#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:14:47 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179745 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/41/7004148.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_7004148
loop_
_publ_author_name
'Havlíčková, Jana'
'Medová, Hana'
'Vitha, Tomáš'
'Kotek, Jan'
'Císařová, Ivana'
'Hermann, Petr'
_publ_section_title
;
 Coordination properties of cyclam (1,4,8,11-tetraazacyclotetradecane)
 endowed with two methylphosphonic acid pendant arms in the
 1,4-positions
;
_journal_issue                   39
_journal_name_full               'Dalton Transactions'
_journal_page_first              5378
_journal_page_last               5386
_journal_paper_doi               10.1039/b803235a
_journal_year                    2008
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C24 H40 N4, 2(H2 O), 4(Br)'
_chemical_formula_sum            'C24 H44 Br4 N4 O2'
_chemical_formula_weight         740.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.6839(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.27000(10)
_cell_length_b                   20.5765(4)
_cell_length_c                   20.0208(4)
_cell_measurement_reflns_used    16767
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2952.26(9)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28031
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.480
_exptl_absorpt_correction_T_max  0.7003
_exptl_absorpt_correction_T_min  0.2902
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0273P)²+7.3214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                2854
_reflns_number_total             3408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b803235a.txt
_cod_data_source_block           14bn2cam
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7004148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Br1 Br 0.14596(3) 0.328075(12) 0.103487(12) 0.02413(8) Uani 1 1 d . . .
Br2 Br 0.0000 0.118648(16) 0.2500 0.02475(9) Uani 1 2 d S . .
Br3 Br 0.5000 0.027003(18) 0.2500 0.04737(14) Uani 1 2 d S . .
N1 N 0.6403(3) 0.44690(9) 0.17788(9) 0.0178(4) Uani 1 1 d . . .
H11 H 0.7159 0.4819 0.1939 0.021 Uiso 1 1 calc R . .
C2 C 0.7567(3) 0.38607(11) 0.19303(12) 0.0203(5) Uani 1 1 d . . .
H21 H 0.8672 0.3891 0.1703 0.024 Uiso 1 1 calc R . .
H22 H 0.8018 0.3835 0.2424 0.024 Uiso 1 1 calc R . .
C3 C 0.6506(4) 0.32467(11) 0.17006(16) 0.0319(6) Uani 1 1 d . . .
H31 H 0.6232 0.3236 0.1199 0.038 Uiso 1 1 calc R . .
H32 H 0.5303 0.3245 0.1870 0.038 Uiso 1 1 calc R . .
C4 C 0.7620(3) 0.26500(11) 0.19592(12) 0.0211(5) Uani 1 1 d . . .
H41 H 0.8749 0.2625 0.1745 0.025 Uiso 1 1 calc R . .
H42 H 0.8030 0.2691 0.2455 0.025 Uiso 1 1 calc R . .
N5 N 0.6513(3) 0.20350(9) 0.18126(10) 0.0209(4) Uani 1 1 d . . .
H51 H 0.6189 0.1994 0.1350 0.025 Uiso 1 1 calc R . .
H52 H 0.7277 0.1690 0.1963 0.025 Uiso 1 1 calc R . .
C6 C 0.4775(3) 0.19772(11) 0.21159(12) 0.0205(5) Uani 1 1 d . . .
H61 H 0.4119 0.1569 0.1959 0.025 Uiso 1 1 calc R . .
H62 H 0.3933 0.2345 0.1962 0.025 Uiso 1 1 calc R . .
C7 C 0.4716(3) 0.45000(11) 0.21164(11) 0.0175(4) Uani 1 1 d . . .
H71 H 0.3902 0.4121 0.1976 0.021 Uiso 1 1 calc R . .
H72 H 0.4000 0.4900 0.1972 0.021 Uiso 1 1 calc R . .
C10 C 0.5844(4) 0.45601(12) 0.10192(12) 0.0249(5) Uani 1 1 d . . .
H101 H 0.6961 0.4506 0.0802 0.030 Uiso 1 1 calc R . .
H102 H 0.4939 0.4217 0.0840 0.030 Uiso 1 1 calc R . .
C11 C 0.4985(4) 0.52154(12) 0.08283(12) 0.0237(5) Uani 1 1 d . . .
C12 C 0.3061(4) 0.52813(13) 0.06622(13) 0.0298(6) Uani 1 1 d . . .
H121 H 0.2280 0.4915 0.0684 0.036 Uiso 1 1 calc R . .
C13 C 0.2269(4) 0.58824(14) 0.04636(14) 0.0359(6) Uani 1 1 d . . .
H131 H 0.0953 0.5926 0.0348 0.043 Uiso 1 1 calc R . .
