#------------------------------------------------------------------------------
#$Date: 2022-09-28 17:08:17 +0200 (Wed 28 de Sep de 2022) $
#$Revision: 278247 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003532.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_2003532
loop_
_publ_author_name
'Baughman, R. G.'
'Chang, S.-C.'
'Utecht, R. E.'
'Lewis, D. E.'
_publ_section_title
;
 Two Related Potent Antiviral Compounds:
 3-Bromo-N-butyl-4-butylamino-1,8-naphthalenedicarboximide (1)
 and 4-Amino-3-bromo-N-butyl-1,8-naphthalenedicarboximide (2)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1189
_journal_page_last               1193
_journal_paper_doi               10.1107/S0108270194011005
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'synthesized, recrystallized from EtOAc'
_chemical_formula_sum            'C20 H23 Br N2 O2'
_chemical_formula_weight         403.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                87.84(2)
_cell_angle_beta                 88.13(2)
_cell_angle_gamma                80.61(2)
_cell_formula_units_Z            2
_cell_length_a                   8.374(2)
_cell_length_b                   9.935(2)
_cell_length_c                   11.139(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      13.1
_cell_measurement_theta_min      5.1
_cell_volume                     913.3(3)
_diffrn_measurement_device       'Siemens P3'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6359
_diffrn_reflns_theta_max         25.04
_diffrn_standards_decay_%        +-2.8
_diffrn_standards_interval_count 50
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.249
_refine_ls_goodness_of_fit_obs   1.050
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3227
_refine_ls_R_factor_obs          0.0379
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_obs         0.0912
_reflns_number_total             3228
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cr1107.cif
_cod_data_source_block           1
_cod_original_cell_volume        913.3(4)
_cod_database_code               2003532
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Br -.0491(1) .3733(1) -.1918(1) .057(1)
O(1) -.1362(3) -.0200(2) .1375(2) .051(1)
O(2) -.4283(3) .1663(3) .4562(2) .057(1)
N(1) -.2895(3) .0715(3) .2938(2) .036(1)
N(2) -.2522(4) .5999(3) -.0580(3) .059(1)
C(1) -.2098(4) .0831(3) .1837(3) .036(1)
C(2) -.1447(4) .2347(3) .0163(3) .037(1)
C(3) -.1589(4) .3622(3) -.0409(3) .039(1)
C(4) -.2475(4) .4821(3) .0076(3) .042(1)
C(5) -.4193(5) .5764(4) .1855(3) .056(1)
C(6) -.4905(5) .5572(4) .2960(3) .059(1)
C(7) -.4765(5) .4284(3) .3505(3) .047(1)
C(8) -.3720(4) .1828(3) .3564(3) .040(1)
C(9) -.2200(4) .2193(3) .1265(3) .033(1)
C(10) -.3264(4) .4666(3) .1235(3) .037(1)
C(11) -.3864(4) .3182(3) .2949(3) .037(1)
C(12) -.3108(4) .3349(3) .1815(3) .033(1)
C(13) -.2864(4) -.0663(3) .3500(3) .041(1)
C(14) -.1411(4) -.1118(3) .4272(3) .042(1)
C(15) -.1434(5) -.2515(4) .4858(3) .052(1)
C(16) .0063(6) -.3033(5) .5580(4) .081(1)
C(17) -.3206(5) .7415(3) -.0366(3) .047(1)
C(18) -.2772(5) .8277(3) -.1447(3) .047(1)
