#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:20:53 +0100 (mar 22 de mar de 2016) $
#$Revision: 178895 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/24/4112453.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_4112453
loop_
_publ_author_name
'Jiangli Yan'
'Frank Delaglio'
'Andreas Kaerner'
'Allen D. Kline'
'Huaping Mo'
'Michael J. Shapiro'
'Tim A. Smitka'
'Gregory A. Stephenson'
'Edward R. Zartler'
_publ_section_title
;
 Complete Relative Stereochemistry of Multiple Stereocenters Using Only
 Residual Dipolar Couplings
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5008
_journal_page_last               5017
_journal_paper_doi               10.1021/ja037605q
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C8 H10 F N O4'
_chemical_formula_weight         203.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 96.042(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.065(11)
_cell_length_b                   5.741(3)
_cell_length_c                   7.394(4)
_cell_measurement_temperature    150(2)
_cell_volume                     847.0(8)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.1339
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2920
_diffrn_reflns_theta_full        28.14
_diffrn_reflns_theta_max         28.14
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       Bladed
_exptl_crystal_F_000             424
_exptl_crystal_size_max          .11
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .42
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.260
_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   -0.8(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.817
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0198P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                1036
_reflns_number_total             1691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037605qsi20030731_044008.cif
_cod_data_source_block           2061xm
_cod_database_code               4112453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
O7B O 0.96186(11) 0.7410(4) 0.2713(3) 0.0220(6) Uani 1 1 d .
F4 F 1.19487(9) 0.6691(3) 0.5661(2) 0.0302(5) Uani 1 1 d .
O9B O 1.12392(11) 0.2643(3) -0.1447(3) 0.0224(6) Uani 1 1 d .
O9A O 1.19361(10) 0.1474(3) 0.0975(3) 0.0186(5) Uani 1 1 d .
N8 N 1.16523(12) 0.7142(4) -0.0665(3) 0.0143(6) Uani 1 1 d .
H8A H 1.1644 0.8628 -0.0239 0.021 Uiso 1 1 calc R
H8B H 1.1313 0.6942 -0.1570 0.021 Uiso 1 1 calc R
H8C H 1.2052 0.6871 -0.1106 0.021 Uiso 1 1 calc R
O7A O 1.00116(11) 1.1047(4) 0.2392(3) 0.0298(6) Uani 1 1 d .
H7AA H 0.9606 1.1360 0.2100 0.045 Uiso 1 1 calc R
C2 C 1.15660(16) 0.5466(5) 0.0857(4) 0.0136(8) Uani 1 1 d .
C5 C 1.09725(15) 0.5684(5) 0.3605(4) 0.0164(8) Uani 1 1 d .
H5A H 1.0632 0.4850 0.4262 0.020 Uiso 1 1 calc R
C9 C 1.15838(17) 0.2975(5) 0.0039(5) 0.0199(8) Uani 1 1 d .
C1 C 1.08888(15) 0.5790(5) 0.1563(4) 0.0153(7) Uani 1 1 d .
H1A H 1.0486 0.5042 0.0889 0.018 Uiso 1 1 calc R
C7 C 1.00846(19) 0.8740(5) 0.2616(5) 0.0193(9) Uani 1 1 d .
C4 C 1.17096(16) 0.5298(6) 0.4160(4) 0.0190(8) Uani 1 1 d .
H4A H 1.1793 0.3618 0.4461 0.023 Uiso 1 1 calc R
C6 C 1.07936(16) 0.8009(5) 0.2671(4) 0.0155(8) Uani 1 1 d .
H6A H 1.1146 0.9244 0.2709 0.019 Uiso 1 1 calc R
C3 C 1.20725(14) 0.5968(5) 0.2523(4) 0.0143(7) Uani 1 1 d .
