#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:14:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180067 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/13/7051359.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_7051359
loop_
_publ_author_name
'Laurent Frémond'
'Enrique Espinosa'
'Michel Meyer'
'Franck Denat'
'Roger Guilard'
'Volker Huch'
'Michael Veith'
_publ_section_title
;
 Synthesis, characterization and X-ray crystal structures of cyclam
 derivatives. Part IV. 1,4,8,11-Tetraazacyclotetradecane-5,12-dione and
 its diprotonated forms
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              959
_journal_page_last               966
_journal_paper_doi               10.1039/b005052k
_journal_volume                  24
_journal_year                    2000
_chemical_formula_moiety         'C10 H20 N4 O2,2(H2 O)'
_chemical_formula_sum            'C10 H24 N4 O4'
_chemical_formula_weight         264.33
_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                116.96(3)
_cell_angle_beta                 91.55(3)
_cell_angle_gamma                100.31(3)
_cell_formula_units_Z            1
_cell_length_a                   7.559(2)
_cell_length_b                   4.997(2)
_cell_length_c                   10.293(2)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.5
_cell_measurement_theta_min      9.5
_cell_volume                     338.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Stoe AED2'
_diffrn_measurement_method       ω-Θ-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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1163
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.24
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0328
_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)+(0.0507P)²+0.0915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                1063
_reflns_number_total             1163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005052k.txt
_cod_data_source_block           L
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        338.34(18)
_cod_database_code               7051359
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76783(16) 0.0161(2) 0.05547(12) 0.0437(3) Uani 1 1 d . . .
N1 N 0.69717(15) 0.3677(3) -0.01086(13) 0.0315(3) Uani 1 1 d . . .
H1 H 0.701(2) 0.557(5) 0.0171(19) 0.043(5) Uiso 1 1 d . . .
N2 N 0.87485(15) 0.4440(3) -0.25694(13) 0.0302(3) Uani 1 1 d . . .
H2 H 0.885(2) 0.610(4) -0.1671(19) 0.035(4) Uiso 1 1 d . . .
C1 C 0.74990(17) 0.2857(3) 0.08896(15) 0.0284(3) Uani 1 1 d . . .
C2 C 0.65938(19) 0.1491(3) -0.16614(16) 0.0339(4) Uani 1 1 d . . .
H2A H 0.562(2) 0.203(4) -0.2077(19) 0.045(5) Uiso 1 1 d . . .
H2B H 0.617(2) -0.061(4) -0.1772(18) 0.038(4) Uiso 1 1 d . . .
C3 C 0.82456(19) 0.1525(3) -0.24489(16) 0.0325(4) Uani 1 1 d . . .
H3A H 0.920(2) 0.120(4) -0.1890(18) 0.039(4) Uiso 1 1 d . . .
H3B H 0.796(2) -0.034(4) -0.3471(18) 0.035(4) Uiso 1 1 d . . .
C4 C 1.0411(2) 0.4681(3) -0.32399(15) 0.0329(4) Uani 1 1 d . . .
H4A H 1.064(2) 0.666(4) -0.3290(18) 0.040(4) Uiso 1 1 d . . .
H4B H 1.022(2) 0.294(4) -0.4244(19) 0.039(4) Uiso 1 1 d . . .
C5 C 0.78699(19) 0.5401(3) 0.24581(16) 0.0324(3) Uani 1 1 d . . .
H5A H 0.689(3) 0.503(4) 0.2961(19) 0.047(5) Uiso 1 1 d . . .
H5B H 0.789(2) 0.739(4) 0.2485(18) 0.039(4) Uiso 1 1 d . . .
O3 O 0.5922(2) 0.2890(4) -0.48607(18) 0.0652(5) Uani 1 1 d . . .
H6 H 0.650(3) 0.351(5) -0.427(2) 0.056(7) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0613(7) 0.0251(6) 0.0466(7) 0.0185(5) -0.0010(5) 0.0101(5)
N1 0.0351(7) 0.0249(7) 0.0372(7) 0.0162(5) 0.0035(5) 0.0085(5)
N2 0.0338(6) 0.0258(6) 0.0311(6) 0.0134(5) 0.0008(5) 0.0071(5)
C1 0.0239(6) 0.0251(7) 0.0392(8) 0.0182(6) 0.0046(5) 0.0032(5)
C2 0.0308(7) 0.0331(8) 0.0370(8) 0.0172(6) -0.0016(6) 0.0034(6)
C3 0.0354(8) 0.0262(7) 0.0361(8) 0.0148(6) 0.0024(6) 0.0068(6)
C4 0.0416(8) 0.0311(8) 0.0284(7) 0.0158(6) 0.0051(6) 0.0082(6)
C5 0.0332(7) 0.0307(8) 0.0366(8) 0.0175(6) 0.0097(6) 0.0090(6)
O3 0.0598(9) 0.0715(10) 0.0607(9) 0.0353(8) -0.0225(7) -0.0026(7)
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
C1 N1 C2 121.36(12) . . ?
C4 N2 C3 113.57(11) . . ?
O1 C1 N1 122.89(13) . . ?
O1 C1 C5 121.98(13) . . ?
N1 C1 C5 115.13(12) . . ?
N1 C2 C3 112.09(12) . . ?
N2 C3 C2 111.30(12) . . ?
N2 C4 C5 116.44(11) . 2_765 ?
C1 C5 C4 110.84(12) . 2_765 ?
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
O1 C1 1.2644(17) . ?
N1 C1 1.3420(18) . ?
N1 C2 1.453(2) . ?
N2 C4 1.4625(19) . ?
N2 C3 1.4998(19) . ?
C1 C5 1.513(2) . ?
C2 C3 1.509(2) . ?
C4 C5 1.526(2) 2_765 ?
C5 C4 1.526(2) 2_765 ?
