#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/74/2017489.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_2017489
loop_
_publ_author_name
'Abonía, Rodrigo'
'Cuervo, Paola'
'Hursthouse, Michael B.'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;1-(6-Amino-1,3-benzodioxol-5-yl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)prop-2-enone:
 a sheet built by π-stacking of hydrogen-bonded chains of rings
;
_journal_coeditor_code           SK3356
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o44
_journal_page_last               o46
_journal_paper_doi               10.1107/S0108270109053554
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H14 N2 O4'
_chemical_formula_moiety         'C19 H14 N2 O4'
_chemical_formula_sum            'C19 H14 N2 O4'
_chemical_formula_weight         334.32
_chemical_name_systematic
;
1-(6-Amino-1,3-benzodioxol-5-yl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)prop-2-
enone
;
_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                83.343(2)
_cell_angle_beta                 86.652(2)
_cell_angle_gamma                77.128(2)
_cell_formula_units_Z            2
_cell_length_a                   5.7799(2)
_cell_length_b                   9.9485(3)
_cell_length_c                   13.0849(5)
_cell_measurement_reflns_used    2858
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.14
_cell_volume                     728.13(4)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9539
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0470P)²+0.3719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                2377
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3356.cif
_cod_data_source_block           I
_cod_database_code               2017489
_cod_database_fobs_code          2017489
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
C C1 0.4679(3) 0.35681(16) 0.28016(12) 0.0202(3) Uani d . 1 . .
O O1 0.6323(2) 0.25307(11) 0.29335(9) 0.0263(3) Uani d . 1 . .
C C2 0.2513(3) 0.36683(16) 0.34788(12) 0.0201(3) Uani d . 1 . .
H H2 0.1277 0.4479 0.3411 0.024 Uiso calc R 1 . .
C C3 0.2306(3) 0.26117(16) 0.41869(12) 0.0204(3) Uani d . 1 . .
H H3 0.3612 0.1837 0.4220 0.024 Uiso calc R 1 . .
O O11 0.5005(2) 0.80979(12) -0.01246(9) 0.0296(3) Uani d . 1 . .
C C12 0.2516(3) 0.87584(17) -0.01063(13) 0.0284(4) Uani d . 1 . .
H H12A 0.2306 0.9742 0.0019 0.034 Uiso calc R 1 . .
H H12B 0.1824 0.8726 -0.0775 0.034 Uiso calc R 1 . .
O O13 0.1356(2) 0.80294(11) 0.07047(9) 0.0278(3) Uani d . 1 . .
C C13a 0.3034(3) 0.68551(16) 0.10278(12) 0.0206(3) Uani d . 1 . .
C C14 0.2805(3) 0.58113(16) 0.17678(12) 0.0198(3) Uani d . 1 . .
H H14 0.1331 0.5815 0.2130 0.024 Uiso calc R 1 . .
C C15 0.4821(3) 0.47068(15) 0.19914(11) 0.0188(3) Uani d . 1 . .
C C16 0.7002(3) 0.47498(16) 0.14383(12) 0.0200(3) Uani d . 1 . .
C C17 0.7196(3) 0.59005(16) 0.07181(12) 0.0220(4) Uani d . 1 . .
H H17 0.8671 0.5970 0.0379 0.026 Uiso calc R 1 . .
C C17a 0.5198(3) 0.69051(16) 0.05271(12) 0.0212(3) Uani d . 1 . .
N N16 0.8976(3) 0.36867(15) 0.15665(11) 0.0239(3) Uani d . 1 . .
H H16A 1.038(4) 0.3888(19) 0.1399(14) 0.029 Uiso d . 1 . .
H H16B 0.887(3) 0.307(2) 0.2128(15) 0.029 Uiso d . 1 . .
N N31 -0.3581(2) 0.33571(13) 0.56186(10) 0.0199(3) Uani d . 1 . .
H H31 -0.4889 0.4008 0.5635 0.024 Uiso calc R 1 . .
C C32 -0.1853(3) 0.35897(15) 0.49073(11) 0.0192(3) Uani d . 1 . .
O O32 -0.21982(19) 0.46824(11) 0.43087(8) 0.0228(3) Uani d . 1 . .
C C33 0.0333(3) 0.25025(16) 0.49099(11) 0.0189(3) Uani d . 1 . .
C C34 0.0485(3) 0.13472(16) 0.56019(12) 0.0201(3) Uani d . 1 . .
H H34 0.1895 0.0642 0.5597 0.024 Uiso calc R 1 . .
C C34a -0.1377(3) 0.11534(16) 0.63298(12) 0.0194(3) Uani d . 1 . .
C C35 -0.1241(3) -0.00296(16) 0.70490(12) 0.0237(4) Uani d . 1 . .
