#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102195.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2102195
loop_
_publ_author_name
'Burchell, Colin J.'
'Ferguson, George'
'Lough, Alan J.'
'Glidewell, Christopher'
_publ_section_title
;
 Adducts of meso and racemic
 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane with
 trigonally trisubstituted benzene carboxylic acids: supramolecular
 structures in one and two dimensions
;
_journal_coeditor_code           NA0108
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              1054
_journal_page_last               1062
_journal_paper_doi               10.1107/S0108768100008302
_journal_volume                  56
_journal_year                    2000
_chemical_compound_source        'Synthesised by authors, see text'
_chemical_formula_moiety         'C16 H38 N4, 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C30 H44 N8 O12'
_chemical_formula_weight         708.73
_chemical_name_systematic
;
 meso-5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane--3,5-
dinitrobenzoic acid(1/2)

;
_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
_cell_angle_alpha                114.5800(17)
_cell_angle_beta                 91.9660(18)
_cell_angle_gamma                111.6740(18)
_cell_formula_units_Z            1
_cell_length_a                   8.7336(3)
_cell_length_b                   10.9388(3)
_cell_length_c                   11.0284(3)
_cell_measurement_reflns_used    12749
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.03
_cell_volume                     868.09(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'NRCVAX-96, ORTEP (Johnson, 1976), PLATON (Spek, 2000)'
_computing_publication_material
'NRCVAX-96, SHELXL-97  and WordPerfect macro PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'NRCVAX-96 and SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12749
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0542P)²+0.1566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                3651
_reflns_number_total             5013
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            na0108.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        868.09(4)
_cod_database_code               2102195
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
N1 N 0.38165(12) 0.63318(10) 0.55172(10) 0.0214(2) Uani 1 1 d .
C2 C 0.23199(16) 0.54780(13) 0.58511(13) 0.0252(3) Uani 1 1 d .
C3 C 0.27683(16) 0.47571(13) 0.66386(12) 0.0259(3) Uani 1 1 d .
N4 N 0.35154(13) 0.37403(10) 0.58203(10) 0.0214(2) Uani 1 1 d .
C5 C 0.39028(16) 0.28369(13) 0.64208(12) 0.0242(3) Uani 1 1 d .
C51 C 0.22302(19) 0.17058(15) 0.64215(15) 0.0351(3) Uani 1 1 d .
C52 C 0.4994(2) 0.38603(16) 0.78661(13) 0.0356(3) Uani 1 1 d .
C6 C 0.48122(16) 0.20053(13) 0.54566(13) 0.0254(3) Uani 1 1 d .
C7 C 0.64938(16) 0.28992(13) 0.52269(12) 0.0238(3) Uani 1 1 d .
C71 C 0.73192(18) 0.18624(15) 0.44979(15) 0.0344(3) Uani 1 1 d .
O1 O 0.12100(13) 0.17636(11) 0.34034(9) 0.0387(3) Uani 1 1 d .
O2 O 0.30300(12) 0.31943(12) 0.26448(10) 0.0399(3) Uani 1 1 d .
O3 O 0.06891(16) 0.39464(13) -0.09511(12) 0.0507(3) Uani 1 1 d .
O4 O -0.18082(19) 0.24172(18) -0.22159(14) 0.0710(4) Uani 1 1 d .
O5 O -0.52769(12) -0.15405(11) -0.12954(10) 0.0399(3) Uani 1 1 d .
O6 O -0.42798(15) -0.18797(13) 0.02998(12) 0.0545(3) Uani 1 1 d .
N3 N -0.06477(18) 0.28683(16) -0.12643(13) 0.0422(3) Uani 1 1 d .
N5 N -0.41460(15) -0.12071(13) -0.03649(11) 0.0353(3) Uani 1 1 d .
C11 C 0.01922(16) 0.17937(14) 0.14061(12) 0.0256(3) Uani 1 1 d .
C12 C 0.04189(17) 0.25421(15) 0.06233(13) 0.0289(3) Uani 1 1 d .
C13 C -0.08773(18) 0.20456(15) -0.04618(13) 0.0305(3) Uani 1 1 d .
C14 C -0.23778(17) 0.08107(15) -0.08256(12) 0.0310(3) Uani 1 1 d .
C15 C -0.25553(16) 0.00957(14) -0.00260(12) 0.0275(3) Uani 1 1 d .
C16 C -0.13147(16) 0.05700(14) 0.10921(12) 0.0261(3) Uani 1 1 d .
C17 C 0.16098(16) 0.23011(14) 0.25890(12) 0.0286(3) Uani 1 1 d .
