#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152055.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_7152055
loop_
_publ_author_name
'Aitken, David J.'
'Drouin, Ludovic'
'Goretta, Sarah'
'Guillot, Régis'
'Ollivier, Jean'
'Spiga, Marco'
_publ_section_title
;
 Stereoselective preparation of β,γ-methano-GABA derivatives.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7517
_journal_page_last               7524
_journal_paper_doi               10.1039/c1ob06095c
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H16 N O4, C10 H16 N O'
_chemical_formula_sum            'C20 H32 N2 O5'
_chemical_formula_weight         380.48
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1131(17)
_cell_length_b                   10.109(2)
_cell_length_c                   25.357(6)
_cell_measurement_reflns_used    2614
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      21.17
_cell_measurement_theta_min      3.14
_cell_volume                     2079.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_sigmaI/netI    0.0710
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18000
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         24.26
_diffrn_reflns_theta_min         2.17
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.7(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0532
_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)+(0.0586P)²+0.2544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2643
_reflns_number_total             3359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06095c.txt
_cod_data_source_block           1067GuillotICMMO
_cod_original_cell_volume        2079.6(8)
_cod_database_code               7152055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.3148(3) 0.6275(2) 0.92787(9) 0.0254(6) Uani 1 1 d .
H1 H 0.2230 0.6103 0.9396 0.038 Uiso 1 1 calc R
C1 C 0.2022(4) 0.7919(3) 0.86715(12) 0.0181(7) Uani 1 1 d .
C8 C 0.4979(4) 0.7918(3) 0.89494(12) 0.0181(7) Uani 1 1 d .
H8 H 0.4997 0.8811 0.8799 0.022 Uiso 1 1 calc R
C6 C 0.1678(4) 0.9244(3) 0.85545(13) 0.0211(8) Uani 1 1 d .
H6 H 0.2206 0.9911 0.8742 0.025 Uiso 1 1 calc R
C4 C -0.0211(4) 0.8596(4) 0.78791(14) 0.0307(9) Uani 1 1 d .
H4 H -0.0969 0.8814 0.7618 0.037 Uiso 1 1 calc R
C2 C 0.1261(4) 0.6957(4) 0.83756(13) 0.0247(8) Uani 1 1 d .
H2 H 0.1499 0.6072 0.8440 0.030 Uiso 1 1 calc R
C5 C 0.0566(4) 0.9575(4) 0.81641(13) 0.0263(8) Uani 1 1 d .
H5 H 0.0340 1.0459 0.8093 0.032 Uiso 1 1 calc R
C7 C 0.3196(4) 0.7610(3) 0.91160(13) 0.0180(7) Uani 1 1 d .
H7 H 0.2914 0.8170 0.9418 0.022 Uiso 1 1 calc R
C9 C 0.5631(4) 0.6972(3) 0.85371(13) 0.0255(8) Uani 1 1 d .
H9A H 0.5649 0.6091 0.8679 0.038 Uiso 1 1 calc R
H9B H 0.6728 0.7228 0.8439 0.038 Uiso 1 1 calc R
H9C H 0.4930 0.6996 0.8232 0.038 Uiso 1 1 calc R
C3 C 0.0148(4) 0.7285(4) 0.79850(13) 0.0280(9) Uani 1 1 d .
H3 H -0.0363 0.6620 0.7792 0.034 Uiso 1 1 calc R
N1 N 0.6075(3) 0.7911(2) 0.94211(10) 0.0173(6) Uani 1 1 d .
H1A H 0.6384 0.7073 0.9489 0.021 Uiso 1 1 calc R
H1B H 0.5502 0.8205 0.9702 0.021 Uiso 1 1 calc R
C10 C 0.7577(4) 0.8743(3) 0.93546(14) 0.0242(8) Uani 1 1 d .
H10A H 0.7257 0.9644 0.9291 0.036 Uiso 1 1 calc R
H10B H 0.8208 0.8423 0.9061 0.036 Uiso 1 1 calc R
H10C H 0.8233 0.8699 0.9669 0.036 Uiso 1 1 calc R
O2 O 0.4487(3) 0.1281(2) 0.91375(9) 0.0220(5) Uani 1 1 d .
O3 O 0.5763(3) 0.3026(2) 0.87378(8) 0.0255(6) Uani 1 1 d .
O4 O 0.2402(3) -0.0467(2) 1.03915(9) 0.0223(5) Uani 1 1 d .
O5 O 0.5024(2) -0.1135(2) 1.03511(9) 0.0216(5) Uani 1 1 d .
C15 C 0.5129(4) 0.2358(3) 0.91584(13) 0.0206(7) Uani 1 1 d .
C12 C 0.5490(4) 0.2598(3) 0.82008(13) 0.0215(8) Uani 1 1 d .
