#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153919.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7153919
loop_
_publ_author_name
'Murphy, Samantha'
'Bright, Sandra A.'
'Poynton, Fergus E.'
'McCabe, Thomas'
'Kitchen, Jonathan A.'
'Veale, Emma B.'
'Williams, D. Clive'
'Gunnlaugsson, Thorfinnur'
_publ_section_title
;
 Synthesis, photophysical and cytotoxicity evaluations of DNA targeting
 agents based on 3-amino-1,8-naphthalimide derived Tröger's bases.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6610
_journal_page_last               6623
_journal_paper_doi               10.1039/c3ob42213e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C18 H19 N3 O2'
_chemical_formula_weight         309.36
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.174(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6599(17)
_cell_length_b                   21.310(5)
_cell_length_c                   11.054(3)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    118(2)
_cell_measurement_theta_max      31.2862
_cell_measurement_theta_min      1.8639
_cell_volume                     1548.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      118(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12422
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1073P)²+0.1417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.1973
_reflns_number_gt                2202
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42213e2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7153917--7153919.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153919
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.6954(3) 0.04191(8) 0.95694(15) 0.0293(5) Uani 1 1 d .
O2 O 0.1260(2) 0.04022(7) 0.67119(14) 0.0245(4) Uani 1 1 d .
N1 N 0.4920(3) 0.18203(9) 0.82748(17) 0.0255(5) Uani 1 1 d .
N2 N 0.4107(3) 0.04112(9) 0.81305(16) 0.0204(5) Uani 1 1 d .
N6 N 0.2563(3) -0.11841(9) 0.35063(18) 0.0282(5) Uani 1 1 d .
H6A H 0.3069 -0.1472 0.3071 0.034 Uiso 1 1 calc R
H6B H 0.1335 -0.1035 0.3258 0.034 Uiso 1 1 calc R
C19 C 0.6752(5) 0.27464(13) 0.8024(3) 0.0426(8) Uani 1 1 d .
H19A H 0.6627 0.3206 0.8115 0.051 Uiso 1 1 calc R
H19B H 0.7606 0.2659 0.7387 0.051 Uiso 1 1 calc R
C20 C 0.4668(5) 0.24417(12) 0.7700(2) 0.0338(7) Uani 1 1 d .
H20A H 0.3620 0.2688 0.8032 0.041 Uiso 1 1 calc R
H20B H 0.4273 0.2405 0.6801 0.041 Uiso 1 1 calc R
C21 C 0.7658(5) 0.24403(14) 0.9250(3) 0.0451(8) Uani 1 1 d .
H21A H 0.8967 0.2233 0.9188 0.054 Uiso 1 1 calc R
H21B H 0.7887 0.2758 0.9912 0.054 Uiso 1 1 calc R
C22 C 0.6073(4) 0.19597(12) 0.9499(2) 0.0332(7) Uani 1 1 d .
H22A H 0.6733 0.1577 0.9882 0.040 Uiso 1 1 calc R
H22B H 0.5172 0.2137 1.0043 0.040 Uiso 1 1 calc R
C23 C 0.2969(4) 0.15239(11) 0.8309(2) 0.0256(6) Uani 1 1 d .
H23A H 0.2206 0.1506 0.7464 0.031 Uiso 1 1 calc R
H23B H 0.2182 0.1789 0.8800 0.031 Uiso 1 1 calc R
C24 C 0.3107(4) 0.08671(11) 0.8841(2) 0.0242(6) Uani 1 1 d .
H24A H 0.3868 0.0885 0.9686 0.029 Uiso 1 1 calc R
H24B H 0.1717 0.0716 0.8890 0.029 Uiso 1 1 calc R
C25 C 0.6066(4) 0.02013(11) 0.8610(2) 0.0222(5) Uani 1 1 d .
C26 C 0.2965(3) 0.01924(10) 0.7044(2) 0.0202(5) Uani 1 1 d .
C27 C 0.3896(3) -0.02892(10) 0.63519(19) 0.0190(5) Uani 1 1 d .
C28 C 0.5868(3) -0.05107(10) 0.67996(19) 0.0193(5) Uani 1 1 d .
C29 C 0.6963(3) -0.02855(10) 0.7913(2) 0.0207(5) Uani 1 1 d .
