#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225389.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_2225389
loop_
_publ_author_name
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
'Padaki, Mahesh'
'Suwunwong, Thitipone'
'Isloor, Arun M.'
_publ_section_title
;
 6-(4-Bromophenyl)-2-ethoxy-4-(2,4,5-trimethoxyphenyl)nicotinonitrile
;
_journal_coeditor_code           TK2622
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o641
_journal_page_last               o642
_journal_paper_doi               10.1107/S1600536810005210
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H21 Br N2 O4'
_chemical_formula_moiety         'C23 H21 Br N2 O4'
_chemical_formula_sum            'C23 H21 Br N2 O4'
_chemical_formula_weight         469.32
_chemical_melting_point_gt       460
_chemical_melting_point_lt       461
_chemical_name_common
;
6-(4-Bromophenyl)-2-ethoxy-4-(2,4,5-trimethoxyphenyl)nicotinonitrile
;
_chemical_name_systematic
;
6-(4-Bromophenyl)-2-ethoxy-4-(2,4,5-trimethoxyphenyl)nicotinonitrile
;
_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                92.2010(10)
_cell_angle_beta                 91.9680(10)
_cell_angle_gamma                99.5860(10)
_cell_formula_units_Z            4
_cell_length_a                   7.9631(2)
_cell_length_b                   11.0499(3)
_cell_length_c                   23.9690(6)
_cell_measurement_reflns_used    9488
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     2076.31(9)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_av_sigmaI/netI    0.053
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31800
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         0.9
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.013
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.79
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         9488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.7288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.098
_reflns_number_gt                7074
_reflns_number_total             9488
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2622.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2225389
_cod_database_fobs_code          2225389
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 Br1A -0.17700(4) -0.35388(2) 0.439858(11) 0.02094(8) Uani d . 1 . .
O O1A 0.5666(2) 0.35133(16) 0.42626(7) 0.0190(4) Uani d . 1 . .
O O2A 0.2036(3) 0.48545(17) 0.28313(7) 0.0229(4) Uani d . 1 . .
O O3A 0.2540(3) 0.46349(17) 0.08142(7) 0.0227(4) Uani d . 1 . .
O O4A 0.3749(3) 0.26013(17) 0.08836(7) 0.0211(4) Uani d . 1 . .
N N1A 0.3634(3) 0.18217(19) 0.40057(8) 0.0161(5) Uani d . 1 . .
N N2A 0.6447(4) 0.5362(2) 0.30967(10) 0.0304(6) Uani d . 1 . .
C C1A 0.1472(3) -0.0213(2) 0.43550(10) 0.0171(6) Uani d . 1 . .
H H1AA 0.2118 0.0341 0.4613 0.021 Uiso calc R 1 . .
C C2A 0.0518(4) -0.1272(2) 0.45413(11) 0.0183(6) Uani d . 1 . .
H H2AA 0.0519 -0.1434 0.4919 0.022 Uiso calc R 1 . .
C C3A -0.0433(3) -0.2081(2) 0.41548(11) 0.0160(5) Uani d . 1 . .
C C4A -0.0472(3) -0.1856(2) 0.35901(11) 0.0177(6) Uani d . 1 . .
H H4AA -0.1134 -0.2411 0.3337 0.021 Uiso calc R 1 . .
C C5A 0.0488(4) -0.0796(2) 0.34091(10) 0.0179(6) Uani d . 1 . .
H H5AA 0.0470 -0.0639 0.3031 0.022 Uiso calc R 1 . .
C C6A 0.1488(3) 0.0047(2) 0.37885(10) 0.0145(5) Uani d . 1 . .
C C7A 0.2528(3) 0.1189(2) 0.36092(10) 0.0153(5) Uani d . 1 . .
C C8A 0.2379(3) 0.1613(2) 0.30754(10) 0.0157(5) Uani d . 1 . .
H H8AA 0.1637 0.1154 0.2809 0.019 Uiso calc R 1 . .
