#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/30/2233092.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_2233092
loop_
_publ_author_name
'Pei, Shuchen'
'Li, Jie'
'Qu, Boyi'
'Hai, Li'
'Wu, Yong'
_publ_section_title
;
 N-(2,3,4-Trifluorophenyl)pyrrolidine-1-carboxamide
;
_journal_coeditor_code           BT5716
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o12
_journal_paper_doi               10.1107/S1600536811051385
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H11 F3 N2 O'
_chemical_formula_moiety         'C11 H11 F3 N2 O'
_chemical_formula_sum            'C11 H11 F3 N2 O'
_chemical_formula_weight         244.22
_chemical_name_systematic
;
N-(2,3,4-Trifluorophenyl)pyrrolidine-1-carboxamide
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.508(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0708(4)
_cell_length_b                   24.2124(15)
_cell_length_c                   7.4232(6)
_cell_measurement_reflns_used    1445
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9055
_cell_measurement_theta_min      2.9090
_cell_volume                     1072.83(13)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2007)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2007)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2007)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4465
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0544
_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)+(0.0550P)²+0.3084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                1374
_reflns_number_total             2190
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5716.cif
_cod_data_source_block           I
_cod_database_code               2233092
_cod_database_fobs_code          2233092
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_symmetry_multiplicity
F F1 0.1373(2) -0.04074(6) 0.1339(2) 0.0855(6) Uani d . 1 1
F F2 0.2120(3) -0.14684(7) 0.2355(3) 0.0987(7) Uani d . 1 1
F F3 0.6185(3) -0.17950(6) 0.4120(2) 0.0908(6) Uani d . 1 1
O O1 0.7849(3) 0.08144(8) 0.2954(3) 0.0827(6) Uani d . 1 1
N N1 0.4504(4) 0.03783(9) 0.2033(3) 0.0586(6) Uani d . 1 1
H H1 0.325(4) 0.0407(10) 0.159(4) 0.061(9) Uiso d . 1 1
N N2 0.4818(3) 0.13161(8) 0.1745(3) 0.0577(6) Uani d . 1 1
C C1 0.3428(4) -0.05587(11) 0.2237(3) 0.0577(6) Uani d . 1 1
C C2 0.3786(5) -0.10989(11) 0.2741(4) 0.0626(7) Uani d . 1 1
C C3 0.5855(5) -0.12546(11) 0.3645(4) 0.0649(7) Uani d . 1 1
C C4 0.7542(5) -0.08815(11) 0.4034(4) 0.0676(7) Uani d . 1 1
H H4 0.8950 -0.0992 0.4640 0.081 Uiso calc R 1 1
C C5 0.7159(4) -0.03335(11) 0.3522(4) 0.0645(7) Uani d . 1 1
H H5 0.8315 -0.0078 0.3799 0.077 Uiso calc R 1 1
C C6 0.5075(4) -0.01615(10) 0.2603(3) 0.0521(6) Uani d . 1 1
C C7 0.5845(4) 0.08395(10) 0.2289(3) 0.0558(6) Uani d . 1 1
C C8 0.2441(4) 0.13970(10) 0.1006(4) 0.0637(7) Uani d . 1 1
H H8A 0.1513 0.1238 0.1807 0.076 Uiso calc R 1 1
H H8B 0.2032 0.1234 -0.0203 0.076 Uiso calc R 1 1
C C9 0.2219(5) 0.20173(12) 0.0924(5) 0.0955(11) Uani d . 1 1
H H9A 0.1181 0.2128 -0.0170 0.115 Uiso calc R 1 1
H H9B 0.1664 0.2153 0.1987 0.115 Uiso calc R 1 1
C C10 0.4431(5) 0.22379(13) 0.0893(5) 0.0987(11) Uani d . 1 1
H H10A 0.4614 0.2594 0.1501 0.118 Uiso calc R 1 1
H H10B 0.4652 0.2284 -0.0359 0.118 Uiso calc R 1 1
C C11 0.6072(5) 0.18321(11) 0.1877(4) 0.0744(8) Uani d . 1 1
H H11A 0.7371 0.1800 0.1293 0.089 Uiso calc R 1 1
H H11B 0.6562 0.1939 0.3146 0.089 Uiso calc R 1 1
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
C6 N1 H1 112.6(19)
C7 N1 H1 120(2)
C7 N1 C6 127.6(2)
C7 N2 C8 127.1(2)
C7 N2 C11 120.7(2)
C11 N2 C8 112.3(2)
F1 C1 C2 118.7(2)
F1 C1 C6 118.6(2)
C2 C1 C6 122.7(2)
F2 C2 C1 120.2(2)
F2 C2 C3 120.7(2)
C3 C2 C1 119.0(2)
F3 C3 C2 118.2(3)
C4 C3 F3 121.0(3)
C4 C3 C2 120.8(3)
C3 C4 H4 120.1
C3 C4 C5 119.7(3)
C5 C4 H4 120.1
C4 C5 H5 119.5
C6 C5 C4 120.9(3)
C6 C5 H5 119.5
C1 C6 N1 117.5(2)
C1 C6 C5 116.8(2)
C5 C6 N1 125.7(2)
O1 C7 N1 122.3(2)
O1 C7 N2 122.5(2)
N2 C7 N1 115.3(2)
N2 C8 H8A 111.2
N2 C8 H8B 111.2
N2 C8 C9 102.9(2)
H8A C8 H8B 109.1
C9 C8 H8A 111.2
C9 C8 H8B 111.2
C8 C9 H9A 110.3
C8 C9 H9B 110.3
H9A C9 H9B 108.6
C10 C9 C8 106.9(2)
C10 C9 H9A 110.3
C10 C9 H9B 110.3
C9 C10 H10A 110.4
C9 C10 H10B 110.4
C9 C10 C11 106.7(3)
H10A C10 H10B 108.6
C11 C10 H10A 110.4
C11 C10 H10B 110.4
N2 C11 C10 103.7(2)
N2 C11 H11A 111.0
N2 C11 H11B 111.0
C10 C11 H11A 111.0
C10 C11 H11B 111.0
H11A C11 H11B 109.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.353(3)
F2 C2 1.341(3)
F3 C3 1.360(3)
O1 C7 1.228(3)
N1 H1 0.77(3)
N1 C6 1.398(3)
N1 C7 1.375(3)
N2 C7 1.338(3)
N2 C8 1.461(3)
N2 C11 1.457(3)
C1 C2 1.367(4)
C1 C6 1.378(3)
C2 C3 1.365(4)
C3 C4 1.357(4)
C4 H4 0.9300
C4 C5 1.388(4)
C5 H5 0.9300
C5 C6 1.387(3)
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.508(4)
C9 H9A 0.9700
C9 H9B 0.9700
C9 C10 1.449(4)
C10 H10A 0.9700
C10 H10B 0.9700
C10 C11 1.492(4)
C11 H11A 0.9700
C11 H11B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 F1 0.77(3) 2.27(3) 2.672(3) 113(2)
