#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/73/2007304.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_2007304
loop_
_publ_author_name
'Kandasamy Chinnakali'
'Hoong-Kun Fun'
'Ibrahim Abdul Razak'
'Periyasamy Murugan'
'Vayalakkavoor T.Ramakrishnan'
_publ_section_title
;
 5-Amino-2,4-diphenyl-7-(pyrrolidin-1-yl)-1,6-naphthyridine-8-carbonitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              781
_journal_page_last               783
_journal_paper_doi               10.1107/S0108270197019574
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C25 H21 N5'
_chemical_formula_sum            'C25 H21 N5'
_chemical_formula_weight         391.47
_chemical_melting_point          509.1(10)
_chemical_name_systematic
;
5-Amino-8-cyano-2,4-diphenyl-7-(pyrrolidin-1yl)-1,6-naphthyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                98.956(7)
_cell_angle_beta                 109.026(6)
_cell_angle_gamma                103.602(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0996(7)
_cell_length_b                   10.9985(9)
_cell_length_c                   11.3214(8)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.478
_cell_measurement_theta_min      5.412
_cell_volume                     1007.29(15)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL93, PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       'θ/2θ scans'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5406
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.158
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_method     SHELXL93_(Sheldrick,_1993)
_refine_ls_goodness_of_fit_all   0.938
_refine_ls_goodness_of_fit_obs   1.078
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4560
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.938
_refine_ls_restrained_S_obs      1.078
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_obs          .0448
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0804P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1341
_refine_ls_wR_factor_obs         .1207
_reflns_number_observed          2916
_reflns_number_total             4560
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            bm1213.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '235-237\%C' was changed to
'509.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '235-237\%C' was changed to
'509.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0804P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0804P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1007.3(2)
_cod_database_code               2007304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .29046(14) .00214(11) .10055(11) .0436(3) Uani d . 1 . N
C2 .1710(2) -.10248(13) .08607(13) .0434(3) Uani d . 1 . C
C3 .0538(2) -.17446(14) -.03518(14) .0483(4) Uani d . 1 . C
C4 .0598(2) -.14131(13) -.14615(13) .0433(3) Uani d . 1 . C
C5 .2074(2) .02632(14) -.23656(14) .0468(3) Uani d . 1 . C
N6 .32043(15) .13653(12) -.21590(12) .0502(3) Uani d . 1 . N
C7 .4264(2) .20332(14) -.09440(14) .0441(3) Uani d . 1 . C
C8 .4196(2) .15765(13) .01352(13) .0433(3) Uani d . 1 . C
C9 .2956(2) .04056(13) -.00706(12) .0402(3) Uani d . 1 . C
C10 .1841(2) -.02860(13) -.13346(13) .0408(3) Uani d . 1 . C
N11 .1104(2) -.0303(2) -.36157(13) .0680(5) Uani d . 1 . N
C12 .5218(2) .2243(2) .1448(2) .0529(4) Uani d . 1 . C
N13 .6008(2) .2772(2) .25034(14) .0799(5) Uani d . 1 . N
N14 .5331(2) .31447(13) -.08964(13) .0547(3) Uani d . 1 . N
C15 .5196(3) .3639(2) -.2056(2) .0664(5) Uani d D 1 . C
C16A .6618(8) .4897(6) -.1520(7) .076(2) Uani d PDU .60 1 C
H16A .7019(8) .5110(6) -.2181(7) .092 Uiso calc PR .60 1 H
H16B .6296(8) .5610(6) -.1175(7) .092 Uiso calc PR .60 1 H
C17A .7880(4) .4597(4) -.0472(4) .0713(10) Uani d PDU .60 1 C
