#------------------------------------------------------------------------------
#$Date: 2018-07-31 15:06:23 +0300 (Tue, 31 Jul 2018) $
#$Revision: 209312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/11/2211194.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_2211194
loop_
_publ_author_name
'Atwell, Graham '
'Boyd, Peter D.W.'
'Denny, William A. '
'Yang, Shangjin  '
_publ_section_title
;
 2-[Bis(2-bromoethyl)amino]-N-(2-hydroxyethyl)-3,5-dinitrobenzamide
;
_journal_coeditor_code           SG2073
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5080
_journal_page_last               o5082
_journal_paper_doi               10.1107/S1600536806042188
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H16 Br2 N4 O6'
_chemical_formula_moiety         'C13 H16 Br2 N4 O6'
_chemical_formula_sum            'C13 H16 Br2 N4 O6'
_chemical_formula_weight         484.10
_chemical_name_systematic
;
2-[Bis(2-bromoethyl)amino]-N-(2-hydroxyethyl)-3,5-dinitrobenzamide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.29500(10)
_cell_length_b                   9.9641(2)
_cell_length_c                   19.1575(2)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    86(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.13
_cell_volume                     1774.30(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'MERCURY (Macrae et al.,  2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      86(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'Area-detector ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10742
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.606
_exptl_absorpt_correction_T_max  0.550935
_exptl_absorpt_correction_T_min  0.390921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.264
_refine_ls_abs_structure_details 'Flack (1983), 1548 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0157
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0164P)²+0.6655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0377
_refine_ls_wR_factor_ref         0.0382
_reflns_number_gt                3541
_reflns_number_total             3643
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2073.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-07-31

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

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 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C13 H16 Br2  N4 O6'
_cod_database_code               2211194
_cod_database_fobs_code          2211194
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
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
Br Br1 0.40751(2) 0.249349(19) 0.929613(9) 0.01727(5) Uani d . 1
Br Br2 -0.28556(2) 0.41618(2) 0.890082(10) 0.01951(5) Uani d . 1
N N3 0.12881(16) 0.57574(16) 0.91274(7) 0.0122(3) Uani d . 1
O O6 -0.07343(15) 0.81594(13) 1.03355(7) 0.0166(3) Uani d . 1
O O4 0.15459(17) 0.56843(14) 0.75554(7) 0.0220(3) Uani d . 1
O O1 0.19398(19) 1.15503(14) 0.77670(7) 0.0252(4) Uani d . 1
N N4 0.15130(18) 0.73137(16) 1.05021(8) 0.0136(3) Uani d . 1
H H15 0.2330 0.7141 1.0311 0.016 Uiso calc R 1
