#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:29:44 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266175 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158028.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_7158028 loop_ _publ_author_name 'Natho, Philipp' 'Yang, Zeyu' 'Allen, Lewis A. T.' 'Rey, Juliette' 'White, Andrew J. P.' 'Parsons, Philip J.' _publ_section_title ; An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4048 _journal_page_last 4053 _journal_paper_doi 10.1039/d1ob00430a _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.24 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-01-21 deposited with the CCDC. 2021-04-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.5334(11) _cell_length_b 9.3516(8) _cell_length_c 17.8360(15) _cell_measurement_reflns_used 1440 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.7070 _cell_measurement_theta_min 3.5060 _cell_volume 2090.5(3) _computing_cell_refinement 'CrysAlisPro, Rigaku OD' _computing_data_collection 'CrysAlisPro, Rigaku OD' _computing_data_reduction 'CrysAlisPro, Rigaku OD' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CIFTAB-2014 (Sheldrick, 2017)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2017)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 16.0382 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_device_type 'Agilent Xcalibur 3 E' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_unetI/netI 0.0586 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.863 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 2325 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.863 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.136 _diffrn_reflns_theta_min 2.284 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.266 _exptl_crystal_description 'blocky needles' _exptl_crystal_F_000 848 _exptl_crystal_size_max 0.644 _exptl_crystal_size_mid 0.223 _exptl_crystal_size_min 0.074 _refine_diff_density_max 0.155 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 142 _refine_ls_number_reflns 2325 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.883 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0415 _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^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.0951 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1294 _reflns_number_total 2325 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00430a2.cif _cod_data_source_block 2d _cod_depositor_comments 'Adding full bibliography for 7158028.cif.' _cod_database_code 7158028 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL PJP1904 in Pbca PJP1904.res created by SHELXL-2018/3 at 09:21:18 on 29-Jul-2019 REM Pbca (#61, found as Pcab in ba-c setting) REM PN-IV-17S CELL 0.71073 12.533424 9.351648 17.835996 90.0000 90.0000 90.0000 ZERR 8.00 0.001074 0.000794 0.001538 0.0000 0.0000 0.0000 LATT 1 SYMM -x+1/2,-y, z+1/2 SYMM -x, y+1/2,-z+1/2 SYMM x+1/2,-y+1/2,-z SFAC C H N O UNIT 104 104 8 8 TEMP -100 L.S. 6 OMIT 0 0 -2 FMAP 2 PLAN 10 ACTA DFIX 0.9000 0.0001 N1 H1 REM Modelled as 2 component twin, then using hklf5 file with BASF parameter REM The crystal was modelled as a two component twin in a ca. 54:46 ratio, REM with the two major lattices related by the approximate twin law REM [1.00 0.00 -0.01 0.00 -1.00 0.00 -0.04 0.00 -1.00] REM Unit cell from twin data processing. REM Instructions for potential hydrogen bonds EQIV $1 x+1/2, y, -z+3/2 HTAB N1 O14_$1 WGHT 0.050800 BASF 0.45957 FVAR 4.42826 N1 3 1.112762 0.238821 0.680929 11.00000 0.03443 0.03677 = 0.02752 0.00468 -0.00539 0.00527 