#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:48:10 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239932.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_7239932
loop_
_publ_author_name
'Li, Yinghua'
'Zhu, Yingzu'
'Xiang, Shiqun'
'Fan, Weibin'
'Jin, Jiang'
'Huang, Deguang'
_publ_section_title
;
 Temperature controlled condensation of nitriles: efficient and convenient
 synthesis of β-enaminonitriles, 4-aminopyrimidines and
 4-amidinopyrimidines in one system
;
_journal_issue                   11
_journal_name_full               'RSC Advances'
_journal_page_first              6576
_journal_page_last               6583
_journal_paper_doi               10.1039/C9RA10866A
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C25 H22 N4'
_chemical_formula_sum            'C25 H22 N4'
_chemical_formula_weight         378.47
_space_group_IT_number           33
_space_group_name_Hall           'P -2ac -2n'
_space_group_name_H-M_alt        'P n 21 a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-09-27 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7806(4)
_cell_length_b                   14.4288(4)
_cell_length_c                   11.4659(3)
_cell_measurement_reflns_used    2523
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.4350
_cell_measurement_theta_min      4.9030
_cell_volume                     1948.97(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      100(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4784
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         4.93
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_correction_T_min  0.8390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0308
_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)+(0.0412P)²+0.0932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0754
_reflns_number_gt                2413
_reflns_number_total             2552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra10866a2.cif
_cod_data_source_block           Compound6b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7239928--7239936.cif.
;
_cod_database_code               7239932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.32886(12) 0.24673(11) 0.84381(13) 0.0157(3) Uani 1 1 d . . .
N2 N 0.47633(12) 0.29319(11) 0.97382(12) 0.0149(3) Uani 1 1 d . . .
N3 N 0.60344(12) 0.41470(11) 0.92039(13) 0.0159(3) Uani 1 1 d . . .
N4 N 0.35092(13) 0.13733(11) 0.99639(13) 0.0188(3) Uani 1 1 d . . .
H4A H 0.4143 0.1624 1.0219 0.023 Uiso 1 1 calc R . .
H4B H 0.3228 0.0881 1.0314 0.023 Uiso 1 1 calc R . .
C1 C 0.42379(15) 0.29904(13) 0.86920(15) 0.0153(4) Uani 1 1 d . . .
C2 C 0.46149(15) 0.36234(12) 0.78318(15) 0.0152(4) Uani 1 1 d . . .
C3 C 0.40592(15) 0.36785(13) 0.66542(15) 0.0178(4) Uani 1 1 d . . .
H3B H 0.4208 0.4297 0.6312 0.021 Uiso 1 1 calc R . .
H3C H 0.3228 0.3612 0.6749 0.021 Uiso 1 1 calc R . .
C4 C 0.44835(18) 0.29364(16) 0.58191(16) 0.0274(4) Uani 1 1 d . . .
H4C H 0.4097 0.3002 0.5067 0.041 Uiso 1 1 calc R . .
H4D H 0.4323 0.2322 0.6145 0.041 Uiso 1 1 calc R . .
H4E H 0.5304 0.3007 0.5708 0.041 Uiso 1 1 calc R . .
C5 C 0.55391(15) 0.41693(12) 0.81319(15) 0.0150(4) Uani 1 1 d . . .
C6 C 0.60842(15) 0.48297(13) 0.72960(16) 0.0159(4) Uani 1 1 d . . .
C7 C 0.69080(15) 0.45093(14) 0.65238(16) 0.0200(4) Uani 1 1 d . . .
H7A H 0.7067 0.3865 0.6481 0.024 Uiso 1 1 calc R . .
C8 C 0.75014(16) 0.51235(15) 0.58137(17) 0.0226(4) Uani 1 1 d . . .
H8A H 0.8067 0.4900 0.5295 0.027 Uiso 1 1 calc R . .
C9 C 0.72623(17) 0.60646(15) 0.58668(17) 0.0235(4) Uani 1 1 d . . .
H9A H 0.7675 0.6489 0.5396 0.028 Uiso 1 1 calc R . .
C10 C 0.64231(18) 0.63830(14) 0.66058(16) 0.0236(4) Uani 1 1 d . . .
H10A H 0.6247 0.7025 0.6627 0.028 Uiso 1 1 calc R . .
C11 C 0.58364(17) 0.57731(13) 0.73164(15) 0.0208(4) Uani 1 1 d . . .
