#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:44:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179594 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/58/4505831.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4505831
loop_
_publ_author_name
'Fomulu, Shella L.'
'Hendi, Mukta S.'
'Davis, Raymond E.'
'Wheeler, Kraig A.'
_publ_section_title
;
 Structural Studies of Enantiomers, Racemates, and Quasiracemates.
 2-(2,4,5-Trichloroanilino)propanoic Acid and
 2-(2,4,5-Trichlorophenoxy)propanoic Acid
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              637
_journal_paper_doi               10.1021/cg0255570
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C9 H8 Cl3 N O2'
_chemical_formula_weight         268.51
_chemical_name_systematic
; 
(R)-2-(2,4,5-Trichloroanilino)propionic Acid 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.6692(5)
_cell_length_b                   7.7834(15)
_cell_length_c                   21.5744(18)
_cell_measurement_reflns_used    27
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.271
_cell_measurement_theta_min      19.260
_cell_volume                     1119.9(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'siemens P4'
_diffrn_measurement_method       '2θ/θ 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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2082
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.78
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          1.102
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1202
_reflns_number_total             1899
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0255570-2_s1.cif
_cod_data_source_block           c:\structs\15-16\y98\y98
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4505831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.3572(2) 0.3095(2) 0.86506(7) 0.0595(5) Uani 1 1 d .
Cl2 Cl 0.6792(2) 0.3087(3) 0.63829(7) 0.0628(5) Uani 1 1 d .
Cl3 Cl 1.0621(2) 0.1147(3) 0.69131(7) 0.0621(5) Uani 1 1 d .
N N 0.7162(7) 0.1112(8) 0.9023(2) 0.0481(14) Uani 1 1 d .
O2 O 0.9903(6) 0.2743(6) 0.97876(18) 0.0508(11) Uani 1 1 d .
O1 O 1.1741(5) 0.0363(5) 0.98578(19) 0.0533(11) Uani 1 1 d .
HO1 H 1.2508 0.1002 1.0045 0.080 Uiso 1 1 calc R
C1 C 1.0151(8) 0.1243(9) 0.9673(2) 0.0389(14) Uani 1 1 d .
C2 C 0.8682(7) 0.0089(8) 0.9323(2) 0.0411(14) Uani 1 1 d .
H2 H 0.9424 -0.0545 0.9004 0.049 Uiso 1 1 calc R
C3 C 0.7768(9) -0.1194(9) 0.9772(3) 0.0630(19) Uani 1 1 d .
H3A H 0.6902 -0.1963 0.9549 0.094 Uiso 1 1 calc R
H3B H 0.7007 -0.0591 1.0080 0.094 Uiso 1 1 calc R
H3C H 0.8817 -0.1838 0.9969 0.094 Uiso 1 1 calc R
C4 C 0.7164(7) 0.1588(7) 0.8412(2) 0.0362(13) Uani 1 1 d .
C5 C 0.5545(7) 0.2497(7) 0.8169(2) 0.0383(13) Uani 1 1 d .
C6 C 0.5438(7) 0.2940(8) 0.7549(2) 0.0421(14) Uani 1 1 d .
H6 H 0.4319 0.3520 0.7400 0.051 Uiso 1 1 calc R
C7 C 0.6964(8) 0.2529(8) 0.7156(2) 0.0428(15) Uani 1 1 d .
C8 C 0.8602(7) 0.1667(8) 0.7382(2) 0.0415(14) Uani 1 1 d .
C9 C 0.8711(7) 0.1210(8) 0.8009(2) 0.0411(13) Uani 1 1 d .
H9 H 0.9843 0.0643 0.8156 0.049 Uiso 1 1 calc R
HN H 0.630(7) 0.143(7) 0.921(2) 0.028(16) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0440(8) 0.0763(12) 0.0582(9) 0.0080(10) 0.0065(7) 0.0196(9)
Cl2 0.0590(9) 0.0853(13) 0.0441(8) 0.0211(9) -0.0062(7) 0.0009(11)
Cl3 0.0473(8) 0.0846(13) 0.0545(9) 0.0064(9) 0.0123(7) 0.0102(9)
N 0.040(3) 0.070(4) 0.034(3) -0.002(3) -0.002(2) 0.016(3)
O2 0.038(2) 0.052(3) 0.062(3) -0.012(2) 0.0017(19) 0.002(2)
O1 0.0361(19) 0.060(3) 0.063(2) -0.004(2) -0.0159(19) 0.000(2)
C1 0.035(3) 0.050(4) 0.032(3) 0.006(3) -0.001(2) 0.000(3)
C2 0.033(3) 0.051(4) 0.039(3) -0.005(3) -0.009(2) 0.006(3)
C3 0.043(3) 0.058(4) 0.088(5) 0.026(4) -0.018(3) -0.018(3)
C4 0.030(2) 0.040(4) 0.039(3) -0.001(3) -0.007(2) -0.004(3)
C5 0.028(2) 0.042(3) 0.045(3) 0.000(3) -0.001(2) 0.002(3)
C6 0.030(2) 0.047(4) 0.050(3) 0.010(3) -0.008(2) 0.001(3)
C7 0.045(3) 0.049(4) 0.034(3) 0.009(3) -0.006(2) -0.007(3)
C8 0.031(2) 0.050(4) 0.043(3) -0.002(3) 0.000(2) 0.000(3)
C9 0.031(2) 0.049(4) 0.043(3) 0.003(3) -0.010(2) 0.005(3)
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'
Cl Cl 0.1484 0.1585 '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
C4 N C2 125.4(5)
O2 C1 O1 123.4(6)
O2 C1 C2 125.6(5)
O1 C1 C2 111.0(5)
N C2 C3 111.5(5)
N C2 C1 110.3(5)
C3 C2 C1 109.1(5)
N C4 C9 123.3(5)
N C4 C5 119.9(5)
C9 C4 C5 116.8(5)
C6 C5 C4 122.0(5)
C6 C5 Cl1 118.1(4)
C4 C5 Cl1 119.9(4)
C7 C6 C5 120.3(5)
C6 C7 C8 119.3(5)
C6 C7 Cl2 119.5(4)
C8 C7 Cl2 121.2(4)
C7 C8 C9 120.5(5)
C7 C8 Cl3 121.8(4)
C9 C8 Cl3 117.6(4)
C4 C9 C8 121.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.740(5)
Cl2 C7 1.728(5)
Cl3 C8 1.732(5)
N C4 1.370(7)
N C2 1.442(7)
O2 C1 1.205(7)
O1 C1 1.324(6)
C1 C2 1.529(8)
C2 C3 1.519(8)
C4 C9 1.381(7)
C4 C5 1.392(7)
C5 C6 1.384(7)
C6 C7 1.362(7)
C7 C8 1.371(7)
C8 C9 1.402(7)