O O2 0.04981(17) 1.19592(14) 0.86354(8) 0.0238(3) Uani d . 1
O O5 0.14132(18) 0.46394(14) 1.10588(8) 0.0254(3) Uani d . 1
H H16 0.1682 0.4131 1.1369 0.038 Uiso calc R 1
O O3 0.35545(18) 0.67865(15) 0.74433(8) 0.0262(3) Uani d . 1
C C4 0.1362(2) 0.98017(19) 0.85101(10) 0.0147(4) Uani d . 1
N N2 0.23823(19) 0.65829(17) 0.77227(8) 0.0167(4) Uani d . 1
C C2 0.19306(19) 0.7535(2) 0.82703(8) 0.0131(3) Uani d . 1
C C7 0.23616(19) 0.47445(17) 0.89267(10) 0.0124(3) Uani d . 1
H H1 0.3231 0.5181 0.8763 0.015 Uiso calc R 1
H H2 0.1988 0.4190 0.8552 0.015 Uiso calc R 1
C C5 0.0816(2) 0.94452(18) 0.91548(9) 0.0134(4) Uani d . 1
H H3 0.0417 1.0093 0.9446 0.016 Uiso calc R 1
C C13 0.0571(2) 0.5693(2) 1.13547(10) 0.0210(4) Uani d . 1
H H4 0.0442 0.5532 1.1850 0.025 Uiso calc R 1
H H5 -0.0371 0.5708 1.1137 0.025 Uiso calc R 1
C C6 0.0866(2) 0.81095(18) 0.93645(9) 0.0125(3) Uani d . 1
C C8 0.2695(2) 0.38799(18) 0.95618(10) 0.0162(4) Uani d . 1
H H6 0.1819 0.3467 0.9734 0.019 Uiso calc R 1
H H7 0.3095 0.4432 0.9931 0.019 Uiso calc R 1
C C3 0.1980(2) 0.88677(18) 0.80689(10) 0.0146(4) Uani d . 1
H H8 0.2413 0.9125 0.7652 0.018 Uiso calc R 1
C C12 0.1305(2) 0.7025(2) 1.12466(10) 0.0191(4) Uani d . 1
H H9 0.0728 0.7730 1.1455 0.023 Uiso calc R 1
H H10 0.2232 0.7016 1.1479 0.023 Uiso calc R 1
N N1 0.12710(19) 1.12055(15) 0.82881(9) 0.0179(4) Uani d . 1
C C10 -0.0999(2) 0.49488(19) 0.86562(10) 0.0174(4) Uani d . 1
H H11 -0.0463 0.4330 0.8364 0.021 Uiso calc R 1
H H12 -0.1148 0.5771 0.8395 0.021 Uiso calc R 1
C C9 -0.0148(2) 0.52491(19) 0.93136(10) 0.0138(4) Uani d . 1
H H13 -0.0653 0.5913 0.9591 0.017 Uiso calc R 1
H H14 -0.0053 0.4439 0.9590 0.017 Uiso calc R 1
C C1 0.13690(19) 0.70845(17) 0.89094(10) 0.0115(3) Uani d . 1
C C11 0.0458(2) 0.78393(17) 1.01141(9) 0.0129(4) 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'
Ho Ho -0.2175 4.6783 '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
_geom_angle_publ_flag
C1 N3 C7 122.56(15) ?
C1 N3 C9 116.73(15) ?
C7 N3 C9 116.27(15) ?
C11 N4 C12 121.34(17) ?
C11 N4 H15 119.3 ?
C12 N4 H15 119.3 ?
C13 O5 H16 109.5 ?
C5 C4 C3 121.74(17) y
C5 C4 N1 118.94(17) ?
C3 C4 N1 119.32(17) ?
O4 N2 O3 124.55(17) ?
O4 N2 C2 118.29(16) ?
O3 N2 C2 117.08(17) ?
C3 C2 C1 124.19(17) y
C3 C2 N2 114.16(16) ?
C1 C2 N2 121.35(17) ?
N3 C7 C8 108.52(15) ?
N3 C7 H1 110.0 ?
C8 C7 H1 110.0 ?
N3 C7 H2 110.0 ?
C8 C7 H2 110.0 ?
H1 C7 H2 108.4 ?
C4 C5 C6 119.45(17) y
C4 C5 H3 120.3 ?
C6 C5 H3 120.3 ?
O5 C13 C12 110.20(17) ?
O5 C13 H4 109.6 ?
C12 C13 H4 109.6 ?
O5 C13 H5 109.6 ?
C12 C13 H5 109.6 ?
H4 C13 H5 108.1 ?
C5 C6 C1 121.43(17) y
C5 C6 C11 115.90(16) ?
C1 C6 C11 122.54(16) ?
C7 C8 Br1 109.02(13) ?
C7 C8 H6 109.9 ?
Br1 C8 H6 109.9 ?
C7 C8 H7 109.9 ?
Br1 C8 H7 109.9 ?
H6 C8 H7 108.3 ?
C4 C3 C2 117.52(17) y
C4 C3 H8 121.2 ?
C2 C3 H8 121.2 ?
N4 C12 C13 111.46(16) ?
N4 C12 H9 109.3 ?
C13 C12 H9 109.3 ?
N4 C12 H10 109.3 ?
C13 C12 H10 109.3 ?
H9 C12 H10 108.0 ?
O1 N1 O2 124.33(16) ?
O1 N1 C4 118.37(17) ?
O2 N1 C4 117.28(16) ?
C9 C10 Br2 109.93(13) ?
C9 C10 H11 109.7 ?
Br2 C10 H11 109.7 ?
C9 C10 H12 109.7 ?
Br2 C10 H12 109.7 ?
H11 C10 H12 108.2 ?
