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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507528.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_1507528
loop_
_publ_author_name
'Tukada, Hideyuki'
'Mochizuki, Katsura'
_publ_section_title
;
 Long-Range Magnetic Interactions intrans-1,4-Cyclohexylene- and
 1,3-Adamantylene-bis(p-nitrenylbenzene) by π−σ−π
 Hyperconjugation
;
_journal_issue                   21
_journal_name_full               'Organic Letters'
_journal_page_first              3305
_journal_paper_doi               10.1021/ol0165241
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C18 H20'
_chemical_formula_weight         236.40
_chemical_name_systematic
;1,4-diphenylcyclohexane  
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.236(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0690(16)
_cell_length_b                   18.263(4)
_cell_length_c                   5.6180(17)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      17.50
_cell_measurement_theta_min      14.99
_cell_volume                     680.5(3)
_computing_cell_refinement       'MXC (MAC Science)'
_computing_data_collection       'MXC (MAC Science)'
_computing_data_reduction        'MXC (MAC Science)'
_computing_molecular_graphics    Ortep-3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir-92 in MAXUS'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.875
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device_type  'Mac Science MXC3K'
_diffrn_measurement_method       2theta-Omega
_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  0.012
_diffrn_reflns_av_sigmaI/netI    1.0761
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1373
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        non
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0638
_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)+(0.0475P)²+0.3788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1483
_reflns_number_gt                1248
_reflns_number_total             1373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0165241_s1.cif
_cod_data_source_block           tsukada2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Psi-Scan'
changed to 'psi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n        '
_cod_database_code               1507528
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C3 C 0.3766(3) 0.06036(10) 0.3445(4) 0.0407(4) Uani 1 1 d .
H3 H 0.4651 0.0731 0.2495 0.049 Uiso 1 1 calc R
C4 C 0.1960(3) 0.11090(10) 0.2541(4) 0.0401(4) Uani 1 1 d .
C5 C 0.1692(3) 0.15809(11) 0.0520(4) 0.0477(5) Uani 1 1 d .
H5 H 0.2635 0.1585 -0.0294 0.057 Uiso 1 1 calc R
C2 C 0.3178(3) -0.01990(11) 0.2886(4) 0.0506(5) Uani 1 1 d .
H2A H 0.2254 -0.0337 0.3745 0.061 Uiso 1 1 calc R
H2B H 0.2484 -0.0261 0.1077 0.061 Uiso 1 1 calc R
C1 C 0.5014(3) -0.07005(11) 0.3751(4) 0.0523(6) Uani 1 1 d .
H1A H 0.4573 -0.1206 0.3440 0.063 Uiso 1 1 calc R
H1B H 0.5866 -0.0596 0.2761 0.063 Uiso 1 1 calc R
C9 C 0.0512(3) 0.11155(12) 0.3704(4) 0.0480(5) Uani 1 1 d .
H9 H 0.0648 0.0802 0.5057 0.058 Uiso 1 1 calc R
C7 C -0.1363(3) 0.20470(12) 0.0855(5) 0.0540(6) Uani 1 1 d .
H7 H -0.2470 0.2358 0.0287 0.065 Uiso 1 1 calc R
C8 C -0.1132(3) 0.15841(12) 0.2869(5) 0.0534(5) Uani 1 1 d .
H8 H -0.2082 0.1585 0.3674 0.064 Uiso 1 1 calc R
C6 C 0.0056(4) 0.20454(12) -0.0309(4) 0.0560(6) Uani 1 1 d .
H6 H -0.0088 0.2359 -0.1664 0.067 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C3 0.0377(9) 0.0379(10) 0.0466(10) 0.0012(8) 0.0147(8) 0.0015(7)
C4 0.0367(9) 0.0352(9) 0.0444(10) -0.0039(8) 0.0087(8) -0.0030(7)
C5 0.0514(11) 0.0470(11) 0.0440(10) -0.0001(9) 0.0157(9) 0.0042(9)
C2 0.0429(10) 0.0430(11) 0.0535(12) -0.0111(9) 0.0008(9) 0.0024(8)
C1 0.0481(11) 0.0418(11) 0.0556(12) -0.0120(9) 0.0034(9) 0.0050(9)
C9 0.0422(10) 0.0489(11) 0.0525(12) 0.0041(9) 0.0160(9) -0.0007(9)
C7 0.0442(11) 0.0436(11) 0.0647(13) -0.0027(10) 0.0066(10) 0.0073(9)
C8 0.0400(11) 0.0531(12) 0.0670(14) -0.0024(11) 0.0184(10) 0.0011(9)
C6 0.0626(13) 0.0482(12) 0.0512(12) 0.0075(10) 0.0122(10) 0.0080(10)
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'
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
C4 C3 C1 112.74(16) . 3_656
C4 C3 C2 112.24(15) . .
C1 C3 C2 109.93(16) 3_656 .
C4 C3 H3 107.2 . .
C1 C3 H3 107.2 3_656 .
C2 C3 H3 107.2 . .
C5 C4 C9 117.71(18) . .
C5 C4 C3 120.98(17) . .
C9 C4 C3 121.31(18) . .
C6 C5 C4 121.4(2) . .
C6 C5 H5 119.3 . .
C4 C5 H5 119.3 . .
C1 C2 C3 111.72(16) . .
C1 C2 H2A 109.3 . .
C3 C2 H2A 109.3 . .
C1 C2 H2B 109.3 . .
C3 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
C3 C1 C2 112.05(17) 3_656 .
C3 C1 H1A 109.2 3_656 .
C2 C1 H1A 109.2 . .
C3 C1 H1B 109.2 3_656 .
C2 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
C8 C9 C4 120.8(2) . .
C8 C9 H9 119.6 . .
C4 C9 H9 119.6 . .
C6 C7 C8 119.5(2) . .
C6 C7 H7 120.3 . .
C8 C7 H7 120.3 . .
C7 C8 C9 120.2(2) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C7 C6 C5 120.4(2) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 C4 1.513(2) .
C3 C1 1.522(3) 3_656
C3 C2 1.526(3) .
C3 H3 0.9800 .
C4 C5 1.385(3) .
C4 C9 1.392(3) .
C5 C6 1.379(3) .
C5 H5 0.9300 .
C2 C1 1.524(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 C3 1.522(3) 3_656
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C9 C8 1.388(3) .
C9 H9 0.9300 .
C7 C6 1.374(3) .
C7 C8 1.376(3) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C6 H6 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 140800
