#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/04/2220405.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_2220405
loop_
_publ_author_name
'Zhu, Hai-Bin'
'Ji, Jun-Feng'
'Wang, Hai'
_publ_section_title
;(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine--(R)-2-hydroxybutanedioic
 acid (1/1)
;
_journal_coeditor_code           AT2692
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o197
_journal_paper_doi               10.1107/S1600536808043201
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C11 H11 F6 N, C4 H6 O5'
_chemical_formula_sum            'C15 H17 F6 N O5'
_chemical_formula_weight         405.30
_chemical_name_systematic
;
(S)-1-[3,5-Bis(trifluoromethyl)phenyl]-N-methylethylamine--
(R)-2-hydroxybutanedioic acid (1/1)
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6770(13)
_cell_length_b                   8.4510(17)
_cell_length_c                   16.366(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     909.3(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius,1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1915
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         1757
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0628
_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)+(0.0600P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                1067
_reflns_number_total             1757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            at2692.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220405
_cod_database_fobs_code          2220405
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
F F1 0.9058(17) 0.4852(16) 0.9973(8) 0.112 Uani d P 0.50 A 1
F F3 0.9270(13) 0.6270(13) 0.8772(6) 0.083 Uani d P 0.50 A 1
F F2 1.0892(15) 0.4013(14) 0.9084(6) 0.101 Uani d P 0.50 A 1
F F1' 0.7985(16) 0.6070(16) 0.9651(7) 0.111 Uani d P 0.50 A 2
F F2' 1.000(2) 0.4376(16) 0.9758(7) 0.111 Uani d P 0.50 A 2
F F3' 0.9991(17) 0.5461(16) 0.8769(7) 0.115 Uani d P 0.50 A 2
F F4 0.5055(13) -0.0158(14) 0.9651(7) 0.085 Uani d P 0.50 B 1
F F5 0.3781(15) -0.0926(12) 0.8429(6) 0.080 Uani d P 0.50 B 1
F F6 0.6975(13) -0.0918(12) 0.8664(6) 0.078 Uani d PD 0.50 B 1
F F4' 0.5831(15) -0.0443(15) 0.9665(8) 0.097 Uani d P 0.50 B 2
F F5' 0.3083(15) -0.0556(14) 0.8707(6) 0.095 Uani d P 0.50 B 2
F F6' 0.6174(16) -0.1374(14) 0.8609(7) 0.093 Uani d P 0.50 B 2
N N 0.3387(7) 0.3503(6) 0.6045(3) 0.0464(12) Uani d . 1 A .
H H0A 0.2534 0.2888 0.5744 0.056 Uiso calc R 1 . .
C C1 0.8859(12) 0.4933(11) 0.9164(5) 0.081 Uani d . 1 . .
C C2 0.5244(14) -0.0104(14) 0.8816(5) 0.094(3) Uani d D 1 . .
C C3 0.5326(11) 0.1454(10) 0.8548(4) 0.063(2) Uani d . 1 A .
C C4 0.4157(10) 0.2037(8) 0.7869(4) 0.0543(17) Uani d . 1 . .
H H4A 0.3136 0.1408 0.7574 0.065 Uiso calc R 1 B .
C C5 0.4445(9) 0.3611(9) 0.7587(4) 0.0527(16) Uani d . 1 A .
C C6 0.5931(11) 0.4465(10) 0.8000(4) 0.072(2) Uani d . 1 . .
H H6A 0.6137 0.5488 0.7821 0.087 Uiso calc R 1 A .
C C7 0.7249(13) 0.3856(12) 0.8723(5) 0.080(2) Uani d . 1 A .
C C8 0.6962(12) 0.2426(12) 0.8978(5) 0.079(3) Uani d . 1 . .
H H8A 0.7817 0.2026 0.9441 0.095 Uiso calc R 1 A .
C C9 0.3017(8) 0.4239(8) 0.6855(3) 0.0482(15) Uani d . 1 . .
H H9A 0.3274 0.5377 0.6823 0.058 Uiso calc R 1 A .
C C10 0.0783(9) 0.4033(9) 0.6903(4) 0.0646(19) Uani d . 1 A .
H H10A 0.0507 0.4508 0.7405 0.097 Uiso calc R 1 . .
H H10B 0.0461 0.2926 0.6902 0.097 Uiso calc R 1 . .
H H10C -0.0033 0.4535 0.6433 0.097 Uiso calc R 1 . .
C C11 0.5373(9) 0.3961(9) 0.5832(4) 0.0606(18) Uani d . 1 . .
H H11A 0.5542 0.3455 0.5323 0.091 Uiso calc R 1 A .
H H11B 0.6447 0.3636 0.6269 0.091 Uiso calc R 1 . .
H H11C 0.5419 0.5088 0.5766 0.091 Uiso calc R 1 . .
O O1 0.6777(8) 0.0742(7) 0.6474(4) 0.0869(18) Uani d . 1 . .
O O2 0.5220(7) -0.1471(5) 0.6689(3) 0.0652(13) Uani d . 1 . .
H H2A 0.4226 -0.0912 0.6526 0.098 Uiso calc R 1 . .
