#------------------------------------------------------------------------------ #$Date: 2017-10-13 09:03:29 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$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-N^2^-(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-N^2^-(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 '\f and \w' _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/[\s^2^(Fo^2^)+(0.0549P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/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>2\s(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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0497(3) 0.0763(4) 0.0457(3) -0.0021(3) 0.0209(2) 0.0055(3) O1 0.0470(8) 0.0700(10) 0.0372(7) -0.0010(7) -0.0050(6) -0.0001(7) N1 0.0337(8) 0.0479(10) 0.0386(9) -0.0018(7) 0.0062(7) 0.0017(7) N2 0.0345(9) 0.0487(10) 0.0317(8) 0.0000(7) 0.0058(7) -0.0015(7) N3 0.0315(8) 0.0501(10) 0.0325(8) -0.0008(7) 0.0029(6) -0.0006(7) N4 0.0319(8) 0.0616(11) 0.0310(8) -0.0034(7) 0.0036(7) -0.0017(8) N5 0.0317(9) 0.0696(12) 0.0356(9) -0.0029(8) -0.0001(7) 0.0061(8) C1 0.0362(10) 0.0365(10) 0.0362(10) 0.0020(8) 0.0044(8) 0.0018(8) C2 0.0388(10) 0.0379(11) 0.0369(10) 0.0012(8) 0.0114(8) -0.0008(8) C3 0.0320(9) 0.0380(11) 0.0325(9) 0.0006(8) 0.0053(8) -0.0019(8) C4 0.0396(11) 0.0823(17) 0.0363(11) 0.0022(10) 0.0048(9) 0.0043(11) C5 0.0512(13) 0.0620(14) 0.0416(11) -0.0059(10) 0.0012(9) 0.0019(10) C6 0.0386(11) 0.0620(14) 0.0497(12) 0.0023(10) -0.0029(9) -0.0047(11) C7 0.0397(11) 0.0608(14) 0.0461(11) -0.0087(10) -0.0032(9) 0.0011(10) C8 0.0326(9) 0.0482(12) 0.0367(10) -0.0047(8) 0.0082(8) 0.0016(9) C9 0.0423(12) 0.0892(18) 0.0562(13) -0.0200(12) 0.0114(10) -0.0147(13) C10 0.0591(14) 0.0479(14) 0.0699(14) 0.0007(10) 0.0244(11) 0.0082(11) C11 0.0342(10) 0.0456(12) 0.0396(10) -0.0004(8) 0.0061(8) 0.0061(9) C12 0.0399(11) 0.0559(14) 0.0432(11) -0.0027(9) 0.0119(9) -0.0034(10) C13 0.0656(15) 0.0692(17) 0.0730(16) 0.0102(13) 0.0182(12) -0.0128(13) C14 0.0497(14) 0.099(2) 0.0697(16) -0.0147(13) 0.0286(12) -0.0141(14) C15 0.0684(15) 0.0829(18) 0.0412(12) -0.0026(13) 0.0122(11) 0.0033(12) 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