#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226795.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_2226795
loop_
_publ_author_name
'Arman, Hadi D.'
'Kaulgud, Trupta'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Benzoic acid--2,9-dimethylphenanthroline (1/1)
;
_journal_coeditor_code           BT5303
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2117
_journal_paper_doi               10.1107/S1600536810029065
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H6 O2 , C14 H12 N2'
_chemical_formula_moiety         'C7 H6 O2 , C14 H12 N2'
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_chemical_name_systematic
;
Benzoic acid--2,9-dimethylphenanthroline (1/1)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 104.832(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.575(5)
_cell_length_b                   11.645(4)
_cell_length_c                   11.148(4)
_cell_measurement_reflns_used    6463
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.6
_cell_measurement_theta_min      2.1
_cell_volume                     1703.6(11)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_reduction
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_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  0.035
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13167
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.8352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.152
_refine_ls_wR_factor_ref         0.156
_reflns_number_gt                3589
_reflns_number_total             3907
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5303.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226795
_cod_database_fobs_code          2226795
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.25983(16) 0.62242(12) 0.73806(12) 0.0586(5) Uani d D 1 . .
H H1O 0.276(2) 0.5534(8) 0.733(2) 0.088 Uiso d D 1 . .
O O2 0.22317(11) 0.60724(11) 0.53150(11) 0.0383(3) Uani d . 1 . .
N N1 0.20135(10) 0.37901(11) 0.76126(12) 0.0224(3) Uani d . 1 . .
N N2 0.39950(10) 0.44243(10) 0.79467(11) 0.0203(3) Uani d . 1 . .
C C1 0.22858(14) 0.66340(14) 0.62456(15) 0.0290(4) Uani d . 1 . .
C C2 0.20107(11) 0.78707(13) 0.62330(14) 0.0223(3) Uani d . 1 . .
C C3 0.22051(12) 0.85085(14) 0.73285(15) 0.0252(3) Uani d . 1 . .
H H3 0.2497 0.8147 0.8102 0.030 Uiso calc R 1 . .
C C4 0.19729(14) 0.96692(15) 0.72878(18) 0.0335(4) Uani d . 1 . .
H H4 0.2113 1.0104 0.8033 0.040 Uiso calc R 1 . .
C C5 0.15377(16) 1.01962(16) 0.6164(2) 0.0409(5) Uani d . 1 . .
H H5 0.1376 1.0991 0.6138 0.049 Uiso calc R 1 . .
C C6 0.13392(15) 0.95635(17) 0.50764(19) 0.0388(4) Uani d . 1 . .
H H6 0.1037 0.9926 0.4307 0.047 Uiso calc R 1 . .
C C7 0.15784(12) 0.84071(15) 0.51025(16) 0.0290(4) Uani d . 1 . .
H H7 0.1448 0.7980 0.4352 0.035 Uiso calc R 1 . .
C C8 0.02727(13) 0.41778(19) 0.65105(17) 0.0383(4) Uani d . 1 . .
H H8A 0.0627 0.4698 0.6070 0.058 Uiso calc R 1 . .
H H8B -0.0154 0.4626 0.6926 0.058 Uiso calc R 1 . .
H H8C -0.0156 0.3648 0.5916 0.058 Uiso calc R 1 . .
C C9 0.10420(12) 0.35052(15) 0.74590(15) 0.0270(3) Uani d . 1 . .
C C10 0.07329(13) 0.26372(16) 0.81689(16) 0.0320(4) Uani d . 1 . .
H H10 0.0032 0.2450 0.8033 0.038 Uiso calc R 1 . .
C C11 0.14511(14) 0.20691(15) 0.90530(16) 0.0307(4) Uani d . 1 . .
H H11 0.1252 0.1483 0.9535 0.037 Uiso calc R 1 . .
C C12 0.24909(12) 0.23568(13) 0.92478(14) 0.0241(3) Uani d . 1 . .
