#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/42/2224234.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_2224234
loop_
_publ_author_name
'Heng, Lin-Sen'
'Li, Yong-Hong'
'Mei, Xiang-Dong'
'Ning, Jun'
_publ_section_title
;
 4-(4-Bromo-3-methyl-1H-pyrazol-1-yl)-6-(but-3-ynyloxy)pyrimidine
;
_journal_coeditor_code           HB5193
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3031
_journal_paper_doi               10.1107/S1600536809046194
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H11 Br N4 O'
_chemical_formula_moiety         'C12 H11 Br N4 O'
_chemical_formula_sum            'C12 H11 Br N4 O'
_chemical_formula_weight         307.16
_chemical_name_systematic
;
4-(4-Bromo-3-methyl-1H-pyrazol-1-yl)-6-(but-3-ynyloxy)pyrimidine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.34(3)
_cell_angle_beta                 77.98(3)
_cell_angle_gamma                80.78(3)
_cell_formula_units_Z            4
_cell_length_a                   7.9053(16)
_cell_length_b                   10.045(2)
_cell_length_c                   16.807(3)
_cell_measurement_reflns_used    536
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1254.7(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15373
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    3.270
_exptl_absorpt_correction_T_max  0.803
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.404
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5693
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0360P)²+1.1156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                4988
_reflns_number_total             5693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5193.cif
_cod_data_source_block           I
_cod_original_cell_volume        1254.7(4)
_cod_database_code               2224234
_cod_database_fobs_code          2224234
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.84764(4) 0.85935(4) -0.01999(2) 0.04160(12) Uani d . 1 . .
Br Br2 -0.32369(4) 0.71052(4) 0.25637(2) 0.04014(12) Uani d . 1 . .
O O1 -0.0831(3) 0.4253(2) 0.12494(14) 0.0390(6) Uani d . 1 . .
N N1 0.4057(3) 0.4528(3) 0.15609(17) 0.0313(6) Uani d . 1 . .
N N2 0.1464(3) 0.3392(3) 0.19584(17) 0.0329(6) Uani d . 1 . .
N N3 0.4330(3) 0.6484(3) 0.04879(16) 0.0275(6) Uani d . 1 . .
N N4 0.3723(4) 0.7482(3) -0.01432(16) 0.0319(6) Uani d . 1 . .
N N5 0.0933(3) 0.3312(3) 0.46819(17) 0.0311(6) Uani d . 1 . .
N N6 0.3526(4) 0.2288(3) 0.52183(18) 0.0364(7) Uani d . 1 A .
N N7 0.0905(3) 0.5264(3) 0.36020(15) 0.0267(5) Uani d . 1 . .
N N8 0.1708(3) 0.6315(3) 0.30304(17) 0.0322(6) Uani d . 1 . .
C C1 0.3082(4) 0.3559(3) 0.2019(2) 0.0323(7) Uani d . 1 . .
H H1A 0.3588 0.2898 0.2443 0.039 Uiso calc R 1 . .
C C2 0.3293(4) 0.5457(3) 0.09735(18) 0.0262(6) Uani d . 1 . .
C C3 0.1647(4) 0.5414(3) 0.0840(2) 0.0309(7) Uani d . 1 . .
H H3A 0.1140 0.6078 0.0418 0.037 Uiso calc R 1 . .
C C4 0.0784(4) 0.4343(3) 0.1362(2) 0.0313(7) Uani d . 1 . .
C C5 0.5956(4) 0.6658(3) 0.0570(2) 0.0315(7) Uani d . 1 . .
H H5A 0.6636 0.6096 0.0961 0.038 Uiso calc R 1 . .
C C6 0.6397(4) 0.7794(3) -0.0020(2) 0.0304(7) Uani d . 1 . .
C C7 0.4990(4) 0.8284(3) -0.04569(19) 0.0302(7) Uani d . 1 . .
C C8 0.4879(5) 0.9490(4) -0.1191(2) 0.0400(8) Uani d . 1 . .
H H8A 0.3742 0.9589 -0.1359 0.060 Uiso calc R 1 . .
