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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/91/1519151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519151
loop_
_publ_author_name
'McCalman, Lesley'
'Hibbs, Dai. E.'
'Hursthouse, Michael B.'
'Lamond, Steven J.'
_publ_section_title
;
 C9H10O3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              818
_journal_year                    1994
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 108.85(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.336(9)
_cell_length_b                   12.996(3)
_cell_length_c                   11.379(2)
_cell_measurement_temperature    120(2)
_cell_volume                     1586.5(14)
_computing_cell_refinement       REFINE
_computing_data_collection       'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_data_reduction        'ABSURD (Karaulov, 1992)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.607
_diffrn_measured_fraction_theta_max 0.607
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.4766
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_max       -2
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2394
_diffrn_reflns_theta_full        27.15
_diffrn_reflns_theta_max         27.15
_diffrn_reflns_theta_min         3.98
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                1245
_reflns_number_total             2136
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-818.cif
_cod_data_source_block           resolve
_cod_depositor_comments
;
Citation :
McCalman, Lesley and Hibbs, Dai. E. and Hursthouse, Michael B. and 
Lamond, Steven J. (1994) University of Southampton, 
Crystal Structure Report Archive. 


http://ecrystals.chem.soton.ac.uk/818/
;
_cod_original_cell_volume        1586.5(13)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1519151
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.69462(13) -0.02933(13) 0.53905(14) 0.0251(4) Uani 1 1 d . . .
O2 O 0.89742(14) -0.02091(14) 0.83378(16) 0.0347(5) Uani 1 1 d . . .
O3 O 0.80446(13) 0.03753(13) 0.96134(14) 0.0267(4) Uani 1 1 d . . .
O5 O 0.59885(13) -0.09000(14) 0.66361(14) 0.0301(4) Uani 1 1 d . . .
O4 O 0.55947(16) 0.39180(14) 0.71223(17) 0.0370(5) Uani 1 1 d . . .
H4 H 0.5173 0.3970 0.7606 0.055 Uiso 1 1 calc R . .
O1 O 0.97936(16) 0.45842(15) 0.82581(17) 0.0398(5) Uani 1 1 d . . .
H1 H 1.0152 0.4640 0.7721 0.060 Uiso 1 1 calc R . .
C15 C 0.6278(2) 0.2684(2) 0.6027(2) 0.0284(6) Uani 1 1 d . . .
H15 H 0.6509 0.3219 0.5575 0.034 Uiso 1 1 calc R . .
C13 C 0.61403(18) 0.08962(19) 0.6419(2) 0.0221(6) Uani 1 1 d . . .
C7 C 0.8676(2) 0.0512(2) 0.8844(2) 0.0246(6) Uani 1 1 d . . .
C14 C 0.64653(19) 0.16927(19) 0.5782(2) 0.0250(6) Uani 1 1 d . . .
H14 H 0.6828 0.1540 0.5157 0.030 Uiso 1 1 calc R . .
C4 C 0.89465(18) 0.15788(19) 0.8687(2) 0.0223(6) Uani 1 1 d . . .
C17 C 0.7172(2) -0.13362(19) 0.5103(2) 0.0284(6) Uani 1 1 d . . .
H17A H 0.6383 -0.1733 0.4844 0.034 Uiso 1 1 calc R . .
H17B H 0.7762 -0.1675 0.5838 0.034 Uiso 1 1 calc R . .
C6 C 0.8946(2) 0.3357(2) 0.9215(2) 0.0318(6) Uani 1 1 d . . .
H6 H 0.8745 0.3884 0.9697 0.038 Uiso 1 1 calc R . .
C2 C 0.97900(19) 0.2834(2) 0.7669(2) 0.0273(6) Uani 1 1 d . . .
H2 H 1.0177 0.3002 0.7068 0.033 Uiso 1 1 calc R . .
C11 C 0.5429(2) 0.2148(2) 0.7564(2) 0.0255(6) Uani 1 1 d . . .
H11 H 0.5061 0.2308 0.8183 0.031 Uiso 1 1 calc R . .
C18 C 0.7704(2) -0.1282(2) 0.4082(2) 0.0367(7) Uani 1 1 d . . .
H18A H 0.7130 -0.0911 0.3379 0.055 Uiso 1 1 calc R . .
H18B H 0.7833 -0.1980 0.3821 0.055 Uiso 1 1 calc R . .
H18C H 0.8505 -0.0919 0.4367 0.055 Uiso 1 1 calc R . .
C8 C 0.7743(2) -0.0670(2) 0.9803(2) 0.0293(6) Uani 1 1 d . . .
H8A H 0.8513 -0.1081 1.0148 0.035 Uiso 1 1 calc R . .