H11A H 0.5261 0.6000 0.7822 0.025 Uiso 1 1 calc R . .
C12 C 0.56270(14) 0.35166(13) 0.99469(15) 0.0145(4) Uani 1 1 d . . .
C13 C 0.61812(16) 0.34435(12) 1.11081(15) 0.0157(4) Uani 1 1 d . . .
C14 C 0.72303(16) 0.38572(14) 1.13110(16) 0.0172(4) Uani 1 1 d . . .
H14A H 0.7594 0.4191 1.0702 0.021 Uiso 1 1 calc R . .
C15 C 0.77521(16) 0.37881(14) 1.23943(16) 0.0203(4) Uani 1 1 d . . .
H15A H 0.8465 0.4079 1.2524 0.024 Uiso 1 1 calc R . .
C16 C 0.72345(17) 0.32956(14) 1.32874(17) 0.0217(4) Uani 1 1 d . . .
H16A H 0.7592 0.3248 1.4028 0.026 Uiso 1 1 calc R . .
C17 C 0.61928(16) 0.28735(14) 1.30947(16) 0.0210(4) Uani 1 1 d . . .
H17A H 0.5837 0.2532 1.3702 0.025 Uiso 1 1 calc R . .
C18 C 0.56697(15) 0.29504(13) 1.20118(15) 0.0182(4) Uani 1 1 d . . .
H18A H 0.4954 0.2663 1.1886 0.022 Uiso 1 1 calc R . .
C19 C 0.29714(15) 0.17405(13) 0.90423(15) 0.0153(4) Uani 1 1 d . . .
C20 C 0.19013(15) 0.12812(13) 0.86613(16) 0.0166(4) Uani 1 1 d . . .
C21 C 0.15759(15) 0.13362(14) 0.74935(16) 0.0201(4) Uani 1 1 d . . .
H21A H 0.2038 0.1658 0.6948 0.024 Uiso 1 1 calc R . .
C22 C 0.05779(16) 0.09201(14) 0.71339(17) 0.0228(4) Uani 1 1 d . . .
H22A H 0.0361 0.0953 0.6337 0.027 Uiso 1 1 calc R . .
C23 C -0.01110(16) 0.04555(14) 0.79232(19) 0.0238(4) Uani 1 1 d . . .
H23A H -0.0796 0.0174 0.7668 0.029 Uiso 1 1 calc R . .
C24 C 0.02060(16) 0.04048(13) 0.90876(18) 0.0217(4) Uani 1 1 d . . .
H24A H -0.0263 0.0089 0.9631 0.026 Uiso 1 1 calc R . .
C25 C 0.12097(15) 0.08166(13) 0.94578(17) 0.0189(4) Uani 1 1 d . . .
H25A H 0.1425 0.0782 1.0255 0.023 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 0.0181 0.0091 '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 0.0311 0.0180 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C1 123.83(15) . . ?
C12 N2 C1 117.75(15) . . ?
C12 N3 C5 115.98(15) . . ?
C19 N4 H4A 120.0 . . ?
C19 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
N2 C1 N1 121.59(16) . . ?
N2 C1 C2 120.97(16) . . ?
N1 C1 C2 117.38(16) . . ?
C5 C2 C1 116.09(15) . . ?
C5 C2 C3 122.33(16) . . ?
C1 C2 C3 121.57(16) . . ?
C2 C3 C4 112.67(16) . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3C 109.1 . . ?
C4 C3 H3C 109.1 . . ?
H3B C3 H3C 107.8 . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N3 C5 C2 123.17(16) . . ?
N3 C5 C6 114.18(16) . . ?
C2 C5 C6 122.65(16) . . ?
C11 C6 C7 118.77(17) . . ?
C11 C6 C5 121.45(17) . . ?
C7 C6 C5 119.66(17) . . ?
C8 C7 C6 120.70(18) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C9 C8 C7 119.69(19) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C10 C9 C8 119.85(19) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.48(19) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C6 120.46(18) . . ?
C10 C11 H11A 119.8 . . ?
C6 C11 H11A 119.8 . . ?
N3 C12 N2 125.90(15) . . ?
N3 C12 C13 117.50(16) . . ?
N2 C12 C13 116.59(15) . . ?
C14 C13 C18 118.58(16) . . ?
C14 C13 C12 120.60(16) . . ?
C18 C13 C12 120.81(16) . . ?
C15 C14 C13 120.75(17) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 120.14(18) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 119.73(17) . . ?
