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#$Date: 2022-10-29 11:06:14 +0300 (Sat, 29 Oct 2022) $
#$Revision: 278862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/09/7130929.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_7130929
loop_
_publ_author_name
'Lefarth, Jens'
'Haseloer, Alexander'
'Kletsch, Lukas'
'Klein, Axel'
'Neudörfl, Jörg-Martin'
'Griesbeck, Axel'
_publ_section_title
;
 From energy transfer to electron transfer photocatalysis
 (PenT→ PET): oxidative cyclobutane cleavage alters the product
 composition
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04693H
_journal_year                    2022
_chemical_formula_moiety         'C19 H18 O2'
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_weight         278.33
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-07-27 deposited with the CCDC.	2022-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.1592(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1123(4)
_cell_length_b                   5.8889(2)
_cell_length_c                   19.6384(5)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.06
_cell_measurement_theta_min      3.48
_cell_volume                     1470.35(8)
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_collection       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17310
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'micro focus'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       platelet
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0359
_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)+(0.0295P)²+0.7578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             2898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04693h2.cif
_cod_data_source_block           jle296c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7130929
_shelx_shelxl_version_number     2014/7
_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   0.786
_shelx_estimated_absorpt_t_max   0.987
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
O1 O 0.80364(7) 0.69235(16) 0.88513(4) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.91599(9) 0.7057(2) 0.89420(6) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.9496 0.7830 0.9388 0.024 Uiso 1 1 calc R U . . .
H1AB H 0.9334 0.7898 0.8549 0.024 Uiso 1 1 calc R U . . .
C2 C 0.95247(9) 0.4599(2) 0.89527(6) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.9595 0.3903 0.9421 0.023 Uiso 1 1 calc R U . . .
H2AB H 1.0204 0.4479 0.8820 0.023 Uiso 1 1 calc R U . . .
O2 O 0.87042(7) 0.03270(15) 0.72862(5) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.86353(9) 0.3506(2) 0.84026(6) 0.0157(2) Uani 1 1 d . . . . .
H3 H 0.8522 0.1855 0.8478 0.019 Uiso 1 1 calc R U . . .
C4 C 0.85698(9) 0.4183(2) 0.76321(6) 0.0135(2) Uani 1 1 d . . . . .
H4 H 0.9154 0.5251 0.7611 0.016 Uiso 1 1 calc R U . . .
C6 C 0.76721(9) 0.5053(2) 0.83975(6) 0.0168(2) Uani 1 1 d . . . . .
H6 H 0.7067 0.4228 0.8510 0.020 Uiso 1 1 calc R U . . .
C5 C 0.75205(9) 0.5558(2) 0.76000(6) 0.0143(2) Uani 1 1 d . . . . .
H5 H 0.7614 0.7210 0.7515 0.017 Uiso 1 1 calc R U . . .
C8 C 0.61227(9) 0.2522(2) 0.72291(7) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.6481 0.1606 0.7611 0.022 Uiso 1 1 calc R U . . .
C7 C 0.65305(9) 0.4650(2) 0.71202(6) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.51984(10) 0.1735(2) 0.67839(8) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.4926 0.0294 0.6866 0.030 Uiso 1 1 calc R U . . .
C10 C 0.46725(10) 0.3043(3) 0.62212(8) 0.0300(3) Uani 1 1 d . . . . .
H10 H 0.4040 0.2504 0.5918 0.036 Uiso 1 1 calc R U . . .
C11 C 0.50750(10) 0.5147(3) 0.61024(8) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.4722 0.6045 0.5714 0.035 Uiso 1 1 calc R U . . .
C12 C 0.59936(9) 0.5938(2) 0.65515(7) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.6261 0.7384 0.6469 0.024 Uiso 1 1 calc R U . . .
C13 C 0.85153(8) 0.2302(2) 0.71065(6) 0.0144(2) Uani 1 1 d . . . . .
C14 C 0.82182(9) 0.2923(2) 0.63456(6) 0.0142(2) Uani 1 1 d . . . . .
C15 C 0.77242(9) 0.1306(2) 0.58602(6) 0.0184(3) Uani 1 1 d . . . . .
H15 H 0.7573 -0.0152 0.6017 0.022 Uiso 1 1 calc R U . . .
C16 C 0.74507(10) 0.1807(2) 0.51478(7) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.7104 0.0702 0.4819 0.027 Uiso 1 1 calc R U . . .
C17 C 0.76855(10) 0.3934(2) 0.49163(6) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.7511 0.4272 0.4428 0.024 Uiso 1 1 calc R U . . .
C18 C 0.81729(10) 0.5553(2) 0.53964(6) 0.0198(3) Uani 1 1 d . . . . .
H18 H 0.8333 0.7002 0.5237 0.024 Uiso 1 1 calc R U . . .
C19 C 0.84303(9) 0.5071(2) 0.61122(6) 0.0176(2) Uani 1 1 d . . . . .
H19 H 0.8750 0.6201 0.6441 0.021 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'
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
C6 O1 C1 107.20(9) . . ?
O1 C1 C2 104.94(10) . . ?
O1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
O1 C1 H1AB 110.8 . . ?
C2 C1 H1AB 110.8 . . ?
H1A C1 H1AB 108.8 . . ?
C1 C2 C3 102.02(9) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2AB 111.4 . . ?
C3 C2 H2AB 111.4 . . ?
H2A C2 H2AB 109.2 . . ?
C2 C3 C4 115.73(10) . . ?
