#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:13:44 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301852 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/00/7060011.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_7060011
loop_
_publ_author_name
'Shahrokhi, Farshid'
'Fazli Estabragh, Roxana'
'Zhao, Yuming'
_publ_section_title
;
 Synthesis and comparative studies of K-region functionalized pyrene
 derivatives
;
_journal_issue                   39
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16786
_journal_page_last               16794
_journal_paper_doi               10.1039/D0NJ03897K
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C17 H8 Br2 O'
_chemical_formula_sum            'C17 H8 Br2 O'
_chemical_formula_weight         388.05
_chemical_name_systematic        5-(dibromomethylene)pyren-4(5H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-11 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4372(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.88283(4)
_cell_length_b                   18.75250(17)
_cell_length_c                   17.4959(2)
_cell_measurement_reflns_used    8163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9260
_cell_measurement_theta_min      3.4500
_cell_volume                     1272.77(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  39.00   0.50    0.06    --   47.95 -29.00 -82.00  130
  2  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 -90.00   88
  3  ω     35.00 131.00   0.50    0.25    --  107.75 -77.00 -90.00  192
  4  ω     94.00 178.00   0.50    0.25    --  107.75  15.00  30.00  168
  5  ω     95.00 178.00   0.50    0.25    --  107.75  29.00  78.00  166
  6  ω     95.00 178.00   0.50    0.25    --  107.75  30.00 120.00  166
  7  ω     36.00 122.00   0.50    0.06    --   47.95  29.00  78.00  172
  8  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00  30.00  142
  9  ω     35.00 112.00   0.50    0.25    --  107.75-125.00 -90.00  154
 10  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00-180.00  142
 11  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00-150.00   88
 12  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 -60.00   88
 13  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00   0.00   88
 14  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00  90.00   88
 15  ω     35.00  79.00   0.50    0.25    --  107.75 -61.00 150.00   88
 16  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00 150.00  142
 17  ω     35.00 106.00   0.50    0.25    --  107.75 -94.00 120.00  142
 18  ω     25.00 120.00   0.50    0.06    --   47.95  77.00-120.00  190
 19  ω     95.00 178.00   0.50    0.25    --  107.75  45.00-150.00  166
 20  ω     25.00 120.00   0.50    0.06    --   47.95  77.00 150.00  190
 21  ω    -25.00  27.00   0.50    0.06    --  -47.95  29.00  78.00  104
 22  ω    -43.00 -14.00   0.50    0.25    --  -86.25  45.00 -90.00   58
 23  ω    -43.00 -14.00   0.50    0.25    --  -86.25  45.00-150.00   58
 24  ω    -34.00  25.00   0.50    0.06    --  -47.95  37.00-150.00  118
 25  ω   -122.00 -35.00   0.50    0.06    --  -47.95 -29.00 -82.00  174
 26  ω   -120.00 -73.00   0.50    0.06    --  -47.95-125.00  30.00   94
 27  ω   -120.00 -64.00   0.50    0.06    --  -47.95 -77.00  60.00  112
 28  ω   -161.00 -74.00   0.50    0.25    --  -86.25 -29.00 -82.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2068081000
_diffrn_orient_matrix_UB_12      0.0310645000
_diffrn_orient_matrix_UB_13      0.0693512000
_diffrn_orient_matrix_UB_21      -0.3274410000
_diffrn_orient_matrix_UB_22      -0.0008591000
_diffrn_orient_matrix_UB_23      0.0467632000
_diffrn_orient_matrix_UB_31      0.0880137000
_diffrn_orient_matrix_UB_32      -0.0760387000
_diffrn_orient_matrix_UB_33      0.0277651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16339
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.239
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.025
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane/DCM'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+0.8889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             2654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj03897k2.cif
_cod_data_source_block           fs67
_cod_depositor_comments
'Adding full bibliography for 7060010--7060012.cif.'
