##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2007-11-14
_journal_date_accepted     2007-11-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o160
_journal_page_last     o160
_journal_paper_category     QO
_journal_coeditor_code     PK2071
_publ_contact_author_name     'Dr Yu Peng'
_publ_contact_author_address
;
State Key Laboratory of Applied Organic Chemstry
College of Chemistry & Chemical Engineering
Lanzhou University
Lanzhou 730000
P.R.China
;
_publ_contact_author_email     pengyu@lzu.edu.cn
_publ_contact_author_fax     '+86-931-8912582'
_publ_contact_author_phone     '+86-931-8912595'
_publ_section_title
;
<i>N</i>-(4-Bromobenzoyl)-<i>N</i>,<i>N</i>'-dicyclohexylurea
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ya-Wen Wang' .
;
State Key Laboratory of Applied Organic Chemistry
College of Chemistry and Chemical Engineering
Lanzhou University
Lanzhou 730000
People's Republic of China
;
    'Yu Peng' .
;
State Key Laboratory of Applied Organic Chemistry
College of Chemistry and Chemical Engineering
Lanzhou University
Lanzhou 730000
People's Republic of China
;
data_I
_chemical_name_systematic
;
<i>N</i>-(4-Bromobenzoyl)-<i>N</i>,<i>N</i>'-dicyclohexylurea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H27 Br N2 O2'
_chemical_formula_sum     'C20 H27 Br N2 O2'
_chemical_formula_iupac     'C20 H27 Br N2 O2'
_chemical_formula_weight     407.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     13.501(2)
_cell_length_b     9.5621(10)
_cell_length_c     16.306(2)
_cell_angle_alpha     90.00
_cell_angle_beta     114.443(6)
_cell_angle_gamma     90.00
_cell_volume     1916.3(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4164
_cell_measurement_theta_min     1.7
_cell_measurement_theta_max     27.9
_cell_measurement_temperature     113(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.412
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     2.161
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(REQABS; Jacobson, 1998)'
_exptl_absorpt_correction_T_min     0.484
_exptl_absorpt_correction_T_max     0.739
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'Rotating anode'
_diffrn_radiation_monochromator     confocal
_diffrn_measurement_device_type     'Rigaku Saturn CCD diffractometer'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     7.31
_diffrn_reflns_number     17461
_diffrn_reflns_av_R_equivalents     0.0436
_diffrn_reflns_av_sigmaI/netI     0.0431
_diffrn_reflns_theta_min     1.66
_diffrn_reflns_theta_max     27.90
_diffrn_reflns_theta_full     27.90
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     4526
_reflns_number_gt     3651
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0492
_refine_ls_R_factor_gt     0.0364
_refine_ls_wR_factor_gt     0.0737
_refine_ls_wR_factor_ref     0.0781
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     4526
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.003
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.451
_refine_diff_density_min     -0.437
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrystalClear (Jacobson, 1999)'
_computing_cell_refinement     CrystalClear
_computing_data_reduction     CrystalClear
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'CrystalStructure (Rigaku, 1999)'
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 Br1 0.615319(17) 0.39160(2) 1.092233(14) 0.03591(9) Uani d . 1 . .
    N N1 0.86443(11) 0.53780(15) 0.80694(9) 0.0172(3) Uani d . 1 . .
    N N2 0.67615(11) 0.53992(16) 0.73657(10) 0.0180(3) Uani d D 1 . .
    O O1 0.95485(9) 0.68643(13) 0.92419(8) 0.0226(3) Uani d . 1 . .
    O O2 0.76754(10) 0.34042(13) 0.73292(8) 0.0234(3) Uani d . 1 . .
    C C1 0.69576(14) 0.4583(2) 1.02792(12) 0.0233(4) Uani d . 1 . .
    C C2 0.69278(15) 0.5987(2) 1.00682(13) 0.0267(4) Uani d . 1 . .
    H H2 0.6508 0.6624 1.0240 0.032 Uiso calc R 1 . .
    C C3 0.75215(15) 0.6450(2) 0.96011(13) 0.0246(4) Uani d . 1 . .
    H H3 0.7519 0.7414 0.9460 0.029 Uiso calc R 1 . .