C2 C3 C6 103.67(10) . . ?
C4 C3 C6 89.55(8) . . ?
C2 C3 H3 114.9 . . ?
C4 C3 H3 114.9 . . ?
C6 C3 H3 114.9 . . ?
C13 C4 C3 117.62(10) . . ?
C13 C4 C5 117.02(9) . . ?
C3 C4 C5 90.59(8) . . ?
C13 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
O1 C6 C3 107.55(9) . . ?
O1 C6 C5 114.96(10) . . ?
C3 C6 C5 91.26(8) . . ?
O1 C6 H6 113.6 . . ?
C3 C6 H6 113.6 . . ?
C5 C6 H6 113.6 . . ?
C7 C5 C6 116.12(10) . . ?
C7 C5 C4 116.83(9) . . ?
C6 C5 C4 88.08(8) . . ?
C7 C5 H5 111.3 . . ?
C6 C5 H5 111.3 . . ?
C4 C5 H5 111.3 . . ?
C9 C8 C7 120.63(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C12 C7 C8 118.28(11) . . ?
C12 C7 C5 119.96(11) . . ?
C8 C7 C5 121.76(11) . . ?
C10 C9 C8 120.29(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.67(12) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.92(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 121.19(12) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C13 C14 120.41(11) . . ?
O2 C13 C4 122.02(10) . . ?
C14 C13 C4 117.57(10) . . ?
C15 C14 C19 119.48(11) . . ?
C15 C14 C13 118.78(11) . . ?
C19 C14 C13 121.73(11) . . ?
C16 C15 C14 120.51(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.80(12) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.99(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.35(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.84(11) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
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 C6 1.4240(15) . ?
O1 C1 1.4421(15) . ?
C1 C2 1.5230(18) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.5249(16) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
O2 C13 1.2228(15) . ?
C3 C4 1.5468(15) . ?
C3 C6 1.5553(16) . ?
C3 H3 1.0000 . ?
C4 C13 1.5036(16) . ?
C4 C5 1.5846(15) . ?
C4 H4 1.0000 . ?
C6 C5 1.5584(16) . ?
C6 H6 1.0000 . ?
C5 C7 1.5034(15) . ?
C5 H5 1.0000 . ?
C8 C9 1.3890(18) . ?
C8 C7 1.3995(17) . ?
C8 H8 0.9500 . ?
C7 C12 1.3904(17) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3877(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4947(16) . ?
C14 C15 1.3903(17) . ?
C14 C19 1.3963(17) . ?
C15 C16 1.3883(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3922(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3829(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3923(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
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
C6 O1 C1 C2 -36.01(12) . . . . ?
O1 C1 C2 C3 37.94(12) . . . . ?
C1 C2 C3 C4 70.72(12) . . . . ?
C1 C2 C3 C6 -25.50(12) . . . . ?
C2 C3 C4 C13 128.40(11) . . . . ?
C6 C3 C4 C13 -126.62(10) . . . . ?
C2 C3 C4 C5 -110.40(11) . . . . ?
C6 C3 C4 C5 -5.41(9) . . . . ?
C1 O1 C6 C3 18.97(12) . . . . ?
C1 O1 C6 C5 -80.98(12) . . . . ?
C2 C3 C6 O1 5.19(12) . . . . ?
C4 C3 C6 O1 -111.22(10) . . . . ?
C2 C3 C6 C5 121.91(9) . . . . ?
C4 C3 C6 C5 5.50(9) . . . . ?
O1 C6 C5 C7 -136.21(10) . . . . ?
C3 C6 C5 C7 113.73(10) . . . . ?
O1 C6 C5 C4 104.68(10) . . . . ?
C3 C6 C5 C4 -5.37(9) . . . . ?
C13 C4 C5 C7 8.65(15) . . . . ?
C3 C4 C5 C7 -113.06(11) . . . . ?
C13 C4 C5 C6 127.12(10) . . . . ?
C3 C4 C5 C6 5.40(9) . . . . ?
C9 C8 C7 C12 -0.76(18) . . . . ?
C9 C8 C7 C5 179.08(11) . . . . ?
C6 C5 C7 C12 141.24(11) . . . . ?
C4 C5 C7 C12 -116.86(12) . . . . ?
C6 C5 C7 C8 -38.59(15) . . . . ?
C4 C5 C7 C8 63.30(15) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 0.20(19) . . . . ?
C5 C7 C12 C11 -179.64(12) . . . . ?
C3 C4 C13 O2 -13.02(16) . . . . ?
C5 C4 C13 O2 -119.28(12) . . . . ?
C3 C4 C13 C14 166.95(9) . . . . ?
C5 C4 C13 C14 60.69(13) . . . . ?
O2 C13 C14 C15 27.61(16) . . . . ?
C4 C13 C14 C15 -152.36(11) . . . . ?
O2 C13 C14 C19 -151.94(11) . . . . ?
C4 C13 C14 C19 28.08(15) . . . . ?
C19 C14 C15 C16 0.57(18) . . . . ?
C13 C14 C15 C16 -179.00(11) . . . . ?
C14 C15 C16 C17 0.89(19) . . . . ?
C15 C16 C17 C18 -1.15(19) . . . . ?
C16 C17 C18 C19 -0.07(19) . . . . ?
C17 C18 C19 C14 1.53(19) . . . . ?
C15 C14 C19 C18 -1.77(17) . . . . ?
C13 C14 C19 C18 177.78(11) . . . . ?
