#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151377.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_7151377
loop_
_publ_author_name
'Klimova, Elena I.'
'García, Marcos Martínez'
'Klimova, Tatiana'
'Ortega, S. Hernandez'
'Bakinovsky, Leon V.'
_publ_section_title
;
 1,3-Bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition
 and cyclodimerization reactions. The role of stereoelectronic factors
;
_journal_issue                   7
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1210
_journal_paper_doi               10.1039/b210890a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C23 H26 O4'
_chemical_formula_weight         366.44
_chemical_name_common
;2-hydroxy-6-(4-methoxybencyliden)-2-(1-(4-
methoxyphenyl)ethyl)cyclohexanone
;
_chemical_name_systematic
; 
2-hydroxy-6-(4-methoxybencyliden)-2-[1-(4-methoxyphenyl)ethyl]cyclohexanone 
;
_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                 98.69
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.915(2)
_cell_length_b                   5.6940(10)
_cell_length_c                   27.080(3)
_cell_measurement_reflns_used    38
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      7.21
_cell_volume                     1968.5(5)
_computing_cell_refinement       'XSCANS v2.1b (SIEMENS Software 1993)'
_computing_data_collection       'XSCANS v2.1b (SIEMENS Software 1993)'
_computing_data_reduction        'XSCANS v2.1b (SIEMENS software 1993)'
_computing_molecular_graphics    'XP (SHELXTL PC: SIEMENS, 1990)'
_computing_publication_material  'SHELXTL PC: (SIEMENS,1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4/PC'
_diffrn_measurement_method       'q/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3740
_diffrn_reflns_theta_full        56.70
_diffrn_reflns_theta_max         56.70
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        >2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Prism laminar'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    'No Refined except H2 on O2'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.3373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                2154
_reflns_number_total             2626
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b210890a.txt
_cod_data_source_block           B210890A
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'NO' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7151377
_solved_by                       'Simon Hernandez-Ortega'
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38470(12) 0.8757(3) -0.03569(5) 0.0633(5) Uani 1 1 d . . .
O2 O 0.38044(14) 1.1018(3) 0.05081(7) 0.0642(5) Uani 1 1 d . . .
H2 H 0.424(2) 1.079(6) 0.0377(11) 0.077 Uiso 1 1 d . . .
O3 O -0.00682(14) -0.0765(3) -0.20623(7) 0.0791(6) Uani 1 1 d . . .
O4 O 0.34329(15) 0.7181(4) 0.28170(6) 0.0868(6) Uani 1 1 d . . .
C1 C 0.31172(16) 0.8254(4) -0.01370(7) 0.0489(5) Uani 1 1 d . . .
C2 C 0.31522(16) 0.9020(4) 0.04073(8) 0.0485(5) Uani 1 1 d . . .
C3 C 0.20587(18) 0.9743(4) 0.04962(9) 0.0635(6) Uani 1 1 d . . .
H3A H 0.2074 1.0088 0.0848 0.076 Uiso 1 1 calc R . .
H3B H 0.1855 1.1166 0.0309 0.076 Uiso 1 1 calc R . .
C4 C 0.12482(17) 0.7852(5) 0.03409(9) 0.0661(7) Uani 1 1 d . . .
H4A H 0.0572 0.8377 0.0413 0.079 Uiso 1 1 calc R . .
H4B H 0.1438 0.6442 0.0534 0.079 Uiso 1 1 calc R . .
C5 C 0.11624(18) 0.7281(5) -0.02134(9) 0.0651(7) Uani 1 1 d . . .
H5A H 0.0726 0.5900 -0.0285 0.078 Uiso 1 1 calc R . .
H5B H 0.0820 0.8577 -0.0405 0.078 Uiso 1 1 calc R . .
C6 C 0.22099(16) 0.6839(4) -0.03791(7) 0.0484(5) Uani 1 1 d . . .
C7 C 0.35927(15) 0.6875(4) 0.07342(7) 0.0436(5) Uani 1 1 d . . .
H7 H 0.3176 0.5502 0.0610 0.052 Uiso 1 1 calc R . .
C8 C 0.24015(15) 0.5293(4) -0.07258(7) 0.0480(5) Uani 1 1 d . . .
H8 H 0.3103 0.5172 -0.0764 0.058 Uiso 1 1 calc R . .
C9 C 0.47284(17) 0.6353(4) 0.06748(8) 0.0543(5) Uani 1 1 d . . .
H9A H 0.4782 0.6200 0.0326 0.065 Uiso 1 1 calc R . .
H9B H 0.4947 0.4915 0.0844 0.065 Uiso 1 1 calc R . .
H9C H 0.5169 0.7615 0.0816 0.065 Uiso 1 1 calc R . .
C10 C 0.16961(15) 0.3756(4) -0.10558(7) 0.0483(5) Uani 1 1 d . . .
C11 C 0.21028(17) 0.1710(4) -0.12397(8) 0.0554(6) Uani 1 1 d . . .
H11 H 0.2803 0.1335 -0.1137 0.066 Uiso 1 1 calc R . .
C12 C 0.15009(18) 0.0243(4) -0.15666(9) 0.0613(6) Uani 1 1 d . . .
H12 H 0.1792 -0.1112 -0.1679 0.074 Uiso 1 1 calc R . .
C13 C 0.04574(18) 0.0778(4) -0.17293(8) 0.0566(6) Uani 1 1 d . . .
C14 C 0.00344(17) 0.2806(5) -0.15612(8) 0.0596(6) Uani 1 1 d . . .
H14 H -0.0663 0.3184 -0.1670 0.072 Uiso 1 1 calc R . .
