#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510411.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_4510411
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 H7 O2, C8 H12 N '
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-11-09 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.798(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7910(11)
_cell_length_b                   6.0752(4)
_cell_length_c                   15.8571(11)
_cell_measurement_temperature    296(2)
_cell_volume                     1470.77(17)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13580
_diffrn_reflns_theta_full        22.21
_diffrn_reflns_theta_max         22.21
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NIDDLE
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.053
_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   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0801P)²+0.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                2900
_reflns_number_total             3425
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401863s_si_002.cif
_cod_data_source_block           tapas1802a
_cod_depositor_comments
'Adding full bibliography for 4510410--4510441.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4510411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.90989(14) 0.6069(4) 0.42435(12) 0.0549(5) Uani 1 1 d .
C2 C 0.8350(2) 0.5215(6) 0.41075(17) 0.0467(8) Uani 1 1 d .
O3 O 0.82171(15) 0.3196(4) 0.40603(15) 0.0684(7) Uani 1 1 d .
C4 C 0.7571(2) 0.6726(6) 0.40511(19) 0.0583(9) Uani 1 1 d .
H4A H 0.7668 0.8118 0.3791 0.070 Uiso 1 1 calc R
H4B H 0.7046 0.6060 0.3686 0.070 Uiso 1 1 calc R
C5 C 0.74541(19) 0.7112(5) 0.49542(19) 0.0502(8) Uani 1 1 d .
C6 C 0.7101(2) 0.5493(6) 0.5372(2) 0.0668(9) Uani 1 1 d .
H6 H 0.6905 0.4186 0.5081 0.080 Uiso 1 1 calc R
C7 C 0.7035(3) 0.5795(8) 0.6227(3) 0.0822(12) Uani 1 1 d .
H7 H 0.6800 0.4686 0.6501 0.099 Uiso 1 1 calc R
C8 C 0.7315(3) 0.7708(8) 0.6661(2) 0.0820(12) Uani 1 1 d .
H8 H 0.7276 0.7904 0.7231 0.098 Uiso 1 1 calc R
C9 C 0.7652(3) 0.9327(8) 0.6249(2) 0.0813(11) Uani 1 1 d .
H9 H 0.7835 1.0643 0.6538 0.098 Uiso 1 1 calc R
C10 C 0.7724(2) 0.9034(6) 0.5405(2) 0.0655(9) Uani 1 1 d .
H10 H 0.7960 1.0156 0.5137 0.079 Uiso 1 1 calc R
C11 C 1.0673(2) -0.1049(8) 0.3469(2) 0.0772(11) Uani 1 1 d .
H11A H 1.1078 -0.1138 0.4034 0.116 Uiso 1 1 calc R
H11B H 1.0987 -0.0766 0.3037 0.116 Uiso 1 1 calc R
H11C H 1.0361 -0.2414 0.3340 0.116 Uiso 1 1 calc R
C12 C 1.00291(19) 0.0801(6) 0.34650(18) 0.0543(8) Uani 1 1 d .
H12 H 1.0362 0.2177 0.3587 0.065 Uiso 1 1 calc R
N13 N 0.95843(16) 0.0444(4) 0.41814(14) 0.0504(6) Uani 1 1 d .
H13A H 0.9350 -0.0896 0.4133 0.076 Uiso 1 1 calc R
H13B H 0.9165 0.1446 0.4142 0.076 Uiso 1 1 calc R
H13C H 0.9974 0.0571 0.4695 0.076 Uiso 1 1 calc R
C14 C 0.93611(19) 0.1059(6) 0.25966(17) 0.0515(8) Uani 1 1 d .
C15 C 0.8784(2) -0.0612(7) 0.22554(19) 0.0679(9) Uani 1 1 d .
H15 H 0.8791 -0.1905 0.2571 0.082 Uiso 1 1 calc R
C16 C 0.8200(2) -0.0385(9) 0.1453(2) 0.0865(13) Uani 1 1 d .
H16 H 0.7808 -0.1517 0.1235 0.104 Uiso 1 1 calc R
C17 C 0.8189(3) 0.1468(11) 0.0979(3) 0.0929(15) Uani 1 1 d .
