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#$Date: 2022-11-10 12:46:43 +0200 (Thu, 10 Nov 2022) $
#$Revision: 279209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106069.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_8106069
loop_
_publ_author_name
'Huang, Qiu-Ying'
'Wang, Hong-Ying'
'Ren, Su-Juan'
'Meng, Xiang-Ru'
_publ_section_title
;
 Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one,
 C24H15NO
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              123
_journal_page_last               124
_journal_paper_doi               10.1515/ncrs-2017-0213
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C24 H15 N O'
_chemical_formula_sum            'C24 H15 N O'
_chemical_formula_weight         333.37
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 97.3410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3161(3)
_cell_length_b                   5.53330(10)
_cell_length_c                   29.2019(7)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.40
_cell_volume                     1653.24(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18178
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.398
_diffrn_reflns_theta_min         3.052
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.6705
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0895P)²+0.1991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2697
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0213_suppl.cif
_cod_data_source_block           exp_I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106069
_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.
;
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
C1 C 1.13266(18) 0.4802(3) 0.69654(5) 0.0734(5) Uani 1 1 d . . . . .
H1A H 1.1843 0.6183 0.7000 0.088 Uiso 1 1 calc R U . . .
C2 C 1.05016(17) 0.4520(3) 0.65563(5) 0.0662(4) Uani 1 1 d . . . . .
H2A H 1.0471 0.5692 0.6327 0.079 Uiso 1 1 calc R U . . .
C3 C 0.97281(11) 0.2493(2) 0.64914(4) 0.0432(3) Uani 1 1 d . . . . .
C4 C 0.98248(14) 0.0860(3) 0.68488(5) 0.0595(4) Uani 1 1 d . . . . .
H4A H 0.9320 -0.0538 0.6824 0.071 Uiso 1 1 calc R U . . .
C5 C 1.06724(16) 0.1301(3) 0.72436(5) 0.0684(4) Uani 1 1 d . . . . .
H5A H 1.0719 0.0166 0.7480 0.082 Uiso 1 1 calc R U . . .
C6 C 0.88559(12) 0.1946(2) 0.60518(4) 0.0469(3) Uani 1 1 d . . . . .
C7 C 0.85779(12) 0.3846(2) 0.57063(4) 0.0488(3) Uani 1 1 d . . . . .
H7A H 0.8927 0.5378 0.5769 0.059 Uiso 1 1 calc R U . . .
C8 C 0.78414(11) 0.3453(2) 0.53054(4) 0.0456(3) Uani 1 1 d . . . . .
H8A H 0.7435 0.1955 0.5266 0.055 Uiso 1 1 calc R U . . .
C9 C 0.76119(11) 0.5157(2) 0.49218(4) 0.0427(3) Uani 1 1 d . . . . .
C10 C 0.84922(12) 0.7051(2) 0.48882(4) 0.0514(3) Uani 1 1 d . . . . .
H10A H 0.9188 0.7246 0.5121 0.062 Uiso 1 1 calc R U . . .
C11 C 0.83639(13) 0.8630(2) 0.45240(5) 0.0554(3) Uani 1 1 d . . . . .
H11A H 0.8967 0.9874 0.4516 0.066 Uiso 1 1 calc R U . . .
C12 C 0.73426(12) 0.8399(2) 0.41647(4) 0.0484(3) Uani 1 1 d . . . . .
C13 C 0.72046(15) 0.9974(3) 0.37723(5) 0.0630(4) Uani 1 1 d . . . . .
H13A H 0.7810 1.1207 0.3756 0.076 Uiso 1 1 calc R U . . .
C14 C 0.62250(16) 0.9714(3) 0.34280(5) 0.0668(4) Uani 1 1 d . . . . .
H14A H 0.6167 1.0762 0.3177 0.080 Uiso 1 1 calc R U . . .
C15 C 0.52691(13) 0.7862(3) 0.34387(4) 0.0570(4) Uani 1 1 d . . . . .
C16 C 0.42289(16) 0.7567(4) 0.30861(5) 0.0712(4) Uani 1 1 d . . . . .
H16A H 0.4145 0.8614 0.2835 0.085 Uiso 1 1 calc R U . . .
C17 C 0.33301(16) 0.5749(4) 0.31061(5) 0.0763(5) Uani 1 1 d . . . . .
H17A H 0.2650 0.5575 0.2867 0.092 Uiso 1 1 calc R U . . .
C18 C 0.34197(14) 0.4180(3) 0.34758(5) 0.0669(4) Uani 1 1 d . . . . .
H18A H 0.2801 0.2963 0.3483 0.080 Uiso 1 1 calc R U . . .
C19 C 0.44338(12) 0.4404(3) 0.38405(4) 0.0516(3) Uani 1 1 d . . . . .
