#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008459.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_2008459
loop_
_publ_author_name
'Jene, P. G.'
'Chan, D. S.'
'Cooke, B. L.'
'Ibers, J. A.'
_publ_section_title
;
 Capped-porphyrin precursors
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              801
_journal_page_last               806
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          'C16 H16 O5 S, 0.5H2 O1'
_chemical_formula_moiety         'C16 H16 O5 S, 0.5H2 O1'
_chemical_formula_sum            'C16 H17 O5.5 S'
_chemical_formula_weight         329.36
_chemical_name_systematic
;
2-[3-(Tosyloxy)-ethoxy]benzaldehyde hemihydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4150(10)
_cell_length_b                   6.6930(10)
_cell_length_c                   31.692(2)
_cell_measurement_reflns_used    3194
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.91
_cell_volume                     3057.6(5)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1997)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXTL/PC (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART1000 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15612
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        <2
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  .98
_exptl_absorpt_correction_T_min  .95
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face-indexed (Sheldrick, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          .276
_exptl_crystal_size_mid          .144
_exptl_crystal_size_min          .082
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.070
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_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         0.097
_reflns_number_gt                1948
_reflns_number_total             2844
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    fr1170.cif
_[local]_cod_data_source_block   III
_[local]_cod_chemical_formula_sum_orig 'C16 H17 O5.50 S'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_original_cell_volume        3057.5(4)
_cod_database_code               2008459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
S1 0.59887(4) 0.64604(9) 0.047174(18) 0.02932(18) Uani d . 1 S
O1 0.35744(13) 0.7374(3) 0.21591(5) 0.0460(5) Uani d . 1 O
O2 0.34090(10) 0.7767(2) 0.09099(4) 0.0273(4) Uani d . 1 O
O3 0.49030(10) 0.6285(2) 0.04401(4) 0.0265(4) Uani d . 1 O
O4 0.63282(12) 0.7600(2) 0.01223(5) 0.0384(4) Uani d . 1 O
O5 0.62923(11) 0.4453(2) 0.05279(5) 0.0389(4) Uani d . 1 O
O6 0.5000 0.4850(4) 0.2500 0.0667(9) Uani d S 1 O
C1 0.34989(18) 0.7538(3) 0.17782(7) 0.0339(6) Uani d . 1 C
H1A 0.4051 0.7620 0.1616 0.041 Uiso calc R 1 H
C2 0.26137(16) 0.7618(3) 0.15553(7) 0.0256(5) Uani d . 1 C
C3 0.17858(17) 0.7584(3) 0.17811(7) 0.0322(6) Uani d . 1 C
H3A 0.1805 0.7545 0.2081 0.039 Uiso calc R 1 H
C4 0.09371(18) 0.7604(4) 0.15788(8) 0.0366(6) Uani d . 1 C
H4B 0.0377 0.7570 0.1737 0.044 Uiso calc R 1 H
C5 0.09162(17) 0.7676(3) 0.11444(7) 0.0321(6) Uani d . 1 C
H5B 0.0334 0.7686 0.1004 0.038 Uiso calc R 1 H
C6 0.17218(16) 0.7735(3) 0.09089(7) 0.0262(5) Uani d . 1 C
H6A 0.1693 0.7797 0.0610 0.031 Uiso calc R 1 H
C7 0.25746(16) 0.7703(3) 0.11136(7) 0.0250(5) Uani d . 1 C
C8 0.34115(15) 0.7817(3) 0.04599(7) 0.0261(5) Uani d . 1 C
H8A 0.3026 0.8938 0.0357 0.031 Uiso calc R 1 H
H8B 0.3158 0.6554 0.0345 0.031 Uiso calc R 1 H
C9 0.43942(16) 0.8086(3) 0.03246(7) 0.0280(6) Uani d . 1 C
H9A 0.4425 0.8298 0.0016 0.034 Uiso calc R 1 H
H9B 0.4668 0.9264 0.0466 0.034 Uiso calc R 1 H
C10 0.61654(15) 0.7830(3) 0.09353(7) 0.0263(5) Uani d . 1 C
C11 0.59672(16) 0.6950(3) 0.13226(7) 0.0307(6) Uani d . 1 C
H11A 0.5740 0.5619 0.1335 0.037 Uiso calc R 1 H
