#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239279.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239279
loop_
_publ_author_name
'Corfield, Peter W. R.'
'Paccagnini, Michele L.'
'Balija, Amy M.'
_publ_section_title
;
 Methyl 3,5-bis(cyclohexylmethoxy)benzoate
;
_journal_coeditor_code           PK2519
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o400
_journal_page_last               o401
_journal_paper_doi               10.1107/S1600536814004607
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C22 H32 O4'
_chemical_formula_moiety         'C22 H32 O4'
_chemical_formula_sum            'C22 H32 O4'
_chemical_formula_weight         360.48
_chemical_melting_point          344.8
_chemical_melting_point_gt       343.7
_chemical_melting_point_lt       345.9
_chemical_name_systematic
;
Methyl 3,5-bis(cyclohexylmethoxy)benzoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.640(10)
_cell_angle_beta                 79.460(10)
_cell_angle_gamma                75.060(10)
_cell_formula_units_Z            2
_cell_length_a                   6.6490(10)
_cell_length_b                   12.6680(10)
_cell_length_c                   12.8730(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      9.7
_cell_measurement_theta_min      3.2
_cell_volume                     1029.9(2)
_computing_cell_refinement       'CAD-4 (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 (Enraf--Nonius, 1994)'
_computing_data_reduction
;
followed procedures in Corfield et al. (1973) and
data were averaged with a local version of SORTAV (Blessing,
1989)
;
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'θ/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0082
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5155
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.31
_diffrn_standards_decay_%        1.3(5)
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.53
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                3013
_reflns_number_total             4051
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2519sup1.cif
_cod_data_source_block           I
_cod_database_code               2239279
_cod_database_fobs_code          2239279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 -0.2343(2) 0.20265(10) 0.34241(8) 0.0613(3) Uani d . 1 1
O O2 -0.0616(2) 0.25640(11) 0.67501(8) 0.0628(4) Uani d . 1 1
O O3 0.2878(2) 0.42136(12) 0.25302(9) 0.0756(4) Uani d . 1 1
O O4 0.37753(19) 0.44700(10) 0.40594(8) 0.0602(3) Uani d . 1 1
C C1 0.1250(2) 0.34685(12) 0.40804(11) 0.0450(4) Uani d . 1 1
C C2 0.0091(3) 0.30219(13) 0.35244(11) 0.0486(4) Uani d . 1 1
H H2 0.0217 0.3118 0.2797 0.058 Uiso calc R 1 1
C C3 -0.1264(3) 0.24282(13) 0.40479(11) 0.0490(4) Uani d . 1 1
C C4 -0.1455(3) 0.22817(14) 0.51302(12) 0.0512(4) Uani d . 1 1
H H4 -0.2355 0.1878 0.5482 0.061 Uiso calc R 1 1
C C5 -0.0280(3) 0.27471(13) 0.56870(11) 0.0495(4) Uani d . 1 1
C C6 0.1076(3) 0.33363(13) 0.51749(11) 0.0485(4) Uani d . 1 1
H H6 0.1862 0.3641 0.5549 0.058 Uiso calc R 1 1
C C7 0.2697(3) 0.40810(13) 0.34645(12) 0.0483(4) Uani d . 1 1
