#------------------------------------------------------------------------------ #$Date: 2017-06-09 08:19:15 +0300 (Fri, 09 Jun 2017) $ #$Revision: 197680 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/84/7228451.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_7228451 loop_ _publ_author_name 'Aksenov, Alexander V.' 'Ovcharov, Dmitrii S.' 'Aksenov, Nicolai A.' 'Aksenov, Dmitrii A.' 'Nadein, Oleg N.' 'Rubin, Michael' _publ_section_title ; Dual role of polyphosphoric acid-activated nitroalkanes in oxidative peri-annulations: efficient synthesis of 1,3,6,8-tetraazapyrenes ; _journal_issue 48 _journal_name_full 'RSC Adv.' _journal_page_first 29927 _journal_paper_doi 10.1039/C7RA04751G _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C14 H10 N4' _chemical_formula_sum 'C14 H10 N4' _chemical_formula_weight 234.26 _chemical_name_systematic 2,7-dimethyl-1,3,6,8-Tetraazapyrene _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _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 dual _audit_creation_date 2017-04-15 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _audit_update_record ; 2017-04-15 deposited with the CCDC. 2017-06-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.335(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.8706(2) _cell_length_b 7.4727(4) _cell_length_c 18.9360(12) _cell_measurement_reflns_used 2767 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 73.3260 _cell_measurement_theta_min 5.9400 _cell_volume 547.69(5) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2529 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -116.00 -17.00 1.00 3.17 -- -41.60 -38.00 0.00 99 2 \w -33.00 66.00 1.00 3.17 -- 41.60 -38.00 150.00 99 3 \w 26.00 99.00 1.00 3.17 -- 41.60-128.00 116.00 73 4 \w 94.00 178.00 1.00 12.67 -- 106.96 125.00-180.00 84 5 \w 25.00 109.00 1.00 12.67 -- 106.96 -95.00 0.00 84 6 \w 25.00 160.00 1.00 12.67 -- 106.96 -15.00 0.00 135 7 \w -118.00 -9.00 1.00 3.17 -- -41.60 -77.00-120.00 109 8 \w -70.00 32.00 1.00 3.17 -- -41.60 57.00 -30.00 102 9 \w -114.00 -13.00 1.00 3.17 -- -41.60 -57.00 120.00 101 10 \w 54.00 117.00 1.00 12.67 -- 106.96 15.00 150.00 63 11 \w 94.00 178.00 1.00 12.67 -- 106.96 125.00 0.00 84 12 \w 87.00 126.00 1.00 12.67 -- 106.96 45.00-150.00 39 13 \w 87.00 119.00 1.00 12.67 -- 106.96 -77.00-150.00 32 14 \w -118.00 -9.00 1.00 3.17 -- -41.85 -77.00 -30.00 109 15 \w -114.00 -62.00 1.00 3.17 -- -41.85-143.00 -52.00 52 16 \w 9.00 118.00 1.00 3.17 -- 41.85 77.00 150.00 109 17 \w 9.00 118.00 1.00 3.17 -- 41.85 77.00-120.00 109 18 \w 23.00 98.00 1.00 3.17 -- 41.85-125.00 150.00 75 19 \w 94.00 178.00 1.00 12.67 -- 106.96 125.00 -60.00 84 20 \w 78.00 178.00 1.00 12.67 -- 106.96 61.00 150.00 100 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0264376000 _diffrn_orient_matrix_UB_12 0.1870967000 _diffrn_orient_matrix_UB_13 0.0337144000 _diffrn_orient_matrix_UB_21 -0.0067232000 _diffrn_orient_matrix_UB_22 -0.0859924000 _diffrn_orient_matrix_UB_23 0.0739296000 _diffrn_orient_matrix_UB_31 0.3970391000 _diffrn_orient_matrix_UB_32 0.0108655000 _diffrn_orient_matrix_UB_33 0.0039740000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0171 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 5093 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.631 _diffrn_reflns_theta_min 4.670 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear yellowish yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier yellowish _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.420 _exptl_crystal_description needle _exptl_crystal_F_000 244 _exptl_crystal_recrystallization_method 'Crystallized by slow evaporation method with CDCl3 as slovent' _exptl_crystal_size_max 0.511 _exptl_crystal_size_mid 