#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:44:50 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179672 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/25/4512571.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_4512571
loop_
_publ_author_name
'Nath, Jayanta K.'
'Kirillov, Alexander M.'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Synthesis, Structure, and Topological Studies of Solvates and Salts of a
 Chiral Zwitterionic
 HostN-(2-Imidazol-5-yl-1-carboxyethyl)-1,8-naphthalimide
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              737
_journal_paper_doi               10.1021/cg5018054
_journal_volume                  15
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H13 N3 O4, C2 H6 O S'
_chemical_formula_sum            'C20 H19 N3 O5 S'
_chemical_formula_weight         413.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1474(3)
_cell_length_b                   9.1474(3)
_cell_length_c                   45.447(2)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.8059
_cell_measurement_theta_min      3.1313
_cell_volume                     3802.8(2)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            7589
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         3.15
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0631
_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)+(0.0777P)²+2.9612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                1857
_reflns_number_total             2099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5018054_si_004.cif
_cod_data_source_block           L.DMSO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4512567--4512578.cif.
;
_cod_original_cell_volume        3802.8(3)
_cod_database_code               4512571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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
S1 S 0.36215(18) 0.33044(17) 0.45729(3) 0.0669(4) Uani 1 1 d .
O2 O 0.9886(3) 0.6950(3) 0.40285(6) 0.0366(7) Uani 1 1 d .
O4 O 0.9155(3) 1.0039(3) 0.40044(6) 0.0398(7) Uani 1 1 d .
O1 O 0.9026(3) 0.7054(3) 0.35694(6) 0.0386(7) Uani 1 1 d .
N3 N 0.7502(3) 0.8561(4) 0.42298(7) 0.0274(7) Uani 1 1 d .
O3 O 0.5799(4) 0.7116(4) 0.44519(7) 0.0501(9) Uani 1 1 d .
N2 N 0.4277(3) 0.9625(4) 0.39834(7) 0.0320(8) Uani 1 1 d .
H2A H 0.4732 1.0415 0.4029 0.038 Uiso 1 1 calc R
N1 N 0.2571(4) 0.8001(4) 0.39481(7) 0.0364(8) Uani 1 1 d .
H1A H 0.1744 0.7563 0.3965 0.044 Uiso 1 1 calc R
C6 C 0.8926(4) 0.7231(4) 0.38411(9) 0.0305(9) Uani 1 1 d .
C18 C 0.8479(4) 0.9729(4) 0.42314(8) 0.0292(8) Uani 1 1 d .
C3 C 0.4854(4) 0.8481(4) 0.38233(8) 0.0303(8) Uani 1 1 d .
C1 C 0.2909(4) 0.9310(5) 0.40549(9) 0.0346(9) Uani 1 1 d .
H1 H 0.2286 0.9909 0.4163 0.042 Uiso 1 1 calc R
C7 C 0.6634(4) 0.8150(5) 0.44711(8) 0.0329(9) Uani 1 1 d .
C5 C 0.7391(4) 0.7685(4) 0.39562(8) 0.0260(8) Uani 1 1 d .
H5 H 0.6895 0.6775 0.4011 0.031 Uiso 1 1 calc R
O5 O 0.3293(6) 0.1809(5) 0.44589(10) 0.0917(15) Uani 1 1 d .
C2 C 0.3785(4) 0.7475(5) 0.38057(9) 0.0363(10) Uani 1 1 d .
H2 H 0.3857 0.6573 0.3712 0.044 Uiso 1 1 calc R
C4 C 0.6420(4) 0.8416(4) 0.37261(8) 0.0299(8) Uani 1 1 d .
H4B H 0.6772 0.9400 0.3690 0.036 Uiso 1 1 calc R
H4A H 0.6484 0.7875 0.3543 0.036 Uiso 1 1 calc R
C13 C 0.7823(5) 1.0157(4) 0.47579(8) 0.0337(9) Uani 1 1 d .
C8 C 0.6799(5) 0.9014(5) 0.47423(8) 0.0357(10) Uani 1 1 d .
C17 C 0.8663(4) 1.0527(4) 0.45122(9) 0.0330(9) Uani 1 1 d .
C9 C 0.5960(6) 0.8653(5) 0.49856(10) 0.0490(12) Uani 1 1 d .
H9 H 0.5268 0.7910 0.4974 0.059 Uiso 1 1 calc R
C16 C 0.9700(5) 1.1624(5) 0.45317(10) 0.0450(11) Uani 1 1 d .
