#------------------------------------------------------------------------------
#$Date: 2016-05-23 10:37:24 +0300 (Mon, 23 May 2016) $
#$Revision: 183084 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218455.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_7218455
loop_
_publ_author_name
'Coles, S. J.'
'Ellis, A. L.'
'Leung, K.'
'Sarson, J.'
'Threlfall, T. L.'
'Tizzard, G. J.'
_publ_section_title
;
 Relationships between the racemic structures of substituted mandelic
 acids containing 8- and 10-membered hydrogen bonded dimer rings
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10816
_journal_paper_doi               10.1039/C4CE01832J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C9 H10 O3'
_chemical_formula_sum            'C9 H10 O3'
_chemical_formula_weight         166.17
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.230(5)
_cell_angle_beta                 81.067(5)
_cell_angle_gamma                77.849(5)
_cell_formula_units_Z            4
_cell_length_a                   8.833(5)
_cell_length_b                   9.263(5)
_cell_length_c                   10.750(5)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     819.1(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16751
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            light_yellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.035(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0443
_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)+(0.0567P)²+0.1844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2824
_reflns_number_total             3744
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01832j2.cif
_cod_data_source_block           race2methylma-RS-2MeMA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218452--7218470.cif.
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O 1.54756(15) 0.33106(13) 1.43727(11) 0.0342(3) Uani 1 1 d .
H2 H 1.5546 0.3641 1.5008 0.051 Uiso 1 1 calc R
O5 O 1.48538(12) 0.19447(12) 0.95724(10) 0.0264(3) Uani 1 1 d .
O6 O 1.29689(12) 0.05204(12) 1.02405(11) 0.0265(3) Uani 1 1 d .
H9 H 1.3728 -0.0206 1.0292 0.040 Uiso 1 1 calc R
O2 O 1.41897(13) 0.56876(12) 1.36165(10) 0.0272(3) Uani 1 1 d .
O4 O 1.27431(13) 0.45769(12) 0.92207(10) 0.0245(3) Uani 1 1 d .
H7 H 1.2983 0.4751 0.9883 0.037 Uiso 1 1 calc R
O1 O 1.38739(12) 0.51210(12) 1.13344(9) 0.0235(3) Uani 1 1 d .
H1 H 1.4472 0.5767 1.1127 0.035 Uiso 1 1 calc R
C12 C 0.91805(18) 0.23849(17) 0.77800(14) 0.0230(3) Uani 1 1 d .
H12 H 0.8244 0.1979 0.7958 0.028 Uiso 1 1 calc R
C7 C 1.33084(18) 0.27606(17) 1.27647(13) 0.0222(3) Uani 1 1 d .
C15 C 1.18999(18) 0.35647(18) 0.72295(14) 0.0250(4) Uani 1 1 d .
H15 H 1.2837 0.3970 0.7040 0.030 Uiso 1 1 calc R
C11 C 0.98897(17) 0.24930(16) 0.88183(14) 0.0201(3) Uani 1 1 d .
C9 C 1.46858(17) 0.43972(18) 1.35091(14) 0.0228(3) Uani 1 1 d .
C6 C 1.17238(18) 0.33879(18) 1.28072(14) 0.0238(3) Uani 1 1 d .
H6 H 1.1409 0.4469 1.2592 0.029 Uiso 1 1 calc R
C16 C 1.12689(17) 0.30946(16) 0.85247(13) 0.0199(3) Uani 1 1 d .
C17 C 1.21567(17) 0.31897(17) 0.95941(14) 0.0212(3) Uani 1 1 d .
H17 H 1.1445 0.3140 1.0419 0.025 Uiso 1 1 calc R
C14 C 1.11737(19) 0.34467(19) 0.62185(15) 0.0273(4) Uani 1 1 d .
H14 H 1.1610 0.3770 0.5340 0.033 Uiso 1 1 calc R
C13 C 0.98138(19) 0.28568(18) 0.64969(15) 0.0262(4) Uani 1 1 d .
H13 H 0.9310 0.2774 0.5808 0.031 Uiso 1 1 calc R
C2 C 1.3790(2) 0.11646(18) 1.31036(14) 0.0277(4) Uani 1 1 d .
C8 C 1.44621(18) 0.38630(17) 1.23458(14) 0.0228(3) Uani 1 1 d .
H8 H 1.5484 0.3330 1.2013 0.027 Uiso 1 1 calc R
C3 C 1.2630(2) 0.02571(19) 1.34600(15) 0.0332(4) Uani 1 1 d .
H3 H 1.2929 -0.0826 1.3696 0.040 Uiso 1 1 calc R
C10 C 0.91514(18) 0.19787(18) 1.02018(14) 0.0260(4) Uani 1 1 d .