C C9A 0.3339(4) 0.2727(2) 0.29383(10) 0.0163(5) Uani d . 1 . .
C C10A 0.4480(3) 0.3366(2) 0.33414(10) 0.0160(5) Uani d . 1 . .
C C11A 0.4564(3) 0.2863(2) 0.38748(10) 0.0158(5) Uani d . 1 . .
C C12A 0.3084(3) 0.3240(2) 0.23801(10) 0.0166(6) Uani d . 1 . .
C C13A 0.2479(3) 0.4339(2) 0.23373(11) 0.0183(6) Uani d . 1 . .
C C14A 0.2272(3) 0.4832(2) 0.18187(11) 0.0186(6) Uani d . 1 . .
H H14A 0.1854 0.5566 0.1793 0.022 Uiso calc R 1 . .
C C15A 0.2695(3) 0.4223(2) 0.13403(10) 0.0180(6) Uani d . 1 . .
C C16A 0.3318(3) 0.3113(2) 0.13770(10) 0.0180(6) Uani d . 1 . .
C C17A 0.3479(3) 0.2623(2) 0.18950(10) 0.0166(5) Uani d . 1 . .
H H17A 0.3856 0.1873 0.1920 0.020 Uiso calc R 1 . .
C C18A 0.5755(4) 0.2961(2) 0.48023(10) 0.0206(6) Uani d . 1 . .
H H18A 0.6219 0.2205 0.4764 0.025 Uiso calc R 1 . .
H H18B 0.4625 0.2770 0.4949 0.025 Uiso calc R 1 . .
C C19A 0.6888(4) 0.3869(3) 0.51911(11) 0.0244(6) Uani d . 1 . .
H H19A 0.6960 0.3531 0.5552 0.037 Uiso calc R 1 . .
H H19B 0.6423 0.4615 0.5224 0.037 Uiso calc R 1 . .
H H19C 0.8007 0.4042 0.5045 0.037 Uiso calc R 1 . .
C C20A 0.1635(5) 0.6051(3) 0.28312(13) 0.0425(9) Uani d . 1 . .
H H20A 0.1407 0.6307 0.3204 0.064 Uiso calc R 1 . .
H H20B 0.0645 0.6053 0.2591 0.064 Uiso calc R 1 . .
H H20C 0.2579 0.6607 0.2698 0.064 Uiso calc R 1 . .
C C21A 0.1906(4) 0.5766(3) 0.07668(12) 0.0281(7) Uani d . 1 . .
H H21A 0.1801 0.5945 0.0380 0.042 Uiso calc R 1 . .
H H21B 0.2683 0.6418 0.0960 0.042 Uiso calc R 1 . .
H H21C 0.0810 0.5695 0.0929 0.042 Uiso calc R 1 . .
C C22A 0.4189(4) 0.1406(2) 0.09113(11) 0.0243(6) Uani d . 1 . .
H H22A 0.4428 0.1117 0.0544 0.036 Uiso calc R 1 . .
H H22B 0.3256 0.0854 0.1053 0.036 Uiso calc R 1 . .
H H22C 0.5179 0.1440 0.1155 0.036 Uiso calc R 1 . .
C C23A 0.5564(4) 0.4488(3) 0.32183(10) 0.0215(6) Uani d . 1 . .
Br Br1B 0.38606(4) 0.11796(3) 0.926074(11) 0.02560(9) Uani d . 1 . .
O O1B 0.0191(3) 0.84937(17) 0.92736(7) 0.0231(4) Uani d . 1 . .
O O2B 0.4260(3) 0.98663(17) 0.78188(7) 0.0240(4) Uani d . 1 . .
O O3B 0.2913(3) 0.96201(16) 0.58180(7) 0.0210(4) Uani d . 1 . .
O O4B 0.0815(3) 0.75855(16) 0.59168(7) 0.0209(4) Uani d . 1 . .
N N1B 0.1491(3) 0.68209(19) 0.90306(8) 0.0164(5) Uani d . 1 . .
N N2B -0.0051(3) 1.0323(2) 0.81419(10) 0.0279(6) Uani d . 1 . .