H H8B 0.5802 0.9331 -0.1657 0.060 Uiso calc R 1 . .
H H8C 0.5020 1.0337 -0.1035 0.060 Uiso calc R 1 . .
C C9 -0.1643(5) 0.3004(4) 0.1696(2) 0.0388(8) Uani d . 1 . .
H H9A -0.0746 0.2192 0.1722 0.047 Uiso calc R 1 . .
H H9B -0.2516 0.2868 0.1387 0.047 Uiso calc R 1 . .
C C10 -0.2516(5) 0.3097(4) 0.2568(2) 0.0387(8) Uani d . 1 . .
H H10A -0.1668 0.3282 0.2874 0.046 Uiso calc R 1 . .
H H10B -0.3476 0.3863 0.2548 0.046 Uiso calc R 1 . .
C C11 -0.3206(4) 0.1772(4) 0.2997(2) 0.0404(8) Uani d . 1 . .
C C12 -0.3688(5) 0.0678(4) 0.3306(2) 0.0461(9) Uani d . 1 . .
H H12 -0.4077 -0.0205 0.3555 0.055 Uiso calc R 1 . .
C C13 0.1847(4) 0.2382(3) 0.5180(2) 0.0324(7) Uani d . 1 . .
H H13A 0.1221 0.1683 0.5563 0.039 Uiso calc R 1 . .
C C14 0.1859(4) 0.4271(3) 0.41388(19) 0.0259(6) Uani d . 1 . .
C C15 0.3608(4) 0.4307(3) 0.4096(2) 0.0319(7) Uani d . 1 A .
H H15A 0.4244 0.4988 0.3701 0.038 Uiso calc R 1 . .
C C16 0.4367(4) 0.3271(4) 0.4674(2) 0.0384(8) Uani d . 1 . .
C C17 -0.0815(4) 0.5332(3) 0.35647(19) 0.0285(7) Uani d . 1 . .
H H17A -0.1629 0.4726 0.3900 0.034 Uiso calc R 1 . .
C C18 -0.1110(4) 0.6466(3) 0.2937(2) 0.0294(7) Uani d . 1 . .
C C19 0.0468(4) 0.7055(3) 0.2624(2) 0.0315(7) Uani d . 1 . .
C C20 0.0820(5) 0.8313(4) 0.1948(2) 0.0460(9) Uani d . 1 . .
H H20A 0.2043 0.8464 0.1873 0.069 Uiso calc R 1 . .
H H20B 0.0071 0.9119 0.2101 0.069 Uiso calc R 1 . .
H H20C 0.0578 0.8183 0.1426 0.069 Uiso calc R 1 . .
O O2 0.6027(4) 0.3390(4) 0.4735(3) 0.0316(10) Uani d PU 0.714(8) A 1
C C21 0.6792(6) 0.2448(5) 0.5416(3) 0.0337(13) Uani d PU 0.714(8) A 1
H H21A 0.5903 0.2319 0.5931 0.040 Uiso calc PR 0.714(8) A 1
H H21B 0.7758 0.2861 0.5521 0.040 Uiso calc PR 0.714(8) A 1
C C22 0.7475(7) 0.1058(6) 0.5210(3) 0.0374(13) Uani d PU 0.714(8) A 1
H H22A 0.6528 0.0660 0.5078 0.045 Uiso calc PR 0.714(8) A 1
H H22B 0.8417 0.1173 0.4716 0.045 Uiso calc PR 0.714(8) A 1
C C23 0.8143(6) 0.0124(5) 0.5927(3) 0.0347(13) Uani d PU 0.714(8) A 1
O O2' 0.6200(12) 0.3001(11) 0.4464(6) 0.027(2) Uiso d PU 0.286(8) A 2
C C21' 0.7129(14) 0.1783(13) 0.4919(7) 0.027(3) Uiso d PU 0.286(8) A 2
H H21C 0.8333 0.1649 0.4611 0.032 Uiso calc PR 0.286(8) A 2
H H21D 0.6554 0.0960 0.4953 0.032 Uiso calc PR 0.286(8) A 2
C C22' 0.7188(17) 0.1897(14) 0.5783(9) 0.035(3) Uiso d PU 0.286(8) A 2
H H22C 0.7883 0.2653 0.5750 0.042 Uiso calc PR 0.286(8) A 2
H H22D 0.5993 0.2135 0.6070 0.042 Uiso calc PR 0.286(8) A 2
C C23' 0.7965(16) 0.0586(14) 0.6274(9) 0.034(3) Uiso d PU 0.286(8) A 2
C C24 0.8639(5) -0.0575(4) 0.6544(3) 0.0473(10) Uani d . 1 . .
