#------------------------------------------------------------------------------
#$Date: 2021-01-06 05:02:12 +0200 (Wed, 06 Jan 2021) $
#$Revision: 260549 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/02/7060229.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_7060229
loop_
_publ_author_name
'Ahmed, Ruby'
'Ali, Abid'
'Ahmad, Musheer'
'Alsalme, Ali'
'Khan, Rais Ahmad'
'Ali, Farman'
_publ_section_title
;
 Phenanthroimidazole derivatives as a chemosensor for picric acid: a first
 realistic approach
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20092
_journal_page_last               20100
_journal_paper_doi               10.1039/D0NJ03422C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 N3 O7, C21 H15 N2, H2 O'
_chemical_formula_sum            'C27 H19 N5 O8'
_chemical_formula_weight         541.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2020-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2020-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                115.283(3)
_cell_angle_beta                 100.531(3)
_cell_angle_gamma                94.796(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1550(7)
_cell_length_b                   13.5698(12)
_cell_length_c                   13.6958(13)
_cell_measurement_reflns_used    3463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.13
_cell_measurement_theta_min      3.17
_cell_volume                     1162.41(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18582
_diffrn_reflns_theta_full        25.0468
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1567 before and 0.0760 after correction.
The Ratio of minimum to maximum transmission is 0.7237.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.5469
_exptl_crystal_description       block
_exptl_crystal_F_000             560.3293
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3866
_refine_diff_density_min         -0.4499
_refine_diff_density_rms         0.1012
_refine_ls_d_res_high            0.8394
_refine_ls_d_res_low             7.0663
_refine_ls_goodness_of_fit_ref   1.1120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1120
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0537P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -16
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2877
_reflns_number_total             4119
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0nj03422c2.cif
_cod_data_source_block           FAC149_0m_a
_cod_database_code               7060229
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4a), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-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_refinement_flags_posn
O1 O 0.6719(3) 0.46996(16) 0.47424(17) 0.0333(5) Uani 1.000000 .
O2 O 0.9333(3) 0.45105(17) 0.56827(16) 0.0301(5) Uani 1.000000 .
O3 O 0.8550(3) 0.12830(17) 0.62807(17) 0.0361(6) Uani 1.000000 .
O4 O 0.6944(4) -0.02731(19) 0.49336(19) 0.0627(8) Uani 1.000000 .
O5 O 0.4322(3) -0.05541(16) 0.14191(16) 0.0346(5) Uani 1.000000 .
O6 O 0.4079(3) 0.08627(17) 0.11025(17) 0.0362(6) Uani 1.000000 .
O7 O 0.5728(3) 0.28806(15) 0.27134(15) 0.0229(5) Uani 1.000000 .
N1 N 0.7773(3) 0.4129(2) 0.4985(2) 0.0243(6) Uani 1.000000 .
N2 N 0.7546(4) 0.0725(2) 0.5330(2) 0.0316(6) Uani 1.000000 .
N3 N 0.4610(3) 0.0463(2) 0.1733(2) 0.0251(6) Uani 1.000000 .
N4 N -0.0338(3) 0.37119(19) 0.16697(19) 0.0207(5) Uani 1.000000 .
N5 N 0.2652(3) 0.39420(19) 0.25366(19) 0.0214(6) Uani 1.000000 .
C1 C 0.7120(4) 0.2931(2) 0.4448(2) 0.0199(6) Uani 1.000000 .
C2 C 0.7585(4) 0.2420(2) 0.5106(2) 0.0213(6) Uani 1.000000 .
H2 H 0.8276(4) 0.2837(2) 0.5862(2) 0.0256(8) Uiso 1.000000 R
C3 C 0.7030(4) 0.1282(2) 0.4649(2) 0.0233(7) Uani 1.000000 .
C4 C 0.6058(4) 0.0663(2) 0.3547(2) 0.0245(7) Uani 1.000000 .
H4a H 0.5696(4) -0.0118(2) 0.3246(2) 0.0294(8) Uiso 1.000000 R
C5 C 0.5614(4) 0.1183(2) 0.2886(2) 0.0210(6) Uani 1.000000 .
C6 C 0.6094(4) 0.2370(2) 0.3285(2) 0.0192(6) Uani 1.000000 .
C7 C 0.0923(4) 0.3276(2) 0.2142(2) 0.0212(6) Uani 1.000000 .
C8 C 0.0526(4) 0.2249(2) 0.2237(2) 0.0218(6) Uani 1.000000 .
C9 C 0.1342(4) 0.2229(2) 0.3231(2) 0.0253(7) Uani 1.000000 .
H9 H 0.2080(4) 0.2886(2) 0.3850(2) 0.0303(8) Uiso 1.000000 R
C10 C 0.1071(4) 0.1245(2) 0.3314(3) 0.0275(7) Uani 1.000000 .
