#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:44:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178441 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/62/4026291.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_4026291
loop_
_publ_author_name
'Alexis Kotland'
'Fabien Accadbled'
'Koen Robeyns'
'Jean-Bernard Behr'
_publ_section_title
;
 Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine
 Alkaloid 4-epi-(+)-Codonopsinine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4094
_journal_page_last               4098
_journal_paper_doi               10.1021/jo200176u
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H19 N O3'
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_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                 92.924(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8438(3)
_cell_length_b                   6.9463(3)
_cell_length_c                   12.6905(7)
_cell_measurement_reflns_used    11166
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.7134
_cell_measurement_theta_min      2.9266
_cell_volume                     602.51(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '200 images, ΔΦ 3°'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1538
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14054
_diffrn_reflns_theta_full        25.77
_diffrn_reflns_theta_max         25.77
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            translucent
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0458
_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)+(0.0709P)²+0.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2296
_reflns_number_total             2305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200176u_si_001.cif
_cod_data_source_block           jbk73
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026291
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 -0.1196(2) 0.4000(2) 0.65260(11) 0.0115(3) Uani 1 1 d .
C2 C 0.0594(2) 0.2893(3) 0.69174(13) 0.0117(4) Uani 1 1 d .
H2 H 0.1698 0.3296 0.6480 0.014 Uiso 1 1 calc R
C3 C 0.0107(2) 0.0783(3) 0.66354(13) 0.0115(4) Uani 1 1 d .
H3 H -0.0386 0.0125 0.7271 0.014 Uiso 1 1 calc R
C4 C -0.1561(2) 0.0926(3) 0.57889(13) 0.0120(4) Uani 1 1 d .
H4 H -0.2335 -0.0295 0.5737 0.014 Uiso 1 1 calc R
C5 C -0.2741(2) 0.2553(3) 0.62549(13) 0.0123(4) Uani 1 1 d .
H5 H -0.3274 0.2081 0.6927 0.015 Uiso 1 1 calc R
C6 C 0.1260(2) 0.3182(2) 0.80671(14) 0.0119(4) Uani 1 1 d .
C7 C 0.2923(2) 0.4260(3) 0.83253(14) 0.0140(4) Uani 1 1 d .
H7 H 0.3572 0.4888 0.7777 0.017 Uiso 1 1 calc R
C8 C 0.3674(3) 0.4454(3) 0.93664(14) 0.0148(4) Uani 1 1 d .
H8 H 0.4824 0.5190 0.9521 0.018 Uiso 1 1 calc R
C9 C 0.2715(3) 0.3557(3) 1.01704(13) 0.0139(4) Uani 1 1 d .
C10 C 0.0991(3) 0.2531(3) 0.99347(14) 0.0159(4) Uani 1 1 d .
H10 H 0.0305 0.1960 1.0487 0.019 Uiso 1 1 calc R
C11 C 0.0278(3) 0.2346(3) 0.88953(15) 0.0144(4) Uani 1 1 d .
H11 H -0.0893 0.1642 0.8743 0.017 Uiso 1 1 calc R
O12 O 0.18115(18) -0.0173(2) 0.63263(10) 0.0175(3) Uani 1 1 d .
H12 H 0.154(3) -0.131(4) 0.6003(19) 0.021 Uiso 1 1 d .
O13 O -0.08834(19) 0.14816(19) 0.47884(9) 0.0147(3) Uani 1 1 d .
H13 H -0.004(3) 0.059(4) 0.4581(18) 0.018 Uiso 1 1 d .
C14 C -0.4440(2) 0.3325(3) 0.55576(14) 0.0156(4) Uani 1 1 d .
H14A H -0.5030 0.4426 0.5905 0.023 Uiso 1 1 calc R
H14B H -0.5423 0.2311 0.5441 0.023 Uiso 1 1 calc R
H14C H -0.3961 0.3734 0.4878 0.023 Uiso 1 1 calc R
C15 C -0.1831(3) 0.5543(3) 0.72116(14) 0.0160(4) Uani 1 1 d .
H15A H -0.2307 0.4988 0.7860 0.024 Uiso 1 1 calc R
H15B H -0.2886 0.6275 0.6846 0.024 Uiso 1 1 calc R
H15C H -0.0726 0.6402 0.7388 0.024 Uiso 1 1 calc R
O16 O 0.33372(19) 0.3584(2) 1.12146(10) 0.0179(3) Uani 1 1 d .
C17 C 0.5218(3) 0.4414(3) 1.14684(15) 0.0213(4) Uani 1 1 d .
