#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:48:10 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239929.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_7239929
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         'C15 H21 N3'
_chemical_formula_sum            'C15 H21 N3'
_chemical_formula_weight         243.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 93.032(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8970(3)
_cell_length_b                   9.8470(3)
_cell_length_c                   14.2912(5)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.7310
_cell_measurement_theta_min      5.3000
_cell_volume                     1390.81(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4954
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         5.31
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0482
_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)+(0.0775P)²+0.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                2216
_reflns_number_total             2605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra10866a2.cif
_cod_data_source_block           Compound4a
_cod_depositor_comments
'Adding full bibliography for 7239928--7239936.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7239929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.06674(13) -0.13317(15) 0.06619(10) 0.0312(3) Uani 1 1 d . . .
N2 N 0.24648(12) 0.15768(13) -0.01076(8) 0.0208(3) Uani 1 1 d . . .
H2A H 0.1647 0.1881 -0.0013 0.025 Uiso 1 1 calc R . .
N3 N 0.45208(12) 0.15774(13) 0.07606(9) 0.0212(3) Uani 1 1 d . . .
H3A H 0.5187 0.1024 0.0934 0.025 Uiso 1 1 calc R . .
C1 C 0.16263(14) -0.07174(16) 0.08826(10) 0.0217(3) Uani 1 1 d . . .
C2 C 0.28035(14) 0.00111(15) 0.11879(10) 0.0198(3) Uani 1 1 d . . .
C3 C 0.35226(14) -0.04644(16) 0.20690(10) 0.0206(3) Uani 1 1 d . . .
C4 C 0.37852(15) -0.18492(17) 0.22024(11) 0.0257(4) Uani 1 1 d . . .
H4A H 0.3522 -0.2476 0.1721 0.031 Uiso 1 1 calc R . .
C5 C 0.44225(16) -0.23196(19) 0.30248(12) 0.0322(4) Uani 1 1 d . . .
H5A H 0.4589 -0.3264 0.3104 0.039 Uiso 1 1 calc R . .
C6 C 0.48187(17) -0.1420(2) 0.37333(12) 0.0352(4) Uani 1 1 d . . .
H6A H 0.5262 -0.1743 0.4296 0.042 Uiso 1 1 calc R . .
C7 C 0.45640(17) -0.0046(2) 0.36151(11) 0.0322(4) Uani 1 1 d . . .
H7A H 0.4831 0.0574 0.4099 0.039 Uiso 1 1 calc R . .
C8 C 0.39191(15) 0.04305(17) 0.27911(11) 0.0252(4) Uani 1 1 d . . .
H8A H 0.3746 0.1375 0.2718 0.030 Uiso 1 1 calc R . .
C9 C 0.32456(14) 0.10476(15) 0.06271(10) 0.0187(3) Uani 1 1 d . . .
C10 C 0.29881(14) 0.16390(15) -0.10535(10) 0.0201(3) Uani 1 1 d . . .
H10A H 0.3999 0.1664 -0.0990 0.024 Uiso 1 1 calc R . .
C11 C 0.25633(17) 0.03818(17) -0.16150(12) 0.0283(4) Uani 1 1 d . . .
H11A H 0.2886 -0.0433 -0.1279 0.042 Uiso 1 1 calc R . .
H11B H 0.2956 0.0416 -0.2230 0.042 Uiso 1 1 calc R . .
H11C H 0.1574 0.0353 -0.1698 0.042 Uiso 1 1 calc R . .
C12 C 0.25001(18) 0.29131(17) -0.15600(11) 0.0300(4) Uani 1 1 d . . .
H12A H 0.2781 0.3712 -0.1190 0.045 Uiso 1 1 calc R . .
H12B H 0.1511 0.2894 -0.1643 0.045 Uiso 1 1 calc R . .
H12C H 0.2893 0.2957 -0.2175 0.045 Uiso 1 1 calc R . .
C13 C 0.48356(15) 0.30265(15) 0.06297(10) 0.0214(3) Uani 1 1 d . . .
H13A H 0.4406 0.3325 0.0015 0.026 Uiso 1 1 calc R . .
C14 C 0.42795(18) 0.39020(18) 0.13952(13) 0.0346(4) Uani 1 1 d . . .
