#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/45/2224579.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_2224579
loop_
_publ_author_name
'Jing, Lin-Hai'
_publ_section_title
;
 N,N'-Bis(4-bromophenyl)naphthalene-1,4-dicarboxamide
 N,N-dimethylacetamide disolvate
;
_journal_coeditor_code           CI2967
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o27
_journal_paper_doi               10.1107/S1600536809051447
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C24 H16 Br2 N2 O2, 2C4 H9 N O'
_chemical_formula_moiety         'C24 H16 Br2 N2 O2, 2(C4 H9 N O)'
_chemical_formula_sum            'C32 H34 Br2 N4 O4'
_chemical_formula_weight         698.45
_chemical_name_systematic
;
N,N'-Bis(4-bromophenyl)naphthalene-1,4-dicarboxamide
N,N-dimethylacetamide disolvate
;
_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                90.775(2)
_cell_angle_beta                 111.370(4)
_cell_angle_gamma                92.944(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4589(9)
_cell_length_b                   12.4485(5)
_cell_length_c                   12.8439(11)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.15
_cell_volume                     1554.3(2)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 2004)'
_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      93(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+ diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12655
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.637
_exptl_absorpt_correction_T_min  0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.725
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         6836
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0291
_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)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                5420
_reflns_number_total             6836
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2967.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               2224579
_cod_database_fobs_code          2224579
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 0.53236(2) 0.112534(16) 0.932514(17) 0.02903(7) Uani d . 1 . .
Br Br2 0.22415(2) 1.394801(16) 0.057404(18) 0.03060(7) Uani d . 1 . .
O O1 0.32331(13) 0.45436(10) 0.48313(11) 0.0177(3) Uani d . 1 . .
O O2 0.31551(13) 1.04379(10) 0.50572(11) 0.0191(3) Uani d . 1 . .
N N1 0.34837(17) 0.50996(13) 0.66106(14) 0.0168(3) Uani d . 1 . .
H H1N 0.348(2) 0.5650(19) 0.700(2) 0.039(7) Uiso d . 1 . .
N N2 0.23601(17) 0.99105(13) 0.32026(14) 0.0189(4) Uani d . 1 . .
H H2N 0.203(2) 0.9395(17) 0.2781(19) 0.024(6) Uiso d . 1 . .
C C1 0.30036(18) 0.63948(14) 0.51685(15) 0.0143(4) Uani d . 1 . .
C C2 0.39398(19) 0.68975(15) 0.47878(16) 0.0171(4) Uani d . 1 . .
H H2 0.4670 0.6508 0.4729 0.021 Uiso calc R 1 . .
C C3 0.38368(19) 0.79752(15) 0.44845(16) 0.0172(4) Uani d . 1 . .
H H3 0.4495 0.8307 0.4222 0.021 Uiso calc R 1 . .
C C4 0.27922(18) 0.85564(14) 0.45630(15) 0.0145(4) Uani d . 1 . .
C C5 0.06363(19) 0.86155(15) 0.49518(16) 0.0170(4) Uani d . 1 . .
H H5 0.0559 0.9348 0.4750 0.020 Uiso calc R 1 . .
C C6 -0.03434(19) 0.81135(15) 0.52719(16) 0.0183(4) Uani d . 1 . .
H H6 -0.1095 0.8499 0.5291 0.022 Uiso calc R 1 . .
C C7 -0.02522(19) 0.70304(15) 0.55738(16) 0.0178(4) Uani d . 1 . .
H H7 -0.0940 0.6690 0.5798 0.021 Uiso calc R 1 . .
C C8 0.08240(18) 0.64638(15) 0.55463(16) 0.0159(4) Uani d . 1 . .
H H8 0.0872 0.5731 0.5746 0.019 Uiso calc R 1 . .
C C9 0.18715(18) 0.69610(14) 0.52222(15) 0.0130(4) Uani d . 1 . .
C C10 0.17723(18) 0.80569(14) 0.49159(15) 0.0136(4) Uani d . 1 . .
