##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1R)-methyl 6-bromo-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-
octahydrophenanthrene-1-carboxylate
;
_chemical_name_common     'Methyl 12-bromodehydroabietate'
_chemical_formula_moiety     'C21 H29 Br O2'
_chemical_formula_sum     'C21 H29 Br O2'
_chemical_formula_iupac     'C21 H29 Br O2'
_chemical_formula_weight     393.35
_chemical_melting_point     416
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2'
_symmetry_space_group_name_hall     'C 2y'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z'
_cell_length_a     13.888(3)
_cell_length_b     6.1260(12)
_cell_length_c     23.382(5)
_cell_angle_alpha     90.00
_cell_angle_beta     103.19(3)
_cell_angle_gamma     90.00
_cell_volume     1936.8(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     13
_cell_measurement_temperature     293(2)
_exptl_crystal_description     rod
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.349
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     824
_exptl_absorpt_coefficient_mu     2.132
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.5672
_exptl_absorpt_correction_T_max     0.6751
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3657
_diffrn_reflns_av_R_equivalents     0.0350
_diffrn_reflns_av_sigmaI/netI     0.0493
_diffrn_reflns_theta_min     1.79
_diffrn_reflns_theta_max     25.30
_diffrn_reflns_theta_full     25.30
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those based on
F, and R- factors based on ALL data will be even larger.
;
_reflns_number_total     3505
_reflns_number_gt     2754
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0705
_refine_ls_R_factor_gt     0.0466
_refine_ls_wR_factor_gt     0.1104
_refine_ls_wR_factor_ref     0.1280
_refine_ls_goodness_of_fit_ref     1.006
_refine_ls_restrained_S_all     1.006
_refine_ls_number_reflns     3505
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0830P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.635
_refine_diff_density_min     -0.398
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0175(13)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 1563 Friedel pairs'
_refine_ls_abs_structure_Flack     0.010(15)
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'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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_disorder_assembly
    _atom_site_disorder_group
    Br Br 0.52734(4) 0.20204(10) 0.41747(2) 0.0569(3) Uani d . 1 . .
    C C1 0.4547(4) -0.1955(9) 0.2063(2) 0.0396(12) Uani d . 1 . .
    H H1A 0.4131 -0.2111 0.2342 0.048 Uiso calc R 1 . .
    H H1B 0.4601 -0.0409 0.1985 0.048 Uiso calc R 1 . .
    O O1 0.6426(4) -0.1241(7) 0.0769(2) 0.0621(13) Uani d . 1 . .
    O O2 0.6696(4) -0.4626(8) 0.0554(2) 0.0841(17) Uani d . 1 . .
    C C2 0.4054(3) -0.3087(14) 0.1497(2) 0.0478(12) Uani d . 1 . .
    H H2A 0.3425 -0.2385 0.1334 0.057 Uiso calc R 1 . .
    H H2B 0.3922 -0.4594 0.1581 0.057 Uiso calc R 1 . .
    C C3 0.4686(3) -0.3032(13) 0.10451(19) 0.0448(11) Uani d . 1 . .
    H H3A 0.4744 -0.1532 0.0924 0.054 Uiso calc R 1 . .
    H H3B 0.4354 -0.3851 0.0701 0.054 Uiso calc R 1 . .
    C C4 0.5724(4) -0.3975(9) 0.1272(2) 0.0387(12) Uani d . 1 . .
    C C5 0.6204(3) -0.2861(11) 0.18667(18) 0.0324(9) Uani d . 1 . .
    H H5A 0.6258 -0.1318 0.1768 0.039 Uiso calc R 1 . .
    C C6 0.7266(4) -0.3588(9) 0.2118(2) 0.0423(14) Uani d . 1 . .
    H H6A 0.7269 -0.4996 0.2309 0.051 Uiso calc R 1 . .
    H H6B 0.7614 -0.3732 0.1805 0.051 Uiso calc R 1 . .
    C C7 0.7773(4) -0.1913(11) 0.2557(3) 0.0502(15) Uani d . 1 . .
    H H7A 0.7984 -0.0709 0.2346 0.060 Uiso calc R 1 . .
    H H7B 0.8361 -0.2568 0.2801 0.060 Uiso calc R 1 . .
    C C8 0.7139(3) -0.1013(9) 0.2953(2) 0.0361(11) Uani d . 1 . .
    C C9 0.6128(3) -0.1423(8) 0.2847(2) 0.0320(11) Uani d . 1 . .
    C C10 0.5593(3) -0.2863(11) 0.23428(18) 0.0319(9) Uani d . 1 . .
