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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/07/7220707.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_7220707
loop_
_publ_author_name
'Yao, Ching-Fa'
'R. R, Rajawinslin.'
'Ichake, Sachin S.'
'Kavala, Veerababurao'
'Gawande, Sachin D.'
'Huang, Yi-Hsiang'
'Kuo, Chun-Wei'
_publ_section_title
;
 Iron/acetic acid mediated synthesis of 6,7-dihydrodibenzo [b,j] [1,7]
 phenanthroline derivatives via intramolecular reductive cylization
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA06395G
_journal_year                    2015
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-19 deposited with the CCDC.
2015-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5670(10)
_cell_length_b                   11.716(3)
_cell_length_c                   26.496(7)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1417.7(6)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0965
_diffrn_reflns_av_sigmaI/netI    0.1203
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8126
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9501
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0701
_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)+(0.1093P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1596
_refine_ls_wR_factor_ref         0.2262
_reflns_number_gt                1427
_reflns_number_total             2515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra06395g2.cif
_cod_data_source_block           ch16265
_cod_database_code               7220707
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
C1 C 0.9779(10) 0.1839(4) 0.91454(19) 0.0320(12) Uani 1 1 d .
C2 C 1.1130(12) 0.1638(4) 0.9616(2) 0.0414(14) Uani 1 1 d .
H2 H 1.0839 0.2160 0.9885 0.050 Uiso 1 1 calc R
C3 C 1.2844(12) 0.0703(4) 0.9686(2) 0.0466(14) Uani 1 1 d .
H3 H 1.3714 0.0571 1.0006 0.056 Uiso 1 1 calc R
C4 C 1.3344(13) -0.0073(5) 0.9290(2) 0.0535(17) Uani 1 1 d .
H4 H 1.4563 -0.0719 0.9342 0.064 Uiso 1 1 calc R
C5 C 1.2079(12) 0.0104(4) 0.8833(2) 0.0486(15) Uani 1 1 d .
H5 H 1.2417 -0.0426 0.8568 0.058 Uiso 1 1 calc R
C6 C 1.0279(11) 0.1057(4) 0.87442(19) 0.0375(13) Uani 1 1 d .
C7 C 0.8895(11) 0.1294(4) 0.8279(2) 0.0450(14) Uani 1 1 d .
H7 H 0.9179 0.0793 0.8002 0.054 Uiso 1 1 calc R
C8 C 0.7150(11) 0.2236(4) 0.82227(18) 0.0360(13) Uani 1 1 d .
C9 C 0.6807(11) 0.2975(4) 0.86516(17) 0.0318(12) Uani 1 1 d .
C10 C 0.4885(11) 0.3984(4) 0.86006(17) 0.0321(12) Uani 1 1 d .
C11 C 0.3869(10) 0.4343(4) 0.81158(17) 0.0359(13) Uani 1 1 d .
C12 C 0.5110(13) 0.3767(4) 0.76554(19) 0.0518(16) Uani 1 1 d .
H12A H 0.7032 0.4110 0.7572 0.062 Uiso 1 1 calc R
H12B H 0.3783 0.3892 0.7365 0.062 Uiso 1 1 calc R
C13 C 0.5486(13) 0.2491(5) 0.77437(19) 0.0480(15) Uani 1 1 d .
H13A H 0.3531 0.2128 0.7762 0.058 Uiso 1 1 calc R
H13B H 0.6544 0.2154 0.7454 0.058 Uiso 1 1 calc R
C14 C 0.3950(10) 0.4592(4) 0.90227(17) 0.0337(12) Uani 1 1 d .
H14 H 0.4578 0.4373 0.9350 0.040 Uiso 1 1 calc R
C15 C 0.2074(11) 0.5531(4) 0.89609(18) 0.0355(12) Uani 1 1 d .
C16 C 0.1117(13) 0.6215(4) 0.9371(2) 0.0455(14) Uani 1 1 d .