C15 C 0.06506(17) 0.4270(4) -0.12300(8) 0.0579(6) Uani 1 1 d . . .
H15 H 0.0359 0.5633 -0.1121 0.070 Uiso 1 1 calc R . .
C16 C 0.35100(15) 0.7115(4) 0.12835(7) 0.0449(5) Uani 1 1 d . . .
C17 C 0.39925(18) 0.8920(4) 0.15767(8) 0.0576(6) Uani 1 1 d . . .
H17 H 0.4332 1.0102 0.1426 0.069 Uiso 1 1 calc R . .
C18 C 0.39827(19) 0.9012(5) 0.20887(8) 0.0615(6) Uani 1 1 d . . .
H18 H 0.4310 1.0245 0.2276 0.074 Uiso 1 1 calc R . .
C19 C 0.34885(17) 0.7279(5) 0.23170(8) 0.0596(6) Uani 1 1 d . . .
C20 C 0.30072(19) 0.5464(5) 0.20344(8) 0.0649(7) Uani 1 1 d . . .
H20 H 0.2674 0.4281 0.2188 0.078 Uiso 1 1 calc R . .
C21 C 0.30152(17) 0.5388(4) 0.15262(8) 0.0552(6) Uani 1 1 d . . .
H21 H 0.2682 0.4153 0.1341 0.066 Uiso 1 1 calc R . .
C22 C -0.1114(2) -0.0188(6) -0.22714(11) 0.0837(9) Uani 1 1 d . . .
H22A H -0.1395 -0.1404 -0.2499 0.100 Uiso 1 1 calc R . .
H22B H -0.1119 0.1275 -0.2448 0.100 Uiso 1 1 calc R . .
H22C H -0.1534 -0.0047 -0.2009 0.100 Uiso 1 1 calc R . .
C23 C 0.3900(3) 0.9007(7) 0.31255(10) 0.0996(11) Uani 1 1 d . . .
H23A H 0.3802 0.8717 0.3465 0.120 Uiso 1 1 calc R . .
H23B H 0.3581 1.0476 0.3016 0.120 Uiso 1 1 calc R . .
H23C H 0.4636 0.9068 0.3106 0.120 Uiso 1 1 calc R . .
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
C13 O3 C22 117.6(2) . . yes
C19 O4 C23 118.3(2) . . yes
O1 C1 C6 121.70(19) . . yes
O1 C1 C2 119.30(19) . . yes
C6 C1 C2 118.97(18) . . yes
O2 C2 C3 106.89(18) . . yes
O2 C2 C1 110.12(17) . . yes
C3 C2 C1 109.60(17) . . yes
O2 C2 C7 111.28(16) . . yes
C3 C2 C7 112.83(18) . . yes
C1 C2 C7 106.14(16) . . yes
C4 C3 C2 112.43(19) . . yes
C3 C4 C5 111.7(2) . . yes
C6 C5 C4 113.17(18) . . yes
C8 C6 C1 116.63(18) . . yes
C8 C6 C5 126.0(2) . . yes
C1 C6 C5 117.36(19) . . yes
C16 C7 C9 109.41(16) . . yes
C16 C7 C2 114.34(16) . . yes
C9 C7 C2 111.41(17) . . yes
C6 C8 C10 131.09(19) . . yes
C15 C10 C11 116.8(2) . . yes
C15 C10 C8 124.2(2) . . yes
C11 C10 C8 118.79(18) . . yes
C12 C11 C10 122.0(2) . . yes
C11 C12 C13 120.0(2) . . yes
O3 C13 C14 125.0(2) . . yes
O3 C13 C12 115.5(2) . . yes
C14 C13 C12 119.5(2) . . yes
C13 C14 C15 119.9(2) . . yes
C14 C15 C10 121.7(2) . . yes
C17 C16 C21 116.87(19) . . yes
C17 C16 C7 122.48(19) . . yes
C21 C16 C7 120.41(18) . . yes
C16 C17 C18 121.9(2) . . yes
C19 C18 C17 119.8(2) . . yes
O4 C19 C18 125.0(2) . . yes
O4 C19 C20 115.6(2) . . yes
C18 C19 C20 119.4(2) . . yes
C19 C20 C21 120.5(2) . . yes
C20 C21 C16 121.5(2) . . yes
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 C1 1.222(3) . yes
O2 C2 1.417(3) . yes
O3 C13 1.364(3) . yes
O3 C22 1.422(3) . yes
O4 C19 1.368(3) . yes
O4 C23 1.411(4) . yes
C1 C6 1.490(3) . yes
C1 C2 1.531(3) . yes
C2 C3 1.525(3) . yes
C2 C7 1.564(3) . yes
C3 C4 1.516(4) . yes
C4 C5 1.523(3) . yes
C5 C6 1.509(3) . yes
C6 C8 1.337(3) . yes
C7 C16 1.513(3) . yes
C7 C9 1.529(3) . yes
C8 C10 1.466(3) . yes
C10 C15 1.392(3) . yes
C10 C11 1.400(3) . yes
C11 C12 1.370(3) . yes
C12 C13 1.387(3) . yes
C13 C14 1.383(3) . yes
C14 C15 1.385(3) . yes
C16 C17 1.388(3) . yes
C16 C21 1.391(3) . yes
C17 C18 1.389(3) . yes
C18 C19 1.372(4) . yes
C19 C20 1.377(3) . yes
C20 C21 1.379(3) . yes
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
O2 H2 O1 0.72(3) 2.29(3) 2.681(2) 116(3) .
O2 H2 O1 0.72(3) 2.50(3) 3.124(2) 147(3) 3_675
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9985342
2 PubChem 139190481
