#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/87/7008774.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_7008774
loop_
_publ_author_name
'Glaser, Thorsten'
'Liratzis, Ioannis'
'Fröhlich, Roland'
_publ_section_title
;
 A 1,8-naphthalenediol-based unsymmetrical dinucleating ligand.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2892
_journal_page_last               2898
_journal_paper_doi               10.1039/b507579c
_journal_year                    2005
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.45
_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
'at nitrogen and oxygen from difmap, other geom'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.91(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.731(1)
_cell_length_b                   8.650(1)
_cell_length_c                   16.954(1)
_cell_measurement_temperature    223(2)
_cell_volume                     2031.2(3)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11122
_diffrn_reflns_theta_full        63.65
_diffrn_reflns_theta_max         63.65
_diffrn_reflns_theta_min         5.38
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.9285
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.034
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0484
_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)+(0.0776P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                1845
_reflns_number_total             3209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507579c.txt
_cod_data_source_block           han2527
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7008774
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.11716(11) 0.59906(17) -0.33626(10) 0.0679(5) Uani 1 1 d . . .
O2 O 1.13394(14) 0.7541(2) -0.45711(13) 0.0918(6) Uani 1 1 d . . .
H2 H 1.1061 0.7078 -0.4290 0.138 Uiso 1 1 calc R . .
N1 N 1.10205(15) 0.4366(2) -0.21134(13) 0.0608(5) Uani 1 1 d . . .
H1 H 1.0683(16) 0.483(2) -0.2652(15) 0.073 Uiso 1 1 d . . .
C1 C 1.01496(18) 0.4822(3) -0.11088(15) 0.0653(7) Uani 1 1 d . . .
H1A H 0.9783 0.4278 -0.0808 0.078 Uiso 1 1 calc R . .
H1B H 1.0732 0.5250 -0.0691 0.078 Uiso 1 1 calc R . .
C2 C 1.04403(17) 0.3680(3) -0.16624(15) 0.0664(7) Uani 1 1 d . . .
H2A H 1.0806 0.2834 -0.1312 0.080 Uiso 1 1 calc R . .
H2B H 0.9855 0.3237 -0.2069 0.080 Uiso 1 1 calc R . .
C3 C 1.19577(18) 0.4289(3) -0.18817(16) 0.0662(7) Uani 1 1 d . . .
H3 H 1.2281 0.3738 -0.1388 0.079 Uiso 1 1 calc R . .
C4 C 1.25208(17) 0.4952(3) -0.23022(16) 0.0659(7) Uani 1 1 d . . .
C5 C 1.20866(17) 0.5819(2) -0.30530(15) 0.0589(6) Uani 1 1 d . . .
C6 C 1.26983(18) 0.6516(3) -0.34647(17) 0.0680(7) Uani 1 1 d . . .
C7 C 1.2305(2) 0.7396(3) -0.4198(2) 0.0751(8) Uani 1 1 d . . .
C8 C 1.2890(3) 0.8083(3) -0.4585(2) 0.1023(11) Uani 1 1 d . . .
H8 H 1.2620 0.8657 -0.5081 0.123 Uiso 1 1 calc R . .
C9 C 1.3872(3) 0.7909(4) -0.4232(3) 0.1338(15) Uani 1 1 d . . .
H9 H 1.4272 0.8392 -0.4487 0.161 Uiso 1 1 calc R . .
C10 C 1.4296(3) 0.7039(5) -0.3505(3) 0.1366(15) Uani 1 1 d . . .
H10 H 1.4971 0.6929 -0.3282 0.164 Uiso 1 1 calc R . .
C11 C 1.3712(2) 0.6333(3) -0.3111(2) 0.0963(10) Uani 1 1 d . . .
C12 C 1.4110(2) 0.5446(4) -0.2365(3) 0.1171(12) Uani 1 1 d . . .
H12 H 1.4783 0.5321 -0.2132 0.141 Uiso 1 1 calc R . .
C13 C 1.3540(2) 0.4782(4) -0.1989(2) 0.1007(10) Uani 1 1 d . . .
H13 H 1.3825 0.4188 -0.1503 0.121 Uiso 1 1 calc R . .
O21 O 0.91250(11) 0.88724(16) 0.00978(9) 0.0636(5) Uani 1 1 d . . .
O22 O 0.91568(13) 1.0557(2) 0.13229(12) 0.0840(6) Uani 1 1 d . . .
H22 H 0.9338 1.0249 0.0937 0.126 Uiso 1 1 calc R . .
N21 N 0.90729(15) 0.6990(2) -0.11278(13) 0.0628(5) Uani 1 1 d . . .
H21 H 0.9486(16) 0.764(2) -0.0640(15) 0.075 Uiso 1 1 d . . .
