#------------------------------------------------------------------------------
#$Date: 2024-04-27 04:55:05 +0300 (Sat, 27 Apr 2024) $
#$Revision: 291380 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023094.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_2023094
loop_
_publ_author_name
'Abu-Zaied, Mamdouh A.'
'Mohamed-Ezzat, Reham A.'
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 (E)-N-(4-bromophenyl)-2-cyano-3-[3-(2-methylpropyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enamide
;
_journal_coeditor_code           JP2004
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003086
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C23 H21 Br N4 O'
_chemical_formula_moiety         'C23 H21 Br N4 O'
_chemical_formula_sum            'C23 H21 Br N4 O'
_chemical_formula_weight         449.35
_chemical_name_systematic
(E)-N-(4-Bromophenyl)-2-cyano-3-[3-(2-methylpropyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                109.790(6)
_cell_angle_beta                 96.720(6)
_cell_angle_gamma                90.657(6)
_cell_formula_units_Z            4
_cell_length_a                   9.2260(6)
_cell_length_b                   12.7703(9)
_cell_length_c                   18.6607(13)
_cell_measurement_reflns_used    28092
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      80.0220
_cell_measurement_theta_min      4.8200
_cell_volume                     2051.4(3)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
XP, Version 5.1 (Bruker, 1998)
;
_computing_publication_material
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8658
_diffrn_reflns_theta_full        77.500
_diffrn_reflns_theta_max         80.675
_diffrn_reflns_theta_min         2.537
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       lath
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.451
_refine_diff_density_min         -0.753
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         8658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0504P)²+3.4902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                8436
_reflns_number_total             8658
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp2004.cif
_cod_data_source_block           I
_cod_database_code               2023094
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.670
_shelx_estimated_absorpt_t_max   0.944
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.8296(3) 0.93208(19) 0.80174(13) 0.0195(5) Uani d 1 . .
N N2 0.8728(3) 1.0434(2) 0.83283(14) 0.0223(5) Uani d 1 . .
C C3 0.7898(3) 1.0913(2) 0.79189(16) 0.0204(5) Uani d 1 . .
C C4 0.6899(3) 1.0129(2) 0.73414(15) 0.0192(5) Uani d 1 . .
C C5 0.7208(3) 0.9108(2) 0.74228(15) 0.0194(5) Uani d 1 . .
H H5 0.674853 0.840171 0.712139 0.023 Uiso calc 1 . .
C C6 0.8085(3) 1.2144(2) 0.80848(17) 0.0234(6) Uani d 1 . .
H H6A 0.814865 1.227362 0.759512 0.028 Uiso calc 1 . .
H H6B 0.902540 1.242139 0.841653 0.028 Uiso calc 1 . .
C C7 0.6856(4) 1.2837(3) 0.84792(18) 0.0269(6) Uani d 1 . .
H H7 0.592945 1.261373 0.811598 0.032 Uiso calc 1 . .
C C8 0.6612(5) 1.2636(3) 0.9211(2) 0.0364(8) Uani d 1 . .
H H8A 0.633489 1.184622 0.909325 0.055 Uiso calc 1 . .
H H8B 0.582845 1.309233 0.944196 0.055 Uiso calc 1 . .
H H8C 0.751428 1.283761 0.957285 0.055 Uiso calc 1 . .
C C9 0.7220(4) 1.4066(3) 0.8637(2) 0.0331(7) Uani d 1 . .
H H9A 0.814866 1.429449 0.897552 0.050 Uiso calc 1 . .
H H9B 0.644192 1.450826 0.888617 0.050 Uiso calc 1 . .
H H9C 0.730456 1.418601 0.815190 0.050 Uiso calc 1 . .
C C10 0.5809(3) 1.0408(2) 0.68333(15) 0.0188(5) Uani d 1 . .
H H10 0.581156 1.117548 0.688873 0.023 Uiso calc 1 . .
C C11 0.4770(3) 0.9745(2) 0.62836(16) 0.0191(5) Uani d 1 . .
C C12 0.3728(3) 1.0298(2) 0.58637(15) 0.0188(5) Uani d 1 . .
C C13 0.4618(3) 0.8564(2) 0.60891(16) 0.0215(6) Uani d 1 . .
N N3 0.4422(3) 0.7617(2) 0.59075(15) 0.0274(5) Uani d 1 . .