C C1B 0.3117(4) 0.4800(2) 0.93221(11) 0.0199(6) Uani d . 1 . .
H H1BA 0.3184 0.5436 0.9592 0.024 Uiso calc R 1 . .
C C2B 0.3487(4) 0.3679(2) 0.94771(11) 0.0202(6) Uani d . 1 . .
H H2BA 0.3800 0.3556 0.9845 0.024 Uiso calc R 1 . .
C C3B 0.3378(4) 0.2743(2) 0.90675(11) 0.0199(6) Uani d . 1 . .
C C4B 0.2924(4) 0.2911(3) 0.85171(11) 0.0230(6) Uani d . 1 . .
H H4BA 0.2850 0.2270 0.8250 0.028 Uiso calc R 1 . .
C C5B 0.2584(4) 0.4043(2) 0.83709(11) 0.0226(6) Uani d . 1 . .
H H5BA 0.2310 0.4170 0.8000 0.027 Uiso calc R 1 . .
C C6B 0.2645(3) 0.5004(2) 0.87740(10) 0.0173(6) Uani d . 1 . .
C C7B 0.2157(3) 0.6191(2) 0.86213(11) 0.0178(6) Uani d . 1 . .
C C8B 0.2394(4) 0.6627(2) 0.80881(10) 0.0187(6) Uani d . 1 . .
H H8BA 0.2854 0.6167 0.7818 0.022 Uiso calc R 1 . .
C C9B 0.1946(3) 0.7745(2) 0.79583(10) 0.0165(5) Uani d . 1 . .
C C10B 0.1183(3) 0.8366(2) 0.83705(10) 0.0179(6) Uani d . 1 . .
C C11B 0.0976(4) 0.7856(2) 0.88999(10) 0.0179(6) Uani d . 1 . .
C C12B 0.2257(3) 0.8253(2) 0.74001(10) 0.0164(5) Uani d . 1 . .
C C13B 0.3413(4) 0.9333(2) 0.73404(11) 0.0185(6) Uani d . 1 . .
C C14B 0.3669(4) 0.9808(2) 0.68134(10) 0.0178(6) Uani d . 1 . .
H H14B 0.4443 1.0526 0.6774 0.021 Uiso calc R 1 . .
C C15B 0.2768(4) 0.9209(2) 0.63469(10) 0.0170(6) Uani d . 1 . .
C C16B 0.1637(3) 0.8103(2) 0.64004(10) 0.0160(5) Uani d . 1 . .
C C17B 0.1417(3) 0.7636(2) 0.69231(10) 0.0172(6) Uani d . 1 . .
H H17B 0.0693 0.6893 0.6959 0.021 Uiso calc R 1 . .
C C18B -0.0121(4) 0.8016(3) 0.98201(11) 0.0262(7) Uani d . 1 . .
H H18C -0.0237 0.7127 0.9796 0.031 Uiso calc R 1 . .
H H18D -0.1179 0.8227 0.9951 0.031 Uiso calc R 1 . .
C C19B 0.1320(5) 0.8537(3) 1.02274(13) 0.0367(8) Uani d . 1 . .
H H19D 0.1053 0.8262 1.0594 0.055 Uiso calc R 1 . .
H H19E 0.1481 0.9418 1.0233 0.055 Uiso calc R 1 . .
H H19F 0.2346 0.8265 1.0115 0.055 Uiso calc R 1 . .
C C20B 0.5570(4) 1.0900(3) 0.77626(12) 0.0278(7) Uani d . 1 . .
H H20D 0.6111 1.1153 0.8122 0.042 Uiso calc R 1 . .
H H20E 0.5081 1.1564 0.7614 0.042 Uiso calc R 1 . .
H H20F 0.6400 1.0679 0.7514 0.042 Uiso calc R 1 . .
C C21B 0.4143(4) 1.0690(3) 0.57435(11) 0.0233(6) Uani d . 1 . .
