##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Trimesic acid dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C9 H6 O6, 2H2 O'
_chemical_formula_sum     'C9 H10 O8'
_chemical_formula_iupac     'C9 H6 O6, 2H2 O'
_chemical_formula_weight     246.17
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     21.000(4)
_cell_length_b     13.343(2)
_cell_length_c     3.6863(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1032.9(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5259
_cell_measurement_theta_min     1.81
_cell_measurement_theta_max     25.09
_cell_measurement_temperature     298(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.583
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.143
_exptl_absorpt_correction_type     'numerical'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.98
_exptl_absorpt_correction_T_max     0.99
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5259
_diffrn_reflns_av_R_equivalents     0.0590
_diffrn_reflns_av_sigmaI/netI     0.0446
_diffrn_reflns_theta_min     1.81
_diffrn_reflns_theta_max     25.09
_diffrn_reflns_theta_full     25.09
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     25
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -4
_diffrn_reflns_limit_l_max     4
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1079
_reflns_number_gt     950
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0920
_refine_ls_R_factor_gt     0.0788
_refine_ls_wR_factor_gt     0.1507
_refine_ls_wR_factor_ref     0.1563
_refine_ls_goodness_of_fit_ref     1.196
_refine_ls_restrained_S_all     1.196
_refine_ls_number_reflns     1079
_refine_ls_number_parameters     169
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0444P)²+2.4467P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.044
_refine_ls_shift/su_mean     0.007
_refine_diff_density_max     0.304
_refine_diff_density_min     -0.276
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 0.0000
                         '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'
    'O' 'O' 0.0106 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2002)'
_computing_publication_material     'SHELXL97'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C7 0.4883(3) 0.1629(5) 0.260(2) 0.0179(15) Uani d . 1 . . C
    H7 0.5096 0.1063 0.3439 0.021 Uiso calc R 1 . . H
    C3 0.4900(3) 0.3336(5) 0.062(2) 0.0179(15) Uani d . 1 . . C
    H3 0.5126 0.3916 0.0067 0.021 Uiso calc R 1 . . H
    O5 0.62084(18) 0.3316(3) 0.2449(18) 0.0300(13) Uani d . 1 . . O
    H5A 0.6534 0.3340 0.1221 0.045 Uiso calc R 1 . . H
    C6 0.4223(3) 0.1602(4) 0.226(2) 0.0167(14) Uani d . 1 . . C
    C4 0.4242(3) 0.3330(5) 0.035(2) 0.0191(15) Uani d . 1 . . C
    O2 0.32837(19) 0.0603(3) 0.2789(19) 0.0360(14) Uani d . 1 . . O
    C8 0.3854(3) 0.0690(5) 0.315(2) 0.0233(16) Uani d . 1 . . C
    O6 0.62475(19) 0.1683(3) 0.1802(18) 0.0337(16) Uani d . 1 . . O
    C9 0.3896(3) 0.4276(4) -0.0623(19) 0.0189(15) Uani d . 1 . . C
    O4 0.4262(2) 0.5062(3) -0.023(2) 0.0405(16) Uani d . 1 . . O
    H4 0.4112 0.5535 -0.1365 0.061 Uiso calc R 1 . . H