N N4 0.3098(3) 0.9632(2) 0.51592(14) 0.0204(5) Uani d 1 . .
H H4 0.334(4) 0.899(3) 0.497(2) 0.026(9) Uiso d 1 . .
O O1 0.3486(2) 1.12794(16) 0.61581(11) 0.0224(4) Uani d 1 . .
C C14 0.8933(3) 0.8565(2) 0.83581(16) 0.0217(6) Uani d 1 . .
C C15 0.8624(3) 0.7422(2) 0.80079(17) 0.0242(6) Uani d 1 . .
H H15 0.801738 0.713321 0.752930 0.029 Uiso calc 1 . .
C C16 0.9223(4) 0.6715(3) 0.83729(18) 0.0279(6) Uani d 1 . .
H H16 0.901761 0.593388 0.814056 0.033 Uiso calc 1 . .
C C17 1.0113(4) 0.7126(3) 0.90700(18) 0.0282(6) Uani d 1 . .
H H17 1.050090 0.663052 0.931612 0.034 Uiso calc 1 . .
C C18 1.0436(4) 0.8263(3) 0.94063(18) 0.0301(7) Uani d 1 . .
H H18 1.105799 0.854788 0.988046 0.036 Uiso calc 1 . .
C C19 0.9854(4) 0.8986(3) 0.90518(18) 0.0278(6) Uani d 1 . .
H H19 1.008014 0.976494 0.928011 0.033 Uiso calc 1 . .
C C20 0.2082(3) 0.9978(2) 0.46651(15) 0.0181(5) Uani d 1 . .
C C21 0.2181(3) 1.1050(2) 0.46342(16) 0.0197(5) Uani d 1 . .
H H21 0.294543 1.156414 0.494685 0.024 Uiso calc 1 . .
C C22 0.1169(3) 1.1369(2) 0.41490(16) 0.0211(5) Uani d 1 . .
H H22 0.122820 1.209905 0.412529 0.025 Uiso calc 1 . .
C C23 0.0071(3) 1.0600(2) 0.36994(16) 0.0205(5) Uani d 1 . .
Br Br1 -0.13165(3) 1.10741(2) 0.30445(2) 0.02507(8) Uani d 1 . .
C C24 -0.0026(3) 0.9522(2) 0.37003(17) 0.0227(6) Uani d 1 . .
H H24 -0.076916 0.900263 0.337075 0.027 Uiso calc 1 . .
C C25 0.0985(3) 0.9211(2) 0.41927(16) 0.0220(6) Uani d 1 . .
H H25 0.092915 0.847572 0.420802 0.026 Uiso calc 1 . .
N N1' 0.6634(3) 0.5581(2) 0.19407(13) 0.0212(5) Uani d 1 . .
N N2' 0.6975(3) 0.4479(2) 0.16639(14) 0.0232(5) Uani d 1 . .
C C3' 0.6367(3) 0.4009(2) 0.20969(16) 0.0219(6) Uani d 1 . .
C C4' 0.5604(3) 0.4795(2) 0.26490(16) 0.0206(5) Uani d 1 . .
C C5' 0.5837(3) 0.5796(2) 0.25271(16) 0.0204(5) Uani d 1 . .
H H5' 0.549638 0.649800 0.280581 0.024 Uiso calc 1 . .
C C6' 0.6537(3) 0.2800(2) 0.19788(18) 0.0237(6) Uani d 1 . .
H H6A' 0.675875 0.271529 0.248784 0.028 Uiso calc 1 . .
H H6B' 0.738793 0.255432 0.169796 0.028 Uiso calc 1 . .
C C7' 0.5204(4) 0.2024(3) 0.15374(18) 0.0290(7) Uani d 1 . .
H H7' 0.437221 0.223875 0.184710 0.035 Uiso calc 1 . .
C C8' 0.4739(6) 0.2124(4) 0.0759(2) 0.0559(13) Uani d 1 . .
H H8A' 0.448415 0.289057 0.082456 0.067 Uiso calc 1 . .
H H8B' 0.388753 0.161378 0.050055 0.067 Uiso calc 1 . .
H H8C' 0.554472 0.193070 0.044653 0.067 Uiso calc 1 . .
C C9' 0.5519(4) 0.0823(3) 0.1454(2) 0.0364(8) Uani d 1 . .
H H9A' 0.579375 0.076961 0.196370 0.044 Uiso calc 1 . .