H10 H 0.1626(4) 0.1228(2) 0.3991(3) 0.0330(8) Uiso 1.000000 R
C11 C -0.0009(4) 0.0285(2) 0.2410(2) 0.0269(7) Uani 1.000000 .
H11 H -0.0181(4) -0.0389(2) 0.2466(2) 0.0323(8) Uiso 1.000000 R
C12 C -0.0838(4) 0.0311(2) 0.1423(3) 0.0271(7) Uani 1.000000 .
H12 H -0.1584(4) -0.0345(2) 0.0807(3) 0.0326(8) Uiso 1.000000 R
C13 C -0.0579(4) 0.1291(2) 0.1335(2) 0.0244(7) Uani 1.000000 .
H13 H -0.1154(4) 0.1310(2) 0.0662(2) 0.0293(8) Uiso 1.000000 R
C14 C 0.0619(4) 0.4696(2) 0.1764(2) 0.0194(6) Uani 1.000000 .
C15 C -0.0077(4) 0.5457(2) 0.1387(2) 0.0197(6) Uani 1.000000 .
C16 C -0.1993(4) 0.5309(2) 0.0825(2) 0.0214(6) Uani 1.000000 .
H16 H -0.2894(4) 0.4683(2) 0.0690(2) 0.0257(8) Uiso 1.000000 R
C17 C -0.2589(4) 0.6060(2) 0.0465(2) 0.0247(7) Uani 1.000000 .
H17 H -0.3891(4) 0.5951(2) 0.0075(2) 0.0296(8) Uiso 1.000000 R
C18 C -0.1251(4) 0.6989(2) 0.0682(2) 0.0253(7) Uani 1.000000 .
H18 H -0.1662(4) 0.7520(2) 0.0450(2) 0.0303(8) Uiso 1.000000 R
C19 C 0.0640(4) 0.7141(2) 0.1222(2) 0.0214(6) Uani 1.000000 .
H19 H 0.1523(4) 0.7770(2) 0.1347(2) 0.0256(8) Uiso 1.000000 R
C20 C 0.1299(4) 0.6385(2) 0.1595(2) 0.0193(6) Uani 1.000000 .
C21 C 0.3319(4) 0.6528(2) 0.2172(2) 0.0198(6) Uani 1.000000 .
C22 C 0.4719(4) 0.7429(2) 0.2385(2) 0.0248(7) Uani 1.000000 .
H22 H 0.4363(4) 0.7953(2) 0.2130(2) 0.0298(8) Uiso 1.000000 R
C23 C 0.6592(4) 0.7574(2) 0.2955(2) 0.0289(7) Uani 1.000000 .
H23 H 0.7513(4) 0.8189(2) 0.3082(2) 0.0347(9) Uiso 1.000000 R
C24 C 0.7149(4) 0.6822(2) 0.3347(2) 0.0291(7) Uani 1.000000 .
H24 H 0.8436(4) 0.6940(2) 0.3762(2) 0.0349(9) Uiso 1.000000 R
C25 C 0.5851(4) 0.5915(2) 0.3136(2) 0.0252(7) Uani 1.000000 .
H25 H 0.6243(4) 0.5395(2) 0.3388(2) 0.0302(8) Uiso 1.000000 R
C26 C 0.3938(4) 0.5754(2) 0.2546(2) 0.0207(6) Uani 1.000000 .
C27 C 0.2506(4) 0.4837(2) 0.2308(2) 0.0198(6) Uani 1.000000 .
O8 O 0.5883(3) 0.26588(16) 0.06654(17) 0.0264(5) Uani 1.000000 .
H8a H 0.575(4) 0.2491(18) 0.1183(13) 0.0396(7) Uiso 1.000000 G
H8b H 0.568(4) 0.2039(9) 0.0088(11) 0.0396(7) Uiso 1.000000 G
H5 H 0.385(5) 0.377(3) 0.281(3) 0.051(10) Uiso 1.000000 .
H4 H -0.171(5) 0.334(3) 0.134(3) 0.051(10) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
O2 N1 O1 123.8(2) . . ?
C1 N1 O1 118.5(2) . . ?
C1 N1 O2 117.7(2) . . ?
O4 N2 O3 123.4(2) . . ?
C3 N2 O3 118.1(2) . . ?
C3 N2 O4 118.5(3) . . ?
O6 N3 O5 121.9(2) . . ?
C5 N3 O5 118.0(2) . . ?
C5 N3 O6 120.0(2) . . ?
C14 N4 C7 108.6(2) . . ?
H4 N4 C7 120.5(18) . . ?
H4 N4 C14 130.8(18) . . ?
C27 N5 C7 109.0(2) . . ?
