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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/7/22/50/7225000.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_7225000
loop_
_publ_author_name
'Rajagopal, Shinaj K.'
'Reddy, V. Sivaranjana'
'Hariharan, Mahesh'
_publ_section_title
;
 Crystallization induced green-yellow-orange emitters based on
 benzoylpyrenes
;
_journal_issue                   27
_journal_name_full               CrystEngComm
_journal_page_first              5089
_journal_paper_doi               10.1039/C6CE00610H
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C44 H26 O4'
_chemical_formula_sum            'C44 H26 O4'
_chemical_formula_weight         618.65
_chemical_melting_point          561.15
_chemical_name_common            Tetrabenzoylpyrene
_chemical_name_systematic        pyrene-1,3,6,8-tetrayltetrakis(phenylmethanone)
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-12-03 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.506(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6503(16)
_cell_length_b                   20.897(5)
_cell_length_c                   12.787(3)
_cell_measurement_reflns_used    3898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.81
_cell_measurement_theta_min      2.54
_cell_volume                     1479.5(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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14254
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.538
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      1.388
_exptl_crystal_density_method    NONE
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             644
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3:Acetone'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0706P)²+0.2577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2655
_reflns_number_total             3578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00610h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224995--7225000.cif.
;
_cod_database_code               7225000
_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   0.978
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014-3
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
C1 C 0.8775(3) 0.08469(6) 0.75771(11) 0.0317(3) Uani 1 1 d . .
H1 H 0.8506 0.1081 0.6946 0.038 Uiso 1 1 calc R U
C2 C 1.0452(3) 0.03525(6) 0.77034(10) 0.0292(3) Uani 1 1 d . .
C3 C 1.1005(2) 0.00169(6) 0.86772(10) 0.0267(3) Uani 1 1 d . .
C4 C 0.9723(2) 0.01676(5) 0.95003(10) 0.0250(3) Uani 1 1 d . .
C5 C 0.7896(2) 0.06533(6) 0.93319(10) 0.0257(3) Uani 1 1 d . .
C6 C 0.7487(3) 0.10038(6) 0.83597(10) 0.0288(3) Uani 1 1 d . .
C7 C 0.6586(3) 0.07684(6) 1.01652(10) 0.0290(3) Uani 1 1 d . .
H7 H 0.5346 0.1069 1.0057 0.035 Uiso 1 1 calc R U
C8 C 1.2892(2) -0.04524(6) 0.88988(10) 0.0297(3) Uani 1 1 d . .
H8 H 1.3785 -0.0541 0.8379 0.036 Uiso 1 1 calc R U
C9 C 1.1696(3) 0.02243(6) 0.67860(11) 0.0325(3) Uani 1 1 d . .
C10 C 1.1759(3) -0.04406(7) 0.63671(10) 0.0315(3) Uani 1 1 d . .
C11 C 1.3522(3) -0.05935(8) 0.57857(12) 0.0426(4) Uani 1 1 d . .
H11 H 1.4643 -0.0286 0.5683 0.051 Uiso 1 1 calc R U
C12 C 1.3618(4) -0.11962(9) 0.53624(14) 0.0530(5) Uani 1 1 d . .
H12 H 1.4803 -0.1296 0.4978 0.064 Uiso 1 1 calc R U
C13 C 1.1953(4) -0.16521(9) 0.55096(14) 0.0562(5) Uani 1 1 d . .
H13 H 1.2015 -0.2059 0.5221 0.067 Uiso 1 1 calc R U
C14 C 1.0198(4) -0.15093(8) 0.60820(14) 0.0515(4) Uani 1 1 d . .
H14 H 0.9078 -0.1819 0.6177 0.062 Uiso 1 1 calc R U
C15 C 1.0098(3) -0.09039(7) 0.65176(12) 0.0390(4) Uani 1 1 d . .
H15 H 0.8922 -0.0809 0.6909 0.047 Uiso 1 1 calc R U
C16 C 0.5664(3) 0.15334(6) 0.81229(11) 0.0315(3) Uani 1 1 d . .
C17 C 0.6080(3) 0.20533(6) 0.73712(11) 0.0318(3) Uani 1 1 d . .
C18 C 0.8281(3) 0.23734(7) 0.74986(13) 0.0408(4) Uani 1 1 d . .
H18 H 0.9602 0.2232 0.8000 0.049 Uiso 1 1 calc R U
C19 C 0.8490(3) 0.29061(8) 0.68697(16) 0.0506(4) Uani 1 1 d . .
H19 H 0.9934 0.3133 0.6972 0.061 Uiso 1 1 calc R U
C20 C 0.6556(4) 0.30983(8) 0.60937(16) 0.0543(5) Uani 1 1 d . .