H H9B' 0.632326 0.058781 0.114547 0.044 Uiso calc 1 . .
H H9C' 0.464345 0.033882 0.120015 0.044 Uiso calc 1 . .
C C10' 0.4783(3) 0.4527(2) 0.31708(16) 0.0197(5) Uani d 1 . .
H H10' 0.475359 0.376301 0.312449 0.024 Uiso calc 1 . .
C C11' 0.4033(3) 0.5191(2) 0.37249(16) 0.0190(5) Uani d 1 . .
C C12' 0.3216(3) 0.4648(2) 0.41656(16) 0.0201(5) Uani d 1 . .
C C13' 0.3989(3) 0.6369(2) 0.39099(16) 0.0209(5) Uani d 1 . .
N N3' 0.3903(3) 0.7323(2) 0.40865(15) 0.0274(5) Uani d 1 . .
N N4' 0.2974(3) 0.5319(2) 0.48735(14) 0.0206(5) Uani d 1 . .
H H4' 0.328(5) 0.597(3) 0.504(3) 0.046(13) Uiso d 1 . .
O O1' 0.2807(2) 0.36590(16) 0.38837(11) 0.0221(4) Uani d 1 . .
C C14' 0.7091(3) 0.6320(2) 0.15749(17) 0.0227(6) Uani d 1 . .
C C15' 0.7193(3) 0.7463(2) 0.19677(17) 0.0234(6) Uani d 1 . .
H H15' 0.696881 0.775749 0.247998 0.028 Uiso calc 1 . .
C C16' 0.7630(4) 0.8168(3) 0.15950(18) 0.0276(6) Uani d 1 . .
H H16' 0.770824 0.895077 0.185682 0.033 Uiso calc 1 . .
C C17' 0.7951(4) 0.7743(3) 0.08488(19) 0.0288(6) Uani d 1 . .
H H17' 0.824273 0.823276 0.059927 0.035 Uiso calc 1 . .
C C18' 0.7847(4) 0.6603(3) 0.04658(19) 0.0322(7) Uani d 1 . .
H H18' 0.807749 0.631370 -0.004554 0.039 Uiso calc 1 . .
C C19' 0.7409(4) 0.5874(3) 0.08222(18) 0.0290(7) Uani d 1 . .
H H19' 0.732788 0.509238 0.055784 0.035 Uiso calc 1 . .
C C20' 0.2234(3) 0.4972(2) 0.53829(15) 0.0184(5) Uani d 1 . .
C C21' 0.2400(3) 0.3921(2) 0.54385(16) 0.0199(5) Uani d 1 . .
H H21' 0.302404 0.342360 0.513082 0.024 Uiso calc 1 . .
C C22' 0.1665(3) 0.3593(2) 0.59383(16) 0.0216(6) Uani d 1 . .
H H22' 0.176915 0.287245 0.597366 0.026 Uiso calc 1 . .
C C23' 0.0771(3) 0.4338(2) 0.63876(16) 0.0207(5) Uani d 1 . .
Br Br1' -0.02465(4) 0.38496(3) 0.70597(2) 0.02632(8) Uani d 1 . .
C C24' 0.0621(3) 0.5396(2) 0.63612(17) 0.0237(6) Uani d 1 . .
H H24' 0.002619 0.589873 0.668537 0.028 Uiso calc 1 . .
C C25' 0.1352(3) 0.5716(2) 0.58544(17) 0.0221(6) Uani d 1 . .
H H25' 0.125442 0.644200 0.582714 0.026 Uiso calc 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'
N N 0.0311 0.0180 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 N2 . . 112.2(2) y
C5 N1 C14 . . 128.3(2) y
N2 N1 C14 . . 119.4(2) ?
C3 N2 N1 . . 104.9(2) y
N2 C3 C4 . . 111.9(2) y
N2 C3 C6 . . 120.1(3) ?
C4 C3 C6 . . 128.0(3) y
C5 C4 C3 . . 104.5(2) y
C5 C4 C10 . . 130.7(3) y
C3 C4 C10 . . 124.8(3) ?
N1 C5 C4 . . 106.5(2) y
C3 C6 C7 . . 115.1(3) ?
C8 C7 C9 . . 110.8(3) ?
C8 C7 C6 . . 112.3(3) ?
C9 C7 C6 . . 109.2(3) ?
