#------------------------------------------------------------------------------ #$Date: 2020-05-04 22:27:52 +0300 (Mon, 04 May 2020) $ #$Revision: 251497 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240446.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_7240446 loop_ _publ_author_name 'Hadian, Mojgan' 'Shaabani, Shabnam' 'Patil, Pravin' 'Shishkina, Svitlana V.' 'B\"oltz, Harry' 'D\"omling, Alexander' _publ_section_title ; Sustainability by design: automated nanoscale 2,3,4-trisubstituted quinazoline diversity ; _journal_issue 8 _journal_name_full 'Green Chemistry' _journal_page_first 2459 _journal_paper_doi 10.1039/D0GC00363H _journal_volume 22 _journal_year 2020 _chemical_formula_sum 'C11 H9 N O4' _chemical_formula_weight 219.19 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-11-29 deposited with the CCDC. 2020-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.39(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.522(5) _cell_length_b 3.8101(12) _cell_length_c 26.193(8) _cell_measurement_reflns_used 465 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.807 _cell_measurement_theta_min 4.009 _cell_volume 2000.4(10) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1005 _diffrn_reflns_av_unetI/netI 0.1078 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 9140 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.999 _diffrn_reflns_theta_min 3.391 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.03238 _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 1.456 _exptl_crystal_description stick _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.238 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.858 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 2930 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.858 _refine_ls_R_factor_all 0.2002 _refine_ls_R_factor_gt 0.0758 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0940P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1904 _refine_ls_wR_factor_ref 0.2470 _reflns_Friedel_coverage 0.000 _reflns_number_gt 933 _reflns_number_total 2930 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc00363h2.cif _cod_data_source_block ad26 _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7240446 _shelx_shelxl_version_number 2016/6 _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 0.967 _shelx_estimated_absorpt_t_max 0.994 _shelx_res_file ; TITL ad26_a.res in C2/c ad26.res created by SHELXL-2016/6 at 14:55:00 on 11-Jul-2019 CELL 0.71073 20.5218 3.8101 26.1932 90 102.388 90 ZERR 8 0.005 0.0012 0.0079 0 0.029 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 88 72 8 32 L.S. 4 0 0 PLAN 20 BOND $H list 4 fmap 2 53 ACTA OMIT 0 60 conf size 0.3 0.08 0.05 temp 20 htab