#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/88/2238826.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_2238826
loop_
_publ_author_name
'Bimoussa, Abdoullah'
'Auhmani, Aziz'
'Ait Itto, My Youssef'
'Daran, Jean-Claude'
'Auhmani, Abdelwahed'
_publ_section_title
;
 Absolute configuration of
 (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.0^1,3^]dodec-9-ene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1692
_journal_page_last               o1693
_journal_paper_doi               10.1107/S1600536813028183
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H23 Br Cl2'
_chemical_formula_moiety         'C16 H23 Br Cl2'
_chemical_formula_sum            'C16 H23 Br Cl2'
_chemical_formula_weight         366.15
_chemical_name_systematic
(1S,3R,8R)-10-Bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.0^1,3^]dodec-9-ene
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1000(2)
_cell_length_b                   12.5490(4)
_cell_length_c                   14.4070(5)
_cell_measurement_reflns_used    5474
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.77
_cell_measurement_theta_min      3.065
_cell_volume                     1645.22(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.1978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9248
_diffrn_reflns_theta_full        70.90
_diffrn_reflns_theta_max         70.90
_diffrn_reflns_theta_min         4.67
_exptl_absorpt_coefficient_mu    6.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       box
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.459
_refine_ls_abs_structure_details 'Flack (1983), 1307 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.015(17)
_refine_ls_extinction_coef       0.0037(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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0267
_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)+(0.0372P)²+0.3180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                3012
_reflns_number_total             3127
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yk2099.cif
_cod_data_source_block           I
_cod_database_code               2238826
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
C C1 0.3341(3) 0.3344(2) 0.29478(17) 0.0200(5) Uani d . 1 1
C C2 0.4125(3) 0.2394(2) 0.33667(17) 0.0245(5) Uani d . 1 1
C C3 0.3927(3) 0.3389(2) 0.39476(17) 0.0264(5) Uani d . 1 1
C C4 0.2786(4) 0.3369(2) 0.47129(18) 0.0356(6) Uani d . 1 1
H H4A 0.3274 0.3208 0.5311 0.043 Uiso calc R 1 1
H H4B 0.2068 0.2795 0.4586 0.043 Uiso calc R 1 1
C C5 0.1975(4) 0.4434(2) 0.47910(19) 0.0372(6) Uani d . 1 1
H H5A 0.2572 0.4925 0.5175 0.045 Uiso calc R 1 1
H H5B 0.1035 0.4314 0.5120 0.045 Uiso calc R 1 1
C C6 0.1646(3) 0.4980(2) 0.38583(18) 0.0312(6) Uani d . 1 1
H H6A 0.1074 0.5634 0.3989 0.037 Uiso calc R 1 1
H H6B 0.2594 0.5208 0.3586 0.037 Uiso calc R 1 1
C C7 0.0814(3) 0.4344(2) 0.31168(19) 0.0295(6) Uani d . 1 1
C C8 0.1674(3) 0.3298(2) 0.28177(17) 0.0226(5) Uani d . 1 1
H H8 0.1312 0.2714 0.3231 0.027 Uiso calc R 1 1
C C9 0.1316(3) 0.2964(2) 0.18373(18) 0.0259(5) Uani d . 1 1
H H9 0.0338 0.2742 0.1709 0.031 Uiso calc R 1 1
C C10 0.2264(3) 0.2957(2) 0.11464(16) 0.0249(5) Uani d . 1 1
C C11 0.3846(3) 0.3268(2) 0.12612(16) 0.0234(5) Uani d . 1 1
H H11A 0.4155 0.3702 0.0721 0.028 Uiso calc R 1 1
H H11B 0.4460 0.2617 0.1273 0.028 Uiso calc R 1 1
C C12 0.4109(2) 0.39027(19) 0.21497(16) 0.0222(5) Uani d . 1 1
