#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/16/7101608.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_7101608
loop_
_publ_author_name
'Enders, Dieter'
'Gasperi, Tecla'
_publ_section_title
;
 Proline organocatalysis as a new tool for the asymmetric synthesis of
 ulosonic acid precursors.
;
_journal_issue                   1
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              88
_journal_page_last               90
_journal_paper_doi               10.1039/b611265j
_journal_year                    2007
_chemical_formula_moiety         'C16 H29 N O7'
_chemical_formula_sum            'C16 H29 N O7'
_chemical_formula_weight         347.40
_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                 96.077(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7551(14)
_cell_length_b                   6.1499(5)
_cell_length_c                   13.849(3)
_cell_measurement_reflns_used    202
_cell_measurement_temperature    159(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     910.8(2)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      159(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16581
_diffrn_reflns_theta_full        33.52
_diffrn_reflns_theta_max         33.52
_diffrn_reflns_theta_min         1.90
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         335
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.046P)²+0.08P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                3365
_reflns_number_total             3651
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b611265j.txt
_cod_data_source_block           gasperi1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7101608
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
O7 O 0.65675(7) 0.43743(17) 0.21593(6) 0.02506(17) Uani 1 1 d .
O5 O 0.50573(8) 0.43327(16) -0.00481(6) 0.02322(16) Uani 1 1 d .
O2 O 0.82643(8) 0.42945(18) -0.38207(6) 0.02639(18) Uani 1 1 d .
O6 O 0.45425(7) 0.31305(15) 0.16897(6) 0.02313(17) Uani 1 1 d .
C11 C 0.73996(9) 0.4243(2) -0.07892(7) 0.01859(18) Uani 1 1 d .
H11A H 0.6645 0.4097 -0.1273 0.022 Uiso 1 1 calc R
N N 0.86599(8) 0.42112(18) -0.22036(6) 0.02033(17) Uani 1 1 d .
C12 C 0.71698(10) 0.2996(2) 0.01244(8) 0.0229(2) Uani 1 1 d .
H12A H 0.7207 0.1417 -0.0007 0.028 Uiso 1 1 calc R
H12B H 0.7841 0.3345 0.0647 0.028 Uiso 1 1 calc R
C14 C 0.58011(10) 0.29856(19) 0.15373(8) 0.02015(19) Uani 1 1 d .
H14A H 0.6085 0.1453 0.1660 0.024 Uiso 1 1 calc R
C1 C 0.85324(10) 0.3315(2) -0.12364(8) 0.0203(2) Uani 1 1 d .
H1A H 0.8456 0.1697 -0.1281 0.024 Uiso 1 1 calc R
O4 O 0.75919(8) 0.64903(15) -0.05687(7) 0.02437(17) Uani 1 1 d .
O3 O 0.70408(8) 0.22235(17) -0.29280(7) 0.02828(19) Uani 1 1 d .
C3 C 0.97837(10) 0.5619(2) -0.22032(8) 0.0218(2) Uani 1 1 d .
O1 O 1.01824(8) 0.58170(19) -0.11925(6) 0.0291(2) Uani 1 1 d .
C13 C 0.59175(10) 0.35376(19) 0.04667(8) 0.01878(18) Uani 1 1 d .
C6 C 0.79150(10) 0.3460(2) -0.29848(8) 0.0212(2) Uani 1 1 d .
C2 C 0.98086(11) 0.3910(3) -0.07101(9) 0.0292(3) Uani 1 1 d .
H2A H 0.9742 0.4210 -0.0015 0.035 Uiso 1 1 calc R
H2B H 1.0416 0.2717 -0.0761 0.035 Uiso 1 1 calc R
C7 C 0.75640(12) 0.3776(2) -0.47600(8) 0.0265(2) Uani 1 1 d .
C16 C 0.62150(14) 0.6624(2) 0.20573(12) 0.0349(3) Uani 1 1 d .
H16A H 0.6458 0.7186 0.1442 0.052 Uiso 1 1 calc R
H16B H 0.6639 0.7460 0.2598 0.052 Uiso 1 1 calc R
H16C H 0.5308 0.6759 0.2062 0.052 Uiso 1 1 calc R
C15 C 0.43127(13) 0.2479(3) 0.26461(9) 0.0308(3) Uani 1 1 d .
H15A H 0.4620 0.0993 0.2769 0.046 Uiso 1 1 calc R
H15B H 0.3412 0.2529 0.2702 0.046 Uiso 1 1 calc R
H15C H 0.4748 0.3468 0.3123 0.046 Uiso 1 1 calc R
C4 C 0.94831(13) 0.7900(2) -0.25711(11) 0.0315(3) Uani 1 1 d .
H4A H 0.8813 0.8512 -0.2227 0.047 Uiso 1 1 calc R
H4B H 0.9211 0.7850 -0.3269 0.047 Uiso 1 1 calc R
H4C H 1.0231 0.8813 -0.2456 0.047 Uiso 1 1 calc R
C5 C 1.08091(11) 0.4541(3) -0.27180(10) 0.0320(3) Uani 1 1 d .
H5A H 1.1009 0.3115 -0.2426 0.048 Uiso 1 1 calc R
H5B H 1.1559 0.5458 -0.2650 0.048 Uiso 1 1 calc R
H5C H 1.0518 0.4358 -0.3408 0.048 Uiso 1 1 calc R
C8 C 0.62566(14) 0.4718(3) -0.48040(11) 0.0415(4) Uani 1 1 d .
