#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/66/2016699.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_2016699
loop_
_publ_author_name
'Tagg, Tei'
'McAdam, C. John'
'Robinson, Brian H.'
'Simpson, Jim'
_publ_section_title
;
 N-(2-Bromoethyl)-4-piperidino-1,8-naphthalimide and
 N-(3-bromopropyl)-4-piperidino-1,8-naphthalimide
;
_journal_coeditor_code           SU3024
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o388
_journal_page_last               o391
_journal_paper_doi               10.1107/S0108270108016120
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H21 Br N2 O2'
_chemical_formula_moiety         'C20 H21 Br N2 O2'
_chemical_formula_sum            'C20 H21 Br N2 O2'
_chemical_formula_weight         401.30
_chemical_name_systematic
;
N-(3-bromopropyl)-4-piperidino-1,8-naphthalimide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5690(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4165(3)
_cell_length_b                   17.7709(5)
_cell_length_c                   7.9618(2)
_cell_measurement_reflns_used    9183
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      31.89
_cell_measurement_theta_min      2.29
_cell_volume                     1751.21(8)
_computing_cell_refinement
'APEX2 (Bruker 2005) and SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al.,  2004) and PLATON
(Spek, 2003)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson,
1999)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson,
1999)
;
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius APEXII CCD'
_diffrn_measurement_method       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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30759
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.363
_exptl_absorpt_correction_T_max  0.9114
_exptl_absorpt_correction_T_min  0.2009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.124
_refine_diff_density_min         -0.993
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0407P)²+1.4674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                4434
_reflns_number_total             5571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su3024.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016699
_cod_database_fobs_code          2016699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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 -0.527590(16) 0.344479(14) -0.08936(3) 0.03387(8) Uani d . 1
C C1 -0.07010(12) 0.21710(9) 0.13372(19) 0.0101(3) Uani d . 1
C C2 -0.05950(13) 0.13995(9) 0.1262(2) 0.0117(3) Uani d . 1
H H2 -0.1127 0.1087 0.1699 0.014 Uiso calc R 1
C C3 0.02862(12) 0.10695(9) 0.0549(2) 0.0119(3) Uani d . 1
H H3 0.0339 0.0537 0.0508 0.014 Uiso calc R 1
C C4 0.10850(12) 0.15060(9) -0.00995(19) 0.0106(3) Uani d . 1
C C5 0.17083(13) 0.28019(9) -0.0824(2) 0.0123(3) Uani d . 1
H H5 0.2295 0.2597 -0.1371 0.015 Uiso calc R 1
C C6 0.15774(13) 0.35695(9) -0.0764(2) 0.0139(3) Uani d . 1
H H6 0.2083 0.3888 -0.1248 0.017 Uiso calc R 1
C C7 0.07062(13) 0.38882(9) 0.0005(2) 0.0128(3) Uani d . 1
H H7 0.0628 0.4420 0.0047 0.015 Uiso calc R 1
C C8 -0.00351(13) 0.34286(9) 0.07011(19) 0.0107(3) Uani d . 1
C C9 0.00834(12) 0.26353(9) 0.06657(18) 0.0095(3) Uani d . 1
C C10 0.09767(12) 0.23118(9) -0.00795(19) 0.0101(3) Uani d . 1
C C11 -0.16305(12) 0.24960(9) 0.21211(19) 0.0112(3) Uani d . 1
O O11 -0.23120(10) 0.21141(7) 0.27405(16) 0.0172(2) Uani d . 1
C C12 -0.09637(13) 0.37712(9) 0.1471(2) 0.0125(3) Uani d . 1
O O12 -0.10989(10) 0.44520(7) 0.15472(17) 0.0187(3) Uani d . 1
N N1 -0.17076(11) 0.32831(7) 0.21262(17) 0.0112(2) Uani d . 1
C C13 -0.26345(13) 0.36280(9) 0.2877(2) 0.0143(3) Uani d . 1
H H13A -0.2389 0.4087 0.3501 0.017 Uiso calc R 1
H H13B -0.2914 0.3272 0.3694 0.017 Uiso calc R 1
C C14 -0.35487(14) 0.38371(10) 0.1556(2) 0.0178(3) Uani d . 1
H H14A -0.4106 0.4126 0.2104 0.021 Uiso calc R 1
H H14B -0.3258 0.4165 0.0693 0.021 Uiso calc R 1
