#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:57:15 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180324 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/38/7153881.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_7153881
loop_
_publ_author_name
'Tian, Xiang-Yin'
'Han, Jian-Wei'
'Zhao, Qiong'
'Wong, Henry N. C.'
_publ_section_title
;
 Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total
 synthesis of epiplakinic acid F.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3686
_journal_page_last               3700
_journal_paper_doi               10.1039/c4ob00448e
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H25 N O5'
_chemical_formula_weight         311.37
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.632(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4633(8)
_cell_length_b                   11.8774(17)
_cell_length_c                   12.6900(18)
_cell_measurement_reflns_used    5864
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      55.073
_cell_measurement_theta_min      4.702
_cell_volume                     821.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5307
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       0.056(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     204
_refine_ls_number_reflns         3156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0250
_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)+(0.0492P)²+0.0740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                3141
_reflns_number_total             3156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00448e3.cif
_cod_data_source_block           mo_dm11163_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7153881
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.17134(16) 0.70907(8) 0.36377(7) 0.0205(2) Uani 1 1 d .
O1 O 0.48591(15) 0.84105(7) 0.39324(6) 0.02606(18) Uani 1 1 d .
O2 O 0.46977(16) 0.68438(8) 0.49008(7) 0.0297(2) Uani 1 1 d .
O3 O -0.17093(14) 0.70557(7) 0.25652(6) 0.02327(18) Uani 1 1 d .
O4 O -0.08197(13) 0.88471(6) 0.14049(6) 0.02124(18) Uani 1 1 d .
O5 O 0.00123(13) 0.81553(7) 0.05393(6) 0.02137(18) Uani 1 1 d .
C1 C 0.1064(2) 0.60035(9) 0.41133(9) 0.0222(2) Uani 1 1 d .
H1 H -0.0644 0.6049 0.4352 0.027 Uiso 1 1 calc R
C2 C 0.2891(3) 0.59867(11) 0.50856(10) 0.0334(3) Uani 1 1 d .
H2A H 0.2044 0.6156 0.5734 0.040 Uiso 1 1 calc R
H2B H 0.3680 0.5239 0.5166 0.040 Uiso 1 1 calc R
C3 C 0.3847(2) 0.75432(10) 0.41217(8) 0.0220(2) Uani 1 1 d .
C4 C 0.01724(18) 0.75449(9) 0.28187(8) 0.0182(2) Uani 1 1 d .
C5 C 0.09472(18) 0.86354(9) 0.22677(8) 0.0186(2) Uani 1 1 d .
C6 C 0.33861(18) 0.84761(9) 0.17356(8) 0.0193(2) Uani 1 1 d .
H6A H 0.4505 0.9119 0.1890 0.023 Uiso 1 1 calc R
H6B H 0.4215 0.7773 0.1978 0.023 Uiso 1 1 calc R
C7 C 0.26022(18) 0.84170(9) 0.05515(8) 0.0196(2) Uani 1 1 d .
C8 C 0.3043(2) 0.95162(10) -0.00021(9) 0.0260(2) Uani 1 1 d .
H8 H 0.4692 0.9771 -0.0001 0.031 Uiso 1 1 calc R
C9 C 0.1358(3) 1.01524(11) -0.04843(10) 0.0338(3) Uani 1 1 d .
H9A H -0.0316 0.9932 -0.0505 0.041 Uiso 1 1 calc R
H9B H 0.1812 1.0834 -0.0812 0.041 Uiso 1 1 calc R
C10 C 0.3773(2) 0.74232(11) 0.00007(9) 0.0269(2) Uani 1 1 d .
H10A H 0.5567 0.7546 0.0012 0.032 Uiso 1 1 calc R
H10B H 0.3490 0.6729 0.0407 0.032 Uiso 1 1 calc R
C11 C 0.2796(3) 0.72458(14) -0.11369(12) 0.0431(3) Uani 1 1 d .