H10A H 0.8132 0.1727 1.0188 0.039 Uiso 1 1 calc R
H10B H 0.9022 0.2804 1.0630 0.039 Uiso 1 1 calc R
H10C H 0.9822 0.1071 1.0684 0.039 Uiso 1 1 calc R
C5 C 1.0604(2) 0.24556(19) 1.31597(14) 0.0282(4) Uani 1 1 d .
H5 H 0.9530 0.2893 1.3181 0.034 Uiso 1 1 calc R
C4 C 1.1067(2) 0.0882(2) 1.34803(15) 0.0324(4) Uani 1 1 d .
H4 H 1.0309 0.0233 1.3714 0.039 Uiso 1 1 calc R
C1 C 1.5479(2) 0.0419(2) 1.30827(17) 0.0371(4) Uani 1 1 d .
H1A H 1.5560 -0.0694 1.3281 0.056 Uiso 1 1 calc R
H1B H 1.5963 0.0669 1.3738 0.056 Uiso 1 1 calc R
H1C H 1.6015 0.0798 1.2215 0.056 Uiso 1 1 calc R
C18 C 1.34755(18) 0.18266(17) 0.98053(13) 0.0210(3) Uani 1 1 d .
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
C9 O3 H2 109.5
C18 O6 H9 109.5
C17 O4 H7 109.5
C8 O1 H1 109.5
C13 C12 C11 121.47(14)
C13 C12 H12 119.3
C11 C12 H12 119.3
C6 C7 C2 120.14(14)
C6 C7 C8 117.66(14)
C2 C7 C8 122.20(15)
C14 C15 C16 120.72(15)
C14 C15 H15 119.6
C16 C15 H15 119.6
C12 C11 C16 117.92(13)
C12 C11 C10 119.73(13)
C16 C11 C10 122.35(13)
O2 C9 O3 124.16(14)
O2 C9 C8 123.39(13)
O3 C9 C8 112.44(13)
C5 C6 C7 120.94(15)
C5 C6 H6 119.5
C7 C6 H6 119.5
C15 C16 C11 120.22(13)
C15 C16 C17 118.22(13)
C11 C16 C17 121.51(12)
O4 C17 C18 110.67(12)
O4 C17 C16 110.11(11)
C18 C17 C16 107.65(12)
O4 C17 H17 109.5
C18 C17 H17 109.5
C16 C17 H17 109.5
C13 C14 C15 119.52(14)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C13 C12 120.14(14)
C14 C13 H13 119.9
C12 C13 H13 119.9
C3 C2 C7 117.43(16)
C3 C2 C1 119.91(15)
C7 C2 C1 122.66(15)
O1 C8 C7 108.45(12)
O1 C8 C9 110.66(13)
C7 C8 C9 109.67(12)
O1 C8 H8 109.3
C7 C8 H8 109.3
C9 C8 H8 109.3
C4 C3 C2 122.23(16)
C4 C3 H3 118.9
C2 C3 H3 118.9
C11 C10 H10A 109.5
C11 C10 H10B 109.5
H10A C10 H10B 109.5
C11 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 C5 C6 119.38(16)
C4 C5 H5 120.3
C6 C5 H5 120.3
C3 C4 C5 119.86(15)
C3 C4 H4 120.1
C5 C4 H4 120.1
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O5 C18 O6 124.34(14)
O5 C18 C17 123.37(13)
O6 C18 C17 112.29(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C9 1.3145(19)
O3 H2 0.8400
O5 C18 1.2258(19)
O6 C18 1.3112(19)
O6 H9 0.8400
O2 C9 1.2155(19)
O4 C17 1.4137(19)
O4 H7 0.8400
O1 C8 1.4139(18)
O1 H1 0.8400
C12 C13 1.386(2)
C12 C11 1.399(2)
C12 H12 0.9500
C7 C6 1.397(2)
C7 C2 1.404(2)
C7 C8 1.521(2)
C15 C14 1.385(2)
C15 C16 1.397(2)
C15 H15 0.9500
C11 C16 1.400(2)
C11 C10 1.512(2)
C9 C8 1.524(2)
C6 C5 1.386(2)
C6 H6 0.9500
C16 C17 1.520(2)
C17 C18 1.517(2)
C17 H17 1.0000
C14 C13 1.379(2)
C14 H14 0.9500
C13 H13 0.9500
C2 C3 1.399(2)
C2 C1 1.506(3)
C8 H8 1.0000
C3 C4 1.380(3)
C3 H3 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C5 C4 1.383(3)
C5 H5 0.9500
C4 H4 0.9500
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H2 O2 0.84 1.82 2.6631(18) 176.9 2_868
O6 H9 O5 0.84 1.80 2.6381(18) 171.4 2_857
O4 H7 O1 0.84 1.99 2.8271(18) 171.6 .
O1 H1 O5 0.84 2.21 3.003(2) 157.2 2_867
O1 H1 O4 0.84 2.40 3.011(2) 130.4 2_867
