#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/47/2204763.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_2204763
loop_
_publ_author_name
'Daqing Shi'
'Lihui Niu'
'Xiangshan Wang'
'Qiya Zhuang'
'Yong Zhang'
_publ_section_title
;2-Amino-7-methyl-4-(3,4-methylenedioxyphenyl)-5-oxopyrano[3,2-c]pyran-3-carbonitrile
 N,N-dimethylformamide solvate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2371
_journal_page_last               o2373
_journal_paper_doi               10.1107/S1600536804029289
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H12 N2 O5, C3 H7 N O'
_chemical_formula_moiety         'C17 H12 N2 O5, C3 H7 N O'
_chemical_formula_sum            'C20 H19 N3 O6'
_chemical_formula_weight         397.38
_chemical_melting_point          502.0(10)
_chemical_name_systematic
;
2-Amino-7-methyl-4-(3,4-methylenedioxyphenyl)-5-oxopyrano[3,2-c]pyran-3-
carbonitrile N,N-dimethylformamide solvate
;
_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                107.117(5)
_cell_angle_beta                 93.142(3)
_cell_angle_gamma                104.813(5)
_cell_formula_units_Z            2
_cell_length_a                   6.7513(18)
_cell_length_b                   11.010(3)
_cell_length_c                   13.740(4)
_cell_measurement_reflns_used    3676
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     934.2(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9243
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0392
_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)+(0.0516P)²+0.295P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                3042
_reflns_number_total             3391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6426.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '501-503' was changed to '502.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '501-503' was changed to '502.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        934.2(5)
_cod_database_code               2204763
_cod_database_fobs_code          2204763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.33414(14) 0.46108(9) 0.35445(7) 0.0246(2) Uani d . 1 O
O2 -0.27104(16) 0.20080(11) 0.11811(8) 0.0357(3) Uani d . 1 O
O3 -0.00581(15) 0.12007(9) 0.13271(7) 0.0273(2) Uani d . 1 O
O4 -0.47277(17) 0.65512(15) 0.08459(11) 0.0553(4) Uani d . 1 O
O5 -0.19544(16) 0.72972(12) 0.00578(9) 0.0394(3) Uani d . 1 O
O6 0.6460(2) 1.12501(13) 0.35697(11) 0.0585(4) Uani d . 1 O
N1 0.3683(2) 0.63387(13) 0.49442(10) 0.0301(3) Uani d . 1 N
N2 -0.1505(2) 0.69377(13) 0.49341(10) 0.0345(3) Uani d . 1 N
N3 0.7918(2) 0.95910(14) 0.35120(11) 0.0430(4) Uani d . 1 N
C1 0.2395(2) 0.55010(13) 0.41067(10) 0.0226(3) Uani d . 1 C
C2 0.0407(2) 0.54365(13) 0.38109(10) 0.0226(3) Uani d . 1 C
C3 -0.0834(2) 0.45022(13) 0.27893(10) 0.0226(3) Uani d . 1 C
H3 -0.2252 0.4091 0.2921 0.027 Uiso calc R 1 H
C4 0.0176(2) 0.34165(13) 0.24049(10) 0.0222(3) Uani d . 1 C
C5 0.2114(2) 0.35018(13) 0.27866(10) 0.0218(3) Uani d . 1 C
C6 -0.0986(2) 0.22205(14) 0.16108(11) 0.0256(3) Uani d . 1 C
C7 0.1924(2) 0.13364(14) 0.17196(11) 0.0254(3) Uani d . 1 C
C8 0.3039(2) 0.24590(14) 0.24386(10) 0.0243(3) Uani d . 1 C
H8 0.4416 0.2555 0.2709 0.029 Uiso calc R 1 H
C9 -0.0581(2) 0.62911(14) 0.44479(11) 0.0254(3) Uani d . 1 C
C10 -0.1056(2) 0.52469(13) 0.20279(10) 0.0226(3) Uani d . 1 C
C11 -0.2952(2) 0.54806(16) 0.18254(12) 0.0310(3) Uani d . 1 C
