#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203154.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_2203154
loop_
_publ_author_name
'Duffy, Marina'
'Gallagher, John F.'
'Lough, Alan J.'
_publ_section_title
;C---H···O and C---H···π(arene)
 interactions in
 (2S,4S,5R)-(--)-2-(4-propoxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o234
_journal_page_last               o236
_journal_paper_doi               10.1107/S1600536803028733
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C20 H25 N O2'
_chemical_formula_moiety         'C20 H25 N O2'
_chemical_formula_sum            'C20 H25 N O2'
_chemical_formula_weight         311.41
_chemical_melting_point          344
_chemical_name_systematic
;
(2S,4S,5R)-(-)-2-(4-propoxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.0830(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2962(2)
_cell_length_b                   8.2755(2)
_cell_length_c                   11.4267(3)
_cell_measurement_reflns_used    14364
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.55
_cell_volume                     878.91(4)
_computing_cell_refinement       'DENZO--SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO--SMN
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_av_sigmaI/netI    0.038
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8081
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.11
_refine_ls_extinction_coef       0.068(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0392P)²+0.0616P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.076
_refine_ls_wR_factor_ref         0.079
_reflns_number_gt                1988
_reflns_number_total             2136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6304.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_Hall     p_2yb
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2203154
_cod_database_fobs_code          2203154
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_type_symbol
O1 0.62951(11) 0.25267(14) -0.13941(9) 0.0336(3) Uani d . 1 O
C2 0.64463(15) 0.37668(18) -0.05284(12) 0.0284(3) Uani d . 1 C
N3 0.79419(13) 0.42830(16) -0.06489(10) 0.0298(3) Uani d . 1 N
C31 0.82173(18) 0.5817(2) -0.00494(14) 0.0400(4) Uani d . 1 C
C4 0.80871(16) 0.4413(2) -0.19220(13) 0.0319(3) Uani d . 1 C
C41 0.96437(19) 0.4422(2) -0.22974(17) 0.0447(4) Uani d . 1 C
C5 0.71528(16) 0.2981(2) -0.23745(13) 0.0316(3) Uani d . 1 C
C11 0.79682(16) 0.15241(19) -0.27952(13) 0.0335(3) Uani d . 1 C
C12 0.86946(17) 0.0513(2) -0.20172(15) 0.0384(4) Uani d . 1 C
C13 0.9480(2) -0.0799(2) -0.2413(2) 0.0504(5) Uani d . 1 C
C14 0.9534(2) -0.1127(3) -0.3595(2) 0.0595(6) Uani d . 1 C
C15 0.8799(2) -0.0135(3) -0.43796(19) 0.0602(6) Uani d . 1 C
C16 0.80236(19) 0.1184(3) -0.39881(14) 0.0456(4) Uani d . 1 C
C21 0.60989(15) 0.31007(18) 0.06553(12) 0.0282(3) Uani d . 1 C
C22 0.49376(16) 0.36969(19) 0.12624(13) 0.0296(3) Uani d . 1 C
C23 0.45726(15) 0.30686(19) 0.23513(13) 0.0298(3) Uani d . 1 C
C24 0.53876(15) 0.1832(2) 0.28387(12) 0.0287(3) Uani d . 1 C
C25 0.65725(16) 0.1231(2) 0.22425(13) 0.0345(3) Uani d . 1 C
C26 0.69145(15) 0.1862(2) 0.11617(13) 0.0337(3) Uani d . 1 C
O31 0.51184(12) 0.11104(15) 0.38943(9) 0.0361(3) Uani d . 1 O
C32 0.39621(16) 0.1753(2) 0.45720(13) 0.0327(3) Uani d . 1 C
