##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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
_journal_date_recd_electronic     2014-06-18
_journal_date_accepted     2014-06-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      7
_journal_page_first     o822
_journal_page_last     o823
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814014433
_journal_coeditor_code     JJ2190
_publ_contact_author_name     'Ray J. Butcher'
_publ_contact_author_address
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059
USA
;
_publ_contact_author_email     'rbutcher99@yahoo.com'
_publ_contact_author_fax     '202-806-5442'
_publ_contact_author_phone     '202-806-9892'
_publ_section_title
;\
2-Bromo-5-<i>tert</i>-butyl-<i>N</i>-methyl-<i>N</i>-[2-(methylamino)phenyl]-3-\
(1-methyl-1<i>H</i>-benzimidazol-2-yl)benzamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Prasad, Poonam Rajesh' .
;
Department of Chemistry, Indian Institute of Technology Bombay, Powai,
Mumbai 400 076,
India
;
    'Das, Shikha' .
;
Department of Chemistry, Indian Institute of Technology Bombay, Powai,
Mumbai 400 076,
India
;
    'Singh, Harkesh B.' .
;
Department of Chemistry, Indian Institute of Technology Bombay, Powai,
Mumbai 400 076,
India
;
    'Butcher, Ray J.' .
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059
USA
;
_database_code_depnum_ccdc_archive     'CCDC 1009070'
_chemical_name_systematic
;\
2-Bromo-5-<i>tert</i>-butyl-<i>N</i>-methyl-<i>N</i>-[2-(methylamino)phenyl]-\
3-(1-methyl-1<i>H</i>-benzimidazol-2-yl)benzamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H29 Br N4 O'
_chemical_formula_sum     'C27 H29 Br N4 O'
_chemical_formula_iupac     'C27 H29 Br N4 O'
_chemical_formula_weight     505.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     34.4327(13)
_cell_length_b     9.4152(2)
_cell_length_c     17.1092(7)
_cell_angle_alpha     90.00
_cell_angle_beta     118.312(5)
_cell_angle_gamma     90.00
_cell_volume     4883.2(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4036
_cell_measurement_theta_min     2.9130
_cell_measurement_theta_max     75.4556
_cell_measurement_temperature     123(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.23
_exptl_crystal_density_diffrn     1.375
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2096
_exptl_absorpt_coefficient_mu     2.497
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_absorpt_correction_T_min     0.78804
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
^1^H NMR (400 MHz, CDCl~3~): \d (ppm) 7.87-7.71 (1H, m), 7.46-7.31
(4H, m), 7.09-7.07 (1H, m), 6.54-6.48 (1H, m), 3.53 (2H, s), 3.45
(2H, s), 2.89 (2H, s), 1.38 (1H, s), 1.13 (6H, s). ^13^C NMR
(CDCl~3~): \d 29.4, 30.9, 31.1, 31.9, 31.2, 34.7, 35.1, 35.5, 53.9,
109.7, 109.9, 120.2, 122.1, 122.5, 122.7, 123.1, 123.3, 129.4, 129.7,
131.2, 133.0, 135.6, 142.8, 151.7, 152.6, 152.8.
;
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Agilent Xcalibur Ruby Gemini'
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     10.5081
_diffrn_reflns_number     9307
_diffrn_reflns_av_R_equivalents     0.0282
_diffrn_reflns_av_sigmaI/netI     0.0382
_diffrn_reflns_theta_min     2.92
_diffrn_reflns_theta_max     75.64
_diffrn_reflns_theta_full     67.50
_diffrn_measured_fraction_theta_max     0.971
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -42
_diffrn_reflns_limit_h_max     42
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4929
_reflns_number_gt     4100
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0442
_refine_ls_R_factor_gt     0.0340
_refine_ls_wR_factor_gt     0.0858
_refine_ls_wR_factor_ref     0.0932
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.029
_refine_ls_number_reflns     4929
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.4711P] 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     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.430
_refine_diff_density_min     -0.349
_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' 0.0181 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'
    'N' 'N' 0.0311 0.0180
                         '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'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br 0.630352(8) 0.53882(3) 0.543344(15) 0.03435(9) Uani d . 1 1 . .
    O O1 0.52147(5) 0.66100(17) 0.36987(11) 0.0338(3) Uani d . 1 1 . .
    N N1 0.70366(6) 0.3018(2) 0.53797(13) 0.0370(4) Uani d . 1 1 . .
    N N2 0.65609(7) 0.1320(2) 0.53017(14) 0.0380(4) Uani d . 1 1 . .
