#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/56/2235652.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_2235652
loop_
_publ_author_name
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Tahir, Muhammad N.'
'Abdelhamid, Antar A.'
'Younes, Sabry H. H.'
_publ_section_title
;
 2-Amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
 1,4-dioxane hemisolvate
;
_journal_coeditor_code           TK5115
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2178
_journal_page_last               o2179
_journal_paper_doi               10.1107/S1600536812027729
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H16 N2 O3, 0.5C4 H8 O2'
_chemical_formula_moiety         'C17 H16 N2 O3, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_chemical_name_systematic
;
2-Amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-
carbonitrile 1,4-dioxane hemisolvate
;
_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                94.376(2)
_cell_angle_beta                 102.8270(10)
_cell_angle_gamma                95.972(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0876(4)
_cell_length_b                   9.2013(4)
_cell_length_c                   12.1613(6)
_cell_measurement_reflns_used    420
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      3.6
_cell_volume                     873.00(7)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.81
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14186
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0591
_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)+(0.0997P)²+0.2730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1941
_reflns_number_gt                3134
_reflns_number_total             4108
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5115.cif
_cod_data_source_block           I
_cod_original_cell_volume        873.01(7)
_cod_database_code               2235652
_cod_database_fobs_code          2235652
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.1813(2) 0.42680(19) 0.00491(15) 0.0760(6) Uani d . 1.000
O O2 0.93204(16) 0.95097(14) 0.33842(12) 0.0512(4) Uani d . 1.000
O O3 0.36871(18) 0.99158(15) 0.37001(14) 0.0595(5) Uani d . 1.000
N N1 1.0877(2) 0.77420(19) 0.39337(15) 0.0563(6) Uani d . 1.000
N N2 0.8057(3) 0.5088(2) 0.49805(19) 0.0712(7) Uani d . 1.000
C C1 0.5009(2) 0.70436(17) 0.26984(14) 0.0389(5) Uani d . 1.000
C C2 0.4984(3) 0.7302(2) 0.15944(17) 0.0531(6) Uani d . 1.000
C C3 0.3939(3) 0.6405(2) 0.06812(18) 0.0583(7) Uani d . 1.000
C C4 0.2893(3) 0.5219(2) 0.08782(18) 0.0537(6) Uani d . 1.000
C C5 0.2917(3) 0.4941(2) 0.19793(19) 0.0563(7) Uani d . 1.000
C C6 0.3951(2) 0.58441(19) 0.28771(17) 0.0476(6) Uani d . 1.000
C C7 0.1568(4) 0.4634(3) -0.1082(2) 0.0809(9) Uani d . 1.000
C C8 0.6180(2) 0.79962(17) 0.37058(14) 0.0387(5) Uani d . 1.000
C C9 0.7912(2) 0.74660(18) 0.40311(14) 0.0405(5) Uani d . 1.000
C C10 0.9333(2) 0.81758(19) 0.38054(14) 0.0420(5) Uani d . 1.000
C C11 0.8019(2) 0.6148(2) 0.45477(17) 0.0487(6) Uani d . 1.000
C C12 0.7895(2) 1.02140(18) 0.33096(14) 0.0422(5) Uani d . 1.000
C C13 0.6429(2) 0.95783(18) 0.34927(14) 0.0403(5) Uani d . 1.000
C C14 0.5022(2) 1.04491(19) 0.35100(15) 0.0461(6) Uani d . 1.000
C C15 0.5308(3) 1.2042(2) 0.3328(2) 0.0634(8) Uani d . 1.000