C22 C 0.95515(19) 0.6110(3) -0.16084(15) 0.0700(7) Uani 1 1 d . . .
H22A H 0.9965 0.6806 -0.1793 0.084 Uiso 1 1 calc R . .
H22B H 0.9063 0.5684 -0.2110 0.084 Uiso 1 1 calc R . .
C23 C 0.81718(18) 0.6839(2) -0.12034(16) 0.0666(7) Uani 1 1 d . . .
H23 H 0.7797 0.6162 -0.1622 0.080 Uiso 1 1 calc R . .
C24 C 0.77063(16) 0.7595(2) -0.07165(16) 0.0596(6) Uani 1 1 d . . .
C25 C 0.82277(16) 0.8607(2) -0.00600(14) 0.0543(6) Uani 1 1 d . . .
C26 C 0.77218(17) 0.9306(2) 0.04501(15) 0.0609(6) Uani 1 1 d . . .
C27 C 0.82138(19) 1.0294(3) 0.11245(16) 0.0703(7) Uani 1 1 d . . .
C28 C 0.7728(2) 1.0969(3) 0.16019(19) 0.0997(10) Uani 1 1 d . . .
H28 H 0.8058 1.1625 0.2050 0.120 Uiso 1 1 calc R . .
C29 C 0.6767(3) 1.0685(4) 0.1423(2) 0.1196(13) Uani 1 1 d . . .
H29 H 0.6441 1.1174 0.1744 0.144 Uiso 1 1 calc R . .
C30 C 0.6264(2) 0.9701(4) 0.0786(2) 0.1084(11) Uani 1 1 d . . .
H30 H 0.5609 0.9493 0.0691 0.130 Uiso 1 1 calc R . .
C31 C 0.67305(19) 0.9005(3) 0.02747(18) 0.0792(8) Uani 1 1 d . . .
C32 C 0.62393(19) 0.7996(3) -0.0394(2) 0.0939(9) Uani 1 1 d . . .
H32 H 0.5580 0.7790 -0.0510 0.113 Uiso 1 1 calc R . .
C33 C 0.67068(18) 0.7328(3) -0.08673(19) 0.0858(9) Uani 1 1 d . . .
H33 H 0.6363 0.6668 -0.1308 0.103 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 N1 C2 125.0(2) . . ?
C22 C1 C2 111.7(2) . . ?
N1 C2 C1 113.56(18) . . ?
N1 C3 C4 125.6(2) . . ?
C3 C4 C13 120.4(3) . . ?
C3 C4 C5 120.7(2) . . ?
C13 C4 C5 118.9(2) . . ?
O1 C5 C4 121.1(2) . . ?
O1 C5 C6 119.8(2) . . ?
C4 C5 C6 119.1(2) . . ?
C7 C6 C11 119.6(3) . . ?
C7 C6 C5 121.1(2) . . ?
C11 C6 C5 119.3(3) . . ?
O2 C7 C8 117.7(3) . . ?
O2 C7 C6 121.1(2) . . ?
C8 C7 C6 121.2(3) . . ?
C9 C8 C7 118.7(4) . . ?
C8 C9 C10 122.2(3) . . ?
C9 C10 C11 119.6(4) . . ?
C10 C11 C6 118.8(4) . . ?
C10 C11 C12 121.7(4) . . ?
C6 C11 C12 119.5(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 C4 122.1(3) . . ?
C23 N21 C22 124.4(2) . . ?
N21 C22 C1 112.12(19) . . ?
N21 C23 C24 125.8(2) . . ?
C23 C24 C25 120.5(2) . . ?
C23 C24 C33 120.1(2) . . ?
C25 C24 C33 119.4(2) . . ?
O21 C25 C24 121.38(19) . . ?
O21 C25 C26 120.3(2) . . ?
C24 C25 C26 118.3(2) . . ?
C31 C26 C27 119.4(2) . . ?
C31 C26 C25 120.1(2) . . ?
C27 C26 C25 120.5(2) . . ?
O22 C27 C28 118.9(3) . . ?
O22 C27 C26 120.7(2) . . ?
C28 C27 C26 120.3(3) . . ?
C29 C28 C27 120.0(3) . . ?
C28 C29 C30 121.8(3) . . ?
C29 C30 C31 120.0(3) . . ?
C30 C31 C26 118.5(3) . . ?
C30 C31 C32 122.1(3) . . ?
C26 C31 C32 119.4(2) . . ?
C33 C32 C31 120.9(3) . . ?
C32 C33 C24 121.9(3) . . ?
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
O1 C5 1.278(2) . ?
O2 C7 1.351(3) . ?
N1 C3 1.302(3) . ?