C C15 -0.40682(15) 0.31494(11) 0.0701(2) 0.0203(3) Uani d . 1
H H15A -0.4332 0.2809 0.1562 0.024 Uiso calc R 1
H H15B -0.3524 0.2874 0.0097 0.024 Uiso calc R 1
N N2 0.19869(11) 0.11816(8) -0.07946(17) 0.0114(2) Uani d . 1
C C16 0.18654(13) 0.03899(9) -0.1283(2) 0.0133(3) Uani d . 1
H H16A 0.1158 0.0316 -0.1928 0.016 Uiso calc R 1
H H16B 0.1881 0.0073 -0.0259 0.016 Uiso calc R 1
C C17 0.27673(13) 0.01469(9) -0.2355(2) 0.0156(3) Uani d . 1
H H17A 0.2711 0.0432 -0.3426 0.019 Uiso calc R 1
H H17B 0.2688 -0.0395 -0.2627 0.019 Uiso calc R 1
C C18 0.38716(14) 0.02853(10) -0.1428(2) 0.0188(3) Uani d . 1
H H18A 0.4446 0.0166 -0.2179 0.023 Uiso calc R 1
H H18B 0.3966 -0.0048 -0.0430 0.023 Uiso calc R 1
C C19 0.39682(13) 0.11066(10) -0.0871(2) 0.0179(3) Uani d . 1
H H19A 0.4664 0.1185 -0.0195 0.022 Uiso calc R 1
H H19B 0.3956 0.1437 -0.1874 0.022 Uiso calc R 1
C C20 0.30362(13) 0.13121(10) 0.0176(2) 0.0148(3) Uani d . 1
H H20A 0.3077 0.1004 0.1215 0.018 Uiso calc R 1
H H20B 0.3095 0.1848 0.0510 0.018 Uiso calc R 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
C2 C1 C9 119.53(14)
C2 C1 C11 119.27(14)
C9 C1 C11 121.20(14)
C1 C2 C3 120.95(14)
C1 C2 H2 119.5
C3 C2 H2 119.5
C4 C3 C2 121.34(14)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 N2 121.97(14)
C3 C4 C10 118.76(14)
N2 C4 C10 119.27(13)
C6 C5 C10 120.79(14)
C6 C5 H5 119.6
C10 C5 H5 119.6
C5 C6 C7 120.86(15)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 119.87(15)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C9 120.48(14)
C7 C8 C12 119.32(14)
C9 C8 C12 120.20(13)
C1 C9 C8 119.81(14)
C1 C9 C10 120.41(14)
C8 C9 C10 119.77(13)
C9 C10 C5 118.19(14)
C9 C10 C4 118.97(13)
C5 C10 C4 122.81(14)
O11 C11 N1 120.30(14)
O11 C11 C1 123.06(14)
N1 C11 C1 116.64(13)
O12 C12 N1 119.83(14)
O12 C12 C8 122.83(14)
N1 C12 C8 117.34(14)
C12 N1 C11 124.79(13)
C12 N1 C13 117.03(13)
C11 N1 C13 118.18(13)
N1 C13 C14 112.53(13)
N1 C13 H13A 109.1
C14 C13 H13A 109.1
N1 C13 H13B 109.1
C14 C13 H13B 109.1
H13A C13 H13B 107.8
C15 C14 C13 112.21(14)
C15 C14 H14A 109.2
C13 C14 H14A 109.2
C15 C14 H14B 109.2
C13 C14 H14B 109.2
H14A C14 H14B 107.9
C14 C15 Br1 110.55(13)
C14 C15 H15A 109.5
Br1 C15 H15A 109.5
C14 C15 H15B 109.5
Br1 C15 H15B 109.5
H15A C15 H15B 108.1
C4 N2 C16 115.37(13)
C4 N2 C20 115.11(13)
C16 N2 C20 110.93(13)
N2 C16 C17 110.87(13)
N2 C16 H16A 109.5
C17 C16 H16A 109.5
N2 C16 H16B 109.5
C17 C16 H16B 109.5
H16A C16 H16B 108.1
C16 C17 C18 110.85(14)
C16 C17 H17A 109.5
C18 C17 H17A 109.5
C16 C17 H17B 109.5
C18 C17 H17B 109.5
H17A C17 H17B 108.1
C17 C18 C19 109.97(14)
C17 C18 H18A 109.7
C19 C18 H18A 109.7
C17 C18 H18B 109.7
C19 C18 H18B 109.7
H18A C18 H18B 108.2
C20 C19 C18 110.02(14)
C20 C19 H19A 109.7
C18 C19 H19A 109.7
C20 C19 H19B 109.7
C18 C19 H19B 109.7
H19A C19 H19B 108.2
N2 C20 C19 110.61(14)
N2 C20 H20A 109.5
C19 C20 H20A 109.5
N2 C20 H20B 109.5
C19 C20 H20B 109.5
H20A C20 H20B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.9579(18)
C1 C2 1.379(2)
C1 C9 1.414(2)
C1 C11 1.473(2)
C2 C3 1.401(2)
C2 H2 0.9500
C3 C4 1.391(2)
C3 H3 0.9500
C4 N2 1.411(2)
C4 C10 1.438(2)
C5 C6 1.375(2)
C5 C10 1.422(2)
C5 H5 0.9500
C6 C7 1.404(2)
C6 H6 0.9500
C7 C8 1.379(2)
C7 H7 0.9500
C8 C9 1.418(2)
C8 C12 1.479(2)
C9 C10 1.420(2)
C11 O11 1.2192(19)
C11 N1 1.402(2)
C12 O12 1.224(2)
C12 N1 1.398(2)
N1 C13 1.472(2)
C13 C14 1.531(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.517(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9900
C15 H15B 0.9900
N2 C16 1.464(2)
N2 C20 1.479(2)
C16 C17 1.524(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.525(2)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.527(3)
C18 H18A 0.9900
C18 H18B 0.9900
C19 C20 1.524(2)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9900
C20 H20B 0.9900
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
C7 H7 O12 3_565 0.95 2.47 3.250(2) 139.5
C15 H15B O11 4_565 0.99 2.50 3.369(2) 146.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654116
