#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/21/2012189.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_2012189
loop_
_publ_author_name
'Parvez, Masood'
'Yadav, Veejendra K.'
'Balamurugan, Rengarajan'
_publ_section_title
;
 π-Facial selectivities of diastereotopic ketones:
 p-bromobenzoates of 4-hetero-1-decalinols
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1084
_journal_page_last               1088
_journal_paper_doi               10.1107/S0108270101009544
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C16 H19 Br O3'
_chemical_formula_sum            'C16 H19 Br O3'
_chemical_formula_weight         339.22
_chemical_name_common            'trans-4-oxa-1-decalinol  p-bromobenzoate'
_chemical_name_systematic        'trans-4-oxa-1-decalinyl p-bromobenzoate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.32(2)
_cell_angle_beta                 111.32(2)
_cell_angle_gamma                110.49(2)
_cell_formula_units_Z            2
_cell_length_a                   9.643(2)
_cell_length_b                   10.679(2)
_cell_length_c                   8.772(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     758.5(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Rigaku AFC-6S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .03
_diffrn_reflns_av_sigmaI/netI    .12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2702
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 0.8'
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.71
_exptl_absorpt_correction_T_max  .67
_exptl_absorpt_correction_T_min  .28
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'ψ-scan (3 reflections) (North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .15
_refine_diff_density_max         .42
_refine_diff_density_min         -.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .98
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .98
_refine_ls_R_factor_all          .165
_refine_ls_R_factor_gt           .039
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0513P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .130
_reflns_number_gt                1169
_reflns_number_total             2702
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1192.cif
_cod_data_source_block           XVII
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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_database_code               2012189
_cod_database_fobs_code          2012189
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 .62706(9) 1.28442(7) .24217(9) .0785(3) Uani d . 1 . . Br
O1 -.0142(4) .1901(4) .1044(5) .0590(10) Uani d . 1 . . O
