#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/89/2008975.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_2008975
loop_
_publ_author_name
'H. Surya Prakash Rao'
'S. Rajamathe'
'S. Shanmuga Sundara Raj'
'Kandasamy Chinnakali'
'Ibrahim Abdul Razak'
'Hoong-Kun Fun'
_publ_section_title
;Methyl 1-(4-chlorobenzyl)-2-oxocyclohexane-1-carboxylate and methyl
 (2RS,4aRS,8aRS)-2-(4-chlorobenzyl)-3-oxoperhydronaphthalene-2-carboxylate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1519
_journal_page_last               1522
_journal_paper_doi               10.1107/S0108270199007003
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C19 H23 Cl O3'
_chemical_formula_weight         334.82
_chemical_name_systematic
;
Methyl (2R,4aR,8aR)-2-(4-chlorobenzyl)-3-oxoperhydro-2-cyclohexanecarboxylate
(II)
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.9050(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7762(3)
_cell_length_b                   11.8495(4)
_cell_length_c                   13.0464(4)
_cell_measurement_reflns_used    4448
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.11
_cell_volume                     1774.54(9)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 1990)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measurement_device       'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.057
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11499
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(empirical using SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.111
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0506P)²+0.3434P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                2436
_reflns_number_total             4316
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1299.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2008975
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_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.94513(7) 0.19570(6) 0.05568(6) 0.0825(3) Uani d . 1 . . Cl
O1 1.15544(16) -0.14810(17) -0.50176(14) 0.0774(5) Uani d . 1 . . O
O2 1.07261(15) -0.26151(13) -0.30171(16) 0.0748(5) Uani d . 1 . . O
O3 0.96194(13) -0.12059(13) -0.38256(14) 0.0649(5) Uani d . 1 . . O
C1 1.26350(16) -0.11919(15) -0.22959(15) 0.0414(5) Uani d . 1 . . C
H1A 1.2387 -0.1009 -0.1655 0.050 Uiso calc R 1 . . H
H1B 1.2734 -0.2004 -0.2312 0.050 Uiso calc R 1 . . H
C2 1.16601(17) -0.08436(15) -0.32450(15) 0.0409(4) Uani d . 1 . . C
C3 1.2123(2) -0.09951(18) -0.42588(17) 0.0498(5) Uani d . 1 . . C
C4 1.3317(2) -0.0533(2) -0.42320(18) 0.0594(6) Uani d . 1 . . C
H4A 1.3279 0.0284 -0.4247 0.071 Uiso calc R 1 . . H
H4B 1.3562 -0.0779 -0.4858 0.071 Uiso calc R 1 . . H
C5 1.5435(2) -0.0404(2) -0.3232(2) 0.0707(8) Uani d . 1 . . C
