#------------------------------------------------------------------------------
#$Date: 2025-08-21 12:25:49 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301846 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/87/7008776.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_7008776
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            'C15 H16 O5'
_chemical_formula_weight         276.28
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.422(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5003(7)
_cell_length_b                   13.713(2)
_cell_length_c                   21.761(4)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      1
_cell_volume                     1340.5(4)
_computing_cell_refinement       'SAINT (Bruker AXS, 2000)'
_computing_data_collection       'SMART (Bruker AXS, 2000)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2000)'
_computing_molecular_graphics
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 80
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12720
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_correction_T_min  0.9465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Corrections were done with the SADABS program, utilizing the none merged
raw data obtained from the integration process. Integration and final cell
refinement were done with SAINT.

SADABS reports ratio of Tmin/Tmax = 0.852113

;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needles'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0447
_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)+(0.0566P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                2126
_reflns_number_total             3059
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507579c.txt
_cod_data_source_block           sad
_cod_original_cell_volume        1340.6(4)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7008776
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 0.2665(2) 0.26138(7) 0.19930(4) 0.0270(2) Uani 1 1 d . . .
O2 O -0.0587(2) 0.37994(7) 0.12890(5) 0.0308(3) Uani 1 1 d . . .
C2 C 0.2760(3) 0.09542(11) 0.17029(7) 0.0297(3) Uani 1 1 d . . .
O3 O -0.2481(2) 0.52507(7) 0.08340(5) 0.0336(3) Uani 1 1 d . . .
C6 C -0.0482(3) 0.20844(10) 0.11019(6) 0.0248(3) Uani 1 1 d . . .
O4 O 0.0786(2) 0.23202(8) 0.29521(4) 0.0358(3) Uani 1 1 d . . .
C1 C 0.1645(3) 0.18826(10) 0.16022(6) 0.0247(3) Uani 1 1 d . . .
C8 C -0.3844(3) 0.31351(12) 0.04786(7) 0.0317(4) Uani 1 1 d . . .
C7 C -0.1703(3) 0.30260(10) 0.09515(6) 0.0260(3) Uani 1 1 d . . .
C5 C -0.1460(3) 0.12804(11) 0.07235(6) 0.0289(3) Uani 1 1 d . . .
C3 C 0.1764(4) 0.01789(12) 0.13150(8) 0.0357(4) Uani 1 1 d . . .
O5 O 0.5823(3) -0.00521(9) 0.23537(6) 0.0561(4) Uani 1 1 d . . .
C9 C -0.4804(4) 0.23289(13) 0.01249(7) 0.0359(4) Uani 1 1 d . . .
C15 C 0.4958(4) 0.07554(13) 0.22138(8) 0.0371(4) Uani 1 1 d . . .
C13 C 0.0577(4) 0.29139(12) 0.24307(7) 0.0293(3) Uani 1 1 d . . .
C4 C -0.0269(4) 0.03365(11) 0.08455(8) 0.0346(4) Uani 1 1 d . . .
C11 C -0.2418(4) 0.46431(11) 0.13457(8) 0.0332(4) Uani 1 1 d . . .
C10 C -0.3615(4) 0.14322(13) 0.02344(7) 0.0354(4) Uani 1 1 d . . .
C14 C 0.3197(4) 0.25838(15) 0.33751(8) 0.0422(4) Uani 1 1 d . . .
C12 C 0.0338(4) 0.56749(14) 0.07376(10) 0.0435(4) Uani 1 1 d . . .
H13A H -0.147(3) 0.2842(11) 0.2241(6) 0.025(4) Uiso 1 1 d . . .
H11A H -0.451(4) 0.4434(11) 0.1400(7) 0.031(4) Uiso 1 1 d . . .
H11B H -0.155(3) 0.4962(11) 0.1723(7) 0.029(4) Uiso 1 1 d . . .
H13B H 0.109(3) 0.3592(12) 0.2539(6) 0.026(4) Uiso 1 1 d . . .
H12A H 0.172(4) 0.5184(13) 0.0587(8) 0.045(5) Uiso 1 1 d . . .
H4 H -0.093(4) -0.0169(12) 0.0582(7) 0.034(4) Uiso 1 1 d . . .
H12B H 0.001(4) 0.6153(13) 0.0412(8) 0.044(5) Uiso 1 1 d . . .
H9 H -0.630(4) 0.2436(11) -0.0224(7) 0.035(4) Uiso 1 1 d . . .
H3 H 0.262(4) -0.0442(12) 0.1409(7) 0.037(4) Uiso 1 1 d . . .
H14A H 0.509(5) 0.2643(13) 0.3173(8) 0.053(5) Uiso 1 1 d . . .
H8 H -0.462(3) 0.3763(12) 0.0381(7) 0.031(4) Uiso 1 1 d . . .
H14B H 0.276(4) 0.3241(15) 0.3578(9) 0.062(6) Uiso 1 1 d . . .
H15 H 0.574(4) 0.1304(14) 0.2457(7) 0.042(5) Uiso 1 1 d . . .