H H21D 0.4166 1.0868 0.5355 0.035 Uiso calc R 1 . .
H H21E 0.5248 1.0550 0.5871 0.035 Uiso calc R 1 . .
H H21F 0.3845 1.1373 0.5955 0.035 Uiso calc R 1 . .
C C22B -0.0187(4) 0.6395(2) 0.59614(11) 0.0227(6) Uani d . 1 . .
H H22D -0.0687 0.6101 0.5601 0.034 Uiso calc R 1 . .
H H22E -0.1074 0.6447 0.6218 0.034 Uiso calc R 1 . .
H H22F 0.0526 0.5839 0.6095 0.034 Uiso calc R 1 . .
C C23B 0.0514(4) 0.9469(3) 0.82524(11) 0.0212(6) Uani d . 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
C11A O1A C18A . . 115.60(19) ?
C13A O2A C20A . . 118.5(2) ?
C15A O3A C21A . . 116.7(2) ?
C16A O4A C22A . . 115.9(2) ?
C11A N1A C7A . . 118.5(2) ?
C2A C1A C6A . . 121.6(2) ?
C2A C1A H1AA . . 119.2 ?
C6A C1A H1AA . . 119.2 ?
C3A C2A C1A . . 118.5(2) ?
C3A C2A H2AA . . 120.8 ?
C1A C2A H2AA . . 120.8 ?
C2A C3A C4A . . 121.9(2) ?
C2A C3A Br1A . . 119.47(19) ?
C4A C3A Br1A . . 118.59(19) ?
C5A C4A C3A . . 119.0(2) ?
C5A C4A H4AA . . 120.5 ?
C3A C4A H4AA . . 120.5 ?
C4A C5A C6A . . 120.9(2) ?
C4A C5A H5AA . . 119.6 ?
C6A C5A H5AA . . 119.6 ?
C1A C6A C5A . . 118.1(2) ?
C1A C6A C7A . . 119.7(2) ?
C5A C6A C7A . . 122.3(2) ?
N1A C7A C8A . . 121.5(2) ?
N1A C7A C6A . . 115.7(2) ?
C8A C7A C6A . . 122.7(2) ?
C7A C8A C9A . . 120.1(2) ?
C7A C8A H8AA . . 119.9 ?
C9A C8A H8AA . . 119.9 ?
C10A C9A C8A . . 118.3(2) ?
C10A C9A C12A . . 121.2(2) ?
C8A C9A C12A . . 120.5(2) ?
C9A C10A C11A . . 118.0(2) ?
C9A C10A C23A . . 121.0(2) ?
C11A C10A C23A . . 121.0(2) ?
N1A C11A O1A . . 119.7(2) ?
N1A C11A C10A . . 123.5(2) ?
O1A C11A C10A . . 116.8(2) ?
C13A C12A C17A . . 119.3(2) ?
C13A C12A C9A . . 120.6(2) ?
C17A C12A C9A . . 120.1(2) ?
O2A C13A C12A . . 115.6(2) ?
O2A C13A C14A . . 123.6(2) ?
C12A C13A C14A . . 120.7(2) ?
C15A C14A C13A . . 119.6(2) ?
C15A C14A H14A . . 120.2 ?
C13A C14A H14A . . 120.2 ?
O3A C15A C14A . . 123.9(2) ?
O3A C15A C16A . . 115.8(2) ?
C14A C15A C16A . . 120.4(2) ?
O4A C16A C17A . . 124.8(2) ?
O4A C16A C15A . . 116.0(2) ?
C17A C16A C15A . . 119.2(2) ?
C16A C17A C12A . . 120.8(2) ?
C16A C17A H17A . . 119.6 ?
C12A C17A H17A . . 119.6 ?
O1A C18A C19A . . 107.7(2) ?
O1A C18A H18A . . 110.2 ?
C19A C18A H18A . . 110.2 ?
O1A C18A H18B . . 110.2 ?
C19A C18A H18B . . 110.2 ?
H18A C18A H18B . . 108.5 ?
C18A C19A H19A . . 109.5 ?
