#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010288.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_2010288
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1994
_journal_volume 50
_journal_page_first  1935
_journal_page_last  1938
_publ_section_title
;
Two N-Aminoazolylmethylene Derivatives of Meldrum's Acid
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Blake, Alexander J.'
  'Gould, Robert O.'
  'Irving, Iain'
  'McNab, Hamish'
  'Morrow, Mark'
_chemical_name_common  '5-(1-aminopyrrolylmethylene)-Meldrum's acid'
_chemical_formula_moiety  'C11 H12 N2 O4'
_chemical_formula_sum  'C11 H12 N2 O4'
_chemical_formula_weight  236.23
_symmetry_cell_setting  Monoclinic
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'
_cell_length_a  16.7900(11)
_cell_length_b  12.6423(8)
_cell_length_c  11.1014(6)
_cell_angle_alpha  90.00
_cell_angle_beta  94.31(6)
_cell_angle_gamma  90.00
_cell_volume  2349.8(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.335
_diffrn_ambient_temperature  295(2)
_refine_ls_R_factor_obs  0.0563
_refine_ls_wR_factor_obs  0.1475
loop_
_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
_atom_site_disorder_group
_atom_site_type_symbol
  O1 0.18522(15) 0.0447(2) 0.5331(3) 0.0675(8) Uani d . 1 . O
  C2 0.2254(2) -0.0012(3) 0.6387(4) 0.0580(11) Uani d . 1 . C
  C2A 0.2485(3) 0.0832(3) 0.7302(4) 0.0681(12) Uani d . 1 . C
  H2A1 0.2754(3) 0.0514(3) 0.8005(4) 0.082 Uiso calc R 1 . H
  H2A2 0.2014(3) 0.1190(3) 0.7525(4) 0.082 Uiso calc R 1 . H
  H2A3 0.2835(3) 0.1331(3) 0.6959(4) 0.082 Uiso calc R 1 . H
  C2B 0.1695(3) -0.0830(4) 0.6821(4) 0.0806(14) Uani d . 1 . C
  H2B1 0.1936(3) -0.1165(4) 0.7533(4) 0.097 Uiso calc R 1 . H
  H2B2 0.1585(3) -0.1351(4) 0.6202(4) 0.097 Uiso calc R 1 . H
  H2B3 0.1205(3) -0.0496(4) 0.7006(4) 0.097 Uiso calc R 1 . H
  O3 0.2956(2) -0.0570(2) 0.6080(2) 0.0599(8) Uani d . 1 . O
  C4 0.3459(2) -0.0059(3) 0.5373(4) 0.0579(11) Uani d . 1 . C
  O4 0.4138(2) -0.0372(2) 0.5355(3) 0.0789(9) Uani d . 1 . O
  C5 0.3115(2) 0.0796(3) 0.4662(4) 0.0580(11) Uani d . 1 . C
  C6 0.2273(3) 0.0994(4) 0.4559(4) 0.0641(11) Uani d . 1 . C
  O6 0.1911(2) 0.1569(3) 0.3840(3) 0.0992(12) Uani d . 1 . O
  C7 0.3560(3) 0.1510(4) 0.3970(4) 0.085(2) Uani d . 1 . C
  H7 0.3279(3) 0.2035(4) 0.3531(4) 0.102 Uiso calc R 1 . H
  N8 0.4296(3) 0.1475(3) 0.3916(4) 0.0862(12) Uani d . 1 . N
  H8 0.465(3)  0.093(4)  0.451(4)  0.103 Uiso d . 1 . H
  N9 0.4623(3) 0.2377(4) 0.3338(4) 0.0885(13) Uani d . 1 . N
  C10 0.4982(4) 0.2322(6) 0.2286(5) 0.113(2) Uani d . 1 . C
  H10 0.5065(4) 0.1714(6) 0.1840(5) 0.136 Uiso calc R 1 . H
  C11 0.5191(4) 0.3296(7) 0.2016(6) 0.114(2) Uani d . 1 . C
  H11 0.5457(4) 0.3494(7) 0.1347(6) 0.13(2)  Uiso calc R 1 . H
