#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/18/2211816.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_2211816
loop_
_publ_author_name
'Ray J. Butcher'
'Narasegowda, R. S.'
'Yathirajan, H. S.'
'Anilkumar, H. G.'
'Mohan, B. M.'
_publ_section_title
;
 N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide:
 a bicalutamide intermediate
;
_journal_coeditor_code           GK2038
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o33
_journal_page_last               o35
_journal_paper_doi               10.1107/S1600536806050574
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H9 F3 N2 O2'
_chemical_formula_moiety         'C12 H9 F3 N2 O2'
_chemical_formula_sum            'C12 H9 F3 N2 O2'
_chemical_formula_weight         270.21
_chemical_melting_point          422
_chemical_name_systematic
;
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.9440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2636(5)
_cell_length_b                   11.5179(6)
_cell_length_c                   10.4182(5)
_cell_measurement_reflns_used    5756
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      2.52
_cell_volume                     1200.29(10)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0121
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10248
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_correction_T_min  0.9144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0379
_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)+(0.0522P)²+0.266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                2043
_reflns_number_total             2352
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211816
_cod_database_fobs_code          2211816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1A -0.0192(5) 1.4133(7) 0.3638(12) 0.112(2) Uani d PD 0.460(17) A 1
F F2A 0.1096(12) 1.3882(7) 0.2348(4) 0.097(2) Uani d PD 0.460(17) A 1
F F3A 0.1819(7) 1.4534(5) 0.4173(6) 0.0958(19) Uani d PD 0.460(17) A 1
F F1B 0.0144(10) 1.4194(6) 0.4202(12) 0.133(2) Uani d PD 0.540(17) A 2
F F2B 0.2084(6) 1.4354(6) 0.3930(8) 0.117(2) Uani d PD 0.540(17) A 2
F F3B 0.0472(14) 1.3869(6) 0.2308(3) 0.131(3) Uani d PD 0.540(17) A 2
O O1 0.08946(12) 0.79487(9) 0.35031(10) 0.0640(3) Uani d . 1 . .
O O2 -0.04035(14) 0.86410(10) 0.01087(10) 0.0732(4) Uani d . 1 . .
N N1 0.05625(12) 0.96802(10) 0.24202(11) 0.0496(3) Uani d . 1 . .
H H1N 0.0284(16) 0.9944(16) 0.1659(17) 0.059 Uiso d . 1 . .
C C1 0.10289(13) 1.04821(11) 0.34244(12) 0.0423(3) Uani d . 1 A .
C C11 0.04782(13) 0.85064(11) 0.25120(13) 0.0443(3) Uani d . 1 . .
C C12 -0.02468(15) 0.79203(12) 0.12562(13) 0.0480(3) Uani d . 1 . .
C C13 0.01051(18) 0.66736(14) 0.11129(18) 0.0657(4) Uani d . 1 . .
H H13A -0.0392 0.6383 0.0284 0.099 Uiso calc R 1 . .
H H13B -0.0112 0.6229 0.1816 0.099 Uiso calc R 1 . .
H H13C 0.1045 0.6609 0.1147 0.099 Uiso calc R 1 . .
C C14 -0.15676(17) 0.83715(15) 0.06210(16) 0.0664(5) Uani d . 1 . .
H H14A -0.2216 0.7831 0.0128 0.080 Uiso calc R 1 . .
H H14B -0.1941 0.8985 0.1066 0.080 Uiso calc R 1 . .
C C2 0.08724(13) 1.16493(12) 0.30784(13) 0.0458(3) Uani d . 1 . .
H H2A 0.0503 1.1851 0.2208 0.055 Uiso calc R 1 . .
C C3 0.12538(13) 1.25097(12) 0.40009(13) 0.0456(3) Uani d . 1 A .
C C31 0.09872(14) 1.37465(14) 0.35674(13) 0.0639(4) Uani d D 1 . .
C C4 0.18292(13) 1.22119(13) 0.53101(12) 0.0463(3) Uani d . 1 . .
C C41 0.22361(15) 1.30732(14) 0.63252(14) 0.0562(4) Uani d . 1 A .
N N41 0.25692(16) 1.37267(15) 0.71500(15) 0.0784(5) Uani d . 1 . .
C C5 0.20025(14) 1.10469(13) 0.56393(13) 0.0501(3) Uani d . 1 A .
H H5A 0.2398 1.0844 0.6503 0.060 Uiso calc R 1 . .
C C6 0.16050(14) 1.01818(12) 0.47226(13) 0.0476(3) Uani d . 1 . .
H H6A 0.1720 0.9406 0.4968 0.057 Uiso calc R 1 A .
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
_geom_angle_publ_flag
C12 O2 C14 61.07(10) y
C11 N1 C1 128.41(12) ?
C11 N1 H1N 114.4(12) ?
C1 N1 H1N 117.2(12) ?
C2 C1 C6 119.38(12) ?
C2 C1 N1 116.38(11) ?
C6 C1 N1 124.23(12) ?
