#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:18:43 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/05/7060539.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_7060539
loop_
_publ_author_name
'Tabasi, Zahra A.'
'Walsh, Joshua C.'
'Bodwell, Graham J.'
'Thompson, David W.'
'Zhao, Yuming'
_publ_section_title
;
 Comparative study of the photophysical and crystallographic properties of
 4-(9H-pyreno[4,5-d]imidazol-10-yl)phenol and its alkylated derivatives
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7647
_journal_page_last               7658
_journal_paper_doi               10.1039/D1NJ01102B
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C23 H14 N2 O, C H4 O'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-08-28 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.1087(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6038(2)
_cell_length_b                   8.2717(2)
_cell_length_c                   18.3638(4)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.85
_cell_measurement_theta_min      3.75
_cell_volume                     1809.02(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12501
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.138
_diffrn_reflns_theta_min         3.751
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0741P)²+0.6757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3231
_reflns_number_total             3591
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj01102b2.cif
_cod_data_source_block           mun1923
_cod_depositor_comments
'Adding full bibliography for 7060539--7060541.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060539
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47587(8) 0.69800(14) 0.30451(6) 0.0314(3) Uani 1 1 d . . . . .
H1O H 0.4535(19) 0.722(3) 0.2479(14) 0.055(6) Uiso 1 1 d . . . . .
N1 N 0.14121(10) 0.36887(14) 0.46148(7) 0.0242(3) Uani 1 1 d . . . . .
H1N H 0.1932(17) 0.416(2) 0.5040(12) 0.037(5) Uiso 1 1 d . . . . .
N2 N 0.05833(10) 0.27932(14) 0.34200(7) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.14372(12) 0.36426(17) 0.38796(8) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.04792(11) 0.28325(16) 0.46268(8) 0.0234(3) Uani 1 1 d . . . . .
C3 C -0.00239(11) 0.22833(16) 0.38853(8) 0.0235(3) Uani 1 1 d . . . . .
C4 C -0.10343(12) 0.13331(16) 0.36864(8) 0.0248(3) Uani 1 1 d . . . . .
C5 C -0.15863(13) 0.07444(18) 0.29461(9) 0.0298(3) Uani 1 1 d . . . . .
H5 H -0.129017 0.095964 0.254219 0.036 Uiso 1 1 calc R U . . .
C6 C -0.25681(13) -0.01561(19) 0.27963(9) 0.0340(3) Uani 1 1 d . . . . .
H6 H -0.293561 -0.055145 0.229053 0.041 Uiso 1 1 calc R U . . .
C7 C -0.30128(13) -0.04802(19) 0.33745(10) 0.0340(4) Uani 1 1 d . . . . .
H7 H -0.368427 -0.109441 0.326166 0.041 Uiso 1 1 calc R U . . .
C8 C -0.24866(12) 0.00852(18) 0.41268(9) 0.0294(3) Uani 1 1 d . . . . .
C9 C -0.29548(13) -0.0197(2) 0.47290(10) 0.0357(4) Uani 1 1 d . . . . .
H9 H -0.362115 -0.082081 0.462234 0.043 Uiso 1 1 calc R U . . .
C10 C -0.24705(13) 0.0405(2) 0.54441(10) 0.0348(4) Uani 1 1 d . . . . .
H10 H -0.281019 0.021254 0.582779 0.042 Uiso 1 1 calc R U . . .
C11 C -0.14477(12) 0.13331(18) 0.56376(9) 0.0288(3) Uani 1 1 d . . . . .
C12 C -0.09332(14) 0.19528(19) 0.63784(9) 0.0322(3) Uani 1 1 d . . . . .
H12 H -0.126313 0.176002 0.676722 0.039 Uiso 1 1 calc R U . . .
C13 C 0.00483(14) 0.28417(19) 0.65542(9) 0.0322(3) Uani 1 1 d . . . . .
H13 H 0.038624 0.324525 0.706202 0.039 Uiso 1 1 calc R U . . .
C14 C 0.05444(12) 0.31499(18) 0.59955(8) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.121832 0.376175 0.612197 0.033 Uiso 1 1 calc R U . . .
C15 C 0.00516(11) 0.25591(16) 0.52464(8) 0.0240(3) Uani 1 1 d . . . . .
C16 C -0.09558(12) 0.16291(17) 0.50564(8) 0.0246(3) Uani 1 1 d . . . . .
C17 C -0.14791(11) 0.10098(16) 0.42922(8) 0.0248(3) Uani 1 1 d . . . . .
C18 C 0.22959(12) 0.44883(17) 0.36463(8) 0.0255(3) Uani 1 1 d . . . . .
