#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510424.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_4510424
loop_
_publ_author_name
'Adalder, Tapas Kumar'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Crystal Engineering Approach toward Selective Formation of an Asymmetric
 Supramolecular Synthon in Primary Ammonium Monocarboxylate (PAM) Salts
 and Their Gelation Studies
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2254
_journal_paper_doi               10.1021/cg401863s
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration S
_chemical_formula_moiety         'C8 H6 N O4, C8 H12 N'
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 94.277(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.4839(6)
_cell_length_b                   5.86480(10)
_cell_length_c                   14.7362(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1593.02(7)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'MERCURY 3.1, PLATON'
_computing_publication_material  'MERCURY 3.1, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10454
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NIDDLE
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0669P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                2848
_reflns_number_total             3060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401863s_si_002.cif
_cod_data_source_block           (S)-PEA.4NPA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4510410--4510441.cif.
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4510424
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O1 O 0.72963(6) 0.6195(2) 0.60699(7) 0.0552(3) Uani 1 1 d .
C2 C 0.75951(8) 0.7104(3) 0.67628(10) 0.0511(4) Uani 1 1 d .
O3 O 0.77401(9) 0.9149(3) 0.68187(10) 0.0828(4) Uani 1 1 d .
C4 C 0.77809(11) 0.5603(4) 0.75923(11) 0.0657(5) Uani 1 1 d .
H4A H 0.7739 0.4012 0.7416 0.079 Uiso 1 1 calc R
H4B H 0.8279 0.5881 0.7821 0.079 Uiso 1 1 calc R
C5 C 0.72823(9) 0.6081(3) 0.83341(10) 0.0510(4) Uani 1 1 d .
C6 C 0.67570(11) 0.4546(4) 0.85400(13) 0.0677(5) Uani 1 1 d .
H6 H 0.6701 0.3196 0.8211 0.081 Uiso 1 1 calc R
C7 C 0.63079(12) 0.4991(5) 0.92347(15) 0.0800(6) Uani 1 1 d .
H7 H 0.5960 0.3937 0.9383 0.096 Uiso 1 1 calc R
C8 C 0.63868(10) 0.6997(5) 0.96934(11) 0.0713(5) Uani 1 1 d .
O9 O 0.58715(17) 0.9505(8) 1.0670(2) 0.1732(14) Uani 1 1 d .
N10 N 0.59196(13) 0.7518(7) 1.04362(15) 0.1104(10) Uani 1 1 d .
O11 O 0.56170(17) 0.5980(8) 1.07763(18) 0.1757(15) Uani 1 1 d .
C12 C 0.68912(12) 0.8581(4) 0.94925(12) 0.0698(5) Uani 1 1 d .
H12 H 0.6930 0.9953 0.9809 0.084 Uiso 1 1 calc R
C13 C 0.73388(11) 0.8114(3) 0.88182(12) 0.0608(4) Uani 1 1 d .
H13 H 0.7688 0.9177 0.8681 0.073 Uiso 1 1 calc R
C14 C 0.89253(9) 0.4393(4) 0.52759(12) 0.0589(4) Uani 1 1 d .
H14A H 0.8775 0.3104 0.4907 0.088 Uiso 1 1 calc R
H14B H 0.8651 0.4441 0.5803 0.088 Uiso 1 1 calc R
H14C H 0.9432 0.4259 0.5463 0.088 Uiso 1 1 calc R
C15 C 0.87955(7) 0.6571(3) 0.47282(9) 0.0483(3) Uani 1 1 d .
H15 H 0.8949 0.7856 0.5122 0.058 Uiso 1 1 calc R
N16 N 0.80033(6) 0.6838(2) 0.44703(8) 0.0474(3) Uani 1 1 d .
H16A H 0.7758 0.6725 0.4966 0.071 Uiso 1 1 calc R
H16B H 0.7858 0.5751 0.4077 0.071 Uiso 1 1 calc R
H16C H 0.7922 0.8198 0.4215 0.071 Uiso 1 1 calc R
C17 C 0.92198(7) 0.6689(3) 0.38858(10) 0.0486(3) Uani 1 1 d .
C18 C 0.96396(10) 0.8593(3) 0.37359(14) 0.0620(4) Uani 1 1 d .
H18 H 0.9652 0.9805 0.4144 0.074 Uiso 1 1 calc R
C19 C 1.00408(11) 0.8691(4) 0.29789(16) 0.0779(6) Uani 1 1 d .
H19 H 1.0324 0.9968 0.2883 0.093 Uiso 1 1 calc R
C20 C 1.00244(10) 0.6928(5) 0.23722(14) 0.0780(6) Uani 1 1 d .
