#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151375.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_7151375
loop_
_publ_author_name
'Mathias Düggeli'
'Catherine Goujon-Ginglinger'
'Sarah Richard Ducotterd'
'David Mauron'
'Christophe Bonte'
'Alexander von Zelewsky'
'Helen Stoeckli-Evans'
'Antonia Neels'
_publ_section_title
;
 Synthetic routes for a new family of chiral tetradentate ligands
 containing pyridine rings
;
_journal_issue                   11
_journal_name_full               'Org. Biomol. Chem.'
_journal_page_first              1894
_journal_page_last               1899
_journal_paper_doi               10.1039/b210625f
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C34 H50 N4'
_chemical_formula_sum            'C34 H50 N4'
_chemical_formula_weight         514.78
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.4893(8)
_cell_length_b                   20.8542(16)
_cell_length_c                   6.4198(4)
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      1.95
_cell_volume                     1538.19(19)
_computing_cell_refinement       'CELL (Stoe IPDS Software, 2000)'
_computing_data_collection       'EXPOSE (Stoe IPDS Software, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS Software, 2000)'
_computing_molecular_graphics    'PLATON99 (Spek, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_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  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12014
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.834
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.834
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0417
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                1789
_reflns_number_total             2938
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b210625f.txt
_cod_data_source_block           cpd3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7151375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, 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
N1 N 0.13020(14) 0.41124(8) 0.2106(3) 0.0266(4) Uani 1 1 d . . .
N2 N 0.35112(15) 0.30393(10) 0.4161(4) 0.0411(5) Uani 1 1 d . . .
C1 C 0.19659(18) 0.35825(10) 0.2257(4) 0.0279(5) Uani 1 1 d . . .
C2 C 0.16894(18) 0.30235(11) 0.1240(4) 0.0324(6) Uani 1 1 d . . .
H2 H 0.2156 0.2651 0.1420 0.039 Uiso 1 1 calc R . .
C3 C 0.07138(19) 0.30078(11) -0.0063(4) 0.0326(6) Uani 1 1 d . . .
H3 H 0.0505 0.2624 -0.0767 0.039 Uiso 1 1 calc R . .
C4 C 0.00577(19) 0.35568(10) -0.0315(4) 0.0287(6) Uani 1 1 d . . .
C5 C 0.03685(16) 0.40935(10) 0.0836(4) 0.0241(5) Uani 1 1 d . . .
C6 C -0.03672(16) 0.46930(9) 0.0677(4) 0.0240(5) Uani 1 1 d . . .
H6 H -0.0844 0.4708 0.1979 0.029 Uiso 1 1 calc R . .
C7 C -0.12401(17) 0.46154(10) -0.1128(4) 0.0273(5) Uani 1 1 d . . .
H7A H -0.1700 0.5008 -0.1477 0.033 Uiso 1 1 calc R . .
C8 C -0.19770(18) 0.39891(10) -0.0805(4) 0.0303(6) Uani 1 1 d . . .
C9 C -0.09290(18) 0.36357(10) -0.1854(4) 0.0319(6) Uani 1 1 d . . .
H9A H -0.1120 0.3255 -0.2739 0.038 Uiso 1 1 calc R . .
C10 C -0.06709(19) 0.42724(10) -0.3013(4) 0.0326(6) Uani 1 1 d . . .
H10B H -0.1101 0.4324 -0.4339 0.039 Uiso 1 1 calc R . .
H10A H 0.0168 0.4366 -0.3191 0.039 Uiso 1 1 calc R . .
C11 C -0.23412(19) 0.37984(11) 0.1376(4) 0.0383(7) Uani 1 1 d . . .
H11C H -0.2779 0.3395 0.1321 0.057 Uiso 1 1 calc R . .
H11B H -0.2833 0.4135 0.1974 0.057 Uiso 1 1 calc R . .
H11A H -0.1648 0.3741 0.2245 0.057 Uiso 1 1 calc R . .
C12 C -0.3064(2) 0.39866(12) -0.2207(4) 0.0431(7) Uani 1 1 d . . .
