#------------------------------------------------------------------------------ #$Date: 2016-09-28 09:33:02 +0300 (Wed, 28 Sep 2016) $ #$Revision: 186819 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/66/7226668.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_7226668 loop_ _publ_author_name 'Nelyubina, Yu. V.' 'Ananyev, I. V.' 'Novikov, V. V.' 'Lyssenko, K. A.' _publ_section_title ; Invariom approach to electron density studies of open-shell compounds: the case of an organic nitroxide radical ; _journal_issue 94 _journal_name_full 'RSC Adv.' _journal_page_first 91694 _journal_paper_doi 10.1039/C6RA21365K _journal_volume 6 _journal_year 2016 _chemical_formula_moiety 'C9 H16 N O2' _chemical_formula_sum 'C9 H16 N O2' _chemical_formula_weight 170.23 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2014/6 _audit_update_record ; 2016-08-23 deposited with the CCDC. 2016-09-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.8102(2) _cell_length_b 11.8025(3) _cell_length_c 10.2102(2) _cell_measurement_reflns_used 6066 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 3 _cell_volume 941.18(4) _computing_cell_refinement 'APEX2 (Bruker, 2005)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'APEX2 (Bruker, 2005)' _computing_molecular_graphics 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_publication_material 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' _computing_structure_solution 'APEX2 (Bruker, 2005)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX2 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_unetI/netI 0.0152 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 180671 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 60.000 _diffrn_reflns_theta_min 1.725 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'APEX2 (Bruker, 2005)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.201 _exptl_crystal_description prism _exptl_crystal_F_000 372 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.320 _refine_diff_density_max 0.389 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details ; Flack x determined using 5477 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 14287 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0303 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.0145P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.0809 _reflns_Friedel_coverage 0.940 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 12326 _reflns_number_total 14287 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra21365k1.cif _cod_data_source_block tempone _cod_database_code 7226668 _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 0.963 _shelx_estimated_absorpt_t_max 0.974 _shelxl_version_number 2014/6 _shelx_res_file ; TITL b in Pca2(1) CELL 0.71073 7.8102 11.8025 10.2102 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0003 0.0002 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 0.5+Z SYMM 0.5+X, -Y, Z SYMM 0.5-X, Y, 0.5+Z SFAC C H N O UNIT 36 64 4 8 TEMP -173 bond $h size 0.45 0.35 0.32 omit -4 120 omit 0 1 -6 L.S. 4 acta BOND FMAP 2 PLAN 20 WGHT 0.044300 0.014500 FVAR 0.95161 O1 4 0.228853 0.680220 0.919708 11.00000 0.02141 0.02109 = 0.02879 -0.00769 0.01281 0.00035 O2 4 -0.247510 0.865966 1.238589 11.00000 0.01664 0.02478 = 0.02087 -0.00637 0.00631 0.00187 N1 3 0.116781 0.723367 0.996292 11.00000 0.01299 0.01246 = 0.01422 -0.00122 0.00308 0.00063 C1 1 -0.046470 0.660690 1.017314 11.00000 0.01358 0.01159 = 0.01303 -0.00008 0.00002 0.00003 C2 1 -0.186646 