#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2010591.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_2010591
loop_
_publ_author_name
'Jene, Paul G.'
'Ibers, James A.'
_publ_section_title
;
 Model porphyrin precursors: 1,2,4,5-tetrakis(cyanomethyl)benzene,
 methyl 3,4,5-triacetoxybenzoate and
 2-(<i>N</i>-phthalimidomethyl)benzoic acid
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              246
_journal_page_last               249
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C14 H14 O8'
_chemical_formula_weight         310.25
_chemical_melting_point          404.8(8)
_chemical_name_systematic
;
methyl 3,4,5-triacetoxybenzenoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2233(7)
_cell_length_b                   11.7470(10)
_cell_length_c                   13.9360(10)
_cell_measurement_reflns_used    4507
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.27
_cell_volume                     1509.9(2)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .995
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .016
_diffrn_reflns_av_sigmaI/netI    .016
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8088
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        <2
_exptl_absorpt_coefficient_mu    .114
_exptl_absorpt_correction_T_max  .976
_exptl_absorpt_correction_T_min  .959
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face-indexed (SHELXTL/PC; Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'truncated block'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          .41
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .27
_refine_diff_density_max         .27
_refine_diff_density_min         -.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.84
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.84
_refine_ls_R_factor_all          .050
_refine_ls_R_factor_gt           .043
_refine_ls_shift/su_max          .008
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'calc w = 1/[\s^2^(Fo^2^)+(0.04Fo^2^)^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .116
_reflns_number_gt                2320
_reflns_number_total             2789
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bk1493.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '404.0-405.5' was changed to
'404.8(8)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2010591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 .24362(16) .01512(12) .49717(10) .0264(3) Uani d . 1 C
C2 .25287(16) -.02827(12) .40426(10) .0286(3) Uani d . 1 C
H2A .3222 -.0853 .3893 .034 Uiso calc R 1 H
C3 .16064(16) .01251(12) .33484(10) .0284(3) Uani d . 1 C
C4 .05958(15) .09620(12) .35551(10) .0265(3) Uani d . 1 C
C5 .05181(15) .13963(12) .44761(10) .0256(3) Uani d . 1 C
C6 .14299(15) .09897(12) .51927(10) .0262(3) Uani d . 1 C
H6A .1368 .1280 .5827 .031 Uiso calc R 1 H
C7 .34029(17) -.03716(13) .57130(11) .0320(4) Uani d . 1 C
C8 .4074(2) -.04109(17) .73536(13) .0515(5) Uani d . 1 C
H8A .3743 -.0108 .7969 .077 Uiso calc R 1 H
H8B .5103 -.0229 .7270 .077 Uiso calc R 1 H
H8C .3945 -.1239 .7344 .077 Uiso calc R 1 H
C9 .09629(17) -.12726(13) .22126(11) .0346(4) Uani d . 1 C
C10 .1143(2) -.16000(16) .11909(12) .0446(4) Uani d . 1 C
H10A .0646 -.2324 .1070 .067 Uiso calc R 1 H
H10B .2177 -.1684 .1051 .067 Uiso calc R 1 H
H10C .0726 -.1008 .0778 .067 Uiso calc R 1 H
C11 .00377(18) .20723(13) .22017(11) .0340(4) Uani d . 1 C
C12 -.1041(2) .21837(16) .14101(13) .0492(5) Uani d . 1 C
H12A -.0655 .2687 .0913 .074 Uiso calc R 1 H