H8A H 0.5784 0.3953 -0.4341 0.062 Uiso 1 1 calc R
H8B H 0.5833 0.4544 -0.5462 0.062 Uiso 1 1 calc R
H8C H 0.6308 0.6267 -0.4638 0.062 Uiso 1 1 calc R
C9 C 0.75511(17) 0.1327(3) -0.49454(12) 0.0397(3) Uani 1 1 d .
H9A H 0.7056 0.0605 -0.4484 0.059 Uiso 1 1 calc R
H9B H 0.8409 0.0770 -0.4861 0.059 Uiso 1 1 calc R
H9C H 0.7180 0.1037 -0.5610 0.059 Uiso 1 1 calc R
C10 C 0.83207(16) 0.4929(3) -0.54736(10) 0.0401(3) Uani 1 1 d .
H10A H 0.8331 0.6495 -0.5342 0.060 Uiso 1 1 calc R
H10B H 0.7940 0.4664 -0.6138 0.060 Uiso 1 1 calc R
H10C H 0.9179 0.4371 -0.5401 0.060 Uiso 1 1 calc R
H4O H 0.694(2) 0.711(5) -0.0738(16) 0.048(6) Uiso 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 0.0033 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
C14 O7 C16 112.99(9)
C6 O2 C7 120.81(10)
C14 O6 C15 112.83(9)
O4 C11 C12 110.06(9)
O4 C11 C1 110.11(9)
C12 C11 C1 110.73(9)
C6 N C1 119.67(9)
C6 N C3 127.58(9)
C1 N C3 111.88(9)
C13 C12 C11 112.23(9)
O6 C14 O7 112.43(9)
O6 C14 C13 108.12(9)
O7 C14 C13 110.61(9)
N C1 C2 100.32(9)
N C1 C11 112.55(9)
C2 C1 C11 115.45(10)
O1 C3 N 102.14(8)
O1 C3 C4 106.40(10)
N C3 C4 113.23(10)
O1 C3 C5 109.80(10)
N C3 C5 111.99(11)
C4 C3 C5 112.58(11)
C3 O1 C2 108.60(10)
O5 C13 C12 123.74(10)
O5 C13 C14 121.45(9)
C12 C13 C14 114.81(9)
O3 C6 O2 125.25(10)
O3 C6 N 123.75(10)
O2 C6 N 110.99(10)
O1 C2 C1 104.87(9)
O2 C7 C8 109.84(10)
O2 C7 C10 102.42(10)
C8 C7 C10 110.72(13)
O2 C7 C9 110.96(12)
C8 C7 C9 112.22(14)
C10 C7 C9 110.26(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7 C14 1.4145(14)
O7 C16 1.4375(19)
O5 C13 1.2098(14)
O2 C6 1.3553(14)
O2 C7 1.4675(14)
O6 C14 1.3947(13)
O6 C15 1.4302(14)
C11 O4 1.4256(15)
C11 C12 1.5218(15)
C11 C1 1.5341(15)
N C6 1.3572(14)
N C1 1.4683(14)
N C3 1.4866(14)
C12 C13 1.5116(15)
C14 C13 1.5389(15)
C1 C2 1.5289(16)
O3 C6 1.2181(15)
C3 O1 1.4250(14)
C3 C4 1.5156(19)
C3 C5 1.5265(16)
O1 C2 1.4282(18)
C7 C8 1.5160(19)
C7 C10 1.520(2)
C7 C9 1.528(2)
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
O4 C11 C12 C13 70.06(12)
C1 C11 C12 C13 -167.97(9)
C15 O6 C14 O7 -62.29(13)
C15 O6 C14 C13 175.32(10)
C16 O7 C14 O6 -58.41(13)
C16 O7 C14 C13 62.57(13)
C6 N C1 C2 158.85(11)
C3 N C1 C2 -11.30(12)
C6 N C1 C11 -77.89(13)
C3 N C1 C11 111.97(11)
O4 C11 C1 N -67.94(11)
C12 C11 C1 N 170.12(9)
O4 C11 C1 C2 46.42(13)
C12 C11 C1 C2 -75.53(13)
C6 N C3 O1 -178.64(11)
C1 N C3 O1 -9.46(12)
C6 N C3 C4 67.38(15)
C1 N C3 C4 -123.44(11)
C6 N C3 C5 -61.22(16)
C1 N C3 C5 107.96(11)
N C3 O1 C2 28.53(12)
C4 C3 O1 C2 147.46(10)
C5 C3 O1 C2 -90.45(12)
C11 C12 C13 O5 20.24(17)
C11 C12 C13 C14 -160.14(10)
O6 C14 C13 O5 12.11(15)
O7 C14 C13 O5 -111.39(12)
O6 C14 C13 C12 -167.52(10)
O7 C14 C13 C12 68.97(12)
C7 O2 C6 O3 1.30(19)
C7 O2 C6 N -177.71(10)
C1 N C6 O3 7.94(18)
C3 N C6 O3 176.38(12)
C1 N C6 O2 -173.03(10)
C3 N C6 O2 -4.59(17)
C3 O1 C2 C1 -36.94(12)
N C1 C2 O1 28.07(12)
C11 C1 C2 O1 -93.15(11)
C6 O2 C7 C8 65.53(17)
C6 O2 C7 C10 -176.78(12)
C6 O2 C7 C9 -59.13(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21198157