O O3 0.8263(6) -0.2740(5) 0.5576(3) 0.0579(12) Uani d . 1 . .
H H3A 0.8825 -0.3437 0.5351 0.087 Uiso calc R 1 . .
O O4 1.1965(6) 0.0264(5) 0.6157(3) 0.0540(11) Uani d . 1 . .
O O5 0.9516(7) 0.0076(6) 0.5086(3) 0.0678(15) Uani d . 1 . .
H H5A 1.0184 0.0743 0.4888 0.102 Uiso calc R 1 . .
C C12 0.6858(11) -0.0671(9) 0.6676(4) 0.0551(17) Uani d . 1 . .
C C13 0.8797(9) -0.1508(8) 0.6891(4) 0.0522(15) Uani d . 1 . .
H H13A 0.8587 -0.2481 0.7179 0.063 Uiso calc R 1 . .
H H13B 0.9744 -0.0857 0.7265 0.063 Uiso calc R 1 . .
C C14 0.9715(8) -0.1898(7) 0.6122(3) 0.0428(14) Uani d . 1 . .
H H14A 1.0894 -0.2588 0.6292 0.051 Uiso calc R 1 . .
C C15 1.0461(9) -0.0360(7) 0.5766(4) 0.0464(15) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N C9 . . 112.7(5) ?
C11 N H0A . . 123.6 ?
C9 N H0A . . 123.6 ?
F3' C1 F2' . . 102.5(11) ?
F3' C1 F1 . . 128.3(11) ?
F2' C1 F3 . . 123.5(10) ?
F1 C1 F3 . . 122.1(10) ?
F3' C1 F1' . . 114.7(11) ?
F2' C1 F1' . . 94.2(9) ?
F1 C1 F1' . . 56.8(8) ?
F3 C1 F1' . . 80.8(8) ?
F3' C1 C7 . . 116.5(10) ?
F2' C1 C7 . . 116.5(9) ?
F1 C1 C7 . . 113.2(9) ?
F3 C1 C7 . . 117.9(7) ?
F1' C1 C7 . . 110.3(8) ?
F3' C1 F2 . . 59.7(8) ?
F2' C1 F2 . . 56.9(8) ?
F1 C1 F2 . . 96.9(8) ?
F3 C1 F2 . . 97.0(8) ?
F1' C1 F2 . . 144.0(8) ?
C7 C1 F2 . . 102.4(8) ?
F5 C2 F6' . . 77.4(9) ?
F5 C2 C3 . . 115.3(9) ?
F6' C2 C3 . . 130.1(9) ?
F5 C2 F4 . . 106.1(10) ?
F6' C2 F4 . . 110.7(10) ?
C3 C2 F4 . . 110.8(10) ?
F5 C2 F6 . . 103.2(10) ?
C3 C2 F6 . . 109.2(9) ?
F4 C2 F6 . . 112.1(8) ?
F5 C2 F4' . . 116.0(10) ?
F6' C2 F4' . . 91.5(9) ?
C3 C2 F4' . . 119.0(10) ?
F6 C2 F4' . . 88.8(8) ?
F6' C2 F5' . . 104.7(10) ?
C3 C2 F5' . . 107.4(9) ?
F4 C2 F5' . . 81.7(8) ?
F6 C2 F5' . . 132.1(11) ?
F4' C2 F5' . . 99.5(9) ?
C4 C3 C2 . . 124.2(8) ?
C4 C3 C8 . . 118.5(8) ?
C2 C3 C8 . . 116.8(8) ?
C3 C4 C5 . . 121.2(7) ?
C3 C4 H4A . . 119.4 ?
C5 C4 H4A . . 119.4 ?
C6 C5 C4 . . 118.4(7) ?
C6 C5 C9 . . 122.5(7) ?
C4 C5 C9 . . 119.1(6) ?
C5 C6 C7 . . 121.6(8) ?
C5 C6 H6A . . 119.2 ?
C7 C6 H6A . . 119.2 ?
C8 C7 C6 . . 119.4(8) ?
C8 C7 C1 . . 122.9(8) ?
C6 C7 C1 . . 117.6(8) ?
C7 C8 C3 . . 120.8(8) ?
C7 C8 H8A . . 119.6 ?
C3 C8 H8A . . 119.6 ?
C5 C9 C10 . . 114.4(5) ?
C5 C9 N . . 112.1(5) ?
C10 C9 N . . 108.0(5) ?
C5 C9 H9A . . 107.3 ?
C10 C9 H9A . . 107.3 ?
N C9 H9A . . 107.3 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N C11 H11A . . 109.5 ?
N C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C12 O2 H2A . . 109.5 ?
C14 O3 H3A . . 109.5 ?
C15 O5 H5A . . 109.5 ?
O1 C12 O2 . . 120.8(7) ?
O1 C12 C13 . . 121.8(7) ?
O2 C12 C13 . . 117.4(7) ?
C12 C13 C14 . . 111.8(5) ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
O3 C14 C13 . . 107.7(4) ?
O3 C14 C15 . . 115.0(5) ?
C13 C14 C15 . . 109.4(5) ?
O3 C14 H14A . . 108.2 ?