C C11 0.32325(18) 0.52500(14) 0.55106(16) 0.0144(4) Uani d . 1 . .
C C12 0.38661(19) 0.41416(14) 0.71995(16) 0.0153(4) Uani d . 1 . .
C C13 0.44442(19) 0.42461(15) 0.83616(16) 0.0184(4) Uani d . 1 . .
H H13 0.4552 0.4937 0.8717 0.022 Uiso calc R 1 . .
C C14 0.48654(19) 0.33506(15) 0.90073(16) 0.0187(4) Uani d . 1 . .
H H14 0.5262 0.3420 0.9800 0.022 Uiso calc R 1 . .
C C15 0.46910(19) 0.23536(15) 0.84642(16) 0.0175(4) Uani d . 1 . .
C C16 0.40962(18) 0.22272(14) 0.73121(16) 0.0158(4) Uani d . 1 . .
H H16 0.3972 0.1532 0.6962 0.019 Uiso calc R 1 . .
C C17 0.36833(18) 0.31242(14) 0.66737(16) 0.0145(4) Uani d . 1 . .
H H17 0.3278 0.3048 0.5882 0.017 Uiso calc R 1 . .
C C18 0.27844(18) 0.97352(14) 0.43114(16) 0.0147(4) Uani d . 1 . .
C C19 0.23255(19) 1.08886(15) 0.26482(16) 0.0162(4) Uani d . 1 . .
C C20 0.27827(18) 1.18916(15) 0.31961(16) 0.0169(4) Uani d . 1 . .
H H20 0.3117 1.1949 0.3990 0.020 Uiso calc R 1 . .
C C21 0.27480(19) 1.28043(15) 0.25775(16) 0.0180(4) Uani d . 1 . .
H H21 0.3053 1.3490 0.2944 0.022 Uiso calc R 1 . .
C C22 0.2264(2) 1.27038(15) 0.14216(17) 0.0195(4) Uani d . 1 . .
C C23 0.1782(2) 1.17201(15) 0.08598(17) 0.0236(5) Uani d . 1 . .
H H23 0.1433 1.1669 0.0066 0.028 Uiso calc R 1 . .
C C24 0.1820(2) 1.08126(15) 0.14807(17) 0.0222(4) Uani d . 1 . .
H H24 0.1500 1.0132 0.1108 0.027 Uiso calc R 1 . .
O O3 0.9394(16) 0.1698(9) 0.8232(17) 0.021(2) Uani d PDU 0.444(7) A 1
N N3 0.8990(5) 0.3438(4) 0.7831(4) 0.0226(14) Uani d PD 0.444(7) A 1
C C25 1.0986(17) 0.2599(10) 0.7668(15) 0.025(2) Uani d PD 0.444(7) A 1
H H25A 1.1649 0.3154 0.8142 0.030 Uiso calc PR 0.444(7) A 1
H H25B 1.0762 0.2764 0.6879 0.030 Uiso calc PR 0.444(7) A 1
H H25C 1.1387 0.1896 0.7810 0.030 Uiso calc PR 0.444(7) A 1
C C26 0.9712(6) 0.2573(4) 0.7930(4) 0.0205(15) Uani d PDU 0.444(7) A 1
C C27 0.9413(14) 0.4520(8) 0.7573(15) 0.024(2) Uani d PD 0.444(7) A 1
H H27A 0.9882 0.4942 0.8271 0.029 Uiso calc PR 0.444(7) A 1
H H27B 0.8599 0.4881 0.7108 0.029 Uiso calc PR 0.444(7) A 1
H H27C 1.0041 0.4454 0.7168 0.029 Uiso calc PR 0.444(7) A 1
C C28 0.7799(19) 0.3420(14) 0.8162(18) 0.024(3) Uani d PD 0.444(7) A 1
H H28A 0.7246 0.2743 0.7893 0.029 Uiso calc PR 0.444(7) A 1
H H28B 0.7242 0.4026 0.7837 0.029 Uiso calc PR 0.444(7) A 1
H H28C 0.8107 0.3478 0.8980 0.029 Uiso calc PR 0.444(7) A 1
O O3' 0.9084(13) 0.1781(7) 0.8283(14) 0.0227(19) Uani d PDU 0.556(7) A 2