  C12 0.4950(4) 0.3964(5) 0.2889(8) 0.119(2) Uani d . 1 . C
  H12 0.5031(4) 0.4691(5) 0.2915(8) 0.143 Uiso calc R 1 . H
  C13 0.4575(3) 0.3396(5) 0.3705(6) 0.092(2) Uani d . 1 . C
  H13 0.4336(3) 0.3649(5) 0.4376(6) 0.110 Uiso calc R 1 . H
  O1' 0.31446(14) -0.0024(2) 0.0485(3) 0.0620(8) Uani d . 1 . O
  C2' 0.2772(2) -0.1038(3) 0.0605(4) 0.0613(11) Uani d . 1 . C
  C2A' 0.2680(3) -0.1273(4) 0.1912(4) 0.089(2) Uani d . 1 . C
  H2A4 0.2431(3) -0.1951(4) 0.1984(4) 0.107 Uiso calc R 1 . H
  H2A5 0.2354(3) -0.0738(4) 0.2242(4) 0.107 Uiso calc R 1 . H
  H2A6 0.3196(3) -0.1279(4) 0.2348(4) 0.107 Uiso calc R 1 . H
  C2B' 0.3273(3) -0.1815(4) -0.0026(5) 0.091(2) Uani d . 1 . C
  H2B4 0.3049(3) -0.2510(4) 0.0027(5) 0.109 Uiso calc R 1 . H
  H2B5 0.3807(3) -0.1813(4) 0.0350(5) 0.109 Uiso calc R 1 . H
  H2B6 0.3285(3) -0.1618(4) -0.0860(5) 0.109 Uiso calc R 1 . H
  O3' 0.20018(14) -0.1043(2) -0.0063(2) 0.0590(8) Uani d . 1 . O
  C4' 0.1509(2) -0.0223(3) 0.0107(3) 0.0488(10) Uani d . 1 . C
  O4' 0.07989(15) -0.0331(2) -0.0206(2) 0.0618(8) Uani d . 1 . O
  C5' 0.1857(2) 0.0724(3) 0.0601(3) 0.0474(9) Uani d . 1 . C
  C6' 0.2716(2) 0.0853(3) 0.0721(4) 0.0569(10) Uani d . 1 . C
  O6' 0.3073(2) 0.1662(2) 0.0954(3) 0.0792(10) Uani d . 1 . O
  C7' 0.1400(2) 0.1556(3) 0.0914(3) 0.0523(10) Uani d . 1 . C
  H7' 0.1674(2) 0.2152(3) 0.1212(3) 0.063 Uiso calc R 1 . H
  N8' 0.0614(2) 0.1613(3) 0.0842(3) 0.0580(9) Uani d . 1 . N
  H8' 0.034(2)  0.104(3)  0.060(4)  0.070 Uiso d . 1 . H
  N9' 0.0244(2) 0.2479(3) 0.1302(3) 0.0589(9) Uani d . 1 . N
  C10' -0.0173(3) 0.3201(5) 0.0653(5) 0.109(2) Uani d . 1 . C
  H10' -0.0268(3) 0.3202(5) -0.0184(5) 0.131 Uiso calc R 1 . H
  C11' -0.0435(3) 0.3928(5) 0.1412(5) 0.101(2) Uani d . 1 . C
  H11' -0.0749(3) 0.4515(5) 0.1200(5) 0.122 Uiso calc R 1 . H
  C12' -0.0158(3) 0.3645(5) 0.2541(5) 0.104(2) Uani d . 1 . C
  H12' -0.0246(3) 0.4011(5) 0.3245(5) 0.125 Uiso calc R 1 . H
  C13' 0.0264(3) 0.2747(5) 0.2477(4) 0.092(2) Uani d . 1 . C
  H13' 0.0521(3) 0.2381(5) 0.3121(4) 0.111 Uiso calc R 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1 0.051(2) 0.088(2) 0.063(2) 0.0002(15) -0.0015(14) 0.015(2)
  C2 0.050(2) 0.066(3) 0.059(3) 0.004(2) 0.009(2) 0.008(2)
  C2A 0.080(3) 0.068(3) 0.057(3) 0.007(2) 0.010(2) -0.001(2)
  C2B 0.074(3) 0.089(3) 0.081(3) -0.015(3) 0.023(2) 0.010(3)
  O3 0.063(2) 0.051(2) 0.067(2) 0.0027(14) 0.0127(14) -0.0006(14)
  C4 0.051(2) 0.062(3) 0.062(3) -0.007(2) 0.011(2) -0.017(2)
  O4 0.056(2) 0.084(2) 0.098(2) 0.010(2) 0.015(2) -0.021(2)
  C5 0.067(3) 0.060(3) 0.049(2) -0.011(2) 0.018(2) -0.001(2)
  C6 0.066(3) 0.073(3) 0.053(3) -0.003(2) 0.003(2) 0.004(2)
  O6 0.101(3) 0.120(3) 0.074(2) 0.011(2) -0.010(2) 0.037(2)
  C7 0.060(3) 0.115(4) 0.080(3) 0.008(3) 0.001(2) -0.043(3)