C11 C10 C4 . . 130.1(3) y
C10 C11 C13 . . 123.8(3) ?
C10 C11 C12 . . 117.5(2) ?
C13 C11 C12 . . 118.7(2) ?
O1 C12 N4 . . 124.3(3) ?
O1 C12 C11 . . 120.4(2) ?
N4 C12 C11 . . 115.3(2) ?
N3 C13 C11 . . 176.0(3) ?
C12 N4 C20 . . 124.9(2) ?
C15 C14 C19 . . 120.6(3) ?
C15 C14 N1 . . 120.3(3) ?
C19 C14 N1 . . 119.0(3) ?
C16 C15 C14 . . 118.5(3) ?
C17 C16 C15 . . 121.3(3) ?
C16 C17 C18 . . 119.7(3) ?
C19 C18 C17 . . 120.1(3) ?
C18 C19 C14 . . 119.7(3) ?
C21 C20 C25 . . 120.1(3) ?
C21 C20 N4 . . 121.4(2) ?
C25 C20 N4 . . 118.5(2) ?
C22 C21 C20 . . 120.2(3) ?
C23 C22 C21 . . 118.6(3) ?
C24 C23 C22 . . 122.5(3) ?
C24 C23 Br1 . . 120.1(2) ?
C22 C23 Br1 . . 117.4(2) ?
C23 C24 C25 . . 118.6(3) ?
C24 C25 C20 . . 120.0(3) ?
C5' N1' N2' . . 112.5(2) y
C5' N1' C14' . . 128.5(2) y
N2' N1' C14' . . 118.9(2) ?
C3' N2' N1' . . 104.6(2) y
N2' C3' C4' . . 111.5(3) y
N2' C3' C6' . . 120.3(3) ?
C4' C3' C6' . . 128.2(3) y
C5' C4' C10' . . 131.0(3) y
C5' C4' C3' . . 104.3(2) y
C10' C4' C3' . . 124.6(3) ?
N1' C5' C4' . . 107.0(2) y
C3' C6' C7' . . 115.2(3) ?
C8' C7' C9' . . 110.5(3) ?
C8' C7' C6' . . 112.6(3) ?
C9' C7' C6' . . 110.0(3) ?
C11' C10' C4' . . 130.4(3) y
C10' C11' C13' . . 123.8(3) ?
C10' C11' C12' . . 117.7(2) ?
C13' C11' C12' . . 118.5(2) ?
O1' C12' N4' . . 124.0(3) ?
O1' C12' C11' . . 120.5(3) ?
N4' C12' C11' . . 115.5(2) ?
N3' C13' C11' . . 176.4(3) ?
C12' N4' C20' . . 124.6(2) ?
C15' C14' C19' . . 121.5(3) ?
C15' C14' N1' . . 119.8(3) ?
C19' C14' N1' . . 118.7(3) ?
C14' C15' C16' . . 118.6(3) ?
C17' C16' C15' . . 120.8(3) ?
C16' C17' C18' . . 119.9(3) ?
C17' C18' C19' . . 120.7(3) ?
C14' C19' C18' . . 118.5(3) ?
C21' C20' C25' . . 119.7(3) ?
C21' C20' N4' . . 121.2(2) ?
C25' C20' N4' . . 119.1(2) ?
C22' C21' C20' . . 120.5(3) ?
C21' C22' C23' . . 118.7(3) ?
C24' C23' C22' . . 122.0(3) ?
C24' C23' Br1' . . 120.4(2) ?
C22' C23' Br1' . . 117.5(2) ?
C23' C24' C25' . . 119.0(3) ?
C24' C25' C20' . . 120.1(3) ?
N1 C5 H5 . . 126.7 ?
C4 C5 H5 . . 126.7 ?
C3 C6 H6A . . 108.5 ?
C7 C6 H6A . . 108.5 ?
C3 C6 H6B . . 108.5 ?
C7 C6 H6B . . 108.5 ?
H6A C6 H6B . . 107.5 ?
C8 C7 H7 . . 108.1 ?
C9 C7 H7 . . 108.1 ?
C6 C7 H7 . . 108.1 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 H10 . . 115.0 ?
C4 C10 H10 . . 115.0 ?
C12 N4 H4 . . 121(3) ?
C20 N4 H4 . . 114(3) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 H19 . . 120.1 ?
C14 C19 H19 . . 120.1 ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C23 C22 H22 . . 120.7 ?