H17A H 0.6218 0.3712 1.1098 0.032 Uiso 1 1 calc R
H17B H 0.5509 0.4332 1.2231 0.032 Uiso 1 1 calc R
H17C H 0.5215 0.5768 1.1250 0.032 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
C15 N1 C5 113.83(14)
C15 N1 C2 116.06(13)
C5 N1 C2 106.72(13)
N1 C2 C6 116.58(14)
N1 C2 C3 104.22(13)
C6 C2 C3 113.54(14)
N1 C2 H2 107.3
C6 C2 H2 107.3
C3 C2 H2 107.3
O12 C3 C4 115.59(14)
O12 C3 C2 109.80(14)
C4 C3 C2 104.27(13)
O12 C3 H3 109.0
C4 C3 H3 109.0
C2 C3 H3 109.0
O13 C4 C5 110.30(14)
O13 C4 C3 112.17(13)
C5 C4 C3 99.58(13)
O13 C4 H4 111.4
C5 C4 H4 111.4
C3 C4 H4 111.4
N1 C5 C14 114.20(15)
N1 C5 C4 101.90(13)
C14 C5 C4 116.05(15)
N1 C5 H5 108.1
C14 C5 H5 108.1
C4 C5 H5 108.1
C7 C6 C11 117.74(16)
C7 C6 C2 120.02(15)
C11 C6 C2 122.22(15)
C6 C7 C8 122.17(16)
C6 C7 H7 118.9
C8 C7 H7 118.9
C9 C8 C7 119.04(15)
C9 C8 H8 120.5
C7 C8 H8 120.5
O16 C9 C8 124.68(16)
O16 C9 C10 115.52(15)
C8 C9 C10 119.81(15)
C11 C10 C9 120.17(16)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C6 120.97(16)
C10 C11 H11 119.5
C6 C11 H11 119.5
C3 O12 H12 112.4(15)
C4 O13 H13 108.6(15)
C5 C14 H14A 109.5
C5 C14 H14B 109.5
H14A C14 H14B 109.5
C5 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N1 C15 H15A 109.5
N1 C15 H15B 109.5
H15A C15 H15B 109.5
N1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C9 O16 C17 116.99(14)
O16 C17 H17A 109.5
O16 C17 H17B 109.5
H17A C17 H17B 109.5
O16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C15 1.461(2)
N1 C5 1.487(2)
N1 C2 1.509(2)
C2 C6 1.520(2)
C2 C3 1.541(3)
C2 H2 1.0000
C3 O12 1.415(2)
C3 C4 1.530(2)
C3 H3 1.0000
C4 O13 1.427(2)
C4 C5 1.526(2)
C4 H4 1.0000
C5 C14 1.522(2)
C5 H5 1.0000
C6 C7 1.387(2)
C6 C11 1.402(2)
C7 C8 1.400(2)
C7 H7 0.9500
C8 C9 1.389(2)
C8 H8 0.9500
C9 O16 1.3711(19)
C9 C10 1.398(3)
C10 C11 1.389(2)
C10 H10 0.9500
C11 H11 0.9500
O12 H12 0.91(3)
O13 H13 0.90(3)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
O16 C17 1.432(2)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 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
C15 N1 C2 C6 13.4(2)
C5 N1 C2 C6 -114.70(16)
C15 N1 C2 C3 139.36(15)
C5 N1 C2 C3 11.29(16)
N1 C2 C3 O12 143.35(13)
C6 C2 C3 O12 -88.77(17)
N1 C2 C3 C4 18.93(16)
C6 C2 C3 C4 146.81(13)
O12 C3 C4 O13 -44.8(2)
C2 C3 C4 O13 75.82(17)
O12 C3 C4 C5 -161.47(15)
C2 C3 C4 C5 -40.85(16)
C15 N1 C5 C14 67.49(18)
C2 N1 C5 C14 -163.15(14)
C15 N1 C5 C4 -166.59(13)
C2 N1 C5 C4 -37.23(15)
O13 C4 C5 N1 -70.38(16)
C3 C4 C5 N1 47.69(15)
O13 C4 C5 C14 54.3(2)
C3 C4 C5 C14 172.39(14)
N1 C2 C6 C7 -106.56(18)
C3 C2 C6 C7 132.26(16)
N1 C2 C6 C11 75.2(2)
C3 C2 C6 C11 -46.0(2)
C11 C6 C7 C8 3.0(3)
C2 C6 C7 C8 -175.36(16)
C6 C7 C8 C9 -0.7(3)
C7 C8 C9 O16 177.75(16)
C7 C8 C9 C10 -2.0(3)
O16 C9 C10 C11 -177.30(16)
C8 C9 C10 C11 2.5(3)
C9 C10 C11 C6 -0.2(3)
C7 C6 C11 C10 -2.5(3)
C2 C6 C11 C10 175.80(17)
C8 C9 O16 C17 -7.3(3)
C10 C9 O16 C17 172.49(16)