H17 H 0.7795 0.1610 0.0435 0.112 Uiso 1 1 calc R
C18 C 0.8759(4) 0.3123(10) 0.1304(3) 0.1029(15) Uani 1 1 d .
H18 H 0.8756 0.4397 0.0978 0.124 Uiso 1 1 calc R
C19 C 0.9338(3) 0.2927(7) 0.2109(3) 0.0798(11) Uani 1 1 d .
H19 H 0.9720 0.4078 0.2325 0.096 Uiso 1 1 calc R
O1' O 0.62753(16) 0.0953(5) 0.91905(17) 0.0813(7) Uani 1 1 d .
C2' C 0.6087(2) 0.2877(7) 0.9008(2) 0.0609(9) Uani 1 1 d .
O3' O 0.5535(2) 0.3905(5) 0.92914(17) 0.0897(9) Uani 1 1 d .
C4' C 0.6495(2) 0.4091(11) 0.8378(3) 0.114(2) Uani 1 1 d .
H4'1 H 0.6359 0.3299 0.7828 0.137 Uiso 1 1 calc R
H4'2 H 0.6226 0.5533 0.8268 0.137 Uiso 1 1 calc R
C5' C 0.7470(2) 0.4382(6) 0.86785(19) 0.0577(9) Uani 1 1 d .
C6' C 0.8022(3) 0.2752(8) 0.8554(2) 0.0812(12) Uani 1 1 d .
H6' H 0.7799 0.1423 0.8301 0.097 Uiso 1 1 calc R
C7' C 0.8949(5) 0.3118(15) 0.8818(4) 0.127(2) Uani 1 1 d .
H7' H 0.9345 0.2044 0.8749 0.153 Uiso 1 1 calc R
C8' C 0.9225(4) 0.5142(19) 0.9180(5) 0.133(3) Uani 1 1 d .
H8' H 0.9822 0.5442 0.9346 0.160 Uiso 1 1 calc R
C9' C 0.8684(6) 0.6633(12) 0.9296(4) 0.135(3) Uani 1 1 d .
H9' H 0.8900 0.7968 0.9549 0.162 Uiso 1 1 calc R
C10' C 0.7821(4) 0.6294(8) 0.9059(3) 0.0902(13) Uani 1 1 d .
H10' H 0.7449 0.7396 0.9157 0.108 Uiso 1 1 calc R
C11' C 0.3575(3) 1.0266(8) 0.8461(3) 0.0956(14) Uani 1 1 d .
H11D H 0.3926 1.1518 0.8400 0.143 Uiso 1 1 calc R
H11E H 0.3440 1.0322 0.9018 0.143 Uiso 1 1 calc R
H11F H 0.3041 1.0285 0.8006 0.143 Uiso 1 1 calc R
C12' C 0.4077(2) 0.8170(7) 0.8397(2) 0.0669(10) Uani 1 1 d .
H12' H 0.3699 0.6925 0.8450 0.080 Uiso 1 1 calc R
N13' N 0.48736(18) 0.8057(5) 0.91499(16) 0.0641(7) Uani 1 1 d .
H13D H 0.5138 0.6766 0.9144 0.096 Uiso 1 1 calc R
H13E H 0.4716 0.8199 0.9647 0.096 Uiso 1 1 calc R
H13F H 0.5240 0.9139 0.9105 0.096 Uiso 1 1 calc R
C14' C 0.4336(2) 0.7898(6) 0.7555(2) 0.0587(8) Uani 1 1 d .
C15' C 0.4797(2) 0.9508(7) 0.7249(2) 0.0742(10) Uani 1 1 d .
H15' H 0.4944 1.0806 0.7564 0.089 Uiso 1 1 calc R
C16' C 0.5046(3) 0.9213(10) 0.6478(2) 0.0920(13) Uani 1 1 d .
H16' H 0.5367 1.0297 0.6284 0.110 Uiso 1 1 calc R
C17' C 0.4820(3) 0.7339(10) 0.6008(3) 0.0922(14) Uani 1 1 d .
H17' H 0.4989 0.7137 0.5493 0.111 Uiso 1 1 calc R
C18' C 0.4349(3) 0.5759(9) 0.6287(3) 0.0997(14) Uani 1 1 d .
H18' H 0.4185 0.4495 0.5955 0.120 Uiso 1 1 calc R
C19' C 0.4109(2) 0.6014(8) 0.7061(3) 0.0801(11) Uani 1 1 d .