H H35 0.0171 -0.0736 0.7079 0.028 Uiso calc R 1 . .
C C36 -0.3125(3) -0.01683(16) 0.77048(12) 0.0259(4) Uani d . 1 . .
H H36 -0.3025 -0.0973 0.8182 0.031 Uiso calc R 1 . .
C C37 -0.5210(3) 0.08794(17) 0.76722(12) 0.0244(4) Uani d . 1 . .
H H37 -0.6517 0.0774 0.8126 0.029 Uiso calc R 1 . .
C C38 -0.5377(3) 0.20550(16) 0.69906(12) 0.0217(3) Uani d . 1 . .
H H38 -0.6782 0.2766 0.6979 0.026 Uiso calc R 1 . .
C C38a -0.3461(3) 0.21947(15) 0.63141(11) 0.0187(3) Uani d . 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
O1 C1 C15 . . 121.80(14) ?
O1 C1 C2 . . 119.23(14) ?
C15 C1 C2 . . 118.97(13) ?
C3 C2 C1 . . 119.74(14) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C33 . . 128.11(14) ?
C2 C3 H3 . . 115.9 ?
C33 C3 H3 . . 115.9 ?
C17a O11 C12 . . 105.71(12) ?
O13 C12 O11 . . 107.92(12) ?
O13 C12 H12A . . 110.1 ?
O11 C12 H12A . . 110.1 ?
O13 C12 H12B . . 110.1 ?
O11 C12 H12B . . 110.1 ?
H12A C12 H12B . . 108.4 ?
C13a O13 C12 . . 105.42(12) ?
C14 C13a O13 . . 128.65(14) ?
C14 C13a C17a . . 121.43(14) ?
O13 C13a C17a . . 109.77(13) ?
C13a C14 C15 . . 118.86(14) ?
C13a C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C16 C15 C14 . . 118.74(14) ?
C16 C15 C1 . . 120.27(14) ?
C14 C15 C1 . . 120.96(14) ?
N16 C16 C17 . . 117.54(14) ?
N16 C16 C15 . . 122.06(14) ?
C17 C16 C15 . . 120.40(14) ?
C17a C17 C16 . . 117.81(14) ?
C17a C17 H17 . . 121.1 ?
C16 C17 H17 . . 121.1 ?
C17 C17a O11 . . 127.16(15) ?
C17 C17a C13a . . 122.58(14) ?
O11 C17a C13a . . 110.22(14) ?
C16 N16 H16A . . 117.4(12) ?
C16 N16 H16B . . 113.9(12) ?
H16A N16 H16B . . 118.1(17) ?
C32 N31 C38a . . 125.85(13) ?
C32 N31 H31 . . 117.1 ?
C38a N31 H31 . . 117.1 ?
O32 C32 N31 . . 119.54(14) ?
O32 C32 C33 . . 124.36(14) ?
N31 C32 C33 . . 116.10(13) ?
C34 C33 C3 . . 119.49(14) ?
C34 C33 C32 . . 118.69(14) ?
C3 C33 C32 . . 121.81(13) ?
C33 C34 C34a . . 123.01(14) ?
C33 C34 H34 . . 118.5 ?
C34a C34 H34 . . 118.5 ?
C38a C34a C35 . . 118.71(15) ?
C38a C34a C34 . . 117.71(14) ?
C35 C34a C34 . . 123.58(14) ?
C36 C35 C34a . . 120.51(15) ?
C36 C35 H35 . . 119.7 ?
C34a C35 H35 . . 119.7 ?
C35 C36 C37 . . 120.04(14) ?
C35 C36 H36 . . 120.0 ?
C37 C36 H36 . . 120.0 ?
C38 C37 C36 . . 120.70(15) ?
C38 C37 H37 . . 119.7 ?
C36 C37 H37 . . 119.7 ?
C37 C38 C38a . . 119.39(15) ?
C37 C38 H38 . . 120.3 ?
C38a C38 H38 . . 120.3 ?
N31 C38a C38 . . 120.73(14) ?
N31 C38a C34a . . 118.62(14) ?
C38 C38a C34a . . 120.65(14) ?
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
O11 C17a . 1.3657(18) ?
O11 C12 . 1.442(2) ?
C12 O13 . 1.434(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
O13 C13a . 1.3832(19) ?
C13a C14 . 1.359(2) y
C14 C15 . 1.430(2) y
C14 H14 . 0.9500 ?
C15 C16 . 1.423(2) y
C16 C17 . 1.416(2) y
C17 C17a . 1.363(2) y
C13a C17a . 1.386(2) y
C16 N16 . 1.375(2) y
C15 C1 . 1.472(2) y
C1 O1 . 1.2403(19) y
C1 C2 . 1.483(2) y
C2 C3 . 1.340(2) y
C2 H2 . 0.9500 ?
