#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510422.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_4510422
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 R
_chemical_formula_moiety         'C8 H6 F O2, C8 H12 N'
_chemical_formula_sum            'C16 H18 F N O2'
_chemical_formula_weight         275.31
_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                 92.249(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.1479(17)
_cell_length_b                   6.3269(5)
_cell_length_c                   12.3797(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1576.9(2)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, 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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9798
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NIDDLE
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.059
_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   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                2008
_reflns_number_total             2735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401863s_si_002.cif
_cod_data_source_block           (R)-PEA.4FPA
_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      'C 2'
_cod_database_code               4510422
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 0.28328(10) 0.3771(3) 0.61567(14) 0.0803(6) Uani 1 1 d .
C2 C 0.28691(12) 0.4848(4) 0.69942(18) 0.0666(6) Uani 1 1 d .
O3 O 0.27636(16) 0.6738(3) 0.70000(18) 0.1249(10) Uani 1 1 d .
C4 C 0.30246(16) 0.3691(6) 0.8047(2) 0.0929(9) Uani 1 1 d .
H4A H 0.3317 0.2507 0.7915 0.111 Uiso 1 1 calc R
H4B H 0.3253 0.4638 0.8553 0.111 Uiso 1 1 calc R
C5 C 0.23982(13) 0.2897(4) 0.85313(17) 0.0675(7) Uani 1 1 d .
C6 C 0.21700(16) 0.0906(5) 0.8290(2) 0.0802(8) Uani 1 1 d .
H6 H 0.2414 0.0045 0.7843 0.096 Uiso 1 1 calc R
C7 C 0.1588(2) 0.0147(7) 0.8694(3) 0.1080(13) Uani 1 1 d .
H7 H 0.1429 -0.1196 0.8521 0.130 Uiso 1 1 calc R
C8 C 0.12538(18) 0.1473(11) 0.9365(3) 0.1189(17) Uani 1 1 d .
F9 F 0.06935(13) 0.0685(9) 0.9773(2) 0.215(2) Uani 1 1 d .
C10 C 0.1478(2) 0.3440(10) 0.9633(3) 0.1192(16) Uani 1 1 d .
H10 H 0.1246 0.4293 1.0100 0.143 Uiso 1 1 calc R
C11 C 0.20505(18) 0.4131(6) 0.9203(2) 0.0892(9) Uani 1 1 d .
H11 H 0.2206 0.5479 0.9373 0.107 Uiso 1 1 calc R
C12 C 0.38755(18) 0.7714(7) 0.4512(3) 0.1063(11) Uani 1 1 d .
H12A H 0.3811 0.6522 0.4976 0.159 Uiso 1 1 calc R
H12B H 0.4322 0.7702 0.4268 0.159 Uiso 1 1 calc R
H12C H 0.3569 0.7635 0.3900 0.159 Uiso 1 1 calc R
C13 C 0.37572(13) 0.9736(5) 0.5129(2) 0.0748(7) Uani 1 1 d .
H13 H 0.3804 1.0919 0.4628 0.090 Uiso 1 1 calc R
N14 N 0.30615(10) 0.9746(3) 0.54962(15) 0.0641(5) Uani 1 1 d .
H14A H 0.3012 0.8719 0.5978 0.096 Uiso 1 1 calc R
H14B H 0.2782 0.9537 0.4932 0.096 Uiso 1 1 calc R
H14C H 0.2975 1.0987 0.5798 0.096 Uiso 1 1 calc R
C15 C 0.42280(14) 1.0120(5) 0.6096(2) 0.0802(8) Uani 1 1 d .
C16 C 0.43429(16) 0.8595(7) 0.6871(3) 0.1030(11) Uani 1 1 d .
H16 H 0.4136 0.7285 0.6801 0.124 Uiso 1 1 calc R
C17 C 0.4769(2) 0.9003(11) 0.7766(4) 0.1363(18) Uani 1 1 d .
H17 H 0.4851 0.7962 0.8284 0.164 Uiso 1 1 calc R
C18 C 0.5060(3) 1.0920(13) 0.7873(5) 0.164(2) Uani 1 1 d .
H18 H 0.5332 1.1205 0.8479 0.197 Uiso 1 1 calc R
C19 C 0.4961(2) 1.2403(9) 0.7123(5) 0.158(2) Uani 1 1 d .