C18A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C18A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
O2A C20A H20A . . 109.5 ?
O2A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
O2A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
O3A C21A H21A . . 109.5 ?
O3A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
O3A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
O4A C22A H22A . . 109.5 ?
O4A C22A H22B . . 109.5 ?
H22A C22A H22B . . 109.5 ?
O4A C22A H22C . . 109.5 ?
H22A C22A H22C . . 109.5 ?
H22B C22A H22C . . 109.5 ?
N2A C23A C10A . . 176.9(3) ?
C11B O1B C18B . . 119.1(2) ?
C13B O2B C20B . . 117.6(2) ?
C15B O3B C21B . . 117.0(2) ?
C16B O4B C22B . . 115.60(19) ?
C11B N1B C7B . . 117.5(2) ?
C2B C1B C6B . . 121.9(2) ?
C2B C1B H1BA . . 119.1 ?
C6B C1B H1BA . . 119.1 ?
C1B C2B C3B . . 118.1(2) ?
C1B C2B H2BA . . 121.0 ?
C3B C2B H2BA . . 121.0 ?
C4B C3B C2B . . 121.9(2) ?
C4B C3B Br1B . . 118.4(2) ?
C2B C3B Br1B . . 119.7(2) ?
C5B C4B C3B . . 119.0(2) ?
C5B C4B H4BA . . 120.5 ?
C3B C4B H4BA . . 120.5 ?
C4B C5B C6B . . 120.9(2) ?
C4B C5B H5BA . . 119.6 ?
C6B C5B H5BA . . 119.6 ?
C1B C6B C5B . . 118.3(2) ?
C1B C6B C7B . . 121.1(2) ?
C5B C6B C7B . . 120.6(2) ?
N1B C7B C8B . . 122.5(2) ?
N1B C7B C6B . . 116.2(2) ?
C8B C7B C6B . . 121.3(2) ?
C9B C8B C7B . . 120.1(2) ?
C9B C8B H8BA . . 119.9 ?
C7B C8B H8BA . . 119.9 ?
C8B C9B C10B . . 117.4(2) ?
C8B C9B C12B . . 121.1(2) ?
C10B C9B C12B . . 121.5(2) ?
C9B C10B C11B . . 118.8(2) ?
C9B C10B C23B . . 121.1(2) ?
C11B C10B C23B . . 120.0(2) ?
N1B C11B O1B . . 121.1(2) ?
N1B C11B C10B . . 123.4(2) ?
O1B C11B C10B . . 115.5(2) ?
C13B C12B C17B . . 119.0(2) ?
C13B C12B C9B . . 120.9(2) ?
C17B C12B C9B . . 120.1(2) ?
O2B C13B C14B . . 123.4(2) ?
O2B C13B C12B . . 116.5(2) ?
C14B C13B C12B . . 120.1(2) ?
C15B C14B C13B . . 120.1(2) ?
C15B C14B H14B . . 120.0 ?
C13B C14B H14B . . 120.0 ?
O3B C15B C14B . . 124.0(2) ?
O3B C15B C16B . . 115.7(2) ?
C14B C15B C16B . . 120.3(2) ?
O4B C16B C17B . . 125.3(2) ?
O4B C16B C15B . . 115.8(2) ?
C17B C16B C15B . . 118.9(2) ?
C16B C17B C12B . . 121.5(2) ?
C16B C17B H17B . . 119.2 ?
C12B C17B H17B . . 119.2 ?
O1B C18B C19B . . 110.5(2) ?
O1B C18B H18C . . 109.6 ?
C19B C18B H18C . . 109.6 ?
O1B C18B H18D . . 109.6 ?
C19B C18B H18D . . 109.6 ?
H18C C18B H18D . . 108.1 ?
C18B C19B H19D . . 109.5 ?
C18B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C18B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
O2B C20B H20D . . 109.5 ?
O2B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
O2B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
O3B C21B H21D . . 109.5 ?
O3B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
O3B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
O4B C22B H22D . . 109.5 ?