H11 -0.4121 0.5154 0.2127 0.037 Uiso calc R 1 H
C12 -0.3050(2) 0.62038(16) 0.11710(12) 0.0323(3) Uani d . 1 C
C13 -0.1388(2) 0.66641(14) 0.07117(11) 0.0270(3) Uani d . 1 C
C14 0.0483(2) 0.64486(15) 0.08949(12) 0.0295(3) Uani d . 1 C
H14 0.1632 0.6770 0.0579 0.035 Uiso calc R 1 H
C15 0.0618(2) 0.57320(14) 0.15703(11) 0.0271(3) Uani d . 1 C
H15 0.1899 0.5571 0.1721 0.032 Uiso calc R 1 H
C16 -0.3901(3) 0.7472(2) 0.03162(16) 0.0520(5) Uani d . 1 C
H16A -0.4854 0.7299 -0.0314 0.062 Uiso calc R 1 H
H16B -0.3720 0.8391 0.0763 0.062 Uiso calc R 1 H
C17 0.2586(2) 0.01296(15) 0.12703(12) 0.0349(4) Uani d . 1 C
H17A 0.3980 0.0255 0.1600 0.052 Uiso calc R 1 H
H17B 0.2595 -0.0032 0.0530 0.052 Uiso calc R 1 H
H17C 0.1620 -0.0632 0.1383 0.052 Uiso calc R 1 H
C18 0.7951(3) 1.07960(16) 0.34992(12) 0.0427(4) Uani d . 1 C
H18 0.9229 1.1353 0.3430 0.051 Uiso calc R 1 H
C19 0.9804(3) 0.91828(19) 0.34974(16) 0.0521(5) Uani d . 1 C
H19A 1.0964 0.9904 0.3455 0.078 Uiso calc R 1 H
H19B 0.9637 0.8395 0.2899 0.078 Uiso calc R 1 H
H19C 1.0083 0.8974 0.4128 0.078 Uiso calc R 1 H
C20 0.6037(4) 0.8691(2) 0.3640(2) 0.0738(7) Uani d . 1 C
H20A 0.4879 0.9067 0.3599 0.111 Uiso calc R 1 H
H20B 0.6215 0.8563 0.4312 0.111 Uiso calc R 1 H
H20C 0.5748 0.7835 0.3096 0.111 Uiso calc R 1 H
H1A 0.497(3) 0.6310(17) 0.5003(13) 0.035(4) Uiso d . 1 H
H1B 0.333(3) 0.706(2) 0.5340(15) 0.046(5) Uiso d . 1 H
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
_geom_angle_publ_flag
C1 O1 C5 117.85(10) no
C7 O3 C6 122.60(11) no
C12 O4 C16 104.75(12) ?
C13 O5 C16 104.45(11) ?
C1 N1 H1A 118.1(11) ?
C1 N1 H1B 119.5(12) ?
H1A N1 H1B 120.1(16) ?
C18 N3 C20 120.76(17) ?
C18 N3 C19 120.89(16) ?
C20 N3 C19 118.10(15) ?
N1 C1 C2 128.45(13) no
N1 C1 O1 110.10(12) no
C2 C1 O1 121.41(12) no
C1 C2 C9 120.13(13) ?
C1 C2 C3 123.02(12) no
C9 C2 C3 116.82(12) ?
C4 C3 C2 107.77(11) no
C4 C3 C10 113.72(11) ?
C2 C3 C10 111.42(11) ?
C4 C3 H3 107.9 ?
C2 C3 H3 107.9 ?
C10 C3 H3 107.9 ?
C5 C4 C6 118.50(12) ?
C5 C4 C3 122.91(12) ?
C6 C4 C3 118.57(12) ?
C4 C5 O1 122.48(12) ?
C4 C5 C8 122.63(13) ?
O1 C5 C8 114.89(11) ?
O2 C6 O3 116.85(12) no
O2 C6 C4 126.18(13) no
O3 C6 C4 116.95(12) no
C8 C7 O3 120.78(12) ?
C8 C7 C17 126.80(13) ?
O3 C7 C17 112.42(12) ?
C7 C8 C5 118.40(13) ?
C7 C8 H8 120.8 ?
C5 C8 H8 120.8 ?
N2 C9 C2 175.74(15) no
C15 C10 C11 120.00(13) ?
C15 C10 C3 120.76(12) ?
C11 C10 C3 119.20(12) ?
C12 C11 C10 117.06(13) ?
C12 C11 H11 121.5 ?
C10 C11 H11 121.5 ?
C11 C12 C13 122.40(13) ?
C11 C12 O4 128.06(13) ?
C13 C12 O4 109.52(13) ?
C14 C13 C12 121.77(13) ?
C14 C13 O5 128.30(13) ?
C12 C13 O5 109.91(12) ?
C13 C14 C15 116.58(13) ?
C13 C14 H14 121.7 ?
C15 C14 H14 121.7 ?
C10 C15 C14 122.19(12) ?
C10 C15 H15 118.9 ?
C14 C15 H15 118.9 ?
O5 C16 O4 107.43(12) ?
O5 C16 H16A 110.2 ?
O4 C16 H16A 110.2 ?
O5 C16 H16B 110.2 ?
O4 C16 H16B 110.2 ?
H16A C16 H16B 108.5 ?
C7 C17 H17A 109.5 ?
C7 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C7 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
O6 C18 N3 125.26(19) ?
O6 C18 H18 117.4 ?
N3 C18 H18 117.4 ?
N3 C19 H19A 109.5 ?
N3 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
N3 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
N3 C20 H20A 109.5 ?
N3 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
N3 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3762(16) y
O1 C5 1.3791(16) y
O2 C6 1.2096(17) y
O3 C7 1.3694(17) y
O3 C6 1.3905(17) y
O4 C12 1.3768(18) ?