C33 0.38810(17) 0.0773(2) 0.56802(14) 0.0377(4) Uani d . 1 C
C34 0.2810(2) 0.1468(3) 0.65260(16) 0.0527(5) Uani d . 1 C
H2 0.5785 0.4685 -0.0724 0.034 Uiso calc R 1 H
H31A 0.7556 0.6642 -0.0358 0.060 Uiso calc R 1 H
H31B 0.9212 0.6155 -0.0180 0.060 Uiso calc R 1 H
H31C 0.8068 0.5682 0.0792 0.060 Uiso calc R 1 H
H4 0.7625 0.5444 -0.2187 0.038 Uiso calc R 1 H
H41A 1.0110 0.5420 -0.2027 0.067 Uiso calc R 1 H
H41B 0.9681 0.4364 -0.3153 0.067 Uiso calc R 1 H
H41C 1.0146 0.3489 -0.1955 0.067 Uiso calc R 1 H
H5 0.6503 0.3374 -0.3021 0.038 Uiso calc R 1 H
H12 0.8655 0.0722 -0.1201 0.046 Uiso calc R 1 H
H13 0.9980 -0.1472 -0.1869 0.060 Uiso calc R 1 H
H14 1.0070 -0.2025 -0.3868 0.071 Uiso calc R 1 H
H15 0.8828 -0.0361 -0.5194 0.072 Uiso calc R 1 H
H16 0.7528 0.1857 -0.4535 0.055 Uiso calc R 1 H
H22 0.4379 0.4549 0.0932 0.036 Uiso calc R 1 H
H23 0.3770 0.3487 0.2755 0.036 Uiso calc R 1 H
H25 0.7142 0.0392 0.2579 0.041 Uiso calc R 1 H
H26 0.7718 0.1444 0.0758 0.040 Uiso calc R 1 H
H32A 0.3043 0.1679 0.4124 0.039 Uiso calc R 1 H
H32B 0.4146 0.2903 0.4761 0.039 Uiso calc R 1 H
H33A 0.4844 0.0737 0.6064 0.045 Uiso calc R 1 H
H33B 0.3599 -0.0349 0.5481 0.045 Uiso calc R 1 H
H34A 0.3124 0.2549 0.6771 0.079 Uiso calc R 1 H
H34B 0.2752 0.0766 0.7214 0.079 Uiso calc R 1 H
H34C 0.1861 0.1540 0.6141 0.079 Uiso calc R 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 0.0033 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'
N N 0.0061 0.0033 '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_publ_flag
C2 O1 C5 107.60(11) yes
O1 C2 N3 103.03(11) yes
O1 C2 C21 109.85(12) ?
N3 C2 C21 114.38(12) ?
C31 N3 C2 111.56(12) ?
C31 N3 C4 112.46(12) ?
C2 N3 C4 102.71(11) yes
N3 C4 C41 112.76(13) ?
N3 C4 C5 102.30(11) yes
C41 C4 C5 116.15(14) ?
O1 C5 C11 109.19(12) ?
O1 C5 C4 104.80(12) yes
C11 C5 C4 115.79(12) ?
C12 C11 C16 118.58(16) ?
C12 C11 C5 121.31(14) ?
C16 C11 C5 120.10(15) ?
C11 C12 C13 121.01(17) ?
C14 C13 C12 120.1(2) ?
C13 C14 C15 119.34(19) ?
C14 C15 C16 120.68(19) ?
C15 C16 C11 120.2(2) ?
C22 C21 C26 118.49(13) ?
C22 C21 C2 120.22(13) ?
C26 C21 C2 121.28(13) ?
C21 C22 C23 121.23(14) ?
C24 C23 C22 119.58(13) ?
O31 C24 C23 124.58(13) yes
O31 C24 C25 115.60(13) yes
C23 C24 C25 119.82(13) yes
C26 C25 C24 119.85(14) ?
C25 C26 C21 121.03(14) ?
C24 O31 C32 117.55(12) yes
O31 C32 C33 107.64(13) yes
C32 C33 C34 112.06(15) yes
O1 C2 H2 109.8 ?
N3 C2 H2 109.8 ?
C21 C2 H2 109.8 ?
N3 C31 H31A 109.5 ?
N3 C31 H31B 109.5 ?
H31A C31 H31B 109.5 ?
N3 C31 H31C 109.5 ?
H31A C31 H31C 109.5 ?
H31B C31 H31C 109.5 ?
N3 C4 H4 108.4 ?
C41 C4 H4 108.4 ?
C5 C4 H4 108.4 ?
C4 C41 H41A 109.5 ?
C4 C41 H41B 109.5 ?
H41A C41 H41B 109.5 ?
C4 C41 H41C 109.5 ?
H41A C41 H41C 109.5 ?
H41B C41 H41C 109.5 ?
O1 C5 H5 108.9 ?
C11 C5 H5 108.9 ?
C4 C5 H5 108.9 ?
C11 C12 H12 119.5 ?
C13 C12 H12 119.5 ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
C14 C15 H15 119.7 ?
C16 C15 H15 119.7 ?
C15 C16 H16 119.9 ?
C11 C16 H16 119.9 ?
C21 C22 H22 119.4 ?
C23 C22 H22 119.4 ?
C24 C23 H23 120.2 ?
C22 C23 H23 120.2 ?
C26 C25 H25 120.1 ?
C24 C25 H25 120.1 ?
C25 C26 H26 119.5 ?
C21 C26 H26 119.5 ?
O31 C32 H32A 110.2 ?
C33 C32 H32A 110.2 ?
O31 C32 H32B 110.2 ?
C33 C32 H32B 110.2 ?
H32A C32 H32B 108.5 ?
C32 C33 H33A 109.2 ?
C34 C33 H33A 109.2 ?
C32 C33 H33B 109.2 ?
C34 C33 H33B 109.2 ?
H33A C33 H33B 107.9 ?