C(19) -.3453(5) .9769(3) -.1367(3) .049(1)
C(20) -.2912(6) 1.0612(4) -.2408(4) .067(1)
H(2A) -.2022(4) .5883(3) -.1305(3) .080
H(2B) -.0821(4) .1569(3) -.0210(3) .080
H(5A) -.4325(5) .6665(4) .1491(3) .080
H(6A) -.5507(5) .6340(4) .3361(3) .080
H(7A) -.5296(5) .4158(3) .4268(3) .080
H(13A) -.2865(4) -.1307(3) .2880(3) .080
H(13B) -.3832(4) -.0667(3) .3986(3) .080
H(14A) -.1394(4) -.0467(3) .4885(3) .080
H(14B) -.0441(4) -.1139(3) .3784(3) .080
H(15A) -.1520(5) -.3152(4) .4246(3) .080
H(15B) -.2375(5) -.2477(4) .5379(3) .080
H(16A) -.0018(6) -.3919(5) .5928(4) .080
H(16B) .1008(6) -.3095(5) .5061(4) .080
H(16C) .0144(6) -.2412(5) .6207(4) .080
H(17A) -.2772(5) .7708(3) .0349(3) .080
H(17B) -.4361(5) .7509(3) -.0261(3) .080
H(18A) -.3164(5) .7936(3) -.2157(3) .080
H(18B) -.1614(5) .8178(3) -.1530(3) .080
H(19A) -.3122(5) 1.0100(3) -.0632(3) .080
H(19C) -.4614(5) .9878(3) -.1344(3) .080
H(20D) -.3377(6) 1.1552(4) -.2316(4) .080
H(20A) -.1752(6) 1.0523(4) -.2426(4) .080
H(20B) -.3260(6) 1.0298(4) -.3146(4) .080
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(1) N(1) C(8) 124.0(3)
C(1) N(1) C(13) 118.5(3)
C(8) N(1) C(13) 117.5(3)
C(4) N(2) C(17) 133.8(3)
O(1) C(1) N(1) 119.3(3)
O(1) C(1) C(9) 122.8(3)
N(1) C(1) C(9) 117.9(3)
C(9) C(2) C(3) 120.1(3)
C(2) C(3) C(4) 123.8(3)
C(2) C(3) Br 117.0(2)
C(4) C(3) Br 119.2(2)
N(2) C(4) C(3) 117.7(3)
N(2) C(4) C(10) 125.9(3)
C(3) C(4) C(10) 116.3(3)
C(6) C(5) C(10) 121.8(3)
C(5) C(6) C(7) 120.8(3)
C(11) C(7) C(6) 119.9(3)
O(2) C(8) N(1) 120.5(3)
O(2) C(8) C(11) 122.5(3)
N(1) C(8) C(11) 117.0(3)
C(2) C(9) C(12) 119.5(3)
C(2) C(9) C(1) 119.6(3)
C(12) C(9) C(1) 120.8(3)
C(5) C(10) C(12) 116.9(3)
C(5) C(10) C(4) 123.8(3)
C(12) C(10) C(4) 119.4(3)
C(7) C(11) C(12) 120.5(3)
C(7) C(11) C(8) 118.5(3)
C(12) C(11) C(8) 121.0(3)
C(11) C(12) C(9) 119.1(3)
C(11) C(12) C(10) 120.1(3)
C(9) C(12) C(10) 120.9(3)
N(1) C(13) C(14) 113.3(3)
C(13) C(14) C(15) 112.1(3)
C(14) C(15) C(16) 113.2(3)
N(2) C(17) C(18) 108.0(3)
C(19) C(18) C(17) 113.8(3)
C(18) C(19) C(20) 112.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C(3) 1.898(3)
O(1) C(1) 1.228(4)
O(2) C(8) 1.209(4)
N(1) C(1) 1.387(4)
N(1) C(8) 1.401(4)
N(1) C(13) 1.481(4)
N(2) C(4) 1.351(4)
N(2) C(17) 1.455(4)
C(1) C(9) 1.464(4)
C(2) C(9) 1.377(4)
C(2) C(3) 1.385(4)
C(3) C(4) 1.413(4)
C(4) C(10) 1.446(4)
C(5) C(6) 1.370(5)
C(5) C(10) 1.420(5)
C(6) C(7) 1.385(5)
C(7) C(11) 1.380(5)
C(8) C(11) 1.475(5)
C(9) C(12) 1.418(4)
C(10) C(12) 1.426(4)
C(11) C(12) 1.411(4)
C(13) C(14) 1.511(5)
C(14) C(15) 1.515(5)
C(15) C(16) 1.518(6)
C(17) C(18) 1.521(5)
C(18) C(19) 1.503(5)
C(19) C(20) 1.506(5)
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
C(4) C(10) C(12) C(9) -0.4(5)
C(4) C(10) C(12) C(11) 179.7(3)
C(5) C(10) C(12) C(9) -179.9(3)
C(6) C(7) C(11) C(12) -1.4(5)
C(1) N(1) C(13) C(14) 87.6(3)
C(8) N(1) C(13) C(14) -91.7(3)
N(1) C(13) C(14) C(15) 178.6(3)
C(13) C(14) C(15) C(16) 176.6(3)
C(3) C(4) N(2) C(17) -175.9(3)
C(10) C(4) N(2) C(17) 4.6(6)
C(4) N(2) C(17) C(18) 177.2(4)
N(2) C(17) C(18) C(19) 178.0(3)
C(17) C(18) C(19) C(20) 176.1(3)