N N3' 0.9840(5) 0.3352(3) 0.7788(3) 0.0245(12) Uani d PD 0.556(7) A 2
C C25' 0.7828(18) 0.3251(12) 0.8320(16) 0.040(4) Uani d PD 0.556(7) A 2
H H25D 0.7252 0.2693 0.8500 0.048 Uiso calc PR 0.556(7) A 2
H H25E 0.7272 0.3612 0.7646 0.048 Uiso calc PR 0.556(7) A 2
H H25F 0.8198 0.3778 0.8946 0.048 Uiso calc PR 0.556(7) A 2
C C26' 0.8982(4) 0.2748(4) 0.8120(3) 0.0197(12) Uani d PD 0.556(7) A 2
C C27' 0.9802(11) 0.4515(7) 0.7669(13) 0.036(3) Uani d PDU 0.556(7) A 2
H H27D 0.9253 0.4673 0.6894 0.043 Uiso calc PR 0.556(7) A 2
H H27E 1.0740 0.4832 0.7864 0.043 Uiso calc PR 0.556(7) A 2
H H27F 0.9387 0.4821 0.8169 0.043 Uiso calc PR 0.556(7) A 2
C C28' 1.0974(13) 0.2903(8) 0.7562(12) 0.034(3) Uani d PDU 0.556(7) A 2
H H28D 1.1842 0.3113 0.8174 0.041 Uiso calc PR 0.556(7) A 2
H H28E 1.1003 0.3177 0.6858 0.041 Uiso calc PR 0.556(7) A 2
H H28F 1.0841 0.2116 0.7501 0.041 Uiso calc PR 0.556(7) A 2
O O4 0.3394(12) 0.6785(6) 0.8119(18) 0.0205(19) Uani d PD 0.654(7) . 1
N N4 0.2121(3) 0.8208(3) 0.8085(2) 0.0229(10) Uani d PD 0.654(7) . 1
C C29 0.4147(11) 0.8427(10) 0.7597(11) 0.028(3) Uani d PD 0.654(7) . 1
H H29A 0.4752 0.8870 0.8243 0.033 Uiso calc PR 0.654(7) . 1
H H29B 0.3635 0.8896 0.7000 0.033 Uiso calc PR 0.654(7) . 1
H H29C 0.4701 0.7967 0.7327 0.033 Uiso calc PR 0.654(7) . 1
C C30 0.3170(4) 0.7747(3) 0.7932(3) 0.0205(10) Uani d PD 0.654(7) . 1
C C31 0.1860(9) 0.9350(5) 0.7976(8) 0.0283(17) Uani d PD 0.654(7) . 1
H H31A 0.2042 0.9679 0.8717 0.034 Uiso calc PR 0.654(7) . 1
H H31B 0.0898 0.9430 0.7499 0.034 Uiso calc PR 0.654(7) . 1
H H31C 0.2465 0.9706 0.7639 0.034 Uiso calc PR 0.654(7) . 1
C C32 0.1180(15) 0.7532(12) 0.8495(11) 0.030(2) Uani d PD 0.654(7) . 1
H H32A 0.1453 0.6787 0.8559 0.036 Uiso calc PR 0.654(7) . 1
H H32B 0.0231 0.7554 0.7965 0.036 Uiso calc PR 0.654(7) . 1
H H32C 0.1243 0.7814 0.9229 0.036 Uiso calc PR 0.654(7) . 1
O O4' 0.312(2) 0.6646(12) 0.810(3) 0.019(3) Uani d PD 0.346(7) . 2
N N4' 0.2828(6) 0.8424(5) 0.7762(4) 0.0184(18) Uani d PD 0.346(7) . 2
C C29' 0.142(3) 0.748(2) 0.858(2) 0.034(5) Uani d PD 0.346(7) . 2
H H29D 0.1246 0.6751 0.8791 0.041 Uiso calc PR 0.346(7) . 2
H H29E 0.0585 0.7721 0.8007 0.041 Uiso calc PR 0.346(7) . 2
H H29F 0.1708 0.7969 0.9235 0.041 Uiso calc PR 0.346(7) . 2
C C30' 0.2524(8) 0.7475(5) 0.8120(5) 0.022(2) Uani d PD 0.346(7) . 2
