#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:45:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180354 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/23/7202310.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_7202310
loop_
_publ_author_name
'Lemmerer, Andreas'
'Bourne, Susan A.'
'Fernandes, Manuel A.'
_publ_section_title
;
 Structural and melting point characterisation of six chiral ammonium
 naphthalene carboxylate salts
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1605
_journal_paper_doi               10.1039/b810068c
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C8 H12 N, C11 H7 O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_name_common
'bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate'
_chemical_name_systematic
;
bis((RS)-1-phenylethylammonium) 26-naphthalenedicarboxylate
;
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-07-28T18:32:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.398(4)
_cell_angle_beta                 101.879(3)
_cell_angle_gamma                98.163(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1388(5)
_cell_length_b                   10.6194(5)
_cell_length_c                   12.8861(9)
_cell_measurement_reflns_used    17035
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      0.41
_cell_volume                     775.14(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '2.0° ω and π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14817
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.1709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.0972
_reflns_number_gt                2588
_reflns_number_total             2849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810068c.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7202310
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.07642(17) 0.03190(10) 0.22281(8) 0.0214(2) Uani 1 1 d . . .
H1 H -0.2016 0.0364 0.2554 0.026 Uiso 1 1 calc R . .
C2 C 0.09932(17) 0.14092(10) 0.25549(8) 0.0201(2) Uani 1 1 d . . .
C3 C 0.28499(18) 0.13471(10) 0.20618(9) 0.0240(2) Uani 1 1 d . . .
H3 H 0.4076 0.2098 0.229 0.029 Uiso 1 1 calc R . .
C4 C 0.28961(18) 0.02162(11) 0.12587(9) 0.0251(2) Uani 1 1 d . . .
H4A H 0.4143 0.0198 0.0928 0.03 Uiso 1 1 calc R . .
C4A C 0.11120(18) -0.09268(10) 0.09144(8) 0.0233(2) Uani 1 1 d . . .
C5 C 0.1130(2) -0.21278(11) 0.01077(9) 0.0297(3) Uani 1 1 d . . .
H5 H 0.2357 -0.2175 -0.0236 0.036 Uiso 1 1 calc R . .
C6 C -0.0602(2) -0.32181(11) -0.01791(9) 0.0337(3) Uani 1 1 d . . .
H6 H -0.0563 -0.4019 -0.0716 0.04 Uiso 1 1 calc R . .
C7 C -0.2441(2) -0.31636(11) 0.03148(10) 0.0327(3) Uani 1 1 d . . .
H7 H -0.3636 -0.3927 0.0106 0.039 Uiso 1 1 calc R . .
C8 C -0.25242(19) -0.20208(11) 0.10939(9) 0.0274(2) Uani 1 1 d . . .
H8 H -0.3775 -0.1995 0.1422 0.033 Uiso 1 1 calc R . .
C8A C -0.07491(17) -0.08755(10) 0.14123(8) 0.0220(2) Uani 1 1 d . . .
C9 C 0.08888(17) 0.26544(10) 0.34257(8) 0.0206(2) Uani 1 1 d . . .
O1 O 0.24762(12) 0.36737(7) 0.36788(6) 0.0266(2) Uani 1 1 d . . .
O2 O -0.07805(12) 0.26288(7) 0.38428(6) 0.0269(2) Uani 1 1 d . . .
C10 C 0.64831(18) 0.66773(10) 0.34922(9) 0.0240(2) Uani 1 1 d . . .
C11 C 0.41672(19) 0.64061(11) 0.29692(10) 0.0302(3) Uani 1 1 d . . .
H11 H 0.3372 0.5507 0.2613 0.036 Uiso 1 1 calc R . .
C12 C 0.3016(2) 0.74391(12) 0.29647(10) 0.0343(3) Uani 1 1 d . . .
H12 H 0.1442 0.7245 0.26 0.041 Uiso 1 1 calc R . .
