#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/96/2019688.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_2019688
loop_
_publ_author_name
'Nayak, Prakash S.'
'Narayana, Badiadka'
'Yathirajan, Hemmige S.'
'Hosten, Eric C.'
'Betz, Richard'
'Glidewell, Christopher'
_publ_section_title
;
 (2E)-3-(6-Methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one
 and its cyclocondensation product with guanidine,
 (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine
 monohydrate: two types of hydrogen-bonded sheet
;
_journal_coeditor_code           SK3565
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1011
_journal_page_last               1016
_journal_paper_doi               10.1107/S2053229614021524
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H18 N4 O , H2 O'
_chemical_formula_moiety         'C20 H18 N4 O, H2 O'
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40
_chemical_name_systematic
'(RS)-2-Amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL2014
_cell_angle_alpha                90
_cell_angle_beta                 112.8300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2244(5)
_cell_length_b                   5.9552(2)
_cell_length_c                   18.5173(6)
_cell_measurement_reflns_used    4319
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.289
_cell_measurement_theta_min      2.228
_cell_volume                     1750.61(10)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009) and SHELXL2014 (Sheldrick, 2014)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         2.228
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.539
_exptl_crystal_size_min          0.317
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0554P)²+0.5610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                3596
_reflns_number_total             4319
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3565sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2019687--2019688.cif.'
_cod_database_code               2019688
_cod_database_fobs_code          2019688
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2.014
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_occupancy
N N1 0.89139(6) 0.52266(17) 0.41737(5) 0.0298(2) Uani d 1
C C2 0.87565(7) 0.3476(2) 0.45317(6) 0.0277(2) Uani d 1
N N3 0.80838(6) 0.21208(18) 0.42197(6) 0.0316(2) Uani d 1
H H3 0.8063 0.0906 0.4520 0.038 Uiso d 1
C C4 0.73670(7) 0.2640(2) 0.34898(7) 0.0314(3) Uani d 1
H H4 0.7175 0.1223 0.3182 0.038 Uiso calc 1
C C5 0.76718(7) 0.4235(2) 0.30296(7) 0.0326(3) Uani d 1
H H5 0.7360 0.4394 0.2482 0.039 Uiso calc 1
C C6 0.83758(7) 0.5437(2) 0.33777(6) 0.0286(2) Uani d 1
N N21 0.92997(6) 0.29906(19) 0.52711(6) 0.0340(2) Uani d 1
H H211 0.9280 0.1599 0.5450 0.041 Uiso d 1
H H212 0.9812 0.3593 0.5417 0.041 Uiso d 1
C C41 0.58418(7) 0.2716(2) 0.33298(7) 0.0313(3) Uani d 1
H H41 0.5752 0.1391 0.3023 0.038 Uiso calc 1
C C42 0.66312(7) 0.3639(2) 0.36432(7) 0.0308(3) Uani d 1
C C43 0.67574(8) 0.5617(2) 0.40969(9) 0.0421(3) Uani d 1
H H43 0.7302 0.6276 0.4311 0.051 Uiso calc 1
C C44 0.61107(8) 0.6597(3) 0.42323(9) 0.0455(3) Uani d 1
H H44 0.6213 0.7918 0.4543 0.055 Uiso calc 1
C C44a 0.52881(7) 0.5675(2) 0.39167(7) 0.0344(3) Uani d 1
C C45 0.46096(8) 0.6671(2) 0.40564(8) 0.0405(3) Uani d 1
H H45 0.4701 0.7986 0.4369 0.049 Uiso calc 1
C C46 0.38268(8) 0.5734(3) 0.37404(8) 0.0404(3) Uani d 1
C C47 0.36847(8) 0.3804(3) 0.32683(9) 0.0446(3) Uani d 1
H H47 0.3134 0.3188 0.3042 0.054 Uiso calc 1
C C48 0.43269(8) 0.2804(3) 0.31298(8) 0.0406(3) Uani d 1
H H48 0.4220 0.1494 0.2813 0.049 Uiso calc 1
C C48a 0.51539(7) 0.3709(2) 0.34562(7) 0.0311(3) Uani d 1
O O146 0.31249(6) 0.6528(2) 0.38374(7) 0.0538(3) Uani d 1
C C146 0.32473(11) 0.8329(3) 0.43708(10) 0.0573(4) Uani d 1
H H46A 0.2715 0.8665 0.4425 0.086 Uiso calc 1
H H46B 0.3438 0.9659 0.4174 0.086 Uiso calc 1
H H46C 0.3674 0.7908 0.4883 0.086 Uiso calc 1
N N61 0.87654(7) 0.8262(2) 0.17333(7) 0.0429(3) Uani d 1
C C62 0.85457(8) 0.6778(2) 0.21618(7) 0.0356(3) Uani d 1
H H62 0.8297 0.5405 0.1921 0.043 Uiso calc 1
C C63 0.86594(7) 0.7125(2) 0.29423(6) 0.0293(2) Uani d 1
C C64 0.90497(7) 0.9109(2) 0.32890(7) 0.0331(3) Uani d 1
H H64 0.9159 0.9400 0.3824 0.040 Uiso calc 1
C C65 0.92794(9) 1.0666(2) 0.28517(8) 0.0402(3) Uani d 1
H H65 0.9539 1.2042 0.3079 0.048 Uiso calc 1
C C66 0.91230(9) 1.0179(3) 0.20805(9) 0.0437(3) Uani d 1
H H66 0.9276 1.1256 0.1781 0.052 Uiso calc 1
O O71 0.86814(7) -0.15413(16) 0.53121(6) 0.0436(2) Uani d 1
H H711 0.8726 -0.2222 0.5751 0.065 Uiso d 1
H H712 0.8813 -0.2572 0.5020 0.065 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
C2 N1 C6 114.59(10) ?
