#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/35/2233594.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_2233594
loop_
_publ_author_name
'He, Jian-Ling'
_publ_section_title
;
 4-Methoxy-3-(trifluoromethyl)aniline
;
_journal_coeditor_code           PV2499
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o377
_journal_paper_doi               10.1107/S160053681200030X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H8 F3 N O'
_chemical_formula_moiety         'C8 H8 F3 N O'
_chemical_formula_sum            'C8 H8 F3 N O'
_chemical_formula_weight         191.15
_chemical_name_systematic
;
4-Methoxy-3-(trifluoromethyl)aniline
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   5.4140(11)
_cell_length_b                   14.880(3)
_cell_length_c                   21.304(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      3.3
_cell_volume                     1716.3(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1722
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.34
_diffrn_standards_interval_time  120
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9860
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0590
_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)+(0.0740P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                1389
_reflns_number_total             1722
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2499.cif
_cod_data_source_block           I
_cod_database_code               2233594
_cod_database_fobs_code          2233594
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 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
N N 0.0910(3) 0.09833(11) 0.20799(9) 0.0642(5) Uani d . 1 1
H H0A 0.1826 0.0524 0.2003 0.077 Uiso calc R 1 1
H H0B 0.0020 0.0998 0.2414 0.077 Uiso calc R 1 1
F F3 -0.3126(4) 0.39455(11) 0.21116(7) 0.1021(6) Uani d . 1 1
F F2 -0.3656(3) 0.42452(10) 0.11387(8) 0.0906(5) Uani d . 1 1
C C7 -0.0486(4) 0.32133(13) 0.13969(9) 0.0548(5) Uani d . 1 1
F F1 -0.0537(3) 0.47609(9) 0.16277(8) 0.0924(6) Uani d . 1 1
O O 0.0805(4) 0.39518(12) 0.04733(8) 0.0872(6) Uani d . 1 1
C C6 -0.0515(4) 0.24725(13) 0.17919(10) 0.0550(5) Uani d . 1 1
H H6A -0.1479 0.2487 0.2153 0.066 Uiso calc R 1 1
C C5 0.0868(4) 0.17085(13) 0.16592(9) 0.0557(5) Uani d . 1 1
C C8 -0.1937(4) 0.40274(15) 0.15659(10) 0.0643(6) Uani d . 1 1
C C2 0.0907(4) 0.32022(15) 0.08453(10) 0.0653(6) Uani d . 1 1
C C4 0.2268(5) 0.17158(16) 0.11146(11) 0.0719(7) Uani d . 1 1
H H4A 0.3216 0.1214 0.1016 0.086 Uiso calc R 1 1
C C3 0.2297(5) 0.24452(18) 0.07140(11) 0.0767(7) Uani d . 1 1
H H3A 0.3260 0.2427 0.0353 0.092 Uiso calc R 1 1
C C1 0.2463(6) 0.4017(2) -0.00398(11) 0.0865(8) Uani d . 1 1
H H1A 0.2177 0.4570 -0.0260 0.130 Uiso calc R 1 1
H H1B 0.2203 0.3520 -0.0319 0.130 Uiso calc R 1 1
H H1C 0.4131 0.4005 0.0113 0.130 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N 0.0752(12) 0.0474(10) 0.0699(11) 0.0025(8) 0.0031(9) 0.0081(8)
F3 0.1383(15) 0.0767(10) 0.0912(11) 0.0339(10) 0.0413(10) 0.0151(8)
F2 0.0887(10) 0.0811(11) 0.1018(11) 0.0177(8) -0.0227(9) 0.0065(8)
C7 0.0605(11) 0.0477(11) 0.0562(11) -0.0037(9) -0.0035(10) 0.0018(8)
F1 0.1106(12) 0.0541(8) 0.1124(12) -0.0104(8) -0.0073(9) -0.0123(7)
O 0.1094(14) 0.0758(11) 0.0763(11) 0.0142(10) 0.0150(10) 0.0304(9)
C6 0.0620(12) 0.0492(11) 0.0539(11) -0.0033(9) 0.0009(10) 0.0014(8)
C5 0.0625(12) 0.0482(11) 0.0563(11) -0.0046(9) -0.0058(10) 0.0021(8)
C8 0.0757(15) 0.0539(12) 0.0632(12) 0.0042(10) 0.0003(11) 0.0069(10)
C2 0.0782(14) 0.0604(13) 0.0572(12) 0.0005(11) 0.0006(11) 0.0119(10)
C4 0.0852(16) 0.0629(14) 0.0674(13) 0.0141(12) 0.0126(13) 0.0032(10)
C3 0.0922(17) 0.0765(16) 0.0614(13) 0.0136(13) 0.0179(13) 0.0116(11)
C1 0.0955(18) 0.0942(19) 0.0697(15) -0.0139(15) 0.0077(15) 0.0258(14)
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
C5 N H0A 120.0
C5 N H0B 120.0
H0A N H0B 120.0
C6 C7 C2 120.48(19)
C6 C7 C8 119.62(19)
C2 C7 C8 119.89(18)
C2 O C1 118.4(2)
C7 C6 C5 121.37(19)
C7 C6 H6A 119.3
C5 C6 H6A 119.3
C4 C5 C6 117.27(18)
C4 C5 N 122.13(19)
C6 C5 N 120.53(19)
F3 C8 F1 105.23(19)
F3 C8 F2 106.14(19)
F1 C8 F2 105.25(18)
F3 C8 C7 113.03(18)
F1 C8 C7 112.9(2)
F2 C8 C7 113.50(19)
O C2 C3 124.6(2)
O C2 C7 117.1(2)
C3 C2 C7 118.27(19)
C3 C4 C5 122.0(2)
C3 C4 H4A 119.0
C5 C4 H4A 119.0
C4 C3 C2 120.6(2)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
O C1 H1A 109.5
O C1 H1B 109.5
H1A C1 H1B 109.5
O C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C5 1.403(3)
N H0A 0.8600
N H0B 0.8600
F3 C8 1.335(3)
F2 C8 1.342(3)
C7 C6 1.387(3)
C7 C2 1.396(3)
C7 C8 1.488(3)
F1 C8 1.335(3)
O C2 1.369(3)
O C1 1.418(3)
C6 C5 1.390(3)
C6 H6A 0.9300
C5 C4 1.386(3)
C2 C3 1.383(3)
C4 C3 1.381(3)
C4 H4A 0.9300
C3 H3A 0.9300
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
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
_geom_hbond_publ_flag
C1 H1C F2 1_655 0.96 2.52 3.292(3) 138 yes
C6 H6A F3 . 0.93 2.35 2.696(3) 102 no
N H0A F1 7_545 0.86 2.44 3.242(2) 155 yes
N H0B N 6_455 0.86 2.47 3.245(3) 150 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 522251
