#------------------------------------------------------------------------------
#$Date: 2017-01-15 01:53:32 +0200 (Sun, 15 Jan 2017) $
#$Revision: 190528 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/49/2004967.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2004967
loop_
_publ_author_name
'Pèpe, G.'
'Pfefer, G.'
'Astier, J. P.'
'Marchal, P.'
'Bossy, A.'
_publ_section_title
;
 Flurtamone
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1514
_journal_page_last               1516
_journal_paper_doi               10.1107/S0108270196000868
_journal_volume                  52
_journal_year                    1996
_chemical_formula_analytical     'C18 H14 F3 N O2'
_chemical_formula_structural     'C18 H14 F3 N O2'
_chemical_formula_sum            'C18 H14 F3 N O2'
_chemical_formula_weight         333.3
_chemical_melting_point          423.15
_chemical_name_common            Flurtamone
_chemical_name_systematic
;
Flurtamone, 5-methylamino-2-phenyl-4 (a,a,a,-trifluoro-m-tolyl)
furan-3(2H)-one.
;
_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'
_cell_angle_alpha                90.
_cell_angle_beta                 110.64(3)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   10.359(2)
_cell_length_b                   12.218(2)
_cell_length_c                   13.530(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      45
_cell_measurement_theta_min      15
_cell_volume                     1602.5(6)
_computing_cell_refinement       'CAD-4 Operations Manual'
_computing_data_collection
'CAD-4 Operations Manual (Enraf-Nonius, 1977)'
_computing_data_reduction        'DATARED (Pèpe, 1979)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'AME (Software Systems, 1988)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'MULTAN80 (Main et al., 1980)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3254
_diffrn_reflns_reduction_process 'SDP system'
_diffrn_reflns_theta_max         45
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.87
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_meas      1.37(2)
_exptl_crystal_density_method    'flotation in CH~2~Cl~2~/CHCl~3~'
_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.78
_refine_ls_goodness_of_fit_obs   0.78
_refine_ls_hydrogen_treatment    'H atoms riding with fixed U~iso~'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.78
_refine_ls_restrained_S_obs      0.78
_refine_ls_R_factor_all          .0560
_refine_ls_R_factor_obs          .0560
_refine_ls_shift/esd_max         0.16
_refine_ls_shift/esd_mean        0.16
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .0560
_refine_ls_wR_factor_obs         .0560
_reflns_number_observed          2214
_reflns_number_total             3254
_reflns_observed_criterion       refl_obs_if_I_>_3.0_sigma(I)
_cod_data_source_file            cf1058.cif
_cod_data_source_block           structure
_cod_depositor_comments
;
 Changing the value of the _atom_site_type_symbol data
 item for hydrogen atoms from '?' to 'H'.

 Antanas Vaitkus,
 2017-01-15

The following automatic conversions were performed:

