#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:04:21 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268737 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/78/7707880.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_7707880
loop_
_publ_author_name
'Hiti, E. A.'
'Wilkinson, G. R.'
'Ariyarathna, I. R.'
'Tutson, C. D.'
'Hardy, E. E.'
'Maynard, B. A.'
'Miliordos, E.'
'Gorden, A. E. V.'
_publ_section_title
;
 Comparing coordination uranyl(vi) complexes with
 2-(1H-imidazo[4,5-b]phenazin-2-yl)phenol and derivatives.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11113
_journal_page_last               11122
_journal_paper_doi               10.1039/d1dt02359d
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C19 H12 N4 O'
_chemical_formula_sum            'C19 H12 N4 O'
_chemical_formula_weight         312.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2017-07-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-03-01 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.293(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6597(6)
_cell_length_b                   30.064(3)
_cell_length_c                   7.2617(6)
_cell_measurement_reflns_used    3320
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.467
_cell_measurement_theta_min      2.710
_cell_volume                     1380.4(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13927
_diffrn_reflns_theta_full        27.4803
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.0671 before and 0.0479 after correction. The Ratio of minimum to maximum transmission is 0.8880. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.5027
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             648.2625
_exptl_crystal_preparation       'Single crystal cut to size'
_exptl_crystal_recrystallization_method
'Grown from a solution of ligand in DMSO layered with a UO2 solution (EtOH)'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.4138
_refine_diff_density_min         -0.3338
_refine_diff_density_rms         0.0882
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             7.5161
_refine_ls_goodness_of_fit_ref   1.0665
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0665
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0514P)²+1.0683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -8
_reflns_limit_k_max              38
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -4
_reflns_number_gt                2482
_reflns_number_total             3173
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1dt02359d5.cif
_cod_data_source_block           Hiti070117_0m
_cod_depositor_comments
'Adding full bibliography for 7707878--7707880.cif.'
_cod_original_cell_volume        1380.5(2)
_cod_database_code               7707880
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C9(H9), C15(H15), C12(H12), C2(H2), C5(H5), C3(H3), C4(H4),
 C14(H14), C13(H13), N1(H1a)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Mounted on a thin glass fiber using Paratone oil.'
_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+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
N2 N -0.4687(3) -0.10978(6) 0.0395(2) 0.0212(4) Uani 1.000000 .
C10 C -0.2987(3) -0.08296(6) 0.0990(3) 0.0183(4) Uani 1.000000 .
N3 N -0.0604(3) -0.14021(5) 0.0500(2) 0.0202(4) Uani 1.000000 .
C17 C -0.0898(3) -0.09840(6) 0.1035(3) 0.0183(4) Uani 1.000000 .
C16 C -0.2314(3) -0.16655(6) -0.0096(3) 0.0202(4) Uani 1.000000 .
C6 C 0.1733(3) 0.08482(6) 0.3842(3) 0.0181(4) Uani 1.000000 .
C8 C -0.1524(3) -0.01251(6) 0.2144(3) 0.0187(4) Uani 1.000000 .
C11 C -0.4373(3) -0.15127(7) -0.0140(3) 0.0205(4) Uani 1.000000 .
C18 C 0.0868(3) -0.06940(6) 0.1630(3) 0.0190(4) Uani 1.000000 .
H18 H 0.2206(3) -0.07887(6) 0.1654(3) 0.0228(5) Uiso 1.000000 R
C19 C 0.0544(3) -0.02705(6) 0.2168(3) 0.0179(4) Uani 1.000000 .
C9 C -0.3263(3) -0.03912(6) 0.1575(3) 0.0199(4) Uani 1.000000 .
H9 H -0.4582(3) -0.02887(6) 0.1571(3) 0.0238(5) Uiso 1.000000 R
C15 C -0.2101(3) -0.21066(7) -0.0730(3) 0.0248(5) Uani 1.000000 .
H15 H -0.0778(3) -0.22097(7) -0.0714(3) 0.0298(5) Uiso 1.000000 R
C1 C 0.3918(3) 0.09194(6) 0.4238(3) 0.0188(4) Uani 1.000000 .
C12 C -0.6124(3) -0.18115(7) -0.0771(3) 0.0264(5) Uani 1.000000 .
H12 H -0.7459(3) -0.17208(7) -0.0771(3) 0.0317(6) Uiso 1.000000 R
C2 C 0.4797(3) 0.13293(7) 0.4971(3) 0.0236(4) Uani 1.000000 .
H2 H 0.6244(3) 0.13754(7) 0.5259(3) 0.0283(5) Uiso 1.000000 R
C5 C 0.0486(3) 0.11968(7) 0.4146(3) 0.0236(4) Uani 1.000000 .
H5 H -0.0961(3) 0.11545(7) 0.3872(3) 0.0283(5) Uiso 1.000000 R
C7 C 0.0834(3) 0.04164(6) 0.3138(3) 0.0174(4) Uani 1.000000 .