H19' H 0.3794 0.4911 0.7251 0.096 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
O3 C2 O3 0.0(2) 1 .
O3 C2 O1 123.6(3) 1 .
O3 C2 O1 123.6(3) . .
O3 C2 C4 118.1(3) 1 .
O3 C2 C4 118.1(3) . .
O1 C2 C4 118.2(3) . .
O3 O3 C2 0(10) 1 .
C5 C4 C2 109.4(2) . .
C5 C4 H4A 109.8 . .
C2 C4 H4A 109.8 . .
C5 C4 H4B 109.8 . .
C2 C4 H4B 109.8 . .
H4A C4 H4B 108.2 . .
C10 C5 C6 117.6(3) . .
C10 C5 C4 121.8(3) . .
C6 C5 C4 120.5(3) . .
C5 C6 C7 120.7(4) . .
C5 C6 H6 119.6 . .
C7 C6 H6 119.6 . .
C8 C7 C6 120.4(4) . .
C8 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
C9 C8 C7 119.2(3) . .
C9 C8 H8 120.4 . .
C7 C8 H8 120.4 . .
C8 C9 C10 120.7(4) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C5 C10 C9 121.3(3) . .
C5 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C12 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C12 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N13 C12 C11 109.5(3) . .
N13 C12 C14 110.6(2) . .
C11 C12 C14 113.1(2) . .
N13 C12 H12 107.8 . .
C11 C12 H12 107.8 . .
C14 C12 H12 107.8 . .
C12 N13 H13A 109.5 . .
C12 N13 H13B 109.5 . .
H13A N13 H13B 109.5 . .
C12 N13 H13C 109.5 . .
H13A N13 H13C 109.5 . .
H13B N13 H13C 109.5 . .
C19 C14 C15 118.0(3) . .
C19 C14 C12 120.8(3) . .
C15 C14 C12 121.2(3) . .
C16 C15 C14 120.6(4) . .
C16 C15 H15 119.7 . .
C14 C15 H15 119.7 . .
C17 C16 C15 120.6(4) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C16 C17 C18 119.4(4) . .
C16 C17 H17 120.3 . .
C18 C17 H17 120.3 . .
C17 C18 C19 120.5(4) . .
C17 C18 H18 119.7 . .
C19 C18 H18 119.7 . .
C14 C19 C18 120.8(4) . .
C14 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
O1' C2' O3' 122.9(3) . 1
O1' C2' O3' 122.9(3) . .
O3' C2' O3' 0.0(2) 1 .
O1' C2' C4' 120.3(4) . .
O3' C2' C4' 116.7(4) 1 .
O3' C2' C4' 116.7(4) . .
O3' O3' C2' 0(10) 1 .
C5' C4' C2' 115.0(3) . .
C5' C4' H4'1 108.5 . .
C2' C4' H4'1 108.5 . .
C5' C4' H4'2 108.5 . .
C2' C4' H4'2 108.5 . .
H4'1 C4' H4'2 107.5 . .
C10' C5' C6' 118.7(4) . .
C10' C5' C4' 120.7(4) . .
C6' C5' C4' 120.6(4) . .
C5' C6' C7' 119.1(5) . .
C5' C6' H6' 120.4 . .
C7' C6' H6' 120.4 . .
C8' C7' C6' 116.8(6) . .
C8' C7' H7' 121.6 . .
C6' C7' H7' 121.6 . .
C9' C8' C7' 122.3(7) . .
C9' C8' H8' 118.8 . .
C7' C8' H8' 118.8 . .
C8' C9' C10' 121.1(7) . .
C8' C9' H9' 119.4 . .
C10' C9' H9' 119.4 . .
C9' C10' C5' 121.9(5) . .
C9' C10' H10' 119.0 . .
C5' C10' H10' 119.1 . .
C12' C11' H11D 109.5 . .
C12' C11' H11E 109.5 . .
H11D C11' H11E 109.5 . .
C12' C11' H11F 109.5 . .
H11D C11' H11F 109.5 . .
H11E C11' H11F 109.5 . .
N13' C12' C14' 109.9(3) . .
N13' C12' C11' 109.4(3) . .