'_chemical_melting_point' value '150.0 C' was changed to '423.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1602.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2004967
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
C1 .1264(4) .3428(3) .7366(3) 0.05(1) Uani d C
C2 .0540(4) .4307(3) .7557(3) 0.06(2) Uani d C
C3 .0446(6) .5264(4) .7023(5) 0.11(4) Uani d C
C4 .1154(8) .5366(4) .6361(6) 0.13(5) Uani d C
C5 .1837(5) .4507(4) .6118(4) 0.09(3) Uani d C
C6 .1948(3) .3512(3) .6651(2) 0.05(1) Uani d C
C7 -.0167(5) .4218(5) .8320(4) 0.08(3) Uani d C
F8 -.0489(5) .3208(3) .8482(3) 0.17(3) Uani d F
F9 .0625(4) .4460(4) .9283(3) 0.17(3) Uani d F
F10 -.1263(4) .4743(4) .8120(3) 0.19(3) Uani d F
C11 .2717(3) .2599(3) .6410(2) 0.04(1) Uani d C
C12 .3389(3) .1752(3) .7053(2) 0.05(1) Uani d C
O13 .4051(2) .1063(2) .6604(2) 0.05(1) Uani d O
C14 .3786(4) .1441(3) .5533(2) 0.05(2) Uani d C
C15 .2942(3) .2462(3) .5436(3) 0.07(2) Uani d C
O16 .2526(3) .3016(2) .4606(2) 0.06(1) Uani d O
N17 .3534(3) .1492(2) .8023(2) 0.05(1) Uani d N
C18 .4375(6) .0599(4) .8616(3) 0.08(3) Uani d C
C19 .5110(4) .1645(3) .5355(3) 0.06(2) Uani d C
C20 .6155(5) .2172(5) .6075(4) 0.10(3) Uani d C
C21 .7350(5) .2416(6) .5838(5) 0.12(5) Uani d C
C22 .7488(7) .2083(5) .4953(6) 0.11(4) Uani d C
C23 .6426(6) .1564(4) .4222(4) 0.08(3) Uani d C
C24 .5257(5) .1334(3) .4416(3) 0.07(2) Uani d C
H1 0.129(3) 0.277(1) 0.767(2) ? ? ? H
H3 0.001(3) 0.586(2) 0.716(2) ? ? ? H
H4 0.116(3) 0.599(2) 0.600(2) ? ? ? H
H5 0.225(3) 0.455(3) 0.563(2) ? ? ? H
H14 0.331(3) 0.093(2) 0.507(2) ? ? ? H
H17 0.315(3) 0.196(2) 0.836(2) ? ? ? H
H181 0.442(3) -0.003(2) 0.829(2) ? ? ? H
H182 0.520(2) 0.072(3) 0.854(3) ? ? ? H
H183 0.436(3) 0.043(3) 0.926(1) ? ? ? H
H20 0.601(3) 0.242(3) 0.665(2) ? ? ? H
H21 0.811(2) 0.267(3) 0.635(2) ? ? ? H
H22 0.825(2) 0.215(3) 0.478(2) ? ? ? H
H23 0.659(3) 0.142(3) 0.362(1) ? ? ? H
H24 0.466(3) 0.093(2) 0.390(2) ? ? ? H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F .069 .053 International_Tables_Vol_IV_Table_2.3.1
O .047 .003 International_Tables_Vol_IV_Table_2.3.1
N .029 .002 International_Tables_Vol_IV_Table_2.3.1
C .000 .001 International_Tables_Vol_IV_Table_2.3.1
H .000 .000 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 3 -7
5 -2 -6
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 C2 C3 120.7(4) no
C1 C2 C7 120.8(3) no
C3 C2 C7 118.6(4) no
C2 C3 C4 118.6(5) no
C3 C4 C5 122.4(5) no
C4 C5 C6 119.9(4) no
C1 C6 C5 117.0(3) no
C1 C6 C11 123.1(3) no
C5 C6 C11 119.8(3) no
C2 C7 F8 113.9(4) no
C2 C7 F9 113.1(4) no
C2 C7 F10 116.8(4) no
F8 C7 F9 98.8(4) no
F8 C7 F10 104.7(4) no
F9 C7 F10 107.7(4) no
C6 C11 C12 128.6(3) no
C12 C11 C15 106.6(2) yes
C6 C11 C15 124.8(3) no
C11 C12 O13 114.0(2) yes
C11 C12 N17 132.3(3) yes
O13 C12 N17 113.7(2) yes
C12 O13 C14 107.6(2) yes
O13 C14 C15 104.5(2) yes
C15 C14 C19 112.7(3) no
O13 C14 C19 110.6(3) no
C11 C15 C14 107.2(3) yes
C11 C15 O16 130.5(3) yes
C14 C15 O16 122.3(3) yes
C12 N17 C18 125.0(3) yes
C14 C19 C20 121.0(3) no
C14 C19 C24 120.4(3) no
C20 C19 C24 118.5(4) no
C19 C20 C21 118.9(4) no
C20 C21 C22 121.6(5) no
C21 C22 C23 119.3(5) no
C22 C23 C24 120.5(5) no
C19 C24 C23 121.0(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.385(5) no
C1 C6 1.389(4) no
C11 C6 1.472(4) no
C2 C3 1.360(6) no
C2 C7 1.465(6) no
C3 C4 1.348(8) no
C4 C5 1.369(7) no
C5 C6 1.397(5) no
C7 F8 1.317(6) no
C7 F9 1.306(6) no
C7 F10 1.248(6) no
C11 C12 1.373(4) yes
C11 C15 1.427(4) yes
C12 O13 1.357(3) yes
C12 N17 1.307(4) yes
C14 O13 1.452(4) yes
C14 C15 1.502(4) yes
C14 C19 1.494(5) no
C15 O16 1.251(4) no
C18 N17 1.449(5) yes
C19 C20 1.339(6) no
C19 C24 1.385(5) no
C20 C21 1.415(7) no
C21 C22 1.319(8) no
C22 C23 1.351(8) no
C23 C24 1.355(6) no
