#------------------------------------------------------------------------------
#$Date: 2022-02-09 12:40:21 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104562.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_8104562
loop_
_publ_author_name
'Ran, Zhang'
'Hui, Wang'
'Bao-Xi, Miao'
'Li-Fang, Zhang'
_publ_section_title
;
 Synthesis and crystal structure of 4-acetylpyrene, C18H12O
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1187
_journal_page_last               1190
_journal_paper_doi               10.1515/ncrs-2021-0272
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C18 H12 O'
_chemical_formula_sum            'C18 H12 O'
_chemical_formula_weight         244.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.31(3)
_cell_angle_beta                 102.38(3)
_cell_angle_gamma                104.81(3)
_cell_formula_units_Z            4
_cell_length_a                   10.132(2)
_cell_length_b                   10.654(2)
_cell_length_c                   11.730(2)
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.97
_cell_volume                     1193.2(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT-Plus
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX II CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9761
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0529
_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)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3742
_reflns_number_total             5251
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0272_suppl.cif
_cod_data_source_block           3
_cod_database_code               8104562
_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, -y, -z'
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 0.59444(9) 0.16236(9) 0.05203(8) 0.0343(2) Uani 1 1 d . . . . .
C1 C 0.66692(12) 0.19276(11) -0.01931(10) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.60684(13) 0.23671(14) -0.13607(11) 0.0337(3) Uani 1 1 d . . . . .
H2A H 0.5078 0.2239 -0.1451 0.051 Uiso 1 1 calc R U . . .
H2B H 0.6239 0.1870 -0.1972 0.051 Uiso 1 1 calc R U . . .
H2C H 0.6504 0.3273 -0.1405 0.051 Uiso 1 1 calc R U . . .
C3 C 0.81763(11) 0.19112(11) 0.00927(9) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.91177(11) 0.28638(11) -0.03050(9) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.8785 0.3441 -0.0808 0.024 Uiso 1 1 calc R U . . .
C5 C 1.05921(11) 0.30121(11) 0.00188(9) 0.0185(2) Uani 1 1 d . . . . .
C6 C 1.15481(12) 0.40113(11) -0.03725(10) 0.0233(3) Uani 1 1 d . . . . .
H6 H 1.1225 0.4617 -0.0845 0.028 Uiso 1 1 calc R U . . .
C7 C 1.29674(12) 0.41111(12) -0.00663(11) 0.0267(3) Uani 1 1 d . . . . .
H7 H 1.3591 0.4781 -0.0335 0.032 Uiso 1 1 calc R U . . .
C8 C 1.34681(12) 0.32185(12) 0.06384(10) 0.0246(3) Uani 1 1 d . . . . .
H8 H 1.4426 0.3294 0.0833 0.029 Uiso 1 1 calc R U . . .
C9 C 1.25569(11) 0.22064(11) 0.10624(9) 0.0197(3) Uani 1 1 d . . . . .
C10 C 1.30359(12) 0.12492(12) 0.17701(10) 0.0228(3) Uani 1 1 d . . . . .
H10 H 1.3990 0.1309 0.1979 0.027 Uiso 1 1 calc R U . . .
C11 C 1.21295(12) 0.02645(12) 0.21375(10) 0.0226(3) Uani 1 1 d . . . . .
H11 H 1.2473 -0.0344 0.2592 0.027 Uiso 1 1 calc R U . . .
C12 C 1.06446(12) 0.01286(11) 0.18461(9) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.96960(12) -0.08923(11) 0.22113(10) 0.0231(3) Uani 1 1 d . . . . .
H13 H 1.0024 -0.1508 0.2667 0.028 Uiso 1 1 calc R U . . .
C14 C 0.82800(12) -0.10031(11) 0.19074(10) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.7664 -0.1692 0.2162 0.030 Uiso 1 1 calc R U . . .
C15 C 0.77563(12) -0.01004(11) 0.12252(10) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.6795 -0.0198 0.1023 0.027 Uiso 1 1 calc R U . . .
C16 C 0.86579(11) 0.09525(10) 0.08394(9) 0.0178(2) Uani 1 1 d . . . . .
C17 C 1.01284(11) 0.10661(10) 0.11494(9) 0.0162(2) Uani 1 1 d . . . . .
C18 C 1.10954(11) 0.21003(10) 0.07529(9) 0.0171(2) Uani 1 1 d . . . . .
O2 O -0.37033(9) 0.14448(9) 0.55836(8) 0.0350(2) Uani 1 1 d . . . . .
C19 C -0.29545(12) 0.14518(11) 0.48936(10) 0.0226(3) Uani 1 1 d . . . . .
C20 C -0.35154(12) 0.06341(12) 0.37635(10) 0.0285(3) Uani 1 1 d . . . . .