C19 C 0.32860(13) 0.5027(2) 0.41994(9) 0.0348(4) Uani 1 1 d . . . . .
H19 H 0.341178 0.480059 0.472830 0.042 Uiso 1 1 calc R U . . .
C20 C 0.40854(13) 0.5882(2) 0.39912(9) 0.0371(4) Uani 1 1 d . . . . .
H20 H 0.474576 0.625439 0.437645 0.045 Uiso 1 1 calc R U . . .
C21 C 0.39226(12) 0.61975(18) 0.32183(8) 0.0272(3) Uani 1 1 d . . . . .
C22 C 0.29339(12) 0.57002(17) 0.26618(8) 0.0273(3) Uani 1 1 d . . . . .
H22 H 0.280870 0.593493 0.213386 0.033 Uiso 1 1 calc R U . . .
C23 C 0.21276(12) 0.48594(17) 0.28768(8) 0.0275(3) Uani 1 1 d . . . . .
H23 H 0.145161 0.453328 0.249285 0.033 Uiso 1 1 calc R U . . .
O1S O 0.67778(10) 0.53918(16) 0.39919(7) 0.0393(3) Uani 1 1 d . . . . .
H1OS H 0.624(3) 0.614(4) 0.3656(18) 0.092(10) Uiso 1 1 d . . . . .
C1S C 0.63810(18) 0.3799(2) 0.37808(13) 0.0512(5) Uani 1 1 d . . . . .
H1SA H 0.652921 0.314680 0.423577 0.061 Uiso 1 1 calc R U . . .
H1SB H 0.675780 0.334410 0.345113 0.061 Uiso 1 1 calc R U . . .
H1SC H 0.558712 0.382631 0.351243 0.061 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 107.35(12) . . ?
C1 N2 C3 105.36(12) . . ?
N2 C1 N1 111.55(12) . . ?
N2 C1 C18 126.03(13) . . ?
N1 C1 C18 122.39(13) . . ?
C3 C2 N1 105.83(12) . . ?
C3 C2 C15 124.33(13) . . ?
N1 C2 C15 129.82(13) . . ?
C2 C3 N2 109.91(12) . . ?
C2 C3 C4 120.95(13) . . ?
N2 C3 C4 129.14(13) . . ?
C5 C4 C17 119.77(13) . . ?
C5 C4 C3 123.75(14) . . ?
C17 C4 C3 116.49(13) . . ?
C6 C5 C4 120.41(15) . . ?
C7 C6 C5 120.70(15) . . ?
C6 C7 C8 120.87(14) . . ?
C7 C8 C17 119.28(14) . . ?
C7 C8 C9 121.64(14) . . ?
C17 C8 C9 119.05(14) . . ?
C10 C9 C8 121.46(14) . . ?
C9 C10 C11 121.30(15) . . ?
C12 C11 C16 119.36(14) . . ?
C12 C11 C10 121.83(14) . . ?
C16 C11 C10 118.81(14) . . ?
C13 C12 C11 121.07(14) . . ?
C12 C13 C14 120.64(14) . . ?
C13 C14 C15 120.00(14) . . ?
C14 C15 C16 120.12(13) . . ?
C14 C15 C2 124.50(13) . . ?
C16 C15 C2 115.37(13) . . ?
C11 C16 C15 118.80(13) . . ?
C11 C16 C17 119.95(13) . . ?
C15 C16 C17 121.24(13) . . ?
C4 C17 C8 118.96(13) . . ?
C4 C17 C16 121.59(13) . . ?
C8 C17 C16 119.42(13) . . ?
C23 C18 C19 118.03(13) . . ?
C23 C18 C1 121.33(13) . . ?
C19 C18 C1 120.55(13) . . ?
C20 C19 C18 121.29(14) . . ?
C19 C20 C21 120.03(14) . . ?
O1 C21 C22 123.06(13) . . ?
O1 C21 C20 117.47(13) . . ?
C22 C21 C20 119.47(13) . . ?
C21 C22 C23 120.11(13) . . ?
C22 C23 C18 121.02(13) . . ?
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 C21 1.3602(17) . ?
N1 C1 1.3615(18) . ?
N1 C2 1.3788(17) . ?
N2 C1 1.3302(18) . ?
N2 C3 1.3864(18) . ?
C1 C18 1.4655(19) . ?
C2 C3 1.3773(19) . ?
C2 C15 1.4276(19) . ?
C3 C4 1.4382(19) . ?
C4 C5 1.396(2) . ?
C4 C17 1.425(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.380(2) . ?
C7 C8 1.403(2) . ?
