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#$Date: 2016-03-25 23:14:31 +0100 (vie 25 de mar de 2016) $
#$Revision: 180067 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/13/7051361.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_7051361
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 H22 O2 N4,2(Cl1 O4)'
_chemical_formula_sum            'C10 H22 Cl2 N4 O10'
_chemical_formula_weight         429.22
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.900(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2700(2)
_cell_length_b                   16.1690(4)
_cell_length_c                   10.8995(2)
_cell_measurement_temperature    112(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1731.76(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      112(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7487
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0166(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0301P)²+1.1613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                4493
_reflns_number_total             4881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005052k.txt
_cod_data_source_block           H2L(ClO4)2
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7051361
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
O1A O 0.46382(9) 0.05327(6) 0.87663(8) 0.01816(18) Uani 1 1 d . . .
N1A N 0.44654(13) 0.14998(7) 1.02085(11) 0.0213(2) Uani 1 1 d . . .
HN1A H 0.4895(19) 0.1862(12) 1.0778(18) 0.026 Uiso 1 1 d . . .
N2A N 0.28757(11) 0.01535(8) 1.09312(10) 0.0194(2) Uani 1 1 d . . .
HN2A H 0.3792(19) 0.0141(11) 1.1227(17) 0.023 Uiso 1 1 d . . .
HN3A H 0.2590(18) -0.0061(12) 1.1562(18) 0.023 Uiso 1 1 d . . .
C1A C 0.51831(14) 0.10493(7) 0.96006(11) 0.0176(2) Uani 1 1 d . . .
C2A C 0.29853(16) 0.14977(9) 0.98090(13) 0.0253(3) Uani 1 1 d . . .
H2A1 H 0.2656 0.1248 0.8944 0.0259(11) Uiso 1 1 calc R . .
H2A2 H 0.2657 0.2076 0.9747 0.0259(11) Uiso 1 1 calc R . .
C3A C 0.23823(14) 0.10258(10) 1.07160(13) 0.0254(3) Uani 1 1 d . . .
H3A1 H 0.2615 0.1317 1.1551 0.0259(11) Uiso 1 1 calc R . .
H3A2 H 0.1379 0.1023 1.0363 0.0259(11) Uiso 1 1 calc R . .
C4A C 0.24655(14) -0.04083(9) 0.97901(12) 0.0222(3) Uani 1 1 d . . .
H4A1 H 0.2606 -0.0123 0.9035 0.0259(11) Uiso 1 1 calc R . .
H4A2 H 0.1487 -0.0544 0.9597 0.0259(11) Uiso 1 1 calc R . .
C5A C 0.67025(15) 0.12005(9) 0.99556(13) 0.0232(3) Uani 1 1 d . . .
H5A1 H 0.6974 0.1552 1.0732 0.0259(11) Uiso 1 1 calc R . .
H5A2 H 0.6914 0.1507 0.9251 0.0259(11) Uiso 1 1 calc R . .
O1B O 0.42926(9) 0.04809(6) 0.35448(9) 0.01766(18) Uani 1 1 d . . .
N1B N 0.62338(11) 0.11961(6) 0.44232(10) 0.01417(19) Uani 1 1 d . . .
HN1B H 0.6599(18) 0.1563(11) 0.4889(17) 0.017 Uiso 1 1 d . . .
N2B N 0.75210(11) -0.04348(7) 0.50288(10) 0.01490(19) Uani 1 1 d . . .
HN2B H 0.7153(17) -0.0195(11) 0.5585(17) 0.018 Uiso 1 1 d . . .
HN3B H 0.8234(18) -0.0729(11) 0.5503(16) 0.018 Uiso 1 1 d . . .
C1B C 0.49232(12) 0.10274(7) 0.42824(11) 0.0134(2) Uani 1 1 d . . .
C2B C 0.69907(12) 0.08233(7) 0.36206(11) 0.0150(2) Uani 1 1 d . . .
H2B1 H 0.7429 0.1267 0.3256 0.0259(11) Uiso 1 1 calc R . .
H2B2 H 0.6345 0.0531 0.2898 0.0259(11) Uiso 1 1 calc R . .
C3B C 0.80802(12) 0.02156(8) 0.43448(12) 0.0157(2) Uani 1 1 d . . .
H3B1 H 0.8492 -0.0054 0.3732 0.0259(11) Uiso 1 1 calc R . .
H3B2 H 0.8807 0.0523 0.4976 0.0259(11) Uiso 1 1 calc R . .
C4B C 0.65075(13) -0.10106(7) 0.41782(12) 0.0164(2) Uani 1 1 d . . .
H4B1 H 0.6979 -0.1374 0.3713 0.0259(11) Uiso 1 1 calc R . .
H4B2 H 0.5821 -0.0684 0.3535 0.0259(11) Uiso 1 1 calc R . .
C5B C 0.42079(13) 0.15422(7) 0.50544(12) 0.0159(2) Uani 1 1 d . . .
H5B1 H 0.3529 0.1904 0.4465 0.0259(11) Uiso 1 1 calc R . .
H5B2 H 0.4883 0.1902 0.5651 0.0259(11) Uiso 1 1 calc R . .
Cl1 Cl 0.02268(3) 0.187029(17) 0.28166(3) 0.01342(8) Uani 1 1 d . . .
O2 O 0.11254(10) 0.23303(6) 0.22729(10) 0.0225(2) Uani 1 1 d . . .
O3 O -0.11050(9) 0.22361(7) 0.24073(10) 0.0264(2) Uani 1 1 d . . .
O4 O 0.07371(11) 0.18951(6) 0.42016(9) 0.0254(2) Uani 1 1 d . . .
