#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:58:16 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179606 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/70/4507018.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_4507018
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         'C18 H12 N2 O4, 2(C8 H20 N)'
_chemical_formula_sum            'C34 H52 N4 O4'
_chemical_formula_weight         580.80
_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                108.919(3)
_cell_angle_beta                 109.462(3)
_cell_angle_gamma                101.428(4)
_cell_formula_units_Z            1
_cell_length_a                   8.1405(13)
_cell_length_b                   11.1094(18)
_cell_length_c                   11.6064(19)
_cell_measurement_temperature    293(2)
_cell_volume                     879.3(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      293(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2612
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         1831
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1909
_refine_ls_R_factor_gt           0.1536
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1984P)²+1.7777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3830
_refine_ls_wR_factor_ref         0.4161
_reflns_number_gt                1283
_reflns_number_total             1831
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301245c_si_006.cif
_cod_data_source_block           07104lm
_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_cell_volume        879.3(2)
_cod_database_code               4507018
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 1.0110(10) -0.0123(7) -0.2867(7) 0.080(2) Uani 1 1 d .
O2 O 0.8470(12) 0.1158(8) -0.3404(7) 0.093(3) Uani 1 1 d .
C3 C 0.9366(16) 0.0726(10) -0.2618(11) 0.068(3) Uani 1 1 d .
C4 C 0.9483(13) 0.1322(10) -0.1226(9) 0.063(3) Uani 1 1 d .
H4 H 0.9849 0.0870 -0.0691 0.076 Uiso 1 1 calc R
C5 C 0.9130(13) 0.2400(9) -0.0682(9) 0.061(3) Uani 1 1 d .
H5 H 0.8666 0.2793 -0.1257 0.073 Uiso 1 1 calc R
C6 C 0.9345(13) 0.3080(9) 0.0673(9) 0.058(3) Uani 1 1 d .
C7 C 0.9113(15) 0.4332(10) 0.1104(9) 0.073(3) Uani 1 1 d .
H7 H 0.8759 0.4694 0.0480 0.087 Uiso 1 1 calc R
C8 C 0.9373(15) 0.5056(10) 0.2383(10) 0.074(3) Uani 1 1 d .
H8 H 0.9261 0.5909 0.2641 0.089 Uiso 1 1 calc R
C9 C 0.9813(14) 0.4475(11) 0.3295(9) 0.073(3) Uani 1 1 d .
C10 C 1.0043(13) 0.3245(10) 0.2939(9) 0.065(3) Uani 1 1 d .
H10 H 1.0341 0.2881 0.3566 0.078 Uiso 1 1 calc R
C11 C 0.9834(13) 0.2546(10) 0.1654(9) 0.063(3) Uani 1 1 d .
H11 H 1.0012 0.1714 0.1421 0.076 Uiso 1 1 calc R
N12A N 0.9988(11) 0.5304(8) 0.4646(8) 0.048(2) Uiso 0.82 1 d P
N12B N 1.006(4) 0.652(3) 0.474(3) 0.031(8) Uiso 0.18 1 d P
N13 N 0.2672(12) -0.0008(9) 0.6085(7) 0.076(3) Uani 1 1 d .
H13A H 0.2097 -0.0261 0.5191 0.092 Uiso 1 1 calc R
H13B H 0.1802 -0.0026 0.6403 0.092 Uiso 1 1 calc R
C14 C 0.3602(18) -0.1030(16) 0.6336(13) 0.106(4) Uani 1 1 d .
H14A H 0.2705 -0.1936 0.5759 0.128 Uiso 1 1 calc R
H14B H 0.4612 -0.0944 0.6068 0.128 Uiso 1 1 calc R
C15 C 0.4325(17) -0.0887(14) 0.7708(13) 0.104(4) Uani 1 1 d .
H15A H 0.3346 -0.0922 0.8009 0.124 Uiso 1 1 calc R
H15B H 0.5302 -0.0014 0.8288 0.124 Uiso 1 1 calc R
C16 C 0.5103(17) -0.2024(15) 0.7822(16) 0.117(5) Uani 1 1 d .
H16A H 0.4180 -0.2894 0.7149 0.140 Uiso 1 1 calc R
H16B H 0.6190 -0.1912 0.7640 0.140 Uiso 1 1 calc R
C17 C 0.562(2) -0.2014(18) 0.9188(17) 0.152(6) Uani 1 1 d .