O2 .2942(4) .6079(4) .2383(5) .0635(11) Uani d . 1 . . O
O3 .5457(5) .6687(4) .4412(5) .0817(14) Uani d . 1 . . O
C1 .0561(7) .2611(6) .2776(7) .0618(16) Uani d . 1 . . C
H1A .1439 .2365 .3410 .074 Uiso calc R 1 . . H
H1B -.0263 .2323 .3206 .074 Uiso calc R 1 . . H
C2 .1241(7) .4177(6) .3055(7) .0669(17) Uani d . 1 . . C
H2A .1763 .4638 .4262 .080 Uiso calc R 1 . . H
H2B .0354 .4440 .2505 .080 Uiso calc R 1 . . H
C3 .2466(6) .4616(5) .2328(7) .0526(15) Uani d . 1 . . C
H3 .3433 .4465 .2980 .063 Uiso calc R 1 . . H
C4 .1697(7) .3806(5) .0479(7) .0545(15) Uani d . 1 . . C
H4 .0761 .4013 -.0121 .065 Uiso calc R 1 . . H
C5 .2765(8) .4151(7) -.0409(9) .083(2) Uani d . 1 . . C
H5A .3736 .4004 .0188 .099 Uiso calc R 1 . . H
H5B .3117 .5127 -.0380 .099 Uiso calc R 1 . . H
C6 .1901(9) .3276(8) -.2258(9) .091(2) Uani d . 1 . . C
H6A .1014 .3510 -.2899 .109 Uiso calc R 1 . . H
H6B .2672 .3481 -.2761 .109 Uiso calc R 1 . . H
C7 .1229(9) .1762(8) -.2353(9) .088(2) Uani d . 1 . . C
H7A .2134 .1511 -.1837 .105 Uiso calc R 1 . . H
H7B .0619 .1228 -.3537 .105 Uiso calc R 1 . . H
C8 .0128(8) .1386(6) -.1477(8) .0769(18) Uani d . 1 . . C
H8A -.0215 .0411 -.1507 .092 Uiso calc R 1 . . H
H8B -.0846 .1531 -.2070 .092 Uiso calc R 1 . . H
C9 .1009(7) .2262(5) .0354(7) .0565(15) Uani d . 1 . . C
H9 .1913 .2026 .0979 .068 Uiso calc R 1 . . H
C10 .4493(7) .6999(6) .3404(7) .0511(14) Uani d . 1 . . C
C11 .4874(6) .8392(5) .3144(6) .0418(13) Uani d . 1 . . C
C12 .3821(6) .8653(5) .1799(6) .0486(14) Uani d . 1 . . C
H12 .2823 .7935 .1035 .058 Uiso calc R 1 . . H
C13 .4238(7) .9973(6) .1577(7) .0579(16) Uani d . 1 . . C
H13 .3526 1.0138 .0659 .070 Uiso calc R 1 . . H
C14 .5702(7) 1.1043(5) .2710(7) .0487(14) Uani d . 1 . . C
C15 .6768(7) 1.0807(6) .4077(7) .0558(15) Uani d . 1 . . C
H15 .7752 1.1533 .4854 .067 Uiso calc R 1 . . H
C16 .6356(6) .9484(6) .4274(7) .0528(15) Uani d . 1 . . C
H16 .7081 .9317 .5179 .063 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 '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
C9 O1 C1 111.9(4) y
C10 O2 C3 119.2(4) y
O1 C1 C2 111.7(4) n
O1 C1 H1A 109.3 n
C2 C1 H1A 109.3 n
O1 C1 H1B 109.3 n
C2 C1 H1B 109.3 n
H1A C1 H1B 107.9 n
C1 C2 C3 109.3(5) n
C1 C2 H2A 109.8 n
C3 C2 H2A 109.8 n
C1 C2 H2B 109.8 n
C3 C2 H2B 109.8 n
H2A C2 H2B 108.3 n
O2 C3 C2 109.1(5) n
O2 C3 C4 107.3(4) n
C2 C3 C4 110.1(4) n
O2 C3 H3 110.1 n
C2 C3 H3 110.1 n
C4 C3 H3 110.1 n
C5 C4 C9 111.1(5) n
C5 C4 C3 115.9(5) n
C9 C4 C3 108.7(4) n
C5 C4 H4 106.9 n
C9 C4 H4 106.9 n
C3 C4 H4 106.9 n
C4 C5 C6 112.4(5) n
C4 C5 H5A 109.1 n
C6 C5 H5A 109.1 n
C4 C5 H5B 109.1 n
C6 C5 H5B 109.1 n
H5A C5 H5B 107.9 n
C7 C6 C5 110.4(5) n
C7 C6 H6A 109.6 n
C5 C6 H6A 109.6 n
