#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178377 $
#$URL: svn://www.crystallography.net/cod/cif/4/00/04/4000449.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_4000449
_journal_name_full               'Chemistry of Materials'
_journal_paper_doi               10.1021/cm0492989
_journal_year                    2004
_chemical_formula_sum            'C19 H16 F3 N O3 S'
_chemical_formula_weight         395.39
_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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 116.656(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7486(16)
_cell_length_b                   11.4058(15)
_cell_length_c                   13.7122(18)
_cell_measurement_temperature    160(2)
_cell_volume                     1781.9(4)
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'XCALIBUR KAPPA CCD'
_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  0.0813
_diffrn_reflns_av_sigmaI/netI    0.1318
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14284
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   refdelf
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.1749
_refine_ls_R_factor_gt           0.0698
_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)+(0.0613P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1723
_reflns_number_gt                1893
_reflns_number_total             4411
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4000449
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 0.3120(3) -0.2996(3) 0.2712(2) 0.0284(7) Uani 1 1 d . . .
C1 C -0.0148(3) 0.0141(4) 0.1139(3) 0.0308(9) Uani 1 1 d . . .
C2 C -0.1241(3) 0.0746(3) 0.0631(3) 0.0281(9) Uani 1 1 d . . .
C3 C -0.1376(3) 0.1982(3) 0.0503(3) 0.0280(9) Uani 1 1 d . . .
C4 C -0.0493(3) 0.2805(3) 0.0828(3) 0.0298(9) Uani 1 1 d . . .
H4 H 0.0266 0.2508 0.1170 0.036 Uiso 1 1 calc R . .
C5 C -0.0577(4) 0.4024(3) 0.0716(3) 0.0358(10) Uani 1 1 d . . .
H5 H 0.0133 0.4425 0.0999 0.043 Uiso 1 1 calc R . .
C6 C -0.1570(3) 0.4712(4) 0.0243(3) 0.0369(10) Uani 1 1 d . . .
H6 H -0.1426 0.5511 0.0240 0.044 Uiso 1 1 calc R . .
C7 C -0.2736(3) 0.4412(3) -0.0224(3) 0.0356(10) Uani 1 1 d . . .
H7 H -0.3269 0.5027 -0.0493 0.043 Uiso 1 1 calc R . .
C8 C -0.3212(3) 0.3294(4) -0.0340(3) 0.0325(10) Uani 1 1 d . . .
H8 H -0.4028 0.3265 -0.0665 0.039 Uiso 1 1 calc R . .
C9 C -0.2660(3) 0.2225(4) -0.0047(3) 0.0307(9) Uani 1 1 d . . .
C10 C -0.3218(3) 0.1128(4) -0.0231(3) 0.0363(10) Uani 1 1 d . . .
H10 H -0.4026 0.1010 -0.0569 0.044 Uiso 1 1 calc R . .
C11 C -0.2382(3) 0.0251(3) 0.0168(3) 0.0333(10) Uani 1 1 d . . .
H11 H -0.2545 -0.0547 0.0137 0.040 Uiso 1 1 calc R . .
C12 C -0.0030(4) -0.1020(3) 0.1326(3) 0.0325(9) Uani 1 1 d . . .
C13 C 0.1070(3) -0.1673(3) 0.1825(3) 0.0280(9) Uani 1 1 d . . .
C14 C 0.2183(3) -0.1156(3) 0.2184(3) 0.0310(9) Uani 1 1 d . . .
H14 H 0.2243 -0.0350 0.2125 0.037 Uiso 1 1 calc R . .
C15 C 0.3169(3) -0.1823(3) 0.2616(3) 0.0320(9) Uani 1 1 d . . .
H15 H 0.3896 -0.1462 0.2853 0.038 Uiso 1 1 calc R . .
C16 C 0.2073(3) -0.3528(3) 0.2386(3) 0.0325(9) Uani 1 1 d . . .
H16 H 0.2040 -0.4337 0.2454 0.039 Uiso 1 1 calc R . .
C17 C 0.1053(3) -0.2885(3) 0.1954(3) 0.0312(9) Uani 1 1 d . . .
H17 H 0.0338 -0.3265 0.1743 0.037 Uiso 1 1 calc R . .
C18 C 0.4197(3) -0.3707(4) 0.3174(3) 0.0400(10) Uani 1 1 d . . .
H18A H 0.4423 -0.3855 0.3932 0.060 Uiso 1 1 calc R . .
H18B H 0.4815 -0.3291 0.3104 0.060 Uiso 1 1 calc R . .
H18C H 0.4055 -0.4438 0.2789 0.060 Uiso 1 1 calc R . .
H1 H 0.058(3) 0.058(3) 0.136(2) 0.023(9) Uiso 1 1 d . . .
H12 H -0.076(3) -0.154(3) 0.109(3) 0.025(9) Uiso 1 1 d . . .
C100 C 0.3215(4) 0.2088(5) 0.3528(4) 0.0514(12) Uani 1 1 d . . .
F1 F 0.2182(2) 0.1780(3) 0.3477(2) 0.0892(11) Uani 1 1 d . . .
F2 F 0.3847(2) 0.1096(2) 0.3730(2) 0.0785(10) Uani 1 1 d . . .
F3 F 0.3766(3) 0.2733(3) 0.4392(2) 0.0939(11) Uani 1 1 d . . .
S1 S 0.30428(8) 0.27901(10) 0.22996(8) 0.0354(3) Uani 1 1 d . . .
O1 O 0.2514(3) 0.1908(3) 0.1508(3) 0.0643(10) Uani 1 1 d . . .
O2 O 0.2287(2) 0.3759(3) 0.2218(3) 0.0588(9) Uani 1 1 d . . .
O3 O 0.4221(2) 0.3122(3) 0.2522(2) 0.0545(9) Uani 1 1 d . . .
