#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/21/2012190.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_2012190
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         'C23 H26 Br N O2'
_chemical_formula_sum            'C23 H26 Br N O2'
_chemical_formula_weight         428.36
_chemical_name_common
'N-benzyl-cis-4-aza-1-decalinol p-bromobenzoate'
_chemical_name_systematic
'N-benzyl-cis-4-aza-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                96.06(2)
_cell_angle_beta                 106.22(2)
_cell_angle_gamma                100.42(3)
_cell_formula_units_Z            2
_cell_length_a                   11.914(3)
_cell_length_b                   13.144(3)
_cell_length_c                   6.922(2)
_cell_measurement_reflns_used    12
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1009.6(5)
_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      170(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  .09
_diffrn_reflns_av_sigmaI/netI    .23
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3574
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        <1.1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.05
_exptl_absorpt_correction_T_max  .52
_exptl_absorpt_correction_T_min  .39
_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    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             444
_exptl_crystal_size_max          .60
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .32
_refine_diff_density_max         .43
_refine_diff_density_min         -.76
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .95
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .95
_refine_ls_R_factor_all          .207
_refine_ls_R_factor_gt           .040
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.018P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .110
_reflns_number_gt                1407
_reflns_number_total             3574
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1192.cif
_cod_data_source_block           XVIII
_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               2012190
_cod_database_fobs_code          2012190
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 .42113(7) .14473(6) .24555(11) .0465(2) Uani d . 1 . . Br
O1 .6728(3) .4668(3) -.2993(6) .0341(11) Uani d . 1 . . O
O2 .7113(4) .3176(3) -.4277(6) .0430(12) Uani d . 1 . . O
N1 .8553(4) .7240(3) -.4752(6) .0246(12) Uani d . 1 . . N
C1 .7295(5) .6837(4) -.5911(9) .0348(16) Uani d . 1 . . C
H1A .7232 .6443 -.7251 .042 Uiso calc R 1 . . H
H1B .6894 .7429 -.6155 .042 Uiso calc R 1 . . H
C2 .6676(5) .6120(4) -.4755(9) .0338(16) Uani d . 1 . . C
H2A .6676 .6529 -.3469 .041 Uiso calc R 1 . . H
H2B .5832 .5826 -.5587 .041 Uiso calc R 1 . . H
C3 .7303(5) .5240(4) -.4280(9) .0304(16) Uani d . 1 . . C
H3 .7191 .4763 -.5576 .036 Uiso calc R 1 . . H
C4 .8648(5) .5656(4) -.3186(8) .0279(15) Uani d . 1 . . C
H4 .9037 .5042 -.3122 .034 Uiso calc R 1 . . H
C5 .8946(5) .6231(4) -.1002(8) .0323(16) Uani d . 1 . . C
H5A .8563 .6840 -.1017 .039 Uiso calc R 1 . . H
H5B .8620 .5754 -.0178 .039 Uiso calc R 1 . . H
C6 1.0306(5) .6610(5) -.0026(9) .0441(18) Uani d . 1 . . C
H6A 1.0478 .7014 .1353 .053 Uiso calc R 1 . . H
