#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:14:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180067 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/13/7051360.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_7051360
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 N4 O2,Br2'
_chemical_formula_sum            'C10 H22 Br2 N4 O2'
_chemical_formula_weight         390.14
_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                109.126(3)
_cell_angle_beta                 104.189(3)
_cell_angle_gamma                97.989(3)
_cell_formula_units_Z            1
_cell_length_a                   5.2851(2)
_cell_length_b                   8.0718(4)
_cell_length_c                   9.5424(5)
_cell_measurement_temperature    112(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     362.03(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2142
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    5.600
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0255
_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)+(0.0285P)²+0.4758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0682
_reflns_number_gt                1550
_reflns_number_total             1619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005052k.txt
_cod_data_source_block           H2LBr2
_cod_database_code               7051360
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 0.3900(4) 0.3529(3) 0.0477(2) 0.0193(4) Uani 1 1 d . . .
N1 N -0.0197(4) 0.2623(3) 0.0663(3) 0.0135(4) Uani 1 1 d . . .
HN1 H -0.110(6) 0.258(4) 0.130(4) 0.016 Uiso 1 1 d . . .
N2 N -0.4582(4) 0.2541(3) -0.2268(3) 0.0123(4) Uani 1 1 d . . .
HN2 H -0.468(6) 0.317(4) -0.138(4) 0.015 Uiso 1 1 d . . .
HN3 H -0.580(6) 0.150(5) -0.258(4) 0.015 Uiso 1 1 d . . .
C1 C 0.2361(5) 0.3592(3) 0.1268(3) 0.0125(5) Uani 1 1 d . . .
C2 C -0.1172(5) 0.1273(3) -0.0923(3) 0.0148(5) Uani 1 1 d . . .
H2A H -0.2736 0.0403 -0.1024 0.014(3) Uiso 1 1 calc R . .
H2B H 0.0208 0.0632 -0.1111 0.014(3) Uiso 1 1 calc R . .
C3 C -0.1921(5) 0.2084(3) -0.2154(3) 0.0145(5) Uani 1 1 d . . .
H3A H -0.0555 0.3168 -0.1891 0.014(3) Uiso 1 1 calc R . .
H3B H -0.1980 0.1230 -0.3158 0.014(3) Uiso 1 1 calc R . .
C4 C -0.5394(5) 0.3507(3) -0.3345(3) 0.0141(5) Uani 1 1 d . . .
H4A H -0.7076 0.3824 -0.3273 0.014(3) Uiso 1 1 calc R . .
H4B H -0.5700 0.2697 -0.4410 0.014(3) Uiso 1 1 calc R . .
C5 C 0.3300(5) 0.4787(3) 0.2980(3) 0.0130(5) Uani 1 1 d . . .
H5A H 0.4059 0.4115 0.3585 0.014(3) Uiso 1 1 calc R . .
H5B H 0.1768 0.5120 0.3289 0.014(3) Uiso 1 1 calc R . .
Br1 Br 0.78961(4) 0.16479(3) 0.35859(3) 0.01510(12) Uani 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 0.0221(9) 0.0178(9) 0.0182(9) 0.0037(8) 0.0124(7) 0.0018(7)
N1 0.0169(10) 0.0115(10) 0.0138(10) 0.0049(8) 0.0079(8) 0.0031(8)
N2 0.0153(10) 0.0092(9) 0.0125(10) 0.0026(8) 0.0072(8) 0.0017(8)
C1 0.0180(12) 0.0074(10) 0.0154(12) 0.0061(9) 0.0073(9) 0.0051(9)
C2 0.0195(12) 0.0093(11) 0.0150(12) 0.0043(9) 0.0052(9) 0.0030(9)
C3 0.0170(12) 0.0122(11) 0.0172(12) 0.0052(9) 0.0096(9) 0.0051(9)
C4 0.0151(11) 0.0140(11) 0.0132(11) 0.0056(9) 0.0041(9) 0.0029(9)
C5 0.0173(11) 0.0110(11) 0.0123(11) 0.0050(9) 0.0066(9) 0.0033(9)
Br1 0.01765(17) 0.01022(16) 0.01682(17) 0.00342(11) 0.00792(10) 0.00094(10)
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'
Br Br -0.2901 2.4595 '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 120.5(2) . . ?
C3 N2 C4 115.50(19) . . ?
O1 C1 N1 122.3(2) . . ?
O1 C1 C5 120.7(2) . . ?
N1 C1 C5 117.0(2) . . ?
N1 C2 C3 113.0(2) . . ?
N2 C3 C2 111.29(19) . . ?
N2 C4 C5 113.0(2) . 2_565 ?
C1 C5 C4 112.3(2) . 2_565 ?
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 1.233(3) . ?
N1 C1 1.342(3) . ?
N1 C2 1.458(3) . ?
N2 C3 1.490(3) . ?
N2 C4 1.501(3) . ?
C1 C5 1.511(3) . ?
C2 C3 1.521(3) . ?
C4 C5 1.522(3) 2_565 ?
C5 C4 1.522(3) 2_565 ?
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
N1 HN1 Br1 0.87(3) 2.67(3) 3.466(2) 153(3) 1_455
N2 HN2 O1 0.85(3) 2.04(3) 2.825(3) 153(3) 1_455
N2 HN2 O1 0.85(3) 2.46(3) 2.990(3) 121(3) 2_565
N2 HN3 Br1 0.89(3) 2.39(3) 3.251(2) 162(3) 2
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
C2 N1 C1 O1 7.7(4) . . . . ?
C2 N1 C1 C5 -172.4(2) . . . . ?
C1 N1 C2 C3 -81.2(3) . . . . ?
C4 N2 C3 C2 174.6(2) . . . . ?
N1 C2 C3 N2 -77.7(3) . . . . ?
C3 N2 C4 C5 -54.3(3) . . . 2_565 ?
O1 C1 C5 C4 32.2(3) . . . 2_565 ?
N1 C1 C5 C4 -147.7(2) . . . 2_565 ?
