#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/85/2208527.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_2208527
loop_
_publ_author_name
'Bardajee, Ghasem Rezanejad'
'Winnik, Mitchell A.'
'Lough, Alan J.'
_publ_section_title
4-[N-(2-Hydroxyethyl)-N-methylamino]-N-isopropyl-1,8-naphthalimide
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1615
_journal_page_last               o1617
_journal_paper_doi               10.1107/S1600536806010294
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C18 H20 N2 O3'
_chemical_formula_sum            'C18 H20 N2 O3'
_chemical_formula_weight         312.36
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.086(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6894(4)
_cell_length_b                   11.2312(8)
_cell_length_c                   10.2511(9)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     1514.38(18)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL (Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.1038
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9870
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0543
_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)+(0.0822P)²+0.0395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1610
_reflns_number_gt                1688
_reflns_number_total             2660
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2038.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

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

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208527
_cod_database_fobs_code          2208527
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
O O1 0.22279(13) 0.45475(16) 0.53599(16) 0.0370(5) Uani d . 1
O O2 0.19004(13) 0.68847(16) 0.88498(17) 0.0368(5) Uani d . 1
O O3 0.76076(15) 0.71153(18) 0.66244(18) 0.0407(5) Uani d . 1
N N1 0.20533(15) 0.57393(18) 0.70837(19) 0.0277(5) Uani d . 1
N N2 0.69569(16) 0.53328(18) 0.83712(19) 0.0300(5) Uani d . 1
C C1 0.26501(19) 0.5120(2) 0.6392(2) 0.0276(6) Uani d . 1
C C2 0.37495(18) 0.5188(2) 0.6932(2) 0.0241(6) Uani d . 1
C C3 0.43682(19) 0.4551(2) 0.6329(2) 0.0272(6) Uani d . 1
H H3B 0.4066 0.4072 0.5558 0.033 Uiso calc R 1
C C4 0.5420(2) 0.4589(2) 0.6818(2) 0.0282(6) Uani d . 1
H H4A 0.5819 0.4122 0.6387 0.034 Uiso calc R 1
C C5 0.59059(18) 0.5296(2) 0.7926(2) 0.0251(6) Uani d . 1
C C6 0.52793(19) 0.5914(2) 0.8642(2) 0.0241(6) Uani d . 1
C C7 0.56732(18) 0.6485(2) 0.9909(2) 0.0253(6) Uani d . 1
H H7A 0.6385 0.6469 1.0326 0.030 Uiso calc R 1
C C8 0.50533(19) 0.7061(2) 1.0552(2) 0.0269(6) Uani d . 1
H H8A 0.5341 0.7459 1.1388 0.032 Uiso calc R 1
C C9 0.40037(19) 0.7062(2) 0.9982(2) 0.0254(6) Uani d . 1
H H9A 0.3580 0.7485 1.0416 0.030 Uiso calc R 1
C C10 0.35774(18) 0.6453(2) 0.8792(2) 0.0241(6) Uani d . 1
C C11 0.24646(19) 0.6396(2) 0.8272(2) 0.0276(6) Uani d . 1
C C12 0.42023(18) 0.5866(2) 0.8103(2) 0.0240(6) Uani d . 1
C C13 0.09246(19) 0.5648(2) 0.6543(3) 0.0334(7) Uani d . 1
H H13A 0.0794 0.5165 0.5693 0.040 Uiso calc R 1
C C14 0.0424(2) 0.6849(3) 0.6123(3) 0.0434(7) Uani d . 1
H H14A 0.0744 0.7238 0.5491 0.065 Uiso calc R 1
H H14B 0.0506 0.7351 0.6928 0.065 Uiso calc R 1
H H14C -0.0302 0.6733 0.5678 0.065 Uiso calc R 1
C C15 0.0473(2) 0.4947(3) 0.7503(3) 0.0420(7) Uani d . 1
H H15A 0.0856 0.4206 0.7763 0.063 Uiso calc R 1
H H15B -0.0239 0.4759 0.7049 0.063 Uiso calc R 1
H H15C 0.0512 0.5422 0.8317 0.063 Uiso calc R 1
C C16 0.7539(2) 0.4374(2) 0.7983(3) 0.0365(7) Uani d . 1
H H16A 0.7199 0.3612 0.8017 0.055 Uiso calc R 1
H H16B 0.8224 0.4354 0.8612 0.055 Uiso calc R 1
H H16C 0.7586 0.4513 0.7058 0.055 Uiso calc R 1
C C17 0.75225(18) 0.6433(2) 0.8830(2) 0.0296(6) Uani d . 1
H H17A 0.7956 0.6315 0.9770 0.035 Uiso calc R 1
H H17B 0.7032 0.7075 0.8852 0.035 Uiso calc R 1
C C18 0.81877(19) 0.6831(2) 0.7953(2) 0.0317(6) Uani d . 1
H H18A 0.8586 0.7537 0.8370 0.038 Uiso calc R 1
H H18B 0.8673 0.6187 0.7913 0.038 Uiso calc R 1
H H3O 0.758(2) 0.650(3) 0.602(3) 0.061(10) Uiso 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'
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
C18 O3 H3O 113(2) ?
