#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:58:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179606 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/70/4507015.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_4507015
loop_
_publ_author_name
'Sahoo, Pathik'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Secondary Ammonium Dicarboxylate (SAD)---A Supramolecular Synthon in
 Designing Low Molecular Weight Gelators Derived from Azo-Dicarboxylates
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5917
_journal_paper_doi               10.1021/cg301245c
_journal_volume                  12
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H8 N2 O4, 2(C8 H20 N)'
_chemical_formula_sum            'C30 H48 N4 O4'
_chemical_formula_weight         528.72
_chemical_name_systematic
; 
 ? 
;
_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_creation_method           SHELXL-97
_cell_angle_alpha                98.503(14)
_cell_angle_beta                 105.534(14)
_cell_angle_gamma                103.485(14)
_cell_formula_units_Z            1
_cell_length_a                   8.568(10)
_cell_length_b                   9.238(10)
_cell_length_c                   10.972(12)
_cell_measurement_temperature    100(2)
_cell_volume                     792.9(15)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'SHELXL-97, PLATON, MERCURY 2.2'
_computing_publication_material  'SHELXL-97, PLATON, MERCURY 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3767
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            BROWN
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.037
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1693
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.605
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.1186
_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)+(0.1698P)²+0.1986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3442
_refine_ls_wR_factor_ref         0.3589
_reflns_number_gt                1383
_reflns_number_total             1693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301245c_si_003.cif
_cod_data_source_block           619dl_0m
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4507015
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
O1 O 0.2102(6) 0.8168(5) 0.0311(4) 0.1010(17) Uani 1 1 d .
O2 O 0.4476(6) 0.9264(5) 0.1944(4) 0.0920(15) Uani 1 1 d .
C3 C 0.2988(8) 0.8381(6) 0.1450(6) 0.0679(16) Uani 1 1 d .
C4 C 0.2258(7) 0.7533(6) 0.2345(5) 0.0617(15) Uani 1 1 d .
C5 C 0.3036(8) 0.7879(7) 0.3655(6) 0.0790(18) Uani 1 1 d .
H5 H 0.4052 0.8649 0.4020 0.095 Uiso 1 1 calc R
C6 C 0.2314(11) 0.7084(9) 0.4448(6) 0.097(2) Uani 1 1 d .
H6 H 0.2831 0.7337 0.5343 0.116 Uiso 1 1 calc R
C7 C 0.0816(12) 0.5909(9) 0.3889(9) 0.105(3) Uani 1 1 d .
C8 C 0.0052(9) 0.5518(8) 0.2567(8) 0.097(2) Uani 1 1 d .
H8 H -0.0925 0.4705 0.2191 0.116 Uiso 1 1 calc R
C9 C 0.0760(8) 0.6353(7) 0.1807(6) 0.0775(18) Uani 1 1 d .
H9 H 0.0225 0.6123 0.0916 0.093 Uiso 1 1 calc R
N10 N -0.0293(13) 0.4770(11) 0.4448(7) 0.097(3) Uiso 0.73 1 d P
N10' N -0.075(2) 0.4382(19) 0.4813(19) 0.058(4) Uiso 0.27 1 d P
N11 N 0.2746(5) 0.0192(4) 0.8841(4) 0.0625(14) Uani 1 1 d .
H11A H 0.3792 0.0354 0.8768 0.075 Uiso 1 1 calc R
H11B H 0.2658 -0.0436 0.9388 0.075 Uiso 1 1 calc R
C12 C 0.2561(8) 0.1682(6) 0.9427(6) 0.0826(18) Uani 1 1 d .
H12A H 0.2451 0.2297 0.8782 0.099 Uiso 1 1 calc R
H12B H 0.1528 0.1491 0.9661 0.099 Uiso 1 1 calc R
C13 C 0.3997(7) 0.2557(6) 1.0593(6) 0.0824(18) Uani 1 1 d .
H13A H 0.5033 0.2749 1.0364 0.099 Uiso 1 1 calc R
H13B H 0.4105 0.1949 1.1245 0.099 Uiso 1 1 calc R
C14 C 0.3778(9) 0.4075(7) 1.1167(7) 0.102(2) Uani 1 1 d .
H14A H 0.3658 0.4673 1.0509 0.123 Uiso 1 1 calc R
H14B H 0.2742 0.3876 1.1395 0.123 Uiso 1 1 calc R
C15 C 0.5229(10) 0.5005(8) 1.2357(8) 0.128(3) Uani 1 1 d .
