#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/19/7101967.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_7101967
loop_
_publ_author_name
'Zhang, Jing'
'Gembicky, Milan'
'Messerschmidt, Marc'
'Coppens, Philip'
_publ_section_title
;
 Hydrogen-bond quenching of photodecarbonylation in the solid state and
 recovery of reactivity by co-crystallization
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   23
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2399
_journal_page_last               2401
_journal_paper_doi               10.1039/b700073a
_journal_year                    2007
_chemical_formula_moiety         'C20 H24 O3, 0.5(C12 H18 O2)'
_chemical_formula_sum            'C26 H33 O4'
_chemical_formula_weight         409.52
_chemical_name_common            'MonoHOTMK, 4,4'-biscyclohexanone'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9470(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2893(2)
_cell_length_b                   7.9701(2)
_cell_length_c                   43.7044(11)
_cell_measurement_reflns_used    7288
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.261
_cell_measurement_theta_min      2.721
_cell_volume                     2187.84(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            29627
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   'empirical SADABS'
_exptl_absorpt_process_details
'Blessing, R. (1995) Acta Crystallogr., A51, 33-38'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.9835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                4936
_reflns_number_total             5390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b700073a.txt
_cod_data_source_block           MonoHO-biscyclohexanone
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7101967
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
O1 O -0.36875(13) 0.28880(11) 0.15275(2) 0.02428(19) Uani 1 1 d
O2 O 0.30237(13) -0.17530(11) 0.253407(18) 0.02243(18) Uani 1 1 d
O3 O 0.07201(15) 0.79132(12) 0.047377(19) 0.0262(2) Uani 1 1 d
H3A H 0.195(3) 0.838(3) 0.0477(4) 0.047(5) Uiso 1 1 d
O4 O 0.44697(14) -0.03878(11) 0.04771(2) 0.0282(2) Uani 1 1 d
C1 C -0.17569(17) 0.28736(13) 0.15272(2) 0.0154(2) Uani 1 1 d
C2 C -0.06163(16) 0.12286(13) 0.14398(2) 0.0148(2) Uani 1 1 d
C3 C -0.05193(16) 0.45155(13) 0.16032(2) 0.0149(2) Uani 1 1 d
C4 C 0.09702(18) 0.15499(14) 0.11890(2) 0.0183(2) Uani 1 1 d
H4C H 0.146(2) 0.0470(19) 0.1109(3) 0.022(3) Uiso 1 1 d
H4B H 0.222(2) 0.220(2) 0.1259(3) 0.024(4) Uiso 1 1 d
H4A H 0.025(2) 0.2157(18) 0.1015(3) 0.021(3) Uiso 1 1 d
C5 C -0.23018(19) -0.00273(15) 0.13140(3) 0.0206(2) Uani 1 1 d
H5C H -0.305(3) 0.041(2) 0.1125(4) 0.030(4) Uiso 1 1 d
H5B H -0.155(2) -0.107(2) 0.1260(4) 0.028(4) Uiso 1 1 d
H5A H -0.334(2) -0.0287(19) 0.1470(3) 0.024(4) Uiso 1 1 d