C14 C 0.3421(5) 0.64164(14) 0.04357(15) 0.0385(7) Uani 1 1 d . . .
H141 H 0.2890 0.6827 0.0298 0.046 Uiso 1 1 calc R . .
C15 C 0.5319(4) 0.63555(13) 0.06055(15) 0.0368(7) Uani 1 1 d . . .
H151 H 0.6095 0.6725 0.0590 0.044 Uiso 1 1 calc R . .
C16 C 0.6115(4) 0.57561(13) 0.08008(13) 0.0295(6) Uani 1 1 d . . .
H161 H 0.7432 0.5716 0.0916 0.035 Uiso 1 1 calc R . .
O1W O 0.4580(3) 0.22483(10) 0.05355(10) 0.0377(5) Uani 1 1 d . . .
H11W H 0.4226 0.2138 0.0106 0.045 Uiso 1 1 d R . .
H12W H 0.3731 0.2602 0.0588 0.045 Uiso 1 1 d 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'
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
C7 N1 C2 114.69(17) . . ?
C7 N1 C10 110.20(18) . . ?
C2 N1 C10 110.45(17) . . ?
C7 N1 H11 107.0 . . ?
C2 N1 H11 107.0 . . ?
C10 N1 H11 107.0 . . ?
C3 C2 N1 113.01(19) . . ?
C3 C2 H21 109.0 . . ?
N1 C2 H21 109.0 . . ?
C3 C2 H22 109.0 . . ?
N1 C2 H22 109.0 . . ?
H21 C2 H22 107.8 . . ?
C2 C3 C4 111.0(2) . . ?
C2 C3 H31 109.4 . . ?
C4 C3 H31 109.4 . . ?
C2 C3 H32 109.4 . . ?
C4 C3 H32 109.4 . . ?
H31 C3 H32 108.0 . . ?
N5 C4 C3 112.24(19) . . ?
N5 C4 H41 109.2 . . ?
C3 C4 H41 109.2 . . ?
N5 C4 H42 109.2 . . ?
C3 C4 H42 109.2 . . ?
H41 C4 H42 107.9 . . ?
C6 N5 C4 116.67(18) . . ?
C6 N5 H51 108.1 . . ?
C4 N5 H51 108.1 . . ?
C6 N5 H52 108.1 . . ?
C4 N5 H52 108.1 . . ?
H51 N5 H52 107.3 . . ?
N5 C6 C6 111.0(2) . 2_655 ?
N5 C6 H61 109.4 . . ?
C6 C6 H61 109.4 2_655 . ?
N5 C6 H62 109.4 . . ?
C6 C6 H62 109.4 2_655 . ?
H61 C6 H62 108.0 . . ?
N1 C7 C7 110.6(2) . 2_655 ?
N1 C7 H71 109.5 . . ?
C7 C7 H71 109.5 2_655 . ?
N1 C7 H72 109.5 . . ?
C7 C7 H72 109.5 2_655 . ?
H71 C7 H72 108.1 . . ?
C11 C10 N1 113.20(19) . . ?
C11 C10 H101 108.9 . . ?
N1 C10 H101 108.9 . . ?
C11 C10 H102 108.9 . . ?
N1 C10 H102 108.9 . . ?
H101 C10 H102 107.8 . . ?
C12 C11 C16 119.4(2) . . ?
C12 C11 C10 120.3(2) . . ?
C16 C11 C10 120.3(2) . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H121 119.8 . . ?
C13 C12 H121 119.8 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H131 120.3 . . ?
C12 C13 H131 120.3 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H141 119.8 . . ?
C13 C14 H141 119.8 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H151 119.8 . . ?
C16 C15 H151 119.8 . . ?
C11 C16 C15 120.1(3) . . ?
C11 C16 H161 120.0 . . ?
C15 C16 H161 120.0 . . ?
H11W O1W H12W 102.2 . . ?
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 C7 1.498(3) . ?
N1 C2 1.513(3) . ?
N1 C10 1.518(3) . ?
N1 H11 0.9300 . ?
C2 C3 1.511(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 C4 1.513(3) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 N5 1.502(3) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
N5 C6 1.496(3) . ?
N5 H51 0.9200 . ?
N5 H52 0.9200 . ?
C6 C6 1.518(5) 2_655 ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 C7 1.522(4) 2_655 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C10 C11 1.508(3) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 C12 1.389(4) . ?
C11 C16 1.389(4) . ?
C12 C13 1.393(4) . ?
C12 H121 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H131 0.9500 . ?
C14 C15 1.370(4) . ?
C14 H141 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
O1W H11W 0.8841 . ?
O1W H12W 0.9718 . ?
