#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154135.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_7154135
loop_
_publ_author_name
'Shah, Sayali'
'White, Jonathan M.'
'Williams, Spencer J.'
_publ_section_title
;
 Total syntheses of cis-cyclopropane fatty acids: dihydromalvalic acid,
 dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic
 acid.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9427
_journal_paper_doi               10.1039/c4ob01863j
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C22 H31 N O3'
_chemical_formula_weight         357.48
_chemical_melting_point          335
_chemical_name_common
(4S)-4-Benzyl-3-[(1R,2S)-2-octylcyclopropane-1-oyl]oxazolidinone
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 91.786(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.485(3)
_cell_length_b                   5.3094(4)
_cell_length_c                   11.6620(7)
_cell_measurement_reflns_used    1399
_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      72.8150
_cell_measurement_theta_min      4.7330
_cell_volume                     2010.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5781
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.431
_diffrn_reflns_theta_min         3.792
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0586P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1387
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.712
_reflns_Friedel_fraction_max     0.715
_reflns_number_gt                2594
_reflns_number_total             3169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob01863j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7154135.cif.'
_cod_original_cell_volume        2010.5(3)
_cod_database_code               7154135
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_usercomment     'Sample S53-162 (Spencer/Sayali)'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.33793(12) -0.2044(7) 0.5158(3) 0.0289(7) Uani 1 1 d . .
C2 C 0.35456(13) -0.1822(8) 0.4000(3) 0.0344(8) Uani 1 1 d . .
H2 H 0.3390 -0.0789 0.3441 0.041 Uiso 1 1 calc R U
C3 C 0.40197(13) -0.1818(8) 0.3930(3) 0.0360(9) Uani 1 1 d . .
H3 H 0.4125 -0.0792 0.3305 0.043 Uiso 1 1 calc R U
C4 C 0.42968(12) -0.1899(7) 0.4980(3) 0.0342(8) Uani 1 1 d . .
H4A H 0.4557 -0.2652 0.4780 0.041 Uiso 1 1 calc R U
H4B H 0.4173 -0.2977 0.5546 0.041 Uiso 1 1 calc R U
C5 C 0.43811(13) 0.0680(7) 0.5519(3) 0.0348(8) Uani 1 1 d . .
H5A H 0.4501 0.1773 0.4953 0.042 Uiso 1 1 calc R U
H5B H 0.4122 0.1424 0.5737 0.042 Uiso 1 1 calc R U
C6 C 0.46692(14) 0.0533(7) 0.6567(4) 0.0368(8) Uani 1 1 d . .
H6A H 0.4914 -0.0397 0.6366 0.044 Uiso 1 1 calc R U
H6B H 0.4534 -0.0407 0.7161 0.044 Uiso 1 1 calc R U
C7 C 0.48008(13) 0.3102(7) 0.7052(4) 0.0367(8) Uani 1 1 d . .
H7A H 0.4910 0.4112 0.6440 0.044 Uiso 1 1 calc R U
H7B H 0.4560 0.3962 0.7331 0.044 Uiso 1 1 calc R U
C8 C 0.51244(13) 0.2915(7) 0.8027(3) 0.0356(8) Uani 1 1 d . .
H8A H 0.5356 0.1950 0.7762 0.043 Uiso 1 1 calc R U
H8B H 0.5008 0.1998 0.8658 0.043 Uiso 1 1 calc R U
C9 C 0.52808(13) 0.5462(7) 0.8469(3) 0.0357(8) Uani 1 1 d . .
H9A H 0.5391 0.6403 0.7835 0.043 Uiso 1 1 calc R U
H9B H 0.5051 0.6409 0.8759 0.043 Uiso 1 1 calc R U
C10 C 0.56102(14) 0.5228(8) 0.9409(4) 0.0395(9) Uani 1 1 d . .
H10A H 0.5836 0.4236 0.9126 0.047 Uiso 1 1 calc R U
H10B H 0.5497 0.4333 1.0052 0.047 Uiso 1 1 calc R U
C11 C 0.57756(16) 0.7765(8) 0.9824(4) 0.0508(11) Uani 1 1 d . .