H6B 1.0680 .5997 .0117 .053 Uiso calc R 1 . . H
C7 1.0843(5) .7299(5) -.1330(9) .0397(18) Uani d . 1 . . C
H7A 1.0534 .7949 -.1350 .048 Uiso calc R 1 . . H
H7B 1.1726 .7499 -.0725 .048 Uiso calc R 1 . . H
C8 1.0528(5) .6724(4) -.3489(9) .0364(16) Uani d . 1 . . C
H8A 1.0888 .6101 -.3468 .044 Uiso calc R 1 . . H
H8B 1.0877 .7190 -.4307 .044 Uiso calc R 1 . . H
C9 .9177(5) .6375(4) -.4502(8) .0271(15) Uani d . 1 . . C
H9 .9026 .5957 -.5879 .032 Uiso calc R 1 . . H
C10 .9084(5) .8056(4) -.5720(8) .0291(15) Uani d . 1 . . C
H10A .8963 .7765 -.7160 .035 Uiso calc R 1 . . H
H10B .9958 .8267 -.5023 .035 Uiso calc R 1 . . H
C11 .8556(5) .9003(4) -.5654(9) .0293(15) Uani d . 1 . . C
C12 .8504(5) .9502(5) -.3834(10) .0433(18) Uani d . 1 . . C
H12 .8808 .9241 -.2609 .052 Uiso calc R 1 . . H
C13 .8017(6) 1.0370(5) -.3769(12) .057(2) Uani d . 1 . . C
H13 .7965 1.0690 -.2510 .068 Uiso calc R 1 . . H
C14 .7601(6) 1.0783(5) -.5517(14) .061(2) Uani d . 1 . . C
H14 .7287 1.1396 -.5459 .074 Uiso calc R 1 . . H
C15 .7647(6) 1.0300(6) -.7330(13) .055(2) Uani d . 1 . . C
H15 .7348 1.0569 -.8548 .066 Uiso calc R 1 . . H
C16 .8130(5) .9419(5) -.7394(10) .0371(17) Uani d . 1 . . C
H16 .8167 .9094 -.8661 .044 Uiso calc R 1 . . H
C17 .6702(5) .3632(5) -.3126(9) .0263(14) Uani d . 1 . . C
C18 .6095(5) .3139(5) -.1750(8) .0252(15) Uani d . 1 . . C
C19 .5804(5) .3723(5) -.0246(9) .0341(16) Uani d . 1 . . C
H19 .5987 .4467 -.0075 .041 Uiso calc R 1 . . H
C20 .5238(5) .3212(5) .1023(9) .0407(18) Uani d . 1 . . C
H20 .5033 .3604 .2056 .049 Uiso calc R 1 . . H
C21 .4985(5) .2126(5) .0742(9) .0337(16) Uani d . 1 . . C
C22 .5246(5) .1556(5) -.0765(9) .0367(17) Uani d . 1 . . C
H22 .5041 .0812 -.0959 .044 Uiso calc R 1 . . H
C23 .5807(5) .2051(4) -.2011(8) .0290(15) Uani d . 1 . . C
H23 .5996 .1648 -.3051 .035 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'
N N .0061 .0033 '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
C17 O1 C3 117.3(4) y
C1 N1 C10 109.5(4) y
C1 N1 C9 110.1(4) y
C10 N1 C9 113.9(4) y
N1 C1 C2 110.4(4) n
N1 C1 H1A 109.6 n
C2 C1 H1A 109.6 n
N1 C1 H1B 109.6 n
C2 C1 H1B 109.6 n
H1A C1 H1B 108.1 n
C3 C2 C1 110.7(4) n
C3 C2 H2A 109.5 n
C1 C2 H2A 109.5 n
C3 C2 H2B 109.5 n
C1 C2 H2B 109.5 n
H2A C2 H2B 108.1 n
O1 C3 C2 106.5(4) n
O1 C3 C4 110.8(4) n
C2 C3 C4 111.4(5) n
O1 C3 H3 109.4 n
C2 C3 H3 109.4 n
C4 C3 H3 109.4 n
C3 C4 C5 114.4(5) n
C3 C4 C9 108.4(4) n
C5 C4 C9 110.7(4) n
C3 C4 H4 107.7 n
C5 C4 H4 107.7 n
C9 C4 H4 107.7 n
C6 C5 C4 110.8(5) n
C6 C5 H5A 109.5 n
C4 C5 H5A 109.5 n
C6 C5 H5B 109.5 n
C4 C5 H5B 109.5 n
H5A C5 H5B 108.1 n
C7 C6 C5 110.6(5) n
C7 C6 H6A 109.5 n
C5 C6 H6A 109.5 n
C7 C6 H6B 109.5 n
C5 C6 H6B 109.5 n
H6A C6 H6B 108.1 n
C8 C7 C6 110.7(5) n
C8 C7 H7A 109.5 n
C6 C7 H7A 109.5 n
C8 C7 H7B 109.5 n
C6 C7 H7B 109.5 n
H7A C7 H7B 108.1 n
C7 C8 C9 112.3(5) n
C7 C8 H8A 109.2 n
C9 C8 H8A 109.2 n
C7 C8 H8B 109.2 n
C9 C8 H8B 109.2 n
H8A C8 H8B 107.9 n
N1 C9 C8 114.2(4) n
N1 C9 C4 108.7(4) n
C8 C9 C4 108.3(5) n
N1 C9 H9 108.5 n
C8 C9 H9 108.5 n
C4 C9 H9 108.5 n
N1 C10 C11 112.7(4) n
N1 C10 H10A 109.1 n
C11 C10 H10A 109.1 n
N1 C10 H10B 109.1 n
C11 C10 H10B 109.1 n
H10A C10 H10B 107.8 n
C12 C11 C16 117.9(6) n
C12 C11 C10 120.8(6) n
C16 C11 C10 121.3(6) n
C13 C12 C11 120.9(6) n