    N N3 0.56938(7) 0.7887(2) 0.19074(15) 0.0406(5) Uani d . 1 1 . .
    H H3B 0.5490(9) 0.765(3) 0.1989(18) 0.033(7) Uiso d . 1 1 . .
    N N4 0.57538(6) 0.78517(19) 0.36118(13) 0.0315(4) Uani d . 1 1 . .
    C C1 0.72063(8) 0.4328(3) 0.52039(19) 0.0447(6) Uani d . 1 1 . .
    H H1A 0.6998 0.4684 0.4614 0.067 Uiso calc R 1 1 . .
    H H1B 0.7492 0.4142 0.5227 0.067 Uiso calc R 1 1 . .
    H H1C 0.7244 0.5039 0.5653 0.067 Uiso calc R 1 1 . .
    C C2 0.72791(8) 0.2049(3) 0.60366(16) 0.0401(5) Uani d . 1 1 . .
    C C3 0.77297(9) 0.1991(4) 0.66449(19) 0.0541(7) Uani d . 1 1 . .
    H H3A 0.7929 0.2717 0.6682 0.065 Uiso calc R 1 1 . .
    C C4 0.78664(11) 0.0803(4) 0.7190(2) 0.0620(9) Uani d . 1 1 . .
    H H4A 0.8171 0.0697 0.7600 0.074 Uiso calc R 1 1 . .
    C C5 0.75708(12) -0.0240(4) 0.7155(2) 0.0615(8) Uani d . 1 1 . .
    H H5A 0.7679 -0.1020 0.7554 0.074 Uiso calc R 1 1 . .
    C C6 0.71279(11) -0.0174(3) 0.6561(2) 0.0542(7) Uani d . 1 1 . .
    H H6A 0.6929 -0.0892 0.6541 0.065 Uiso calc R 1 1 . .
    C C7 0.69805(8) 0.1004(3) 0.59819(16) 0.0402(5) Uani d . 1 1 . .
    C C8 0.66112(7) 0.2518(2) 0.49703(15) 0.0323(4) Uani d . 1 1 . .
    C C9 0.62557(7) 0.3270(2) 0.42009(14) 0.0292(4) Uani d . 1 1 . .
    C C10 0.60873(7) 0.2663(2) 0.33589(15) 0.0300(4) Uani d . 1 1 . .
    H H10A 0.6198 0.1769 0.3297 0.036 Uiso calc R 1 1 . .
    C C11 0.57614(7) 0.3331(2) 0.26044(14) 0.0292(4) Uani d . 1 1 . .
    C C12 0.55997(7) 0.4627(2) 0.27251(15) 0.0294(4) Uani d . 1 1 . .
    H H12A 0.5371 0.5086 0.2224 0.035 Uiso calc R 1 1 . .
    C C13 0.57612(6) 0.5266(2) 0.35517(14) 0.0264(4) Uani d . 1 1 . .
    C C14 0.60895(7) 0.4577(2) 0.42851(14) 0.0276(4) Uani d . 1 1 . .
    C C15 0.55815(8) 0.2676(2) 0.16780(16) 0.0358(5) Uani d . 1 1 . .
    C C16 0.59482(11) 0.1859(3) 0.15917(19) 0.0543(7) Uani d . 1 1 . .
    H H16A 0.6042 0.1043 0.1996 0.081 Uiso calc R 1 1 . .
    H H16B 0.6200 0.2490 0.1744 0.081 Uiso calc R 1 1 . .
    H H16C 0.5835 0.1524 0.0980 0.081 Uiso calc R 1 1 . .
    C C17 0.52108(12) 0.1646(4) 0.1534(2) 0.0693(11) Uani d . 1 1 . .
    H H17A 0.4978 0.2157 0.1592 0.104 Uiso calc R 1 1 . .
    H H17B 0.5328 0.0888 0.1979 0.104 Uiso calc R 1 1 . .
    H H17C 0.5089 0.1232 0.0938 0.104 Uiso calc R 1 1 . .
    C C18 0.54015(8) 0.3820(3) 0.09601(15) 0.0363(5) Uani d . 1 1 . .
    H H18A 0.5131 0.4223 0.0925 0.054 Uiso calc R 1 1 . .
    H H18B 0.5336 0.3400 0.0387 0.054 Uiso calc R 1 1 . .
    H H18C 0.5622 0.4573 0.1108 0.054 Uiso calc R 1 1 . .
    C C19 0.55554(7) 0.6638(2) 0.36324(13) 0.0275(4) Uani d . 1 1 . .