H11A H 0.5985 0.7502 1.0412 0.076 Uiso 1 1 calc R U
H11B H 0.5555 0.8737 1.0129 0.076 Uiso 1 1 calc R U
H11C H 0.5891 0.8654 0.9194 0.076 Uiso 1 1 calc R U
C12 C 0.37786(14) -0.4060(8) 0.3543(4) 0.0403(9) Uani 1 1 d . .
H12A H 0.3796 -0.5558 0.4018 0.048 Uiso 1 1 calc R U
H12B H 0.3756 -0.4383 0.2725 0.048 Uiso 1 1 calc R U
C13 C 0.29287(12) 0.1782(7) 0.4905(3) 0.0291(8) Uani 1 1 d . .
C14 C 0.26830(13) 0.2062(8) 0.6722(3) 0.0354(8) Uani 1 1 d . .
H14A H 0.2416 0.1409 0.6926 0.042 Uiso 1 1 calc R U
H14B H 0.2762 0.3384 0.7259 0.042 Uiso 1 1 calc R U
C15 C 0.30067(12) -0.0050(7) 0.6740(3) 0.0283(7) Uani 1 1 d . .
H15 H 0.2875 -0.1662 0.6913 0.034 Uiso 1 1 calc R U
C16 C 0.33669(13) 0.0416(8) 0.7592(3) 0.0342(8) Uani 1 1 d . .
H16A H 0.3565 -0.0939 0.7528 0.041 Uiso 1 1 calc R U
H16B H 0.3503 0.1974 0.7391 0.041 Uiso 1 1 calc R U
C17 C 0.32348(12) 0.0582(7) 0.8818(3) 0.0329(8) Uani 1 1 d . .
C18 C 0.29884(17) -0.1257(8) 0.9296(4) 0.0447(11) Uani 1 1 d . .
H18 H 0.2898 -0.2605 0.8846 0.054 Uiso 1 1 calc R U
C19 C 0.2875(2) -0.1121(9) 1.0432(4) 0.0538(13) Uani 1 1 d . .
H19 H 0.2707 -0.2365 1.0731 0.065 Uiso 1 1 calc R U
C20 C 0.30063(16) 0.0824(10) 1.1112(4) 0.0496(11) Uani 1 1 d . .
H20 H 0.2930 0.0914 1.1873 0.059 Uiso 1 1 calc R U
C21 C 0.32528(16) 0.2647(10) 1.0661(4) 0.0535(12) Uani 1 1 d . .
H21 H 0.3347 0.3967 1.1123 0.064 Uiso 1 1 calc R U
C22 C 0.33638(15) 0.2538(9) 0.9508(4) 0.0440(10) Uani 1 1 d . .
H22 H 0.3526 0.3805 0.9209 0.053 Uiso 1 1 calc R U
N1 N 0.31367(10) -0.0044(5) 0.5555(2) 0.0288(7) Uani 1 1 d . .
O1 O 0.34547(9) -0.3767(5) 0.5815(2) 0.0338(6) Uani 1 1 d . .
O2 O 0.29566(9) 0.2276(5) 0.3903(2) 0.0365(6) Uani 1 1 d . .
