#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:12:28 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179050 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/12/4301202.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_4301202
loop_
_publ_author_name
'Miloslav Polášek'
'Miroslava Šedinová'
'Jan Kotek'
'Luce Vander Elst'
'Robert N. Muller'
'Petr Hermann'
'Ivan Lukeš'
_publ_section_title
;
Pyridine-N-oxide Analogues of DOTA and Their Gadolinium(III) Complexes
Endowed with a Fast Water Exchange on the Square-Antiprismatic Isomer
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              455
_journal_page_last               465
_journal_paper_doi               10.1021/ic801596v
_journal_volume                  48
_journal_year                    2009
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C8 H10 N O3, Cl'
_chemical_formula_sum            'C8 H10 Cl N O3'
_chemical_formula_weight         203.62
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 93.1750(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9361(3)
_cell_length_b                   6.5821(2)
_cell_length_c                   12.9236(4)
_cell_measurement_reflns_used    2289
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     928.85(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4260
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0327
_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)+(0.0386P)²+0.2766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                1900
_reflns_number_total             2318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801596v_si_002_1.cif
_cod_data_source_block           2-olhcl
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4301202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
Cl1 Cl -0.00933(4) 0.2500 0.59479(4) 0.02944(14) Uani 1 2 d S . .
Cl2 Cl 0.48327(4) 0.2500 0.35616(4) 0.02681(14) Uani 1 2 d S . .
N1A N -0.08056(15) 0.2500 0.36193(13) 0.0257(4) Uani 1 2 d S . .
H11A H -0.0594 0.2500 0.4332 0.031 Uiso 1 2 d SR . .
C2A C 0.01154(17) 0.2500 0.29742(15) 0.0233(4) Uani 1 2 d S . .
C3A C -0.01644(18) 0.2500 0.19188(16) 0.0259(4) Uani 1 2 d S . .
H31A H 0.0458 0.2500 0.1457 0.031 Uiso 1 2 calc SR . .
C4A C -0.13821(18) 0.2500 0.15542(16) 0.0263(4) Uani 1 2 d S . .
C5A C -0.23048(18) 0.2500 0.22481(17) 0.0293(5) Uani 1 2 d S . .
H51A H -0.3123 0.2500 0.2010 0.035 Uiso 1 2 calc SR . .
C6A C -0.19916(18) 0.2500 0.32890(17) 0.0293(5) Uani 1 2 d S . .
H61A H -0.2598 0.2500 0.3766 0.035 Uiso 1 2 calc SR . .
C7A C 0.13925(17) 0.2500 0.34556(16) 0.0273(4) Uani 1 2 d S . .
H71A H 0.1524 0.3696 0.3886 0.033 Uiso 0.50 1 calc PR . .
H72A H 0.1524 0.1304 0.3886 0.033 Uiso 0.50 1 calc PR . .
O71A O 0.22097(13) 0.2500 0.26483(11) 0.0381(4) Uani 1 2 d S . .
H7A H 0.2879 0.2500 0.2901 0.046 Uiso 1 2 d SR . .
C8A C -0.17161(18) 0.2500 0.04122(17) 0.0299(5) Uani 1 2 d S . .
O81A O -0.07213(13) 0.2500 -0.01307(11) 0.0365(4) Uani 1 2 d S . .
C9A C -0.0923(2) 0.2500 -0.12488(16) 0.0396(6) Uani 1 2 d S . .
H91A H -0.1402 0.1314 -0.1464 0.048 Uiso 1 1 d R . .
H92A H -0.0146 0.2500 -0.1537 0.048 Uiso 1 2 d SR . .
O82A O -0.27553(13) 0.2500 0.00484(13) 0.0410(4) Uani 1 2 d S . .
N1B N 0.47393(15) 0.2500 0.59590(13) 0.0255(4) Uani 1 2 d S . .
H11B H 0.5066 0.2500 0.5327 0.031 Uiso 1 2 d SR . .
C2B C 0.55063(18) 0.2500 0.67968(16) 0.0260(4) Uani 1 2 d S . .
C3B C 0.50302(18) 0.2500 0.77696(16) 0.0260(4) Uani 1 2 d S . .
H31B H 0.5553 0.2500 0.8362 0.031 Uiso 1 2 calc SR . .
C4B C 0.37847(18) 0.2500 0.78541(16) 0.0252(4) Uani 1 2 d S . .
C5B C 0.30080(18) 0.2500 0.69622(16) 0.0291(5) Uani 1 2 d S . .
H51B H 0.2162 0.2500 0.7009 0.035 Uiso 1 2 calc SR . .
C6B C 0.35114(19) 0.2500 0.60166(17) 0.0297(5) Uani 1 2 d S . .
H61B H 0.3007 0.2500 0.5413 0.036 Uiso 1 2 calc SR . .
C7B C 0.68570(18) 0.2500 0.66896(17) 0.0332(5) Uani 1 2 d S . .
H71B H 0.7214 0.3693 0.7027 0.040 Uiso 0.50 1 calc PR . .
H72B H 0.7214 0.1307 0.7027 0.040 Uiso 0.50 1 calc PR . .
O71B O 0.71232(14) 0.2500 0.56385(12) 0.0530(5) Uani 1 2 d S . .
H7B H 0.7862 0.2500 0.5608 0.064 Uiso 1 2 d SR . .
C8B C 0.32414(19) 0.2500 0.88964(17) 0.0300(5) Uani 1 2 d S . .