    C C4 0.81235(13) 0.55047(19) 0.93373(11) 0.0176(4) Uani d . 1 . .
    C C5 0.81418(14) 0.40955(19) 0.95585(12) 0.0205(4) Uani d . 1 . .
    H H5 0.8551 0.3450 0.9381 0.025 Uiso calc R 1 . .
    C C6 0.75616(14) 0.3634(2) 1.00396(12) 0.0223(4) Uani d . 1 . .
    H H6 0.7581 0.2677 1.0202 0.027 Uiso calc R 1 . .
    C C7 0.88221(13) 0.60122(18) 0.88777(12) 0.0179(4) Uani d . 1 . .
    C C8 0.94261(14) 0.55666(19) 0.76516(12) 0.0199(4) Uani d . 1 . .
    H H8 0.9907 0.6372 0.7963 0.024 Uiso calc R 1 . .
    C C9 1.01578(15) 0.4287(2) 0.77921(14) 0.0259(4) Uani d . 1 . .
    H H9A 0.9702 0.3452 0.7531 0.031 Uiso calc R 1 . .
    H H9B 1.0574 0.4122 0.8445 0.031 Uiso calc R 1 . .
    C C10 1.09504(16) 0.4493(2) 0.73482(14) 0.0331(5) Uani d . 1 . .
    H H10A 1.1462 0.5260 0.7656 0.040 Uiso calc R 1 . .
    H H10B 1.1380 0.3628 0.7415 0.040 Uiso calc R 1 . .
    C C11 1.03445(17) 0.4842(2) 0.63510(14) 0.0361(5) Uani d . 1 . .
    H H11A 0.9878 0.4043 0.6032 0.043 Uiso calc R 1 . .
    H H11B 1.0874 0.5007 0.6086 0.043 Uiso calc R 1 . .
    C C12 0.96424(17) 0.6143(2) 0.62288(14) 0.0341(5) Uani d . 1 . .
    H H12A 0.9238 0.6338 0.5578 0.041 Uiso calc R 1 . .
    H H12B 1.0117 0.6956 0.6507 0.041 Uiso calc R 1 . .
    C C13 0.88348(15) 0.5955(2) 0.66570(13) 0.0268(4) Uani d . 1 . .
    H H13A 0.8424 0.6834 0.6599 0.032 Uiso calc R 1 . .
    H H13B 0.8308 0.5210 0.6335 0.032 Uiso calc R 1 . .
    C C14 0.76568(14) 0.4618(2) 0.75616(11) 0.0180(4) Uani d . 1 . .
    C C15 0.56540(13) 0.48403(19) 0.69141(12) 0.0180(4) Uani d . 1 . .
    H H15 0.5702 0.3853 0.6733 0.022 Uiso calc R 1 . .
    C C16 0.50196(16) 0.5682(2) 0.60708(13) 0.0313(5) Uani d . 1 . .
    H H16A 0.5392 0.5639 0.5661 0.038 Uiso calc R 1 . .
    H H16B 0.4987 0.6673 0.6233 0.038 Uiso calc R 1 . .
    C C17 0.38642(16) 0.5099(2) 0.55931(15) 0.0399(6) Uani d . 1 . .
    H H17A 0.3452 0.5668 0.5051 0.048 Uiso calc R 1 . .
    H H17B 0.3899 0.4128 0.5396 0.048 Uiso calc R 1 . .
    C C18 0.32755(16) 0.5114(2) 0.62076(18) 0.0509(7) Uani d . 1 . .
    H H18A 0.3189 0.6091 0.6368 0.061 Uiso calc R 1 . .
    H H18B 0.2542 0.4702 0.5890 0.061 Uiso calc R 1 . .
    C C19 0.39104(16) 0.4288(2) 0.70547(16) 0.0403(6) Uani d . 1 . .
    H H19A 0.3934 0.3293 0.6896 0.048 Uiso calc R 1 . .
    H H19B 0.3535 0.4344 0.7462 0.048 Uiso calc R 1 . .
    C C20 0.50804(16) 0.4842(2) 0.75473(14) 0.0296(5) Uani d . 1 . .
    H H20A 0.5063 0.5805 0.7764 0.036 Uiso calc R 1 . .
    H H20B 0.5487 0.4245 0.8077 0.036 Uiso calc R 1 . .
