#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:58:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179606 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/70/4507014.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_4507014
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(C7 H16 N)'
_chemical_formula_sum            'C28 H40 N4 O4'
_chemical_formula_weight         496.64
_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                101.840(4)
_cell_angle_beta                 95.145(5)
_cell_angle_gamma                103.562(4)
_cell_formula_units_Z            1
_cell_length_a                   6.4485(17)
_cell_length_b                   8.177(2)
_cell_length_c                   13.989(4)
_cell_measurement_temperature    100(2)
_cell_volume                     694.4(3)
_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 0.904
_diffrn_measured_fraction_theta_max 0.904
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2071
_diffrn_reflns_theta_full        22.49
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.000(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          1.944
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1097P)²+0.5613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2081
_refine_ls_wR_factor_ref         0.2211
_reflns_number_gt                1278
_reflns_number_total             1635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301245c_si_002.cif
_cod_data_source_block           PS0619fkm
_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               4507014
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 0.2695(6) 0.7804(4) 0.5512(2) 0.0770(12) Uani 1 1 d .
O2 O 0.4816(6) 0.6569(4) 0.6295(2) 0.0774(12) Uani 1 1 d .
N10 N 0.0727(7) 0.9747(6) 1.0070(4) 0.0926(17) Uani 1 1 d .
C12 C 0.7323(9) 0.7965(8) 0.4559(3) 0.0844(17) Uani 1 1 d .
H12A H 0.8382 0.7598 0.4188 0.127 Uiso 1 1 calc R
H12B H 0.7605 0.7857 0.5225 0.127 Uiso 1 1 calc R
H12C H 0.7392 0.9151 0.4559 0.127 Uiso 1 1 calc R
C3 C 0.3424(8) 0.7402(5) 0.6264(3) 0.0552(12) Uani 1 1 d .
C4 C 0.2622(7) 0.8031(5) 0.7215(3) 0.0461(11) Uani 1 1 d .
C9 C 0.0804(8) 0.8642(6) 0.7223(4) 0.0599(13) Uani 1 1 d .
C8 C 0.0091(11) 0.9183(7) 0.8128(5) 0.0714(16) Uani 1 1 d .
C7 C 0.1232(11) 0.9133(6) 0.8996(3) 0.0716(16) Uani 1 1 d .
C6 C 0.3013(10) 0.8528(6) 0.8985(4) 0.0682(15) Uani 1 1 d .
C5 C 0.3702(9) 0.7987(6) 0.8109(3) 0.0584(13) Uani 1 1 d .
C15 C 0.4832(11) 0.6854(8) 0.1358(4) 0.0747(16) Uani 1 1 d .
C16 C 0.2606(10) 0.5656(8) 0.1045(4) 0.0764(17) Uani 1 1 d .
C17 C 0.1140(10) 0.6037(9) 0.1787(4) 0.0759(16) Uani 1 1 d .
C18 C 0.2070(8) 0.5953(7) 0.2802(4) 0.0633(14) Uani 1 1 d .
C13 C 0.4320(7) 0.7131(6) 0.3131(3) 0.0483(12) Uani 1 1 d .
C14 C 0.5785(8) 0.6780(7) 0.2372(3) 0.0568(13) Uani 1 1 d .
N11 N 0.5145(7) 0.6867(6) 0.4102(3) 0.0561(11) Uani 1 1 d .
H9 H 0.004(6) 0.872(4) 0.665(3) 0.039(10) Uiso 1 1 d .
H8 H -0.100(7) 0.948(5) 0.799(3) 0.048(14) Uiso 1 1 d .
H5 H 0.488(9) 0.764(7) 0.810(4) 0.084(19) Uiso 1 1 d .
H6 H 0.383(10) 0.849(8) 0.969(5) 0.13(2) Uiso 1 1 d .
H17A H 0.099(7) 0.712(7) 0.175(3) 0.070(16) Uiso 1 1 d .
H17B H -0.036(10) 0.528(7) 0.158(4) 0.096(17) Uiso 1 1 d .
H16A H 0.211(8) 0.574(6) 0.043(4) 0.081(15) Uiso 1 1 d .
H16B H 0.267(8) 0.440(7) 0.100(4) 0.083(16) Uiso 1 1 d .
H15A H 0.460(9) 0.811(8) 0.138(4) 0.100(18) Uiso 1 1 d .
H14A H 0.719(8) 0.759(6) 0.258(3) 0.076(15) Uiso 1 1 d .
H14B H 0.583(6) 0.561(6) 0.239(3) 0.049(11) Uiso 1 1 d .
H13 H 0.436(7) 0.836(6) 0.325(3) 0.075(14) Uiso 1 1 d .
H18B H 0.212(8) 0.468(7) 0.280(4) 0.094(17) Uiso 1 1 d .
H18A H 0.118(8) 0.625(6) 0.327(4) 0.069(14) Uiso 1 1 d .
H11A H 0.519(7) 0.572(7) 0.404(3) 0.071(15) Uiso 1 1 d .