H17A H 0.6452 -0.1130 0.9862 0.228 Uiso 1 1 calc R
H17B H 0.6211 -0.2671 0.9251 0.228 Uiso 1 1 calc R
H17C H 0.4519 -0.2235 0.9328 0.228 Uiso 1 1 calc R
C18 C 0.396(2) 0.1355(14) 0.6712(14) 0.133(5) Uani 1 1 d D
H18A H 0.5050 0.1343 0.6549 0.160 Uiso 1 1 calc R
H18B H 0.4346 0.1710 0.7678 0.160 Uiso 1 1 calc R
C19 C 0.317(2) 0.2258(15) 0.6209(17) 0.165(8) Uani 1 1 d D
C20 C 0.455(3) 0.3669(18) 0.705(2) 0.202(9) Uiso 1 1 d D
C21 C 0.550(4) 0.412(3) 0.631(3) 0.274(13) 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'
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'
H H 0.0000 0.0000 '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
O1 C3 O2 127.8(9) .
O1 C3 C4 117.8(10) .
O2 C3 C4 114.3(8) .
C5 C4 C3 127.2(10) .
C5 C4 H4 116.4 .
C3 C4 H4 116.4 .
C4 C5 C6 130.0(10) .
C4 C5 H5 115.0 .
C6 C5 H5 115.0 .
C7 C6 C11 116.1(8) .
C7 C6 C5 120.8(9) .
C11 C6 C5 123.1(9) .
C8 C7 C6 123.8(10) .
C8 C7 H7 118.1 .
C6 C7 H7 118.1 .
C7 C8 C9 117.7(9) .
C7 C8 H8 121.1 .
C9 C8 H8 121.1 .
C10 C9 C8 121.6(8) .
C10 C9 N12A 124.3(10) .
C8 C9 N12A 114.2(9) .
C9 C10 C11 120.0(9) .
C9 C10 H10 120.0 .
C11 C10 H10 120.0 .
C10 C11 C6 120.7(9) .
C10 C11 H11 119.6 .
C6 C11 H11 119.6 .
N12A N12A N12B 137.5(17) 2_766
N12A N12A C9 114.0(11) 2_766
N12B N12A C9 108.5(15) .
C18 N13 C14 113.1(10) .
C18 N13 H13A 109.0 .
C14 N13 H13A 109.0 .
C18 N13 H13B 109.0 .
C14 N13 H13B 109.0 .
H13A N13 H13B 107.8 .
C15 C14 N13 115.5(10) .
C15 C14 H14A 108.4 .
N13 C14 H14A 108.4 .
C15 C14 H14B 108.4 .
N13 C14 H14B 108.4 .
H14A C14 H14B 107.5 .
C14 C15 C16 110.9(11) .
C14 C15 H15A 109.5 .
C16 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
C16 C15 H15B 109.5 .
H15A C15 H15B 108.0 .
C17 C16 C15 111.9(13) .
C17 C16 H16A 109.2 .
C15 C16 H16A 109.2 .
C17 C16 H16B 109.2 .
C15 C16 H16B 109.2 .
H16A C16 H16B 107.9 .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
N13 C18 C19 112.8(12) .
N13 C18 H18A 109.0 .
C19 C18 H18A 109.0 .
N13 C18 H18B 109.0 .
C19 C18 H18B 109.0 .
H18A C18 H18B 107.8 .
C18 C19 C20 107.5(14) .
C21 C20 C19 112(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.228(10) .
O2 C3 1.254(11) .
C3 C4 1.496(13) .
C4 C5 1.297(12) .
C4 H4 0.9300 .
C5 C6 1.438(12) .
C5 H5 0.9300 .
C6 C7 1.391(12) .
C6 C11 1.428(13) .
C7 C8 1.358(13) .
C7 H7 0.9300 .
C8 C9 1.396(14) .
C8 H8 0.9300 .
C9 C10 1.364(13) .
C9 N12A 1.480(12) .
C10 C11 1.372(12) .
C10 H10 0.9300 .
C11 H11 0.9300 .
N12A N12A 1.219(14) 2_766
N12A N12B 1.31(3) .
N13 C18 1.438(15) .
N13 C14 1.534(14) .
N13 H13A 0.9000 .
N13 H13B 0.9000 .
C14 C15 1.442(15) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.544(16) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.494(18) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C19 1.465(9) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.500(10) .
C20 C21 1.474(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
N13 H13A O2 0.90 1.83 2.684(10) 157.7 2_655
N13 H13B O1 0.90 1.85 2.743(11) 175.6 1_456