H16 H 0.1800 0.6055 0.9702 0.055 Uiso 1 1 calc R
C17 C -0.0762(13) 0.7095(4) 0.9294(2) 0.0509(16) Uani 1 1 d .
H17 H -0.1396 0.7544 0.9572 0.061 Uiso 1 1 calc R
C18 C -0.1774(14) 0.7343(5) 0.8807(2) 0.0550(17) Uani 1 1 d .
H18 H -0.3108 0.7955 0.8758 0.066 Uiso 1 1 calc R
C19 C -0.0874(11) 0.6720(4) 0.8404(2) 0.0472(15) Uani 1 1 d .
H19 H -0.1573 0.6906 0.8076 0.057 Uiso 1 1 calc R
C20 C 0.1094(11) 0.5798(4) 0.84664(19) 0.0387(13) Uani 1 1 d .
N1 N 0.8070(9) 0.2790(3) 0.90912(14) 0.0339(10) Uani 1 1 d .
N2 N 0.2027(9) 0.5204(4) 0.80482(16) 0.0414(11) Uani 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'
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
N1 C1 C2 118.6(4)
N1 C1 C6 122.6(5)
C2 C1 C6 118.8(4)
C3 C2 C1 120.5(5)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.8(5)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 119.9(5)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.2(5)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C7 124.3(5)
C5 C6 C1 118.8(5)
C7 C6 C1 117.0(4)
C8 C7 C6 121.0(5)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 117.6(5)
C7 C8 C13 123.0(5)
C9 C8 C13 119.4(4)
N1 C9 C8 123.5(4)
N1 C9 C10 118.2(4)
C8 C9 C10 118.3(4)
C14 C10 C11 118.1(4)
C14 C10 C9 121.2(4)
C11 C10 C9 120.7(4)
N2 C11 C10 123.5(4)
N2 C11 C12 118.1(4)
C10 C11 C12 118.3(4)
C11 C12 C13 111.0(4)
C11 C12 H12A 109.4
C13 C12 H12A 109.4
C11 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
C8 C13 C12 112.4(4)
C8 C13 H13A 109.1
C12 C13 H13A 109.1
C8 C13 H13B 109.1
C12 C13 H13B 109.1
H13A C13 H13B 107.9
C10 C14 C15 119.6(4)
C10 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 122.7(5)
C14 C15 C20 118.2(5)
C16 C15 C20 119.1(5)
C17 C16 C15 120.6(5)
C17 C16 H16 119.7
C15 C16 H16 119.7
C16 C17 C18 120.3(5)
C16 C17 H17 119.9
C18 C17 H17 119.9
C19 C18 C17 120.9(5)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C20 120.7(5)
C18 C19 H19 119.6
C20 C19 H19 119.6
N2 C20 C19 119.2(5)
N2 C20 C15 122.3(5)
C19 C20 C15 118.4(5)
C9 N1 C1 118.5(4)
C11 N2 C20 118.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.368(6)
C1 C2 1.410(7)
C1 C6 1.422(6)
C2 C3 1.359(6)
C2 H2 0.9500
C3 C4 1.406(7)
C3 H3 0.9500
C4 C5 1.359(7)
C4 H4 0.9500
C5 C6 1.406(7)
C5 H5 0.9500
C6 C7 1.412(7)
C7 C8 1.369(6)
C7 H7 0.9500
C8 C9 1.438(6)
C8 C13 1.510(7)
C9 N1 1.318(5)
C9 C10 1.478(6)
C10 C14 1.393(6)
C10 C11 1.429(6)
C11 N2 1.326(6)
C11 C12 1.505(6)
C12 C13 1.523(7)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.404(6)
C14 H14 0.9500
C15 C16 1.419(7)
C15 C20 1.419(6)
C16 C17 1.357(7)
C16 H16 0.9500
C17 C18 1.402(8)
C17 H17 0.9500
C18 C19 1.357(7)
C18 H18 0.9500
C19 C20 1.416(6)
C19 H19 0.9500
C20 N2 1.376(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139200400
