#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:44:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178791 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104525.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_4104525
loop_
_publ_author_name
'Christopher J. Hayes'
'Nigel S. Simpkins'
'Douglas T. Kirk'
'Lee Mitchell'
'Jerome Baudoux'
'Alexander J. Blake'
'Claire Wilson'
_publ_section_title
;
 Bridgehead Lithiation-Substitution of Bridged Ketones, Lactones, Lactams,
 and Imides: Experimental Observations and Computational Insights
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8196
_journal_page_last               8210
_journal_paper_doi               10.1021/ja9009875
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25
_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   'geometrically placed, Me delta-F'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.095(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4886(9)
_cell_length_b                   7.9502(10)
_cell_length_c                   11.2672(14)
_cell_measurement_reflns_used    3783
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.7
_cell_volume                     670.68(14)
_computing_cell_refinement       'Bruker SAINT version 6.02a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_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  0.026
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5994
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        none
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    'riding model, Me rigid rotating group'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0293
_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)+(0.0536P)²+0.0337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                1603
_reflns_number_total             1699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9009875_si_001.cif
_cod_data_source_block           occnme
_cod_database_code               4104525
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
O1 O 0.33433(15) -0.04931(15) 0.19115(9) 0.0223(2) Uani 1 1 d .
N1 N -0.0713(2) 0.1029(3) 0.27402(15) 0.0400(4) Uani 1 1 d .
C1 C 0.1720(2) -0.2684(2) 0.29419(13) 0.0218(3) Uani 1 1 d .
O2 O 0.38747(19) 0.21845(16) 0.25168(12) 0.0355(3) Uani 1 1 d .
C2 C 0.3287(2) -0.3828(2) 0.26942(15) 0.0246(3) Uani 1 1 d .
H2A H 0.3034 -0.4820 0.2252 0.030 Uiso 1 1 calc R
O3 O 0.52263(16) 0.09994(18) 0.09522(10) 0.0290(3) Uani 1 1 d .
C3 C 0.5002(2) -0.3585(2) 0.30347(15) 0.0277(4) Uani 1 1 d .
H3A H 0.5802 -0.4449 0.2807 0.033 Uiso 1 1 calc R
O4 O -0.08528(18) -0.4306(2) 0.23407(13) 0.0430(4) Uani 1 1 d .
C4 C 0.5816(2) -0.2210(3) 0.36959(15) 0.0292(4) Uani 1 1 d .
H4A H 0.7079 -0.2267 0.3786 0.035 Uiso 1 1 calc R
O5 O 0.01781(17) -0.2348(2) 0.10976(11) 0.0376(3) Uani 1 1 d .
C5 C 0.5049(2) -0.0871(2) 0.41976(15) 0.0279(4) Uani 1 1 d .
H5A H 0.5812 -0.0115 0.4619 0.034 Uiso 1 1 calc R
C6 C 0.3084(2) -0.0456(2) 0.41546(13) 0.0245(3) Uani 1 1 d .
H6A H 0.2868 0.0726 0.4420 0.029 Uiso 1 1 calc R
C7 C 0.2061(2) -0.1696(2) 0.49007(15) 0.0280(4) Uani 1 1 d .
H7A H 0.1973 -0.1624 0.5739 0.034 Uiso 1 1 calc R
C8 C 0.1299(2) -0.2897(2) 0.42469(14) 0.0274(4) Uani 1 1 d .
H8 H 0.0584 -0.3776 0.4555 0.033 Uiso 1 1 calc R
C9 C 0.2220(2) -0.0783(2) 0.29044(13) 0.0208(3) Uani 1 1 d .
C10 C 0.0574(2) 0.0256(2) 0.27948(14) 0.0263(4) Uani 1 1 d .
C11 C 0.0177(2) -0.3212(2) 0.21188(15) 0.0268(4) Uani 1 1 d .
C12 C -0.1269(3) -0.2741(4) 0.0268(2) 0.0551(6) Uani 1 1 d .
H12A H -0.1232 -0.3940 0.0067 0.083 Uiso 1 1 calc R
H12B H -0.1139 -0.2070 -0.0455 0.083 Uiso 1 1 calc R
H12C H -0.2414 -0.2477 0.0631 0.083 Uiso 1 1 calc R
C13 C 0.4144(2) 0.1036(2) 0.18651(14) 0.0235(3) Uani 1 1 d .
C14 C 0.6187(3) 0.2562(3) 0.07608(17) 0.0359(4) Uani 1 1 d .