_cod_database_code               7060011
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H8Br2O
_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_max   0.691
_shelx_estimated_absorpt_t_min   0.447
_diffrn_oxdiff_digest_frames
;
01127b13eb444f30c7dc3e5dbefd6e25af0010179b9
;
_diffrn_oxdiff_digest_hkl
;
01088e8dc8b49cf33a314fe9075a889eebf5d3
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.579
_oxdiff_exptl_absorpt_empirical_full_min 0.564
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.34490(7) 0.40924(2) 0.76594(2) 0.01867(10) Uani 1 1 d . . . . .
Br2 Br 0.10561(7) 0.47745(2) 0.61195(2) 0.01724(10) Uani 1 1 d . . . . .
O1 O 0.6748(5) 0.27231(10) 0.72542(11) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.4729(7) 0.26918(13) 0.67009(14) 0.0147(5) Uani 1 1 d . . . . .
C2 C 0.3707(6) 0.33430(13) 0.62323(14) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.3061(7) 0.32197(13) 0.54037(15) 0.0147(5) Uani 1 1 d . . . . .
C4 C 0.3769(7) 0.37223(13) 0.48475(15) 0.0160(5) Uani 1 1 d . . . . .
H4 H 0.487318 0.415695 0.499169 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2865(7) 0.35924(14) 0.40742(15) 0.0178(5) Uani 1 1 d . . . . .
H5 H 0.343154 0.393358 0.369838 0.021 Uiso 1 1 calc R . . . .
C6 C 0.1169(7) 0.29768(14) 0.38546(15) 0.0178(5) Uani 1 1 d . . . . .
H6 H 0.039713 0.291156 0.333683 0.021 Uiso 1 1 calc R . . . .
C7 C 0.0580(6) 0.24416(14) 0.44032(15) 0.0162(5) Uani 1 1 d . . . . .
C8 C -0.1072(7) 0.17831(15) 0.41797(16) 0.0197(5) Uani 1 1 d . . . . .
H8 H -0.194473 0.172260 0.366830 0.024 Uiso 1 1 calc R . . . .
C9 C -0.1396(7) 0.12468(14) 0.46939(17) 0.0212(6) Uani 1 1 d . . . . .
H9 H -0.255532 0.082079 0.454049 0.025 Uiso 1 1 calc R . . . .
C10 C -0.0021(7) 0.13126(14) 0.54625(16) 0.0189(5) Uani 1 1 d . . . . .
C11 C -0.0020(8) 0.07372(14) 0.59887(18) 0.0225(6) Uani 1 1 d . . . . .
H11 H -0.111032 0.030176 0.584220 0.027 Uiso 1 1 calc R . . . .
C12 C 0.1527(8) 0.07981(14) 0.67053(18) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.150838 0.040614 0.704909 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3129(7) 0.14359(14) 0.69299(16) 0.0198(5) Uani 1 1 d . . . . .
H13 H 0.426057 0.147109 0.742067 0.024 Uiso 1 1 calc R . . . .
C14 C 0.3078(7) 0.20164(13) 0.64421(15) 0.0161(5) Uani 1 1 d . . . . .
C15 C 0.1492(7) 0.19682(13) 0.57043(15) 0.0154(5) Uani 1 1 d . . . . .
C16 C 0.1684(6) 0.25513(13) 0.51706(15) 0.0142(5) Uani 1 1 d . . . . .
C17 C 0.3011(7) 0.39505(14) 0.65943(15) 0.0155(5) 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 0.0181 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'
Br Br -0.6763 1.2805 '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
O1 C1 C2 122.4(2) . . ?
O1 C1 C14 122.6(2) . . ?
C14 C1 C2 115.1(2) . . ?
C3 C2 C1 115.7(2) . . ?
C17 C2 C1 119.0(2) . . ?
C17 C2 C3 124.6(2) . . ?
C4 C3 C2 123.3(2) . . ?
C4 C3 C16 118.8(2) . . ?
C16 C3 C2 117.8(2) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.5(2) . . ?
C16 C7 C6 119.5(2) . . ?
C16 C7 C8 120.0(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 C15 118.5(3) . . ?
C15 C10 C9 119.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C1 119.3(3) . . ?
C13 C14 C15 120.6(3) . . ?
C15 C14 C1 120.1(2) . . ?
C10 C15 C16 119.7(2) . . ?
C14 C15 C10 119.2(2) . . ?