C C13 0.27308(11) 0.32317(12) 0.84953(13) 0.0202(3) Uani d . 1 . .
C C14 0.32829(14) 0.18039(14) 1.01699(14) 0.0280(4) Uani d . 1 . .
H H14 0.3116 0.1210 1.0668 0.034 Uiso calc R 1 . .
C C15 0.42676(13) 0.21252(14) 1.03328(14) 0.0278(4) Uani d . 1 . .
H H15 0.4784 0.1751 1.0945 0.033 Uiso calc R 1 . .
C C16 0.45439(12) 0.30185(13) 0.95988(14) 0.0225(3) Uani d . 1 . .
C C17 0.37851(11) 0.35697(12) 0.86771(13) 0.0192(3) Uani d . 1 . .
C C18 0.55556(12) 0.33981(14) 0.97563(14) 0.0260(3) Uani d . 1 . .
H H18 0.6092 0.3058 1.0372 0.031 Uiso calc R 1 . .
C C19 0.57615(12) 0.42575(14) 0.90205(15) 0.0261(3) Uani d . 1 . .
H H19 0.6441 0.4520 0.9123 0.031 Uiso calc R 1 . .
C C20 0.49563(12) 0.47512(13) 0.81070(14) 0.0225(3) Uani d . 1 . .
C C21 0.51601(14) 0.56796(15) 0.72651(16) 0.0315(4) Uani d . 1 . .
H H21A 0.4683 0.5603 0.6445 0.047 Uiso calc R 1 . .
H H21B 0.5860 0.5609 0.7186 0.047 Uiso calc R 1 . .
H H21C 0.5071 0.6433 0.7615 0.047 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1O . . 108(2) ?
C9 N1 C13 . . 118.52(14) ?
C20 N2 C17 . . 118.58(13) ?
O2 C1 O1 . . 124.10(16) ?
O2 C1 C2 . . 123.66(15) ?
O1 C1 C2 . . 112.24(14) ?
C7 C2 C3 . . 119.61(15) ?
C7 C2 C1 . . 119.28(15) ?
C3 C2 C1 . . 121.09(14) ?
C4 C3 C2 . . 120.00(15) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C5 C4 C3 . . 120.17(17) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C4 C5 C6 . . 119.92(17) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 120.49(17) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C2 . . 119.82(17) ?
C6 C7 H7 . . 120.1 ?
C2 C7 H7 . . 120.1 ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 122.31(16) ?
N1 C9 C8 . . 116.68(15) ?
C10 C9 C8 . . 120.99(15) ?
C11 C10 C9 . . 119.42(15) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C12 . . 119.76(15) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C13 C12 C11 . . 117.00(15) ?
C13 C12 C14 . . 120.36(15) ?
C11 C12 C14 . . 122.64(15) ?
N1 C13 C12 . . 122.99(14) ?
N1 C13 C17 . . 118.06(13) ?
C12 C13 C17 . . 118.94(14) ?
C15 C14 C12 . . 120.29(15) ?
C15 C14 H14 . . 119.9 ?
C12 C14 H14 . . 119.9 ?
C14 C15 C16 . . 121.19(15) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C17 C16 C18 . . 117.04(14) ?
C17 C16 C15 . . 119.87(15) ?
C18 C16 C15 . . 123.08(14) ?
N2 C17 C16 . . 122.89(14) ?
N2 C17 C13 . . 117.76(13) ?
C16 C17 C13 . . 119.34(13) ?
C19 C18 C16 . . 119.79(14) ?
C19 C18 H18 . . 120.1 ?
C16 C18 H18 . . 120.1 ?
C18 C19 C20 . . 119.44(15) ?
C18 C19 H19 . . 120.3 ?
C20 C19 H19 . . 120.3 ?
N2 C20 C19 . . 122.25(14) ?
N2 C20 C21 . . 117.01(14) ?
C19 C20 C21 . . 120.74(14) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.317(2) ?
O1 H1O . 0.839(12) ?
O2 C1 . 1.213(2) ?
