#------------------------------------------------------------------------------ #$Date: 2018-05-23 16:55:33 +0300 (Wed, 23 May 2018) $ #$Revision: 207940 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/74/7057453.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_7057453 loop_ _publ_author_name 'Fouchet, Julien' 'Heinrich, Beno\^it' 'L'Her, Matthieu' 'Voirin, Emilie' 'Karmazin, Lydia' 'Bailly, Corinne' 'Welter, Richard' 'Mirjafari, Arsalan' 'Douce, Laurent' _publ_section_title ; Heterogeneous Microwave-assisted Ullmann type Methodology for Synthesis of Rigid-core Ionic Liquid Crystals. ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C8NJ01609G _journal_year 2018 _chemical_formula_moiety 'C22 H35 N2, Br' _chemical_formula_sum 'C22 H35 Br N2' _chemical_formula_weight 407.43 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-03-16 deposited with the CCDC. 2018-05-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.385(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 20.4743(10) _cell_length_b 14.5386(6) _cell_length_c 7.5277(4) _cell_measurement_reflns_used 52865 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 0.998 _cell_volume 2204.05(18) _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_molecular_graphics 'PLATON 2003 (Spek, 2003)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_unetI/netI 0.0763 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 16002 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.449 _diffrn_reflns_theta_min 1.011 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 1.872 _exptl_absorpt_correction_T_max 0.75162 _exptl_absorpt_correction_T_min 0.58705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.228 _exptl_crystal_description plate _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.347 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.129 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 5009 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.162 _refine_ls_R_factor_all 0.1026 _refine_ls_R_factor_gt 0.0608 _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^)+(0.0777P)^2^+0.6219P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1316 _refine_ls_wR_factor_ref 0.1647 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3628 _reflns_number_total 5009 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8nj01609g2.cif _cod_data_source_block jlgld110215 _cod_database_code 7057453 _shelx_shelxl_version_number 2014/7 _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 ; shelx.res created by SHELXL-2014/7 TITL import in P 21/a CELL 0.71073 20.4743 14.5386 7.5277 90.000 100.385 90.000 ZERR 4.00 0.0010 0.0006 0.0004 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N BR UNIT 88 140 8 4 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF L.S. 12 TEMP -100.00 WGHT 0.077700 0.621900 FVAR 0.35215 