#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012355.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_2012355
loop_
_publ_author_name
'Laphookhieo, Surat'
'Karalai, Chatchanok'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Usman, Anwar'
'Rat-a-pa, Yanisa'
'Chantrapromma, Kan'
_publ_section_title
;
 Atomic charges of cerbinal
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1352
_journal_page_last               1353
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C11 H8 O4'
_chemical_formula_moiety         'C11 H8 O4'
_chemical_formula_sum            'C11 H8 O4'
_chemical_formula_weight         204.17
_chemical_melting_point          450.0(10)
_chemical_name_common            Cerbinal
_chemical_name_systematic
;
Methyl 1-formyl-6-oxa-6H-indene-4-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8622(2)
_cell_length_b                   10.82440(10)
_cell_length_c                   12.3446(3)
_cell_measurement_reflns_used    3144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.50
_cell_volume                     916.95(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0829
_diffrn_reflns_av_sigmaI/netI    .0635
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6418
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_refine_diff_density_max         .354
_refine_diff_density_min         -.446
_refine_ls_extinction_coef       .015(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          .0782
_refine_ls_R_factor_gt           .0561
_refine_ls_shift/su_max          .036
_refine_ls_shift/su_mean         .002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0799P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1446
_reflns_number_gt                900
_reflns_number_total             1323
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ta1345.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '449-451 K' was changed to
'450.0(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_database_code               2012355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 .1363(5) .3189(2) .16333(19) .0618(7) Uani d . 1 O
O2 .1100(5) .12325(19) .72795(17) .0553(7) Uani d . 1 O
O3 .1279(4) .47706(16) .49857(15) .0410(6) Uani d . 1 O
O4 .1314(4) .3151(2) .79461(16) .0433(6) Uani d . 1 O
C1 .1279(5) .2860(3) .4065(2) .0287(6) Uani d . 1 C
C2 .1313(6) .4101(3) .4055(2) .0366(7) Uani d . 1 C
H2A .1361 .4513 .3394 .044 Uiso calc R 1 H
C3 .1239(6) .4169(3) .5954(2) .0356(7) Uani d . 1 C
H3A .1218 .4641 .6583 .043 Uiso calc R 1 H
C4 .1229(5) .2919(2) .6052(2) .0276(6) Uani d . 1 C
C5 .1243(5) .2191(2) .5093(2) .0275(6) Uani d . 1 C
C6 .1225(5) .0940(3) .4859(2) .0360(7) Uani d . 1 C
H6A .1193 .0301 .5362 .043 Uiso calc R 1 H
C7 .1263(6) .0807(3) .3717(2) .0398(7) Uani d . 1 C
H7A .1266 .0054 .3354 .048 Uiso calc R 1 H
C8 .1296(5) .1955(3) .3213(2) .0337(7) Uani d . 1 C
C9 .1345(6) .2176(3) .2059(3) .0445(8) Uani d . 1 C
H9A .1365 .1489 .1606 .053 Uiso calc R 1 H
C10 .1214(5) .2336(3) .7136(2) .0339(6) Uani d . 1 C
C11 .1271(7) .2634(3) .9036(2) .0490(9) Uani d . 1 C
H11A .1352 .3291 .9557 .074 Uiso calc R 1 H
H11B .2355 .2084 .9130 .074 Uiso calc R 1 H
H11C .0076 .2188 .9139 .074 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 .0816(18) .0745(16) .0293(12) .004(2) .0014(14) .0078(12)
O2 .0955(19) .0390(12) .0316(12) -.0035(16) -.0027(17) .0100(10)
O3 .0637(14) .0296(9) .0298(11) -.0017(12) -.0017(14) .0028(9)
O4 .0647(13) .0451(11) .0201(10) -.0038(15) -.0014(12) .0009(9)
C1 .0267(13) .0351(13) .0242(13) -.0013(18) -.0014(14) .0001(12)
C2 .0476(16) .0380(15) .0242(14) .000(2) .0031(17) .0060(12)
C3 .0500(16) .0321(14) .0246(14) -.004(2) -.0007(18) -.0012(12)
C4 .0288(13) .0312(13) .0227(13) -.0011(16) -.0002(15) .0012(11)
C5 .0235(12) .0333(13) .0256(13) .0040(17) .0010(15) .0000(13)
C6 .0415(15) .0311(13) .0354(16) -.0019(17) -.0005(19) -.0024(13)
C7 .0441(16) .0403(16) .0349(16) .0051(19) -.0014(19) -.0118(13)
C8 .0327(14) .0436(16) .0248(13) -.0013(19) .0015(15) -.0036(12)
C9 .0468(18) .0605(19) .0261(15) -.001(2) .0032(18) -.0062(16)
C10 .0360(15) .0414(16) .0243(13) -.0023(18) -.0012(18) .0037(12)
C11 .064(2) .063(2) .0195(14) -.004(2) -.0014(18) .0049(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C2 O3 C3 119.2(2) yes
C10 O4 C11 115.9(2) yes
C2 C1 C8 132.4(3) ?
C2 C1 C5 120.3(3) ?
C8 C1 C5 107.3(2) ?
C1 C2 O3 121.6(2) ?
C1 C2 H2A 119.2 ?
O3 C2 H2A 119.2 ?
C4 C3 O3 123.7(3) ?
C4 C3 H3A 118.1 ?
O3 C3 H3A 118.1 ?
C3 C4 C5 118.5(2) ?
C3 C4 C10 120.4(2) ?
C5 C4 C10 121.1(2) ?
C6 C5 C4 135.6(3) ?
C6 C5 C1 107.7(3) ?
C4 C5 C1 116.7(2) ?
C5 C6 C7 107.8(3) ?
C5 C6 H6A 126.1 ?
C7 C6 H6A 126.1 ?
C8 C7 C6 110.8(3) ?
C8 C7 H7A 124.6 ?
C6 C7 H7A 124.6 ?
C7 C8 C1 106.3(2) ?
C7 C8 C9 126.1(3) ?
C1 C8 C9 127.6(3) ?
O1 C9 C8 125.1(3) yes
O1 C9 H9A 117.5 ?
C8 C9 H9A 117.5 ?
O2 C10 O4 123.1(3) ?
O2 C10 C4 123.7(3) ?
O4 C10 C4 113.2(2) ?
O4 C11 H11A 109.5 ?
O4 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
O4 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.217(4) yes
O2 C10 1.210(3) yes
O3 C2 1.359(3) yes
O3 C3 1.361(3) yes
O4 C10 1.336(4) yes
O4 C11 1.457(4) yes
C1 C2 1.344(4) yes
C1 C8 1.438(4) ?
C1 C5 1.461(4) ?
C2 H2A .9300 ?
C3 C4 1.359(4) yes
C3 H3A .9300 ?
C4 C5 1.423(4) ?
C4 C10 1.479(4) ?
C5 C6 1.384(4) ?
C6 C7 1.417(4) ?
C6 H6A .9300 ?
C7 C8 1.390(4) ?
C7 H7A .9300 ?
C8 C9 1.445(4) ?
C9 H9A .9300 ?
C11 H11A .9600 ?
C11 H11B .9600 ?
C11 H11C .9600 ?
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
C11 H11A O1 1_556 .96 2.5658 3.262(3) 130 yes