0.078 _exptl_crystal_size_min 0.041 _refine_diff_density_max 0.207 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 83 _refine_ls_number_reflns 1087 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0455 _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^)+(0.0786P)^2^+0.0866P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1312 _refine_ls_wR_factor_ref 0.1457 _reflns_Friedel_coverage 0.000 _reflns_number_gt 942 _reflns_number_total 1087 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; anna_me_14042017_2.res created by SHELXL-2014/7 TITL anna_me_14042017_2_a.res in P2(1)/n REM Old TITL ANNA_ME_14042017_2 in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.241, Rweak 0.212, Alpha 0.020, Orientation as input REM Formula found by SHELXT: C8 N CELL 1.54184 3.8706 7.4727 18.936 90 90.335 90 ZERR 2 0.0002 0.0004 0.0012 0 0.006 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 28 20 8 L.S. 33 0 0 PLAN 20 BOND $H list 4 fmap 2 53 acta OMIT 3 4 13 REM REM REM WGHT 0.078600 0.086600 FVAR 1.13786 N4 3 0.263475 0.164895 0.573536 11.00000 0.04688 0.04083 = 0.05237 -0.00083 0.00019 -0.00724 N3 3 0.527849 0.378991 0.651990 11.00000 0.04851 0.04884 = 0.04516 -0.00203 -0.00151 -0.00413 C11 1 0.474816 0.442018 0.528706 11.00000 0.03323 0.03576 = 0.04525 -0.00580 -0.00027 -0.00139 C5 1 0.315894 0.274545 0.518540 11.00000 0.03620 0.03624 = 0.04838 -0.00512 -0.00086 -0.00268 C7 1 0.578178 0.489791 0.597104 11.00000 0.03678 0.04084 = 0.04495 -0.00587 -0.00109 -0.00134 C9 1 0.210620 0.225537 0.448175 11.00000 0.04668 0.03873 = 0.05359 -0.00861 -0.00472 -0.00872 AFIX 43 H9 2 0.106722 0.115018 0.440377 11.00000 -1.20000 AFIX 0 C13 1 0.369624 0.222707 0.637006 11.00000 0.04449 0.04751 = 0.05151 0.00003 0.00010 -0.00421 C8 1 0.260563 0.337792 0.393279 11.00000 0.04910 0.04527 = 0.04708 -0.01095 -0.00609 -0.00560 AFIX 43 H8 2 0.189474 0.303205 0.348309 11.00000 -1.20000 AFIX 0 C12 1 0.305937 0.100266 0.698084 11.00000 0.07268 0.06668 = 0.05757 0.01148 -0.00247 -0.01627 AFIX 137 H12C 2 0.166977 0.001025 0.682763 11.00000 -1.50000 H12A 2 0.187307 0.164327 0.734591 11.00000 -1.50000 H12B 2 0.522666 0.056890 0.716084 11.00000 -1.50000 AFIX 0 HKLF 4 REM anna_me_14042017_2_a.res in P2(1)/n REM R1 = 0.0455 for 942 Fo > 4sig(Fo) and 0.0518 for all 1087 data REM 83 parameters refined using 0 restraints END WGHT 0.0786 0.0866 REM Highest difference peak 0.207, deepest hole -0.227, 1-sigma level 0.062 Q1 1 0.0472 0.0873 0.7045 11.00000 0.05 0.21 Q2 1 -0.0345 0.1184 0.7140 11.00000 0.05 0.19 Q3 1 0.4136 0.1378 0.7435 11.00000 0.05 0.18 Q4 1 0.4186 -0.0435 0.6958 11.00000 0.05 0.18 Q5 1 0.0782 0.3484 0.7598 11.00000 0.05 0.15 Q6 1 0.4732 0.2464 0.2960 11.00000 0.05 0.15 Q7 1 0.8003 0.0374 0.6988 11.00000 0.05 0.14 Q8 1 0.6791 0.3799 0.6999 11.00000 0.05 0.14 Q9 1 -0.0973 0.0538 0.7544 11.00000 0.05 0.13 Q10 1 -0.0338 0.2353 0.7404 11.00000 0.05 0.13 Q11 1 0.7633 0.3750 0.6862 11.00000 0.05 0.13 Q12 1 -0.1513 0.2385 0.6972 11.00000 0.05 0.12 Q13 1 0.4156 -0.1602 0.6821 11.00000 0.05 0.12 Q14 1 0.7287 0.2388 0.7187 11.00000 0.05 0.12 Q15 1 0.6623 -0.1253 0.7048 11.00000 0.05 0.12 Q16 1 0.1091 0.2551 0.7857 11.00000 0.05 0.12 Q17 1 0.4527 0.3464 0.5200 11.00000 0.05 0.11 Q18 1 0.7671 0.5429 0.6022 11.00000 0.05 0.11 Q19 1 0.0852 0.3735 0.7016 11.00000 0.05 0.11 Q20 1 0.6975 0.3671 0.7370 11.00000 0.05 0.11 REM The information below was added by Olex2. REM REM R1 = 0.0455 for 942 Fo > 4sig(Fo) and 0.0518 for all 5380 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.21, deepest hole -0.23 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0518 REM R1_gt = 0.0455 REM wR_ref = 0.1457 REM GOOF = 1.139 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 5380 REM