C13 C14 H14A . . 108.2 ?
C15 C14 H14A . . 108.2 ?
O4 C15 O5 . . 126.3(6) ?
O4 C15 C14 . . 117.3(5) ?
O5 C15 C14 . . 116.3(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 . 1.309(14) ?
F3 C1 . 1.352(13) ?
F2 C1 . 1.589(14) ?
F1' C1 . 1.436(13) ?
F2' C1 . 1.219(13) ?
F3' C1 . 1.167(12) ?
F4 C2 . 1.395(13) ?
F5 C2 . 1.274(12) ?
F6 C2 . 1.404(11) ?
F4' C2 . 1.405(14) ?
F5' C2 . 1.474(13) ?
F6' C2 . 1.313(15) ?
N C11 . 1.480(7) ?
N C9 . 1.523(7) ?
N H0A . 0.8600 ?
C1 C7 . 1.495(11) ?
C2 C3 . 1.392(13) ?
C3 C4 . 1.336(9) ?
C3 C8 . 1.447(11) ?
C4 C5 . 1.432(10) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.315(9) ?
C5 C9 . 1.492(8) ?
C6 C7 . 1.441(10) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.304(13) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.517(8) ?
C9 H9A . 0.9800 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
O1 C12 . 1.237(9) ?
O2 C12 . 1.290(8) ?
O2 H2A . 0.8200 ?
O3 C14 . 1.394(7) ?
O3 H3A . 0.8200 ?
O4 C15 . 1.213(7) ?
O5 C15 . 1.236(7) ?
O5 H5A . 0.8200 ?
C12 C13 . 1.463(9) ?
C13 C14 . 1.530(8) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.543(8) ?
C14 H14A . 0.9800 ?
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 H0A O4 1_455 0.86 2.37 2.914(7) 121.7
N H0A O3 2_656 0.86 2.20 2.887(7) 137.0
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F5 C2 C3 C4 . . . . -8.6(14) ?
F6' C2 C3 C4 . . . . 86.2(14) ?
F4 C2 C3 C4 . . . . -129.1(9) ?
F6 C2 C3 C4 . . . . 107.0(10) ?
F4' C2 C3 C4 . . . . -153.3(8) ?
F5' C2 C3 C4 . . . . -41.5(11) ?
F5 C2 C3 C8 . . . . 179.6(8) ?
F6' C2 C3 C8 . . . . -85.6(13) ?
F4 C2 C3 C8 . . . . 59.1(11) ?
F6 C2 C3 C8 . . . . -64.8(10) ?
F4' C2 C3 C8 . . . . 34.8(13) ?
F5' C2 C3 C8 . . . . 146.6(8) ?
C2 C3 C4 C5 . . . . -174.3(8) ?
C8 C3 C4 C5 . . . . -2.6(11) ?
C3 C4 C5 C6 . . . . 1.8(11) ?
C3 C4 C5 C9 . . . . -176.3(6) ?
C4 C5 C6 C7 . . . . -0.3(11) ?
C9 C5 C6 C7 . . . . 177.8(7) ?
C5 C6 C7 C8 . . . . -0.3(13) ?
C5 C6 C7 C1 . . . . -178.4(8) ?
F3' C1 C7 C8 . . . . 125.5(13) ?
F2' C1 C7 C8 . . . . 4.3(17) ?
F1 C1 C7 C8 . . . . -39.9(15) ?
F3 C1 C7 C8 . . . . 168.3(10) ?
F1' C1 C7 C8 . . . . -101.5(12) ?
F2 C1 C7 C8 . . . . 63.3(12) ?
F3' C1 C7 C6 . . . . -56.5(14) ?
F2' C1 C7 C6 . . . . -177.7(11) ?
F1 C1 C7 C6 . . . . 138.1(10) ?
F3 C1 C7 C6 . . . . -13.7(14) ?
F1' C1 C7 C6 . . . . 76.5(10) ?
F2 C1 C7 C6 . . . . -118.7(8) ?
C6 C7 C8 C3 . . . . -0.6(14) ?
C1 C7 C8 C3 . . . . 177.4(8) ?
C4 C3 C8 C7 . . . . 2.0(13) ?
C2 C3 C8 C7 . . . . 174.3(9) ?
C6 C5 C9 C10 . . . . -128.2(7) ?
C4 C5 C9 C10 . . . . 49.9(8) ?
C6 C5 C9 N . . . . 108.5(7) ?
C4 C5 C9 N . . . . -73.5(7) ?
C11 N C9 C5 . . . . -66.8(7) ?
C11 N C9 C10 . . . . 166.3(5) ?
O1 C12 C13 C14 . . . . -75.2(9) ?
O2 C12 C13 C14 . . . . 103.5(7) ?
C12 C13 C14 O3 . . . . -55.0(7) ?
C12 C13 C14 C15 . . . . 70.6(7) ?
O3 C14 C15 O4 . . . . -167.3(5) ?
C13 C14 C15 O4 . . . . 71.4(6) ?
O3 C14 C15 O5 . . . . 9.4(7) ?
C13 C14 C15 O5 . . . . -111.9(6) ?