C6 C -0.19701(19) 0.56911(14) 0.17808(3) 0.0198(2) Uani 1 1 d
H6C H -0.237(2) 0.517(2) 0.1973(4) 0.028(4) Uiso 1 1 d
H6B H -0.333(2) 0.5950(19) 0.1657(3) 0.023(4) Uiso 1 1 d
H6A H -0.120(3) 0.675(2) 0.1823(4) 0.030(4) Uiso 1 1 d
C7 C 0.15154(18) 0.42291(14) 0.18067(3) 0.0183(2) Uani 1 1 d
H7C H 0.222(2) 0.533(2) 0.1857(3) 0.024(4) Uiso 1 1 d
H7B H 0.260(2) 0.352(2) 0.1711(3) 0.027(4) Uiso 1 1 d
H7A H 0.113(2) 0.371(2) 0.2003(4) 0.028(4) Uiso 1 1 d
C8 C 0.04446(16) 0.04496(12) 0.17299(2) 0.0146(2) Uani 1 1 d
C9 C 0.23708(17) -0.03992(13) 0.17263(2) 0.0171(2) Uani 1 1 d
H9A H 0.311(2) -0.0452(19) 0.1538(3) 0.023(4) Uiso 1 1 d
C10 C 0.32823(17) -0.11747(13) 0.19877(3) 0.0176(2) Uani 1 1 d
H10A H 0.462(3) -0.174(2) 0.1978(4) 0.028(4) Uiso 1 1 d
C11 C 0.22559(17) -0.10884(13) 0.22608(2) 0.0171(2) Uani 1 1 d
C12 C 0.03139(18) -0.02429(15) 0.22706(3) 0.0198(2) Uani 1 1 d
H12A H -0.051(2) -0.0227(17) 0.2501(3) 0.015(3) Uiso 1 1 d
C13 C -0.05775(17) 0.04971(14) 0.20070(2) 0.0182(2) Uani 1 1 d
H13A H -0.192(2) 0.1057(19) 0.2017(3) 0.025(4) Uiso 1 1 d
C14 C -0.00854(17) 0.53499(12) 0.12952(2) 0.0147(2) Uani 1 1 d
C15 C 0.19169(17) 0.59500(14) 0.12260(2) 0.0175(2) Uani 1 1 d
H15A H 0.311(2) 0.5785(18) 0.1373(3) 0.019(3) Uiso 1 1 d
C16 C 0.22285(18) 0.67989(14) 0.09527(3) 0.0190(2) Uani 1 1 d
H16A H 0.361(2) 0.7241(19) 0.0916(3) 0.026(4) Uiso 1 1 d
C17 C 0.05278(18) 0.70606(14) 0.07419(2) 0.0186(2) Uani 1 1 d
C18 C -0.14778(18) 0.64407(14) 0.08044(2) 0.0186(2) Uani 1 1 d
H18A H -0.267(2) 0.6687(19) 0.0660(3) 0.023(4) Uiso 1 1 d
C19 C -0.17659(17) 0.56011(13) 0.10773(2) 0.0164(2) Uani 1 1 d
H19A H -0.316(2) 0.5204(18) 0.1120(3) 0.018(3) Uiso 1 1 d
C20 C 0.5006(2) -0.26069(17) 0.25343(3) 0.0262(3) Uani 1 1 d
H20B H 0.491(3) -0.359(2) 0.2399(4) 0.032(4) Uiso 1 1 d
H20A H 0.615(2) -0.186(2) 0.2463(4) 0.028(4) Uiso 1 1 d
H20C H 0.534(3) -0.295(2) 0.2746(4) 0.033(4) Uiso 1 1 d
C21 C 0.44536(19) 0.11404(16) 0.04469(3) 0.0241(2) Uani 1 1 d
C22 C 0.6427(2) 0.21820(16) 0.05010(3) 0.0248(2) Uani 1 1 d
H22B H 0.766(3) 0.138(2) 0.0538(4) 0.033(4) Uiso 1 1 d
H22A H 0.621(3) 0.290(2) 0.0692(4) 0.034(4) Uiso 1 1 d
C23 C 0.67769(18) 0.33731(15) 0.02314(3) 0.0195(2) Uani 1 1 d
H23B H 0.716(2) 0.270(2) 0.0051(4) 0.026(4) Uiso 1 1 d
H23A H 0.800(3) 0.408(2) 0.0282(4) 0.029(4) Uiso 1 1 d
C24 C 0.48085(17) 0.44241(14) 0.01377(2) 0.0196(2) Uani 1 1 d
H24A H 0.448(2) 0.518(2) 0.0322(4) 0.027(4) Uiso 1 1 d
C25 C 0.29098(18) 0.32494(16) 0.00742(3) 0.0232(2) Uani 1 1 d
H25B H 0.161(3) 0.389(2) 0.0025(4) 0.031(4) Uiso 1 1 d
H25A H 0.323(3) 0.249(2) -0.0103(4) 0.036(4) Uiso 1 1 d
C26 C 0.2484(2) 0.21098(18) 0.03481(3) 0.0290(3) Uani 1 1 d
H26A H 0.129(3) 0.124(2) 0.0286(4) 0.039(4) Uiso 1 1 d
H26B H 0.214(3) 0.288(2) 0.0525(4) 0.041(5) Uiso 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
C11 O2 C20 117.09(9) . .
