#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/45/2204590.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_2204590
loop_
_publ_author_name
'Mughal, Robila K.'
'Pritchard, Robin G.'
'Davey, Roger J.'
_publ_section_title
;
 (RS)-Benzyl mandelate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1984
_journal_page_last               o1986
_journal_paper_doi               10.1107/S1600536804025024
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H14 O3'
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.15
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.1300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0627(3)
_cell_length_b                   5.6494(2)
_cell_length_c                   26.7944(11)
_cell_measurement_reflns_used    19781
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      1
_cell_volume                     1217.30(8)
_computing_cell_refinement       'HKL SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2000)'
_computing_data_reduction
;
HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            7192
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        26.51
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.178
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0342P)²+0.1653P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0893
_reflns_number_gt                1732
_reflns_number_total             2425
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6292.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204590
_cod_database_fobs_code          2204590
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_occupancy
_atom_site_type_symbol
C1 0.45128(18) 0.6686(2) 0.20888(5) 0.0254(3) Uani d 1 C
C2 0.59343(18) 0.4981(3) 0.20329(5) 0.0266(4) Uani d 1 C
C3 0.62714(17) 0.4970(2) 0.14824(5) 0.0245(3) Uani d 1 C
C4 0.70938(18) 0.6880(3) 0.12828(6) 0.0283(4) Uani d 1 C
C5 0.7309(2) 0.6970(3) 0.07748(6) 0.0332(4) Uani d 1 C
C6 0.6696(2) 0.5168(3) 0.04634(6) 0.0349(4) Uani d 1 C
C7 0.5876(2) 0.3270(3) 0.06609(6) 0.0336(4) Uani d 1 C
C8 0.56580(19) 0.3168(3) 0.11684(6) 0.0283(4) Uani d 1 C
C9 0.16228(19) 0.7244(3) 0.19014(6) 0.0287(4) Uani d 1 C
C10 0.15042(17) 0.8770(2) 0.14424(5) 0.0243(3) Uani d 1 C
C11 0.06166(19) 1.0879(2) 0.14517(6) 0.0293(4) Uani d 1 C
C12 0.0375(2) 1.2255(3) 0.10280(6) 0.0345(4) Uani d 1 C
C13 0.1025(2) 1.1563(3) 0.05884(7) 0.0352(4) Uani d 1 C
C14 0.1933(2) 0.9489(3) 0.05773(6) 0.0350(4) Uani d 1 C
C15 0.21728(19) 0.8091(3) 0.10006(6) 0.0294(4) Uani d 1 C
O1 0.30683(12) 0.57077(16) 0.19239(4) 0.0278(3) Uani d 1 O
O2 0.46677(12) 0.86900(17) 0.22456(4) 0.0339(3) Uani d 1 O
O3 0.72933(13) 0.58119(18) 0.23477(4) 0.0356(3) Uani d 1 O
H2 0.5569(16) 0.344(2) 0.2129(5) 0.020(3) Uiso d 1 H
H3 0.798(3) 0.452(4) 0.2455(8) 0.090(7) Uiso d 1 H
H4 0.7517(18) 0.817(3) 0.1497(5) 0.032(4) Uiso d 1 H
H5 0.789(2) 0.832(3) 0.0638(6) 0.041(4) Uiso d 1 H
H6 0.683(2) 0.524(3) 0.0117(6) 0.042(5) Uiso d 1 H
H7 0.5475(19) 0.197(3) 0.0447(6) 0.034(4) Uiso d 1 H
H8 0.5101(19) 0.187(3) 0.1302(5) 0.034(4) Uiso d 1 H
H9A 0.0632(19) 0.610(2) 0.1888(5) 0.030(4) Uiso d 1 H
