#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/44/2214452.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_2214452
loop_
_publ_author_name
'Yi-Ping Jiang'
'Ting Qiu'
'Liang-En Wang'
'Jia-Ning Wang'
_publ_section_title
4-Chloro-6-morpholino-N²-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine
_journal_coeditor_code           XU2270
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3173
_journal_page_last               o3173
_journal_paper_doi               10.1107/S1600536807027924
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H26 Cl N5 O'
_chemical_formula_moiety         'C15 H26 Cl N5 O'
_chemical_formula_sum            'C15 H26 Cl N5 O'
_chemical_formula_weight         327.86
_chemical_melting_point          .369E-305
_chemical_name_systematic
;
4-Chloro-6-morpholino-N²-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine
;
_space_group_IT_number           14
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.939(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.119(3)
_cell_length_b                   7.4964(17)
_cell_length_c                   17.083(4)
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.9
_cell_volume                     1769.0(7)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.035
_diffrn_reflns_av_sigmaI/netI    0.040
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9840
_diffrn_reflns_theta_full        26.4
_diffrn_reflns_theta_max         26.7
_diffrn_reflns_theta_min         1.7
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.074
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0549P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.114
_reflns_number_gt                2385
_reflns_number_total             3618
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2270.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214452
_cod_database_fobs_code          2214452
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_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_refinement_flags
_atom_site_occupancy
Cl Cl1 0.43258(4) 0.68022(8) 1.16149(3) 0.05564(19) Uani d . 1
O O1 0.31616(10) 0.8309(2) 0.72604(8) 0.0534(4) Uani d . 1
N N1 0.43414(11) 0.7080(2) 1.01064(9) 0.0402(4) Uani d . 1
N N2 0.58416(11) 0.7425(2) 1.10318(8) 0.0385(4) Uani d . 1
N N3 0.57800(10) 0.7775(2) 0.96303(8) 0.0385(4) Uani d . 1
N N4 0.72149(11) 0.8004(2) 1.05739(9) 0.0419(4) Uani d D 1
N N5 0.43047(11) 0.7482(2) 0.87630(9) 0.0466(4) Uani d . 1
C C1 0.48256(13) 0.7441(2) 0.95198(10) 0.0368(4) Uani d . 1
C C2 0.49106(13) 0.7137(2) 1.08183(11) 0.0373(4) Uani d . 1
C C3 0.62534(12) 0.7724(2) 1.03887(10) 0.0344(4) Uani d . 1
C C4 0.47478(15) 0.7818(3) 0.80787(11) 0.0532(6) Uani d . 1
H H4A 0.4837 0.6699 0.7818 0.064 Uiso calc R 1
H H4B 0.5378 0.8366 0.8257 0.064 Uiso calc R 1
C C5 0.41114(15) 0.9024(3) 0.75028(12) 0.0528(5) Uani d . 1
H H5A 0.4075 1.0178 0.7752 0.063 Uiso calc R 1
H H5B 0.4392 0.9197 0.7036 0.063 Uiso calc R 1
C C6 0.27284(14) 0.8130(3) 0.79388(12) 0.0518(5) Uani d . 1
H H6A 0.2075 0.7675 0.7768 0.062 Uiso calc R 1
H H6B 0.2688 0.9294 0.8178 0.062 Uiso calc R 1
C C7 0.32985(14) 0.6891(3) 0.85542(12) 0.0506(5) Uani d . 1
H H7A 0.3022 0.6883 0.9029 0.061 Uiso calc R 1
H H7B 0.3269 0.5688 0.8342 0.061 Uiso calc R 1
C C8 0.78825(13) 0.8290(3) 1.00235(10) 0.0390(4) Uani d . 1
C C9 0.88419(15) 0.8807(3) 1.05725(13) 0.0624(6) Uani d . 1
H H9A 0.8739 0.9798 1.0901 0.094 Uiso calc R 1
H H9B 0.9300 0.9137 1.0254 0.094 Uiso calc R 1
H H9C 0.9088 0.7812 1.0907 0.094 Uiso calc R 1
C C10 0.75325(16) 0.9854(3) 0.94675(13) 0.0574(6) Uani d . 1
H H10A 0.6952 0.9521 0.9096 0.086 Uiso calc R 1
H H10B 0.8024 1.0169 0.9179 0.086 Uiso calc R 1
H H10C 0.7401 1.0858 0.9778 0.086 Uiso calc R 1
C C11 0.79641(13) 0.6485(2) 0.96018(11) 0.0400(4) Uani d . 1
H H11A 0.7311 0.6017 0.9451 0.048 Uiso calc R 1