C8 C17 1.4273(19) . ?
C8 C9 1.433(2) . ?
C9 C10 1.349(3) . ?
C10 C11 1.442(2) . ?
C11 C12 1.399(2) . ?
C11 C16 1.420(2) . ?
C12 C13 1.383(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.399(2) . ?
C15 C16 1.4267(19) . ?
C16 C17 1.436(2) . ?
C18 C23 1.393(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.384(2) . ?
C20 C21 1.391(2) . ?
C21 C22 1.390(2) . ?
C22 C23 1.391(2) . ?
O1S C1S 1.418(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1O N2 1.00(2) 1.68(2) 2.6678(15) 168(2) 2 yes
N1 H1N O1S 0.92(2) 2.01(2) 2.9169(17) 165.3(18) 3_666 yes
O1S H1OS O1 0.97(3) 1.96(3) 2.8859(16) 157(3) . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C1 N1 0.56(15) . . . . ?
C3 N2 C1 C18 -177.54(13) . . . . ?
C2 N1 C1 N2 -0.69(16) . . . . ?
C2 N1 C1 C18 177.49(12) . . . . ?
C1 N1 C2 C3 0.51(15) . . . . ?
C1 N1 C2 C15 -177.78(14) . . . . ?
N1 C2 C3 N2 -0.19(15) . . . . ?
C15 C2 C3 N2 178.23(12) . . . . ?
N1 C2 C3 C4 -179.94(12) . . . . ?
C15 C2 C3 C4 -1.5(2) . . . . ?
C1 N2 C3 C2 -0.22(15) . . . . ?
C1 N2 C3 C4 179.51(14) . . . . ?
C2 C3 C4 C5 179.82(13) . . . . ?
N2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C17 0.40(19) . . . . ?
N2 C3 C4 C17 -179.30(13) . . . . ?
C17 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C6 -179.40(13) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C17 0.1(2) . . . . ?
C6 C7 C8 C9 178.03(15) . . . . ?
C7 C8 C9 C10 -177.29(15) . . . . ?
C17 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 -179.52(15) . . . . ?
C9 C10 C11 C16 0.8(2) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C10 C11 C12 C13 -179.99(14) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C13 C14 C15 C2 178.72(14) . . . . ?
C3 C2 C15 C14 -178.29(13) . . . . ?
N1 C2 C15 C14 -0.3(2) . . . . ?
C3 C2 C15 C16 1.0(2) . . . . ?
N1 C2 C15 C16 178.97(13) . . . . ?
C12 C11 C16 C15 -0.2(2) . . . . ?
C10 C11 C16 C15 179.50(13) . . . . ?
C12 C11 C16 C17 -179.58(13) . . . . ?
C10 C11 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C11 0.6(2) . . . . ?
C2 C15 C16 C11 -178.68(12) . . . . ?
C14 C15 C16 C17 179.96(12) . . . . ?
C2 C15 C16 C17 0.68(19) . . . . ?
C5 C4 C17 C8 0.0(2) . . . . ?
C3 C4 C17 C8 179.41(12) . . . . ?
C5 C4 C17 C16 -178.26(13) . . . . ?
C3 C4 C17 C16 1.19(19) . . . . ?
C7 C8 C17 C4 0.0(2) . . . . ?
C9 C8 C17 C4 -178.00(13) . . . . ?
C7 C8 C17 C16 178.24(13) . . . . ?
C9 C8 C17 C16 0.3(2) . . . . ?
C11 C16 C17 C4 177.59(13) . . . . ?
C15 C16 C17 C4 -1.8(2) . . . . ?
C11 C16 C17 C8 -0.6(2) . . . . ?
C15 C16 C17 C8 -179.98(12) . . . . ?
N2 C1 C18 C23 18.3(2) . . . . ?
N1 C1 C18 C23 -159.64(14) . . . . ?
N2 C1 C18 C19 -165.37(15) . . . . ?
N1 C1 C18 C19 16.7(2) . . . . ?
C23 C18 C19 C20 -1.0(2) . . . . ?
C1 C18 C19 C20 -177.44(15) . . . . ?
C18 C19 C20 C21 -1.2(3) . . . . ?
C19 C20 C21 O1 -177.13(15) . . . . ?
C19 C20 C21 C22 2.4(3) . . . . ?
O1 C21 C22 C23 177.95(13) . . . . ?
C20 C21 C22 C23 -1.6(2) . . . . ?
C21 C22 C23 C18 -0.6(2) . . . . ?
C19 C18 C23 C22 1.8(2) . . . . ?
C1 C18 C23 C22 178.28(13) . . . . ?