    C C20 0.55836(9) 0.9201(2) 0.3754(2) 0.0426(6) Uani d . 1 1 . .
    H H20A 0.5362 0.9011 0.3947 0.064 Uiso calc R 1 1 . .
    H H20B 0.5448 0.9743 0.3199 0.064 Uiso calc R 1 1 . .
    H H20C 0.5827 0.9751 0.4212 0.064 Uiso calc R 1 1 . .
    C C21 0.61458(7) 0.7918(2) 0.35017(17) 0.0326(5) Uani d . 1 1 . .
    C C22 0.65527(8) 0.8083(3) 0.42439(18) 0.0414(5) Uani d . 1 1 . .
    H H22A 0.6574 0.8092 0.4818 0.050 Uiso calc R 1 1 . .
    C C23 0.69305(8) 0.8234(3) 0.4155(2) 0.0511(7) Uani d . 1 1 . .
    H H23A 0.7211 0.8336 0.4664 0.061 Uiso calc R 1 1 . .
    C C24 0.68929(8) 0.8235(3) 0.3315(2) 0.0507(7) Uani d . 1 1 . .
    H H24A 0.7151 0.8333 0.3251 0.061 Uiso calc R 1 1 . .
    C C25 0.64900(8) 0.8098(3) 0.2569(2) 0.0435(6) Uani d . 1 1 . .
    H H25A 0.6474 0.8101 0.2000 0.052 Uiso calc R 1 1 . .
    C C26 0.60991(7) 0.7951(2) 0.26395(17) 0.0346(5) Uani d . 1 1 . .
    C C27 0.56379(9) 0.7866(3) 0.10141(18) 0.0464(6) Uani d . 1 1 . .
    H H27A 0.5323 0.7794 0.0588 0.070 Uiso calc R 1 1 . .
    H H27B 0.5795 0.7047 0.0945 0.070 Uiso calc R 1 1 . .
    H H27C 0.5758 0.8743 0.0905 0.070 Uiso calc R 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
    Br 0.03690(13) 0.03680(13) 0.02700(13) 0.00268(9) 0.01323(10) -0.00251(9)
    O1 0.0297(7) 0.0358(8) 0.0387(8) -0.0016(6) 0.0186(7) -0.0021(7)
    N1 0.0310(9) 0.0397(10) 0.0355(10) 0.0022(8) 0.0118(8) 0.0008(9)
    N2 0.0409(10) 0.0310(9) 0.0377(10) 0.0037(8) 0.0151(9) 0.0023(8)
    N3 0.0332(10) 0.0481(12) 0.0406(11) -0.0087(9) 0.0175(9) -0.0048(9)
    N4 0.0269(9) 0.0257(8) 0.0416(10) 0.0007(7) 0.0159(8) -0.0004(8)
    C1 0.0359(12) 0.0481(14) 0.0495(15) -0.0062(11) 0.0196(12) -0.0017(12)
    C2 0.0389(12) 0.0445(13) 0.0324(12) 0.0115(10) 0.0132(10) 0.0003(10)
    C3 0.0398(14) 0.072(2) 0.0381(14) 0.0112(13) 0.0085(12) -0.0019(14)
    C4 0.0498(16) 0.083(2) 0.0357(14) 0.0283(16) 0.0059(13) 0.0053(15)
    C5 0.071(2) 0.0625(19) 0.0414(15) 0.0313(17) 0.0189(15) 0.0140(14)
    C6 0.0675(19) 0.0453(15) 0.0460(15) 0.0195(14) 0.0237(15) 0.0108(12)
    C7 0.0439(13) 0.0377(12) 0.0349(12) 0.0119(10) 0.0153(11) 0.0026(10)
    C8 0.0334(11) 0.0304(10) 0.0312(11) 0.0043(9) 0.0138(9) -0.0007(9)
    C9 0.0270(10) 0.0282(10) 0.0307(11) -0.0011(8) 0.0124(9) 0.0003(8)
    C10 0.0302(10) 0.0243(9) 0.0355(11) -0.0010(8) 0.0155(9) -0.0012(8)
    C11 0.0321(10) 0.0241(9) 0.0313(11) -0.0072(8) 0.0150(9) -0.0027(8)
    C12 0.0292(10) 0.0267(10) 0.0294(10) -0.0019(8) 0.0115(9) 0.0023(8)
    C13 0.0246(9) 0.0239(9) 0.0302(10) -0.0031(8) 0.0125(8) -0.0007(8)
    C14 0.0279(10) 0.0289(10) 0.0249(10) -0.0031(8) 0.0117(8) -0.0022(8)
    C15 0.0483(13) 0.0268(10) 0.0300(11) -0.0073(10) 0.0167(10) -0.0028(9)
    C16 0.082(2) 0.0392(13) 0.0388(14) 0.0177(14) 0.0262(15) 0.0001(11)