N3 C9 C10 109.85(15) ?
N3 C9 H13 109.7 ?
C10 C9 H13 109.7 ?
N3 C9 H14 109.7 ?
C10 C9 H14 109.7 ?
H13 C9 H14 108.2 ?
N3 C1 C2 125.90(16) ?
N3 C1 C6 118.81(16) ?
C2 C1 C6 115.28(16) y
O6 C11 N4 124.84(17) ?
O6 C11 C6 120.60(17) ?
N4 C11 C6 114.45(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C8 1.9524(19) ?
Br2 C10 1.953(2) ?
N3 C1 1.389(2) ?
N3 C7 1.470(2) ?
N3 C9 1.471(2) ?
O6 C11 1.229(2) ?
O4 N2 1.228(2) ?
O1 N1 1.225(2) ?
N4 C11 1.337(2) ?
N4 C12 1.468(2) ?
N4 H15 0.8600 ?
O2 N1 1.234(2) ?
O5 C13 1.427(3) ?
O5 H16 0.8200 ?
O3 N2 1.231(2) ?
C4 C5 1.382(3) y
C4 C3 1.382(3) y
C4 N1 1.464(2) ?
N2 C2 1.475(2) ?
C2 C3 1.384(3) y
C2 C1 1.405(3) y
C7 C8 1.523(3) ?
C7 H1 0.9700 ?
C7 H2 0.9700 ?
C5 C6 1.391(3) y
C5 H3 0.9300 ?
C13 C12 1.507(3) ?
C13 H4 0.9700 ?
C13 H5 0.9700 ?
C6 C1 1.422(3) y
C6 C11 1.510(3) ?
C8 H6 0.9700 ?
C8 H7 0.9700 ?
C3 H8 0.9300 ?
C12 H9 0.9700 ?
C12 H10 0.9700 ?
C10 C9 1.517(3) ?
C10 H11 0.9700 ?
C10 H12 0.9700 ?
C9 H13 0.9700 ?
C9 H14 0.9700 ?
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 H15 O6 3_567 0.86 2.21 3.057(2) 171 yes
O5 H16 O3 2_565 0.82 2.26 3.009(2) 152 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
O4 N2 C2 C3 -124.40(19)
O3 N2 C2 C3 52.4(2)
O4 N2 C2 C1 49.6(2)
O3 N2 C2 C1 -133.55(18)
C1 N3 C7 C8 138.33(17)
C9 N3 C7 C8 -66.1(2)
C3 C4 C5 C6 -1.0(3)
N1 C4 C5 C6 178.55(17)
C4 C5 C6 C1 -4.8(3)
C4 C5 C6 C11 171.05(17)
N3 C7 C8 Br1 178.24(12)
C5 C4 C3 C2 5.1(3)
N1 C4 C3 C2 -174.38(18)
C1 C2 C3 C4 -3.8(3)
N2 C2 C3 C4 169.99(17)
C11 N4 C12 C13 82.7(2)
O5 C13 C12 N4 59.7(2)
C5 C4 N1 O1 169.40(17)
C3 C4 N1 O1 -11.1(3)
C5 C4 N1 O2 -11.9(3)
C3 C4 N1 O2 167.65(18)
C1 N3 C9 C10 77.18(19)
C7 N3 C9 C10 -79.83(19)
Br2 C10 C9 N3 176.23(12)
C7 N3 C1 C2 32.4(3)
C9 N3 C1 C2 -123.06(19)
C7 N3 C1 C6 -146.67(17)
C9 N3 C1 C6 57.9(2)
C3 C2 C1 N3 179.36(18)
N2 C2 C1 N3 6.0(3)
C3 C2 C1 C6 -1.6(3)
N2 C2 C1 C6 -174.94(16)
C5 C6 C1 N3 -174.93(17)
C11 C6 C1 N3 9.5(3)
C5 C6 C1 C2 5.9(3)
C11 C6 C1 C2 -169.69(17)
C12 N4 C11 O6 2.2(3)
C12 N4 C11 C6 178.33(16)
C5 C6 C11 O6 58.7(2)
C1 C6 C11 O6 -125.44(19)
C5 C6 C11 N4 -117.59(18)
C1 C6 C11 N4 58.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9617955
