#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:36:30 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179148 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/09/4310903.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_4310903
loop_
_publ_author_name
'Carmen Anda'
'Antoni Llobet'
'Arthur E. Martell'
'Joseph Reibenspies'
'Emanuela Berni'
'Xavier Solans'
_publ_contact_author
;
Prof. Antoni Llobet,
Departament de Quimica
Universitat de Girona
Campus Montilivi
E-17071 Girona. Spain 
tel. int+34-972.418.272
fax int+34-972.418.150
;
_publ_contact_author_email       'antoni.llobet@udg.es '
_publ_section_title
;
 A Systematic Evaluation of Molecular Recognition Phenomena. 4. Selective
 Binding of Dicarboxylic Acids to Hexaazamacrocyclic Ligands Based on
 Molecular Flexibility
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2793
_journal_page_last               2802
_journal_paper_doi               10.1021/ic035121p
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C18 H36 Br N3 O8'
_chemical_formula_weight         502.41
_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                74.22(2)
_cell_angle_beta                 65.170(10)
_cell_angle_gamma                68.070(10)
_cell_formula_units_Z            2
_cell_length_a                   10.460(5)
_cell_length_b                   11.650(5)
_cell_length_c                   12.115(6)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    162(2)
_cell_measurement_theta_max      50.5
_cell_measurement_theta_min      3.0
_cell_volume                     1231.2(10)
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      162(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5350
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_type   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0784P)²+2.9154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.2092
_reflns_number_gt                3204
_reflns_number_total             5350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic035121psi20030924_033718_1.cif
_cod_data_source_block           am78
_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_database_code               4310903
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
Br1 Br -1.02008(13) 0.82699(12) -0.47981(13) 0.0458(4) Uani 0.50 1 d P . .
Br1' Br -1.02549(17) 0.89849(13) -0.03509(17) 0.0654(5) Uani 0.50 1 d P . .
O1 O -0.6810(4) 0.3691(4) 0.2099(4) 0.0434(11) Uani 1 1 d . . .
O2 O -0.8766(4) 0.5322(3) 0.2622(3) 0.0293(9) Uani 1 1 d . . .
O3 O -1.0315(4) 0.4557(3) 0.1858(3) 0.0301(9) Uani 1 1 d . . .
O4 O -1.3090(4) 0.5900(3) 0.2089(3) 0.0261(8) Uani 1 1 d . . .
O5 O -1.3541(4) 0.4344(3) 0.1721(3) 0.0309(9) Uani 1 1 d . . .
O6 O -0.3931(9) 0.9699(8) -0.1223(9) 0.147(3) Uani 1 1 d . . .
H6D H -0.3875 0.9315 -0.0532 0.176 Uiso 1 1 d R . .
H6C H -0.3661 0.9274 -0.1794 0.176 Uiso 1 1 d R . .
O7 O -0.6941(13) 0.1686(6) 0.9299(6) 0.132(6) Uani 0.80(2) 1 d P . .
H7C H -0.6414 0.2006 0.9427 0.159 Uiso 1 1 d R . .
H7D H -0.7843 0.1816 0.9425 0.159 Uiso 1 1 d R . .
O8 O -0.1013(4) 0.9797(5) -0.2802(4) 0.0559(12) Uani 1 1 d . . .
H8C H -0.0842 1.0492 -0.3139 0.067 Uiso 1 1 d R . .
H8D H -0.0752 0.9264 -0.3274 0.067 Uiso 1 1 d R . .
N1 N -0.6011(4) 0.7811(4) -0.1520(4) 0.0210(9) Uani 1 1 d . . .
H1A H -0.6557 0.7350 -0.1522 0.025 Uiso 1 1 calc R . .
H1D H -0.5034 0.7348 -0.1794 0.025 Uiso 1 1 calc R . .
N2 N -0.6416(4) 0.5883(4) 0.2725(4) 0.0227(10) Uani 1 1 d . . .