    C2 0.5227(3) 0.2472(5) 0.1736(19) 0.0183(14) Uani d . 1 . . C
    O1 0.4214(2) -0.0008(3) 0.4503(19) 0.0433(18) Uani d . 1 . . O
    H1 0.4008 -0.0527 0.4702 0.065 Uiso calc R 1 . . H
    C5 0.3908(3) 0.2454(5) 0.1108(19) 0.0204(15) Uani d . 1 . . C
    H5 0.3468 0.2442 0.0836 0.024 Uiso calc R 1 . . H
    O3 0.3348(2) 0.4319(3) -0.1540(18) 0.0372(16) Uani d . 1 . . O
    C1 0.5944(2) 0.2473(5) 0.203(2) 0.0180(14) Uani d . 1 . . C
    O7 0.7462(2) 0.2071(5) 0.464(3) 0.0536(18) Uani d D 1 . . O
    O8 0.7253(3) 0.3919(5) 0.805(2) 0.0632(19) Uani d D 1 . . O
    H8A 0.729(5) 0.334(5) 0.69(3) 0.095 Uiso d D 1 . . H
    H7A 0.768(4) 0.155(5) 0.54(4) 0.095 Uiso d D 1 . . H
    H7B 0.708(3) 0.194(8) 0.43(4) 0.095 Uiso d D 1 . . H
    H8B 0.760(3) 0.421(7) 0.91(3) 0.095 Uiso d D 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
    C7 0.021(3) 0.022(3) 0.011(4) 0.001(3) 0.004(3) -0.002(3)
    C3 0.024(3) 0.006(3) 0.024(4) -0.005(3) -0.001(3) 0.005(3)
    O5 0.017(2) 0.022(2) 0.050(4) -0.0028(19) 0.009(3) -0.009(3)
    C6 0.023(3) 0.010(3) 0.017(3) 0.004(3) -0.002(4) 0.003(3)
    C4 0.028(3) 0.015(3) 0.015(3) 0.000(3) -0.003(3) -0.003(3)
    O2 0.020(2) 0.027(3) 0.062(4) -0.003(2) -0.008(3) 0.011(3)
    C8 0.025(3) 0.020(4) 0.024(4) -0.001(3) 0.004(3) 0.002(3)
    O6 0.020(2) 0.008(2) 0.073(5) 0.0020(19) -0.016(3) -0.013(3)
    C9 0.025(3) 0.011(3) 0.021(4) -0.003(3) -0.001(3) 0.003(3)
    O4 0.037(3) 0.013(2) 0.071(5) -0.004(2) -0.017(3) 0.015(3)
    C2 0.024(3) 0.012(3) 0.019(4) -0.009(3) 0.003(3) -0.005(3)
    O1 0.028(2) 0.017(3) 0.084(5) -0.008(2) -0.009(3) 0.025(3)
    C5 0.015(3) 0.021(3) 0.025(4) -0.005(3) -0.002(3) -0.001(3)
    O3 0.023(2) 0.019(3) 0.070(5) 0.001(2) -0.018(3) 0.018(3)
    C1 0.017(3) 0.011(3) 0.026(4) 0.000(3) -0.001(3) -0.004(3)
    O7 0.024(2) 0.053(4) 0.083(5) 0.005(3) -0.008(4) -0.005(4)
    O8 0.046(3) 0.079(5) 0.064(5) -0.013(3) 0.006(4) -0.014(4)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C8 . 1.298(8) yes
    O2 C8 . 1.211(7) yes
    O3 C9 . 1.201(7) yes
    O4 C9 . 1.309(7) yes
    O5 C1 . 1.264(7) yes
    O6 C1 . 1.234(7) yes
    C7 C2 . 1.374(8) ?
    C7 C6 . 1.393(8) ?
    C7 H7 . 0.9300 ?
    C3 C4 . 1.386(8) ?
    C3 C2 . 1.404(9) ?
    C3 H3 . 0.9300 ?
    O5 H5A . 0.8200 ?
    C6 C5 . 1.382(8) ?
    C6 C8 . 1.480(8) ?
    C4 C5 . 1.390(8) ?
    C4 C9 . 1.501(8) ?
    O4 H4 . 0.8200 ?
    C2 C1 . 1.509(7) ?
    O1 H1 . 0.8200 ?
    C5 H5 . 0.9300 ?
    O7 H7A . 0.89(5) ?
    O7 H7B . 0.84(5) ?
    O8 H8A . 0.89(5) ?
    O8 H8B . 0.90(5) ?
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
    O6 C1 O5 . . 122.8(5) yes
    O2 C8 O1 . . 123.4(6) yes
    O3 C9 C4 . . 124.8(6) yes
    C2 C7 C6 . . 121.5(6) ?
    C2 C7 H7 . . 119.2 ?
    C6 C7 H7 . . 119.2 ?
    C4 C3 C2 . . 120.3(5) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C1 O5 H5A . . 109.5 ?
    C5 C6 C7 . . 118.9(6) ?
    C5 C6 C8 . . 119.7(5) ?
    C7 C6 C8 . . 121.4(5) ?
    C3 C4 C5 . . 119.5(6) ?
    C3 C4 C9 . . 119.7(5) ?
    C5 C4 C9 . . 120.8(5) ?
    O2 C8 C6 . . 124.8(6) ?