H17A .8718(4) .5377(4) .0112(4) .086 Uiso calc PR .60 1 H
H17B .8386(4) .4026(4) -.0822(4) .086 Uiso calc PR .60 1 H
C16B .6882(12) .4539(9) -.1732(10) .074(3) Uani d PDU .40 2 C
H16C .6856(12) .5199(9) -.2210(10) .089 Uiso calc PR .40 2 H
H16D .7611(12) .4074(9) -.1889(10) .089 Uiso calc PR .40 2 H
C17B .7355(7) .5108(5) -.0298(5) .0661(13) Uani d PDU .40 2 C
H17C .8524(7) .5525(5) .0128(5) .079 Uiso calc PR .40 2 H
H17D .6792(7) .5730(5) -.0158(5) .079 Uiso calc PR .40 2 H
C18 .6809(2) .3920(2) .0195(2) .0644(5) Uani d D 1 . C
C19 .1732(2) -.14280(13) .20612(14) .0461(3) Uani d . 1 . C
C20 .3202(2) -.1110(2) .3107(2) .0569(4) Uani d . 1 . C
C21 .3245(3) -.1534(2) .4206(2) .0672(5) Uani d . 1 . C
C22 .1843(3) -.2277(2) .4270(2) .0722(5) Uani d . 1 . C
C23 .0379(3) -.2573(2) .3253(2) .0721(5) Uani d . 1 . C
C24 .0318(2) -.2145(2) .2153(2) .0580(4) Uani d . 1 . C
C25 -.0635(2) -.23134(13) -.27103(13) .0434(3) Uani d . 1 . C
C26 -.2221(2) -.2248(2) -.3188(2) .0614(4) Uani d . 1 . C
C27 -.3383(2) -.3145(2) -.4290(2) .0706(5) Uani d . 1 . C
C28 -.2988(2) -.4110(2) -.4926(2) .0607(4) Uani d . 1 . C
C29 -.1446(2) -.4205(2) -.4441(2) .0594(4) Uani d . 1 . C
C30 -.0266(2) -.3314(2) -.3341(2) .0549(4) Uani d . 1 . C
H3 -.0273(19) -.2509(16) -.0403(15) .058(4) Uiso d . 1 . H
H11A .145(2) -.0009(18) -.4128(18) .068(6) Uiso d . 1 . H
H11B .032(3) -.115(3) -.389(2) .112(8) Uiso d . 1 . H
H15A .418(3) .395(2) -.231(2) .095(7) Uiso d . 1 . H
H15B .512(3) .299(2) -.273(2) .088(7) Uiso d . 1 . H
H18A .662(3) .443(2) .090(2) .103(8) Uiso d . 1 . H
H18B .743(3) .336(2) .0542(19) .086(7) Uiso d . 1 . H
H20 .420(2) -.0627(17) .3043(16) .063(5) Uiso d . 1 . H
H21 .418(2) -.1373(19) .486(2) .081(6) Uiso d . 1 . H
H22 .189(2) -.256(2) .501(2) .087(6) Uiso d . 1 . H
H23 -.062(3) -.311(2) .3308(19) .086(6) Uiso d . 1 . H
H24 -.069(2) -.2323(17) .1483(17) .070(5) Uiso d . 1 . H
H26 -.249(2) -.156(2) -.2708(19) .085(6) Uiso d . 1 . H
H27 -.461(2) -.3143(19) -.4651(19) .087(6) Uiso d . 1 . H
H28 -.382(2) -.4767(17) -.5720(17) .065(5) Uiso d . 1 . H
H29 -.118(2) -.488(2) -.492(2) .081(6) Uiso d . 1 . H
H30 .081(2) -.3362(18) -.2977(17) .075(6) Uiso d . 1 . H
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'
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
C2 N1 C9 118.12(12) ?
N1 C2 C3 122.29(13) ?
N1 C2 C19 116.13(12) ?
C3 C2 C19 121.52(13) ?
C4 C3 C2 120.97(13) ?
C3 C4 C10 117.94(13) ?
C3 C4 C25 116.36(12) ?
C10 C4 C25 125.66(12) ?
N6 C5 N11 115.15(14) ?
N6 C5 C10 123.07(13) ?
N11 C5 C10 121.75(14) ?
C5 N6 C7 121.13(12) ?
N14 C7 N6 113.84(13) ?
N14 C7 C8 125.02(13) yes
N6 C7 C8 121.14(12) ?
C7 C8 C9 118.32(12) ?
C7 C8 C12 124.74(13) ?
C9 C8 C12 116.81(12) ?
N1 C9 C10 123.06(12) ?
N1 C9 C8 116.29(12) ?
C10 C9 C8 120.64(12) ?
C9 C10 C4 117.53(12) ?
C9 C10 C5 115.64(12) ?
C4 C10 C5 126.81(12) yes
N13 C12 C8 178.6(2) ?
C7 N14 C18 126.79(14) ?
C7 N14 C15 121.68(14) ?
C18 N14 C15 111.20(13) ?
C16B C15 N14 104.1(5) ?
N14 C15 C16A 102.3(3) ?
C17A C16A C15 103.2(5) ?
C16A C17A C18 100.4(4) ?
C15 C16B C17B 100.0(6) ?
C18 C17B C16B 103.4(5) ?
N14 C18 C17B 101.5(2) ?
N14 C18 C17A 102.3(2) ?
C24 C19 C20 118.82(15) ?
C24 C19 C2 121.45(14) ?
C20 C19 C2 119.71(14) ?
C21 C20 C19 120.0(2) ?
C22 C21 C20 120.5(2) ?
C23 C22 C21 119.8(2) ?
C22 C23 C24 120.2(2) ?
C19 C24 C23 120.5(2) ?
C30 C25 C26 118.48(14) ?
C30 C25 C4 120.46(13) ?
C26 C25 C4 120.72(14) ?
C27 C26 C25 120.3(2) ?
C28 C27 C26 120.6(2) ?
C29 C28 C27 119.5(2) ?
C28 C29 C30 120.7(2) ?
C29 C30 C25 120.4(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.330(2) yes
N1 C9 . 1.361(2) yes
C2 C3 . 1.399(2) yes
C2 C19 . 1.489(2) ?
C3 C4 . 1.376(2) yes
C4 C10 . 1.420(2) yes
C4 C25 . 1.498(2) ?
C5 N6 . 1.323(2) yes
C5 N11 . 1.350(2) ?