Reflections_gt = 942 REM Parameters = n/a REM Hole = -0.23 REM Peak = 0.21 REM Flack = n/a ; _cod_data_source_file c7ra04751g2.cif _cod_data_source_block anna_me_14042017_2 _cod_database_code 7228451 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'C11 H10 N O' _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. ; _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C9(H9), C8(H8) 2.b Idealised Me refined as rotating group: C12(H12C,H12A,H12B) ; _olex2_date_sample_data_collection 2017-04-14 _olex2_exptl_crystal_mounting_method 'Mounted by acrylic glue on the glass stick' _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.843 _oxdiff_exptl_absorpt_empirical_full_min 0.574 loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn N4 N 0.2635(3) 0.16489(16) 0.57354(7) 0.0467(4) Uani 1 1 d . N3 N 0.5278(3) 0.37899(17) 0.65199(6) 0.0475(4) Uani 1 1 d . C11 C 0.4748(3) 0.44202(17) 0.52871(7) 0.0381(4) Uani 1 1 d . C5 C 0.3159(3) 0.27455(18) 0.51854(7) 0.0403(4) Uani 1 1 d . C7 C 0.5782(3) 0.48979(19) 0.59710(7) 0.0409(4) Uani 1 1 d . C9 C 0.2106(4) 0.22554(19) 0.44818(8) 0.0464(4) Uani 1 1 d . H9 H 0.1067 0.1150 0.4404 0.056 Uiso 1 1 calc R C13 C 0.3696(4) 0.2227(2) 0.63701(8) 0.0478(4) Uani 1 1 d . C8 C 0.2606(4) 0.3378(2) 0.39328(8) 0.0472(4) Uani 1 1 d . H8 H 0.1895 0.3032 0.3483 0.057 Uiso 1 1 calc R C12 C 0.3059(5) 0.1003(3) 0.69808(9) 0.0657(5) Uani 1 1 d . H12C H 0.1670 0.0010 0.6828 0.098 Uiso 1 1 calc GR H12A H 0.1873 0.1643 0.7346 0.098 Uiso 1 1 calc GR H12B H 0.5227 0.0569 0.7161 0.098 Uiso 1 1 calc GR 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 N4 0.0469(7) 0.0408(7) 0.0524(7) -0.0008(5) 0.0002(5) -0.0072(5) N3 0.0485(7) 0.0488(7) 0.0452(7) -0.0020(5) -0.0015(5) -0.0041(5) C11 0.0332(7) 0.0358(7) 0.0453(8) -0.0058(6) -0.0003(5) -0.0014(5) C5 0.0362(7) 0.0362(7) 0.0484(8) -0.0051(6) -0.0009(6) -0.0027(5) C7 0.0368(7) 0.0408(7) 0.0450(8) -0.0059(6) -0.0011(5) -0.0013(5) C9 0.0467(8) 0.0387(7) 0.0536(9) -0.0086(6) -0.0047(6) -0.0087(6) C13 0.0445(8) 0.0475(8) 0.0515(9) 0.0000(6) 0.0001(6) -0.0042(6) C8 0.0491(8) 0.0453(8) 0.0471(8) -0.0109(6) -0.0061(6) -0.0056(6) C12 0.0727(11) 0.0667(11) 0.0576(10) 0.0115(9) -0.0025(8) -0.0163(9) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 5 -2 0.0193 -3 0 -1 0.2691 0 -5 2 0.0214 2 0 2 0.2275 0 -1 78 0.0364 0 1 -65 0.0299 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 C13 N4 C5 116.91(13) . . C7 N3 C13 116.02(13) . . C11 C11 C5 120.35(15) 3_666 . C7 C11 C11 121.24(15) . 3_666 C7 C11 C5 118.41(13) . . N4 C5 C11 120.33(13) . . N4 C5 C9 121.35(13) . . C11 C5 C9 118.32(13) . . N3 C7 C11 121.10(13) . . N3 C7 C8 121.14(13) . 3_666 C11 C7 C8 117.76(13) . 3_666 C5 C9 H9 119.5 . . C8 C9 C5 120.92(13) . . C8 C9 H9 119.5 . . N4 C13 N3 127.22(14) . . N4 C13 C12 116.44(14) . . N3 C13 C12 116.34(14) . . C7 C8 H8 119.3 3_666 . C9 C8 C7 121.42(13) . 3_666 C9 C8 H8 119.3 . . C13 C12 H12C 109.5 . . C13 C12 H12A 109.5 . . C13 C12 H12B 109.5 . . H12C C12 H12A 109.5 . . H12C C12 H12B 109.5 . . H12A C12 H12B 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N4 C5 1.3415(18) . N4 C13 1.3395(19) . N3 C7 1.3439(19) . N3 C13 1.348(2) . C11 C11 1.405(3) 3_666 C11 C5 1.4072(19) . C11 C7 1.3996(19) . C5 C9 1.4385(19) . C7 C8 1.4427(19) 3_666 C9 H9 0.9300 . C9 C8 1.351(2) . C13 C12 1.496(2) . C8 C7 1.4427(19) 3_666 C8 H8 0.9300 . C12 H12C 0.9600 . C12 H12A 0.9600 . C12 H12B 0.9600 . loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0237 4.7429 -1.8379 0.8248 -0.5439 0.0536 -2.5010 -0.3833 -0.6231 -0.0266 0.0037 -0.9996 -0.0280 -4.7517 1.7985 -0.8276 0.5418 -0.0556 2.4851 0.0971 1.7319 0.0109 0.1030 0.9946 0.1316 -1.3490 78.2514 2.3823 5.9002 0.3486 -0.0142 1.3522 -65.1442 -1.9429 -4.9323 -0.2498