C33 C34 H34A 109.5 ?
C33 C34 H34B 109.5 ?
H34A C34 H34B 109.5 ?
C33 C34 H34C 109.5 ?
H34A C34 H34C 109.5 ?
H34B C34 H34C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.4305(18) yes
O1 C5 1.4373(17) yes
C2 N3 1.4635(18) yes
C2 C21 1.5014(19) ?
N3 C31 1.463(2) ?
N3 C4 1.4676(18) yes
C4 C41 1.517(2) ?
C4 C5 1.552(2) yes
C5 C11 1.508(2) ?
C11 C12 1.387(2) ?
C11 C16 1.394(2) ?
C12 C13 1.389(3) ?
C13 C14 1.379(3) ?
C14 C15 1.386(3) ?
C15 C16 1.387(3) ?
C21 C22 1.385(2) ?
C21 C26 1.394(2) ?
C22 C23 1.396(2) ?
C23 C24 1.384(2) ?
C24 O31 1.3731(17) yes
C24 C25 1.398(2) ?
C25 C26 1.383(2) ?
O31 C32 1.4386(17) yes
C32 C33 1.507(2) yes
C33 C34 1.514(2) yes
C2 H2 1.000 ?
C31 H31A 0.980 ?
C31 H31B 0.980 ?
C31 H31C 0.980 ?
C4 H4 1.000 ?
C41 H41A 0.980 ?
C41 H41B 0.980 ?
C41 H41C 0.980 ?
C5 H5 1.000 ?
C12 H12 0.950 ?
C13 H13 0.950 ?
C14 H14 0.950 ?
C15 H15 0.950 ?
C16 H16 0.950 ?
C22 H22 0.950 ?
C23 H23 0.950 ?
C25 H25 0.950 ?
C26 H26 0.950 ?
C32 H32A 0.990 ?
C32 H32B 0.990 ?
C33 H33A 0.990 ?
C33 H33B 0.990 ?
C34 H34A 0.980 ?
C34 H34B 0.980 ?
C34 H34C 0.980 ?
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
_geom_hbond_publ_flag
C22 H22 O1 2_655 0.95 2.60 3.3745(19) 139 yes
C23 H23 Cg1 2_655 0.95 2.79 3.6987(16) 161 yes
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
_geom_torsion_publ_flag
C5 O1 C2 N3 -35.09(14) yes
C5 O1 C2 C21 -157.36(12) ?
O1 C2 N3 C31 165.60(11) ?
C21 C2 N3 C31 -75.22(16) ?
O1 C2 N3 C4 44.92(14) yes
C21 C2 N3 C4 164.10(13) ?
C31 N3 C4 C41 77.85(18) ?
C2 N3 C4 C41 -162.09(14) ?
C31 N3 C4 C5 -156.66(12) ?
C2 N3 C4 C5 -36.61(14) yes
C2 O1 C5 C11 136.36(12) ?
C2 O1 C5 C4 11.71(15) yes
N3 C4 C5 O1 15.80(15) yes
C41 C4 C5 O1 139.03(14) ?
N3 C4 C5 C11 -104.55(14) ?
C41 C4 C5 C11 18.68(19) ?
O1 C5 C11 C12 -46.28(18) ?
C4 C5 C11 C12 71.67(18) yes
O1 C5 C11 C16 134.80(14) ?
C4 C5 C11 C16 -107.25(16) ?
C16 C11 C12 C13 0.9(2) ?
C5 C11 C12 C13 -178.03(15) ?
C11 C12 C13 C14 -0.7(3) ?
C12 C13 C14 C15 0.0(3) ?
C13 C14 C15 C16 0.5(3) ?
C14 C15 C16 C11 -0.3(3) ?
C12 C11 C16 C15 -0.4(2) ?
C5 C11 C16 C15 178.55(16) ?
O1 C2 C21 C22 -116.58(15) ?
N3 C2 C21 C22 128.16(15) ?
O1 C2 C21 C26 62.48(17) yes
N3 C2 C21 C26 -52.78(19) ?
C26 C21 C22 C23 -0.7(2) ?
C2 C21 C22 C23 178.39(14) ?
C21 C22 C23 C24 0.3(2) ?
C22 C23 C24 O31 -179.17(14) ?
C22 C23 C24 C25 0.5(2) ?
O31 C24 C25 C26 178.86(15) ?
C23 C24 C25 C26 -0.8(2) ?
C24 C25 C26 C21 0.4(3) ?
C22 C21 C26 C25 0.4(2) ?
C2 C21 C26 C25 -178.72(15) ?
C23 C24 O31 C32 -4.0(2) ?
C25 C24 O31 C32 176.37(14) ?
C24 O31 C32 C33 -179.93(13) yes
O31 C32 C33 C34 173.36(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174514
