data_2003319 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 734 _journal_page_last 736 _publ_section_title ; Ethylenediamine-N,N'-dimethyl-N,N'-2,2'-di-6-tert-butyl-1,4-benzoquinone ; _chemical_formula_sum 'C24 H32 N2 O4' _chemical_formula_weight 412.52 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_space_group_name_H-M 'P-1' _cell_length_a 6.1970(10) _cell_length_b 9.348(2) _cell_length_c 9.713(2) _cell_angle_alpha 83.90(1) _cell_angle_beta 84.97(1) _cell_angle_gamma 85.85(2) _cell_volume 556.2(2) _cell_formula_units_Z 1 _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 17 _exptl_absorpt_coefficient_mu 0.084 _cell_measurement_temperature 293(2) _exptl_crystal_description 'Transparent blocs' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_colour Red _chemical_compound_source 'see text' _diffrn_measurement_device 'Siemens P4/RA 4-circle' _diffrn_measurement_method \w _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 3732 _reflns_number_total 2949 _reflns_number_observed 2148 _reflns_observed_criterion >2\s(I) _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_theta_max 29.03 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_obs 0.0531 _refine_ls_wR_factor_obs 0.1372 _refine_ls_wR_factor_all 0.1598 _refine_ls_goodness_of_fit_obs 1.054 _refine_ls_goodness_of_fit_all 1.021 _refine_ls_number_reflns 2941 _refine_ls_number_parameters 136 _refine_ls_hydrogen_treatment 'H atoms riding, C-H = 0.96\%A' _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0731P)^2^ + 0.1064P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_shift/esd_max 0.014 _refine_diff_density_max 0.308 _refine_diff_density_min -0.233 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'C' 'C' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 'H' 'H' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 'N' 'N' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003 'O' 'O' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv C1 1 0.6554(2) 0.46352(14) 0.72286(14) 0.0344(3) C2 1 0.5261(2) 0.37590(15) 0.8102(2) 0.0407(3) H2A 1 0.5644 0.27422 0.8213 0.049 C3 1 0.3320(2) 0.4311(2) 0.8827(2) 0.0412(3) C4 1 0.2790(2) 0.5885(2) 0.87007(15) 0.0382(3) H4A 1 0.1584 0.6263 0.92719 0.046 C5 1 0.3934(2) 0.68110(14) 0.78238(14) 0.0333(3) C6 1 0.5691(2) 0.61730(14) 0.68736(15) 0.0399(3) O1 1 0.2124(2) 0.35140(14) 0.9597(2) 0.0660(4) O2 1 0.6329(3) 0.68388(14) 0.57901(14) 0.0756(5) N1 1 0.8482(2) 0.41617(13) 0.66042(13) 0.0429(3) C7 1 1.0069(2) 0.5047(2) 0.57713(14) 0.0389(3) H7A 1 1.1518 0.4722 0.60211 0.047 H7B 1 0.9801 0.6042 0.59698 0.047 C8 1 0.9209(3) 0.2649(2) 0.6892(2) 0.0552(5) H8A 1 1.0566 0.2460 0.6365 0.083 H8B 1 0.8145 0.2052 0.6634 0.083 H8C 1 0.9396(3) 0.2440(2) 0.7865(2) 0.083 C10 1 0.3479(2) 0.84453(14) 0.76812(15) 0.0386(3) C11 1 0.5585(2) 0.91824(14) 0.77722(15) 0.0667(6) H11A 1 0.5277(2) 1.02060(14) 0.77435(15) 0.100 H11B 1 0.6597 0.89699 0.70035 0.100 H11C 1 0.6200 0.88326 0.86272 0.100 C12 1 0.2509(2) 0.89601(14) 0.62999(15) 0.0610(5) H12A 1 0.2312 0.99930 0.62056 0.091 H12B 1 0.1132 0.85551 0.62852 0.091 H12C 1 0.3476 0.86540 0.55449 0.091 C13 1 0.1859(3) 0.8905(2) 0.8861(2) 0.0601(5) H13A 1 0.1679 0.9938 0.8795 0.090 H13B 1 0.2397 0.8549 0.9738 0.090 H13C 1 0.0486 0.8517 0.8788 0.090 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.0370(7) 0.0018(5) 0.0059(5) 0.0298(6) -0.0015(5) 0.0340(6) C2 0.0420(8) -0.0015(6) 0.0081(6) 0.0298(6) 0.0024(5) 0.0467(8) C3 0.0362(7) -0.0053(6) 0.0072(6) 0.0373(7) 0.0041(6) 0.0468(8) C4 0.0317(6) -0.0010(5) 0.0082(5) 0.0395(7) -0.0023(5) 0.0408(7) C5 0.0306(6) 0.0018(5) 0.0046(5) 0.0318(6) -0.0024(5) 0.0356(6) C6 0.0415(8) 0.0044(5) 0.0127(6) 0.0320(6) 0.0029(5) 0.0408(7) O1 0.0511(7) -0.0090(6) 0.0262(7) 0.0500(7) 0.0153(6) 0.0873(10) O2 0.0894(11) 0.0271(7) 0.0454(8) 0.0521(7) 0.0233(6) 0.0652(8) N1 0.0460(7) 0.0061(5) 0.0176(5) 0.0302(6) 0.0019(5) 0.0461(7) C7 0.0377(7) -0.0019(6) 0.0082(6) 0.0378(7) -0.0052(5) 0.0393(7) C8 0.0618(10) 0.0120(7) 0.0190(8) 0.0328(7) 0.0034(7) 0.0627(10) C10 0.0374(7) 0.0038(5) 0.0074(6) 0.0304(6) -0.0015(5) 0.0447(8) C11 0.0563(11) -0.0126(8) 0.0024(11) 0.0439(9) -0.0056(9) 0.100(2) C12 0.0737(13) 0.0174(9) -0.0049(9) 0.0483(9) 0.0046(7) 0.0557(10) C13 0.0664(12) 0.0129(8) 0.0210(9) 0.0450(9) -0.0067(7) 0.0622(10)