C C31' 0.2132(17) 0.9405(10) 0.7792(16) 0.023(3) Uani d PDU 0.346(7) . 2
H H31D 0.1200 0.9215 0.7765 0.028 Uiso calc PR 0.346(7) . 2
H H31E 0.2084 0.9836 0.7147 0.028 Uiso calc PR 0.346(7) . 2
H H31F 0.2647 0.9823 0.8484 0.028 Uiso calc PR 0.346(7) . 2
C C32' 0.4106(17) 0.854(2) 0.746(2) 0.019(4) Uani d PDU 0.346(7) . 2
H H32D 0.4930 0.8586 0.8142 0.023 Uiso calc PR 0.346(7) . 2
H H32E 0.4078 0.9197 0.7038 0.023 Uiso calc PR 0.346(7) . 2
H H32F 0.4132 0.7915 0.6995 0.023 Uiso calc PR 0.346(7) . 2
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
C11 N1 C12 . . 127.23(16) ?
C11 N1 H1N . . 116.2(16) ?
C12 N1 H1N . . 116.3(16) ?
C18 N2 C19 . . 129.45(17) ?
C18 N2 H2N . . 117.0(15) ?
C19 N2 H2N . . 113.5(15) ?
C2 C1 C9 . . 119.96(16) ?
C2 C1 C11 . . 116.99(15) ?
C9 C1 C11 . . 123.05(15) ?
C1 C2 C3 . . 121.09(16) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 120.59(17) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C10 . . 120.19(16) ?
C3 C4 C18 . . 118.68(16) ?
C10 C4 C18 . . 121.09(15) ?
C6 C5 C10 . . 120.79(16) ?
C6 C5 H5 . . 119.6 ?
C10 C5 H5 . . 119.6 ?
C5 C6 C7 . . 120.67(16) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 120.29(17) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C9 . . 120.74(16) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C8 C9 C10 . . 118.71(15) ?
C8 C9 C1 . . 122.53(16) ?
C10 C9 C1 . . 118.74(15) ?
C4 C10 C5 . . 121.84(16) ?
C4 C10 C9 . . 119.35(15) ?
C5 C10 C9 . . 118.80(15) ?
O1 C11 N1 . . 125.01(17) ?
O1 C11 C1 . . 120.76(16) ?
N1 C11 C1 . . 114.18(16) ?
C13 C12 C17 . . 119.83(16) ?
C13 C12 N1 . . 116.77(17) ?
C17 C12 N1 . . 123.41(17) ?
C14 C13 C12 . . 120.73(18) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 118.27(18) ?
C15 C14 H14 . . 120.9 ?
C13 C14 H14 . . 120.9 ?
C16 C15 C14 . . 122.03(17) ?
C16 C15 Br1 . . 118.91(14) ?
C14 C15 Br1 . . 119.05(15) ?
C15 C16 C17 . . 119.36(17) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C16 C17 C12 . . 119.76(17) ?
C16 C17 H17 . . 120.1 ?
C12 C17 H17 . . 120.1 ?
O2 C18 N2 . . 125.32(17) ?
O2 C18 C4 . . 121.85(17) ?
N2 C18 C4 . . 112.82(16) ?
C24 C19 C20 . . 119.70(17) ?
C24 C19 N2 . . 116.18(17) ?
C20 C19 N2 . . 124.11(17) ?
C21 C20 C19 . . 119.86(18) ?
C21 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
C22 C21 C20 . . 119.26(18) ?
C22 C21 H21 . . 120.4 ?
C20 C21 H21 . . 120.4 ?
C21 C22 C23 . . 121.86(17) ?