H H11B 0.8315 0.5688 1.0008 0.048 Uiso calc R 1
C C12 0.84258(13) 0.6268(3) 0.88572(11) 0.0458(5) Uani d . 1
C C13 0.85638(17) 0.4252(3) 0.87652(14) 0.0687(7) Uani d . 1
H H13A 0.7955 0.3656 0.8732 0.103 Uiso calc R 1
H H13B 0.9022 0.3813 0.9220 0.103 Uiso calc R 1
H H13C 0.8801 0.4028 0.8287 0.103 Uiso calc R 1
C C14 0.94073(16) 0.7175(3) 0.89346(15) 0.0703(7) Uani d . 1
H H14A 0.9672 0.6897 0.8475 0.105 Uiso calc R 1
H H14B 0.9838 0.6757 0.9409 0.105 Uiso calc R 1
H H14C 0.9329 0.8443 0.8968 0.105 Uiso calc R 1
C C15 0.77405(17) 0.6911(3) 0.80975(12) 0.0640(6) Uani d . 1
H H15A 0.7701 0.8189 0.8104 0.096 Uiso calc R 1
H H15B 0.7109 0.6412 0.8073 0.096 Uiso calc R 1
H H15C 0.7981 0.6536 0.7638 0.096 Uiso calc R 1
H H4 0.7492(13) 0.778(2) 1.1082(6) 0.046(6) Uiso d 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'
Cl Cl 0.1484 0.1585 '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
C5 O1 C6 109.63(14)
C2 N1 C1 111.93(15)
C2 N2 C3 111.97(15)
C3 N3 C1 114.73(15)
C3 N4 C8 128.20(14)
C3 N4 H4 114.7(13)
C8 N4 H4 116.0(13)
C1 N5 C4 122.23(16)
C1 N5 C7 122.48(16)
C4 N5 C7 114.44(15)
N3 C1 N5 117.51(16)
N3 C1 N1 125.37(16)
N5 C1 N1 117.12(16)
N2 C2 N1 130.66(17)
N2 C2 Cl1 114.57(14)
N1 C2 Cl1 114.77(14)
N3 C3 N4 120.26(16)
N3 C3 N2 125.28(16)
N4 C3 N2 114.46(15)
N5 C4 C5 109.48(16)
N5 C4 H4A 109.8
C5 C4 H4A 109.8
N5 C4 H4B 109.8
C5 C4 H4B 109.8
H4A C4 H4B 108.2
O1 C5 C4 111.46(18)
O1 C5 H5A 109.3
C4 C5 H5A 109.3
O1 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 108.0
O1 C6 C7 111.63(16)
O1 C6 H6A 109.3
C7 C6 H6A 109.3
O1 C6 H6B 109.3
C7 C6 H6B 109.3
H6A C6 H6B 108.0
N5 C7 C6 109.64(17)
N5 C7 H7A 109.7
C6 C7 H7A 109.7
N5 C7 H7B 109.7
C6 C7 H7B 109.7
H7A C7 H7B 108.2
N4 C8 C10 109.89(15)
N4 C8 C9 104.31(14)
C10 C8 C9 108.56(17)
N4 C8 C11 106.76(14)
C10 C8 C11 115.32(15)
C9 C8 C11 111.43(16)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 C12 123.87(15)
C8 C11 H11A 106.4
C12 C11 H11A 106.4
C8 C11 H11B 106.4
C12 C11 H11B 106.4
H11A C11 H11B 106.4
C14 C12 C15 109.72(19)
C14 C12 C13 108.39(18)
C15 C12 C13 107.16(19)
C14 C12 C11 114.21(17)
C15 C12 C11 111.30(16)
C13 C12 C11 105.71(16)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 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
Cl1 C2 1.7497(18)
O1 C5 1.424(2)
O1 C6 1.424(2)
N1 C2 1.312(2)
N1 C1 1.352(2)
N2 C2 1.307(2)
N2 C3 1.364(2)
N3 C3 1.330(2)
N3 C1 1.345(2)
N4 C3 1.345(2)
N4 C8 1.478(2)
N4 H4 0.891(9)
N5 C1 1.349(2)
N5 C4 1.457(2)
N5 C7 1.460(2)
C4 C5 1.493(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.505(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9700
C7 H7B 0.9700
C8 C10 1.526(3)
C8 C9 1.530(3)
C8 C11 1.548(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.553(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C14 1.525(3)
C12 C15 1.528(3)
C12 C13 1.536(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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
N4 H4 O1 4_676 0.891(9) 2.197(10) 3.076(2) 168.9(17)
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
C3 N3 C1 N5 179.69(17)
C3 N3 C1 N1 0.3(3)
C4 N5 C1 N3 1.9(3)
C7 N5 C1 N3 170.86(17)
C4 N5 C1 N1 -178.61(17)
C7 N5 C1 N1 -9.7(3)
C2 N1 C1 N3 1.7(3)
C2 N1 C1 N5 -177.68(17)
C3 N2 C2 N1 0.7(3)
C3 N2 C2 Cl1 -178.35(12)
C1 N1 C2 N2 -2.3(3)
C1 N1 C2 Cl1 176.73(13)
C1 N3 C3 N4 178.78(17)
C1 N3 C3 N2 -2.2(3)
C8 N4 C3 N3 -3.7(3)
C8 N4 C3 N2 177.19(17)
C2 N2 C3 N3 1.8(3)
C2 N2 C3 N4 -179.15(17)
C1 N5 C4 C5 -139.1(2)
C7 N5 C4 C5 51.2(2)
C6 O1 C5 C4 61.8(2)
N5 C4 C5 O1 -56.2(2)
C5 O1 C6 C7 -60.6(2)
C1 N5 C7 C6 140.15(19)
C4 N5 C7 C6 -50.1(2)
O1 C6 C7 N5 54.1(2)
C3 N4 C8 C10 55.6(2)
C3 N4 C8 C9 171.8(2)
C3 N4 C8 C11 -70.1(2)
N4 C8 C11 C12 167.39(15)
C10 C8 C11 C12 45.0(2)
C9 C8 C11 C12 -79.3(2)
C8 C11 C12 C14 48.2(3)
C8 C11 C12 C15 -76.7(2)
C8 C11 C12 C13 167.27(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124050
2 PubChem 139072586