H H24 0.9032 -0.1129 0.7034 0.057 Uiso calc R 1 A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 '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'
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
C4 O1 C9 . . 118.1(2) ?
C1 N1 C2 . . 114.5(3) ?
C4 N2 C1 . . 114.5(3) ?
C5 N3 N4 . . 112.1(2) ?
C5 N3 C2 . . 127.4(3) ?
N4 N3 C2 . . 120.5(2) ?
C7 N4 N3 . . 104.9(2) ?
C13 N5 C14 . . 114.2(3) ?
C16 N6 C13 . . 114.3(3) ?
C17 N7 N8 . . 112.7(2) ?
C17 N7 C14 . . 127.3(3) ?
N8 N7 C14 . . 120.0(2) ?
C19 N8 N7 . . 104.9(2) ?
N1 C1 N2 . . 128.1(3) ?
N1 C1 H1A . . 116.0 ?
N2 C1 H1A . . 116.0 ?
N1 C2 C3 . . 123.8(3) ?
N1 C2 N3 . . 114.4(3) ?
C3 C2 N3 . . 121.8(3) ?
C2 C3 C4 . . 115.4(3) ?
C2 C3 H3A . . 122.3 ?
C4 C3 H3A . . 122.3 ?
N2 C4 O1 . . 118.8(3) ?
N2 C4 C3 . . 123.7(3) ?
O1 C4 C3 . . 117.5(3) ?
C6 C5 N3 . . 105.7(3) ?
C6 C5 H5A . . 127.2 ?
N3 C5 H5A . . 127.2 ?
C5 C6 C7 . . 107.3(3) ?
C5 C6 Br1 . . 125.9(3) ?
C7 C6 Br1 . . 126.8(2) ?
N4 C7 C6 . . 110.0(3) ?
N4 C7 C8 . . 122.3(3) ?
C6 C7 C8 . . 127.7(3) ?
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 ?
O1 C9 C10 . . 111.5(3) ?
O1 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
O1 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C9 . . 108.5(3) ?
C11 C10 H10A . . 110.0 ?
C9 C10 H10A . . 110.0 ?
C11 C10 H10B . . 110.0 ?
C9 C10 H10B . . 110.0 ?
H10A C10 H10B . . 108.4 ?
C12 C11 C10 . . 176.1(4) ?
C11 C12 H12 . . 180.0 ?
N5 C13 N6 . . 128.8(3) ?
N5 C13 H13A . . 115.6 ?
N6 C13 H13A . . 115.6 ?
N5 C14 C15 . . 124.0(3) ?
N5 C14 N7 . . 114.8(3) ?
C15 C14 N7 . . 121.2(3) ?
C14 C15 C16 . . 114.6(3) ?
C14 C15 H15A . . 122.7 ?
C16 C15 H15A . . 122.7 ?
N6 C16 O2 . . 119.1(3) ?
N6 C16 C15 . . 124.1(3) ?
O2 C16 C15 . . 116.3(3) ?
N6 C16 O2' . . 117.6(5) ?
O2 C16 O2' . . 27.1(3) ?
C15 C16 O2' . . 114.6(5) ?
N7 C17 C18 . . 104.8(3) ?
N7 C17 H17A . . 127.6 ?
C18 C17 H17A . . 127.6 ?
C17 C18 C19 . . 107.6(3) ?
C17 C18 Br2 . . 125.8(2) ?
C19 C18 Br2 . . 126.6(2) ?
N8 C19 C18 . . 110.0(3) ?
N8 C19 C20 . . 121.6(3) ?
C18 C19 C20 . . 128.5(3) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C16 O2 C21 . . 118.4(3) ?