H8B H 0.7236 -0.0983 0.9007 0.035 Uiso 1 1 calc R . .
C10 C 0.5760(2) 0.2922(2) 0.6917(2) 0.0243(6) Uani 1 1 d . . .
C1 C 0.9513(2) 0.3594(2) 0.8364(2) 0.0285(6) Uani 1 1 d . . .
C3 C 0.95157(19) 0.1843(2) 0.7834(2) 0.0267(6) Uani 1 1 d . . .
H3 H 0.9721 0.1320 0.7350 0.032 Uiso 1 1 calc R . .
C9 C 0.7035(3) -0.0645(2) 1.0681(3) 0.0456(8) Uani 1 1 d . . .
H9A H 0.7537 -0.0311 1.1453 0.068 Uiso 1 1 calc R . .
H9B H 0.6835 -0.1349 1.0860 0.068 Uiso 1 1 calc R . .
H9C H 0.6261 -0.0257 1.0315 0.068 Uiso 1 1 calc R . .
C12 C 0.56252(18) 0.11468(19) 0.73218(19) 0.0244(6) Uani 1 1 d . . .
H12 H 0.5403 0.0615 0.7783 0.029 Uiso 1 1 calc R . .
C16 C 0.6339(2) -0.0168(2) 0.6180(2) 0.0238(6) Uani 1 1 d . . .
C5 C 0.86699(19) 0.2363(2) 0.9370(2) 0.0269(6) Uani 1 1 d . . .
H5 H 0.8274 0.2202 0.9967 0.032 Uiso 1 1 calc R . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 O6 C17 116.48(19) . .
C7 O3 C8 115.9(2) . .
C10 O4 H4 109.5 . .
C1 O1 H1 109.5 . .
C14 C15 C10 120.4(2) . .
C14 C15 H15 119.8 . .
C10 C15 H15 119.8 . .
C12 C13 C14 117.7(2) . .
C12 C13 C16 119.9(2) . .
C14 C13 C16 122.4(2) . .
O2 C7 O3 120.9(2) . .
O2 C7 C4 125.8(2) . .
O3 C7 C4 113.4(2) . .
C15 C14 C13 121.4(2) . .
C15 C14 H14 119.3 . .
C13 C14 H14 119.3 . .
C3 C4 C5 117.3(2) . .
C3 C4 C7 119.7(2) . .
C5 C4 C7 123.0(2) . .
O6 C17 C18 106.4(2) . .
O6 C17 H17A 110.4 . .
C18 C17 H17A 110.4 . .
O6 C17 H17B 110.4 . .
C18 C17 H17B 110.4 . .
H17A C17 H17B 108.6 . .
C5 C6 C1 119.4(2) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
C3 C2 C1 120.2(2) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C12 C11 C10 120.1(2) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O3 C8 C9 106.8(2) . .
O3 C8 H8A 110.4 . .
C9 C8 H8A 110.4 . .
O3 C8 H8B 110.4 . .
C9 C8 H8B 110.4 . .
H8A C8 H8B 108.6 . .
O4 C10 C15 117.9(2) . .
O4 C10 C11 122.6(2) . .
C15 C10 C11 119.5(2) . .
O1 C1 C6 117.5(2) . .
O1 C1 C2 122.5(2) . .
C6 C1 C2 120.0(3) . .
C2 C3 C4 121.2(2) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C12 C13 120.9(2) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
O5 C16 O6 121.1(2) . .
O5 C16 C13 125.4(2) . .
O6 C16 C13 113.5(2) . .
C6 C5 C4 121.9(2) . .
C6 C5 H5 119.1 . .
C4 C5 H5 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C16 1.306(3) .
O6 C17 1.436(3) .
O2 C7 1.204(3) .
O3 C7 1.310(3) .
O3 C8 1.434(3) .
O5 C16 1.211(3) .
O4 C10 1.340(3) .
O4 H4 0.8400 .
O1 C1 1.340(3) .
O1 H1 0.8400 .
C15 C14 1.349(3) .
C15 C10 1.360(3) .
C15 H15 0.9500 .
C13 C12 1.374(3) .
C13 C14 1.381(3) .
C13 C16 1.442(3) .
C7 C4 1.444(4) .
C14 H14 0.9500 .
C4 C3 1.371(3) .
C4 C5 1.378(3) .
C17 C18 1.475(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C6 C5 1.354(4) .
C6 C1 1.360(3) .
C6 H6 0.9500 .
C2 C3 1.353(4) .
C2 C1 1.364(4) .
C2 H2 0.9500 .
C11 C12 1.363(3) .
C11 C10 1.369(3) .
C11 H11 0.9500 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C8 C9 1.470(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C3 H3 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C12 H12 0.9500 .
C5 H5 0.9500 .