H5 N5 C7 125.6(19) . . ?
H5 N5 C27 124.5(19) . . ?
C2 C1 N1 115.5(2) . . ?
C6 C1 N1 119.5(2) . . ?
C6 C1 C2 125.0(3) . . ?
H2 C2 C1 120.67(17) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.67(16) . . ?
C2 C3 N2 119.3(3) . . ?
C4 C3 N2 119.4(3) . . ?
C4 C3 C2 121.3(3) . . ?
H4a C4 C3 120.14(16) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4a 120.14(17) . . ?
C4 C5 N3 115.9(2) . . ?
C6 C5 N3 120.6(2) . . ?
C6 C5 C4 123.5(3) . . ?
C1 C6 O7 122.4(2) . . ?
C5 C6 O7 125.8(3) . . ?
C5 C6 C1 111.8(2) . . ?
N5 C7 N4 108.8(2) . . ?
C8 C7 N4 126.9(2) . . ?
C8 C7 N5 124.4(2) . . ?
C9 C8 C7 118.9(3) . . ?
C13 C8 C7 120.8(2) . . ?
C13 C8 C9 120.3(3) . . ?
H9 C9 C8 120.19(17) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.19(18) . . ?
H10 C10 C9 119.91(18) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.91(17) . . ?
H11 C11 C10 119.97(17) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.97(17) . . ?
H12 C12 C11 119.94(17) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.94(18) . . ?
C12 C13 C8 119.8(3) . . ?
H13 C13 C8 120.11(16) . . ?
H13 C13 C12 120.11(18) . . ?
C15 C14 N4 130.3(2) . . ?
C27 C14 N4 106.9(2) . . ?
C27 C14 C15 122.9(3) . . ?
C16 C15 C14 122.9(3) . . ?
C20 C15 C14 116.4(2) . . ?
C20 C15 C16 120.7(2) . . ?
H16 C16 C15 119.66(16) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.66(17) . . ?
H17 C17 C16 120.42(17) . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H17 120.42(16) . . ?
H18 C18 C17 119.55(16) . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.55(17) . . ?
H19 C19 C18 119.34(17) . . ?
C20 C19 C18 121.3(3) . . ?
C20 C19 H19 119.34(16) . . ?
C19 C20 C15 117.2(2) . . ?
C21 C20 C15 120.5(2) . . ?
C21 C20 C19 122.3(2) . . ?
C22 C21 C20 122.1(3) . . ?
C26 C21 C20 121.0(2) . . ?
C26 C21 C22 116.9(3) . . ?
H22 C22 C21 119.17(16) . . ?
C23 C22 C21 121.7(3) . . ?
C23 C22 H22 119.17(18) . . ?
H23 C23 C22 119.84(18) . . ?
C24 C23 C22 120.3(3) . . ?
C24 C23 H23 119.84(17) . . ?
H24 C24 C23 119.88(17) . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.88(17) . . ?
H25 C25 C24 120.05(17) . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.05(17) . . ?
C25 C26 C21 120.9(3) . . ?
C27 C26 C21 116.2(2) . . ?
C27 C26 C25 122.9(3) . . ?
C14 C27 N5 106.7(2) . . ?
C26 C27 N5 130.2(2) . . ?
C26 C27 C14 123.1(2) . . ?
H8b O8 H8a 104.5 . . ?
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 N1 1.226(3) . ?
O2 N1 1.232(3) . ?
O3 N2 1.229(3) . ?
O4 N2 1.226(3) . ?
O5 N3 1.243(3) . ?
O6 N3 1.224(3) . ?
O7 C6 1.257(3) . ?
N1 C1 1.459(3) . ?
N2 C3 1.448(3) . ?
N3 C5 1.454(3) . ?
N4 C7 1.336(3) . ?
N4 C14 1.392(3) . ?
N4 H4 0.99(3) . ?
N5 C7 1.338(3) . ?
N5 C27 1.385(3) . ?
N5 H5 0.96(3) . ?
C1 C2 1.366(4) . ?
C1 C6 1.449(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C3 C4 1.379(4) . ?
C4 H4a 0.9500 . ?
C4 C5 1.377(4) . ?
C5 C6 1.449(4) . ?
C7 C8 1.463(4) . ?
C8 C9 1.393(4) . ?
C8 C13 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.424(4) . ?
C14 C27 1.372(4) . ?
C15 C16 1.396(4) . ?
C15 C20 1.421(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.404(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.370(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.407(4) . ?
C20 C21 1.468(4) . ?
C21 C22 1.403(4) . ?
C21 C26 1.421(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.373(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.396(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.366(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.403(4) . ?
C26 C27 1.422(4) . ?
O8 H8a 0.8501 . ?
O8 H8b 0.8500 . ?