    H H2A 0.6851(15) 0.6326(10) 0.7456(12) 0.023(5) Uiso d D 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
    Br1 0.03720(13) 0.04748(17) 0.03229(13) -0.01255(10) 0.02362(10)
                                                                    -0.00410(10)
    N1 0.0147(7) 0.0164(8) 0.0206(8) -0.0024(6) 0.0075(6) -0.0004(6)
    N2 0.0154(7) 0.0136(9) 0.0238(8) -0.0013(6) 0.0070(6) -0.0024(7)
    O1 0.0190(6) 0.0223(7) 0.0233(7) -0.0054(6) 0.0056(5) -0.0015(6)
    O2 0.0213(6) 0.0140(7) 0.0322(8) 0.0006(5) 0.0084(6) -0.0032(6)
    C1 0.0217(9) 0.0320(12) 0.0174(9) -0.0071(8) 0.0093(8) -0.0027(9)
    C2 0.0257(10) 0.0269(12) 0.0320(11) -0.0048(8) 0.0165(9) -0.0102(9)
    C3 0.0259(10) 0.0198(11) 0.0297(10) -0.0034(8) 0.0132(8) -0.0030(9)
    C4 0.0141(8) 0.0212(10) 0.0151(8) -0.0030(7) 0.0037(7) -0.0019(8)
    C5 0.0164(8) 0.0239(11) 0.0194(9) 0.0003(8) 0.0057(7) 0.0005(8)
    C6 0.0218(9) 0.0244(11) 0.0191(9) -0.0012(8) 0.0067(8) 0.0040(8)
    C7 0.0145(8) 0.0166(10) 0.0198(9) 0.0026(7) 0.0045(7) 0.0037(8)
    C8 0.0171(9) 0.0203(10) 0.0252(10) -0.0019(7) 0.0117(8) -0.0001(8)
    C9 0.0188(9) 0.0267(11) 0.0306(11) 0.0044(8) 0.0087(8) 0.0030(9)
    C10 0.0221(10) 0.0396(13) 0.0405(12) 0.0087(9) 0.0159(9) 0.0002(11)
    C11 0.0321(11) 0.0479(14) 0.0351(12) 0.0045(10) 0.0209(10) -0.0050(11)
    C12 0.0348(11) 0.0463(14) 0.0290(11) 0.0046(10) 0.0210(10) 0.0048(10)
    C13 0.0245(10) 0.0332(12) 0.0264(10) 0.0058(9) 0.0144(8) 0.0065(9)
    C14 0.0176(9) 0.0184(10) 0.0179(9) -0.0019(7) 0.0074(7) 0.0019(8)
    C15 0.0141(8) 0.0162(10) 0.0219(9) -0.0008(7) 0.0055(7) -0.0019(8)
    C16 0.0314(11) 0.0229(11) 0.0270(11) -0.0040(9) -0.0006(9) 0.0023(9)
    C17 0.0268(11) 0.0284(13) 0.0408(13) 0.0028(9) -0.0096(10) 0.0015(10)
    C18 0.0150(10) 0.0391(14) 0.0841(19) 0.0034(10) 0.0060(12) -0.0301(14)
    C19 0.0277(11) 0.0528(15) 0.0518(15) -0.0179(10) 0.0279(11) -0.0276(12)
    C20 0.0262(10) 0.0367(13) 0.0304(11) -0.0088(9) 0.0163(9) -0.0101(10)
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 C1 . 1.9048(18) ?
    N1 C7 . 1.379(2) ?
    N1 C14 . 1.441(2) ?
    N1 C8 . 1.485(2) ?
    N2 C14 . 1.342(2) ?
    N2 C15 . 1.467(2) ?
    N2 H2A . 0.898(9) ?
    O1 C7 . 1.223(2) ?
    O2 C14 . 1.225(2) ?
    C1 C6 . 1.380(3) ?
    C1 C2 . 1.382(3) ?
    C2 C3 . 1.387(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.397(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.393(3) ?
    C4 C7 . 1.507(2) ?
    C5 C6 . 1.390(2) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C8 C13 . 1.528(2) ?
    C8 C9 . 1.529(3) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.532(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.524(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.526(3) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.529(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C15 C16 . 1.516(2) ?