N1 C2 N3 124.70(10) ?
N1 C2 N21 118.69(10) ?
N3 C2 N21 116.61(10) ?
C2 N3 C4 123.13(10) ?
C2 N3 H3 116.1 ?
C4 N3 H3 120.3 ?
N3 C4 C5 107.56(9) ?
N3 C4 C42 111.98(10) ?
C5 C4 C42 111.00(10) ?
N3 C4 H4 108.7 ?
C5 C4 H4 108.7 ?
C42 C4 H4 108.7 ?
C6 C5 C4 121.08(10) ?
C6 C5 H5 119.5 ?
C4 C5 H5 119.5 ?
C5 C6 N1 124.13(11) ?
C5 C6 C63 121.87(10) ?
N1 C6 C63 114.00(10) ?
C2 N21 H211 117.3 ?
C2 N21 H212 115.8 ?
H211 N21 H212 115.8 ?
C42 C41 C48a 121.14(11) ?
C42 C41 H41 119.4 ?
C48a C41 H41 119.4 ?
C41 C42 C43 118.98(11) ?
C41 C42 C4 121.70(11) ?
C43 C42 C4 119.28(10) ?
C44 C43 C42 121.15(12) ?
C44 C43 H43 119.4 ?
C42 C43 H43 119.4 ?
C43 C44 C44a 121.04(13) ?
C43 C44 H44 119.5 ?
C44a C44 H44 119.5 ?
C48a C44a C44 118.23(11) ?
C48a C44a C45 120.15(11) ?
C44 C44a C45 121.63(12) ?
C46 C45 C44a 119.80(13) ?
C46 C45 H45 120.1 ?
C44a C45 H45 120.1 ?
C45 C46 O146 125.24(14) y
C45 C46 C47 120.38(12) ?
C47 C46 O146 114.39(12) y
C48 C47 C46 120.99(12) ?
C48 C47 H47 119.5 ?
C46 C47 H47 119.5 ?
C47 C48 C48a 120.42(13) ?
C47 C48 H48 119.8 ?
C48a C48 H48 119.8 ?
C44a C48a C48 118.25(12) ?
C44a C48a C41 119.46(11) ?
C48 C48a C41 122.29(12) ?
C46 O146 C146 116.82(12) ?
O146 C146 H46A 109.5 ?
O146 C146 H46B 109.5 ?
H46A C146 H46B 109.5 ?
O146 C146 H46C 109.5 ?
H46A C146 H46C 109.5 ?
H46B C146 H46C 109.5 ?
C62 N61 C66 117.56(12) ?
N61 C62 C63 123.91(13) ?
N61 C62 H62 118.0 ?
C63 C62 H62 118.0 ?
C64 C63 C62 116.95(11) ?
C64 C63 C6 121.84(10) ?
C62 C63 C6 121.20(11) ?
C65 C64 C63 119.75(12) ?
C65 C64 H64 120.1 ?
C63 C64 H64 120.1 ?
C66 C65 C64 118.66(14) ?
C66 C65 H65 120.7 ?
C64 C65 H65 120.7 ?
N61 C66 C65 123.12(13) ?
N61 C66 H66 118.4 ?
C65 C66 H66 118.4 ?
H711 O71 H712 106.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.3189(15) y
C2 N3 1.3447(15) y
N3 C4 1.4668(15) y
N3 H3 0.9212 ?
C4 C5 1.5005(17) y
C4 C42 1.5232(16) ?
C4 H4 1.0000 ?
C5 C6 1.3389(17) y
C5 H5 0.9500 ?