C1 1 1.041978 0.798425 0.073192 11.00000 0.02572 0.02575 = 0.01965 0.00112 0.00148 0.00377 C2 1 1.094950 0.852614 0.045349 11.00000 0.03304 0.02641 = 0.03253 0.00058 0.00425 -0.00226 AFIX 43 H2 2 1.092753 0.917664 0.054679 11.00000 -1.20000 AFIX 0 C3 1 1.150843 0.811016 0.003970 11.00000 0.02802 0.03728 = 0.02866 -0.00101 0.00580 -0.00727 AFIX 43 H3 2 1.186730 0.848410 -0.017077 11.00000 -1.20000 AFIX 0 C4 1 1.156257 0.715946 -0.007877 11.00000 0.02805 0.03593 = 0.02003 -0.00224 0.00226 0.00236 C5 1 1.101936 0.663799 0.016185 11.00000 0.03597 0.02657 = 0.02601 0.00029 0.00174 0.00402 AFIX 43 H5 2 1.103680 0.598870 0.003630 11.00000 -1.20000 AFIX 0 C6 1 1.045018 0.703645 0.058114 11.00000 0.03220 0.02316 = 0.02308 -0.00078 0.00383 -0.00277 AFIX 43 H6 2 1.008647 0.666427 0.076222 11.00000 -1.20000 AFIX 0 C7 1 1.218844 0.671596 -0.042112 11.00000 0.03141 0.05286 = 0.03973 -0.00421 0.00718 0.00572 AFIX 137 H7A 2 1.252273 0.672809 0.068853 11.00000 -1.50000 H7B 2 1.235537 0.705253 -0.137505 11.00000 -1.50000 H7C 2 1.209672 0.607707 -0.080084 11.00000 -1.50000 AFIX 0 C8 1 0.927074 0.799495 0.127709 11.00000 0.03020 0.02286 = 0.03187 -0.00041 0.00381 0.00200 AFIX 43 H8 2 0.916231 0.738156 0.089982 11.00000 -1.20000 AFIX 0 C9 1 0.980655 0.930713 0.185678 11.00000 0.03554 0.02178 = 0.03139 -0.00442 0.00486 -0.00115 AFIX 43 H9 2 1.014235 0.976492 0.195917 11.00000 -1.20000 AFIX 0 C10 1 0.919619 0.940030 0.228679 11.00000 0.03250 0.02457 = 0.03813 -0.00546 0.00595 0.00079 AFIX 43 H10 2 0.902350 0.993805 0.275037 11.00000 -1.20000 AFIX 0 C11 1 0.819655 0.835558 0.223874 11.00000 0.03119 0.03242 = 0.03558 0.00209 0.01263 0.00172 AFIX 23 H11A 2 0.816411 0.851309 0.349936 11.00000 -1.20000 H11B 2 0.811899 0.768609 0.207960 11.00000 -1.20000 AFIX 0 C12 1 0.766112 0.887186 0.096041 11.00000 0.02976 0.05814 = 0.02817 0.00913 0.00583 0.00547 AFIX 23 H12A 2 0.770004 0.873474 -0.030450 11.00000 -1.20000 H12B 2 0.772163 0.954219 0.115540 11.00000 -1.20000 AFIX 0 C13 1 0.696860 0.858707 0.128653 11.00000 0.03289 0.06306 = 0.03035 0.00288 0.00286 0.00159 AFIX 23 H13A 2 0.663000 0.884528 0.030791 11.00000 -1.20000 H13B 2 0.693282 0.790848 0.121622 11.00000 -1.20000 AFIX 0 C14 1 0.681433 0.889967 0.308847 11.00000 0.02620 0.04493 = 0.04154 -0.00256 0.00776 -0.00060 AFIX 23 H14A 2 0.683993 0.957912 0.315463 11.00000 -1.20000 H14B 2 0.715466 0.864906 0.407162 11.00000 -1.20000 AFIX 0 C15 1 0.612770 0.859221 0.338126 11.00000 0.02753 0.04196 = 0.03973 -0.00084 0.00546 0.00045 AFIX 23 H15A 2 0.578958 0.882935 0.237790 11.00000 -1.20000 H15B 2 0.610699 0.791205 0.334040 11.00000 -1.20000 AFIX 0 C16 1 0.595721 0.891589 0.515032 11.00000 0.03029 0.04017 = 0.04189 -0.00081 0.00953 -0.00080 AFIX 23 H16A 2 0.596622 0.959662 0.517792 11.00000 -1.20000 H16B 2 0.630154 0.869231 0.615252 11.00000 -1.20000 AFIX 0 C17 1 0.527470 