n1 o1 htab o4 o2 WGHT 0.094000 FVAR 0.38189 O1 4 0.569408 -0.006747 0.538765 11.00000 0.07884 0.13770 = 0.08075 -0.00425 0.01648 0.02948 O2 4 0.431114 0.439430 0.656666 11.00000 0.06526 0.11581 = 0.06577 -0.00226 0.01437 0.01687 O3 4 0.240935 0.856724 0.572434 11.00000 0.06610 0.12105 = 0.10364 0.00333 0.01159 0.03023 O4 4 0.316293 0.710183 0.641427 11.00000 0.06666 0.13466 = 0.07884 -0.01369 0.01439 0.02437 AFIX 147 H4O 2 0.352542 0.610548 0.648262 11.00000 -1.50000 AFIX 0 N1 3 0.501123 0.223622 0.608634 11.00000 0.05478 0.07742 = 0.06388 -0.00030 0.01284 0.00771 AFIX 43 H1N 2 0.504932 0.189628 0.576947 11.00000 -1.20000 AFIX 0 C1 1 0.555994 0.110281 0.647565 11.00000 0.05235 0.06176 = 0.07091 -0.00035 0.00854 0.00015 C2 1 0.557556 0.145727 0.699976 11.00000 0.06483 0.08319 = 0.07965 -0.00026 0.01784 0.00823 AFIX 43 H2 2 0.521610 0.245063 0.711116 11.00000 -1.20000 AFIX 0 C3 1 0.613771 0.030998 0.736588 11.00000 0.07378 0.08578 = 0.07930 -0.00084 0.00510 0.00890 AFIX 43 H3 2 0.614872 0.055022 0.772096 11.00000 -1.20000 AFIX 0 C4 1 0.666729 -0.114995 0.720873 11.00000 0.05665 0.08034 = 0.09376 0.01202 -0.00122 0.00255 AFIX 43 H4 2 0.703832 -0.188423 0.745560 11.00000 -1.20000 AFIX 0 C5 1 0.665328 -0.153743 0.668579 11.00000 0.05311 0.06901 = 0.10410 0.00694 0.00937 0.00409 AFIX 43 H5 2 0.701560 -0.254180 0.657982 11.00000 -1.20000 AFIX 0 C6 1 0.610142 -0.044050 0.631212 11.00000 0.05284 0.06051 = 0.07762 0.00038 0.01618 0.00095 C7 1 0.612053 -0.091791 0.576963 11.00000 0.06187 0.08741 = 0.09577 0.00138 0.02716 0.00598 AFIX 43 H7 2 0.650011 -0.199456 0.570241 11.00000 -1.20000 AFIX 0 C8 1 0.443656 0.377323 0.613924 11.00000 0.05709 0.07148 = 0.06118 0.00114 0.01137 0.00442 C9 1 0.397903 0.460162 0.563701 11.00000 0.06139 0.08624 = 0.06340 -0.00138 0.01168 0.01221 AFIX 43 H9 2 0.413796 0.406243 0.533950 11.00000 -1.20000 AFIX 0 C10 1 0.336938 0.601524 0.554934 11.00000 0.07282 0.08162 = 0.07264 -0.00455 0.00823 0.01374 AFIX 43 H10 2 0.317079 0.625475 0.519697 11.00000 -1.20000 AFIX 0 C11 1 0.295036 0.727143 0.590611 11.00000 0.05970 0.07735 = 0.08854 -0.00586 0.01092 0.00115 HKLF 4 REM ad26_a.res in C2/c REM R1 = 0.0758 for 933 Fo > 4sig(Fo) and 0.2002 for all 2930 data REM 146 parameters refined using 0 restraints END WGHT 0.0965 0.0000 REM Highest difference peak 0.238, deepest hole -0.180, 1-sigma level 0.053 Q1 1 0.5212 -0.1065 0.5606 11.00000 0.05 0.20 Q2 1 0.6565 -0.3871 0.5832 11.00000 0.05 0.16 Q3 1 0.4803 0.3406 0.7028 11.00000 0.05 0.16 Q4 1 0.7034 -0.4561 0.6413 11.00000 0.05 0.16 Q5 1 0.5261 0.6786 0.5780 11.00000 0.05 0.15 Q6 1 0.5394 -0.2707 0.6390 11.00000 0.05 0.14 Q7 1 0.5993 0.1391 0.7957 11.00000 0.05 0.14 Q8 1 0.5993 -0.5179 0.5624 11.00000 0.05 0.14 