C30 C 0.8875(4) -0.05135(11) 0.8346(2) 0.0238(6) Uani 1 1 d .
H30 H 0.9600 -0.0363 0.9101 0.029 Uiso 1 1 calc R
C31 C 0.9757(4) -0.09676(11) 0.7676(2) 0.0256(6) Uani 1 1 d .
H31 H 1.1076 -0.1124 0.7981 0.031 Uiso 1 1 calc R
C32 C 0.8730(4) -0.11874(11) 0.6584(2) 0.0240(6) Uani 1 1 d .
H32 H 0.9358 -0.1491 0.6137 0.029 Uiso 1 1 calc R
C33 C 0.6746(3) -0.09696(10) 0.61101(19) 0.0197(5) Uani 1 1 d .
C34 C 0.5626(4) -0.11868(10) 0.5001(2) 0.0211(5) Uani 1 1 d .
H34 H 0.6214 -0.1491 0.4537 0.025 Uiso 1 1 calc R
C35 C 0.2833(3) -0.05123(10) 0.5270(2) 0.0206(5) Uani 1 1 d .
H35 H 0.1502 -0.0359 0.4986 0.025 Uiso 1 1 calc R
C36 C 0.3690(3) -0.09675(11) 0.4572(2) 0.0208(5) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C23 N1 C20 111.3(2)
C23 N1 C22 113.64(19)
C20 N1 C22 102.86(19)
C26 N2 C25 124.5(2)
C26 N2 C24 116.63(19)
C25 N2 C24 118.78(18)
C36 N6 H6A 120.0
C36 N6 H6B 120.0
H6A N6 H6B 120.0
C20 C19 C21 104.0(2)
C20 C19 H19A 111.0
C21 C19 H19A 111.0
C20 C19 H19B 111.0
C21 C19 H19B 111.0
H19A C19 H19B 109.0
N1 C20 C19 104.2(2)
N1 C20 H20A 110.9
C19 C20 H20A 110.9
N1 C20 H20B 110.9
C19 C20 H20B 110.9
H20A C20 H20B 108.9
C22 C21 C19 105.0(2)
C22 C21 H21A 110.8
C19 C21 H21A 110.8
C22 C21 H21B 110.8
C19 C21 H21B 110.8
H21A C21 H21B 108.8
N1 C22 C21 104.1(2)
N1 C22 H22A 110.9
C21 C22 H22A 110.9
N1 C22 H22B 110.9
C21 C22 H22B 110.9
H22A C22 H22B 109.0
N1 C23 C24 114.4(2)
N1 C23 H23A 108.7
C24 C23 H23A 108.7
N1 C23 H23B 108.7
C24 C23 H23B 108.7
H23A C23 H23B 107.6
N2 C24 C23 114.01(19)
N2 C24 H24A 108.8
C23 C24 H24A 108.8
N2 C24 H24B 108.8
C23 C24 H24B 108.8
H24A C24 H24B 107.6
O1 C25 N2 120.1(2)
O1 C25 C29 122.7(2)
N2 C25 C29 117.2(2)
O2 C26 N2 119.3(2)
O2 C26 C27 123.1(2)
N2 C26 C27 117.5(2)
C35 C27 C28 120.8(2)
C35 C27 C26 119.4(2)
C28 C27 C26 119.8(2)
C27 C28 C29 121.1(2)
C27 C28 C33 118.8(2)
C29 C28 C33 120.1(2)
C30 C29 C28 120.3(2)
C30 C29 C25 119.8(2)
C28 C29 C25 119.9(2)
C29 C30 C31 120.1(2)
C29 C30 H30 119.9
C31 C30 H30 119.9
C32 C31 C30 120.6(2)
C32 C31 H31 119.7
C30 C31 H31 119.7
C31 C32 C33 121.2(2)
C31 C32 H32 119.4
C33 C32 H32 119.4
C34 C33 C32 123.2(2)
C34 C33 C28 119.1(2)
C32 C33 C28 117.7(2)
C36 C34 C33 121.6(2)
C36 C34 H34 119.2
C33 C34 H34 119.2
C27 C35 C36 121.0(2)
C27 C35 H35 119.5
C36 C35 H35 119.5
N6 C36 C34 122.2(2)
N6 C36 C35 119.1(2)