0.745396 1.056555 11.00000 0.01132 0.01535 = 0.01366 -0.00089 -0.00079 0.00044 C3 1 -0.139320 0.822985 1.168308 11.00000 0.01238 0.01442 = 0.01166 -0.00043 0.00162 0.00082 C4 1 0.049247 0.844290 1.187781 11.00000 0.01295 0.01702 = 0.01092 -0.00147 -0.00036 -0.00055 C5 1 0.158532 0.832105 1.063350 11.00000 0.01090 0.01345 = 0.01227 0.00004 0.00039 -0.00037 C6 1 -0.097168 0.602932 0.889388 11.00000 0.02456 0.01927 = 0.01872 -0.00678 -0.00196 -0.00157 C7 1 -0.017078 0.571317 1.124241 11.00000 0.02084 0.01549 = 0.02217 0.00652 0.00036 0.00066 C8 1 0.123644 0.929917 0.967854 11.00000 0.01909 0.01387 = 0.01604 0.00233 0.00206 -0.00025 C9 1 0.347618 0.830434 1.102123 11.00000 0.01116 0.02657 = 0.02176 0.00014 -0.00109 -0.00124 H2A 2 -0.216028 0.791931 0.983116 11.00000 0.02376 H2B 2 -0.289828 0.708480 1.076412 11.00000 0.02737 H4A 2 0.063275 0.921091 1.218338 11.00000 0.02740 H4B 2 0.089144 0.790760 1.251728 11.00000 0.02295 H6A 2 -0.106402 0.658377 0.816846 11.00000 0.04411 H6B 2 -0.018313 0.547578 0.861736 11.00000 0.04054 H6C 2 -0.201825 0.561494 0.900770 11.00000 0.04245 H7A 2 0.072502 0.520026 1.096692 11.00000 0.03094 H7B 2 -0.116898 0.524115 1.133363 11.00000 0.03131 H7C 2 0.015755 0.602719 1.208134 11.00000 0.03726 H8A 2 0.000365 0.930608 0.943325 11.00000 0.02946 H8B 2 0.192175 0.924515 0.890886 11.00000 0.02645 H8C 2 0.149046 1.003328 1.007783 11.00000 0.02542 H9C 2 0.377154 0.900641 1.148091 11.00000 0.02792 H9A 2 0.417536 0.821788 1.022548 11.00000 0.03124 H9B 2 0.366773 0.766708 1.157063 11.00000 0.02504 HKLF 4 REM b in Pca2(1) REM R1 = 0.0303 for 12326 Fo > 4sig(Fo) and 0.0402 for all 14287 data REM 173 parameters refined using 1 restraints END WGHT 0.0466 0.0074 REM Highest difference peak 0.389, deepest hole -0.222, 1-sigma level 0.051 Q1 1 -0.1974 0.8445 1.2008 11.00000 0.05 0.39 Q2 1 0.2732 0.8261 1.0865 11.00000 0.05 0.27 Q3 1 -0.2010 0.8546 1.2563 11.00000 0.05 0.27 Q4 1 0.2335 0.8421 1.0733 11.00000 0.05 0.27 Q5 1 0.1889 0.6492 0.8990 11.00000 0.05 0.26 Q6 1 0.2401 0.6655 0.9624 11.00000 0.05 0.26 Q7 1 0.0593 0.6973 1.0017 11.00000 0.05 0.25 Q8 1 -0.0625 0.6378 0.9667 11.00000 0.05 0.25 Q9 1 -0.3151 0.8602 1.2394 11.00000 0.05 0.25 Q10 1 -0.1669 0.7730 1.1014 11.00000 0.05 0.25 Q11 1 -0.0531 0.8349 1.1760 11.00000 0.05 0.24 Q12 1 0.1541 0.8726 1.0210 11.00000 0.05 0.24 Q13 1 -0.1635 0.7896 1.1314 11.00000 0.05 0.24 Q14 1 0.2767 0.7195 0.9211 11.00000 0.05 0.24 Q15 1 0.1321 0.9004 1.0023 11.00000 0.05 0.23 Q16 1 0.1401 0.7514 1.0339 11.00000 0.05 0.23 Q17 1 0.1732 0.7016 0.9664 11.00000 0.05 0.22 Q18 1 -0.0189 0.6050 1.0844 11.00000 0.05 0.22 Q19 1 -0.0352 0.6250 1.0612 11.00000 0.05 0.21 Q20 1 0.3975 0.8314 1.0628 11.00000 0.05 0.20 ; _shelx_res_checksum 34953 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 O1 O 0.22885(5) 0.68022(3) 0.91971(4) 0.02376(7) Uani 1 1 d O2 O -0.24751(5) 0.86597(3) 1.23859(4) 0.02076(5) Uani 1 1 d N1 N 0.11678(4) 0.72337(2) 0.99629(3) 0.01322(4) Uani 1 1 d C1 C -0.04647(4) 0.66069(3) 1.01731(3) 0.01273(4) Uani 1 1 d C2 C -0.18665(4) 0.74540(3) 1.05655(4) 0.01344(4) Uani 1 1 d C3 C -0.13932(4) 0.82299(3) 1.16831(3) 0.01282(4) Uani 1 1 d C4 C 0.04925(4) 0.84429(3) 1.18778(3) 0.01363(4) Uani 1 1 d C5 C 0.15853(4) 0.83210(3) 1.06335(3) 0.01220(4) Uani 1 1 d C6 C -0.09717(7) 0.60293(4) 0.88939(5) 0.02085(7) Uani 1 1 d C7 C -0.01708(6) 0.57132(4) 1.12424(5) 0.01950(6) Uani 1 1 d C8 C 0.12364(5) 0.92992(3) 0.96785(4) 0.01634(5) Uani 1 1 d C9 C 0.34762(5) 0.83043(4) 1.10212(5) 0.01983(6) Uani 