O81B O 0.41050(14) 0.2500 0.96532(11) 0.0389(4) Uani 1 2 d S . .
C9B C 0.3690(2) 0.2500 1.07033(18) 0.0465(6) Uani 1 2 d S . .
H91B H 0.4384 0.2500 1.1123 0.056 Uiso 1 2 d SR . .
H92B H 0.3195 0.1309 1.0770 0.056 Uiso 1 1 d R . .
O82B O 0.21566(14) 0.2500 0.90162(13) 0.0455(4) Uani 1 2 d S . .
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
C2A N1A C6A 123.18(18) . . ?
C2A N1A H11A 117.2 . . ?
C6A N1A H11A 119.6 . . ?
N1A C2A C3A 118.71(17) . . ?
N1A C2A C7A 117.17(17) . . ?
C3A C2A C7A 124.12(17) . . ?
C2A C3A C4A 119.42(18) . . ?
C2A C3A H31A 120.3 . . ?
C4A C3A H31A 120.3 . . ?
C5A C4A C3A 119.96(19) . . ?
C5A C4A C8A 119.33(18) . . ?
C3A C4A C8A 120.71(18) . . ?
C6A C5A C4A 118.94(18) . . ?
C6A C5A H51A 120.5 . . ?
C4A C5A H51A 120.5 . . ?
N1A C6A C5A 119.78(18) . . ?
N1A C6A H61A 120.1 . . ?
C5A C6A H61A 120.1 . . ?
O71A C7A C2A 107.89(16) . . ?
O71A C7A H71A 110.1 . . ?
C2A C7A H71A 110.1 . . ?
O71A C7A H72A 110.1 . . ?
C2A C7A H72A 110.1 . . ?
H71A C7A H72A 108.4 . . ?
C7A O71A H7A 107.9 . . ?
O82A C8A O81A 125.2(2) . . ?
O82A C8A C4A 123.8(2) . . ?
O81A C8A C4A 110.98(17) . . ?
C8A O81A C9A 116.29(16) . . ?
O81A C9A H91A 109.6 . . ?
O81A C9A H92A 107.5 . . ?
H91A C9A H92A 111.6 . . ?
C2B N1B C6B 122.61(18) . . ?
C2B N1B H11B 118.0 . . ?
C6B N1B H11B 119.4 . . ?
N1B C2B C3B 119.05(18) . . ?
N1B C2B C7B 120.44(18) . . ?
C3B C2B C7B 120.51(18) . . ?
C4B C3B C2B 119.74(19) . . ?
C4B C3B H31B 120.1 . . ?
C2B C3B H31B 120.1 . . ?
C3B C4B C5B 119.76(19) . . ?
C3B C4B C8B 120.99(18) . . ?
C5B C4B C8B 119.24(18) . . ?
C6B C5B C4B 118.81(19) . . ?
C6B C5B H51B 120.6 . . ?
C4B C5B H51B 120.6 . . ?
N1B C6B C5B 120.02(19) . . ?
N1B C6B H61B 120.0 . . ?
C5B C6B H61B 120.0 . . ?
O71B C7B C2B 110.44(18) . . ?
O71B C7B H71B 109.6 . . ?
C2B C7B H71B 109.6 . . ?
O71B C7B H72B 109.6 . . ?
C2B C7B H72B 109.6 . . ?
H71B C7B H72B 108.1 . . ?
C7B O71B H7B 107.9 . . ?
O82B C8B O81B 125.0(2) . . ?
O82B C8B C4B 123.8(2) . . ?
O81B C8B C4B 111.21(17) . . ?
C8B O81B C9B 116.30(17) . . ?
O81B C9B H91B 105.2 . . ?
O81B C9B H92B 106.9 . . ?
H91B C9B H92B 113.8 . . ?
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
N1A C2A 1.342(2) . ?
N1A C6A 1.343(3) . ?
N1A H11A 0.9368 . ?
C2A C3A 1.381(3) . ?
C2A C7A 1.497(3) . ?
C3A C4A 1.388(3) . ?
C3A H31A 0.9300 . ?
C4A C5A 1.387(3) . ?
C4A C8A 1.501(3) . ?
C5A C6A 1.370(3) . ?
C5A H51A 0.9300 . ?
C6A H61A 0.9300 . ?
C7A O71A 1.411(2) . ?
C7A H71A 0.9700 . ?
C7A H72A 0.9700 . ?
O71A H7A 0.7851 . ?
C8A O82A 1.206(2) . ?
C8A O81A 1.327(3) . ?
O81A C9A 1.450(3) . ?
C9A H91A 0.9718 . ?
C9A H92A 0.9467 . ?
N1B C2B 1.332(3) . ?
N1B C6B 1.349(3) . ?
N1B H11B 0.9088 . ?
C2B C3B 1.387(3) . ?
C2B C7B 1.491(3) . ?
C3B C4B 1.372(3) . ?
C3B H31B 0.9300 . ?
C4B C5B 1.393(3) . ?
C4B C8B 1.502(3) . ?
C5B C6B 1.368(3) . ?
C5B H51B 0.9300 . ?
C6B H61B 0.9300 . ?
C7B O71B 1.405(3) . ?
C7B H71B 0.9700 . ?
C7B H72B 0.9700 . ?
O71B H7B 0.8111 . ?
C8B O82B 1.205(3) . ?
C8B O81B 1.321(3) . ?
O81B C9B 1.455(3) . ?
C9B H91B 0.9083 . ?
C9B H92B 0.9592 . ?
