#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:50:03 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295815 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160207.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_7160207 loop_ _publ_author_name 'He, Kun' 'Zeng, Weikun' 'Yu, Xianglin' 'Zhou, Jun' 'Jin, Yi' _publ_section_title ; Direct synthesis of Enone-Hydrazones under solvent free and additives free conditions ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01578A _journal_year 2024 _chemical_formula_moiety 'C16 H14 N2 O' _chemical_formula_sum 'C16 H14 N2 O' _chemical_formula_weight 250.29 _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_date 2021-12-16 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2022-07-15 deposited with the CCDC. 2024-11-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.568(3) _cell_length_b 7.6379(19) _cell_length_c 30.481(7) _cell_measurement_reflns_used 2020 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 21.20 _cell_measurement_theta_min 2.21 _cell_volume 2693.2(11) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_unetI/netI 0.0390 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 15473 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.498 _diffrn_reflns_theta_min 1.336 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.235 _exptl_crystal_description block _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.212 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 3069 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0548 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1584 _refine_ls_wR_factor_ref 0.1834 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1885 _reflns_number_total 3069 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01578a2.cif _cod_data_source_block YY _cod_original_cell_volume 2693.3(11) _cod_database_code 7160207 _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. ; _olex2_refinement_description ; 1. Others Fixed Uiso: H1(0.077) H2(0.082) H3(0.082) H4(0.083) H5(0.073) H7(0.073) H8(0.073) H9(0.067) H12(0.069) H13(0.081) H14(0.082) H15(0.081) H16(0.068) Fixed X: H1(0.460441) H2(0.47295) H3(0.616813) H4(0.751396) H5(0.741792) H7(0.532487) H8(0.767917) H9(0.756744) H12(0.741944) H13(0.726713) H14(0.593925) H15(0.47425) H16(0.486607) Fixed Y: H1(0.529382) H2(0.433259) H3(0.245857) H4(0.153518) H5(0.246205) H7(0.539227) H8(0.34213) H9(0.429292) H12(0.485979) H13(0.560105) H14(0.765065) H15(0.895451) H16(0.819186) Fixed Z: H1(0.220005) H2(0.147966) H3(0.127167) H4(0.177526) H5(0.249324) H7(0.295282) H8(0.383772) H9(0.453202) H12(0.518816) H13(0.591888) H14(0.614053) H15(0.563422) H16(0.490306) ; _shelx_res_file ; TITL YY_a.res in Pbca YY.res created by SHELXL-2016/6 at 09:49:31 on 16-Dec-2021 CELL 0.71073 11.5684 7.6379 30.4811 90.000 90.000 90.000 ZERR 8.00 0.0028 0.0019 0.0071 0.000 0.000 0.000 LATT 1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 128 112 16 8 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP 23.000 ACTA L.S. 4 FMAP 2 PLAN -3 0 0.00 HTAB BOND $H CONF WGHT 0.100000 FVAR 0.44886 O1 4 0.557861 0.678279 0.422811 11.00000 0.07197 0.07071 = 0.05104 -0.00323 -0.01064 0.01563 N1 3 0.659260 0.408115 0.317048 11.00000 0.07379 0.06273 = 0.04427 -0.00835 0.00655 -0.00068 N2 