#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:02:48 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216369 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/17/1551757.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_1551757
loop_
_publ_author_name
'FUKUYOSHI, Shuichi'
'OOI, Takashi'
'NAKAGAKI, Ryoichi'
_publ_section_title
;
 Crystal Structure of 2-[1-(2,4-Dinitrophenyl)ethyl]-1,10-Phenanthroline
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              55
_journal_paper_doi               10.2116/xraystruct.26.55
_journal_volume                  26
_journal_year                    2010
_chemical_formula_moiety         'C20 H14 N4 O4 '
_chemical_formula_sum            'C20 H14 N4 O4'
_chemical_formula_weight         374.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 96.295(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.477(2)
_cell_length_b                   5.1818(6)
_cell_length_c                   21.754(2)
_cell_measurement_reflns_used    6894
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1734.1(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.095
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16988
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776.00
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.51
_refine_ls_extinction_coef       80(25)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3944
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.7480σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                1286
_reflns_number_total             3944
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            26_55_1.cif
_cod_data_source_block           '_fky0910Mo_FKY090905-3'
_cod_original_formula_sum        'C20 H14 N4 O4 '
_cod_database_code               1551757
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 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
O(1) O 0.2943(1) 0.3150(5) 0.3463(1) 0.078(1) Uani 1.00 1 d .
O(2) O 0.3108(1) 0.0805(5) 0.2654(1) 0.093(1) Uani 1.00 1 d .
O(3) O 0.3879(3) 0.5881(9) 0.0904(2) 0.145(2) Uani 1.00 1 d .
O(4) O 0.4617(2) 0.9386(9) 0.1085(1) 0.116(1) Uani 1.00 1 d .
N(1) N 0.5936(1) 0.3610(5) 0.3874(1) 0.0462(8) Uani 1.00 1 d .
N(2) N 0.6871(2) -0.0074(6) 0.3319(1) 0.0554(9) Uani 1.00 1 d .
N(3) N 0.3278(2) 0.2696(6) 0.2975(2) 0.065(1) Uani 1.00 1 d .
N(4) N 0.4261(3) 0.735(1) 0.1248(2) 0.093(2) Uani 1.00 1 d .
C(1) C 0.4543(2) 0.5663(6) 0.3885(1) 0.046(1) Uani 1.00 1 d .
C(2) C 0.4445(2) 0.6007(6) 0.3191(1) 0.043(1) Uani 1.00 1 d .
C(3) C 0.4943(2) 0.7905(7) 0.2936(2) 0.055(1) Uani 1.00 1 d .
C(4) C 0.7281(2) 0.1313(7) 0.3786(2) 0.049(1) Uani 1.00 1 d .
C(9) C 0.5501(2) 0.5503(6) 0.4128(1) 0.044(1) Uani 1.00 1 d .
C(10) C 0.4345(2) 0.6922(9) 0.1924(2) 0.066(1) Uani 1.00 1 d .
C(11) C 0.6796(2) 0.3305(6) 0.4078(1) 0.045(1) Uani 1.00 1 d .
C(12) C 0.3883(2) 0.4617(6) 0.2769(2) 0.049(1) Uani 1.00 1 d .
C(14) C 0.5898(2) 0.7141(7) 0.4585(1) 0.054(1) Uani 1.00 1 d .
C(15) C 0.6747(2) 0.6801(7) 0.4805(1) 0.061(1) Uani 1.00 1 d .
C(16) C 0.4054(2) 0.7833(6) 0.4171(1) 0.058(1) Uani 1.00 1 d .
C(17) C 0.3838(2) 0.4987(8) 0.2132(2) 0.064(1) Uani 1.00 1 d .
C(18) C 0.7318(2) -0.1915(7) 0.3068(2) 0.066(1) Uani 1.00 1 d .
C(19) C 0.7223(2) 0.4831(7) 0.4554(1) 0.053(1) Uani 1.00 1 d .
C(20) C 0.8166(2) 0.0889(7) 0.4016(2) 0.058(1) Uani 1.00 1 d .
C(21) C 0.8564(2) 0.2415(9) 0.4516(2) 0.068(1) Uani 1.00 1 d .
C(22) C 0.8125(2) 0.4284(8) 0.4770(2) 0.069(1) Uani 1.00 1 d .
C(23) C 0.4886(2) 0.8388(8) 0.2317(2) 0.066(1) Uani 1.00 1 d .