O1 C11 N1 124.90(13) y
O1 C11 C12 120.86(12) y
N1 C11 C12 114.20(11) y
O2 C12 C14 59.89(10) y
O2 C12 C13 117.17(13) ?
C14 C12 C13 121.01(13) ?
O2 C12 C11 113.86(11) ?
C14 C12 C11 117.33(12) ?
C13 C12 C11 115.59(13) ?
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
O2 C14 C12 59.04(10) ?
O2 C14 H14A 117.9 ?
C12 C14 H14A 117.9 ?
O2 C14 H14B 117.9 ?
C12 C14 H14B 117.9 ?
H14A C14 H14B 115.0 ?
C3 C2 C1 121.12(12) ?
C3 C2 H2A 119.4 ?
C1 C2 H2A 119.4 ?
C2 C3 C4 119.71(13) ?
C2 C3 C31 118.01(11) ?
C4 C3 C31 122.24(12) ?
F3A C31 F1A 104.5(5) ?
F1B C31 F2B 105.5(4) ?
F1B C31 F3B 107.5(4) ?
F2B C31 F3B 111.1(5) ?
F3A C31 F2A 101.4(4) ?
F1A C31 F2A 107.1(4) ?
F3A C31 C3 117.3(3) ?
F1A C31 C3 114.5(4) ?
F1B C31 C3 108.6(3) ?
F2B C31 C3 109.5(3) ?
F3B C31 C3 114.2(3) ?
F2A C31 C3 110.9(4) ?
C5 C4 C3 118.69(12) ?
C5 C4 C41 118.97(12) ?
C3 C4 C41 122.33(13) ?
N41 C41 C4 178.03(18) y
C6 C5 C4 121.80(12) ?
C6 C5 H5A 119.1 ?
C4 C5 H5A 119.1 ?
C5 C6 C1 119.28(13) ?
C5 C6 H6A 120.4 ?
C1 C6 H6A 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1A C31 1.3071(16) ?
F2A C31 1.3096(16) ?
F3A C31 1.3071(16) ?
F1B C31 1.3075(16) ?
F2B C31 1.3075(16) ?
F3B C31 1.3078(16) ?
O1 C11 1.2098(16) y
O2 C12 1.4346(17) y
O2 C14 1.447(2) y
N1 C11 1.3595(18) y
N1 C1 1.3972(16) y
N1 H1N 0.838(17) ?
C1 C2 1.3918(19) ?
C1 C6 1.3930(18) ?
C11 C12 1.5116(18) ?
C12 C14 1.464(2) y
C12 C13 1.496(2) ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C2 C3 1.3749(18) ?
C2 H2A 0.9300 ?
C3 C4 1.4021(19) ?
C3 C31 1.501(2) ?
C4 C5 1.387(2) ?
C4 C41 1.4419(19) y
C41 N41 1.136(2) y
C5 C6 1.3773(19) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O2 3_575 0.84(2) 2.48(2) 3.243(2) 151.0(10)
C2 H2A O2 3_575 0.93 2.46 3.264(2) 145
C14 H14A O1 4_575 0.97 2.44 3.375(2) 161
C6 H6A O1 . 0.93 2.30 2.889(2) 121
N1 H1N O2 . 0.84(2) 2.20(2) 2.673(2) 116(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
C11 N1 C1 C2 -173.36(14)
C11 N1 C1 C6 5.5(2)
C1 N1 C11 O1 -5.5(2)
C1 N1 C11 C12 172.25(13)
C14 O2 C12 C13 111.83(16)
C14 O2 C12 C11 -108.90(14)
O1 C11 C12 O2 -166.44(13)
N1 C11 C12 O2 15.75(18)
O1 C11 C12 C14 126.44(16)
N1 C11 C12 C14 -51.37(17)
O1 C11 C12 C13 -26.5(2)
N1 C11 C12 C13 155.69(13)
C13 C12 C14 O2 -105.50(15)
C11 C12 C14 O2 103.10(13)
C6 C1 C2 C3 -1.2(2)
N1 C1 C2 C3 177.70(12)
C1 C2 C3 C4 1.0(2)
C1 C2 C3 C31 -176.84(12)
C2 C3 C31 F3A -149.4(5)
C4 C3 C31 F3A 32.9(6)
C2 C3 C31 F1A 87.7(6)
C4 C3 C31 F1A -90.1(6)
C2 C3 C31 F1B 116.3(7)
C4 C3 C31 F1B -61.4(7)
C2 C3 C31 F2B -128.9(5)
C4 C3 C31 F2B 53.3(5)
C2 C3 C31 F3B -3.6(7)
C4 C3 C31 F3B 178.7(7)
C2 C3 C31 F2A -33.7(6)
C4 C3 C31 F2A 148.6(6)
C2 C3 C4 C5 0.2(2)
C31 C3 C4 C5 177.90(13)
C2 C3 C4 C41 -179.30(13)
C31 C3 C4 C41 -1.6(2)
C3 C4 C5 C6 -1.1(2)
C41 C4 C5 C6 178.40(13)
C4 C5 C6 C1 0.9(2)
C2 C1 C6 C5 0.3(2)
N1 C1 C6 C5 -178.52(13)