O4B C22B H22E . . 109.5 ?
H22D C22B H22E . . 109.5 ?
O4B C22B H22F . . 109.5 ?
H22D C22B H22F . . 109.5 ?
H22E C22B H22F . . 109.5 ?
N2B C23B C10B . . 177.5(3) ?
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
Br1A C3A . 1.901(2) ?
O1A C11A . 1.354(3) ?
O1A C18A . 1.456(3) ?
O2A C13A . 1.377(3) ?
O2A C20A . 1.411(3) ?
O3A C15A . 1.366(3) ?
O3A C21A . 1.431(3) ?
O4A C16A . 1.370(3) ?
O4A C22A . 1.426(3) ?
N1A C11A . 1.316(3) ?
N1A C7A . 1.362(3) ?
N2A C23A . 1.150(3) ?
C1A C2A . 1.384(4) ?
C1A C6A . 1.398(3) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.376(4) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.386(4) ?
C4A C5A . 1.381(4) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.402(3) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.477(4) ?
C7A C8A . 1.387(3) ?
C8A C9A . 1.393(4) ?
C8A H8AA . 0.9300 ?
C9A C10A . 1.390(4) ?
C9A C12A . 1.494(3) ?
C10A C11A . 1.417(3) ?
C10A C23A . 1.435(4) ?
C12A C13A . 1.384(4) ?
C12A C17A . 1.398(4) ?
C13A C14A . 1.392(4) ?
C14A C15A . 1.387(4) ?
C14A H14A . 0.9300 ?
C15A C16A . 1.402(4) ?
C16A C17A . 1.384(3) ?
C17A H17A . 0.9300 ?
C18A C19A . 1.503(4) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A H19A . 0.9600 ?
C19A H19B . 0.9600 ?
C19A H19C . 0.9600 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H20C . 0.9600 ?
C21A H21A . 0.9600 ?
C21A H21B . 0.9600 ?
C21A H21C . 0.9600 ?
C22A H22A . 0.9600 ?
C22A H22B . 0.9600 ?
C22A H22C . 0.9600 ?
Br1B C3B . 1.902(3) ?
O1B C11B . 1.352(3) ?
O1B C18B . 1.445(3) ?
O2B C13B . 1.371(3) ?
O2B C20B . 1.427(3) ?
O3B C15B . 1.365(3) ?
O3B C21B . 1.425(3) ?
O4B C16B . 1.368(3) ?
O4B C22B . 1.430(3) ?
N1B C11B . 1.322(3) ?
N1B C7B . 1.354(3) ?
N2B C23B . 1.147(4) ?
C1B C2B . 1.381(4) ?
C1B C6B . 1.391(3) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.388(4) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.383(4) ?
C4B C5B . 1.379(4) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.402(4) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.485(4) ?
C7B C8B . 1.391(3) ?
C8B C9B . 1.385(4) ?
C8B H8BA . 0.9300 ?
C9B C10B . 1.394(4) ?
C9B C12B . 1.484(3) ?
C10B C11B . 1.412(3) ?
C10B C23B . 1.443(4) ?
C12B C13B . 1.396(4) ?
C12B C17B . 1.399(4) ?
C13B C14B . 1.395(3) ?
C14B C15B . 1.390(4) ?
C14B H14B . 0.9300 ?
C15B C16B . 1.406(4) ?
C16B C17B . 1.379(3) ?
C17B H17B . 0.9300 ?
C18B C19B . 1.504(4) ?
C18B H18C . 0.9700 ?
C18B H18D . 0.9700 ?
C19B H19D . 0.9600 ?
C19B H19E . 0.9600 ?
C19B H19F . 0.9600 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
C21B H21D . 0.9600 ?
C21B H21E . 0.9600 ?
C21B H21F . 0.9600 ?
C22B H22D . 0.9600 ?
C22B H22E . 0.9600 ?
C22B H22F . 0.9600 ?
