#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238789.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_2238789
loop_
_publ_author_name
'Sreenivasa, S.'
'Mohan, N. R.'
'Kumar, Vijith'
'Palakshamurthy, B. S.'
'Arunakumar, D. B.'
'Suchetan, P. A.'
_publ_section_title
;
 4-Methoxy-N-(pyridin-4-ylmethyl)-3-(trifluoromethyl)benzamide
 monohydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1717
_journal_page_last               o1718
_journal_paper_doi               10.1107/S1600536813029103
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H13 F3 N2 O2, H2 O'
_chemical_formula_moiety         'C15 H13 F3 N2 O2, H2 O'
_chemical_formula_sum            'C15 H15 F3 N2 O3'
_chemical_formula_weight         328.29
_chemical_melting_point          485
_chemical_name_systematic
;
4-Methoxy-N-(pyridin-4-ylmethyl)-3-(trifluoromethyl)benzamide monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.071(10)
_cell_angle_beta                 99.672(10)
_cell_angle_gamma                97.210(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2687(13)
_cell_length_b                   7.8758(14)
_cell_length_c                   14.177(3)
_cell_measurement_reflns_used    1167
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.5
_cell_volume                     764.2(3)
_computing_cell_refinement       'APEX2 and SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus and XPREP (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      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11967
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.51
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 2
_diffrn_standards_number         1012
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         11967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                9619
_reflns_number_total             11967
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5360.cif
_cod_data_source_block           I
_cod_original_cell_volume        764.2(2)
_cod_database_code               2238789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C C4 0.20712(13) -0.16715(12) 0.35758(7) 0.0408(2) Uani d . 1 1
C C1 0.26262(13) 0.00741(12) 0.56032(7) 0.0417(3) Uani d . 1 1
C C6 0.24913(15) 0.10202(13) 0.48940(8) 0.0468(3) Uani d . 1 1
H H6 0.2589 0.2249 0.5092 0.056 Uiso calc R 1 1
C C5 0.22150(14) 0.01550(13) 0.39008(8) 0.0468(3) Uani d . 1 1
H H5 0.2123 0.0812 0.3437 0.056 Uiso calc R 1 1
C C7 0.2577(2) -0.28518(15) 0.60207(9) 0.0678(4) Uani d . 1 1
C C3 0.22117(14) -0.26116(13) 0.42910(8) 0.0471(3) Uani d . 1 1
H H3 0.2120 -0.3840 0.4090 0.057 Uiso calc R 1 1
C C11 0.32767(14) -0.24851(13) 0.04242(7) 0.0430(3) Uani d . 1 1
C C12 0.49099(15) -0.13759(13) 0.09862(7) 0.0471(3) Uani d . 1 1
H H12 0.4928 -0.0702 0.1626 0.057 Uiso calc R 1 1
C C9 0.18106(15) -0.26938(14) 0.25155(8) 0.0488(3) Uani d . 1 1
C C2 0.24823(14) -0.17729(13) 0.52871(8) 0.0452(3) Uani d . 1 1
C C10 0.14376(16) -0.26534(16) 0.07791(8) 0.0605(3) Uani d . 1 1
H H10A 0.0539 -0.2148 0.0390 0.073 Uiso calc R 1 1
H H10B 0.0931 -0.3906 0.0649 0.073 Uiso calc R 1 1
C C13 0.65231(16) -0.12678(14) 0.05948(8) 0.0538(3) Uani d . 1 1
H H13 0.7607 -0.0502 0.0988 0.065 Uiso calc R 1 1
C C8 0.30246(17) 0.26947(13) 0.69388(8) 0.0567(3) Uani d . 1 1
H H8A 0.4111 0.3276 0.6766 0.085 Uiso calc R 1 1
H H8B 0.3154 0.3032 0.7648 0.085 Uiso calc R 1 1
H H8C 0.1901 0.3042 0.6635 0.085 Uiso calc R 1 1
C C14 0.50371(19) -0.32623(15) -0.08476(9) 0.0641(3) Uani d . 1 1
H H14 0.5059 -0.3927 -0.1484 0.077 Uiso calc R 1 1
C C15 0.33680(17) -0.34444(14) -0.05187(8) 0.0558(3) Uani d . 1 1
H H15 0.2301 -0.4212 -0.0929 0.067 Uiso calc R 1 1
N N1 0.15688(12) -0.18044(12) 0.18228(6) 0.0520(2) Uani d . 1 1