C21 C22 H22 . . 120.7 ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C24 C25 H25 . . 120.0 ?
C20 C25 H25 . . 120.0 ?
N1' C5' H5' . . 126.5 ?
C4' C5' H5' . . 126.5 ?
C3' C6' H6A' . . 108.5 ?
C7' C6' H6A' . . 108.5 ?
C3' C6' H6B' . . 108.5 ?
C7' C6' H6B' . . 108.5 ?
H6A' C6' H6B' . . 107.5 ?
C8' C7' H7' . . 107.9 ?
C9' C7' H7' . . 107.9 ?
C6' C7' H7' . . 107.9 ?
C7' C8' H8A' . . 109.5 ?
C7' C8' H8B' . . 109.5 ?
H8A' C8' H8B' . . 109.5 ?
C7' C8' H8C' . . 109.5 ?
H8A' C8' H8C' . . 109.5 ?
H8B' C8' H8C' . . 109.5 ?
C7' C9' H9A' . . 109.5 ?
C7' C9' H9B' . . 109.5 ?
H9A' C9' H9B' . . 109.5 ?
C7' C9' H9C' . . 109.5 ?
H9A' C9' H9C' . . 109.5 ?
H9B' C9' H9C' . . 109.5 ?
C11' C10' H10' . . 114.8 ?
C4' C10' H10' . . 114.8 ?
C12' N4' H4' . . 120(3) ?
C20' N4' H4' . . 115(3) ?
C14' C15' H15' . . 120.7 ?
C16' C15' H15' . . 120.7 ?
C17' C16' H16' . . 119.6 ?
C15' C16' H16' . . 119.6 ?
C16' C17' H17' . . 120.1 ?
C18' C17' H17' . . 120.1 ?
C17' C18' H18' . . 119.6 ?
C19' C18' H18' . . 119.6 ?
C14' C19' H19' . . 120.8 ?
C18' C19' H19' . . 120.8 ?
C22' C21' H21' . . 119.8 ?
C20' C21' H21' . . 119.8 ?
C21' C22' H22' . . 120.6 ?
C23' C22' H22' . . 120.6 ?
C23' C24' H24' . . 120.5 ?
C25' C24' H24' . . 120.5 ?
C24' C25' H25' . . 120.0 ?
C20' C25' H25' . . 120.0 ?
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
N1 C5 . 1.357(4) y
N1 N2 . 1.375(3) y
N1 C14 . 1.423(4) ?
N2 C3 . 1.317(4) y
C3 C4 . 1.424(4) y
C3 C6 . 1.499(4) ?
C4 C5 . 1.392(4) y
C4 C10 . 1.432(4) ?
C6 C7 . 1.545(4) ?
C7 C8 . 1.514(5) ?
C7 C9 . 1.521(4) ?
C10 C11 . 1.361(4) ?
C11 C13 . 1.428(4) ?
C11 C12 . 1.500(4) ?
C12 O1 . 1.221(3) y
C12 N4 . 1.357(4) ?
C13 N3 . 1.145(4) y
N4 C20 . 1.417(4) ?
C14 C15 . 1.392(4) ?
C14 C19 . 1.395(4) ?
C15 C16 . 1.387(4) ?
C16 C17 . 1.386(5) ?
C17 C18 . 1.386(5) ?
C18 C19 . 1.385(4) ?
C20 C21 . 1.391(4) ?
C20 C25 . 1.395(4) ?
C21 C22 . 1.385(4) ?
C22 C23 . 1.384(4) ?
C23 C24 . 1.379(4) ?
C23 Br1 . 1.911(3) y
C24 C25 . 1.388(4) ?
N1' C5' . 1.343(4) y
N1' N2' . 1.380(3) y
N1' C14' . 1.425(4) ?
N2' C3' . 1.324(4) y
C3' C4' . 1.432(4) y
C3' C6' . 1.497(4) ?
C4' C5' . 1.390(4) y
C4' C10' . 1.425(4) ?
C6' C7' . 1.534(4) ?
C7' C8' . 1.514(5) ?
C7' C9' . 1.523(5) ?
C10' C11' . 1.361(4) ?
C11' C13' . 1.427(4) ?
C11' C12' . 1.498(4) ?
C12' O1' . 1.228(3) y
C12' N4' . 1.355(4) ?