0.858575 0.546292 11.00000 0.03019 0.04160 = 0.03935 -0.00113 0.00462 -0.00304 AFIX 23 H17A 2 0.493134 0.880125 0.445045 11.00000 -1.20000 H17B 2 0.526823 0.790487 0.545281 11.00000 -1.20000 AFIX 0 C18 1 0.509734 0.892062 0.722423 11.00000 0.03043 0.03921 = 0.03600 -0.00012 0.00377 -0.00294 AFIX 23 H18A 2 0.510941 0.960135 0.723884 11.00000 -1.20000 H18B 2 0.543884 0.869971 0.823597 11.00000 -1.20000 AFIX 0 C19 1 0.441936 0.860563 0.753707 11.00000 0.03316 0.04197 = 0.04296 0.00163 0.00482 -0.00761 AFIX 23 H19A 2 0.440482 0.792503 0.751382 11.00000 -1.20000 H19B 2 0.407634 0.883243 0.653486 11.00000 -1.20000 AFIX 0 C20 1 0.425218 0.894004 0.931948 11.00000 0.03025 0.03857 = 0.03755 -0.00147 0.00517 -0.00178 AFIX 23 H20A 2 0.459902 0.871817 1.031716 11.00000 -1.20000 H20B 2 0.426528 0.962072 0.933547 11.00000 -1.20000 AFIX 0 C21 1 0.358050 0.862868 0.967009 11.00000 0.03593 0.05837 = 0.03627 0.00183 0.00174 -0.01061 AFIX 23 H21A 2 0.356383 0.794817 0.964655 11.00000 -1.20000 H21B 2 0.323127 0.885787 0.868600 11.00000 -1.20000 AFIX 0 C22 1 0.343153 0.896521 1.147360 11.00000 0.03801 0.07334 = 0.04330 0.00236 0.01335 -0.00867 AFIX 137 H22A 2 0.376635 0.872295 1.245847 11.00000 -1.50000 H22B 2 0.299067 0.874996 1.161935 11.00000 -1.50000 H22C 2 0.344181 0.963902 1.150216 11.00000 -1.50000 AFIX 0 N1 3 0.984742 0.841121 0.123557 11.00000 0.02751 0.02278 = 0.02056 -0.00074 0.00137 -0.00219 N2 3 0.887143 0.857457 0.193035 11.00000 0.02548 0.02949 = 0.02794 -0.00202 0.00703 0.00205 BR1 4 0.872307 0.920866 0.696646 11.00000 0.04218 0.02633 = 0.03733 -0.00306 0.00782 -0.00386 HKLF 4 REM import in P 21/a REM R1 = 0.0608 for 3628 Fo > 4sig(Fo) and 0.1026 for all 5009 data REM 228 parameters refined using 0 restraints END WGHT 0.0777 0.6219 REM Highest difference peak 0.347, deepest hole -0.475, 1-sigma level 0.129 Q1 1 1.2657 0.7200 0.0001 11.00000 0.05 0.35 Q2 1 0.3213 0.7656 0.8208 11.00000 0.05 0.35 Q3 1 1.1491 0.7578 -0.0195 11.00000 0.05 0.33 Q4 1 0.3282 0.8214 0.9187 11.00000 0.05 0.33 Q5 1 1.2532 0.7495 0.1452 11.00000 0.05 0.32 Q6 1 0.3101 0.8230 1.1648 11.00000 0.05 0.32 Q7 1 0.2948 0.9372 0.7145 11.00000 0.05 0.32 Q8 1 0.3504 0.8808 1.0502 11.00000 0.05 0.31 Q9 1 0.3375 0.7629 0.9700 11.00000 0.05 0.31 Q10 1 1.2653 0.7027 -0.2884 11.00000 0.05 0.30 ; _shelx_res_checksum 57848 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 1.04198(17) 0.7984(2) 0.0732(5) 0.0240(8) Uani 1 1 d . . C2 C 1.09495(19) 0.8526(3) 0.0453(5) 0.0309(9) Uani 1 1 d . . H2 H 1.0928 0.9177 0.0547 0.037 Uiso 1 1 calc R U C3 C 1.15084(19) 0.8110(3) 0.0040(5) 0.0312(9) Uani 1 1 d . . H3 H 1.1867 0.8484 -0.0171 0.037 Uiso 1 1 calc R U C4 C 1.15626(19) 0.7159(3) -0.0079(5) 0.0283(9) Uani 1 1 d . . C5 C 1.10194(19) 0.6638(3) 0.0162(5) 0.0300(9) Uani 1 1 d . . H5 H 1.1037 0.5989 0.0036 0.036 Uiso 1 1 calc R U C6 C 