C13 C12 H12 119.6 n
C11 C12 H12 119.6 n
C14 C13 C12 120.6(7) n
C14 C13 H13 119.7 n
C12 C13 H13 119.7 n
C15 C14 C13 119.3(7) n
C15 C14 H14 120.4 n
C13 C14 H14 120.4 n
C14 C15 C16 120.0(7) n
C14 C15 H15 120.0 n
C16 C15 H15 120.0 n
C15 C16 C11 121.3(6) n
C15 C16 H16 119.4 n
C11 C16 H16 119.4 n
O2 C17 O1 122.6(5) n
O2 C17 C18 125.2(5) n
O1 C17 C18 112.2(5) n
C19 C18 C23 119.7(5) n
C19 C18 C17 122.4(5) n
C23 C18 C17 117.9(5) n
C18 C19 C20 119.8(6) n
C18 C19 H19 120.1 n
C20 C19 H19 120.1 n
C21 C20 C19 118.8(6) n
C21 C20 H20 120.6 n
C19 C20 H20 120.6 n
C22 C21 C20 121.1(5) n
C22 C21 Br1 120.5(5) n
C20 C21 Br1 118.3(5) n
C21 C22 C23 120.4(5) n
C21 C22 H22 119.8 n
C23 C22 H22 119.8 n
C22 C23 C18 120.0(5) n
C22 C23 H23 120.0 n
C18 C23 H23 120.0 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 C21 . 1.894(5) y
O1 C17 . 1.348(6) y
O1 C3 . 1.457(6) y
O2 C17 . 1.207(6) y
N1 C1 . 1.457(6) y
N1 C10 . 1.464(6) y
N1 C9 . 1.467(6) y
C1 C2 . 1.520(6) n
C1 H1A . .9900 n
C1 H1B . .9900 n
C2 C3 . 1.503(7) n
C2 H2A . .9900 n
C2 H2B . .9900 n
C3 C4 . 1.536(7) n
C3 H3 . 1.0000 n
C4 C5 . 1.531(7) n
C4 C9 . 1.551(7) n
C4 H4 . 1.0000 n
C5 C6 . 1.535(7) n
C5 H5A . .9900 n
C5 H5B . .9900 n
C6 C7 . 1.527(7) n
C6 H6A . .9900 n
C6 H6B . .9900 n
C7 C8 . 1.513(7) n
C7 H7A . .9900 n
C7 H7B . .9900 n
C8 C9 . 1.526(7) n
C8 H8A . .9900 n
C8 H8B . .9900 n
C9 H9 . 1.0000 n
C10 C11 . 1.495(7) n
C10 H10A . .9900 n
C10 H10B . .9900 n
C11 C12 . 1.380(7) n
C11 C16 . 1.381(7) n
C12 C13 . 1.373(8) n
C12 H12 . .9500 n
C13 C14 . 1.379(9) n
C13 H13 . .9500 n
C14 C15 . 1.365(9) n
C14 H14 . .9500 n
C15 C16 . 1.385(8) n
C15 H15 . .9500 n
C16 H16 . .9500 n
C17 C18 . 1.482(7) n
C18 C19 . 1.387(7) n
C18 C23 . 1.389(7) n
C19 C20 . 1.403(7) n
C19 H19 . .9500 n
C20 C21 . 1.386(7) n
C20 H20 . .9500 n
C21 C22 . 1.359(7) n
C22 C23 . 1.377(7) n
C22 H22 . .9500 n
C23 H23 . .9500 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
C10 N1 C1 C2 -170.8(4) n
C9 N1 C1 C2 63.2(6) n
N1 C1 C2 C3 -56.6(6) n
C17 O1 C3 C2 149.8(5) n
C17 O1 C3 C4 -88.9(6) n
C1 C2 C3 O1 174.0(4) n
C1 C2 C3 C4 53.1(6) n
O1 C3 C4 C5 -48.7(6) n
C2 C3 C4 C5 69.7(6) n
O1 C3 C4 C9 -172.8(4) n
C2 C3 C4 C9 -54.4(6) n
C3 C4 C5 C6 179.5(5) n
C9 C4 C5 C6 -57.6(6) n
C4 C5 C6 C7 56.0(7) n
C5 C6 C7 C8 -55.6(7) n
C6 C7 C8 C9 58.1(7) n
C1 N1 C9 C8 174.3(4) n
C10 N1 C9 C8 50.8(6) n
C1 N1 C9 C4 -64.8(5) n
C10 N1 C9 C4 171.8(4) n
C7 C8 C9 N1 62.9(6) n
C7 C8 C9 C4 -58.3(6) n
C3 C4 C9 N1 59.4(6) n
C5 C4 C9 N1 -66.8(6) n
C3 C4 C9 C8 -176.0(5) n
C5 C4 C9 C8 57.7(6) n
C1 N1 C10 C11 65.4(6) n
C9 N1 C10 C11 -170.8(5) n
N1 C10 C11 C12 52.6(7) n
N1 C10 C11 C16 -128.7(5) n
C16 C11 C12 C13 1.4(9) n
C10 C11 C12 C13 -179.8(5) n
C11 C12 C13 C14 -2.0(10) n
C12 C13 C14 C15 1.9(10) n
C13 C14 C15 C16 -1.3(10) n
C14 C15 C16 C11 .8(9) n
C12 C11 C16 C15 -.9(8) n
C10 C11 C16 C15 -179.6(5) n
C3 O1 C17 O2 -1.3(8) n
C3 O1 C17 C18 -179.9(4) n
O2 C17 C18 C19 170.0(6) n
O1 C17 C18 C19 -11.4(8) n
O2 C17 C18 C23 -10.6(9) n
O1 C17 C18 C23 168.1(5) n
C23 C18 C19 C20 1.1(9) n
C17 C18 C19 C20 -179.5(5) n
C18 C19 C20 C21 .2(9) n
C19 C20 C21 C22 -1.7(9) n
C19 C20 C21 Br1 -179.6(4) n
C20 C21 C22 C23 2.0(9) n
Br1 C21 C22 C23 179.9(4) n
C21 C22 C23 C18 -.8(9) n
C19 C18 C23 C22 -.8(8) n
C17 C18 C23 C22 179.7(5) n
