#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/57/2015776.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015776
loop_
_publ_author_name
'Bortoluzzi, Adailton J.'
'Neves, Ademir'
'Rey, Nicolas A.'
_publ_section_title
;2-{[Bis(2-pyridylmethyl)amino]methyl}-6-[(2-hydroxyanilino)methyl]-4-methylphenol:
 a novel binucleating asymmetric ligand as a precursor to synthetic models for
 metalloenzymes
;
_journal_coeditor_code           BM3018
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o84
_journal_page_last               o86
_journal_paper_doi               10.1107/S0108270106050517
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C27 H28 N4 O2'
_chemical_formula_moiety         'C27 H28 N4 O2'
_chemical_formula_sum            'C27 H28 N4 O2'
_chemical_formula_weight         440.53
_chemical_name_systematic
;
2-[N,N-Bis(2-pyridylmethyl)aminomethyl]-6-[N-(2-hydroxyanilino)methyl]-
4-methylphenol
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6510(10)
_cell_length_b                   21.071(5)
_cell_length_c                   9.2620(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.66
_cell_measurement_theta_min      6.66
_cell_volume                     2372.2(7)
_computing_cell_refinement       'SET4 in CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4338
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.0072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.151
_refine_ls_R_factor_gt           0.0531
_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)+(0.056P)²+0.792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.121
_refine_ls_wR_factor_ref         0.155
_reflns_number_gt                2138
_reflns_number_total             4142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3018.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015776
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.68229(18) 0.12805(9) 0.7041(3) 0.0599(6) Uani d . 1
H H1O 0.7370 0.1234 0.6741 0.090 Uiso calc R 1
O O20 0.47861(18) 0.24240(11) 0.5095(2) 0.0643(7) Uani d . 1
H H20O 0.4700 0.2585 0.4264 0.096 Uiso calc R 1
N N1 0.4876(2) 0.18120(13) 0.7641(3) 0.0509(7) Uani d D 1
H H1N 0.5396(17) 0.1931(13) 0.728(3) 0.050(9) Uiso d D 1
N N4 0.84061(19) 0.05914(12) 0.6194(3) 0.0485(7) Uani d . 1
N N32 1.1004(3) 0.03344(17) 0.8827(4) 0.0802(10) Uani d . 1
N N42 0.8029(3) 0.17139(15) 0.4450(3) 0.0786(10) Uani d . 1
C C2 0.5232(3) 0.12487(15) 0.8595(3) 0.0553(9) Uani d . 1
H H2A 0.4649 0.1134 0.9040 0.066 Uiso calc R 1
H H2B 0.5869 0.1365 0.9409 0.066 Uiso calc R 1
C C3 0.7420(2) 0.02186(15) 0.5442(3) 0.0506(8) Uani d . 1
H H3A 0.7644 -0.0205 0.5241 0.061 Uiso calc R 1
H H3B 0.7059 0.0415 0.4485 0.061 Uiso calc R 1
C C5 0.4781(3) -0.10945(16) 0.7337(4) 0.0635(10) Uani d . 1
H H5A 0.4261 -0.1052 0.7914 0.076 Uiso calc PR 0.50
H H5B 0.5336 -0.1396 0.7814 0.076 Uiso calc PR 0.50
H H5C 0.4408 -0.1239 0.6343 0.076 Uiso calc PR 0.50
H H5D 0.5076 -0.1406 0.6800 0.076 Uiso calc PR 0.50
H H5E 0.4000 -0.1062 0.6900 0.076 Uiso calc PR 0.50
H H5F 0.4929 -0.1219 0.8371 0.076 Uiso calc PR 0.50