H2A H -0.7123 0.5542 0.2815 0.027 Uiso 1 1 calc R . .
H2D H -0.5509 0.5327 0.2387 0.027 Uiso 1 1 calc R . .
N3 N -0.8268(4) 0.3662(4) 0.6477(4) 0.0220(9) Uani 1 1 d . . .
H3A H -0.9262 0.3875 0.6934 0.026 Uiso 1 1 calc R . .
H3D H -0.7800 0.3765 0.6921 0.026 Uiso 1 1 calc R . .
C1 C -0.6222(6) 0.8967(5) -0.2386(5) 0.0339(13) Uani 1 1 d . . .
H1B H -0.5644 0.9471 -0.2381 0.041 Uiso 1 1 calc R . .
H1C H -0.7276 0.9462 -0.2103 0.041 Uiso 1 1 calc R . .
C2 C -0.6430(6) 0.8011(5) -0.0252(5) 0.0293(13) Uani 1 1 d . . .
H2B H -0.7477 0.8520 0.0044 0.035 Uiso 1 1 calc R . .
H2C H -0.5826 0.8487 -0.0240 0.035 Uiso 1 1 calc R . .
C3 C -0.6228(5) 0.6814(5) 0.0600(5) 0.0249(12) Uani 1 1 d . . .
H3B H -0.5200 0.6275 0.0274 0.030 Uiso 1 1 calc R . .
H3C H -0.6894 0.6369 0.0645 0.030 Uiso 1 1 calc R . .
C4 C -0.6551(5) 0.7044(4) 0.1864(5) 0.0238(12) Uani 1 1 d . . .
H4A H -0.5858 0.7461 0.1821 0.029 Uiso 1 1 calc R . .
H4B H -0.7564 0.7614 0.2174 0.029 Uiso 1 1 calc R . .
C5 C -0.6570(5) 0.6027(4) 0.3945(5) 0.0230(12) Uani 1 1 d . . .
H5A H -0.7490 0.6700 0.4265 0.028 Uiso 1 1 calc R . .
H5B H -0.5737 0.6299 0.3857 0.028 Uiso 1 1 calc R . .
C6 C -0.6607(5) 0.4872(5) 0.4874(4) 0.0239(12) Uani 1 1 d . . .
H6A H -0.6439 0.4987 0.5577 0.029 Uiso 1 1 calc R . .
H6B H -0.5789 0.4157 0.4498 0.029 Uiso 1 1 calc R . .
C7 C -0.8040(5) 0.4562(5) 0.5345(5) 0.0252(12) Uani 1 1 d . . .
H7A H -0.8866 0.5343 0.5498 0.030 Uiso 1 1 calc R . .
H7B H -0.8072 0.4218 0.4697 0.030 Uiso 1 1 calc R . .
C8 C -0.7769(5) 0.2318(5) 0.6361(5) 0.0267(12) Uani 1 1 d . . .
H8A H -0.8358 0.2169 0.5983 0.032 Uiso 1 1 calc R . .
H8B H -0.7952 0.1829 0.7191 0.032 Uiso 1 1 calc R . .
C9 C -0.6161(5) 0.1862(4) 0.5600(5) 0.0220(11) Uani 1 1 d . . .
C10 C -0.5078(6) 0.1652(4) 0.6064(5) 0.0248(12) Uani 1 1 d . . .
H10A H -0.5355 0.1761 0.6891 0.030 Uiso 1 1 calc R . .
C11 C -0.3612(6) 0.1288(5) 0.5350(5) 0.0264(12) Uani 1 1 d . . .
H11A H -0.2883 0.1168 0.5678 0.032 Uiso 1 1 calc R . .
C12 C -0.3202(6) 0.1100(5) 0.4184(5) 0.0307(13) Uani 1 1 d . . .
H12A H -0.2181 0.0847 0.3700 0.037 Uiso 1 1 calc R . .