Q9 1 0.3024 1.0056 0.6614 11.00000 0.05 0.14 Q10 1 0.5403 0.4266 0.5763 11.00000 0.05 0.13 Q11 1 0.5739 0.5552 0.7412 11.00000 0.05 0.13 Q12 1 0.2831 1.1255 0.5799 11.00000 0.05 0.13 Q13 1 0.6354 -0.3965 0.7782 11.00000 0.05 0.13 Q14 1 0.2544 0.8755 0.6237 11.00000 0.05 0.13 Q15 1 0.2968 0.7509 0.6566 11.00000 0.05 0.12 Q16 1 0.7198 0.0415 0.8010 11.00000 0.05 0.12 Q17 1 0.7165 -0.2551 0.7549 11.00000 0.05 0.12 Q18 1 0.5990 0.3678 0.5763 11.00000 0.05 0.12 Q19 1 0.2147 0.8633 0.5358 11.00000 0.05 0.12 Q20 1 0.4231 0.4686 0.7202 11.00000 0.05 0.12 ; _shelx_res_checksum 92962 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.56941(13) -0.0067(8) 0.53876(10) 0.0992(9) Uani 1 1 d . . . . . O2 O 0.43111(10) 0.4394(6) 0.65667(8) 0.0822(7) Uani 1 1 d . . . . . O3 O 0.24094(12) 0.8567(7) 0.57243(10) 0.0979(9) Uani 1 1 d . . . . . O4 O 0.31629(12) 0.7102(8) 0.64143(9) 0.0936(8) Uani 1 1 d . . . . . H4O H 0.352542 0.610548 0.648262 0.140 Uiso 1 1 calc R U . . . N1 N 0.50112(11) 0.2236(6) 0.60863(9) 0.0653(7) Uani 1 1 d . . . . . H1N H 0.504932 0.189628 0.576947 0.078 Uiso 1 1 calc R U . . . C1 C 0.55599(14) 0.1103(8) 0.64757(12) 0.0624(8) Uani 1 1 d . . . . . C2 C 0.55756(17) 0.1457(9) 0.69998(13) 0.0755(9) Uani 1 1 d . . . . . H2 H 0.521610 0.245063 0.711116 0.091 Uiso 1 1 calc R U . . . C3 C 0.61377(17) 0.0310(9) 0.73659(14) 0.0813(10) Uani 1 1 d . . . . . H3 H 0.614872 0.055022 0.772096 0.098 Uiso 1 1 calc R U . . . C4 C 0.66673(17) -0.1150(9) 0.72087(15) 0.0795(10) Uani 1 1 d . . . . . H4 H 0.703832 -0.188423 0.745560 0.095 Uiso 1 1 calc R U . . . C5 C 0.66533(16) -0.1537(8) 0.66858(15) 0.0765(9) Uani 1 1 d . . . . . H5 H 0.701560 -0.254180 0.657982 0.092 Uiso 1 1 calc R U . . . C6 C 0.61014(14) -0.0441(8) 0.63121(12) 0.0633(8) Uani 1 1 d . . . . . C7 C 0.61205(17) -0.0918(9) 0.57696(15) 0.0801(10) Uani 1 1 d . . . . . H7 H 0.650011 -0.199456 0.570241 0.096 Uiso 1 1 calc R U . . . C8 C 0.44366(15) 0.3773(8) 0.61392(12) 0.0634(8) Uani 1 1 d . . . . . C9 C 0.39790(15) 0.4602(8) 0.56370(11) 0.0706(9) Uani 1 1 d . . . . . H9 H 0.413796 0.406243 0.533950 0.085 Uiso 1 1 calc R U . . . C10 C 0.33694(16) 0.6015(9) 0.55493(13) 0.0768(10) Uani 1 1 d . . . . . H10 H 0.317079 0.625475 0.519697 0.092 Uiso 1 1 calc R U . . . C11 C 0.29504(17) 0.7271(9) 0.59061(14) 0.0759(9) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0788(17) 0.138(2) 0.0807(16) -0.0043(14) 0.0165(14) 0.0295(16) O2 0.0653(15) 0.1158(19) 0.0658(14) -0.0023(12) 0.0144(11) 0.0169(13) O3 0.0661(16) 0.121(2) 0.1036(19) 0.0033(15) 0.0116(14) 0.0302(14) O4 0.0667(16) 0.135(2) 0.0788(16) -0.0137(14) 0.0144(13) 0.0244(14) N1 0.0548(15) 0.0774(17) 0.0639(15) -0.0003(12) 0.0128(12) 0.0077(12) C1 0.0523(17) 0.0618(18) 