#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:06:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180123 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/21/7102113.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_7102113
loop_
_publ_author_name
'Wang, Jian'
'Onions, Stuart'
'Pilkington, Melanie'
'Stoeckli-Evans, Helen'
'Halfpenny, Joan C'
'Wallis, John D'
_publ_section_title
;
 Metal catalyzed rearrangement of a 2,2'-bipyridine Schiff-base ligand
 to a quaterpyridine-type complex.
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3628
_journal_page_last               3630
_journal_paper_doi               10.1039/b705555b
_journal_year                    2007
_chemical_formula_moiety         'C16 H14 N5, Cl'
_chemical_formula_sum            'C16 H14 Cl N5'
_chemical_formula_weight         311.77
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.248(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9931(15)
_cell_length_b                   12.4406(14)
_cell_length_c                   9.5280(11)
_cell_measurement_temperature    173(2)
_cell_volume                     1454.0(3)
_computing_cell_refinement       'HKL Scalepack (Otinowinski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction        'HKL Scalepack (Otinowinski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice and scans'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15114
_diffrn_reflns_theta_full        30.61
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4458
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0385
_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)+(0.0545P)²+0.4411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                3731
_reflns_number_total             4458
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b705555b.txt
_cod_data_source_block           rearrangedligand
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7102113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 0.75474(2) 0.18639(2) 0.63162(3) 0.01589(9) Uani 1 1 d
N1 N 0.65866(9) 0.65150(9) 0.73978(11) 0.0164(2) Uani 1 1 d
N2 N 0.78941(9) 0.43684(9) 0.59633(11) 0.0149(2) Uani 1 1 d
N3 N 0.65342(8) 0.52438(8) 0.39351(11) 0.01253(19) Uani 1 1 d
N4 N 0.48139(10) 0.70870(10) 0.51247(14) 0.0230(2) Uani 1 1 d
N5 N 0.81769(8) 0.61795(9) 0.30968(11) 0.0168(2) Uani 1 1 d
C1 C 0.70477(11) 0.63529(11) 0.88551(14) 0.0195(3) Uani 1 1 d
C2 C 0.77522(11) 0.55031(11) 0.94527(14) 0.0201(3) Uani 1 1 d
C3 C 0.80422(11) 0.48198(11) 0.85052(13) 0.0183(2) Uani 1 1 d
C4 C 0.76119(10) 0.49970(10) 0.69744(13) 0.0141(2) Uani 1 1 d
C5 C 0.68467(9) 0.58330(10) 0.64617(12) 0.0130(2) Uani 1 1 d
C6 C 0.61975(9) 0.58718(9) 0.48773(13) 0.0125(2) Uani 1 1 d
C7 C 0.51919(10) 0.64290(10) 0.42858(13) 0.0147(2) Uani 1 1 d
C8 C 0.45857(10) 0.62654(10) 0.27721(14) 0.0159(2) Uani 1 1 d
C9 C 0.49560(10) 0.55900(11) 0.19040(13) 0.0172(2) Uani 1 1 d
C10 C 0.59535(10) 0.50795(10) 0.24978(13) 0.0159(2) Uani 1 1 d
C11 C 0.76707(10) 0.47935(10) 0.45116(13) 0.0131(2) Uani 1 1 d
C12 C 0.84442(9) 0.56979(9) 0.44239(12) 0.0125(2) Uani 1 1 d