H19 H 0.5178 1.3696 0.7198 0.189 Uiso 1 1 calc R
C20 C 0.45388(18) 1.2043(7) 0.6231(3) 0.1122(12) Uani 1 1 d .
H20 H 0.4465 1.3107 0.5722 0.135 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'
F F 0.0171 0.0103 '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
O3 C2 O3 0.0(3) 1
O3 C2 O1 122.8(3) 1
O3 C2 O1 122.8(3) .
O3 C2 C4 120.0(3) 1
O3 C2 C4 120.0(3) .
O1 C2 C4 117.2(3) .
O3 O3 C2 0(10) 1
C5 C4 C2 110.8(2) .
C5 C4 H4A 109.5 .
C2 C4 H4A 109.5 .
C5 C4 H4B 109.5 .
C2 C4 H4B 109.5 .
H4A C4 H4B 108.1 .
C11 C5 C6 119.1(3) .
C11 C5 C4 120.9(3) .
C6 C5 C4 120.0(3) .
C5 C6 C7 121.6(3) .
C5 C6 H6 119.2 .
C7 C6 H6 119.2 .
C8 C7 C6 116.8(4) .
C8 C7 H7 121.6 .
C6 C7 H7 121.6 .
F9 C8 C10 121.4(6) .
F9 C8 C7 116.0(6) .
C10 C8 C7 122.6(4) .
C11 C10 C8 118.5(4) .
C11 C10 H10 120.8 .
C8 C10 H10 120.8 .
C5 C11 C10 121.4(4) .
C5 C11 H11 119.3 .
C10 C11 H11 119.3 .
C13 C12 H12A 109.5 .
C13 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C13 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
N14 C13 C12 109.0(2) .
N14 C13 C15 109.0(2) .
C12 C13 C15 115.3(3) .
N14 C13 H13 107.7 .
C12 C13 H13 107.7 .
C15 C13 H13 107.7 .
C13 N14 H14A 109.5 .
C13 N14 H14B 109.5 .
H14A N14 H14B 109.5 .
C13 N14 H14C 109.5 .
H14A N14 H14C 109.5 .
H14B N14 H14C 109.5 .
C16 C15 C20 118.2(3) .
C16 C15 C13 121.4(3) .
C20 C15 C13 120.3(3) .
C15 C16 C17 120.3(4) .
C15 C16 H16 119.8 .
C17 C16 H16 119.8 .
C18 C17 C16 119.6(5) .
C18 C17 H17 120.2 .
C16 C17 H17 120.2 .
C19 C18 C17 120.9(4) .
C19 C18 H18 119.6 .
C17 C18 H18 119.6 .
C18 C19 C20 120.7(5) .
C18 C19 H19 119.7 .
C20 C19 H19 119.7 .
C15 C20 C19 120.3(4) .
C15 C20 H20 119.9 .
C19 C20 H20 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.240(3) .
C2 O3 1.215(3) 1
C2 O3 1.215(3) .
C2 C4 1.517(4) .
O3 O3 0.000(8) 1
C4 C5 1.504(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C11 1.355(4) .
C5 C6 1.370(4) .
C6 C7 1.379(5) .
C6 H6 0.9300 .
C7 C8 1.374(7) .
C7 H7 0.9300 .
C8 F9 1.350(5) .
C8 C10 1.362(7) .
C10 C11 1.361(6) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.514(5) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 N14 1.490(3) .
C13 C15 1.517(4) .
C13 H13 0.9800 .
N14 H14A 0.8900 .
N14 H14B 0.8900 .
N14 H14C 0.8900 .
C15 C16 1.374(5) .
C15 C20 1.376(5) .
C16 C17 1.398(6) .
C16 H16 0.9300 .
C17 C18 1.351(9) .
C17 H17 0.9300 .
C18 C19 1.329(8) .
C18 H18 0.9300 .
C19 C20 1.386(6) .
C19 H19 0.9300 .
C20 H20 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
N14 H14C O1 0.89 1.84 2.719(3) 168.6 1_565
N14 H14B O1 0.89 1.86 2.743(3) 172.4 4_556
N14 H14A O3 0.89 1.86 2.745(3) 170.5 1
