#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200785.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_2200785
loop_
_publ_author_name
S.Ramaswamy
B.Sridhar
V.Ramakrishnan
R.K.Rajaram
_publ_section_title
;
 <small>D</small>-Phenylglycinium perchlorate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1149
_journal_page_last               o1151
_journal_paper_doi               10.1107/S160053680101858X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C8 H10 N O2 +. Cl O4 -'
_chemical_formula_sum            'C8 H10 Cl N O6'
_chemical_formula_weight         251.62
_chemical_name_common            'D-phenylglycinium perchlorate'
_chemical_name_systematic
;
D-phenylglycinium perchlorate
;
_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'
_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                   5.4510(10)
_cell_length_b                   8.807(2)
_cell_length_c                   22.649(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      13.58
_cell_volume                     1087.3(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'PLATON (Spek, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .896
_diffrn_measured_fraction_theta_max .896
_diffrn_measurement_device_type  'Enraf-Nonis sealed tube'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0230
_diffrn_reflns_av_sigmaI/netI    .0154
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1485
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .365
_exptl_absorpt_correction_T_max  .947
_exptl_absorpt_correction_T_min  .864
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      1.530
_exptl_crystal_density_method
'flotation technique using a mixture of carbon tetrachloride and xylene'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .15
_refine_diff_density_max         .326
_refine_diff_density_min         -.222
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -.98(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          .0580
_refine_ls_R_factor_gt           .0556
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1125P)²+0.6721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1612
_reflns_number_gt                1193
_reflns_number_total             1261
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6065.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_database_code               2200785
_cod_database_fobs_code          2200785
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_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
_atom_site_type_symbol
Cl1 .0200(2) .18151(14) .31252(5) .0558(4) Uani d . 1 . . Cl
O1 .079(3) .328(3) .3277(8) .101(6) Uani d P .50 A 1 O
O2 -.027(4) .143(4) .2544(10) .146(11) Uani d P .50 A 1 O
O3 -.149(6) .135(2) .3507(10) .139(12) Uani d P .50 A 1 O
O4 .187(5) .078(3) .3430(15) .227(14) Uani d P .50 A 1 O
O1' -.016(3) .340(2) .3052(8) .092(4) Uani d P .50 A 2 O
O2' .017(4) .119(3) .2570(12) .132(9) Uani d P .50 A 2 O
O3' -.200(5) .132(2) .3420(11) .120(8) Uani d P .50 A 2 O
O4' .269(3) .156(2) .3260(6) .134(7) Uani d P .50 A 2 O
O1A .5190(9) .8079(4) .29331(15) .0712(11) Uani d . 1 . . O
O1B .7712(8) .8274(4) .36966(14) .0682(11) Uani d . 1 . . O
H12 .7769 .9174 .3606 .102 Uiso calc R 1 . . H
C11 .6297(9) .7563(5) .33355(16) .0453(11) Uani d . 1 . . C
C12 .6124(9) .5885(5) .34892(16) .0449(11) Uani d . 1 . . C
H12A .7788 .5494 .3550 .054 Uiso calc R 1 . . H
N11 .5040(9) .5103(5) .29656(14) .0588(11) Uani d . 1 . . N
H11A .5953 .5294 .2648 .088 Uiso calc R 1 . . H
H11B .3523 .5443 .2906 .088 Uiso calc R 1 . . H
H11C .5000 .4107 .3030 .088 Uiso calc R 1 . . H
C13 .4637(9) .5580(5) .40412(16) .0450(11) Uani d . 1 . . C
C14 .2607(9) .6449(6) .41674(19) .0540(12) Uani d . 1 . . C
H14 .2174 .7246 .3919 .065 Uiso calc R 1 . . H
C15 .1211(12) .6143(8) .4662(2) .0700(16) Uani d . 1 . . C
H15 -.0167 .6727 .4746 .084 Uiso calc R 1 . . H
C16 .1871(14) .4966(8) .5031(2) .081(2) Uani d . 1 . . C
H16 .0939 .4761 .5366 .097 Uiso calc R 1 . . H
C17 .3888(18) .4099(9) .4908(2) .091(2) Uani d . 1 . . C
H17 .4322 .3302 .5156 .109 Uiso calc R 1 . . H
C18 .5280(13) .4417(6) .4411(2) .0666(15) Uani d . 1 . . C
