#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/42/1514212.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_1514212
loop_
_publ_author_name
'Zhang, Xiaofei'
'Cividino, Pascale'
'Poisson, Jean-François'
'Shpak-Kraievskyi, Pavlo'
'Laurent, Mathieu Y'
'Martel, Arnaud'
'Dujardin, Gilles'
'Py, Sandrine'
_publ_section_title
;
 Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition
 of (E)-Ketonitrones with Vinyl Ethers.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1936
_journal_page_last               1939
_journal_paper_doi               10.1021/ol500483t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H25 N O6'
_chemical_formula_sum            'C18 H25 N O6'
_chemical_formula_weight         351.39
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-20
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_cell_angle_alpha                90.89(3)
_cell_angle_beta                 94.28(3)
_cell_angle_gamma                112.44(3)
_cell_formula_units_Z            1
_cell_length_a                   6.5131(13)
_cell_length_b                   7.9315(16)
_cell_length_c                   9.954(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.546
_cell_measurement_theta_min      19.175
_cell_volume                     473.4(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      297
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_detector_type            'scintillation LiI'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker-Enraf-Nonius MACH3'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.052753
_diffrn_orient_matrix_UB_12      -0.051233
_diffrn_orient_matrix_UB_13      -0.131058
_diffrn_orient_matrix_UB_21      -0.063419
_diffrn_orient_matrix_UB_22      -0.065925
_diffrn_orient_matrix_UB_23      0.038214
_diffrn_orient_matrix_UB_31      -0.058504
_diffrn_orient_matrix_UB_32      0.042313
_diffrn_orient_matrix_UB_33      -0.003596
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1972
_diffrn_reflns_theta_full        72.96
_diffrn_reflns_theta_max         72.96
_diffrn_reflns_theta_min         4.46
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             188
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.219(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0526
_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)+(0.1049P)²+0.0599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1529
_reflns_number_gt                1672
_reflns_number_total             1972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500483t_si_002.cif
_cod_data_source_block           transf
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-8800/cifs/1514212.cif.
;
_cod_original_cell_volume        473.41(16)
_cod_database_code               1514212
#BEGIN Tags that were not found in dictionaries:
_diffrn_standards_decay_corr_max 1.004
_diffrn_standards_decay_corr_min 0.904
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, 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 1.0332(4) 0.8171(4) 0.5207(3) 0.0642(8) Uani 1 1 d .
O4 O 0.5071(4) 0.3533(4) 0.7110(3) 0.0599(7) Uani 1 1 d .
N1 N 0.8272(4) 0.7197(4) 0.5208(3) 0.0463(7) Uani 1 1 d .
O2 O 0.3627(4) 0.4590(5) 0.5387(3) 0.0709(9) Uani 1 1 d .
C2 C 0.7595(5) 0.5792(5) 0.5980(3) 0.0435(7) Uani 1 1 d .
C1 C 0.5222(5) 0.4639(5) 0.6086(3) 0.0433(7) Uani 1 1 d .
O6 O 0.7429(7) 0.5847(5) 0.2650(3) 0.0797(10) Uani 1 1 d .
O3 O 0.9933(6) 0.7770(5) 0.8427(3) 0.0749(9) Uani 1 1 d .
C3 C 0.9411(5) 0.5401(5) 0.6742(4) 0.0497(8) Uani 1 1 d .
H3A H 1.0487 0.5386 0.6123 0.060 Uiso 1 1 calc R
H3B H 0.8779 0.4192 0.7093 0.060 Uiso 1 1 calc R
O5 O 1.2527(5) 0.6590(5) 0.8264(4) 0.0764(10) Uani 1 1 d .
C4 C 1.0608(6) 0.6751(5) 0.7892(4) 0.0550(9) Uani 1 1 d .
C17 C 0.2854(8) 0.2267(7) 0.7300(7) 0.0791(14) Uani 1 1 d .
H17A H 0.2177 0.1589 0.6467 0.119 Uiso 1 1 calc R
H17B H 0.1980 0.2927 0.7580 0.119 Uiso 1 1 calc R
H17C H 0.2925 0.1441 0.7980 0.119 Uiso 1 1 calc R
C5 C 0.6780(6) 0.7789(5) 0.4272(4) 0.0524(9) Uani 1 1 d .
H5 H 0.5228 0.6955 0.4325 0.063 Uiso 1 1 calc R
C6 C 0.7036(7) 0.9730(6) 0.4709(5) 0.0639(11) Uani 1 1 d .
H6 H 0.8592 1.0551 0.4649 0.077 Uiso 1 1 calc R
C9 C 0.7440(13) 0.7616(10) 0.2866(5) 0.0903(13) Uani 1 1 d .
H9A H 0.6397 0.7818 0.2203 0.108 Uiso 1 1 calc R
H9B H 0.8916 0.8526 0.2769 0.108 Uiso 1 1 calc R
C11 C 0.8926(9) 0.4163(7) 0.1290(4) 0.0713(12) Uani 1 1 d .
C13 C 0.9449(11) 0.1656(8) 0.0142(7) 0.0891(18) Uani 1 1 d .
H13 H 0.9087 0.0798 -0.0575 0.107 Uiso 1 1 calc R
C7 C 0.5562(11) 1.0381(9) 0.3782(7) 0.0914(17) Uani 1 1 d .
H7A H 0.6039 1.0463 0.2888 0.137 Uiso 1 1 calc R
H7B H 0.5672 1.1561 0.4106 0.137 Uiso 1 1 calc R
H7C H 0.4043 0.9531 0.3767 0.137 Uiso 1 1 calc R
C16 C 1.0530(9) 0.4179(8) 0.2248(5) 0.0782(14) Uani 1 1 d .