C5 C10 . 1.447(2) yes
N6 C7 . 1.360(2) yes
C7 N14 . 1.352(2) ?
C7 C8 . 1.405(2) yes
C8 C9 . 1.427(2) yes
C8 C12 . 1.432(2) ?
C9 C10 . 1.417(2) yes
C12 N13 . 1.144(2) ?
N14 C18 . 1.453(2) ?
N14 C15 . 1.477(2) ?
C15 C16B . 1.508(10) ?
C15 C16A . 1.530(7) ?
C16A C17A . 1.499(8) ?
C17A C18 . 1.546(4) ?
C16B C17B . 1.521(10) ?
C17B C18 . 1.539(5) ?
C19 C24 . 1.387(2) ?
C19 C20 . 1.390(2) ?
C20 C21 . 1.388(2) ?
C21 C22 . 1.374(3) ?
C22 C23 . 1.373(3) ?
C23 C24 . 1.388(2) ?
C25 C30 . 1.385(2) ?
C25 C26 . 1.390(2) ?
C26 C27 . 1.384(2) ?
C27 C28 . 1.372(3) ?
C28 C29 . 1.367(3) ?
C29 C30 . 1.385(2) ?
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
C9 N1 C2 C3 1.2(2)
C9 N1 C2 C19 178.34(12)
N1 C2 C3 C4 1.6(2)
C19 C2 C3 C4 -175.43(14)
C2 C3 C4 C10 -2.7(2)
C2 C3 C4 C25 175.13(13)
N11 C5 N6 C7 -179.83(15)
C10 C5 N6 C7 2.2(2)
C5 N6 C7 N14 -179.33(13)
C5 N6 C7 C8 0.0(2)
N14 C7 C8 C9 177.70(13)
N6 C7 C8 C9 -1.6(2)
N14 C7 C8 C12 1.9(2)
N6 C7 C8 C12 -177.34(14)
C2 N1 C9 C10 -2.7(2)
C2 N1 C9 C8 176.25(12)
C7 C8 C9 N1 -178.02(12)
C12 C8 C9 N1 -1.9(2)
C7 C8 C9 C10 1.0(2)
C12 C8 C9 C10 177.08(13)
N1 C9 C10 C4 1.5(2)
C8 C9 C10 C4 -177.43(13)
N1 C9 C10 C5 179.91(13)
C8 C9 C10 C5 1.0(2)
C3 C4 C10 C9 1.3(2)
C25 C4 C10 C9 -176.40(13)
C3 C4 C10 C5 -176.96(14)
C25 C4 C10 C5 5.4(2)
N6 C5 C10 C9 -2.6(2)
N11 C5 C10 C9 179.51(15)
N6 C5 C10 C4 175.62(14)
N11 C5 C10 C4 -2.2(2)
C7 C8 C12 N13 132.(8)
C9 C8 C12 N13 -44.(8)
N6 C7 N14 C18 -165.8(2)
C8 C7 N14 C18 14.9(3)
N6 C7 N14 C15 7.0(2)
C8 C7 N14 C15 -172.4(2)
C7 N14 C15 C16B -159.0(4)
C18 N14 C15 C16B 14.8(4)
C7 N14 C15 C16A 179.0(3)
C18 N14 C15 C16A -7.2(3)
C16B C15 C16A C17A -64.6(17)
N14 C15 C16A C17A 32.8(4)
C15 C16A C17A C18 -44.9(4)
N14 C15 C16B C17B -35.9(6)
C16A C15 C16B C17B 51.7(15)
C15 C16B C17B C18 44.4(7)
C7 N14 C18 C17B -173.8(3)
C15 N14 C18 C17B 12.8(3)
C7 N14 C18 C17A 153.2(2)
C15 N14 C18 C17A -20.2(3)
C16B C17B C18 N14 -35.5(5)
C16B C17B C18 C17A 59.3(6)
C16A C17A C18 N14 39.7(4)
C16A C17A C18 C17B -52.5(5)
N1 C2 C19 C24 155.11(14)
C3 C2 C19 C24 -27.7(2)
N1 C2 C19 C20 -26.4(2)
C3 C2 C19 C20 150.8(2)
C24 C19 C20 C21 1.5(2)
C2 C19 C20 C21 -177.0(2)
C19 C20 C21 C22 0.5(3)
C20 C21 C22 C23 -1.8(3)
C21 C22 C23 C24 1.2(3)
C20 C19 C24 C23 -2.1(2)
C2 C19 C24 C23 176.3(2)
C22 C23 C24 C19 0.8(3)
C3 C4 C25 C30 -91.8(2)
C10 C4 C25 C30 85.9(2)
C3 C4 C25 C26 81.4(2)
C10 C4 C25 C26 -100.9(2)
C30 C25 C26 C27 -1.9(3)
C4 C25 C26 C27 -175.1(2)
C25 C26 C27 C28 0.0(3)
C26 C27 C28 C29 2.0(3)
C27 C28 C29 C30 -2.1(3)
C28 C29 C30 C25 0.3(3)
C26 C25 C30 C29 1.7(2)
C4 C25 C30 C29 175.00(14)