H18 .6662 .3835 .4328 .080 Uiso calc R 1 . . H
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
Cl1 .0486(6) .0514(8) .0674(7) -.0024(6) .0163(6) -.0056(5)
O1 .084(10) .083(11) .136(13) -.035(10) .029(9) -.026(10)
O2 .086(10) .26(3) .088(11) -.080(14) -.007(8) -.053(13)
O3 .18(3) .088(12) .152(14) -.041(12) .108(15) -.075(11)
O4 .14(2) .159(17) .38(4) .049(14) -.04(2) .11(2)
O1' .087(10) .048(5) .140(13) .007(9) .000(8) -.006(8)
O2' .122(14) .131(12) .143(17) .023(10) .079(11) -.074(11)
O3' .096(10) .083(11) .182(17) -.016(8) .073(11) .057(11)
O4' .079(8) .23(2) .096(7) .061(12) .003(6) .067(10)
O1A .088(3) .071(2) .0542(17) -.003(3) -.009(2) .0152(16)
O1B .089(3) .060(2) .0556(18) -.024(2) -.0085(19) .0006(16)
C11 .054(3) .053(2) .0292(16) -.007(2) .0099(19) .0023(19)
C12 .043(2) .056(3) .0365(18) .007(2) .0020(19) .0021(18)
N11 .063(3) .073(3) .0394(17) -.010(3) .011(2) -.0123(17)
C13 .047(2) .055(2) .0330(17) -.011(2) .0015(18) -.0018(17)
C14 .049(2) .071(3) .042(2) .003(3) .001(2) -.004(2)
C15 .054(3) .098(4) .058(3) -.007(3) .013(3) -.018(3)
C16 .096(5) .107(5) .040(2) -.041(5) .020(3) -.009(3)
C17 .122(7) .096(5) .055(3) -.013(5) .010(4) .023(3)
C18 .074(4) .067(3) .059(3) -.001(3) .008(3) .016(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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
O3 Cl1 O1 106.7(10)
O3 Cl1 O2' 117.6(14)
O1 Cl1 O2' 127.6(16)
O3 Cl1 O2 114.6(16)
O1 Cl1 O2 120.8(16)
O2' Cl1 O2 14(2)
O3 Cl1 O4' 118.5(16)
O1 Cl1 O4' 82.6(11)
O2' Cl1 O4' 98.4(11)
O2 Cl1 O4' 110.2(12)
O3 Cl1 O1' 106.2(13)
O1 Cl1 O1' 30.5(8)
O2' Cl1 O1' 106.6(15)
O2 Cl1 O1' 95.9(17)
O4' Cl1 O1' 108.6(11)
O3 Cl1 O3' 13(2)
O1 Cl1 O3' 111.2(11)
O2' Cl1 O3' 107.0(15)
O2 Cl1 O3' 102.3(14)
O4' Cl1 O3' 130.8(13)
O1' Cl1 O3' 103.5(11)
O3 Cl1 O4 86.2(18)
O1 Cl1 O4 108.8(14)
O2' Cl1 O4 101.0(18)
O2 Cl1 O4 114(2)
O4' Cl1 O4 36.6(10)
O1' Cl1 O4 139.1(13)
O3' Cl1 O4 96.4(16)
C11 O1B H12 109.5
O1A C11 O1B 127.5(4)
O1A C11 C12 121.2(4)
O1B C11 C12 111.4(4)
N11 C12 C13 111.2(4)
N11 C12 C11 106.9(3)
C13 C12 C11 113.2(3)
N11 C12 H12A 108.5
C13 C12 H12A 108.5
C11 C12 H12A 108.5
C12 N11 H11A 109.5
C12 N11 H11B 109.5
H11A N11 H11B 109.5
C12 N11 H11C 109.5
H11A N11 H11C 109.5
H11B N11 H11C 109.5
C18 C13 C14 119.7(5)
C18 C13 C12 120.0(5)
C14 C13 C12 120.3(4)
C13 C14 C15 120.2(5)
C13 C14 H14 119.9
C15 C14 H14 119.9
C16 C15 C14 119.6(6)
C16 C15 H15 120.2
C14 C15 H15 120.2
C17 C16 C15 120.4(5)
C17 C16 H16 119.8
C15 C16 H16 119.8
C16 C17 C18 119.5(6)
C16 C17 H17 120.2
C18 C17 H17 120.2
C13 C18 C17 120.5(6)
C13 C18 H18 119.8
C17 C18 H18 119.8
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
Cl1 O3 . 1.33(2) ?
Cl1 O1 . 1.37(2) ?
Cl1 O2' . 1.37(2) ?
Cl1 O2 . 1.383(19) ?
Cl1 O4' . 1.409(15) ?
Cl1 O1' . 1.417(19) ?
Cl1 O3' . 1.44(2) ?
Cl1 O4 . 1.46(2) ?
O1A C11 . 1.184(5) yes
O1B C11 . 1.287(6) yes
O1B H12 . .8200 ?
C11 C12 . 1.521(6) ?
C12 N11 . 1.493(5) ?
C12 C13 . 1.514(6) ?
C12 H12A . .9800 ?
N11 H11A . .8900 ?
N11 H11B . .8900 ?
N11 H11C . .8900 ?
C13 C18 . 1.369(7) ?
C13 C14 . 1.375(7) ?
C14 C15 . 1.382(7) ?
C14 H14 . .9300 ?
C15 C16 . 1.378(9) ?
C15 H15 . .9300 ?
C16 C17 . 1.367(11) ?
C16 H16 . .9300 ?
C17 C18 . 1.386(8) ?
C17 H17 . .9300 ?
C18 H18 . .9300 ?
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
O1B H12 O3 1_665 .82 1.97 2.78(2) 168
O1B H12 O3' 1_665 .82 1.94 2.76(2) 178
N11 H11A O2' 4_655 .89 2.31 3.036(17) 139
N11 H11A O4' 4_655 .89 2.45 3.297(16) 159
N11 H11A O2 4_655 .89 2.60 3.29(2) 136
N11 H11B O2 4 .89 2.22 3.076(17) 161
N11 H11B O2' 4 .89 2.37 3.23(2) 162
N11 H11C O1 . .89 2.47 2.906(18) 111
N11 H11C O4' . .89 2.63 3.44(2) 153
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
_geom_torsion_publ_flag
O1A C11 C12 N11 16.1(6) yes
O1B C11 C12 N11 -164.9(4) ?
O1A C11 C12 C13 -106.8(5) ?
O1B C11 C12 C13 72.2(5) ?
N11 C12 C13 C18 94.3(6) yes
C11 C12 C13 C18 -145.3(5) ?
N11 C12 C13 C14 -84.4(5) yes
C11 C12 C13 C14 36.0(6) ?
C18 C13 C14 C15 -.5(8) ?
C12 C13 C14 C15 178.2(5) ?
C13 C14 C15 C16 .4(8) ?
C14 C15 C16 C17 -.3(10) ?
C15 C16 C17 C18 .5(10) ?
C14 C13 C18 C17 .7(8) ?
C12 C13 C18 C17 -178.0(5) ?
C16 C17 C18 C13 -.6(10) ?