C34 C36 C35 118.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C25 1.220(3)
O2 C26 1.221(3)
N1 C23 1.451(3)
N1 C20 1.467(3)
N1 C22 1.475(3)
N2 C26 1.395(3)
N2 C25 1.401(3)
N2 C24 1.473(3)
N6 C36 1.372(3)
N6 H6A 0.8800
N6 H6B 0.8800
C19 C20 1.523(4)
C19 C21 1.538(4)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9900
C20 H20B 0.9900
C21 C22 1.527(4)
C21 H21A 0.9900
C21 H21B 0.9900
C22 H22A 0.9900
C22 H22B 0.9900
C23 C24 1.516(3)
C23 H23A 0.9900
C23 H23B 0.9900
C24 H24A 0.9900
C24 H24B 0.9900
C25 C29 1.475(3)
C26 C27 1.475(3)
C27 C35 1.374(3)
C27 C28 1.409(3)
C28 C29 1.411(3)
C28 C33 1.422(3)
C29 C30 1.376(3)
C30 C31 1.403(3)
C30 H30 0.9500
C31 C32 1.371(3)
C31 H31 0.9500
C32 C33 1.420(3)
C32 H32 0.9500
C33 C34 1.408(3)
C34 C36 1.382(3)
C34 H34 0.9500
C35 C36 1.415(3)
C35 H35 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N1 0.88 2.28 3.094(3) 154.2 3_656
N6 H6B O2 0.88 2.20 3.020(3) 155.8 3_556
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
C23 N1 C20 C19 166.21(19)
C22 N1 C20 C19 44.2(2)
C21 C19 C20 N1 -28.6(3)
C20 C19 C21 C22 2.9(3)
C23 N1 C22 C21 -162.4(2)
C20 N1 C22 C21 -42.0(2)
C19 C21 C22 N1 23.5(3)
C20 N1 C23 C24 177.46(19)
C22 N1 C23 C24 -67.0(3)
C26 N2 C24 C23 -75.9(3)
C25 N2 C24 C23 107.6(2)
N1 C23 C24 N2 -63.0(3)
C26 N2 C25 O1 -179.9(2)
C24 N2 C25 O1 -3.7(3)
C26 N2 C25 C29 -0.1(3)
C24 N2 C25 C29 176.09(19)
C25 N2 C26 O2 179.2(2)
C24 N2 C26 O2 2.9(3)
C25 N2 C26 C27 -0.5(3)
C24 N2 C26 C27 -176.84(18)
O2 C26 C27 C35 1.0(3)
N2 C26 C27 C35 -179.24(19)
O2 C26 C27 C28 -179.6(2)
N2 C26 C27 C28 0.2(3)
C35 C27 C28 C29 -179.71(19)
C26 C27 C28 C29 0.9(3)
C35 C27 C28 C33 0.1(3)
C26 C27 C28 C33 -179.27(19)
C27 C28 C29 C30 179.0(2)
C33 C28 C29 C30 -0.8(3)
C27 C28 C29 C25 -1.6(3)
C33 C28 C29 C25 178.6(2)
O1 C25 C29 C30 0.4(4)
N2 C25 C29 C30 -179.4(2)
O1 C25 C29 C28 -179.0(2)
N2 C25 C29 C28 1.2(3)
C28 C29 C30 C31 0.7(3)
C25 C29 C30 C31 -178.7(2)
C29 C30 C31 C32 0.2(4)
C30 C31 C32 C33 -0.8(4)
C31 C32 C33 C34 -179.3(2)
C31 C32 C33 C28 0.7(3)
C27 C28 C33 C34 0.2(3)
C29 C28 C33 C34 -179.9(2)
C27 C28 C33 C32 -179.7(2)
C29 C28 C33 C32 0.2(3)
C32 C33 C34 C36 179.5(2)
C28 C33 C34 C36 -0.4(3)
C28 C27 C35 C36 -0.4(3)
C26 C27 C35 C36 179.1(2)
C33 C34 C36 N6 -178.6(2)
C33 C34 C36 C35 0.2(3)
C27 C35 C36 N6 179.0(2)
C27 C35 C36 C34 0.2(3)