H1 2 1.165188 0.204830 0.710448 11.00000 0.05116 C2 1 1.128618 0.340059 0.625872 11.00000 0.03977 0.02631 = 0.02320 -0.00258 0.00034 0.00003 C3 1 1.031582 0.375751 0.596070 11.00000 0.04169 0.03283 = 0.02617 0.00542 -0.00163 0.00448 AFIX 43 H3A 2 1.019480 0.444308 0.557696 11.00000 -1.20000 AFIX 0 C4 1 0.951951 0.292451 0.632480 11.00000 0.03770 0.02858 = 0.02232 -0.00044 0.00225 0.00522 C5 1 0.840985 0.278325 0.623638 11.00000 0.03739 0.03345 = 0.02770 0.00018 -0.00053 0.00793 AFIX 43 H5A 2 0.803022 0.337100 0.589350 11.00000 -1.20000 AFIX 0 C6 1 0.788914 0.177269 0.665900 11.00000 0.03421 0.03436 = 0.03037 -0.00674 0.00649 0.00546 C7 1 0.843967 0.091364 0.717349 11.00000 0.04359 0.03505 = 0.02977 0.00304 0.01004 0.00090 AFIX 43 H7A 2 0.805569 0.022377 0.745644 11.00000 -1.20000 AFIX 0 C8 1 0.951887 0.104437 0.727851 11.00000 0.04526 0.03580 = 0.02718 0.00696 0.00171 0.00877 AFIX 43 H8A 2 0.988752 0.046119 0.762936 11.00000 -1.20000 AFIX 0 C9 1 1.005553 0.206580 0.685092 11.00000 0.03569 0.03059 = 0.02324 -0.00231 0.00138 0.00548 C10 1 1.233766 0.387086 0.603717 11.00000 0.04178 0.03121 = 0.02754 -0.00405 0.00061 0.00021 C11 1 1.334339 0.359408 0.624436 11.00000 0.03705 0.05687 = 0.04362 0.00763 0.00130 0.00013 AFIX 43 H11A 2 1.363747 0.304437 0.664176 11.00000 -1.20000 AFIX 0 C12 1 1.384324 0.445831 0.562754 11.00000 0.04560 0.05312 = 0.04309 -0.00875 0.00774 -0.01419 AFIX 23 H12A 2 1.423264 0.388541 0.524940 11.00000 -1.20000 H12B 2 1.427352 0.528051 0.580311 11.00000 -1.20000 AFIX 0 C13 1 1.268186 0.484014 0.540541 11.00000 0.05937 0.03618 = 0.03548 -0.00190 -0.00162 -0.01144 AFIX 23 H13A 2 1.249433 0.585876 0.547944 11.00000 -1.20000 H13B 2 1.247016 0.450231 0.490084 11.00000 -1.20000 AFIX 0 O14 4 0.680476 0.150067 0.662137 11.00000 0.03470 0.04925 = 0.04579 0.00011 0.00715 0.00388 C15 1 0.617954 0.240082 0.614560 11.00000 0.03415 0.05470 = 0.05166 -0.00793 -0.00083 0.00865 AFIX 137 H15A 2 0.643523 0.231808 0.562817 11.00000 -1.50000 H15B 2 0.624467 0.339558 0.631225 11.00000 -1.50000 H15C 2 0.543002 0.210602 0.617015 11.00000 -1.50000 AFIX 0 HKLF 5 REM PJP1904 in Pbca REM wR2 = 0.0951, GooF = S = 0.883, Restrained GooF = 0.883 for all data REM R1 = 0.0415 for 1294 Fo > 4sig(Fo) and 0.0916 for all 2325 data REM 142 parameters refined using 1 restraints END WGHT 0.0507 0.0000 REM Highest difference peak 0.155, deepest hole -0.179, 1-sigma level 0.037 Q1 1 0.7999 0.2813 0.6737 11.00000 0.05 0.15 Q2 1 0.5490 0.2440 0.6455 11.00000 0.05 0.13 Q3 1 0.6353 0.1343 0.7093 11.00000 0.05 0.12 Q4 1 0.5971 0.3399 0.6544 11.00000 0.05 0.12 Q5 1 0.8413 -0.0730 0.7679 11.00000 0.05 0.12 Q6 1 1.0297 -0.0174 0.7571 11.00000 0.05 0.12 Q7 1 0.8800 0.1211 0.7472 11.00000 0.05 0.12 Q8 1 1.3563 0.2238 0.6381 11.00000 0.05 0.11 Q9 1 0.6801 0.4274 0.5606 11.00000 0.05 0.11 Q10 1 0.5574 0.1594 0.6485 11.00000 0.05 0.11 ; _shelx_res_checksum 12612 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 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 N1 N 1.11276(10) 0.23882(13) 0.68093(7) 0.0329(4) Uani 1 1 d D . . . . H1 H 1.1652(3) 0.2048(9) 0.7104(3) 0.051(5) Uiso 1 1 d D . . . . C2 C 1.12862(13) 0.34006(16) 0.62587(9) 0.0298(4) Uani 1 1 d . . . . . C3 C 1.03158(13) 0.37575(16) 0.59607(9) 0.0336(4) Uani 1 1 d . . . . . H3A H 1.019480 0.444308 0.557696 0.040 Uiso 1 1 calc R U . . . C4 C 0.95195(13) 0.29245(16) 0.63248(8) 0.0295(4) Uani 1 1 d . . . . . C5 C 0.84098(13) 0.27832(16) 0.62364(9) 0.0328(4) Uani 1 1 d . . . . . H5A H 0.803022 0.337100 0.589350 0.039 Uiso 1 1 calc R U . . . C6 C 0.78891(13) 0.17727(17) 0.66590(9) 