0.0709(19) -0.0004(15) 0.0085(14) 0.0002(14) C2 0.065(2) 0.083(2) 0.080(2) -0.0003(17) 0.0178(17) 0.0082(16) C3 0.074(2) 0.086(2) 0.079(2) -0.0008(18) 0.0051(18) 0.0089(19) C4 0.0566(19) 0.080(2) 0.094(3) 0.0120(19) -0.0012(17) 0.0025(17) C5 0.0531(18) 0.069(2) 0.104(3) 0.0069(18) 0.0094(17) 0.0041(15) C6 0.0528(17) 0.0605(18) 0.078(2) 0.0004(15) 0.0162(15) 0.0010(13) C7 0.062(2) 0.087(2) 0.096(3) 0.001(2) 0.027(2) 0.0060(18) C8 0.0571(18) 0.0715(19) 0.0612(19) 0.0011(14) 0.0114(15) 0.0044(14) C9 0.061(2) 0.086(2) 0.0634(18) -0.0014(16) 0.0117(16) 0.0122(16) C10 0.073(2) 0.082(2) 0.073(2) -0.0046(16) 0.0082(18) 0.0137(17) C11 0.060(2) 0.077(2) 0.089(3) -0.0059(18) 0.0109(19) 0.0012(16) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O4 H4O 109.5 . . ? C8 N1 C1 129.5(3) . . ? C8 N1 H1N 115.3 . . ? C1 N1 H1N 115.3 . . ? C2 C1 C6 119.8(3) . . ? C2 C1 N1 122.3(3) . . ? C6 C1 N1 117.9(3) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.3(3) . . ? C5 C6 C7 117.7(3) . . ? C1 C6 C7 123.0(3) . . ? O1 C7 C6 127.4(3) . . ? O1 C7 H7 116.3 . . ? C6 C7 H7 116.3 . . ? O2 C8 N1 122.5(3) . . ? O2 C8 C9 123.7(3) . . ? N1 C8 C9 113.8(3) . . ? C10 C9 C8 129.2(3) . . ? C10 C9 H9 115.4 . . ? C8 C9 H9 115.4 . . ? C9 C10 C11 132.2(3) . . ? C9 C10 H10 113.9 . . ? C11 C10 H10 113.9 . . ? O3 C11 O4 119.7(3) . . ? O3 C11 C10 119.4(3) . . ? O4 C11 C10 120.9(3) . . ? 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 O1 C7 1.223(4) . ? O2 C8 1.224(3) . ? O3 C11 1.215(4) . ? O4 C11 1.310(4) . ? O4 H4O 0.8200 . ? N1 C8 1.350(4) . ? N1 C1 1.415(4) . ? N1 H1N 0.8600 . ? C1 C2 1.373(4) . ? C1 C6 1.403(4) . ? C2 C3 1.402(4) . ? C2 H2 0.9300 . ? C3 C4 1.361(5) . ? C3 H3 0.9300 . ? C4 C5 1.372(5) . ? C4 H4 0.9300 . ? C5 C6 1.393(4) . ? C5 H5 0.9300 . ? C6 C7 1.441(5) . ? C7 H7 0.9300 . ? C8 C9 1.477(4) . ? C9 C10 1.336(4) . ? C9 H9 0.9300 . ? C10 C11 1.479(4) . ? C10 H10 0.9300 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O1 0.86 1.97 2.680(3) 139.2 . O4 H4O O2 0.82 1.71 2.524(3) 172.4 . 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 C8 N1 C1 C2 0.1(5) . . . . ? C8 N1 C1 C6 179.9(3) . . . . ? C6 C1 C2 C3 0.8(5) . . . . ? N1 C1 C2 C3 -179.4(3) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C2 C3 C4 C5 -0.5(5) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C4 C5 C6 C7 179.8(3) . . . . ? C2 C1 C6 C5 -1.1(5) . . . . ? N1 C1 C6 C5 179.1(3) . . . . ? C2 C1 C6 C7 179.7(3) . . . . ? N1 C1 C6 C7 -0.1(4) . . . . ? C5 C6 C7 O1 -178.4(3) . . . . ? C1 C6 C7 O1 0.8(6) . . . . ? C1 N1 C8 O2 -0.6(5) . . . . ? C1 N1 C8 C9 179.7(3) . . . . ? O2 C8 C9 C10 -1.8(6) . . . . ? N1 C8 C9 C10 177.9(3) . . . . ? C8 C9 C10 C11 1.1(7) . . . . ? C9 C10 C11 O3 177.9(4) . . . . ? C9 C10 C11 O4 0.0(6) . . . . ?