    C17 0.089(2) 0.071(2) 0.0360(14) -0.053(2) 0.0204(16) -0.0103(14)
    C18 0.0436(12) 0.0350(11) 0.0307(11) 0.0006(10) 0.0179(10) -0.0003(9)
    C19 0.0249(9) 0.0289(10) 0.0242(10) 0.0005(8) 0.0080(8) -0.0015(8)
    C20 0.0406(12) 0.0276(11) 0.0617(16) 0.0050(10) 0.0261(12) 0.0003(11)
    C21 0.0271(10) 0.0223(9) 0.0484(13) -0.0001(8) 0.0179(10) 0.0013(9)
    C22 0.0332(12) 0.0383(12) 0.0450(14) -0.0049(10) 0.0123(11) 0.0063(11)
    C23 0.0282(12) 0.0508(15) 0.0623(18) -0.0053(11) 0.0116(12) 0.0077(13)
    C24 0.0316(12) 0.0470(14) 0.077(2) -0.0034(11) 0.0282(13) 0.0031(14)
    C25 0.0407(13) 0.0375(12) 0.0617(16) -0.0055(10) 0.0320(13) -0.0044(12)
    C26 0.0310(11) 0.0244(9) 0.0477(13) -0.0018(8) 0.0182(10) -0.0021(9)
    C27 0.0515(15) 0.0427(13) 0.0443(14) -0.0125(12) 0.0221(12) -0.0076(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C14 . 1.901(2) ?
    O1 C19 . 1.232(3) ?
    N1 C8 . 1.373(3) ?
    N1 C2 . 1.379(3) ?
    N1 C1 . 1.456(3) ?
    N2 C8 . 1.310(3) ?
    N2 C7 . 1.391(3) ?
    N3 C26 . 1.365(3) ?
    N3 C27 . 1.447(3) ?
    N3 H3B . 0.81(3) ?
    N4 C19 . 1.340(3) ?
    N4 C21 . 1.450(3) ?
    N4 C20 . 1.467(3) ?
    C1 H1A . 0.9800 ?
    C1 H1B . 0.9800 ?
    C1 H1C . 0.9800 ?
    C2 C7 . 1.394(4) ?
    C2 C3 . 1.401(4) ?
    C3 C4 . 1.388(5) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.395(5) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.376(5) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.412(4) ?
    C6 H6A . 0.9500 ?
    C8 C9 . 1.484(3) ?
    C9 C14 . 1.393(3) ?
    C9 C10 . 1.395(3) ?
    C10 C11 . 1.395(3) ?
    C10 H10A . 0.9500 ?
    C11 C12 . 1.396(3) ?
    C11 C15 . 1.531(3) ?
    C12 C13 . 1.388(3) ?
    C12 H12A . 0.9500 ?
    C13 C14 . 1.389(3) ?
    C13 C19 . 1.510(3) ?
    C15 C18 . 1.526(3) ?
    C15 C17 . 1.527(3) ?
    C15 C16 . 1.545(4) ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 C22 . 1.383(3) ?
    C21 C26 . 1.406(3) ?
    C22 C23 . 1.387(3) ?
    C22 H22A . 0.9500 ?
    C23 C24 . 1.379(4) ?
    C23 H23A . 0.9500 ?
    C24 C25 . 1.375(4) ?
    C24 H24A . 0.9500 ?
    C25 C26 . 1.414(3) ?
    C25 H25A . 0.9500 ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
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
    C8 N1 C2 . . 106.0(2) ?
    C8 N1 C1 . . 128.4(2) ?
    C2 N1 C1 . . 125.5(2) ?
    C8 N2 C7 . . 104.4(2) ?
    C26 N3 C27 . . 122.4(2) ?
    C26 N3 H3B . . 117(2) ?
    C27 N3 H3B . . 119(2) ?
    C19 N4 C21 . . 123.86(18) ?
    C19 N4 C20 . . 119.04(18) ?
    C21 N4 C20 . . 117.02(18) ?
    N1 C1 H1A . . 109.5 ?
    N1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    N1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 C7 . . 105.7(2) ?
