data_2003532
_journal_name_full    'Acta Crystallographica'
_journal_year         1995
_journal_volume    	C51
_journal_page_first    	1189
_journal_page_last    	1193
_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)
;
_chemical_formula_sum    	'C20 H23 Br N2 O2'
_chemical_formula_weight    	403.31
_symmetry_space_group_name_H-M    	'P -1'
_cell_length_a    	8.374(2)
_cell_length_b    	9.935(2)
_cell_length_c    	11.139(2)
_cell_angle_alpha    	87.84(2)
_cell_angle_beta    	88.13(2)
_cell_angle_gamma    	80.61(2)
_cell_volume    	913.3(4)
_cell_formula_units_Z    	2
_exptl_crystal_density_diffrn    	1.467
_exptl_crystal_density_meas    	?
_diffrn_radiation_type    	'MoK\a'
_diffrn_radiation_wavelength    	0.71073
_cell_measurement_reflns_used    	25
_cell_measurement_theta_min    	5.1
_cell_measurement_theta_max    	13.1
_exptl_absorpt_coefficient_mu    	2.266
_cell_measurement_temperature    	290(2)
_exptl_crystal_description    	Prism
_exptl_crystal_size_max    	0.375
_exptl_crystal_size_mid    	0.23
_exptl_crystal_size_min    	0.11
_exptl_crystal_size_rad    	?
_exptl_crystal_colour    	'yellow'
_chemical_compound_source    	'synthesized, recrystallized from EtOAc'
_diffrn_measurement_device    	'Siemens P3'
_diffrn_measurement_method    	'\w/2\q'
_exptl_absorpt_correction_type    	'empirical'
_exptl_absorpt_correction_T_min    	0.428
_exptl_absorpt_correction_T_max    	0.775
_diffrn_reflns_number    	6359
_reflns_number_total    	3228
_reflns_number_observed    	?
_reflns_observed_criterion    	I>2\s(I)
_diffrn_reflns_av_R_equivalents    	0.0318
_diffrn_reflns_theta_max    	25.04
_diffrn_reflns_limit_h_min    	-9
_diffrn_reflns_limit_h_max    	9
_diffrn_reflns_limit_k_min    	-11
_diffrn_reflns_limit_k_max    	11
_diffrn_reflns_limit_l_min    	-13
_diffrn_reflns_limit_l_max    	13
_diffrn_standards_number    	3
_diffrn_standards_interval_count    	50
_diffrn_standards_interval_time    	?
_diffrn_standards_decay_%    	+-2.8
_refine_ls_structure_factor_coef    	Fsqd
_refine_ls_R_factor_obs    	0.0379
_refine_ls_wR_factor_obs    	0.0912
_refine_ls_goodness_of_fit_obs    	1.050
_refine_ls_number_reflns    	3227
_refine_ls_number_parameters    	226
_refine_ls_hydrogen_treatment    	?
_refine_ls_weighting_scheme    	?
_refine_ls_shift/esd_max    	?
_refine_diff_density_max    	0.316
_refine_diff_density_min    	-0.249
_refine_ls_extinction_method    	?
_refine_ls_extinction_coef    	?
_atom_type_scat_source    	?
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