#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$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 '\w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0372P)^2^+0.3180P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_iucr_refine_instructions_details
;
TITL RN2 in P2(1)2(1)2(1)
CELL 1.54184 9.1000 12.5490 14.4070 90.000 90.000 90.000
ZERR 4.00 0.0002 0.0004 0.0005 0.000 0.000 0.000
LATT -1
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 1/2 + X, 1/2 - Y, - Z
SYMM - X, 1/2 + Y, 1/2 - Z
SFAC C H CL BR
UNIT 64 92 8 4
MERG 2
FMAP 2
PLAN 25
ACTA
BOND $H
L.S. 8
TEMP -100.00
WGHT 0.037200 0.318000
EXTI 0.003658
FVAR 5.95620
C1 1 0.334070 0.334354 0.294779 11.00000 0.02267 0.01748 =
0.01993 -0.00030 0.00044 0.00074
C2 1 0.412518 0.239369 0.336672 11.00000 0.02430 0.02265 =
0.02658 0.00185 -0.00065 0.00088
C3 1 0.392728 0.338943 0.394757 11.00000 0.03425 0.02173 =
0.02324 -0.00041 -0.00334 0.00332
C4 1 0.278642 0.336938 0.471291 11.00000 0.05484 0.02997 =
0.02187 0.00072 0.00458 0.00215
AFIX 23
H4A 2 0.327354 0.320833 0.531112 11.00000 -1.20000
H4B 2 0.206788 0.279527 0.458587 11.00000 -1.20000
AFIX 0
C5 1 0.197481 0.443438 0.479101 11.00000 0.05165 0.03503 =
0.02487 -0.00421 0.00368 0.00372
AFIX 23
H5A 2 0.257218 0.492465 0.517501 11.00000 -1.20000
H5B 2 0.103466 0.431378 0.512045 11.00000 -1.20000
AFIX 0
C6 1 0.164557 0.497996 0.385828 11.00000 0.03409 0.02690 =
0.03270 -0.00635 0.00327 0.00287
AFIX 23
H6A 2 0.107358 0.563392 0.398942 11.00000 -1.20000
H6B 2 0.259386 0.520794 0.358627 11.00000 -1.20000
AFIX 0
C7 1 0.081406 0.434435 0.311682 11.00000 0.02227 0.03201 =
0.03419 -0.00696 0.00417 0.00482
C8 1 0.167419 0.329772 0.281773 11.00000 0.01970 0.02097 =
0.02722 -0.00292 0.00331 -0.00457
AFIX 13
H8 2 0.131152 0.271370 0.323069 11.00000 -1.20000
AFIX 0
C9 1 0.131588 0.296358 0.183725 11.00000 0.01868 0.02442 =
0.03470 -0.00518 -0.00399 0.00173
AFIX 43
H9 2 0.033824 0.274237 0.170935 11.00000 -1.20000
AFIX 0
C10 1 0.226405 0.295722 0.114636 11.00000 0.02835 0.02169 =
0.02469 -0.00226 -0.00642 0.00598
C11 1 0.384620 0.326841 0.126123 11.00000 0.02514 0.02461 =
0.02032 0.00189 0.00364 0.00182
AFIX 23
H11A 2 0.415450 0.370192 0.072114 11.00000 -1.20000
H11B 2 0.445988 0.261712 0.127270 11.00000 -1.20000
AFIX 0
C12 1 0.410909 0.390274 0.214971 11.00000 0.01784 0.02081 =
0.02805 0.00141 0.00063 -0.00030
AFIX 23
H12A 2 0.517619 0.395177 0.227648 11.00000 -1.20000
H12B 2 0.371749 0.463427 0.207898 11.00000 -1.20000
AFIX 0
C13 1 0.525874 0.405797 0.418113 11.00000 0.04023 0.03472 =
0.03832 -0.00794 -0.01666 0.00044
AFIX 137
H13A 2 0.494322 0.477759 0.435458 11.00000 -1.50000
H13B 2 0.590741 0.409719 0.363922 11.00000 -1.50000
H13C 2 0.578878 0.373253 0.470100 11.00000 -1.50000
AFIX 0
C14 1 -0.069153 0.400265 0.346733 11.00000 0.02834 0.05695 =
0.08392 -0.02135 0.02250 -0.00185
AFIX 137
H14A 2 -0.057696 0.358194 0.403582 11.00000 -1.50000
H14B 2 -0.118069 0.357027 0.299257 11.00000 -1.50000
H14C 2 -0.128648 0.463572 0.359932 11.00000 -1.50000
AFIX 0
C15 1 0.057571 0.510547 0.228633 11.00000 0.04094 0.03799 =
0.04075 -0.00826 -0.00750 0.01560
AFIX 137
H15A 2 0.000170 0.474151 0.180596 11.00000 -1.50000
H15B 2 0.153036 0.531669 0.203086 11.00000 -1.50000
H15C 2 0.004403 0.574059 0.249579 11.00000 -1.50000
AFIX 0
C16 1 0.174808 0.264610 0.019853 11.00000 0.04136 0.02916 =
