#------------------------------------------------------------------------------
#$Date: 2017-01-18 08:39:01 +0100 (Wed 18 de Jan de 2017) $
#$Revision: 190613 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/94/7119498.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_7119498
loop_
_publ_author_name
'Ahmed, Basil M.'
'Mezei, Gellert'
_publ_section_title
;
 Accessing the inaccessible: discrete multinuclear coordination complexes
 and selective anion binding attainable only by tethering ligands
 together.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1029
_journal_page_last               1032
_journal_paper_doi               10.1039/c6cc09197k
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C12 H20 N2 O2'
_chemical_formula_weight         224.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-10-06 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.3620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6684(3)
_cell_length_b                   5.43570(10)
_cell_length_c                   14.3613(3)
_cell_measurement_reflns_used    6922
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      32.14
_cell_measurement_theta_min      2.47
_cell_volume                     1287.36(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18079
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.576
_diffrn_reflns_theta_min         2.470
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, hexanes'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         2348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1015P)²+0.3317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1821
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1870
_reflns_number_total             2348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc09197k2.cif
_cod_data_source_block           7
_cod_database_code               7119498
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.35734(5) 0.1425(2) 0.47604(7) 0.0658(3) Uani 1 1 d . .
N1 N 0.31834(5) 0.68947(17) 0.66467(6) 0.0439(2) Uani 1 1 d . .
C3 C 0.33521(6) 0.51310(19) 0.60585(6) 0.0383(2) Uani 1 1 d . .
H3 H 0.2930 0.4665 0.5595 0.046 Uiso 1 1 calc R U
C5 C 0.41399(6) 0.2078(2) 0.53538(7) 0.0414(2) Uani 1 1 d . .
C4 C 0.40701(6) 0.3931(2) 0.60561(7) 0.0435(3) Uani 1 1 d . .
H4 H 0.4513 0.4306 0.6506 0.052 Uiso 1 1 calc R U
C6 C 0.49760(6) 0.0963(3) 0.53679(8) 0.0517(3) Uani 1 1 d . .
H6A H 0.5355 0.2269 0.5283 0.062 Uiso 1 1 calc R U
H6B H 0.5146 0.0239 0.5982 0.062 Uiso 1 1 calc R U
C1 C 0.24204(8) 0.8208(2) 0.64888(9) 0.0536(3) Uani 1 1 d . .
H1A H 0.2512 0.9855 0.6287 0.080 Uiso 1 1 calc R U
H1B H 0.2189 0.8259 0.7063 0.080 Uiso 1 1 calc R U
H1C H 0.2055 0.7381 0.6012 0.080 Uiso 1 1 calc R U
C2 C 0.37880(8) 0.7785(3) 0.73987(10) 0.0609(4) Uani 1 1 d . .
H2A H 0.4120 0.6437 0.7658 0.091 Uiso 1 1 calc R U
H2B H 0.3523 0.8511 0.7882 0.091 Uiso 1 1 calc R U
H2C H 0.4121 0.8995 0.7154 0.091 Uiso 1 1 calc R U
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'
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
C3 N1 C1 121.09(9) .
C3 N1 C2 121.60(10) .
C1 N1 C2 116.89(10) .
N1 C3 C4 127.66(10) .
N1 C3 H3 116.2 .
C4 C3 H3 116.2 .
O1 C5 C4 123.71(9) .
O1 C5 C6 120.36(10) .
C4 C5 C6 115.92(9) .
C3 C4 C5 119.73(9) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
C6 C6 C5 114.40(11) 5_656
C6 C6 H6A 108.7 5_656
C5 C6 H6A 108.7 .
C6 C6 H6B 108.7 5_656
C5 C6 H6B 108.7 .
H6A C6 H6B 107.6 .
N1 C1 H1A 109.5 .
N1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
N1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N1 C2 H2A 109.5 .
N1 C2 H2B 109.5 .
H2A C2 H2B 109.5 .
N1 C2 H2C 109.5 .
H2A C2 H2C 109.5 .
H2B C2 H2C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.2288(13) .
N1 C3 1.3345(13) .
N1 C1 1.4472(14) .
N1 C2 1.4490(15) .
C3 C4 1.3634(13) .
C3 H3 0.9300 .
C5 C4 1.4420(15) .
C5 C6 1.5173(14) .
C4 H4 0.9300 .
C6 C6 1.498(2) 5_656
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