H1 H 0.4610 0.7026 0.6316 0.026 Uiso 1 1 calc R
H2A H 0.1470 0.4702 0.4997 0.030 Uiso 1 1 calc R
H2B H 0.1816 0.6141 0.6407 0.030 Uiso 1 1 calc R
H3A H 0.3587 0.5534 0.7509 0.031 Uiso 1 1 calc R
H3B H 0.1739 0.4192 0.6860 0.031 Uiso 1 1 calc R
H4A H 0.4503 0.4297 0.5672 0.026 Uiso 1 1 calc R
H4B H 0.2785 0.3092 0.4980 0.026 Uiso 1 1 calc R
H51A H 0.1631 0.2226 0.7016 0.053 Uiso 1 1 calc R
H51B H 0.2452 0.1076 0.6761 0.053 Uiso 1 1 calc R
H51C H 0.1534 0.1089 0.5488 0.053 Uiso 1 1 calc R
H52A H 0.5929 0.4706 0.7871 0.053 Uiso 1 1 calc R
H52B H 0.5447 0.3314 0.8171 0.053 Uiso 1 1 calc R
H52C H 0.4306 0.4219 0.8485 0.053 Uiso 1 1 calc R
H6A H 0.5014 0.1367 0.5808 0.030 Uiso 1 1 calc R
H6B H 0.4021 0.1338 0.4552 0.030 Uiso 1 1 calc R
H7 H 0.7255 0.3666 0.6141 0.029 Uiso 1 1 calc R
H71A H 0.6581 0.1090 0.3606 0.052 Uiso 1 1 calc R
H71B H 0.7496 0.1401 0.5053 0.052 Uiso 1 1 calc R
H71C H 0.8410 0.2431 0.4368 0.052 Uiso 1 1 calc R
H12 H 0.1446 0.3380 0.0829 0.035 Uiso 1 1 calc R
H14 H -0.3243 0.0471 -0.1587 0.037 Uiso 1 1 calc R
H16 H -0.1494 0.0066 0.1634 0.031 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'
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
_geom_angle_publ_flag
C2 N1 C7 114.71(9) . 2_666 no
C2 N1 H1 108.6 . . no
C7 N1 H1 108.6 2_666 . no
N1 C2 C3 110.90(10) . . no
N1 C2 H2A 109.5 . . no
C3 C2 H2A 109.5 . . no
N1 C2 H2B 109.5 . . no
C3 C2 H2B 109.5 . . no
H2A C2 H2B 108.0 . . no
N4 C3 C2 110.67(10) . . no
N4 C3 H3A 109.5 . . no
C2 C3 H3A 109.5 . . no
N4 C3 H3B 109.5 . . no
C2 C3 H3B 109.5 . . no
H3A C3 H3B 108.1 . . no
C3 N4 C5 117.10(9) . . no
C3 N4 H4A 108.0 . . no
C5 N4 H4A 108.0 . . no
C3 N4 H4B 108.0 . . no
C5 N4 H4B 108.0 . . no
H4A N4 H4B 107.3 . . no
N4 C5 C52 109.85(10) . . no
N4 C5 C51 108.22(10) . . no
C52 C5 C51 111.06(11) . . no
N4 C5 C6 106.76(9) . . no
C52 C5 C6 111.86(11) . . no
C51 C5 C6 108.93(10) . . no
C5 C51 H51A 109.5 . . no
C5 C51 H51B 109.5 . . no
H51A C51 H51B 109.5 . . no
C5 C51 H51C 109.5 . . no
H51A C51 H51C 109.5 . . no
H51B C51 H51C 109.5 . . no
C5 C52 H52A 109.5 . . no
C5 C52 H52B 109.5 . . no
H52A C52 H52B 109.5 . . no
C5 C52 H52C 109.5 . . no
H52A C52 H52C 109.5 . . no
H52B C52 H52C 109.5 . . no
C7 C6 C5 119.13(10) . . no
C7 C6 H6A 107.5 . . no
C5 C6 H6A 107.5 . . no
C7 C6 H6B 107.5 . . no
C5 C6 H6B 107.5 . . no
H6A C6 H6B 107.0 . . no
N1 C7 C71 114.04(10) 2_666 . no
N1 C7 C6 108.96(10) 2_666 . no
C71 C7 C6 108.99(10) . . no
N1 C7 H7 108.2 2_666 . no
C71 C7 H7 108.2 . . no
C6 C7 H7 108.2 . . no
C7 C71 H71A 109.5 . . no
C7 C71 H71B 109.5 . . no
H71A C71 H71B 109.5 . . no
C7 C71 H71C 109.5 . . no
H71A C71 H71C 109.5 . . no
H71B C71 H71C 109.5 . . no
O3 N3 O4 123.91(14) . . no
O3 N3 C13 118.27(12) . . no
O4 N3 C13 117.82(14) . . no
O6 N5 O5 123.84(12) . . no
O6 N5 C15 118.41(11) . . no
O5 N5 C15 117.74(12) . . no
C16 C11 C12 119.86(11) . . no
C16 C11 C17 120.16(12) . . no
C12 C11 C17 119.97(12) . . no
C13 C12 C11 118.96(12) . . no