C13 C 0.4151(2) 0.87483(12) 0.34891(10) 0.0348(3) Uani 1 1 d . . .
H13 H 0.336 0.9455 0.3486 0.042 Uiso 1 1 calc R . .
C14 C 0.6440(2) 0.90272(12) 0.40182(10) 0.0351(3) Uani 1 1 d . . .
H14 H 0.7221 0.9927 0.4384 0.042 Uiso 1 1 calc R . .
C15 C 0.7606(2) 0.79961(11) 0.40182(9) 0.0291(3) Uani 1 1 d . . .
H15 H 0.9182 0.8196 0.4381 0.035 Uiso 1 1 calc R . .
C16 C 0.77979(17) 0.55673(10) 0.34559(9) 0.0241(2) Uani 1 1 d . . .
H16 H 0.945 0.5987 0.3778 0.029 Uiso 1 1 calc R . .
C17 C 0.7507(2) 0.46667(12) 0.22812(9) 0.0334(3) Uani 1 1 d . . .
H17A H 0.5906 0.4215 0.196 0.05 Uiso 1 1 calc R . .
H17B H 0.8452 0.3999 0.2303 0.05 Uiso 1 1 calc R . .
H17C H 0.7975 0.5205 0.1823 0.05 Uiso 1 1 calc R . .
N1 N 0.70974(15) 0.47275(9) 0.41505(7) 0.0215(2) Uani 1 1 d . . .
H1A H 0.550(2) 0.4312(13) 0.3907(11) 0.032 Uiso 1 1 d . . .
H1B H 0.732(2) 0.5269(13) 0.4902(12) 0.032 Uiso 1 1 d . . .
H1C H 0.791(2) 0.4038(13) 0.4114(11) 0.032 Uiso 1 1 d . . .
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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.264
0 0 -1 0.16
1 0 0 0.25
-1 -8 12 0.099
2 1 -13 0.25
-1 2 4 0.269
-1 8 0 0.25
0 1 -1 0.239
-1 1 0 0.226
-6 -7 2 0.34
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8A 121.30(10) . . ?
C2 C1 H1 119.4 . . ?
C8A C1 H1 119.4 . . ?
C1 C2 C3 119.41(9) . . ?
C1 C2 C9 119.08(9) . . ?
C3 C2 C9 121.51(9) . . ?
C4 C3 C2 120.68(9) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.97(10) . . ?
C3 C4 H4A 119.5 . . ?
C4A C4 H4A 119.5 . . ?
C4 C4A C5 122.58(10) . . ?
C4 C4A C8A 118.66(9) . . ?
C5 C4A C8A 118.75(10) . . ?
C6 C5 C4A 120.59(10) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C7 120.50(10) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.65(10) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 120.18(10) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C8 C8A C1 121.69(10) . . ?
C8 C8A C4A 119.33(10) . . ?
C1 C8A C4A 118.98(9) . . ?
O2 C9 O1 123.77(9) . . ?
O2 C9 C2 118.05(9) . . ?
O1 C9 C2 118.17(9) . . ?
C15 C10 C11 118.83(10) . . ?
C15 C10 C16 119.86(10) . . ?
C11 C10 C16 121.27(10) . . ?
C12 C11 C10 120.47(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.23(11) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.76(10) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.25(11) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.45(11) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C10 110.80(8) . . ?
N1 C16 C17 108.88(9) . . ?
C10 C16 C17 112.93(9) . . ?
N1 C16 H16 108 . . ?
C10 C16 H16 108 . . ?
C17 C16 H16 108 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 N1 H1A 113.0(8) . . ?
C16 N1 H1B 110.4(8) . . ?
H1A N1 H1B 104.9(11) . . ?
C16 N1 H1C 109.9(8) . . ?
H1A N1 H1C 107.1(11) . . ?
H1B N1 H1C 111.3(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3715(15) . ?
C1 C8A 1.4189(15) . ?
C1 H1 0.95 . ?
