#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:38:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178475 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029681.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_4029681
loop_
_publ_author_name
'Abate, Agnese'
'Brenna, Elisabetta'
'Fuganti, Claudio'
'Gatti, Francesco G.'
'Giovenzana, Tommaso'
'Malpezzi, Luciana'
'Serra, Stefano'
_publ_section_title
;
 Chirality and fragrance chemistry: stereoisomers of the commercial chiral
 odorants Muguesia and Pamplefleur.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1281
_journal_page_last               1290
_journal_paper_doi               10.1021/jo048445j
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C11 H16 O2'
_chemical_formula_weight         180.24
_chemical_name_systematic
;
(1R,2S,3S)-1-Phenyl-2-methyl-1,3-butanediol-(1R,2S,3S)-syn,anti-5
;
_space_group_IT_number           19
_symmetry_cell_setting           'P 2(1)2(1)2(1) '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.211(2)
_cell_length_b                   9.483(2)
_cell_length_c                   17.825(3)
_cell_measurement_reflns_used    59
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      6.85
_cell_volume                     1049.9(4)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_sigmaI/netI    0.0767
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1436
_diffrn_reflns_theta_full        64.96
_diffrn_reflns_theta_max         64.96
_diffrn_reflns_theta_min         4.96
_diffrn_standards_decay_%        <3%
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_coef       0.0051(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0988P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1769
_reflns_number_gt                898
_reflns_number_total             1285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo048445jsi20040903_114536.cif
_cod_data_source_block           aa486
_cod_database_code               4029681
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.1606(5) -0.1067(4) 0.55944(19) 0.0556(10) Uani 1 1 d .
H1O H 0.1882 -0.1678 0.5283 0.15(3) Uiso 1 1 calc R
O2 O 0.7284(6) -0.1856(3) 0.54244(18) 0.0594(10) Uani 1 1 d .
H2O H 0.8634 -0.1626 0.5450 0.14(3) Uiso 1 1 d R
C5 C 0.2831(8) 0.1300(5) 0.5870(2) 0.0435(12) Uani 1 1 d .
C1 C 0.3476(8) -0.0207(4) 0.5715(2) 0.0429(11) Uani 1 1 d .
H1 H 0.4326 -0.0313 0.5276 0.037(11) Uiso 1 1 d R
C2 C 0.4876(8) -0.0821(5) 0.6345(2) 0.0445(12) Uani 1 1 d .
H2 H 0.5992 -0.0146 0.6458 0.043(12) Uiso 1 1 d R
C10 C 0.0840(9) 0.1658(6) 0.6162(3) 0.0586(14) Uani 1 1 d .
H10 H -0.0179 0.0964 0.6259 0.070 Uiso 1 1 calc R
C6 C 0.4251(10) 0.2359(5) 0.5723(3) 0.0581(14) Uani 1 1 d .
H6 H 0.5578 0.2125 0.5516 0.070 Uiso 1 1 calc R
C3 C 0.6049(9) -0.2135(5) 0.6080(3) 0.0548(14) Uani 1 1 d .
H3 H 0.4970 -0.2882 0.5957 0.081(17) Uiso 1 1 d R
C9 C 0.0375(10) 0.3071(7) 0.6309(3) 0.0713(17) Uani 1 1 d .
H9 H -0.0953 0.3315 0.6513 0.086 Uiso 1 1 calc R
C7 C 0.3826(11) 0.3753(5) 0.5863(3) 0.0701(17) Uani 1 1 d .
H7 H 0.4842 0.4448 0.5762 0.084 Uiso 1 1 calc R
C11 C 0.3540(10) -0.1091(6) 0.7049(3) 0.0662(15) Uani 1 1 d .
H11A H 0.4449 -0.1467 0.7436 0.099 Uiso 1 1 calc R
H11B H 0.2417 -0.1754 0.6937 0.099 Uiso 1 1 calc R
H11C H 0.2913 -0.0221 0.7218 0.099 Uiso 1 1 calc R
C8 C 0.1840(11) 0.4090(6) 0.6159(3) 0.0726(17) Uani 1 1 d .