0.0330(4) Uani 1 1 d . . . . . C7 C 0.84397(14) 0.09136(17) 0.71735(9) 0.0361(4) Uani 1 1 d . . . . . H7A H 0.805569 0.022377 0.745644 0.043 Uiso 1 1 calc R U . . . C8 C 0.95189(14) 0.10444(16) 0.72785(9) 0.0361(4) Uani 1 1 d . . . . . H8A H 0.988752 0.046119 0.762936 0.043 Uiso 1 1 calc R U . . . C9 C 1.00555(12) 0.20658(16) 0.68509(9) 0.0298(4) Uani 1 1 d . . . . . C10 C 1.23377(13) 0.38709(17) 0.60372(9) 0.0335(4) Uani 1 1 d . . . . . C11 C 1.33434(14) 0.3594(2) 0.62444(10) 0.0458(5) Uani 1 1 d . . . . . H11A H 1.363747 0.304437 0.664176 0.055 Uiso 1 1 calc R U . . . C12 C 1.38432(13) 0.4458(2) 0.56275(10) 0.0473(5) Uani 1 1 d . . . . . H12A H 1.423264 0.388541 0.524940 0.057 Uiso 1 1 calc R U . . . H12B H 1.427352 0.528051 0.580311 0.057 Uiso 1 1 calc R U . . . C13 C 1.26819(14) 0.48401(18) 0.54054(10) 0.0437(5) Uani 1 1 d . . . . . H13A H 1.249433 0.585876 0.547944 0.052 Uiso 1 1 calc R U . . . H13B H 1.247016 0.450231 0.490084 0.052 Uiso 1 1 calc R U . . . O14 O 0.68048(9) 0.15007(12) 0.66214(7) 0.0432(3) Uani 1 1 d . . . . . C15 C 0.61795(13) 0.24008(19) 0.61456(11) 0.0468(5) Uani 1 1 d . . . . . H15A H 0.643523 0.231808 0.562817 0.070 Uiso 1 1 calc R U . . . H15B H 0.624467 0.339558 0.631225 0.070 Uiso 1 1 calc R U . . . H15C H 0.543002 0.210602 0.617015 0.070 Uiso 1 1 calc R U . . . 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 N1 0.0344(9) 0.0368(8) 0.0275(8) 0.0047(7) -0.0054(7) 0.0053(7) C2 0.0398(10) 0.0263(8) 0.0232(9) -0.0026(7) 0.0003(8) 0.0000(8) C3 0.0417(10) 0.0328(9) 0.0262(9) 0.0054(8) -0.0016(8) 0.0045(8) C4 0.0377(10) 0.0286(8) 0.0223(9) -0.0004(7) 0.0023(8) 0.0052(8) C5 0.0374(10) 0.0334(9) 0.0277(10) 0.0002(8) -0.0005(8) 0.0079(8) C6 0.0342(11) 0.0344(10) 0.0304(10) -0.0067(8) 0.0065(8) 0.0055(8) C7 0.0436(11) 0.0350(9) 0.0298(9) 0.0030(8) 0.0100(8) 0.0009(9) C8 0.0453(12) 0.0358(10) 0.0272(10) 0.0070(8) 0.0017(8) 0.0088(9) C9 0.0357(10) 0.0306(9) 0.0232(9) -0.0023(7) 0.0014(8) 0.0055(8) C10 0.0418(11) 0.0312(9) 0.0275(9) -0.0040(8) 0.0006(9) 0.0002(8) C11 0.0370(11) 0.0569(12) 0.0436(12) 0.0076(10) 0.0013(9) 0.0001(9) C12 0.0456(12) 0.0531(11) 0.0431(12) -0.0088(9) 0.0077(10) -0.0142(9) C13 0.0594(13) 0.0362(10) 0.0355(11) -0.0019(8) -0.0016(9) -0.0114(9) O14 0.0347(8) 0.0493(7) 0.0458(8) 0.0001(6) 0.0071(6) 0.0039(6) C15 0.0342(10) 0.0547(11) 0.0517(13) -0.0079(10) -0.0008(9) 0.0087(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C2 N1 C9 109.21(12) . . ? C3 C2 N1 108.43(14) . . ? C3 C2 C10 129.07(15) . . ? N1 C2 C10 122.38(14) . . ? C2 C3 C4 108.21(14) . . ? C5 C4 C9 119.60(15) . . ? C5 C4 C3 133.96(15) . . ? C9 C4 C3 106.39(14) . . ? C6 C5 C4 118.23(15) . . ? C5 C6 O14 124.49(15) . . ? C5 C6 C7 121.32(16) . . ? O14 C6 C7 114.19(14) . . ? C8 C7 C6 121.61(15) . . ? C7 C8 C9 117.52(15) . . ? N1 C9 C8 130.45(15) . . ? N1 C9 C4 107.74(14) . . ? C8 C9 C4 121.70(15) . . ? C11 C10 C2 136.44(16) . . ? C11 C10 C13 93.04(14) . . ? C2 C10 C13 130.39(15) . . ? C10 C11 C12 94.96(15) . . ? C11 C12 C13 85.38(13) . . ? C10 C13 C12 86.52(13) . . ? C6 O14 C15 117.31(13) . . ? 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 N1 C2 1.3785(19) . ? N1 C9 1.3791(18) . ? C2 C3 1.369(2) . ? C2 C10 1.444(2) . ? C3 C4 1.423(2) . ? C4 C5 1.406(2) . ? C4 C9 1.406(2) . ? C5 C6 1.374(2) . ? C6 O14 1.3843(18) . ? C6 C7 1.401(2) . ? C7 C8 1.371(2) . ? C8 C9 1.395(2) . ? C10 C11 1.339(2) . ? C10 C13 1.509(2) . ? C11 C12 1.502(2) . ? C12 C13 1.550(2) . ? O14 C15 1.429(2) . ? 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 _geom_hbond_publ_flag N1 H1 O14 0.9000(1) 2.337(4) 3.0404(18) 134.9(5) 6_657 yes