C13 C 0.3661(4) 0.2644(5) 0.80841(15) 0.0426(11) Uani 1 1 d .
H13A H 0.3241 0.3508 0.8166 0.064 Uiso 1 1 calc R
H13B H 0.3101 0.1996 0.8295 0.064 Uiso 1 1 calc R
H13C H 0.3479 0.2458 0.7717 0.064 Uiso 1 1 calc R
C14 C 0.6404(5) 0.3622(4) 0.78833(15) 0.0367(10) Uani 1 1 d .
H14A H 0.7554 0.3593 0.7971 0.055 Uiso 1 1 calc R
H14B H 0.5974 0.4484 0.7962 0.055 Uiso 1 1 calc R
H14C H 0.6266 0.3441 0.7514 0.055 Uiso 1 1 calc R
C11 C 0.6209(5) 0.1235(4) 0.81032(16) 0.0449(11) Uani 1 1 d .
H11A H 0.5546 0.0582 0.8278 0.067 Uiso 1 1 calc R
H11B H 0.7314 0.1200 0.8238 0.067 Uiso 1 1 calc R
H11C H 0.6223 0.1059 0.7731 0.067 Uiso 1 1 calc R
N2 N 0.5370(3) 0.3075(3) 0.95945(10) 0.0217(6) Uani 1 1 d .
H2A H 0.5965 0.3778 0.9574 0.026 Uiso 1 1 calc R
C19 C 0.4468(4) 0.0885(3) 1.07931(13) 0.0187(7) Uani 1 1 d .
H19A H 0.3510 0.1374 1.0913 0.022 Uiso 1 1 calc R
H19B H 0.5086 0.0608 1.1101 0.022 Uiso 1 1 calc R
C16 C 0.4679(4) 0.2721(3) 1.00910(12) 0.0209(8) Uani 1 1 d .
H16 H 0.3472 0.2715 1.0107 0.025 Uiso 1 1 calc R
C18 C 0.5525(4) 0.3232(3) 1.05680(14) 0.0229(8) Uani 1 1 d .
H18A H 0.4844 0.3547 1.0856 0.027 Uiso 1 1 calc R
H18B H 0.6548 0.3712 1.0519 0.027 Uiso 1 1 calc R
C20 C 0.3911(4) -0.0323(3) 1.04912(13) 0.0198(8) Uani 1 1 d .
C17 C 0.5531(4) 0.1775(3) 1.04575(13) 0.0207(8) Uani 1 1 d .
H17 H 0.6574 0.1400 1.0333 0.025 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
C2 C1 C6 118.1(3)
C2 C1 C7 123.0(3)
C6 C1 C7 118.8(3)
N1 C8 C9 110.0(2)
N1 C8 C7 109.9(2)
C9 C8 C7 113.0(3)
C5 C6 C1 120.9(3)
C5 C4 C3 119.3(3)
C1 C2 C3 121.0(3)
C4 C5 C6 120.1(3)
O1 C7 C1 113.5(3)
O1 C7 C8 107.4(2)
C1 C7 C8 110.3(2)
C2 C3 C4 120.5(3)
C8 N1 C10 113.2(2)
C15 O3 C12 122.1(2)
O2 C15 N2 126.0(3)
O2 C15 O3 125.1(3)
N2 C15 O3 108.9(3)
O3 C12 C14 102.9(3)
O3 C12 C13 109.0(3)
C14 C12 C13 110.9(3)
O3 C12 C11 111.5(3)
C14 C12 C11 110.3(3)
C13 C12 C11 111.9(3)
C15 N2 C16 122.5(3)
C17 C19 C20 111.6(3)
N2 C16 C18 116.8(3)
N2 C16 C17 121.8(3)
C18 C16 C17 60.3(2)
C16 C18 C17 60.5(2)
O4 C20 O5 124.1(3)
O4 C20 C19 119.1(3)
O5 C20 C19 116.8(3)
C18 C17 C16 59.3(2)
C18 C17 C19 118.6(3)
C16 C17 C19 117.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.412(4)
C1 C2 1.375(4)
C1 C6 1.400(4)
C1 C7 1.508(4)
C8 N1 1.490(4)
C8 C9 1.513(4)
C8 C7 1.538(4)
C6 C5 1.381(5)
C4 C5 1.378(5)
C4 C3 1.383(5)
C2 C3 1.380(5)
N1 C10 1.491(4)
O2 C15 1.208(4)
O3 C15 1.363(4)
O3 C12 1.446(4)
O4 C20 1.258(4)
O5 C20 1.272(4)
C15 N2 1.337(4)
C12 C14 1.506(5)
C12 C13 1.514(5)
C12 C11 1.517(5)
N2 C16 1.424(4)
C19 C17 1.510(4)
C19 C20 1.510(4)
C16 C18 1.483(5)
C16 C17 1.502(4)
C18 C17 1.499(4)
