#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223372.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_2223372
loop_
_publ_author_name
'Br\"uning, J\"urgen'
'Bats, Jan W.'
'Schmidt, Martin U.'
_publ_section_title
;
 2-Aminoterephthalic acid dimethyl ester
;
_journal_coeditor_code           FK2004
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2468
_journal_page_last               o2469
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H11 N O4'
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_name_common
;
Dimethyl-2-amino-terephthalate
;
_chemical_name_systematic
;
2-Aminoterephthalic acid dimethyl ester
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.88(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7721(12)
_cell_length_b                   16.928(5)
_cell_length_c                   11.841(5)
_cell_measurement_reflns_used    57
_cell_measurement_temperature    166(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     954.3(6)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>,  2008)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      166(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens SMART 1K CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1400
_diffrn_reflns_av_sigmaI/netI    0.0958
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11829
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         62
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.06P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                884
_reflns_number_total             1687
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fk2004.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        954.4(6)
_cod_database_code               2223372
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
O O1 -0.2268(4) 0.60319(11) 0.30114(17) 0.0341(6) Uani d . 1
O O2 -0.1912(5) 0.58551(12) 0.11612(18) 0.0421(7) Uani d . 1
O O3 0.7681(5) 0.32502(11) 0.44342(17) 0.0328(6) Uani d . 1
O O4 0.8629(4) 0.29952(12) 0.26489(18) 0.0333(6) Uani d . 1
N N1 0.5292(7) 0.36927(18) 0.0986(3) 0.0402(8) Uani d . 1
C C1 0.4228(7) 0.40860(18) 0.1867(3) 0.0280(8) Uani d . 1
C C2 0.2108(7) 0.46595(17) 0.1622(3) 0.0298(8) Uani d . 1
H H2A 0.1487 0.4762 0.0857 0.036 Uiso calc R 1
C C3 0.0944(6) 0.50678(17) 0.2471(3) 0.0258(8) Uani d . 1
C C4 0.1783(6) 0.49355(17) 0.3592(3) 0.0287(8) Uani d . 1
H H4A 0.0967 0.5224 0.4175 0.034 Uiso calc R 1
C C5 0.3823(6) 0.43779(17) 0.3851(2) 0.0277(8) Uani d . 1
H H5A 0.4401 0.4281 0.4622 0.033 Uiso calc R 1
C C6 0.5072(6) 0.39497(17) 0.3004(3) 0.0263(8) Uani d . 1
C C7 -0.1217(7) 0.56897(17) 0.2121(3) 0.0281(8) Uani d . 1
C C8 -0.4282(6) 0.66622(18) 0.2753(3) 0.0386(9) Uani d . 1
H H8A -0.3290 0.7134 0.2514 0.058 Uiso calc R 1
H H8B -0.5277 0.6785 0.3429 0.058 Uiso calc R 1
H H8C -0.5636 0.6492 0.2142 0.058 Uiso calc R 1
C C9 0.7296(7) 0.33575(17) 0.3320(3) 0.0267(8) Uani d . 1
C C10 0.9869(7) 0.26942(18) 0.4801(3) 0.0381(9) Uani d . 1
H H10A 0.9394 0.2170 0.4495 0.057 Uiso calc R 1
H H10B 1.0030 0.2670 0.5630 0.057 Uiso calc R 1
H H10C 1.1661 0.2867 0.4527 0.057 Uiso calc R 1