C7 C6 H6B 109.6 n
C5 C6 H6B 109.6 n
H6A C6 H6B 108.1 n
C6 C7 C8 112.7(6) n
C6 C7 H7A 109.1 n
C8 C7 H7A 109.1 n
C6 C7 H7B 109.1 n
C8 C7 H7B 109.1 n
H7A C7 H7B 107.8 n
C7 C8 C9 110.6(6) n
C7 C8 H8A 109.5 n
C9 C8 H8A 109.5 n
C7 C8 H8B 109.5 n
C9 C8 H8B 109.5 n
H8A C8 H8B 108.1 n
O1 C9 C8 106.7(5) n
O1 C9 C4 111.4(4) n
C8 C9 C4 111.7(4) n
O1 C9 H9 109.0 n
C8 C9 H9 109.0 n
C4 C9 H9 109.0 n
O3 C10 O2 122.3(5) n
O3 C10 C11 124.3(5) n
O2 C10 C11 113.4(5) n
C12 C11 C16 118.7(5) n
C12 C11 C10 122.2(5) n
C16 C11 C10 119.1(4) n
C11 C12 C13 120.5(5) n
C11 C12 H12 119.8 n
C13 C12 H12 119.8 n
C14 C13 C12 120.1(5) n
C14 C13 H13 119.9 n
C12 C13 H13 119.9 n
C13 C14 C15 120.3(5) n
C13 C14 Br1 120.3(4) n
C15 C14 Br1 119.3(4) n
C16 C15 C14 119.2(5) n
C16 C15 H15 120.4 n
C14 C15 H15 120.4 n
C15 C16 C11 121.1(5) n
C15 C16 H16 119.4 n
C11 C16 H16 119.4 n
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
Br1 C14 . 1.880(5) y
O1 C9 . 1.410(6) y
O1 C1 . 1.407(6) y
O2 C10 . 1.344(6) y
O2 C3 . 1.456(6) y
O3 C10 . 1.200(6) y
C1 C2 . 1.520(7) n
C1 H1A . .9700 n
C1 H1B . .9700 n
C2 C3 . 1.500(7) n
C2 H2A . .9700 n
C2 H2B . .9700 n
C3 C4 . 1.516(7) n
C3 H3 . .9800 n
C4 C5 . 1.477(7) n
C4 C9 . 1.521(7) n
C4 H4 . .9800 n
C5 C6 . 1.529(9) n
C5 H5A . .9700 n
C5 H5B . .9700 n
C6 C7 . 1.497(9) n
C6 H6A . .9700 n
C6 H6B . .9700 n
C7 C8 . 1.497(8) n
C7 H7A . .9700 n
C7 H7B . .9700 n
C8 C9 . 1.516(8) n
C8 H8A . .9700 n
C8 H8B . .9700 n
C9 H9 . .9800 n
C10 C11 . 1.468(7) n
C11 C12 . 1.378(7) n
C11 C16 . 1.390(7) n
C12 C13 . 1.381(7) n
C12 H12 . .9300 n
C13 C14 . 1.373(7) n
C13 H13 . .9300 n
C14 C15 . 1.382(7) n
C15 C16 . 1.377(7) n
C15 H15 . .9300 n
C16 H16 . .9300 n
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 O1 C1 C2 59.9(6) n
O1 C1 C2 C3 -56.7(6) n
C10 O2 C3 C2 113.6(5) n
C10 O2 C3 C4 -127.1(5) n
C1 C2 C3 O2 172.1(4) n
C1 C2 C3 C4 54.6(6) n
O2 C3 C4 C5 60.4(6) n
C2 C3 C4 C5 179.1(5) n
O2 C3 C4 C9 -173.6(4) n
C2 C3 C4 C9 -55.0(6) n
C9 C4 C5 C6 54.6(7) n
C3 C4 C5 C6 179.3(5) n
C4 C5 C6 C7 -54.5(8) n
C5 C6 C7 C8 54.7(8) n
C6 C7 C8 C9 -55.4(8) n
C1 O1 C9 C8 177.4(5) n
C1 O1 C9 C4 -60.5(6) n
C7 C8 C9 O1 176.4(5) n
C7 C8 C9 C4 54.5(7) n
C5 C4 C9 O1 -173.9(5) n
C3 C4 C9 O1 57.4(6) n
C5 C4 C9 C8 -54.7(7) n
C3 C4 C9 C8 176.6(5) n
C3 O2 C10 O3 -8.3(8) n
C3 O2 C10 C11 171.2(4) n
O3 C10 C11 C12 169.5(5) n
O2 C10 C11 C12 -9.9(7) n
O3 C10 C11 C16 -9.4(8) n
O2 C10 C11 C16 171.1(5) n
C16 C11 C12 C13 .3(8) n
C10 C11 C12 C13 -178.7(5) n
C11 C12 C13 C14 -.7(8) n
C12 C13 C14 C15 .1(8) n
C12 C13 C14 Br1 -179.7(4) n
C13 C14 C15 C16 .9(8) n
Br1 C14 C15 C16 -179.3(4) n
C14 C15 C16 C11 -1.3(8) n
C12 C11 C16 C15 .7(8) n
C10 C11 C16 C15 179.7(5) n