C(24) C 0.8189(2) -0.2467(8) 0.3259(2) 0.072(1) Uani 1.00 1 d .
C(27) C 0.8606(2) -0.1062(8) 0.3722(2) 0.071(1) Uani 1.00 1 d .
H(1) H 0.4276 0.4083 0.3980 0.054 Uiso 1.00 1 c R
H(2) H 0.5339 0.8894 0.3205 0.066 Uiso 1.00 1 c R
H(3) H 0.5571 0.8478 0.4749 0.065 Uiso 1.00 1 c R
H(4) H 0.7020 0.7894 0.5119 0.072 Uiso 1.00 1 c R
H(5) H 0.3470 0.3939 0.1857 0.075 Uiso 1.00 1 c R
H(6) H 0.7031 -0.2903 0.2739 0.080 Uiso 1.00 1 c R
H(7) H 0.9147 0.2064 0.4678 0.080 Uiso 1.00 1 c R
H(8) H 0.8413 0.5298 0.5095 0.082 Uiso 1.00 1 c R
H(9) H 0.5223 0.9713 0.2158 0.079 Uiso 1.00 1 c R
H(10) H 0.8481 -0.3797 0.3063 0.088 Uiso 1.00 1 c R
H(11) H 0.9197 -0.1433 0.3859 0.085 Uiso 1.00 1 c R
H(12) H 0.4286 0.9444 0.4061 0.070 Uiso 1.00 1 c R
H(13) H 0.3454 0.7755 0.4023 0.070 Uiso 1.00 1 c R
H(14) H 0.4122 0.7659 0.4609 0.070 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, 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
O(1) N(3) O(2) 123.6(3)
O(1) N(3) C(12) 117.8(3)
O(2) N(3) C(12) 118.5(3)
O(3) N(4) O(4) 124.4(4)
O(3) N(4) C(10) 121.3(5)
O(4) N(4) C(10) 114.3(4)
N(1) C(9) C(1) 114.3(3)
C(11) N(1) C(9) 117.8(3)
N(1) C(9) C(14) 122.3(3)
N(1) C(11) C(4) 118.0(3)
N(1) C(11) C(19) 122.4(3)
N(2) C(4) C(11) 118.9(3)
C(18) N(2) C(4) 118.0(3)
N(2) C(4) C(20) 122.7(3)
N(2) C(18) C(24) 123.6(3)
N(3) C(12) C(2) 121.4(3)
N(3) C(12) C(17) 115.6(3)
N(4) C(10) C(17) 116.3(4)
N(4) C(10) C(23) 121.5(4)
C(1) C(2) C(12) 125.8(3)
C(16) C(1) C(2) 108.7(2)
C(1) C(2) C(3) 118.6(3)
C(9) C(1) C(2) 110.0(2)
C(16) C(1) C(9) 114.0(3)
C(1) C(9) C(14) 123.4(3)
C(12) C(2) C(3) 115.6(3)
C(2) C(3) C(23) 122.8(3)
C(2) C(12) C(17) 123.0(3)
C(3) C(23) C(10) 119.2(4)
C(4) C(11) C(19) 119.6(3)
C(20) C(4) C(11) 118.4(3)
C(4) C(20) C(27) 116.4(3)
C(4) C(20) C(21) 120.0(3)
C(9) C(14) C(15) 120.3(3)
C(10) C(17) C(12) 117.2(3)
C(23) C(10) C(17) 122.2(4)
C(11) C(19) C(15) 118.0(3)
C(11) C(19) C(22) 119.0(3)
C(14) C(15) C(19) 119.1(3)
C(15) C(19) C(22) 122.9(3)
C(18) C(24) C(27) 118.6(4)
C(19) C(22) C(21) 121.4(3)
C(27) C(20) C(21) 123.6(3)
C(20) C(21) C(22) 121.4(3)
C(20) C(27) C(24) 120.7(3)
N(2) C(18) H(6) 118.3846
H(1) C(1) C(2) 108.6235
H(1) C(1) C(9) 108.0147
H(1) C(1) C(16) 107.3948
C(1) C(16) H(13) 109.9136
C(1) C(16) H(12) 109.0076
C(1) C(16) H(14) 109.4850
C(2) C(3) H(2) 118.6733
C(3) C(23) H(9) 120.8876
H(2) C(3) C(23) 118.5463
C(9) C(14) H(3) 119.9663