C21 C22 Br2 . . 119.34(15) ?
C23 C22 Br2 . . 118.80(15) ?
C24 C23 C22 . . 118.63(19) ?
C24 C23 H23 . . 120.7 ?
C22 C23 H23 . . 120.7 ?
C23 C24 C19 . . 120.67(18) ?
C23 C24 H24 . . 119.7 ?
C19 C24 H24 . . 119.7 ?
C26 N3 C28 . . 120.6(9) ?
C26 N3 C27 . . 124.9(8) ?
C28 N3 C27 . . 113.7(10) ?
O3 C26 N3 . . 123.8(9) ?
O3 C26 C25 . . 114.8(9) ?
N3 C26 C25 . . 121.3(7) ?
C26' N3' C28' . . 122.0(6) ?
C26' N3' C27' . . 124.8(7) ?
C28' N3' C27' . . 113.1(7) ?
C26' C25' H25D . . 109.6 ?
C26' C25' H25E . . 109.5 ?
H25D C25' H25E . . 109.5 ?
C26' C25' H25F . . 109.3 ?
H25D C25' H25F . . 109.5 ?
H25E C25' H25F . . 109.5 ?
O3' C26' N3' . . 123.7(7) ?
O3' C26' C25' . . 116.7(9) ?
N3' C26' C25' . . 119.5(8) ?
N3' C27' H27D . . 109.5 ?
N3' C27' H27E . . 109.5 ?
H27D C27' H27E . . 109.5 ?
N3' C27' H27F . . 109.5 ?
H27D C27' H27F . . 109.5 ?
H27E C27' H27F . . 109.5 ?
N3' C28' H28D . . 109.5 ?
N3' C28' H28E . . 109.5 ?
H28D C28' H28E . . 109.5 ?
N3' C28' H28F . . 109.4 ?
H28D C28' H28F . . 109.5 ?
H28E C28' H28F . . 109.5 ?
C30 N4 C31 . . 125.5(5) ?
C30 N4 C32 . . 118.6(7) ?
C31 N4 C32 . . 115.7(7) ?
O4 C30 N4 1 . 122.4(8) ?
O4 C30 N4 . . 122.4(8) ?
O4 C30 C29 1 . 118.9(9) ?
O4 C30 C29 . . 118.9(9) ?
N4 C30 C29 . . 118.6(6) ?
C30' N4' C31' . . 124.2(8) ?
C30' N4' C32' . . 118.4(11) ?
C31' N4' C32' . . 116.8(11) ?
C30' C29' H29D . . 109.5 ?
C30' C29' H29E . . 109.4 ?
H29D C29' H29E . . 109.5 ?
C30' C29' H29F . . 109.5 ?
H29D C29' H29F . . 109.5 ?
H29E C29' H29F . . 109.5 ?
O4' C30' N4' . . 124.1(16) ?
O4' C30' C29' . . 120.9(18) ?
N4' C30' C29' . . 115.0(12) ?
N4' C31' H31D . . 109.5 ?
N4' C31' H31E . . 109.5 ?
H31D C31' H31E . . 109.5 ?
N4' C31' H31F . . 109.5 ?
H31D C31' H31F . . 109.5 ?
H31E C31' H31F . . 109.5 ?
N4' C32' H32D . . 109.5 ?
N4' C32' H32E . . 109.5 ?
H32D C32' H32E . . 109.5 ?
N4' C32' H32F . . 109.5 ?
H32D C32' H32F . . 109.5 ?
H32E C32' H32F . . 109.5 ?
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 C15 . 1.9013(18) ?
Br2 C22 . 1.9014(18) ?
O1 C11 . 1.231(2) ?
O2 C18 . 1.227(2) ?
N1 C11 . 1.357(2) ?
N1 C12 . 1.417(2) ?
N1 H1N . 0.84(2) ?
N2 C18 . 1.353(2) ?
N2 C19 . 1.414(2) ?
N2 H2N . 0.81(2) ?
C1 C2 . 1.372(2) ?
