#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:57:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178797 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/51/4105160.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_4105160
loop_
_publ_author_name
'S. Corey Valdez'
'James L. Leighton'
_publ_section_title
;
 Tandem Asymmetric Aza-Darzens/Ring-Opening Reactions: Dual Functionality
 from the Silane Lewis Acid
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14638
_journal_page_last               14639
_journal_paper_doi               10.1021/ja9066354
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   5.7656(4)
_cell_length_b                   8.9612(6)
_cell_length_c                   29.955(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.37
_cell_volume                     1547.68(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_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_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            24939
_diffrn_reflns_theta_full        30.58
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9686
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                4425
_reflns_number_total             4756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9066354_si_002.cif
_cod_data_source_block           ky87s10
_cod_database_code               4105160
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 0.96777(12) 1.79872(8) 1.85673(2) 0.01745(15) Uani 1 1 d .
O2 O 1.17661(14) 1.69304(10) 1.96966(3) 0.02393(17) Uani 1 1 d .
O3 O 0.82747(14) 1.59451(8) 1.95387(3) 0.02106(16) Uani 1 1 d .
N1 N 0.64441(15) 1.85053(11) 1.92290(3) 0.01766(17) Uani 1 1 d .
H1 H 0.564(3) 1.8086(18) 1.9451(5) 0.021(3) Uiso 1 1 d .
N2 N 0.58519(15) 1.77130(10) 1.88398(3) 0.01780(17) Uani 1 1 d .
C1 C 0.74139(16) 1.75383(11) 1.85412(3) 0.01569(18) Uani 1 1 d .
C2 C 1.03159(17) 1.89336(11) 1.89378(3) 0.01524(17) Uani 1 1 d .
H2 H 1.1981 1.8729 1.9008 0.018 Uiso 1 1 calc R
C3 C 0.88917(17) 1.84922(11) 1.93489(3) 0.01612(18) Uani 1 1 d .
H3 H 0.9128 1.9288 1.9578 0.019 Uiso 1 1 calc R
C4 C 0.98280(18) 1.70409(11) 1.95443(3) 0.01712(18) Uani 1 1 d .
C5 C 0.8951(2) 1.45635(12) 1.97555(4) 0.0247(2) Uani 1 1 d .
H5A H 0.9228 1.4734 2.0078 0.030 Uiso 1 1 calc R
H5B H 1.0391 1.4167 1.9620 0.030 Uiso 1 1 calc R
C6 C 0.6982(2) 1.34849(15) 1.96898(5) 0.0335(3) Uani 1 1 d .
H6A H 0.7360 1.2534 1.9834 0.050 Uiso 1 1 calc R
H6B H 0.6735 1.3322 1.9370 0.050 Uiso 1 1 calc R
H6C H 0.5567 1.3896 1.9823 0.050 Uiso 1 1 calc R
C11 C 0.68908(17) 1.67383(11) 1.81229(3) 0.01600(18) Uani 1 1 d .
C12 C 0.85097(19) 1.66864(13) 1.77776(3) 0.0215(2) Uani 1 1 d .
H12A H 0.9928 1.7219 1.7804 0.026 Uiso 1 1 calc R
C13 C 0.8052(2) 1.58555(15) 1.73947(4) 0.0277(2) Uani 1 1 d .
H13A H 0.9158 1.5824 1.7160 0.033 Uiso 1 1 calc R
C14 C 0.5978(2) 1.50699(14) 1.73554(4) 0.0281(2) Uani 1 1 d .
H14A H 0.5683 1.4484 1.7097 0.034 Uiso 1 1 calc R
C15 C 0.4343(2) 1.51469(14) 1.76955(4) 0.0272(2) Uani 1 1 d .
H15A H 0.2914 1.4628 1.7667 0.033 Uiso 1 1 calc R
C16 C 0.47879(19) 1.59770(13) 1.80769(4) 0.0223(2) Uani 1 1 d .
H16A H 0.3660 1.6028 1.8308 0.027 Uiso 1 1 calc R
C21 C 1.01279(17) 2.05655(11) 1.88131(3) 0.01665(18) Uani 1 1 d .
C22 C 0.81911(19) 2.11418(13) 1.85919(4) 0.0214(2) Uani 1 1 d .
H22A H 0.6911 2.0512 1.8526 0.026 Uiso 1 1 calc R
C23 C 0.8136(2) 2.26416(14) 1.84681(4) 0.0270(2) Uani 1 1 d .
H23A H 0.6827 2.3028 1.8314 0.032 Uiso 1 1 calc R
C24 C 0.9986(2) 2.35701(13) 1.85695(4) 0.0287(2) Uani 1 1 d .
H24A H 0.9937 2.4593 1.8487 0.034 Uiso 1 1 calc R
C25 C 1.1907(2) 2.30086(14) 1.87913(4) 0.0279(2) Uani 1 1 d .
H25A H 1.3171 2.3647 1.8862 0.033 Uiso 1 1 calc R
C26 C 1.19823(19) 2.15009(13) 1.89109(4) 0.0218(2) Uani 1 1 d .
H26A H 1.3307 2.1114 1.9060 0.026 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
C1 O1 C2 117.36(8)
C4 O3 C5 116.33(8)
H1 N1 N2 106.1(10)
H1 N1 C3 108.4(10)
N2 N1 C3 115.81(8)
C1 N2 N1 118.06(9)
N2 C1 O1 126.58(9)
N2 C1 C11 120.64(9)
O1 C1 C11 112.74(8)
O1 C2 C21 111.06(8)
O1 C2 C3 109.24(8)
C21 C2 C3 114.18(8)
N1 C3 C4 116.40(9)
N1 C3 C2 108.62(8)
C4 C3 C2 109.82(8)
O2 C4 O3 124.48(9)
O2 C4 C3 122.75(10)
O3 C4 C3 112.75(8)
O3 C5 C6 106.66(10)
C12 C11 C16 119.42(9)
C12 C11 C1 120.65(9)
C16 C11 C1 119.89(9)
C13 C12 C11 120.15(10)
C12 C13 C14 120.16(11)
C15 C14 C13 119.70(11)
C16 C15 C14 120.33(11)
C15 C16 C11 120.21(10)
C26 C21 C22 119.45(10)
C26 C21 C2 118.41(9)
C22 C21 C2 122.11(10)
C23 C22 C21 120.03(11)
C24 C23 C22 120.17(11)
C25 C24 C23 120.13(11)
C24 C25 C26 119.88(12)
C21 C26 C25 120.33(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3680(12)
O1 C2 1.4445(11)
O2 C4 1.2110(13)
O3 C4 1.3292(13)
O3 C5 1.4515(13)
N1 H1 0.892(16)
N1 N2 1.4072(12)
N1 C3 1.4562(13)
N2 C1 1.2789(13)
C1 C11 1.4747(14)
C2 C21 1.5132(14)
C2 C3 1.5319(14)
C3 C4 1.5250(14)
C5 C6 1.5041(17)
C11 C12 1.3941(14)
C11 C16 1.3980(15)
C12 C13 1.3926(15)
C13 C14 1.3926(18)
C14 C15 1.3897(19)
C15 C16 1.3873(16)
C21 C26 1.3898(15)
C21 C22 1.3974(14)
C22 C23 1.3945(16)
C23 C24 1.3866(19)
C24 C25 1.3861(18)
C25 C26 1.3984(16)