1.04502(19) 0.7036(2) 0.0581(5) 0.0263(8) Uani 1 1 d . . H6 H 1.0086 0.6664 0.0762 0.032 Uiso 1 1 calc R U C7 C 1.2188(2) 0.6716(3) -0.0421(6) 0.0412(11) Uani 1 1 d . . H7A H 1.2523 0.6728 0.0689 0.062 Uiso 1 1 calc R U H7B H 1.2355 0.7053 -0.1375 0.062 Uiso 1 1 calc R U H7C H 1.2097 0.6077 -0.0801 0.062 Uiso 1 1 calc R U C8 C 0.92707(18) 0.7995(3) 0.1277(5) 0.0285(9) Uani 1 1 d . . H8 H 0.9162 0.7382 0.0900 0.034 Uiso 1 1 calc R U C9 C 0.9807(2) 0.9307(2) 0.1857(6) 0.0297(9) Uani 1 1 d . . H9 H 1.0142 0.9765 0.1959 0.036 Uiso 1 1 calc R U C10 C 0.9196(2) 0.9400(3) 0.2287(6) 0.0318(9) Uani 1 1 d . . H10 H 0.9024 0.9938 0.2750 0.038 Uiso 1 1 calc R U C11 C 0.81966(19) 0.8356(3) 0.2239(6) 0.0322(9) Uani 1 1 d . . H11A H 0.8164 0.8513 0.3499 0.039 Uiso 1 1 calc R U H11B H 0.8119 0.7686 0.2080 0.039 Uiso 1 1 calc R U C12 C 0.7661(2) 0.8872(3) 0.0960(6) 0.0386(10) Uani 1 1 d . . H12A H 0.7700 0.8735 -0.0304 0.046 Uiso 1 1 calc R U H12B H 0.7722 0.9542 0.1155 0.046 Uiso 1 1 calc R U C13 C 0.6969(2) 0.8587(3) 0.1287(6) 0.0425(11) Uani 1 1 d . . H13A H 0.6630 0.8845 0.0308 0.051 Uiso 1 1 calc R U H13B H 0.6933 0.7908 0.1216 0.051 Uiso 1 1 calc R U C14 C 0.6814(2) 0.8900(3) 0.3088(6) 0.0374(10) Uani 1 1 d . . H14A H 0.6840 0.9579 0.3155 0.045 Uiso 1 1 calc R U H14B H 0.7155 0.8649 0.4072 0.045 Uiso 1 1 calc R U C15 C 0.6128(2) 0.8592(3) 0.3381(6) 0.0365(10) Uani 1 1 d . . H15A H 0.5790 0.8829 0.2378 0.044 Uiso 1 1 calc R U H15B H 0.6107 0.7912 0.3340 0.044 Uiso 1 1 calc R U C16 C 0.5957(2) 0.8916(3) 0.5150(6) 0.0371(10) Uani 1 1 d . . H16A H 0.5966 0.9597 0.5178 0.044 Uiso 1 1 calc R U H16B H 0.6302 0.8692 0.6153 0.044 Uiso 1 1 calc R U C17 C 0.5275(2) 0.8586(3) 0.5463(6) 0.0373(10) Uani 1 1 d . . H17A H 0.4931 0.8801 0.4450 0.045 Uiso 1 1 calc R U H17B H 0.5268 0.7905 0.5453 0.045 Uiso 1 1 calc R U C18 C 0.5097(2) 0.8921(3) 0.7224(6) 0.0355(10) Uani 1 1 d . . H18A H 0.5109 0.9601 0.7239 0.043 Uiso 1 1 calc R U H18B H 0.5439 0.8700 0.8236 0.043 Uiso 1 1 calc R U C19 C 0.4419(2) 0.8606(3) 0.7537(6) 0.0396(11) Uani 1 1 d . . H19A H 0.4405 0.7925 0.7514 0.048 Uiso 1 1 calc R U H19B H 0.4076 0.8832 0.6535 0.048 Uiso 1 1 calc R U C20 C 0.4252(2) 0.8940(3) 0.9319(6) 0.0356(10) Uani 1 1 d . . H20A H 0.4599 0.8718 1.0317 0.043 Uiso 1 1 calc R U H20B H 0.4265 0.9621 0.9335 0.043 Uiso 1 1 calc R U C21 C 0.3581(2) 0.8629(3) 0.9670(6) 0.0441(11) Uani 1 1 d . . H21A H 0.3564 0.7948 0.9647 0.053 Uiso 1 1 calc R U H21B H 0.3231 0.8858 0.8686 0.053 Uiso 1 1 calc R U C22 C 0.3432(2) 0.8965(4) 1.1474(7) 0.0508(13) Uani 1 1 d . . H22A H 0.3766 0.8723 1.2458 0.076 Uiso 1 1 calc R U H22B H 0.2991 0.8750 1.1619 0.076 Uiso 1 1 calc R U H22C H 0.3442 0.9639 1.1502 0.076 Uiso 1 1 calc R U N1 N 0.98474(15) 0.8411(2) 0.1236(4) 0.0240(7) Uani 1 1 d . . N2 N 0.88714(15) 0.8575(2) 0.1930(4) 0.0274(7) Uani 1 1 d . . Br1 Br 