C C8 0.5185(3) 0.50921(17) 0.35207(14) 0.0655(5) Uani d . 1 1
H H8A 0.6079 0.4683 0.2922 0.079 Uiso calc R 1 1
H H8B 0.6042 0.5236 0.3995 0.079 Uiso calc R 1 1
H H8C 0.4372 0.5771 0.3286 0.079 Uiso calc R 1 1
C C9 -0.3584(3) 0.13030(15) 0.38765(12) 0.0554(4) Uani d . 1 1
H H9A -0.4655 0.1661 0.4459 0.067 Uiso calc R 1 1
H H9B -0.2692 0.0658 0.4145 0.067 Uiso calc R 1 1
C C10 -0.4621(3) 0.09842(14) 0.30275(12) 0.0516(4) Uani d . 1 1
H H10 -0.5436 0.1657 0.2746 0.062 Uiso calc R 1 1
C C11 -0.3030(3) 0.03691(16) 0.21158(14) 0.0621(5) Uani d . 1 1
H H11A -0.2114 0.0823 0.1795 0.075 Uiso calc R 1 1
H H11B -0.2157 -0.0286 0.2379 0.075 Uiso calc R 1 1
C C12 -0.4151(4) 0.00567(19) 0.12867(16) 0.0777(6) Uani d . 1 1
H H12A -0.3110 -0.0377 0.0735 0.093 Uiso calc R 1 1
H H12B -0.4894 0.0714 0.0967 0.093 Uiso calc R 1 1
C C13 -0.5711(4) -0.05892(19) 0.17717(19) 0.0862(7) Uani d . 1 1
H H13A -0.6463 -0.0733 0.1237 0.103 Uiso calc R 1 1
H H13B -0.4946 -0.1286 0.2016 0.103 Uiso calc R 1 1
C C14 -0.7281(4) 0.00134(19) 0.26845(18) 0.0795(6) Uani d . 1 1
H H14A -0.8190 -0.0444 0.3005 0.095 Uiso calc R 1 1
H H14B -0.8163 0.0670 0.2428 0.095 Uiso calc R 1 1
C C15 -0.6158(3) 0.03203(17) 0.35076(15) 0.0665(5) Uani d . 1 1
H H15A -0.7197 0.0742 0.4067 0.080 Uiso calc R 1 1
H H15B -0.5395 -0.0339 0.3816 0.080 Uiso calc R 1 1
C C16 0.0433(3) 0.30659(15) 0.73897(11) 0.0525(4) Uani d . 1 1
H H16A 0.0098 0.3849 0.7276 0.063 Uiso calc R 1 1
H H16B 0.1953 0.2778 0.7200 0.063 Uiso calc R 1 1
C C17 -0.0299(3) 0.28262(14) 0.85363(11) 0.0500(4) Uani d . 1 1
H H17 0.0038 0.2032 0.8626 0.060 Uiso calc R 1 1
C C18 -0.2652(3) 0.32768(16) 0.88989(12) 0.0571(4) Uani d . 1 1
H H18A -0.3025 0.4059 0.8784 0.069 Uiso calc R 1 1
H H18B -0.3411 0.2949 0.8482 0.069 Uiso calc R 1 1
C C19 -0.3324(3) 0.3047(2) 1.00661(13) 0.0713(6) Uani d . 1 1
H H19A -0.4822 0.3385 1.0281 0.086 Uiso calc R 1 1
H H19B -0.3101 0.2265 1.0167 0.086 Uiso calc R 1 1
C C20 -0.2097(3) 0.3479(2) 1.07503(13) 0.0755(6) Uani d . 1 1
H H20A -0.2480 0.4271 1.0729 0.091 Uiso calc R 1 1
H H20B -0.2473 0.3259 1.1476 0.091 Uiso calc R 1 1
C C21 0.0244(3) 0.3063(2) 1.03912(14) 0.0855(7) Uani d . 1 1
H H21A 0.0658 0.2281 1.0511 0.103 Uiso calc R 1 1
H H21B 0.0976 0.3409 1.0807 0.103 Uiso calc R 1 1
C C22 0.0908(3) 0.3291(2) 0.92233(13) 0.0706(6) Uani d . 1 1
H H22A 0.0649 0.4073 0.9117 0.085 Uiso calc R 1 1
H H22B 0.2413 0.2969 0.9010 0.085 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 2 -4
3 0 0
-2 -2 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C9 118.71(12)
C5 O2 C16 117.86(12)
C7 O4 C8 116.24(12)
C2 C1 C6 120.88(14)
C2 C1 C7 116.97(13)
C6 C1 C7 122.15(13)
C1 C2 C3 119.89(14)
C1 C2 H2 120.1
C3 C2 H2 120.1
O1 C3 C4 124.58(14)
O1 C3 C2 115.13(13)
C4 C3 C2 120.28(14)
C3 C4 C5 119.23(15)
C3 C4 H4 120.4
C5 C4 H4 120.4
O2 C5 C6 124.79(13)
O2 C5 C4 114.21(14)
C6 C5 C4 121.00(13)
C5 C6 C1 118.70(14)
C5 C6 H6 120.6
C1 C6 H6 120.6
O3 C7 O4 123.11(15)
O3 C7 C1 123.90(14)
O4 C7 C1 112.99(12)
O4 C8 H8A 109.5
O4 C8 H8B 109.5
H8A C8 H8B 109.5
O4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 C10 108.22(13)
O1 C9 H9A 110.1
C10 C9 H9A 110.1