H9B 0.1662(18) 0.818(2) 0.2197(5) 0.026(4) Uiso d 1 H
H11 0.0162(19) 1.137(3) 0.1761(6) 0.036(4) Uiso d 1 H
H12 -0.025(2) 1.368(3) 0.1032(6) 0.040(4) Uiso d 1 H
H13 0.083(2) 1.247(3) 0.0281(6) 0.042(4) Uiso d 1 H
H14 0.241(2) 0.899(3) 0.0274(6) 0.040(5) Uiso d 1 H
H15 0.2794(19) 0.659(3) 0.0991(5) 0.033(4) Uiso d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 '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 0.011 0.006 '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
O2 C1 O1 124.58(13)
O2 C1 C2 124.72(13)
O1 C1 C2 110.66(11)
O3 C2 C1 106.85(11)
O3 C2 C3 113.31(12)
C1 C2 C3 106.78(11)
O3 C2 H2 112.4(8)
C1 C2 H2 107.5(8)
C3 C2 H2 109.6(8)
C8 C3 C4 119.58(14)
C8 C3 C2 120.71(13)
C4 C3 C2 119.52(12)
C5 C4 C3 120.14(14)
C5 C4 H4 119.3(9)
C3 C4 H4 120.6(9)
C6 C5 C4 120.04(15)
C6 C5 H5 120.5(9)
C4 C5 H5 119.5(9)
C7 C6 C5 119.91(15)
C7 C6 H6 120.3(10)
C5 C6 H6 119.8(10)
C6 C7 C8 120.36(15)
C6 C7 H7 120.5(9)
C8 C7 H7 119.2(9)
C7 C8 C3 119.97(14)
C7 C8 H8 120.1(9)
C3 C8 H8 119.9(9)
O1 C9 C10 112.44(12)
O1 C9 H9A 104.2(8)
C10 C9 H9A 109.2(8)
O1 C9 H9B 108.6(9)
C10 C9 H9B 111.1(8)
H9A C9 H9B 111.1(12)
C15 C10 C11 118.90(14)
C15 C10 C9 122.29(13)
C11 C10 C9 118.72(13)
C12 C11 C10 120.71(15)
C12 C11 H11 120.3(9)
C10 C11 H11 119.0(9)
C11 C12 C13 120.25(15)
C11 C12 H12 120.8(9)
C13 C12 H12 119.0(9)
C12 C13 C14 119.52(15)
C12 C13 H13 121.6(10)
C14 C13 H13 118.8(10)
C13 C14 C15 120.56(16)
C13 C14 H14 120.5(9)
C15 C14 H14 118.9(9)
C14 C15 C10 120.05(14)
C14 C15 H15 120.6(9)
C10 C15 H15 119.3(8)
C1 O1 C9 116.43(11)
C2 O3 H3 109.7(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.2110(16)
C1 O1 1.3352(17)
C1 C2 1.513(2)
C2 O3 1.4139(17)
C2 C3 1.519(2)
C2 H2 0.959(13)
C3 C8 1.389(2)
C3 C4 1.394(2)
C4 C5 1.385(2)
C4 H4 0.974(15)
C5 C6 1.385(2)
C5 H5 0.980(17)
C6 C7 1.385(2)
C6 H6 0.944(16)
C7 C8 1.385(2)
C7 H7 0.970(15)
C8 H8 0.945(16)
C9 O1 1.4508(17)
C9 C10 1.499(2)
C9 H9A 1.026(15)
C9 H9B 0.950(14)
C10 C15 1.390(2)
C10 C11 1.391(2)
C11 C12 1.378(2)
C11 H11 0.971(15)
C12 C13 1.379(2)
C12 H12 0.953(16)
C13 C14 1.383(2)
C13 H13 0.974(16)
C14 C15 1.384(2)
C14 H14 0.964(17)
C15 H15 0.984(15)
O3 H3 0.95(2)
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
O3 H3 O2 2_645 0.94(2) 2.08(2) 2.8711(15) 141.2(18)
O3 H3 O3 2_645 0.94(2) 2.17(2) 2.9522(6) 140.1(19)
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
O2 C1 C2 O3 20.15(19)
O1 C1 C2 O3 -162.16(11)
O2 C1 C2 C3 -101.39(15)
O1 C1 C2 C3 76.30(14)
O3 C2 C3 C8 142.87(13)
C1 C2 C3 C8 -99.78(15)
O3 C2 C3 C4 -42.13(17)
C1 C2 C3 C4 75.22(16)
C8 C3 C4 C5 -0.5(2)
C2 C3 C4 C5 -175.59(13)
C3 C4 C5 C6 0.5(2)
C4 C5 C6 C7 -0.4(2)
C5 C6 C7 C8 0.4(2)
C6 C7 C8 C3 -0.4(2)
C4 C3 C8 C7 0.5(2)
C2 C3 C8 C7 175.46(13)
O1 C9 C10 C15 27.5(2)
O1 C9 C10 C11 -156.07(12)
C15 C10 C11 C12 1.2(2)
C9 C10 C11 C12 -175.39(14)
C10 C11 C12 C13 -0.5(2)
C11 C12 C13 C14 -0.6(2)
C12 C13 C14 C15 1.0(2)
C13 C14 C15 C10 -0.3(2)
C11 C10 C15 C14 -0.8(2)
C9 C10 C15 C14 175.64(14)
O2 C1 O1 C9 4.6(2)
C2 C1 O1 C9 -173.07(11)
C10 C9 O1 C1 80.69(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12884