C3 C33 . 1.453(2) y
C3 H3 . 0.9500 ?
C17 H17 . 0.9500 ?
N16 H16A . 0.89(2) ?
N16 H16B . 0.91(2) ?
N31 C32 . 1.364(2) y
N31 H31 . 0.8800 ?
C32 C33 . 1.469(2) y
C33 C34 . 1.368(2) y
C34 C34a . 1.426(2) y
C34 H34 . 0.9500 ?
C34a C35 . 1.410(2) y
C35 C36 . 1.368(2) y
C35 H35 . 0.9500 ?
C36 C37 . 1.406(2) y
C36 H36 . 0.9500 ?
C37 C38 . 1.375(2) y
C37 H37 . 0.9500 ?
C38 C38a . 1.398(2) y
C38 H38 . 0.9500 ?
C38a N31 . 1.3777(19) y
C34a C38a . 1.403(2) y
C32 O32 . 1.2488(18) y
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
N16 H16B O1 . 0.91(2) 1.90(2) 2.620(2) 135(2) y
N31 H31 O32 2_466 0.88 1.89 2.768(2) 176 y
C35 H35 O1 2_656 0.95 2.38 3.334(2) 177 y
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
O1 C1 C2 C3 . . . . -3.4(2) ?
C17a O11 C12 O13 . . . . 9.62(17) ?
O11 C12 O13 C13a . . . . -9.42(17) ?
C12 O13 C13a C17a . . . . 5.76(17) ?
O13 C13a C14 C15 . . . . -178.41(15) ?
C17a C13a C14 C15 . . . . -3.3(2) ?
C13a C14 C15 C16 . . . . 0.7(2) ?
C13a C14 C15 C1 . . . . 178.64(14) ?
O1 C1 C15 C16 . . . . -9.8(2) ?
C2 C1 C15 C16 . . . . 170.02(14) ?
O1 C1 C15 C14 . . . . 172.27(15) ?
C14 C15 C16 N16 . . . . -176.04(14) ?
C1 C15 C16 N16 . . . . 6.0(2) ?
C14 C15 C16 C17 . . . . 3.1(2) ?
C1 C15 C16 C17 . . . . -174.81(13) ?
N16 C16 C17 C17a . . . . 174.87(14) ?
C15 C16 C17 C17a . . . . -4.3(2) ?
C16 C17 C17a O11 . . . . 179.15(14) ?
C16 C17 C17a C13a . . . . 1.8(2) ?
C12 O11 C17a C13a . . . . -6.14(18) ?
C14 C13a C17a C17 . . . . 2.1(3) ?
O13 C13a C17a C17 . . . . 178.04(14) ?
C14 C13a C17a O11 . . . . -175.64(14) ?
O13 C13a C17a O11 . . . . 0.26(18) ?
C38a N31 C32 O32 . . . . 178.93(14) ?
C38a N31 C32 C33 . . . . -1.3(2) ?
C2 C3 C33 C34 . . . . -177.95(15) ?
C1 C2 C3 C33 . . . . -179.29(14) y
C2 C3 C33 C32 . . . . 3.3(3) y
C3 C2 C1 C15 . . . . 176.75(14) y
C2 C1 C15 C14 . . . . -7.9(2) y
C12 O13 C13a C14 . . . . -178.72(16) y
C12 O11 C17a C17 . . . . 176.21(16) y
O32 C32 C33 C34 . . . . -179.55(15) ?
N31 C32 C33 C34 . . . . 0.7(2) ?
O32 C32 C33 C3 . . . . -0.8(2) ?
N31 C32 C33 C3 . . . . 179.41(13) ?
C3 C33 C34 C34a . . . . -179.41(14) ?
C32 C33 C34 C34a . . . . -0.6(2) ?
C33 C34 C34a C38a . . . . 1.1(2) ?
C33 C34 C34a C35 . . . . -179.78(15) ?
C38a C34a C35 C36 . . . . 1.2(2) ?
C34 C34a C35 C36 . . . . -177.92(15) ?
C34a C35 C36 C37 . . . . -0.7(2) ?
C35 C36 C37 C38 . . . . -0.5(2) ?
C36 C37 C38 C38a . . . . 1.0(2) ?
C32 N31 C38a C38 . . . . -178.25(14) ?
C32 N31 C38a C34a . . . . 1.7(2) ?
C37 C38 C38a N31 . . . . 179.64(14) ?
C37 C38 C38a C34a . . . . -0.3(2) ?
C35 C34a C38a N31 . . . . 179.27(14) ?
C34 C34a C38a N31 . . . . -1.5(2) ?
C35 C34a C38a C38 . . . . -0.7(2) ?
C34 C34a C38a C38 . . . . 178.47(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726576