    C C11 0.5608(4) -0.0505(9) 0.3232(2) 0.0357(11) Uani d . 1 . .
    H H11A 0.4930 -0.0738 0.3170 0.043 Uiso calc R 1 . .
    C C12 0.6087(4) 0.0746(8) 0.3703(2) 0.0339(11) Uani d . 1 . .
    C C13 0.7099(3) 0.1180(8) 0.3821(2) 0.0347(11) Uani d . 1 . .
    C C14 0.7593(4) 0.0265(9) 0.3430(2) 0.0406(12) Uani d . 1 . .
    H H14A 0.8269 0.0517 0.3490 0.049 Uiso calc R 1 . .
    C C15 0.7620(4) 0.2626(9) 0.4324(2) 0.0419(14) Uani d . 1 . .
    H H15A 0.7239 0.2576 0.4629 0.050 Uiso calc R 1 . .
    C C16 0.8676(4) 0.1866(15) 0.4603(3) 0.0641(15) Uani d . 1 . .
    H H16A 0.8662 0.0379 0.4730 0.096 Uiso calc R 1 . .
    H H16B 0.8952 0.2774 0.4934 0.096 Uiso calc R 1 . .
    H H16C 0.9076 0.1969 0.4318 0.096 Uiso calc R 1 . .
    C C17 0.7635(5) 0.5004(10) 0.4120(3) 0.0601(17) Uani d . 1 . .
    H H17A 0.6973 0.5469 0.3946 0.090 Uiso calc R 1 . .
    H H17B 0.8033 0.5113 0.3834 0.090 Uiso calc R 1 . .
    H H17C 0.7909 0.5918 0.4450 0.090 Uiso calc R 1 . .
    C C18 0.6337(4) -0.3401(9) 0.0833(2) 0.0398(14) Uani d . 1 . .
    C C19 0.5695(5) -0.6506(9) 0.1291(3) 0.0527(16) Uani d . 1 . .
    H H19A 0.5388 -0.7056 0.0908 0.079 Uiso calc R 1 . .
    H H19B 0.5321 -0.6966 0.1568 0.079 Uiso calc R 1 . .
    H H19C 0.6357 -0.7063 0.1408 0.079 Uiso calc R 1 . .
    C C20 0.5494(4) -0.5132(8) 0.2616(2) 0.0421(13) Uani d . 1 . .
    H H20A 0.6140 -0.5693 0.2789 0.063 Uiso calc R 1 . .
    H H20B 0.5160 -0.6113 0.2316 0.063 Uiso calc R 1 . .
    H H20C 0.5121 -0.4995 0.2913 0.063 Uiso calc R 1 . .
    C C21 0.6987(5) -0.0491(12) 0.0371(3) 0.0620(18) Uani d . 1 . .
    H H21A 0.6992 0.1076 0.0368 0.093 Uiso calc R 1 . .
    H H21B 0.6697 -0.1020 -0.0016 0.093 Uiso calc R 1 . .
    H H21C 0.7653 -0.1021 0.0492 0.093 Uiso calc R 1 . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Br C12 . 1.916(5) ?
    C1 C2 . 1.512(8) ?
    C1 C10 . 1.553(7) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    O1 C18 . 1.340(8) ?
    O1 C21 . 1.420(7) ?
    O2 C18 . 1.178(7) ?
    C2 C3 . 1.520(6) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.532(7) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C18 . 1.517(7) ?
    C4 C19 . 1.552(8) ?
    C4 C5 . 1.555(7) ?
    C5 C6 . 1.524(6) ?
    C5 C10 . 1.547(5) ?
    C5 H5A . 0.9800 ?
    C6 C7 . 1.507(8) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.519(7) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C14 . 1.391(7) ?
    C8 C9 . 1.391(7) ?
    C9 C11 . 1.393(7) ?
    C9 C10 . 1.524(7) ?
    C10 C20 . 1.549(8) ?
    C11 C12 . 1.382(7) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.396(7) ?
    C13 C14 . 1.381(7) ?
    C13 C15 . 1.517(7) ?
    C14 H14A . 0.9300 ?
    C15 C17 . 1.535(8) ?
    C15 C16 . 1.535(8) ?
    C15 H15A . 0.9800 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C10 . . 113.4(4) ?
    C2 C1 H1A . . 108.9 ?
    C10 C1 H1A . . 108.9 ?
    C2 C1 H1B . . 108.9 ?
    C10 C1 H1B . . 108.9 ?
    H1A C1 H1B . . 107.7 ?
    C18 O1 C21 . . 118.1(5) ?
    C1 C2 C3 . . 112.3(5) ?