H12B -.1942 .2506 .1661 .074 Uiso calc R 1 H
H12C -.1237 .1432 .1134 .074 Uiso calc R 1 H
C13 -.03401(18) .31419(13) .51374(11) .0330(4) Uani d . 1 C
C14 -.1729(2) .37179(15) .53903(14) .0492(5) Uani d . 1 C
H14A -.1970 .3548 .6059 .074 Uiso calc R 1 H
H14B -.2506 .3442 .4967 .074 Uiso calc R 1 H
H14C -.1621 .4542 .5311 .074 Uiso calc R 1 H
O1 .32352(13) .00964(10) .65800(7) .0393(3) Uani d . 1 O
O2 .42358(13) -.11383(10) .55515(8) .0441(3) Uani d . 1 O
O3 .16832(12) -.02718(9) .24024(7) .0339(3) Uani d . 1 O
O4 .03011(14) -.17685(11) .28123(8) .0510(4) Uani d . 1 O
O5 -.04070(11) .12782(9) .28506(7) .0329(3) Uani d . 1 O
O6 .11505(15) .25684(12) .22943(10) .0599(4) Uani d . 1 O
O7 -.06210(11) .21413(9) .46635(7) .0313(3) Uani d . 1 O
O8 .08541(13) .34788(9) .53050(8) .0402(3) Uani d . 1 O
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
C1 .0262(8) .0261(7) .0269(8) -.0037(6) .0002(6) .0023(6)
C2 .0286(8) .0254(8) .0319(8) -.0003(6) .0051(6) .0006(6)
C3 .0326(8) .0296(8) .0230(7) -.0075(6) .0036(6) -.0028(6)
C4 .0259(8) .0279(8) .0258(7) -.0054(6) -.0020(6) .0038(6)
C5 .0235(8) .0220(7) .0312(8) -.0026(5) .0012(6) .0008(6)
C6 .0271(8) .0268(8) .0248(7) -.0045(6) .0006(6) .0001(6)
C7 .0315(9) .0323(9) .0321(9) -.0016(7) .0013(7) .0050(6)
C8 .0514(11) .0702(13) .0329(9) .0059(10) -.0069(8) .0175(9)
C9 .0350(9) .0360(9) .0328(9) -.0057(7) .0042(7) -.0058(7)
C10 .0499(11) .0519(11) .0321(9) -.0128(8) .0058(8) -.0122(8)
C11 .0408(10) .0297(8) .0313(8) -.0004(7) -.0031(7) .0041(6)
C12 .0567(12) .0489(11) .0418(10) -.0029(9) -.0148(9) .0116(8)
C13 .0386(9) .0261(8) .0343(8) .0014(7) .0044(7) .0028(6)
C14 .0438(11) .0377(10) .0664(12) .0089(8) .0121(9) -.0043(8)
O1 .0445(7) .0473(7) .0260(6) .0055(5) -.0040(5) .0059(5)
O2 .0415(7) .0455(7) .0453(7) .0139(6) -.0026(5) .0056(5)
O3 .0435(7) .0339(6) .0243(5) -.0088(5) .0045(5) -.0042(4)
O4 .0666(9) .0484(7) .0382(7) -.0254(6) .0172(6) -.0125(6)
O5 .0325(6) .0373(6) .0288(6) -.0068(5) -.0068(5) .0077(4)
O6 .0539(9) .0628(9) .0628(9) -.0273(7) -.0194(7) .0331(7)
O7 .0265(6) .0282(6) .0392(6) .0015(4) -.0004(5) -.0023(4)
O8 .0385(7) .0319(6) .0502(7) -.0032(5) -.0013(5) -.0056(5)
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
C6 C1 C2 120.71(14) ?
C6 C1 C7 122.35(13) ?
C2 C1 C7 116.86(13) ?
C3 C2 C1 119.05(14) ?
C2 C3 C4 121.06(13) ?
C2 C3 O3 120.84(14) ?
C4 C3 O3 118.08(13) ?
C5 C4 C3 119.61(13) ?
C5 C4 O5 121.08(13) ?
C3 C4 O5 119.08(13) ?
C4 C5 C6 120.40(13) ?
C4 C5 O7 116.75(13) ?
C6 C5 O7 122.38(13) ?
C5 C6 C1 119.16(13) ?
O2 C7 O1 123.63(14) yes
O2 C7 C1 123.81(14) ?
O1 C7 C1 112.56(13) ?
O4 C9 O3 122.19(14) ?
O4 C9 C10 127.43(15) yes
O3 C9 C10 110.37(13) ?
O6 C11 O5 121.87(14) ?
O6 C11 C12 127.67(15) yes
O5 C11 C12 110.46(14) ?
O8 C13 O7 123.34(14) ?
O8 C13 C14 126.61(15) yes
O7 C13 C14 110.05(14) ?
C7 O1 C8 115.96(13) yes
C9 O3 C3 115.95(11) yes
C11 O5 C4 116.60(11) yes
C13 O7 C5 119.24(12) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.395(2) yes
C2 C3 1.370(2) yes
C3 C4 1.387(2) yes
C4 C5 1.383(2) yes
C5 C6 1.386(2) yes
C1 C6 1.390(2) yes
C1 C7 1.492(2) yes
C7 O2 1.2061(18) yes
C9 O4 1.1910(19) yes
C11 O6 1.186(2) yes
C13 O8 1.1918(19) yes
C3 O3 1.4006(17) yes
C4 O5 1.3939(17) yes
C5 O7 1.3937(17) yes
C7 O1 1.3375(19) ?
C8 O1 1.4504(19) ?
C9 O3 1.3751(18) yes
C9 C10 1.485(2) ?
C11 O5 1.3646(18) yes
C11 C12 1.485(2) ?
C13 O7 1.3719(19) yes
C13 C14 1.493(2) ?
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
C2 C3 O3 C9 83.22(17) yes
C3 C4 O5 C11 -84.37(17) yes
C4 C5 O7 C13 -133.03(14) yes
C6 C1 C7 O1 -3.2(2) yes