    O1 C8 C6 . . 111.7(5) ?
    O3 C9 O4 . . 123.8(6) ?
    O4 C9 C4 . . 111.3(5) ?
    C9 O4 H4 . . 109.5 ?
    C7 C2 C3 . . 118.9(5) ?
    C7 C2 C1 . . 120.6(6) ?
    C3 C2 C1 . . 120.5(6) ?
    C8 O1 H1 . . 109.5 ?
    C6 C5 C4 . . 120.8(5) ?
    C6 C5 H5 . . 119.6 ?
    C4 C5 H5 . . 119.6 ?
    O6 C1 C2 . . 120.6(6) ?
    O5 C1 C2 . . 116.6(5) ?
    H7A O7 H7B . . 113(10) ?
    H8A O8 H8B . . 120(9) ?
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
    C2 C7 C6 C5 . . . . -1.8(11) ?
    C2 C7 C6 C8 . . . . 179.3(7) ?
    C2 C3 C4 C5 . . . . -1.5(11) ?
    C2 C3 C4 C9 . . . . 176.4(7) ?
    C5 C6 C8 O2 . . . . 4.0(13) ?
    C7 C6 C8 O2 . . . . -177.2(8) ?
    C5 C6 C8 O1 . . . . -174.0(7) ?
    C7 C6 C8 O1 . . . . 4.9(10) ?
    C3 C4 C9 O3 . . . . 166.4(8) ?
    C5 C4 C9 O3 . . . . -15.7(13) ?
    C3 C4 C9 O4 . . . . -15.8(10) ?
    C5 C4 C9 O4 . . . . 162.1(7) ?
    C6 C7 C2 C3 . . . . 2.7(12) ?
    C6 C7 C2 C1 . . . . -178.2(6) ?
    C4 C3 C2 C7 . . . . -1.0(11) ?
    C4 C3 C2 C1 . . . . 179.9(7) ?
    C7 C6 C5 C4 . . . . -0.9(11) ?
    C8 C6 C5 C4 . . . . 178.0(7) ?
    C3 C4 C5 C6 . . . . 2.5(11) ?
    C9 C4 C5 C6 . . . . -175.4(6) ?
    C7 C2 C1 O6 . . . . 25.2(11) ?
    C3 C2 C1 O6 . . . . -155.7(7) ?
    C7 C2 C1 O5 . . . . -155.9(7) ?
    C3 C2 C1 O5 . . . . 23.1(11) ?
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
    O8 H8B O2 3_556 0.90(5) 2.01(7) 2.853(9) 157(11)
    O7 H7B O6 . 0.84(5) 2.00(7) 2.805(7) 162(14)
    O7 H7A O3 3_556 0.89(5) 2.13(6) 2.980(8) 160(10)
    O8 H8A O7 . 0.89(5) 1.91(5) 2.801(9) 173(11)
    O1 H1 O6 2_655 0.82 1.81 2.580(6) 156
    O4 H4 O5 2_664 0.82 1.73 2.528(6) 164
    O5 H5A O8 1_554 0.82 2.06 2.845(9) 160
data_global
_journal_date_recd_electronic     2005-04-15
_journal_date_accepted     2005-05-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      6
_journal_page_first     o1607
_journal_page_last     o1608
_journal_paper_category     EO
_publ_contact_author_name     'Xin-Hua, Li'
_publ_contact_author_address
;
 School of Chemistry and Materials Science
 Wenzhou Normal College
 Zhejiang, Wenzhou 325027
 People's Republic of China
;
_publ_contact_author_email     lixinhua01@126.com
_publ_contact_author_fax     '86-577-88339081'
_publ_contact_author_phone     '86-577-88339081'
_publ_section_title
;
Trimesic acid dihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhen-Zhong Fan'
;
    Department Of Petroleum Engineering
    Daqing Petroleum Institute
    Daqing 163318
    People's Republic of China
;
    'Xin-Hua Li'
;
    School of Chemistry and Materials Science
    Wenzhou Normal College
    Zhejiang, Wenzhou 325027
    People's Republic of China
;
    'Guo-Ping Wang'
;
    Department Of Chemistry
    Zhejiang University
    Zhejiang, Hangzhou 310027
    People's Republic of China
;