    C1 C2 H2A . . 109.1 ?
    C3 C2 H2A . . 109.1 ?
    C1 C2 H2B . . 109.1 ?
    C3 C2 H2B . . 109.1 ?
    H2A C2 H2B . . 107.9 ?
    C2 C3 C4 . . 113.4(4) ?
    C2 C3 H3A . . 108.9 ?
    C4 C3 H3A . . 108.9 ?
    C2 C3 H3B . . 108.9 ?
    C4 C3 H3B . . 108.9 ?
    H3A C3 H3B . . 107.7 ?
    C18 C4 C3 . . 107.9(4) ?
    C18 C4 C19 . . 105.9(4) ?
    C3 C4 C19 . . 111.0(5) ?
    C18 C4 C5 . . 108.1(4) ?
    C3 C4 C5 . . 108.8(4) ?
    C19 C4 C5 . . 115.0(5) ?
    C6 C5 C10 . . 111.3(4) ?
    C6 C5 C4 . . 113.4(4) ?
    C10 C5 C4 . . 116.7(4) ?
    C6 C5 H5A . . 104.7 ?
    C10 C5 H5A . . 104.7 ?
    C4 C5 H5A . . 104.7 ?
    C7 C6 C5 . . 109.0(4) ?
    C7 C6 H6A . . 109.9 ?
    C5 C6 H6A . . 109.9 ?
    C7 C6 H6B . . 109.9 ?
    C5 C6 H6B . . 109.9 ?
    H6A C6 H6B . . 108.3 ?
    C6 C7 C8 . . 114.6(4) ?
    C6 C7 H7A . . 108.6 ?
    C8 C7 H7A . . 108.6 ?
    C6 C7 H7B . . 108.6 ?
    C8 C7 H7B . . 108.6 ?
    H7A C7 H7B . . 107.6 ?
    C14 C8 C9 . . 119.9(5) ?
    C14 C8 C7 . . 118.2(4) ?
    C9 C8 C7 . . 121.8(5) ?
    C8 C9 C11 . . 117.6(5) ?
    C8 C9 C10 . . 122.4(4) ?
    C11 C9 C10 . . 120.0(4) ?
    C9 C10 C20 . . 105.9(4) ?
    C9 C10 C5 . . 107.8(4) ?
    C20 C10 C5 . . 114.4(5) ?
    C9 C10 C1 . . 111.3(5) ?
    C20 C10 C1 . . 109.5(4) ?
    C5 C10 C1 . . 108.1(4) ?
    C12 C11 C9 . . 120.8(4) ?
    C12 C11 H11A . . 119.6 ?
    C9 C11 H11A . . 119.6 ?
    C11 C12 C13 . . 122.9(4) ?
    C11 C12 Br . . 116.5(4) ?
    C13 C12 Br . . 120.5(4) ?
    C14 C13 C12 . . 114.9(5) ?
    C14 C13 C15 . . 122.0(4) ?
    C12 C13 C15 . . 123.1(5) ?
    C13 C14 C8 . . 123.8(4) ?
    C13 C14 H14A . . 118.1 ?
    C8 C14 H14A . . 118.1 ?
    C13 C15 C17 . . 110.5(4) ?
    C13 C15 C16 . . 113.1(5) ?
    C17 C15 C16 . . 109.9(5) ?
    C13 C15 H15A . . 107.7 ?
    C17 C15 H15A . . 107.7 ?
    C16 C15 H15A . . 107.7 ?
    C15 C16 H16A . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C15 C17 H17A . . 109.5 ?
    C15 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C15 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O2 C18 O1 . . 120.4(5) ?
    O2 C18 C4 . . 126.9(5) ?
    O1 C18 C4 . . 112.6(4) ?
    C4 C19 H19A . . 109.5 ?
    C4 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C4 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C10 C20 H20A . . 109.5 ?
    C10 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C10 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O1 C21 H21A . . 109.5 ?
    O1 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O1 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 C1 C2 C3 . . . . -55.4(8) ?
    C1 C2 C3 C4 . . . . 55.2(9) ?
    C2 C3 C4 C18 . . . . -168.5(6) ?
    C2 C3 C4 C19 . . . . 76.0(7) ?
    C2 C3 C4 C5 . . . . -51.4(7) ?
    C18 C4 C5 C6 . . . . -60.0(6) ?
    C3 C4 C5 C6 . . . . -176.8(5) ?
    C19 C4 C5 C6 . . . . 58.0(6) ?
    C18 C4 C5 C10 . . . . 168.7(5) ?
    C3 C4 C5 C10 . . . . 51.8(6) ?
