#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/16/2011630.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_2011630
loop_
_publ_author_name
'Harper, James K.'
'Arif, Atta M.'
'Li, J. Y.'
'Strobel, Gary'
'Grant, David M.'
_publ_section_title
;
 Terrein
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e570
_journal_page_last               e571
_journal_paper_doi               10.1107/S0108270100014803
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C8 H10 O3'
_chemical_formula_sum            'C8 H10 O3'
_chemical_formula_weight         154.16
_chemical_melting_point          393.5(15)
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.372(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5377(2)
_cell_length_b                   6.9065(2)
_cell_length_c                   12.3009(5)
_cell_measurement_reflns_used    7566
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      32.58
_cell_measurement_theta_min      1.02
_cell_volume                     385.50(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO-SMN
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_measured_fraction_theta_full .986
_diffrn_measured_fraction_theta_max .986
_diffrn_measurement_device_type  'Nonius KappaCCD '
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0159
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7566
_diffrn_reflns_theta_full        32.58
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         4.44
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    .102
_exptl_absorpt_correction_T_max  .988
_exptl_absorpt_correction_T_min  .968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             164
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .12
_refine_diff_density_max         .214
_refine_diff_density_min         -.155
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   .5(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_gt           .035
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0429P)²+0.0370P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .090
_reflns_number_gt                1344
_reflns_number_total             1479
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0418.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '392-395' was changed to '393.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '392-395' was changed to '393.5(15)'
- the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_sg_symbol_H-M      'P 21'
_cod_database_code               2011630
_cod_database_fobs_code          2011630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .4299(2) .46199(19) .50948(9) .0391(3) Uani d . 1 . . O
O2 .5205(2) .21511(18) .32289(9) .0327(2) Uani d . 1 . . O
H2 .566(5) .143(5) .382(2) .064(7) Uiso d . 1 . . H
O3 -.0447(2) .31692(18) .17100(8) .0321(2) Uani d . 1 . . O
H3 -.184(4) .290(4) .2068(17) .040(5) Uiso d . 1 . . H
C1 .2852(3) .4793(2) .42493(11) .0284(3) Uani d . 1 . . C
C2 .2578(3) .3202(2) .33958(9) .0253(2) Uani d . 1 . . C
H2A .1014 .2276 .3633 .03 Uiso calc R 1 . . H
C3 .1469(3) .4268(2) .23769(10) .0259(3) Uani d . 1 . . C
H3A .3226 .4627 .1933 .031 Uiso calc R 1 . . H
C4 .0184(3) .6132(2) .28472(11) .0280(3) Uani d . 1 . . C
C5 .1109(3) .6412(2) .38841(12) .0328(3) Uani d . 1 . . C
H5 .067 .7521 .431 .039 Uiso calc R 1 . . H
C6 -.1680(3) .7484(2) .22604(12) .0320(3) Uani d . 1 . . C
H6 -.2538 .8506 .2668 .038 Uiso calc R 1 . . H
C7 -.2295(3) .7422(2) .12017(12) .0331(3) Uani d . 1 . . C
H7 -.1527 .6379 .0787 .04 Uiso calc R 1 . . H
C8 -.4136(4) .8910(3) .06311(14) .0418(4) Uani d . 1 . . C
H8A -.5711 .8266 .0219 .063 Uiso calc R 1 . . H
H8B -.2898 .9654 .0132 .063 Uiso calc R 1 . . H
H8C -.5004 .9785 .1168 .063 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 .0506(7) .0366(6) .0299(5) -.0021(6) -.0110(5) -.0011(4)
O2 .0316(5) .0342(5) .0324(5) .0081(4) .0024(4) .0034(4)
O3 .0357(5) .0322(6) .0282(5) -.0042(5) -.0048(4) -.0036(4)
C1 .0297(6) .0292(6) .0262(6) -.0026(5) .0007(4) -.0016(5)
C2 .0259(5) .0262(6) .0239(5) -.0006(5) .0004(4) .0004(5)
C3 .0265(5) .0272(6) .0241(5) -.0014(5) -.0010(4) -.0002(5)
C4 .0287(6) .0256(6) .0295(6) -.0005(5) -.0002(5) .0005(5)
C5 .0382(7) .0299(7) .0304(7) .0031(6) -.0001(5) -.0055(5)
C6 .0359(7) .0265(7) .0338(7) .0037(6) -.0005(5) -.0007(5)
C7 .0347(7) .0298(7) .0347(7) .0001(6) -.0015(5) .0024(6)
C8 .0483(9) .0375(9) .0394(8) .0024(7) -.0101(7) .0075(6)
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 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .006 '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
C2 O2 H2 111.0(15)
C3 O3 H3 107.1(15)
O1 C1 C5 128.84(14)
O1 C1 C2 123.52(14)
C5 C1 C2 107.62(11)
O2 C2 C1 113.92(11)
O2 C2 C3 113.60(10)
C1 C2 C3 103.96(12)
O2 C2 H2A 108.4
C1 C2 H2A 108.4
C3 C2 H2A 108.4
O3 C3 C4 115.94(11)
O3 C3 C2 114.41(12)
C4 C3 C2 102.64(10)
O3 C3 H3A 107.8
C4 C3 H3A 107.8
C2 C3 H3A 107.8
C5 C4 C6 123.59(13)
C5 C4 C3 111.11(12)
C6 C4 C3 125.25(11)
C4 C5 C1 110.44(13)
C4 C5 H5 124.8
C1 C5 H5 124.8
C7 C6 C4 125.77(14)
C7 C6 H6 117.1
C4 C6 H6 117.1
C6 C7 C8 123.35(15)
C6 C7 H7 118.3
C8 C7 H7 118.3
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
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 C1 . 1.2320(17) ?
O2 C2 . 1.4117(16) ?
O2 H2 . .90(3) ?
O3 C3 . 1.4127(16) ?
O3 H3 . .80(2) ?
C1 C5 . 1.440(2) ?
C1 C2 . 1.5243(19) ?
C2 C3 . 1.5358(18) ?
C2 H2A . 1.00 ?
C3 C4 . 1.528(2) ?
C3 H3A . 1.00 ?
C4 C5 . 1.3541(19) ?
C4 C6 . 1.4494(19) ?
C5 H5 . .95 ?
C6 C7 . 1.331(2) ?
C6 H6 . .95 ?
C7 C8 . 1.496(2) ?
C7 H7 . .95 ?
C8 H8A . .98 ?
C8 H8B . .98 ?
C8 H8C . .98 ?
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
O2 H2 O1 2_646 .90(3) 1.83(3) 2.7115(16) 165(2)
O3 H3 O2 1_455 .80(2) 2.03(2) 2.8155(15) 168.4(18)
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
O1 C1 C2 O2 -38.46(18)
C5 C1 C2 O2 142.77(12)
O1 C1 C2 C3 -162.62(13)
C5 C1 C2 C3 18.61(13)
O2 C2 C3 O3 89.37(14)
C1 C2 C3 O3 -146.26(11)
O2 C2 C3 C4 -144.19(11)
C1 C2 C3 C4 -19.82(12)
O3 C3 C4 C5 141.02(12)
C2 C3 C4 C5 15.57(15)
O3 C3 C4 C6 -41.50(18)
C2 C3 C4 C6 -166.94(12)
C6 C4 C5 C1 178.33(12)
C3 C4 C5 C1 -4.14(17)
O1 C1 C5 C4 171.88(14)
C2 C1 C5 C4 -9.44(16)
C5 C4 C6 C7 169.59(15)
C3 C4 C6 C7 -7.6(2)
C4 C6 C7 C8 -177.32(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652312
