 C10 H10A . . 122.9 ?
N2 C11 C12 . . 113.65(15) ?
N2 C11 H11A . . 108.8 ?
C12 C11 H11A . . 108.8 ?
N2 C11 H11B . . 108.8 ?
C12 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C11 C12 C14 . . 111.44(16) ?
C11 C12 C13 . . 109.34(16) ?
C14 C12 C13 . . 111.73(17) ?
C11 C12 H12A . . 108.1 ?
C14 C12 H12A . . 108.1 ?
C13 C12 H12A . . 108.1 ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N4 C15 H15A . . 109.5 ?
N4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N4 C16 H16A . . 109.5 ?
N4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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
N1 C7 . 1.325(2) ?
N1 C6 . 1.376(2) ?
N3 C10 . 1.305(2) ?
N3 C8 . 1.388(2) ?
N2 C10 . 1.365(2) ?
N2 C9 . 1.384(2) ?
N2 C11 . 1.461(2) ?
N4 C7 . 1.361(2) ?
N4 C15 . 1.427(2) ?
N4 C16 . 1.450(2) ?
C7 C8 . 1.439(2) ?
C6 C5 . 1.406(2) ?
C6 C1 . 1.426(2) ?
C5 C4 . 1.368(2) ?
C5 H5A . 0.9300 ?
C4 C3 . 1.393(3) ?
C4 H4A . 0.9300 ?
C3 C2 . 1.368(2) ?
C3 H3A . 0.9300 ?
C2 C1 . 1.405(2) ?
C2 H2A . 0.9300 ?
C1 C9 . 1.425(2) ?
C9 C8 . 1.385(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.519(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C14 . 1.521(3) ?
C12 C13 . 1.521(3) ?
C12 H12A . 0.9800 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
_geom_hbond_publ_flag
C15 H15A N3 . 0.96 2.16 2.918(3) 135 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C7 N4 . . . . 177.51(15) ?
C6 N1 C7 C8 . . . . -2.0(2) ?
C15 N4 C7 N1 . . . . -175.07(19) ?
C16 N4 C7 N1 . . . . 1.9(3) ?
C15 N4 C7 C8 . . . . 4.4(3) ?
C16 N4 C7 C8 . . . . -178.62(18) ?
C7 N1 C6 C5 . . . . 179.12(15) ?
C7 N1 C6 C1 . . . . -2.1(3) ?
N1 C6 C5 C4 . . . . 179.43(17) ?
C1 C6 C5 C4 . . . . 0.5(3) ?
C6 C5 C4 C3 . . . . -0.6(3) ?
C5 C4 C3 C2 . . . . -0.1(3) ?
C4 C3 C2 C1 . . . . 0.8(3) ?
C3 C2 C1 C9 . . . . 177.63(17) ?
C3 C2 C1 C6 . . . . -0.8(3) ?
N1 C6 C1 C2 . . . . -178.65(15) ?
C5 C6 C1 C2 . . . . 0.1(2) ?
N1 C6 C1 C9 . . . . 2.7(2) ?
C5 C6 C1 C9 . . . . -178.54(15) ?
C10 N2 C9 C8 . . . . 1.26(18) ?
C11 N2 C9 C8 . . . . -175.65(16) ?
C10 N2 C9 C1 . . . . -176.54(18) ?
C11 N2 C9 C1 . . . . 6.5(3) ?
C2 C1 C9 N2 . . . . -0.3(3) ?
C6 C1 C9 N2 . . . . 178.26(16) ?
C2 C1 C9 C8 . . . . -177.77(16) ?
C6 C1 C9 C8 . . . . 0.8(2) ?
N2 C9 C8 N3 . . . . -1.55(19) ?
C1 C9 C8 N3 . . . . 176.52(15) ?
N2 C9 C8 C7 . . . . 177.37(14) ?
C1 C9 C8 C7 . . . . -4.6(2) ?
C10 N3 C8 C9 . . . . 1.2(2) ?
C10 N3 C8 C7 . . . . -177.58(18) ?
N1 C7 C8 C9 . . . . 5.2(2) ?
N4 C7 C8 C9 . . . . -174.26(16) ?
N1 C7 C8 N3 . . . . -176.11(17) ?
N4 C7 C8 N3 . . . . 4.4(3) ?
C8 N3 C10 N2 . . . . -0.4(2) ?
C9 N2 C10 N3 . . . . -0.6(2) ?
C11 N2 C10 N3 . . . . 176.48(16) ?
C10 N2 C11 C12 . . . . 100.8(2) ?
C9 N2 C11 C12 . . . . -82.9(2) ?
N2 C11 C12 C14 . . . . -67.1(2) ?
N2 C11 C12 C13 . . . . 168.91(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656471