C1 C9 . 1.431(2) ?
C1 C11 . 1.502(2) ?
C2 C3 . 1.401(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.95 ?
C4 C10 . 1.422(3) ?
C4 C18 . 1.507(2) ?
C5 C6 . 1.363(3) ?
C5 C10 . 1.422(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.406(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.369(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.423(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.423(2) ?
C12 C13 . 1.393(3) ?
C12 C17 . 1.398(3) ?
C13 C14 . 1.391(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.384(3) ?
C16 C17 . 1.386(2) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C19 C24 . 1.397(3) ?
C19 C20 . 1.397(3) ?
C20 C21 . 1.390(2) ?
C20 H20 . 0.95 ?
C21 C22 . 1.384(3) ?
C21 H21 . 0.95 ?
C22 C23 . 1.386(3) ?
C23 C24 . 1.385(3) ?
C23 H23 . 0.95 ?
C24 H24 . 0.95 ?
O3 C26 . 1.231(10) ?
N3 C26 . 1.328(8) ?
N3 C28 . 1.455(16) ?
N3 C27 . 1.476(10) ?
C25 C26 . 1.487(16) ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
O3' C26' . 1.229(8) ?
N3' C26' . 1.330(6) ?
N3' C28' . 1.457(13) ?
N3' C27' . 1.458(8) ?
C25' C26' . 1.488(14) ?
C25' H25D . 0.98 ?
C25' H25E . 0.98 ?
C25' H25F . 0.98 ?
C27' H27D . 0.98 ?
C27' H27E . 0.98 ?
C27' H27F . 0.98 ?
C28' H28D . 0.98 ?
C28' H28E . 0.98 ?
C28' H28F . 0.98 ?
O4 C30 . 1.242(8) ?
N4 C30 . 1.337(5) ?
N4 C31 . 1.460(7) ?
N4 C32 . 1.503(11) ?
C29 C30 . 1.479(11) ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?
C30 O4 1 1.242(8) ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
O4' C30' . 1.236(13) ?
N4' C30' . 1.338(9) ?
N4' C31' . 1.461(11) ?
N4' C32' . 1.525(16) ?
C29' C30' . 1.468(18) ?
C29' H29D . 0.98 ?
C29' H29E . 0.98 ?
C29' H29F . 0.98 ?
C31' H31D . 0.98 ?
C31' H31E . 0.98 ?
C31' H31F . 0.98 ?
C32' H32D . 0.98 ?
C32' H32E . 0.98 ?
C32' H32F . 0.98 ?
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
N1 H1N O4 . 0.84(2) 2.03(3) 2.865(13) 170(2)
N2 H2N O3' 2_666 0.81(2) 2.00(3) 2.797(13) 171(2)
C2 H2 O1 2_666 0.95 2.50 3.423(2) 163
C6 H6 O2 2_576 0.95 2.49 3.426(2) 169
C14 H14 O4 2_667 0.95 2.55 3.48(2) 167
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
C9 C1 C2 C3 . . . . 2.3(3) ?
C11 C1 C2 C3 . . . . -177.90(18) ?
C1 C2 C3 C4 . . . . 0.1(3) ?
C2 C3 C4 C10 . . . . -2.3(3) ?
C2 C3 C4 C18 . . . . 175.41(18) ?
C10 C5 C6 C7 . . . . 0.0(3) ?
C5 C6 C7 C8 . . . . -0.2(3) ?
C6 C7 C8 C9 . . . . 0.5(3) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
C7 C8 C9 C1 . . . . -179.19(18) ?
C2 C1 C9 C8 . . . . 176.20(17) ?
C11 C1 C9 C8 . . . . -3.6(3) ?
C2 C1 C9 C10 . . . . -2.4(3) ?
C11 C1 C9 C10 . . . . 177.81(17) ?
C3 C4 C10 C5 . . . . -176.67(18) ?
C18 C4 C10 C5 . . . . 5.7(3) ?
C3 C4 C10 C9 . . . . 2.1(3) ?
C18 C4 C10 C9 . . . . -175.54(17) ?