H11B H 0.413(8) 0.714(6) 0.460(4) 0.079(15) Uiso 1 1 d .
H15B H 0.586(9) 0.664(7) 0.096(4) 0.090(19) Uiso 1 1 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 O1 C3 0(10) 1 .
O2 O2 C3 0(10) 1 .
N10 N10 C7 102.2(7) 2_577 .
N11 C12 H12A 109.5 . .
N11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C3 O2 0.0(3) 1 .
O2 C3 O1 125.2(4) 1 .
O2 C3 O1 125.2(4) . .
O2 C3 O1 125.2(4) 1 1
O2 C3 O1 125.2(4) . 1
O1 C3 O1 0.0(3) . 1
O2 C3 C4 117.5(4) 1 .
O2 C3 C4 117.5(4) . .
O1 C3 C4 117.3(4) . .
O1 C3 C4 117.3(4) 1 .
C9 C4 C5 118.4(4) . .
C9 C4 C3 121.4(4) . .
C5 C4 C3 120.2(4) . .
C4 C9 C8 119.4(5) . .
C4 C9 H9 122(2) . .
C8 C9 H9 119(2) . .
C7 C8 C9 120.0(6) . .
C7 C8 H8 135(3) . .
C9 C8 H8 105(3) . .
C6 C7 C8 120.4(5) . .
C6 C7 N10 112.7(5) . .
C8 C7 N10 126.9(6) . .
C7 C6 C5 119.9(5) . .
C7 C6 H6 117(3) . .
C5 C6 H6 123(3) . .
C6 C5 C4 121.9(6) . .
C6 C5 H5 120(4) . .
C4 C5 H5 118(4) . .
C16 C15 C14 111.6(4) . .
C16 C15 H15A 104(3) . .
C14 C15 H15A 110(3) . .
C16 C15 H15B 116(3) . .
C14 C15 H15B 104(3) . .
H15A C15 H15B 110(4) . .
C17 C16 C15 111.2(5) . .
C17 C16 H16A 113(3) . .
C15 C16 H16A 108(3) . .
C17 C16 H16B 106(3) . .
C15 C16 H16B 110(3) . .
H16A C16 H16B 108(4) . .
C16 C17 C18 111.1(5) . .
C16 C17 H17A 104(3) . .
C18 C17 H17A 114(3) . .
C16 C17 H17B 112(3) . .
C18 C17 H17B 112(3) . .
H17A C17 H17B 103(4) . .
C17 C18 C13 112.1(4) . .
C17 C18 H18B 110(3) . .
C13 C18 H18B 109(3) . .
C17 C18 H18A 111(3) . .
C13 C18 H18A 109(3) . .
H18B C18 H18A 106(4) . .
N11 C13 C14 111.5(4) . .
N11 C13 C18 108.0(4) . .
C14 C13 C18 111.2(4) . .
N11 C13 H13 106(3) . .
C14 C13 H13 107(3) . .
C18 C13 H13 113(3) . .
C15 C14 C13 111.7(5) . .
C15 C14 H14A 111(3) . .
C13 C14 H14A 110(3) . .
C15 C14 H14B 111(2) . .
C13 C14 H14B 101(2) . .
H14A C14 H14B 112(4) . .
C12 N11 C13 115.6(4) . .
C12 N11 H11A 107(3) . .
C13 N11 H11A 110(3) . .
C12 N11 H11B 106(3) . .
C13 N11 H11B 109(3) . .
H11A N11 H11B 109(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.250(5) .
O2 C3 1.250(5) .
N10 N10 1.127(9) 2_577
N10 C7 1.571(8) .
C12 N11 1.483(6) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C3 O2 1.250(5) 1
C3 O1 1.250(5) 1
C3 C4 1.506(6) .
C4 C9 1.378(6) .
C4 C5 1.387(6) .
C9 C8 1.407(7) .
C9 H9 0.93(4) .
C8 C7 1.375(9) .
C8 H8 0.81(4) .
C7 C6 1.353(8) .
C6 C5 1.364(7) .
C6 H6 1.09(6) .
C5 H5 0.87(6) .
C15 C16 1.505(8) .
C15 C14 1.513(7) .
C15 H15A 1.07(6) .
C15 H15B 0.93(6) .
C16 C17 1.500(8) .
C16 H16A 0.91(5) .
C16 H16B 1.03(5) .
C17 C18 1.512(7) .
C17 H17A 0.93(5) .
C17 H17B 1.00(6) .
C18 C13 1.513(6) .
C18 H18B 1.05(6) .
C18 H18A 0.94(5) .
C13 N11 1.491(5) .
C13 C14 1.511(6) .
C13 H13 0.98(5) .
C14 H14A 0.97(5) .
C14 H14B 0.97(4) .
N11 H11A 0.93(5) .
N11 H11B 1.02(6) .
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 0.93(5) 1.84(6) 2.757(6) 171(4) 2_666
N11 H11B O1 1.02(6) 1.72(6) 2.735(5) 173(4) 1
N11 H11B O2 1.02(6) 2.53(5) 3.149(5) 118(3) 1