C17 O3 H3A 108.7(13) . .
O1 C1 C3 118.88(9) . .
O1 C1 C2 118.90(10) . .
C3 C1 C2 122.19(9) . .
C8 C2 C5 107.13(8) . .
C8 C2 C4 112.66(9) . .
C5 C2 C4 108.25(9) . .
C8 C2 C1 109.00(8) . .
C5 C2 C1 108.59(9) . .
C4 C2 C1 111.05(8) . .
C7 C3 C14 112.99(9) . .
C7 C3 C6 107.17(9) . .
C14 C3 C6 108.26(8) . .
C7 C3 C1 113.12(9) . .
C14 C3 C1 106.68(8) . .
C6 C3 C1 108.47(9) . .
C2 C4 H4C 109.5(9) . .
C2 C4 H4B 113.8(9) . .
H4C C4 H4B 108.5(12) . .
C2 C4 H4A 109.8(8) . .
H4C C4 H4A 107.0(12) . .
H4B C4 H4A 108.1(12) . .
C2 C5 H5C 110.9(9) . .
C2 C5 H5B 107.4(9) . .
H5C C5 H5B 107.9(13) . .
C2 C5 H5A 111.0(9) . .
H5C C5 H5A 110.2(13) . .
H5B C5 H5A 109.2(13) . .
C3 C6 H6C 111.1(9) . .
C3 C6 H6B 111.3(9) . .
H6C C6 H6B 107.2(12) . .
C3 C6 H6A 108.5(9) . .
H6C C6 H6A 110.1(13) . .
H6B C6 H6A 108.7(13) . .
C3 C7 H7C 110.0(9) . .
C3 C7 H7B 114.2(9) . .
H7C C7 H7B 106.5(12) . .
C3 C7 H7A 109.2(9) . .
H7C C7 H7A 107.4(13) . .
H7B C7 H7A 109.3(13) . .
C9 C8 C13 117.56(10) . .
C9 C8 C2 122.05(9) . .
C13 C8 C2 120.29(9) . .
C8 C9 C10 121.88(10) . .
C8 C9 H9A 119.3(9) . .
C10 C9 H9A 118.9(9) . .
C11 C10 C9 119.50(10) . .
C11 C10 H10A 120.7(9) . .
C9 C10 H10A 119.8(9) . .
O2 C11 C10 124.85(10) . .
O2 C11 C12 115.38(10) . .
C10 C11 C12 119.76(10) . .
C13 C12 C11 119.74(10) . .
C13 C12 H12A 122.6(7) . .
C11 C12 H12A 117.6(7) . .
C12 C13 C8 121.53(10) . .
C12 C13 H13A 118.6(9) . .
C8 C13 H13A 119.9(9) . .
C15 C14 C19 117.51(10) . .
C15 C14 C3 122.73(9) . .
C19 C14 C3 119.69(9) . .
C14 C15 C16 121.34(10) . .
C14 C15 H15A 119.0(8) . .
C16 C15 H15A 119.6(8) . .
C17 C16 C15 120.17(10) . .
C17 C16 H16A 120.4(9) . .
C15 C16 H16A 119.4(9) . .
O3 C17 C16 122.96(10) . .
O3 C17 C18 117.73(10) . .
C16 C17 C18 119.31(10) . .
C19 C18 C17 119.90(10) . .
C19 C18 H18A 121.4(9) . .
C17 C18 H18A 118.5(9) . .
C18 C19 C14 121.75(10) . .
C18 C19 H19A 119.1(9) . .
C14 C19 H19A 119.1(8) . .
O2 C20 H20B 110.7(10) . .
O2 C20 H20A 111.2(9) . .
H20B C20 H20A 108.2(13) . .
O2 C20 H20C 106.5(10) . .
H20B C20 H20C 110.3(14) . .