H8 H 0.1503 0.5028 0.6257 0.087 Uiso 1 1 calc R
C4 C 0.7477(11) -0.2783(6) 0.6682(3) 0.089(2) Uani 1 1 d .
H4A H 0.8151 -0.3618 0.6488 0.133 Uiso 1 1 calc R
H4B H 0.6617 -0.3024 0.7111 0.133 Uiso 1 1 calc R
H4C H 0.8563 -0.2116 0.6827 0.133 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0391(18) 0.0614(19) 0.0663(19) -0.0213(18) -0.0075(18) -0.0042(19)
O2 0.043(2) 0.064(2) 0.072(2) -0.0212(18) 0.010(2) 0.0051(19)
C5 0.043(3) 0.046(2) 0.042(2) -0.0043(19) 0.001(2) 0.003(2)
C1 0.036(3) 0.051(2) 0.041(2) -0.005(2) 0.000(2) -0.006(2)
C2 0.045(3) 0.039(2) 0.050(2) -0.007(2) -0.005(2) -0.002(2)
C10 0.048(3) 0.062(3) 0.067(3) -0.005(3) 0.004(3) 0.006(3)
C6 0.060(4) 0.051(3) 0.062(3) 0.003(2) 0.004(3) 0.005(3)
C3 0.054(3) 0.038(2) 0.072(3) -0.005(2) -0.002(3) 0.000(3)
C9 0.061(4) 0.078(4) 0.075(4) -0.017(3) 0.005(3) 0.020(4)
C7 0.076(4) 0.043(3) 0.091(4) 0.004(3) -0.005(4) 0.002(3)
C11 0.074(4) 0.079(3) 0.045(2) 0.002(2) 0.010(3) 0.010(4)
C8 0.086(5) 0.049(3) 0.084(4) -0.010(3) -0.003(4) 0.013(4)
C4 0.086(5) 0.076(4) 0.106(5) 0.019(3) -0.011(4) 0.027(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C6 C5 C10 118.0(4)
C6 C5 C1 119.4(4)
C10 C5 C1 122.6(5)
O1 C1 C5 110.5(4)
O1 C1 C2 110.6(3)
C5 C1 C2 112.0(4)
C3 C2 C11 112.3(4)
C3 C2 C1 110.8(3)
C11 C2 C1 111.0(4)
C5 C10 C9 119.4(5)
C5 C6 C7 123.4(6)
O2 C3 C2 111.2(4)
O2 C3 C4 109.9(4)
C2 C3 C4 113.1(4)
C8 C9 C10 120.6(5)
C6 C7 C8 117.7(6)
C9 C8 C7 120.8(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.436(5)
O2 C3 1.423(6)
C5 C6 1.362(6)
C5 C10 1.384(7)
C5 C1 1.510(6)
C1 C2 1.535(6)
C2 C3 1.519(6)
C2 C11 1.527(7)
C10 C9 1.396(8)
C6 C7 1.371(7)
C3 C4 1.521(7)
C9 C8 1.354(8)
C7 C8 1.379(9)
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
O1 H1O O2 0.82 1.89 2.712(4) 175.3 3_446
O2 H2O O1 0.87 1.94 2.803(5) 175.1 1_655
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
C6 C5 C1 O1 -155.4(4)
C10 C5 C1 O1 24.8(6)
C6 C5 C1 C2 80.8(5)
C10 C5 C1 C2 -99.0(5)
O1 C1 C2 C3 73.4(5)
C5 C1 C2 C3 -162.8(4)
O1 C1 C2 C11 -52.0(5)
C5 C1 C2 C11 71.8(5)
C6 C5 C10 C9 -1.4(7)
C1 C5 C10 C9 178.4(5)
C10 C5 C6 C7 1.5(8)
C1 C5 C6 C7 -178.3(5)
C11 C2 C3 O2 -179.9(4)
C1 C2 C3 O2 55.4(5)
C11 C2 C3 C4 -55.7(6)
C1 C2 C3 C4 179.6(4)
C5 C10 C9 C8 1.0(8)
C5 C6 C7 C8 -1.0(9)
C10 C9 C8 C7 -0.5(9)
C6 C7 C8 C9 0.5(9)