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
C1A H1AA N1A 1_555 0.93 2.43 2.770(3) 102 y
C18B H18C N1B 1_555 0.97 2.38 2.741(4) 101 y
C22A H22C Cg2 2_666 0.96 2.74 3.585(3) 147 y
C22B H22E Cg1 2_566 0.96 2.68 3.511(3) 145 y
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
C6A C1A C2A C3A . . . . -0.1(4) ?
C1A C2A C3A C4A . . . . -0.7(4) ?
C1A C2A C3A Br1A . . . . -179.6(2) ?
C2A C3A C4A C5A . . . . 0.7(4) ?
Br1A C3A C4A C5A . . . . 179.6(2) ?
C3A C4A C5A C6A . . . . -0.1(4) ?
C2A C1A C6A C5A . . . . 0.7(4) ?
C2A C1A C6A C7A . . . . -180.0(2) ?
C4A C5A C6A C1A . . . . -0.6(4) ?
C4A C5A C6A C7A . . . . -180.0(2) ?
C11A N1A C7A C8A . . . . 0.6(4) ?
C11A N1A C7A C6A . . . . -178.3(2) ?
C1A C6A C7A N1A . . . . 10.6(4) ?
C5A C6A C7A N1A . . . . -170.1(2) ?
C1A C6A C7A C8A . . . . -168.3(2) ?
C5A C6A C7A C8A . . . . 11.0(4) ?
N1A C7A C8A C9A . . . . -1.8(4) ?
C6A C7A C8A C9A . . . . 177.1(2) ?
C7A C8A C9A C10A . . . . 2.4(4) ?
C7A C8A C9A C12A . . . . -175.0(2) ?
C8A C9A C10A C11A . . . . -1.8(4) ?
C12A C9A C10A C11A . . . . 175.5(2) ?
C8A C9A C10A C23A . . . . 177.0(3) ?
C12A C9A C10A C23A . . . . -5.7(4) ?
C7A N1A C11A O1A . . . . 179.6(2) ?
C7A N1A C11A C10A . . . . -0.1(4) ?
C18A O1A C11A N1A . . . . 1.7(3) ?
C18A O1A C11A C10A . . . . -178.6(2) ?
C9A C10A C11A N1A . . . . 0.7(4) ?
C23A C10A C11A N1A . . . . -178.1(3) ?
C9A C10A C11A O1A . . . . -179.0(2) ?
C23A C10A C11A O1A . . . . 2.2(4) ?
C10A C9A C12A C13A . . . . -61.4(4) ?
C8A C9A C12A C13A . . . . 115.8(3) ?
C10A C9A C12A C17A . . . . 117.6(3) ?
C8A C9A C12A C17A . . . . -65.2(4) ?
C20A O2A C13A C12A . . . . 171.4(3) ?
C20A O2A C13A C14A . . . . -11.6(4) ?
C17A C12A C13A O2A . . . . 176.7(2) ?
C9A C12A C13A O2A . . . . -4.2(4) ?
C17A C12A C13A C14A . . . . -0.3(4) ?
C9A C12A C13A C14A . . . . 178.7(2) ?
O2A C13A C14A C15A . . . . -177.5(2) ?
C12A C13A C14A C15A . . . . -0.7(4) ?
C21A O3A C15A C14A . . . . 0.2(4) ?
C21A O3A C15A C16A . . . . 180.0(2) ?
C13A C14A C15A O3A . . . . -179.9(2) ?
C13A C14A C15A C16A . . . . 0.3(4) ?
C22A O4A C16A C17A . . . . 8.1(4) ?
C22A O4A C16A C15A . . . . -172.8(2) ?
O3A C15A C16A O4A . . . . 2.1(4) ?
C14A C15A C16A O4A . . . . -178.0(2) ?
O3A C15A C16A C17A . . . . -178.7(2) ?
C14A C15A C16A C17A . . . . 1.1(4) ?
O4A C16A C17A C12A . . . . 176.9(2) ?
C15A C16A C17A C12A . . . . -2.1(4) ?
C13A C12A C17A C16A . . . . 1.8(4) ?