H3A H 1.2483 0.5022 0.2482 0.017 Uiso 1 1 calc R
H3B H 1.2198 0.7636 0.2573 0.017 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O7B 0.0132(14) 0.0265(14) 0.0263(15) 0.0030(10) 0.0020(11) -0.0005(11)
F4 0.0248(12) 0.0462(14) 0.0184(12) -0.0077(9) -0.0031(9) -0.0054(11)
O9B 0.0241(15) 0.0195(12) 0.0217(14) -0.0054(11) -0.0061(12) -0.0041(12)
O9A 0.0200(14) 0.0135(12) 0.0221(13) 0.0032(10) 0.0015(10) 0.0029(11)
N8 0.0124(15) 0.0150(15) 0.0152(15) -0.0004(11) 0.0006(12) 0.0013(11)
O7A 0.0181(14) 0.0178(12) 0.0528(16) 0.0024(10) 0.0006(11) 0.0037(11)
C2 0.018(2) 0.0122(17) 0.0107(17) 0.0000(13) 0.0016(15) -0.0001(14)
C5 0.0163(19) 0.0174(18) 0.0160(18) 0.0009(14) 0.0044(15) -0.0014(16)
C9 0.020(2) 0.0180(19) 0.023(2) 0.0033(16) 0.0101(18) -0.0035(16)
C1 0.0154(19) 0.0148(16) 0.0156(19) -0.0021(14) 0.0017(14) -0.0032(15)
C7 0.020(2) 0.024(2) 0.015(2) -0.0020(14) 0.0061(18) 0.0002(17)
C4 0.022(2) 0.0177(19) 0.0160(19) -0.0033(14) -0.0038(16) -0.0013(16)
C6 0.011(2) 0.0151(18) 0.021(2) -0.0044(14) 0.0068(16) -0.0019(15)
C3 0.0118(18) 0.0128(16) 0.0179(17) -0.0006(14) -0.0007(14) 0.0004(14)
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'
F F 0.0171 0.0103 '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
N8 C2 C1 110.9(2)
N8 C2 C3 111.1(2)
C1 C2 C3 104.0(2)
N8 C2 C9 106.8(2)
C1 C2 C9 107.7(2)
C3 C2 C9 116.3(3)
C1 C5 C4 106.4(3)
C1 C5 C6 60.96(19)
C4 C5 C6 115.3(3)
O9B C9 O9A 126.8(3)
O9B C9 C2 116.7(3)
O9A C9 C2 116.5(3)
C5 C1 C2 109.3(2)
C5 C1 C6 60.33(18)
C2 C1 C6 116.8(2)
O7B C7 O7A 123.6(3)
O7B C7 C6 124.3(3)
O7A C7 C6 112.1(3)
F4 C4 C5 111.9(2)
F4 C4 C3 109.3(3)
C5 C4 C3 106.5(3)
C7 C6 C5 116.1(3)
C7 C6 C1 113.2(3)
C5 C6 C1 58.71(18)
C4 C3 C2 104.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7B C7 1.215(4)
F4 C4 1.410(3)
O9B C9 1.250(4)
O9A C9 1.272(3)
N8 C2 1.505(4)
O7A C7 1.341(4)
C2 C1 1.517(4)
C2 C3 1.539(4)
C2 C9 1.555(4)
C5 C1 1.503(4)
C5 C4 1.509(4)
C5 C6 1.529(4)
C1 C6 1.538(4)
C7 C6 1.480(4)
C4 C3 1.526(4)
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
N8 C2 C9 O9B -46.1(4)
C1 C2 C9 O9B 73.0(3)
C3 C2 C9 O9B -170.8(3)
N8 C2 C9 O9A 135.4(3)
C1 C2 C9 O9A -105.4(3)
C3 C2 C9 O9A 10.8(4)
C4 C5 C1 C2 0.2(3)
C6 C5 C1 C2 110.5(3)
C4 C5 C1 C6 -110.3(3)
N8 C2 C1 C5 -137.5(2)
C3 C2 C1 C5 -18.0(3)
C9 C2 C1 C5 106.0(3)
N8 C2 C1 C6 -71.7(3)
C3 C2 C1 C6 47.8(3)
C9 C2 C1 C6 171.8(3)
C1 C5 C4 F4 137.4(3)
C6 C5 C4 F4 72.3(3)
C1 C5 C4 C3 18.1(3)
C6 C5 C4 C3 -47.1(3)
O7B C7 C6 C5 -24.0(5)
O7A C7 C6 C5 157.8(3)
O7B C7 C6 C1 41.2(4)
O7A C7 C6 C1 -137.0(3)
C1 C5 C6 C7 102.4(3)
C4 C5 C6 C7 -162.2(3)
C4 C5 C6 C1 95.4(3)
C5 C1 C6 C7 -107.5(3)
C2 C1 C6 C7 154.6(3)
C2 C1 C6 C5 -98.0(3)
F4 C4 C3 C2 -150.3(2)
C5 C4 C3 C2 -29.2(3)
N8 C2 C3 C4 147.9(2)
C1 C2 C3 C4 28.6(3)
C9 C2 C3 C4 -89.7(3)