C13' N3' . 1.155(4) y
N4' C20' . 1.413(4) ?
C14' C15' . 1.390(4) ?
C14' C19' . 1.393(4) ?
C15' C16' . 1.392(4) ?
C16' C17' . 1.382(5) ?
C17' C18' . 1.384(5) ?
C18' C19' . 1.395(4) ?
C20' C21' . 1.390(4) ?
C20' C25' . 1.399(4) ?
C21' C22' . 1.382(4) ?
C22' C23' . 1.388(4) ?
C23' C24' . 1.377(4) ?
C23' Br1' . 1.906(3) y
C24' C25' . 1.386(4) ?
C5 H5 . 0.9500 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 H10 . 0.9500 ?
N4 H4 . 0.82(3) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
C5' H5' . 0.9500 ?
C6' H6A' . 0.9900 ?
C6' H6B' . 0.9900 ?
C7' H7' . 1.0000 ?
C8' H8A' . 0.9800 ?
C8' H8B' . 0.9800 ?
C8' H8C' . 0.9800 ?
C9' H9A' . 0.9800 ?
C9' H9B' . 0.9800 ?
C9' H9C' . 0.9800 ?
C10' H10' . 0.9500 ?
N4' H4' . 0.82(3) ?
C15' H15' . 0.9500 ?
C16' H16' . 0.9500 ?
C17' H17' . 0.9500 ?
C18' H18' . 0.9500 ?
C19' H19' . 0.9500 ?
C21' H21' . 0.9500 ?
C22' H22' . 0.9500 ?
C24' H24' . 0.9500 ?
C25' H25' . 0.9500 ?
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
N4 H4 N3' . 0.82(3) 2.31(3) 3.107(3) 162(3) yes
N4' H4' N3 . 0.82(3) 2.32(4) 3.097(3) 158(4) yes
C15 H15 O1' 2_666 0.95 2.50 3.417(4) 161.7 yes
C15' H15' O1 2_676 0.95 2.51 3.455(4) 174.0 yes
C16' H16' Br1 1_655 0.95 2.91 3.813(3) 158.7 yes
C16 H16 Br1' 1_655 0.95 2.89 3.726(3) 147.8 yes
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
C5 N1 N2 C3 . . . . -0.1(3) ?
C14 N1 N2 C3 . . . . -176.7(2) ?
N1 N2 C3 C4 . . . . 0.7(3) ?
N1 N2 C3 C6 . . . . -178.7(2) ?
N2 C3 C4 C5 . . . . -1.0(3) ?
C6 C3 C4 C5 . . . . 178.3(3) ?
N2 C3 C4 C10 . . . . 176.7(3) ?
C6 C3 C4 C10 . . . . -4.0(5) ?
N2 N1 C5 C4 . . . . -0.5(3) ?
C14 N1 C5 C4 . . . . 175.6(3) ?
C3 C4 C5 N1 . . . . 0.9(3) ?
C10 C4 C5 N1 . . . . -176.6(3) ?
N2 C3 C6 C7 . . . . -107.2(3) y
C4 C3 C6 C7 . . . . 73.5(4) y
C3 C6 C7 C8 . . . . 54.6(4) ?
C3 C6 C7 C9 . . . . 177.9(3) ?
C5 C4 C10 C11 . . . . -0.3(5) ?
C3 C4 C10 C11 . . . . -177.4(3) ?
C4 C10 C11 C13 . . . . -2.5(5) ?
C4 C10 C11 C12 . . . . 177.3(3) ?
C10 C11 C12 O1 . . . . -24.1(4) ?
C13 C11 C12 O1 . . . . 155.7(3) ?
C10 C11 C12 N4 . . . . 156.4(3) y
C13 C11 C12 N4 . . . . -23.8(4) ?
O1 C12 N4 C20 . . . . 0.4(5) ?
C11 C12 N4 C20 . . . . 179.9(3) ?
C5 N1 C14 C15 . . . . 10.7(5) y
N2 N1 C14 C15 . . . . -173.4(3) y
C5 N1 C14 C19 . . . . -168.4(3) ?
N2 N1 C14 C19 . . . . 7.5(4) ?
C19 C14 C15 C16 . . . . 1.6(5) ?
N1 C14 C15 C16 . . . . -177.6(3) ?
C14 C15 C16 C17 . . . . -0.2(5) ?
C15 C16 C17 C18 . . . . -1.0(5) ?