C C16 0.6528(3) 1.2323(2) 0.2563(2) 0.0660(8) Uani d . 1.000
C C17 0.8203(3) 1.1737(2) 0.29963(18) 0.0537(6) Uani d . 1.000
O O4 0.8992(4) 0.9746(4) 1.0758(2) 0.1475(16) Uani d . 1.000
C C18 0.8279(5) 0.9756(5) 0.9615(4) 0.1243(19) Uani d . 1.000
C C19 0.9322(6) 1.0707(6) 0.9113(4) 0.138(2) Uani d . 1.000
H H1A 1.10620 0.69140 0.41900 0.0680 Uiso c R 1.000
H H1B 1.16900 0.82900 0.37610 0.0680 Uiso c R 1.000
H H2 0.56870 0.81000 0.14570 0.0640 Uiso c R 1.000
H H3 0.39450 0.66020 -0.00570 0.0700 Uiso c R 1.000
H H5 0.22270 0.41340 0.21170 0.0680 Uiso c R 1.000
H H6 0.39390 0.56470 0.36140 0.0570 Uiso c R 1.000
H H7A 0.11860 0.55860 -0.11240 0.1210 Uiso c R 1.000
H H7B 0.07240 0.39170 -0.15710 0.1210 Uiso c R 1.000
H H7C 0.26270 0.46480 -0.13150 0.1210 Uiso c R 1.000
H H8 0.56480 0.79380 0.43530 0.0460 Uiso c R 1.000
H H15A 0.57660 1.26170 0.40550 0.0760 Uiso c R 1.000
H H15B 0.42210 1.23650 0.29930 0.0760 Uiso c R 1.000
H H16A 0.60040 1.18570 0.18050 0.0790 Uiso c R 1.000
H H16B 0.67420 1.33710 0.25170 0.0790 Uiso c R 1.000
H H17A 0.88530 1.17380 0.24150 0.0640 Uiso c R 1.000
H H17B 0.88670 1.23700 0.36540 0.0640 Uiso c R 1.000
H H18A 0.71550 1.00780 0.95170 0.1500 Uiso c R 1.000
H H18B 0.81450 0.87690 0.92390 0.1500 Uiso c R 1.000
H H19A 0.94160 1.17020 0.94680 0.1660 Uiso c R 1.000
H H19B 0.87970 1.07000 0.83140 0.1660 Uiso c R 1.000
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
C4 O1 C7 . . 117.78(19) no
C10 O2 C12 . . 118.91(14) no
C18 O4 C19 . 2_777 108.6(3) no
H1A N1 H1B . . 120.00 no
C10 N1 H1B . . 120.00 no
C10 N1 H1A . . 120.00 no
C2 C1 C6 . . 117.77(17) no
C6 C1 C8 . . 119.84(15) no
C2 C1 C8 . . 122.37(15) no
C1 C2 C3 . . 121.88(19) no
C2 C3 C4 . . 119.41(19) no
O1 C4 C5 . . 116.23(19) no
C3 C4 C5 . . 119.3(2) no
O1 C4 C3 . . 124.49(19) no
C4 C5 C6 . . 120.73(19) no
C1 C6 C5 . . 120.93(18) no
C9 C8 C13 . . 108.63(14) no
C1 C8 C13 . . 112.38(14) no
C1 C8 C9 . . 111.95(13) no
C8 C9 C10 . . 122.54(15) no
C10 C9 C11 . . 119.42(16) no
C8 C9 C11 . . 118.00(14) no
O2 C10 N1 . . 110.30(15) no
N1 C10 C9 . . 128.22(17) no
O2 C10 C9 . . 121.48(15) no
N2 C11 C9 . . 177.6(2) no
O2 C12 C13 . . 122.91(15) no
C13 C12 C17 . . 125.75(17) no
O2 C12 C17 . . 111.34(16) no
C8 C13 C14 . . 118.19(14) no
C8 C13 C12 . . 122.27(15) no
C12 C13 C14 . . 119.54(15) no
C13 C14 C15 . . 117.57(16) no
O3 C14 C13 . . 121.28(16) no
O3 C14 C15 . . 121.11(17) no
C14 C15 C16 . . 112.24(17) no
C15 C16 C17 . . 111.57(18) no
C12 C17 C16 . . 110.51(18) no
C1 C2 H2 . . 119.00 no
C3 C2 H2 . . 119.00 no
C4 C3 H3 . . 120.00 no
C2 C3 H3 . . 120.00 no
C6 C5 H5 . . 120.00 no
C4 C5 H5 . . 120.00 no
C1 C6 H6 . . 120.00 no
C5 C6 H6 . . 120.00 no
O1 C7 H7A . . 109.00 no
O1 C7 H7B . . 109.00 no
H7A C7 H7B . . 109.00 no
H7A C7 H7C . . 109.00 no
H7B C7 H7C . . 110.00 no
O1 C7 H7C . . 109.00 no
C9 C8 H8 . . 108.00 no
C13 C8 H8 . . 108.00 no
C1 C8 H8 . . 108.00 no
C14 C15 H15B . . 109.00 no
C16 C15 H15A . . 109.00 no
C16 C15 H15B . . 109.00 no
H15A C15 H15B . . 108.00 no
C14 C15 H15A . . 109.00 no
C15 C16 H16B . . 109.00 no
C17 C16 H16A . . 109.00 no
C15 C16 H16A . . 109.00 no
H16A C16 H16B . . 108.00 no
C17 C16 H16B . . 109.00 no
C12 C17 H17A . . 110.00 no
C12 C17 H17B . . 110.00 no
C16 C17 H17B . . 110.00 no