H20A H -0.3068 -0.0061 0.3781 0.043 Uiso 1 1 calc R U . . .
H20B H -0.3329 0.1162 0.3126 0.043 Uiso 1 1 calc R U . . .
H20C H -0.4508 0.0278 0.3660 0.043 Uiso 1 1 calc R U . . .
C21 C -0.14643(11) 0.22500(11) 0.51765(9) 0.0187(2) Uani 1 1 d . . . . .
C22 C -0.04921(12) 0.17927(11) 0.47795(9) 0.0201(3) Uani 1 1 d . . . . .
H22 H -0.0796 0.1039 0.4287 0.024 Uiso 1 1 calc R U . . .
C23 C 0.09716(12) 0.24236(11) 0.50888(10) 0.0200(3) Uani 1 1 d . . . . .
C24 C 0.19561(12) 0.19259(12) 0.47034(10) 0.0266(3) Uani 1 1 d . . . . .
H24 H 0.1662 0.1157 0.4233 0.032 Uiso 1 1 calc R U . . .
C25 C 0.33696(13) 0.25644(14) 0.50134(12) 0.0334(3) Uani 1 1 d . . . . .
H25 H 0.4017 0.2222 0.4752 0.040 Uiso 1 1 calc R U . . .
C26 C 0.38188(13) 0.37103(14) 0.57113(11) 0.0326(3) Uani 1 1 d . . . . .
H26 H 0.4770 0.4126 0.5917 0.039 Uiso 1 1 calc R U . . .
C27 C 0.28734(12) 0.42572(12) 0.61139(10) 0.0254(3) Uani 1 1 d . . . . .
C28 C 0.32979(14) 0.54629(13) 0.68121(11) 0.0314(3) Uani 1 1 d . . . . .
H28 H 0.4243 0.5901 0.7022 0.038 Uiso 1 1 calc R U . . .
C29 C 0.23609(13) 0.59723(12) 0.71692(10) 0.0292(3) Uani 1 1 d . . . . .
H29 H 0.2672 0.6758 0.7616 0.035 Uiso 1 1 calc R U . . .
C30 C 0.08917(13) 0.53329(11) 0.68770(9) 0.0236(3) Uani 1 1 d . . . . .
C31 C -0.00893(14) 0.58545(12) 0.72430(10) 0.0286(3) Uani 1 1 d . . . . .
H31 H 0.0205 0.6649 0.7676 0.034 Uiso 1 1 calc R U . . .
C32 C -0.14908(14) 0.52042(12) 0.69705(10) 0.0292(3) Uani 1 1 d . . . . .
H32 H -0.2130 0.5561 0.7230 0.035 Uiso 1 1 calc R U . . .
C33 C -0.19622(13) 0.40255(12) 0.63146(10) 0.0244(3) Uani 1 1 d . . . . .
H33 H -0.2913 0.3606 0.6139 0.029 Uiso 1 1 calc R U . . .
C34 C -0.10292(12) 0.34554(11) 0.59116(9) 0.0193(3) Uani 1 1 d . . . . .
C35 C 0.04227(12) 0.41232(11) 0.61981(9) 0.0188(3) Uani 1 1 d . . . . .
C36 C 0.14259(11) 0.35991(11) 0.58090(9) 0.0195(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
O1 C1 C3 120.71(11) . .
O1 C1 C2 120.24(11) . .
C3 C1 C2 119.02(11) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 C3 C16 120.01(10) . .
C4 C3 C1 118.48(10) . .
C16 C3 C1 121.40(11) . .
C3 C4 C5 122.74(11) . .
C3 C4 H4 118.6 . .
C5 C4 H4 118.6 . .
C6 C5 C18 119.25(10) . .
C6 C5 C4 122.18(10) . .
C18 C5 C4 118.57(11) . .
C7 C6 C5 120.83(11) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 120.39(12) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C7 C8 C9 121.07(11) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C8 C9 C18 118.80(11) . .
C8 C9 C10 122.52(11) . .
C18 C9 C10 118.65(11) . .
C11 C10 C9 121.16(11) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C10 C11 C12 121.76(11) . .
C10 C11 H11 119.1 . .
C12 C11 H11 119.1 . .
C13 C12 C17 118.98(10) . .
C13 C12 C11 122.28(10) . .
C17 C12 C11 118.73(11) . .
C14 C13 C12 120.89(11) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C15 120.96(11) . .
C13 C14 H14 119.5 . .
C15 C14 H14 119.5 . .
C14 C15 C16 120.81(11) . .
C14 C15 H15 119.6 . .
C16 C15 H15 119.6 . .
C15 C16 C17 118.32(10) . .
C15 C16 C3 123.61(10) . .
C17 C16 C3 118.01(11) . .