C15 C16 H16A 120.1 . . ?
C17 C16 H16A 120.1 . . ?
C16 C17 C18 119.94(18) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 120.86(17) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?
N1 C19 N4 126.71(16) . . ?
N1 C19 C20 116.23(15) . . ?
N4 C19 C20 117.06(16) . . ?
C21 C20 C25 119.67(17) . . ?
C21 C20 C19 119.25(16) . . ?
C25 C20 C19 121.06(16) . . ?
C22 C21 C20 119.67(18) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C21 C22 C23 120.82(18) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C22 C23 C24 119.68(18) . . ?
C22 C23 H23A 120.2 . . ?
C24 C23 H23A 120.2 . . ?
C23 C24 C25 120.00(18) . . ?
C23 C24 H24A 120.0 . . ?
C25 C24 H24A 120.0 . . ?
C24 C25 C20 120.15(17) . . ?
C24 C25 H25A 119.9 . . ?
C20 C25 H25A 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C19 1.311(2) . ?
N1 C1 1.380(2) . ?
N2 C12 1.343(2) . ?
N2 C1 1.352(2) . ?
N3 C12 1.335(2) . ?
N3 C5 1.361(2) . ?
N4 C19 1.341(2) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C2 1.416(3) . ?
C2 C5 1.387(3) . ?
C2 C3 1.503(2) . ?
C3 C4 1.521(3) . ?
C3 H3B 0.9900 . ?
C3 H3C 0.9900 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 C6 1.496(3) . ?
C6 C11 1.392(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.392(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.388(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.487(2) . ?
C13 C14 1.392(3) . ?
C13 C18 1.394(2) . ?
C14 C15 1.389(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.490(2) . ?
C20 C21 1.395(3) . ?
C20 C25 1.395(3) . ?
C21 C22 1.383(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.388(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 C1 N1 -174.90(15) . . . . ?
C12 N2 C1 C2 2.3(3) . . . . ?
C19 N1 C1 N2 -16.1(3) . . . . ?
C19 N1 C1 C2 166.55(16) . . . . ?
N2 C1 C2 C5 -0.2(2) . . . . ?
N1 C1 C2 C5 177.17(15) . . . . ?
N2 C1 C2 C3 178.35(16) . . . . ?
N1 C1 C2 C3 -4.3(3) . . . . ?
C5 C2 C3 C4 96.8(2) . . . . ?
C1 C2 C3 C4 -81.6(2) . . . . ?
C12 N3 C5 C2 4.3(2) . . . . ?
C12 N3 C5 C6 -175.16(15) . . . . ?
C1 C2 C5 N3 -3.3(3) . . . . ?
C3 C2 C5 N3 178.19(17) . . . . ?
C1 C2 C5 C6 176.14(16) . . . . ?
C3 C2 C5 C6 -2.4(3) . . . . ?
N3 C5 C6 C11 -81.4(2) . . . . ?
C2 C5 C6 C11 99.1(2) . . . . ?
N3 C5 C6 C7 94.7(2) . . . . ?
C2 C5 C6 C7 -84.8(2) . . . . ?
C11 C6 C7 C8 2.2(3) . . . . ?
C5 C6 C7 C8 -174.03(17) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
C7 C6 C11 C10 -1.9(3) . . . . ?
C5 C6 C11 C10 174.28(17) . . . . ?
C5 N3 C12 N2 -2.0(3) . . . . ?
C5 N3 C12 C13 177.36(16) . . . . ?
C1 N2 C12 N3 -1.3(3) . . . . ?
C1 N2 C12 C13 179.39(16) . . . . ?
N3 C12 C13 C14 -14.3(3) . . . . ?
N2 C12 C13 C14 165.08(16) . . . . ?
N3 C12 C13 C18 166.48(16) . . . . ?
N2 C12 C13 C18 -14.1(3) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 -179.82(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C12 C13 C18 C17 179.33(18) . . . . ?
C1 N1 C19 N4 -1.8(3) . . . . ?
C1 N1 C19 C20 178.02(16) . . . . ?
N1 C19 C20 C21 28.1(3) . . . . ?
N4 C19 C20 C21 -152.03(18) . . . . ?
N1 C19 C20 C25 -150.43(17) . . . . ?
N4 C19 C20 C25 29.4(3) . . . . ?
C25 C20 C21 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 -179.34(17) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 0.5(3) . . . . ?
C19 C20 C25 C24 179.02(17) . . . . ?