H11A H 0.1008 0.7164 -0.1162 0.065 Uiso 1 1 calc R
H11B H 0.3525 0.6563 -0.1418 0.065 Uiso 1 1 calc R
H11C H 0.3226 0.7896 -0.1564 0.065 Uiso 1 1 calc R
C12 C 0.0622(2) 0.96549(9) 0.29983(9) 0.0251(2) Uani 1 1 d .
H12A H -0.1135 0.9866 0.2961 0.030 Uiso 1 1 calc R
H12B H 0.1081 0.9425 0.3734 0.030 Uiso 1 1 calc R
C13 C 0.2115(3) 1.06854(10) 0.27410(11) 0.0324(3) Uani 1 1 d .
H13A H 0.3863 1.0524 0.2884 0.049 Uiso 1 1 calc R
H13B H 0.1643 1.1319 0.3179 0.049 Uiso 1 1 calc R
H13C H 0.1801 1.0878 0.1994 0.049 Uiso 1 1 calc R
C14 C 0.1244(2) 0.50011(10) 0.33576(10) 0.0268(2) Uani 1 1 d .
H14 H 0.0047 0.5133 0.2741 0.032 Uiso 1 1 calc R
C15 C 0.3781(3) 0.48810(14) 0.29326(15) 0.0502(4) Uani 1 1 d .
H15A H 0.4996 0.4744 0.3520 0.075 Uiso 1 1 calc R
H15B H 0.4199 0.5575 0.2566 0.075 Uiso 1 1 calc R
H15C H 0.3778 0.4247 0.2438 0.075 Uiso 1 1 calc R
C16 C 0.0474(3) 0.39182(11) 0.39060(11) 0.0354(3) Uani 1 1 d .
H16A H 0.1657 0.3749 0.4498 0.053 Uiso 1 1 calc R
H16B H 0.0432 0.3294 0.3400 0.053 Uiso 1 1 calc R
H16C H -0.1158 0.4020 0.4170 0.053 Uiso 1 1 calc R
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
C3 N1 C4 128.70(9)
C3 N1 C1 111.94(9)
C4 N1 C1 119.33(8)
C3 O2 C2 110.14(9)
C5 O4 O5 104.35(7)
C7 O5 O4 102.75(7)
N1 C1 C2 100.28(8)
N1 C1 C14 113.31(9)
C2 C1 C14 115.28(10)
N1 C1 H1 109.2
C2 C1 H1 109.2
C14 C1 H1 109.2
O2 C2 C1 106.01(9)
O2 C2 H2A 110.5
C1 C2 H2A 110.5
O2 C2 H2B 110.5
C1 C2 H2B 110.5
H2A C2 H2B 108.7
O1 C3 O2 122.16(10)
O1 C3 N1 128.84(10)
O2 C3 N1 108.99(10)
O3 C4 N1 118.26(10)
O3 C4 C5 122.46(9)
N1 C4 C5 119.28(9)
O4 C5 C12 102.92(8)
O4 C5 C6 104.20(8)
C12 C5 C6 119.67(9)
O4 C5 C4 107.58(8)
C12 C5 C4 109.94(8)
C6 C5 C4 111.37(8)
C7 C6 C5 103.79(7)
C7 C6 H6A 111.0
C5 C6 H6A 111.0
C7 C6 H6B 111.0
C5 C6 H6B 111.0
H6A C6 H6B 109.0
O5 C7 C8 111.44(9)
O5 C7 C10 105.41(8)
C8 C7 C10 111.75(9)
O5 C7 C6 103.40(8)
C8 C7 C6 111.88(9)
C10 C7 C6 112.49(9)
C9 C8 C7 125.97(11)
C9 C8 H8 117.0
C7 C8 H8 117.0
C8 C9 H9A 120.0
C8 C9 H9B 120.0
H9A C9 H9B 120.0
C11 C10 C7 114.07(10)
C11 C10 H10A 108.7
C7 C10 H10A 108.7
C11 C10 H10B 108.7
C7 C10 H10B 108.7
H10A C10 H10B 107.6
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C5 114.83(10)