C6 C5 C10 C4 . . . . 178.69(18) ?
C6 C5 C10 C9 . . . . -0.1(3) ?
C8 C9 C10 C4 . . . . -178.42(17) ?
C1 C9 C10 C4 . . . . 0.2(3) ?
C8 C9 C10 C5 . . . . 0.4(3) ?
C1 C9 C10 C5 . . . . 179.02(17) ?
C12 N1 C11 O1 . . . . 3.9(3) ?
C12 N1 C11 C1 . . . . -173.45(16) ?
C2 C1 C11 O1 . . . . -61.0(2) ?
C9 C1 C11 O1 . . . . 118.8(2) ?
C2 C1 C11 N1 . . . . 116.43(19) ?
C9 C1 C11 N1 . . . . -63.8(2) ?
C11 N1 C12 C13 . . . . 162.24(18) ?
C11 N1 C12 C17 . . . . -18.1(3) ?
C17 C12 C13 C14 . . . . 1.1(3) ?
N1 C12 C13 C14 . . . . -179.22(16) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
C13 C14 C15 C16 . . . . -1.0(3) ?
C13 C14 C15 Br1 . . . . 177.59(14) ?
C14 C15 C16 C17 . . . . 1.3(3) ?
Br1 C15 C16 C17 . . . . -177.35(13) ?
C15 C16 C17 C12 . . . . -0.3(3) ?
C13 C12 C17 C16 . . . . -0.9(3) ?
N1 C12 C17 C16 . . . . 179.49(16) ?
C19 N2 C18 O2 . . . . 4.7(3) ?
C19 N2 C18 C4 . . . . -174.05(17) ?
C3 C4 C18 O2 . . . . -102.4(2) ?
C10 C4 C18 O2 . . . . 75.2(2) ?
C3 C4 C18 N2 . . . . 76.3(2) ?
C10 C4 C18 N2 . . . . -106.0(2) ?
C18 N2 C19 C24 . . . . -179.70(19) ?
C18 N2 C19 C20 . . . . 1.6(3) ?
C24 C19 C20 C21 . . . . -0.8(3) ?
N2 C19 C20 C21 . . . . 177.91(17) ?
C19 C20 C21 C22 . . . . -0.3(3) ?
C20 C21 C22 C23 . . . . 1.5(3) ?
C20 C21 C22 Br2 . . . . -179.05(13) ?
C21 C22 C23 C24 . . . . -1.5(3) ?
Br2 C22 C23 C24 . . . . 179.00(15) ?
C22 C23 C24 C19 . . . . 0.4(3) ?
C20 C19 C24 C23 . . . . 0.7(3) ?
N2 C19 C24 C23 . . . . -178.07(18) ?
C28 N3 C26 O3 . . . . 4.5(17) ?
C27 N3 C26 O3 . . . . 174.0(15) ?
C28 N3 C26 C25 . . . . -175.8(13) ?
C27 N3 C26 C25 . . . . -6.4(13) ?
C28' N3' C26' O3' . . . . 1.5(13) ?
C27' N3' C26' O3' . . . . -175.2(12) ?
C28' N3' C26' C25' . . . . -179.0(12) ?
C27' N3' C26' C25' . . . . 4.3(12) ?
O4 O4 C30 N4 1 . . . 0(3) ?
O4 O4 C30 C29 1 . . . 0(4) ?
C31 N4 C30 O4 . . . 1 174.5(12) ?
C32 N4 C30 O4 . . . 1 -0.1(13) ?
C31 N4 C30 O4 . . . . 174.5(12) ?
C32 N4 C30 O4 . . . . -0.1(13) ?
C31 N4 C30 C29 . . . . -1.6(9) ?
C32 N4 C30 C29 . . . . -176.2(9) ?
C31' N4' C30' O4' . . . . -180(2) ?
C32' N4' C30' O4' . . . . -9(2) ?
C31' N4' C30' C29' . . . . -0.9(17) ?
C32' N4' C30' C29' . . . . 170.0(16) ?