C3 C 0.3531(3) 0.16650(7) 0.5267(3) 0.0264(5) Uani 1.000000 .
H3 H 0.4127(3) 0.19372(7) 0.5756(3) 0.0317(6) Uiso 1.000000 R
C4 C 0.1360(4) 0.16001(7) 0.4840(3) 0.0282(5) Uani 1.000000 .
H4 H 0.0507(4) 0.18297(7) 0.5026(3) 0.0339(6) Uiso 1.000000 R
C14 C -0.3809(3) -0.23770(7) -0.1358(3) 0.0282(5) Uani 1.000000 .
H14 H -0.3652(3) -0.26627(7) -0.1785(3) 0.0338(6) Uiso 1.000000 R
C13 C -0.5840(3) -0.22275(7) -0.1369(3) 0.0290(5) Uani 1.000000 .
H13 H -0.6993(3) -0.24183(7) -0.1794(3) 0.0348(6) Uiso 1.000000 R
O1 O 0.5211(2) 0.05982(5) 0.3953(2) 0.0258(3) Uani 1.000000 .
H1 H 0.4528(8) 0.0370(3) 0.358(4) 0.0387(5) Uiso 1.000000 GR
N1 N -0.1249(2) 0.03098(5) 0.2782(2) 0.0203(4) Uani 1.000000 .
H1a H -0.2216(2) 0.04829(5) 0.2929(2) 0.0243(4) Uiso 1.000000 R
N4 N 0.1956(2) 0.00816(5) 0.2797(2) 0.0190(4) Uani 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
C11 N2 C10 117.24(17) . . ?
C17 C10 N2 121.17(17) . . ?
C9 C10 N2 118.62(17) . . ?
C9 C10 C17 120.21(17) . . ?
C16 N3 C17 117.24(17) . . ?
N3 C17 C10 120.95(17) . . ?
C18 C17 C10 120.38(17) . . ?
C18 C17 N3 118.67(17) . . ?
C11 C16 N3 121.73(18) . . ?
C15 C16 N3 119.49(18) . . ?
C15 C16 C11 118.77(18) . . ?
C5 C6 C1 118.74(18) . . ?
C7 C6 C1 119.51(17) . . ?
C7 C6 C5 121.75(17) . . ?
C9 C8 C19 123.03(18) . . ?
N1 C8 C19 104.96(16) . . ?
N1 C8 C9 132.01(18) . . ?
C16 C11 N2 121.66(18) . . ?
C12 C11 N2 119.44(18) . . ?
C12 C11 C16 118.90(18) . . ?
C19 C18 C17 117.97(17) . . ?
C18 C19 C8 120.99(17) . . ?
N4 C19 C8 108.50(16) . . ?
N4 C19 C18 130.52(17) . . ?
C8 C9 C10 117.41(17) . . ?
C14 C15 C16 120.5(2) . . ?
C2 C1 C6 119.67(18) . . ?
O1 C1 C6 121.80(17) . . ?
O1 C1 C2 118.53(17) . . ?
C13 C12 C11 120.1(2) . . ?
C3 C2 C1 120.22(19) . . ?
C4 C5 C6 121.15(19) . . ?
N1 C7 C6 123.86(17) . . ?
N4 C7 C6 123.47(17) . . ?
N4 C7 N1 112.66(17) . . ?
C4 C3 C2 120.4(2) . . ?
C3 C4 C5 119.75(19) . . ?
C13 C14 C15 120.6(2) . . ?
C14 C13 C12 121.1(2) . . ?
C7 N1 C8 107.78(16) . . ?
C7 N4 C19 106.10(16) . . ?
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
N2 C10 1.346(2) . ?
N2 C11 1.343(3) . ?
C10 C17 1.457(3) . ?
C10 C9 1.415(3) . ?
N3 C17 1.348(2) . ?
N3 C16 1.342(2) . ?
C17 C18 1.418(3) . ?
C16 C11 1.437(3) . ?
C16 C15 1.426(3) . ?
C6 C1 1.408(3) . ?
C6 C5 1.397(3) . ?
C6 C7 1.453(3) . ?
C8 C19 1.440(3) . ?
C8 C9 1.361(3) . ?
C8 N1 1.380(2) . ?
C11 C12 1.429(3) . ?
C18 C19 1.368(3) . ?
C19 N4 1.394(2) . ?
C15 C14 1.356(3) . ?
C1 C2 1.396(3) . ?
C1 O1 1.352(2) . ?
C12 C13 1.356(3) . ?
C2 C3 1.375(3) . ?
C5 C4 1.371(3) . ?
C7 N1 1.367(2) . ?
C7 N4 1.322(2) . ?
C3 C4 1.394(3) . ?
C14 C13 1.423(3) . ?