    N1 C2 C3 . . 131.4(3) ?
    C7 C2 C3 . . 123.0(3) ?
    C4 C3 C2 . . 115.7(3) ?
    C4 C3 H3A . . 122.1 ?
    C2 C3 H3A . . 122.1 ?
    C3 C4 C5 . . 122.0(3) ?
    C3 C4 H4A . . 119.0 ?
    C5 C4 H4A . . 119.0 ?
    C6 C5 C4 . . 122.0(3) ?
    C6 C5 H5A . . 119.0 ?
    C4 C5 H5A . . 119.0 ?
    C5 C6 C7 . . 117.2(3) ?
    C5 C6 H6A . . 121.4 ?
    C7 C6 H6A . . 121.4 ?
    N2 C7 C2 . . 110.2(2) ?
    N2 C7 C6 . . 129.8(3) ?
    C2 C7 C6 . . 120.0(3) ?
    N2 C8 N1 . . 113.7(2) ?
    N2 C8 C9 . . 124.9(2) ?
    N1 C8 C9 . . 121.4(2) ?
    C14 C9 C10 . . 118.6(2) ?
    C14 C9 C8 . . 122.40(19) ?
    C10 C9 C8 . . 119.00(19) ?
    C9 C10 C11 . . 121.9(2) ?
    C9 C10 H10A . . 119.0 ?
    C11 C10 H10A . . 119.0 ?
    C10 C11 C12 . . 117.3(2) ?
    C10 C11 C15 . . 121.96(19) ?
    C12 C11 C15 . . 120.7(2) ?
    C13 C12 C11 . . 122.3(2) ?
    C13 C12 H12A . . 118.8 ?
    C11 C12 H12A . . 118.8 ?
    C12 C13 C14 . . 118.62(19) ?
    C12 C13 C19 . . 119.05(19) ?
    C14 C13 C19 . . 122.21(19) ?
    C13 C14 C9 . . 121.17(19) ?
    C13 C14 Br . . 119.78(16) ?
    C9 C14 Br . . 119.01(16) ?
    C18 C15 C17 . . 109.2(2) ?
    C18 C15 C11 . . 111.07(18) ?
    C17 C15 C11 . . 108.6(2) ?
    C18 C15 C16 . . 108.3(2) ?
    C17 C15 C16 . . 109.0(3) ?
    C11 C15 C16 . . 110.6(2) ?
    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 ?
    C15 C18 H18A . . 109.5 ?
    C15 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C15 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O1 C19 N4 . . 122.7(2) ?
    O1 C19 C13 . . 119.92(19) ?
    N4 C19 C13 . . 117.37(17) ?
    N4 C20 H20A . . 109.5 ?
    N4 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    N4 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C22 C21 C26 . . 121.5(2) ?
    C22 C21 N4 . . 119.1(2) ?
    C26 C21 N4 . . 119.1(2) ?
    C21 C22 C23 . . 120.3(3) ?
    C21 C22 H22A . . 119.8 ?
    C23 C22 H22A . . 119.8 ?
    C24 C23 C22 . . 119.0(3) ?
    C24 C23 H23A . . 120.5 ?
    C22 C23 H23A . . 120.5 ?
    C25 C24 C23 . . 121.4(2) ?
    C25 C24 H24A . . 119.3 ?
    C23 C24 H24A . . 119.3 ?
    C24 C25 C26 . . 120.8(3) ?
    C24 C25 H25A . . 119.6 ?
    C26 C25 H25A . . 119.6 ?
    N3 C26 C21 . . 121.4(2) ?
    N3 C26 C25 . . 121.8(2) ?
    C21 C26 C25 . . 116.8(2) ?
    N3 C27 H27A . . 109.5 ?
    N3 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    N3 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 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
    C8 N1 C2 C7 . . . . 0.1(2) ?
    C1 N1 C2 C7 . . . . 177.6(2) ?
    C8 N1 C2 C3 . . . . 178.1(3) ?
    C1 N1 C2 C3 . . . . -4.3(4) ?
    N1 C2 C3 C4 . . . . -176.7(3) ?
    C7 C2 C3 C4 . . . . 1.0(4) ?
    C2 C3 C4 C5 . . . . -2.2(4) ?
    C3 C4 C5 C6 . . . . 1.9(5) ?
    C4 C5 C6 C7 . . . . -0.2(5) ?
    C8 N2 C7 C2 . . . . -0.3(3) ?
    C8 N2 C7 C6 . . . . -178.8(3) ?
    N1 C2 C7 N2 . . . . 0.1(3) ?