C C11 0.5522(2) 0.06693(14) 0.7822(3) 0.0448(7) Uani d . 1
C C12 0.6327(2) 0.07022(14) 0.7071(3) 0.0450(7) Uani d . 1
C C13 0.6613(2) 0.01699(14) 0.6364(3) 0.0432(7) Uani d . 1
C C14 0.6101(2) -0.04015(14) 0.6476(3) 0.0466(8) Uani d . 1
H H14 0.6296 -0.0759 0.6019 0.056 Uiso calc R 1
C C15 0.5310(2) -0.04600(14) 0.7243(3) 0.0461(8) Uani d . 1
C C16 0.5027(2) 0.00816(15) 0.7886(3) 0.0491(8) Uani d . 1
H H16 0.4483 0.0054 0.8383 0.059 Uiso calc R 1
C C21 0.3899(2) 0.17803(14) 0.6457(3) 0.0464(8) Uani d . 1
C C22 0.3845(3) 0.21213(14) 0.5142(4) 0.0491(8) Uani d . 1
C C23 0.2884(3) 0.21430(17) 0.3998(4) 0.0674(10) Uani d . 1
H H23 0.2860 0.2368 0.3126 0.081 Uiso calc R 1
C C24 0.1961(3) 0.18349(19) 0.4132(5) 0.0793(12) Uani d . 1
H H24 0.1314 0.1851 0.3353 0.095 Uiso calc R 1
C C25 0.1997(3) 0.15053(19) 0.5411(5) 0.0778(12) Uani d . 1
H H25 0.1367 0.1303 0.5508 0.093 Uiso calc R 1
C C26 0.2960(3) 0.14690(16) 0.6563(4) 0.0624(9) Uani d . 1
H H26 0.2978 0.1233 0.7418 0.075 Uiso calc R 1
C C30 0.9078(3) 0.02456(16) 0.7502(4) 0.0624(9) Uani d . 1
H H30A 0.9355 -0.0140 0.7162 0.075 Uiso calc R 1
H H30B 0.8619 0.0124 0.8138 0.075 Uiso calc R 1
C C31 1.0032(3) 0.06306(19) 0.8409(4) 0.0625(9) Uani d . 1
C C33 1.1866(4) 0.0661(3) 0.9666(5) 0.0963(15) Uani d . 1
H H33 1.2546 0.0460 0.9959 0.116 Uiso calc R 1
C C34 1.1802(5) 0.1264(3) 1.0107(5) 0.1101(18) Uani d . 1
H H34 1.2421 0.1467 1.0708 0.132 Uiso calc R 1
C C35 1.0820(5) 0.1573(3) 0.9664(6) 0.1223(18) Uani d . 1
H H35 1.0758 0.1996 0.9921 0.147 Uiso calc R 1
C C36 0.9915(4) 0.1240(2) 0.8817(5) 0.0980(14) Uani d . 1
H H36 0.9228 0.1433 0.8528 0.118 Uiso calc R 1
C C40 0.9037(3) 0.07305(17) 0.5122(4) 0.0631(10) Uani d . 1
H H40A 0.9115 0.0343 0.4594 0.076 Uiso calc R 1
H H40B 0.9769 0.0870 0.5673 0.076 Uiso calc R 1
C C41 0.8518(2) 0.12308(15) 0.3990(4) 0.0515(8) Uani d . 1
C C43 0.7592(4) 0.21651(18) 0.3444(4) 0.0839(13) Uani d . 1
H H43 0.7233 0.2500 0.3763 0.101 Uiso calc R 1
C C44 0.7633(4) 0.2172(2) 0.2025(5) 0.0857(13) Uani d . 1
H H44 0.7354 0.2510 0.1387 0.103 Uiso calc R 1
C C45 0.8102(4) 0.1662(3) 0.1551(5) 0.120(2) Uani d . 1
H H45 0.8128 0.1640 0.0558 0.144 Uiso calc R 1
C C46 0.8540(4) 0.1176(2) 0.2534(4) 0.0937(14) Uani d . 1
H H46 0.8843 0.0820 0.2209 0.112 Uiso calc R 1
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_publ_flag
C12 O1 H1O 109.5 ?
C22 O20 H20O 109.5 ?
C21 N1 C2 119.0(3) y
C21 N1 H1N 108(2) ?
C2 N1 H1N 109(2) ?
C40 N4 C30 111.0(2) y
C40 N4 C3 109.6(2) y
C30 N4 C3 110.2(2) y
C31 N32 C33 117.6(4) ?
C41 N42 C43 117.5(3) ?
N1 C2 C11 116.1(2) y
N1 C2 H2A 108.3 ?
C11 C2 H2A 108.3 ?
N1 C2 H2B 108.3 ?
C11 C2 H2B 108.3 ?
H2A C2 H2B 107.4 ?
N4 C3 C13 112.7(2) y
N4 C3 H3A 109.0 ?
C13 C3 H3A 109.0 ?
N4 C3 H3B 109.0 ?
C13 C3 H3B 109.0 ?
H3A C3 H3B 107.8 ?
C15 C5 H5A 109.5 ?
C15 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C15 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C15 C5 H5D 109.5 ?
H5A C5 H5D 141.1 ?
H5B C5 H5D 56.3 ?
H5C C5 H5D 56.3 ?
C15 C5 H5E 109.5 ?
H5A C5 H5E 56.3 ?
H5B C5 H5E 141.1 ?
H5C C5 H5E 56.3 ?
H5D C5 H5E 109.5 ?
C15 C5 H5F 109.5 ?
