#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238627.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_2238627
loop_
_publ_author_name
'Suchetan, P. A.'
'Sreenivasa, S.'
'Palakshamurthy, B. S.'
'ManojKumar, K. E.'
'Madan Kumar, S.'
'Lokanath, N. K.'
_publ_section_title
;
 Methyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1566
_journal_paper_doi               10.1107/S160053681302549X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H6 F3 N O2'
_chemical_formula_moiety         'C7 H6 F3 N O2'
_chemical_formula_sum            'C7 H6 F3 N O2'
_chemical_formula_weight         193.13
_chemical_melting_point          405
_chemical_name_systematic
;
Methyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 98.903(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.643(2)
_cell_length_b                   7.1118(10)
_cell_length_c                   6.9618(11)
_cell_measurement_reflns_used    645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      3.0
_cell_volume                     814.1(2)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 1.08
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0762
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            3752
_diffrn_reflns_theta_full        24.43
_diffrn_reflns_theta_max         24.43
_diffrn_reflns_theta_min         2.96
_diffrn_standards_decay_%        1.5
_diffrn_standards_interval_count 15
_diffrn_standards_interval_time  15
_diffrn_standards_number         743
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9689
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.316
_refine_ls_extinction_coef       0.08(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     81
_refine_ls_number_reflns         707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0649
_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)+(0.1299P)²+0.3175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1797
_reflns_number_gt                645
_reflns_number_total             707
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7136.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2238627
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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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_symmetry_multiplicity
H H 0.275(3) 0.0000 -0.341(8) 0.073(13) Uiso d S 1 2
C C1 0.0515(2) 0.0000 0.2701(6) 0.0765(12) Uani d S 1 2
H H1A 0.0456 0.1254 0.3171 0.115 Uiso calc PR 0.50 1
H H1B 0.0701 -0.0816 0.3777 0.115 Uiso calc PR 0.50 1
H H1C 0.0000 -0.0438 0.2042 0.115 Uiso calc PR 0.50 1
C C2 0.18890(17) 0.0000 0.2149(4) 0.0436(9) Uani d S 1 2
C C3 0.24211(16) 0.0000 0.0673(4) 0.0391(8) Uani d S 1 2
C C4 0.21641(19) 0.0000 -0.1280(4) 0.0480(8) Uani d S 1 2
H H4 0.1625 0.0000 -0.1881 0.058 Uiso calc SR 1 2
C C5 0.3504(2) 0.0000 -0.0863(5) 0.0563(10) Uani d S 1 2
H H5 0.4034 0.0000 -0.1137 0.068 Uiso calc SR 1 2
C C6 0.32889(16) 0.0000 0.0952(4) 0.0443(8) Uani d S 1 2
C C7 0.38690(18) 0.0000 0.2762(5) 0.0544(9) Uani d S 1 2
F F1 0.46353(14) 0.0000 0.2439(4) 0.1048(12) Uani d S 1 2
F F2 0.38017(10) 0.1475(2) 0.3904(2) 0.0853(8) Uani d . 1 1
N N 0.28189(18) 0.0000 -0.2200(5) 0.0587(9) Uani d S 1 2
O O1 0.20994(15) 0.0000 0.3872(3) 0.0718(9) Uani d S 1 2
O O2 0.11034(12) 0.0000 0.1358(3) 0.0586(8) Uani d S 1 2
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 C1 H1A . . 109.5
O2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
O2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
O1 C2 O2 . . 121.9(3)
O1 C2 C3 . . 126.3(3)
O2 C2 C3 . . 111.8(3)
C4 C3 C6 . . 106.9(3)
C4 C3 C2 . . 125.0(3)
C6 C3 C2 . . 128.1(3)
N C4 C3 . . 108.8(3)