    C3 C2 C7 N2 . . . . -178.1(2) ?
    N1 C2 C7 C6 . . . . 178.7(2) ?
    C3 C2 C7 C6 . . . . 0.5(4) ?
    C5 C6 C7 N2 . . . . 177.4(3) ?
    C5 C6 C7 C2 . . . . -0.9(4) ?
    C7 N2 C8 N1 . . . . 0.4(3) ?
    C7 N2 C8 C9 . . . . 177.9(2) ?
    C2 N1 C8 N2 . . . . -0.3(3) ?
    C1 N1 C8 N2 . . . . -177.8(2) ?
    C2 N1 C8 C9 . . . . -177.9(2) ?
    C1 N1 C8 C9 . . . . 4.6(4) ?
    N2 C8 C9 C14 . . . . 112.4(3) ?
    N1 C8 C9 C14 . . . . -70.3(3) ?
    N2 C8 C9 C10 . . . . -68.9(3) ?
    N1 C8 C9 C10 . . . . 108.4(2) ?
    C14 C9 C10 C11 . . . . 0.4(3) ?
    C8 C9 C10 C11 . . . . -178.28(19) ?
    C9 C10 C11 C12 . . . . -1.6(3) ?
    C9 C10 C11 C15 . . . . 179.03(19) ?
    C10 C11 C12 C13 . . . . 2.0(3) ?
    C15 C11 C12 C13 . . . . -178.63(19) ?
    C11 C12 C13 C14 . . . . -1.2(3) ?
    C11 C12 C13 C19 . . . . -177.46(18) ?
    C12 C13 C14 C9 . . . . 0.0(3) ?
    C19 C13 C14 C9 . . . . 176.10(18) ?
    C12 C13 C14 Br . . . . -177.74(14) ?
    C19 C13 C14 Br . . . . -1.6(3) ?
    C10 C9 C14 C13 . . . . 0.4(3) ?
    C8 C9 C14 C13 . . . . 179.08(19) ?
    C10 C9 C14 Br . . . . 178.12(15) ?
    C8 C9 C14 Br . . . . -3.2(3) ?
    C10 C11 C15 C18 . . . . -154.3(2) ?
    C12 C11 C15 C18 . . . . 26.3(3) ?
    C10 C11 C15 C17 . . . . 85.6(3) ?
    C12 C11 C15 C17 . . . . -93.8(3) ?
    C10 C11 C15 C16 . . . . -34.1(3) ?
    C12 C11 C15 C16 . . . . 146.5(2) ?
    C21 N4 C19 O1 . . . . -177.7(2) ?
    C20 N4 C19 O1 . . . . 5.7(3) ?
    C21 N4 C19 C13 . . . . 1.1(3) ?
    C20 N4 C19 C13 . . . . -175.5(2) ?
    C12 C13 C19 O1 . . . . 82.7(3) ?
    C14 C13 C19 O1 . . . . -93.4(2) ?
    C12 C13 C19 N4 . . . . -96.1(2) ?
    C14 C13 C19 N4 . . . . 87.7(2) ?
    C19 N4 C21 C22 . . . . -98.6(3) ?
    C20 N4 C21 C22 . . . . 78.2(3) ?
    C19 N4 C21 C26 . . . . 87.6(3) ?
    C20 N4 C21 C26 . . . . -95.7(3) ?
    C26 C21 C22 C23 . . . . -2.4(4) ?
    N4 C21 C22 C23 . . . . -176.1(2) ?
    C21 C22 C23 C24 . . . . 0.8(4) ?
    C22 C23 C24 C25 . . . . 0.4(4) ?
    C23 C24 C25 C26 . . . . 0.1(4) ?
    C27 N3 C26 C21 . . . . -177.6(2) ?
    C27 N3 C26 C25 . . . . 4.3(4) ?
    C22 C21 C26 N3 . . . . -175.4(2) ?
    N4 C21 C26 N3 . . . . -1.7(3) ?
    C22 C21 C26 C25 . . . . 2.8(3) ?
    N4 C21 C26 C25 . . . . 176.5(2) ?
    C24 C25 C26 N3 . . . . 176.5(2) ?
    C24 C25 C26 C21 . . . . -1.6(4) ?
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
    N3 H3B O1 2_655 0.81(3) 2.35(3) 3.038(3) 143(3)
    C4 H4A Br 4_646 0.95 2.98 3.719(3) 135.2
    C12 H12A O1 2_655 0.95 2.37 3.287(3) 163.3