C20 C 0.45603(12) 0.2846(3) 0.42343(4) 0.0550(3) Uani 1 1 d . . . . .
H20A H 0.3938 0.1647 0.4254 0.066 Uiso 1 1 calc R U . . .
C21 C 0.55567(12) 0.3066(2) 0.45787(4) 0.0493(3) Uani 1 1 d . . . . .
H21A H 0.5606 0.2014 0.4829 0.059 Uiso 1 1 calc R U . . .
C22 C 0.65441(10) 0.4888(2) 0.45682(4) 0.0405(3) Uani 1 1 d . . . . .
C23 C 0.64225(11) 0.6509(2) 0.41870(4) 0.0418(3) Uani 1 1 d . . . . .
C24 C 0.53697(11) 0.6257(2) 0.38224(4) 0.0459(3) Uani 1 1 d . . . . .
N1 N 1.14263(13) 0.3243(2) 0.73074(4) 0.0640(3) Uani 1 1 d . . . . .
O1 O 0.84364(12) -0.01056(18) 0.59898(4) 0.0743(4) 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'
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
N1 C1 C2 124.20(13) . .
N1 C1 H1A 117.9 . .
C2 C1 H1A 117.9 . .
C3 C2 C1 119.51(12) . .
C3 C2 H2A 120.2 . .
C1 C2 H2A 120.2 . .
C2 C3 C4 116.55(11) . .
C2 C3 C6 123.78(11) . .
C4 C3 C6 119.61(11) . .
C5 C4 C3 119.73(13) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
N1 C5 C4 124.04(13) . .
N1 C5 H5A 118.0 . .
C4 C5 H5A 118.0 . .
O1 C6 C7 122.19(11) . .
O1 C6 C3 118.49(11) . .
C7 C6 C3 119.28(10) . .
C8 C7 C6 122.05(11) . .
C8 C7 H7A 119.0 . .
C6 C7 H7A 119.0 . .
C7 C8 C9 126.05(11) . .
C7 C8 H8A 117.0 . .
C9 C8 H8A 117.0 . .
C10 C9 C22 118.58(11) . .
C10 C9 C8 119.66(10) . .
C22 C9 C8 121.71(10) . .
C11 C10 C9 122.23(11) . .
C11 C10 H10A 118.9 . .
C9 C10 H10A 118.9 . .
C10 C11 C12 120.98(12) . .
C10 C11 H11A 119.5 . .
C12 C11 H11A 119.5 . .
C11 C12 C23 118.57(11) . .
C11 C12 C13 122.32(12) . .
C23 C12 C13 119.10(12) . .
C14 C13 C12 121.58(14) . .
C14 C13 H13A 119.2 . .
C12 C13 H13A 119.2 . .
C13 C14 C15 121.24(12) . .
C13 C14 H14A 119.4 . .
C15 C14 H14A 119.4 . .
C16 C15 C24 118.60(14) . .
C16 C15 C14 122.40(13) . .
C24 C15 C14 119.01(12) . .
C17 C16 C15 120.84(14) . .
C17 C16 H16A 119.6 . .
C15 C16 H16A 119.6 . .
C16 C17 C18 121.05(13) . .
C16 C17 H17A 119.5 . .
C18 C17 H17A 119.5 . .
C17 C18 C19 120.58(16) . .
C17 C18 H18A 119.7 . .
C19 C18 H18A 119.7 . .
C18 C19 C24 118.89(13) . .
C18 C19 C20 122.76(13) . .
C24 C19 C20 118.35(11) . .
C21 C20 C19 121.86(12) . .
C21 C20 H20A 119.1 . .
C19 C20 H20A 119.1 . .
C20 C21 C22 121.50(11) . .
C20 C21 H21A 119.2 . .
C22 C21 H21A 119.2 . .
C9 C22 C23 119.09(10) . .
C9 C22 C21 123.04(10) . .
C23 C22 C21 117.86(10) . .
C12 C23 C22 120.52(11) . .
C12 C23 C24 119.16(11) . .
C22 C23 C24 120.32(11) . .
C19 C24 C15 120.04(11) . .
C19 C24 C23 120.06(11) . .
C15 C24 C23 119.89(12) . .
C1 N1 C5 115.97(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3136(19) .
C1 C2 1.3843(18) .
C1 H1A 0.9300 .
C2 C3 1.3755(18) .
C2 H2A 0.9300 .
C3 C4 1.3745(18) .
C3 C6 1.5015(15) .
C4 C5 1.3768(19) .
C4 H4A 0.9300 .
C5 N1 1.326(2) .
C5 H5A 0.9300 .
C6 O1 1.2200(15) .
C6 C7 1.4599(17) .
C7 C8 1.3295(16) .
C7 H7A 0.9300 .
C8 C9 1.4599(17) .
C8 H8A 0.9300 .
C9 C10 1.3987(17) .