N1 C2 1.453(3) . ?
C1 C22 1.493(3) . ?
C1 C2 1.521(3) . ?
C3 C4 1.388(3) . ?
C4 C13 1.419(3) . ?
C4 C5 1.427(3) . ?
C5 C6 1.446(3) . ?
C6 C7 1.404(4) . ?
C6 C11 1.415(4) . ?
C7 C8 1.382(3) . ?
C8 C9 1.373(5) . ?
C9 C10 1.397(5) . ?
C10 C11 1.398(4) . ?
C11 C12 1.424(4) . ?
C12 C13 1.344(4) . ?
O21 C25 1.277(2) . ?
O22 C27 1.333(3) . ?
N21 C23 1.296(3) . ?
N21 C22 1.460(3) . ?
C23 C24 1.402(3) . ?
C24 C25 1.418(3) . ?
C24 C33 1.425(3) . ?
C25 C26 1.452(3) . ?
C26 C31 1.412(3) . ?
C26 C27 1.414(3) . ?
C27 C28 1.379(4) . ?
C28 C29 1.365(4) . ?
C29 C30 1.377(4) . ?
C30 C31 1.412(4) . ?
C31 C32 1.419(4) . ?
C32 C33 1.352(3) . ?
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
C3 N1 C2 C1 98.4(3) . . . . ?
C22 C1 C2 N1 61.1(3) . . . . ?
C2 N1 C3 C4 -179.3(2) . . . . ?
N1 C3 C4 C13 -179.7(2) . . . . ?
N1 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 O1 -0.9(3) . . . . ?
C13 C4 C5 O1 179.4(2) . . . . ?
C3 C4 C5 C6 178.9(2) . . . . ?
C13 C4 C5 C6 -0.9(3) . . . . ?
O1 C5 C6 C7 0.6(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
O1 C5 C6 C11 179.3(2) . . . . ?
C4 C5 C6 C11 -0.5(3) . . . . ?
C11 C6 C7 O2 177.3(2) . . . . ?
C5 C6 C7 O2 -4.1(4) . . . . ?
C11 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 179.0(2) . . . . ?
O2 C7 C8 C9 -178.0(3) . . . . ?
C6 C7 C8 C9 -0.9(4) . . . . ?
C7 C8 C9 C10 1.3(6) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C6 0.3(5) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
C7 C6 C11 C10 -0.1(4) . . . . ?
C5 C6 C11 C10 -178.7(3) . . . . ?
C7 C6 C11 C12 179.8(3) . . . . ?
C5 C6 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 179.5(3) . . . . ?
C6 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C4 -1.2(5) . . . . ?
C3 C4 C13 C12 -178.0(3) . . . . ?
C5 C4 C13 C12 1.7(4) . . . . ?
C23 N21 C22 C1 -101.7(3) . . . . ?
C2 C1 C22 N21 165.8(2) . . . . ?
C22 N21 C23 C24 175.8(2) . . . . ?
N21 C23 C24 C25 -1.5(4) . . . . ?
N21 C23 C24 C33 179.8(2) . . . . ?
C23 C24 C25 O21 1.0(3) . . . . ?
C33 C24 C25 O21 179.7(2) . . . . ?
C23 C24 C25 C26 -177.2(2) . . . . ?
C33 C24 C25 C26 1.5(3) . . . . ?
O21 C25 C26 C31 -179.80(19) . . . . ?
C24 C25 C26 C31 -1.6(3) . . . . ?
O21 C25 C26 C27 0.3(3) . . . . ?
C24 C25 C26 C27 178.51(19) . . . . ?
C31 C26 C27 O22 177.7(2) . . . . ?
C25 C26 C27 O22 -2.4(3) . . . . ?
C31 C26 C27 C28 -0.6(4) . . . . ?
C25 C26 C27 C28 179.3(2) . . . . ?
O22 C27 C28 C29 -178.4(3) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C27 C28 C29 C30 1.7(5) . . . . ?
C28 C29 C30 C31 -2.6(5) . . . . ?
C29 C30 C31 C26 1.9(5) . . . . ?
C29 C30 C31 C32 -179.3(3) . . . . ?
C27 C26 C31 C30 -0.3(4) . . . . ?
C25 C26 C31 C30 179.8(2) . . . . ?
C27 C26 C31 C32 -179.1(2) . . . . ?
C25 C26 C31 C32 1.0(4) . . . . ?
C30 C31 C32 C33 -179.1(3) . . . . ?
C26 C31 C32 C33 -0.3(4) . . . . ?
C31 C32 C33 C24 0.3(5) . . . . ?
C23 C24 C33 C32 177.8(3) . . . . ?
C25 C24 C33 C32 -0.9(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652713