O2 C21 C22 . . 111.2(5) ?
O2 C21 H21A . . 109.4 ?
C22 C21 H21A . . 109.4 ?
O2 C21 H21B . . 109.4 ?
C22 C21 H21B . . 109.4 ?
H21A C21 H21B . . 108.0 ?
C23 C22 C21 . . 109.4(5) ?
C23 C22 H22A . . 109.8 ?
C21 C22 H22A . . 109.8 ?
C23 C22 H22B . . 109.8 ?
C21 C22 H22B . . 109.8 ?
H22A C22 H22B . . 108.2 ?
C24 C23 C22 . . 175.5(6) ?
C16 O2' C21' . . 120.6(8) ?
O2' C21' C22' . . 112.0(12) ?
O2' C21' H21C . . 109.2 ?
C22' C21' H21C . . 109.2 ?
O2' C21' H21D . . 109.2 ?
C22' C21' H21D . . 109.2 ?
H21C C21' H21D . . 107.9 ?
C23' C22' C21' . . 111.4(12) ?
C23' C22' H22C . . 109.3 ?
C21' C22' H22C . . 109.3 ?
C23' C22' H22D . . 109.3 ?
C21' C22' H22D . . 109.3 ?
H22C C22' H22D . . 108.0 ?
C24 C23' C22' . . 168.1(14) ?
C23 C24 C23' . . 39.2(6) ?
C23 C24 H24 . . 180.0 ?
C23' C24 H24 . . 140.8 ?
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 C6 . 1.879(3) ?
Br2 C18 . 1.877(3) ?
O1 C4 . 1.349(4) ?
O1 C9 . 1.460(4) ?
N1 C1 . 1.322(4) ?
N1 C2 . 1.346(4) ?
N2 C4 . 1.335(4) ?
N2 C1 . 1.344(4) ?
N3 C5 . 1.363(4) ?
N3 N4 . 1.371(3) ?
N3 C2 . 1.404(4) ?
N4 C7 . 1.324(4) ?
N5 C13 . 1.318(4) ?
N5 C14 . 1.341(4) ?
N6 C16 . 1.324(4) ?
N6 C13 . 1.330(4) ?
N7 C17 . 1.364(4) ?
N7 N8 . 1.374(3) ?
N7 C14 . 1.402(4) ?
N8 C19 . 1.329(4) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.374(4) ?
C3 C4 . 1.379(4) ?
C3 H3A . 0.9500 ?
C5 C6 . 1.348(4) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.415(4) ?
C7 C8 . 1.500(4) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.503(5) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.474(5) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.177(5) ?
C12 H12 . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C15 . 1.375(4) ?
C15 C16 . 1.385(4) ?
C15 H15A . 0.9500 ?
C16 O2 . 1.363(4) ?
C16 O2' . 1.417(10) ?
C17 C18 . 1.369(4) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.410(4) ?
C19 C20 . 1.490(4) ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
O2 C21 . 1.458(6) ?
C21 C22 . 1.512(8) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C22 C23 . 1.464(7) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.198(6) ?
O2' C21' . 1.448(16) ?
C21' C22' . 1.496(18) ?
C21' H21C . 0.9900 ?
C21' H21D . 0.9900 ?
C22' C23' . 1.481(19) ?
C22' H22C . 0.9900 ?
C22' H22D . 0.9900 ?
C23' C24 . 1.218(13) ?
C24 H24 . 0.9500 ?
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 N3 N4 C7 . . . . 0.0(4) ?
C2 N3 N4 C7 . . . . 178.9(3) ?
C17 N7 N8 C19 . . . . -0.2(4) ?
C14 N7 N8 C19 . . . . 179.6(3) ?
C2 N1 C1 N2 . . . . 0.8(5) ?
C4 N2 C1 N1 . . . . -0.5(5) ?
C1 N1 C2 C3 . . . . -0.8(5) ?
C1 N1 C2 N3 . . . . -180.0(3) ?
C5 N3 C2 N1 . . . . -2.5(5) ?
N4 N3 C2 N1 . . . . 178.8(3) ?