H16 H 1.0257 1.1860 0.4367 0.054 Uiso 1 1 calc R
C12 C 0.8028(5) 1.0926(5) 0.50292(9) 0.0448(11) Uani 1 1 d .
C11 C 0.7158(7) 1.0512(6) 0.52713(10) 0.0598(15) Uani 1 1 d .
H11 H 0.7270 1.1003 0.5449 0.072 Uiso 1 1 calc R
C10 C 0.6165(6) 0.9423(6) 0.52523(10) 0.0562(14) Uani 1 1 d .
H10 H 0.5610 0.9176 0.5416 0.067 Uiso 1 1 calc R
C15 C 0.9922(6) 1.2382(6) 0.47955(12) 0.0599(14) Uani 1 1 d .
H15 H 1.0624 1.3116 0.4807 0.072 Uiso 1 1 calc R
C14 C 0.9093(6) 1.2032(6) 0.50385(11) 0.0576(14) Uani 1 1 d .
H14 H 0.9241 1.2541 0.5213 0.069 Uiso 1 1 calc R
C20 C 0.5535(7) 0.3451(7) 0.46103(14) 0.0798(18) Uani 1 1 d .
H20A H 0.5853 0.2868 0.4774 0.120 Uiso 1 1 calc R
H20B H 0.5795 0.4454 0.4644 0.120 Uiso 1 1 calc R
H20C H 0.5999 0.3111 0.4434 0.120 Uiso 1 1 calc R
C19 C 0.3512(8) 0.4384(8) 0.42694(13) 0.087(2) Uani 1 1 d .
H19A H 0.4179 0.4032 0.4122 0.130 Uiso 1 1 calc R
H19B H 0.3763 0.5370 0.4321 0.130 Uiso 1 1 calc R
H19C H 0.2534 0.4359 0.4193 0.130 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
O5 S1 C19 103.8(3)
O5 S1 C20 107.6(3)
C19 S1 C20 95.3(3)
C18 N3 C7 124.3(3)
C18 N3 C5 117.6(3)
C7 N3 C5 118.1(3)
C1 N2 C3 109.0(3)
C1 N1 C2 107.5(3)
O1 C6 O2 126.5(4)
O1 C6 C5 115.7(3)
O2 C6 C5 117.4(3)
O4 C18 N3 119.5(3)
O4 C18 C17 123.4(4)
N3 C18 C17 117.1(3)
C2 C3 N2 105.8(3)
C2 C3 C4 130.5(4)
N2 C3 C4 123.4(3)
N2 C1 N1 109.0(3)
O3 C7 N3 120.4(4)
O3 C7 C8 122.7(4)
N3 C7 C8 116.8(4)
N3 C5 C4 112.2(3)
N3 C5 C6 111.4(3)
C4 C5 C6 114.3(3)
C3 C2 N1 108.7(4)
C3 C4 C5 111.8(3)
C17 C13 C8 120.4(4)
C17 C13 C12 119.8(4)
C8 C13 C12 119.8(4)
C9 C8 C13 120.4(4)
C9 C8 C7 118.9(4)
C13 C8 C7 120.7(4)
C16 C17 C13 120.1(4)
C16 C17 C18 119.4(4)
C13 C17 C18 120.5(4)
C8 C9 C10 119.5(5)
C17 C16 C15 120.9(5)
C14 C12 C11 124.1(5)
C14 C12 C13 118.1(4)
C11 C12 C13 117.8(5)
C10 C11 C12 121.9(5)
C11 C10 C9 120.7(5)
C14 C15 C16 119.4(5)
C15 C14 C12 121.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.493(4)
S1 C19 1.699(7)
S1 C20 1.764(6)
O2 C6 1.250(5)
O4 C18 1.235(5)
O1 C6 1.249(5)
N3 C18 1.393(5)
N3 C7 1.405(5)
N3 C5 1.483(5)
O3 C7 1.218(5)
N2 C1 1.324(5)
N2 C3 1.380(5)
N1 C1 1.329(5)
N1 C2 1.372(5)
C6 C5 1.555(5)
C18 C17 1.480(5)
C3 C2 1.345(5)
C3 C4 1.500(5)
C7 C8 1.472(6)
C5 C4 1.526(5)
C13 C17 1.397(6)
C13 C8 1.405(6)
C13 C12 1.432(5)
C8 C9 1.386(6)
C17 C16 1.383(6)
C9 C10 1.414(7)
C16 C15 1.400(6)
C12 C14 1.405(7)
C12 C11 1.410(7)
C11 C10 1.351(8)
C15 C14 1.377(8)