3 0.643008 0.477175 0.358667 11.00000 0.07128 0.06356 = 0.04664 -0.00738 -0.00108 0.00581 C1 1 0.519451 0.453536 0.211752 11.00000 0.07010 0.06083 = 0.06065 -0.00292 -0.00451 0.00475 AFIX 43 H1 2 0.460441 0.529382 0.220005 11.00000 -1.20000 AFIX 0 C2 1 0.526978 0.395546 0.168488 11.00000 0.07747 0.07362 = 0.05275 0.00492 -0.01350 -0.01661 AFIX 43 H2 2 0.472950 0.433259 0.147966 11.00000 -1.20000 AFIX 0 C3 1 0.612558 0.284431 0.156061 11.00000 0.08021 0.07784 = 0.04687 -0.00738 0.00855 -0.01930 AFIX 43 H3 2 0.616813 0.245857 0.127167 11.00000 -1.20000 AFIX 0 C4 1 0.692686 0.229194 0.186177 11.00000 0.07051 0.07968 = 0.05648 -0.01155 0.01128 -0.00025 AFIX 43 H4 2 0.751396 0.153518 0.177526 11.00000 -1.20000 AFIX 0 C5 1 0.687070 0.284759 0.229168 11.00000 0.06572 0.06826 = 0.04783 -0.00234 0.00171 0.00387 AFIX 43 H5 2 0.741792 0.246205 0.249324 11.00000 -1.20000 AFIX 0 C6 1 0.599890 0.398208 0.242487 11.00000 0.06673 0.04982 = 0.04639 -0.00563 0.00279 -0.00464 C7 1 0.590430 0.460115 0.287912 11.00000 0.07279 0.06088 = 0.04939 -0.00935 0.00034 0.00375 AFIX 43 H7 2 0.532487 0.539227 0.295282 11.00000 -1.20000 AFIX 0 C8 1 0.711030 0.423460 0.390804 11.00000 0.06572 0.06285 = 0.05340 0.00257 0.00395 0.00642 AFIX 43 H8 2 0.767917 0.342130 0.383772 11.00000 -1.20000 AFIX 0 C9 1 0.704863 0.476970 0.433190 11.00000 0.06356 0.06040 = 0.04337 -0.00079 -0.00336 0.00660 AFIX 43 H9 2 0.756744 0.429292 0.453202 11.00000 -1.20000 AFIX 0 C10 1 0.623254 0.602206 0.448716 11.00000 0.05239 0.04659 = 0.04237 0.00291 -0.00636 -0.00632 C11 1 0.617116 0.646876 0.496462 11.00000 0.04866 0.04249 = 0.04481 -0.00047 -0.00209 -0.00681 C12 1 0.687805 0.568977 0.527544 11.00000 0.06612 0.05541 = 0.05012 -0.00577 -0.00751 0.00512 AFIX 43 H12 2 0.741944 0.485979 0.518816 11.00000 -1.20000 AFIX 0 C13 1 0.678739 0.613245 0.571344 11.00000 0.08396 0.06591 = 0.05148 -0.00241 -0.01443 -0.00176 AFIX 43 H13 2 0.726713 0.560105 0.591888 11.00000 -1.20000 AFIX 0 C14 1 0.599464 0.734915 0.584567 11.00000 0.08507 0.07466 = 0.04421 -0.01076 0.00448 -0.01050 AFIX 43 H14 2 0.593925 0.765065 0.614053 11.00000 -1.20000 AFIX 0 C15 1 0.528114 0.812537 0.554404 11.00000 0.07198 0.06748 = 0.06322 -0.01236 0.00900 0.00674 AFIX 43 H15 2 0.474250 0.895451 0.563422 11.00000 -1.20000 AFIX 0 C16 1 0.536189 0.767595 0.510546 11.00000 0.05889 0.05999 = 0.05169 -0.00426 -0.00293 0.00383 AFIX 43 H16 2 0.486607 0.819186 0.490306 11.00000 -1.20000 REM ##### AFIX 0 H1D 2 0.587603 0.564939 0.366206 11.00000 0.07789 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM YY_a.res in Pbca REM R1 = 0.0548 for 1885 Fo > 4sig(Fo) and 0.0911 for all 3069 data REM 176 parameters refined using 0 restraints END WGHT 0.0805 0.2338 REM Instructions for potential hydrogen bonds EQIV $1 -x+3/2, y-1/2, z HTAB C8 O1_$1 HTAB N2 O1 REM Highest difference peak 0.212, deepest hole -0.192, 1-sigma level 0.035 Q1 1 0.5203 0.4616 0.3130 11.00000 0.05 0.21 Q2 1 0.7353 0.3321 0.3190 11.00000 0.05 0.20 Q3 1 0.7275 0.3619 0.3609 11.00000 0.05 0.16 ; _shelx_res_checksum 20491 _shelx_shelxl_version_number 2016/6 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' '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 _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 0.55786(12) 0.67828(18) 0.42281(4) 