C9A C12A C17A C16A . . . . -177.3(2) ?
C11A O1A C18A C19A . . . . -174.0(2) ?
C6B C1B C2B C3B . . . . 0.0(4) ?
C1B C2B C3B C4B . . . . 0.4(4) ?
C1B C2B C3B Br1B . . . . -179.6(2) ?
C2B C3B C4B C5B . . . . 0.5(5) ?
Br1B C3B C4B C5B . . . . -179.5(2) ?
C3B C4B C5B C6B . . . . -1.8(5) ?
C2B C1B C6B C5B . . . . -1.3(4) ?
C2B C1B C6B C7B . . . . 176.5(3) ?
C4B C5B C6B C1B . . . . 2.2(4) ?
C4B C5B C6B C7B . . . . -175.6(3) ?
C11B N1B C7B C8B . . . . 3.5(4) ?
C11B N1B C7B C6B . . . . -177.2(2) ?
C1B C6B C7B N1B . . . . -27.5(4) ?
C5B C6B C7B N1B . . . . 150.2(3) ?
C1B C6B C7B C8B . . . . 151.9(3) ?
C5B C6B C7B C8B . . . . -30.4(4) ?
N1B C7B C8B C9B . . . . 0.1(4) ?
C6B C7B C8B C9B . . . . -179.2(2) ?
C7B C8B C9B C10B . . . . -3.1(4) ?
C7B C8B C9B C12B . . . . 177.3(2) ?
C8B C9B C10B C11B . . . . 2.6(4) ?
C12B C9B C10B C11B . . . . -177.8(2) ?
C8B C9B C10B C23B . . . . -173.4(3) ?
C12B C9B C10B C23B . . . . 6.2(4) ?
C7B N1B C11B O1B . . . . 175.4(2) ?
C7B N1B C11B C10B . . . . -4.0(4) ?
C18B O1B C11B N1B . . . . -1.4(4) ?
C18B O1B C11B C10B . . . . 178.0(2) ?
C9B C10B C11B N1B . . . . 1.0(4) ?
C23B C10B C11B N1B . . . . 177.1(2) ?
C9B C10B C11B O1B . . . . -178.5(2) ?
C23B C10B C11B O1B . . . . -2.4(4) ?
C8B C9B C12B C13B . . . . -114.5(3) ?
C10B C9B C12B C13B . . . . 66.0(4) ?
C8B C9B C12B C17B . . . . 64.1(4) ?
C10B C9B C12B C17B . . . . -115.5(3) ?
C20B O2B C13B C14B . . . . -5.5(4) ?
C20B O2B C13B C12B . . . . 173.9(2) ?
C17B C12B C13B O2B . . . . -176.9(2) ?
C9B C12B C13B O2B . . . . 1.6(4) ?
C17B C12B C13B C14B . . . . 2.5(4) ?
C9B C12B C13B C14B . . . . -179.0(3) ?
O2B C13B C14B C15B . . . . 179.6(2) ?
C12B C13B C14B C15B . . . . 0.3(4) ?
C21B O3B C15B C14B . . . . 3.8(4) ?
C21B O3B C15B C16B . . . . -175.5(2) ?
C13B C14B C15B O3B . . . . 178.7(2) ?
C13B C14B C15B C16B . . . . -2.1(4) ?
C22B O4B C16B C17B . . . . -7.7(4) ?
C22B O4B C16B C15B . . . . 173.3(2) ?
O3B C15B C16B O4B . . . . -0.6(3) ?
C14B C15B C16B O4B . . . . -179.9(2) ?
O3B C15B C16B C17B . . . . -179.6(2) ?
C14B C15B C16B C17B . . . . 1.1(4) ?
O4B C16B C17B C12B . . . . -177.2(2) ?
C15B C16B C17B C12B . . . . 1.7(4) ?
C13B C12B C17B C16B . . . . -3.5(4) ?
C9B C12B C17B C16B . . . . 177.9(2) ?
C11B O1B C18B C19B . . . . 92.8(3) ?