H5A 1.5695 -0.0641 -0.3853 0.085 Uiso calc R 1 . . H
H5B 1.5381 0.0413 -0.3244 0.085 Uiso calc R 1 . . H
C6 1.6326(2) -0.0772(2) -0.2254(2) 0.0801(9) Uani d . 1 . . C
H6A 1.7063 -0.0397 -0.2237 0.096 Uiso calc R 1 . . H
H6B 1.6451 -0.1579 -0.2282 0.096 Uiso calc R 1 . . H
C7 1.5909(2) -0.0483(3) -0.1261(2) 0.0817(9) Uani d . 1 . . C
H7A 1.6469 -0.0758 -0.0651 0.098 Uiso calc R 1 . . H
H7B 1.5858 0.0331 -0.1199 0.098 Uiso calc R 1 . . H
C8 1.4721(2) -0.1006(2) -0.12838(19) 0.0610(6) Uani d . 1 . . C
H8A 1.4465 -0.0786 -0.0656 0.073 Uiso calc R 1 . . H
H8B 1.4789 -0.1822 -0.1283 0.073 Uiso calc R 1 . . H
C9 1.38132(16) -0.06328(16) -0.22555(15) 0.0423(5) Uani d . 1 . . C
H9A 1.3714 0.0186 -0.2218 0.051 Uiso calc R 1 . . H
C10 1.42318(18) -0.09038(18) -0.32614(16) 0.0486(5) Uani d . 1 . . C
H10A 1.4304 -0.1726 -0.3298 0.058 Uiso calc R 1 . . H
C11 1.12850(18) 0.04199(16) -0.31982(16) 0.0442(5) Uani d . 1 . . C
H11A 1.1952 0.0893 -0.3218 0.053 Uiso calc R 1 . . H
H11B 1.0690 0.0583 -0.3825 0.053 Uiso calc R 1 . . H
C12 1.08193(17) 0.07506(15) -0.22428(16) 0.0422(5) Uani d . 1 . . C
C13 1.15759(19) 0.10394(17) -0.12943(17) 0.0478(5) Uani d . 1 . . C
H13A 1.2376 0.0999 -0.1240 0.057 Uiso calc R 1 . . H
C14 1.1158(2) 0.13872(18) -0.04283(18) 0.0544(6) Uani d . 1 . . C
H14A 1.1672 0.1569 0.0201 0.065 Uiso calc R 1 . . H
C15 0.9972(2) 0.14580(17) -0.05155(19) 0.0543(6) Uani d . 1 . . C
C16 0.9202(2) 0.11839(18) -0.1441(2) 0.0597(6) Uani d . 1 . . C
H16A 0.8403 0.1233 -0.1491 0.072 Uiso calc R 1 . . H
C17 0.96299(19) 0.08328(18) -0.23001(19) 0.0541(6) Uani d . 1 . . C
H17A 0.9109 0.0650 -0.2925 0.065 Uiso calc R 1 . . H
C18 1.06355(19) -0.16603(18) -0.33362(18) 0.0499(5) Uani d . 1 . . C
C19 0.8609(2) -0.1937(2) -0.3959(3) 0.0877(9) Uani d . 1 . . C
H19A 0.7917 -0.1507 -0.4235 0.131 Uiso calc R 1 . . H
H19B 0.8565 -0.2253 -0.3292 0.131 Uiso calc R 1 . . H
H19C 0.8676 -0.2534 -0.4440 0.131 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C18 O3 C19 116.1(2) y
C9 C1 C2 114.73(15) ?
C18 C2 C1 108.98(16) ?
C18 C2 C3 106.37(17) ?
C1 C2 C3 108.25(16) ?
C18 C2 C11 112.53(16) ?
C1 C2 C11 112.94(16) ?
C3 C2 C11 107.46(16) ?
O1 C3 C4 122.4(2) ?
O1 C3 C2 121.2(2) ?
C4 C3 C2 116.35(19) ?
C3 C4 C10 113.37(17) ?
C6 C5 C10 111.8(2) ?
C5 C6 C7 110.8(2) ?
C8 C7 C6 111.1(2) ?
C7 C8 C9 111.5(2) ?
C1 C9 C8 111.37(17) ?
C1 C9 C10 110.02(16) ?
C8 C9 C10 110.45(17) ?
C5 C10 C4 112.73(19) ?
C5 C10 C9 111.73(18) ?
C4 C10 C9 110.24(17) ?
C12 C11 C2 115.77(16) ?
C17 C12 C13 117.81(19) ?
C17 C12 C11 121.2(2) ?
C13 C12 C11 120.93(18) ?
C14 C13 C12 121.4(2) ?
C15 C14 C13 119.1(2) ?
C16 C15 C14 121.0(2) ?
C16 C15 Cl1 120.06(18) ?
C14 C15 Cl1 118.9(2) ?
C15 C16 C17 119.4(2) ?
C12 C17 C16 121.3(2) ?