C12 0.61042(17) 0.8028(4) 0.16883(7) 0.0345(6) Uani d . 1 C
H12A 0.5972 0.7426 0.1953 0.041 Uiso calc R 1 H
C13 0.64346(16) 0.9991(3) 0.16764(7) 0.0321(6) Uani d . 1 C
C14 0.66244(16) 1.0838(4) 0.12852(7) 0.0313(6) Uani d . 1 C
H14A 0.6848 1.2172 0.1272 0.038 Uiso calc R 1 H
C15 0.64941(15) 0.9776(3) 0.09151(7) 0.0278(6) Uani d . 1 C
H15A 0.6628 1.0373 0.0650 0.033 Uiso calc R 1 H
C16 0.65870(18) 1.1144(4) 0.20792(7) 0.0434(7) Uani d . 1 C
H16A 0.7148 1.0652 0.2220 0.065 Uiso calc R 1 H
H16B 0.6051 1.0964 0.2266 0.065 Uiso calc R 1 H
H16C 0.6661 1.2566 0.2014 0.065 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
S1 0.0273(3) 0.0356(3) 0.0251(3) 0.0005(3) 0.0017(3) -0.0051(3)
O1 0.0553(13) 0.0546(12) 0.0280(11) 0.0096(10) -0.0097(8) 0.0022(8)
O2 0.0284(10) 0.0316(9) 0.0219(9) -0.0005(7) 0.0006(6) -0.0004(7)
O3 0.0253(9) 0.0260(8) 0.0284(8) -0.0012(7) -0.0003(7) -0.0017(7)
O4 0.0354(10) 0.0544(11) 0.0254(9) -0.0072(9) 0.0064(7) -0.0060(8)
O5 0.0387(11) 0.0376(10) 0.0404(11) 0.0101(8) -0.0034(8) -0.0086(8)
O6 0.068(2) 0.063(2) 0.069(2) 0.000 -0.0106(16) 0.000
C1 0.0374(16) 0.0338(14) 0.0306(15) 0.0054(12) -0.0024(11) -0.0020(11)
C2 0.0317(14) 0.0197(12) 0.0254(13) 0.0023(10) -0.0002(10) 0.0017(10)
C3 0.0414(16) 0.0301(13) 0.0251(14) 0.0032(12) 0.0039(11) 0.0012(11)
C4 0.0328(15) 0.0381(14) 0.0390(16) 0.0024(12) 0.0101(12) -0.0016(12)
C5 0.0303(14) 0.0313(13) 0.0346(14) 0.0009(11) -0.0012(11) -0.0019(11)
C6 0.0304(14) 0.0231(13) 0.0251(13) 0.0012(10) -0.0009(10) 0.0005(10)
C7 0.0280(13) 0.0190(12) 0.0279(13) -0.0004(10) 0.0034(10) -0.0018(9)
C8 0.0271(13) 0.0278(12) 0.0235(12) 0.0003(10) -0.0009(10) -0.0006(10)
C9 0.0328(14) 0.0254(13) 0.0259(13) -0.0010(10) -0.0011(10) 0.0041(10)
C10 0.0218(13) 0.0349(14) 0.0223(12) 0.0005(10) -0.0009(9) -0.0024(10)
C11 0.0299(14) 0.0340(13) 0.0282(13) -0.0037(11) -0.0003(11) 0.0017(10)
C12 0.0334(15) 0.0469(16) 0.0233(13) -0.0019(12) 0.0024(10) 0.0038(11)
C13 0.0247(14) 0.0419(16) 0.0297(14) 0.0038(11) -0.0023(10) -0.0076(11)
C14 0.0285(14) 0.0309(13) 0.0344(14) 0.0000(11) -0.0015(11) -0.0034(11)
C15 0.0243(14) 0.0355(15) 0.0237(13) 0.0012(11) 0.0002(10) 0.0025(10)
C16 0.0420(17) 0.0560(18) 0.0323(15) -0.0014(14) -0.0022(12) -0.0129(13)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
O1 O6 O1 3_655 107.92(11) yes
O5 S1 O4 . 119.64(10) yes
O5 S1 O3 . 104.08(9) yes
O4 S1 O3 . 109.32(9) yes
O5 S1 C10 . 110.15(10) yes
O4 S1 C10 . 108.70(10) yes
O3 S1 C10 . 103.74(9) yes
C7 O2 C8 . 118.40(16) yes
C9 O3 S1 . 117.06(13) yes
O1 C1 C2 . 124.2(2) yes
C3 C2 C7 . 118.7(2) no
C3 C2 C1 . 120.0(2) no
C7 C2 C1 . 121.3(2) no
C4 C3 C2 . 121.4(2) no
C5 C4 C3 . 118.9(2) no
C4 C5 C6 . 121.5(2) no
C5 C6 C7 . 119.4(2) no
O2 C7 C6 . 123.89(19) yes
O2 C7 C2 . 115.97(19) yes
C6 C7 C2 . 120.1(2) yes
O2 C8 C9 . 107.02(17) yes
O3 C9 C8 . 107.82(17) yes
C15 C10 C11 . 120.6(2) yes
C15 C10 S1 . 120.17(17) yes
C11 C10 S1 . 119.27(18) yes
C12 C11 C10 . 119.3(2) no
C11 C12 C13 . 121.2(2) no
C14 C13 C12 . 118.3(2) no
C14 C13 C16 . 121.2(2) no
C12 C13 C16 . 120.5(2) no
C15 C14 C13 . 121.3(2) no
C14 C15 C10 . 119.3(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O5 1.4243(16) yes
S1 O4 1.4311(16) yes
S1 O3 1.5726(15) yes
S1 C10 1.750(2) yes
O1 C1 1.217(3) yes
O6 O1 2.871(2) yes
O2 C7 1.366(3) yes
O2 C8 1.426(2) yes
O3 C9 1.458(2) yes
C1 C2 1.460(3) yes
C2 C3 1.392(3) no
C2 C7 1.402(3) no
C3 C4 1.381(3) no
C4 C5 1.378(3) no
C5 C6 1.381(3) no
C6 C7 1.390(3) no
C8 C9 1.491(3) yes
C10 C15 1.387(3) no
C10 C11 1.391(3) no
C11 C12 1.380(3) no
C12 C13 1.397(3) no
C13 C14 1.391(3) no
C13 C16 1.508(3) no
C14 C15 1.384(3) no
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
S1 O3 C9 C8 -160.10(10) y
O3 C9 C8 O2 66.80(10) y
C9 C8 O2 C7 174.50(10) y