0.0646(4) Uani 1 1 d . . . . . N1 N 0.65926(15) 0.4081(2) 0.31705(5) 0.0603(5) Uani 1 1 d . . . . . N2 N 0.64301(15) 0.4772(2) 0.35867(5) 0.0605(5) Uani 1 1 d . . . . . C1 C 0.51945(18) 0.4535(3) 0.21175(6) 0.0639(6) Uani 1 1 d . . . . . H1 H 0.460441 0.529382 0.220005 0.077 Uiso 1 1 calc R U . . . C2 C 0.52698(19) 0.3955(3) 0.16849(6) 0.0679(6) Uani 1 1 d . . . . . H2 H 0.472950 0.433259 0.147966 0.082 Uiso 1 1 calc R U . . . C3 C 0.6126(2) 0.2844(3) 0.15606(7) 0.0683(6) Uani 1 1 d . . . . . H3 H 0.616813 0.245857 0.127167 0.082 Uiso 1 1 calc R U . . . C4 C 0.69269(19) 0.2292(3) 0.18618(6) 0.0689(6) Uani 1 1 d . . . . . H4 H 0.751396 0.153518 0.177526 0.083 Uiso 1 1 calc R U . . . C5 C 0.68707(17) 0.2848(3) 0.22917(6) 0.0606(5) Uani 1 1 d . . . . . H5 H 0.741792 0.246205 0.249324 0.073 Uiso 1 1 calc R U . . . C6 C 0.59989(17) 0.3982(2) 0.24249(6) 0.0543(5) Uani 1 1 d . . . . . C7 C 0.59043(19) 0.4601(3) 0.28791(6) 0.0610(5) Uani 1 1 d . . . . . H7 H 0.532487 0.539227 0.295282 0.073 Uiso 1 1 calc R U . . . C8 C 0.71103(17) 0.4235(3) 0.39080(6) 0.0607(5) Uani 1 1 d . . . . . H8 H 0.767917 0.342130 0.383772 0.073 Uiso 1 1 calc R U . . . C9 C 0.70486(16) 0.4770(3) 0.43319(6) 0.0558(5) Uani 1 1 d . . . . . H9 H 0.756744 0.429292 0.453202 0.067 Uiso 1 1 calc R U . . . C10 C 0.62325(15) 0.6022(2) 0.44872(5) 0.0471(4) Uani 1 1 d . . . . . C11 C 0.61712(14) 0.6469(2) 0.49646(5) 0.0453(4) Uani 1 1 d . . . . . C12 C 0.68780(17) 0.5690(3) 0.52754(6) 0.0572(5) Uani 1 1 d . . . . . H12 H 0.741944 0.485979 0.518816 0.069 Uiso 1 1 calc R U . . . C13 C 0.67874(19) 0.6132(3) 0.57134(6) 0.0671(6) Uani 1 1 d . . . . . H13 H 0.726713 0.560105 0.591888 0.081 Uiso 1 1 calc R U . . . C14 C 0.59946(19) 0.7349(3) 0.58457(6) 0.0680(6) Uani 1 1 d . . . . . H14 H 0.593925 0.765065 0.614053 0.082 Uiso 1 1 calc R U . . . C15 C 0.52811(19) 0.8125(3) 0.55440(6) 0.0676(6) Uani 1 1 d . . . . . H15 H 0.474250 0.895451 0.563422 0.081 Uiso 1 1 calc R U . . . C16 C 0.53619(16) 0.7676(3) 0.51055(6) 0.0569(5) Uani 1 1 d . . . . . H16 H 0.486607 0.819186 0.490306 0.068 Uiso 1 1 calc R U . . . H1D H 0.5876(19) 0.565(3) 0.3662(6) 0.078(7) 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 0.0720(9) 0.0707(10) 0.0510(8) -0.0032(6) -0.0106(6) 0.0156(7) N1 0.0738(11) 0.0627(11) 0.0443(9) -0.0083(8) 0.0065(8) -0.0007(8) N2 0.0713(11) 0.0636(11) 0.0466(9) -0.0074(8) -0.0011(8) 0.0058(9) C1 0.0701(13) 0.0608(13) 0.0607(12) -0.0029(10) -0.0045(10) 0.0047(10) C2 0.0775(14) 0.0736(14) 0.0527(12) 0.0049(11) -0.0135(10) -0.0166(12) C3 0.0802(15) 0.0778(15) 0.0469(11) -0.0074(10) 0.0085(10) -0.0193(12) C4 0.0705(13) 0.0797(16) 0.0565(12) -0.0116(11) 0.0113(10) -0.0003(11) C5 0.0657(12) 0.0683(14) 0.0478(11) -0.0023(9) 0.0017(9) 0.0039(10) C6 0.0667(12) 0.0498(11) 0.0464(10) -0.0056(8) 0.0028(9) -0.0046(9) C7 0.0728(13) 0.0609(13) 0.0494(11) -0.0093(9) 0.0003(9) 0.0037(10) C8 0.0657(12) 0.0628(13) 0.0534(11) 0.0026(10) 0.0039(9) 0.0064(10) C9 0.0636(12) 0.0604(12) 0.0434(10) -0.0008(8) -0.0034(8) 0.0066(9) C10 0.0524(10) 0.0466(10) 0.0424(9) 0.0029(8) -0.0064(8) -0.0063(8) C11 0.0487(10) 0.0425(10) 0.0448(10) -0.0005(7) -0.0021(8) -0.0068(8) C12 0.0661(12) 0.0554(12) 0.0501(11) -0.0058(9) -0.0075(9) 0.0051(9) C13 0.0840(15) 0.0659(14) 0.0515(12) -0.0024(10) -0.0144(10) -0.0018(12) C14 0.0851(15) 0.0747(15) 0.0442(11) -0.0108(10) 0.0045(10) -0.0105(12) C15 0.0720(14) 0.0675(14) 0.0632(13) -0.0124(10) 0.0090(11) 0.0067(11) C16 0.0589(11) 0.0600(12) 0.0517(11) -0.0043(9) -0.0029(9) 0.0038(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 C7 N1 N2 116.12(18) . . ? N1 N2 H1D 125.3(12) . . ? C8 N2 N1 118.63(18) . . ? C8 N2 H1D 116.0(11) . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C6 C1 C2 120.0(2) . . ? C1 C2 H2 119.7 . . ? C3 C2 C1 120.53(19) . . ? C3 C2 H2 119.7 . . ? C2 C3 H3 120.1 . . ? C2 C3 C4 119.90(18) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.6(2) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.23(19) . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.66(17) . . ? C1 C6 C7 119.30(19) . . ? C5 C6 C7 122.04(18) . . ? N1 C7 C6 121.17(19) . . ? N1 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? N2 C8 H8 117.2 . . ? N2 C8 C9 125.51(19) . . ? C9 C8 H8 117.2 . . ? C8 C9 H9 118.2 . . ? C8 C9 C10 123.59(17) . . ? C10 C9 H9 118.2 . . ? O1 C10 C9 120.53(16) . . ? O1 C10 C11 118.96(16) . . ? C9 C10 C11 120.50(16) . . ? C12 C11 C10 122.62(16) . . ? C16 C11 C10 119.09(16) . . ? C16 C11 C12 118.28(16) . . ? C11 C12 H12 119.6 . . ? C13 C12 C11 120.73(19) . . ? C13 C12 H12 119.6 . . ? C12 C13 H13 119.9 . . ? C14 C13 C12 120.17(19) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.0 . . ? C13 C14 C15 120.04(18) . . ? C15 C14 H14 120.0 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.02(19) . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 120.75(18) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? 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 C10 1.238(2) . ? N1 N2 1.387(2) . ? N1 C7 1.257(2) . ? N2 C8 1.322(2) . ? N2 H1D 0.96(2) . ? C1 H1 0.9300 . ? C1 C2 1.394(2) . ? C1 C6 1.386(3) . ? C2 H2 0.9300 . ? C2 C3 1.358(3) . ? C3 H3 0.9300 . ? C3 C4 1.371(3) . ? C4 H4 0.9300 . ? C4 C5 1.379(3) . ? C5 H5 0.9300 . ? C5 C6 1.390(3) . ? C6 C7 1.467(2) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C8 C9 1.357(2) . ? C9 H9 0.9300 . ? C9 C10 1.425(3) . ? C10 C11 1.496(2) . ? C11 C12 1.386(2) . ? C11 C16 1.382(3) . ? C12 H12 0.9300 . ? C12 C13 1.381(2) . ? C13 H13 0.9300 . ? C13 C14 1.366(3) . ? C14 H14 0.9300 . ? C14 C15 1.370(3) . ? C15 H15 0.9300 . ? C15 C16 1.383(3) . ? C16 H16 0.9300 . ? 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 O1 C10 C11 C12 -179.46(17) . . . . ? O1 C10 C11 C16 2.1(3) . . . . ? N1 N2 C8 C9 -179.12(18) . . . . ? N2 N1 C7 C6 179.18(17) . . . . ? N2 C8 C9 C10 -0.7(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C1 C6 C7 N1 177.49(19) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C2 C1 C6 C7 -179.80(18) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C7 179.79(19) . . . . ? C5 C6 C7 N1 -2.3(3) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? C7 N1 N2 C8 178.23(18) . . . . ? C8 C9 C10 O1 -5.1(3) . . . . ? C8 C9 C10 C11 176.37(18) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C9 C10 C11 C16 -179.35(17) . . . . ? C10 C11 C12 C13 -179.57(17) . . . . ? C10 C11 C16 C15 -179.84(17) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C11 C16 C15 1.6(3) . . . . ? C12 C13 C14 C15 0.5(3) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C11 -1.1(3) . . . . ? C16 C11 C12 C13 -1.1(3) . . . . ?