C13 C12 H12A 108.6
C5 C12 H12A 108.6
C13 C12 H12B 108.6
C5 C12 H12B 108.6
H12A C12 H12B 107.5
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C15 C14 C16 111.31(11)
C15 C14 C1 112.89(11)
C16 C14 C1 109.66(10)
C15 C14 H14 107.6
C16 C14 H14 107.6
C1 C14 H14 107.6
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.3906(14)
N1 C4 1.4032(13)
N1 C1 1.4782(14)
O1 C3 1.2006(15)
O2 C3 1.3512(14)
O2 C2 1.4475(15)
O3 C4 1.2066(14)
O4 C5 1.4352(12)
O4 O5 1.4668(10)
O5 C7 1.4478(12)
C1 C2 1.5373(16)
C1 C14 1.5359(16)
C1 H1 1.0000
C2 H2A 0.9900
C2 H2B 0.9900
C4 C5 1.5438(14)
C5 C12 1.5422(14)
C5 C6 1.5431(13)
C6 C7 1.5378(14)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5092(15)
C7 C10 1.5321(15)
C8 C9 1.3121(19)
C8 H8 0.9500
C9 H9A 0.9500
C9 H9B 0.9500
C10 C11 1.5218(18)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.5177(17)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.5254(19)
C14 C16 1.5338(17)
C14 H14 1.0000
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
C5 O4 O5 C7 -47.79(9)
C3 N1 C1 C2 9.72(12)
C4 N1 C1 C2 -168.52(10)
C3 N1 C1 C14 -113.70(10)
C4 N1 C1 C14 68.07(12)
C3 O2 C2 C1 16.32(14)
N1 C1 C2 O2 -14.98(12)
C14 C1 C2 O2 107.05(11)
C2 O2 C3 O1 168.96(11)
C2 O2 C3 N1 -10.27(13)
C4 N1 C3 O1 -1.47(18)
C1 N1 C3 O1 -179.50(10)
C4 N1 C3 O2 177.69(10)
C1 N1 C3 O2 -0.34(12)
C3 N1 C4 O3 -174.21(10)
C1 N1 C4 O3 3.70(14)
C3 N1 C4 C5 6.52(15)
C1 N1 C4 C5 -175.57(9)
O5 O4 C5 C12 160.05(7)
O5 O4 C5 C6 34.47(9)
O5 O4 C5 C4 -83.86(8)
O3 C4 C5 O4 -4.77(13)
N1 C4 C5 O4 174.46(8)
O3 C4 C5 C12 106.60(11)
N1 C4 C5 C12 -74.16(11)
O3 C4 C5 C6 -118.38(11)
N1 C4 C5 C6 60.86(11)
O4 C5 C6 C7 -9.65(11)
C12 C5 C6 C7 -123.82(10)
C4 C5 C6 C7 106.05(9)
O4 O5 C7 C8 -80.46(9)
O4 O5 C7 C10 158.13(7)
O4 O5 C7 C6 39.87(10)
C5 C6 C7 O5 -18.74(11)
C5 C6 C7 C8 101.30(10)
C5 C6 C7 C10 -131.96(9)
O5 C7 C8 C9 -2.94(16)
C10 C7 C8 C9 114.71(14)
C6 C7 C8 C9 -118.15(14)
O5 C7 C10 C11 60.60(12)
C8 C7 C10 C11 -60.61(13)
C6 C7 C10 C11 172.58(10)
O4 C5 C12 C13 -86.46(11)
C6 C5 C12 C13 28.40(14)
C4 C5 C12 C13 159.16(10)
N1 C1 C14 C15 56.77(14)
C2 C1 C14 C15 -57.96(14)
N1 C1 C14 C16 -178.50(9)
C2 C1 C14 C16 66.77(13)