C12 C17 C18 119.18(10) . .
C12 C17 C16 120.03(11) . .
C18 C17 C16 120.79(10) . .
C5 C18 C9 119.65(11) . .
C5 C18 C17 119.82(10) . .
C9 C18 C17 120.51(10) . .
O2 C19 C21 120.50(11) . .
O2 C19 C20 120.09(11) . .
C21 C19 C20 119.39(11) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C22 C21 C34 119.98(10) . .
C22 C21 C19 118.54(10) . .
C34 C21 C19 121.39(10) . .
C21 C22 C23 122.71(11) . .
C21 C22 H22 118.6 . .
C23 C22 H22 118.6 . .
C24 C23 C36 119.46(11) . .
C24 C23 C22 122.09(11) . .
C36 C23 C22 118.45(11) . .
C25 C24 C23 120.75(12) . .
C25 C24 H24 119.6 . .
C23 C24 H24 119.6 . .
C26 C25 C24 120.10(12) . .
C26 C25 H25 119.9 . .
C24 C25 H25 119.9 . .
C25 C26 C27 121.45(12) . .
C25 C26 H26 119.3 . .
C27 C26 H26 119.3 . .
C26 C27 C36 118.64(12) . .
C26 C27 C28 122.96(11) . .
C36 C27 C28 118.40(12) . .
C29 C28 C27 121.49(11) . .
C29 C28 H28 119.3 . .
C27 C28 H28 119.3 . .
C28 C29 C30 121.54(11) . .
C28 C29 H29 119.2 . .
C30 C29 H29 119.2 . .
C31 C30 C35 119.07(11) . .
C31 C30 C29 121.97(11) . .
C35 C30 C29 118.96(11) . .
C32 C31 C30 120.67(11) . .
C32 C31 H31 119.7 . .
C30 C31 H31 119.7 . .
C31 C32 C33 120.92(12) . .
C31 C32 H32 119.5 . .
C33 C32 H32 119.5 . .
C32 C33 C34 121.15(12) . .
C32 C33 H33 119.4 . .
C34 C33 H33 119.4 . .
C33 C34 C35 118.02(11) . .
C33 C34 C21 123.79(11) . .
C35 C34 C21 118.13(10) . .
C34 C35 C30 120.16(11) . .
C34 C35 C36 120.81(10) . .
C30 C35 C36 119.03(10) . .
C27 C36 C23 119.59(11) . .
C27 C36 C35 120.56(11) . .
C23 C36 C35 119.83(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2203(14) .
C1 C3 1.4963(16) .
C1 C2 1.5036(17) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 C4 1.3632(16) .
C3 C16 1.4593(15) .
C4 C5 1.4270(16) .
C4 H4 0.9300 .
C5 C6 1.3968(16) .
C5 C18 1.4210(15) .
C6 C7 1.3814(17) .
C6 H6 0.9300 .
C7 C8 1.3858(17) .
C7 H7 0.9300 .
C8 C9 1.3986(17) .
C8 H8 0.9300 .
C9 C18 1.4215(16) .
C9 C10 1.4333(16) .
C10 C11 1.3460(17) .
C10 H10 0.9300 .
C11 C12 1.4384(17) .
C11 H11 0.9300 .
C12 C13 1.3919(16) .
C12 C17 1.4254(15) .
C13 C14 1.3759(17) .
C13 H13 0.9300 .
C14 C15 1.3907(16) .
C14 H14 0.9300 .
C15 C16 1.3987(16) .
C15 H15 0.9300 .
C16 C17 1.4289(16) .
C17 C18 1.4281(16) .
O2 C19 1.2211(14) .
C19 C21 1.4963(16) .
C19 C20 1.5002(17) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 C22 1.3653(15) .
C21 C34 1.4570(16) .
C22 C23 1.4282(16) .
C22 H22 0.9300 .
C23 C24 1.3936(16) .
C23 C36 1.4216(16) .
C24 C25 1.3864(18) .
C24 H24 0.9300 .
C25 C26 1.3831(19) .
C25 H25 0.9300 .
C26 C27 1.3987(18) .
C26 H26 0.9300 .
C27 C36 1.4202(17) .
C27 C28 1.4356(18) .
C28 C29 1.3427(18) .
C28 H28 0.9300 .
C29 C30 1.4345(18) .
C29 H29 0.9300 .
C30 C31 1.3943(17) .
C30 C35 1.4263(16) .
C31 C32 1.3779(18) .
C31 H31 0.9300 .
C32 C33 1.3865(17) .
C32 H32 0.9300 .
C33 C34 1.4029(16) .
C33 H33 0.9300 .
C34 C35 1.4260(17) .
C35 C36 1.4283(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
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
C20 H20C O2 0.96 2.54 3.3446(19) 141.5 2_456