    C15 C20 . 1.526(2) ?
    C15 H15 . 1.0000 ?
    C16 C17 . 1.531(3) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C18 . 1.515(3) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 C19 . 1.512(3) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.540(3) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
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
    C7 N1 C14 . . 121.65(14) ?
    C7 N1 C8 . . 120.63(14) ?
    C14 N1 C8 . . 117.50(14) ?
    C14 N2 C15 . . 123.18(15) ?
    C14 N2 H2A . . 117.5(12) ?
    C15 N2 H2A . . 118.8(12) ?
    C6 C1 C2 . . 121.85(17) ?
    C6 C1 Br1 . . 118.30(15) ?
    C2 C1 Br1 . . 119.85(14) ?
    C1 C2 C3 . . 118.86(18) ?
    C1 C2 H2 . . 120.6 ?
    C3 C2 H2 . . 120.6 ?
    C2 C3 C4 . . 120.33(18) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 119.75(17) ?
    C5 C4 C7 . . 119.52(16) ?
    C3 C4 C7 . . 120.56(17) ?
    C6 C5 C4 . . 119.98(17) ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C1 C6 C5 . . 119.22(18) ?
    C1 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    O1 C7 N1 . . 122.99(16) ?
    O1 C7 C4 . . 120.93(16) ?
    N1 C7 C4 . . 115.88(15) ?
    N1 C8 C13 . . 110.98(14) ?
    N1 C8 C9 . . 111.83(15) ?
    C13 C8 C9 . . 112.02(16) ?
    N1 C8 H8 . . 107.2 ?
    C13 C8 H8 . . 107.2 ?
    C9 C8 H8 . . 107.2 ?
    C8 C9 C10 . . 111.13(16) ?
    C8 C9 H9A . . 109.4 ?
    C10 C9 H9A . . 109.4 ?
    C8 C9 H9B . . 109.4 ?
    C10 C9 H9B . . 109.4 ?
    H9A C9 H9B . . 108.0 ?
    C11 C10 C9 . . 111.13(16) ?
    C11 C10 H10A . . 109.4 ?
    C9 C10 H10A . . 109.4 ?
    C11 C10 H10B . . 109.4 ?
    C9 C10 H10B . . 109.4 ?
    H10A C10 H10B . . 108.0 ?
    C10 C11 C12 . . 110.37(17) ?
    C10 C11 H11A . . 109.6 ?
    C12 C11 H11A . . 109.6 ?
    C10 C11 H11B . . 109.6 ?
    C12 C11 H11B . . 109.6 ?
    H11A C11 H11B . . 108.1 ?
    C11 C12 C13 . . 111.49(17) ?
    C11 C12 H12A . . 109.3 ?
    C13 C12 H12A . . 109.3 ?
    C11 C12 H12B . . 109.3 ?
    C13 C12 H12B . . 109.3 ?
    H12A C12 H12B . . 108.0 ?
    C8 C13 C12 . . 110.81(16) ?
    C8 C13 H13A . . 109.5 ?
    C12 C13 H13A . . 109.5 ?
    C8 C13 H13B . . 109.5 ?
    C12 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 108.1 ?
    O2 C14 N2 . . 125.83(16) ?
    O2 C14 N1 . . 121.54(16) ?
    N2 C14 N1 . . 112.60(16) ?
    N2 C15 C16 . . 109.75(14) ?
    N2 C15 C20 . . 110.93(14) ?
    C16 C15 C20 . . 111.03(16) ?
    N2 C15 H15 . . 108.3 ?
    C16 C15 H15 . . 108.3 ?
    C20 C15 H15 . . 108.3 ?
    C15 C16 C17 . . 110.02(16) ?
    C15 C16 H16A . . 109.7 ?
    C17 C16 H16A . . 109.7 ?
    C15 C16 H16B . . 109.7 ?
    C17 C16 H16B . . 109.7 ?
    H16A C16 H16B . . 108.2 ?
    C18 C17 C16 . . 111.28(18) ?
    C18 C17 H17A . . 109.4 ?
    C16 C17 H17A . . 109.4 ?
    C18 C17 H17B . . 109.4 ?
    C16 C17 H17B . . 109.4 ?
    H17A C17 H17B . . 108.0 ?
