#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:45:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180354 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/23/7202313.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_7202313
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         'C12 H6 O4, 2(C8 H12 N)'
_chemical_formula_sum            'C28 H30 N2 O4'
_chemical_formula_weight         458.54
_chemical_name_common
'bis((RS)-1-phenylethylammonium) naphthalenedicarboxylate'
_chemical_name_systematic
;
bis((RS)-1-phenylethylammonium) 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             2008-07-28T18:56:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                94.483(4)
_cell_angle_beta                 98.503(4)
_cell_angle_gamma                103.126(5)
_cell_formula_units_Z            1
_cell_length_a                   6.1211(5)
_cell_length_b                   9.6478(8)
_cell_length_c                   10.5813(11)
_cell_measurement_reflns_used    8221
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      0.21
_cell_volume                     597.80(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 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1.5° ω and π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7594
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker XPREP (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.097(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0504
_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)+(0.0427P)²+0.1827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                1521
_reflns_number_total             2192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810068c.txt
_cod_data_source_block           6
_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               7202313
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 1.0876(3) 0.3579(2) 0.90326(18) 0.0268(5) Uani 1 1 d . . .
H1 H 1.2117 0.3137 0.9059 0.032 Uiso 1 1 calc R . .
C2 C 0.9075(3) 0.3149(2) 0.80377(18) 0.0249(5) Uani 1 1 d . . .
C3 C 0.7230(3) 0.3814(2) 0.80014(19) 0.0292(5) Uani 1 1 d . . .
H3 H 0.5966 0.3512 0.732 0.035 Uiso 1 1 calc R . .
C4 C 1.2757(3) 0.5118(2) 1.10678(19) 0.0295(5) Uani 1 1 d . . .
H4 H 1.3996 0.4672 1.1122 0.035 Uiso 1 1 calc R . .
C4A C 1.0926(3) 0.4667(2) 1.00239(18) 0.0258(5) Uani 1 1 d . . .
C9 C 0.9104(3) 0.1999(2) 0.69971(18) 0.0266(5) Uani 1 1 d . . .
O1 O 0.7483(2) 0.16698(15) 0.60556(13) 0.0336(4) Uani 1 1 d . . .
O2 O 1.0766(2) 0.14258(15) 0.71030(13) 0.0332(4) Uani 1 1 d . . .
C10 C 0.3498(4) 0.2016(2) 0.2972(2) 0.0341(5) Uani 1 1 d . . .
C11 C 0.5761(4) 0.2738(3) 0.3150(2) 0.0393(6) Uani 1 1 d . . .
H11 H 0.6495 0.3229 0.3969 0.047 Uiso 1 1 calc R . .
C12 C 0.6977(4) 0.2751(3) 0.2135(2) 0.0449(6) Uani 1 1 d . . .
H12 H 0.8531 0.3258 0.2264 0.054 Uiso 1 1 calc R . .
C13 C 0.5937(5) 0.2033(3) 0.0948(2) 0.0474(6) Uani 1 1 d . . .
H13 H 0.6769 0.204 0.0257 0.057 Uiso 1 1 calc R . .
C14 C 0.3683(5) 0.1305(3) 0.0764(2) 0.0466(6) Uani 1 1 d . . .
H14 H 0.2957 0.0806 -0.0054 0.056 Uiso 1 1 calc R . .
C15 C 0.2470(4) 0.1299(2) 0.1774(2) 0.0404(6) Uani 1 1 d . . .
H15 H 0.0914 0.0795 0.164 0.048 Uiso 1 1 calc R . .
C16 C 0.2114(4) 0.2017(2) 0.4045(2) 0.0339(5) Uani 1 1 d . . .
H16 H 0.0484 0.1569 0.367 0.041 Uiso 1 1 calc R . .
C17 C 0.2256(4) 0.3506(2) 0.4691(2) 0.0416(6) Uani 1 1 d . . .
H17A H 0.1157 0.3444 0.5283 0.062 Uiso 1 1 calc R . .
H17B H 0.1906 0.4123 0.4034 0.062 Uiso 1 1 calc R . .
H17C H 0.3797 0.3912 0.5171 0.062 Uiso 1 1 calc R . .
N1 N 0.2864(3) 0.1125(2) 0.50478(17) 0.0288(4) Uani 1 1 d . . .
H1A H 0.443(5) 0.146(3) 0.542(2) 0.043 Uiso 1 1 d . . .