  N8 0.088(3) 0.084(3) 0.085(3) 0.007(3) -0.004(2) 0.004(3)
  N9 0.096(3) 0.088(3) 0.084(3) -0.036(3) 0.022(2) 0.019(3)
  C10 0.136(5) 0.138(6) 0.069(4) -0.058(4) 0.034(3) 0.006(4)
  C11 0.076(4) 0.164(7) 0.100(5) -0.036(4) -0.007(3) 0.068(5)
  C12 0.088(4) 0.089(5) 0.179(8) -0.011(4) -0.002(5) 0.066(5)
  C13 0.071(3) 0.082(4) 0.122(5) 0.004(3) 0.009(3) 0.023(4)
  O1' 0.0419(14) 0.061(2) 0.083(2) 0.0004(14) 0.0071(13) -0.001(2)
  C2' 0.047(2) 0.055(3) 0.080(3) 0.002(2) -0.004(2) 0.008(2)
  C2A' 0.085(3) 0.093(4) 0.086(4) -0.003(3) -0.012(3) 0.028(3)
  C2B' 0.071(3) 0.074(3) 0.126(5) 0.022(3) 0.001(3) -0.011(3)
  O3' 0.049(2) 0.053(2) 0.073(2) 0.0043(13) -0.0013(13) -0.0075(14)
  C4' 0.045(2) 0.057(3) 0.045(2) -0.001(2) 0.004(2) 0.004(2)
  O4' 0.044(2) 0.070(2) 0.071(2) -0.0041(13) -0.0011(13) -0.0091(15)
  C5' 0.041(2) 0.051(2) 0.051(2) 0.002(2) 0.006(2) -0.003(2)
  C6' 0.051(2) 0.054(3) 0.066(3) -0.002(2) 0.006(2) -0.002(2)
  O6' 0.053(2) 0.065(2) 0.120(3) -0.014(2) 0.010(2) -0.017(2)
  C7' 0.050(2) 0.056(2) 0.051(2) -0.007(2) 0.004(2) -0.002(2)
  N8' 0.044(2) 0.061(2) 0.069(2) 0.001(2) 0.005(2) -0.013(2)
  N9' 0.053(2) 0.068(2) 0.055(2) 0.016(2) 0.002(2) -0.011(2)
  C10' 0.134(5) 0.124(5) 0.067(3) 0.075(4) -0.005(3) -0.012(3)
  C11' 0.098(4) 0.109(4) 0.094(4) 0.053(3) -0.012(3) -0.012(4)
  C12' 0.098(4) 0.129(5) 0.086(4) 0.050(4) 0.006(3) -0.036(4)
  C13' 0.104(4) 0.116(4) 0.057(3) 0.042(4) 0.006(3) -0.003(3)
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 C6 . 1.343(5) y
  O1 C2 . 1.430(5) y
  C2 O3 . 1.436(4) y
  C2 C2B . 1.500(5) y
  C2 C2A . 1.504(6) y
  C2A H2A1 . 0.96 n
  C2A H2A2 . 0.96 n
  C2A H2A3 . 0.96 n
  C2B H2B1 . 0.96 n
  C2B H2B2 . 0.96 n
  C2B H2B3 . 0.96 n
  O3 C4 . 1.360(5) y
  C4 O4 . 1.208(5) y
  C4 C5 . 1.434(6) y
  C5 C6 . 1.432(6) y
  C5 C7 . 1.432(6) y
  C6 O6 . 1.209(5) y
  C7 N8 . 1.242(5) y
  C7 H7 . 0.93 n
  N8 N9 . 1.438(5) y
  N8 H8 . 1.10(5) y
  N9 C13 . 1.355(6) y
  N9 C10 . 1.355(6) y
  C10 C11 . 1.321(8) y
  C10 H10 . 0.93 n
  C11 C12 . 1.370(9) y
  C11 H11 . 0.93 n
  C12 C13 . 1.348(8) y
  C12 H12 . 0.93 n
  C13 H13 . 0.93 n
  O1' C6' . 1.359(5) y
  O1' C2' . 1.436(5) y
  C2' O3' . 1.442(4) y
  C2' C2B' . 1.500(6) y
  C2' C2A' . 1.501(6) y
  C2A' H2A4 . 0.96 n
  C2A' H2A5 . 0.96 n
  C2A' H2A6 . 0.96 n
  C2B' H2B4 . 0.96 n
  C2B' H2B5 . 0.96 n
  C2B' H2B6 . 0.96 n
  O3' C4' . 1.349(4) y
  C4' O4' . 1.224(4) y
  C4' C5' . 1.424(5) y
  C5' C7' . 1.363(5) y
  C5' C6' . 1.446(5) y
  C6' O6' . 1.204(4) y
  C7' N8' . 1.318(5) y
  C7' H7' . 0.93 n
  N8' N9' . 1.375(4) y
  N8' H8' . 0.90(4) y
  N9' C10' . 1.330(6) y
  N9' C13' . 1.345(5) y
  C10' C11' . 1.343(7) y
  C10' H10' . 0.93 n
  C11' C12' . 1.352(7) y
  C11' H11' . 0.93 n
  C12' C13' . 1.344(7) y
  C12' H12' . 0.93 n
  C13' H13' . 0.93 n