    C19 C18 C17 . . 110.18(17) ?
    C19 C18 H18A . . 109.6 ?
    C17 C18 H18A . . 109.6 ?
    C19 C18 H18B . . 109.6 ?
    C17 C18 H18B . . 109.6 ?
    H18A C18 H18B . . 108.1 ?
    C18 C19 C20 . . 111.59(18) ?
    C18 C19 H19A . . 109.3 ?
    C20 C19 H19A . . 109.3 ?
    C18 C19 H19B . . 109.3 ?
    C20 C19 H19B . . 109.3 ?
    H19A C19 H19B . . 108.0 ?
    C15 C20 C19 . . 110.18(16) ?
    C15 C20 H20A . . 109.6 ?
    C19 C20 H20A . . 109.6 ?
    C15 C20 H20B . . 109.6 ?
    C19 C20 H20B . . 109.6 ?
    H20A C20 H20B . . 108.1 ?
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
    C6 C1 C2 C3 . . . . 0.1(3) ?
    Br1 C1 C2 C3 . . . . 179.88(14) ?
    C1 C2 C3 C4 . . . . 1.0(3) ?
    C2 C3 C4 C5 . . . . -1.1(3) ?
    C2 C3 C4 C7 . . . . -176.41(17) ?
    C3 C4 C5 C6 . . . . 0.0(3) ?
    C7 C4 C5 C6 . . . . 175.39(15) ?
    C2 C1 C6 C5 . . . . -1.2(3) ?
    Br1 C1 C6 C5 . . . . 179.06(13) ?
    C4 C5 C6 C1 . . . . 1.1(3) ?
    C14 N1 C7 O1 . . . . -166.44(16) ?
    C8 N1 C7 O1 . . . . 7.9(2) ?
    C14 N1 C7 C4 . . . . 18.6(2) ?
    C8 N1 C7 C4 . . . . -167.06(14) ?
    C5 C4 C7 O1 . . . . -117.18(19) ?
    C3 C4 C7 O1 . . . . 58.1(2) ?
    C5 C4 C7 N1 . . . . 57.9(2) ?
    C3 C4 C7 N1 . . . . -126.75(18) ?
    C7 N1 C8 C13 . . . . -131.60(17) ?
    C14 N1 C8 C13 . . . . 43.0(2) ?
    C7 N1 C8 C9 . . . . 102.52(19) ?
    C14 N1 C8 C9 . . . . -82.87(19) ?
    N1 C8 C9 C10 . . . . 179.38(15) ?
    C13 C8 C9 C10 . . . . 54.1(2) ?
    C8 C9 C10 C11 . . . . -55.5(2) ?
    C9 C10 C11 C12 . . . . 57.0(2) ?
    C10 C11 C12 C13 . . . . -57.3(2) ?
    N1 C8 C13 C12 . . . . -179.79(15) ?
    C9 C8 C13 C12 . . . . -54.0(2) ?
    C11 C12 C13 C8 . . . . 55.7(2) ?
    C15 N2 C14 O2 . . . . 6.6(3) ?
    C15 N2 C14 N1 . . . . -175.26(14) ?
    C7 N1 C14 O2 . . . . -125.42(18) ?
    C8 N1 C14 O2 . . . . 60.0(2) ?
    C7 N1 C14 N2 . . . . 56.4(2) ?
    C8 N1 C14 N2 . . . . -118.19(17) ?
    C14 N2 C15 C16 . . . . -124.11(18) ?
    C14 N2 C15 C20 . . . . 112.83(19) ?
    N2 C15 C16 C17 . . . . 179.70(16) ?
    C20 C15 C16 C17 . . . . -57.3(2) ?
    C15 C16 C17 C18 . . . . 57.9(2) ?
    C16 C17 C18 C19 . . . . -57.3(2) ?
    C17 C18 C19 C20 . . . . 56.3(2) ?
    N2 C15 C20 C19 . . . . 178.56(17) ?
    C16 C15 C20 C19 . . . . 56.2(2) ?
    C18 C19 C20 C15 . . . . -55.8(2) ?
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
    _geom_hbond_publ_flag
    N2 H2A O2 2_656 0.898(10) 2.072(11) 2.961(2) 170(2) y