H20A C20 H20C 109.9(13) . .
O4 C21 C22 122.03(11) . .
O4 C21 C26 122.93(11) . .
C22 C21 C26 115.03(11) . .
C21 C22 C23 111.71(9) . .
C21 C22 H22B 107.3(9) . .
C23 C22 H22B 111.9(9) . .
C21 C22 H22A 107.0(9) . .
C23 C22 H22A 107.9(9) . .
H22B C22 H22A 110.9(13) . .
C24 C23 C22 113.38(9) . .
C24 C23 H23B 107.9(9) . .
C22 C23 H23B 109.0(9) . .
C24 C23 H23A 111.3(9) . .
C22 C23 H23A 109.1(9) . .
H23B C23 H23A 105.9(13) . .
C25 C24 C23 109.01(9) . .
C25 C24 C24 111.95(11) . 3_665
C23 C24 C24 112.17(11) . 3_665
C25 C24 H24A 108.0(9) . .
C23 C24 H24A 107.6(9) . .
C24 C24 H24A 107.9(9) 3_665 .
C24 C25 C26 112.67(10) . .
C24 C25 H25B 110.9(10) . .
C26 C25 H25B 107.6(10) . .
C24 C25 H25A 108.8(10) . .
C26 C25 H25A 107.0(10) . .
H25B C25 H25A 109.8(13) . .
C21 C26 C25 110.67(10) . .
C21 C26 H26A 107.8(10) . .
C25 C26 H26A 109.8(10) . .
C21 C26 H26B 107.1(10) . .
C25 C26 H26B 106.8(10) . .
H26A C26 H26B 114.6(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2143(13) .
O2 C11 1.3716(13) .
O2 C20 1.4202(15) .
O3 C17 1.3653(13) .
O3 H3A 0.86(2) .
O4 C21 1.2252(16) .
C1 C3 1.5499(14) .
C1 C2 1.5516(14) .
C2 C8 1.5333(14) .
C2 C5 1.5389(15) .
C2 C4 1.5413(14) .
C3 C7 1.5373(14) .
C3 C14 1.5386(14) .
C3 C6 1.5446(15) .
C4 H4C 0.985(15) .
C4 H4B 0.975(16) .
C4 H4A 0.990(15) .
C5 H5C 0.994(17) .
C5 H5B 0.991(16) .
C5 H5A 0.990(16) .
C6 H6C 0.981(16) .
C6 H6B 1.010(15) .
C6 H6A 0.988(17) .
C7 H7C 1.000(16) .
C7 H7B 0.993(16) .
C7 H7A 0.993(16) .
C8 C9 1.3883(15) .
C8 C13 1.4004(15) .
C9 C10 1.3961(15) .
C9 H9A 0.967(15) .
C10 C11 1.3873(15) .
C10 H10A 0.955(16) .
C11 C12 1.3975(15) .
C12 C13 1.3868(15) .
C12 H12A 1.155(13) .
C13 H13A 0.960(16) .
C14 C15 1.3948(15) .
C14 C19 1.4002(15) .
C15 C16 1.3951(15) .
C15 H15A 0.971(14) .
C16 C17 1.3911(16) .
C16 H16A 0.957(16) .
C17 C18 1.3947(16) .
C18 C19 1.3876(15) .
C18 H18A 0.975(15) .
C19 H19A 0.961(14) .
C20 H20B 0.979(17) .
C20 H20A 0.995(16) .
C20 H20C 0.978(17) .
C21 C22 1.5020(17) .
C21 C26 1.5043(17) .
C22 C23 1.5378(16) .
C22 H22B 1.008(17) .
C22 H22A 1.030(17) .
C23 C24 1.5329(15) .
C23 H23B 0.994(16) .
C23 H23A 0.973(16) .
C24 C25 1.5315(15) .
C24 C24 1.543(2) 3_665
C24 H24A 1.034(16) .
C25 C26 1.5373(16) .
C25 H25B 0.975(16) .
C25 H25A 1.010(18) .
C26 H26A 1.049(18) .
C26 H26B 1.020(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180014
