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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/39/4503909.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_4503909
loop_
_publ_author_name
'Beer, Leanne'
'Mandal, Swadhin K.'
'Reed, Robert W.'
'Oakley, Richard T.'
'Tham, Fook S.'
'Donnadieu, Bruno'
'Haddon, Robert C.'
_publ_section_title
;
 The First Electronically Stabilized Phenalenyl Radical:  Effect of
 Substituents on Solution Chemistry and Solid-State Structure
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              802
_journal_paper_doi               10.1021/cg0603366
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.731(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9301(16)
_cell_length_b                   7.9101(11)
_cell_length_c                   14.804(2)
_cell_measurement_temperature    90(2)
_cell_volume                     1384.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7472
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9734
_exptl_absorpt_correction_T_min  0.9600
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0699
_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)+(0.1025P)²+1.4053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1915
_refine_ls_wR_factor_ref         0.2129
_reflns_number_gt                1497
_reflns_number_total             1984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0603366si20060605_092223.cif
_cod_data_source_block           rh34_0m
_cod_database_code               4503909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.2456(3) 1.1770(4) 0.4702(3) 0.1058(12) Uani 1 1 d .
O2 O 0.3849(2) 1.0266(3) 0.7774(2) 0.0832(9) Uani 1 1 d .
O3 O 0.47938(19) 0.7487(3) 0.8112(2) 0.0721(8) Uani 1 1 d .
O4 O 0.31267(19) 1.0148(3) 0.3446(2) 0.0780(9) Uani 1 1 d .
C1 C 0.3068(3) 1.0700(4) 0.5314(4) 0.0712(12) Uani 1 1 d .
C2 C 0.3149(3) 1.1014(4) 0.6224(4) 0.0764(13) Uani 1 1 d .
H2 H 0.2807 1.2003 0.6428 0.092 Uiso 1 1 calc R
C3 C 0.3722(3) 0.9917(4) 0.6864(3) 0.0666(11) Uani 1 1 d .
C3A C 0.4193(2) 0.8400(4) 0.6585(3) 0.0590(10) Uani 1 1 d .
C4 C 0.4732(2) 0.7132(4) 0.7202(3) 0.0593(10) Uani 1 1 d .
C5 C 0.5136(2) 0.5677(4) 0.6889(3) 0.0569(10) Uani 1 1 d .
H5 H 0.5475 0.4870 0.7316 0.068 Uiso 1 1 calc R
C6 C 0.5069(2) 0.5316(4) 0.5950(3) 0.0511(9) Uani 1 1 d .
C6A C 0.4571(2) 0.6535(3) 0.5307(3) 0.0509(9) Uani 1 1 d .
C7 C 0.4509(2) 0.6224(4) 0.4367(3) 0.0501(9) Uani 1 1 d .
C8 C 0.4028(2) 0.7488(4) 0.3740(3) 0.0540(9) Uani 1 1 d .
H8 H 0.4022 0.7310 0.3105 0.065 Uiso 1 1 calc R
C9 C 0.3583(2) 0.8929(4) 0.4028(3) 0.0587(10) Uani 1 1 d .
C9A C 0.3567(2) 0.9266(4) 0.4977(3) 0.0601(11) Uani 1 1 d .
C9B C 0.4113(2) 0.8083(4) 0.5638(3) 0.0537(10) Uani 1 1 d .
C10 C 0.2162(4) 1.3359(5) 0.4973(4) 0.0929(15) Uani 1 1 d .
H10A H 0.1755 1.3218 0.5508 0.112 Uiso 1 1 calc R
H10B H 0.2871 1.3977 0.5184 0.112 Uiso 1 1 calc R
C11 C 0.1590(11) 1.4256(15) 0.4434(9) 0.151(5) Uani 0.50 1 d P
H11A H 0.1981 1.4444 0.3901 0.227 Uiso 0.50 1 calc PR
H11B H 0.1465 1.5343 0.4721 0.227 Uiso 0.50 1 calc PR
H11C H 0.0860 1.3708 0.4241 0.227 Uiso 0.50 1 calc PR
C12 C 0.3408(4) 1.1840(6) 0.8056(4) 0.1007(17) Uani 1 1 d .