C2 C3 1.4158(15) . ?
C2 C9 1.5091(14) . ?
C3 C4 1.3696(15) . ?
C3 H3 0.95 . ?
C4 C4A 1.4164(15) . ?
C4 H4A 0.95 . ?
C4A C5 1.4185(15) . ?
C4A C8A 1.4215(15) . ?
C5 C6 1.3672(17) . ?
C5 H5 0.95 . ?
C6 C7 1.4061(18) . ?
C6 H6 0.95 . ?
C7 C8 1.3694(16) . ?
C7 H7 0.95 . ?
C8 C8A 1.4176(15) . ?
C8 H8 0.95 . ?
C9 O2 1.2515(12) . ?
C9 O1 1.2688(12) . ?
C10 C15 1.3877(16) . ?
C10 C11 1.3945(16) . ?
C10 C16 1.5163(14) . ?
C11 C12 1.3871(16) . ?
C11 H11 0.95 . ?
C12 C13 1.3810(18) . ?
C12 H12 0.95 . ?
C13 C14 1.3810(19) . ?
C13 H13 0.95 . ?
C14 C15 1.3905(17) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.5016(13) . ?
C16 C17 1.5197(15) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 0.967(14) . ?
N1 H1B 0.956(14) . ?
N1 H1C 0.940(14) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.97(1) 1.82(1) 2.774(1) 170.6(1) .
N1 H1B O1 0.96(1) 1.84(2) 2.797(1) 175.6(1) 2_666
N1 H1C O2 0.94(1) 1.79(1) 2.718(1) 171.8(1) 1_655
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A C1 C2 C3 0.59(15) . . . . ?
C8A C1 C2 C9 179.97(8) . . . . ?
C1 C2 C3 C4 0.51(15) . . . . ?
C9 C2 C3 C4 -178.85(9) . . . . ?
C2 C3 C4 C4A -1.11(16) . . . . ?
C3 C4 C4A C5 -178.23(10) . . . . ?
C3 C4 C4A C8A 0.59(15) . . . . ?
C4 C4A C5 C6 178.34(10) . . . . ?
C8A C4A C5 C6 -0.48(16) . . . . ?
C4A C5 C6 C7 0.51(17) . . . . ?
C5 C6 C7 C8 -0.26(18) . . . . ?
C6 C7 C8 C8A -0.02(17) . . . . ?
C7 C8 C8A C1 -179.09(10) . . . . ?
C7 C8 C8A C4A 0.04(15) . . . . ?
C2 C1 C8A C8 178.05(9) . . . . ?
C2 C1 C8A C4A -1.09(15) . . . . ?
C4 C4A C8A C8 -178.66(9) . . . . ?
C5 C4A C8A C8 0.20(15) . . . . ?
C4 C4A C8A C1 0.49(14) . . . . ?
C5 C4A C8A C1 179.36(9) . . . . ?
C1 C2 C9 O2 2.11(14) . . . . ?
C3 C2 C9 O2 -178.53(9) . . . . ?
C1 C2 C9 O1 -176.68(8) . . . . ?
C3 C2 C9 O1 2.68(14) . . . . ?
C15 C10 C11 C12 0.75(16) . . . . ?
C16 C10 C11 C12 -176.84(10) . . . . ?
C10 C11 C12 C13 -0.65(17) . . . . ?
C11 C12 C13 C14 0.07(17) . . . . ?
C12 C13 C14 C15 0.41(17) . . . . ?
C11 C10 C15 C14 -0.27(16) . . . . ?
C16 C10 C15 C14 177.36(9) . . . . ?
C13 C14 C15 C10 -0.31(17) . . . . ?
C15 C10 C16 N1 112.15(11) . . . . ?
C11 C10 C16 N1 -70.28(12) . . . . ?
C15 C10 C16 C17 -125.40(11) . . . . ?
C11 C10 C16 C17 52.17(13) . . . . ?