H15A H 0.5265 0.4480 1.3052 0.191 Uiso 1 1 calc R
H15B H 0.5071 0.5986 1.2613 0.191 Uiso 1 1 calc R
H15C H 0.6273 0.5138 1.2160 0.191 Uiso 1 1 calc R
C16 C 0.1494(9) -0.0594(8) 0.7541(6) 0.095(2) Uani 1 1 d .
H16A H 0.1620 0.0068 0.6944 0.114 Uiso 1 1 calc R
H16B H 0.1765 -0.1513 0.7230 0.114 Uiso 1 1 calc R
C17 C -0.0278(9) -0.1016(9) 0.7502(6) 0.112(3) Uani 1 1 d D
C18 C -0.1376(14) -0.1591(13) 0.6058(9) 0.181(4) Uiso 1 1 d D
C19 C -0.3101(19) -0.2363(18) 0.5964(16) 0.251(7) Uiso 1 1 d 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 0.0000 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 C3 O2 125.2(5) . .
O1 C3 C4 118.4(6) . .
O2 C3 C4 116.4(6) . .
C5 C4 C9 119.2(5) . .
C5 C4 C3 122.1(6) . .
C9 C4 C3 118.7(5) . .
C4 C5 C6 120.4(6) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C7 C6 C5 119.4(6) . .
C7 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C8 C7 C6 120.7(5) . .
C8 C7 N10' 147.1(10) . 2_566
C6 C7 N10' 92.2(9) . 2_566
C8 C7 N10 105.8(8) . .
C6 C7 N10 133.5(8) . .
N10' C7 N10 41.3(6) 2_566 .
C7 C8 C9 118.8(7) . .
C7 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
C8 C9 C4 121.4(6) . .
C8 C9 H9 119.3 . .
C4 C9 H9 119.3 . .
N10' N10 N10' 103(2) . 2_566
N10' N10 N10 66.2(17) . 2_566
N10' N10 N10 36.9(10) 2_566 2_566
N10' N10 C7 168(2) . .
N10' N10 C7 66.6(16) 2_566 .
N10 N10 C7 103.3(14) 2_566 .
N10 N10' N10 77(2) . 2_566
N10 N10' N10' 47.8(16) . 2_566
N10 N10' N10' 29.1(8) 2_566 2_566
N10 N10' C7 148(3) . 2_566
N10 N10' C7 72.1(15) 2_566 2_566
N10' N10' C7 101.0(19) 2_566 2_566
C16 N11 C12 115.2(4) . .
C16 N11 H11A 108.5 . .
C12 N11 H11A 108.5 . .
C16 N11 H11B 108.5 . .
C12 N11 H11B 108.5 . .
H11A N11 H11B 107.5 . .
C13 C12 N11 113.5(5) . .
C13 C12 H12A 108.9 . .
N11 C12 H12A 108.9 . .
C13 C12 H12B 108.9 . .
N11 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
C12 C13 C14 112.3(5) . .
C12 C13 H13A 109.1 . .
C14 C13 H13A 109.1 . .
C12 C13 H13B 109.1 . .
C14 C13 H13B 109.1 . .
H13A C13 H13B 107.9 . .
C15 C14 C13 113.7(6) . .
C15 C14 H14A 108.8 . .
C13 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C13 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 N11 115.5(5) . .
C17 C16 H16A 108.4 . .
N11 C16 H16A 108.4 . .
C17 C16 H16B 108.4 . .
N11 C16 H16B 108.4 . .
H16A C16 H16B 107.5 . .
C16 C17 C18 107.5(7) . .
C19 C18 C17 109.9(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.235(7) .
O2 C3 1.265(7) .
C3 C4 1.516(7) .
C4 C5 1.365(8) .
C4 C9 1.391(8) .
C5 C6 1.394(9) .
C5 H5 0.9300 .
C6 C7 1.391(11) .
C6 H6 0.9300 .
C7 C8 1.375(10) .
C7 N10' 1.50(2) 2_566
C7 N10 1.556(13) .
C8 C9 1.379(8) .
C8 H8 0.9300 .
C9 H9 0.9300 .
N10 N10' 0.709(17) .
N10 N10' 1.080(14) 2_566
N10 N10 1.150(15) 2_566
N10' N10 1.080(14) 2_566
N10' N10' 1.42(4) 2_566
N10' C7 1.50(2) 2_566
N11 C16 1.491(7) .
N11 C12 1.492(7) .
N11 H11A 0.9000 .
N11 H11B 0.9000 .
C12 C13 1.481(8) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.525(8) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.513(9) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.463(10) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.549(8) .
C18 C19 1.451(10) .
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
N11 H11A O2 0.90 1.84 2.706(6) 160.0 2_666
N11 H11B O1 0.90 1.81 2.701(6) 170.0 1_546