0.87231(2) 0.92087(3) 0.69665(6) 0.03520(17) 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 C1 0.026(2) 0.0258(19) 0.0197(19) 0.0011(15) 0.0015(16) 0.0038(15) C2 0.033(2) 0.026(2) 0.033(2) 0.0006(17) 0.0043(18) -0.0023(16) C3 0.028(2) 0.037(2) 0.029(2) -0.0010(18) 0.0058(18) -0.0073(17) C4 0.028(2) 0.036(2) 0.020(2) -0.0022(17) 0.0023(17) 0.0024(16) C5 0.036(2) 0.0266(19) 0.026(2) 0.0003(17) 0.0017(18) 0.0040(16) C6 0.032(2) 0.0232(18) 0.023(2) -0.0008(15) 0.0038(17) -0.0028(15) C7 0.031(2) 0.053(3) 0.040(3) -0.004(2) 0.007(2) 0.0057(19) C8 0.030(2) 0.0229(18) 0.032(2) -0.0004(17) 0.0038(18) 0.0020(16) C9 0.036(2) 0.0218(19) 0.031(2) -0.0044(17) 0.0049(18) -0.0011(15) C10 0.033(2) 0.025(2) 0.038(2) -0.0055(17) 0.0059(19) 0.0008(15) C11 0.031(2) 0.032(2) 0.036(2) 0.0021(18) 0.0126(19) 0.0017(16) C12 0.030(2) 0.058(3) 0.028(2) 0.009(2) 0.0058(19) 0.005(2) C13 0.033(2) 0.063(3) 0.030(2) 0.003(2) 0.003(2) 0.002(2) C14 0.026(2) 0.045(2) 0.042(3) -0.003(2) 0.008(2) -0.0006(18) C15 0.028(2) 0.042(2) 0.040(3) -0.001(2) 0.0055(19) 0.0004(17) C16 0.030(2) 0.040(2) 0.042(3) -0.001(2) 0.010(2) -0.0008(17) C17 0.030(2) 0.042(2) 0.039(3) -0.001(2) 0.0046(19) -0.0030(18) C18 0.030(2) 0.039(2) 0.036(3) -0.0001(19) 0.0038(19) -0.0029(17) C19 0.033(2) 0.042(2) 0.043(3) 0.002(2) 0.005(2) -0.0076(19) C20 0.030(2) 0.039(2) 0.038(3) -0.0015(19) 0.0052(19) -0.0018(17) C21 0.036(2) 0.058(3) 0.036(3) 0.002(2) 0.002(2) -0.011(2) C22 0.038(3) 0.073(3) 0.043(3) 0.002(3) 0.013(2) -0.009(2) N1 0.0275(17) 0.0228(15) 0.0206(16) -0.0007(13) 0.0014(14) -0.0022(12) N2 0.0255(17) 0.0295(17) 0.0279(18) -0.0020(14) 0.0070(15) 0.0020(13) Br1 0.0422(3) 0.0263(2) 0.0373(3) -0.00306(18) 0.00782(19) -0.00386(17) 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' Br Br -0.2901 2.4595 '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 C6 C1 C2 120.3(3) C6 C1 N1 120.2(3) C2 C1 N1 119.5(3) C3 C2 C1 119.2(4) C3 C2 H2 120.4 C1 C2 H2 120.4 C2 C3 C4 122.0(4) C2 C3 H3 119.0 C4 C3 H3 119.0 C5 C4 C3 117.4(4) C5 C4 C7 121.3(4) C3 C4 C7 121.3(4) C4 C5 C6 121.9(4) C4 C5 H5 119.1 C6 C5 H5 119.1 C1 C6 C5 119.1(4) C1 C6 H6 120.5 C5 C6 H6 120.5 C4 C7 H7A 109.5 C4 C7 H7B 109.5 H7A C7 H7B 109.5 C4 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 N2 C8 N1 109.1(3) N2 C8 H8 125.4 N1 C8 H8 125.4 C10 C9 N1 106.7(3) C10 C9 H9 126.6 N1 C9 H9 126.6 C9 C10 N2 107.5(3) C9 C10 H10 126.2 N2 C10 H10 126.2 N2 C11 C12 112.5(3) N2 C11 H11A 109.1 C12 C11 H11A 109.1 N2 C11 H11B 109.1 C12 C11 H11B 109.1 H11A C11 H11B 107.8 C11 C12 C13 110.3(4) C11 C12 H12A 109.6 C13 C12 H12A 109.6 C11 C12 H12B 109.6 C13 C12 H12B 109.6 H12A C12 H12B 108.1 C14 C13 C12 114.1(4) C14 C13 H13A 108.7 C12 C13 H13A 108.7 C14 C13 H13B 108.7 C12 C13 H13B 108.7 H13A C13 H13B 107.6 C13 C14 C15 112.7(4) C13 C14 H14A 109.0 C15 C14 H14A 109.0 C13 C14 H14B 109.0 C15 C14 H14B 109.0 