H14A H 0.5332 0.3488 0.0669 0.054 Uiso 1 1 calc R
H14B H 0.6895 0.2466 0.0041 0.054 Uiso 1 1 calc R
H14C H 0.6983 0.2785 0.1444 0.054 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
C13 O1 C9 116.19(12)
C2 C1 C8 106.68(13)
C2 C1 C11 107.64(13)
C8 C1 C11 112.85(13)
C2 C1 C9 112.97(13)
C8 C1 C9 100.89(13)
C11 C1 C9 115.46(13)
C3 C2 C1 126.81(16)
C13 O3 C14 114.17(14)
C2 C3 C4 130.03(16)
C5 C4 C3 129.48(15)
C11 O5 C12 115.47(17)
C4 C5 C6 125.92(15)
C5 C6 C7 110.09(14)
C5 C6 C9 112.34(13)
C7 C6 C9 100.77(13)
C8 C7 C6 112.15(14)
C7 C8 C1 111.21(15)
O1 C9 C10 110.15(13)
O1 C9 C1 108.81(12)
C10 C9 C1 110.01(13)
O1 C9 C6 116.01(13)
C10 C9 C6 108.13(13)
C1 C9 C6 103.47(12)
N1 C10 C9 177.87(19)
O4 C11 O5 124.43(16)
O4 C11 C1 123.95(17)
O5 C11 C1 111.55(14)
O2 C13 O3 127.57(17)
O2 C13 O1 125.63(15)
O3 C13 O1 106.77(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.357(2)
O1 C9 1.4313(18)
N1 C10 1.143(2)
C1 C2 1.515(2)
C1 C8 1.519(2)
C1 C11 1.527(2)
C1 C9 1.558(2)
O2 C13 1.192(2)
C2 C3 1.347(2)
O3 C13 1.322(2)
O3 C14 1.454(2)
C3 C4 1.451(3)
O4 C11 1.192(2)
C4 C5 1.340(3)
O5 C11 1.340(2)
O5 C12 1.452(2)
C5 C6 1.508(2)
C6 C7 1.514(2)
C6 C9 1.561(2)
C7 C8 1.328(3)
C9 C10 1.487(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
C8 C1 C2 C3 -73.5(2)
C11 C1 C2 C3 165.08(17)
C9 C1 C2 C3 36.4(2)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 4.3(3)
C3 C4 C5 C6 -1.9(3)
C4 C5 C6 C7 70.1(2)
C4 C5 C6 C9 -41.3(2)
C5 C6 C7 C8 -99.21(17)
C9 C6 C7 C8 19.58(18)
C6 C7 C8 C1 1.2(2)
C2 C1 C8 C7 96.70(17)
C11 C1 C8 C7 -145.29(15)
C9 C1 C8 C7 -21.51(18)
C13 O1 C9 C10 70.12(16)
C13 O1 C9 C1 -169.21(12)
C13 O1 C9 C6 -53.10(18)
C2 C1 C9 O1 42.53(16)
C8 C1 C9 O1 156.05(12)
C11 C1 C9 O1 -81.97(15)
C2 C1 C9 C10 163.28(13)
C8 C1 C9 C10 -83.20(15)
C11 C1 C9 C10 38.78(18)
C2 C1 C9 C6 -81.40(15)
C8 C1 C9 C6 32.13(15)
C11 C1 C9 C6 154.11(13)
C5 C6 C9 O1 -33.4(2)
C7 C6 C9 O1 -150.51(13)
C5 C6 C9 C10 -157.64(15)
C7 C6 C9 C10 85.22(16)
C5 C6 C9 C1 85.71(16)
C7 C6 C9 C1 -31.44(15)
O1 C9 C10 N1 172(5)
C1 C9 C10 N1 52(5)
C6 C9 C10 N1 -60(5)
C12 O5 C11 O4 4.2(3)
C12 O5 C11 C1 -178.69(18)
C2 C1 C11 O4 85.5(2)
C8 C1 C11 O4 -32.0(2)
C9 C1 C11 O4 -147.28(17)
C2 C1 C11 O5 -91.61(17)
C8 C1 C11 O5 150.94(15)
C9 C1 C11 O5 35.62(19)
C14 O3 C13 O2 0.7(2)
C14 O3 C13 O1 179.28(13)
C9 O1 C13 O2 -6.6(2)
C9 O1 C13 O3 174.79(12)