H20 H 1.0299 0.7001 0.1869 0.094 Uiso 1 1 calc R
C21 C 0.96020(11) 0.5047(4) 0.25049(13) 0.0713(5) Uani 1 1 d .
H21 H 0.9585 0.3858 0.2086 0.086 Uiso 1 1 calc R
C22 C 0.92009(9) 0.4916(3) 0.32617(12) 0.0587(4) Uani 1 1 d .
H22 H 0.8918 0.3635 0.3351 0.070 Uiso 1 1 calc R
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'
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
O1 O1 C2 0(10) 1 .
O3 C2 O1 123.63(16) . 1
O3 C2 O1 123.63(16) . .
O1 C2 O1 0.00(14) 1 .
O3 C2 C4 118.32(17) . .
O1 C2 C4 118.04(17) 1 .
O1 C2 C4 118.04(17) . .
C5 C4 C2 111.13(14) . .
C5 C4 H4A 109.4 . .
C2 C4 H4A 109.4 . .
C5 C4 H4B 109.4 . .
C2 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
C6 C5 C13 118.43(16) . .
C6 C5 C4 121.22(17) . .
C13 C5 C4 120.34(16) . .
C5 C6 C7 120.67(19) . .
C5 C6 H6 119.7 . .
C7 C6 H6 119.7 . .
C8 C7 C6 118.8(2) . .
C8 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
C7 C8 C12 122.08(18) . .
C7 C8 N10 120.1(2) . .
C12 C8 N10 117.9(2) . .
O11 N10 O9 123.9(3) . .
O11 N10 C8 118.3(4) . .
O9 N10 C8 117.8(3) . .
C8 C12 C13 118.81(19) . .
C8 C12 H12 120.6 . .
C13 C12 H12 120.6 . .
C12 C13 C5 121.23(18) . .
C12 C13 H13 119.4 . .
C5 C13 H13 119.4 . .
C15 C14 H14A 109.5 . .
C15 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C15 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N16 C15 C17 110.10(11) . .
N16 C15 C14 109.64(13) . .
C17 C15 C14 113.68(13) . .
N16 C15 H15 107.7 . .
C17 C15 H15 107.7 . .
C14 C15 H15 107.7 . .
C15 N16 H16A 109.5 . .
C15 N16 H16B 109.5 . .
H16A N16 H16B 109.5 . .
C15 N16 H16C 109.5 . .
H16A N16 H16C 109.5 . .
H16B N16 H16C 109.5 . .
C22 C17 C18 118.98(14) . .
C22 C17 C15 121.26(15) . .
C18 C17 C15 119.75(16) . .
C19 C18 C17 120.06(19) . .
C19 C18 H18 120.0 . .
C17 C18 H18 120.0 . .
C20 C19 C18 120.6(2) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C21 119.99(16) . .
C19 C20 H20 120.0 . .
C21 C20 H20 120.0 . .
C20 C21 C22 120.2(2) . .
C20 C21 H21 119.9 . .
C22 C21 H21 119.9 . .
C21 C22 C17 120.23(18) . .
C21 C22 H22 119.9 . .
C17 C22 H22 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 O1 0.000(3) 1
O1 C2 1.244(2) .
C2 O3 1.230(2) .
C2 O1 1.244(2) 1
C2 C4 1.525(2) .
C4 C5 1.508(2) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.374(3) .
C5 C13 1.390(3) .
C6 C7 1.390(3) .
C6 H6 0.9300 .
C7 C8 1.359(4) .
C7 H7 0.9300 .
C8 C12 1.364(3) .
C8 N10 1.476(3) .
O9 N10 1.220(5) .
N10 O11 1.192(5) .
C12 C13 1.367(3) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C15 1.520(2) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 N16 1.4933(18) .
C15 C17 1.5184(18) .
C15 H15 0.9800 .
N16 H16A 0.8900 .
N16 H16B 0.8900 .
N16 H16C 0.8900 .
C17 C22 1.387(2) .
C17 C18 1.387(3) .
C18 C19 1.386(3) .
C18 H18 0.9300 .
C19 C20 1.365(4) .
C19 H19 0.9300 .
C20 C21 1.374(4) .
C20 H20 0.9300 .
C21 C22 1.387(3) .
C21 H21 0.9300 .
C22 H22 0.9300 .
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
N16 H16A O1 0.89 1.92 2.8045(15) 173.6 1
N16 H16B O3 0.89 1.90 2.756(2) 159.4 4_646
N16 H16C O1 0.89 1.84 2.7211(18) 167.8 4_656