O3 O 0.26689(8) 0.3004(5) 0.5575(2) 0.0340(6) 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 0.0181 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'
N N 0.0311 0.0180 '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
O1 C1 N1 117.7(3)
O1 C1 C2 124.5(3)
N1 C1 C2 117.7(3)
C1 C2 C12 117.5(4)
C1 C2 C3 116.3(3)
C12 C2 C3 58.2(3)
C12 C3 C4 121.5(4)
C12 C3 C2 59.9(3)
C4 C3 C2 122.1(3)
C3 C4 C5 113.9(3)
C6 C5 C4 112.5(3)
C5 C6 C7 114.2(3)
C8 C7 C6 113.2(3)
C7 C8 C9 114.0(3)
C10 C9 C8 113.1(3)
C9 C10 C11 113.1(3)
C3 C12 C2 61.9(3)
O2 C13 O3 122.0(4)
O2 C13 N1 129.0(4)
O3 C13 N1 109.0(3)
O3 C14 C15 105.7(3)
N1 C15 C16 112.1(3)
N1 C15 C14 101.7(3)
C16 C15 C14 113.6(3)
C17 C16 C15 112.9(3)
C22 C17 C18 117.7(4)
C22 C17 C16 120.6(4)
C18 C17 C16 121.6(4)
C19 C18 C17 121.3(4)
C20 C19 C18 120.4(5)
C19 C20 C21 119.2(4)
C20 C21 C22 120.5(4)
C17 C22 C21 120.7(4)
C13 N1 C1 127.8(3)
C13 N1 C15 111.5(3)
C1 N1 C15 119.4(3)
C13 O3 C14 112.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.213(5)
C1 N1 1.409(5)
C1 C2 1.475(5)
C2 C12 1.514(6)
C2 C3 1.545(6)
C3 C12 1.487(6)
C3 C4 1.497(6)
C4 C5 1.528(5)
C5 C6 1.518(6)
C6 C7 1.533(5)
C7 C8 1.527(6)
C8 C9 1.529(5)
C9 C10 1.512(6)
C10 C11 1.524(6)
C13 O2 1.204(4)
C13 O3 1.336(5)
C13 N1 1.392(5)
C14 O3 1.428(5)
C14 C15 1.537(5)
C15 N1 1.459(4)
C15 C16 1.531(5)
C16 C17 1.508(5)
C17 C22 1.372(6)
C17 C18 1.390(6)
C18 C19 1.388(6)
C19 C20 1.363(7)
C20 C21 1.371(8)
C21 C22 1.404(6)
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
O1 C1 C2 C12 8.6(6)
N1 C1 C2 C12 -175.4(3)
O1 C1 C2 C3 -57.4(5)
N1 C1 C2 C3 118.5(4)
C1 C2 C3 C12 107.4(4)
C1 C2 C3 C4 -3.1(5)
C12 C2 C3 C4 -110.4(4)
C12 C3 C4 C5 -156.8(4)
C2 C3 C4 C5 -84.8(4)
C3 C4 C5 C6 -178.9(3)
C4 C5 C6 C7 173.4(3)
C5 C6 C7 C8 -174.0(3)
C6 C7 C8 C9 176.1(3)
C7 C8 C9 C10 -178.3(3)
C8 C9 C10 C11 178.2(4)
C4 C3 C12 C2 111.5(4)
C1 C2 C12 C3 -105.3(4)
O3 C14 C15 N1 -0.4(4)
O3 C14 C15 C16 120.3(3)
N1 C15 C16 C17 176.3(3)
C14 C15 C16 C17 61.7(4)
C15 C16 C17 C22 -130.8(4)
C15 C16 C17 C18 50.8(5)
C22 C17 C18 C19 0.3(7)
C16 C17 C18 C19 178.7(4)
C17 C18 C19 C20 -0.6(8)
C18 C19 C20 C21 0.0(8)
C19 C20 C21 C22 1.0(8)
C18 C17 C22 C21 0.7(7)
C16 C17 C22 C21 -177.7(4)
C20 C21 C22 C17 -1.3(7)
O2 C13 N1 C1 -11.9(7)
O3 C13 N1 C1 167.3(3)
O2 C13 N1 C15 -179.0(4)
O3 C13 N1 C15 0.1(4)
O1 C1 N1 C13 -162.9(4)
C2 C1 N1 C13 20.9(5)
O1 C1 N1 C15 3.4(5)
C2 C1 N1 C15 -172.9(3)
C16 C15 N1 C13 -121.5(3)
C14 C15 N1 C13 0.2(4)
C16 C15 N1 C1 70.1(4)
C14 C15 N1 C1 -168.2(3)
O2 C13 O3 C14 178.8(4)
N1 C13 O3 C14 -0.4(4)
C15 C14 O3 C13 0.5(4)