C14' C12' C11' 114.7(3) . .
N13' C12' H12' 107.6 . .
C14' C12' H12' 107.6 . .
C11' C12' H12' 107.6 . .
C12' N13' H13D 109.5 . .
C12' N13' H13E 109.5 . .
H13D N13' H13E 109.5 . .
C12' N13' H13F 109.5 . .
H13D N13' H13F 109.5 . .
H13E N13' H13F 109.5 . .
C15' C14' C19' 118.2(3) . .
C15' C14' C12' 121.5(3) . .
C19' C14' C12' 120.3(4) . .
C14' C15' C16' 120.8(4) . .
C14' C15' H15' 119.6 . .
C16' C15' H15' 119.6 . .
C17' C16' C15' 119.8(4) . .
C17' C16' H16' 120.1 . .
C15' C16' H16' 120.1 . .
C16' C17' C18' 120.3(4) . .
C16' C17' H17' 119.9 . .
C18' C17' H17' 119.9 . .
C17' C18' C19' 120.5(4) . .
C17' C18' H18' 119.7 . .
C19' C18' H18' 119.7 . .
C14' C19' C18' 120.4(4) . .
C14' C19' H19' 119.8 . .
C18' C19' H19' 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.258(4) .
C2 O3 1.243(4) 1
C2 O3 1.243(4) .
C2 C4 1.520(4) .
O3 O3 0.000(7) 1
C4 C5 1.508(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C10 1.379(5) .
C5 C6 1.380(5) .
C6 C7 1.398(5) .
C6 H6 0.9300 .
C7 C8 1.365(6) .
C7 H7 0.9300 .
C8 C9 1.362(6) .
C8 H8 0.9300 .
C9 C10 1.383(5) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C12 1.514(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 N13 1.496(3) .
C12 C14 1.514(4) .
C12 H12 0.9800 .
N13 H13A 0.8900 .
N13 H13B 0.8900 .
N13 H13C 0.8900 .
C14 C19 1.369(5) .
C14 C15 1.379(5) .
C15 C16 1.375(5) .
C15 H15 0.9300 .
C16 C17 1.352(7) .
C16 H16 0.9300 .
C17 C18 1.360(7) .
C17 H17 0.9300 .
C18 C19 1.372(6) .
C18 H18 0.9300 .
C19 H19 0.9300 .
O1' C2' 1.223(5) .
C2' O3' 1.247(4) 1
C2' O3' 1.247(4) .
C2' C4' 1.512(5) .
O3' O3' 0.000(8) 1
C4' C5' 1.501(5) .
C4' H4'1 0.9700 .
C4' H4'2 0.9700 .
C5' C10' 1.360(6) .
C5' C6' 1.367(5) .
C6' C7' 1.433(8) .
C6' H6' 0.9300 .
C7' C8' 1.379(10) .
C7' H7' 0.9300 .
C8' C9' 1.290(10) .
C8' H8' 0.9300 .
C9' C10' 1.334(8) .
C9' H9' 0.9300 .
C10' H10' 0.9300 .
C11' C12' 1.517(6) .
C11' H11D 0.9600 .
C11' H11E 0.9600 .
C11' H11F 0.9600 .
C12' N13' 1.498(4) .
C12' C14' 1.503(5) .
C12' H12' 0.9800 .
N13' H13D 0.8900 .
N13' H13E 0.8900 .
N13' H13F 0.8900 .
C14' C15' 1.379(5) .
C14' C19' 1.380(6) .
C15' C16' 1.388(5) .
C15' H15' 0.9300 .
C16' C17' 1.358(7) .
C16' H16' 0.9300 .
C17' C18' 1.356(7) .
C17' H17' 0.9300 .
C18' C19' 1.382(6) .
C18' H18' 0.9300 .
C19' H19' 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
N13 H13A O1 0.89 1.90 2.775(3) 166.0 1_545
N13 H13B O3 0.89 1.81 2.699(3) 172.8 1
N13 H13C O1 0.89 1.95 2.838(3) 173.6 2_746
N13' H13D O3' 0.89 1.84 2.717(4) 167.3 1
N13' H13E O3' 0.89 1.87 2.758(4) 171.5 2_657
N13' H13F O1' 0.89 1.95 2.815(4) 164.4 1_565