C(10) C(17) H(5) 122.1331
C(10) C(23) H(9) 119.9506
C(12) C(17) H(5) 120.6289
H(3) C(14) C(15) 119.7535
C(14) C(15) H(4) 120.7356
H(4) C(15) C(19) 120.1887
H(13) C(16) H(12) 109.4800
H(14) C(16) H(12) 109.4654
H(14) C(16) H(13) 109.4745
H(6) C(18) C(24) 118.0113
C(18) C(24) H(10) 120.3857
C(19) C(22) H(8) 119.1832
C(20) C(21) H(7) 119.2993
C(20) C(27) H(11) 119.9084
H(7) C(21) C(22) 119.3136
C(21) C(22) H(8) 119.3909
H(10) C(24) C(27) 121.0201
C(24) C(27) H(11) 119.3333
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) N(3) 1.255(5)
O(2) N(3) 1.214(4)
O(3) N(4) 1.179(6)
O(4) N(4) 1.261(7)
N(1) C(9) 1.342(4)
N(1) C(11) 1.365(4)
N(2) C(4) 1.345(4)
N(2) C(18) 1.330(5)
N(3) C(12) 1.469(5)
N(4) O(3) 1.179(6)
N(4) O(4) 1.261(7)
N(4) C(10) 1.478(6)
C(1) C(2) 1.510(4)
C(1) C(9) 1.520(4)
C(1) C(16) 1.526(5)
C(2) C(3) 1.402(5)
C(2) C(12) 1.394(4)
C(3) C(23) 1.363(5)
C(4) C(11) 1.462(5)
C(4) C(20) 1.423(4)
C(9) C(14) 1.398(4)
C(10) N(4) 1.478(6)
C(10) C(17) 1.380(6)
C(10) C(23) 1.361(5)
C(11) C(19) 1.408(4)
C(12) C(17) 1.393(5)
C(14) C(15) 1.360(5)
C(15) C(19) 1.403(5)
C(18) C(24) 1.397(5)
C(19) C(22) 1.452(5)
C(20) C(21) 1.428(5)
C(20) C(27) 1.411(6)
C(21) C(22) 1.337(6)
C(24) C(27) 1.348(6)
C(1) H(1) 0.9500
C(3) H(2) 0.9500
C(14) H(3) 0.9499
C(15) H(4) 0.9500
C(16) H(12) 0.9500
C(16) H(13) 0.9500
C(16) H(14) 0.9500
C(17) H(5) 0.9500
C(18) H(6) 0.9500
C(21) H(7) 0.9500
C(22) H(8) 0.9500
C(23) H(9) 0.9500
C(24) H(10) 0.9499
C(27) H(11) 0.9500
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
C(11) N(1) C(9) C(1) -178.6(2)
C(11) N(1) C(9) C(14) 0.1(4)
C(9) N(1) C(11) C(4) -177.6(3)
C(9) N(1) C(11) C(19) 2.4(4)
C(18) N(2) C(4) C(11) -178.6(3)
C(18) N(2) C(4) C(20) 0.1(4)
C(4) N(2) C(18) C(24) -0.6(5)
C(4) N(2) C(18) H(6) 179.9
O(1) N(3) C(12) C(2) 35.8(4)
O(1) N(3) C(12) C(17) -142.7(3)
O(2) N(3) C(12) C(2) -146.6(3)
O(2) N(3) C(12) C(17) 34.9(4)
O(3) N(4) C(10) C(17) -10.5(7)
O(3) N(4) C(10) C(23) 170.4(5)
O(4) N(4) C(10) C(17) 168.6(4)
O(4) N(4) C(10) C(23) -10.5(6)
C(9) C(1) C(2) C(3) -48.6(4)
C(9) C(1) C(2) C(12) 132.5(3)
C(16) C(1) C(2) C(3) 76.8(3)
C(16) C(1) C(2) C(12) -102.0(3)
H(1) C(1) C(2) C(3) -166.6
H(1) C(1) C(2) C(12) 14.5
C(2) C(1) C(9) N(1) -57.2(4)
C(2) C(1) C(9) C(14) 124.1(3)
C(16) C(1) C(9) N(1) -179.5(3)
C(16) C(1) C(9) C(14) 1.7(4)
H(1) C(1) C(9) N(1) 61.2
H(1) C(1) C(9) C(14) -117.5
C(2) C(1) C(16) H(12) -59.0
