#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510426.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_4510426
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 Br O2, C8 H12 N'
_chemical_formula_sum            'C16 H18 Br N O2'
_chemical_formula_weight         336.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4741(3)
_cell_length_b                   12.1369(5)
_cell_length_c                   20.5318(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1613.30(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20563
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    2.549
_exptl_absorpt_correction_T_max  0.8221
_exptl_absorpt_correction_T_min  0.3622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NIDDLE
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.992
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0767
_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)+(0.1572P)²+2.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.25
_reflns_number_gt                2323
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401863s_si_002.cif
_cod_data_source_block           (S)-PEA.3BPA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'ORTHORhOMBIC' changed to
'orthorhombic' 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_database_code               4510426
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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 0.4391(7) 0.8161(4) 0.4330(2) 0.0565(13) Uani 1 1 d .
C2 C 0.3235(9) 0.8346(5) 0.3860(3) 0.0405(13) Uani 1 1 d .
O3 O 0.1383(7) 0.8106(4) 0.3837(2) 0.0533(12) Uani 1 1 d .
C4 C 0.4258(11) 0.8880(10) 0.3255(4) 0.082(3) Uani 1 1 d .
H4A H 0.5344 0.9369 0.3405 0.098 Uiso 1 1 calc R
H4B H 0.4910 0.8300 0.3003 0.098 Uiso 1 1 calc R
C5 C 0.2873(12) 0.9519(7) 0.2810(3) 0.0554(18) Uani 1 1 d .
C6 C 0.3264(18) 1.0662(8) 0.2658(5) 0.080(2) Uani 1 1 d U
H6 H 0.4353 1.1037 0.2853 0.096 Uiso 1 1 calc R
C7 C 0.1982(19) 1.1187(8) 0.2215(5) 0.083(3) Uani 1 1 d U
H7 H 0.2287 1.1914 0.2107 0.099 Uiso 1 1 calc R
C8 C 0.0386(18) 1.0737(7) 0.1940(4) 0.073(2) Uani 1 1 d .
H8 H -0.0436 1.1128 0.1649 0.088 Uiso 1 1 calc R
C9 C -0.0036(13) 0.9667(7) 0.2094(3) 0.0552(18) Uani 1 1 d .
Br10 Br -0.23670(17) 0.89577(11) 0.17178(4) 0.0979(5) Uani 1 1 d .
C11 C 0.1211(11) 0.9059(6) 0.2516(3) 0.0503(15) Uani 1 1 d .
H11 H 0.0895 0.8325 0.2597 0.060 Uiso 1 1 calc R
N14 N 0.3390(7) 0.6581(4) 0.5231(2) 0.0374(11) Uani 1 1 d .
H12A H 0.2125 0.6676 0.5391 0.056 Uiso 1 1 calc R
H12B H 0.3684 0.7127 0.4957 0.056 Uiso 1 1 calc R
H12C H 0.4300 0.6580 0.5556 0.056 Uiso 1 1 calc R
C13 C 0.3493(10) 0.5515(5) 0.4880(3) 0.0426(13) Uani 1 1 d .
H13 H 0.2496 0.5542 0.4522 0.051 Uiso 1 1 calc R
C12 C 0.5670(14) 0.5414(7) 0.4582(4) 0.0631(19) Uani 1 1 d .
H14A H 0.6678 0.5386 0.4925 0.095 Uiso 1 1 calc R
H14B H 0.5938 0.6040 0.4310 0.095 Uiso 1 1 calc R
H14C H 0.5752 0.4753 0.4327 0.095 Uiso 1 1 calc R
C15 C 0.2915(10) 0.4572(5) 0.5311(3) 0.0457(14) Uani 1 1 d .
C16 C 0.1197(11) 0.3935(6) 0.5168(4) 0.0585(17) Uani 1 1 d .
H16 H 0.0386 0.4108 0.4808 0.070 Uiso 1 1 calc R
C17 C 0.0674(16) 0.3038(8) 0.5559(5) 0.077(3) Uani 1 1 d .
H17 H -0.0488 0.2621 0.5458 0.093 Uiso 1 1 calc R
C18 C 0.1850(18) 0.2762(7) 0.6089(5) 0.080(3) Uani 1 1 d .
H18 H 0.1519 0.2150 0.6341 0.096 Uiso 1 1 calc R
C19 C 0.3505(17) 0.3397(7) 0.6240(5) 0.078(3) Uani 1 1 d .
