#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:17:07 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178378 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/00/4020092.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_4020092
loop_
_publ_author_name
'Gary A. Molander'
'Elizabeth Pollina Cormier'
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2622
_journal_page_last               2626
_journal_paper_doi               10.1021/jo047887s
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C9 H14 F3 N O3'
_chemical_formula_weight         241.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90.00
_cell_angle_beta                 91.146(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.545(2)
_cell_length_b                   17.790(6)
_cell_length_c                   8.415(3)
_cell_measurement_temperature    143(1)
_cell_volume                     1129.3(6)
_diffrn_ambient_temperature      143(1)
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6469
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7758
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_ls_extinction_coef       0.002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0558
_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)+(0.0807P)²+0.6815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                1692
_reflns_number_total             2051
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020092
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4895(2) 0.14394(9) 0.6734(2) 0.0311(5) Uani 1 1 d . . .
H1A H 0.5374 0.1846 0.7213 0.041 Uiso 1 1 calc R . .
H1B H 0.5372 0.1392 0.5767 0.041 Uiso 1 1 calc R . .
C2 C 0.2930(3) 0.15287(11) 0.6576(3) 0.0318(5) Uani 1 1 d . . .
H2A H 0.2591 0.1711 0.5527 0.042 Uiso 1 1 calc R . .
H2B H 0.2489 0.1874 0.7368 0.042 Uiso 1 1 calc R . .
C3 C 0.2232(3) 0.07392(11) 0.6843(2) 0.0277(5) Uani 1 1 d . . .
C4 C 0.3463(3) 0.04560(11) 0.8220(2) 0.0285(5) Uani 1 1 d . . .
H4 H 0.3478 -0.0095 0.8211 0.038 Uiso 1 1 calc R . .
C5 C 0.5269(3) 0.07456(12) 0.7712(3) 0.0309(5) Uani 1 1 d . . .
H5A H 0.6006 0.0868 0.8634 0.041 Uiso 1 1 calc R . .
H5B H 0.5873 0.0370 0.7086 0.041 Uiso 1 1 calc R . .
C6 C 0.0273(3) 0.07026(14) 0.7147(3) 0.0406(6) Uani 1 1 d . . .
H6A H -0.0070 0.0189 0.7308 0.061 Uiso 1 1 calc R . .
H6B H -0.0371 0.0904 0.6248 0.061 Uiso 1 1 calc R . .
H6C H 0.0011 0.0991 0.8077 0.061 Uiso 1 1 calc R . .
C7 C 0.2891(3) 0.07218(14) 0.9824(3) 0.0371(6) Uani 1 1 d . . .
H7 H 0.1917 0.0478 1.0247 0.049 Uiso 1 1 calc R . .
C8 C 0.3598(4) 0.12560(16) 1.0699(3) 0.0502(7) Uani 1 1 d . . .
H8A H 0.4574 0.1520 1.0338 0.067 Uiso 1 1 calc R . .
H8B H 0.3123 0.1371 1.1681 0.067 Uiso 1 1 calc R . .
O1 O 0.2661(2) 0.03423(8) 0.54266(18) 0.0368(4) Uani 1 1 d . . .
H1 H 0.2364 -0.0099 0.5512 0.055 Uiso 1 1 calc R . .
C9 C 0.8584(3) 0.30995(13) 0.7286(3) 0.0368(6) Uani 1 1 d . . .
C10 C 0.6999(3) 0.31895(11) 0.8383(2) 0.0281(5) Uani 1 1 d . . .
O2 O 0.5955(2) 0.26580(9) 0.84785(19) 0.0410(5) Uani 1 1 d . . .
O3 O 0.6945(2) 0.38008(8) 0.90866(18) 0.0365(4) Uani 1 1 d . . .
F1 F 0.8603(2) 0.24436(10) 0.6531(2) 0.0718(6) Uani 1 1 d . . .
F2 F 0.8599(3) 0.36197(11) 0.6165(2) 0.0758(6) Uani 1 1 d . . .
F3 F 1.0107(2) 0.31389(13) 0.8079(2) 0.0811(7) Uani 1 1 d . . .