H16 H 1.0924 0.5016 0.2980 0.094 Uiso 1 1 calc R
C8 C 0.6498(10) 0.9789(7) 0.6159(6) 0.0767(13) Uani 1 1 d .
H8A H 0.4953 0.9051 0.6226 0.115 Uiso 1 1 calc R
H8B H 0.6793 1.1027 0.6447 0.115 Uiso 1 1 calc R
H8C H 0.7406 0.9328 0.6723 0.115 Uiso 1 1 calc R
C15 C 1.1564(11) 0.3000(10) 0.2154(7) 0.0936(17) Uani 1 1 d .
H15 H 1.2659 0.3042 0.2824 0.112 Uiso 1 1 calc R
C10 C 0.7747(12) 0.5437(9) 0.1312(5) 0.0903(13) Uani 1 1 d .
H10A H 0.8612 0.6557 0.0897 0.108 Uiso 1 1 calc R
H10B H 0.6312 0.4889 0.0793 0.108 Uiso 1 1 calc R
C14 C 1.1042(12) 0.1761(9) 0.1110(7) 0.0928(17) Uani 1 1 d .
H14 H 1.1794 0.0976 0.1062 0.111 Uiso 1 1 calc R
C12 C 0.8316(9) 0.2864(10) 0.0219(5) 0.0872(17) Uani 1 1 d .
H12 H 0.7184 0.2791 -0.0435 0.105 Uiso 1 1 calc R
C18 C 1.3820(12) 0.7698(13) 0.9415(7) 0.120(3) Uani 1 1 d .
H18A H 1.4102 0.8958 0.9267 0.180 Uiso 1 1 calc R
H18B H 1.5212 0.7544 0.9550 0.180 Uiso 1 1 calc R
H18C H 1.3013 0.7336 1.0200 0.180 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 0.0181 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -1 -3
3 1 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O4 C17 115.3(3)
O1 N1 C2 120.2(3)
O1 N1 C5 114.5(3)
C2 N1 C5 125.3(3)
N1 C2 C1 123.6(3)
N1 C2 C3 115.1(3)
C1 C2 C3 121.3(3)
O4 C1 C2 109.0(3)
O2 C1 O4 122.4(3)
O2 C1 C2 128.6(3)
C9 O6 C10 114.3(4)
C2 C3 H3A 108.7
C2 C3 H3B 108.7
C2 C3 C4 114.1(3)
H3A C3 H3B 107.6
C4 C3 H3A 108.7
C4 C3 H3B 108.7
C4 O5 C18 116.6(5)
O3 C4 C3 126.1(4)
O3 C4 O5 124.7(4)
O5 C4 C3 109.2(4)
O4 C17 H17A 109.5
O4 C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17B 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N1 C5 H5 109.1
N1 C5 C6 109.2(3)
N1 C5 C9 106.1(3)
C6 C5 H5 109.1
C9 C5 H5 109.1
C9 C5 C6 114.2(4)
C5 C6 H6 108.3
C7 C6 C5 110.7(4)
C7 C6 H6 108.3
C8 C6 C5 110.2(4)
C8 C6 H6 108.3
C8 C6 C7 110.8(4)
O6 C9 C5 108.9(4)
O6 C9 H9A 109.9
O6 C9 H9B 109.9
C5 C9 H9A 109.9
C5 C9 H9B 109.9
H9A C9 H9B 108.3
C16 C11 C10 124.0(5)
C16 C11 C12 118.6(5)
C12 C11 C10 117.3(5)
C14 C13 H13 120.3
C14 C13 C12 119.5(6)
C12 C13 H13 120.3
C6 C7 H7A 109.5
C6 C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7B 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C11 C16 H16 119.5
C15 C16 C11 121.0(5)
C15 C16 H16 119.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C16 C15 H15 119.3
C14 C15 C16 121.5(6)
C14 C15 H15 119.3
O6 C10 C11 110.9(4)
O6 C10 H10A 109.5
O6 C10 H10B 109.5
C11 C10 H10A 109.5
C11 C10 H10B 109.5
H10A C10 H10B 108.1
C13 C14 C15 120.4(6)
C13 C14 H14 119.8
C15 C14 H14 119.8
C11 C12 C13 119.0(6)
C11 C12 H12 120.5
C13 C12 H12 120.5
O5 C18 H18A 109.5
O5 C18 H18B 109.5
O5 C18 H18C 109.5
H18A C18 H18B 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.267(4)
O4 C1 1.340(4)
O4 C17 1.438(5)
N1 C2 1.315(4)
N1 C5 1.503(5)
O2 C1 1.194(4)
C2 C1 1.478(4)
C2 C3 1.492(4)
O6 C9 1.413(8)
O6 C10 1.415(6)
O3 C4 1.193(5)
C3 H3A 0.9700
C3 H3B 0.9700
C3 C4 1.502(6)
O5 C4 1.330(5)
O5 C18 1.433(7)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C5 H5 0.9800
C5 C6 1.536(6)
C5 C9 1.513(7)
C6 H6 0.9800
C6 C7 1.517(7)
C6 C8 1.515(8)
C9 H9A 0.9700
C9 H9B 0.9700
C11 C16 1.357(7)
C11 C10 1.485(8)
C11 C12 1.395(8)
C13 H13 0.9300
C13 C14 1.340(9)
C13 C12 1.420(10)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C16 H16 0.9300
C16 C15 1.351(9)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C15 H15 0.9300
C15 C14 1.350(9)
C10 H10A 0.9700
C10 H10B 0.9700
C14 H14 0.9300
C12 H12 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O2 0.98 2.11 2.887(5) 134.9