H14C H 0.342(4) 0.2095(14) 0.3697(9) 0.057(6) Uiso 1 1 d . . .
H10 H -0.424(3) 0.0895(11) -0.0021(7) 0.032(4) Uiso 1 1 d . . .
H12C H 0.125(4) 0.5966(14) 0.1117(9) 0.062(6) 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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 114.28(11) . . ?
C7 O2 C11 118.58(12) . . ?
C1 C2 C3 119.95(14) . . ?
C1 C2 C15 120.86(14) . . ?
C3 C2 C15 119.18(14) . . ?
C11 O3 C12 112.80(13) . . ?
C5 C6 C1 117.21(13) . . ?
C5 C6 C7 117.55(13) . . ?
C1 C6 C7 125.24(12) . . ?
C13 O4 C14 112.88(13) . . ?
O1 C1 C2 117.98(13) . . ?
O1 C1 C6 120.80(12) . . ?
C2 C1 C6 121.22(13) . . ?
C7 C8 C9 120.32(16) . . ?
C7 C8 H8 119.9(9) . . ?
C9 C8 H8 119.8(9) . . ?
O2 C7 C8 122.39(13) . . ?
O2 C7 C6 116.87(12) . . ?
C8 C7 C6 120.71(13) . . ?
C10 C5 C4 120.66(14) . . ?
C10 C5 C6 119.63(14) . . ?
C4 C5 C6 119.71(14) . . ?
C4 C3 C2 120.59(15) . . ?
C4 C3 H3 123.6(10) . . ?
C2 C3 H3 115.8(10) . . ?
C10 C9 C8 120.89(15) . . ?
C10 C9 H9 120.6(9) . . ?
C8 C9 H9 118.4(9) . . ?
O5 C15 C2 123.62(17) . . ?
O5 C15 H15 118.1(10) . . ?
C2 C15 H15 118.3(10) . . ?
O4 C13 O1 110.90(12) . . ?
O4 C13 H13A 107.3(8) . . ?
O1 C13 H13A 108.8(8) . . ?
O4 C13 H13B 110.8(8) . . ?
O1 C13 H13B 106.0(8) . . ?
H13A C13 H13B 113.1(12) . . ?
C3 C4 C5 121.30(15) . . ?
C3 C4 H4 121.4(10) . . ?
C5 C4 H4 117.2(10) . . ?
O3 C11 O2 113.60(12) . . ?
O3 C11 H11A 107.0(9) . . ?
O2 C11 H11A 109.3(9) . . ?
O3 C11 H11B 112.9(9) . . ?
O2 C11 H11B 103.1(9) . . ?
H11A C11 H11B 110.9(12) . . ?
C9 C10 C5 120.81(15) . . ?
C9 C10 H10 119.8(9) . . ?
C5 C10 H10 119.4(9) . . ?
O4 C14 H14A 112.3(11) . . ?
O4 C14 H14B 109.9(11) . . ?
H14A C14 H14B 108.3(16) . . ?
O4 C14 H14C 109.4(11) . . ?
H14A C14 H14C 109.0(16) . . ?
H14B C14 H14C 108.0(15) . . ?
O3 C12 H12A 110.8(10) . . ?
O3 C12 H12B 106.7(10) . . ?
H12A C12 H12B 106.9(14) . . ?
O3 C12 H12C 112.0(12) . . ?
H12A C12 H12C 108.4(15) . . ?
H12B C12 H12C 112.1(15) . . ?
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 C1 1.3757(17) . ?
O1 C13 1.4376(18) . ?
O2 C7 1.3686(17) . ?
O2 C11 1.4300(18) . ?
C2 C1 1.381(2) . ?
C2 C3 1.414(2) . ?
C2 C15 1.469(2) . ?
O3 C11 1.3897(18) . ?
O3 C12 1.423(2) . ?
C6 C5 1.430(2) . ?
C6 C1 1.433(2) . ?
C6 C7 1.433(2) . ?
O4 C13 1.3950(18) . ?
O4 C14 1.427(2) . ?
C8 C7 1.375(2) . ?
C8 C9 1.401(2) . ?
C8 H8 0.948(16) . ?
C5 C10 1.412(2) . ?
C5 C4 1.420(2) . ?
C3 C4 1.347(3) . ?
C3 H3 0.951(17) . ?
O5 C15 1.207(2) . ?
C9 C10 1.356(2) . ?
C9 H9 0.995(17) . ?
C15 H15 0.974(19) . ?
C13 H13A 0.992(15) . ?
C13 H13B 0.984(16) . ?
C4 H4 0.936(17) . ?
C11 H11A 0.999(16) . ?
C11 H11B 0.991(16) . ?
C10 H10 0.955(16) . ?
C14 H14A 0.99(2) . ?
C14 H14B 1.03(2) . ?
C14 H14C 0.97(2) . ?
C12 H12A 0.984(19) . ?
C12 H12B 0.970(18) . ?
C12 H12C 0.99(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21144985
2 PubChem 86073963