C9 C22 1.4183(15) .
C10 C11 1.3694(19) .
C10 H10A 0.9300 .
C11 C12 1.3944(19) .
C11 H11A 0.9300 .
C12 C23 1.4197(17) .
C12 C13 1.4322(18) .
C13 C14 1.339(2) .
C13 H13A 0.9300 .
C14 C15 1.426(2) .
C14 H14A 0.9300 .
C15 C16 1.399(2) .
C15 C24 1.4232(18) .
C16 C17 1.374(3) .
C16 H16A 0.9300 .
C17 C18 1.379(2) .
C17 H17A 0.9300 .
C18 C19 1.3999(17) .
C18 H18A 0.9300 .
C19 C24 1.4137(19) .
C19 C20 1.4298(19) .
C20 C21 1.3485(17) .
C20 H20A 0.9300 .
C21 C22 1.4362(17) .
C21 H21A 0.9300 .
C22 C23 1.4225(16) .
C23 C24 1.4274(16) .
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
C7 H7A O1 0.93 2.65 3.4554(16) 145.8 1_565
C18 H18A O1 0.93 2.65 3.457(2) 146.0 3_656
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
N1 C1 C2 C3 -0.3(3) . . . .
C1 C2 C3 C4 0.6(2) . . . .
C1 C2 C3 C6 -176.52(15) . . . .
C2 C3 C4 C5 -0.4(2) . . . .
C6 C3 C4 C5 176.80(13) . . . .
C3 C4 C5 N1 0.0(3) . . . .
C2 C3 C6 O1 164.05(15) . . . .
C4 C3 C6 O1 -12.9(2) . . . .
C2 C3 C6 C7 -13.6(2) . . . .
C4 C3 C6 C7 169.37(12) . . . .
O1 C6 C7 C8 0.6(2) . . . .
C3 C6 C7 C8 178.19(11) . . . .
C6 C7 C8 C9 -173.69(11) . . . .
C7 C8 C9 C10 21.24(19) . . . .
C7 C8 C9 C22 -161.51(12) . . . .
C22 C9 C10 C11 -0.72(19) . . . .
C8 C9 C10 C11 176.62(12) . . . .
C9 C10 C11 C12 -0.5(2) . . . .
C10 C11 C12 C23 0.9(2) . . . .
C10 C11 C12 C13 -178.03(12) . . . .
C11 C12 C13 C14 179.37(13) . . . .
C23 C12 C13 C14 0.4(2) . . . .
C12 C13 C14 C15 0.4(2) . . . .
C13 C14 C15 C16 179.33(14) . . . .
C13 C14 C15 C24 -0.4(2) . . . .
C24 C15 C16 C17 -0.7(2) . . . .
C14 C15 C16 C17 179.53(15) . . . .
C15 C16 C17 C18 0.6(3) . . . .
C16 C17 C18 C19 0.0(2) . . . .
C17 C18 C19 C24 -0.4(2) . . . .
C17 C18 C19 C20 179.12(14) . . . .
C18 C19 C20 C21 178.89(13) . . . .
C24 C19 C20 C21 -1.6(2) . . . .
C19 C20 C21 C22 0.2(2) . . . .
C10 C9 C22 C23 1.56(16) . . . .
C8 C9 C22 C23 -175.72(10) . . . .
C10 C9 C22 C21 -177.44(11) . . . .
C8 C9 C22 C21 5.28(17) . . . .
C20 C21 C22 C9 -179.37(12) . . . .
C20 C21 C22 C23 1.62(18) . . . .
C11 C12 C23 C22 -0.04(17) . . . .
C13 C12 C23 C22 178.94(11) . . . .
C11 C12 C23 C24 179.79(11) . . . .
C13 C12 C23 C24 -1.23(17) . . . .
C9 C22 C23 C12 -1.20(16) . . . .
C21 C22 C23 C12 177.85(10) . . . .
C9 C22 C23 C24 178.98(9) . . . .
C21 C22 C23 C24 -1.98(16) . . . .
C18 C19 C24 C15 0.26(18) . . . .
C20 C19 C24 C15 -179.28(11) . . . .
C18 C19 C24 C23 -179.28(11) . . . .
C20 C19 C24 C23 1.18(18) . . . .
C16 C15 C24 C19 0.30(19) . . . .
C14 C15 C24 C19 -179.96(12) . . . .
C16 C15 C24 C23 179.83(11) . . . .
C14 C15 C24 C23 -0.43(18) . . . .
C12 C23 C24 C19 -179.24(10) . . . .
C22 C23 C24 C19 0.59(17) . . . .
C12 C23 C24 C15 1.23(17) . . . .
C22 C23 C24 C15 -178.94(10) . . . .
C2 C1 N1 C5 -0.1(3) . . . .
C4 C5 N1 C1 0.2(3) . . . .