C13 C12 H12 120.5 . . no
C11 C12 H12 120.5 . . no
C14 C13 C12 122.80(12) . . no
C14 C13 N3 118.49(12) . . no
C12 C13 N3 118.70(13) . . no
C15 C14 C13 116.54(11) . . no
C15 C14 H14 121.7 . . no
C13 C14 H14 121.7 . . no
C14 C15 C16 122.91(12) . . no
C14 C15 N5 118.19(11) . . no
C16 C15 N5 118.88(12) . . no
C15 C16 C11 118.88(12) . . no
C15 C16 H16 120.6 . . no
C11 C16 H16 120.6 . . no
O2 C17 O1 127.1(2) . . no
O2 C17 C11 116.81(12) . . no
O1 C17 C11 116.07(12) . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.461(2) . no
N1 C7 1.477(2) 2_666 no
N1 H1 0.92 . no
C2 C3 1.5179(17) . no
C2 H2A 0.99 . no
C2 H2B 0.99 . no
C3 N4 1.490(2) . no
C3 H3A 0.99 . no
C3 H3B 0.99 . no
N4 C5 1.518(2) . no
N4 H4A 0.92 . no
N4 H4B 0.92 . no
C5 C52 1.5248(17) . no
C5 C51 1.5267(18) . no
C5 C6 1.5415(17) . no
C51 H51A 0.98 . no
C51 H51B 0.98 . no
C51 H51C 0.98 . no
C52 H52A 0.98 . no
C52 H52B 0.98 . no
C52 H52C 0.98 . no
C6 C7 1.5324(17) . no
C6 H6A 0.99 . no
C6 H6B 0.99 . no
C7 C71 1.5288(18) . no
C7 H7 1.00 . no
C71 H71A 0.98 . no
C71 H71B 0.98 . no
C71 H71C 0.98 . no
O1 C17 1.258(2) . no
O2 C17 1.244(2) . no
O3 N3 1.2204(18) . no
O4 N3 1.2244(18) . no
O5 N5 1.2307(15) . no
O6 N5 1.2179(17) . no
N3 C13 1.4747(18) . no
N5 C15 1.4696(17) . no
C11 C12 1.3910(18) . no
C11 C16 1.3876(18) . no
C11 C17 1.5238(17) . no
C12 C13 1.3859(18) . no
C12 H12 0.95 . no
C13 C14 1.382(2) . no
C14 C15 1.3809(19) . no
C14 H14 0.95 . no
C15 C16 1.3873(17) . no
C16 H16 0.95 . no
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
_geom_hbond_publ_flag
N1 H1 O5 0.92 2.42 3.169(2) 139 1_666 yes
N1 H1 O2 0.92 2.46 3.107(2) 127 2_666 yes
N4 H4A N1 0.92 2.12 2.808(2) 131 2_666 yes
N4 H4B O1 0.92 1.81 2.730(2) 175 . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C2 C3 -178.79(9) 2_666 . . no
N1 C2 C3 N4 -59.6(2) . . . no
C2 C3 N4 C5 -175.2(2) . . . no
C3 N4 C5 C52 -53.2(2) . . . no
C3 N4 C5 C51 68.2(2) . . . no
C3 N4 C5 C6 -174.6(2) . . . no
N4 C5 C6 C7 60.7(2) . . . no
C52 C5 C6 C7 -59.54(14) . . . no
C51 C5 C6 C7 177.29(11) . . . no
C5 C6 C7 N1 -67.1(2) . . 2_666 no
C6 C7 N1 C2 -177.8(2) . 2_666 2_666 no
C5 C6 C7 C71 167.88(11) . . . no
C16 C11 C12 C13 0.06(18) . . . no
C17 C11 C12 C13 178.93(11) . . . no
C11 C12 C13 C14 -1.7(2) . . . no
C11 C12 C13 N3 178.33(11) . . . no
O3 N3 C13 C14 -178.99(13) . . . no
O4 N3 C13 C14 0.3(2) . . . no
O3 N3 C13 C12 0.97(19) . . . no
O4 N3 C13 C12 -179.73(14) . . . no
C12 C13 C14 C15 1.6(2) . . . no
N3 C13 C14 C15 -178.45(11) . . . no
C13 C14 C15 C16 0.15(19) . . . no
C13 C14 C15 N5 178.92(11) . . . no
O6 N5 C15 C14 176.83(13) . . . no
O5 N5 C15 C14 -4.22(18) . . . no
O6 N5 C15 C16 -4.36(19) . . . no
O5 N5 C15 C16 174.60(11) . . . no
C14 C15 C16 C11 -1.71(19) . . . no
N5 C15 C16 C11 179.53(11) . . . no
C12 C11 C16 C15 1.57(18) . . . no
C17 C11 C16 C15 -177.30(11) . . . no
C16 C11 C17 O2 165.61(12) . . . no
C12 C11 C17 O2 -13.25(18) . . . no
C16 C11 C17 O1 -14.25(18) . . . no
C12 C11 C17 O1 166.88(11) . . . no