1 1 d H2A H -0.2160(15) 0.7919(10) 0.9831(13) 0.024(2) Uiso 1 1 d H2B H -0.2898(17) 0.7085(11) 1.0764(14) 0.027(3) Uiso 1 1 d H4A H 0.0633(17) 0.9211(11) 1.2183(13) 0.027(3) Uiso 1 1 d H4B H 0.0891(16) 0.7908(11) 1.2517(13) 0.023(2) Uiso 1 1 d H6A H -0.106(2) 0.6584(15) 0.8168(19) 0.044(4) Uiso 1 1 d H6B H -0.018(2) 0.5476(13) 0.8617(16) 0.041(4) Uiso 1 1 d H6C H -0.2018(19) 0.5615(14) 0.9008(18) 0.042(4) Uiso 1 1 d H7A H 0.0725(19) 0.5200(11) 1.0967(13) 0.031(3) Uiso 1 1 d H7B H -0.1169(17) 0.5241(11) 1.1334(15) 0.031(3) Uiso 1 1 d H7C H 0.0158(17) 0.6027(13) 1.2081(15) 0.037(3) Uiso 1 1 d H8A H 0.0004(16) 0.9306(11) 0.9433(14) 0.029(3) Uiso 1 1 d H8B H 0.1922(16) 0.9245(11) 0.8909(14) 0.026(3) Uiso 1 1 d H8C H 0.1490(16) 1.0033(11) 1.0078(12) 0.025(3) Uiso 1 1 d H9C H 0.3772(16) 0.9006(12) 1.1481(13) 0.028(3) Uiso 1 1 d H9A H 0.4175(19) 0.8218(12) 1.0225(15) 0.031(3) Uiso 1 1 d H9B H 0.3668(16) 0.7667(11) 1.1571(13) 0.025(3) Uiso 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 0.02141(13) 0.02109(12) 0.02879(16) -0.00769(11) 0.01281(12) 0.00035(10) O2 0.01664(10) 0.02478(13) 0.02087(12) -0.00637(10) 0.00631(9) 0.00187(10) N1 0.01299(8) 0.01246(7) 0.01422(8) -0.00122(7) 0.00308(7) 0.00063(6) C1 0.01358(9) 0.01159(8) 0.01303(9) -0.00008(7) 0.00002(7) 0.00003(7) C2 0.01132(8) 0.01535(10) 0.01366(9) -0.00089(8) -0.00079(7) 0.00044(7) C3 0.01238(9) 0.01442(9) 0.01166(9) -0.00043(7) 0.00162(7) 0.00082(7) C4 0.01295(9) 0.01702(11) 0.01092(9) -0.00147(8) -0.00036(7) -0.00055(8) C5 0.01090(8) 0.01345(9) 0.01227(9) 0.00004(7) 0.00039(7) -0.00037(7) C6 0.02456(16) 0.01927(13) 0.01872(14) -0.00678(11) -0.00196(12) -0.00157(12) C7 0.02084(14) 0.01549(11) 0.02217(15) 0.00652(11) 0.00036(12) 0.00066(11) C8 0.01909(12) 0.01387(10) 0.01604(11) 0.00233(9) 0.00206(10) -0.00025(9) C9 0.01116(10) 0.02657(17) 0.02176(15) 0.00014(13) -0.00109(10) -0.00124(10) 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 O1 N1 C1 118.42(3) O1 N1 C5 118.28(3) C1 N1 C5 123.27(3) N1 C1 C6 108.70(3) N1 C1 C7 108.40(3) C6 C1 C7 109.91(3) N1 C1 C2 108.93(3) C6 C1 C2 109.22(3) C7 C1 C2 111.61(3) C3 C2 C1 114.69(3) C3 C2 H2A 107.6(8) C1 C2 H2A 109.9(7) C3 C2 H2B 109.2(9) C1 C2 H2B 111.5(8) H2A C2 H2B 103.3(11) O2 C3 C4 122.02(3) O2 C3 C2 121.86(3) C4 C3 C2 116.12(3) C3 C4 C5 114.70(3) C3 C4 H4A 108.1(8) C5 C4 H4A 107.0(8) C3 C4 H4B 107.3(7) C5 C4 H4B 108.7(8) H4A C4 H4B 111.2(11) N1 C5 C9 108.61(3) N1 C5 C8 108.47(3) C9 C5 C8 110.21(3) N1 C5 C4 109.80(3) C9 C5 C4 108.87(3) C8 C5 C4 110.85(3) C1 C6 H6A 111.3(11) C1 C6 H6B 113.4(10) H6A C6 H6B 106.4(14) C1 C6 H6C 110.2(11) H6A C6 H6C 111.4(14) H6B C6 H6C 103.9(14) C1 C7 H7A 109.4(8) C1 C7 H7B 110.2(8) H7A C7 H7B 104.6(11) C1 C7 H7C 113.9(9) H7A C7 H7C 107.8(12) H7B C7 H7C 110.5(13) C5 C8 H8A 109.7(8) C5 C8 H8B 111.9(8) H8A C8 H8B 109.7(11) C5 C8 H8C 111.4(7) H8A C8 H8C 107.1(10) H8B C8 H8C 106.8(11) C5 C9 H9C 109.9(7) C5 C9 H9A 108.9(9) H9C C9 H9A 110.6(11) C5 C9 H9B 108.4(8) H9C C9 H9B 110.5(12) H9A C9 H9B 108.5(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 N1 1.2794(4) O2 C3 1.2191(4) N1 C1 1.4896(5) N1 C5 1.4907(4) C1 C6 1.5256(5) C1 C7 1.5353(5) C1 C2 1.5358(5) C2 C3 1.5090(5) C2 H2A 0.957(13) C2 H2B 0.938(13) C3 C4 1.5072(5) C4 C5 1.5373(5) C4 H4A 0.965(13) C4 H4B 0.960(13) C5 C9 1.5291(5) C5 C8 1.5355(5) C6 H6A 0.991(19) C6 H6B 0.941(15) C6 H6C 0.960(16) C7 H7A 0.967(14) C7 H7B 0.963(13) C7 H7C 0.968(16) C8 H8A 0.995(12) C8 H8B 0.953(14) C8 H8C 0.978(13) C9 H9C 0.980(14) C9 H9A 0.984(15) C9 H9B 0.950(13)