C11 N1 C1 123.3(2) y
C11 N1 C13 118.9(2) y
C1 N1 C13 117.75(19) y
C5 N2 C16 119.0(2) y
C5 N2 C17 122.6(2) y
C16 N2 C17 115.5(2) y
O1 C1 N1 119.3(2) ?
O1 C1 C2 122.8(2) ?
N1 C1 C2 117.9(2) ?
C3 C2 C12 118.8(2) ?
C3 C2 C1 120.1(2) ?
C12 C2 C1 121.1(2) ?
C2 C3 C4 121.7(2) ?
C2 C3 H3B 119.1 ?
C4 C3 H3B 119.1 ?
C3 C4 C5 121.7(2) ?
C3 C4 H4A 119.2 ?
C5 C4 H4A 119.2 ?
N2 C5 C4 120.2(2) ?
N2 C5 C6 121.7(2) ?
C4 C5 C6 118.0(2) ?
C7 C6 C12 117.6(2) ?
C7 C6 C5 123.6(2) ?
C12 C6 C5 118.6(2) ?
C8 C7 C6 121.7(2) ?
C8 C7 H7A 119.2 ?
C6 C7 H7A 119.2 ?
C7 C8 C9 120.2(2) ?
C7 C8 H8A 119.9 ?
C9 C8 H8A 119.9 ?
C10 C9 C8 120.3(2) ?
C10 C9 H9A 119.9 ?
C8 C9 H9A 119.9 ?
C9 C10 C12 120.4(2) ?
C9 C10 C11 118.9(2) ?
C12 C10 C11 120.6(2) ?
O2 C11 N1 120.0(2) ?
O2 C11 C10 122.3(2) ?
N1 C11 C10 117.6(2) ?
C2 C12 C10 119.5(2) ?
C2 C12 C6 120.9(2) ?
C10 C12 C6 119.5(2) ?
N1 C13 C15 111.1(2) ?
N1 C13 C14 112.5(2) ?
C15 C13 C14 114.3(2) ?
N1 C13 H13A 106.1 ?
C15 C13 H13A 106.1 ?
C14 C13 H13A 106.1 ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C13 C15 H15A 109.5 ?
C13 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C13 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N2 C16 H16A 109.5 ?
N2 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
N2 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
N2 C17 C18 114.2(2) ?
N2 C17 H17A 108.7 ?
C18 C17 H17A 108.7 ?
N2 C17 H17B 108.7 ?
C18 C17 H17B 108.7 ?
H17A C17 H17B 107.6 ?
O3 C18 C17 111.7(2) ?
O3 C18 H18A 109.3 ?
C17 C18 H18A 109.3 ?
O3 C18 H18B 109.3 ?
C17 C18 H18B 109.3 ?
H18A C18 H18B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.237(3) ?
O2 C11 1.225(3) ?
O3 C18 1.410(3) ?
O3 H3O 0.92(3) ?
N1 C11 1.402(3) y
N1 C1 1.405(3) y
N1 C13 1.493(3) y
N2 C5 1.384(3) y
N2 C16 1.459(3) y
N2 C17 1.465(3) y
C1 C2 1.455(4) ?
C2 C3 1.380(3) ?
C2 C12 1.412(3) ?
C3 C4 1.388(4) ?
C3 H3B 0.9500 ?
C4 C5 1.395(3) ?
C4 H4A 0.9500 ?
C5 C6 1.451(3) ?
C6 C7 1.414(3) ?
C6 C12 1.425(3) ?
C7 C8 1.372(3) ?
C7 H7A 0.9500 ?
C8 C9 1.393(3) ?
C8 H8A 0.9500 ?
C9 C10 1.380(3) ?
C9 H9A 0.9500 ?
C10 C12 1.414(3) ?
C10 C11 1.469(3) ?
C13 C15 1.519(4) ?
C13 C14 1.520(4) ?
C13 H13A 1.0000 ?
C14 H14A 0.9800 ?
C14 H14B 0.9800 ?
C14 H14C 0.9800 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 0.9800 ?
C16 H16A 0.9800 ?
C16 H16B 0.9800 ?
C16 H16C 0.9800 ?
C17 C18 1.514(3) ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C18 H18A 0.9900 ?
C18 H18B 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
O3 H3O O1 3_666 0.92(3) 1.92(3) 2.816(3) 166(3)
C7 H7A O3 4_576 0.95 2.42 3.162(3) 135
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128577
2 PubChem 58077940