H H1A 0.702(9) 0.348(2) 0.120(3) 0.074(14) Uiso d . 1
H H1B 0.482(7) 0.385(2) 0.023(3) 0.059(12) Uiso d . 1
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 0.0400(15) 0.0187(12) 0.0440(14) 0.0105(11) 0.0066(11) 0.0034(10)
O2 0.0606(18) 0.0258(14) 0.0392(15) 0.0091(12) -0.0009(12) 0.0034(11)
O3 0.0391(13) 0.0174(11) 0.0416(14) 0.0065(11) 0.0000(11) 0.0041(10)
O4 0.0396(14) 0.0177(12) 0.0431(14) 0.0031(11) 0.0068(11) -0.0042(10)
N1 0.049(2) 0.0357(19) 0.0361(19) 0.0125(16) 0.0027(17) -0.0045(15)
C1 0.032(2) 0.0169(17) 0.0351(19) -0.0029(16) 0.0028(16) -0.0014(14)
C2 0.034(2) 0.0208(18) 0.0347(19) -0.0019(16) 0.0017(16) 0.0027(15)
C3 0.0273(19) 0.0148(17) 0.0354(19) -0.0035(15) 0.0038(15) 0.0009(14)
C4 0.037(2) 0.0129(17) 0.036(2) -0.0012(16) 0.0058(16) -0.0015(14)
C5 0.035(2) 0.0139(17) 0.0334(18) -0.0036(15) -0.0004(15) 0.0010(14)
C6 0.0305(19) 0.0109(16) 0.0376(19) -0.0015(14) 0.0029(16) -0.0005(14)
C7 0.034(2) 0.0133(18) 0.037(2) -0.0050(15) 0.0053(17) 0.0005(16)
C8 0.040(2) 0.0197(19) 0.056(2) 0.0112(16) -0.0004(18) 0.0031(16)
C9 0.035(2) 0.0127(17) 0.0329(19) -0.0090(15) 0.0039(16) -0.0007(14)
C10 0.041(2) 0.0234(18) 0.049(2) 0.0059(17) -0.0031(17) 0.0051(17)
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
C7 O1 C8 115.6(2)
C9 O3 C10 115.7(2)
C1 N1 H1A 111(2)
C1 N1 H1B 120(2)
H1A N1 H1B 122(3)
N1 C1 C6 123.9(3)
N1 C1 C2 118.4(3)
C6 C1 C2 117.7(3)
C3 C2 C1 121.0(3)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 121.3(3)
C2 C3 C7 117.0(3)
C4 C3 C7 121.7(3)
C5 C4 C3 118.7(3)
C5 C4 H4A 120.6
C3 C4 H4A 120.6
C4 C5 C6 121.6(3)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C1 C6 C5 119.6(3)
C1 C6 C9 120.5(3)
C5 C6 C9 119.9(3)
O2 C7 O1 123.8(3)
O2 C7 C3 124.3(3)
O1 C7 C3 111.9(3)
O1 C8 H8A 109.5
O1 C8 H8B 109.5
H8A C8 H8B 109.5
O1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O4 C9 O3 122.3(3)
O4 C9 C6 124.8(3)
O3 C9 C6 112.9(3)
O3 C10 H10A 109.5
O3 C10 H10B 109.5
H10A C10 H10B 109.5
O3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.330(3)
O1 C8 1.455(3)
O2 C7 1.195(3)
O3 C9 1.333(3)
O3 C10 1.450(3)
O4 C9 1.216(3)
N1 C1 1.365(4)
N1 H1A 0.92(4)
N1 H1B 0.94(3)
C1 C6 1.398(4)
C1 C2 1.418(4)
C2 C3 1.368(4)
C2 H2A 0.9500
C3 C4 1.379(4)
C3 C7 1.512(4)
C4 C5 1.376(4)
C4 H4A 0.9500
C5 C6 1.403(4)
C5 H5A 0.9500
C6 C9 1.489(4)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 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
_geom_hbond_publ_flag
N1 H1A O4 1_555 0.92(4) 2.01(4) 2.717(4) 133(3) yes
N1 H1B O2 3_565 0.95(4) 2.14(3) 3.016(4) 153(3) 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
N1 C1 C2 C3 179.4(3)
C6 C1 C2 C3 0.4(4)
C1 C2 C3 C4 -0.1(4)
C1 C2 C3 C7 177.6(3)
C2 C3 C4 C5 -0.3(4)
C7 C3 C4 C5 -178.0(3)
C3 C4 C5 C6 0.5(4)
N1 C1 C6 C5 -179.2(3)
C2 C1 C6 C5 -0.1(4)
N1 C1 C6 C9 1.2(5)
C2 C1 C6 C9 -179.8(3)
C4 C5 C6 C1 -0.3(4)
C4 C5 C6 C9 179.3(3)
C8 O1 C7 O2 -2.7(4)
C8 O1 C7 C3 177.5(2)
C2 C3 C7 O2 -1.7(4)
C4 C3 C7 O2 176.1(3)
C2 C3 C7 O1 178.1(2)
C4 C3 C7 O1 -4.1(4)
C10 O3 C9 O4 2.2(4)
C10 O3 C9 C6 -178.6(2)
C1 C6 C9 O4 4.7(4)
C5 C6 C9 O4 -175.0(3)
C1 C6 C9 O3 -174.5(3)
C5 C6 C9 O3 5.8(4)