C6 N1 1.4096(14) y
C2 N21 1.3563(14) y
N21 H211 0.8981 ?
N21 H212 0.8912 ?
C6 C63 1.4848(16) ?
C41 C42 1.3692(16) y
C41 H41 0.9500 ?
C42 C43 1.4141(18) y
C43 C44 1.3640(19) y
C43 H43 0.9500 ?
C44 C44a 1.4172(17) y
C44 H44 0.9500 ?
C44a C45 1.4211(18) y
C45 C46 1.3637(19) y
C45 H45 0.9500 ?
C46 O146 1.3734(16) ?
C46 C47 1.407(2) y
C47 C48 1.365(2) y
C47 H47 0.9500 ?
C48 C48a 1.4202(16) y
C48a C41 1.4224(17) y
C44a C48a 1.4133(18) y
C48 H48 0.9500 ?
O146 C146 1.417(2) ?
C146 H46A 0.9800 ?
C146 H46B 0.9800 ?
C146 H46C 0.9800 ?
N61 C62 1.3368(17) ?
N61 C66 1.338(2) ?
C62 C63 1.3966(16) ?
C62 H62 0.9500 ?
C63 C64 1.3877(18) ?
C64 C65 1.3857(18) ?
C64 H64 0.9500 ?
C65 C66 1.378(2) ?
C65 H65 0.9500 ?
C66 H66 0.9500 ?
O71 H711 0.8845 ?
O71 H712 0.9034 ?
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
_geom_hbond_publ_flag
N3 H3 O71 . 0.92 2.05 2.8795(14) 149 y
N21 H211 O71 . 0.90 2.10 2.9132(15) 150 y
N21 H212 N1 3_766 0.89 2.14 3.0327(15) 175 y
O71 H711 N61 4_566 0.88 1.90 2.7751(16) 171 y
O71 H712 N1 1_545 0.90 2.10 2.9940(14) 169 y
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
_geom_torsion_publ_flag
C6 N1 C2 N3 -8.17(16) ?
C6 N1 C2 N21 172.54(10) ?
N1 C2 N3 C4 -10.46(18) ?
N21 C2 N3 C4 168.84(10) ?
C2 N3 C4 C5 23.21(15) ?
C2 N3 C4 C42 -99.00(13) ?
N3 C4 C5 C6 -19.82(16) ?
C42 C4 C5 C6 103.00(13) ?
C4 C5 C6 N1 4.27(19) ?
C4 C5 C6 C63 -176.20(11) ?
C2 N1 C6 C5 11.10(17) ?
C2 N1 C6 C63 -168.46(10) ?
C48a C41 C42 C43 -0.24(18) ?
C48a C41 C42 C4 -177.88(11) ?
N3 C4 C42 C41 -124.93(12) ?
C5 C4 C42 C41 114.84(13) ?
N3 C4 C42 C43 57.43(15) ?
C5 C4 C42 C43 -62.80(14) ?
C41 C42 C43 C44 0.7(2) ?
C4 C42 C43 C44 178.40(13) ?
C42 C43 C44 C44a -0.6(2) ?
C43 C44 C44a C48a -0.1(2) ?
C43 C44 C44a C45 179.67(14) ?
C48a C44a C45 C46 -0.4(2) ?
C44 C44a C45 C46 179.85(13) ?
C44a C45 C46 O146 179.50(12) ?
C44a C45 C46 C47 -0.9(2) ?
C45 C46 C47 C48 1.4(2) ?
O146 C46 C47 C48 -178.96(13) ?
C46 C47 C48 C48a -0.5(2) ?
C44 C44a C48a C48 -179.05(13) ?
C45 C44a C48a C48 1.22(18) ?
C44 C44a C48a C41 0.49(18) ?
C45 C44a C48a C41 -179.23(12) ?
C47 C48 C48a C44a -0.7(2) ?
C47 C48 C48a C41 179.73(12) ?
C42 C41 C48a C44a -0.35(18) ?
C42 C41 C48a C48 179.17(12) ?
C45 C46 O146 C146 -6.6(2) y
C47 C46 O146 C146 173.76(13) ?
C66 N61 C62 C63 0.70(19) ?
N61 C62 C63 C64 -2.14(18) ?
N61 C62 C63 C6 178.00(11) ?
C5 C6 C63 C64 144.25(12) ?
N1 C6 C63 C64 -36.18(15) ?
C5 C6 C63 C62 -35.90(17) ?
N1 C6 C63 C62 143.67(11) ?
C62 C63 C64 C65 2.19(17) ?
C6 C63 C64 C65 -177.96(11) ?
C63 C64 C65 C66 -0.94(18) ?
C62 N61 C66 C65 0.7(2) ?
C64 C65 C66 N61 -0.6(2) ?