H17A C17 H17B . . 108.00 no
C16 C17 H17A . . 110.00 no
O4 C18 C19 . . 110.9(4) no
O4 C19 C18 2_777 . 110.8(4) no
O4 C18 H18A . . 109.00 no
O4 C18 H18B . . 109.00 no
C19 C18 H18A . . 109.00 no
C19 C18 H18B . . 109.00 no
H18A C18 H18B . . 108.00 no
C18 C19 H19A . . 109.00 no
C18 C19 H19B . . 109.00 no
H19A C19 H19B . . 108.00 no
O4 C19 H19A 2_777 . 109.00 no
O4 C19 H19B 2_777 . 110.00 no
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
O1 C4 . 1.364(3) no
O1 C7 . 1.417(3) no
O2 C10 . 1.366(2) no
O2 C12 . 1.369(2) no
O3 C14 . 1.216(2) no
O4 C18 . 1.383(5) no
O4 C19 2_777 1.446(6) no
N1 C10 . 1.330(2) no
N2 C11 . 1.143(3) no
N1 H1B . 0.8600 no
N1 H1A . 0.8600 no
C1 C2 . 1.377(3) no
C1 C8 . 1.521(2) no
C1 C6 . 1.386(2) no
C2 C3 . 1.388(3) no
C3 C4 . 1.379(3) no
C4 C5 . 1.379(3) no
C5 C6 . 1.376(3) no
C8 C13 . 1.499(2) no
C8 C9 . 1.511(2) no
C9 C10 . 1.354(2) no
C9 C11 . 1.410(3) no
C12 C13 . 1.338(2) no
C12 C17 . 1.491(3) no
C13 C14 . 1.461(2) no
C14 C15 . 1.501(3) no
C15 C16 . 1.516(3) no
C16 C17 . 1.511(3) no
C2 H2 . 0.9300 no
C3 H3 . 0.9300 no
C5 H5 . 0.9300 no
C6 H6 . 0.9300 no
C7 H7C . 0.9600 no
C7 H7A . 0.9600 no
C7 H7B . 0.9600 no
C8 H8 . 0.9800 no
C15 H15B . 0.9700 no
C15 H15A . 0.9700 no
C16 H16A . 0.9700 no
C16 H16B . 0.9700 no
C17 H17B . 0.9700 no
C17 H17A . 0.9700 no
C18 C19 . 1.417(7) no
C18 H18A . 0.9700 no
C18 H18B . 0.9700 no
C19 H19A . 0.9700 no
C19 H19B . 0.9700 no
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
N1 H1A N2 2_766 0.86 2.27 3.123(3) 171 yes
N1 H1B O3 1_655 0.86 2.10 2.945(2) 167 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_4
_geom_torsion
_geom_torsion_publ_flag
C7 O1 C4 C3 . . . -9.3(3) no
C7 O1 C4 C5 . . . 171.1(2) no
C10 O2 C12 C17 . . . 171.59(15) no
C12 O2 C10 N1 . . . -172.95(15) no
C10 O2 C12 C13 . . . -8.8(2) no
C12 O2 C10 C9 . . . 7.4(2) no
C18 O4 C19 C18 2_777 2_777 . -58.0(5) no
C19 O4 C18 C19 2_777 . . -58.0(5) no
C8 C1 C2 C3 . . . 178.46(19) no
C8 C1 C6 C5 . . . -178.09(17) no
C2 C1 C6 C5 . . . 0.2(3) no
C2 C1 C8 C9 . . . -87.6(2) no
C2 C1 C8 C13 . . . 34.9(2) no
C6 C1 C8 C9 . . . 90.63(19) no
C6 C1 C8 C13 . . . -146.80(16) no
C6 C1 C2 C3 . . . 0.2(3) no
C1 C2 C3 C4 . . . 0.0(3) no
C2 C3 C4 C5 . . . -0.5(3) no
C2 C3 C4 O1 . . . 179.8(2) no
O1 C4 C5 C6 . . . -179.37(19) no
C3 C4 C5 C6 . . . 1.0(3) no
C4 C5 C6 C1 . . . -0.8(3) no
C13 C8 C9 C11 . . . 163.92(15) no
C1 C8 C13 C12 . . . -107.09(18) no
C13 C8 C9 C10 . . . -18.7(2) no
C1 C8 C9 C10 . . . 105.99(18) no
C1 C8 C9 C11 . . . -71.4(2) no
C9 C8 C13 C14 . . . -161.46(15) no
C1 C8 C13 C14 . . . 74.12(19) no
C9 C8 C13 C12 . . . 17.3(2) no
C11 C9 C10 N1 . . . 5.4(3) no
C8 C9 C10 O2 . . . 7.6(3) no
C8 C9 C10 N1 . . . -172.00(17) no
C11 C9 C10 O2 . . . -175.05(16) no
C17 C12 C13 C8 . . . 174.55(17) no
C17 C12 C13 C14 . . . -6.7(3) no
O2 C12 C17 C16 . . . 162.26(16) no
C13 C12 C17 C16 . . . -17.3(3) no
O2 C12 C13 C14 . . . 173.82(15) no
O2 C12 C13 C8 . . . -5.0(3) no
C12 C13 C14 O3 . . . -178.26(18) no
C8 C13 C14 O3 . . . 0.6(3) no
C12 C13 C14 C15 . . . -0.5(3) no
C8 C13 C14 C15 . . . 178.31(16) no
O3 C14 C15 C16 . . . -151.3(2) no
C13 C14 C15 C16 . . . 31.0(3) no
C14 C15 C16 C17 . . . -54.6(2) no
C15 C16 C17 C12 . . . 46.9(2) no
O4 C18 C19 O4 . . 2_777 59.3(5) no