H19 H 0.4299 0.3230 0.6604 0.094 Uiso 1 1 calc R
C20 C 0.4018(15) 0.4287(7) 0.5858(4) 0.070(2) Uani 1 1 d .
H20 H 0.5155 0.4712 0.5974 0.083 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'
Br Br -0.2901 2.4595 '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 125.0(6) . 1
O3 C2 O1 125.0(6) . .
O1 C2 O1 0.0(5) 1 .
O3 C2 C4 118.8(6) . .
O1 C2 C4 116.1(5) 1 .
O1 C2 C4 116.1(5) . .
C5 C4 C2 116.7(6) . .
C5 C4 H4A 108.1 . .
C2 C4 H4A 108.1 . .
C5 C4 H4B 108.1 . .
C2 C4 H4B 108.1 . .
H4A C4 H4B 107.3 . .
C11 C5 C6 116.0(8) . .
C11 C5 C4 122.3(7) . .
C6 C5 C4 121.6(8) . .
C7 C6 C5 118.6(9) . .
C7 C6 H6 120.7 . .
C5 C6 H6 120.7 . .
C8 C7 C6 124.6(9) . .
C8 C7 H7 117.7 . .
C6 C7 H7 117.7 . .
C7 C8 C9 117.3(9) . .
C7 C8 H8 121.3 . .
C9 C8 H8 121.3 . .
C8 C9 C11 122.1(8) . .
C8 C9 Br10 119.7(7) . .
C11 C9 Br10 118.2(6) . .
C5 C11 C9 121.3(7) . .
C5 C11 H11 119.4 . .
C9 C11 H11 119.4 . .
C13 N14 H12A 109.5 . .
C13 N14 H12B 109.5 . .
H12A N14 H12B 109.5 . .
C13 N14 H12C 109.5 . .
H12A N14 H12C 109.5 . .
H12B N14 H12C 109.5 . .
N14 C13 C15 111.7(5) . .
N14 C13 C12 107.6(5) . .
C15 C13 C12 113.8(6) . .
N14 C13 H13 107.8 . .
C15 C13 H13 107.8 . .
C12 C13 H13 107.8 . .
C13 C12 H14A 109.5 . .
C13 C12 H14B 109.5 . .
H14A C12 H14B 109.5 . .
C13 C12 H14C 109.5 . .
H14A C12 H14C 109.5 . .
H14B C12 H14C 109.5 . .
C20 C15 C16 116.7(7) . .
C20 C15 C13 123.1(6) . .
C16 C15 C13 120.2(6) . .
C15 C16 C17 120.6(7) . .
C15 C16 H16 119.7 . .
C17 C16 H16 119.7 . .
C18 C17 C16 120.9(9) . .
C18 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C19 C18 C17 118.9(8) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C18 C19 C20 120.4(8) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C15 C20 C19 122.6(8) . .
C15 C20 H20 118.7 . .
C19 C20 H20 118.7 . .
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(18) 1
O1 C2 1.240(8) .
C2 O3 1.235(8) .
C2 O1 1.240(8) 1
C2 C4 1.551(9) .
C4 C5 1.497(11) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C11 1.354(10) .
C5 C6 1.444(12) .
C6 C7 1.387(15) .
C6 H6 0.9300 .
C7 C8 1.299(15) .
C7 H7 0.9300 .
C8 C9 1.364(12) .
C8 H8 0.9300 .
C9 C11 1.395(10) .
C9 Br10 1.901(8) .
C11 H11 0.9300 .
N14 C13 1.483(8) .
N14 H12A 0.8900 .
N14 H12B 0.8900 .
N14 H12C 0.8900 .
C13 C15 1.493(9) .
C13 C12 1.542(11) .
C13 H13 0.9800 .
C12 H14A 0.9600 .
C12 H14B 0.9600 .
C12 H14C 0.9600 .
C15 C20 1.375(10) .
C15 C16 1.386(10) .
C16 C17 1.395(12) .
C16 H16 0.9300 .
C17 C18 1.369(15) .
C17 H17 0.9300 .
C18 C19 1.356(14) .
C18 H18 0.9300 .
C19 C20 1.376(12) .
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 H12A O1 0.89 1.87 2.759(7) 175.9 4_466
N14 H12B O1 0.89 1.86 2.743(6) 174.4 1
N14 H12C O3 0.89 1.87 2.749(7) 166.9 4_566