H12C H -0.3395 0.3554 -0.2250 0.065 Uiso 1 1 calc R . .
H12B H -0.2848 0.4120 -0.3619 0.065 Uiso 1 1 calc R . .
H12A H -0.3643 0.4285 -0.1645 0.065 Uiso 1 1 calc R . .
C13 C 0.3109(2) 0.36660(11) 0.3500(4) 0.0355(6) Uani 1 1 d . . .
C14 C 0.4001(2) 0.39367(15) 0.1869(6) 0.0673(10) Uani 1 1 d . . .
H14C H 0.3654 0.4303 0.1141 0.101 Uiso 1 1 calc R . .
H14B H 0.4195 0.3601 0.0859 0.101 Uiso 1 1 calc R . .
H14A H 0.4709 0.4075 0.2591 0.101 Uiso 1 1 calc R . .
C15 C 0.2960(2) 0.41529(14) 0.5242(5) 0.0611(10) Uani 1 1 d . . .
H15C H 0.2731 0.4567 0.4650 0.092 Uiso 1 1 calc R . .
H15B H 0.3697 0.4201 0.5994 0.092 Uiso 1 1 calc R . .
H15A H 0.2356 0.4005 0.6206 0.092 Uiso 1 1 calc R . .
C16 C 0.2755(2) 0.27632(16) 0.5745(5) 0.0642(9) Uani 1 1 d . . .
H16C H 0.2923 0.2305 0.5887 0.096 Uiso 1 1 calc R . .
H16B H 0.1940 0.2821 0.5334 0.096 Uiso 1 1 calc R . .
H16A H 0.2892 0.2978 0.7080 0.096 Uiso 1 1 calc R . .
C17 C 0.4711(2) 0.30241(15) 0.4939(5) 0.0556(8) Uani 1 1 d . . .
H17C H 0.4935 0.2580 0.5236 0.083 Uiso 1 1 calc R . .
H17B H 0.4765 0.3279 0.6217 0.083 Uiso 1 1 calc R . .
H17A H 0.5235 0.3203 0.3883 0.083 Uiso 1 1 calc R . .
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'
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
C1 N1 C5 118.07(18) . . ?
C13 N2 C16 111.7(2) . . ?
C13 N2 C17 114.8(2) . . ?
C16 N2 C17 108.3(2) . . ?
N1 C1 C2 122.10(19) . . ?
N1 C1 C13 115.20(18) . . ?
C2 C1 C13 122.51(19) . . ?
C1 C2 C3 119.3(2) . . ?
C4 C3 C2 119.2(2) . . ?
C3 C4 C5 117.78(19) . . ?
C3 C4 C9 125.16(19) . . ?
C5 C4 C9 116.93(19) . . ?
N1 C5 C4 123.39(18) . . ?
N1 C5 C6 117.47(19) . . ?
C4 C5 C6 119.13(18) . . ?
C5 C6 C6 112.5(2) . 2_565 ?
C5 C6 C7 109.12(18) . . ?
C6 C6 C7 116.47(14) 2_565 . ?
C6 C7 C10 111.15(17) . . ?
C6 C7 C8 109.81(18) . . ?
C10 C7 C8 86.95(16) . . ?
C11 C8 C12 108.38(19) . . ?
C11 C8 C9 119.15(19) . . ?
C12 C8 C9 111.8(2) . . ?
C11 C8 C7 119.30(19) . . ?
C12 C8 C7 111.29(18) . . ?
C9 C8 C7 85.41(16) . . ?
C4 C9 C10 105.25(17) . . ?
C4 C9 C8 110.29(19) . . ?
C10 C9 C8 87.15(16) . . ?
C9 C10 C7 86.57(18) . . ?
N2 C13 C15 115.0(2) . . ?
N2 C13 C1 108.68(18) . . ?
C15 C13 C1 111.07(19) . . ?
N2 C13 C14 108.1(2) . . ?
C15 C13 C14 108.9(2) . . ?