0.03133 -0.00939 -0.00747 0.01030
AFIX 23
H16A 2 0.198230 0.322537 -0.024387 11.00000 -1.20000
H16B 2 0.066742 0.255586 0.020843 11.00000 -1.20000
AFIX 0
CL1 3 0.590230 0.205686 0.296484 11.00000 0.02694 0.03279 =
0.04296 -0.00052 -0.00423 0.00905
CL2 3 0.318606 0.120145 0.363211 11.00000 0.04928 0.02049 =
0.04134 0.00459 0.00602 -0.00270
BR1 4 0.266764 0.131071 -0.023464 11.00000 0.03964 0.03661 =
0.04820 -0.01953 -0.00203 0.00297
HKLF 4
REM RN2 in P2(1)2(1)2(1)
REM R1 = 0.0267 for 3012 Fo > 4sig(Fo) and 0.0281 for all 3127 data
REM 176 parameters refined using 0 restraints
END
WGHT 0.0375 0.3075
REM Highest difference peak 0.412, deepest hole -0.459, 1-sigma level 0.058
Q1 1 0.3333 0.1259 0.0222 11.00000 0.05 0.41
Q2 1 0.1925 0.1270 0.0286 11.00000 0.05 0.31
Q3 1 0.2564 0.3359 0.2958 11.00000 0.05 0.26
Q4 1 0.2730 0.1911 -0.0348 11.00000 0.05 0.23
Q5 1 0.2960 0.1189 0.3034 11.00000 0.05 0.21
Q6 1 0.0667 0.4220 0.4454 11.00000 0.05 0.20
Q7 1 0.2313 0.1243 0.3565 11.00000 0.05 0.20
Q8 1 0.2582 0.1242 0.3255 11.00000 0.05 0.20
Q9 1 0.1310 0.3805 0.3026 11.00000 0.05 0.20
Q10 1 0.1385 0.5271 0.2973 11.00000 0.05 0.20
Q11 1 0.2197 0.2778 0.0832 11.00000 0.05 0.19
Q12 1 0.4971 0.2172 0.3267 11.00000 0.05 0.19
Q13 1 0.3478 0.3424 0.4364 11.00000 0.05 0.19
Q14 1 0.3416 0.3529 0.3529 11.00000 0.05 0.18
Q15 1 0.0667 0.1668 0.0195 11.00000 0.05 0.18
Q16 1 0.6612 0.2048 0.3385 11.00000 0.05 0.18
Q17 1 0.3683 0.3560 0.2621 11.00000 0.05 0.18
Q18 1 0.0078 0.2890 -0.0412 11.00000 0.05 0.18
Q19 1 0.5673 0.5556 0.4735 11.00000 0.05 0.18
Q20 1 -0.0331 0.3666 -0.0004 11.00000 0.05 0.17
Q21 1 0.3008 0.3211 0.1200 11.00000 0.05 0.17
Q22 1 0.1575 0.3129 0.2330 11.00000 0.05 0.17
Q23 1 -0.0060 0.2155 0.0383 11.00000 0.05 0.17
Q24 1 0.5511 0.2067 0.2372 11.00000 0.05 0.17
Q25 1 0.4586 0.4568 0.5174 11.00000 0.05 0.17
;
_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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0227(10) 0.0175(11) 0.0199(11) 0.0007(9) 0.0004(10) -0.0003(9)
C2 0.0243(11) 0.0226(12) 0.0266(12) 0.0009(10) -0.0006(10) 0.0019(10)
C3 0.0342(13) 0.0217(12) 0.0232(12) 0.0033(11) -0.0033(10) -0.0004(9)
C4 0.0548(16) 0.0300(14) 0.0219(11) 0.0021(13) 0.0046(14) 0.0007(10)
C5 0.0516(16) 0.0350(15) 0.0249(12) 0.0037(13) 0.0037(13) -0.0042(11)
C6 0.0341(14) 0.0269(14) 0.0327(14) 0.0029(12) 0.0033(12) -0.0063(11)
C7 0.0223(12) 0.0320(14) 0.0342(14) 0.0048(11) 0.0042(11) -0.0070(11)
C8 0.0197(10) 0.0210(13) 0.0272(13) -0.0046(9) 0.0033(10) -0.0029(9)
C9 0.0187(11) 0.0244(12) 0.0347(14) 0.0017(10) -0.0040(10) -0.0052(11)
C10 0.0284(13) 0.0217(11) 0.0247(11) 0.0060(11) -0.0064(10) -0.0023(9)
C11 0.0251(12) 0.0246(13) 0.0203(11) 0.0018(10) 0.0036(9) 0.0019(9)
C12 0.0178(10) 0.0208(12) 0.0280(12) -0.0003(10) 0.0006(9) 0.0014(10)
C13 0.0402(16) 0.0347(16) 0.0383(16) 0.0004(13) -0.0167(13) -0.0079(12)
C14 0.0283(15) 0.057(2) 0.084(3) -0.0018(15) 0.0225(17) -0.021(2)
C15 0.0409(15) 0.0380(17) 0.0408(16) 0.0156(14) -0.0075(13) -0.0083(13)
C16 0.0414(14) 0.0292(14) 0.0313(13) 0.0103(12) -0.0075(13) -0.0094(12)
Cl1 0.0269(3) 0.0328(4) 0.0430(4) 0.0090(3) -0.0042(3) -0.0005(3)
Cl2 0.0493(4) 0.0205(3) 0.0413(3) -0.0027(3) 0.0060(3) 0.0046(3)
Br1 0.03964(16) 0.03661(18) 0.04820(18) 0.00297(14) -0.00203(13) -0.01953(14)
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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086182