H12A H 0.3691 1.2780 0.7708 0.121 Uiso 1 1 calc R
H12B H 0.2572 1.1829 0.7926 0.121 Uiso 1 1 calc R
C13 C 0.3704(7) 1.2067(11) 0.8894(6) 0.079(2) Uani 0.50 1 d P
H13A H 0.3438 1.1121 0.9236 0.119 Uiso 0.50 1 calc PR
H13B H 0.3375 1.3123 0.9083 0.119 Uiso 0.50 1 calc PR
H13C H 0.4531 1.2134 0.9017 0.119 Uiso 0.50 1 calc PR
C14 C 0.5328(3) 0.6275(6) 0.8752(3) 0.0863(13) Uani 1 1 d .
H14A H 0.4911 0.5206 0.8684 0.129 Uiso 1 1 calc R
H14B H 0.5330 0.6704 0.9374 0.129 Uiso 1 1 calc R
H14C H 0.6109 0.6089 0.8637 0.129 Uiso 1 1 calc R
C15 C 0.3165(3) 0.9857(5) 0.2496(4) 0.0818(13) Uani 1 1 d .
H15A H 0.3952 0.9702 0.2391 0.123 Uiso 1 1 calc R
H15B H 0.2840 1.0831 0.2144 0.123 Uiso 1 1 calc R
H15C H 0.2729 0.8840 0.2302 0.123 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'
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
C1 O1 C10 120.2(4) . .
C3 O2 C12 117.8(4) . .
C4 O3 C14 118.2(3) . .
C9 O4 C15 116.5(3) . .
C2 C1 O1 120.0(3) . .
C2 C1 C9A 121.5(4) . .
O1 C1 C9A 118.5(4) . .
C1 C2 C3 121.5(3) . .
O2 C3 C2 121.6(3) . .
O2 C3 C3A 117.8(4) . .
C2 C3 C3A 120.6(4) . .
C3 C3A C9B 117.7(4) . .
C3 C3A C4 124.4(4) . .
C9B C3A C4 117.9(3) . .
C5 C4 O3 122.5(3) . .
C5 C4 C3A 121.4(4) . .
O3 C4 C3A 116.1(3) . .
C4 C5 C6 122.3(3) . .
C5 C6 C7 121.5(3) . 3_666
C5 C6 C6A 118.9(3) . .
C7 C6 C6A 119.6(3) 3_666 .
C7 C6A C6 120.3(3) . .
C7 C6A C9B 120.6(3) . .
C6 C6A C9B 119.1(4) . .
C6A C7 C6 120.2(3) . 3_666
C6A C7 C8 118.9(3) . .
C6 C7 C8 120.9(4) 3_666 .
C9 C8 C7 121.7(4) . .
C8 C9 O4 122.7(4) . .
C8 C9 C9A 121.7(3) . .
O4 C9 C9A 115.7(3) . .
C1 C9A C9 124.1(3) . .
C1 C9A C9B 117.2(4) . .
C9 C9A C9B 118.7(3) . .
C3A C9B C9A 121.4(3) . .
C3A C9B C6A 120.3(3) . .
C9A C9B C6A 118.3(4) . .
C11 C10 O1 119.1(8) . .
C13 C12 O2 110.2(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.375(5) .
O1 C10 1.379(5) .
O2 C3 1.364(5) .
O2 C12 1.436(5) .
O3 C4 1.368(4) .
O3 C14 1.436(5) .
O4 C9 1.358(4) .
O4 C15 1.432(5) .
C1 C2 1.361(6) .
C1 C9A 1.404(5) .
C2 C3 1.395(6) .
C3 C3A 1.410(5) .
C3A C9B 1.414(5) .
C3A C4 1.448(5) .
C4 C5 1.353(5) .
C5 C6 1.410(5) .
C6 C7 1.422(4) 3_666
C6 C6A 1.427(5) .
C6A C7 1.406(5) .
C6A C9B 1.453(4) .
C7 C6 1.422(4) 3_666
C7 C8 1.430(4) .
C8 C9 1.351(5) .
C9 C9A 1.432(5) .
C9A C9B 1.444(5) .
C10 C11 1.208(10) .
C12 C13 1.256(8) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145366