C1 C13 C14 104.5(2) . . ?
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
N1 C1 1.346(3) . ?
N1 C5 1.348(3) . ?
N2 C13 1.450(3) . ?
N2 C16 1.456(3) . ?
N2 C17 1.466(3) . ?
C1 C2 1.373(3) . ?
C1 C13 1.546(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.513(3) . ?
C5 C6 1.513(3) . ?
C6 C6 1.534(4) 2_565 ?
C6 C7 1.541(3) . ?
C7 C10 1.550(3) . ?
C7 C8 1.570(3) . ?
C8 C11 1.515(3) . ?
C8 C12 1.540(3) . ?
C8 C9 1.564(3) . ?
C9 C10 1.551(3) . ?
C13 C15 1.520(3) . ?
C13 C14 1.570(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -3.0(3) . . . . ?
C5 N1 C1 C13 172.1(2) . . . . ?
N1 C1 C2 C3 2.6(4) . . . . ?
C13 C1 C2 C3 -172.1(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 -3.3(3) . . . . ?
C2 C3 C4 C9 172.4(2) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C1 N1 C5 C6 -179.82(19) . . . . ?
C3 C4 C5 N1 3.0(3) . . . . ?
C9 C4 C5 N1 -173.1(2) . . . . ?
C3 C4 C5 C6 -177.0(2) . . . . ?
C9 C4 C5 C6 6.9(3) . . . . ?
N1 C5 C6 C6 38.8(2) . . . 2_565 ?
C4 C5 C6 C6 -141.17(16) . . . 2_565 ?
N1 C5 C6 C7 169.67(19) . . . . ?
C4 C5 C6 C7 -10.3(3) . . . . ?
C5 C6 C7 C10 -39.2(2) . . . . ?
C6 C6 C7 C10 89.5(2) 2_565 . . . ?
C5 C6 C7 C8 55.3(2) . . . . ?
C6 C6 C7 C8 -176.01(18) 2_565 . . . ?
C6 C7 C8 C11 37.2(3) . . . . ?
C10 C7 C8 C11 148.57(19) . . . . ?
C6 C7 C8 C12 164.53(19) . . . . ?
C10 C7 C8 C12 -84.1(2) . . . . ?
C6 C7 C8 C9 -83.84(19) . . . . ?
C10 C7 C8 C9 27.56(16) . . . . ?
C3 C4 C9 C10 -130.3(2) . . . . ?
C5 C4 C9 C10 45.4(3) . . . . ?
C3 C4 C9 C8 137.0(2) . . . . ?
C5 C4 C9 C8 -47.2(3) . . . . ?
C11 C8 C9 C4 -43.5(2) . . . . ?
C12 C8 C9 C4 -171.22(18) . . . . ?
C7 C8 C9 C4 77.67(19) . . . . ?
C11 C8 C9 C10 -148.70(19) . . . . ?
C12 C8 C9 C10 83.6(2) . . . . ?
C7 C8 C9 C10 -27.54(16) . . . . ?
C4 C9 C10 C7 -82.37(19) . . . . ?
C8 C9 C10 C7 27.89(15) . . . . ?
C6 C7 C10 C9 82.30(18) . . . . ?
C8 C7 C10 C9 -27.78(15) . . . . ?
C16 N2 C13 C15 55.8(3) . . . . ?
C17 N2 C13 C15 -68.1(3) . . . . ?
C16 N2 C13 C1 -69.4(3) . . . . ?
C17 N2 C13 C1 166.8(2) . . . . ?
C16 N2 C13 C14 177.7(2) . . . . ?
C17 N2 C13 C14 53.8(3) . . . . ?
N1 C1 C13 N2 160.0(2) . . . . ?
C2 C1 C13 N2 -24.9(3) . . . . ?
N1 C1 C13 C15 32.5(3) . . . . ?
C2 C1 C13 C15 -152.4(2) . . . . ?
N1 C1 C13 C14 -84.8(3) . . . . ?
C2 C1 C13 C14 90.3(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10918306