H HN1 0.1489 -0.0696 0.2003 0.062 Uiso calc R 1 1
N N2 0.66248(14) -0.21897(12) -0.03090(7) 0.0586(3) Uani d . 1 1
O O1 0.28861(11) 0.08100(9) 0.65917(5) 0.0556(2) Uani d . 1 1
O O3 0.89123(14) -0.17560(10) -0.17013(7) 0.0713(3) Uani d G 1 1
H H1O 0.8411 -0.1809 -0.1207 0.107 Uiso d G 1 1
H H2O 0.8934 -0.2802 -0.2039 0.107 Uiso d G 1 1
O O2 0.18367(14) -0.43033(10) 0.22891(6) 0.0790(3) Uani d . 1 1
F F1 0.12080(15) -0.27319(12) 0.65342(7) 0.1170(3) Uani d . 1 1
F F2 0.41714(13) -0.23917(11) 0.67010(6) 0.1046(3) Uani d . 1 1
F F3 0.24329(18) -0.45486(10) 0.55973(6) 0.1459(5) Uani d . 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'
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'
H H 0.0000 0.0000 '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 C4 C3 117.63(9)
C5 C4 C9 124.51(9)
C3 C4 C9 117.85(9)
O1 C1 C6 124.57(9)
O1 C1 C2 116.78(8)
C6 C1 C2 118.65(9)
C5 C6 C1 120.53(9)
C5 C6 H6 119.7
C1 C6 H6 119.7
C6 C5 C4 121.53(9)
C6 C5 H5 119.2
C4 C5 H5 119.2
F3 C7 F2 106.29(11)
F3 C7 F1 105.41(12)
F2 C7 F1 104.90(11)
F3 C7 C2 112.39(10)
F2 C7 C2 113.54(11)
F1 C7 C2 113.58(10)
C2 C3 C4 121.74(9)
C2 C3 H3 119.1
C4 C3 H3 119.1
C12 C11 C15 116.65(10)
C12 C11 C10 123.31(10)
C15 C11 C10 120.02(9)
C11 C12 C13 119.61(10)
C11 C12 H12 120.2
C13 C12 H12 120.2
O2 C9 N1 121.38(10)
O2 C9 C4 120.76(10)
N1 C9 C4 117.85(9)
C3 C2 C1 119.91(9)
C3 C2 C7 119.49(9)
C1 C2 C7 120.59(10)
N1 C10 C11 115.26(9)
N1 C10 H10A 108.5
C11 C10 H10A 108.5
N1 C10 H10B 108.5
C11 C10 H10B 108.5
H10A C10 H10B 107.5
N2 C13 C12 124.12(10)
N2 C13 H13 117.9
C12 C13 H13 117.9
O1 C8 H8A 109.5
O1 C8 H8B 109.5
H8A C8 H8B 109.5
O1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C14 C15 123.86(11)
N2 C14 H14 118.1
C15 C14 H14 118.1
C14 C15 C11 119.91(11)
C14 C15 H15 120.0
C11 C15 H15 120.0
C9 N1 C10 121.98(10)
C9 N1 HN1 119.0
C10 N1 HN1 119.0
C13 N2 C14 115.85(10)
C1 O1 C8 118.17(7)
H1O O3 H2O 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C4 C5 1.3843(13)
C4 C3 1.3914(13)
C4 C9 1.4903(14)
C1 O1 1.3506(12)
C1 C6 1.3875(14)
C1 C2 1.3989(13)
C6 C5 1.3753(14)
C6 H6 0.9300
C5 H5 0.9300
C7 F3 1.3079(13)
C7 F2 1.3240(15)
C7 F1 1.3279(16)
C7 C2 1.4929(15)
C3 C2 1.3746(14)
C3 H3 0.9300
C11 C12 1.3750(14)
C11 C15 1.3832(14)
C11 C10 1.5072(15)
C12 C13 1.3808(15)
C12 H12 0.9300
C9 O2 1.2331(12)
C9 N1 1.3392(13)
C10 N1 1.4495(13)
C10 H10A 0.9700
C10 H10B 0.9700
C13 N2 1.3295(14)
C13 H13 0.9300
C8 O1 1.4305(12)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C14 N2 1.3319(15)
C14 C15 1.3743(16)
C14 H14 0.9300
C15 H15 0.9300
N1 HN1 0.8600
O3 H1O 0.8499
O3 H2O 0.8500
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 HN1 O3 2_655 0.86 2.12 2.9119(14) 152
O3 H1O N2 1 0.85 2.01 2.8402(15) 166
O3 H2O O2 2_645 0.85 2.20 2.9646(13) 149
C6 H6 F3 1_565 0.93 2.46 3.3963(15) 173
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
O1 C1 C6 C5 -179.63(9)
C2 C1 C6 C5 0.23(15)
C1 C6 C5 C4 -0.29(16)
C3 C4 C5 C6 0.15(15)
C9 C4 C5 C6 -178.73(10)
C5 C4 C3 C2 0.05(15)
C9 C4 C3 C2 179.00(9)
C15 C11 C12 C13 0.16(14)
C10 C11 C12 C13 -178.37(9)
C5 C4 C9 O2 174.51(10)
C3 C4 C9 O2 -4.36(15)
C5 C4 C9 N1 -4.80(15)
C3 C4 C9 N1 176.33(9)
C4 C3 C2 C1 -0.10(16)
C4 C3 C2 C7 178.57(10)
O1 C1 C2 C3 179.83(9)
C6 C1 C2 C3 -0.04(15)
O1 C1 C2 C7 1.17(15)
C6 C1 C2 C7 -178.69(10)
F3 C7 C2 C3 1.81(18)
F2 C7 C2 C3 122.49(12)
F1 C7 C2 C3 -117.75(12)
F3 C7 C2 C1 -179.53(12)
F2 C7 C2 C1 -58.85(15)
F1 C7 C2 C1 60.90(15)
C12 C11 C10 N1 -10.41(15)
C15 C11 C10 N1 171.11(10)
C11 C12 C13 N2 -0.43(16)
N2 C14 C15 C11 -0.26(18)
C12 C11 C15 C14 0.16(15)
C10 C11 C15 C14 178.74(10)
O2 C9 N1 C10 -3.73(16)
C4 C9 N1 C10 175.58(9)
C11 C10 N1 C9 -93.86(12)
C12 C13 N2 C14 0.33(16)
C15 C14 N2 C13 0.02(17)
C6 C1 O1 C8 0.32(15)
C2 C1 O1 C8 -179.53(9)