C16 C17 C18 C19 . . . . 0.9(5) ?
C17 C18 C19 C14 . . . . 0.4(5) ?
C15 C14 C19 C18 . . . . -1.7(5) ?
N1 C14 C19 C18 . . . . 177.4(3) ?
C12 N4 C20 C21 . . . . 34.5(4) ?
C12 N4 C20 C25 . . . . -146.8(3) ?
C25 C20 C21 C22 . . . . 1.7(4) ?
N4 C20 C21 C22 . . . . -179.7(3) ?
C20 C21 C22 C23 . . . . -0.1(4) ?
C21 C22 C23 C24 . . . . -2.0(4) ?
C21 C22 C23 Br1 . . . . 179.4(2) ?
C22 C23 C24 C25 . . . . 2.5(4) ?
Br1 C23 C24 C25 . . . . -178.9(2) ?
C23 C24 C25 C20 . . . . -0.9(4) ?
C21 C20 C25 C24 . . . . -1.1(4) ?
N4 C20 C25 C24 . . . . -179.8(3) ?
C5' N1' N2' C3' . . . . -0.1(3) ?
C14' N1' N2' C3' . . . . -177.8(3) ?
N1' N2' C3' C4' . . . . 1.1(3) ?
N1' N2' C3' C6' . . . . -178.4(3) ?
N2' C3' C4' C5' . . . . -1.6(3) ?
C6' C3' C4' C5' . . . . 177.8(3) ?
N2' C3' C4' C10' . . . . 176.9(3) ?
C6' C3' C4' C10' . . . . -3.7(5) ?
N2' N1' C5' C4' . . . . -0.9(3) ?
C14' N1' C5' C4' . . . . 176.5(3) ?
C10' C4' C5' N1' . . . . -176.9(3) ?
C3' C4' C5' N1' . . . . 1.4(3) ?
N2' C3' C6' C7' . . . . -102.1(3) y
C4' C3' C6' C7' . . . . 78.5(4) y
C3' C6' C7' C8' . . . . 56.1(4) ?
C3' C6' C7' C9' . . . . 179.8(3) ?
C5' C4' C10' C11' . . . . -3.0(5) ?
C3' C4' C10' C11' . . . . 178.9(3) ?
C4' C10' C11' C13' . . . . -2.7(5) ?
C4' C10' C11' C12' . . . . 177.6(3) ?
C10' C11' C12' O1' . . . . -24.7(4) ?
C13' C11' C12' O1' . . . . 155.5(3) ?
C10' C11' C12' N4' . . . . 155.5(3) y
C13' C11' C12' N4' . . . . -24.2(4) ?
O1' C12' N4' C20' . . . . 0.6(5) ?
C11' C12' N4' C20' . . . . -179.6(3) ?
C5' N1' C14' C15' . . . . 23.4(5) y
N2' N1' C14' C15' . . . . -159.4(3) y
C5' N1' C14' C19' . . . . -155.8(3) ?
N2' N1' C14' C19' . . . . 21.5(4) ?
C19' C14' C15' C16' . . . . -0.3(5) ?
N1' C14' C15' C16' . . . . -179.5(3) ?
C14' C15' C16' C17' . . . . 0.3(5) ?
C15' C16' C17' C18' . . . . -0.4(5) ?
C16' C17' C18' C19' . . . . 0.6(5) ?
C15' C14' C19' C18' . . . . 0.5(5) ?
N1' C14' C19' C18' . . . . 179.6(3) ?
C17' C18' C19' C14' . . . . -0.6(5) ?
C12' N4' C20' C21' . . . . 37.1(4) ?
C12' N4' C20' C25' . . . . -144.8(3) ?
C25' C20' C21' C22' . . . . 2.1(4) ?
N4' C20' C21' C22' . . . . -179.8(3) ?
C20' C21' C22' C23' . . . . -0.6(4) ?
C21' C22' C23' C24' . . . . -1.4(4) ?
C21' C22' C23' Br1' . . . . 179.1(2) ?
C22' C23' C24' C25' . . . . 1.9(4) ?
Br1' C23' C24' C25' . . . . -178.6(2) ?
C23' C24' C25' C20' . . . . -0.4(4) ?
C21' C20' C25' C24' . . . . -1.5(4) ?
N4' C20' C25' C24' . . . . -179.7(3) ?