O5 O 0.01803(12) 0.10170(6) 0.24264(11) 0.0291(2) Uani 1 1 d . . .
Cl2 Cl 0.40209(3) 0.355077(19) 0.74920(3) 0.01922(9) Uani 1 1 d . . .
O6 O 0.32488(16) 0.29151(8) 0.66957(13) 0.0481(4) Uani 1 1 d . . .
O7 O 0.43546(12) 0.33118(8) 0.88151(10) 0.0310(2) Uani 1 1 d . . .
O8 O 0.52306(14) 0.37143(12) 0.71391(15) 0.0586(5) Uani 1 1 d . . .
O9 O 0.31984(13) 0.42949(6) 0.72873(10) 0.0294(2) Uani 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'
Cl Cl 0.1484 0.1585 '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
C1A N1A C2A 121.85(12) . . ?
C3A N2A C4A 116.19(11) . . ?
O1A C1A N1A 122.14(13) . . ?
O1A C1A C5A 120.49(11) . . ?
N1A C1A C5A 117.37(11) . . ?
N1A C2A C3A 113.29(11) . . ?
N2A C3A C2A 113.16(10) . . ?
N2A C4A C5A 110.62(11) . 3_657 ?
C1A C5A C4A 113.17(11) . 3_657 ?
C1B N1B C2B 122.73(10) . . ?
C3B N2B C4B 115.22(10) . . ?
O1B C1B N1B 122.48(11) . . ?
O1B C1B C5B 120.26(11) . . ?
N1B C1B C5B 117.25(10) . . ?
N1B C2B C3B 113.23(9) . . ?
N2B C3B C2B 112.35(9) . . ?
N2B C4B C5B 111.63(10) . 3_656 ?
C1B C5B C4B 112.48(10) . 3_656 ?
O3 Cl1 O2 109.00(6) . . ?
O3 Cl1 O5 110.84(7) . . ?
O2 Cl1 O5 110.08(6) . . ?
O3 Cl1 O4 109.62(6) . . ?
O2 Cl1 O4 109.50(7) . . ?
O5 Cl1 O4 107.78(6) . . ?
O6 Cl2 O8 110.03(11) . . ?
O6 Cl2 O7 110.20(8) . . ?
O8 Cl2 O7 110.38(8) . . ?
O6 Cl2 O9 107.95(7) . . ?
O8 Cl2 O9 108.58(9) . . ?
O7 Cl2 O9 109.66(7) . . ?
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
O1A C1A 1.2417(15) . ?
N1A C1A 1.3405(16) . ?
N1A C2A 1.454(2) . ?
N2A C3A 1.4940(19) . ?
N2A C4A 1.4983(17) . ?
C1A C5A 1.5144(19) . ?
C2A C3A 1.516(2) . ?
C4A C5A 1.520(2) 3_657 ?
C5A C4A 1.520(2) 3_657 ?
O1B C1B 1.2426(15) . ?
N1B C1B 1.3377(15) . ?
N1B C2B 1.4589(15) . ?
N2B C3B 1.4969(15) . ?
N2B C4B 1.4995(16) . ?
C1B C5B 1.5166(16) . ?
C2B C3B 1.5255(17) . ?
C4B C5B 1.5283(16) 3_656 ?
C5B C4B 1.5283(16) 3_656 ?
Cl1 O3 1.4369(10) . ?
Cl1 O2 1.4402(9) . ?
Cl1 O5 1.4405(10) . ?
Cl1 O4 1.4475(10) . ?
Cl2 O6 1.4276(13) . ?
Cl2 O8 1.4280(13) . ?
Cl2 O7 1.4350(11) . ?
Cl2 O9 1.4496(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
N1A HN1A O2 0.87(2) 2.18(2) 3.0524(16) 174.1(17) 4_666
N1B HN1B O6 0.800(18) 2.349(18) 3.0827(17) 152.7(16) 4_665
N2B HN2B O9 0.891(17) 2.357(17) 2.9909(15) 128.2(14) 4_665
N2A HN2A O1A 0.902(19) 1.944(18) 2.7147(15) 142.3(16) 3_657
N2A HN3A O9 0.892(18) 1.976(19) 2.8565(15) 168.9(17) 2_547
N2B HN2B O1B 0.891(17) 2.034(17) 2.7523(13) 136.9(15) 3_656
N2B HN3B O4 0.900(18) 2.139(18) 2.9337(14) 146.7(15) 3_656
N2B HN3B O5 0.900(18) 2.413(18) 3.2165(16) 148.7(14) 3_656
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2A N1A C1A O1A -8.74(19) . . . . ?
C2A N1A C1A C5A 170.43(12) . . . . ?
C1A N1A C2A C3A 106.97(14) . . . . ?
C4A N2A C3A C2A -65.65(15) . . . . ?
N1A C2A C3A N2A -55.56(15) . . . . ?
C3A N2A C4A C5A 166.29(11) . . . 3_657 ?
O1A C1A C5A C4A -48.68(16) . . . 3_657 ?
N1A C1A C5A C4A 132.13(12) . . . 3_657 ?
C2B N1B C1B O1B 7.31(18) . . . . ?
C2B N1B C1B C5B -171.91(10) . . . . ?
C1B N1B C2B C3B -111.00(13) . . . . ?
C4B N2B C3B C2B 64.90(13) . . . . ?
N1B C2B C3B N2B 53.38(14) . . . . ?
C3B N2B C4B C5B -169.11(10) . . . 3_656 ?
O1B C1B C5B C4B 52.87(15) . . . 3_656 ?
N1B C1B C5B C4B -127.90(12) . . . 3_656 ?