C14 C15 C16 120.8(2) . . ?
C3 C16 C15 120.9(2) . . ?
C7 C16 C3 120.0(2) . . ?
C7 C16 C15 119.0(2) . . ?
Br1 C17 Br2 109.62(13) . . ?
C2 C17 Br1 125.3(2) . . ?
C2 C17 Br2 124.9(2) . . ?
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
Br1 C17 1.883(3) . ?
Br2 C17 1.898(3) . ?
O1 C1 1.221(3) . ?
C1 C2 1.514(3) . ?
C1 C14 1.482(4) . ?
C2 C3 1.479(4) . ?
C2 C17 1.337(4) . ?
C3 C4 1.391(4) . ?
C3 C16 1.416(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.405(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.414(4) . ?
C7 C8 1.438(4) . ?
C7 C16 1.407(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.359(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.431(4) . ?
C10 C11 1.418(4) . ?
C10 C15 1.419(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.372(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(4) . ?
C14 C15 1.409(4) . ?
C15 C16 1.442(4) . ?
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
O1 C1 C2 C3 145.7(2) . . . . ?
O1 C1 C2 C17 -43.1(4) . . . . ?
O1 C1 C14 C13 15.8(4) . . . . ?
O1 C1 C14 C15 -163.8(2) . . . . ?
C1 C2 C3 C4 -147.1(2) . . . . ?
C1 C2 C3 C16 32.2(3) . . . . ?
C1 C2 C17 Br1 4.0(4) . . . . ?
C1 C2 C17 Br2 -170.33(18) . . . . ?
C1 C14 C15 C10 178.9(2) . . . . ?
C1 C14 C15 C16 5.0(4) . . . . ?
C2 C1 C14 C13 -163.7(2) . . . . ?
C2 C1 C14 C15 16.6(3) . . . . ?
C2 C3 C4 C5 -175.4(2) . . . . ?
C2 C3 C16 C7 171.2(2) . . . . ?
C2 C3 C16 C15 -10.8(4) . . . . ?
C3 C2 C17 Br1 174.35(19) . . . . ?
C3 C2 C17 Br2 0.0(4) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
C4 C3 C16 C7 -9.4(4) . . . . ?
C4 C3 C16 C15 168.6(2) . . . . ?
C4 C5 C6 C7 -5.3(4) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C5 C6 C7 C16 1.1(4) . . . . ?
C6 C7 C8 C9 174.8(2) . . . . ?
C6 C7 C16 C3 6.2(4) . . . . ?
C6 C7 C16 C15 -171.8(2) . . . . ?
C7 C8 C9 C10 -1.9(4) . . . . ?
C8 C7 C16 C3 -175.0(2) . . . . ?
C8 C7 C16 C15 7.0(4) . . . . ?
C8 C9 C10 C11 -173.6(3) . . . . ?
C8 C9 C10 C15 4.4(4) . . . . ?
C9 C10 C11 C12 175.4(3) . . . . ?
C9 C10 C15 C14 -175.2(2) . . . . ?
C9 C10 C15 C16 -1.2(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C10 C15 C16 C3 177.6(2) . . . . ?
C10 C15 C16 C7 -4.4(4) . . . . ?
C11 C10 C15 C14 2.9(4) . . . . ?
C11 C10 C15 C16 176.9(2) . . . . ?
C11 C12 C13 C14 2.0(4) . . . . ?
C12 C13 C14 C1 178.6(2) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C13 C14 C15 C10 -0.8(4) . . . . ?
C13 C14 C15 C16 -174.7(2) . . . . ?
C14 C1 C2 C3 -34.7(3) . . . . ?
C14 C1 C2 C17 136.5(3) . . . . ?
C14 C15 C16 C3 -8.5(4) . . . . ?
C14 C15 C16 C7 169.5(2) . . . . ?
C15 C10 C11 C12 -2.7(4) . . . . ?
C16 C3 C4 C5 5.3(4) . . . . ?
C16 C7 C8 C9 -4.0(4) . . . . ?
C17 C2 C3 C4 42.3(4) . . . . ?
C17 C2 C3 C16 -138.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349960