C5 N3 C2 C3 . . . . 178.3(3) ?
N4 N3 C2 C3 . . . . -0.3(5) ?
N1 C2 C3 C4 . . . . 0.6(5) ?
N3 C2 C3 C4 . . . . 179.7(3) ?
C1 N2 C4 O1 . . . . 179.4(3) ?
C1 N2 C4 C3 . . . . 0.2(5) ?
C9 O1 C4 N2 . . . . -9.4(5) ?
C9 O1 C4 C3 . . . . 169.8(3) ?
C2 C3 C4 N2 . . . . -0.3(5) ?
C2 C3 C4 O1 . . . . -179.5(3) ?
N4 N3 C5 C6 . . . . 0.2(4) ?
C2 N3 C5 C6 . . . . -178.5(3) ?
N3 C5 C6 C7 . . . . -0.3(4) ?
N3 C5 C6 Br1 . . . . 178.1(2) ?
N3 N4 C7 C6 . . . . -0.2(3) ?
N3 N4 C7 C8 . . . . 177.7(3) ?
C5 C6 C7 N4 . . . . 0.4(4) ?
Br1 C6 C7 N4 . . . . -178.0(2) ?
C5 C6 C7 C8 . . . . -177.5(3) ?
Br1 C6 C7 C8 . . . . 4.1(5) ?
C4 O1 C9 C10 . . . . 84.4(4) ?
O1 C9 C10 C11 . . . . -176.4(3) ?
C9 C10 C11 C12 . . . . 22(6) ?
C14 N5 C13 N6 . . . . 1.1(5) ?
C16 N6 C13 N5 . . . . -0.3(6) ?
C13 N5 C14 C15 . . . . -0.4(5) ?
C13 N5 C14 N7 . . . . 179.7(3) ?
C17 N7 C14 N5 . . . . -1.6(5) ?
N8 N7 C14 N5 . . . . 178.6(3) ?
C17 N7 C14 C15 . . . . 178.4(3) ?
N8 N7 C14 C15 . . . . -1.3(4) ?
N5 C14 C15 C16 . . . . -0.9(5) ?
N7 C14 C15 C16 . . . . 179.1(3) ?
C13 N6 C16 O2 . . . . 171.0(4) ?
C13 N6 C16 C15 . . . . -1.2(6) ?
C13 N6 C16 O2' . . . . -158.2(6) ?
C14 C15 C16 N6 . . . . 1.8(6) ?
C14 C15 C16 O2 . . . . -170.6(4) ?
C14 C15 C16 O2' . . . . 159.4(6) ?
N8 N7 C17 C18 . . . . 0.7(4) ?
C14 N7 C17 C18 . . . . -179.1(3) ?
N7 C17 C18 C19 . . . . -0.8(4) ?
N7 C17 C18 Br2 . . . . 179.0(2) ?
N7 N8 C19 C18 . . . . -0.3(4) ?
N7 N8 C19 C20 . . . . 179.5(3) ?
C17 C18 C19 N8 . . . . 0.8(4) ?
Br2 C18 C19 N8 . . . . -179.1(2) ?
C17 C18 C19 C20 . . . . -179.0(3) ?
Br2 C18 C19 C20 . . . . 1.1(5) ?
N6 C16 O2 C21 . . . . -1.8(7) ?
C15 C16 O2 C21 . . . . 171.0(4) ?
O2' C16 O2 C21 . . . . -96.0(11) ?
C16 O2 C21 C22 . . . . 81.1(6) ?
O2 C21 C22 C23 . . . . -176.9(4) ?
C21 C22 C23 C24 . . . . 10(7) ?
N6 C16 O2' C21' . . . . -8.8(12) ?
O2 C16 O2' C21' . . . . 91.8(13) ?
C15 C16 O2' C21' . . . . -168.0(8) ?
C16 O2' C21' C22' . . . . -71.7(13) ?
O2' C21' C22' C23' . . . . 173.6(10) ?
C21' C22' C23' C24 . . . . 2(6) ?
C22 C23 C24 C23' . . . . -10(6) ?
C22' C23' C24 C23 . . . . -3(5) ?