N1 C9 . 1.328(2) ?
N1 C13 . 1.3597(19) ?
N2 C20 . 1.327(2) ?
N2 C17 . 1.3614(19) ?
C1 C2 . 1.487(2) ?
C2 C7 . 1.394(2) ?
C2 C3 . 1.396(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.385(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.502(2) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.412(2) ?
C10 C11 . 1.367(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.412(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.410(2) ?
C12 C14 . 1.436(2) ?
C13 C17 . 1.448(2) ?
C14 C15 . 1.355(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.432(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.410(2) ?
C16 C18 . 1.410(2) ?
C18 C19 . 1.367(2) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.411(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.503(2) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
O1 H1o N1 1_555 0.839(12) 2.327(16) 2.973(2) 134(2) y
O1 H1o N2 1_555 0.839(12) 2.09(2) 2.788(2) 141(2) y
C19 H19 Cg 2_646 0.95 2.60 3.426(2) 145 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C7 . . . . 6.1(3) ?
O1 C1 C2 C7 . . . . -174.24(17) ?
O2 C1 C2 C3 . . . . -172.06(17) ?
O1 C1 C2 C3 . . . . 7.6(2) ?
C7 C2 C3 C4 . . . . -0.3(2) ?
C1 C2 C3 C4 . . . . 177.84(15) ?
C2 C3 C4 C5 . . . . 0.7(3) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C7 . . . . -0.4(3) ?
C5 C6 C7 C2 . . . . 0.8(3) ?
C3 C2 C7 C6 . . . . -0.5(2) ?
C1 C2 C7 C6 . . . . -178.63(16) ?
C13 N1 C9 C10 . . . . -0.7(2) ?
C13 N1 C9 C8 . . . . 177.54(14) ?
N1 C9 C10 C11 . . . . 0.4(3) ?
C8 C9 C10 C11 . . . . -177.79(16) ?
C9 C10 C11 C12 . . . . 0.1(2) ?
C10 C11 C12 C13 . . . . -0.3(2) ?
C10 C11 C12 C14 . . . . 179.27(15) ?
C9 N1 C13 C12 . . . . 0.6(2) ?
C9 N1 C13 C17 . . . . -178.42(13) ?
C11 C12 C13 N1 . . . . -0.1(2) ?
C14 C12 C13 N1 . . . . -179.61(14) ?
C11 C12 C13 C17 . . . . 178.91(13) ?
C14 C12 C13 C17 . . . . -0.6(2) ?
C13 C12 C14 C15 . . . . 0.6(2) ?
C11 C12 C14 C15 . . . . -178.93(15) ?
C12 C14 C15 C16 . . . . 0.1(2) ?
C14 C15 C16 C17 . . . . -0.8(2) ?
C14 C15 C16 C18 . . . . 178.49(15) ?
C20 N2 C17 C16 . . . . 0.2(2) ?
C20 N2 C17 C13 . . . . 179.49(12) ?
C18 C16 C17 N2 . . . . 0.7(2) ?
C15 C16 C17 N2 . . . . -179.97(13) ?
C18 C16 C17 C13 . . . . -178.60(13) ?
C15 C16 C17 C13 . . . . 0.7(2) ?
N1 C13 C17 N2 . . . . -0.3(2) ?
C12 C13 C17 N2 . . . . -179.36(13) ?
N1 C13 C17 C16 . . . . 179.01(13) ?
C12 C13 C17 C16 . . . . 0.0(2) ?
C17 C16 C18 C19 . . . . -0.6(2) ?
C15 C16 C18 C19 . . . . -179.93(15) ?
C16 C18 C19 C20 . . . . -0.3(2) ?
C17 N2 C20 C19 . . . . -1.1(2) ?
C17 N2 C20 C21 . . . . 178.74(13) ?
C18 C19 C20 N2 . . . . 1.2(2) ?
C18 C19 C20 C21 . . . . -178.67(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656146
2 PubChem 139079256