H5A C5 H5F 56.3 ?
H5B C5 H5F 56.3 ?
H5C C5 H5F 141.1 ?
H5D C5 H5F 109.5 ?
H5E C5 H5F 109.5 ?
C12 C11 C16 117.8(3) ?
C12 C11 C2 120.4(3) ?
C16 C11 C2 121.7(3) ?
O1 C12 C11 117.2(3) ?
O1 C12 C13 121.6(3) ?
C11 C12 C13 121.2(3) ?
C14 C13 C12 118.4(3) ?
C14 C13 C3 120.4(3) ?
C12 C13 C3 121.1(3) ?
C15 C14 C13 122.4(3) ?
C15 C14 H14 118.8 ?
C13 C14 H14 118.8 ?
C16 C15 C14 117.4(3) ?
C16 C15 C5 122.4(3) ?
C14 C15 C5 120.3(3) ?
C15 C16 C11 122.8(3) ?
C15 C16 H16 118.6 ?
C11 C16 H16 118.6 ?
C26 C21 C22 118.0(3) ?
C26 C21 N1 123.5(3) ?
C22 C21 N1 118.3(3) ?
O20 C22 C23 123.6(3) ?
O20 C22 C21 115.9(3) ?
C23 C22 C21 120.5(3) ?
C24 C23 C22 120.5(4) ?
C24 C23 H23 119.7 ?
C22 C23 H23 119.7 ?
C25 C24 C23 119.7(4) ?
C25 C24 H24 120.2 ?
C23 C24 H24 120.2 ?
C24 C25 C26 120.6(3) ?
C24 C25 H25 119.7 ?
C26 C25 H25 119.7 ?
C25 C26 C21 120.6(3) ?
C25 C26 H26 119.7 ?
C21 C26 H26 119.7 ?
N4 C30 C31 112.7(3) ?
N4 C30 H30A 109.1 ?
C31 C30 H30A 109.1 ?
N4 C30 H30B 109.1 ?
C31 C30 H30B 109.1 ?
H30A C30 H30B 107.8 ?
N32 C31 C36 121.5(4) ?
N32 C31 C30 116.2(4) ?
C36 C31 C30 122.2(4) ?
N32 C33 C34 123.7(5) ?
N32 C33 H33 118.2 ?
C34 C33 H33 118.2 ?
C33 C34 C35 119.2(5) ?
C33 C34 H34 120.4 ?
C35 C34 H34 120.4 ?
C34 C35 C36 117.9(6) ?
C34 C35 H35 121.0 ?
C36 C35 H35 121.0 ?
C31 C36 C35 120.0(5) ?
C31 C36 H36 120.0 ?
C35 C36 H36 120.0 ?
N4 C40 C41 113.4(2) ?
N4 C40 H40A 108.9 ?
C41 C40 H40A 108.9 ?
N4 C40 H40B 108.9 ?
C41 C40 H40B 108.9 ?
H40A C40 H40B 107.7 ?
N42 C41 C46 121.6(3) ?
N42 C41 C40 117.9(3) ?
C46 C41 C40 120.5(3) ?
C44 C43 N42 125.0(4) ?
C44 C43 H43 117.5 ?
N42 C43 H43 117.5 ?
C43 C44 C45 116.8(4) ?
C43 C44 H44 121.6 ?
C45 C44 H44 121.6 ?
C44 C45 C46 120.3(4) ?
C44 C45 H45 119.8 ?
C46 C45 H45 119.8 ?
C41 C46 C45 118.5(4) ?
C41 C46 H46 120.8 ?
C45 C46 H46 120.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 1.374(3) y
O1 H1O 0.8200 ?
O20 C22 1.362(3) y
O20 H20O 0.8200 ?
N1 C21 1.408(4) y
N1 C2 1.474(4) y
N1 H1N 0.860(10) ?
N4 C40 1.465(4) y
N4 C30 1.466(4) y
N4 C3 1.475(4) y
N32 C31 1.337(4) ?
N32 C33 1.341(5) ?
N42 C41 1.322(4) ?
N42 C43 1.338(4) ?
C2 C11 1.511(4) y
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C13 1.505(4) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C5 C15 1.509(4) ?
C5 H5A 0.9600 ?
C5 H5B 0.9600 ?
C5 H5C 0.9600 ?
C5 H5D 0.9600 ?
C5 H5E 0.9600 ?
C5 H5F 0.9600 ?
C11 C12 1.385(4) ?
C11 C16 1.396(4) ?
C12 C13 1.396(4) ?
C13 C14 1.384(4) ?
C14 C15 1.384(4) ?