C13 C -0.4233(6) 0.1266(4) 0.3671(5) 0.0238(11) Uani 1 1 d . . .
C14 C -0.5718(6) 0.1645(4) 0.4396(5) 0.0245(12) Uani 1 1 d . . .
H14A H -0.6443 0.1759 0.4067 0.029 Uiso 1 1 calc R . .
C15 C -0.8103(6) 0.4309(5) 0.2173(5) 0.0269(12) Uani 1 1 d . . .
C16 C -0.8870(5) 0.3794(5) 0.1714(5) 0.0290(12) Uani 1 1 d . . .
H16A H -0.8305 0.3710 0.0834 0.035 Uiso 1 1 calc R . .
H16B H -0.8895 0.2951 0.2167 0.035 Uiso 1 1 calc R . .
C17 C -1.1142(6) 0.4014(5) 0.1574(5) 0.0324(13) Uani 1 1 d . . .
H17A H -1.1140 0.3188 0.2080 0.039 Uiso 1 1 calc R . .
H17B H -1.0665 0.3884 0.0700 0.039 Uiso 1 1 calc R . .
C18 C -1.2693(5) 0.4825(5) 0.1808(5) 0.0234(12) 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'
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
C16 O3 C17 113.5(4) . . ?
C2 N1 C1 114.4(4) . . ?
C5 N2 C4 114.8(4) . . ?
C7 N3 C8 118.2(4) . . ?
N1 C1 C13 113.2(4) . 2_465 ?
N1 C2 C3 112.6(4) . . ?
C2 C3 C4 111.4(4) . . ?
N2 C4 C3 112.1(4) . . ?
N2 C5 C6 115.1(4) . . ?
C5 C6 C7 113.6(4) . . ?
N3 C7 C6 114.5(4) . . ?
N3 C8 C9 112.9(4) . . ?
C14 C9 C10 118.0(5) . . ?
C14 C9 C8 120.8(4) . . ?
C10 C9 C8 121.2(5) . . ?
C11 C10 C9 121.1(5) . . ?
C12 C11 C10 120.1(5) . . ?
C11 C12 C13 121.7(5) . . ?
C14 C13 C12 117.9(5) . . ?
C14 C13 C1 120.4(5) . 2_465 ?
C12 C13 C1 121.6(5) . 2_465 ?
C9 C14 C13 121.1(4) . . ?
O1 C15 O2 122.8(5) . . ?
O1 C15 C16 117.2(5) . . ?
O2 C15 C16 119.9(4) . . ?
O3 C16 C15 112.1(4) . . ?
O3 C17 C18 111.5(4) . . ?
O5 C18 O4 124.3(4) . . ?
O5 C18 C17 115.3(4) . . ?
O4 C18 C17 120.5(4) . . ?
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 C15 1.250(6) . ?
O2 C15 1.261(6) . ?
O3 C16 1.402(6) . ?
O3 C17 1.429(6) . ?
O4 C18 1.257(6) . ?
O5 C18 1.262(6) . ?
N1 C2 1.469(6) . ?
N1 C1 1.472(7) . ?
N2 C5 1.467(6) . ?
N2 C4 1.466(6) . ?
N3 C7 1.472(6) . ?
N3 C8 1.481(6) . ?
C1 C13 1.495(7) 2_465 ?
C2 C3 1.495(7) . ?
C3 C4 1.501(7) . ?
C5 C6 1.502(7) . ?
C6 C7 1.510(7) . ?
C8 C9 1.502(7) . ?
C9 C14 1.396(7) . ?
C9 C10 1.382(7) . ?
C10 C11 1.371(7) . ?
C11 C12 1.348(8) . ?
C12 C13 1.389(7) . ?
C13 C14 1.390(7) . ?
C13 C1 1.495(7) 2_465 ?
C15 C16 1.492(7) . ?
C17 C18 1.490(7) . ?