    C19 C4 C5 C10 . . . . -73.3(6) ?
    C10 C5 C6 C7 . . . . -65.9(6) ?
    C4 C5 C6 C7 . . . . 160.2(5) ?
    C5 C6 C7 C8 . . . . 40.9(7) ?
    C6 C7 C8 C14 . . . . 169.8(5) ?
    C6 C7 C8 C9 . . . . -10.7(8) ?
    C14 C8 C9 C11 . . . . 0.2(7) ?
    C7 C8 C9 C11 . . . . -179.3(5) ?
    C14 C8 C9 C10 . . . . -178.2(5) ?
    C7 C8 C9 C10 . . . . 2.3(8) ?
    C8 C9 C10 C20 . . . . 98.6(5) ?
    C11 C9 C10 C20 . . . . -79.7(6) ?
    C8 C9 C10 C5 . . . . -24.1(7) ?
    C11 C9 C10 C5 . . . . 157.5(5) ?
    C8 C9 C10 C1 . . . . -142.5(5) ?
    C11 C9 C10 C1 . . . . 39.1(6) ?
    C6 C5 C10 C9 . . . . 55.8(6) ?
    C4 C5 C10 C9 . . . . -172.0(5) ?
    C6 C5 C10 C20 . . . . -61.7(6) ?
    C4 C5 C10 C20 . . . . 70.6(6) ?
    C6 C5 C10 C1 . . . . 176.2(5) ?
    C4 C5 C10 C1 . . . . -51.6(7) ?
    C2 C1 C10 C9 . . . . 170.0(5) ?
    C2 C1 C10 C20 . . . . -73.3(6) ?
    C2 C1 C10 C5 . . . . 51.8(7) ?
    C8 C9 C11 C12 . . . . -0.6(7) ?
    C10 C9 C11 C12 . . . . 177.9(5) ?
    C9 C11 C12 C13 . . . . 0.4(8) ?
    C9 C11 C12 Br . . . . 177.2(4) ?
    C11 C12 C13 C14 . . . . 0.1(7) ?
    Br C12 C13 C14 . . . . -176.5(4) ?
    C11 C12 C13 C15 . . . . 177.5(5) ?
    Br C12 C13 C15 . . . . 0.9(7) ?
    C12 C13 C14 C8 . . . . -0.5(8) ?
    C15 C13 C14 C8 . . . . -177.9(5) ?
    C9 C8 C14 C13 . . . . 0.3(8) ?
    C7 C8 C14 C13 . . . . 179.8(5) ?
    C14 C13 C15 C17 . . . . 86.4(6) ?
    C12 C13 C15 C17 . . . . -90.9(6) ?
    C14 C13 C15 C16 . . . . -37.3(7) ?
    C12 C13 C15 C16 . . . . 145.4(5) ?
    C21 O1 C18 O2 . . . . -1.8(10) ?
    C21 O1 C18 C4 . . . . 179.7(5) ?
    C3 C4 C18 O2 . . . . -117.3(7) ?
    C19 C4 C18 O2 . . . . 1.6(9) ?
    C5 C4 C18 O2 . . . . 125.3(7) ?
    C3 C4 C18 O1 . . . . 61.1(6) ?
    C19 C4 C18 O1 . . . . 179.9(5) ?
    C5 C4 C18 O1 . . . . -56.4(6) ?
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
    C21 H21A O2 1_565 0.96 2.72 3.652(10) 165.2
data_global
_journal_date_recd_electronic     2010-03-22
_journal_date_accepted     2010-03-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1207
_journal_page_last     o1207
_journal_paper_category     QO
_journal_coeditor_code     ZQ2035
_publ_contact_author_name     'Professor Zhan-Qian Song'
_publ_contact_author_address
;
Institute of Chemical Industry of Forest Products
Chinese Academy of Forestry
Nanjing, 210042,
People's Republic of China
;
_publ_contact_author_email     songzq@hotmail.com
_publ_contact_author_fax     '+86-25-85482468'
_publ_contact_author_phone     '+86-25-85482468'
_publ_section_title
;
Methyl 12-bromodehydroabietate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gao, Hong'
;
Institute of Chemical Industry of Forest Products
Chinese Academy of Forestry
Nanjing 210042,
People's Republic of China
;
    'Zhan-Qian Song'
;
Institute of Chemical Industry of Forest Products
Chinese Academy of Forestry
Nanjing 210042,
People's Republic of China
;
    'Shi-Bin Shang'
;
Institute of Chemical Industry of Forest Products
Chinese Academy of Forestry
Nanjing 210042,
People's Republic of China
;