O2 C18 O3 123.0(2) y
O2 C18 C2 124.1(2) y
O3 C18 C2 112.9(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C15 . 1.751(2) y
O1 C3 . 1.210(3) y
O2 C18 . 1.202(2) y
O3 C18 . 1.337(3) y
O3 C19 . 1.451(3) y
C1 C9 . 1.528(3) ?
C1 C2 . 1.545(3) ?
C2 C18 . 1.530(3) yes
C2 C3 . 1.549(3) yes
C2 C11 . 1.566(3) ?
C3 C4 . 1.502(3) ?
C4 C10 . 1.532(3) ?
C5 C6 . 1.523(4) ?
C5 C10 . 1.528(3) ?
C6 C7 . 1.524(4) ?
C7 C8 . 1.524(3) ?
C8 C9 . 1.530(3) ?
C9 C10 . 1.535(3) ?
C11 C12 . 1.521(3) ?
C12 C17 . 1.389(3) ?
C12 C13 . 1.396(3) ?
C13 C14 . 1.392(3) ?
C14 C15 . 1.379(3) ?
C15 C16 . 1.377(3) ?
C16 C17 . 1.392(3) ?
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
_geom_hbond_publ_flag
C1 H1B O2 1_555 0.97 2.45 2.800(3) 101 no
C10 H10A \p(Ph) 2_744 0.98 2.64 3.613(3) 172 yes
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_publ_flag
C9 C1 C2 C18 166.43(15) ?
C9 C1 C2 C3 51.1(2) ?
C9 C1 C2 C11 -67.7(2) ?
C18 C2 C3 O1 14.9(3) ?
C1 C2 C3 O1 131.9(2) ?
C11 C2 C3 O1 -105.8(2) ?
C18 C2 C3 C4 -163.59(18) ?
C1 C2 C3 C4 -46.6(2) ?
C11 C2 C3 C4 75.7(2) ?
O1 C3 C4 C10 -128.8(2) ?
C2 C3 C4 C10 49.7(3) ?
C10 C5 C6 C7 -55.1(3) ?
C5 C6 C7 C8 56.2(3) ?
C6 C7 C8 C9 -56.9(3) ?
C2 C1 C9 C8 178.97(16) ?
C2 C1 C9 C10 -58.2(2) ?
C7 C8 C9 C1 177.99(18) ?
C7 C8 C9 C10 55.4(2) ?
C6 C5 C10 C4 179.3(2) ?
C6 C5 C10 C9 54.5(3) ?
C3 C4 C10 C5 -178.57(19) ?
C3 C4 C10 C9 -53.0(2) ?
C1 C9 C10 C5 -177.45(18) ?
C8 C9 C10 C5 -54.1(2) ?
C1 C9 C10 C4 56.4(2) ?
C8 C9 C10 C4 179.73(18) ?
C18 C2 C11 C12 64.2(2) ?
C1 C2 C11 C12 -59.7(2) y
C3 C2 C11 C12 -179.1(2) y
C2 C11 C12 C17 -99.7(2) ?
C2 C11 C12 C13 83.7(2) ?
C17 C12 C13 C14 0.7(3) ?
C11 C12 C13 C14 177.37(18) ?
C12 C13 C14 C15 -0.7(3) ?
C13 C14 C15 C16 0.4(3) ?
C13 C14 C15 Cl1 -177.13(16) ?
C14 C15 C16 C17 -0.1(3) ?
Cl1 C15 C16 C17 177.36(17) ?
C13 C12 C17 C16 -0.4(3) ?
C11 C12 C17 C16 -177.09(19) ?
C15 C16 C17 C12 0.1(3) ?
C19 O3 C18 O2 -0.2(3) ?
C19 O3 C18 C2 178.9(2) y
C1 C2 C18 O2 -25.9(3) ?
C3 C2 C18 O2 90.6(3) ?
C11 C2 C18 O2 -152.0(2) ?
C1 C2 C18 O3 155.0(2) y
C3 C2 C18 O3 -88.5(2) y
C11 C2 C18 O3 28.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4421843