H14A C14 H14B 107.8 C16 C15 C14 113.6(4) C16 C15 H15A 108.8 C14 C15 H15A 108.8 C16 C15 H15B 108.8 C14 C15 H15B 108.8 H15A C15 H15B 107.7 C15 C16 C17 113.5(4) C15 C16 H16A 108.9 C17 C16 H16A 108.9 C15 C16 H16B 108.9 C17 C16 H16B 108.9 H16A C16 H16B 107.7 C18 C17 C16 113.7(3) C18 C17 H17A 108.8 C16 C17 H17A 108.8 C18 C17 H17B 108.8 C16 C17 H17B 108.8 H17A C17 H17B 107.7 C17 C18 C19 114.1(4) C17 C18 H18A 108.7 C19 C18 H18A 108.7 C17 C18 H18B 108.7 C19 C18 H18B 108.7 H18A C18 H18B 107.6 C18 C19 C20 113.4(4) C18 C19 H19A 108.9 C20 C19 H19A 108.9 C18 C19 H19B 108.9 C20 C19 H19B 108.9 H19A C19 H19B 107.7 C21 C20 C19 114.4(4) C21 C20 H20A 108.7 C19 C20 H20A 108.7 C21 C20 H20B 108.7 C19 C20 H20B 108.7 H20A C20 H20B 107.6 C20 C21 C22 113.1(4) C20 C21 H21A 109.0 C22 C21 H21A 109.0 C20 C21 H21B 109.0 C22 C21 H21B 109.0 H21A C21 H21B 107.8 C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C8 N1 C9 108.1(3) C8 N1 C1 125.4(3) C9 N1 C1 126.5(3) C8 N2 C10 108.5(3) C8 N2 C11 125.2(3) C10 N2 C11 126.2(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C6 1.385(5) C1 C2 1.387(5) C1 N1 1.436(5) C2 C3 1.379(6) C2 H2 0.9500 C3 C4 1.391(5) C3 H3 0.9500 C4 C5 1.385(5) C4 C7 1.498(5) C5 C6 1.388(5) C5 H5 0.9500 C6 H6 0.9500 C7 H7A 0.9800 C7 H7B 0.9800 C7 H7C 0.9800 C8 N2 1.329(5) C8 N1 1.332(5) C8 H8 0.9500 C9 C10 1.353(6) C9 N1 1.392(4) C9 H9 0.9500 C10 N2 1.375(5) C10 H10 0.9500 C11 N2 1.477(5) C11 C12 1.520(6) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.539(6) C12 H12A 0.9900 C12 H12B 0.9900 C13 C14 1.517(6) C13 H13A 0.9900 C13 H13B 0.9900 C14 C15 1.529(6) C14 H14A 0.9900 C14 H14B 0.9900 C15 C16 1.511(6) C15 H15A 0.9900 C15 H15B 0.9900 C16 C17 1.535(6) C16 H16A 0.9900 C16 H16B 0.9900 C17 C18 1.517(6) C17 H17A 0.9900 C17 H17B 0.9900 C18 C19 1.520(6) C18 H18A 0.9900 C18 H18B 0.9900 C19 C20 1.523(6) C19 H19A 0.9900 C19 H19B 0.9900 C20 C21 1.515(6) C20 H20A 0.9900 C20 H20B 0.9900 C21 C22 1.525(6) C21 H21A 0.9900 C21 H21B 0.9900 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 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 C6 C1 C2 C3 -0.5(6) N1 C1 C2 C3 177.5(3) C1 C2 C3 C4 -1.1(6) C2 C3 C4 C5 2.6(6) C2 C3 C4 C7 -176.3(4) C3 C4 C5 C6 -2.7(6) C7 C4 C5 C6 176.3(4) C2 C1 C6 C5 0.5(6) N1 C1 C6 C5 -177.5(3) C4 C5 C6 C1 1.2(6) N1 C9 C10 N2 -0.1(5) N2 C11 C12 C13 177.6(3) C11 C12 C13 C14 68.3(5) C12 C13 C14 C15 -179.1(4) C13 C14 C15 C16 -178.6(4) C14 C15 C16 C17 -178.5(4) C15 C16 C17 C18 -179.2(4) C16 C17 C18 C19 179.4(4) C17 C18 C19 C20 179.4(4) C18 C19 C20 C21 -179.5(4) C19 C20 C21 C22 179.3(4) N2 C8 N1 C9 -1.4(4) N2 C8 N1 C1 175.4(3) C10 C9 N1 C8 0.9(5) C10 C9 N1 C1 -175.9(3) C6 C1 N1 C8 -12.7(6) C2 C1 N1 C8 169.3(4) C6 C1 N1 C9 163.5(4) C2 C1 N1 C9 -14.5(6) N1 C8 N2 C10 1.3(4) N1 C8 N2 C11 -177.9(3) C9 C10 N2 C8 -0.8(5) C9 C10 N2 C11 178.5(4) C12 C11 N2 C8 -111.8(4) C12 C11 N2 C10 69.1(5)