C14 H14 0.9300 ?
C15 C16 1.380(4) ?
C16 H16 0.9300 ?
C21 C26 1.384(4) ?
C21 C22 1.399(4) ?
C22 C23 1.374(4) ?
C23 C24 1.371(5) ?
C23 H23 0.9300 ?
C24 C25 1.363(5) ?
C24 H24 0.9300 ?
C25 C26 1.382(5) ?
C25 H25 0.9300 ?
C26 H26 0.9300 ?
C30 C31 1.503(5) ?
C30 H30A 0.9700 ?
C30 H30B 0.9700 ?
C31 C36 1.357(5) ?
C33 C34 1.342(7) ?
C33 H33 0.9300 ?
C34 C35 1.362(7) ?
C34 H34 0.9300 ?
C35 C36 1.386(6) ?
C35 H35 0.9300 ?
C36 H36 0.9300 ?
C40 C41 1.504(4) ?
C40 H40A 0.9700 ?
C40 H40B 0.9700 ?
C41 C46 1.362(5) ?
C43 C44 1.330(5) ?
C43 H43 0.9300 ?
C44 C45 1.358(6) ?
C44 H44 0.9300 ?
C45 C46 1.379(5) ?
C45 H45 0.9300 ?
C46 H46 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 . 0.860(10) 2.32(2) 2.896(3) 124(2) y
N1 H1N O20 . 0.860(10) 2.22(3) 2.662(3) 113(2) y
O1 H1O N4 . 0.82 2.04 2.758(3) 145 y
O1 H1O N42 . 0.82 2.68 3.309(4) 134 y
O20 H20O N1 4_565 0.82 2.03 2.813(3) 160 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C21 N1 C2 C11 63.9(4)
C40 N4 C3 C13 -168.3(2)
C30 N4 C3 C13 69.2(3)
N1 C2 C11 C12 57.2(4)
N1 C2 C11 C16 -125.3(3)
C16 C11 C12 O1 -178.8(3)
C2 C11 C12 O1 -1.2(4)
C16 C11 C12 C13 1.8(4)
C2 C11 C12 C13 179.4(3)
O1 C12 C13 C14 178.2(3)
C11 C12 C13 C14 -2.4(4)
O1 C12 C13 C3 -4.5(4)
C11 C12 C13 C3 174.9(3)
N4 C3 C13 C14 -137.2(3)
N4 C3 C13 C12 45.5(4)
C12 C13 C14 C15 0.9(4)
C3 C13 C14 C15 -176.4(3)
C13 C14 C15 C16 1.1(4)
C13 C14 C15 C5 -179.8(3)
C14 C15 C16 C11 -1.7(4)
C5 C15 C16 C11 179.2(3)
C12 C11 C16 C15 0.3(4)
C2 C11 C16 C15 -177.2(3)
C2 N1 C21 C26 39.0(4)
C2 N1 C21 C22 -146.0(3)
C26 C21 C22 O20 179.4(3)
N1 C21 C22 O20 4.2(4)
C26 C21 C22 C23 0.0(4)
N1 C21 C22 C23 -175.3(3)
O20 C22 C23 C24 -178.9(3)
C21 C22 C23 C24 0.5(5)
C22 C23 C24 C25 0.1(6)
C23 C24 C25 C26 -1.2(6)
C24 C25 C26 C21 1.7(6)
C22 C21 C26 C25 -1.1(5)
N1 C21 C26 C25 173.9(3)
C40 N4 C30 C31 64.4(4)
C3 N4 C30 C31 -174.0(3)
C33 N32 C31 C36 -0.1(5)
C33 N32 C31 C30 -178.5(3)
N4 C30 C31 N32 -134.2(3)
N4 C30 C31 C36 47.4(5)
C31 N32 C33 C34 0.3(6)
N32 C33 C34 C35 -1.5(8)
C33 C34 C35 C36 2.4(8)
N32 C31 C36 C35 1.2(7)
C30 C31 C36 C35 179.5(4)
C34 C35 C36 C31 -2.3(8)
C30 N4 C40 C41 -164.0(3)
C3 N4 C40 C41 74.0(4)
C43 N42 C41 C46 -2.7(6)
C43 N42 C41 C40 178.4(3)
N4 C40 C41 N42 37.6(4)
N4 C40 C41 C46 -141.3(4)
C41 N42 C43 C44 -1.5(7)
N42 C43 C44 C45 3.8(7)
C43 C44 C45 C46 -2.0(8)
N42 C41 C46 C45 4.3(7)
C40 C41 C46 C45 -176.8(4)
C44 C45 C46 C41 -1.9(8)