O1 C9 H9B 110.1
C10 C9 H9B 110.1
H9A C9 H9B 108.4
C9 C10 C15 109.83(14)
C9 C10 C11 112.77(14)
C15 C10 C11 110.74(15)
C9 C10 H10 107.8
C15 C10 H10 107.8
C11 C10 H10 107.8
C12 C11 C10 110.79(15)
C12 C11 H11A 109.5
C10 C11 H11A 109.5
C12 C11 H11B 109.5
C10 C11 H11B 109.5
H11A C11 H11B 108.1
C11 C12 C13 111.22(17)
C11 C12 H12A 109.4
C13 C12 H12A 109.4
C11 C12 H12B 109.4
C13 C12 H12B 109.4
H12A C12 H12B 108.0
C14 C13 C12 111.78(17)
C14 C13 H13A 109.3
C12 C13 H13A 109.3
C14 C13 H13B 109.3
C12 C13 H13B 109.3
H13A C13 H13B 107.9
C13 C14 C15 110.87(17)
C13 C14 H14A 109.5
C15 C14 H14A 109.5
C13 C14 H14B 109.5
C15 C14 H14B 109.5
H14A C14 H14B 108.1
C10 C15 C14 111.39(16)
C10 C15 H15A 109.3
C14 C15 H15A 109.3
C10 C15 H15B 109.3
C14 C15 H15B 109.3
H15A C15 H15B 108.0
O2 C16 C17 108.62(13)
O2 C16 H16A 110.0
C17 C16 H16A 110.0
O2 C16 H16B 110.0
C17 C16 H16B 110.0
H16A C16 H16B 108.3
C16 C17 C22 109.33(14)
C16 C17 C18 113.02(14)
C22 C17 C18 109.76(13)
C16 C17 H17 108.2
C22 C17 H17 108.2
C18 C17 H17 108.2
C19 C18 C17 111.55(15)
C19 C18 H18A 109.3
C17 C18 H18A 109.3
C19 C18 H18B 109.3
C17 C18 H18B 109.3
H18A C18 H18B 108.0
C20 C19 C18 111.71(15)
C20 C19 H19A 109.3
C18 C19 H19A 109.3
C20 C19 H19B 109.3
C18 C19 H19B 109.3
H19A C19 H19B 107.9
C21 C20 C19 111.69(16)
C21 C20 H20A 109.3
C19 C20 H20A 109.3
C21 C20 H20B 109.3
C19 C20 H20B 109.3
H20A C20 H20B 107.9
C20 C21 C22 111.75(17)
C20 C21 H21A 109.3
C22 C21 H21A 109.3
C20 C21 H21B 109.3
C22 C21 H21B 109.3
H21A C21 H21B 107.9
C17 C22 C21 111.58(16)
C17 C22 H22A 109.3
C21 C22 H22A 109.3
C17 C22 H22B 109.3
C21 C22 H22B 109.3
H22A C22 H22B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3608(17)
O1 C9 1.4245(19)
O2 C5 1.3658(18)
O2 C16 1.4322(17)
O3 C7 1.1959(18)
O4 C7 1.3256(18)
O4 C8 1.4415(19)
C1 C2 1.373(2)
C1 C6 1.399(2)
C1 C7 1.487(2)
C2 C3 1.385(2)
C2 H2 0.9300
C3 C4 1.385(2)
C4 C5 1.396(2)
C4 H4 0.9300
C5 C6 1.376(2)
C6 H6 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.513(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.518(2)
C10 C11 1.516(2)
C10 H10 0.9800
C11 C12 1.526(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.514(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.506(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.518(2)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
C16 C17 1.511(2)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C22 1.523(2)
C17 C18 1.512(2)
C17 H17 0.9800
C18 C19 1.526(2)
C18 H18A 0.9700
C18 H18B 0.9700
C19 C20 1.508(2)
C19 H19A 0.9700
C19 H19B 0.9700
C20 C21 1.499(3)
C20 H20A 0.9700
C20 H20B 0.9700
C21 C22 1.525(2)
C21 H21A 0.9700
C21 H21B 0.9700
C22 H22A 0.9700
C22 H22B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8B O4 2_666 0.96 2.58 3.409(2) 145.2
C16 H16A O3 2_566 0.97 2.71 3.573(2) 147.9
C18 H18A O3 2_566 0.97 2.72 3.590(2) 149.4
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
C2 C3 O1 C9 172.88(15)
C4 C3 O1 C9 -7.4(3)
C3 O1 C9 C10 179.66(14)
O1 C9 C10 C11 62.55(19)
O1 C9 C10 C15 -173.41(15)
C4 C5 O2 C16 -176.46(15)
C6 C5 O2 C16 3.3(3)
C5 O2 C16 C17 175.59(14)
O2 C16 C17 C18 -61.10(19)
O2 C16 C17 C22 176.33(15)