H20 H 0.6707 0.3453 0.5672 0.065 Uiso 1 1 calc R U
C21 C 0.4401(3) 0.27675(8) 0.59411(14) 0.0485(4) Uani 1 1 d . .
H21 H 0.3122 0.2891 0.5402 0.058 Uiso 1 1 calc R U
C22 C 0.4136(3) 0.22517(7) 0.65883(12) 0.0382(3) Uani 1 1 d . .
H22 H 0.2665 0.2038 0.6501 0.046 Uiso 1 1 calc R U
O1 O 1.2575(2) 0.06664(5) 0.63781(9) 0.0525(3) Uani 1 1 d . .
O2 O 0.3874(2) 0.15638(5) 0.85195(9) 0.0463(3) 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'
O O 0.0106 0.0060 '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
C6 C1 C2 122.35(12) . .
C6 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C1 C2 C3 119.91(12) . .
C1 C2 C9 117.06(11) . .
C3 C2 C9 122.96(12) . .
C2 C3 C4 119.11(12) . .
C2 C3 C8 122.66(12) . .
C4 C3 C8 118.16(11) . .
C3 C4 C5 120.13(11) . .
C3 C4 C4 119.74(14) . 3_757
C5 C4 C4 120.13(14) . 3_757
C6 C5 C4 118.88(12) . .
C6 C5 C7 123.06(12) . .
C4 C5 C7 118.05(11) . .
C1 C6 C5 119.42(12) . .
C1 C6 C16 117.77(11) . .
C5 C6 C16 122.79(12) . .
C8 C7 C5 121.61(12) 3_757 .
C8 C7 H7 119.2 3_757 .
C5 C7 H7 119.2 . .
C7 C8 C3 122.19(12) 3_757 .
C7 C8 H8 118.9 3_757 .
C3 C8 H8 118.9 . .
O1 C9 C10 120.87(13) . .
O1 C9 C2 119.54(12) . .
C10 C9 C2 119.56(11) . .
C15 C10 C11 119.27(14) . .
C15 C10 C9 122.30(13) . .
C11 C10 C9 118.41(13) . .
C12 C11 C10 120.52(16) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 119.85(16) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C14 C13 C12 120.41(16) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 120.12(17) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C14 C15 C10 119.82(15) . .
C14 C15 H15 120.1 . .
C10 C15 H15 120.1 . .
O2 C16 C17 118.52(12) . .
O2 C16 C6 123.16(12) . .
C17 C16 C6 118.32(12) . .
C18 C17 C22 119.90(13) . .
C18 C17 C16 121.57(13) . .
C22 C17 C16 118.29(14) . .
C19 C18 C17 119.56(15) . .
C19 C18 H18 120.2 . .
C17 C18 H18 120.2 . .
C20 C19 C18 120.11(17) . .
C20 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
C21 C20 C19 120.35(15) . .
C21 C20 H20 119.8 . .
C19 C20 H20 119.8 . .
C20 C21 C22 120.19(16) . .
C20 C21 H21 119.9 . .
C22 C21 H21 119.9 . .
C21 C22 C17 119.81(16) . .
C21 C22 H22 120.1 . .
C17 C22 H22 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.3889(19) .
C1 C2 1.3892(19) .
C1 H1 0.9300 .
C2 C3 1.4088(18) .
C2 C9 1.5070(18) .
C3 C4 1.4266(18) .
C3 C8 1.4349(18) .
C4 C5 1.4329(17) .
C4 C4 1.436(2) 3_757
C5 C6 1.4215(17) .
C5 C7 1.4337(18) .
C6 C16 1.5009(18) .
C7 C8 1.3472(18) 3_757
C7 H7 0.9300 .
C8 C7 1.3472(18) 3_757
C8 H8 0.9300 .
C9 O1 1.2147(17) .
C9 C10 1.4921(19) .
C10 C15 1.388(2) .
C10 C11 1.394(2) .
C11 C12 1.376(2) .
C11 H11 0.9300 .
C12 C13 1.378(3) .
C12 H12 0.9300 .
C13 C14 1.378(3) .
C13 H13 0.9300 .
C14 C15 1.388(2) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 O2 1.2205(18) .
C16 C17 1.4998(19) .
C17 C18 1.392(2) .
C17 C22 1.394(2) .
C18 C19 1.392(2) .
C18 H18 0.9300 .
C19 C20 1.381(3) .
C19 H19 0.9300 .
C20 C21 1.380(3) .
C20 H20 0.9300 .
C21 C22 1.385(2) .
C21 H21 0.9300 .
C22 H22 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129868454