C(2) C(1) C(16) H(13) 61.0
C(2) C(1) C(16) H(14) -178.7
C(9) C(1) C(16) H(12) 64.0
C(9) C(1) C(16) H(13) -176.0
C(9) C(1) C(16) H(14) -55.7
H(1) C(1) C(16) H(12) -176.3
H(1) C(1) C(16) H(13) -56.3
H(1) C(1) C(16) H(14) 64.0
C(1) C(2) C(3) C(23) -178.7(3)
C(1) C(2) C(3) H(2) 1.5
C(12) C(2) C(3) C(23) 0.3(5)
C(12) C(2) C(3) H(2) -179.5
C(1) C(2) C(12) N(3) 3.2(5)
C(1) C(2) C(12) C(17) -178.4(3)
C(3) C(2) C(12) N(3) -175.7(3)
C(3) C(2) C(12) C(17) 2.7(5)
C(2) C(3) C(23) C(10) -2.2(6)
C(2) C(3) C(23) H(9) 178.6
H(2) C(3) C(23) C(10) 177.6
H(2) C(3) C(23) H(9) -1.6
N(2) C(4) C(11) N(1) 1.9(5)
N(2) C(4) C(11) C(19) -178.0(3)
C(20) C(4) C(11) N(1) -176.8(3)
C(20) C(4) C(11) C(19) 3.2(5)
N(2) C(4) C(20) C(21) -179.5(4)
N(2) C(4) C(20) C(27) 0.9(5)
C(11) C(4) C(20) C(21) -0.8(5)
C(11) C(4) C(20) C(27) 179.6(3)
N(1) C(9) C(14) C(15) -2.2(5)
N(1) C(9) C(14) H(3) 179.0
C(1) C(9) C(14) C(15) 176.4(3)
C(1) C(9) C(14) H(3) -2.4
N(4) C(10) C(17) C(12) -177.7(3)
N(4) C(10) C(17) H(5) 2.3
C(23) C(10) C(17) C(12) 1.4(6)
C(23) C(10) C(17) H(5) -178.6
N(4) C(10) C(23) C(3) -179.6(4)
N(4) C(10) C(23) H(9) -0.5
C(17) C(10) C(23) C(3) 1.3(6)
C(17) C(10) C(23) H(9) -179.5
N(1) C(11) C(19) C(15) -2.8(5)
N(1) C(11) C(19) C(22) 176.3(3)
C(4) C(11) C(19) C(15) 177.2(3)
C(4) C(11) C(19) C(22) -3.7(5)
N(3) C(12) C(17) C(10) 174.9(3)
N(3) C(12) C(17) H(5) -5.0
C(2) C(12) C(17) C(10) -3.5(5)
C(2) C(12) C(17) H(5) 176.5
C(9) C(14) C(15) C(19) 1.7(5)
C(9) C(14) C(15) H(4) -179.3
H(3) C(14) C(15) C(19) -179.5
H(3) C(14) C(15) H(4) -0.5
C(14) C(15) C(19) C(11) 0.7(5)
C(14) C(15) C(19) C(22) -178.4(3)
H(4) C(15) C(19) C(11) -178.4
H(4) C(15) C(19) C(22) 2.6
N(2) C(18) C(24) C(27) -0.1(5)
N(2) C(18) C(24) H(10) -179.7
H(6) C(18) C(24) C(27) 179.4
H(6) C(18) C(24) H(10) -0.2
C(11) C(19) C(22) C(21) 1.8(6)
C(11) C(19) C(22) H(8) -179.2
C(15) C(19) C(22) C(21) -179.1(4)
C(15) C(19) C(22) H(8) -0.2
C(4) C(20) C(21) C(22) -1.2(6)
C(4) C(20) C(21) H(7) 177.2
C(27) C(20) C(21) C(22) 178.4(4)
C(27) C(20) C(21) H(7) -3.2
C(4) C(20) C(27) C(24) -1.6(6)
C(4) C(20) C(27) H(11) -179.7
C(21) C(20) C(27) C(24) 178.8(4)
C(21) C(20) C(27) H(11) 0.8
C(20) C(21) C(22) C(19) 0.7(6)
C(20) C(21) C(22) H(8) -178.3
H(7) C(21) C(22) C(19) -177.7
H(7) C(21) C(22) H(8) 3.3
C(18) C(24) C(27) C(20) 1.3(6)
C(18) C(24) C(27) H(11) 179.3
H(10) C(24) C(27) C(20) -179.2
H(10) C(24) C(27) H(11) -1.1