N C4 H4 . . 125.6
C3 C4 H4 . . 125.6
N C5 C6 . . 108.8(3)
N C5 H5 . . 125.6
C6 C5 H5 . . 125.6
C5 C6 C3 . . 106.2(3)
C5 C6 C7 . . 124.3(3)
C3 C6 C7 . . 129.5(3)
F1 C7 F2 . 6 105.81(19)
F1 C7 F2 . . 105.81(19)
F2 C7 F2 6 . 104.0(3)
F1 C7 C6 . . 112.2(3)
F2 C7 C6 6 . 114.12(17)
F2 C7 C6 . . 114.12(17)
C4 N C5 . . 109.3(3)
C4 N H . . 119(3)
C5 N H . . 131(3)
C2 O2 C1 . . 116.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 O2 . 1.455(4)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 O1 . 1.196(4)
C2 O2 . 1.338(4)
C2 C3 . 1.457(4)
C3 C4 . 1.360(4)
C3 C6 . 1.427(4)
C4 N . 1.347(4)
C4 H4 . 0.9300
C5 N . 1.356(5)
C5 C6 . 1.366(5)
C5 H5 . 0.9300
C6 C7 . 1.464(5)
C7 F1 . 1.329(4)
C7 F2 6 1.332(3)
C7 F2 . 1.332(3)
N H . 0.84(5)
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
N H O1 1_554 0.83(6) 2.03(5) 2.810(4) 156
C5 H5 F1 2_655 0.93 2.52 3.442(4) 171
loop_
_iucr_refine_instructions_details
;
TITL sree_m2_0m in C 1 2/m 1
CELL  0.71073  16.6434   7.1118   6.9618   90.000   98.903   90.000
ZERR     4.00   0.0023   0.0010   0.0011    0.000    0.007    0.000
LATT   7
SYMM  - X,   Y, - Z
SFAC  C    H    F    N    O
UNIT  28   24   12   4    8
MERG   2
OMIT     0.00  50.00
OMIT 2 0 2
FMAP   2
PLAN   20
SIZE     0.20   0.22   0.24
ACTA    50.00
BOND   $H
LIST   4
L.S.  10
WGHT      0.1299      0.3175
EXTI    0.076957
FVAR       0.36269
H     2    1.275197    0.000000   -0.341420    10.50000    0.07252
MOLE    1
C1    1    1.051525    0.000000    0.270110    10.50000    0.05736    0.11611 =
         0.05816    0.00000    0.01540    0.00000
AFIX 137
H1A   2    1.045645    0.125378    0.317108    10.50000   -1.50000
H1B   2    1.070137   -0.081609    0.377657    10.50000   -1.50000
H1C   2    0.999977   -0.043768    0.204209    10.50000   -1.50000
AFIX   0
C2    1    1.188896    0.000000    0.214915    10.50000    0.05032    0.05169 =
         0.02573    0.00000   -0.00381    0.00000
C3    1    1.242110    0.000000    0.067294    10.50000    0.04783    0.04219 =
         0.02354    0.00000   -0.00659    0.00000
C4    1    1.216407    0.000000   -0.127955    10.50000    0.05736    0.05891 =
         0.02370    0.00000   -0.00654    0.00000
AFIX  43
H4    2    1.162461    0.000000   -0.188051    10.50000   -1.20000
AFIX   0
C5    1    1.350429    0.000000   -0.086332    10.50000    0.05698    0.07078 =
         0.04168    0.00000    0.00925    0.00000
AFIX  43
H5    2    1.403373    0.000000   -0.113735    10.50000   -1.20000
AFIX   0
C6    1    1.328889    0.000000    0.095211    10.50000    0.04914    0.04835 =
         0.03305    0.00000   -0.00067    0.00000
C7    1    1.386898    0.000000    0.276154    10.50000    0.04811    0.06670 =
         0.04452    0.00000   -0.00517    0.00000
F1    3    1.463529    0.000000    0.243899    10.50000    0.04863    0.18485 =
         0.07606    0.00000   -0.00564    0.00000
F2    3    1.380171    0.147548    0.390385    11.00000    0.09588    0.09031 =
         0.05704   -0.02396   -0.02777   -0.00193
N     4    1.281892    0.000000   -0.219983    10.50000    0.07653    0.07807 =
         0.02026    0.00000    0.00345    0.00000
O1    5    1.209942    0.000000    0.387191    10.50000    0.06452    0.12530 =
         0.02300    0.00000   -0.00129    0.00000
O2    5    1.110338    0.000000    0.135801    10.50000    0.04701    0.09139 =
         0.03518    0.00000   -0.00065    0.00000
HKLF 4
REM Highest difference peak  0.372,  deepest hole -0.316,  1-sigma level  0.076
REM  sree_m2_0m in C 1 2/m 1
REM R1 =  0.0649 for    645 Fo > 4sig(Fo)  and  0.0854 for all    707 data
REM     81 parameters refined using      0 restraints
END
;