H14A H 0.3298 0.3778 0.1402 0.052 Uiso 1 1 calc R . .
H14B H 0.4482 0.4858 0.1274 0.052 Uiso 1 1 calc R . .
H14C H 0.4700 0.3635 0.2004 0.052 Uiso 1 1 calc R . .
C15 C 0.63596(16) 0.31795(17) 0.05875(13) 0.0293(4) Uani 1 1 d . . .
H15A H 0.6682 0.2602 0.0087 0.044 Uiso 1 1 calc R . .
H15B H 0.6799 0.2906 0.1189 0.044 Uiso 1 1 calc R . .
H15C H 0.6580 0.4129 0.0459 0.044 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
C9 N2 C10 120.41(11) . . ?
C9 N2 H2A 119.8 . . ?
C10 N2 H2A 119.8 . . ?
C9 N3 C13 123.38(12) . . ?
C9 N3 H3A 118.3 . . ?
C13 N3 H3A 118.3 . . ?
N1 C1 C2 177.77(16) . . ?
C9 C2 C1 118.37(13) . . ?
C9 C2 C3 124.79(13) . . ?
C1 C2 C3 116.72(13) . . ?
C8 C3 C4 118.10(14) . . ?
C8 C3 C2 121.96(14) . . ?
C4 C3 C2 119.91(14) . . ?
C5 C4 C3 120.99(16) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 120.33(16) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C7 C6 C5 119.51(15) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
C6 C7 C8 120.35(17) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C3 120.72(16) . . ?
C7 C8 H8A 119.6 . . ?
C3 C8 H8A 119.6 . . ?
N3 C9 N2 116.05(13) . . ?
N3 C9 C2 121.18(13) . . ?
N2 C9 C2 122.74(13) . . ?
N2 C10 C12 110.73(12) . . ?
N2 C10 C11 110.42(12) . . ?
C12 C10 C11 110.46(13) . . ?
N2 C10 H10A 108.4 . . ?
C12 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 111.77(13) . . ?
N3 C13 C15 108.53(12) . . ?
C14 C13 C15 111.74(13) . . ?
N3 C13 H13A 108.2 . . ?
C14 C13 H13A 108.2 . . ?
C15 C13 H13A 108.2 . . ?
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 . . ?
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 C1 1.155(2) . ?
N2 C9 1.3730(18) . ?
N2 C10 1.4743(18) . ?
N2 H2A 0.8800 . ?
N3 C9 1.3697(19) . ?
N3 C13 1.4745(19) . ?
N3 H3A 0.8800 . ?
C1 C2 1.417(2) . ?
C2 C9 1.383(2) . ?
C2 C3 1.489(2) . ?
C3 C8 1.397(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.384(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C10 C12 1.515(2) . ?
C10 C11 1.522(2) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(2) . ?
C13 C15 1.520(2) . ?
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 . ?
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
N1 C1 C2 C9 -171(4) . . . . ?
N1 C1 C2 C3 12(4) . . . . ?
C9 C2 C3 C8 52.5(2) . . . . ?
C1 C2 C3 C8 -131.56(15) . . . . ?
C9 C2 C3 C4 -129.36(16) . . . . ?
C1 C2 C3 C4 46.62(19) . . . . ?
C8 C3 C4 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -178.41(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C4 C3 C8 C7 0.4(2) . . . . ?
C2 C3 C8 C7 178.62(14) . . . . ?
C13 N3 C9 N2 37.9(2) . . . . ?
C13 N3 C9 C2 -144.05(14) . . . . ?
C10 N2 C9 N3 52.09(19) . . . . ?
C10 N2 C9 C2 -125.91(15) . . . . ?
C1 C2 C9 N3 -164.71(13) . . . . ?
C3 C2 C9 N3 11.2(2) . . . . ?
C1 C2 C9 N2 13.2(2) . . . . ?
C3 C2 C9 N2 -170.88(13) . . . . ?
C9 N2 C10 C12 -144.05(14) . . . . ?
C9 N2 C10 C11 93.29(16) . . . . ?
C9 N3 C13 C14 70.89(18) . . . . ?
C9 N3 C13 C15 -165.43(13) . . . . ?