O4 C16 1.434(2) ?
O5 C13 1.3808(17) ?
O5 C16 1.425(2) ?
O6 C18 1.229(2) ?
N1 C1 1.3364(19) y
N1 H1A 0.874(18) ?
N1 H1B 0.92(2) ?
N2 C9 1.1552(19) y
N3 C18 1.327(2) ?
N3 C20 1.452(3) ?
N3 C19 1.454(2) ?
C1 C2 1.3592(19) y
C2 C9 1.4128(19) ?
C2 C3 1.5200(19) y
C3 C4 1.5028(19) y
C3 C10 1.5296(19) ?
C3 H3 1.0000 ?
C4 C5 1.3518(19) y
C4 C6 1.4394(19) ?
C5 C8 1.4189(19) ?
C7 C8 1.339(2) ?
C7 C17 1.482(2) ?
C8 H8 0.9500 ?
C10 C15 1.3876(19) ?
C10 C11 1.3975(19) ?
C11 C12 1.374(2) ?
C11 H11 0.9500 ?
C12 C13 1.374(2) ?
C13 C14 1.367(2) ?
C14 C15 1.397(2) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 H16A 0.9900 ?
C16 H16B 0.9900 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 H18 0.9500 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
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
N1 H1B O6 2_676 0.92(2) 1.98(2) 2.862(2) 160(2)
N1 H1A N2 1_655 0.87(2) 2.32(2) 3.147(2) 158(2)
C18 H18 N2 2_676 0.95 2.57 3.135(2) 118
C16 H16A O2 2_465 0.99 2.38 3.262(2) 148
C14 H14 O4 1_655 0.95 2.55 3.212(2) 127
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
_geom_torsion_publ_flag
C5 O1 C1 N1 165.90(11) no
C5 O1 C1 C2 -12.22(18) y
N1 C1 C2 C9 -3.2(2) no
O1 C1 C2 C9 174.60(12) no
N1 C1 C2 C3 174.79(13) no
O1 C1 C2 C3 -7.5(2) y
C1 C2 C3 C4 20.08(17) y
C9 C2 C3 C4 -161.93(12) ?
C1 C2 C3 C10 -105.34(14) ?
C9 C2 C3 C10 72.66(15) ?
C2 C3 C4 C5 -15.53(17) y
C10 C3 C4 C5 108.51(14) ?
C2 C3 C4 C6 163.08(11) ?
C10 C3 C4 C6 -72.88(15) ?
C6 C4 C5 O1 179.71(12) no
C3 C4 C5 O1 -1.7(2) y
C6 C4 C5 C8 -0.3(2) y
C3 C4 C5 C8 178.33(12) ?
C1 O1 C5 C4 16.98(18) y
C1 O1 C5 C8 -163.03(11) no
C7 O3 C6 O2 176.85(12) no
C7 O3 C6 C4 -4.61(18) y
C5 C4 C6 O2 -178.40(14) no
C3 C4 C6 O2 2.9(2) no
C5 C4 C6 O3 3.21(18) y
C3 C4 C6 O3 -175.46(11) no
C6 O3 C7 C8 2.92(19) y
C6 O3 C7 C17 -177.90(12) no
O3 C7 C8 C5 0.3(2) y
C17 C7 C8 C5 -178.80(13) ?
C4 C5 C8 C7 -1.5(2) yes
O1 C5 C8 C7 178.48(12) ?
C1 C2 C9 N2 -162.9(19) no
C3 C2 C9 N2 19(2) no
C4 C3 C10 C15 -49.56(17) ?
C2 C3 C10 C15 72.48(16) ?
C4 C3 C10 C11 132.89(14) ?
C2 C3 C10 C11 -105.07(15) ?
C15 C10 C11 C12 -0.4(2) ?
C3 C10 C11 C12 177.21(13) ?
C10 C11 C12 C13 1.3(2) ?
C10 C11 C12 O4 179.27(16) ?
C16 O4 C12 C11 170.89(18) ?
C16 O4 C12 C13 -10.9(2) ?
C11 C12 C13 C14 -1.2(3) ?
O4 C12 C13 C14 -179.56(15) ?
C11 C12 C13 O5 177.00(15) ?
O4 C12 C13 O5 -1.35(19) ?
C16 O5 C13 C14 -168.90(17) ?
C16 O5 C13 C12 13.03(18) ?
C12 C13 C14 C15 0.2(2) ?
O5 C13 C14 C15 -177.64(14) ?
C11 C10 C15 C14 -0.6(2) ?
C3 C10 C15 C14 -178.13(13) ?
C13 C14 C15 C10 0.7(2) ?
C13 O5 C16 O4 -19.6(2) ?
C12 O4 C16 O5 18.9(2) ?
C20 N3 C18 O6 -1.5(3) ?
C19 N3 C18 O6 -175.55(17) ?