H H12A 0.5176 0.3952 0.2276 0.027 Uiso calc R 1 1
H H12B 0.3717 0.4634 0.2079 0.027 Uiso calc R 1 1
C C13 0.5259(3) 0.4058(2) 0.4181(2) 0.0378(7) Uani d . 1 1
H H13A 0.4943 0.4778 0.4355 0.057 Uiso calc R 1 1
H H13B 0.5907 0.4097 0.3639 0.057 Uiso calc R 1 1
H H13C 0.5789 0.3733 0.4701 0.057 Uiso calc R 1 1
C C14 -0.0692(3) 0.4003(3) 0.3467(3) 0.0564(10) Uani d . 1 1
H H14A -0.0577 0.3582 0.4036 0.085 Uiso calc R 1 1
H H14B -0.1181 0.3570 0.2993 0.085 Uiso calc R 1 1
H H14C -0.1286 0.4636 0.3599 0.085 Uiso calc R 1 1
C C15 0.0576(4) 0.5105(2) 0.2286(2) 0.0399(7) Uani d . 1 1
H H15A 0.0002 0.4742 0.1806 0.060 Uiso calc R 1 1
H H15B 0.1530 0.5317 0.2031 0.060 Uiso calc R 1 1
H H15C 0.0044 0.5741 0.2496 0.060 Uiso calc R 1 1
C C16 0.1748(3) 0.2646(2) 0.01985(19) 0.0339(6) Uani d . 1 1
H H16A 0.1982 0.3225 -0.0244 0.041 Uiso calc R 1 1
H H16B 0.0667 0.2556 0.0208 0.041 Uiso calc R 1 1
Cl Cl1 0.59023(7) 0.20569(6) 0.29648(5) 0.03423(16) Uani d . 1 1
Cl Cl2 0.31861(8) 0.12015(5) 0.36321(5) 0.03703(17) Uani d . 1 1
Br Br1 0.26676(3) 0.13107(2) -0.02346(2) 0.04148(11) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 C1 C12 116.7(2)
C2 C1 C8 119.1(2)
C12 C1 C8 112.4(2)
C2 C1 C3 59.50(16)
C12 C1 C3 122.2(2)
C8 C1 C3 117.4(2)
C3 C2 C1 60.98(16)
C3 C2 Cl2 121.47(19)
C1 C2 Cl2 121.68(18)
C3 C2 Cl1 119.12(19)
C1 C2 Cl1 119.24(18)
Cl2 C2 Cl1 108.12(14)
C13 C3 C4 113.4(2)
C13 C3 C2 119.0(2)
C4 C3 C2 118.0(2)
C13 C3 C1 120.5(2)
C4 C3 C1 116.3(2)
C2 C3 C1 59.51(16)
C3 C4 C5 111.7(2)
C3 C4 H4A 109.3
C5 C4 H4A 109.3
C3 C4 H4B 109.3
C5 C4 H4B 109.3
H4A C4 H4B 107.9
C4 C5 C6 114.7(2)
C4 C5 H5A 108.6
C6 C5 H5A 108.6
C4 C5 H5B 108.6
C6 C5 H5B 108.6
H5A C5 H5B 107.6
C7 C6 C5 118.3(2)
C7 C6 H6A 107.7
C5 C6 H6A 107.7
C7 C6 H6B 107.7
C5 C6 H6B 107.7
H6A C6 H6B 107.1
C14 C7 C6 111.1(2)
C14 C7 C15 107.7(3)
C6 C7 C15 106.7(2)
C14 C7 C8 107.5(2)
C6 C7 C8 112.1(2)
C15 C7 C8 111.7(2)
C9 C8 C1 109.8(2)
C9 C8 C7 112.2(2)
C1 C8 C7 115.1(2)
C9 C8 H8 106.4
C1 C8 H8 106.4
C7 C8 H8 106.4
C10 C9 C8 124.6(2)
C10 C9 H9 117.7
C8 C9 H9 117.7
C9 C10 C16 119.1(2)
C9 C10 C11 122.9(2)
C16 C10 C11 118.0(2)
C10 C11 C12 112.2(2)
C10 C11 H11A 109.2
C12 C11 H11A 109.2
C10 C11 H11B 109.2
C12 C11 H11B 109.2
H11A C11 H11B 107.9
C1 C12 C11 108.8(2)
C1 C12 H12A 109.9
C11 C12 H12A 109.9
C1 C12 H12B 109.9
C11 C12 H12B 109.9
H12A C12 H12B 108.3
C3 C13 H13A 109.5
C3 C13 H13B 109.5
H13A C13 H13B 109.5
C3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C7 C14 H14A 109.5
C7 C14 H14B 109.5
H14A C14 H14B 109.5
C7 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 C15 H15A 109.5
C7 C15 H15B 109.5
H15A C15 H15B 109.5
C7 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C10 C16 Br1 112.15(18)
C10 C16 H16A 109.2
Br1 C16 H16A 109.2
C10 C16 H16B 109.2
Br1 C16 H16B 109.2
H16A C16 H16B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.515(3)
C1 C12 1.518(3)
C1 C8 1.529(3)
C1 C3 1.537(3)
C2 C3 1.515(3)
C2 Cl2 1.765(3)
C2 Cl1 1.769(3)
C3 C13 1.512(4)
C3 C4 1.515(4)
C4 C5 1.531(4)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.538(4)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.533(4)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C14 1.522(4)
C7 C15 1.546(4)
C7 C8 1.589(4)
C8 C9 1.509(3)
C8 H8 1.0000
C9 C10 1.317(4)
C9 H9 0.9500
C10 C16 1.496(3)
C10 C11 1.501(3)
C11 C12 1.526(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 Br1 1.974(3)
C16 H16A 0.9900
C16 H16B 0.9900