H1B H 0.262(4) 0.012(3) 0.468(2) 0.043 Uiso 1 1 d . . .
H1C H 0.206(4) 0.119(3) 0.573(2) 0.043 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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 1 0 0.079
0 -1 0 0.171
1 0 0 0.121
-1 0 0 0.18
0 -2 3 0.075
0 2 -3 0.008
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 C4A 121.42(17) . . ?
C2 C1 H1 119.3 . . ?
C4A C1 H1 119.3 . . ?
C1 C2 C3 119.08(18) . . ?
C1 C2 C9 119.63(17) . . ?
C3 C2 C9 121.29(17) . . ?
C4 C3 C2 120.94(18) 2_767 . ?
C4 C3 H3 119.5 2_767 . ?
C2 C3 H3 119.5 . . ?
C3 C4 C4A 120.94(18) 2_767 . ?
C3 C4 H4 119.5 2_767 . ?
C4A C4 H4 119.5 . . ?
C4 C4A C1 122.39(17) . . ?
C4 C4A C4A 118.5(2) . 2_767 ?
C1 C4A C4A 119.1(2) . 2_767 ?
O2 C9 O1 123.24(18) . . ?
O2 C9 C2 118.15(17) . . ?
O1 C9 C2 118.60(17) . . ?
C11 C10 C15 118.8(2) . . ?
C11 C10 C16 121.69(19) . . ?
C15 C10 C16 119.5(2) . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C10 C15 C14 120.8(2) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N1 C16 C10 110.11(16) . . ?
N1 C16 C17 108.84(18) . . ?
C10 C16 C17 113.65(18) . . ?
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(15) . . ?
C16 N1 H1B 110.6(14) . . ?
H1A N1 H1B 108(2) . . ?
C16 N1 H1C 108.9(14) . . ?
H1A N1 H1C 106(2) . . ?
H1B N1 H1C 111(2) . . ?
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 1.370(3) . ?
C1 C4A 1.417(3) . ?
C1 H1 0.95 . ?
C2 C3 1.417(3) . ?
C2 C9 1.506(3) . ?
C3 C4 1.367(3) 2_767 ?
C3 H3 0.95 . ?
C4 C3 1.367(3) 2_767 ?
C4 C4A 1.415(3) . ?
C4 H4 0.95 . ?
C4A C4A 1.421(4) 2_767 ?
C9 O2 1.259(2) . ?
C9 O1 1.262(2) . ?
C10 C11 1.380(3) . ?
C10 C15 1.383(3) . ?
C10 C16 1.513(3) . ?
C11 C12 1.393(3) . ?
C11 H11 0.95 . ?
C12 C13 1.375(4) . ?
C12 H12 0.95 . ?
C13 C14 1.376(4) . ?
C13 H13 0.95 . ?
C14 C15 1.388(3) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
C16 N1 1.502(3) . ?
C16 C17 1.521(3) . ?
C16 H16 1 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 H1A 0.95(3) . ?
N1 H1B 0.98(3) . ?
N1 H1C 0.94(3) . ?
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 0.95(3) 1.85(3) 2.784(2) 167(2) .
N1 H1B O1 0.98(3) 1.82(3) 2.802(2) 173(2) 2_656
N1 H1C O2 0.94(3) 1.78(3) 2.713(2) 174(2) 1_455
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
C4A C1 C2 C3 0.2(3) . . . . ?
C4A C1 C2 C9 179.36(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . 2_767 ?
C9 C2 C3 C4 -178.33(18) . . . 2_767 ?
C3 C4 C4A C1 179.0(2) 2_767 . . . ?
C3 C4 C4A C4A -1.1(3) 2_767 . . 2_767 ?
C2 C1 C4A C4 179.35(19) . . . . ?
C2 C1 C4A C4A -0.5(3) . . . 2_767 ?
C1 C2 C9 O2 2.6(3) . . . . ?
C3 C2 C9 O2 -178.22(18) . . . . ?
C1 C2 C9 O1 -176.46(18) . . . . ?
C3 C2 C9 O1 2.7(3) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C16 C10 C11 C12 -178.2(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C16 C10 C15 C14 178.6(2) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C16 N1 -71.2(2) . . . . ?
C15 C10 C16 N1 110.0(2) . . . . ?
C11 C10 C16 C17 51.2(3) . . . . ?
C15 C10 C16 C17 -127.6(2) . . . . ?