C13 C 0.93714(10) 0.59601(10) 0.56063(13) 0.0153(2) Uani 1 1 d
C14 C 1.00458(10) 0.67722(11) 0.54031(14) 0.0176(2) Uani 1 1 d
C15 C 0.97777(10) 0.72781(11) 0.40377(15) 0.0190(2) Uani 1 1 d
C16 C 0.88401(11) 0.69534(11) 0.29194(15) 0.0197(3) Uani 1 1 d
H1 H 0.8538(15) 0.4198(15) 0.889(2) 0.027(5) Uiso 1 1 d
H2 H 0.8021(14) 0.5398(14) 1.055(2) 0.025(4) Uiso 1 1 d
H3 H 0.6855(16) 0.6850(15) 0.951(2) 0.031(5) Uiso 1 1 d
H4 H 0.5201(16) 0.7194(16) 0.605(2) 0.032(5) Uiso 1 1 d
H5 H 0.4156(16) 0.7337(16) 0.474(2) 0.031(5) Uiso 1 1 d
H6 H 0.3905(15) 0.6621(15) 0.235(2) 0.027(5) Uiso 1 1 d
H7 H 0.4519(14) 0.5500(14) 0.0872(19) 0.020(4) Uiso 1 1 d
H8 H 0.6280(14) 0.4657(14) 0.1962(19) 0.022(4) Uiso 1 1 d
H9 H 0.8644(14) 0.7275(15) 0.196(2) 0.026(4) Uiso 1 1 d
H10 H 1.0213(15) 0.7847(15) 0.386(2) 0.027(4) Uiso 1 1 d
H11 H 1.0689(16) 0.6953(14) 0.620(2) 0.030(5) Uiso 1 1 d
H12 H 0.9549(14) 0.5601(14) 0.6521(19) 0.023(4) Uiso 1 1 d
H13 H 0.7863(15) 0.3679(16) 0.604(2) 0.027(5) Uiso 1 1 d
H14 H 0.7702(13) 0.4222(14) 0.3864(18) 0.018(4) Uiso 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'
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
C1 N1 C5 117.88(11)
C4 N2 C11 116.94(10)
C4 N2 H13 118.3(12)
C11 N2 H13 116.8(12)
C10 N3 C6 124.25(11)
C10 N3 C11 118.00(10)
C6 N3 C11 117.49(9)
C7 N4 H4 119.5(13)
C7 N4 H5 118.0(13)
H4 N4 H5 122.2(18)
C12 N5 C16 117.64(11)
N1 C1 C2 123.36(12)
N1 C1 H3 116.8(11)
C2 C1 H3 119.8(11)
C3 C2 C1 119.02(11)
C3 C2 H2 121.9(10)
C1 C2 H2 119.0(10)
C2 C3 C4 118.97(12)
C2 C3 H1 121.6(11)
C4 C3 H1 119.4(11)
N2 C4 C3 122.15(11)
N2 C4 C5 119.67(10)
C3 C4 C5 118.16(11)
N1 C5 C4 122.36(10)
N1 C5 C6 118.29(11)
C4 C5 C6 118.77(10)
N3 C6 C7 118.03(10)
N3 C6 C5 117.20(10)
C7 C6 C5 124.44(10)
N4 C7 C8 120.32(12)
N4 C7 C6 121.96(11)
C8 C7 C6 117.72(11)
C9 C8 C7 121.04(11)
C9 C8 H6 119.7(11)
C7 C8 H6 119.3(11)
C8 C9 C10 120.06(11)
C8 C9 H7 118.6(10)
C10 C9 H7 121.3(10)
N3 C10 C9 118.81(11)
N3 C10 H8 116.3(10)
C9 C10 H8 124.8(10)
N2 C11 N3 110.84(10)
N2 C11 C12 113.62(10)
N3 C11 C12 106.85(9)
N2 C11 H14 108.4(10)
N3 C11 H14 106.7(10)
C12 C11 H14 110.2(10)
N5 C12 C13 123.14(11)
N5 C12 C11 114.25(10)
C13 C12 C11 122.55(11)
C12 C13 C14 118.35(12)
C12 C13 H12 121.5(11)
C14 C13 H12 120.1(11)
C15 C14 C13 119.10(11)
C15 C14 H11 121.8(11)
C13 C14 H11 119.0(11)
C14 C15 C16 118.36(12)
C14 C15 H10 121.8(11)
C16 C15 H10 119.8(11)
N5 C16 C15 123.41(12)
N5 C16 H9 116.3(11)
C15 C16 H9 120.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3338(16)
N1 C5 1.3522(15)
N2 C4 1.3810(15)
N2 C11 1.4185(15)
N2 H13 0.86(2)
N3 C10 1.3436(15)
N3 C6 1.3663(15)
N3 C11 1.5038(15)
N4 C7 1.3449(17)
N4 H4 0.87(2)
N4 H5 0.87(2)
N5 C12 1.3375(15)
N5 C16 1.3395(16)
C1 C2 1.391(2)
C1 H3 0.969(19)
C2 C3 1.3798(19)
C2 H2 0.995(17)
C3 C4 1.3967(16)
C3 H1 0.995(18)
C4 C5 1.4101(17)
C5 C6 1.4674(16)
C6 C7 1.4212(17)
C7 C8 1.4117(17)
C8 C9 1.3725(18)
C8 H6 0.951(19)
C9 C10 1.3856(18)
C9 H7 0.966(17)
C10 H8 0.928(18)
C11 C12 1.5292(17)
C11 H14 0.951(17)
C12 C13 1.3900(16)
C13 C14 1.3920(18)
C13 H12 0.938(17)
C14 C15 1.3825(19)
C14 H11 0.954(19)
C15 C16 1.3881(18)
C15 H10 0.957(19)
C16 H9 0.952(18)
